Organic compound and mixture, composition and organic electronic device comprising the same

Abstract

The present application discloses an organic compound having the following structure: In addition, the present application also discloses a mixture, a composition and an organic electronic device. The organic compound of the present application contains a group and has a larger conjugated system. Its combination with triarylamine is conducive to enhancing the hole transport ability of the molecule. In particular, the incompletely conjugated five-membered ring is conducive to further improving the hole transport properties of the molecule through the interaction between the non-conjugated group and the conjugated group; the above characteristics of the organic compound of the present application are conducive to improving the exciton utilization rate and device stability of the OLED device using the organic compound as an electron blocking layer material, thereby achieving the effect of improving the luminous efficiency and life of the device.

Description

Technical Field

[0001] The present application relates to the technical field of organic electroluminescence, 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 optoelectronic materials offer diverse synthesis, relatively low manufacturing costs, and excellent optical and electrical properties. Organic light-emitting diodes (OLEDs) have broad potential for development in optoelectronic devices (such as flat-panel displays and lighting) due to their advantages, including wide viewing angles, fast response times, low operating voltages, and thin panels.

[0003] Organic electroluminescence refers to the phenomenon of converting electrical energy into light energy using organic substances. Organic electroluminescent elements generally have a structure with a positive electrode and a negative electrode and an organic functional layer in between. In order to improve the efficiency and lifespan of organic electroluminescent elements, the organic functional layer has a multilayer structure, with each layer containing different organic substances. Specifically, it can include a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, etc. In such an organic electroluminescent element, when a voltage is applied between the two electrodes, holes are injected from the positive electrode into the organic functional layer, and electrons are injected from the negative electrode into the organic 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. Such organic electroluminescent elements have the characteristics of self-luminescence, high brightness, high efficiency, low driving voltage, wide viewing angle, and high contrast.

[0004] In order to realize efficient organic electroluminescent devices, in addition to developing high-performance emitting layer materials, the development of corresponding electron blocking layer materials is also very important. In order to improve the efficiency and lifespan of organic electroluminescent devices, especially the efficiency and lifespan of red light OLED devices, new electron blocking layer materials are urgently needed. Summary of the Invention

[0005] In view of this, the present application provides an organic compound, aiming to improve the problems of low luminous efficiency and short life of existing organic electronic devices.

[0006] This application is implemented through the following technical solutions:

[0007] An organic compound having a structure as shown in general formula (1):

[0008]

[0009] wherein Y1 is selected from O, S or CR1R2;

[0010] R1 and R2 are independently selected from hydrogen, deuterium, a linear alkyl group having 1 to 10 C atoms, a branched or cyclic alkyl group having 3 to 10 C atoms, a substituted or unsubstituted aromatic group having 6 to 13 ring atoms, a substituted or unsubstituted heteroaromatic group having 5 to 13 ring atoms, or a combination of these groups;

[0011] Ar1 and Ar2 are independently selected from a substituted or unsubstituted aromatic group having 6 to 40 ring atoms, a substituted or unsubstituted heteroaromatic group having 5 to 40 ring atoms, or a substituted or unsubstituted non-aromatic ring system having 5 to 40 ring atoms.

[0012] Correspondingly, the present application also provides a mixture comprising the organic compound as described above and at least one organic functional material, wherein the organic functional material is selected from hole injection materials, hole transport materials, electron transport materials, electron injection materials, electron blocking materials, hole blocking materials, luminescent materials, host materials, guest materials or organic dyes.

[0013] The present application also provides a composition, which comprises the above organic compound or the above mixture, and at least one organic solvent.

[0014] The present application also provides an organic electronic device, comprising at least one functional layer, wherein the functional layer comprises the above-mentioned organic compound or the above-mentioned mixture, or the functional layer is prepared from the above-mentioned composition.

[0015] The present application also provides an organic electronic device, which comprises an anode, a cathode, a light-emitting layer located between the cathode and the anode, a hole transport layer located between the anode and the light-emitting layer, and an electron blocking layer located between the light-emitting layer and the hole transport layer; wherein the electron blocking layer comprises the above-mentioned organic compound or the above-mentioned mixture, or the functional layer is prepared from the above-mentioned composition.

[0016] Compared with the prior art, the organic compound of the present invention has the following beneficial effects:

[0017] The organic compound described in this application contains The group has a larger conjugated system, and its combination with triarylamine is beneficial to enhance the hole transport ability of the molecule. The incompletely conjugated five-membered ring is beneficial to improving the hole transport properties of the molecule through the interaction between the non-conjugated group and the conjugated group; the above characteristics of the organic compound of the present application are beneficial to improving the exciton utilization rate and device stability of the OLED device using the compound as the electron blocking layer material, thereby achieving the purpose of improving the luminous efficiency and life of the device. BRIEF DESCRIPTION OF THE DRAWINGS

[0018] 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. For those skilled in the art, other drawings can be obtained based on these drawings without creative work.

[0019] Figure 1 is a schematic structural diagram of an embodiment of an organic electronic device provided by the present application;

[0020] Among them, 101 is the substrate, 102 is the anode, 103 is the hole injection layer, 104 is the hole transport layer, 105 is the electron blocking layer, 106 is the light-emitting layer, 107 is the electron transport layer, 108 is the electron injection layer, and 109 is the cathode. DETAILED DESCRIPTION

[0021] The following, in conjunction with the accompanying drawings, provides a clear and complete description of the technical solutions in the embodiments of the present application. It should be understood that the embodiments described are only some of the embodiments of the present application, and not all of them. Based on the embodiments of the present application, all other embodiments derived by persons skilled in the art without inventive effort are within the scope of protection of the present application. Furthermore, it should be understood that the specific embodiments described herein are merely illustrative and explanatory of the present application and are not intended to limit the present application. Throughout the description of the present application, the term "including" means "including but not limited to," and the term "plurality" means "two or more." Various embodiments of the present application may be presented in the form of a range. It should be understood that describing a range in this format is merely for convenience and brevity and should not be construed as a rigid limitation on the scope of the present application. Therefore, the range description should be considered to specifically disclose all possible subranges and individual numerical values ​​within the range. For example, a range description of 1 to 6 should be considered to specifically disclose subranges, such as 1 to 3, 1 to 4, 1 to 5, 2 to 4, 2 to 6, 3 to 6, etc., as well as individual numerical values ​​within the range, such as 1, 2, 3, 4, 5, and 6, regardless of the range. Additionally, whenever a numerical range is indicated herein, it is meant to include any cited numeral (fractional or integral) within the indicated range.

