Organic Compounds and Mixtures, Compositions, and Organic Electronic Devices Comprising the Same

Abstract

The present invention discloses an organic compound with the following structure: #imgabs0# In the organic compound of the present invention, the phosphoryl oxygen is connected to the imidazole through an aromatic group, and a fluorine-containing group is connected to the imidazole. The organic compound containing three electron-transporting groups, namely phosphoryl oxygen, imidazole, and fluorine, can provide transmission channels with multiple energy level gradients for the transmission of electrons, and has good electron-transporting ability. When used as an electron-transporting material in the electron-transporting layer of an electronic device, it can effectively improve the device efficiency and stability, and further improve the device performance and lifespan. Additionally, the present invention also discloses a mixture, a composition, and an organic electronic device.

Description

Technical Field

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

[0002] Due to the diversity of organic semiconductor materials, relatively low manufacturing costs, and excellent optical and electrical properties, etc., they have great potential in the preparation of organic light-emitting diodes (OLEDs) or optoelectronic devices, such as organic electronic devices like flat panel displays and lighting devices. The principle of light emission of organic electronic devices is organic electroluminescence, which refers to the phenomenon of converting electrical energy into light energy using organic substances. An organic electroluminescent device using organic electroluminescence usually has a positive electrode and a negative electrode, and a functional layer containing an organic substance between them. In order to improve the efficiency and lifespan of the organic electroluminescent element, the functional layer has a multi-layer structure, and each functional layer contains different organic substances. Specifically, it includes a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, or an electron injection layer, etc. In an organic electroluminescent device, when a voltage is applied between the two electrodes, holes are injected into the organic layer from the positive electrode, and electrons are injected into the organic layer from the negative electrode. When the injected holes and electrons meet, excitons are formed, and light is emitted when the excitons transition back to the ground state. Such an organic electroluminescent element has characteristics such as self-luminescence, high brightness, high efficiency, low driving voltage, wide viewing angle, high contrast, and high responsiveness.

[0003] In order to improve the light-emitting efficiency of organic electroluminescent devices, the development and combination of transport layer materials are crucial. By using hole transport and electron transport layer materials with appropriate transport capabilities, the organic electroluminescent device can achieve a balance in carrier transport, enabling electrons and holes to recombine at the center of the light-emitting layer, reducing exciton quenching, and thus effectively improving the light-emitting efficiency and the lifespan of the device.

[0004] Currently, although a large number of electron transport materials have been developed, the corresponding devices still have many problems such as unbalanced carrier transport and insufficient device lifespan. How to design new materials with better performance for adjustment to achieve the effects of adjusting transport balance, improving the efficiency and lifespan of the device has always been an urgent problem for those skilled in the art. Summary of the Invention

[0005] In view of this, the present invention provides an organic compound, aiming to provide new organic functional materials to improve the performance of the device.

[0006] The present invention is achieved through the following technical solutions:

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

[0008]

[0009] Wherein, Ar1 and Ar2 are 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;

[0010] Ar3 and Ar4 are independently selected from: a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, 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;

[0011] Each occurrence of L 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;

[0012] Each occurrence of R1 and R2 is independently selected from: hydrogen, deuterium, or a substituted or unsubstituted straight-chain alkyl group having 1 to 20 C atoms, or a substituted or unsubstituted straight-chain alkoxy group having 1 to 20 C atoms, or a substituted or unsubstituted straight-chain thioalkoxy group having 1 to 20 C atoms, or a substituted or unsubstituted branched-chain alkyl group having 3 to 20 C atoms, or a substituted or unsubstituted branched-chain alkoxy group having 3 to 20 C atoms, or a substituted or unsubstituted branched-chain thioalkoxy group having 3 to 20 C atoms, or a substituted or unsubstituted cyclic alkyl group having 3 to 20 C atoms, or a substituted or unsubstituted cyclic alkoxy group having 3 to 20 C atoms, or a substituted or unsubstituted 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 halocarbonyl 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, -CF3, -OCF3, -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 of these groups;

[0013] And at least one of R1 and R2 contains an F atom; n is an integer selected from 0 - 6; m is an integer selected from 0 - 8.

[0014] Correspondingly, the present invention further provides a mixture, comprising the above-mentioned organic compound and at least one organic functional material, and the organic functional material is 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 light-emitting guest material, a light-emitting host material or an organic dye.

[0015] Correspondingly, the present invention further provides a composition, comprising the above-mentioned organic compound or the above-mentioned mixture, and at least one organic solvent.

[0016] Correspondingly, the present invention further provides an organic electronic device, comprising at least one functional layer, and the functional layer contains the above-mentioned organic compound or the above-mentioned mixture, or the functional layer is prepared from the above-mentioned composition.

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

[0018] In the organic compound of the present invention, the phosphine oxide is connected to the imidazole through an aryl group, and a fluorine-containing group is connected to the imidazole. The organic compound containing three electron transport groups of phosphine oxide, imidazole and fluorine can provide multiple gradient transport channels for the transport of electrons, has good electron transport ability, and can effectively improve the device efficiency and stability when used as an electron transport material in the electron transport layer of an electronic device, thereby improving the device performance and lifespan. BRIEF DESCRIPTION OF THE DRAWINGS

[0019] In order to more clearly illustrate the technical solutions in the embodiments of the present invention, the following will briefly introduce the drawings required for the description of the embodiments. Obviously, the following drawings are only some embodiments of the present invention. For those skilled in the art, without creative efforts, other drawings can be obtained based on these drawings.

[0020] Figure 1 It is a schematic diagram of the OLED device shown in Embodiment 1 of the device of the present invention;

[0021] Among them, 101 is a substrate; 102 is an anode; 103 is a hole injection layer; 104 is a hole transport layer; 105 is a light-emitting layer; 106 is an electron transport layer; 107 is an electron injection layer; 108 is a cathode. DETAILED DESCRIPTION OF THE INVENTION

[0022] The technical solutions in the embodiments of the present invention will be clearly and completely described below with reference to the accompanying drawings in the embodiments of the present invention. It is obvious that the described embodiments are only a part of the embodiments of the present invention, rather than all of the embodiments. All other embodiments obtained by those skilled in the art based on the embodiments of the present invention without creative efforts belong to the scope of protection of the present invention. In addition, it should be understood that the specific embodiments described herein are only used to illustrate and explain the present invention, and are not used to limit the present invention.

[0023] In the description of the present invention, the term "comprising" means "including but not limited to", and the term "a plurality of" means "two or more". The various embodiments of the present invention 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 brevity, and should not be construed as a rigid limitation on the scope of the present invention; therefore, it should be considered that the description of the range has specifically disclosed all possible sub-ranges and single values within that range. For example, it should be considered that the description of the range 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 that range, such as 1, 2, 3, 4, 5, and 6, regardless of the range. Additionally, whenever a numerical range is indicated herein, it means including any cited number (fraction or integer) within the indicated range.

[0024] Unless otherwise defined, all technical and scientific terms used herein have the same meaning as commonly understood by those skilled in the technical field to which the present invention belongs. The terms used in the description of the present invention herein are only for the purpose of describing specific embodiments, and are not intended to limit the present invention.

[0025] The terms "and / or", "or / and", and "and / or" used in the present invention cover any one of two or more related listed items, as well as any and all combinations of the related listed items. The said any and all combinations include combinations of any two related listed items, any more related listed items, or all related listed items. It should be noted that when at least three items are connected by at least two conjunctive combinations selected from "and / or", "or / and", and "and / or", it should be understood that in the present invention, this technical solution undoubtedly includes the technical solution connected by "logical AND", and also undoubtedly includes the technical solution connected by "logical OR". For example, "A and / or B" includes three parallel solutions: A, B, and A + B. Another example, the technical solution of "A, and / or, B, and / or, C, and / or, D" includes any one of A, B, C, and D (i.e., the technical solution connected by "logical OR"), and also includes any and all combinations of A, B, C, and D, that is, it includes combinations of any two or any three of A, B, C, and D, and also includes the combination of the four items A, B, C, and D (i.e., the technical solution connected by "logical AND").

