CN116143793A - 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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CN116143793A
CN116143793A CN202111372224.1A CN202111372224A CN116143793A CN 116143793 A CN116143793 A CN 116143793A CN 202111372224 A CN202111372224 A CN 202111372224A CN 116143793 A CN116143793 A CN 116143793A
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夏泽铭
黄增
宋晶尧
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Guangzhou Chinaray Optoelectronic Materials Ltd
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Abstract

The application discloses an organic compound, which has the following structure:
Figure DDA0003362724380000011
Ar 1 selected from the group consisting of
Figure DDA0003362724380000012
In addition, the application also discloses a mixture, a composition and an organic electronic device. The anthracene derivative containing heterocyclic condensed rings can be used as a main body material and used for the hair of organic electronic devicesIn the optical layer. The organic matters have fluorescence emission at blue light wavelength, can be used as luminescent materials in blue light organic luminescent electronic devices, and can enable the organic electronic devices to have higher device luminous efficiency and longer device service life.

Description

Organic compound, mixture, composition and organic electronic device comprising same
Technical Field
The present application relates to the technical field of luminescent materials, and in particular, to an organic compound, and a mixture, a composition and an organic electronic device including the organic compound.
Background
Organic semiconductor materials are synthetically diverse, relatively low in cost to manufacture, and excellent in optical and electrical properties. Organic Light Emitting Diodes (OLEDs) have advantages of wide viewing angle, fast reaction time, low operating voltage, thin panel thickness, etc. in applications of optoelectronic devices such as flat panel displays and illumination, and thus have a wide development potential.
The organic electroluminescence refers to a phenomenon in which electric energy is converted into light energy using an organic substance. An organic electroluminescent element utilizing the organic electroluminescent phenomenon generally has a structure in which a positive electrode and a negative electrode have an organic layer therebetween. In order to improve the efficiency and lifetime of the organic electroluminescent device, the organic layers have a multi-layered structure, and each layer contains a different organic material. Specifically, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and the like may be included. In such an organic electroluminescent element, 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 element, various luminescent material systems based on fluorescence and phosphorescence have been developed, and the development of excellent blue light materials, whether fluorescent materials or phosphorescent materials, is a great challenge, and in general, the reliability of the organic light emitting diode of the currently used blue light fluorescent materials is higher. However, most blue fluorescent materials have over-wide emission spectrum, poor color purity, unfavorable high-end display, complex synthesis of the fluorescent materials, unfavorable mass production, and further improvement of OLED stability of the blue fluorescent materials. Therefore, the development of the blue fluorescent material with narrow-band emission spectrum and good stability is beneficial to obtaining a blue light device with longer service life and higher efficiency on one hand, and is beneficial to improving the color gamut on the other hand, so as to improve the display effect.
At present, a main guest doping structure is adopted in a light-emitting layer of the blue light organic electroluminescent element, and most of blue light main materials adopt condensed ring derivatives based on anthracene, but the stability of the light-emitting layer material is poor, so that the service life of the device is short. Meanwhile, the materials are difficult to realize deep blue luminescence, and the requirements of full-color display are difficult to meet.
Accordingly, there is still a need for further improvements in materials to improve the performance of organic electroluminescent devices.
Disclosure of Invention
In view of the above, the present application provides a blue light fluorescent organic compound, which aims to solve the problems of low light emitting efficiency and short service life of the existing blue light fluorescent organic electronic device.
The application is realized by the following technical scheme:
an organic compound having a structure represented by the general formula (1):
Figure BDA0003362724360000011
wherein:
Ar 1 selected from structures represented by general formula (2):
Figure BDA0003362724360000012
Ar 2 selected from a substituted or unsubstituted aromatic group containing 6 to 60 ring atoms, or a substituted or unsubstituted heteroaromatic group containing 5 to 60 ring atoms, or a combination of these groups;
g is selected from a linear alkyl group having 1 to 20C atoms, or a branched alkyl group having 3 to 20C atoms, or a cyclic alkyl group having 3 to 20C atoms, 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 combination of such groups;
L 1 、L 2 Independently selected from a single bond, or a substituted or unsubstituted aromatic group containing 6 to 60 ring atoms, or a substituted or unsubstituted heteroaromatic group containing 5 to 60 ring atoms;
R 1 、R 2 and R is 3 Each occurrence is independently selected from the group consisting of-D, or a linear alkyl group having 1 to 20C atoms, a linear alkoxy group having 1 to 20C atoms, or a linear thioalkoxy group having 1 to 20C atoms, or a branched alkyl group having 3 to 20C atoms, or a branched alkoxy group having 3 to 20C atoms, or a branched thioalkoxy group having 3 to 20C atoms, or a cyclic alkyl group having 3 to 20C atoms, or a cyclic alkoxy group having 3 to 20C atoms, or a 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, carbamoyl, haloformyl, formyl, isocyano, isocyanate, thiocyanate, or isothiocyanate groups, hydroxyl, nitro, substituted or unsubstituted amine groups, -CF 3 -Cl, -Br, -F, -I, 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 5 to 60 ring atoms, or a substituted or unsubstituted heteroaryloxy group having 5 to 60 ring atoms, or a combination of these groups;
m1 is 0, 1, 2, 3, 4, 5, 6, 7 or 8;
m2 is 0, 1, 2 or 3;
m3 is 0, 1, 2 or 3.
Correspondingly, the application 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 materials, host materials, guest materials or organic dyes.
Correspondingly, the application also provides a composition which comprises the organic compound or the mixture and at least one organic solvent.
Correspondingly, the application 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:
the anthracene derivative containing the heterocyclic condensed rings can be used as a main body material and used in a light-emitting layer of an organic electronic device. The organic matters have fluorescence emission at blue light wavelength, so the organic matters can be used in blue light organic light-emitting electronic devices, and have higher device luminous efficiency and longer device life.
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In order to more clearly illustrate the technical solutions of the embodiments of the present application, the drawings that are needed in the description of the embodiments will be briefly introduced below, it being obvious that the drawings in the following description are only some embodiments of the present application, 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 example 1 of the device of the present application;
where 101 is a substrate, 102 is an anode, 103 is a Hole Injection Layer (HIL), 104 is a Hole Transport Layer (HTL), 105 is a light emitting layer, 106 is an Electron Transport Layer (ETL), and 107 is a cathode.
Detailed Description
The following description of the embodiments of the present application will be made clearly and fully with reference to the accompanying drawings, in which it is evident that the embodiments described are only some, but not all, of the embodiments of the present application. All other embodiments, based on the embodiments herein, which are obtained by a person skilled in the art without making any inventive effort, are intended to be within the scope of the present application. Furthermore, it should be understood that the detailed description is presented herein for purposes of illustration and explanation only and is not intended to limit the present application.
In the description of the present application, the term "comprising" means "including but not limited to," and the term "plurality" means "two or more. Various embodiments of the present application may exist in a range format; it should be understood that the description in a range format is merely for convenience and brevity and should not be interpreted as a rigid limitation on the scope of the application. 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 application belongs. The terminology used herein in the description of the application is for the purpose of describing particular embodiments only and is not intended to be limiting of the application. The term "and/or" as used herein includes any and all combinations of one or more of the associated listed items.
In this application, compositions, printing inks and inks have the same meaning and are interchangeable.
In the present application, aromatic groups, aromatic ring systems have the same meaning and are interchangeable.
In the present application, heteroaromatic groups, heteroaromatic ring systems have the same meaning and can be interchanged.
In the present application, "substituted" means that a hydrogen atom in a substituted group is substituted with a substituent.
In the present application, "substituted or unsubstituted" means that the defined group may or may not be substituted. When the defined groups are substituted, it is understood that the defined groups may be substituted with one or more substituents R selected from, but not limited to, deuterium atoms, cyano groups, isocyano groups, nitro groups, halogens, alkyl groups containing 1 to 20C 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, -NR' R ", silane groups, carbonyl groups, alkoxycarbonyl groups, aryloxycarbonyl groups, carbamoyl groups, haloformyl groups, formyl groups, isocyanate groups, thiocyanate groups, isothiocyanate groups, hydroxyl groups and trifluoromethyl groups, and the above groups may be further substituted with substituents acceptable in the art; it will be appreciated that R 'and R "in-NR' R" are each independently selected from, but not limited to, H, deuterium, cyano, isocyano, nitro or halogen, alkyl containing 1-10C atoms, heterocyclyl containing 3-20 ring atoms, aromatic containing 6-20 ring atoms, heteroaromatic containing 5-20 ring atoms. Preferably, R is selected from, but not limited to, deuterium, cyano, isocyano, nitro or halogen, alkyl containing 1-10C atoms, heterocyclyl containing 3-10 ring atoms, aromatic containing 6-20 ring atoms, heteroaromatic containing 5-20 ring atoms, silyl, carbonyl, alkoxycarbonyl, aryloxycarbonyl, carbamoyl, haloformyl, formyl, isocyanate, thiocyanate, isothiocyanate, hydroxyl and trifluoromethyl, and the above groups may be further substituted with substituents acceptable in the art.
In the present application, the "number of ring atoms" means the number of atoms among atoms constituting the ring itself of a structural compound (for example, a monocyclic compound, a condensed ring compound, a crosslinked compound, a carbocyclic compound, a heterocyclic compound) in which atoms are bonded to form a ring. When the ring is substituted with a substituent, the atoms contained in the substituent are not included in the ring-forming atoms. 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, and 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 example, "substituted or unsubstituted aryl group having 6 to 40 ring atoms" means an aryl group having 6 to 40 ring atoms, preferably a substituted or unsubstituted aryl group having 6 to 30 ring atoms, more preferably a substituted or unsubstituted aryl group having 6 to 18 ring atoms, 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), and that in particular acenaphthene, fluorene, 9-diaryl fluorene, triarylamine or diaryl ether systems 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, benzothienyl, benzofuranyl, indolyl, pyrroloimidazoyl, pyrrolopyrrolyl, thienopyrrolyl, furopyrrolyl, furofuranyl, benzisoxazolyl, benzoisoxazolyl, benzothiazolyl, naphthyridinyl, phthalazinyl, benzofuranyl, and derivatives thereof.
In this application, "alkyl" may mean straight, branched, and/or cyclic alkyl. 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. 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, adamantyl, and the like.
In this application, "halogen" or "halo" refers to F, cl, br or I.
In the present application, the term "alkoxy" refers to a group having an-O-alkyl group, i.e. an alkyl group as defined above is attached to the parent core structure 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 this application, "×" indicates a ligation site.