[0022] Unless otherwise defined, all technical and scientific terms used herein have the same meaning as commonly understood by those skilled in the art to which this application pertains. The terms used herein in the specification of this application are for the purpose of describing specific embodiments only and are not intended to limit this application. The term "and / or" as used herein includes any and all combinations of one or more of the associated listed items.

[0023] In this application, composition, printing ink and ink have the same meaning and can be used interchangeably.

[0024] In this application, aromatic group, aromatic series and aromatic ring system have the same meaning and can be used interchangeably.

[0025] In the present application, heteroaromatic group, heteroaromatic series and heteroaromatic ring system have the same meaning and can be used interchangeably.

[0026] In the present application, "D" represents a deuterium atom; and "H" represents a hydrogen atom.

[0027] In the present application, "substituted" means that a hydrogen atom in a substituted group is replaced by a substituent.

[0028] 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.

[0029] In the present application, "substituted or unsubstituted" means that the defined group may be substituted or unsubstituted. When the defined group is substituted, it should be understood that the defined group may be substituted by one or more substituents R, wherein R is selected from but not limited to deuterium atoms, cyano groups, isocyano groups, nitro groups, halogen groups, alkyl groups containing 1-20 C atoms, heterocyclic groups containing 3-20 ring atoms, aromatic groups containing 6-20 ring atoms, heteroaromatic groups containing 5-20 ring atoms, -NR'R", silanyl groups, carbonyl groups, alkoxycarbonyl groups, aryloxycarbonyl groups, carbamoyl groups, haloformyl groups, formyl groups, isocyanate groups, thiocyanate groups, isothiocyanate groups, hydroxyl groups and trifluoromethyl groups, 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 atoms, thiocyanate groups, isothiocyanate groups, hydroxyl groups and trifluoromethyl groups. Preferably, R is selected from, but not limited to, a deuterium atom, a cyano group, an isocyano group, a nitro group or a halogen group, an alkyl group containing 1 to 10 carbon atoms, a heterocyclic group containing 3 to 20 ring atoms, an aromatic group containing 6 to 20 ring atoms, or a heteroaromatic group containing 5 to 20 ring atoms, a deuterium atom, a cyano group, an isocyano group, a nitro group or a halogen group, an alkyl group containing 1 to 10 carbon atoms, a heterocyclic group containing 3 to 10 ring atoms, an aromatic group containing 6 to 20 ring atoms, or a heteroaromatic group containing 5 to 20 ring atoms, a silane group, a carbonyl group, an alkoxycarbonyl group, an aryloxycarbonyl group, a carbamoyl group, a haloformyl group, a formyl group, an isocyanate group, a thiocyanate group, an isothiocyanate group, a hydroxyl group, and a trifluoromethyl group, and the above groups may be further substituted with substituents acceptable in the art.

[0030] In this application, the "number of ring atoms" refers to the number of atoms in the atoms that constitute the ring itself of a structural compound (e.g., a monocyclic compound, a condensed ring compound, a cross-linked compound, a carbocyclic compound, a heterocyclic compound) formed by atoms bonded together to form a ring. When the ring is substituted with a substituent, the atoms contained in the substituent are not included in the ring atoms. The "number of ring atoms" described below is also the same 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.

[0031] "Aryl or aromatic group" refers to an aromatic hydrocarbon group derived from an aromatic ring compound by removing a hydrogen atom. It can be a monocyclic aromatic group, a condensed aromatic group, or a polycyclic aromatic group. For polycyclic rings, at least one is an aromatic ring system. For example, "substituted or unsubstituted aromatic group having 6 to 40 ring atoms" refers to an aromatic group containing 6 to 40 ring atoms, preferably a substituted or unsubstituted aromatic group having 6 to 30 ring atoms, more preferably a substituted or unsubstituted aromatic group having 6 to 18 ring atoms, and particularly preferably a substituted or unsubstituted aromatic group having 6 to 14 ring atoms, and the aromatic group is optionally further substituted; suitable examples include, but are not limited to, phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, fluoranthenyl, triphenylene, pyrenyl, 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, 9,9-diarylfluorene, triarylamine or diaryl ether systems should also be included in the definition of aromatic groups.

[0032] "Heteroaryl or heteroaromatic group" means that at least one carbon atom on the basis of an aryl group is replaced by a non-carbon atom, and the non-carbon atom may be a 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, pyrimidyl , triazinyl, acridinyl, pyridazinyl, pyrazinyl, quinolyl, isoquinolyl, quinazolinyl, quinoxalinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, benzothiophenyl, benzofuranyl, indolyl, pyrroloimidazolyl, pyrrolopyrrolyl, thienopyrrolyl, thienothiphenyl, furopyrrolyl, furofuranyl, thienofuranyl, benzisoxazolyl, benzisothiazolyl, benzimidazolyl, o-naphthyl, phenanthridinyl, primary pyridyl, quinazolinone, dibenzothiophenyl, dibenzofuranyl, carbazolyl and derivatives thereof.

[0033] "Non-aromatic ring system" refers to cyclic groups other than aromatic groups or heteroaromatic groups. Non-aromatic cyclic groups include non-aromatic carbocycles or non-aromatic heterocycles. Non-aromatic heterocycles refer to non-aromatic cyclic groups that include at least one non-carbon atom, which may be an N atom, an O atom, an S atom, etc. For example, a "substituted or unsubstituted non-aromatic cyclic group having 5 to 30 ring atoms" refers to a non-aromatic carbocycle or non-aromatic heterocycle having 5 to 30 ring atoms, preferably a substituted or unsubstituted non-aromatic carbocycle or non-aromatic heterocycle having 6-14 ring atoms. In some embodiments, the non-aromatic cyclic group may be a saturated carbocycle or an unsaturated carbocycle, such as a substituted or unsubstituted cycloalkyl, cycloalkenyl, or bridged ring group.