[0026] In the present invention, the aromatic group, aromatic, and aromatic ring system have the same meaning and can be interchanged.

[0027] In the present invention, the heteroaromatic group, heteroaromatic, and heteroaromatic ring system have the same meaning and can be interchanged.

[0028] In the present invention, the "heteroatom" is a non-carbon atom and can be an N atom, an O atom, an S atom, etc.

[0029] In the present invention, "substituted" means that the hydrogen atom in the substituent is replaced by the substituent.

[0030] In the present invention, when the same substituent appears multiple times, it can be independently selected from different groups. For example, if the general formula contains multiple Rs, then each R can be independently selected from different groups.

[0031] In the present invention, "substituted or unsubstituted" means that the defined group may be substituted or may not be substituted. When the defined group is substituted, it should be understood that the defined group may be substituted by one or more substituents R, and the R is selected from, but not limited to: deuterium atom, cyano group, isocyano group, nitro group or halogen, alkyl group 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 group, carbonyl group, alkoxycarbonyl group, aryloxycarbonyl group, carbamoyl group, halocarbonyl group, formyl group, isocyanate group, thiocyanate group, isothiocyanate group, hydroxyl group, trifluoromethyl group, and the above groups may also be further substituted by substituents acceptable in the art; it can be understood that R’ and R” in -NR’R” are each independently selected from, but not limited to: H, deuterium atom, cyano group, isocyano group, nitro group or halogen, alkyl group containing 1-10 C atoms, heterocyclic group containing 3-20 ring atoms, aromatic group containing 6-20 ring atoms, heteroaromatic group containing 5-20 ring atoms. Preferably, R is selected from, but not limited to: deuterium atom, cyano group, isocyano group, nitro group or halogen, alkyl group containing 1-10 C atoms, heterocyclic group containing 3-10 ring atoms, aromatic group containing 6-20 ring atoms, heteroaromatic group containing 5-20 ring atoms, silyl group, carbonyl group, alkoxycarbonyl group, aryloxycarbonyl group, carbamoyl group, halocarbonyl group, formyl group, isocyanate group, thiocyanate group, isothiocyanate group, hydroxyl group, trifluoromethyl group, and the above groups may also be further substituted by substituents acceptable in the art.

[0032] In the present invention, "number of ring atoms" means the number of ring atoms that form the ring itself in a structural compound obtained by bonding atoms into a ring (for example, monocyclic compound, fused-ring compound, crosslinked compound, carbocyclic compound, heterocyclic compound), that is, the number of atoms forming the ring. When the ring is substituted by a substituent, the atoms contained in the substituent are not included in the ring atoms. The same applies to the "number of ring atoms" described below under the condition of no special description. 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 thiophenyl group is 5.

[0033] "Aryl or aromatic group" refers to an aromatic hydrocarbon group derived by removing one hydrogen atom from an aromatic ring compound, which can be a monocyclic aryl group, or a fused-ring aryl group, or a polycyclic aryl group. For polycyclic ring species, at least one is an aromatic ring system. For example, "substituted or unsubstituted aryl group having 6 to 40 ring atoms" refers to an aryl group containing 6 to 40 ring atoms, and the aryl group can optionally be further substituted. Preferably, it is a substituted or unsubstituted aryl group having 6 to 30 ring atoms, more preferably a substituted or unsubstituted aryl group having 6 to 18 ring atoms, particularly preferably a substituted or unsubstituted aryl group having 6 to 14 ring atoms, and the aryl group is optionally further substituted; suitable examples include but are not limited to: phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthryl, fluoranthenyl, triphenylenyl, pyrenyl, perylenyl, tetracenyl, fluorenyl, binaphthylenyl, acenaphthylenyl and their derivatives. It can be understood 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 such as acenaphthene, fluorene, or 9,9-diarylfluorene, triarylamine, diaryl ether systems should also be included in the definition of aryl groups.

[0034] "Heteroaryl or heteroaromatic group" refers to a group in which at least one carbon atom in the aryl group is replaced by a non-carbon atom, and the non-carbon atom can be an N atom, an O atom, an 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, particularly preferably a substituted or unsubstituted heteroaryl group 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, dioxazolyl, triazolyl, imidazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, acridinyl, pyridazinyl, pyrazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, benzothienyl, benzofuryl, indolyl, pyrroloimidazolyl, pyrrolopyrrolyl, thienopyrrolyl, thienothienyl, furanopyrrolyl, furanofuryl, thienofuryl, benzisoxazolyl, benzisothiazolyl, benzimidazolyl, phthalazinyl, phenanthridinyl, perimidinyl, quinazolinone, dibenzothienyl, dibenzofuryl, carbazolyl and their derivatives.

[0035] In the present invention, "alkyl" can represent a straight-chain, branched-chain and / or cyclic alkyl group. The number of carbon atoms in 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, "C 1-9"Alkyl" refers to an alkyl group containing 1 to 9 carbon atoms, and each occurrence can independently be a C1 alkyl group, C2 alkyl group, C3 alkyl group, C4 alkyl group, C5 alkyl group, C6 alkyl group, C7 alkyl group, C8 alkyl group or C9 alkyl group. Non-limiting examples of alkyl groups include methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, t-butyl, isobutyl, 2-ethylbutyl, 3,3-dimethylbutyl, n-pentyl, isopentyl, neopentyl, t-pentyl, cyclopentyl, 1-methylpentyl, 3-methylpentyl, 2-ethylpentyl, 4-methyl-2-pentyl, n-hexyl, 1-methylhexyl, 2-ethylhexyl, 2-butylhexyl, cyclohexyl, 4-methylcyclohexyl, 4-t-butylcyclohexyl, n-heptyl, 1-methylheptyl, 2,2-dimethylheptyl, 2-ethylheptyl, 2-butylheptyl, n-octyl, t-octyl, 2-ethyloctyl, 2-butyl octyl, 2-hexyloctyl, 3,7-dimethyloctyl, cyclooctyl, n-nonyl, n-decyl, adamantyl, 2-ethyldecyl, 2-butyldecyl, 2-hexyldecyl, 2-octyldecyl, n-undecyl, n-dodecyl, 2-ethyldodecyl, 2-butyldodecyl, 2-hexyldodecyl, 2-octyldodecyl, n-tridecyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, 2-ethylhexadecyl, 2-butyldecyl, 2-hexyldecyl, 2-octyldecyl, n-heptadecyl, n-octadecyl, n-nonadecyl, n-eicosyl, 2-ethyleicosyl, 2-butyleicosyl, 2-hexyleicosyl, 2-octyleicosyl, n-heneicosyl, n-docosyl, n-tricosyl, n-tetracosyl, n-pentacosyl, n-hexacosyl, n-heptacosyl, n-octacosyl, n-nonacosyl, n-triacontyl, etc.

[0036] In the present invention, the abbreviations of substituents 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.

[0037] In the present invention, "amino group" refers to a derivative of amine, having a structural feature of formula -N(X)2, where each "X" is independently selected from H, substituted or unsubstituted alkyl group, substituted or unsubstituted cycloalkyl group, 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 group)2, -NH(heterocyclic group), -N(aryl)2, -NH(aryl), -N(alkyl)(aryl), -N(alkyl)(heterocyclic group), -N(cycloalkyl)(heterocyclic group), -N(aryl)(heteroaryl), -N(alkyl)(heteroaryl), etc.

