CN116355016A - Organic compound, mixture, composition and organic electronic device comprising same - Google Patents

Organic compound, mixture, composition and organic electronic device comprising same Download PDF

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CN116355016A
CN116355016A CN202111592987.7A CN202111592987A CN116355016A CN 116355016 A CN116355016 A CN 116355016A CN 202111592987 A CN202111592987 A CN 202111592987A CN 116355016 A CN116355016 A CN 116355016A
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何锐锋
吴灿洁
吴学雄
宋晶尧
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Guangzhou Chinaray Optoelectronic Materials Ltd
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Abstract

The invention discloses an organic compound, which has the following structure:
Figure DDA0003430337740000011
in the organic compound, phosphorus oxide and imidazole are connected through an aromatic group, and fluorine-containing groups are connected to the imidazole, so that the organic compound containing three electron-transport groups of phosphorus oxide, imidazole and fluorine can provide multiple energy level gradient transport for electron transportThe channel has better electron transmission capability, and can be used as an electron transmission material in an electron transmission layer in an electronic device to effectively improve the efficiency and stability of the device, thereby improving the performance and service life of the device. In addition, the invention also discloses a mixture, a composition and an organic electronic device.

Description

Organic compound, mixture, composition and organic electronic device comprising same
Technical Field
The invention relates to the technical field of organic materials, in particular to an organic compound, and a mixture, a composition and an organic electronic device comprising the organic compound.
Background
Because of the variety, relatively low manufacturing cost, excellent optical and electrical properties and other characteristics of organic semiconductor materials, the organic semiconductor materials have great potential in the preparation of Organic Light Emitting Diodes (OLEDs) or optoelectronic devices, such as flat panel displays and lighting devices. The principle of luminescence of an organic electronic device is organic electroluminescence, which refers to a phenomenon of converting electric energy into light energy by using an organic substance. Organic electroluminescent devices using organic electroluminescence generally have a positive electrode and a negative electrode, and a functional layer containing an organic substance therebetween. In order to improve the efficiency and the service life of the organic electroluminescent element, the functional layers have a multi-layer structure, and each functional layer contains different organic substances. Specifically, the light-emitting device includes a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, or the like. In an organic electroluminescent device, when a voltage is applied between two electrodes, holes are injected from a positive electrode into an organic layer, electrons are injected from a negative electrode into the organic layer, and when the injected holes meet the electrons, excitons are formed, and light is emitted when the excitons transition back to a ground state. The organic electroluminescent element has the characteristics of self-luminescence, high brightness, high efficiency, low driving voltage, wide viewing angle, high contrast, high responsiveness and the like.
In order to improve the luminous efficiency of the organic electroluminescent device, development and collocation of a transport layer material are important, and the organic electroluminescent device can achieve the balance of carrier transport by adopting a hole transport layer material and an electron transport layer material with proper transport capacity, so that electrons and holes are combined in the center of a luminous layer, quenching of excitons can be reduced, and therefore, the luminous efficiency can be effectively improved, and the service life of the device can be prolonged.
At present, although a large number of electron transport materials have been developed, the corresponding devices still have many problems such as imbalance in carrier transport and insufficient lifetime of the devices. How to design new materials with better performance for adjustment, thereby achieving the effects of adjusting transmission balance and improving the efficiency and service life of devices is always a problem to be solved by the technicians in the field.
Disclosure of Invention
In view of this, the present invention provides an organic compound aimed at providing a novel organic functional material to improve the performance of a device.
The invention is realized by the following technical scheme:
an organic compound having a structure represented by the general formula (1):
Figure BDA0003430337720000011
wherein Ar is 1 、Ar 2 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;
Ar 3 、Ar 4 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;
l is independently selected for each occurrence 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;
R 1 、R 2 each occurrence is independently selected from: hydrogen, deuterium, or a substituted or unsubstituted linear alkyl group having 1 to 20C atoms, or a substituted or unsubstituted linear alkoxy group having 1 to 20C atoms, or a substituted or unsubstituted linear thioalkoxy group having 1 to 20C atoms, or a substituted or unsubstituted branched alkyl group having 3 to 20C atomsBranched alkoxy, or substituted or unsubstituted branched thioalkoxy having 3 to 20C atoms, or substituted or unsubstituted cyclic alkyl having 3 to 20C atoms, or substituted or unsubstituted cyclic alkoxy having 3 to 20C atoms, or substituted or unsubstituted cyclic thioalkoxy having 3 to 20C atoms, or silyl, or keto having 1 to 20C atoms, or alkoxycarbonyl having 2 to 20C atoms, or aryloxycarbonyl having 7 to 20C atoms, cyano, carbamoyl, haloformyl, formyl, isocyano, thiocyanate, isothiocyanate, hydroxy, nitro, amino, -CF 3 、-OCF 3 -Cl, -Br, -F, -I, or an alkenyl group having 2 to 20C atoms, or a substituted or unsubstituted aryl group having 6 to 60 ring atoms, or a substituted or unsubstituted heteroaryl 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;
and R is 1 And R is 2 At least one of which contains an F atom; n is an integer from 0 to 6; m is selected from integers from 0 to 8.
Correspondingly, the invention also provides a mixture which comprises the organic compound and at least one organic functional material, wherein the organic functional material is selected from hole injection materials, hole transport materials, electron injection materials, electron blocking materials, hole blocking materials, luminescent guest materials, luminescent host materials or organic dyes.
Correspondingly, the invention also provides a composition which comprises the organic compound or the mixture and at least one organic solvent.
Correspondingly, the invention also provides an organic electronic device, which comprises at least one functional layer, wherein the functional layer comprises the organic compound or the mixture, or is prepared from the composition.
Compared with the prior art, the organic compound has the following beneficial effects:
in the organic compound, phosphorus oxide and imidazole are connected through an aromatic group, and the imidazole is connected with a fluorine-containing group, so that the organic compound containing three electron-transporting groups of phosphorus oxide, imidazole and fluorine can provide a plurality of gradient transport channels for electron transport, has better electron transport capacity, and can be used as an electron transport material to be applied to an electron transport layer in an electronic device to effectively improve the efficiency and stability of the device, thereby improving the performance and service life of the device.
Drawings
In order to more clearly illustrate the technical solutions of the embodiments of the present invention, the drawings that are needed in the description of the embodiments will be briefly described below, it being obvious that the drawings in the following description are only some embodiments of the present invention, and that other drawings may be obtained according to these drawings without inventive effort for a person skilled in the art.
FIG. 1 is a schematic diagram of an OLED device shown in embodiment 1 of the device of the present invention;
wherein 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 the cathode.
Detailed Description
The following description of the embodiments of the present invention will be made clearly and completely with reference to the accompanying drawings, in which it is apparent that the embodiments described are only some embodiments of the present invention, but not all embodiments. All other embodiments, which can be made by a person skilled in the art without making any inventive effort, are intended to be within the scope of the present invention. Furthermore, it should be understood that the detailed description is presented herein for purposes of illustration and description only, and is not intended to limit the invention.
In the description of the present invention, the term "comprising" means "including but not limited to," and the term "plurality" means "two or more. Various embodiments of the invention may exist in a range of forms; it should be understood that the description in a range format is merely for convenience and brevity and should not be construed as a rigid limitation on the scope of the invention; it is therefore to be understood that the range description has specifically disclosed all possible sub-ranges and individual values within that range. For example, it should be considered that a description of a 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., as well as single numbers within the range, such as 1, 2, 3, 4, 5, and 6, wherever applicable. In addition, whenever a numerical range is referred to herein, it is meant to include any reference number (fractional or integer) within the indicated range.
Unless defined otherwise, 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 invention belongs. The terminology used herein in the description of the invention is for the purpose of describing particular embodiments only and is not intended to be limiting of the invention.
The term "and/or", "and/or" as used in this disclosure includes a selection of any one of two or more of the listed items and also includes any and all combinations of the listed items, including any two or more of the listed items, any or all combinations of the listed items. It should be noted that, when at least three items are connected by a combination of at least two conjunctions selected from the group consisting of "and/or", "and/or", it should be understood that, in the present invention, the technical solutions include technical solutions that all use "logical and" connection, and also include technical solutions that all use "logical or" connection. For example, "a and/or B" includes three parallel schemes A, B and a+b. For another example, the technical schemes of "a, and/or B, and/or C, and/or D" include any one of A, B, C, D (i.e., the technical scheme of "logical or" connection), and also include any and all combinations of A, B, C, D, i.e., any two or three of A, B, C, D, and also include four combinations of A, B, C, D (i.e., the technical scheme of "logical and" connection).
