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

Abstract

The application discloses an organic compound having the following structure: the organic compound of the application has electron blocking characteristics by introducing an indane group on a benzene ring through a fluorene-benzene ring-triarylamine structure, and improves the hole transport characteristics of fluorene and triarylamine, improves the exciton utilization rate and stability, light emitting efficiency and lifetime of a device containing the organic compound through the intermolecular interaction of non-conjugated and conjugated groups. In addition, the application also discloses a mixture, a composition and an organic electronic device.

Description

TECHNICAL FIELD

[0001] The present application relates to the technical field of light-emitting materials, in particular to an organic compound, and a mixture, a composition and an organic electronic device comprising the organic compound. BACKGROUND

[0002] Organic semiconductor materials have diversity in synthesis, relatively low manufacturing cost and excellent optical and electrical properties. Organic light-emitting diodes (OLEDs) have broad development potential in the application of optoelectronic devices (such as flat panel displays and lighting) due to their advantages such as wide viewing angle, fast response time, low operating voltage, thin panel thickness, etc.

[0003] The organic electroluminescence phenomenon refers to the phenomenon of converting electrical energy into light energy by using organic substances. An organic electroluminescence element utilizing the organic electroluminescence phenomenon generally has a structure of a positive electrode and a negative electrode and an organic substance layer therebetween. In order to improve the efficiency and the lifespan of the organic electroluminescence element, the organic substance layer has a multi-layer structure, each layer containing a different organic substance. 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 electroluminescence element, a voltage is applied between the two electrodes, then holes are injected from the positive electrode to the organic substance layer, and electrons are injected from the negative electrode to the organic substance layer, and when the injected holes and electrons meet, an exciton is formed, and when the exciton transitions to the ground state, light is emitted. Such an organic electroluminescence element has characteristics such as self-emission, high brightness, high efficiency, low driving voltage, wide viewing angle, high contrast, high responsiveness, etc.

[0004] In addition to the light-emitting layer, the OLED device also needs a hole transport layer, an electron blocking layer, and other functional layers related to hole transport, in order to achieve balanced transport of holes and electrons, and recombination of holes and electrons in the light-emitting layer, to improve the efficiency and lifespan of the device. In order to achieve a high-efficiency organic electroluminescence device, in addition to developing high-performance light-emitting layer materials, the development of corresponding electron blocking layer materials is also important. In order to improve the efficiency and lifespan of the organic electroluminescence device, especially the efficiency and lifespan of the red OLED device, new electron blocking layer materials need to be developed. SUMMARY

[0005] Therefore, the present application provides an organic compound, aiming to improve the problems of low light-emitting efficiency and short lifespan of the existing organic electronic device.

[0006] The present application is realized by the following technical solutions:

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

[0008]

[0009] wherein:

[0010] Ar1, Ar2are 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 non-aromatic ring system;

[0011] R1, R2are independently selected from -H, -D, or a straight-chain alkyl group having 1 to 20 C atoms, or a straight-chain alkoxy group having 1 to 20 C atoms, or a straight-chain thioalkoxy group having 1 to 20 C atoms, or a branched alkyl group having 3 to 20 C atoms, or a branched alkoxy group having 3 to 20 C atoms, or a branched thioalkoxy group having 3 to 20 C atoms, or a cyclic alkyl group having 3 to 20 C atoms, or a cyclic alkoxy group having 3 to 20 C atoms, or a cyclic thioalkoxy group having 3 to 20 C atoms, or a silyl group, or a keto group having 1 to 20 C atoms, or an alkoxycarbonyl group having 2 to 20 C atoms, or an aryloxycarbonyl group having 7 to 20 C atoms, a cyano group, a carbamoyl group, a halogen formyl group, a formyl group, an isocyano group, an isocyanate group, a thiocyanate group, an isothiocyanate group, a hydroxyl group, a nitro group, an amine group, -CF3, -Cl, -Br, -F, -I, or an alkenyl group having 2 to 20 C atoms, or a substituted or unsubstituted aromatic group having 6 to 60 ring atoms, or a substituted or unsubstituted heteroaromatic group having 5 to 60 ring atoms, or a substituted or unsubstituted aryloxy group having 6 to 60 ring atoms, or a substituted or unsubstituted heteroaryloxy group having 5 to 60 ring atoms, or a combination thereof;

[0012] R1, R2are independently selected from -H, -D, or a straight-chain alkyl group having 1 to 20 C atoms, or a straight-chain alkoxy group having 1 to 20 C atoms, or a straight-chain thioalkoxy group having 1 to 20 C atoms, or a branched alkyl group having 3 to 20 C atoms, or a branched alkoxy group having 3 to 20 C atoms, or a branched thioalkoxy group having 3 to 20 C atoms, or a cyclic alkyl group having 3 to 20 C atoms, or a cyclic alkoxy group having 3 to 20 C atoms, or a cyclic thioalkoxy group having 3 to 20 C atoms, or a silyl group, or a keto group having 1 to 20 C atoms, or an alkoxycarbonyl group having 2 to 20 C atoms, or an aryloxycarbonyl group having 7 to 20 C atoms, a cyano group, a carbamoyl group, a halogen formyl group, a formyl group, an isocyano group, an isocyanate group, a thiocyanate group, an isothiocyanate group, a hydroxyl group, a nitro group, an amine group, -CF3, -Cl, -Br, -F, -I, or an alkenyl group having 2 to 20 C atoms, or a substituted or unsubstituted aromatic group having 6 to 60 ring atoms, or a substituted or unsubstituted heteroaromatic group having 5 to 60 ring atoms, or a substituted or unsubstituted aryloxy group having 6 to 60 ring atoms, or a substituted or unsubstituted heteroaryloxy group having 5 to 60 ring atoms, or a combination thereof;

[0013] Accordingly, the present application also provides a mixture comprising the organic compound and at least one organic functional material selected from a hole injection material, a hole transport material, an electron transport material, an electron injection material, an electron blocking material, a hole blocking material, an emitting material, a host material, a guest material, or an organic dye.

[0014] Accordingly, the present application also provides a composition comprising the organic compound or the mixture and at least one organic solvent.

[0015] Accordingly, the present application also provides an organic electronic device comprising at least one functional layer, wherein the functional layer comprises the organic compound or the mixture, or the functional layer is prepared from the composition.

[0016] Accordingly, this application also provides an organic electronic device comprising 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 electron blocking layer is prepared from the above-mentioned composition.

[0017] Compared with the prior art, the organic compounds of the present invention have the following beneficial effects:

[0018] The organic compounds described in this application employ a fluorene-benzene ring-triarylamine structure and introduce an indenyl group onto the benzene ring. The indenyl group has a partially conjugated five-membered ring structure. The fluorene and triarylamine groups are conjugated groups with good hole transport capabilities. Through intermolecular interactions between the non-conjugated and conjugated groups, the hole transport properties of fluorene and triarylamine are effectively utilized. The organic compound of this application exhibits good hole transport and electron blocking properties, thereby improving the exciton utilization and device stability of organic light-emitting devices incorporating this compound, ultimately achieving the goal of improving device luminous efficiency and lifetime. Attached Figure Description

[0019] To more clearly illustrate the technical solutions in the embodiments of this application, the accompanying drawings used in the description of the embodiments will be briefly introduced below. Obviously, the accompanying drawings described below are only some embodiments of this application. For those skilled in the art, other drawings can be obtained based on these drawings without creative effort.