[0038] In the present invention, unless otherwise defined, a hydroxyl group refers to -OH, a carboxyl group refers to -COOH, a carbonyl group refers to -C(=O)-, an amino group refers to -NH2, a formyl group refers to -C(=O)H, a halocarbonyl group refers to -C(=O)Z (wherein Z represents a halogen), a carbamoyl group refers to -C(=O)NH2, an isocyanate group refers to -NCO, and an isothiocyanate group refers to -NCS.

[0039] In the present invention, an "alkoxy group" refers to a group having the structure "-O-alkyl", that is, the alkyl group defined as above is connected to other groups 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 (-O-C(CH3)3 or -OtBu).

[0040] In the present invention, "*" represents a connection site or a fusion site. When the connection site is not specified in a group, it means that any optional connection site in the group can be used as the connection site. When the fusion site is not specified in a group, it means that any optional fusion site in the group can be used as the fusion site. Preferably, two or more sites adjacent to each other in the group are fusion sites.

[0041] In the present invention, when a group contains multiple substituents with the same symbol, each substituent can be the same as or different from each other. For example the six Rs on the benzene ring can be the same as or different from each other.

[0042] In the present invention, the single bond to which a substituent is attached passes through the corresponding ring, indicating that the substituent can be connected to any optional position of the ring. For example in, R can be connected to any substitutable site of the benzene ring.

[0043] In the present invention, "its combination", "any combination thereof", "any combination mode thereof", etc. include all suitable combination modes of any two or more than two items in the listed items.

[0044] In the present invention, "further", "even further", "especially", etc. are used for descriptive purposes, indicating differences in content, but should not be construed as limiting the scope of protection of the present invention.

[0045] In the present invention, "optionally", "optional", "optional" mean that it can be present or absent, that is, it refers to any one of the two alternative schemes of "present" or "absent". If "optional" appears in multiple places in a technical solution, unless otherwise specified and there is no contradiction or mutual restriction relationship, each "optional" is independent of each other.

[0046] In the present invention, for the technical features described in an open-ended manner, it includes a closed technical solution composed of the listed features, and also includes an open-ended technical solution containing the listed features.

[0047] The present invention provides an organic compound having a structure represented by the general formula (1):

[0048]

[0049] Wherein, Ar1 and Ar2 are 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;

[0050] Ar3 and Ar4 are independently selected from: a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, 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;

[0051] Each occurrence of L 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;

[0052] Each occurrence of R1 and R2 is independently selected from: hydrogen, deuterium, or a substituted or unsubstituted straight-chain alkyl group having 1 to 20 C atoms, or a substituted or unsubstituted straight-chain alkoxy group having 1 to 20 C atoms, or a substituted or unsubstituted straight-chain thioalkoxy group having 1 to 20 C atoms, or a substituted or unsubstituted branched-chain alkyl group having 3 to 20 C atoms, or a substituted or unsubstituted branched-chain alkoxy group having 3 to 20 C atoms, or a substituted or unsubstituted branched-chain thioalkoxy group having 3 to 20 C atoms, or a substituted or unsubstituted cyclic alkyl group having 3 to 20 C atoms, or a substituted or unsubstituted cyclic alkoxy group having 3 to 20 C atoms, or a substituted or unsubstituted 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 halocarbonyl 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, -CF3, -OCF3, -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 of these groups;

[0053] And at least one of R1 and R2 contains an F atom;

[0054] n is an integer selected from 0 - 6; m is an integer selected from 0 - 8.

[0055] In one embodiment, Ar1 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;

[0056] Further, Ar1 is independently selected from a substituted or unsubstituted aromatic group having 6 to 14 ring atoms, or a substituted or unsubstituted heteroaromatic group having 5 to 14 ring atoms.

[0057] In a specific embodiment, Ar1 is selected from the following groups:

[0058]

[0059] Wherein: each occurrence of X is independently selected from CR1 or N; preferably, each occurrence of X is independently selected from CR1;

[0060] Each occurrence of Y is independently selected from NR4, PR4, CR5R6, SiR5R6, O, S, S(=O)2 or S(=O);

[0061] Each occurrence of R4, R5, and R6 is independently selected from: hydrogen, deuterium, or a substituted or unsubstituted straight-chain alkyl having 1 to 20 C atoms, or a substituted or unsubstituted straight-chain alkoxy having 1 to 20 C atoms, or a substituted or unsubstituted straight-chain thioalkoxy having 1 to 20 C atoms, or a substituted or unsubstituted branched-chain alkyl having 3 to 20 C atoms, or a substituted or unsubstituted branched-chain alkoxy having 3 to 20 C atoms, or a substituted or unsubstituted branched-chain thioalkoxy having 3 to 20 C atoms, or a substituted or unsubstituted cyclic alkyl having 3 to 20 C atoms, or a substituted or unsubstituted cyclic alkoxy having 3 to 20 C atoms, or a substituted or unsubstituted cyclic thioalkoxy 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, cyano, carbamoyl, halocarbonyl, formyl, isocyano, isocyanate, thiocyanate, isothiocyanate, hydroxy, nitro, amino, -CF3, -OCF3, -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 of these groups;

[0062] * represents the fusion site.

[0063] In one embodiment, each occurrence of R1 and R2 is independently selected from: hydrogen, deuterium, or a substituted or unsubstituted straight-chain alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted branched-chain alkyl group having 3 to 10 carbon atoms, or a substituted or unsubstituted cyclic alkyl group having 3 to 10 carbon atoms, or a substituted or unsubstituted straight-chain alkoxy group having 1 to 10 carbon atoms, or a substituted or unsubstituted branched-chain alkoxy group having 3 to 10 carbon atoms, cyano, isocyano, nitro, -CF3, -OCF3, -Cl, -Br, -F, -I, or a substituted or unsubstituted aromatic group having 6 to 30 ring atoms, or a substituted or unsubstituted heteroaromatic group having 5 to 30 ring atoms, or a combination of these groups; and at least one of R1 and R2 contains an F atom.

[0064] In one embodiment, each occurrence of R1 and R2 is independently selected from: hydrogen, deuterium, -F, an unsubstituted or one or more F-substituted straight-chain alkyl group having 1 to 10 carbon atoms, an unsubstituted or one or more F-substituted branched-chain alkyl group having 3 to 10 carbon atoms, or an unsubstituted or one or more F-substituted cyclic alkyl group having 3 to 10 carbon atoms, an unsubstituted or one or more F-substituted straight-chain alkoxy group having 1 to 10 carbon atoms, an unsubstituted or one or more F-substituted branched-chain alkoxy group having 3 to 10 carbon atoms; and at least one of R1 and R2 contains an F atom.

[0065] In one specific embodiment, each occurrence of R1 and R2 is independently selected from: hydrogen (-H), deuterium (-D), fluorine (-F), methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl (-CF3), or the following groups:

[0066]

[0067] wherein: a is selected from 1, 2, 3, 4, or 5.

[0068] In one embodiment, R2 is selected from -F, -CF3, or the following groups:

[0069]

[0070] Further, each occurrence of R1 is selected from hydrogen, deuterium, -F, methyl, ethyl, isopropyl, tert-butyl, -CF3, or the following groups:

[0071]

[0072] In another embodiment, at least one of R1 is selected from -F, -CF3, or the following groups:

[0073]

[0074] Further, R2 is selected from hydrogen, deuterium, -F, methyl, ethyl, isopropyl, tert-butyl, -CF3, or a group as follows:

[0075]

[0076] In the above embodiments, a is selected from 1, 2, 3, 4, or 5.