In the present invention, the aromatic groups, aromatic groups and aromatic ring systems have the same meaning and can be interchanged.
In the present invention, the heteroaromatic groups, heteroaromatic ring systems have the same meaning and can be interchanged.
In the present invention, the "heteroatom" is a non-carbon atom, and may be an N atom, an O atom, an S atom, or the like.
In the present invention, "substituted" means that a hydrogen atom in a substituted group is substituted by a substituent.
In the present invention, the same substituent may be independently selected from different groups when it appears multiple times. If the general formula contains a plurality of R, R can be independently selected from different groups.
In the present invention, "substituted or unsubstituted" means that the defined group may or may not be substituted. When a defined group is substituted, it is understood that the defined group may be substituted with one or more substituents R selected from, but not limited to: deuterium, cyano, isocyano, nitro or halogen, alkyl containing 1 to 20C atoms, heterocyclyl containing 3 to 20 ring atoms, aromatic containing 6 to 20 ring atoms, heteroaromatic containing 5 to 20 ring atoms, -NR' R ", silane, carbonyl, alkoxycarbonyl, aryloxycarbonyl, carbamoyl, haloformyl, formyl, isocyanate, thiocyanate, isothiocyanate, hydroxyl, trifluoromethyl, and which may be further substituted with substituents acceptable in the art; it is understood that R 'and R "in-NR' R" are each independently selected from, but not limited to: H. deuterium atoms, cyano groups, isocyano groups, nitro groups or halogen groups, alkyl groups containing 1 to 10C atoms, heterocyclic groups containing 3 to 20 ring atoms, aromatic groups containing 6 to 20 ring atoms, heteroaromatic groups containing 5 to 20 ring atoms. Preferably, R is selected from, but not limited to: deuterium atoms, cyano groups, isocyano groups, nitro groups or halogen groups, alkyl groups containing 1 to 10C atoms, heterocyclic groups containing 3 to 10 ring atoms, aromatic groups containing 6 to 20 ring atoms, heteroaromatic groups containing 5 to 20 ring atoms, silane groups, carbonyl groups, alkoxycarbonyl groups, aryloxycarbonyl groups, carbamoyl groups, haloformyl groups, formyl groups, isocyanate groups, thiocyanate groups, isothiocyanate groups, hydroxyl groups, trifluoromethyl groups, and which may be further substituted with substituents acceptable in the art.
In the present invention, the "number of ring atoms" means the number of ring atoms constituting the ring itself, i.e., the number of ring-forming atoms, in a structural compound (for example, a monocyclic compound, a condensed compound, a crosslinked compound, a carbocyclic compound, or a heterocyclic compound) in which atoms are bonded to form a ring. When the ring is substituted with a substituent, the atom contained in the substituent is not included in the ring atom. The same applies to the "number of ring atoms" described below, unless otherwise specified. For example, the number of ring atoms of the benzene ring is 6, the number of ring atoms of the naphthalene ring is 10, and the number of ring atoms of the thienyl group is 5.
"aryl or aromatic group" refers to an aromatic hydrocarbon group derived from an aromatic ring compound by removal of one hydrogen atom, which may be a monocyclic aryl group, or a fused ring aryl group, or a polycyclic aryl group, at least one of which is an aromatic ring system for a polycyclic species. 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 may be optionally further substituted thereon. Preferably a substituted or unsubstituted aryl group having 6 to 30 ring atoms, more preferably a substituted or unsubstituted aryl group having 6 to 18 ring atoms, 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, anthryl, phenanthryl, fluoranthryl, triphenylenyl, pyrenyl, perylenyl, tetracenyl, fluorenyl, perylenyl, acenaphthylenyl and derivatives thereof. It will be appreciated that a plurality of aryl groups may also be interrupted by short non-aromatic units (e.g. <10% of non-H atoms, such as C, N or O atoms), such as acenaphthene, fluorene, or 9, 9-diaryl fluorene, triarylamine, diaryl ether systems in particular should also be included in the definition of aryl groups.
"heteroaryl or heteroaromatic group" means that at least one carbon atom is replaced by a non-carbon atom on the basis of an aryl group, which may be an N atom, an O atom, an S atom, or the like. For example, "substituted or unsubstituted heteroaryl having 5 to 40 ring atoms" refers to heteroaryl having 5 to 40 ring atoms, preferably substituted or unsubstituted heteroaryl having 6 to 30 ring atoms, more preferably substituted or unsubstituted heteroaryl having 6 to 18 ring atoms, particularly preferably substituted or unsubstituted heteroaryl having 6 to 14 ring atoms, and the heteroaryl is optionally further substituted; suitable examples include, but are not limited to: thienyl, furyl, pyrrolyl, diazolyl, triazolyl, imidazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, acridinyl, pyridazinyl, pyrazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, benzothienyl, benzofuranyl, indolyl, pyrroloimidazolyl, pyrrolopyrrolyl, thienopyrrolyl, thienothiophenoyl, furopyrrolyl, furofuranyl, thienofuranyl, benzisoxazolyl, benzisothiazolyl, benzimidazolyl, phthalazinyl, phenanthridinyl, primary pyridyl, quinazolinonyl, dibenzothienyl, dibenzofuranyl, carbazolyl, and derivatives thereof.
In the present invention, "alkyl" may denote a linear, branched and/or cyclic alkyl group. The carbon number of the alkyl group may be 1 to 50, 1 to 30, 1 to 20, 1 to 10, or 1 to 6. Phrases containing this term, e.g., "C 1-9 Alkyl "means an alkyl group containing 1 to 9 carbon atoms, and each occurrence may be, independently of the other, C 1 Alkyl, C 2 Alkyl, C 3 Alkyl, C 4 Alkyl, C 5 Alkyl, C 6 Alkyl, C 7 Alkyl, C 8 Alkyl or C 9 An alkyl group. Non-limiting examples of alkyl groups include methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, isobutyl, 2-ethylbutyl, 3-dimethylbutyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, cyclopentyl, 1-methylpentyl, 3-methylpentyl, 2-ethylpentyl, 4-methyl-2-pentyl, n-hexyl, 1-methylhexyl, 2-ethylhexyl, 2-butylhexyl, cyclohexyl, 4-methylcyclohexyl, 4-tert-butylcyclohexyl, n-heptyl, 1-methylheptyl, 2-dimethylheptyl, 2-ethylheptyl, 2-butylheptylGroup, n-octyl, tert-octyl, 2-ethyloctyl, 2-butyloctyl, 2-hexyloctyl, 3, 7-dimethyloctyl, cyclooctyl, n-nonyl, n-decyl, adamantyl, 2-ethyldecyl, 2-butyldecyl, 2-hexyldecyl, 2-octyldecyl, n-undecyl, n-dodecyl, 2-ethyldodecyl, 2-butyldodecyl, 2-hexyldodecyl, 2-octyldodecyl, n-tridecyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, 2-ethylhexadecyl 2-butylhexadecyl, 2-hexylhexadecyl, 2-octylhexadecyl, n-heptadecyl, n-octadecyl, n-nonadecyl, n-eicosyl, 2-ethyleicosyl, 2-butyleicosyl, 2-hexyleicosyl, 2-octyleicosyl, n-heneicosyl, n-docosyl, n-tricosyl, n-tetracosyl, n-pentacosyl, n-hexacosyl, n-heptacosyl, n-octacosyl, n-nonacosyl, n-triacontyl, and the like.
In the present invention, the abbreviations of the substituents correspond to: n-n, sec-sec, i-iso, t-tert, o-o, m-m, p-pair, memethyl, et ethyl, pr propyl, bu butyl, am-n-pentyl, hx hexyl, cy cyclohexyl.
In the present invention, "amine group" means a derivative of an amine having the formula-N (X) 2 Wherein each "X" is independently selected from H, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted heterocyclyl, and the like. Non-limiting types of amine groups include-NH 2 -N (alkyl) 2 -NH (alkyl), -N (cycloalkyl) 2 -NH (cycloalkyl), -N (heterocyclyl) 2 -NH (heterocyclyl), -N (aryl) 2 -NH (aryl), -N (alkyl) (heterocyclyl), -N (cycloalkyl) (heterocyclyl), -N (aryl) (heteroaryl), -N (alkyl) (heteroaryl), and the like.