[0020] Figure 1 This is a schematic diagram of the structure of an embodiment of the organic electronic device provided in this application;

[0021] In this design, 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 Implementation

[0022] The technical solutions in the embodiments of this application will be clearly and completely described below with reference to the accompanying drawings. Obviously, the described embodiments are only a part of the embodiments of this application, and not all of the embodiments. Based on the embodiments in this application, all other embodiments obtained by those skilled in the art without creative effort are within the scope of protection of this application. In addition, it should be understood that the specific implementation methods described herein are only for illustration and explanation of this application and are not intended to limit this application. In the description of this application, the term "comprising" means "including but not limited to", and the term "multiple" means "two or more". Various embodiments of this application may exist in the form of a range; it should be understood that the description in the form of a range is only for convenience and conciseness and should not be construed as a hard limitation on the scope of this application; therefore, it should be considered that the range description has specifically disclosed all possible sub-ranges and single numerical values ​​within that range. For example, it should be considered that the range description from 1 to 6 has specifically disclosed sub-ranges, such as from 1 to 3, from 1 to 4, from 1 to 5, from 2 to 4, from 2 to 6, from 3 to 6, etc., and single numbers within the range, such as 1, 2, 3, 4, 5 and 6, which applies regardless of the range. Additionally, whenever a range of numbers is specified in this document, it means including any referenced numbers (fractions or integers) within the range referred to.

[0023] Unless otherwise defined, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this application belongs. The terminology used herein is for the purpose of describing particular embodiments only and is not intended to be limiting of the application. The term "and / or" as used herein includes any and all combinations of one or more of the associated listed items.

[0024] In this application, the terms "composition," "printing ink," and "ink" have the same meaning and are interchangeable.

[0025] In this application, aromatic groups, aromatic families, and aromatic ring systems have the same meaning and can be used interchangeably.

[0026] In this application, heteroaromatic groups, heteroaromatic families, and heteroaromatic ring systems have the same meaning and can be used interchangeably.

[0027] In this application, "D" represents a deuterium atom; "H" represents a hydrogen atom.

[0028] In this application, "substitution" means that the hydrogen atom in the substituent is replaced by the substituent.

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

[0030] In this application, "ring atom number" refers to the number of atoms in the ring itself of a structural compound (e.g., a monocyclic compound, a fused-ring compound, a cross-linked compound, a carbocyclic compound, or a heterocyclic compound) obtained by atomic bonding to form a ring. When the ring is substituted by a substituent, the atoms contained in the substituent are not included in the ring-forming atoms. The same applies to the "ring atom number" described below unless otherwise specified. For example, a benzene ring has 6 ring atoms, a naphthalene ring has 10 ring atoms, and a thiophene group has 5 ring atoms.

[0031] "Aryl or aromatic group" refers to an aromatic hydrocarbon group derived from an aromatic ring compound by removing one hydrogen atom. It can be a monocyclic aryl, a fused-ring aryl, or a polycyclic aryl, and in the case of a polycyclic ring, at least one of the rings is an aromatic ring system. For example, "substituted or unsubstituted aryl having 6 to 40 ring atoms" means an aryl containing 6 to 40 ring atoms, preferably a substituted or unsubstituted aryl having 6 to 30 ring atoms, more preferably a substituted or unsubstituted aryl having 6 to 18 ring atoms, and particularly preferably a substituted or unsubstituted aryl having 6 to 14 ring atoms, and optionally further substituted on the aryl group; suitable examples include, but are not limited to, phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthryl, fluoranyl, triphenylene, pyrene, perylene, tetraphenyl, fluorenyl, dinaphthylphenyl, acenaphthyl and their derivatives. It is understandable that multiple aryl groups can 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 aryl.

[0032] "Heteroaryl or heteroaromatic group" refers to an aryl group in which at least one carbon atom is replaced by a non-carbon atom, which can be an N atom, O atom, S atom, etc. For example, "substituted or unsubstituted heteroaryl group having 5 to 40 ring atoms" refers to a heteroaryl group having 5 to 40 ring atoms, preferably a substituted or unsubstituted heteroaryl group having 6 to 30 ring atoms, more preferably a substituted or unsubstituted heteroaryl group having 6 to 18 ring atoms, and particularly preferably a substituted or unsubstituted heteroaryl group having 6 to 14 ring atoms. The heteroaryl group may optionally be further substituted, and suitable examples include, but are not limited to, thiophene, furanyl, pyrrole, imidazolyl, diazolyl, triazolyl, imidazolyl, pyridyl, bipyridyl, and pyrimidinyl. Triazinyl, acridineyl, pyridazinyl, pyrazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, phthalazinyl, pyridinylpyrimidineyl, pyridinylpyrazinyl, benzothiopheneyl, benzofuranyl, indolyl, pyrroloimidazolyl, pyrrolopyrrolyl, thienopyrrolyl, thienopyrrolyl, furanolyl, furanolyl, thienofuranyl, benzoisoxazolyl, benzoisothiazolyl, benzoimidazolyl, o-diazonyl, phenanthridineyl, primidyl, quinazolinoneyl, dibenzothiopheneyl, dibenzofuranyl, carbazoleyl and their derivatives.

[0033] In this application, "alkyl" can mean straight-chain, branched, and / or cyclic alkyl. The carbon number of an alkyl group can be 1 to 50, 1 to 30, 1 to 20, 1 to 10, or 1 to 6. 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, adamantyl, etc. Straight-chain, branched, and / or cyclic alkyl groups. The carbon number of an alkyl group can be 1 to 50, 1 to 30, 1 to 20, 1 to 10, or 1 to 6. Phrases containing this term, such as "C 1-9 "Alkyl" refers to an alkyl group containing 1 to 9 carbon atoms, and each time it appears, it can independently be 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-butyl... Amyl, 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-pentadecanyl, n-hexadecyl, 2-ethylhexadecyl, 2-butylhexadecyl, 2-hexylhexadecyl, 2-octylhexadecyl, n-heptadecyl, n-octadecyl, n-heptadecyl, n-heptadecyl, n-heptadecyl, n-heptadecyl, 2-ethylhexane, n-butylhexane, 2-hexylhexane, 2-octylhexane, n-monodecyl, n-hepta ...

[0034] In this application, the abbreviations for substituents are: n-n-, sec-sec-, i-iso-, t-tert-, o-ortho-, m-me-, p-para-, Me-methyl, Et-ethyl, Pr-propyl, Bu-butyl, Am-pentyl, Hx-hexyl, Cy-cyclohexyl.