[0077] In one embodiment, each occurrence of Y is independently selected from N-CH3, N-Ph, C(CH3)2, O, or S. Further, Ar2 and L are independently selected from a substituted or unsubstituted aromatic group having 6 to 16 ring atoms, or a substituted or unsubstituted heteroaromatic group having 6 to 16 ring atoms.

[0078] In a specific embodiment, Ar2 and / or L are independently selected from the following groups:

[0079]

[0080] Wherein: each occurrence of X1 is independently selected from CR7 or N;

[0081] Each occurrence of Y1 is independently selected from NR8, PR8, CR9R 10 , SiR9R 10 , O, S, S(=O)2, or S(=O);

[0082] R7, R8, R9, R 10Each occurrence is independently selected from: hydrogen, deuterium, or a substituted or unsubstituted straight-chain alkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted straight-chain alkoxy group having 1 to 20 carbon atoms, or a substituted or unsubstituted straight-chain thioalkoxy group having 1 to 20 carbon atoms, or a substituted or unsubstituted branched-chain alkyl group having 3 to 20 carbon atoms, or a substituted or unsubstituted branched-chain alkoxy group having 3 to 20 carbon atoms, or a substituted or unsubstituted branched-chain thioalkoxy group having 3 to 20 carbon atoms, or a substituted or unsubstituted cyclic alkyl group having 3 to 20 carbon atoms, or a substituted or unsubstituted cyclic alkoxy group having 3 to 20 carbon atoms, or a substituted or unsubstituted cyclic thioalkoxy group having 3 to 20 carbon atoms, or a silyl group, or a keto group having 1 to 20 carbon atoms, or an alkoxycarbonyl group having 2 to 20 carbon atoms, or an aryloxycarbonyl group having 7 to 20 carbon atoms, a cyano group, a carbamoyl group, a halocarbonyl 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, -CF3, -OCF3, -Cl, -Br, -F, -I, or an alkenyl group having 2 to 20 carbon 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 of these groups.

[0083] It should be noted that when X1 is a connection site, X1 is selected from a C atom; when Y1 is a connection site, Y1 is selected from an N atom.

[0084] In some embodiments, in formula (1), Ar2 and / or L are each independently selected from any one of formulas (C-1) to (C-18):

[0085]

[0086] Wherein, * represents a connection site.

[0087] In one embodiment, the organic compound of general formula (1) is selected from the structures shown in formulas (2-1) to (2-11):

[0088] Wherein, m1 is selected from 0, 1, 2, 3 or 4. Wherein X, Y and Y1 can refer to the definitions in the foregoing text.

[0089] In one embodiment, n is selected from 0 or 1.

[0090] In one embodiment, R7, R8, R9, R 10Each occurrence is independently selected from: hydrogen, deuterium, or a substituted or unsubstituted straight-chain alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted branched-chain alkyl group having 3 to 10 carbon atoms, or a substituted or unsubstituted cyclic alkyl group having 3 to 10 carbon atoms, cyano, isocyano, nitro, -CF3, -OCF3, -Cl, -Br, -F, -I, or 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, or a combination of these groups.

[0091] In one embodiment, Ar3 to Ar4 are each independently selected from a substituted or unsubstituted alkyl chain having 1 to 10 carbon atoms, a substituted or unsubstituted alkoxy chain having 1 to 10 carbon atoms, 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.

[0092] In one embodiment, Ar3 to Ar4 are independently selected from the following groups:

[0093]

[0094] Wherein:

[0095] Each occurrence of X2 is independently selected from CR 11 or N;

[0096] Each occurrence of Y2 is independently selected from NR 12 , PR 12 , CR 13 R 14 , SiR 13 R 14 , O, S, S(=O)2 or S(=O);

[0097] R 11 R 12 R 13 R 14Each occurrence is independently selected from: H, D, a straight-chain alkyl group having 1 to 20 C atoms, a straight-chain alkoxy group having 1 to 20 C atoms, a straight-chain thioalkoxy group having 1 to 20 C atoms, a branched-chain alkyl group having 3 to 20 C atoms, a cycloalkyl group having 3 to 20 C atoms, a branched-chain alkoxy group having 3 to 20 C atoms, a cyclic alkoxy group having 3 to 20 C atoms, a branched-chain thioalkoxy group having 3 to 20 C atoms, a cyclic thioalkoxy group having 3 to 20 C atoms, a silyl group, a keto group having 1 to 20 C atoms, an alkoxycarbonyl group having 2 to 20 C atoms, an aryloxycarbonyl group having 7 to 20 C atoms, a cyano group, a carbamoyl group, a halocarbonyl group, a formyl group, an isocyano group, an isocyanate group, a thiocyanate group, an isothiocyanate group, a hydroxyl group, a nitro group, CF3, OCF3, Cl, Br, F, a substituted or unsubstituted aromatic group having 5 to 40 ring atoms, a substituted or unsubstituted heteroaromatic group having 5 to 40 ring atoms, a substituted or unsubstituted aryloxy group having 5 to 40 ring atoms, or a substituted or unsubstituted heteroaryloxy group having 5 to 40 ring atoms, or a combination of these systems;

[0098] Two adjacent Rs 11 Are connected to form a ring or not form a ring with each other.

[0099] In one embodiment, R 11 、R 12 、R 13 、R 14 Each occurrence is independently selected from: hydrogen, deuterium, or a substituted or unsubstituted straight-chain alkyl group having 1 to 10 C atoms, or a substituted or unsubstituted branched-chain alkyl group having 3 to 10 C atoms, or a substituted or unsubstituted cyclic alkyl group having 3 to 10 C atoms, a cyano group, an isocyano group, a nitro group, -CF3, -OCF3, -Cl, -Br, -F, -I, or 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, or a combination of these groups.

[0100] In one embodiment, Ar3 and Ar4 are selected from the same group.

[0101] Furthermore, the organic compounds of the present invention include but are not limited to the structures shown below:

[0102]

[0103]

[0104]

[0105]

[0106] In one embodiment, the hydrogen atoms (H) in the organic compound of the present invention may be partially deuterated (D). Preferably, 10% of the H is deuterated, or 20% of the H is deuterated; more preferably, 30% of the H is deuterated or 40% of the H is deuterated.

[0107] In the organic compound of the present invention, the phosphine oxide is connected to the imidazole through an aromatic group, and a fluorine-containing group is connected to the imidazole. The organic compound containing three electron-transporting groups of phosphine oxide, imidazole, and fluorine can provide multiple gradient transmission channels for electron transmission, has good electron-transporting ability, and can effectively improve the device efficiency and stability when used as an electron-transporting material in the electron-transporting layer of an electronic device, thereby improving the device performance and lifespan.

[0108] The organic compound of the invention can be used as a functional material in the preparation of organic electronic devices, especially OLED devices. Further, the electron-transporting compound of the present invention can be used as an electron-transporting material for preparing an electron-transporting layer.

[0109] The present invention relates to an electron-transporting layer material containing the organic compound as described above.

[0110] The present invention relates to a mixture containing at least one of the above-described organic compounds and at least one other organic functional material; the at least one other organic functional material can be selected from a hole injection material (HIM), a hole transport material (HTM), an electron transport material (ETM), an electron injection material (EIM), an electron blocking material (EBM), a hole blocking material (HBM), a light-emitting guest material (Emitter), a light-emitting host material (Host), and an organic dye. For example, various organic functional materials are described in detail in WO2010135519A1, US20090134784A1, and WO2011110277A1. The entire contents of these three patent documents are hereby incorporated herein by reference.