In the present application, 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 BDA0003362724360000041
6R on benzene ring 1 May be the same or different from each other.
In the present application, 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 on the ring, e.g
Figure BDA0003362724360000042
R in (2) is connected with any substitutable site of benzene ring; for example->
Figure BDA0003362724360000043
Representation->
Figure BDA0003362724360000044
Can be combined with->
Figure BDA0003362724360000045
Optionally forming a fused ring at an optional position on the benzene ring.
Cyclic alkyl or cycloalkyl groups as described herein have the same meaning and are interchangeable.
The technical scheme of the application is as follows:
an organic compound having a structure represented by the general formula (1):
Figure BDA0003362724360000046
wherein:
Ar 1 selected from structures represented by general formula (2):
Figure BDA0003362724360000047
Ar 2 selected from a substituted or unsubstituted aromatic group containing 6 to 60 ring atoms, or a substituted or unsubstituted heteroaromatic group containing 5 to 60 ring atoms, or a combination of these groups;
g is selected from a linear alkyl group having 1 to 20C atoms, or a branched alkyl group having 3 to 20C atoms, or a cyclic alkyl group having 3 to 20C atoms, 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 combination of such groups;
L 1 、L 2 independently selected from a single bond, or a substituted or unsubstituted aromatic group containing 6 to 60 ring atoms, or a substituted or unsubstituted heteroaromatic group containing 5 to 60 ring atoms;
R 1 、R 2 And R is 3 Each occurrence is independently selected from-D, or a linear alkyl group having 1 to 20C atoms, a linear alkyl group having 1 to 20C atomsAn oxy group, or a linear thioalkoxy group having 1 to 20C atoms, or a branched alkyl group having 3 to 20C atoms, or a branched alkoxy group having 3 to 20C atoms, or a branched thioalkoxy group having 3 to 20C atoms, or a cyclic alkyl group having 3 to 20C atoms, or a cyclic alkoxy group having 3 to 20C atoms, or a cyclic thioalkoxy group having 3 to 20C atoms, or a silyl group, or a keto 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, carbamoyl, haloformyl, formyl, isocyano, isocyanate, thiocyanate, or isothiocyanate group, hydroxyl, nitro, substituted or unsubstituted amino, -CF 3 -Cl, -Br, -F, -I, 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 5 to 60 ring atoms, or a substituted or unsubstituted heteroaryloxy group having 5 to 60 ring atoms, or a combination of these groups;
m1 is 0, 1, 2, 3, 4, 5, 6, 7 or 8;
m2 is 0, 1, 2 or 3;
m3 is 0, 1, 2 or 3.
In one embodiment, the organic compound is selected from the structures represented by the general formula (3-1) or the general formula (3-2):
Figure BDA0003362724360000051
in some embodiments, R 1 、R 2 And R is 3 Each occurrence is independently selected from the group consisting of-D, or a linear alkyl group having 1 to 10C atoms, or a linear alkoxy group having 1 to 10C atoms, or a linear thioalkoxy group having 1 to 10C atoms, or a branched alkyl group having 3 to 10C atoms, or a branched alkoxy group having 3 to 10C atoms, or a branched thioalkoxy group having 3 to 10C atoms, or a cyclic alkyl group having 3 to 20C atoms, or a cyclic alkoxy group having 3 to 10C atomsCyclic thioalkoxy groups of 3 to 10C atoms, or silyl groups, or keto groups of 1 to 10C atoms, or alkoxycarbonyl groups of 2 to 10C atoms, or aryloxycarbonyl groups of 7 to 10C atoms, cyano groups, carbamoyl groups, haloformyl groups, formyl groups, isocyano groups, isocyanate groups, thiocyanate groups, or isothiocyanate groups, hydroxyl groups, nitro groups, amine groups, CF groups 3 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 6 to 30 ring atoms, or a substituted or unsubstituted aryloxy group having 6 to 30 ring atoms, or a substituted or unsubstituted heteroaryloxy group having 6 to 30 ring atoms, or a combination of such groups.
In some embodiments, R 1 、R 2 And R is 3 Each occurrence is independently selected from the group consisting of-D, straight chain alkyl having 1 to 8C atoms, branched alkyl having 3 to 8C atoms, cyclic alkyl having 3 to 8C atoms, silyl, cyano, isocyano, hydroxy, nitro, -CF 3 -Cl, -Br, -F, an aromatic group with 6 to 10 ring atoms substituted or unsubstituted, a heteroaromatic group with 5 to 10 ring atoms substituted or unsubstituted, or a combination of these groups.
In some embodiments, R 1 、R 2 And R is 3 Each occurrence is independently selected from the group consisting of-D, straight chain alkyl having 1 to 4C atoms, branched alkyl having 3 to 6C atoms, cyclic alkyl having 3 to 6C atoms, silyl, cyano, isocyano, hydroxy, nitro, -CF 3 -Cl, -Br, -F, an aromatic group with 6 to 10 ring atoms substituted or unsubstituted, a heteroaromatic group with 6 to 10 ring atoms substituted or unsubstituted, or a combination of these groups.
In some specific embodiments, R 1 、R 2 And R is 3 Each occurrence is independently selected from the group consisting of-D, 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 Pentyl, 2-ethylpentyl, 4-methyl-2-pentyl, n-hexyl, 1-methylhexyl, 2-ethylhexyl, 2-butylhexyl, cyclohexyl, adamantyl, phenyl, biphenyl, terphenyl, naphthyl, anthryl, phenanthryl, triazinyl, pyridyl, pyrimidinyl, imidazolyl, furanyl, thienyl, benzofuranyl, benzothienyl, indolyl, carbazolyl, dibenzothienyl, dibenzofuranyl, phenyl-substituted carbazolyl, fluorenyl substituted with an alkyl group having 1 to 6C atoms, phenyl substituted with an alkyl group having 1 to 6C atoms, naphthyl substituted with an alkyl group having 1 to 6C atoms, or phenyl substituted with one or more D's, naphthyl substituted with one or more D's, or naphthyl substituted with phenyl groups.
In one embodiment, m2 is 0 or 1; r is R 2 Each occurrence is independently selected from the group consisting of-D, methyl, isopropyl, tert-butyl, phenyl, biphenyl, naphthyl, phenyl-substituted carbazolyl, dibenzofuranyl, dibenzothiophenyl, fluorenyl substituted with one or more methyl groups, phenanthryl, pyrenyl, fluoranthenyl, pyridinyl, pyrimidinyl, phenyl substituted with an alkyl group having 1 to 6C atoms, naphthyl substituted with an alkyl group having 1 to 6C atoms, phenyl substituted with one or more D groups, naphthyl substituted with one or more D groups, and naphthyl substituted with phenyl groups.
In one embodiment, m3 is 0 or 1.R is R 3 Each occurrence is independently selected from the group consisting of-D, methyl, isopropyl, tert-butyl, phenyl, biphenyl, naphthyl, phenyl-substituted carbazolyl, dibenzofuranyl, dibenzothiophenyl, fluorenyl substituted with one or more methyl groups, phenanthryl, pyrenyl, fluoranthenyl, pyridinyl, pyrimidinyl, phenyl substituted with an alkyl group having 1 to 6C atoms, naphthyl substituted with an alkyl group having 1 to 6C atoms, phenyl substituted with one or more D groups, naphthyl substituted with one or more D groups, and naphthyl substituted with phenyl groups.
In some embodiments, ar 2 Selected from a substituted or unsubstituted aromatic group containing 6 to 30 ring atoms, or a substituted or unsubstituted heteroaromatic group containing 6 to 30 ring atoms.
In some implementationsIn embodiments, ar 2 Selected from a substituted or unsubstituted aromatic group containing 6 to 16 ring atoms, or a substituted or unsubstituted heteroaromatic group containing 6 to 16 ring atoms.
In some embodiments, the Ar 2 Selected from any of the structures shown below:
Figure BDA0003362724360000061
wherein:
x is independently selected from CR for each occurrence 5 Or N;
y is selected from NR 6 、CR 7 R 8 、SiR 7 R 8 O, S, S =o or SO 2 ；
R 5 、R 6 、R 7 、R 8 Each occurrence is independently selected from the group consisting of-H, -D, or a linear alkyl group having 1 to 20C atoms, a linear alkoxy group having 1 to 20C atoms, or a linear thioalkoxy group having 1 to 20C atoms, or a branched alkyl group having 3 to 20C atoms, or a branched alkoxy group having 3 to 20C atoms, or a branched thioalkoxy group having 3 to 20C atoms, or a cyclic alkyl group having 3 to 20C atoms, or a cyclic alkoxy group having 3 to 20C atoms, or a 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, carbamoyl, haloformyl, formyl, isocyano, isocyanate, thiocyanate, or isothiocyanate groups, hydroxyl, nitro, amine, -CF3, -Cl, -Br, -F, -I, or a substituted or unsubstituted aromatic group having 6 to 60 ring atoms, or a substituted or unsubstituted aromatic group having 5 to 60 ring atoms, or a substituted or a combination of 5 to 60 ring atoms, or a substituted or unsubstituted aromatic group having 5 to 60 ring atoms; r is R 7 And R is 8 With or without each other.
It is understood that in the present application, when X is a ligation site, X is C; when Y is a ligation site, Y is N.
In some embodiments, the structure of the organic compound is selected from structures represented by any one of formulas (4-1) - (4-10):
Figure BDA0003362724360000062
Figure BDA0003362724360000071
in some specific examples, R 5 Each occurrence is independently selected from: -H, -D, straight chain alkyl having 1 to 10C atoms, branched alkyl having 3 to 10C atoms, cyclic alkyl having 3 to 10C atoms, silyl, cyano, isocyano, nitro, -CF 3 -Cl, -Br, -F, -I, a substituted or unsubstituted aromatic group having 6 to 20 ring atoms, a substituted or unsubstituted heteroaromatic group having 5 to 20 ring atoms, or a combination of these groups.
Further, R 5 Each occurrence is independently selected from: -H, -D, a linear alkyl group having 1 to 8C atoms, a branched alkyl group having 3 to 8C atoms, a cyclic alkyl group having 3 to 8C atoms, a substituted or unsubstituted aromatic group having 6 to 10 ring atoms, a substituted or unsubstituted heteroaromatic group having 5 to 10 ring atoms, or a combination of these groups. Wherein the definition of the substituted substituents is referred to the relevant description above, and is not repeated here. Preferably, the substituents are selected from-D, straight chain alkyl groups having 1 to 4C atoms, branched chain alkyl groups having 3 to 4C atoms, or phenyl, or pyridyl.