[0034] In this application, "alkyl" can mean a straight chain, branched chain and / or cyclic alkyl group. The carbon number of the alkyl group can be 1 to 50, 1 to 30, 1 to 20, 1 to 10, or 1 to 6. Phrases containing this term, for example, "alkyl containing 1-10 C atoms" means an alkyl group containing 1 to 10 carbon atoms, which can be a straight chain alkyl group containing C1-10 carbon atoms, or a branched alkyl group containing 3-10 carbon atoms, or a cyclic alkyl group. When "alkyl containing 1-10 C atoms" appears each time, it 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, 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 decyl, 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-triacontane, adamantane, and the like.

[0035] In the present application, the substituent abbreviations correspond to: 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.

[0036] In the present application, "*" connected to a single bond indicates a linking site or a fusion site.

[0037] 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 the linking site.

[0038] In this 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.

[0039] 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 above optional substitutable positions form a ring.

[0040] In the present application, "cyclic alkyl" and "cycloalkyl" have the same meaning.

[0041] The terms "combination thereof", "any combination thereof", "any combination thereof", "group combination", etc. used in the present invention include all suitable combinations of any two or more groups in the listed items.

[0042] 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.

[0043] 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.

[0044] 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.

[0045] The technical solution of this application is as follows:

[0046] An organic compound having a structure as shown in general formula (1):

[0047]

[0048] in:

[0049] Y1 is selected from O, S or CR1R2;

[0050] R1 and R2 are each independently selected from hydrogen (-H), deuterium (-D), a linear alkyl group having 1 to 10 C atoms, a branched or cyclic alkyl group having 3 to 10 C atoms, a substituted or unsubstituted aromatic group having 6 to 13 ring atoms, a substituted or unsubstituted heteroaromatic group having 5 to 13 ring atoms, or a combination of these groups;

[0051] Ar1 and Ar2 are independently selected from a substituted or unsubstituted aromatic group having 6 to 40 ring atoms, a substituted or unsubstituted heteroaromatic group having 5 to 40 ring atoms, or a substituted or unsubstituted non-aromatic ring system having 5 to 40 ring atoms.

[0052] In a specific embodiment, R1 and R2 are each independently selected from hydrogen, deuterium, 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, or phenyl, or biphenyl, or pyridyl, or pyrimidinyl, or triazinyl, or naphthyl, or quinolyl, or isoquinolyl, or a combination of these groups.

[0053] In one embodiment, Y1 is selected from O or S.

[0054] In one embodiment, the organic compound is selected from the structure shown in formula (2-1) or (2-2):

[0055]

[0056] In formula (2-1) or (2-2), Y1, Ar1, and Ar2 have the same meanings as described above.

[0057] In one embodiment, Ar1 and Ar2 are independently selected from a substituted or unsubstituted aromatic group having 6 to 20 ring atoms, or a substituted or unsubstituted heteroaromatic group having 6 to 20 ring atoms.

[0058] In a specific embodiment, Ar1 and Ar2 are each independently selected from any one of (B-1) to (B-6):

[0059]

[0060] Wherein, each occurrence of X1 is independently selected from N or CR3;

[0061] Each occurrence of Y2 is independently selected from O, S, S=O, SO2, NR4, PR4, CR5R6 or SiR5R6;

[0062] R3, R4, R5, R6, when present, are independently selected from the group consisting of hydrogen, deuterium, linear alkyl having 1 to 20 C atoms, linear alkoxy having 1 to 20 C atoms, linear thioalkoxy having 1 to 20 C atoms, branched or cyclic alkyl having 3 to 20 C atoms, branched or cyclic alkoxy having 3 to 20 C atoms, branched or cyclic thioalkoxy having 3 to 20 C atoms, silyl, C atom-containing keto group, alkoxycarbonyl group having 2 to 20 C atoms, aryloxycarbonyl group having 7 to 20 C atoms, cyano group, carbamoyl group, haloformyl group, formyl group, isocyano group, isocyanate group, thiocyanate group, isothiocyanate group, hydroxyl group, nitro group, CF3, Cl, Br, F, substituted or unsubstituted aromatic group having 6 to 60 ring atoms, substituted or unsubstituted heteroaromatic group having 5 to 60 ring atoms, or combinations of these groups;

[0063] Ar3 is independently selected from a substituted or unsubstituted aromatic group having 6 to 20 ring atoms, or a substituted or unsubstituted heteroaromatic group having 5 to 20 ring atoms.

[0064] In one embodiment, Ar3 is selected from any one of the following groups:

[0065]

[0066] wherein X1 and Y2 have the same meanings as above.

[0067] It should be noted that when X1 is a connecting site, X1 is selected from a C atom; when Y2 is a connecting site, Y2 is selected from a N atom.

[0068] In one embodiment, each occurrence of R3, R4, R5, and R6 is independently selected from hydrogen, deuterium, a linear alkyl group having 1 to 10 carbon atoms, a branched or cyclic alkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted aromatic group having 6 to 20 ring atoms, a substituted or unsubstituted heteroaromatic group having 6 to 20 ring atoms, or a combination thereof.

[0069] In one embodiment, Ar1 and Ar2 are each independently selected from the following groups:

[0070]

[0071]

[0072] * is the connection site.

[0073] Specifically, each occurrence of R3, R4, R5, and R6 is independently selected from hydrogen, deuterium, methyl, ethyl, isopropyl, tert-butyl, phenyl, pyridyl, pyrimidyl, triazinyl, naphthyl, biphenyl, or a combination of these groups.

[0074] In a specific embodiment, Select one of the following structures:

[0075]

[0076] The above groups may be further substituted.

[0077] As an example, the organic compound in the embodiment of the present application can be selected from but not limited to any one of the following structures, which can be arbitrarily substituted:

[0078]

[0079]

[0080]

[0081]

[0082] In some embodiments, the organic compounds of the present application can be used as organic functional materials in the functional layers of organic electronic devices, particularly in the functional layers of OLED devices. Functional layers include, but are not limited to, hole injection layer (HIL), hole transport layer (HTL), electron transport layer (ETL), electron injection layer (EIL), electron blocking layer (EBL), hole blocking layer (HBL), and emissive layer (EML).

