Organic compounds and mixtures, compositions and organic electronic devices comprising the same

Abstract

The present invention provides an organic compound, a mixture, a composition, and an organic electronic device containing the same, relating to the field of optoelectronics. The organic compound has the structure shown below: #imgabs0# This organic compound exhibits excellent optoelectronic properties, and its application in organic electronic devices can effectively improve the luminous efficiency and lifespan of the devices.

Description

Technical Field

[0001] The present invention relates to the field of optoelectronic technology, and in particular to an organic compound and a mixture, a composition and an organic electronic device comprising the organic compound. Background Art

[0002] Organic semiconductor materials offer diverse synthesis options, low manufacturing costs, and excellent optical and electrical properties. Organic electronic devices using these materials, such as flat-panel displays, lighting devices, and organic light-emitting diodes (OLEDs), are widely used.

[0003] Organic electronic devices are a type of self-luminous display device that generates excitons through the transfer and recombination of carriers between various functional layers. They rely on high-quantum-efficiency organic compounds or metal complexes to emit light. They have excellent characteristics such as self-luminescence, high brightness, high efficiency, low driving voltage, wide viewing angle, and high contrast. The structure of an organic electronic device generally includes a positive electrode, a negative electrode, and a functional layer disposed therebetween. To improve the efficiency and lifespan of organic electronic devices, the functional layers can be arranged into a multilayer structure, with each structural layer containing different organic materials. Specifically, the structural layers can be selected from hole injection layers, hole transport layers, light-emitting layers, electron transport layers, electron injection layers, etc. In organic electronic devices, when a voltage is applied to the two electrodes, the positive electrode injects holes into the functional layer, and the negative electrode injects electrons into the functional layer. When the injected holes and electrons meet, excitons are formed, and when the excitons transition back to the ground state, light is emitted.

[0004] In recent years, the luminous efficiency of organic electronic devices, such as organic light-emitting diodes (OLEDs), has significantly improved. However, their internal quantum efficiency has already approached its theoretical limit. The difference in hole and electron mobility prevents the recombination zone from being evenly dispersed throughout the light-emitting layer, thus reducing the device's luminous efficiency. Further improvements in material and device structure can reduce the difference in hole and electron mobility, preventing the shift in the recombination zone and thus improving the device's luminous efficiency and lifespan. Therefore, designing materials with improved performance and enhancing device performance has become a pressing technical challenge for those skilled in the art. Summary of the Invention

[0005] The object of the present invention is to provide an organic compound having good photoelectric properties, which can effectively improve the luminous efficiency and life of the device when applied to an organic electronic device.

[0006] Another object of the present invention is to provide a mixture, a composition and an organic electronic device.

[0007] The present invention solves the technical problem by adopting the following technical solutions:

[0008] An organic compound having a structure as shown in formula (1):

[0009]

[0010] in,

[0011] R1 and R2 are independently selected from hydrogen, deuterium, an alkyl group having 1 to 10 C atoms, a phenyl group, a biphenyl group, a phenyl group substituted by an alkyl group having 1 to 10 C atoms, a biphenyl group substituted by an alkyl group having 1 to 10 C atoms, or a combination of these groups;

[0012] R3 and R4 are independently selected from alkyl groups having 1 to 4 C atoms;

[0013] L1 and L2 are independently selected from a single bond, or a substituted or unsubstituted aromatic group having 6 to 13 ring atoms;

[0014] Ar1 is selected from a substituted or unsubstituted aromatic group having 6 to 18 ring atoms, or a substituted or unsubstituted heteroaromatic group having 5 to 18 ring atoms.

[0015] The present invention also provides a mixture comprising the above-mentioned organic compound and at least one organic functional material, wherein the organic functional material is selected from one of hole injection materials, hole transport materials, electron transport materials, electron injection materials, electron blocking materials, hole blocking materials, luminescent guest materials, luminescent host materials, and organic dyes.

[0016] The present invention also provides a composition comprising the above organic compound or the above mixture and at least one organic solvent.

[0017] The present invention also provides an organic electronic device comprising at least one functional layer, wherein the functional layer comprises the above organic compound, or the functional layer comprises the above mixture, or the functional layer is prepared by the above composition.

[0018] Compared with the prior art, the present invention has the following beneficial effects: the organic compound provided by the present invention has good photoelectric properties, especially excellent hole transport performance and electron blocking performance. The organic compound can be used as an electron blocking material in organic electronic devices, especially in red organic light-emitting diodes, which is beneficial to improving the luminous efficiency and life of the device. BRIEF DESCRIPTION OF THE DRAWINGS

[0019] In order to more clearly illustrate the technical solutions in the embodiments of the present invention, 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 invention. For those skilled in the art, other drawings can be obtained based on these drawings without creative work.

[0020] Figure 1 is a mass spectrum of the organic compound of Example 1 of the present invention;

[0021] Figure 2 This is a schematic structural diagram of the OLED provided in Example 13 of the present invention.

[0022] Reference numerals:

[0023] Substrate 101; anode 102; hole injection layer 103; hole transport layer 104; electron blocking layer 105; light emitting layer 106; electron transport layer 107; electron injection layer 108; cathode 109. DETAILED DESCRIPTION

[0024] The following will clearly and completely describe the technical solutions in the embodiments of the present invention in conjunction with the accompanying drawings. Obviously, the described embodiments are only part of the embodiments of the present invention, not all of the embodiments. Based on the embodiments of the present invention, all other embodiments obtained by those skilled in the art without making any creative efforts shall fall within the scope of protection of the present invention.

[0025] The technical solution provided by the present invention will be described in detail below. It should be noted that the description order of the following embodiments does not limit the preferred order of the embodiments. In addition, in the description of the present invention, the term "including" means "including but not limited to". Various embodiments of the present invention may be presented in the form of a range; it should be understood that the description in the form of a range is merely for convenience and brevity and should not be understood as a rigid limitation on the scope of the present invention; therefore, it should be considered that the range description has specifically disclosed all possible sub-ranges and single numerical values ​​within the range.

[0026] The terms "and / or", "or / and", and "and / or" used in the present invention include any one of two or more related listed items, and also include any and all combinations of the related listed items, wherein the arbitrary and all combinations include any combination of two related listed items, any more related listed items, or all related listed items. It should be noted that when at least three items are connected by at least two conjunctions selected from "and / or", "or / and", and "and / or", it should be understood that in this application, the technical solution undoubtedly includes technical solutions connected by "logical and" and also undoubtedly includes technical solutions connected by "logical or". For example, "A and / or B" includes three parallel solutions of A, B and A+B. For example, the technical solution of "A, and / or, B, and / or, C, and / or, D" includes any one of A, B, C, and D (that is, the technical solution of all being connected by "logical OR"), and also includes any and all combinations of A, B, C, and D, that is, the combination of any two or any three of A, B, C, and D, and also includes the four-item combination of A, B, C, and D (that is, the technical solution of all being connected by "logical AND").

[0027] In the present invention, aromatic group, aromatic series and aromatic ring system have the same meaning and can be used interchangeably.

[0028] In the present invention, heteroaromatic group, heteroaromatic series and heteroaromatic ring system have the same meaning and can be interchanged.

[0029] In the present invention, "heteroatom" refers to non-carbon atoms, such as N atom, O atom, S atom, etc.

[0030] In the present invention, "substituted" means that a hydrogen atom in a substituted group is replaced by a substituent.

[0031] In the present invention, 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.

[0032] In the present invention, "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 group, isocyano group, nitro group, halogen, alkyl group containing 1 to 20 C atoms, heterocyclic group containing 3 to 20 ring atoms, aromatic group containing 6 to 20 ring atoms, heteroaromatic group containing 5 to 20 ring atoms, -NR'R", 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 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 group containing 1 to 10 C atoms, heterocyclic group containing 3 to 20 ring atoms, aromatic group containing 6 to 20 ring atoms, heteroaromatic group containing 5 to 20 ring atoms. Preferably, R is selected from but not limited to: deuterium atom, cyano, isocyano, nitro, halogen, alkyl group containing 1 to 10 C atoms, heterocyclic group containing 3 to 10 ring atoms, aromatic group containing 6 to 20 ring atoms, heteroaromatic group containing 5 to 20 ring atoms, silanyl, 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.