In one embodiment, X in the general formulae (4-1) - (4-10) is selected from CR 5 ；R 5 Each occurrence is independently selected from: -H, -D, a linear alkyl group having 1 to 6C atoms, a branched alkyl group having 3 to 6C atoms, a cyclic alkyl group having 3 to 6C atoms.
In one embodiment, R 6 Each occurrence is independently selected from: a linear alkyl group having 1 to 10C atoms, a branched alkyl group having 3 to 10C atoms, a cyclic alkyl group having 3 to 10C atoms, a substituted or unsubstituted aromatic group having 6 to 20 ring atoms, a substituted or unsubstituted heteroaromatic group having 5 to 20 ring atoms, or a combination of these groups; further, R 6 Each occurrence is independently selected from: a substituted or unsubstituted aromatic group having 6 to 13 ring atoms, a substituted or unsubstituted heteroaromatic group having 6 to 13 ring atoms, or a combination of such groups. Alternatively, R 6 Each occurrence is independently selected from: methyl, ethyl, isopropyl, tert-butyl, phenyl, pyridyl, pyrimidinyl, triazinyl, biphenyl, terphenyl or naphthyl.
In some specific examples, R 7 、R 8 Each occurrence is independently selected from: -H, -D, a linear alkyl group having 1 to 8C atoms, a branched alkyl group having 3 to 8C atoms, a cyclic alkyl group having 3 to 8C atoms, a substituted or unsubstituted aromatic group having 6 to 10 ring atoms, a substituted or unsubstituted heteroaromatic group having 5 to 10 ring atoms, or a combination of these groups; further, R 7 、R 8 Each occurrence is independently selected from: -H, -D, methyl, ethyl, isopropyl, phenyl, pyridyl, pyrimidinyl, triazinyl, biphenyl, terphenyl or naphthyl.
In a particular embodiment, ar 2 Selected from any of the structures shown below:
Figure BDA0003362724360000081
wherein: * Representing the ligation site.
In one embodiment, G is selected from a linear alkyl group having 1 to 10C atoms, or a branched alkyl group having 3 to 10C atoms, or a cyclic alkyl group having 3 to 10C atoms, a substituted or unsubstituted aromatic group having 6 to 30 ring atoms, or a substituted or unsubstituted heteroaromatic group having 6 to 30 ring atoms, or a combination of such groups.
In one embodiment, G is selected from a substituted or unsubstituted aromatic group containing 6 to 16 ring atoms, or a substituted or unsubstituted heteroaromatic group containing 6 to 16 ring atoms.
In one embodiment, G is selected from any of the structures shown below:
Figure BDA0003362724360000082
/>
wherein:
x, Y is as defined above.
Specifically, in the general formula (3-1) or the general formulae (4-1) to (4-5), G may be selected from the following groups:
Figure BDA0003362724360000083
in the general formula (3-2) or the general formulae (4-6) to (4-10), G is selected from the following groups:
Figure BDA0003362724360000084
wherein: * Representing the ligation site.
Preferably, in formulae (A-1) - (A-7) and/or formulae (B-1) - (B-4), X is independently selected from CR for each occurrence 5 Or N; r is R 5 Each occurrence is independently selected from: -H, -D, a linear alkyl group having 1 to 8C atoms, a branched alkyl group having 3 to 8C atoms, a cyclic alkyl group having 3 to 8C atoms, a substituted or unsubstituted aromatic group having 6 to 10 ring atoms, a substituted or unsubstituted heteroaromatic group having 5 to 10 ring atoms, or a combination of these groups. Wherein the definition of the substituent is as described above. Preferably, the substituents may be selected from-D, straight chain alkyl groups having 1 to 4C atoms, branched alkyl groups having 3 to 4C atoms, or phenyl, or pyridyl.
In the general formulae (A-1) to (A-7) and/or the general formulae (B-1) to (B-4), R 5 Each occurrence is independently selected from: h-D. A linear alkyl group having 1 to 6C atoms, a branched alkyl group having 3 to 6C atoms, a cyclic alkyl group having 3 to 6C atoms, or a phenyl group.
In one embodiment, L 1 、L 2 Independently selected from a single bond, or a substituted or unsubstituted aromatic group containing 6 to 20 ring atoms, or a substituted or unsubstituted heteroaromatic group containing 6 to 20 ring atoms; further, L 1 、L 2 Independently selected from a single bond, or a substituted or unsubstituted aromatic group containing 6 to 14 ring atoms, or a substituted or unsubstituted heteroaromatic group containing 6 to 14 ring atoms.
Further, in some embodiments, L 1 、L 2 Each independently selected from a single bond or a structure represented by any one of the following:
Figure BDA0003362724360000091
wherein:
X 1 each occurrence is independently selected from CR 4 Or N;
R 4 each occurrence is independently selected from the group consisting of-H, -D, or a linear alkyl group having 1 to 20C atoms, a linear alkoxy group having 1 to 20C atoms, or a linear thioalkoxy group having 1 to 20C atoms, or a branched alkyl group having 3 to 20C atoms, or a branched alkoxy group having 3 to 20C atoms, or a branched thioalkoxy group having 3 to 20C atoms, or a cyclic alkyl group having 3 to 20C atoms, or a cyclic alkoxy group having 3 to 20C atoms, or a cyclic thioalkoxy group having 3 to 20C atoms, or a silyl group, or a keto 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, carbamoyl, haloformyl, formyl, isocyano, isocyanate, thiocyanate, or isothiocyanate groups, hydroxyl, nitro, amine, -CF3, -Br, -F, -I, or a substituted or unsubstituted aromatic group having 6 to 60 ring atoms, or a substituted or unsubstituted aromatic group having 5 to 60 hetero atoms Or a substituted or unsubstituted aryloxy group having from 5 to 60 ring atoms, or a substituted or unsubstituted heteroaryloxy group having from 5 to 60 ring atoms, or a combination of such groups.
It is understood that in this application, when X 1 X is a binding site 1 Is C.
In some specific examples, R 4 Each occurrence is independently selected from: -H, -D, a linear alkyl group having 1 to 4C atoms, a branched alkyl group having 3 to 4C atoms, an aromatic group having 6 to 14 ring atoms, a heteroaromatic group having 6 to 14 ring atoms, an aromatic group having 6 to 14 ring atoms substituted with a linear alkyl group having 1 to 4C atoms or a branched alkyl group having 3 to 4C atoms, or a heteroaromatic group having 6 to 14 ring atoms substituted with a linear alkyl group having 1 to 4C atoms or a branched alkyl group having 3 to 6C atoms.
In some embodiments, L 1 And L is equal to 2 Each independently selected from a single bond or a group represented by any one of the following:
Figure BDA0003362724360000092
Figure BDA0003362724360000101
as an example, the organic compound of the present application may be selected from, but is not limited to, any of the following structures:
Figure BDA0003362724360000102
/>
Figure BDA0003362724360000111
/>
Figure BDA0003362724360000121
/>
Figure BDA0003362724360000131
/>
Figure BDA0003362724360000141
in some embodiments, the organic compounds of the present application may be applied as organic functional materials in functional layers of organic electronic devices, in particular OLED devices. The functional material may be, but is not limited to, a Hole Injection Material (HIM), a Hole Transport Material (HTM), an Electron Transport Material (ETM), an Electron Injection Material (EIM), an Electron Blocking Material (EBM), a Hole Blocking Material (HBM), a light Emitter (Emitter), a Host material (Host), or an organic dye.
In some embodiments, the organic compounds of the present application may be used as light emitting materials in the light emitting layer of an organic electronic device. In some preferred embodiments, the organic compounds of the present application are used as host materials in the light emitting layer of an organic electronic device.
The application also relates to a mixture comprising at least one organic compound as described above and at least one other organic functional material. The other organic functional material may be, but is not limited to, a hole injecting material, a hole transporting material, an electron injecting material, an electron blocking material, a hole blocking material, a light emitting material, a host material, a guest material, and an organic dye, which are known in the art for use in an organic electronic device.
In some embodiments, the another organic functional material is selected from guest materials. Further, the another organic functional material is selected from blue light guest materials. Further, the blue light guest may have a structure represented by the following general formula (5).
The present application also relates to a composition comprising at least one organic compound or mixture as described above, and at least one organic solvent.
Specifically, the at least one organic solvent is selected from an aromatic or heteroaromatic based solvent, an ester based solvent, an aromatic ketone based solvent, an aromatic ether based solvent, an aliphatic ketone, an aliphatic ether, a cycloaliphatic compound, an olefinic compound, a borate compound or a phosphate compound.
The aromatic or heteroaromatic based solvent may be selected from, but is 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-difluorodiphenylmethane, 1, 2-dimethoxy-4- (1-propenyl) benzene, diphenylmethane, 2-phenylpyridine, 3-phenylpyridine, N-methyldiphenylamine, 4-isopropylbiphenyl, α -dichlorodiphenylmethane, 4- (3-phenylpropylpyridine, 1, 3-dimethylquinoline, 2-dimethylquinoline, and at least one of the ethyl esters of furan.
The ester-based solvent may be selected from, but is 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. At least one of octyl octanoate, diethyl sebacate, diallyl phthalate and isononyl isononanoate is particularly preferable.
The aromatic ketone-based solvent may be selected from, but is not limited to, at least one of 1-tetralone, 2- (phenylepoxy) tetralone, 6- (methoxy) tetralone, acetophenone, propiophenone, benzophenone, and derivatives thereof, such as 4-methylacetophenone, 3-methylacetophenone, 2-methylacetophenone, 4-methylacetophenone, 3-methylacetophenone, and 2-methylacetophenone.
The aromatic ether-based solvent may be selected from, but is not limited to, at least one of 3-phenoxytoluene, butoxybenzene, p-anisaldehyde dimethyl acetal, tetrahydro-2-phenoxy-2H-pyran, 1, 2-dimethoxy-4- (1-propenyl) benzene, 1, 4-benzodioxane, 1, 3-dipropylbenzene, 2, 5-dimethoxytoluene, 4-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 and ethyl-2-naphthyl ether.