[0083] In one embodiment, the organic compound according to the present application is used in an electron blocking layer. Furthermore, the organic compound according to the present application is used in an electron blocking layer of an organic electronic device.

[0084] In some embodiments, the present application provides an electron blocking layer material comprising the organic compound as described above.

[0085] The present application also relates to a mixture comprising at least one of the organic compounds described above and at least one other organic functional material. The other organic functional material may be, but is not limited to, hole injection materials (HIMs), hole transport materials (HTMs), electron transport materials (ETMs), electron injection materials (EIMs), electron blocking materials (EBMs), hole blocking materials (HBMs), emitters, host materials, and organic dyes known in the art for use in organic electronic devices. For example, various functional materials are described in detail in WO2010135519A1, US20090134784A1, and WO2011110277A1, the entire contents of which are hereby incorporated herein by reference.

[0086] In some embodiments, the another organic functional material is selected from electron transport materials and is used as a co-host in an organic electronic device.

[0087] The present application also relates to a composition comprising at least one organic compound or mixture as described above, and at least one organic solvent, wherein the at least one organic solvent is selected from solvents based on aromatic or heteroaromatic compounds, esters, aromatic ketones or aromatic ethers, aliphatic ketones or aliphatic ethers, alicyclic or olefinic compounds, or borate or phosphate compounds, or a mixture of two or more of the foregoing solvents.

[0088] In one embodiment, the at least one organic solvent is selected from solvents based on aromatic or heteroaromatic compounds.

[0089] Further, the solvent based on aromatic or heteroaromatic compounds can be selected from, but 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, 4-isopropyldiphenylene, 2-isopropylbenzene, 4-isopropyldiphenylene, 2 ... -at least one of isopropylbiphenyl, p-methylisopropylbenzene, 1-methylnaphthalene, 1,2,4-trichlorobenzene, 4,4-difluorodiphenylmethane, 1,2-dimethoxy-4-(1-propenyl)benzene, diphenylmethane, 2-phenylpyridine, 3-phenylpyridine, N-methyldiphenylamine, 4-isopropylbiphenyl, α,α-dichlorodiphenylmethane, 4-(3-phenylpropyl)pyridine, benzyl benzoate, 1,1-bis(3,4-dimethylphenyl)ethane, 2-isopropylnaphthalene, quinoline, isoquinoline, methyl 2-furoate, and ethyl 2-furoate.

[0090] The solvent based on the aromatic ketone compound can be selected from but not limited to 1-tetralone, 2-tetralone, 2-(phenylepoxy)tetralone, 6-(methoxy)tetralone, acetophenone, propiophenone, benzophenone, and their derivatives, such as at least one of 4-methylacetophenone, 3-methylacetophenone, 2-methylacetophenone, 4-methylpropiophenone, 3-methylpropiophenone, and 2-methylpropiophenone.

[0091] The aromatic ether compound-based solvent may be selected from, but is not limited to, at least one of 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-ethylphenethyl ether, 1,3-dipropoxybenzene, 1,2,4-trimethoxybenzene, 4-(1-propenyl)-1,2-dimethoxybenzene, 1,3-dimethoxybenzene, glycidyl phenyl ether, dibenzyl ether, 4-tert-butylanisole, trans-p-propenylanisole, 1,2-dimethoxybenzene, 1-methoxynaphthalene, diphenyl ether, 2-phenoxymethyl ether, 2-phenoxytetrahydrofuran, and ethyl-2-naphthyl ether.

[0092] The solvent based on the aliphatic ketone compound may be selected from at least one of, 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.

[0093] The solvent based on the aliphatic ether compound can be selected from but not limited to at least one of 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.

[0094] The ester-based solvent may be selected from, but not limited to, alkyl octanoate, alkyl sebacate, alkyl stearate, alkyl benzoate, alkyl phenylacetate, alkyl cinnamate, alkyl oxalate, alkyl maleate, alkyl lactone, alkyl oleate, etc. Particularly preferred is at least one of octyl octanoate, diethyl sebacate, diallyl phthalate, and isononyl isononanoate.

[0095] It is understood that the organic solvent may be used alone or as a mixed solvent of two or more organic solvents.

[0096] In some embodiments, the composition of the present application comprises at least one organic compound or mixture as described above, and at least one organic solvent, and may further comprise another organic solvent.

[0097] The other organic solvent can be selected from but not limited to at least one of methanol, ethanol, 2-methoxyethanol, dichloromethane, chloroform, chlorobenzene, o-dichlorobenzene, tetrahydrofuran, anisole, morpholine, toluene, o-xylene, m-xylene, p-xylene, 1,4-dioxane, acetone, methyl ethyl ketone, 1,2-dichloroethane, 3-phenoxytoluene, 1,1,1-trichloroethane, 1,1,2,2-tetrachloroethane, ethyl acetate, butyl acetate, dimethylformamide, dimethylacetamide, dimethyl sulfoxide, tetralin, decalin, and indene.

[0098] In some preferred embodiments, the organic solvent suitable for the present application is a solvent having a Hansen solubility parameter within the following range:

[0099] δd (dispersion force) is in the range of 17.0-23.2 MPa1 / 2, especially in the range of 18.5-21.0 MPa1 / 2;

[0100] δp (polar force) is in the range of 0.2-12.5 MPa1 / 2, especially in the range of 2.0-6.0 MPa1 / 2;

[0101] δh (hydrogen bond force) is in the range of 0.9-14.2 MPa1 / 2, especially in the range of 2.0-6.0 MPa1 / 2.

[0102] In some embodiments, the boiling point of the organic solvent used in the compositions of the present application should be considered when selecting the solvent. In at least some embodiments, the boiling point of the organic solvent is ≥150°C; preferably ≥180°C; more preferably ≥200°C; even more preferably ≥250°C; and most preferably ≥275°C or ≥300°C. Boiling points within these ranges are beneficial for preventing nozzle clogging in inkjet printheads.