[0111] In one embodiment, the other organic functional material is selected from a hole transport material.

[0112] The present invention also relates to a composition containing at least one of the above-described organic compounds or mixtures and at least one organic solvent. Among them, the at least one organic solvent can be selected from aromatic or heteroaromatic, esters, aromatic ketones or aromatic ethers, aliphatic ketones or aliphatic ethers, alicyclic or olefinic compounds, borate or phosphate compounds. That is, the solvent contained in the composition of the present invention can be any one of the above organic solvents, or a mixed solvent of two or more of them. In a preferred embodiment, the at least one organic solvent contained in the composition of the present invention is selected from aromatic or heteroaromatic solvents.

[0113] Specifically, aromatic or heteroaromatic solvents include but are not limited to: p-diisopropylbenzene, amylbenzene, tetralin, cyclohexylbenzene, chloronaphthalene, 1,4-dimethylnaphthalene, 3-isopropylbiphenyl, p-methylcumene, dipentylbenzene, tripentylbenzene, amyltoluene, 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, benzyl butylbenzene, dimethylnaphthalene, 3-isopropylbiphenyl, p-methylcumene, 1-methylnaphthalene, 1,2,4-trichlorobenzene, 4,4-difluorodiphenylmethane, 1,2-dimethoxy-4-(1-propenyl)benzene, diphenylmethane, 2-phenylpyridine, 3-phenylpyridine, N-methyldiphenylamine, 4-isopropylbiphenyl, α,α-dichlorodiphenylmethane, 4-(3-phenylpropyl)pyridine, benzyl benzoate, 1,1-bis(3,4-dimethylphenyl)ethane, 2-isopropylnaphthalene, quinoline, isoquinoline, methyl 2-furoate, ethyl 2-furoate, etc.

[0114] Ester-based solvents include but are not limited to: alkyl octanoates, alkyl sebacates, alkyl stearates, alkyl benzoates, alkyl phenylacetates, alkyl cinnamates, alkyl oxalates, alkyl maleates, alkanolactones, alkyl oleates, etc. Octyl octanoate, diethyl sebacate, diallyl phthalate, isononyl isononanoate, etc. are particularly preferred.

[0115] Aromatic ketone-based solvents include but are not limited to: 1-tetralone, 2-tetralone, 2-(phenyl epoxy)tetralone, 6-(methoxy)tetralone, acetophenone, propiophenone, or benzophenone and its derivatives; such as 4-methylacetophenone, 3-methylacetophenone, 2-methylacetophenone, 4-methylpropiophenone, 3-methylpropiophenone, 2-methylpropiophenone, etc.

[0116] Aromatic ether-based solvents include but are not limited to: 3-phenoxytoluene, butoxybenzene, dimethyl acetal of p-anisaldehyde, tetrahydro-2-phenoxy-2H-pyran, 1,2-dimethoxy-4-(1-propenyl)benzene, 1,4-benzodioxane, 1,3-dipropylbenzene, 2,5-dimethoxytoluene, 4-ethylbenzyl ether, 1,3-dipropoxybenzene, 1,2,4-trimethoxybenzene, 4-(1-propenyl)-1,2-dimethoxybenzene, 1,3-dimethoxybenzene, glycidyl phenyl ether, dibenzyl ether, 4-tert-butylanisole, trans-p-propenylanisole, 1,2-dimethoxybenzene, 1-methoxynaphthalene, diphenyl ether, 2-phenoxymethyl ether, 2-phenoxytetrahydrofuran, ethyl 2-naphthyl ether, etc.

[0117] Aliphatic ketone-based solvents include, but are not limited to: 2-nonanone, 3-nonanone, 5-nonanone, 2-decanone, 2,5-hexanedione, 2,6,8-trimethyl-4-nonanone, fenchone, phorone, isophorone, di-n-pentyl ketone, etc.; or aliphatic ethers, such as, 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, tetraethylene glycol dimethyl ether, etc.

[0118] It can be understood that the solvent can be used alone or as a mixture of two or more organic solvents.

[0119] In some embodiments, the composition of the present invention comprises at least one organic compound or mixture as described above, and at least one organic solvent, and may further comprise another organic solvent.

[0120] Another organic solvent includes, but is 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, indene.

[0121] In some preferred embodiments, the organic solvent suitable for the present invention is a solvent with Hansen solubility parameters in the following ranges:

[0122] δd (dispersion force) is in the range of 17.0 - 23.2 MPa1 / 2, especially in the range of 18.5 - 2l.0 MPa1 / 2;

[0123] 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;

[0124] δh (hydrogen bonding force) is in the range of 0.9 - 14.2 MPa1 / 2, especially in the range of 2.0 - 6.0 MPa1 / 2.

[0125] In some embodiments, for the composition according to the present invention, the boiling point needs to be considered when selecting the organic solvent. In at least some embodiments, the boiling point of the organic solvent ≥ 150 °C; preferably ≥ 180 °C; more preferably ≥ 200 °C; even more preferably ≥ 250 °C; most preferably ≥ 275 °C or ≥ 300 °C. Boiling points within these ranges are beneficial for preventing nozzle blockage of the inkjet print head.

[0126] It is understood that the organic solvent can evaporate from the composition system to form a thin film containing the organic compound of the present invention.

[0127] In some embodiments, the composition is a solution. In other embodiments, the composition is a suspension.

[0128] In the composition, the content of the organic compound or mixture can be 0.01 wt% - 10 wt%, preferably 0.1 wt% - 5 wt%, more preferably 0.2 - 5 wt%, and even more preferably 0.25 - 3 wt%.

[0129] The present invention 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 preparation method of printing or coating. The preparation method of printing or coating can be, but is not limited to, inkjet printing, nozzle printing, letterpress printing, screen printing, intaglio printing, dip coating, spin coating, blade coating, roller printing, reverse roller printing, lithographic printing, flexographic printing, rotary printing, spraying, brush coating, pad printing, slot die coating, etc. Preferably, intaglio printing, nozzle printing and inkjet printing.

[0130] The solution or suspension can additionally include additives for adjusting viscosity, adjusting film-forming properties, improving adhesion, etc. The additives can be selected from at least one of, but not limited to, surface active compounds, lubricants, wetting agents, dispersants, water repellents and adhesives. Different printing or coating methods may have different requirements for the coating or printing ink, and the concentration, viscosity, etc. of the solution or suspension can be adjusted accordingly to adapt to different printing or coating methods.

[0131] The present invention also provides an application of the organic compound, mixture or composition as described above in an organic electronic device. The technical solution is as follows:

[0132] An organic electronic device comprising the organic compound or mixture as described above, or prepared from the composition.

[0133] Furthermore, an organic electronic device comprising a first electrode, a second electrode, and one or more organic functional layers located between the first electrode and the second electrode, the organic functional layer comprising the organic compound, mixture as described above, or prepared from the above composition. Wherein, the first electrode and the second electrode are a pair of electrodes. For example, if the first electrode is an anode, the second electrode is a cathode; vice versa.

[0134] The organic electronic device can be, but is not limited to, an organic light-emitting diode (OLED device), an organic photovoltaic cell (OPV), an organic light-emitting electrochemical cell (OLEEC), an organic field-effect transistor (OFET), an organic light-emitting field-effect transistor, an organic laser, an organic spintronic device, an organic sensor, and an organic plasmon emitting diode, etc. The organic electronic device is preferably an organic electroluminescent device, such as an OLED.

[0135] The organic functional layer is selected from a hole injection layer (HIL), a hole transport layer (HTL), a light-emitting 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, and the entire contents of these three patent documents are hereby incorporated herein by reference.