[0033] As used herein, the term "ring atoms" refers to the number of atoms that make up the ring of a compound (e.g., a monocyclic compound, a fused ring compound, a cross-linked compound, a carbocyclic compound, or a heterocyclic compound) formed by atoms bonded together to form a ring. For example, a benzene ring has 6 ring atoms, a naphthalene ring has 10 ring atoms, and a thienyl group has 5 ring atoms. When a ring is substituted with a substituent, the atoms contained in the substituent are not included in the ring atoms. The term "ring atoms" used below has the same meaning unless otherwise specified.

[0034] In the present invention, "aryl or aromatic group" refers to an aromatic hydrocarbon group derived from an aromatic ring compound by removing a hydrogen atom, and can be a monocyclic aromatic group, a condensed aromatic group, or a polycyclic aromatic group. For polycyclic rings, at least one is an aromatic ring system. For example, "substituted or unsubstituted aryl having 6 to 40 ring atoms" refers to an aryl group containing 6 to 40 ring atoms, preferably a substituted or unsubstituted aryl group having 6 to 30 ring atoms, more preferably a substituted or unsubstituted aryl group having 6 to 18 ring atoms, and particularly preferably a substituted or unsubstituted aryl group having 6 to 14 ring atoms, and the aryl group is optionally further substituted; suitable examples include, but are not limited to, phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, fluoranthenyl, triphenylene, pyrenyl, perylenyl, naphthphenyl, fluorenyl, perylene, acenaphthenyl, and their 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), specifically acenaphthene, fluorene, or 9,9-diarylfluorene, triarylamine, diaryl ether systems should also be included in the definition of aromatic groups.

[0035] In the present invention, "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. Suitable examples include, but are not limited to, thienyl, furyl, pyrrolyl, imidazolyl, oxadiazolyl, triazolyl, imidazolyl, pyridyl, bipyridyl, pyrimidine 1-Hydroxy-1-dopamine, 1-dopamine-1-dopamine, 1-dopamine-1-dopamine, 1-dopamine-1-dopamine, 1-dopamine-1-dopamine, 1-dopamine-1-dopamine, 1-dopamine-1-dopamine, 1-dopamine-1-dopamine, 1-dopamine-1-dopamine, 1-dopamine-1-dopamine, 1-dopamine-1-dopamine, 1-dopamine-1-dopamine, 1-dopamine-1-dopamine, 1-dopamine-1-dopamine, 1-dopamine-1-dopamine, 1-dopamine-1-dopamine, 1-dopamine-1-dopamine, 1-dopamine-1-dopamine, 1-dopamine-1-dopamine, 1-dopamine-1-dopamine, 1-dopamine-1-dopamine, 1-dopamine-1-dopamine, 1-dopamine-1-dopamine, 1-dopamine-1-dopamine,

[0036] In the present invention, "alkyl" may refer to a linear, branched and / or cyclic alkyl group. The number of carbon atoms in the alkyl group may be 1 to 50, 1 to 30, 1 to 20, 1 to 10, or 1 to 6. For example, "C 1-9The phrase "alkyl" refers to an alkyl group containing 1 to 9 carbon atoms, each occurrence of which can 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, pentyl, 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, 3,7-dimethyloctyl, cyclooctyl, n-nonyl, n-decyl, adamantyl, 2-ethyldecyl, 2-butyldecyl, 2-hexyldecyl, 2-octyldecyl, n-undecyl, n-dodecyl, 2-ethyldodecyl, 2-butyldodecyl, 2-hexyldodecyl, 2-octyldodecyl, n-tridecyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, 2-ethylhexadecyl, 2-butylhexadecyl, 2-hexylhexadecyl, 2-octylhexadecyl, n-heptadecyl, n-octadecyl, n-nonadecyl, n-eicosyl, 2-ethyleicosyl, 2-butyleicosyl, 2-hexyleicosyl, 2-octyleicosyl, n-heneicosyl, n-docosyl, n-tricosyl, n-tetracosyl, n-pentacosyl, n-hexacosyl, n-heptacosyl, n-octacosyl, n-nonacosyl, n-triacontyl, etc.

[0037] In the present invention, the abbreviations of substituents are: n-normal, sec-secondary, i-iso, t-tertiary, o-ortho, m-meta, p-para, Me methyl, Et ethyl, Pr propyl, Bu butyl, Am n-pentyl, Hx hexyl, Cy cyclohexyl.

[0038] In the present invention, "amino group" 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 amino groups 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.

[0039] In the present invention, unless otherwise defined, a hydroxyl group refers to -OH, a carboxyl group refers to -COOH, a carbonyl group refers to -C(=O)-, an amino group refers to -NH2, a formyl group refers to -C(=O)H, a haloformyl group refers to -C(=O)Z (wherein Z represents a halogen), a carbamoyl group refers to -C(=O)NH2, an isocyanate group refers to -NCO, and an isothiocyanate group refers to -NCS.

[0040] In the present invention, the term "alkoxy" refers to a group with the structure "-O-alkyl", i.e., an alkyl group as defined above connected to another group via an oxygen atom. Suitable examples of phrases containing this term include, but are not limited to, methoxy (-O-CH3 or -OMe), ethoxy (-O-CH2CH3 or -OEt) and tert-butoxy (-OC(CH3)3 or -OtBu).

[0041] In the present invention, "*" connected to a single bond indicates a connection or fusion site.

[0042] In the present invention, when a linking site is not specified in a group, it means that any linking site in the group can be used as the linking site.

[0043] In the present invention, 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 used as the fusion site.

[0044] In the present invention, 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.

[0045] In the present invention, the single bond connecting the substituent runs through the corresponding ring, indicating that the substituent can be connected to any position of the ring, for example It can mean that R is connected to any substitutable position of the benzene ring; express Can be used with The above optional substitutable positions form a ring.

[0046] In the present invention, "adjacent groups" means that there is no substitutable site between two substituents.

[0047] In the present invention, "combinations thereof", "any combination thereof", "any combination thereof" and the like indicate all suitable combinations of any two or more of the listed items.

[0048] In the present invention, “further”, “further”, “particularly”, etc. are used for descriptive purposes to indicate differences in content, but should not be understood as limiting the scope of protection of the present invention.

[0049] In the present invention, the terms "optionally," "optional," and "optional" mean optional or dispensable, i.e., they refer to either option being selected from two parallel options: "with" or "without." If a technical solution contains multiple "optional" clauses, each "optional" clause is independent unless otherwise specified and there are no conflicts or constraints.

[0050] In the present invention, the technical features described in an open manner include closed technical solutions composed of the listed features, and also include open technical solutions containing the listed features.

[0051] An embodiment of the present invention provides an organic compound having a structure as shown in formula (1):

[0052]

[0053] in,

[0054] R1 and R2 are independently selected from hydrogen, deuterium, an alkyl group having 1 to 10 C atoms, a phenyl group, a biphenyl group, a phenyl group substituted by an alkyl group having 1 to 10 C atoms, a biphenyl group substituted by an alkyl group having 1 to 10 C atoms, or a combination of these groups;

[0055] R3 and R4 are independently selected from alkyl groups having 1 to 4 C atoms;

[0056] L1 and L2 are independently selected from a single bond, or a substituted or unsubstituted aromatic group having 6 to 13 ring atoms;

[0057] Ar1 is selected from a substituted or unsubstituted aromatic group having 6 to 18 ring atoms, or a substituted or unsubstituted heteroaromatic group having 5 to 18 ring atoms.

[0058] In some embodiments, R1 and R2 are independently selected from hydrogen, deuterium, an alkyl group having 1 to 4 C atoms, a phenyl group, a biphenyl group, a phenyl group substituted with an alkyl group having 1 to 4 C atoms, or a biphenyl group substituted with an alkyl group having 1 to 10 C atoms.

[0059] In some embodiments, R1 and R2 are independently selected from an alkyl group having 1 to 4 carbon atoms, or a phenyl group.

[0060] Preferably, the alkyl group having 1 to 4 carbon atoms is selected from a linear alkyl group having 1 to 4 carbon atoms or a branched alkyl group having 3 to 4 carbon atoms.

[0061] In some embodiments, R1 is selected from hydrogen, deuterium, methyl, ethyl, isopropyl, tert-butyl, phenyl, or phenyl substituted with one or more methyl groups.

[0062] In some embodiments, R1 is selected from hydrogen, or phenyl, or phenyl substituted with one or more methyl groups.