In the present invention, hydroxyl means-OH, carboxyl means-COOH, carbonyl means-C (=O) -, and amino means-NH, unless otherwise specified 2 Formyl means-C (=o) H, haloformyl means-C (=o) Z (wherein Z represents halogen), carbamoyl means-C (=o) NH 2 Isocyanate groups refer to-NCO and isothiocyanate groups refer to-NCS.
In the present invention, "alkoxy" refers to a group of the structure "-O-alkyl", i.e., an alkyl group as defined above is attached to other groups via an oxygen atom. Phrases containing this term, suitable examples include, but are not limited to: methoxy (-O-CH) 3 or-OMe), ethoxy (-O-CH 2 CH 3 or-OEt) and t-butoxy (-O-C (CH) 3 ) 3 or-OtBu).
In the present invention, "×" indicates a ligation site or a fusion site. When no attachment site is specified in the group, an optionally attachable site in the group is indicated as attachment site. Where no fused site is indicated in the group, an optionally fused site in the group is indicated as fused site, preferably two or more sites in the group that are ortho to each other are fused sites.
In the present invention, when the same group contains a plurality of substituents of the same symbol, each substituent may be the same or different from each other, for example
Figure BDA0003430337720000041
The 6R groups on the benzene ring may be the same or different from each other.
In the present invention, a single bond to which a substituent is attached extends through the corresponding ring, meaning that the substituent may be attached to an optional position of the ring. For example
Figure BDA0003430337720000042
R in (2) may be attached to any substitutable site of the benzene ring.
As used in this disclosure, "a combination thereof," "any combination thereof," and the like include all suitable combinations of any two or more of the listed items.
In the present invention, "further", "still further", "particularly" and the like are used for descriptive purposes to indicate differences in content but should not be construed as limiting the scope of the invention.
In the present invention, "optional" means optional or not, that is, means any one selected from two parallel schemes of "with" or "without". If multiple "alternatives" occur in a technical solution, if no particular description exists and there is no contradiction or mutual constraint, then each "alternative" is independent.
In the invention, the technical characteristics described in an open mode comprise a closed technical scheme composed of the listed characteristics and also comprise an open technical scheme comprising the listed characteristics.
The invention provides an organic compound, which has a structure shown as a general formula (1):
Figure BDA0003430337720000043
wherein Ar is 1 、Ar 2 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;
Ar 3 、Ar 4 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;
l is independently selected for each occurrence 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;
R 1 、R 2 Each occurrence is independently selected from: hydrogen, deuterium, or a substituted or unsubstituted linear alkyl group having 1 to 20C atoms, or a substituted or unsubstituted linear alkoxy group having 1 to 20C atoms, or a substituted or unsubstituted linear thioalkoxy group having 1 to 20C atoms, or a substituted or unsubstituted branched alkyl group having 3 to 20C atoms, or a substituted or unsubstituted branched alkoxy group having 3 to 20C atoms, or a substituted or unsubstituted branched thioalkoxy group having 3 to 20C atoms, or a substituted or unsubstituted cyclic alkyl group having 3 to 20C atomsOxy, or substituted or unsubstituted cyclic thioalkoxy having 3 to 20C atoms, or silyl, or keto having 1 to 20C atoms, or alkoxycarbonyl having 2 to 20C atoms, or aryloxycarbonyl having 7 to 20C atoms, cyano, carbamoyl, haloformyl, formyl, isocyano, thiocyanate, isothiocyanate, hydroxy, nitro, amino, -CF 3 、-OCF 3 -Cl, -Br, -F, -I, or an alkenyl group having 2 to 20C atoms, or a substituted or unsubstituted aryl group having 6 to 60 ring atoms, or a substituted or unsubstituted heteroaryl 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;
And R is 1 And R is 2 At least one of which contains an F atom;
n is an integer from 0 to 6; m is selected from integers from 0 to 8.
In one embodiment, ar 1 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;
further, ar 1 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.
In a specific embodiment, ar 1 Selected from the following groups:
Figure BDA0003430337720000051
wherein: x is independently selected from CR for each occurrence 1 Or N; preferably, X is independently selected from CR for each occurrence 1 ；
Y is independently selected from NR at each occurrence 4 、PR 4 、CR 5 R 6 、SiR 5 R 6 、O、S、S(＝O) 2 Or S (=o);
R 4 、R 5 、R 6 each occurrence is independently selected from: hydrogen, deuterium, or substituted or unsubstituted straight-chain alkyl having 1 to 20C atoms, or substituted or unsubstituted straight-chain alkoxy having 1 to 20C atoms, or substituted or unsubstituted straight-chain thioalkoxy having 1 to 20C atoms, or substituted or unsubstituted branched alkyl having 3 to 20C atoms, or substituted or unsubstituted branched alkoxy having 3 to 20C atoms, or substituted or unsubstituted branched thioalkoxy having 3 to 20C atoms, or substituted or unsubstituted cyclic alkyl having 3 to 20C atoms, or substituted or unsubstituted cyclic alkoxy having 3 to 20C atoms, or substituted or unsubstituted cyclic thioalkoxy having 3 to 20C atoms, or silyl, or ketone group having 1 to 20C atoms, or alkoxycarbonyl group having 2 to 20C atoms, or aryloxycarbonyl having 7 to 20C atoms, cyano, carbamoyl, haloformyl, formyl, isocyano, thiocyanate, hydroxy, nitro, -CF amine, -isothiocyanate 3 、-OCF 3 -Cl, -Br, -F, -I, or an alkenyl group having 2 to 20C atoms, or a substituted or unsubstituted aryl group having 6 to 60 ring atoms, or a substituted or unsubstituted heteroaryl 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;
* Represents a condensed site.
In one embodiment, R 1 、R 2 Each occurrence is independently selected from: hydrogen, deuterium, or a substituted or unsubstituted straight chain alkyl group having 1 to 10C atoms, or a substituted or unsubstituted branched chain alkyl group having 3 to 10C atoms, or a substituted or unsubstituted cyclic alkyl group having 3 to 10C atoms, or a substituted or unsubstituted straight chain alkoxy group having 1 to 10C atoms, or a substituted or unsubstituted branched chain alkoxy group having 3 to 10C atoms, cyano, isocyano, nitro, -CF 3 、-OCF 3 -Cl, -Br, -F, -I, or a substituted or unsubstituted cyclic antigenAn aromatic group having a number of atoms of 6 to 30, or a substituted or unsubstituted heteroaromatic group having a number of ring atoms of 5 to 30, or a combination of these groups; and R is 1 And R is 2 At least one of which contains an F atom.
In one embodiment, R 1 、R 2 Each occurrence is independently selected from: hydrogen, deuterium, -F, a linear alkyl group having 1 to 10C atoms, unsubstituted or substituted by one or more F, a branched alkyl group having 3 to 10C atoms, unsubstituted or substituted by one or more F, or a cyclic alkyl group having 3 to 10C atoms, unsubstituted or substituted by one or more F, a linear alkoxy group having 1 to 10C atoms, unsubstituted or substituted by one or more F, a branched alkoxy group having 3 to 10C atoms, unsubstituted or substituted by one or more F; and R is 1 And R is 2 At least one of which contains an F atom.
In a specific embodiment, R 1 、R 2 Each occurrence is independently selected from: hydrogen (-H), deuterium (-D), fluorine (-F), methyl, ethyl, isopropyl, t-butyl, trifluoromethyl (-CF) 3 ) Or the following groups:
Figure BDA0003430337720000061
wherein: a is selected from 1, 2, 3, 4 or 5.
In one embodiment, R 2 Selected from the group consisting of-F, -CF 3 Or the following groups:
Figure BDA0003430337720000062
further, R 1 Each occurrence is selected from hydrogen, deuterium, -F, methyl, ethyl, isopropyl, t-butyl, -CF 3 Or the following groups:
Figure BDA0003430337720000063
in another embodimentIn the example, at least one R 1 Selected from the group consisting of-F, -CF 3 Or the following groups:
Figure BDA0003430337720000064
further, R 2 Selected from hydrogen, deuterium, -F, methyl, ethyl, isopropyl, t-butyl, -CF 3 Or the following groups:
Figure BDA0003430337720000065
in the above embodiments, a is selected from 1, 2, 3, 4 or 5.
In one embodiment, Y is independently selected from N-CH at each occurrence 3 、N-Ph、C(CH 3 ) 2 O or S. Further, ar 2 L is 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.