[0035] In this application, "halogen" or "halogen group" refers to F, Cl, Br or I.

[0036] In this application, the term "alkoxy" refers to a group having an -O-alkyl group, i.e., an alkyl group as defined above that is attached to the parent nucleus 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).

[0037] In this application, "amino group" refers to an amine derivative having the structural feature of the formula -N(X)2, wherein each "X" is independently H, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted heterocyclic group, etc. Non-limiting types of amino groups include -NH2, -N(alkyl)2, -NH(alkyl), -N(cycloalkyl)2, -NH(cycloalkyl), -N(heterocyclic)2, -NH(heterocyclic), -N(aryl)2, -NH(aryl), -N(alkyl)(aryl), -N(alkyl)(heterocyclic), -N(cycloalkyl)(heterocyclic), -N(aryl)(heteroaryl), -N(alkyl)(heteroaryl), etc.

[0038] In this application, unless otherwise defined, hydroxyl refers to -OH, carboxyl refers to -COOH, carbonyl refers to -C(=O)-, amino refers to -NH2, formyl refers to -C(=O)H, haloformyl refers to -C(=O)Z (where Z represents halogen), carbamoyl refers to -C(=O)NH2, isocyanate refers to -NCO, and isothiocyanate refers to -NCS.

[0039] In this application, the "*" connected to a single bond indicates a connection site or fusion site.

[0040] In this application, when no linking site is specified in the group, it means that any linkable site in the group is selected as the linking site.

[0041] In this application, when no fusion site is specified in the group, it means that any fusionable site in the group is selected as the fusion site, preferably two or more sites in the adjacent position of the group are fusion sites.

[0042] In this application, when the same group contains multiple substituents with the same symbol, the substituents can be the same as or different from each other, for example... The six R's on the benzene ring 1 They can be the same as or different from each other.

[0043] In this application, the single bond connecting the substituents extends through the corresponding ring, indicating that the substituent can be attached to any position on the ring, for example... R is attached to any substituted site on the benzene ring; such as express Can be with The above can be selected at any replaceable position to form a loop.

[0044] In this application, "adjacent groups" means that there are no substituted sites between two substituents.

[0045] In this application, "two Rs forming a ring" means a ring system formed by the interconnection of two Rs. The ring system can be selected from aliphatic hydrocarbon rings, aliphatic heterocycles, aromatic hydrocarbon rings, or aromatic heterocycles. Preferably, it can form... * indicates a fusion site.

[0046] In this application, "cycloalkyl" and "cycloalkyl" have the same meaning.

[0047] The terms “combinations thereof,” “arbitrary combinations thereof,” “arbitrary combinations thereof,” and “group combinations” used in this invention include all suitable combinations of any two or more groups listed in the items.

[0048] The technical solution of this application is as follows:

[0049] An organic compound having a structure as shown in general formula (1):

[0050]

[0051] in:

[0052] Ar1 and Ar2 are independently selected from aromatic groups with 6 to 40 substituted or unsubstituted ring atoms, heteroaromatic groups with 5 to 40 substituted or unsubstituted ring atoms, or non-aromatic ring systems.

[0053] R1 and R2 are independently selected from -H, -D, or a straight-chain alkyl group having 1 to 20 carbon atoms, or a straight-chain alkoxy group having 1 to 20 carbon atoms, or a straight-chain thioalkoxy group having 1 to 20 carbon atoms, or a branched alkyl group having 3 to 20 carbon atoms, or a branched alkoxy group having 3 to 20 carbon atoms, or a branched thioalkoxy group having 3 to 20 carbon atoms, or a cyclic alkyl group having 3 to 20 carbon atoms, or a cyclic alkoxy group having 3 to 20 carbon atoms, or a cyclic thioalkoxy group having 3 to 20 carbon atoms, or a silyl group, or a ketone group having 1 to 20 carbon atoms, or a group having 2 to 20 carbon atoms. The alkoxycarbonyl group, or an aryloxycarbonyl group having 7 to 20 carbon atoms, a cyano group, a carbamoyl group, a haloformyl group, a formyl group, an isocyano group, an isocyanate group, a thiocyanate group, an isothiocyanate group, a hydroxyl group, a nitro group, an amino group, a -CF3 group, a -Cl group, a -Br group, a -F group, a -I group, or an alkenyl group having 2 to 20 carbon atoms, or an aromatic group having 6 to 60 substituted or unsubstituted ring atoms, or a heteroaromatic group having 5 to 60 substituted or unsubstituted ring atoms, or a heteroaromatic group having 5 to 60 substituted or unsubstituted ring atoms, or a combination of these groups;

[0054] R1 and R2 may be connected to each other to form a loop or not.

[0055] In one embodiment, general formula (1) is selected from the structures shown in general formulas (2-1) to (2-3):

[0056]

[0057] Furthermore, in one embodiment, general formula (1) is selected from the structures shown in general formulas (3-1) to (3-6):

[0058]

[0059] In one embodiment, R1 and R2 are each independently selected from -H, -D, straight-chain alkyl groups having 1 to 10 carbon atoms, branched or cyclic alkyl groups having 3 to 10 carbon atoms, substituted or unsubstituted aromatic groups having 6 to 13 ring atoms, substituted or unsubstituted heteroaromatic groups having 5 to 13 ring atoms, or combinations of these groups;

[0060] Furthermore, R1 and R2 are each independently selected from -H, -D, 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, phenyl, biphenyl, pyridyl, pyrimidinyl, triazine, naphthyl, quinolinyl, isoquinolinyl, or combinations of these groups.

[0061] In one embodiment, R1 and R2 are not cyclic to each other; furthermore, R1 and R2 are each independently selected from methyl or phenyl.

[0062] In one specific embodiment, R1 and R2 are selected from the same group.

[0063] In another embodiment, R1 and R2 form a ring with each other; further, R1 and R2 form a cyclic alkyl group with each other; specifically, R1 and R2 form a ring with each other as shown below:

[0064]

[0065] Where: * indicates a connection site.

[0066] In one embodiment, Ar1 and Ar2 are independently selected from aromatic groups with 6 to 20 substituted or unsubstituted ring atoms, heteroaromatic groups with 6 to 20 substituted or unsubstituted ring atoms, or non-aromatic ring systems; the meaning of "substituted or unsubstituted" is the same as described above.