[0063] In some embodiments, R2 is selected from hydrogen, deuterium, methyl, ethyl, isopropyl, tert-butyl, phenyl, or phenyl substituted with one or more methyl groups.

[0064] In some embodiments, R2 is selected from hydrogen, or phenyl, or phenyl substituted with one or more methyl groups.

[0065] In some embodiments, formula (1) is selected from one of the structures shown in formula (2-1) and formula (2-2):

[0066]

[0067] In some embodiments, R3 and R4 are independently selected from methyl, ethyl or isopropyl.

[0068] In some embodiments, R3 and R4 are selected from the same group; further, R3 and R4 are both selected from methyl.

[0069] In some embodiments, L1 and L2 are independently selected from a single bond, or one of the following structures:

[0070]

[0071] Wherein, * represents the connection site; the H atom of the above group may be further substituted, and the meaning of "substituted" is the same as the "substituted" in "substituted or unsubstituted".

[0072] In some embodiments, L2 is selected from a single bond, or

[0073] In some embodiments, the above formula (2-1) can be selected from one of the structures shown in formula (3-1), formula (3-2), and formula (3-3):

[0074]

[0075] Formula (2-2) can be selected from one of the structures shown in formula (3-4), formula (3-5), and formula (3-6):

[0076]

[0077] In some embodiments, Ar1 is selected from a substituted or unsubstituted aromatic group having 6 to 14 ring atoms, or a substituted or unsubstituted heteroaromatic group having 6 to 14 ring atoms.

[0078] In some embodiments, Ar1 is selected from one of the following structures:

[0079]

[0080] in:

[0081] Each occurrence of Z is independently selected from CR5 or N;

[0082] W is selected from one of O, S, CR6R7, and NR8;

[0083] R5, R6, R7, and R8, when they occur, are each independently selected from a combination of one or more groups selected from hydrogen, deuterium, a straight-chain alkyl group having 1 to 10 C atoms, a straight-chain alkoxy group having 1 to 10 C atoms, a straight-chain thioalkoxy group having 1 to 10 C atoms, a branched-chain alkyl group having 3 to 10 C atoms, a cyclic alkyl group having 3 to 10 C atoms, a silyl group, -CF3, -Cl, -Br, -F, -CN, a substituted or unsubstituted aromatic group having 6 to 10 ring atoms, and a substituted or unsubstituted heteroaromatic group having 5 to 10 ring atoms.

[0084] It should be noted that when Z is a linking site, Z is selected from a C atom; when W is a linking site, W is selected from a N atom.

[0085] Furthermore, Ar1 can be selected from one of the following structures:

[0086]

[0087] Wherein, * represents the connection site; the H atom of the above groups can be further substituted.

[0088] In some embodiments, formula (1) is selected from one of the structures shown in formula (4-1) to formula (4-11):

[0089]

[0090] in,

[0091] Each occurrence of W is independently selected from one of O, S, CR6R7, and NR8;

[0092] R5, R6, R7, and R8, when they occur, are each independently selected from a combination of one or more groups selected from hydrogen, deuterium, a straight-chain alkyl group having 1 to 10 C atoms, a straight-chain alkoxy group having 1 to 10 C atoms, a straight-chain thioalkoxy group having 1 to 10 C atoms, a branched-chain alkyl group having 3 to 10 C atoms, a cyclic alkyl group having 3 to 10 C atoms, a silyl group, -CF3, -Cl, -Br, -F, -CN, a substituted or unsubstituted aromatic group having 6 to 10 ring atoms, and a substituted or unsubstituted heteroaromatic group having 5 to 10 ring atoms.

[0093] In some embodiments, in Formula (4-1) to Formula (4-11), L1 is selected from a single bond or a phenyl group.

[0094] In some embodiments, in formula (4-1) to formula (4-11), R3 and R4 are both selected from methyl groups.

[0095] In some embodiments, in Formula (4-1) to Formula (4-11), R5 is selected from one of hydrogen, deuterium, a straight-chain alkyl group having 1 to 4 C atoms, a branched-chain alkyl group having 3 to 4 C atoms, a cyclic alkyl group having 3 to 4 C atoms, a silyl group, -CF3, -Cl, -Br, -F, -CN, phenyl, and biphenyl.

[0096] The organic compound provided in the embodiment of the present invention is an aromatic amine organic compound, and the aromatic amine organic compound is selected from the following structures:

[0097]

[0098]

[0099]

[0100]

[0101]

[0102]

[0103] In some embodiments, the organic compound provided by the present invention can be applied to an electron blocking layer. Furthermore, the organic compound provided by the present invention can be applied to an electron blocking layer of an organic electronic device.

[0104] An embodiment of the present invention further provides an electron blocking layer material, comprising the above-mentioned organic compound.

[0105] Embodiments of the present invention further provide a mixture comprising the aforementioned organic compound and at least one organic functional material. The organic functional material may be selected from, but not limited to, a hole injection material (HIM), a hole transport material (HTM), an electron transport material (ETM), an electron injection material (EIM), an electron blocking material (EBM), a hole blocking material (HBM), a luminescent guest material, a luminescent host material, and an organic dye. Organic functional materials can be described in detail in, for example, WO2010135519A1, US20090134784A1, and WO2011110277A1, the entire contents of which are incorporated herein by reference.

[0106] In some embodiments, the organic functional material may be selected from electron transport materials.

[0107] An embodiment of the present invention further provides a composition comprising the above-mentioned organic compound or the above-mentioned mixture and at least one organic solvent. The at least one organic solvent is selected from one or more of aromatic or heteroaromatic solvents, aromatic ketone-based solvents, aromatic ether-based solvents, aliphatic ketones, aliphatic ethers, ester-based solvents, alicyclic compounds, olefin compounds, borate ester compounds, and phosphate ester compounds.

[0108] In some embodiments, the at least one organic solvent is selected from aromatic or heteroaromatic based solvents.

[0109] The aromatic or heteroaromatic based solvents may be selected from, 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, Propylbiphenyl, p-methylisopropylbenzene, 1-methylnaphthalene, 1,2,4-trichlorobenzene, 4,4-difluorodiphenylmethane, 1,2-dimethoxy-4-(1-propenyl)benzene, diphenylmethane, 2-phenylpyridine, 3-phenylpyridine, N-methyldiphenylamine, 4-isopropylbiphenyl, α,α-dichlorodiphenylmethane, 4-(3-phenylpropyl)pyridine, benzyl benzoate, 1,1-bis(3,4-dimethylphenyl)ethane, 2-isopropylnaphthalene, quinoline, isoquinoline, methyl 2-furoate, ethyl 2-furoate.

[0110] Aromatic ketone-based solvents may be selected from, but not limited to, 1-tetralone, 2-tetralone, 2-(phenylepoxy)tetralone, 6-(methoxy)tetralone, acetophenone, propiophenone, benzophenone, and derivatives thereof. Derivatives thereof may be selected from, but not limited to, 4-methylacetophenone, 3-methylacetophenone, 2-methylacetophenone, 4-methylpropiophenone, 3-methylpropiophenone, and 2-methylpropiophenone.

[0111] Aromatic ether-based solvents may be selected from, 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.

[0112] The aliphatic ketone may be selected from, but not limited to, 2-nonanone, 3-nonanone, 5-nonanone, 2-decanone, 2,5-hexanedione, 2,6,8-trimethyl-4-nonanone, fenchone, phorone, isophorone, and di-n-amyl ketone.

[0113] The aliphatic ether may be selected from, but not limited to, amyl ether, hexyl ether, dioctyl ether, ethylene glycol dibutyl ether, diethylene glycol diethyl ether, diethylene glycol butyl methyl ether, diethylene glycol dibutyl ether, triethylene glycol dimethyl ether, triethylene glycol ethyl methyl ether, triethylene glycol butyl methyl ether, tripropylene glycol dimethyl ether, and tetraethylene glycol dimethyl ether.

[0114] The ester-based solvent can be selected from, but is not limited to, alkyl octanoate, alkyl sebacate, alkyl stearate, alkyl benzoate, alkyl phenylacetate, alkyl cinnamate, alkyl oxalate, alkyl maleate, alkyl lactone, and alkyl oleate. Preferably, the ester-based solvent is selected from octyl octanoate, diethyl sebacate, diallyl phthalate, and isononyl isononanoate.

[0115] It is understood that the above-mentioned solvents can be used alone or as a mixed solvent of two or more organic solvents.