The aliphatic ketone-based solvent may be selected from, but is not limited to, 2-nonene, 3-nonene, 5-nonene, 2-decanone, 2, 5-hexanedione, 2,6, 8-trimethyl-4-nonene, fenchyl ketone, phorone, isophorone, di-n-amyl ketone, and the like; or aliphatic ethers such as at least one of amyl ether, hexyl ether, dioctyl ether, ethylene glycol dibutyl ether, diethylene glycol diethyl ether, diethylene glycol butyl methyl ether, diethylene glycol dibutyl ether, triethylene glycol dimethyl ether, triethylene glycol ethyl methyl ether, triethylene glycol butyl methyl ether, tripropylene glycol dimethyl ether and tetraethylene glycol dimethyl ether.
It is understood that the organic solvents may be used alone or as a mixed solvent of two or more organic solvents.
In some embodiments, the compositions of the present application comprise at least one organic compound or mixture as described above, and at least one organic solvent, and may further comprise another organic solvent.
The other organic solvent may be selected from, 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 (DMSO), tetrahydronaphthalene, decalin, and indene.
In some preferred embodiments, suitable organic solvents for the present application are solvents 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 application. 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 ℃; the optimal temperature is more than or equal to 300 ℃. Boiling points in these ranges are beneficial in preventing nozzle clogging of inkjet printheads.
It is understood that the organic solvent may be evaporated from the composition system to form a film comprising the organic compound of the present application.
In some embodiments, the composition is a solution. In other embodiments, the composition is a suspension.
The content of the organic compound or mixture in the composition may be 0.01 to 10wt%, preferably 0.1 to 8wt%, more preferably 0.2 to 5wt%, still more preferably 0.25 to 3wt%.
The application also relates to the use of the composition as a coating or printing ink in the preparation of an organic electronic device. In some embodiments, the composition is used to prepare 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, gravure printing, spray printing, letterpress printing, screen printing, dip coating, spin coating, doctor blade coating, roll printing, twist roller printing, offset printing, flexography, rotary printing, spray coating, brush coating, pad printing, slot die coating, and the like. Preferred are gravure printing, inkjet printing and inkjet printing.
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 present application 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 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).
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 OLED device. Further, in an embodiment, the organic compound is preferably used in a light emitting layer of an OLED device, the light emitting layer comprising the organic compound or mixture as described above, or prepared from the composition.
In some embodiments, at least a light emitting layer is included in one or more organic functional layers of the organic electronic device. The material of the light emitting layer comprises a host material and a guest material. The host material includes an organic compound as described above, and the guest material includes a pyrene-based organic compound.
The present application further relates to an organic electronic device comprising: the organic light-emitting device comprises a cathode, an anode and one or more organic functional layers positioned between the cathode and the anode, wherein the organic functional layers at least comprise a light-emitting layer, a light-emitting layer material comprises a host material and a guest material, the host material comprises an organic compound shown as a general formula (1), and the guest material comprises a pyrene organic compound shown as a general formula (5).
The structure of the general formula (5) is as follows:
Figure BDA0003362724360000161
wherein:
Ar 4 、Ar 5 、Ar 6 、Ar 7 each independently selected from a substituted or unsubstituted aromatic group containing 6 to 60 ring atoms, or a substituted or unsubstituted heteroaromatic group containing 6 to 60 ring atoms, or a combination of such groups;
R 9 each occurrence is independently selected from the group consisting of-H, -D, or a linear alkyl group having 1 to 20C atoms, a linear alkoxy group having 1 to 20C atoms, or a linear thioalkoxy group having 1 to 20C atoms, or a branched alkyl group having 3 to 20C atoms, or a branched alkoxy group having 3 to 20C atoms, or a branched thioalkoxy group having 3 to 20C atoms, or a cyclic alkyl group having 3 to 20C atoms, or a cyclic alkoxy group having 3 to 20C atoms, or a cyclic thioalkoxy group having 3 to 20C atoms, or a silyl group, or a keto 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, carbamoyl, haloformyl, formyl, isocyano, isocyanate, thiocyanate, or isothiocyanate, hydroxyl, nitro, amine, CF3, cl, br, F, I, or a substituted or unsubstituted aromatic group having 6 to 60 ring atoms, or a substituted or unsubstituted aromatic group having 5 to 60 hetero atoms Or a substituted or unsubstituted aryloxy group having from 5 to 60 ring atoms, or a substituted or unsubstituted heteroaryloxy group having from 5 to 60 ring atoms, or a combination of such groups;
s is selected from any integer in the range of 0-8.
Further description of the organic compound represented by the general formula (1) is as described above.
In some embodiments, ar 4 、Ar 5 、Ar 6 、Ar 7 Each independently selected from a substituted or unsubstituted aromatic group containing 6 to 14 ring atoms, or a substituted or unsubstituted heteroaromatic group containing 6 to 14 ring atoms, or a combination of such groups.
Further, in some embodiments, ar 4 、Ar 5 、Ar 6 、Ar 7 Each independently includes any of the following structures:
Figure BDA0003362724360000162
wherein:
v is independently selected from CR for each occurrence 10 Or N;
w is selected from NR 11 、CR 11 R 12 、SiR 11 R 12 O, S, S =o or SO 2 ；
R 10 、R 11 、R 12 Each occurrence is independently selected from the group consisting of-H, -D, or a linear alkyl group having 1 to 20C atoms, a linear alkoxy group having 1 to 20C atoms, or a linear thioalkoxy group having 1 to 20C atoms, or a branched alkyl group having 3 to 20C atoms, or a branched alkoxy group having 3 to 20C atoms, or a branched thioalkoxy group having 3 to 20C atoms, or a cyclic alkyl group having 3 to 20C atoms, or a cyclic alkoxy group having 3 to 20C atoms, or a 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, carbamoyl, Haloformyl, formyl, isocyano, thiocyanate, or isothiocyanate, hydroxy, nitro, amine, CF3, cl, br, F, I, or a substituted or unsubstituted aromatic group having from 6 to 60 ring atoms, or a substituted or unsubstituted heteroaromatic group having from 5 to 60 ring atoms, or a substituted or unsubstituted aryloxy group having from 5 to 60 ring atoms, or a substituted or unsubstituted heteroaryloxy group having from 5 to 60 ring atoms, or a combination of such groups.
Further, in some embodiments, R 9 、R 10 、R 11 、R 12 Each occurrence is independently selected from-H, -D, a straight chain alkyl group having 1 to 10C atoms, a branched or cyclic alkyl group having 3 to 10C atoms, or a phenyl group.
Further, in some embodiments, R 13 、R 14 、R 15 、R 16 Each occurrence is independently selected from-H, -D, a straight chain alkyl group having 1 to 10C atoms, a branched or cyclic alkyl group having 3 to 10C atoms, or a phenyl group.
It is understood that in the present application, when V is the attachment site, V is C; when W is the attachment site, W is N.
In some embodiments, the pyrene-based organic compound is selected from the following structural formulas:
Figure BDA0003362724360000171
wherein R is 10 Independently at each occurrence, selected from-H, -D, a straight chain alkyl group having 1 to 10C atoms, or a branched or cyclic alkyl group having 3 to 10C atoms, or phenyl.
Further, in some embodiments, the pyrene-based organic compound of formula (4) is selected from the following formulas:
Figure BDA0003362724360000172
wherein R is 10 Independently at each occurrence, selected from-H, -D, a linear alkyl group having 1 to 10C atoms, or a branched or cyclic alkyl group having 3 to 10C atoms, or phenyl; w is as described above.
As an example, the organic compound of formula (4) of the present application may be selected from, but is not limited to, any one of the following structures:
Figure BDA0003362724360000173
Figure BDA0003362724360000181
it will be appreciated that the organic electronic device may be further provided with functional layers conventionally used in organic electronic devices to help improve device performance, such as electron transport layers, electron injection layers, electron blocking layers, hole transport layers, hole injection layers, hole blocking layers, light extraction layers, and the like.
In one embodiment, the organic electronic device comprises a cathode, an anode, a hole transport layer, a light emitting layer, and an electron transport layer.
In one embodiment, the organic electronic device comprises a cathode, an anode, a hole transport layer, a hole injection layer, a light emitting layer, and an electron transport layer.
In one embodiment, the organic electronic device comprises a cathode, an anode, a hole transport layer, a hole injection layer, a light emitting layer, an electron blocking layer, and an electron transport layer.
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 anode material is 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 application.
The material of the cathode is a cathode material known in the art for use in organic electronic devices, such as a conductive metal or 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 that can be used as cathode of an OLED are possible as cathode materials for the device of the present application. 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 is a material known in the art for hole transport layers 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 (Poly-TPD), poly (3, 4-ethylenedioxythiophene) (ped sulfonic acid); PSS) and at least one of 4,4',4 "-tris (carbazol-9-yl) triphenylamine (TCTX).
The material of the electron transport layer is a material known in the art for an electron transport layer, and may be selected from at least one of ET and Liq, PBD (2- (4-biphenyl) -5-phenyloxadiazole), 8-hydroxyquinoline aluminum (Xlq 3), and graphene, for example.
Wherein, the chemical structural formulas of ET and Liq are as follows:
Figure BDA0003362724360000191
the material of the hole injection layer is a material known in the art for hole injection layers, and may be selected from, for example, 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 has a luminescence wavelength of 300nm to 1000nm, preferably 350nm to 900nm, more preferably 400nm to 800 nm.
The application also relates to an electronic device comprising said organic electronic device. The electronic device may be, but is not limited to, a display device, a lighting device, a light source, a sensor, etc.
The present application is specifically illustrated by the following examples, which are only some of the examples of the present application and are not limiting of the present application.
Example 1
The synthetic route for compound 1 of this example is as follows:
Figure BDA0003362724360000192
synthesis of intermediate 1-1:
2-Nitro-4-bromoiodobenzene (3.3 g,10 mmol), pinacol o-hydroxyphenylborate (2.2 g,10 mmol) were dissolved in a mixed solvent of 1, 4-dioxane and water (100 ml/10 ml), and Pd (PPh) was added 3 ) 4 (0.12 g,0.1 mmol) and potassium carbonate (5.5 g,40 mmol). Stirring is carried out for 12h at 100℃under nitrogen. After cooling, most of the solvent was removed by rotary evaporation, then the solution was extracted and washed with water, and the organic phase was subjected to column chromatography (eluent PE) and was recrystallized to give intermediate 1-1, yield: 83%. MS (ASAP) = 293.0.