[0067] Furthermore, in the organic compound according to the present invention, Ar1 and Ar2 are each independently selected from any one of the general formulas (B-1) to (B-6):

[0068]

[0069] in:

[0070] Each time X appears, it is independently selected from CR3 or N;

[0071] Y is selected from O, S, S=O, SO2, NR4, PR4, CR5R6 or SiR5R6;

[0072] R3, R4, R5, and R6, each appearing independently, are selected from: -H, -D, or a straight-chain alkyl group having 1 to 20 carbon atoms, or a straight-chain alkoxy group having 1 to 20 carbon atoms, or a straight-chain thioalkoxy group having 1 to 20 carbon atoms, or a branched alkyl group having 3 to 20 carbon atoms, or a branched alkoxy group having 3 to 20 carbon atoms, or a branched thioalkoxy group having 3 to 20 carbon atoms, or a cyclic alkyl group having 3 to 20 carbon atoms, or a cyclic alkoxy group having 3 to 20 carbon atoms, or a cyclic thioalkoxy group having 3 to 20 carbon atoms, or a silyl group, or a ketone group having 1 to 20 carbon atoms, or a group having 2 to 20 carbon atoms. An alkoxycarbonyl group with 20 carbon atoms, or an aryloxycarbonyl group with 7 to 20 carbon atoms, a cyano group, a carbamoyl group, a halocarbamoyl group, a formyl group, an isocyano group, an isocyanate group, a thiocyanate group, an isothiocyanate group, a hydroxyl group, a nitro group, an amino group, a -CF3 group, a -Cl group, a -Br group, a -F group, an -I group, or an alkenyl group with 2 to 20 carbon atoms, or an aromatic group with 6 to 60 substituted or unsubstituted ring atoms, or a heteroaromatic group with 5 to 60 substituted or unsubstituted ring atoms, or a heteroaromatic group with 5 to 60 substituted or unsubstituted ring atoms, or a combination of these groups;

[0073] Ar3 is independently selected from aromatic groups with 6 to 20 substituted or unsubstituted ring atoms, or heteroaromatic groups with 6 to 20 substituted or unsubstituted ring atoms.

[0074] It should be noted that when X is a linking site, X is selected from C atoms; when Y is a linking site, Y is selected from N atoms.

[0075] In some preferred embodiments, Ar3 is selected from...

[0076] Furthermore, Ar3 is selected from the following groups:

[0077]

[0078] Where: * indicates a fusion site.

[0079] In a specific embodiment, Ar1 and Ar2 are independently selected from the following groups:

[0080]

[0081]

[0082] The H atoms in the above groups can be further substituted.

[0083] In a specific example, R3, R4, R5, and R6 each appear independently selected from: -H, -D, a straight-chain alkyl group having 1 to 10 carbon atoms, a branched or cyclic alkyl group having 3 to 10 carbon atoms, cyano, nitro, -CF3, -Cl, -Br, -F, -I, a substituted or unsubstituted aromatic or heteroaromatic group having 6 to 10 cyclic atoms, or a combination of these groups.

[0084] In one embodiment, each occurrence of R3 is independently selected from -H, -D, or a straight-chain alkyl group having 1 to 4 carbon atoms, or a branched alkyl group having 3 to 4 carbon atoms, or a cyclic alkyl group having 3 to 6 carbon atoms, or silyl, cyano, isocyano, hydroxy, nitro, -CF3, -Cl, -Br, -F, -I, or phenyl, pyridyl, pyrimidinyl, triazine, biphenyl, naphthyl, quinolinyl, or isoquinolinyl, or combinations of these groups.

[0085] In one embodiment, each occurrence of R4 is independently selected from a straight-chain alkyl group having 1 to 4 carbon atoms, or a branched alkyl group having 3 to 6 carbon atoms, or a cyclic alkyl group having 3 to 6 carbon atoms, or an aromatic group having 6 to 10 substituted or unsubstituted cyclic atoms, or a heteroaromatic group having 6 to 10 substituted or unsubstituted cyclic atoms, or a combination of these groups.

[0086] In one embodiment, each occurrence of R5 and R6 is independently selected from -H, -D, or a straight-chain alkyl group having 1 to 4 carbon atoms, or a branched alkyl group having 3 to 6 carbon atoms, or a cyclic alkyl group having 3 to 6 carbon atoms, or an aromatic group having 6 to 10 substituted or unsubstituted cyclic atoms, or a heteroaromatic group having 6 to 10 substituted or unsubstituted cyclic atoms, or a combination of these groups.

[0087] In a particular embodiment, Independently selected from the following groups:

[0088]

[0089]

[0090] The H atoms in the above groups can be further substituted.

[0091] In some embodiments, Ar1 is selected from the following structures:

[0092]

[0093] Where: n is selected from 0, 1, 2, 3, 4 or 5; R3 can be found in the relevant description above.

[0094] As an example, the organic compound described in this application may be selected from, but is not limited to, any of the following structures, which may be arbitrarily substituted:

[0095]

[0096]

[0097]

[0098]

[0099] In some embodiments, the organic compounds of this 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 light-emitting layer (EML).

[0100] This application also relates to an electron blocking layer material comprising the organic compound described above.

[0101] This application also relates to a mixture comprising at least one of the aforementioned organic compounds and at least one other functional material. The other functional material may be, but is not limited to, hole injection materials (HIM), hole transport materials (HTM), electron transport materials (ETM), electron injection materials (EIM), electron blocking materials (EBM), hole blocking materials (HBM), luminescent materials, 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.

[0102] In some embodiments, the other functional material is selected from electron transport materials and is used as a co-body in organic electronic devices.

[0103] This application also relates to a composition comprising at least one organic compound or mixture as described above, and at least one organic solvent. The at least one organic solvent is selected from aromatic or heteroaromatic solvents, ester-based solvents, aromatic ketone-based solvents, aromatic ether-based solvents, aliphatic ketones, aliphatic ethers, alicyclic compounds, olefin compounds, borate esters, and phosphate esters.

[0104] Furthermore, the aromatic or heteroaromatic solvent may be selected from, but is not limited to, p-diisopropylbenzene, pentobenzene, tetrahydronaphthalene, cyclohexylbenzene, chloronaphthalene, 1,4-dimethylnaphthalene, 3-isopropylbiphenyl, p-methylisopropylbenzene, dipentylbenzene, tripentylbenzene, pentylene, 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-isopropylbenzene, etc. At least one of the following: 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-furanate, and ethyl 2-furanate.

[0105] The ester-based solvent may 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, alkyl oleate, etc. At least one of octanoate, diethyl sebacate, diallyl phthalate, and isononyl isononanoate is particularly preferred.

[0106] The aromatic ketone-based solvent may be selected from, but is not limited to, 1-tetrahydronaphthone, 2-tetrahydronaphthone, 2-(phenylepoxy)tetrahydronaphthone, 6-(methoxy)tetrahydronaphthone, acetophenone, phenylacetone, benzophenone, and their derivatives, such as at least one of 4-methylacetophenone, 3-methylacetophenone, 2-methylacetophenone, 4-methylphenylacetone, 3-methylphenylacetone, and 2-methylphenylacetone.

[0107] The aromatic ether-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, glycidylphenyl 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.

[0108] The aliphatic ketone-based solvent may be selected from, but is not limited to, at least one of 2-nonanone, 3-nonanone, 5-nonanone, 2-decanone, 2,5-hexanedione, 2,6,8-trimethyl-4-nonanone, frankinc, phorone, isophorone, and di-n-pentyl ketone.