[0116] In some embodiments, the composition provided by the present invention may further comprise, in addition to the above-mentioned organic compound or mixture and at least one organic solvent, another organic solvent. Examples of other organic solvents include, but are not limited to, a combination of one or more of methanol, ethanol, 2-methoxyethanol, dichloromethane, chloroform, chlorobenzene, o-dichlorobenzene, tetrahydrofuran, anisole, morpholine, toluene, o-xylene, m-xylene, p-xylene, 1,4-dioxane, acetone, methyl ethyl ketone, 1,2-dichloroethane, 3-phenoxytoluene, 1,1,1-trichloroethane, 1,1,2,2-tetrachloroethane, ethyl acetate, butyl acetate, dimethylformamide, dimethylacetamide, dimethyl sulfoxide, tetralin, decalin, and indene.

[0117] In some embodiments, organic solvents particularly suitable for the present invention are solvents having a Hansen solubility parameter within the following ranges:

[0118] δd (dispersion force) is 17.0~23.2MPa 1 / 2 , preferably 18.5 to 21.0 MPa 1 / 2 ;

[0119] δp (polar force) is 0.2~12.5MPa 1 / 2 , preferably 2.0~6.0MPa 1 / 2 ;

[0120] δh (hydrogen bond strength) is 0.9~14.2MPa 1 / 2 , preferably 2.0~6.0MPa 1 / 2 .

[0121] In the compositions provided in the embodiments of the present invention, the boiling point of the organic solvent must be considered when selecting. In the present invention, the boiling point of the organic solvent is ≥150°C; preferably ≥180°C; more preferably ≥200°C; more preferably ≥250°C; and particularly preferably ≥275°C or ≥300°C. This boiling point is beneficial for preventing nozzle clogging in inkjet printheads. During film formation, the organic solvent can evaporate from the solution to form a film containing the functional material.

[0122] In some embodiments, the composition provided by the embodiments of the present invention may be in a solution state.

[0123] In some embodiments, the composition provided by the embodiments of the present invention may be in a suspension state.

[0124] In some embodiments, the composition may include 0.01 to 10 wt % of the organic compound or mixture according to the present invention, preferably 0.1 to 5 wt %, more preferably 0.2 to 5 wt %, and particularly preferably 0.25 to 3 wt %.

[0125] The present invention also relates to the use of the above composition as a coating or printing ink in the preparation of organic electronic devices, in particular to the use of the composition in the preparation of organic electronic devices by printing or coating processes.

[0126] 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 roll printing, offset printing, flexographic printing, rotary printing, spray coating, brush coating, pad printing, slot die coating, etc. Gravure printing, nozzle printing, and inkjet printing are preferred.

[0127] When the composition is in a solution or suspension state, the composition may further include one or more excipients during application, such as surfactants, lubricants, wetting agents, dispersants, hydrophobic agents, adhesives, etc., to adjust viscosity, film-forming properties, improve adhesion, etc.

[0128] The embodiments of the present invention also provide applications of the above organic compound, mixture or composition in organic electronic devices.

[0129] An embodiment of the present invention further provides an organic electronic device, comprising at least one functional layer, wherein the functional layer comprises the above-mentioned organic compound, or the functional layer comprises the above-mentioned mixture, or the functional layer is prepared from the above-mentioned composition.

[0130] Furthermore, the organic electronic device may include a first electrode, a second electrode, and at least one functional layer, the functional layer being disposed between the first electrode and the second electrode, the functional layer comprising the aforementioned organic compound, or comprising the aforementioned mixture, or being prepared from the aforementioned composition. Furthermore, the organic electronic device may include a cathode, an anode, and at least one functional layer, the functional layer being disposed between the cathode and the anode.

[0131] Organic electronic devices may include but are not limited to: organic light emitting diodes (OLEDs), organic photovoltaic cells (OPVs), organic light emitting cells (OLEECs), organic field effect transistors (OFETs), organic light emitting field effect transistors, organic lasers, organic spintronic devices, organic sensors, organic plasmon emitting diodes (Organic Plasmon Emitting Diodes), etc. Organic electronic devices are particularly preferably organic electroluminescent devices, such as OLEDs, OLEECs, and organic light emitting field effect transistors.

[0132] The at least one functional layer can be selected from a hole injection layer (HIL), a hole transport layer (HTL), an emissive layer (EML), an electron blocking layer (EBL), an electron injection layer (EIL), an electron transport layer (ETL), and a hole blocking layer (HBL). Materials suitable for these functional layers are described in detail above and in patents such as WO2010135519A1, US20090134784A1, and WO2011110277A1, the entire contents of which are incorporated herein by reference.

[0133] In some embodiments, the functional layer includes at least one electron blocking layer, and the electron blocking layer comprises the organic compound or mixture described above. The specific definition of the organic compound can be found in the above description.

[0134] In some embodiments, the organic electronic device includes a cathode, an anode, a light-emitting layer located between the cathode and the anode, a hole transport region located between the anode and the light-emitting layer, the hole transport region comprising a hole transport layer and an electron blocking layer, the hole transport layer being located between the anode and the light-emitting layer, and the electron blocking layer being located between the hole transport layer and the light-emitting layer, wherein the electron blocking layer comprises the above-mentioned organic compound or mixture, or is prepared from the above-mentioned composition.

[0135] Furthermore, the material of the light-emitting layer can be selected from a structure as shown in formula (2):

[0136]

[0137] in:

[0138] q is independently selected from 1 or 2;

[0139] Ar2, at each occurrence, is independently selected from a substituted or unsubstituted heteroaromatic group having 5 to 40 ring atoms;

[0140] Ar3, at each occurrence, is independently selected from a substituted or unsubstituted aromatic group having 6 to 40 ring atoms, or a substituted or unsubstituted heteroaromatic group having 5 to 40 ring atoms;

[0141] R9, R 10 Each occurrence is independently selected from a combination of one or more groups selected from H, D, a straight-chain alkyl group having 1 to 20 C atoms, a branched-chain alkyl group having 3 to 20 C atoms, a cyclic alkyl group having 3 to 20 C atoms, a substituted or unsubstituted aromatic group having 6 to 60 ring atoms, and a substituted or unsubstituted heteroaromatic group having 5 to 60 ring atoms.

[0142] In some embodiments, each occurrence of Ar2 is independently selected from quinolyl, or isoquinolyl, or an isoquinolyl derivative group. Preferably, each occurrence of Ar2 is independently selected from quinolyl, or isoquinolyl, or a quinolyl substituted with an alkyl group having 1 to 8 carbon atoms, or an isoquinolyl substituted with an alkyl group having 1 to 8 carbon atoms.

[0143] In some embodiments, each occurrence of Ar3 is independently selected from phenyl and its derivatives. Preferably, each occurrence of Ar3 is independently selected from phenyl or phenyl substituted by an alkyl group having 1 to 8 C atoms.

[0144] In some embodiments, R9, R 10 Each occurrence is independently selected from H, D, straight-chain alkyl having 1 to 10 C atoms, branched-chain alkyl having 3 to 10 C atoms, or cyclic alkyl having 3 to 10 C atoms.

[0145] Preferably, formula (2) can be selected from one of the structures shown in formula (7-1) to formula (7-3):

[0146]

[0147] in:

[0148] a is any integer selected from 0 to 6, b is any integer selected from 0 to 4;

[0149] R 11 、R 12 Each occurrence is independently selected from D, a straight-chain alkyl group having 1 to 20 C atoms, a branched-chain alkyl group having 3 to 20 C atoms, a cyclic alkyl group having 3 to 20 C atoms, a substituted or unsubstituted aromatic group having 6 to 60 ring atoms, a substituted or unsubstituted heteroaromatic group having 5 to 60 ring atoms, or a combination of these groups.

[0150] In some embodiments, at least one R 11 or R 12 It is selected from a linear alkyl group having 1 to 10 C atoms, a branched alkyl group having 3 to 10 C atoms, or a cyclic alkyl group having 3 to 10 C atoms.

[0151] In some embodiments, at least one R 11 is selected from a linear alkyl group having 1 to 8 C atoms, a branched alkyl group having 3 to 8 C atoms, or a cyclic alkyl group having 3 to 8 C atoms. 12 It is selected from a linear alkyl group having 1 to 8 C atoms, a branched alkyl group having 3 to 8 C atoms, or a cyclic alkyl group having 3 to 8 C atoms.