Synthesis of intermediate 1-2:
in a 250ml two-necked flask were placed intermediate 1-1 (2.9 g,10 mmol), pd (OAc) 2 (0.22 g,1.0 mmol), 3-nitropyridine (0.12 g,1.0 mmol) and tert-butyl peroxybenzoate (3.9 g,20 mmol), and 100mL of hexafluorobenzene and 1, 3-dimethyl were added2-imidazolidinone 10mL. The reaction mixture was reacted at 100℃for 12 hours. After cooling, the solvent is removed by rotary evaporation, the mixture is extracted and washed with water, and the organic phase is taken over MgSO 4 Dried, filtered, and concentrated in vacuo. The organic phase was chromatographed (eluent PE: dcm=5:1) to give a pale yellow solid, intermediate 1-2, 34% yield. MS (ASAP) = 291.0.
Synthesis of intermediate 1-3:
in a 100ml two-necked flask, intermediate 1-2 (5.8 g,20 mmol) was placed, 30ml of dichlorobenzene was added until complete dissolution, triphenylphosphine (15.7 g,60 mmol) was added, and the mixture was stirred under nitrogen at 180℃for 12 hours. After cooling, the solvent was distilled off under reduced pressure, then dichloromethane was added, and the separated liquid was washed with water, and the organic phase was subjected to column chromatography (eluent: PE) and was recrystallized to obtain intermediate 1-3 in 55% yield. MS (ASAP) =259.0.
Synthesis of intermediates 1-4:
intermediate 1-3 (10 g,38.6 mmol), iodobenzene (20.4 g,100 mmol), pd was weighed out 2 (dba) 3 (2.9g，3.2mmol)，t-Bu 3 P (0.78 g,3.9 mmol), sodium t-butoxide (15.5 g,162 mmol) in a 500mL three-necked flask was reacted at 80℃for 12 hours with 200mL of toluene replaced with nitrogen. Spin-drying, washing with water, and column chromatography (eluting with PE) to obtain white solid (intermediate 1-4). The yield of intermediate 1-4 was 80%. MS (ASAP) = 335.0.
Synthesis of intermediates 1-5:
weigh intermediates 1-4 (5 g,15 mmol), (Bpin) 2 (4.6g，18mmol)，AcOK(7.4g，75mmol)，Pd(dppf)Cl 2 (0.74 g,1.0 mmol) in a 250mL three-necked flask, 100mL of 1, 4-dioxane was added, nitrogen was replaced, and the reaction was carried out at 100℃for 12 hours. Spin-drying, washing with water, and column chromatography (eluent: PE: dcm=3:1) to give colorless oil, intermediate 1-5. The yield of intermediate 1-5 was 93%. MS (ASAP) = 383.2.
Synthesis of Compound 1:
intermediate 1-5 (3.8 g,10 mmol), 9-bromo-10- (1-naphthyl) anthracene (5.4 g,14 mmol) were dissolved in a mixed solvent of 1, 4-dioxane and water (100 ml/10 ml), and Pd (PPh) was added 3 ) 4 (0.81 g,0.7 mmol) and potassium carbonate (5.5 g,40 mmol). Under nitrogen atmosphereStirring for 12h at 100 ℃. After cooling, most of the solvent was removed by rotary evaporation, then the separated liquid was extracted and washed with water, and the organic phase was subjected to column chromatography (eluent: PE) and was recrystallized to give compound 1, yield: 63%. MS (ASAP) = 559.2.
Example 2
The synthetic route for compound 2 of this example is as follows:
Figure BDA0003362724360000201
synthesis of intermediate 2-1:
2-nitroiodobenzene (2.5 g,10 mmol), pinacol o-hydroxyphenylborate (2.2 g,10 mmol) were dissolved in a mixed solvent of 1, 4-dioxane and water (100/10 ml), and Pd (PPh) was added 3 ) 4 (0.12 g,0.1 mmol) and potassium carbonate (5.5 g,40 mmol). Stirring is carried out for 12h at 100℃under nitrogen. After cooling, most of the solvent was removed by rotary evaporation, then the solution was extracted and washed with water, and the organic phase was subjected to column chromatography (eluent PE) and was recrystallized to give intermediate 2-1, yield: 76%. MS (ASAP) =215.1.
Synthesis of intermediate 2-2:
in a 250ml two-necked flask was placed intermediate 2-1 (2.2 g,10 mmol), pd (OAc) 2 (0.22 g,1.0 mmol), 3-nitropyridine (0.12 g,1.0 mmol) and tert-butyl peroxybenzoate (3.9 g,20 mmol), and 100mL of hexafluorobenzene and 10mL of 1, 3-dimethyl-2-imidazolidinone were added. The reaction mixture was reacted at 100℃for 12 hours. After cooling, the solvent is removed by rotary evaporation, the mixture is extracted and washed with water, and the organic phase is taken over MgSO 4 Drying, filtering, and concentrating the filtrate in vacuum. The organic phase was chromatographed on a column (eluent PE: dcm=5:1) to give a pale yellow solid, intermediate 2-2, in 37% yield. MS (ASAP) = 213.0.
Synthesis of intermediate 2-3:
in a 100ml two-necked flask, intermediate 2-2 (6.4 g,30 mmol) was added, 30ml dichlorobenzene was added until it was completely dissolved, triphenylphosphine (26.2 g,100 mmol) was added, and the mixture was stirred under nitrogen at 180℃for 12 hours. After cooling, the solvent was distilled off under reduced pressure, then dichloromethane was added, and the separated liquid was washed with water, and the organic phase was subjected to column chromatography (eluent: PE) and was recrystallized to give intermediate 2-3, yield: 58%. MS (ASAP) = 181.1.
Synthesis of intermediate 2-4:
intermediate 2-3 (9.1 g,50 mmol), p-bromoiodobenzene (28 g,100 mmol), pd was weighed out 2 (dba) 3 (2.9g，3.2mmol)，t-Bu 3 P (0.78 g,3.9 mmol), sodium t-butoxide (15.5 g,162 mmol) in a 500mL three-necked flask was reacted at 80℃for 12 hours with 200mL of toluene replaced with nitrogen. Spin-drying, washing with water, and column chromatography (eluting with PE) to obtain white solid (intermediate 2-4) with a yield of 48%. MS (ASAP) = 335.0.
Synthesis of intermediate 2-5:
weigh intermediate 2-4 (10 g,30 mmol), (Bpin) 2 (9.2g，36mmol)，AcOK(15g，150mmol)，Pd(dppf)Cl 2 (1.5 g,2.0 mmol) in a 250mL three-necked flask, 100mL of 1, 4-dioxane was added, nitrogen was replaced, and the reaction was carried out at 100℃for 12 hours. Spin-drying, washing with water, and column chromatography (eluent: PE: dcm=3:1) to obtain colorless oily substance, i.e. intermediate 2-5, yield 82%. MS (ASAP) = 383.2.
Synthesis of Compound 2:
intermediate 2-5 (7.7 g,20 mmol), 9-bromo-10- (phenyl) anthracene (6.7 g,20 mmol) were dissolved in a mixed solvent of 1, 4-dioxane and water (100 ml/10 ml), and Pd (PPh) was added 3 ) 4 (1.2 g,1 mmol) and potassium carbonate (8.3 g,60 mmol). Stirring is carried out for 12h at 100℃under nitrogen. After cooling, most of the solvent was removed by rotary evaporation, then the separated liquid was extracted and washed with water, and the organic phase was subjected to column chromatography (eluent PE) and recrystallized to give compound 2, yield: 67%. MS (ASAP) =509.2.
Example 3
The synthetic route for compound 3 of this example is as follows:
Figure BDA0003362724360000211
Synthesis of intermediate 3-1:
9-bromo-10- (1-phenyl) anthracene (10 g,30 mmol), 4-bromo-1-phenylboronic acid (6.0 g,30 mmol) was dissolved in 1, 4-dioxaneMixed solvent with water (200 ml/20 ml) and Pd (PPh) was added 3 ) 4 (3.5 g,3 mmol) and potassium carbonate (21 g,150 mmol). Stirring is carried out for 12h at 100℃under nitrogen. After cooling, most of the solvent is removed by rotary evaporation, then the solvent is extracted, water is used for washing and separating liquid, the organic phase column chromatography is carried out, and the intermediate 3-1 is obtained by recrystallization, and the yield is: 89%. MS (ASAP) =408.1.
Synthesis of Compound 3:
intermediate 3-1 (6.1 g,15 mmol), intermediate 1-5 (7.7 g,20 mmol) were dissolved in a mixed solvent of 1, 4-dioxane and water (100 ml/10 ml), and Pd (PPh) was added 3 ) 4 (0.87 g,0.75 mmol) and potassium carbonate (6.2 g,45 mmol). Stirring is carried out for 12h at 100℃under nitrogen. After cooling, most of the solvent is removed by rotary evaporation, then the solvent is extracted, water is used for washing and separating liquid, the organic phase column chromatography is carried out, and the compound 3 is obtained by recrystallization, the yield is: 61%. MS (ASAP) = 585.2.
Example 4
The synthetic route for compound 4 of this example is as follows:
Figure BDA0003362724360000212
synthesis of intermediate 4-1:
9-bromo-10- (2-naphthyl) anthracene (3.8 g,10 mmol), 4-bromo-2, 3,5, 6-tetramethyl-1-phenylboronic acid (3.1 g,12 mmol) were dissolved in a mixed solvent of 1, 4-dioxane and water (100 ml/10 ml), and Pd (PPh) was added 3 ) 4 (1.15 g,1 mmol) and potassium carbonate (4.1 g,30 mmol). Stirring is carried out for 12h at 100℃under nitrogen. After cooling, most of the solvent is removed by rotary evaporation, then the solvent is extracted, water is used for washing and separating liquid, the organic phase column chromatography is carried out, and the intermediate 4-1 is obtained by recrystallization, and the yield is: 42%. MS (ASAP) =514.1.
Synthesis of Compound 4:
intermediate 2-3 (9.1 g,50 mmol), intermediate 4-1 (25.7 g,50 mmol), pd were weighed out 2 (dba) 3 (2.9g，3.2mmol)，t-Bu 3 P (0.78 g,3.9 mmol), sodium t-butoxide (15.5 g,162 mmol) in a 500mL three-necked flask was reacted at 80℃for 12 hours with 200mL of toluene replaced with nitrogen. Spin-drying, washing with water,column chromatography (eluent PE) gave a white solid in 88% yield. MS (ASAP) = 615.3.