In a specific embodiment, ar 2 And/or L is independently selected from the following groups:
Figure BDA0003430337720000066
wherein: x is X 1 Each occurrence is independently selected from CR 7 Or N;
Y 1 each occurrence is independently selected from NR 8 、PR 8 、CR 9 R 10 、SiR 9 R 10 、O、S、S(＝O) 2 Or S (=o);
R 7 、R 8 、R 9 、R 10 each occurrence is independently selected from: hydrogen, deuterium, or a substituted or unsubstituted linear alkyl group having 1 to 20C atoms, or a substituted or unsubstituted linear alkoxy group having 1 to 20C atoms, or a substituted or unsubstituted linear thioalkoxy groupUnsubstituted branched alkyl group having 3 to 20C atoms, or substituted or unsubstituted branched alkoxy group having 3 to 20C atoms, or substituted or unsubstituted branched thioalkoxy group having 3 to 20C atoms, or substituted or unsubstituted cyclic alkyl group having 3 to 20C atoms, or substituted or unsubstituted cyclic alkoxy group having 3 to 20C atoms, or substituted or unsubstituted cyclic thioalkoxy group having 3 to 20C atoms, or silyl group, or ketone group having 1 to 20C atoms, or alkoxycarbonyl group having 2 to 20C atoms, or aryloxycarbonyl group having 7 to 20C atoms, cyano group, carbamoyl group, haloformyl group, formyl group, isocyano group, isocyanate group, thiocyanate group, isothiocyanate group, hydroxyl group, nitro group, amine group, -CF group 3 、-OCF 3 -Cl, -Br, -F, -I, or an alkenyl group having 2 to 20C atoms, or a substituted or unsubstituted aryl group having 6 to 60 ring atoms, or a substituted or unsubstituted heteroaryl 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.
When X is 1 X is a binding site 1 Selected from the group consisting of C atoms; when Y is 1 When the binding site is, Y 1 Selected from the group consisting of N atoms.
In some of these embodiments, in formula (1), ar 2 And/or L is independently selected from any one of formulas (C-1) to (C-18):
Figure BDA0003430337720000071
wherein, represents the site of attachment.
In one embodiment, the organic compound of formula (1) is selected from structures represented by formulas (2-1) to (2-11):
Figure BDA0003430337720000072
Figure BDA0003430337720000073
wherein m1 is selected from 0, 1, 2, 3 or 4. Wherein X, Y and Y 1 Reference may be made to the definitions hereinbefore.
In a certain embodiment, n is selected from 0 or 1.
In one embodiment, R 7 、R 8 、R 9 、R 10 Each occurrence is independently selected from: hydrogen, deuterium, or a substituted or unsubstituted straight chain alkyl group having 1 to 10C atoms, or a substituted or unsubstituted branched alkyl group having 3 to 10C atoms, or a substituted or unsubstituted cyclic alkyl group having 3 to 10C atoms, cyano, isocyano, nitro, -CF 3 、-OCF 3 -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.
In one embodiment, ar 3 ～Ar 4 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.
In one embodiment, ar 3 ～Ar 4 Independently selected from the following groups:
Figure BDA0003430337720000081
wherein:
X 2 each occurrence is independently selected from CR 11 Or N;
Y 2 each occurrence is independently selected from NR 12 、PR 12 、CR 13 R 14 、SiR 13 R 14 、O、S、S(＝O) 2 Or S (=o);
R 11 、R 12 、R 13 、R 14 each occurrence is independently selected from: H. d, a linear alkyl group having 1 to 20C atoms, a linear alkoxy group having 1 to 20C atoms, a linear thioalkoxy group having 1 to 20C atoms, a branched alkyl group having 3 to 20C atoms, a cycloalkyl group having 3 to 20C atoms, a branched alkoxy group having 3 to 20C atoms, a cyclic alkoxy group having 3 to 20C atoms, a branched thioalkoxy group having 3 to 20C atoms, a cyclic thioalkoxy group having 3 to 20C atoms, a silyl group, a ketone group having 1 to 20C atoms, an alkoxycarbonyl group having 2 to 20C atoms, an aryloxycarbonyl group having 7 to 20C 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, a CF 3 、OCF 3 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;
two adjacent R 11 Are connected with each other to form a ring or not.
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 10C atoms, or a substituted or unsubstituted branched alkyl group having 3 to 10C atoms, or a substituted or unsubstituted cyclic alkyl group having 3 to 10C atoms, cyano, isocyano, nitro, -CF 3 、-OCF 3 -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.
In one embodiment, ar 3 And Ar is a group 4 Selected from the same groups.
Further, the organic compounds of the present invention include, but are not limited to, the structures shown below:
Figure BDA0003430337720000082
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Figure BDA0003430337720000091
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Figure BDA0003430337720000101
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Figure BDA0003430337720000111
in one embodiment, the hydrogen atoms (H) in the organic compounds of the present invention may be partially deuterated (D), preferably 10% of H is deuterated, or 20% of H is deuterated; more preferably, 30% of the H is deuterated or 40% of the H is deuterated.
In the organic compound, phosphorus oxide and imidazole are connected through an aromatic group, and the imidazole is connected with a fluorine-containing group, so that the organic compound containing three electron-transporting groups of phosphorus oxide, imidazole and fluorine can provide a plurality of gradient transport channels for electron transport, has better electron transport capacity, and can be used as an electron transport material to be applied to an electron transport layer in an electronic device to effectively improve the efficiency and stability of the device, thereby improving the performance and service life of the device.
The organic compound can be used as a functional material for preparing organic electronic devices, in particular 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.
The present invention relates to an electron transport layer material comprising an organic compound as described above.
The invention relates to a mixture comprising at least one organic compound as described above and at least one other organic functional material; the at least one other organic functional material may 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. Various organic functional materials are described in detail in, for example, WO2010135519A1, US20090134784A1 and WO2011110277A1, the entire contents of which 3 patent documents are hereby incorporated by reference.
In an embodiment, the further organic functional material is selected from hole transport materials.
The invention also relates to a composition comprising at least one organic compound or mixture as described above, and at least one organic solvent. Wherein the at least one organic solvent may be selected from aromatic or heteroaromatic, esters, aromatic ketones or ethers, aliphatic ketones or ethers, alicyclic or olefinic compounds, borates or phosphates. That is, the solvent contained in the composition of the present invention may be any one of the above-mentioned organic solvents, or a mixed solvent of two or more thereof. In a preferred embodiment, the at least one organic solvent comprised in the composition of the invention is chosen from aromatic or heteroaromatic solvents.
Specifically, aromatic or heteroaromatic-based solvents include, but are not limited to: p-diisopropylbenzene, pentylbenzene, tetrahydronaphthalene, cyclohexylbenzene, chloronaphthalene, 1, 4-dimethylnaphthalene, 3-isopropylbiphenyl, p-methylisopropylbenzene, dipentylbenzene, tripentylbenzene, pentyltoluenes, o-diethylbenzene, m-diethylbenzene, p-diethylbenzene, 1,2,3, 4-tetramethylbenzene, 1,2,3, 5-tetramethylbenzene, 1,2,4, 5-tetramethylbenzene, butylbenzene, dodecylbenzene, dihexylbenzene, dibutylbenzene, p-diisopropylbenzene, cyclohexylbenzene, benzylbutylbenzene, dimethylnaphthalene, 3-isopropylbiphenyl, p-methylisopropylbenzene, 1-methylnaphthalene, 1,2, 4-trichlorobenzene, 4-difluorodiphenyl methane, 1, 2-dimethoxy-4- (1-propenyl) benzene, diphenyl methane, 2-phenylpyridine, 3-phenylpyridine, N-methyldiphenylamine, 4-isopropylbiphenyl, α -dichlorodiphenyl methane, 4- (3-phenylpropyl) pyridine, benzyl benzoate, 1-bis (3, 4-dimethylphenyl) ethane, 2-isopropylnaphthalene, 2-quinolinecarboxylic acid, ethyl ester, 2-methylfuran, etc.
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, alkyl lactones, alkyl oleates, and the like. Particular preference is given to octyl octanoate, diethyl sebacate, diallyl phthalate, isononyl isononanoate and the like.
Aromatic ketone-based solvents include, but are not limited to: 1-tetralone, 2- (phenylepoxy) tetralone, 6- (methoxy) tetralone, acetophenone, propiophenone, or benzophenone, and derivatives thereof; such as 4-methylacetophenone, 3-methylacetophenone, 2-methylacetophenone, 4-methylpropophenone, 3-methylpropophenone, 2-methylpropophenone, etc.