[0152] Furthermore, the material of the light-emitting layer described in formula (2) preferably has, but is not limited to, the following structures, and these structures may be arbitrarily substituted:

[0153]

[0154]

[0155] It can be understood that in addition to the above-mentioned light-emitting layer, electron blocking layer, and hole transport layer, the organic electronic device can also be equipped with some functional layers conventionally used in organic electronic devices to help improve device performance, such as a hole injection layer, an electron transport layer, an electron injection layer, a hole blocking layer, a light extraction layer, etc.

[0156] In some embodiments, the organic electronic device comprises an anode, a hole transport layer, an electron blocking layer, a light-emitting layer, an electron transport layer, and a cathode stacked in sequence.

[0157] In some embodiments, the organic electronic device comprises an anode, a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer, an electron transport layer, an electron injection layer, and a cathode stacked in sequence.

[0158] In some embodiments, the organic electronic device comprises an anode, a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer, and a cathode stacked in sequence.

[0159] Materials suitable for use in these functional layers are described in detail above and in WO2010135519A1, US20090134784A1, and WO2011110277A1, the entire contents of which are hereby incorporated herein by reference.

[0160] In some embodiments, the organic electronic device further comprises a substrate. The substrate may be located on the side of the anode of an upright structure device or the cathode of an inverted structure device away from the light-emitting layer. The substrate may be opaque or transparent. It will be understood that when the substrate is transparent, the organic electronic device is a transparent device. The substrate may also be rigid or flexible, for example, the substrate may be made of plastic, metal, semiconductor wafer or glass. Preferably, the substrate has a smooth surface, and substrates without surface defects are particularly ideal. In a preferred embodiment, the substrate is a flexible substrate. The material of the flexible substrate may be a polymer film or plastic. The glass transition temperature Tg of the flexible substrate is above 150°C, preferably above 200°C, more preferably above 250°C, and particularly preferably above 300°C. As an example, the material of the flexible substrate may be polyethylene terephthalate (PET) or polyethylene glycol (2,6-naphthalene) (PEN).

[0161] The material of the anode is an anode material known in the art for organic electronic devices, such as a conductive metal, a conductive metal oxide or a conductive polymer. In some embodiments, the work function of the anode material, the absolute value of the difference between the HOMO energy level or the valence band energy level of the light-emitting material in the light-emitting layer or the p-type semiconductor material as the hole injection layer or the hole transport layer or the electron blocking layer is less than 0.5 eV, preferably less than 0.3 eV, and particularly preferably less than 0.2 eV. As an example, the material of the anode can be selected from but not limited to at least one of Al, Cu, Au, Ag, Mg, Fe, Co, Ni, Mn, Pd, Pt, ITO and aluminum-doped zinc oxide (AZO). Other suitable anode materials are known and can be easily selected and used by those 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, electron beam (e-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 invention.

[0162] The material of the cathode is a cathode material known in the art for organic electronic devices, such as a conductive metal or a conductive metal oxide. In some embodiments, the work function of the cathode material, the absolute value of the difference between the LUMO energy level or the conduction band energy level of the light-emitting material in the light-emitting layer or the n-type semiconductor material as the electron injection layer, electron transport layer or hole blocking layer is less than 0.5 eV, preferably less than 0.3 eV, and particularly preferably less than 0.2 eV. In principle, all materials that can be used as cathodes of OLEDs can be used as cathode materials for the organic electronic devices of the present application. As an example, the material of the cathode can be selected from but not limited to at least one of Al, Au, Ag, Ca, Ba, Mg, LiF / Al, MgAg alloy, BaF2 / Al, Cu, Fe, Co, Ni, Mn, Pd, Pt and ITO. 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, electron beam (e-beam), etc.

[0163] The material of the hole transport layer is a material known in the art for a hole transport layer, for example, it can be selected from, but not limited to, poly[bis(4-phenyl)(2,4,6-trimethylphenyl)amine] (PTXX), 2,2',7,7'-tetrakis[N,N-di(4-methoxyphenyl)amino]-9,9'-spirobifluorene (spiro-omeTXD), 4,4'-cyclohexylbis[N,N-di(4-methylphenyl)aniline] (TXPC), N,N'-bis(1-naphthyl)-N,N'-diphenyl-1,1'-diphenyl-4-ol ,4′-diamine (NPB), 4,4′-bis(N-carbazole)-1,1′-biphenyl (CBP), poly[(9,9-dioctylfluorenyl-2,7-diyl)-co-(4,4′-(N-(p-butylphenyl))diphenylamine)] (TFB), poly(9-vinylcarbazole) (PVK), polytriphenylamine (Poly-TPD), poly(3,4-ethylenedioxythiophene)-poly(styrenesulfonic acid) (PEDOT:PSS) and 4,4′,4″-tris(carbazole-9-yl)triphenylamine (TCTX).

[0164] The material of the electron transport layer is a material known in the art for electron transport layers, for example, it can be selected from but not limited to at least one of ET and LiQ, PBD (2-(4-biphenyl)-5-phenyloxadiazole), 8-hydroxyquinoline aluminum (Alq3) and graphene.

[0165] Among them, the chemical structures of ET and LiQ are as follows:

[0166]

[0167] The material of the hole injection layer is a material for a hole injection layer known in the art, for example, it can be selected from but not limited to at least one of 2,3,6,7,10,11-hexacyano-1,4,5,8,9,12-hexaazatriphenylene (HAT-CN), F4TCNQ, F6TCNNQ, NDP-9, PEDOT (polyethylenedioxythiophene), PEDOT:PSS and its derivatives doped with s-MoO3 (PEDOT:PSS:s-MoO3).

[0168] The light emitting wavelength of the organic electronic device is between 600 and 700 nm, preferably between 600 and 650 nm, and more preferably between 600 and 630 nm.

[0169] The present invention also relates to applications of the organic electronic device according to the present invention in various electronic devices, including but not limited to applications in display devices, lighting devices, light sources, sensors, and the like.

[0170] Example 1

[0171] This embodiment provides an organic compound, and its synthesis route is as follows:

[0172] Organic compound R2:

[0173]

[0174] Z1 (10.77 g, 30 mmol), Z2 (7.44 g, 30 mmol), potassium carbonate (8.28 g, 60 mmol), and tetrakis(triphenylphosphine)palladium (1.04 g, 0.9 mmol) were weighed into a two-necked flask. A mixed solvent of toluene and methanol was added, the atmosphere was replaced with nitrogen three times, the temperature was raised to 90°C, and the mixture was stirred overnight. After the reaction solution cooled to room temperature, water was added and extracted with ethyl acetate. The mixture was dried over sodium sulfate and the organic solvent was removed by distillation under reduced pressure. The target product Z3 was separated by silica gel column chromatography to obtain 7.06 g of the product, with a yield of 54%.

[0175] Dissolve Z3 (6.54 g, 15 mmol) in anhydrous tetrahydrofuran, cool to -78°C, and slowly add butyl lithium (1.6 M, 9.4 mL). After about 0.5 hours, add acetone (15 mmol) dropwise to the reaction flask. Continue to react at this temperature for half an hour, then warm to room temperature and continue to react for 8 hours. Remove the solvent under reduced pressure, add hydrochloric acid and acetic acid, and reflux for about 2 hours. Cool to room temperature, add deionized water, and extract with ethyl acetate. After concentration, separate on a silica gel column and remove the solvent to obtain 4.24 g of Z4 with a yield of 71%.

[0176] Compounds Z4 (3.98 g, 10 mmol) and Z5 (2.95 g, 10 mmol) were dissolved in anhydrous toluene. Sodium tert-butoxide (1.15 g, 12 mmol) and trisdibenzylideneacetone dipalladium (0.27 g, 0.3 mmol) were added. After nitrogen was replaced three times, tri-tert-butylphosphine (0.3 mmol) was added. The temperature was gradually raised to 80°C and the reaction was stirred for 12 hours. The heat source was then removed. After the system cooled, deionized water was added, the organic layer was separated, and the organic layer was extracted three times with ethyl acetate, concentrated under reduced pressure, and passed through a silica gel column to obtain 4.78 g of product R2, with a yield of 78%; MS: 613 [M + ]. The mass spectrum of organic compound R2 is shown in Figure 1 .