Example 5
The synthetic route for the compounds of this example is as follows:
Figure BDA0003362724360000221
synthesis of intermediate 5-1:
9, 10-dibromoanthracene (6.8 g,20 mmol), deuterated phenylboronic acid (3.0 g,24 mmol) were dissolved in a mixed solvent of 1, 4-dioxane and water (100 ml/10 ml), and Pd (PPh) was added 3 ) 4 (2.3 g,2 mmol) and potassium carbonate (8.3 g,60 mmol). Stirring is carried out for 12h at 100℃under nitrogen. After cooling, most of the solvent is removed by rotary evaporation, then the solvent is extracted, water is used for washing and separating liquid, the organic phase column chromatography is carried out, and the intermediate 5-1 is obtained by recrystallization, and the yield is: 73%. MS (ASAP) =337.1.
Synthesis of Compound 5:
intermediate 5-1 (3.4 g,10 mmol), intermediate 2-5 (3.8 g,10 mmol) were dissolved in a mixed solvent of 1, 4-dioxane and water (100 ml/10 ml), and Pd (PPh) was added 3 ) 4 (1.15 g,1 mmol) and potassium carbonate (4.1 g,30 mmol). Stirring is carried out for 12h at 100℃under nitrogen. After cooling, most of the solvent is removed by rotary evaporation, then the solvent is extracted, water is used for washing and separating liquid, the organic phase column chromatography is carried out, and the compound 5 is obtained by recrystallization, the yield is: 73%. MS (ASAP) =514.2.
Example 6
The synthetic route for compound 6 of this example is as follows:
Figure BDA0003362724360000222
synthesis of intermediate 6-1:
9, 10-dibromoanthracene (3.4 g,10 mmol), deuterated 1-naphthalene boric acid (1.8 g,10 mmol) were dissolved in a mixed solvent of 1, 4-dioxane and water (100 ml/10 ml), and Pd (PPh) was added 3 ) 4 (1.15 g,1 mmol) and potassium carbonate (8.3 g,60 mmol). Under nitrogen atmosphereStirring for 12h at 100 ℃. After cooling, most of the solvent is removed by rotary evaporation, then the solvent is extracted, water is used for washing and separating liquid, the organic phase column chromatography is carried out, and the intermediate 6-1 is obtained by recrystallization, and the yield is: 76%. MS (ASAP) = 389.1.
Synthesis of Compound 6:
intermediate 6-1 (3.9 g,10 mmol), intermediate 1-5 (4.6 g,12 mmol) were dissolved in a mixed solvent of 1, 4-dioxane and water (100 ml/10 ml), and Pd (PPh) was added 3 ) 4 (1.15 g,1 mmol) and potassium carbonate (4.1 g,30 mmol). Stirring is carried out for 12h at 100℃under nitrogen. After cooling, most of the solvent is removed by rotary evaporation, then the solvent is extracted, water is used for washing and separating liquid, the organic phase column chromatography is carried out, and the compound 6 is obtained by recrystallization, the yield is: 53%. MS (ASAP) = 566.2.
Example 7
The synthetic route for compound 7 of this example is as follows:
Figure BDA0003362724360000223
synthesis of intermediate 7-1:
9-bromo-10- (2-naphthyl) anthracene (3.8 g,10 mmol), 2-bromo-pyridine-5-boronic acid (2.0 g,10 mmol) were dissolved in a mixed solvent of 1, 4-dioxane and water (100 ml/10 ml), and Pd (PPh) was added 3 ) 4 (1.15 g,1 mmol) and potassium carbonate (4.1 g,30 mmol). Stirring is carried out for 12h at 100℃under nitrogen. After cooling, most of the solvent is removed by rotary evaporation, then the solvent is extracted, water is used for washing and separating liquid, the organic phase column chromatography is carried out, and the intermediate 7-1 is obtained by recrystallization, and the yield is: 81%. MS (ASAP) = 459.1.
Synthesis of organic compound 7:
weigh intermediate 2-3 (5.4 g,30 mmol), intermediate 7-1 (13.8 g,30 mmol), pd 2 (dba) 3 (2.9g，3.2mmol)，t-Bu 3 P (0.78 g,3.9 mmol), sodium t-butoxide (15.5 g,162 mmol) in a 500mL three-necked flask was reacted at 80℃for 12 hours with 200mL of toluene replaced with nitrogen. Spin-drying, washing with water, and column chromatography (eluting with PE) to obtain white solid with yield of 83%. MS (ASAP) =560.2.
Example 8
The synthetic route for compound 8 of this example is as follows:
Figure BDA0003362724360000231
synthesis of intermediate 8-1:
9, 10-dibromoanthracene (3.4 g,10 mmol), 3, 5-diphenyl-phenylboronic acid (2.8 g,10 mmol) were dissolved in a mixed solvent of 1, 4-dioxane and water (100 ml/10 ml), and Pd (PPh) was added 3 ) 4 (1.15 g,1 mmol) and potassium carbonate (8.3 g,60 mmol). Stirring is carried out for 12h at 100℃under nitrogen. After cooling, most of the solvent is removed by rotary evaporation, then the solvent is extracted, water is used for washing and separating liquid, the organic phase column chromatography is carried out, and the intermediate 8-1 is obtained by recrystallization, and the yield is: 63%. MS (ASAP) = 484.1.
Synthesis of Compound 8:
intermediate 8-1 (4.9 g,10 mmol), intermediate 1-5 (3.8 g,10 mmol) were dissolved in a mixed solvent of 1, 4-dioxane and water (100 ml/10 ml), and Pd (PPh) was added 3 ) 4 (1.15 g,1 mmol) and potassium carbonate (4.1 g,30 mmol). Stirring is carried out for 12h at 100℃under nitrogen. After cooling, most of the solvent is removed by rotary evaporation, then the solvent is extracted, water is used for washing and separating liquid, the organic phase column chromatography is carried out, and the compound 8 is obtained by recrystallization, the yield is: 55%. MS (ASAP) = 661.2.
Example 9
The synthetic route for compound 9 of this example is as follows:
Figure BDA0003362724360000232
synthesis of intermediate 9-1:
intermediate 9, 10-dibromoanthracene (6.7 g,20 mmol), dibenzo [ b, d ]Furan-2-boronic acid (4.3 g,20 mmol) was dissolved in a mixed solvent of 1, 4-dioxane and water (100 ml/10 ml), and Pd (PPh) was added 3 ) 4 (1.2 g,1 mmol) and potassium carbonate (14 g,100 mmol). Stirring is carried out for 12h at 100℃under nitrogen. After cooling, the solvent is removed by rotary evaporation, and then the mixture is extracted, washed with water, separated, and subjected to column chromatography and recrystalizationThe crystals give intermediate 9-1, yield: 55%. MS (ASAP) = 422.0.
Synthesis of compound 9:
intermediate 9-1 (4.2 g,10 mmol), intermediate 1-5 (3.8 g,10 mmol) were dissolved in a mixed solvent of 1, 4-dioxane and water (100 ml/10 ml), and Pd (PPh) was added 3 ) 4 (1.15 g,1 mmol) and potassium carbonate (4.1 g,30 mmol). Stirring is carried out for 12h at 100℃under nitrogen. After cooling, most of the solvent is removed by rotary evaporation, then the solvent is extracted, water is used for washing and separating liquid, the organic phase column chromatography is carried out, and the compound 9 is obtained by recrystallization, the yield is: 74%. MS (ASAP) = 599.2.
Example 10
The synthetic route for the compounds of this example is as follows:
Figure BDA0003362724360000241
synthesis of intermediate 10-1:
9, 10-dibromoanthracene (3.4 g,10 mmol), fluoranthene-3-boric acid (2.5 g,10 mmol) were dissolved in a mixed solvent of 1, 4-dioxane and water (100 ml/10 ml), and Pd (PPh) was added 3 ) 4 (1.15 g,1 mmol) and potassium carbonate (8.3 g,60 mmol). Stirring is carried out for 12h at 100℃under nitrogen. After cooling, most of the solvent is removed by rotary evaporation, then the solvent is extracted, water is used for washing and separating liquid, the organic phase column chromatography is carried out, and the intermediate 10-1 is obtained by recrystallization, and the yield is: 64%. MS (ASAP) = 456.1.
Synthesis of Compound 10:
intermediate 10-1 (4.6 g,10 mmol), intermediate 10-11-5 (3.8 g,10 mmol) were dissolved in a mixed solvent of 1, 4-dioxane and water (100 ml/10 ml), and Pd (PPh) was added 3 ) 4 (1.15 g,1 mmol) and potassium carbonate (4.1 g,30 mmol). Stirring is carried out for 12h at 100℃under nitrogen. After cooling, most of the solvent was removed by rotary evaporation, then the mixture was extracted and separated by water, and the organic phase was subjected to column chromatography and recrystallization to give compound 10 in the yield: 48%. MS (ASAP) = 633.2.
Example 11
The synthetic route for compound 11 of this example is as follows:
Figure BDA0003362724360000242
synthesis of intermediate 11-1:
9, 10-dibromoanthracene (3.4 g,10 mmol), 1-pyrene boric acid (2.5 g,10 mmol) were dissolved in a mixed solvent of 1, 4-dioxane and water (100 ml/10 ml), and Pd (PPh) was added 3 ) 4 (1.15 g,1 mmol) and potassium carbonate (8.3 g,60 mmol). Stirring is carried out for 12h at 100℃under nitrogen. After cooling, most of the solvent is removed by rotary evaporation, then the solvent is extracted, water is used for washing and separating liquid, the organic phase column chromatography is carried out, and the intermediate 11-1 is obtained by recrystallization, and the yield is: 73%. MS (ASAP) = 456.1.
Synthesis of Compound 11:
intermediate 11-1 (6.8 g,15 mmol), intermediate 2-5 (7.7 g,20 mmol) were dissolved in a mixed solvent of 1, 4-dioxane and water (100 ml/10 ml), and Pd (PPh) was added 3 ) 4 (1.7 g,1.5 mmol) and potassium carbonate (6.2 g,45 mmol). Stirring is carried out for 12h at 100℃under nitrogen. After cooling, most of the solvent was removed by rotary evaporation, then the mixture was extracted and separated by water, and the organic phase was subjected to column chromatography and recrystallization to give compound 11 in the yield: 59%. MS (ASAP) = 633.2.
Example 12
The synthetic route for compound 12 of this example is as follows:
Figure BDA0003362724360000243
synthesis of intermediate 12-1:
9-bromo-10- (4-tert-butylphenyl) anthracene (3.9 g,10 mmol), 6-bromo-2-naphthalene boronic acid (2.5 g,10 mmol) were dissolved in a mixed solvent of 1, 4-dioxane and water (100 ml/10 ml), and Pd (PPh) was added 3 ) 4 (1.15 g,1 mmol) and potassium carbonate (4.1 g,30 mmol). Stirring is carried out for 12h at 100℃under nitrogen. After cooling, most of the solvent is removed by rotary evaporation, then the solvent is extracted, water is used for washing and separating liquid, the organic phase column chromatography is carried out, and the intermediate 12-1 is obtained by recrystallization, and the yield is: 71%. MS (ASAP) =514.1.