Aromatic ether-based solvents include, but are not limited to: 3-phenoxytoluene, butoxybenzene, p-anisaldehyde dimethyl acetal, tetrahydro-2-phenoxy-2H-pyran, 1, 2-dimethoxy-4- (1-propenyl) benzene, 1, 4-benzodioxane, 1, 3-dipropylbenzene, 2, 5-dimethoxytoluene, 4-ethylben-ther, 1, 3-dipropoxybenzene, 1,2, 4-trimethoxybenzene, 4- (1-propenyl) -1, 2-dimethoxybenzene, 1, 3-dimethoxybenzene, glycidyl phenyl ether, dibenzyl ether, 4-t-butyl anisole, trans-p-propenyl anisole, 1, 2-dimethoxybenzene, 1-methoxynaphthalene, diphenyl ether, 2-phenoxymethyl ether, 2-phenoxytetrahydrofuran, ethyl-2-naphthyl ether, and the like.
Aliphatic ketone-based solvents include, but are not limited to: 2-nonene, 3-nonene, 5-nonene, 2-decanone, 2, 5-adipone, 2,6, 8-trimethyl-4-nonene, fenchyl ketone, phorone, isophorone, di-n-amyl ketone, and the like; or aliphatic ethers such as amyl ether, hexyl ether, dioctyl ether, ethylene glycol dibutyl ether, diethylene glycol diethyl ether, diethylene glycol butyl methyl ether, diethylene glycol dibutyl ether, triethylene glycol dimethyl ether, triethylene glycol ethyl methyl ether, triethylene glycol butyl methyl ether, tripropylene glycol dimethyl ether, tetraethylene glycol dimethyl ether, and the like.
It will be appreciated that the solvent may be used alone or as a mixture of two or more organic solvents.
In some embodiments, the compositions of the present invention comprise at least one organic compound or mixture as described above, and at least one organic solvent, and may further comprise another organic solvent.
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-trichloroethane, 1, 2-tetrachloroethane, ethyl acetate, butyl acetate, dimethylformamide, dimethylacetamide, dimethylsulfoxide, tetrahydronaphthalene, decalin, and indene.
In some preferred embodiments, the organic solvent suitable for the present invention is a solvent having Hansen (Hansen) solubility parameters within the following ranges:
δd (dispersion force) is in the range of 17.0 to 23.2MPa1/2, particularly in the range of 18.5 to 21.0MPa 1/2;
δp (polar force) is in the range of 0.2-12.5MPa1/2, especially in the range of 2.0-6.0MPa 1/2;
δh (hydrogen bonding force) is in the range of 0.9 to 14.2MPa1/2, particularly in the range of 2.0 to 6.0MPa 1/2.
In some embodiments, the organic solvent is selected with consideration of boiling point in the composition according to the present invention. In at least some embodiments, the organic solvent has a boiling point of ∈deg.C or greater; preferably not less than 180 ℃; more preferably not less than 200 ℃; more preferably not less than 250 ℃; and most preferably at a temperature of 275 ℃ or higher or 300 ℃ or higher. Boiling points in these ranges are beneficial in preventing nozzle clogging of inkjet printheads.
It will be appreciated that the organic solvent may be evaporated from the composition system to form a film comprising the organic compound of the present invention.
In some embodiments, the composition is a solution. In other embodiments, the composition is a suspension.
The organic compound or mixture may be present in the composition in an amount of from 0.01wt% to 10wt%, preferably from 0.1wt% to 5wt%, more preferably from 0.2 to 5wt%, even more preferably from 0.25 to 3wt%.
The invention also relates to the use of said composition as a coating or printing ink in the preparation of an organic electronic device. In some embodiments, the composition is used to prepare organic electronic devices by a print or coating preparation method. The Printing or coating may be prepared by, but is not limited to, ink jet Printing, jet Printing (nozzleprinting), letterpress Printing, screen Printing, gravure Printing, dip coating, spin coating, doctor blade coating, roller Printing, twist roller Printing, offset Printing, flexography, rotogravure Printing, spray coating, brush coating, pad Printing, slot die coating, and the like. Gravure printing, inkjet printing and inkjet printing are preferred.
The solution or suspension may additionally include additives for adjusting viscosity, adjusting film forming properties, improving adhesion, etc. The additive may be selected from at least one of, but not limited to, a surface active compound, a lubricant, a wetting agent, a dispersing agent, a hydrophobizing agent, and a binder. The requirements for the coating or printing ink may be different for different printing or coating modes, and the concentration, viscosity, etc. of the solution or suspension may be adjusted accordingly to accommodate different printing or coating modes.
The invention also provides the use of an organic compound, mixture or composition as described above in an organic electronic device. The technical proposal is as follows:
an organic electronic device comprising or prepared from an organic compound or mixture as described above.
Further, an organic electronic device comprising a first electrode, a second electrode, one or more organic functional layers between the first electrode and the second electrode, said organic functional layers comprising or being prepared from an organic compound, mixture or composition as described above. The first electrode and the second electrode are a pair of electrodes, for example, the first electrode is an anode, and the second electrode is a cathode; and vice versa.
The organic electronic device may be, but is not limited to, an organic light emitting diode (OLED device), an organic photovoltaic cell (OPV), an organic light emitting 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, an organic plasmon emitting diode (Organic Plasmon Emitting Diode), and the like. The organic electronic device is preferably an organic electroluminescent device, such as an OLED.
The organic functional layer is selected from a Hole Injection Layer (HIL), a Hole Transport Layer (HTL), an 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, the entire contents of which 3 patent documents are hereby incorporated by reference.
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, the mixture or is prepared from the composition. Further, the one or more organic functional layers may further include a light emitting layer.
The present invention relates to an organic electronic device comprising: a cathode, an anode, and one or more organic functional layers between the cathode and the anode, the organic functional layers comprising at least one electron transport layer, the material of the electron transport layer comprising an organic compound as described above.
Further, the organic functional layer further includes a light emitting layer 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.
It is understood that the organic functional layer may include other functional layers in addition to the above-mentioned light emitting layer, electron transporting layer, 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 transporting 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, the entire contents of which 3 patent documents are hereby incorporated by reference.
In some embodiments, the organic electronic device further comprises a substrate. The substrate may be located on a side of the anode away from the light emitting layer, or may be located on a side of the cathode 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 light emitting device. The substrate may also be rigid or elastic, for example, the material of the substrate may be plastic, metal, semiconductor wafer or glass. Preferably, the substrate has a smooth surface, and a substrate free of surface defects is a particularly desirable choice. In a preferred embodiment, the substrate is a flexible substrate. The material of the flexible substrate can be a polymer film or plastic. The glass transition temperature Tg of the flexible substrate is 150℃or higher, preferably 200℃or higher, more preferably 250℃or higher, and most preferably 300℃or higher. As an example, the material of the flexible substrate may be poly (ethylene terephthalate) (PET) or polyethylene glycol (2, 6-naphthalene) (PEN).
The material of the anode may be an anode material known in the art for use in organic electronic devices, such as a conductive metal, conductive metal oxide or 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 emitter in the light emitting layer or the p-type semiconductor material as a hole injection layer or hole transport layer or electron blocking layer is less than 0.5eV, preferably less than 0.3eV, and most preferably less than 0.2eV. As an example, the material of the anode may be selected from at least one of, but not limited to, 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 for use by one of ordinary skill in the art. The anode material may 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), and the like. In certain embodiments, the anode is patterned. Patterned ITO conductive substrates are commercially available and can be used to prepare devices according to the present invention.
The material of the cathode may be 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 material of the cathode and the LUMO or conduction band level of the light-emitting body in the light-emitting layer or the n-type semiconductor material as an electron injection layer or an electron transport layer or a hole blocking layer is less than 0.5eV, preferably less than 0.3eV, and most preferably less than 0.2eV. In principle, all materials which can be used as cathode of an OLED are possible as cathode materials for the device according to the invention. As an example, the material of the cathode may be at least one selected from, but not limited to, al, au, ag, ca, ba, mg, liF/Al, mgAg alloy, baF2/Al, cu, fe, co, ni, mn, pd, pt, and ITO. The cathode material may 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), and the like.