[0177] Example 2

[0178] This embodiment provides an organic compound, and its synthesis route is as follows:

[0179] Organic compound R19:

[0180]

[0181] Compounds Z6 (3.5 g, 15 mmol) and Z7 (3.18 g, 15 mmol) were dissolved in anhydrous toluene. Sodium tert-butoxide (1.73 g, 18 mmol) and trisdibenzylideneacetone dipalladium (0.41 g, 0.45 mmol) were added. After nitrogen was replaced three times, tri-tert-butylphosphine (0.45 mmol) was added. The temperature was gradually raised to 80°C, and the reaction was stirred for 12 hours before removing the heat source. After the system cooled, deionized water was added, the organic layer was separated, and the mixture was extracted three times with ethyl acetate. The mixture was concentrated under reduced pressure and passed through a silica gel column to obtain 3.67 g of product Z8, with a yield of 67%.

[0182] Compound Z8 (3.65 g, 10 mmol) and Z4 (4 g, 10 mmol) were dissolved in anhydrous toluene. Sodium tert-butoxide (1.15 g, 12 mmol) and trisdibenzylideneacetone dipalladium (0.27 g, 0.3 mmol) were added. After nitrogen was replaced three times, tri-tert-butylphosphine (0.3 mmol) was added. The temperature was gradually raised to 80°C and the reaction was stirred for 12 hours. The heat source was then removed. After the system cooled, deionized water was added, the organic layer was separated, and the mixture was extracted three times with ethyl acetate. The mixture was concentrated under reduced pressure and passed through a silica gel column to obtain 4.78 g of product R19, with a yield of 70%; MS: 683 [M + ].

[0183] Example 3

[0184] This embodiment provides an organic compound, and its synthesis route is as follows:

[0185] Organic compound R48:

[0186]

[0187] Z1 (10.77 g, 30 mmol), Z9 (7.44 g, 30 mmol), potassium carbonate (8.28 g, 60 mmol), and tetrakis(triphenylphosphine)palladium (1.04 g, 0.9 mmol) were weighed into a two-necked flask. A mixed solvent of toluene and methanol was added. After replacing the nitrogen atmosphere three times, the temperature was raised to 90°C and stirred overnight. After the reaction solution cooled to room temperature, water was added and extracted with ethyl acetate. The mixture was dried over sodium sulfate and the organic solvent was removed by distillation under reduced pressure. The target product Z10 was separated by silica gel column chromatography to obtain 7.58 g of the product, with a yield of 58%.

[0188] Dissolve Z10 (6.54 g, 15 mmol) in anhydrous tetrahydrofuran, cool to -78°C, and slowly add butyl lithium (1.6 M, 9.4 mL). After approximately 0.5 hours, add acetone (15 mmol) dropwise to the reaction flask. Continue the reaction at this temperature for half an hour, then warm to room temperature and continue the reaction for 8 hours. Remove the solvent under reduced pressure, add hydrochloric acid and acetic acid, and reflux for approximately 2 hours. Cool to room temperature, add deionized water, and extract with ethyl acetate. After concentration, separate on a silica gel column, and remove the solvent to obtain 3.58 g of Z11, with a yield of 60%.

[0189] Compounds Z11 (3.18 g, 8 mmol) and Z12 (2.76 g, 8 mmol) were dissolved in anhydrous toluene. Sodium tert-butoxide (0.92 g, 9.6 mmol) and trisdibenzylideneacetone dipalladium (0.22 g, 0.24 mmol) were added. After nitrogen was replaced three times, tri-tert-butylphosphine (0.24 mmol) was added. The temperature was gradually raised to 80°C, and the reaction was stirred for 12 hours. The heat source was then removed. After the system cooled, deionized water was added, the organic layer was separated, and the organic layer was extracted three times with ethyl acetate, concentrated under reduced pressure, and passed through a silica gel column to obtain 3.98 g of product R48, with a yield of 75%; MS: 663 [M + ].

[0190] Example 4

[0191] This embodiment provides an organic compound, and its synthesis route is as follows:

[0192] Organic compound R80:

[0193]

[0194] Z13 (11.28 g, 40 mmol), Z14 (6.24 g, 40 mmol), potassium carbonate (11.04 g, 80 mmol), and tetrakis(triphenylphosphine)palladium (1.39 g, 1.2 mmol) were weighed into a two-necked flask. A mixed solvent of toluene and methanol was added. After replacing the nitrogen atmosphere three times, the temperature was raised to 90°C and stirred overnight. After the reaction solution cooled to room temperature, water was added and extracted with ethyl acetate. The mixture was dried over sodium sulfate and the organic solvent was removed by distillation under reduced pressure. The target product Z15 (10.55 g) was isolated by silica gel column chromatography, yielding 84%.

[0195] Intermediate Z15 (9.42 g, 30 mmol) was dissolved in anhydrous tetrahydrofuran, and potassium acetate (5.88 g, 60 mmol), bis(pinacolato) borate (8.38 g, 33 mmol), and dichlorobis(triphenylphosphine)palladium (0.63 g, 0.9 mmol) were added. The mixture was heated to reflux and stirred for 12 hours. After cooling, water was added to separate the organic phase, which was extracted three times with ethyl acetate and concentrated under reduced pressure. The mixture was then passed through a silica gel column to obtain 9.13 g of intermediate Z16 (75% yield).

[0196] Z16 (8.12 g, 20 mmol), Z1 (7.18 g, 20 mmol), potassium carbonate (5.52 g, 40 mmol), and tetrakis(triphenylphosphine)palladium (0.69 g, 0.6 mmol) were weighed into a two-necked flask. A mixed solvent of toluene and methanol was added, nitrogen was introduced three times, and the temperature was raised to 90°C and stirred overnight. After the reaction solution cooled to room temperature, water was added and extracted with ethyl acetate. The mixture was dried over sodium sulfate and the organic solvent was removed by distillation under reduced pressure. The target product Z17 was separated by silica gel column chromatography to obtain 6.24 g of the product with a yield of 61%.

[0197] Dissolve Z17 (5.12 g, 10 mmol) in anhydrous tetrahydrofuran, cool to -78°C, and slowly add butyl lithium (1.6 M, 6.3 mL). After approximately 0.5 hours, add acetone (10 mmol) dropwise to the reaction flask. Continue the reaction at this temperature for half an hour, then warm to room temperature and continue the reaction for 8 hours. Remove the solvent under reduced pressure, add hydrochloric acid and acetic acid, and reflux for approximately 2 hours. Cool to room temperature, add deionized water, and extract with ethyl acetate. After concentration, separate on a silica gel column, and remove the solvent to obtain 3.03 g of Z18, with a yield of 64%.

[0198] Compounds Z18 (2.37 g, 5 mmol) and Z19 (1.47 g, 5 mmol) were dissolved in anhydrous toluene. Sodium tert-butoxide (0.58 g, 6 mmol) and trisdibenzylideneacetone dipalladium (0.14 g, 0.15 mmol) were added. After nitrogen was replaced three times, tri-tert-butylphosphine (0.15 mmol) was added. The temperature was gradually raised to 80°C and the reaction was stirred for 12 hours. The heat source was then removed. After the system cooled, deionized water was added, the organic layer was separated, and the organic layer was extracted three times with ethyl acetate. The mixture was concentrated under reduced pressure and passed through a silica gel column to obtain 2.38 g of product R80, with a yield of 69%; MS: 689 [M + ].

[0199] Example 5

[0200] This embodiment provides an organic compound, and its synthesis route is as follows:

[0201] Organic compound R86:

[0202]

[0203] Compounds Z20 (1.62 g, 5 mmol) and Z4 (2 g, 5 mmol) were dissolved in anhydrous toluene. Sodium tert-butoxide (0.58 g, 6 mmol) and trisdibenzylideneacetone dipalladium (0.14 g, 0.15 mmol) were added. After nitrogen was replaced three times, tri-tert-butylphosphine (0.15 mmol) was added. The temperature was gradually raised to 80°C and the reaction was stirred for 12 hours. The heat source was then removed. After the system cooled, deionized water was added, the organic layer was separated, and the organic layer was extracted three times with ethyl acetate. The mixture was concentrated under reduced pressure and passed through a silica gel column to obtain 2.35 g of product R86, with a yield of 73%; MS: 643 [M + ].