[0136] In some embodiments, at least an electron transport layer is included in one or more organic functional layers of the organic electronic device. The material of the electron transport layer comprises the organic compound, mixture, or composition prepared from the foregoing as described above. Further, the one or more organic functional layers may further include a light-emitting layer.

[0137] The present invention relates to an organic electronic device, which comprises: a cathode, an anode, and one or more organic functional layers located between the cathode and the anode, the organic functional layer at least comprising an electron transport layer, and the material of the electron transport layer including the organic compound as described above.

[0138] Further, the organic functional layer further includes a light-emitting layer, and the light-emitting layer is located between the electron transport layer and the anode. The material of the light-emitting layer may be a light-emitting layer material known in the art.

[0139] It can be understood that in addition to the above-mentioned light-emitting layer and electron transport layer, the organic functional layer may further include other functional layers to improve the performance of the organic electronic device, such as an electron injection layer, an electron blocking layer, a hole injection layer, a hole transport layer, a hole blocking layer, a light extraction layer, etc. Materials suitable for use in these functional layers are described in detail above and in WO2010135519A1, US20090134784A1, and WO2011110277A1, and the entire contents of these three patent documents are hereby incorporated herein by reference.

[0140] 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 or on the side of the cathode away from the light-emitting layer. The substrate may be opaque or transparent. It can be understood that when the substrate is transparent, the organic electronic device is a transparent light-emitting device. The substrate may also be rigid or flexible. 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 poly(ethylene terephthalate) (PET) or polyethylene(2,6-naphthalene) (PEN).

[0141] The material of the anode may be an anode material known in the art for organic electronic devices, such as a conductive metal, a conductive metal oxide, or a conductive polymer. In some embodiments, the absolute value of the difference between the work function of the material of the anode and the HOMO level or valence band level of the light-emitting body in the light-emitting layer or the p-type semiconductor material serving 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 may 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 those of ordinary skill in the art can easily select and use them. 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 pattern-structured. Patterned ITO conductive substrates are commercially available and can be used to fabricate the devices according to the present invention.

[0142] The material of the cathode can be 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 material of the cathode and the LUMO energy level or the conduction band energy level of the lumophore in the light-emitting layer or the n-type semiconductor material serving as the electron injection layer or the electron transport layer or the 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 the cathode of an OLED can potentially be used as the cathode material of the device of the present invention. By way of 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.

[0143] The material of the hole transport layer can be a material known in the art for use as a hole transport layer material. For example, it can be selected from, but not limited to, at least one of poly[bis(4-phenyl)(2,4,6-trimethylphenyl)amine] (PTXX), 2,2',7,7'-tetrakis[N,N-bis(4-methoxyphenyl)amino]-9,9'-spirobifluorene (spiro-omeTXD), 4,4'-cyclohexylbis[N,N-bis(4-methylphenyl)aniline] (TXPC), N,N′-bis(1-naphthyl)-N,N′-diphenyl-1,1′-biphenyl-4,4′-diamine (NPB), 4,4'-bis(N-carbazolyl)-1,1'-biphenyl (CBP), poly[(9,9-dioctylfluorenyl-2,7-diyl)-co-(4,4'-(N-(p-butylphenyl))diphenylamine)] (TFB), poly(9-vinylcarbazole) (PVK), poly(triphenylamine) (Poly-TPD), poly(3,4-ethylenedioxythiophene)-poly(styrenesulfonic acid) (PEDOT:PSS), and 4,4',4”-tris(carbazol-9-yl)triphenylamine (TCTX).

[0144] The material of the hole injection layer can be a material known in the art for use as a hole injection layer material. For example, it can be selected from, but not limited to, at least one of 2,3,6,7,10,11-hexacyano-anthraquinodimethane (HXT-CN), PEDOT (polyethylenedioxythiophene), PEDOT:PSS, and its derivative doped with s-MoO3 (PEDOT:PSS:s-MoO3).

[0145] In at least one preferred embodiment, the organic electronic device is an OLED device. More preferably, the organic electronic device is a solution-based OLED.

[0146] The organic electronic device of the present invention has an emission wavelength between 300 nm and 1000 nm, preferably between 350 nm and 900 nm, and more preferably between 400 nm and 800 nm.

[0147] The present invention also relates to an electronic device comprising the organic electronic device. The present invention relates to the application of electroluminescent devices in various electronic devices. The electronic device can be, but is not limited to, a display device, a lighting device, a light source, a sensor, etc.

[0148] The present invention will be specifically described below through specific examples. The following examples are only partial examples of the present invention and do not limit the present invention.

[0149] Example 1

[0150] The synthesis route of compound M1 in this example is as follows:

[0151]

[0152] The specific synthesis steps are as follows:

[0153] Synthesis of intermediate M1-3: Under a nitrogen atmosphere, (12.6 g, 100 mmol) of compound M1-1, (5.8 g, 100 mmol) of compound M1-2 and 50 mL of polyphosphoric acid were added to a 250 mL two-necked flask, heated to 160 °C, stirred and reacted for 6 hours, cooled to room temperature, quenched with 150 mL of pure water, the reaction solution was filtered by suction, and the solid was recrystallized with ethyl acetate:ethanol, and the yield was 60%.

[0154] Synthesis of compound M1: Under a nitrogen atmosphere, (4.9 g, 30 mmol) of intermediate M1-3, (10.7 g, 30 mmol) of compound M1-4, (0.2 g, 0.9 mmol) of cuprous iodide, (0.3 g, 1.8 mmol) of 1,10-phenanthroline, (9.8 g, 30 mmol) of cesium carbonate and 80 mL of N,N-dimethylformamide were added to a 250 mL three-necked flask, stirred and refluxed for 72 hours. After the reaction was completed, most of the solvent was removed by rotary evaporation of the reaction solution, dissolved in dichloromethane and washed with water 3 times, and the organic solution was collected and purified by silica gel column chromatography to obtain compound M1, and the yield was 68%. MS(ASAP): 440.

[0155] Example 2

[0156] The synthesis route of compound M2 in this example is as follows:

[0157]

[0158] The specific synthesis steps are as follows:

[0159] Synthesis of Intermediate M2-3: Referring to the synthesis method of Intermediate M1-3, using Compound M2-1 and Compound M2-2 to replace Compound M1-1 and Compound M1-2 respectively, with a yield of 58%.

[0160] Synthesis of Compound M2: Referring to the synthesis method of Compound M1, using Intermediate M2-3 and Compound M2-4 to replace Intermediate M1-3 and Compound M1-4 respectively, with a yield of 63%. MS(ASAP): 512.

[0161] Example 3

[0162] The synthesis route of Compound M3 in this example is as follows:

[0163]

[0164] The specific synthesis steps are as follows:

[0165] Synthesis of Intermediate M3-3: Referring to the synthesis method of Intermediate M1-3, using Compound M3-1 and M3-2 to replace Compound M1-1 and Compound M1-2 respectively, with a yield of 55%.

[0166] Synthesis of Compound M3: Referring to the synthesis method of Compound M1, using Compound M3-3 and M3-4 to replace Intermediate M1-3 and Compound M1-4 respectively, with a yield of 60%. MS(ASAP): 584.

[0167] Example 4

[0168] The synthesis route of Compound M4 in this example is as follows:

[0169]

[0170] The specific synthesis steps are as follows:

[0171] Synthesis of Intermediate M4-3: Under a nitrogen atmosphere, add (23.8 g, 100 mmol) Compound M4-1, (50.4 g, 100 mmol) Compound M4-2, (3.31 g, 3 mmol) tetrakis(triphenylphosphine)palladium, a 50 mL aqueous solution of (27.6 g, 200 mmol) potassium carbonate, and 200 mL of toluene to a 500 mL three-necked flask. Heat and stir at 110 °C for 12 hours to end the reaction. Cool to room temperature, filter the filtrate by suction filtration, rotary evaporate most of the solvent, dissolve with dichloromethane and wash with water 3 times. Collect the organic liquid, mix with silica gel and purify by column chromatography, with a yield of 65%.