The material of the hole transport layer may be a material known in the art for a hole transport layer, and may be selected from, for example, but not limited to, poly [ bis (4-phenyl) (2, 4, 6-trimethylphenyl) amine ] (PTXX), 2', 7' -tetrakis [ N, N-bis (4-methoxyphenyl) amino ] -9,9 '-spirobifluorene (spiro-omeTXD), 4' -cyclohexylbis [ N, N-bis (4-methylphenyl) aniline ] (TXPC), N '-bis (1-naphthyl) -N, N' -diphenyl-1, 1 '-diphenyl-4, 4' -diamine (NPB), 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), poly triphenylamine (Poly (3, 4-ethylenethiophene) -Poly (ethylenethiophene) (pedsulfonic acid); PSS) and at least one of 4,4',4 "-tris (carbazol-9-yl) triphenylamine (TCTX).
The material of the hole injection layer may be a material known in the art for a hole injection layer, for example, may be selected from, but not limited to, 2,3,6,7,10, 11-hexacyano-1, 4,5,8,9, 12-hexaazabenzophenanthrene (HXT-CN), PEDOT (polyethylene dioxythiophene), PEDOT: PSS and s-MoO doped therewith 3 Derivatives of (PEDOT: PSS: s-MoO) 3 ) At least one of them.
In at least one preferred embodiment, the organic electronic device is an OLED device. More preferably, the organic electronic device is a solution type OLED.
The organic electronic device of the present invention has a light emission wavelength of 300nm to 1000nm, preferably 350nm to 900nm, more preferably 400nm to 800 nm.
The invention also relates to an electronic device comprising said organic electronic device. The invention relates to the application of electroluminescent devices in various electronic equipment. The electronic device may be, but is not limited to, a display device, a lighting device, a light source, a sensor, etc.
The present invention will now be described in more detail by way of the following examples, which are intended to be illustrative of the invention and not limiting thereof.
Example 1
The synthetic route for compound M1 of this example is as follows:
Figure BDA0003430337720000141
the specific synthesis steps are as follows:
synthesis of intermediate M1-3: under nitrogen atmosphere, (12.6 g,100 mmol) of compound M1-1, (5.8 g,100 mmol) of compound M1-2 and 50mL of polyphosphoric acid were added into a 250mL two-necked flask, heated to 160℃and stirred for reaction for 6 hours, cooled to room temperature, quenched with 150mL of pure water, the reaction solution was filtered with suction, and the solid was purified with ethyl acetate: ethanol was recrystallized in 60% yield.
Synthesis of compound M1: under 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 80mLN, N-dimethylformamide were added to a 250mL three-necked flask, stirred and refluxed for 72 hours, and after the reaction was completed, most of the solvent was rotationally evaporated, the mixture was washed with dichloromethane for 3 times, and the organic liquid was collected and purified by passing through a column to obtain compound M1 in a yield of 68%. MS (ASAP): 440.
Example 2
The synthetic route for compound M2 of this example is as follows:
Figure BDA0003430337720000142
the specific synthesis steps are as follows:
synthesis of intermediate M2-3: referring to the synthesis of intermediate M1-3, compound M2-1 and compound M2-2 were used in place of compound M1-1 and compound M1-2, respectively, in 58% yield.
Synthesis of compound M2: referring to the synthesis of compound M1, compound intermediate M1-3 and compound M1-4 were replaced with intermediate M2-3 and compound M2-4, respectively, in 63% yield. MS (ASAP): 512.
example 3
The synthetic route for compound M3 of this example is as follows:
Figure BDA0003430337720000151
the specific synthesis steps are as follows:
synthesis of intermediate M3-3: referring to the synthesis of intermediate M1-3, compounds M3-1 and M3-2 were used in place of compounds M1-1 and M1-2, respectively, in 55% yield.
Synthesis of compound M3: referring to the synthesis of compound M1, compounds M3-3 and M3-4 were used in place of intermediate M1-3 and compound M1-4, respectively, in 60% yield. MS (ASAP): 584.
example 4
The synthetic route for compound M4 of this example is as follows:
Figure BDA0003430337720000152
the specific synthesis steps are as follows:
synthesis of intermediate M4-3: under nitrogen atmosphere, 50mL of an aqueous solution of (23.8 g,100 mmol) compound M4-1, (50.4 g,100 mmol) compound M4-2, (3.31 g,3 mmol) tetraphenylphosphine palladium, (27.6 g,200 mmol) potassium carbonate and 200mL of toluene were added to a 500mL three-necked flask, the mixture was heated and stirred to 110℃for reaction for 12 hours, the reaction was completed, the mixture was cooled to room temperature, the filtrate was suction-filtered, most of the solvent was rotary-evaporated, the mixture was washed with dichloromethane and water for 3 times, and an organic solution was collected and purified by passing through a column of silica gel, with a yield of 65%.
Synthesis of intermediate M4-6: referring to the synthesis of intermediate M1-3, compound M4-4 and compound M4-5 were used in place of compound M1-1 and compound M1-2, respectively, in 62% yield.
Synthesis of compound M4: referring to the synthesis of compound M1, intermediate M1-3 and compound M1-4 were replaced with intermediate M4-6 and intermediate M4-3, respectively, in 61% yield. MS (ASAP): 689.
example 5
The synthetic route for compound M5 of this example is as follows:
Figure BDA0003430337720000153
the specific synthesis steps are as follows:
synthesis of intermediate M5-3: under nitrogen atmosphere, (35.2 g,100 mmol) of compound M5-1, (20.2 g,100 mmol) of compound M5-2, (0.7 g,3 mmol) of palladium acetate, (3.3 g,6 mmol) of 1,1' -bis (diphenylphosphine) ferrocene, (19.2 g,200 mmol) of sodium tert-butoxide in 50mL of water and 200mL of xylene were added into a 500mL three-necked flask, heated and stirred to 140 ℃ for reaction for 12 hours, the reaction was completed, cooled to room temperature, the filtrate was suction-filtered, most of the solvent was rotationally evaporated, the solution was washed 3 times with dichloromethane, and the organic solution was collected and purified by column chromatography.
Synthesis of intermediate M5-6: referring to the synthesis of intermediate M1-3, compound M5-4 and compound M5-5 were used in place of compound M1-1 and compound M1-2, respectively, in 64% yield.
Synthesis of compound M5: referring to the synthesis of compound M1, intermediate M1-3 and compound M1-4 were replaced with intermediate M5-6 and intermediate M5-3, respectively, in 62% yield. MS (ASAP): 615.
example 6
The synthetic route for compound M6 of this example is as follows:
Figure BDA0003430337720000161
the specific synthesis steps are as follows:
synthesis of intermediate M6-3: referring to the synthesis of intermediate M5-3, compound M6-1 and compound M6-2 were used in place of compound M5-1 and compound M5-2, respectively, in 56% yield.
Synthesis of intermediate M6-6: referring to the synthesis of intermediate M1-3, compound M6-4 and compound M6-5 were used in place of compound M1-1 and compound M1-2, respectively, in 68% yield.
Synthesis of compound M6: referring to the synthesis of compound M1, intermediate M1-3 and compound M1-4 were replaced with intermediate M6-6 and intermediate M6-3, respectively, in 60% yield. MS (ASAP): 571.
example 7
The synthetic route for compound M7 of this example is as follows:
Figure BDA0003430337720000162
the specific synthesis steps are as follows:
synthesis of intermediate M7-3: referring to the synthesis of intermediate M1-3, compound M7-1 and compound M7-2 were used in place of compound M1-1 and compound M1-2, respectively, in 65% yield.
Synthesis of compound M7: referring to the synthesis of compound M1, intermediate M7-3 and intermediate M7-4 were used in place of intermediate M1-3 and compound M1-4, respectively, in 57% yield. MS (ASAP): 621.
Example 8
The synthetic route for compound M8 of this example is as follows:
Figure BDA0003430337720000171
the specific synthesis steps are as follows:
synthesis of intermediate M8-3: referring to the synthesis of intermediate M1-3, compound M8-1 and compound M8-2 were used in place of compound M1-1 and compound M1-2, respectively, in 63% yield.
Synthesis of compound M8: referring to the synthesis of compound M1, intermediate M1-3 and compound M1-4 were replaced with intermediate M8-3 and compound M8-4, respectively, in 56% yield. MS (ASAP): 632.
example 9
The synthetic route for compound M9 of this example is as follows:
Figure BDA0003430337720000172
the specific synthesis steps are as follows:
synthesis of intermediate M9-3: referring to the synthesis of intermediate M1-3, compound M9-1 and compound M9-2 were used in place of compound M1-1 and compound M1-2, respectively, in 62% yield.