[0109] The aliphatic ether-based solvent may be selected from, but is not limited to, at least one of pentyl 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.

[0110] It is understood that the organic solvent can be used alone or as a mixture of two or more organic solvents.

[0111] In some embodiments, the composition of this 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.

[0112] The other organic solvent may be selected from, but is not limited to, methanol, ethanol, 2-methoxyethanol, dichloromethane, trichloromethane, 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, tetrahydronaphthalene, naphthane, and indene.

[0113] In some preferred embodiments, the organic solvents suitable for this application are solvents with Hansen solubility parameters within the following ranges:

[0114] 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;

[0115] 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;

[0116] δh (hydrogen bond strength) is in the range of 0.9-14.2 MPa1 / 2, especially in the range of 2.0-6.0 MPa1 / 2.

[0117] In some embodiments, the organic solvent is selected based on its boiling point in accordance with the compositions of this application. In at least some embodiments, the organic solvent has a boiling point ≥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 of the inkjet printhead.

[0118] It is understood that the organic solvent can evaporate from the composition system to form a thin film containing the organic compound of this application.

[0119] 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 surfactants, lubricants, wetting agents, dispersants, hydrophobic agents, and adhesives.

[0120] In the composition described in this application, the content of the organic compound or mixture can be 0.01-10 wt%, preferably 0.1-8 wt%, more preferably 0.2-5 wt%, and even more preferably 0.25-3 wt%.

[0121] This application also relates to the use of the composition as a coating or printing ink in the preparation of organic electronic devices. In some embodiments, the composition is used to prepare organic electronic devices by a printing or coating preparation method.

[0122] The printing or coating preparation method can 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, torsional roller printing, offset printing, flexographic printing, rotary printing, spraying, brushing, pad printing, and slot extrusion coating. Gravure printing, nozzle printing, and inkjet printing are preferred.

[0123] Specifically, different printing or coating technologies may have different requirements for the concentration or viscosity of the composition system. The composition system can be adjusted accordingly to suit different printing or coating methods.

[0124] This application also provides the use of the organic compound, mixture, or composition as described above in organic electronic devices. Preferably, the organic compound is used in the hole transport layer or electron blocking layer of an OLED device.

[0125] This application provides an organic electronic device comprising, or prepared from, the organic compound or mixture described above. In one specific embodiment, the organic electronic device may be a red-light organic electronic device.

[0126] In one embodiment, an organic electronic device includes a first electrode, a second electrode, and one or more functional layers located between the first electrode and the second electrode, said functional layers comprising organic compounds, mixtures, or compositions as described above.

[0127] Furthermore, the organic electronic device includes a cathode, an anode, and one or more functional layers located at the cathode and anode, the functional layers comprising the organic compounds, mixtures, or compositions described above.

[0128] The organic electronic device may be selected from, but is 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, and organic plasmon emitting diodes. Organic electroluminescent devices, such as OLEDs, OLEECs, and organic light-emitting field-effect transistors, are particularly preferred.

[0129] The functional layer may 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 herein by reference.

[0130] In some embodiments, one or more functional layers of the organic electronic device include at least one electron blocking layer, the electron blocking layer comprising the organic compounds or mixtures described above, or prepared from the compositions described above. Specific organic compounds are defined as described above.

[0131] In one specific embodiment, the organic electronic device includes 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 an organic compound or mixture as described above, or is prepared from the above-described composition.

[0132] In one embodiment, the hole transport layer is selected from aromatic amine organic compounds.

[0133] In some embodiments, the material of the light-emitting layer may be selected from the structure shown in general formula (5):

[0134]

[0135] in:

[0136] q is selected from 1 or 2;

[0137] Each time Ar4 appears, it is independently selected from a heteroaromatic group with 5-40 substituted or unsubstituted ring atoms;

[0138] Each time Ar5 appears, it is independently selected from an aromatic group with 6-40 substituted or unsubstituted ring atoms, or a heteroaromatic group with 5-40 substituted or unsubstituted ring atoms.

[0139] When R7 and R8 appear, they are each independently selected from: -H, -D, a straight-chain alkyl group having 1 to 20 carbon atoms, a branched or cyclic alkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted aromatic group having 5 to 30 cyclic atoms, a substituted or unsubstituted heteroaromatic group having 5 to 30 cyclic atoms, or a combination of these groups.

[0140] In one embodiment, Ar4 may be selected independently from quinoline or isoquinoline and its derivatives each time it appears.

[0141] In one embodiment, Ar5 is independently selected from phenyl and its derivatives each time it appears.

[0142] Furthermore, in some embodiments, general formula (5) is selected from any structure of general formulas (6-1)-(6-3):

[0143]

[0144] in:

[0145] a is selected from any integer from 0 to 6, and b is selected from any integer from 0 to 4;

[0146] R9, R 10 Each time it appears, it is independently selected from: -D, a straight-chain alkyl group having 1 to 20 carbon atoms, a branched or cyclic alkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted aromatic group having 5 to 60 cyclic atoms, a substituted or unsubstituted heteroaromatic group having 5 to 60 cyclic atoms, or a combination of these groups.

[0147] Furthermore, in some embodiments, at least one R 10It is selected from straight-chain alkyl groups having 1 to 20 carbon atoms or branched or cyclic alkyl groups having 3 to 20 carbon atoms.

[0148] Furthermore, in some embodiments, at least one R9 is selected from straight-chain alkyl groups having 1 to 20 C atoms or branched or cyclic alkyl groups having 3 to 20 C atoms.

[0149] As an example, the material of the light-emitting layer can be selected from, but is not limited to, any of the following structures, which can be arbitrarily replaced:

[0150]

[0151]

[0152] It is understood that, in addition to the above functional layers, the organic electronic device may also have some conventional functional layers used in organic electronic devices that help improve device performance, such as hole injection layer, electron transport layer, electron injection layer, hole blocking layer, light extraction layer, etc.

[0153] In one embodiment, the organic electronic device includes an anode, a hole transport layer, an electron blocking layer, a light-emitting layer, an electron transport layer, and a cathode, which are stacked sequentially.

[0154] In one embodiment, the organic electronic device includes 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, which are stacked sequentially.

[0155] In one embodiment, the organic electronic device includes 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, which are stacked sequentially.

[0156] 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.

[0157] In some embodiments, the organic electronic device further includes 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 is 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 material may be plastic, metal, semiconductor wafer, or glass. Preferably, the substrate has a smooth surface, and a substrate without surface defects is particularly desirable. In a preferred embodiment, the substrate is a flexible substrate. The flexible substrate material 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 flexible substrate material may be polyethylene terephthalate (PET) or polyethylene glycol (2,6-naphthalene) (PEN).

[0158] The anode material is anode material known in the art for use in organic electronic devices, such as conductive metals, conductive metal oxides, or conductive polymers. In some embodiments, the absolute value of the difference between the work function of the anode material and the HOMO level or valence band level of the light emitter in the light-emitting layer or the p-type semiconductor material serving as a 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 anode material may be selected from, but is 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 readily selected by those skilled 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 fabricate devices according to the present invention.