[0172] Synthesis of Intermediate M4-6: Referring to the synthesis method of Intermediate M1-3, using Compound M4-4 and Compound M4-5 to replace Compound M1-1 and Compound M1-2 respectively, with a yield of 62%.

[0173] Synthesis of Compound M4: Referring to the synthesis method of Compound M1, using Intermediate M4-6 and Intermediate M4-3 to replace Intermediate M1-3 and Compound M1-4 respectively, with a yield of 61%. MS(ASAP): 689.

[0174] Example 5

[0175] The synthetic route of Compound M5 in this example is as follows:

[0176]

[0177] The specific synthesis steps are as follows:

[0178] Synthesis of Intermediate M5-3: Under a nitrogen atmosphere, add (35.2 g, 100 mmol) Compound M5-1, (20.2 g, 100 mmol) Compound M5-2, (0.7 g, 3 mmol) palladium acetate, (3.3 g, 6 mmol) 1,1'-bis(diphenylphosphino)ferrocene, a 50 mL aqueous solution of (19.2 g, 200 mmol) sodium tert-butoxide and 200 mL of xylene into a 500 mL three-necked flask, heat with stirring to 140 °C and react for 12 hours. End the reaction, cool to room temperature, filter the filtrate by suction filtration, rotary evaporate most of the solvent, dissolve it with dichloromethane and wash it with water 3 times, collect the organic liquid, mix it with silica gel and purify it by column chromatography, with a yield of 58%.

[0179] Synthesis of Intermediate M5-6: Referring to the synthesis method of Intermediate M1-3, using Compound M5-4 and Compound M5-5 to replace Compound M1-1 and Compound M1-2 respectively, with a yield of 64%.

[0180] Synthesis of Compound M5: Referring to the synthesis method of Compound M1, using Intermediate M5-6 and Intermediate M5-3 to replace Intermediate M1-3 and Compound M1-4 respectively, with a yield of 62%. MS(ASAP): 615.

[0181] Example 6

[0182] The synthetic route of Compound M6 in this example is as follows:

[0183]

[0184] The specific synthesis steps are as follows:

[0185] Synthesis of Intermediate M6-3: Referring to the synthesis method of Intermediate M5-3, using Compound M6-1 and Compound M6-2 to replace Compound M5-1 and Compound M5-2 respectively, with a yield of 56%.

[0186] Synthesis of Intermediate M6-6: Referring to the synthesis method of Intermediate M1-3, using Compound M6-4 and Compound M6-5 to replace Compound M1-1 and Compound M1-2 respectively, with a yield of 68%.

[0187] Synthesis of Compound M6: Referring to the synthesis method of Compound M1, using Intermediate M6-6 and Intermediate M6-3 to replace Intermediate M1-3 and Compound M1-4 respectively, with a yield of 60%. MS(ASAP): 571.

[0188] Example 7

[0189] The synthesis route of Compound M7 in this example is as follows:

[0190]

[0191] The specific synthesis steps are as follows:

[0192] Synthesis of Intermediate M7-3: Referring to the synthesis method of Intermediate M1-3, using Compound M7-1 and Compound M7-2 to replace Compound M1-1 and Compound M1-2 respectively, with a yield of 65%.

[0193] Synthesis of Compound M7: Referring to the synthesis method of Compound M1, using Intermediate M7-3 and Intermediate M7-4 to replace Intermediate M1-3 and Compound M1-4 respectively, with a yield of 57%. MS(ASAP): 621.

[0194] Example 8

[0195] The synthesis route of Compound M8 in this example is as follows:

[0196]

[0197] The specific synthesis steps are as follows:

[0198] Synthesis of Intermediate M8-3: Referring to the synthesis method of Intermediate M1-3, using Compound M8-1 and Compound M8-2 to replace Compound M1-1 and Compound M1-2 respectively, with a yield of 63%.

[0199] Synthesis of Compound M8: Referring to the synthesis method of Compound M1, using Intermediate M8-3 and Compound M8-4 to replace Intermediate M1-3 and Compound M1-4 respectively, with a yield of 56%. MS(ASAP): 632.

[0200] Example 9

[0201] The synthetic route of compound M9 in this example is as follows:

[0202]

[0203] The specific synthesis steps are as follows:

[0204] Synthesis of intermediate M9-3: Referring to the synthesis method of intermediate M1-3, compound M9-1 and compound M9-2 were used to replace compound M1-1 and compound M1-2 respectively, with a yield of 62%.

[0205] Synthesis of Compound M9: Referring to the synthesis method of Compound M1, Intermediate M9-3 and Intermediate M5-3 were used to replace Intermediate M1-3 and Compound M1-4, respectively, with a yield of 54%. MS (ASAP): 665.

[0206] Example 10

[0207] The synthetic route of compound M10 in this example is as follows:

[0208]

[0209] The specific synthesis steps are as follows:

[0210] Synthesis of intermediate M10-3: Referring to the synthesis method of intermediate M5-3, compound M10-1 and compound M10-2 were used to replace compound M5-1 and M5-2, respectively, with a yield of 57%.

[0211] Synthesis of intermediate M10-6: Referring to the synthesis method of intermediate M1-3, compound M10-4 and compound M10-5 were used to replace compound M1-1 and compound M1-2, respectively, with a yield of 63%.

[0212] Synthesis of Compound M10: Referring to the synthesis method of Compound M1, intermediate M10-6 and intermediate M10-3 were used to replace intermediate M1-3 and compound M1-4, respectively, with a yield of 55%. MS (ASAP): 795.

[0213] Example 11

[0214] The synthetic route of compound M11 in this example is as follows:

[0215]

[0216] The specific synthesis steps are as follows:

[0217] Synthesis of intermediate M11-3: Referring to the synthesis method of intermediate M1-3, compound M11-1 and compound M11-2 were used to replace compound M1-1 and compound M1-2, respectively, with a yield of 60%.

[0218] Synthesis of Compound M11: Referring to the synthesis method of Compound M1, using Intermediate M11-3 and Compound M11-4 to replace Intermediate M1-3 and Compound M1-4 respectively, with a yield of 52%. MS(ASAP): 643.

[0219] Example 12

[0220] The synthesis route of Compound M12 in this example is as follows:

[0221]

[0222] The specific synthesis steps are as follows:

[0223] Synthesis of Intermediate M12-3: Referring to the synthesis method of Intermediate M5-3, using Compound M12-1 and Compound M12-2 to replace Compound M5-1 and M5-2 respectively, with a yield of 58%.

[0224] Synthesis of Intermediate M12-6: Referring to the synthesis method of Intermediate M1-3, using Compound M12-4 and Compound M12-5 to replace Compound M1-1 and Compound M1-2 respectively, with a yield of 62%.

[0225] Synthesis of Compound M12: Referring to the synthesis method of Compound M1, using Intermediate M12-6 and M12-3 to replace Intermediate M1-3 and Compound M1-4 respectively, with a yield of 56%. MS(ASAP): 619.

[0226] Example 13

[0227] The synthesis route of Compound M13 in this example is as follows:

[0228]

[0229] The specific synthesis steps are as follows:

[0230] Synthesis of Intermediate M13-3: Referring to the synthesis method of Intermediate M1-3, using Compound M13-1 and Compound M13-2 to replace Compound M1-1 and Compound M1-2 respectively, with a yield of 62%.