Synthesis of compound M9: referring to the synthesis of compound M1, intermediate M9-3 and intermediate M5-3 were used in place of intermediate M1-3 and compound M1-4, respectively, in 54% yield. MS (ASAP): 665.
example 10
The synthetic route for compound M10 of this example is as follows:
Figure BDA0003430337720000173
the specific synthesis steps are as follows:
synthesis of intermediate M10-3: referring to the synthesis of intermediate M5-3, compounds M10-1 and M10-2 were used in place of compounds M5-1 and M5-2, respectively, in 57% yield.
Synthesis of intermediate M10-6: referring to the synthesis of intermediate M1-3, compound M10-4 and compound M10-5 were used in place of compound M1-1 and compound M1-2, respectively, in 63% yield.
Synthesis of compound M10: referring to the synthesis of compound M1, intermediate M10-6 and intermediate M10-3 were used in place of intermediate M1-3 and compound M1-4, respectively, in 55% yield. MS (ASAP): 795.
example 11
The synthetic route for compound M11 of this example is as follows:
Figure BDA0003430337720000181
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the specific synthesis steps are as follows:
synthesis of intermediate M11-3: referring to the synthesis of intermediate M1-3, compound M11-1 and compound M11-2 were used in place of compound M1-1 and compound M1-2, respectively, in 60% yield.
Synthesis of compound M11: referring to the synthesis of compound M1, intermediate M11-3 and compound M11-4 were used in place of intermediate M1-3 and compound M1-4, respectively, in 52% yield. MS (ASAP): 643.
example 12
The synthetic route for compound M12 of this example is as follows:
Figure BDA0003430337720000182
the specific synthesis steps are as follows:
synthesis of intermediate M12-3: referring to the synthesis of intermediate M5-3, compounds M12-1 and M12-2 were used in place of compounds M5-1 and M5-2, respectively, in 58% yield.
Synthesis of intermediate M12-6: referring to the synthesis of intermediate M1-3, compound M12-4 and compound M12-5 were used in place of compound M1-1 and compound M1-2, respectively, in 62% yield.
Synthesis of compound M12: referring to the synthesis of compound M1, intermediates M12-6 and M12-3 were used in place of intermediates M1-3 and compound M1-4, respectively, in 56% yield. MS (ASAP): 619.
example 13
The synthetic route for compound M13 of this example is as follows:
Figure BDA0003430337720000183
the specific synthesis steps are as follows:
synthesis of intermediate M13-3: referring to the synthesis of intermediate M1-3, compound M13-1 and compound M13-2 were used in place of compound M1-1 and compound M1-2, respectively, in 62% yield.
Synthesis of compound M13: referring to the synthesis of compound M1, intermediate M13-3 and compound M13-4 were used in place of intermediate M1-3 and compound M1-4, respectively, in 51% yield. MS (ASAP): 669.
example 14
The synthetic route for compound M14 of this example is as follows:
Figure BDA0003430337720000191
the specific synthesis steps are as follows:
synthesis of intermediate M14-3: referring to the synthesis of intermediate M1-3, compound M14-1 and compound M14-2 were used in place of compound M1-1 and compound M1-2, respectively, in 65% yield.
Synthesis of compound M14: referring to the synthesis of compound M1, intermediate M14-3 and compound M14-4 were used in place of intermediate M1-3 and compound M1-4, respectively, in 55% yield. MS (ASAP): 655.
example 15
The synthetic route for compound M15 of this example is as follows:
Figure BDA0003430337720000192
The specific synthesis steps are as follows:
synthesis of intermediate M15-3: referring to the synthesis of compound M4-3, compound M15-1 and compound M15-2 were used in place of compounds M4-1 and M4-2, respectively, in 72% yield.
Synthesis of intermediate M15-6: referring to the synthesis of intermediate M1-3, compound M15-4 and compound M15-5 were used in place of compound M1-1 and compound M1-2, respectively, in 62% yield.
Synthesis of compound M15: referring to the synthesis of compound M1, intermediate M15-6 and intermediate M15-3 were used in place of intermediate M1-3 and compound M1-4, respectively, in 56% yield. MS (ASAP): 697.
the process of preparing an OLED device including the above-described compounds is described in detail below by way of specific examples. The structure of the OLED device is shown in fig. 1, and 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 the cathode.
The OLED-1 was prepared as follows:
a. an ITO (indium tin oxide) conductive glass substrate was washed with various solvents (e.g., one or more of deionized water, chloroform, acetone, or isopropyl alcohol) for 15 minutes, and then subjected to ultraviolet ozone plasma treatment.
b. The ITO conductive glass substrate was transferred into a vacuum vapor deposition apparatus under high vacuum (1×10) -6 Millibar) and evaporating HIM by resistance heating to form a 40nm thick hole injection layer.
c. High vacuum evaporation of HTM material on the hole injection layer forms a hole transport layer (material: HTM) with a thickness of 100 nm.
d. A light-emitting layer was formed on the hole transport layer by high vacuum deposition of a material for the light-emitting layer (the weight ratio of the light-emitting Host material Host to the light-emitting guest material BD was 95:5) to have a thickness of 50 nm.
e. An electron transport layer of 25nm was formed by high vacuum evaporation of compound M1 on the light-emitting layer.
f. Electron injection layer: in high vacuum (1X 10) -6 Millibar) LiQ was thermally evaporated to form an electron injection layer with a thickness of 1 nm.
g. And (3) cathode: in high vacuum (1X 10) -6 Millibar) of a thermally evaporated metal Al forms a cathode with a thickness of 150 nm.
h. And (3) packaging: the device was encapsulated with an ultraviolet curable resin in a nitrogen glove box.
The preparation schemes of the devices OLED-2 to OLED-15 of the example and OLED-Ref-1 of the comparative example are the same as OLED-1, except that the electron-transporting layer material in the OLED-1 of the example is replaced by the compound M1 with the compound M2-compound M15 or Ref-1 corresponding to the electron-transporting layer material in Table I.
The structures of the compounds that may be involved in the preparation of an OLED are as follows:
Figure BDA0003430337720000201
the current-voltage (J-V) characteristics of each OLED device were characterized by a characterization apparatus while recording LT90 lifetime and luminous efficiency, with the results being referred to in table one below. Where LT90@1000nits is the time at constant current at which the luminance drops from an initial luminance of 1000nits to 90% of the initial luminance. Here, the lt90@1000nits, external Quantum Efficiency (EQE) was calculated with respect to the device OLED-Ref-1 of the comparative example (corresponding electron transport layer material is Ref-1), i.e., with the lifetime lt90@1000nits of OLED-Ref-1 being 1, the external quantum efficiency EQE being 1.
Table one:
Figure BDA0003430337720000202
from Table one can see: compared with the OLED device OLED-Ref-1 prepared by respectively adopting the compound Ref-1 as the electron transport layer material in the comparative example, the OLED devices OLED-1 to OLED-15 prepared by adopting the organic compound of the invention as the electron transport layer material in the embodiment have better external quantum efficiency EQE and longer service life LT90@1000nits, and the EQE and the service life LT90 are more than 1.5 times of that of the OLED device OLED-Ref-1, namely the organic compound of the invention can effectively improve the external quantum efficiency and the service life of the organic electroluminescent device by adopting the organic compound of the invention as the electron transport material. In the organic compound, phosphorus oxide and imidazole are connected through an aromatic group, and the imidazole is connected with a fluorine-containing group, so that the organic compound containing three electron-transporting groups of phosphorus oxide, imidazole and fluorine can provide a plurality of gradient transport channels for electron transport, has better electron transport capacity, and can be used as an electron transport material to be applied to an electron transport layer in an electronic device to effectively improve the efficiency and stability of the device, thereby improving the performance and service life of the device.
The organic compounds, mixtures, compositions and organic electronic devices provided by the embodiments of the present invention have been described in detail, and specific examples have been employed herein to illustrate the principles and embodiments of the present invention, the above examples being provided only to assist in understanding the methods of the present invention and the core ideas thereof; meanwhile, as those skilled in the art will have variations in the specific embodiments and application scope in light of the ideas of the present invention, the present description should not be construed as limiting the present invention.