[0159] The cathode material is a cathode material known in the art for use in organic electronic devices, such as a conductive metal or conductive metal oxide. In some embodiments, the absolute value of the difference between the work function of the cathode material and the LUMO level or conduction band level of the luminescent material or the n-type semiconductor material serving as an electron injection layer, electron transport layer, or hole blocking layer in the light-emitting 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 suitable for use as cathodes in OLEDs can be used as cathode materials for the devices of this application. As an example, the cathode material may be selected from, but is 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.

[0160] The material of the hole transport layer is a material known in the art for hole transport layers, for example, it may be selected from, but is not limited to, poly[bis(4-phenyl)(2,4,6-trimethylphenyl)amine] (PTXX), 2,2',7,7'-tetratetra[N,N-di(4-methoxyphenyl)amino]-9,9'-spiro-bisfluorene (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(carbazole-9-yl)triphenylamine (TCTX).

[0161] The material of the electron transport layer is a material known in the art for use in electron transport layers, for example, it may be selected from, but is not limited to, at least one of ET and Liq, PBD (2-(4-biphenyl)-5-phenyloxadiazole), 8-hydroxyquinoline aluminum (Xlq3) and graphene.

[0162] The chemical structural formulas of ET and Liq are as follows:

[0163]

[0164] The material of the hole injection layer is a material known in the art for hole injection layers, for example, it may be selected from, but is not limited to, at least one of 2,3,6,7,10,11-hexacyano-1,4,5,8,9,12-hexaazabenzophenanthrene (HXT-CN), PEDOT (polyethylene dioxythiophene), PEDOT:PSS and its derivatives doped with s-MoO3 (PEDOT:PSS:s-MoO3).

[0165] The light emission wavelength of the organic electronic device is between 600 and 700 nm, preferably between 600 and 650 nm, and even more preferably between 600 and 630 nm.

[0166] This application also relates to electronic devices incorporating the aforementioned organic electronic devices. The electronic devices may be, but are not limited to, display devices, lighting devices, light sources, and sensors.

[0167] The present application will be described in detail below with reference to specific embodiments. The following embodiments are only some embodiments of the present application and are not intended to limit the present application.

[0168] 1. Synthesis of compounds

[0169] Example 1

[0170] The synthetic route of compound 1 in this embodiment is as follows:

[0171]

[0172] Synthesis of intermediate 1-2: Compound 1-1 (60 mmol), pinacol diborate (60 mmol), Pd(dppf)Cl2 (0.2 mmol), and potassium acetate (70 mmol) were added to 180 mL of 1,4-dioxane and stirred at 100 °C for 8 h under nitrogen atmosphere. After cooling, the solvent was removed by rotary evaporation, the residue was dissolved in dichloromethane and washed with water, and the organic phase was collected. The solvent was removed by rotary evaporation of the organic phase, and the crude product was recrystallized to obtain intermediate 1-2 in 76% yield.

[0173] Synthesis of intermediates 1-5: Compounds 1-3 (45 mmol) and intermediate 1-4 (45 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (200 ml / 20 ml), and Pd(PPh3)4 (0.5 mmol) and potassium carbonate (90 mmol) were added. The mixture was stirred at 80 °C for 5 h under nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation. The product was then extracted with dichloromethane and washed with water. The organic phase was collected and the solvent was removed by rotary evaporation. The crude product was purified by column chromatography to obtain intermediate 1-5 in 80% yield.

[0174] Synthesis of intermediates 1-6: Intermediates 1-5 (30 mmol) and 1-2 (30 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (150 ml / 15 ml), and Pd(PPh3)4 (0.3 mmol) and potassium carbonate (60 mmol) were added. The mixture was stirred at 100 °C for 5 h under nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation. The product was then extracted with dichloromethane and washed with water. The organic phase was collected and the solvent was removed by rotary evaporation. The crude product was purified by column chromatography to obtain intermediates 1-6 in 75% yield.

[0175] Synthesis of Compound 1: Intermediate 1-6 (20 mmol), Compound 1-7 (20 mmol), Pd(dba)2 (0.2 mmol), tri-tert-butylphosphine (0.6 mmol), and sodium tert-butoxide (40 mmol) were dissolved in toluene and stirred at 100 °C for 12 h under nitrogen atmosphere. After cooling, the mixture was washed with water and separated. The organic phase was collected, and the solvent was removed by rotary evaporation. The crude product was purified by column chromatography and recrystallization to obtain Compound 1 in 80% yield. MS (ASAP): 629.

[0176] Example 2

[0177] The synthetic route of compound 2 in this embodiment is as follows:

[0178]

[0179] The synthesis of compound 2 can be performed in the same manner as that of compound 1, except that compounds 1-7 are replaced with compounds 2-1. The yield of compound 2 is 85%. MS (ASAP): 665.

[0180] Example 3

[0181] The synthetic route of compound 3 in this embodiment is as follows:

[0182]

[0183] Synthesis of intermediate 3-3: Compound 3-1 (40 mmol), compound 3-2 (40 mmol), Pd(dba)2 (0.2 mmol), tri-tert-butylphosphine (0.6 mmol), and sodium tert-butoxide (60 mmol) were added to 300 mL of toluene and stirred at 80 °C for 6 h under nitrogen atmosphere. After cooling, the reaction mixture was washed with water, and the organic phase was collected by separation. After removing the solvent by rotary evaporation, the organic phase was purified by column chromatography to obtain intermediate 3-3 in 72% yield.

[0184] The synthesis of compound 3 can be performed in the same manner as that of compound 1, except that compounds 1-7 are replaced with intermediate 3-3. The yield of compound 3 is 82%. MS (ASAP): 725.

[0185] Example 4

[0186] The synthetic route of compound 4 in this embodiment is as follows:

[0187]

[0188] The synthesis of intermediate 4-2 was the same as that of intermediate 1-5, except that compound 1-3 was replaced with compound 4-1. The yield of intermediate 4-2 was 79%.

[0189] The synthesis of intermediate 4-3 is the same as that of intermediate 1-6, except that intermediate 1-5 is replaced with intermediate 4-2, and the yield of intermediate 4-3 is 72%.

[0190] The synthesis of compound 4 was the same as that of compound 1, except that intermediates 1-6 were replaced with intermediate 4-3, and compounds 1-7 were replaced with compounds 4-4. The yield of compound 4 was 75%. MS (ASAP): 643.

[0191] Example 5

[0192] The synthetic route of compound 5 in this embodiment is as follows:

[0193]

[0194] Synthesis of intermediate 5-2:

[0195] Compounds 1-3 (45 mmol) and 5-1 (45 mmol) were dissolved in a mixed solvent of 1,4-dioxane and water (200 ml / 20 ml), and Pd(PPh3)4 (0.5 mmol) and potassium carbonate (90 mmol) were added. The mixture was stirred at 80 °C for 5 h under nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation. The product was then extracted with dichloromethane and washed with water. The organic phase was collected and the solvent was removed by rotary evaporation. The crude product was purified by column chromatography to obtain intermediate 5-2 in 82% yield.