[0204] Example 6

[0205] This embodiment provides an organic compound, and its synthesis route is as follows:

[0206] Organic compound R125:

[0207]

[0208] Compounds Z21 (154 g, 5 mmol) and Z11 (2 g, 5 mmol) were dissolved in anhydrous toluene. Sodium tert-butoxide (0.58 g, 6 mmol) and trisdibenzylideneacetone dipalladium (0.14 g, 0.15 mmol) were added. After nitrogen was replaced three times, tri-tert-butylphosphine (0.15 mmol) was added. The temperature was gradually raised to 80°C, and the reaction was stirred for 12 hours. The heat source was then removed. After the system cooled, deionized water was added, the organic layer was separated, and the organic layer was extracted three times with ethyl acetate. The mixture was concentrated under reduced pressure and passed through a silica gel column to obtain 2.41 g of product R125, with a yield of 77%; MS: 627 [M + ].

[0209] Example 7

[0210] This embodiment provides an organic compound, and its synthesis route is as follows:

[0211] Organic compound R127:

[0212]

[0213] Compounds 2-naphthylamine (2.14 g, 15 mmol) and Z22 (5.22 g, 15 mmol) were dissolved in anhydrous toluene. Sodium tert-butoxide (1.73 g, 18 mmol) and trisdibenzylideneacetone dipalladium (0.41 g, 0.45 mmol) were added. After nitrogen was replaced three times, tri-tert-butylphosphine (0.45 mmol) was added. The temperature was gradually raised to 80°C, and the reaction was stirred for 12 hours before removing the heat source. After the system cooled, deionized water was added, the organic layer was separated, and the product was extracted three times with ethyl acetate. The product was concentrated under reduced pressure and passed through a silica gel column to obtain 3.57 g of product Z23 (58% yield).

[0214] Compounds Z23 (3.29 g, 8 mmol) and Z11 (3.18 g, 8 mmol) were dissolved in anhydrous toluene. Sodium tert-butoxide (0.92 g, 9.6 mmol) and trisdibenzylideneacetone dipalladium (0.22 g, 0.24 mmol) were added. After nitrogen was replaced three times, tri-tert-butylphosphine (0.24 mmol) was added. The temperature was gradually raised to 80°C, and the reaction was stirred for 12 hours. The heat source was then removed. After the system cooled, deionized water was added, the organic layer was separated, and the organic layer was extracted three times with ethyl acetate, concentrated under reduced pressure, and passed through a silica gel column to obtain 3.61 g of product R127, with a yield of 62%; MS: 729 [M + ].

[0215] Example 8

[0216] This embodiment provides an organic compound, and its synthesis route is as follows:

[0217] Organic compound R129:

[0218]

[0219] Dissolve Z10 (4.36 g, 10 mmol) in anhydrous tetrahydrofuran, cool to -78°C, and slowly add butyl lithium (1.6 M, 6.3 mL). After approximately 0.5 hours, add butanone (10 mmol) dropwise to the reaction flask. Continue the reaction at this temperature for half an hour, then warm to room temperature and continue the reaction for 8 hours. Remove the solvent under reduced pressure, add hydrochloric acid and acetic acid, and reflux for approximately 2 hours. Cool to room temperature, add deionized water, and extract with ethyl acetate. After concentration, separate on a silica gel column, remove the solvent, and obtain 2.76 g of Z24, with a yield of 67%.

[0220] Compounds Z24 (2.06 g, 5 mmol) and Z25 (1.47 g, 5 mmol) were dissolved in anhydrous toluene. Sodium tert-butoxide (0.58 g, 6 mmol) and trisdibenzylideneacetone dipalladium (0.14 g, 0.15 mmol) were added. After nitrogen was replaced three times, tri-tert-butylphosphine (0.15 mmol) was added. The temperature was gradually raised to 80°C, and the reaction was stirred for 12 hours. The heat source was then removed. After the system cooled, deionized water was added, the organic layer was separated, and the organic layer was extracted three times with ethyl acetate. The mixture was concentrated under reduced pressure and passed through a silica gel column to obtain 2.7 g of product R129, with a yield of 86%; MS: 627 [M + ].

[0221] Example 9

[0222] This embodiment provides an organic compound, and its synthesis route is as follows:

[0223] Organic compound R156:

[0224]

[0225] Compounds Z26 (3.45 g, 10 mmol) and Z11 (4 g, 10 mmol) were dissolved in anhydrous toluene. Sodium tert-butoxide (1.15 g, 12 mmol) and trisdibenzylideneacetone dipalladium (0.21 g, 0.3 mmol) were added. After nitrogen was replaced three times, tri-tert-butylphosphine (0.3 mmol) was added. The temperature was gradually raised to 80°C and the reaction was stirred for 12 hours. The heat source was then removed. After the system cooled, deionized water was added, the organic layer was separated, and the organic layer was extracted three times with ethyl acetate. The mixture was concentrated under reduced pressure and passed through a silica gel column to obtain 3.38 g of product R156, with a yield of 51%; MS: 663 [M + ].

[0226] Example 10

[0227] This embodiment provides an organic compound, and its synthesis route is as follows:

[0228] Organic compound R164:

[0229]

[0230] Compounds Z27 (2.05 g, 5 mmol) and Z4 (2 g, 5 mmol) were dissolved in anhydrous toluene. Sodium tert-butoxide (0.58 g, 6 mmol) and trisdibenzylideneacetone dipalladium (0.14 g, 0.15 mmol) were added. After nitrogen was replaced three times, tri-tert-butylphosphine (0.15 mmol) was added. The temperature was gradually raised to 80°C, and the reaction was stirred for 12 hours. The heat source was then removed. After the system cooled, deionized water was added, the organic layer was separated, and the organic layer was extracted three times with ethyl acetate. The mixture was concentrated under reduced pressure and passed through a silica gel column to obtain 2.3 g of product R164, with a yield of 63%; MS: 729 [M + ].

[0231] Example 11

[0232] This embodiment provides an organic compound, and its synthesis route is as follows:

[0233] Organic compound R176:

[0234]

[0235] Compounds Z28 (2 g, 5 mmol) and Z11 (2 g, 5 mmol) were dissolved in anhydrous toluene. Sodium tert-butoxide (0.58 g, 6 mmol) and trisdibenzylideneacetone dipalladium (0.14 g, 0.15 mmol) were added. After nitrogen was replaced three times, tri-tert-butylphosphine (0.15 mmol) was added. The temperature was gradually raised to 80°C, and the reaction was stirred for 12 hours. The heat source was then removed. After the system cooled, deionized water was added, the organic layer was separated, and the organic layer was extracted three times with ethyl acetate. The mixture was concentrated under reduced pressure and passed through a silica gel column to obtain 2.19 g of product R176, with a yield of 61%; MS: 719 [M + ].

[0236] Example 12

[0237] This embodiment provides an organic compound, and its synthesis route is as follows:

[0238] Organic compound R181:

[0239]

[0240] Compounds Z29 (1.68 g, 5 mmol) and Z4 (2 g, 5 mmol) were dissolved in anhydrous toluene. Sodium tert-butoxide (0.58 g, 6 mmol) and trisdibenzylideneacetone dipalladium (0.14 g, 0.15 mmol) were added. After nitrogen was replaced three times, tri-tert-butylphosphine (0.15 mmol) was added. The temperature was gradually raised to 80°C, and the reaction was stirred for 12 hours before removal from the heat source. After cooling, deionized water was added, the organic layer was separated, and extracted three times with ethyl acetate. The mixture was concentrated under reduced pressure and passed through a silica gel column to obtain 2.12 g of product R181 (65% yield); MS: 653 [M+].

[0241] Preparation and characterization of OLED devices:

[0242] The following describes in detail the OLED device using the above organic compounds and its preparation process through specific device examples:

[0243] Provide materials having the following structural formulas:

[0244]

[0245] The above-mentioned materials HATCN, HT, RH, RD, ET, LiQ, C1, C2, and C3 compounds can be purchased commercially or synthesized by the synthesis methods in the prior art.

[0246] Example 13 (Device Example 1):

[0247] See also Figure 2 In this embodiment, the OLED device has the following structure: anode 102 / hole injection layer (HIL) 103 / hole transport layer (HTL) 104 / electron blocking layer (EBL) 105 / light emitting layer (EML) 106 / electron transport layer (ETL) 107 / electron injection layer (EIL) 108 / cathode 109. The illustrated structure also includes a substrate 101.