[0103] It is understood that the organic solvent can be evaporated from the composition system to form a film comprising the organic compound of the present application.

[0104] In some embodiments, the composition is a solution. In other embodiments, the composition is a suspension. The solution or suspension may further include additives for adjusting viscosity, adjusting film-forming properties, improving adhesion, etc. The additives may be selected from, but are not limited to, at least one of a surfactant, a lubricant, a wetting agent, a dispersant, a hydrophobic agent, and an adhesive.

[0105] In the composition of the present application, the content of the organic compound or mixture can be 0.01-10 wt %, preferably 0.1-5 wt %, more preferably 0.2-5 wt %, and further preferably 0.25-3 wt %.

[0106] 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. In some embodiments, the composition is used to prepare an organic electronic device by a printing or coating preparation method.

[0107] The printing or coating preparation method may be, but is not limited to, inkjet printing, gravure printing, nozzle printing, letterpress printing, screen printing, dip coating, spin coating, doctor blade coating, roller printing, twist roller printing, offset printing, flexographic printing, rotary printing, spray coating, brush coating, pad printing, slot extrusion coating, etc. Gravure printing, nozzle printing, and inkjet printing are preferred.

[0108] Specifically, different printing or coating technologies may require different concentrations or viscosities of the composition system. The composition system can be adjusted accordingly to suit different printing or coating methods. In one embodiment, the composition is a solution or suspension and may include one or more additional components, such as a surfactant, lubricant, wetting agent, dispersant, hydrophobic agent, adhesive, etc., to adjust viscosity, film-forming properties, and enhance adhesion.

[0109] The present application also provides a use of the organic compound, mixture or composition described above in an organic electronic device. In one embodiment, the organic compound is used in an electron blocking layer of an OLED device.

[0110] The present application provides an organic electronic device comprising at least one functional layer, wherein the functional layer comprises the organic compound or mixture as described above, or is prepared from the composition. In a specific embodiment, the organic electronic device may be a red light organic electronic device.

[0111] In one embodiment, an organic electronic device is provided, comprising a first electrode, a second electrode, and one or more functional layers located between the first electrode and the second electrode, wherein the functional layers comprise the organic compound, mixture, or composition as described above.

[0112] Furthermore, the organic electronic device comprises a cathode, an anode and one or more functional layers located at the cathode and the anode, wherein the functional layers comprise the organic compound or mixture as described above or are prepared from the composition as described above.

[0113] The organic electronic device may be selected from, but is not limited to, an organic light-emitting diode (OLED), an organic photovoltaic cell (OPV), an organic light-emitting cell (OLEEC), an organic field-effect transistor (OFET), an organic light-emitting field-effect transistor (OLED), an organic laser, an organic spintronic device, an organic sensor, and an organic plasmon emitting diode (OPD). The organic electronic device is particularly preferably an organic electroluminescent device, such as an OLED, an OLEEC, and an organic light-emitting field-effect transistor (OLED).

[0114] The 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 use in these functional layers are described in detail above and in WO2010135519A1, US20090134784A1, and WO2011110277A1, the entire contents of which are hereby incorporated by reference.

[0115] In some embodiments, the functional layer of the organic electronic device includes at least one electron blocking layer, and the electron blocking layer comprises the organic compound or mixture described above, or is prepared from the composition described above. The specific definition of the organic compound is as described above.

[0116] In a specific embodiment, the organic electronic device comprises an anode, a cathode, a light-emitting layer located between the cathode and the anode, a hole transport layer located between the anode and the light-emitting layer, and an electron blocking layer located between the light-emitting layer and the hole transport layer; wherein the electron blocking layer comprises the organic compound or mixture as described above, or is prepared from the above-mentioned composition.

[0117] In some embodiments, the material of the light-emitting layer can be selected from the structure shown in formula (3):

[0118]

[0119] in:

[0120] q is selected from 1 or 2;

[0121] Each occurrence of Ar4 is independently selected from a substituted or unsubstituted heteroaromatic group having 5 to 40 ring atoms;

[0122] Ar5, when present, 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;

[0123] R7 and R8, at each occurrence, are independently selected from hydrogen, deuterium, a linear alkyl group having 1 to 20 C atoms, a branched or cyclic alkyl group having 3 to 20 C atoms, a substituted or unsubstituted aromatic group having 5 to 60 ring atoms, a substituted or unsubstituted heteroaromatic group having 5 to 60 ring atoms, or a combination of these groups.

[0124] In one embodiment, each time Ar4 appears, it can be independently selected from quinolyl or isoquinolyl and their derivatives; further, each time Ar4 appears, it can be independently selected from quinolyl or isoquinolyl, or quinolyl substituted by an alkyl group having 1-8 C atoms, or isoquinolyl substituted by an alkyl group having 1-8 C atoms.

[0125] In one embodiment, each occurrence of Ar5 is independently selected from phenyl and its derivatives; each occurrence of Ar5 is independently selected from phenyl or phenyl substituted by an alkyl group having 1-8 carbon atoms.

[0126] In one embodiment, each occurrence of R7 and R8 is independently selected from hydrogen, deuterium, a linear alkyl group having 1 to 10 carbon atoms, or a branched or cyclic alkyl group having 3 to 10 carbon atoms.

[0127] Furthermore, in some embodiments, the general formula (3) is selected from any one of the general formulas (7-1) to (7-3):

[0128]

[0129] in:

[0130] a is selected from any integer from 0 to 6, b is selected from any integer from 0 to 4;

[0131] R9, R 10 Each occurrence is independently selected from: -D, a linear alkyl group having 1 to 20 C atoms, a branched or cyclic alkyl group having 3 to 20 C atoms, a substituted or unsubstituted aromatic group having 5 to 60 ring atoms, a substituted or unsubstituted heteroaromatic group having 5 to 60 ring atoms, or a combination of these groups.

[0132] Further, in some embodiments, at least one R9 or R 10 It is selected from a linear alkyl group having 1 to 20 C atoms or a branched or cyclic alkyl group having 3 to 20 C atoms.