[0231] Synthesis of Compound M13: Referring to the synthesis method of Compound M1, using Intermediate M13-3 and Compound M13-4 to replace Intermediate M1-3 and Compound M1-4 respectively, with a yield of 51%. MS(ASAP): 669.

[0232] Example 14

[0233] The synthesis route of Compound M14 in this example is as follows:

[0234]

[0235] The specific synthesis steps are as follows:

[0236] Synthesis of intermediate M14-3: Referring to the synthesis method of intermediate M1-3, using compound M14-1 and compound M14-2 to replace compound M1-1 and compound M1-2 respectively, with a yield of 65%.

[0237] Synthesis of compound M14: Referring to the synthesis method of compound M1, using intermediate M14-3 and compound M14-4 to replace intermediate M1-3 and compound M1-4 respectively, with a yield of 55%. MS(ASAP): 655.

[0238] Example 15

[0239] The synthesis route of compound M15 in this example is as follows:

[0240]

[0241] The specific synthesis steps are as follows:

[0242] Synthesis of intermediate M15-3: Referring to the synthesis method of compound M4-3, using compound M15-1 and compound M15-2 to replace compound M4-1 and M4-2 respectively, with a yield of 72%.

[0243] Synthesis of intermediate M15-6: Referring to the synthesis method of intermediate M1-3, using compound M15-4 and compound M15-5 to replace compound M1-1 and compound M1-2 respectively, with a yield of 62%.

[0244] Synthesis of compound M15: Referring to the synthesis method of compound M1, using intermediate M15-6 and intermediate M15-3 to replace intermediate M1-3 and compound M1-4 respectively, with a yield of 56%. MS(ASAP): 697.

[0245] The preparation process of the OLED device including the above compounds will be described in detail through specific examples below. The structure of the OLED device 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 a light-emitting layer; 106 is an electron transport layer; 107 is an electron injection layer; 108 is a cathode.

[0246] The preparation steps of OLED-1 are as follows:

[0247] a. Clean the ITO (indium tin oxide) conductive glass substrate with various solvents (such as one or more of deionized water, chloroform, acetone, or isopropanol) for 15 minutes, and then perform ultraviolet ozone plasma treatment.

[0248] b. Transfer the ITO conductive glass substrate into a vacuum vapor deposition equipment. Under high vacuum (1×10 -6 mbar), use resistance heating evaporation to deposit HIM to form a hole injection layer with a thickness of 40 nm.

[0249] c. Deposit the HTM material on the hole injection layer under high vacuum to form a hole transport layer with a thickness of 100 nm (material: HTM).

[0250] d. Deposit the materials of the light-emitting layer (the weight ratio of the light-emitting host material Host and the light-emitting guest material BD is 95:5) on the hole transport layer to form a light-emitting layer with a thickness of 50 nm.

[0251] e. Deposit compound M1 on the light-emitting layer under high vacuum to form an electron transport layer with a thickness of 25 nm.

[0252] f. Electron injection layer: Thermally deposit LiQ in high vacuum (1×10 -6 mbar) to form an electron injection layer with a thickness of 1 nm.

[0253] g. Cathode: Thermally deposit metal Al in high vacuum (1×10 -6 mbar) to form a cathode with a thickness of 150 nm.

[0254] h. Encapsulation: Encapsulate the device with ultraviolet curable resin in a nitrogen glove box.

[0255] The preparation schemes of the devices OLED-2 to OLED-15 in the examples and OLED-Ref-1 in the comparative example are the same as that of OLED-1, except that the electron transport layer material in the example OLED-1 is replaced by the corresponding compound M2 - compound M15 or Ref-1 of the electron transport layer material in Table 1.

[0256] The possible compound structures involved in the OLED preparation process are as follows:

[0257]

[0258] The current-voltage (J-V) characteristics of each OLED device were characterized by a characterization device, while the LT90 lifetime and luminous efficiency were recorded. The results are shown in Table 1 below. Among them, LT90@1000nits is the time when the brightness decreases from the initial brightness of 1000nits to 90% of the initial brightness under a constant current. Here, LT90@1000nits and the external quantum efficiency (EQE) are calculated relative to the device OLED-Ref-1 (corresponding to the electron transport layer material Ref-1) in the comparative example, that is, taking the LT90@1000nits of OLED-Ref-1 as 1 and the external quantum efficiency EQE as 1.

[0259] Table 1:

[0260]

[0261] As can be seen from Table 1: Compared with the OLED device OLED-Ref-1 prepared by using the compound Ref-1 as the electron transport layer material in the comparative example, the OLED devices OLED-1 to OLED-15 prepared by using the organic compound of the present invention as the electron transport layer material have better external quantum efficiency EQE and longer lifetime LT90@1000nits, and the EQE and lifetime LT90 exceed 1.5 times that of the device OLED-Ref-1. That is, the organic compound of the present invention as the electron transport material can effectively improve the external quantum efficiency and lifetime of the organic light-emitting device. In the organic compound of the present invention, phosphine oxide is connected to imidazole through an aromatic group, and a fluorine-containing group is connected to the imidazole. The organic compound containing three electron transport groups of phosphine oxide, imidazole and fluorine can provide multiple gradient transport channels for the transport of electrons, has good electron transport ability, and can effectively improve the device efficiency and stability when applied as an electron transport material in the electron transport layer of an electronic device, thereby improving the device performance and lifetime.

[0262] The above has introduced in detail the organic compound, mixture, composition and organic electronic device provided by the embodiments of the present invention. Specific examples are used in this article to elaborate on the principle and implementation manner of the present invention. The description of the above embodiments is only used to help understand the method and its core idea of the present invention; at the same time, for those skilled in the art, according to the idea of the present invention, there will be changes in the specific implementation manner and application scope. In summary, the content of this specification should not be construed as a limitation to the present invention.

Claims

1. An organic compound, characterized in that, It has a structure represented by the general formula (1): Wherein, Ar1 is selected from any one of the following groups: X is selected from CH; In formula (A-1) and formula (A-6), Y is selected from O or S; In formula (A-7) to formula (A-9), Y is selected from O, S or C(CH3)2; * represents the fusion site; Ar2 is selected from one or a combination of more than one of the following groups: X1 is selected from CH; Y1 is selected from O or C(CH3)2; L is selected from one or a combination of two of formula (B-1) and formula (B-3); Ar3 and Ar4 are selected from phenyl, biphenyl, naphthyl or methyl; R1 is selected from hydrogen or fluorine; R2 is selected from methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl or the following group: a is selected from 1, 2, 3, 4 or 5; And at least one of R1 and R2 contains an F atom; n is selected from 0 or 1; m is an integer from 0 to 8.

2. The organic compound according to claim 1, characterized in that, Ar2 is selected from any of the following structures: L is selected from one or a combination of two of formula (C-3) and formula (C-8); Wherein, * represents the connection site.

3. The organic compound according to any one of claims 1, the organic compound represented by the general formula (1) is selected from the structures represented by any one of formula (2-1) to (2-11): Among them, m1 is selected from 0.

4. The organic compound according to claim 1, wherein The organic compound is selected from any of the following structures:

5. A mixture, characterized in that, The mixture includes the organic compound according to any one of claims 1-4 and at least one organic functional material, and the organic functional material is 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 light-emitting guest material, a light-emitting host material or an organic dye.

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

7. An organic electronic device includes at least one functional layer, characterized in that, The functional layer contains the organic compound according to any one of claims 1-4, or the mixture according to claim 5, or the functional layer is prepared from the composition according to claim 6.

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