[0196] The synthesis of intermediate 5-3 is the same as that of intermediates 1-6, except that intermediate 1-5 is replaced by intermediate 5-2. The yield of intermediate 5-3 is 85%.

[0197] The synthesis of compound 5 was the same as that of compound 1, except that intermediates 1-6 were replaced with intermediate 5-3, and compounds 1-7 were replaced with compound 5-4. The yield of compound 5 was 83%. MS (ASAP): 669.

[0198] Example 6

[0199] The synthetic route of compound 6 in this embodiment is as follows:

[0200]

[0201] The synthesis of intermediate 6-1 was the same as that of intermediate 5-2, except that compound 1-3 was replaced with compound 4-1, with a yield of 86%.

[0202] The synthesis of intermediate 6-2 is the same as that of intermediate 1-6, except that intermediate 1-5 is replaced with intermediate 6-1, with a yield of 80%.

[0203] The synthesis of compound 6 was the same as that of compound 1, except that intermediates 1-6 were replaced with intermediate 6-2, and compounds 1-7 were replaced with compound 6-3. The yield of compound 6 was 71%. MS (ASAP): 603.

[0204] Example 7

[0205] The synthetic route of compound 7 in this embodiment is as follows:

[0206]

[0207] The synthesis of intermediate 7-2 was the same as that of intermediate 3-3, except that compound 3-1 was replaced with compound 7-1, with a yield of 80%.

[0208] The synthesis of intermediate 7-4 was the same as that of intermediate 5-2, except that compound 5-1 was replaced with compound 7-3, with a yield of 80%.

[0209] The synthesis of intermediate 7-5 is the same as that of intermediate 1-6, except that intermediate 1-5 is replaced by intermediate 7-4, with a yield of 75%.

[0210] The synthesis of compound 7 was the same as that of compound 1, except that intermediates 1-6 were replaced with intermediate 7-5, and compounds 1-7 were replaced with intermediate 7-2. The yield of compound 7 was 82%. MS (ASAP): 725.

[0211] Example 8

[0212] The synthetic route of compound 8 in this embodiment is as follows:

[0213]

[0214] The synthesis of intermediate 8-1 was the same as that of intermediate 5-2, except that compound 5-1 was replaced with compound 7-3 and compound 1-3 was replaced with compound 4-1, with a yield of 89%.

[0215] The synthesis of intermediate 8-2 is the same as that of intermediate 1-6, except that intermediate 1-5 is replaced with intermediate 8-1, with a yield of 80%.

[0216] The synthesis of compound 8 was the same as that of compound 1, except that intermediates 1-6 were replaced with intermediate 8-2. The yield of compound 8 was 72%. MS (ASAP): 629.

[0217] Example 9

[0218] The synthetic route of compound 9 in this embodiment is as follows:

[0219]

[0220] The synthesis of intermediate 9-2 was the same as that of intermediate 1-2, except that compound 1-1 was replaced with compound 9-1, with a yield of 80%.

[0221] The synthesis of intermediate 9-3 was the same as that of intermediate 1-5, except that compound 1-4 was replaced with intermediate 9-2, with a yield of 77%.

[0222] The synthesis of intermediate 9-4 is the same as that of intermediate 1-6, except that intermediate 1-5 is replaced with intermediate 9-3, with a yield of 83%.

[0223] The synthesis of compound 9 was the same as that of compound 1, except that intermediates 1-6 were replaced with intermediate 9-4, and compounds 1-7 were replaced with compound 9-5. The yield of compound 9 was 88%. MS (ASAP): 645.

[0224] Example 10

[0225] The synthetic route of the compound in this embodiment is as follows:

[0226]

[0227] The synthesis of intermediate 10-2 was the same as that of intermediate 1-5, except that compound 1-3 was replaced with compound 4-1 and compound 1-4 was replaced with compound 10-1, with a yield of 87%.

[0228] The synthesis of intermediate 10-3 is the same as that of intermediate 1-6, except that intermediate 1-5 is replaced with intermediate 10-2, with a yield of 74%.

[0229] The synthesis of compound 10 was the same as that of compound 1, except that intermediates 1-6 were replaced with intermediate 10-3, and compounds 1-7 were replaced with compounds 9-5. The yield of compound 10 was 82%. MS (ASAP): 677.

[0230] Example 11

[0231] The synthetic route of compound 11 in this embodiment is as follows:

[0232]

[0233] The synthesis of intermediate 11-3 was the same as that of intermediate 3-3, except that compound 3-1 was replaced with compound 11-1 and compound 3-2 was replaced with compound 11-2, with a yield of 76%.

[0234] The synthesis of compound 11 was the same as that of compound 1, except that intermediates 1-6 were replaced with intermediates 7-5, and compounds 1-7 were replaced with compounds 11-3. The yield of compound 11 was 80%. MS (ASAP): 719.

[0235] Example 12

[0236] The synthetic route of compound 12 in this embodiment is as follows:

[0237]

[0238] The synthesis of intermediate 12-2 was the same as that of intermediate 1-2, except that compound 1-1 was replaced with compound 12-1, with a yield of 81%.

[0239] The synthesis of intermediate 12-3 was the same as that of intermediate 1-5, except that compound 1-4 was replaced with intermediate 12-2, with a yield of 80%.

[0240] The synthesis of intermediate 12-4 is the same as that of intermediate 1-6, except that intermediate 1-5 is replaced with intermediate 12-3, with a yield of 85%.

[0241] The synthesis of compound 12 was the same as that of compound 1, except that intermediates 1-6 were replaced with intermediate 12-4, and compounds 1-7 were replaced with compound 12-5. The yield of compound 12 was 80%. MS (ASAP): 719.

[0242] Example 13

[0243] The synthetic route of compound 13 in this embodiment is as follows:

[0244]

[0245] The synthesis of intermediate 13-2 was the same as that of intermediate 1-2, except that compound 1-1 was replaced with compound 13-1, with a yield of 83%.

[0246] The synthesis of intermediate 13-3 was the same as that of intermediate 1-5, except that compound 1-4 was replaced with intermediate 13-2, with a yield of 82%.

[0247] The synthesis of intermediate 13-4 is the same as that of intermediate 1-6, except that intermediate 1-5 is replaced with intermediate 13-3, with a yield of 84%.

[0248] The synthesis of compound 13 was the same as that of compound 1, except that intermediates 1-6 were replaced with intermediate 13-4, and compounds 1-7 were replaced with compounds 13-5. The yield of compound 13 was 85%. MS (ASAP): 687.