Synthesis of organic compound 12:
intermediate 2-3 (3.6 g,20 mmol), intermediate 12-1 (10.3 g,20 mmol), pd were weighed out 2 (dba) 3 (1.8g，2.0mmol)，t-Bu 3 P (0.51 g,2.5 mmol), sodium t-butoxide (9.6 g,100 mmol) in a 500mL three-necked flask was reacted at 80℃for 12 hours with 200mL of toluene replaced with nitrogen. Spin-drying, washing with water, and column chromatography (eluting with PE) to obtain white solid with yield of 83%. MS (ASAP) =560.2.
Example 13
The synthetic route for compound 13 of this example is as follows:
Figure BDA0003362724360000251
synthesis of intermediate 13-1:
intermediate 1-3 (13 g,50 mmol), 2-iododibenzofuran (29.4 g,100 mmol), pd was weighed out 2 (dba) 3 (4.6g，5mmol)，t-Bu 3 P (1.2 g,6.0 mmol), sodium t-butoxide (9.6 g,100 mmol) in a 500mL three-necked flask was reacted at 80℃for 12 hours with 200mL of toluene replaced with nitrogen. Spin-drying, washing with water, and column chromatography (eluting with PE) to obtain white solid with yield of 78%. MS (ASAP) =425.0.
Synthesis of intermediate 13-2:
intermediate 13-1 (8.5 g,20 mmol), (Bpin) was weighed out 2 (6.4g，25mmol)，AcOK(9.8g，100mmol)，Pd(dppf)Cl 2 (1.5 g,2.0 mmol) in a 250mL three-necked flask, 100mL of 1, 4-dioxane was added, nitrogen was replaced, and the reaction was carried out at 100℃for 12 hours. Spin-drying, water washing, column chromatography (eluent PE: dcm=3:1) gave a colorless oil in 92% yield. MS (ASAP) = 473.2.
Synthesis of Compound 13:
intermediate 13-2 (9.5 g,20 mmol), intermediate 6-1 (7.8 g,20 mmol) was dissolved in a mixed solvent of 1, 4-dioxane and water (100 ml/10 ml), and Pd (PPh) was added 3 ) 4 (1.2 g,1 mmol) and potassium carbonate (8.3 g,60 mmol). Stirring is carried out for 12h at 100℃under nitrogen. After cooling, the solvent is removed by rotary evaporation, and then the mixture is extracted and washed with waterSeparating, subjecting the organic phase to column chromatography (eluting solvent is PE) and recrystallizing to obtain a compound 13, wherein the yield is as follows: 69%. MS (ASAP) =656.3.
Example 14
The synthetic route for compound 14 of this example is as follows:
Figure BDA0003362724360000252
synthesis of intermediate 14-1:
intermediate 1-3 (13 g,50 mmol), 2-iodonaphthalene (25.4 g,100 mmol), pd was weighed out 2 (dba) 3 (4.6g，5mmol)，t-Bu 3 P (1.2 g,6.0 mmol), sodium t-butoxide (9.6 g,100 mmol) in a 500mL three-necked flask was reacted at 80℃for 12 hours with 200mL of toluene replaced with nitrogen. Spin-drying, washing with water, and column chromatography (eluting with PE) to obtain white solid with 73% yield. MS (ASAP) =385.0.
Synthesis of intermediate 14-2:
intermediate 14-1 (7.7 g,20 mmol), (Bpin) was weighed out 2 (6.4g，25mmol)，AcOK(9.8g，100mmol)，Pd(dppf)Cl 2 (1.5 g,2.0 mmol) in a 250mL three-necked flask, 100mL of 1, 4-dioxane was added, nitrogen was replaced, and the reaction was carried out at 100℃for 12 hours. Spin-drying, water washing, column chromatography (eluent PE: dcm=3:1) gave a colorless oil, yield 87%. MS (ASAP) = 433.2.
Synthesis of intermediate 14-3:
9, 10-dibromoanthracene (6.8 g,20 mmol), 9-dimethylfluorene-2-boronic acid (4.8 g,20 mmol) were dissolved in a mixed solvent of 1, 4-dioxane and water (100 ml/10 ml), and Pd (PPh) was added 3 ) 4 (2.3 g,2 mmol) and potassium carbonate (14 g,100 mmol). Stirring is carried out for 12h at 100℃under nitrogen. After cooling, most of the solvent is removed by rotary evaporation, then the solvent is extracted, water is used for washing and separating liquid, the organic phase column chromatography is carried out, and the intermediate 14-3 is obtained by recrystallization, and the yield is: 65%. MS (ASAP) = 448.1
Synthesis of Compound 14:
intermediate 14-2 (8.7 g,20 mmol), intermediate 14-3 (9.0 g,20 mmol) were dissolved in a mixed solvent of 1, 4-dioxane and water (100 ml/10 ml), andpd (PPh) was added 3 ) 4 (1.2 g,1.0 mmol) and potassium carbonate (14 g,100 mmol). Stirring is carried out for 12h at 100℃under nitrogen. After cooling, most of the solvent was removed by rotary evaporation, then the mixture was extracted and separated by water washing, and the organic phase was subjected to column chromatography and recrystallization to give compound 14, yield: 55%. MS (ASAP) = 675.3.
Example 15
The synthetic route for compound 15 of this example is as follows:
Figure BDA0003362724360000261
synthesis of intermediate 15-1:
2-Nitro-4-bromoiodobenzene (3.3 g,10 mmol), 2-hydroxy-4-bromophenylboronic acid pinacol ester (3.0 g,10 mmol) were dissolved in a mixed solvent of 1, 4-dioxane and water (100 ml/10 ml), and Pd (PPh) was added 3 ) 4 (0.12 g,0.1 mmol) and potassium carbonate (5.5 g,40 mmol). Stirring is carried out for 12h at 100℃under nitrogen. After cooling, most of the solvent was removed by rotary evaporation, then the solution was extracted and washed with water, and the organic phase was subjected to column chromatography (eluent PE) and was recrystallized to give intermediate 15-1, yield: 78%. MS (ASAP) = 372.9.
Synthesis of intermediate 15-2: :
in a 250ml two-necked flask was added intermediate 15-1 (3.7 g,10 mmol), pd (OAc) 2 (0.22 g,1.0 mmol), 3-nitropyridine (0.12 g,1.0 mmol) and tert-butyl peroxybenzoate (3.9 g,20 mmol), and 100mL and 10mL of 1, 3-dimethyl-2-imidazolidinone were added to hexafluorobenzene. The reaction mixture was reacted at 100℃for 12 hours. After cooling, most of the solvent was removed by rotary evaporation, then the fractions were extracted and washed with water, dried (MgSO 4), filtered, and concentrated in vacuo. The organic phase was chromatographed (eluent PE: dcm=5:1) to give a pale yellow solid in 37% yield. MS (ASAP) = 370.9.
Synthesis of intermediate 15-3:
in a 100ml two-necked flask, intermediate 15-2 (7.4 g,20 mmol) was added, 30ml dichlorobenzene was added until it was completely dissolved, triphenylphosphine (15.7 g,60 mmol) was added, and the mixture was stirred under nitrogen at 180℃for 12 hours. After cooling, the solvent was distilled off under pressure, then dichloromethane was added, and the separated liquid was washed with water, and the organic phase was subjected to column chromatography (eluent: PE) and was recrystallized to give intermediate 15-3, yield: 58%. MS (ASAP) =338.9.
Synthesis of intermediate 15-4:
intermediate 15-3 (10 g,38.6 mmol), methyl iodide (11.4 g,80 mmol), K was weighed out 2 CO 3 (14 g,100 mmol) in a 500mL three-necked flask, 200mL of tetrahydrofuran was added thereto, and the mixture was reacted at 70℃for 12 hours while substituting nitrogen. Spin-drying, washing with water, and column chromatography (eluting with PE) to obtain white solid with 92% yield. MS (ASAP) = 352.9.
Synthesis of intermediate 15-5:
intermediate 15-4 (3.5 g,10 mmol), 10- (1-naphthyl) -9-anthraceneboronic acid (3.5 g,10 mmol) were dissolved in a mixed solvent of 1, 4-dioxane and water (100 ml/10 ml), and Pd (PPh) was added 3 ) 4 (1.2 g,1.0 mmol) and potassium carbonate (6.9 g,50 mmol). Stirring is carried out for 12h at 100℃under nitrogen. After cooling, most of the solvent was removed by rotary evaporation, then the solution was extracted and washed with water, and the organic phase was subjected to column chromatography (eluent PE) and was recrystallized to give intermediate 15-5, yield: 53%. MS (ASAP) = 575.1.
Synthesis of Compound 15:
intermediate 15-5 (5.8 g,10 mmol), 1-naphthalene boronic acid (3.4 g,20 mmol) were dissolved in a mixed solvent of 1, 4-dioxane and water (100 ml/10 ml), and Pd (PPh) was added 3 ) 4 (0.81 g,0.7 mmol) and potassium carbonate (5.5 g,40 mmol). Stirring is carried out for 12h at 100℃under nitrogen. After cooling, most of the solvent was removed by rotary evaporation, then the separated liquid was extracted and washed with water, and the organic phase was subjected to column chromatography (eluent: PE) and recrystallized to give compound 15, yield: 92%. MS (ASAP) = 623.2.
Comparative example
The organic compound of this comparative example is BH-Ref, which has the following chemical structural formula:
Figure BDA0003362724360000271
the process of preparing an OLED device including the above-described compounds is described in detail below by way of specific examples. The OLED device has the structure that: ITO/HIL/HTL/EML/ETL/cathode, an OLED device is schematically shown in fig. 1, where 101 is the substrate, 102 is the anode, 103 is the Hole Injection Layer (HIL), 104 is the Hole Transport Layer (HTL), 105 is the light emitting layer, 106 is the Electron Transport Layer (ETL), and 107 is the cathode.