[0248] In the above-mentioned OLED device, the substrate 101 is a glass substrate; ITO is used as the material of the anode 102; HATCN is used as the material of the hole injection layer 103; HT is used as the material of the hole transport layer 104; the compound prepared in Example 1 of the organic compound is used as the material of the electron blocking layer 105; RH is used as the luminescent host material of the light-emitting layer 106, RD is used as the luminescent guest material, and the mass ratio of RD to RH is 2:98; ET and LiQ are used as the materials of the electron transport layer 107, and the mass ratio of ET to LiQ is 5:5; LiQ is used as the material of the electron injection layer 108; and Al is used as the material of the cathode 109.

[0249] In this device embodiment, the steps for preparing the OLED device are as follows:

[0250] The ITO conductive glass anode 102 was cleaned, and then ultrasonically cleaned with deionized water, acetone, and isopropyl alcohol for 15 minutes, and then treated in a plasma cleaner for 5 minutes to improve the electrode work function;

[0251] On the anode 102, the hole injection layer 103 material HATCN is deposited by vacuum evaporation with a thickness of 5 nm and a deposition rate of

[0252] On the hole injection layer 103, the hole transport layer 104 material HT is deposited by vacuum evaporation to a thickness of 90 nm;

[0253] The electron blocking layer 105 material R2 (the material structure is shown in the organic compound embodiment) is deposited on the hole transport layer 104 by vacuum evaporation to a thickness of 20 nm;

[0254] The light-emitting layer 106 is evaporated on the electron blocking layer 105, with RH as the light-emitting host material and RD as the light-emitting guest material, the mass ratio of RD to RH is 2:98, and the thickness of the light-emitting layer 106 is 40 nm;

[0255] On the light-emitting layer 106, the electron transport layer 107 materials ET and LiQ are evaporated by vacuum evaporation in a weight ratio of 5:5. The thickness of the electron transport layer 107 is 30 nm.

[0256] On the electron transport layer 107, the electron injection layer 108 material LiQ is vacuum evaporated to a thickness of 2 nm;

[0257] On the electron injection layer 108, a cathode 109 Al layer is vacuum-deposited to a thickness of 80 nm.

[0258] Example 14 (Device Example 2): Based on Device Example 1, only the electron blocking layer material is changed to R19 (for the material structure, see the organic compound example).

[0259] Example 15 (Device Example 3): Based on Device Example 1, only the electron blocking layer material is changed to R48 (for the material structure, see the organic compound example).

[0260] Example 16 (Device Example 4): Based on Device Example 1, only the electron blocking layer material is changed to R80 (for the material structure, see the organic compound example).

[0261] Example 17 (Device Example 5): Based on Device Example 1, only the electron blocking layer material is changed to R86 (for the material structure, see the organic compound example).

[0262] Example 18 (Device Example 6): Based on Device Example 1, only the electron blocking layer material is changed to R125 (for the material structure, see the organic compound example).

[0263] Example 19 (Device Example 7): Based on Device Example 1, only the electron blocking layer material is changed to R127 (for the material structure, see the organic compound example).

[0264] Example 20 (Device Example 8): Based on Device Example 1, only the electron blocking layer material is changed to R129 (for the material structure, see the organic compound example).

[0265] Example 21 (Device Example 9): Based on Device Example 1, only the electron blocking layer material is changed to R156 (for the material structure, see the organic compound example).

[0266] Example 22 (Device Example 10): Based on Device Example 1, only the electron blocking layer material is changed to R164 (for the material structure, see the organic compound example).

[0267] Example 23 (Device Example 11): Based on Device Example 1, only the electron blocking layer material is changed to R176 (for the material structure, see the organic compound example).

[0268] Example 24 (Device Example 12): Based on Device Example 1, only the electron blocking layer material is changed to R181 (for the material structure, see the organic compound example).

[0269] Comparative Example 1 (Device Comparative Example 1): Based on the device embodiment 1, only the electron blocking layer material is changed to C1 (for the material structure, see the above content).

[0270] Comparative Example 2 (Device Comparative Example 2): Based on the device embodiment 1, only the electron blocking layer material is changed to C2 (for the material structure, see the above content).

[0271] Comparative Example 3 (Device Comparative Example 3): Based on the device embodiment 1, only the electron blocking layer material is changed to C3 (for the material structure, see the above content).

[0272] Table 1. Device characterization results

[0273] serial number Electron blocking layer materials Luminous efficiency (relative value) LT95 life (relative value) Device Example 1 R2 1.22 1.17 Device Example 2 R19 1.16 1.19 Device Example 3 R48 1.19 1.21 Device Example 4 R80 1.17 1.16 Device Example 5 R86 1.2 1.15 Device Example 6 R125 1.19 1.18 Device Example 7 R127 1.23 1.20 Device Example 8 R129 1.16 1.12 Device Example 9 R156 1.17 1.19 Device Example 10 R164 1.22 1.20 Device Example 11 R176 1.21 1.22 Device Example 12 R181 1.19 1.21 Device Comparative Example 1 C1 1.0 1 Device Comparative Example 2 C2 1.07 1.03 Device Comparative Example 3 C3 1.09 1.02

[0274] The luminous efficiency in Table 1 is the current density of 10mA / cm 2 The relative value obtained when the current density is 10mA / cm 2 The relative value obtained when .

[0275] As can be seen from Table 1, compared with the device comparison example, the organic compound provided by the embodiment of the present invention can effectively improve the luminous efficiency and life of the OLED as an electron blocking layer material. In the organic compound provided by the present invention, the molecular structure will be distorted due to the steric effect between the connecting position groups of fluorene and aromatic amine, which is more favorable for the transmission of carriers after evaporation. The twisting of the group reduces the degree of conjugation between the groups within the molecule and improves the triplet energy level of the molecule. In addition, the addition of naphthyl can adjust the carrier transport ability of the molecule and balance holes and electrons. In the material structure of the device comparison example, the amino groups of C1 and C2 are connected to the naphthyl in a para or meta position, resulting in increased conjugation of the molecule, which has a greater impact on the triplet energy level of the molecule and is not conducive to the restriction of excitons; the alkyl group of C3 is larger in volume, and there is no naphthyl to regulate the carrier transport ability, making it difficult to achieve matching with the electron transport layer.

[0276] The technical solutions provided by the embodiments of the present invention are introduced in detail above. Specific examples are used herein to illustrate the principles and implementation methods of the present invention. The description of the above embodiments is only used to help understand the method of the present invention and its core ideas. At the same time, for those skilled in the art, according to the ideas of the present invention, there may be changes in the specific implementation methods and application scopes. In summary, the contents of this specification should not be understood as limiting the present invention.

Claims

1. An organic compound, characterized in that It has the structure shown in formula (1): in, R1 and R2 are independently selected from hydrogen; R3 and R4 are independently selected from alkyl groups having 1 to 4 C atoms; L1 is selected from a single bond; L2 is selected from a single bond, or Ar1 is selected from: in: Each occurrence of Z is independently selected from CR5; W is selected from one of O and S; R5 is selected from hydrogen.

2. The organic compound according to claim 1, characterized in that The formula (1) is selected from one of the structures shown in formula (2-1) and formula (2-2):

3. The organic compound according to claim 2, characterized in that The formula (2-1) is selected from one of the structures shown in formula (3-1) and formula (3-2): The formula (2-2) is selected from one of the structures shown in formula (3-4) and formula (3-5):

4. The organic compound according to claim 1, characterized in that Ar1 is selected from one of the following structures: Wherein, * indicates the attachment site.

5. The organic compound according to claim 1, characterized in that The formula (1) is selected from one of the structures shown in formula (4-3), formula (4-4), formula (4-7), formula (4-8) and formula (4-11): in, Each occurrence of W is independently selected from one of O and S; Each occurrence of R5 is independently selected from hydrogen.

6. The organic compound according to claim 1, characterized in that The organic compound is selected from the following structures:

7. A mixture, characterized in that The method comprises the organic compound according to any one of claims 1 to 6 and at least one organic functional material, wherein the organic functional material is selected from one of hole injection materials, hole transport materials, electron transport materials, electron injection materials, electron blocking materials, hole blocking materials, luminescent guest materials, luminescent host materials, and organic dyes.

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

9. An organic electronic device, characterized in that: The invention comprises at least one functional layer, wherein the functional layer comprises the organic compound according to any one of claims 1 to 6, or the functional layer comprises the mixture according to claim 7, or the functional layer is prepared by the composition according to claim 8.

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