Claims (12)

1. An organic compound characterized by having a structure represented by the general formula (1):
Figure FDA0003430337710000011
wherein Ar is 1 、Ar 2 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;
Ar 3 、Ar 4 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;
l is independently selected for each occurrence 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;
R 1 、R 2 Each occurrence is independently selected from: hydrogen, deuterium, or substituted or unsubstituted straight chain alkyl groups having 1 to 20C atomsOr a substituted or unsubstituted straight-chain alkoxy group having 1 to 20C atoms, or a substituted or unsubstituted straight-chain thioalkoxy group having 1 to 20C atoms, or a substituted or unsubstituted branched alkyl group having 3 to 20C atoms, or a substituted or unsubstituted branched alkoxy group having 3 to 20C atoms, or a substituted or unsubstituted branched thioalkoxy group having 3 to 20C atoms, or a substituted or unsubstituted cyclic alkyl group having 3 to 20C atoms, or a substituted or unsubstituted cyclic alkoxy group having 3 to 20C atoms, or a substituted or unsubstituted cyclic thioalkoxy group having 3 to 20C atoms, or a silyl group, or a ketone group having 1 to 20C atoms, or an alkoxycarbonyl group having 2 to 20C atoms, or an aryloxycarbonyl group having 7 to 20C atoms, cyano group, carbamoyl group, haloformyl group, formyl group, isocyano group, isocyanate group, thiocyanate group, isothiocyanate group, hydroxyl group, nitro group, amine group, -CF group 3 、-OCF 3 -Cl, -Br, -F, -I, or an alkenyl group having 2 to 20C atoms, or a substituted or unsubstituted aryl group having 6 to 60 ring atoms, or a substituted or unsubstituted heteroaryl 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;
And R is 1 And R is 2 At least one of which contains an F atom;
n is an integer from 0 to 6; m is selected from integers from 0 to 8.
2. The organic compound according to claim 1, wherein Ar 1 Selected from the following groups:
Figure FDA0003430337710000012
wherein: x is independently selected from CR for each occurrence 1 Or N;
y is independently at each occurrence selected from NR 4 、PR 4 、CR 5 R 6 、SiR 5 R 6 、O、S、S(＝O) 2 Or S (=o);
R 4 、R 5 、R 6 each occurrence is independently selected from: hydrogen, deuterium, or substituted or unsubstituted straight-chain alkyl having 1 to 20C atoms, or substituted or unsubstituted straight-chain alkoxy having 1 to 20C atoms, or substituted or unsubstituted straight-chain thioalkoxy having 1 to 20C atoms, or substituted or unsubstituted branched alkyl having 3 to 20C atoms, or substituted or unsubstituted branched alkoxy having 3 to 20C atoms, or substituted or unsubstituted branched thioalkoxy having 3 to 20C atoms, or substituted or unsubstituted cyclic alkyl having 3 to 20C atoms, or substituted or unsubstituted cyclic alkoxy having 3 to 20C atoms, or substituted or unsubstituted cyclic thioalkoxy having 3 to 20C atoms, or silyl, or ketone group having 1 to 20C atoms, or alkoxycarbonyl group having 2 to 20C atoms, or aryloxycarbonyl having 7 to 20C atoms, cyano, carbamoyl, haloformyl, formyl, isocyano, thiocyanate, hydroxy, nitro, -CF amine, -isothiocyanate 3 、-OCF 3 -Cl, -Br, -F, -I, or an alkenyl group having 2 to 20C atoms, or a substituted or unsubstituted aryl group having 6 to 60 ring atoms, or a substituted or unsubstituted heteroaryl 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;
* Represents a condensed site.
3. The organic compound according to claim 1 or 2, wherein R 1 、R 2 Each occurrence is independently selected from: hydrogen, deuterium, fluorine, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, or the following groups:
Figure FDA0003430337710000021
wherein: a is selected from 1, 2, 3, 4 or 5.
4. An organic compound according to claim 3, wherein R 2 Selected from the group consisting of-F, -CF 3 Or the following groups:
Figure FDA0003430337710000022
and/or
At least one R 1 Selected from the group consisting of-F, -CF 3 Or the following groups:
Figure FDA0003430337710000023
5. the organic compound according to claim 2, wherein Ar 2 And L is independently selected from the group consisting of:
Figure FDA0003430337710000024
wherein: x is X 1 Each occurrence is independently selected from CR 7 Or N;
Y 1 each occurrence is independently selected from NR 8 、PR 8 、CR 9 R 10 、SiR 9 R 10 、O、S、S(＝O) 2 Or S (=o);
R 7 、R 8 、R 9 、R 10 each occurrence is independently selected from: hydrogen, deuterium, or a substituted or unsubstituted straight chain alkyl group having 1 to 20C atoms, or a substituted or unsubstituted straight chain alkoxy group having 1 to 20C atoms, or a substituted or unsubstituted straight chain thioalkoxy group having 1 to 20C atoms, or a substituted or unsubstituted branched alkyl group having 3 to 20C atoms, or a substituted or unsubstituted branched alkoxy group having 3 to 20C atoms Branched thioalkoxy group having 3 to 20C atoms, or substituted or unsubstituted cyclic alkyl group having 3 to 20C atoms, or substituted or unsubstituted cyclic alkoxy group having 3 to 20C atoms, or substituted or unsubstituted cyclic thioalkoxy group having 3 to 20C atoms, or silyl group, or ketone group having 1 to 20C atoms, or alkoxycarbonyl group having 2 to 20C atoms, or aryloxycarbonyl group having 7 to 20C atoms, cyano, carbamoyl, haloformyl, formyl, isocyano, thiocyanate, isothiocyanate group, hydroxyl, nitro, amino, -CF 3 、-OCF 3 -Cl, -Br, -F, -I, or an alkenyl group having 2 to 20C atoms, or a substituted or unsubstituted aryl group having 6 to 60 ring atoms, or a substituted or unsubstituted heteroaryl 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.
6. The organic compound according to claim 5, wherein Ar 2 And L is independently selected from any of the structures of formulas (C-1) to (C-18):
Figure FDA0003430337710000031
wherein, represents the site of attachment.
7. The organic compound according to claim 5, wherein the organic compound of the general formula (1) is selected from the structures represented by any one of the formulae (2-1) to (2-11):
Figure FDA0003430337710000032
wherein m1 is selected from 0, 1, 2, 3 or 4.
8. The organic compound according to claim 1, which isCharacterized in that Ar 3 ～Ar 4 Independently selected from the following groups:
Figure FDA0003430337710000041
wherein:
X 2 each occurrence is independently selected from CR 11 Or N;
Y 2 each occurrence is independently selected from NR 12 、PR 12 、CR 13 R 14 、SiR 13 R 14 、O、S、S(＝O) 2 Or S (=o);
R 11 、R 12 、R 13 、R 14 each occurrence is independently selected from: H. d, a linear alkyl group having 1 to 20C atoms, a linear alkoxy group having 1 to 20C atoms, a linear thioalkoxy group having 1 to 20C atoms, a branched alkyl group having 3 to 20C atoms, a cycloalkyl group having 3 to 20C atoms, a branched alkoxy group having 3 to 20C atoms, a cyclic alkoxy group having 3 to 20C atoms, a branched thioalkoxy group having 3 to 20C atoms, a cyclic thioalkoxy group having 3 to 20C atoms, a silyl group, a ketone group having 1 to 20C atoms, an alkoxycarbonyl group having 2 to 20C atoms, an aryloxycarbonyl group having 7 to 20C 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, a CF 3 、OCF 3 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;
two adjacent R 11 Are connected with each other to form a ring or not.
9. The organic compound according to claim 1, wherein the organic compound is selected from any one of the structures shown below:
Figure FDA0003430337710000042
Figure FDA0003430337710000051
Figure FDA0003430337710000061
Figure FDA0003430337710000071
10. a mixture comprising the organic compound according to any one of claims 1 to 9 and at least one organic functional material selected from a hole injection material, a hole transport material, an electron injection material, an electron blocking material, a hole blocking material, a luminescent guest material, a luminescent host material, or an organic dye.
11. A composition comprising the organic compound according to any one of claims 1 to 9 or the mixture according to claim 10, and at least one organic solvent.
12. An organic electronic device comprising at least one functional layer, characterized in that the functional layer comprises an organic compound according to any one of claims 1 to 9, or a mixture according to claim 10, or is prepared from a composition according to claim 11.
CN202111592987.7A 2021-12-23 2021-12-23 Organic compound, mixture, composition and organic electronic device comprising same Pending CN116355016A (en)

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