Liq, ET and BD-1, which may be related to the OLED preparation process, have the following structural formulas:
Figure BDA0003362724360000272
the OLED-1 was prepared as follows:
a. cleaning an ITO (indium tin oxide) conductive glass substrate: cleaning with various solvents (such as chloroform, acetone or isopropanol, or both), and then performing ultraviolet ozone treatment.
b. HIL (hole injection layer, 40 nm): 40nm PEDOT (polyethylene dioxythiophenes, clevelos) TM AI 4083) was spin coated as HIL in an ultra clean room and treated on a hot plate at 180 ℃ for 10 minutes.
c. HTL (hole transport layer, 20 nm): PVK at 20nm (Sigma Aldrich, average Mn 25,000-50,000) was spin coated in a nitrogen glove box using PVK added to toluene solvent at a solution solubility of 5mg/ml followed by treatment on a hot plate at 180℃for 60 minutes.
d. EML (organic light emitting layer, 40 nm): the EML was prepared by spin coating in a nitrogen glove box using solutions of methyl benzoate solutions of different hosts (weight ratio of host to guest 95:5), solution solubility 15mg/ml, followed by treatment on a hot plate at 140℃for 10 minutes, the host using compound 1 of example 1, the guest material selected from BD-1.
e. An electron transport layer and a cathode: the heat-treated substrate was transferred to a vacuum chamber, then ET and Liq were placed in different evaporation units and co-deposited in a high vacuum (1 x 10-6 mbar) at a rate of 50 wt% respectively, forming an electron transport layer of 20nm on the light emitting layer, followed by deposition of an Al cathode of 100nm thickness.
f. 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-OLED-15 and OLED-Ref are the same as OLED-1, except that compound 1 in example OLED-1 is replaced with the corresponding compound in Table I as the host material.
The current-voltage (J-V) characteristics of each OLED device were characterized by a characterization device, while recording the color efficiency (CE@1knits) and lifetime (LT90@1knits), the results of which are given in Table I below.
Table one:
Figure BDA0003362724360000273
Figure BDA0003362724360000281
from Table one can see: the organic compounds 1 to 15 of examples 1 to 15 were used as the host materials in the light-emitting layers to prepare OELD devices having better color coordinates and longer lifetimes than blue OELD devices prepared using the organic compounds of the comparative examples as the host materials in the light-emitting layers.
In addition, the blue light OELD devices prepared by using the compounds 1-15 of examples 1-15 as host materials in the light-emitting layer have light-emitting efficiencies in the range of 5-8cd/A, and have more excellent light-emitting efficiencies, and the effects of the devices OLED-5, OLED-6 are superior to those of other devices. The devices OLED-5 and OLED-6 probably have certain promotion effect on luminescence due to deuterium contained in the main body material of the luminescent layer.
The anthracene organic compound containing the heterocyclic condensed rings has fluorescence emission at blue wavelength, can be used as a main material in a light-emitting layer of an organic electronic device, and the organic electronic device prepared by using the organic compound has better light-emitting efficiency and longer service life.
The organic compounds, mixtures, compositions and organic electronic devices provided in the examples of the present application are described in detail, and specific examples are used herein to illustrate the principles and embodiments of the present application, the description of the examples above being only for aiding in the understanding of the methods of the present application and the core ideas thereof; meanwhile, those skilled in the art will have variations in the specific embodiments and application scope in light of the ideas of the present application, and the present description should not be construed as limiting the present application in view of the above.

Claims (12)

1. An organic compound having a structure represented by the general formula (1):
Figure FDA0003362724350000011
wherein:
Ar 1 selected from structures represented by general formula (2):
Figure FDA0003362724350000012
Ar 2 selected from a substituted or unsubstituted aromatic group containing 6 to 60 ring atoms, or a substituted or unsubstituted heteroaromatic group containing 5 to 60 ring atoms, or a combination of these groups;
g is selected from a linear alkyl group having 1 to 20C atoms, or a branched alkyl group having 3 to 20C atoms, or a cyclic alkyl group having 3 to 20C atoms, 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 combination of such groups;
L 1 、L 2 Independently selected from a single bond, or a substituted or unsubstituted aromatic group containing 6 to 60 ring atoms, or a substituted or unsubstituted heteroaromatic group containing 5 to 60 ring atoms;
R 1 、R 2 and R is 3 Each occurrence is independently selected from-D, or a linear alkyl group having 1 to 20C atoms, a linear alkoxy group having 1 to 20C atoms, or a linear thioalkoxy group having 3 to 20C atomsBranched alkyl of C atoms, or branched alkoxy of 3 to 20C atoms, or branched thioalkoxy of 3 to 20C atoms, or cyclic alkyl of 3 to 20C atoms, or cyclic alkoxy of 3 to 20C atoms, or cyclic thioalkoxy of 3 to 20C atoms, or silyl, or keto of 1 to 20C atoms, or alkoxycarbonyl of 2 to 20C atoms, or aryloxycarbonyl of 7 to 20C atoms, cyano, carbamoyl, haloformyl, formyl, isocyano, thiocyanate, or isothiocyanate, hydroxy, nitro, substituted or unsubstituted amino, -CF 3 -Cl, -Br, -F, -I, 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 5 to 60 ring atoms, or a substituted or unsubstituted heteroaryloxy group having 5 to 60 ring atoms, or a combination of these groups;
m1 is 0, 1, 2, 3, 4, 5, 6, 7 or 8;
m2 is 0, 1, 2 or 3;
m3 is 0, 1, 2 or 3.
2. The organic compound according to claim 1, wherein the organic compound is selected from the structures represented by the general formula (3-1) or the general formula (3-2):
Figure FDA0003362724350000013
3. the organic compound according to claim 1 or 2, wherein R 1 、R 2 And R is 3 Each occurrence is independently selected from the group consisting of-D, 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, n-,1-methylhexyl, 2-ethylhexyl, 2-butylhexyl, cyclohexyl, adamantyl, phenyl, biphenyl, terphenyl, naphthyl, anthryl, phenanthryl, triazinyl, pyridyl, pyrimidinyl, imidazolyl, furanyl, thienyl, benzofuranyl, benzothienyl, indolyl, carbazolyl, dibenzothienyl, dibenzofuranyl, phenyl-substituted carbazolyl, fluorenyl substituted with an alkyl group having 1 to 6C atoms, phenyl substituted with an alkyl group having 1 to 6C atoms, naphthyl substituted with phenyl, phenyl substituted with one or more D, or naphthyl substituted with one or more D.
4. The organic compound according to claim 1, wherein Ar 2 And/or G is selected from any of the structures shown below:
Figure FDA0003362724350000021
wherein:
x is independently selected from CR for each occurrence 5 Or N;
y is selected from NR 6 、CR 7 R 8 、SiR 7 R 8 O, S, S =o or SO 2 ；
R 5 、R 6 、R 7 、R 8 Each occurrence is independently selected from the group consisting of-H, -D, or a linear alkyl group having 1 to 20C atoms, a linear alkoxy group having 1 to 20C atoms, or a linear thioalkoxy group having 1 to 20C atoms, or a branched alkyl group having 3 to 20C atoms, or a branched alkoxy group having 3 to 20C atoms, or a branched thioalkoxy group having 3 to 20C atoms, or a cyclic alkyl group having 3 to 20C atoms, or a cyclic alkoxy group having 3 to 20C atoms, or a 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, carbamoyl, haloformyl, methylmethylAcyl, isocyano, thiocyanate, or isothiocyanate groups, hydroxy, nitro, amino, -CF 3 -Cl, -Br, -F, -I, 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 5 to 60 ring atoms, or a substituted or unsubstituted heteroaryloxy group having 5 to 60 ring atoms, or a combination of these groups;
R 7 And R is 8 With or without each other.
5. The organic compound according to claim 4, wherein the structure of the organic compound is selected from the structures represented by any one of the general formulae (4-1) to (4-10):
Figure FDA0003362724350000022
Figure FDA0003362724350000031
6. an organic compound according to claim 2, 4 or 5, wherein G is selected from any of the structures shown below:
Figure FDA0003362724350000032
wherein, represents the site of attachment.
7. The organic compound according to claim 6, wherein: r is R 5 Each occurrence is independently selected from: -H, -D, a linear alkyl group having 1 to 8C atoms, a branched alkyl group having 3 to 8C atoms, a cyclic alkyl group having 3 to 8C atoms, a substituted or unsubstituted aromatic group having 6 to 10 ring atoms, a substituted or unsubstitutedSubstituted heteroaromatic groups having 5 to 10 ring atoms or combinations of these groups;
wherein the substituted substituent is selected from-D, a straight chain alkyl group having 1 to 4C atoms, a branched alkyl group having 3 to 4C atoms, or a phenyl group, or a pyridyl group.
8. The organic compound according to claim 1, wherein: the L is 1 、L 2 Independently selected from a single bond or a structure as shown in any one of the following:
Figure FDA0003362724350000033
wherein:
X 1 each occurrence is independently selected from CR 4 Or N;
R 4 each occurrence is independently selected from the group consisting of-H, -D, or a linear alkyl group having 1 to 20C atoms, a linear alkoxy group having 1 to 20C atoms, or a linear thioalkoxy group having 1 to 20C atoms, or a branched alkyl group having 3 to 20C atoms, or a branched alkoxy group having 3 to 20C atoms, or a branched thioalkoxy group having 3 to 20C atoms, or a cyclic alkyl group having 3 to 20C atoms, or a cyclic alkoxy group having 3 to 20C atoms, or a 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, carbamoyl, haloformyl, formyl, isocyano, isocyanate, thiocyanate, or isothiocyanate groups, hydroxyl, nitro, amine, -CF3, -Cl, -Br, -F, -I, or a substituted or unsubstituted aromatic group having 6 to 60 ring atoms, or a substituted or unsubstituted aromatic group having 5 to 60 ring atoms, or a substituted or a combination of 5 to 60 ring atoms, or a substituted or unsubstituted aromatic group having 5 to 60 ring atoms.
9. The organic compound of claim 1, wherein the organic compound is selected from any one of the following structures:
Figure FDA0003362724350000041
/>
Figure FDA0003362724350000051
/>
Figure FDA0003362724350000061
/>
Figure FDA0003362724350000071
/>
Figure FDA0003362724350000081
10. a mixture characterized by: the 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 injecting material, a hole transporting material, an electron injecting material, an electron blocking material, a hole blocking material, a light emitting material, a host material, a guest material, or an organic dye.
11. A composition characterized by: the 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 the organic compound according to any one of claims 1 to 9, or the mixture according to claim 10, or is prepared from the composition according to claim 11.
CN202111372224.1A 2021-11-18 2021-11-18 Organic compound, mixture, composition and organic electronic device comprising same Pending CN116143793A (en)

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