[0133] Furthermore, in some embodiments, at least one R9 is selected from a linear alkyl group having 1 to 8 C atoms or a branched or cyclic alkyl group having 3 to 8 C atoms. 10 It is selected from a linear alkyl group having 1 to 8 C atoms or a branched or cyclic alkyl group having 3 to 8 C atoms.

[0134] As an example, the material of the light-emitting layer can be selected from but not limited to any one of the following structures, which can be arbitrarily replaced:

[0135]

[0136]

[0137] It is understood that in addition to the above functional layers, the organic electronic device may also be provided with some functional layers conventionally used in organic electronic devices that 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.

[0138] In one embodiment, 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.

[0139] In one embodiment, 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.

[0140] In one embodiment, 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.

[0141] 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.

[0142] In some embodiments, the organic electronic device further comprises a substrate. The substrate may be located on the side of the anode 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 elastic, for example, the material of the substrate may be plastic, metal, semiconductor wafer or glass. Preferably, the substrate has a smooth surface, and a substrate without surface defects is a particularly ideal choice. 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 most 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).

[0143] The material of the anode is an anode material known in the art for use in organic electronic devices, such as a conductive metal, a conductive metal oxide, or a conductive polymer. In some embodiments, the absolute value of the difference between the work function of the anode material 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 hole injection layer, hole transport layer, or electron blocking layer is less than 0.5 eV, preferably less than 0.3 eV, and most 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 certain embodiments, the anode is patterned. Patterned ITO conductive substrates are commercially available and can be used to prepare devices according to the present invention.

[0144] The material of the cathode is a cathode material known in the art for use in organic electronic devices, such as a conductive metal or a conductive metal oxide. In some embodiments, the absolute value of the difference between the work function of the cathode material and the LUMO energy level or conduction band energy level of the light-emitting body in the light-emitting layer or the n-type semiconductor material used 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 most preferably less than 0.2 eV. In principle, all materials that can be used as cathodes for OLEDs may be used as cathode materials for the device 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.

[0145] The material of the hole transport layer is a hole transport layer material known in the art, 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, At least one of 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(carbazol-9-yl)triphenylamine (TCTX).

[0146] 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.

[0147] Among them, the chemical structures of ET and LiQ are as follows:

[0148]

[0149] The material of the hole injection layer is a material known in the art for a hole injection layer, 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), PEDOT (polyethylenedioxythiophene), PEDOT:PSS and its derivatives doped with s-MoO3 (PEDOT:PSS:s-MoO3).

[0150] 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.

[0151] The present application also relates to electronic devices comprising the organic electronic device, which may be, but are not limited to, display devices, lighting devices, light sources, sensors, and the like.

[0152] The present application will be described in detail below with reference to specific embodiments. The following embodiments are only partial embodiments of the present application and are not intended to limit the present application.

[0153] 1. Synthesis of compounds

[0154] Example 1

[0155] The synthetic route of compound 1 in this example is as follows:

[0156]

[0157] Synthesis of Intermediate 1-2: Compound 1-1 (50 mmol), pinacol diboronate (50 mmol, CAS No. 73183-34-3), Pd(dppf)Cl2 (1,1'-bis(diphenylphosphinoferrocene)palladium dichloride, 0.2 mmol), and potassium acetate (60 mmol) were added to 160 ml of 1,4-dioxane and stirred at 100°C under a nitrogen atmosphere for 5 h. After cooling, the solvent was removed by rotary evaporation. The residue was dissolved in dichloromethane and washed with water. The organic phase was collected and the solvent was removed by rotary evaporation. The resulting crude product was recrystallized to obtain Intermediate 1-2 in an 85% yield.

[0158] Synthesis of Intermediate 1-4: Intermediate 1-2 (40 mmol), compound 1-3 (40 mmol), Pd(PPh3)4 (0.2 mmol), and potassium carbonate (70 mmol) were added to 200 mL of 1,4-dioxane / water (9:1 volume ratio) and stirred at 80°C under a nitrogen atmosphere for 6 h. After cooling, the solvent was mostly removed by rotary evaporation, and the mixture was extracted with dichloromethane and washed with water. The organic phase was collected and the solvent was removed by rotary evaporation. The resulting crude product was purified by column chromatography to obtain Intermediate 1-4 in an 84% yield.

[0159] Synthesis of Intermediate 1-6: Intermediate 1-4 (30 mmol), compound 1-5 (30 mmol), Pd(dba)2 (0.1 mmol), tri-tert-butylphosphine (0.3 mmol), and sodium tert-butoxide (60 mmol) were added to 150 ml of toluene and stirred at 80°C under a nitrogen atmosphere for 5 h. After cooling, the reaction solution was washed with water and the organic phase was separated. The organic phase was rotary evaporated to remove the solvent, and the resulting crude product was purified by column chromatography to obtain Intermediate 1-6 in a yield of 78%.

[0160] Synthesis of Compound 1: Intermediate 1-6 (20 mmol), Compound 1-7 (20 mmol), Pd2(dba)3 (0.1 mmol), tri-tert-butylphosphine (0.6 mmol), and sodium tert-butoxide (40 mmol) were added to 150 ml of toluene and stirred at 100°C under a nitrogen atmosphere for 8 h. After cooling, the reaction mixture was washed with water and the organic phase was separated. The solvent was removed by rotary evaporation, and the resulting crude product was purified by column chromatography and recrystallization to obtain Compound 1 in an 82% yield. MS (ASAP): 618.

[0161] Example 2

[0162] The synthetic route of compound 2 in this embodiment is as follows:

[0163]

[0164] The synthesis of compound 2 was carried out by referring to the synthesis of compound 1, except that compound 1-7 was replaced by compound 2-1 (20 mmol). The yield of compound 2 was 84%. MS (ASAP): 694.

[0165] Example 3

[0166] The synthetic route of compound 3 in this embodiment is as follows:

[0167]

[0168] The synthesis of compound 3 was carried out by referring to the synthesis of compound 1, except that compound 1-7 was replaced by compound 3-1 (20 mmol). The yield of compound 3 was 80%. MS (ASAP): 734.