[0249] 2. Fabrication and Characterization of OLED Devices

[0250] The following detailed embodiments illustrate the OLED device employing the aforementioned compound and its fabrication process. The structure of this OLED device is as follows: Anode / Hole Injection Layer (HIL) / Hole Transport Layer (HTL) / Electron Blocking Layer (EBL) / Emitting Layer (EML) / Electron Transport Layer (ETL) / Electron Injection Layer (EIL) / Cathode. Specifically, a schematic diagram of the OLED device structure is shown below. Figure 1 As shown, 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.

[0251] In OLED devices, the substrate is a glass substrate, ITO is used as the anode, HATCN is used as the hole injection layer material, HT1 is used as the hole transport material, the above compounds 1-13 or Comparative Example 1 are used as the electron blocking layer material, RH1 is used as the host material of the luminescent material, RD1 or RD2 is used as the guest material of the luminescent material, ETM and Liq are used as electron transport materials, and Al is used as the cathode.

[0252] The materials HATCN, HT1, RH1, RD2, RD1, ETM, Liq, and the compound of Comparative Example 1 are all commercially available, or their synthetic methods are existing technologies. The relevant chemical structural formulas are as follows:

[0253]

[0254] The OLED-1 device structure consists of ITO / hole injection layer (5nm) / hole transport layer (90nm) / electron blocking layer (20nm) / host material RH1: red guest material RD2 / ETM: Liq / LiF / Al. The mass ratio of host material RH1 to RD2 is 95:5. The specific fabrication process is as follows:

[0255] a. Cleaning of ITO (Indium Tin Oxide) conductive glass substrate: Clean with various solvents (such as one or more of chloroform, acetone or isopropanol), and then perform ultraviolet ozone plasma treatment.

[0256] b. The compound HATCN was deposited on an ITO layer under high vacuum (1×10⁻⁶). -6 Hole injection layer with a thickness of 5 nm is obtained by thermal evaporation in millibars.

[0257] c. On the hole injection layer, a 90nm thick compound HT1 is deposited as a hole transport layer.

[0258] d. On the hole transport layer, a 20 nm thick layer of the aforementioned compound 1 of this application is deposited as an electron blocking layer;

[0259] e. A 40nm light-emitting layer is vacuum-deposited on the electron blocking layer; the light-emitting layer includes RH1 as the host material and RD2 as the guest material, and the two materials are co-evaporated from multiple sources.

[0260] f. On the light-emitting layer, an ETM / Liq mixture (mass ratio of 1:1) is vapor-deposited to form an electron transport layer with a thickness of 25 nm; on the electron transport layer, a LiF electron injection layer with a thickness of 0.5 nm and an Al cathode with a thickness of 150 nm are formed.

[0261] g. Packaging: The device is encapsulated in a nitrogen glove box using UV-cured resin.

[0262] The preparation schemes for OLED-2, OLED-16, and OLED-Ref are the same as those for OLED-1. The difference is that compound 1 in OLED-1 is replaced with the compound corresponding to the electron blocking layer material in Table 1, and the guest material RD2 of the luminescent material in OLED-1 is replaced with the guest material of the corresponding luminescent material in Table 1.

[0263] The current-voltage (JV) characteristics of each OLED device were characterized using characterization equipment, and the lifetime (LT95@1knits) 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 device's brightness to decrease from an initial brightness of 1000 nits to 95% of its initial brightness under constant current. Here, LT95@1000nits and external quantum efficiency are calculated relative to OLED-Ref (i.e., the comparative example, with the corresponding electron blocking layer material as Comparative Example 1), meaning the lifetime of OLED-Ref is 1 and the external quantum efficiency is 100%.

[0264] Table 1:

[0265]

[0266] As shown in Table 1:

[0267] Compared to the OLED device (OLED-Ref) prepared using the organic compound of Comparative Example 1 as the electron blocking layer material, the OLED devices (OLED-1 to OLED-16) prepared using compounds 1-13 as the electron blocking layer material exhibit better external quantum efficiency and longer lifetime. This demonstrates that the organic compound provided in this application is significantly superior to the organic compound of Comparative Example 1 as an electron blocking material.

[0268] Furthermore, OLED-1 and OLED-14 use the same electron blocking layer material, compound 1, but employ different guest materials RD2 and RD1 for the luminescent material, respectively. The external quantum efficiency and lifetime show no significant change, indicating that the electron blocking layer material compound 1 in this embodiment is applicable to various luminescent materials, achieving electron blocking for the luminescent layer of multiple materials. Combined with OLED-5 and OLED-15, OLED-9 and OLED-16, this demonstrates that the organic compound used as an electron blocking layer material in this application is applicable to various luminescent materials, illustrating the different guest materials for the luminescent layer.

[0269] The organic compounds, mixtures, compositions, and organic electronic devices provided in the embodiments of this application have been described in detail above. Specific examples have been used to illustrate the principles and implementation methods of this application. The descriptions of the above embodiments are only for the purpose of helping to understand the methods and core ideas of this application. At the same time, for those skilled in the art, there will be changes in the specific implementation methods and application scope based on the ideas of this application. Therefore, the content of this specification should not be construed as a limitation of this application.

Claims

1. An organic compound characterized in that, having a structure as shown in general formula (1): （1） wherein: Ar1, Ar2are independently selected from the following groups: ； R1, R2are independently selected from -H, -D, or a linear alkyl group having 1 to 6 C atoms, or an aromatic group having 6 to 14 ring atoms, or R1, R2are connected to each other to form a ring as follows: ； wherein: represents a point of attachment; R3, R4, R5, R6are independently at each occurrence selected from -H, -D, or a linear alkyl group having 1 to 6 C atoms, or a branched alkyl group having 3 to 6 C atoms, or phenyl.

2. The organic compound according to claim 1, wherein the structure of the organic compound is selected from any one of general formula (3-1) to (3-6): 。 3. The organic compound according to claim 1 or 2, wherein R1, R2are independently selected from -H, -D, methyl, ethyl or phenyl.

4. The organic compound according to claim 1, wherein R3is at each occurrence independently selected from -H, -D, or a linear alkyl group having 1 to 4 C atoms, or a branched alkyl group having 3 to 4 C atoms, or phenyl.

5. The organic compound according to claim 1, wherein is independently selected from the group consisting of: 。 6. An organic compound characterized in that, the organic compound is selected from any one of the following structures: 。 7. A mixture characterized in that, the mixture comprises the organic compound according to any one of claims 1 to 6 and at least one organic functional material selected from a hole injection material, a hole transport material, an electron transport material, an electron injection material, an electron blocking material, a hole blocking material, a host material or a guest material.

8. A composition characterized in that, the composition 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 comprising at least one electron blocking layer, characterized in that, the electron blocking layer comprises the organic compound according to any one of claims 1 to 6.

10. 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, 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 6, or the mixture according to claim 7, or the electron blocking layer is prepared from the composition according to claim 8.

11. The organic electronic device according to claim 10, wherein the material of the light-emitting layer is selected from the structures of RD1and RD2as follows: 。

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