[0169] Example 4

[0170] The synthetic route of compound 4 in this embodiment is as follows:

[0171]

[0172] The synthesis of intermediate 4-2 was based on the synthesis of intermediate 1-6, except that compound 1-5 was replaced by compound 4-1, with a yield of 85%.

[0173] The synthesis of compound 4 was carried out by referring to the synthesis of compound 1, except that intermediate 1-6 was replaced by intermediate 4-2, and compound 1-7 was replaced by compound 4-3. The yield of compound 4 was 82%. MS (ASAP): 718.

[0174] Example 5

[0175] The synthetic route of compound 5 in this embodiment is as follows:

[0176]

[0177] The synthesis of compound 5 was carried out by referring to the synthesis of compound 1, except that intermediate 1-6 was replaced by intermediate 4-2, and compound 1-7 was replaced by compound 5-1. The yield of compound 5 was 86%. MS (ASAP): 692.

[0178] Example 6

[0179] The synthetic route of compound 6 in this embodiment is as follows:

[0180]

[0181] The synthesis of compound 6 was carried out by referring to the synthesis of compound 1, except that intermediate 1-6 was replaced by intermediate 4-2, and compound 1-7 was replaced by compound 6-1. The yield of compound 6 was 84%. MS (ASAP): 728.

[0182] Example 7

[0183] The synthetic route of compound 7 in this example is as follows:

[0184]

[0185] Synthesis of Intermediate 7-2: Compound 1-2 (40 mmol), 7-1 (40 mmol), Pd(PPh3)4 (0.2 mmol), and potassium carbonate (70 mmol) were added to 200 mL of 1,4-dioxane / water (9:1 volume ratio) and stirred at 80°C under a nitrogen atmosphere for 6 h. After cooling, the solvent was removed by rotary evaporation, and the mixture was extracted with dichloromethane and washed with water. The organic phase was collected and the solvent was removed by rotary evaporation. The resulting crude product was purified by column chromatography to obtain Intermediate 7-2 in a 75% yield.

[0186] The synthesis of intermediate 7-3 refers to the synthesis of intermediate 1-6, except that intermediate 1-4 is replaced by intermediate 7-2, with a yield of 80%.

[0187] The synthesis of compound 7 was carried out by referring to the synthesis of compound 1, except that intermediate 1-6 was replaced by intermediate 7-3, and compound 1-7 was replaced by compound 7-4. MS (ASAP): 694.

[0188] Example 8

[0189] The synthetic route of compound 8 in this example is as follows:

[0190]

[0191] The synthesis of compound 8 was carried out by referring to the synthesis of compound 1, except that intermediate 1-6 was replaced by intermediate 7-3, and compound 1-7 was replaced by compound 8-1, with a yield of 76%. MS (ASAP): 646.

[0192] Example 9

[0193] The synthetic route of compound 9 in this example is as follows:

[0194]

[0195] The synthesis of compound 9 was carried out by referring to the synthesis of compound 1, except that intermediate 1-6 was replaced by intermediate 7-3, and compound 1-7 was replaced by compound 4-3, with a yield of 72%. MS (ASAP): 734.

[0196] Example 10

[0197] The synthetic route of compound 10 in this example is as follows:

[0198]

[0199] The synthesis of intermediate 10-1 refers to the synthesis of intermediate 1-6, except that intermediate 1-4 is replaced by intermediate 7-2, and compound 1-5 is replaced by compound 4-1, with a yield of 75%.

[0200] The synthesis of compound 10 was carried out by referring to the synthesis of compound 1, except that intermediate 1-6 was replaced by intermediate 10-1, and compound 1-7 was replaced by compound 2-1, with a yield of 76%. MS (ASAP): 678.

[0201] Example 11

[0202] The synthetic route of compound 11 in this example is as follows:

[0203]

[0204] The synthesis of compound 11 was carried out by referring to the synthesis of compound 1, except that intermediate 1-6 was replaced by intermediate 10-1, and compound 1-7 was replaced by compound 4-3, with a yield of 72%. MS (ASAP): 718.

[0205] Example 12

[0206] The synthetic route of compound 12 in this example is as follows:

[0207]

[0208] The synthesis of compound 12 was carried out by referring to the synthesis of compound 1, except that intermediate 1-6 was replaced by intermediate 10-1, and compound 1-7 was replaced by compound 12-1, with a yield of 72%. MS (ASAP): 708.

[0209] Example 13

[0210] The synthetic route of compound 13 in this example is as follows:

[0211]

[0212] Synthesis of Intermediate 13-3: Compounds 13-1 (30 mmol), 13-2 (30 mmol), Pd(dba)2 (0.1 mmol), tri-tert-butylphosphine (0.3 mmol), and sodium tert-butoxide (50 mmol) were added to 150 ml of toluene and stirred at 80°C under a nitrogen atmosphere for 5 h. After cooling, the reaction mixture was washed with water and the organic phase was separated. The solvent was removed by rotary evaporation, and the resulting crude product was purified by column chromatography to obtain Intermediate 13-3 in an 82% yield.

[0213] The synthesis of compound 13 was carried out by referring to the synthesis of compound 1, except that intermediate 1-6 was replaced by intermediate 4-2, and compound 1-7 was replaced by intermediate 13-3, with a yield of 71%. MS (ASAP): 768.

[0214] Example 14

[0215] The synthetic route of compound 14 in this example is as follows:

[0216]

[0217] The synthesis of intermediate 14-2 was based on the synthesis of intermediate 13-3, except that compound 13-1 was replaced by compound 14-1, with a yield of 80%.

[0218] The synthesis of compound 14 was carried out by referring to the synthesis of compound 1, except that intermediate 1-6 was replaced by intermediate 4-2, and compound 1-7 was replaced by intermediate 14-2, with a yield of 70%. MS (ASAP): 808.

[0219] Example 15

[0220] The synthetic route of compound 15 in this example is as follows:

[0221]

[0222] The synthesis of intermediate 15-2 was based on the synthesis of intermediate 13-3, except that compound 13-1 was replaced by compound 15-1, with a yield of 85%.

[0223] The synthesis of compound 15 was carried out by referring to the synthesis of compound 1, except that compound 1-7 was replaced by intermediate 15-2, with a yield of 75%. MS (ASAP): 718.

[0224] 2. Preparation and characterization of OLED devices

[0225] The following is a detailed description of an OLED device using the above-mentioned compound and its preparation process through specific examples. The structure of the OLED device is: anode (Anode) / hole injection layer (HIL) / hole transport layer (HTL) / electron blocking layer (EBL) / light-emitting layer (EML) / electron transport layer (ETL) / electron injection layer (EIL) / cathode (Cathode). Specifically, the schematic diagram of the OLED device structure is as follows: Figure 1 As shown, 101 is a substrate, 102 is an anode, 103 is a hole injection layer, 104 is a hole transport layer, 105 is an electron blocking layer, 106 is a light-emitting layer, 107 is an electron transport layer, 108 is an electron injection layer, and 109 is a cathode.

[0226] The OLED device has a structure consisting of ITO / hole injection layer (5nm) / hole transport layer (90nm) / electron blocking layer (20nm) / host material RH1:red light-emitting guest RD1 or RD2 / ETM:Liq / LiF / Al. The mass ratio of host material RH1 to guest material RD1 or RD2 is 95:5.

[0227] The preparation steps are as follows:

[0228] The ITO conductive glass anode layer was cleaned, and then ultrasonically cleaned with deionized water, acetone, and isopropyl alcohol for 15 minutes, and then subjected to UV-ozone plasma treatment.

[0229] The hole injection layer was formed by thermal evaporation of the compound HATCN on the ITO layer in high vacuum (1×10-6 mbar) with a thickness of 5 nm;

[0230] On the hole injection layer, a 90 nm thick layer of compound HT1 was evaporated as a hole transport layer;

[0231] On the hole transport layer, a 20 nm thick layer of compound 1 of this embodiment was evaporated as an electron blocking layer;

[0232] On the electron blocking layer, a 40nm light-emitting layer is vacuum-deposited; the light-emitting layer includes RH1 as the host material and RD1 or RD2 as the guest material, and the two materials are co-evaporated from multiple sources;

[0233] On the light-emitting layer, a 25nm thick ETM / LiQ (1:1 mass ratio) mixture was evaporated as an electron transport layer; on the electron transport layer, a 0.5nm thick LiF was used as an electron injection layer; and a 150nm thick Al was used as the cathode.

[0234] Packaging: The devices were encapsulated with UV-curable resin in a nitrogen glove box.

[0235] The structures of the compounds involved in the device are as follows:

[0236]

[0237] The above compounds are all commercially available, or their synthesis methods are all prior art.

[0238] The current-voltage (JV) characteristics of each OLED device were characterized by a characterization device, and the lifetime (LT95@1000nits) and external quantum efficiency were recorded. The results are shown in Table 1 below. The lifetime LT95@1000nits refers to the time it takes for the brightness of the device to drop from an initial brightness of 1000nits to 95% of the initial brightness under a constant current. Here, LT95@1000nits and external quantum efficiency are calculated relative to Comparative Example 1, that is, the lifetime of Comparative Example 1 is 1 and the external quantum efficiency is 100%. In addition, the luminous efficiency in Table 1 is calculated when the current density is 10mA / cm 2 The relative value obtained when the current density is 10mA / cm 2 The relative value obtained when .

[0239] Table 1 Device characterization results

[0240]

[0241]

[0242] As shown in Table 1, compared with Comparative Example 1, the compounds of the present application as electron blocking materials can effectively improve the luminous efficiency and life of organic electroluminescent devices. Specifically, the devices of Examples 1 to 19 contain The group has a larger conjugated system, and its combination with triarylamine is beneficial to enhance the hole transport ability of the molecule. The incompletely conjugated five-membered ring is beneficial for improving the hole transport properties of the molecule through the interaction between the non-conjugated group and the conjugated group. The above properties of the organic compound of the present invention are beneficial for improving the exciton utilization rate and device stability of OLED devices using the compound of the present invention as an electron blocking layer material, thereby achieving the purpose of improving the luminous efficiency and life of the device.

[0243] The organic compounds, mixtures, compositions and organic electronic devices provided in the embodiments of the present application are introduced in detail above. Specific examples are used herein to illustrate the principles and implementation methods of the present application. The description of the above embodiments is only used to help understand the method and core ideas of the present application. At the same time, for those skilled in the art, according to the ideas of the present application, 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 application.

Claims

1. An organic compound, characterized in that It has a structure as shown in the general formula (1): （1） in, Y1 is selected from O or S; Ar1 and Ar2 are each independently selected from any one of the following groups: ； Each occurrence of R3 is independently selected from hydrogen, methyl, and phenyl; R5 and R6 are selected from methyl groups; * is the connection site.

2. The organic compound according to claim 1, characterized in that The compound described in general formula (1) is selected from any one of formula (2-1) or (2-2): 。 3. The organic compound according to claim 1, characterized in that The organic compound is selected from any one of the following structures: 。 4. A mixture, characterized in that The mixture comprises the organic compound according to any one of claims 1 to 3 and at least one organic functional material, wherein the organic functional material is selected from hole injection materials, hole transport materials, electron transport materials, electron injection materials, electron blocking materials, hole blocking materials, luminescent materials, host materials, guest materials or organic dyes.

5. A composition, characterized in that The composition comprises the organic compound according to any one of claims 1 to 3 or the mixture according to claim 4, and at least one organic solvent.

6. An organic electronic device comprising at least one functional layer, characterized in that: The functional layer comprises an electron blocking layer, wherein the electron blocking layer comprises the organic compound according to any one of claims 1 to 3, or the mixture according to claim 4, or the electron blocking layer is prepared from the composition according to claim 5.

7. An organic electronic device, characterized in that: The organic electronic device comprises an anode, a cathode, a light-emitting layer between the cathode and the anode, a hole transport layer between the anode and the light-emitting layer, and an electron blocking layer between the light-emitting layer and the hole transport layer; wherein the electron blocking layer comprises the organic compound according to any one of claims 1 to 3, or the mixture according to claim 4, or the electron blocking layer is prepared from the composition according to claim 5.

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