CN115677709A - Organic compounds, mixtures, compositions and organic electronic devices - Google Patents

Organic compounds, mixtures, compositions and organic electronic devices Download PDF

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CN115677709A
CN115677709A CN202211414584.8A CN202211414584A CN115677709A CN 115677709 A CN115677709 A CN 115677709A CN 202211414584 A CN202211414584 A CN 202211414584A CN 115677709 A CN115677709 A CN 115677709A
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夏泽铭
龙志飞
何锐锋
宋晶尧
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Shenzhen China Star Optoelectronics Semiconductor Display Technology Co Ltd
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Abstract

The application discloses an organic compound, a mixture, a composition and an organic electronic device, and belongs to the technical field of luminescent materials. An organic compound has a structure represented by general formula (1). The organic compound can enable the organic electronic device to have higher device luminous efficiency and longer device service life.

Description

Organic compound, mixture, composition and organic electronic device
Technical Field
The application relates to the technical field of luminescent materials, in particular to an organic compound, a mixture, a composition and an organic electronic device.
Background
Organic semiconductor materials are versatile in synthesis, relatively low in manufacturing cost, and excellent in optical and electrical properties. Organic Light-Emitting diodes (OLEDs) have the advantages of wide viewing angle, fast response time, low operating voltage, thin panel thickness, etc. in the application of optoelectronic devices (e.g., flat panel displays and lighting), and thus have a wide potential for development.
The organic electroluminescence phenomenon refers to a phenomenon of converting electric energy into light energy using an organic substance. An organic electroluminescent element utilizing an organic electroluminescent phenomenon generally has a structure including a positive electrode and a negative electrode and an organic layer therebetween. In order to improve the efficiency and lifetime of the organic electroluminescent element, the organic layer has a multi-layer structure, each layer containing a different organic substance. 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 the two electrodes, holes are injected from the positive electrode into the organic layer, electrons are injected from the negative electrode into the organic layer, excitons are formed when the injected holes and electrons meet, and light is emitted when the excitons transition back to the 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 light emitting efficiency of the organic electroluminescent device, various fluorescent and phosphorescent light emitting material systems have been developed, and the development of excellent blue light emitting materials, whether fluorescent materials or phosphorescent materials, is a great challenge, and in general, the organic light emitting diode using the currently used blue light emitting fluorescent materials has higher reliability. However, most of the blue fluorescent materials have too wide emission spectrum, poor color purity, and are not suitable for high-end display, and the synthesis of these fluorescent materials is also complicated, which is not suitable for large-scale mass production, and the stability of the OLED of these blue fluorescent materials needs to be further improved. 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, thereby improving the display effect.
A light emitting layer of the existing blue light organic electroluminescent element adopts a host-guest doped structure, most blue light host materials adopt anthracene-based condensed ring derivatives, but the stability of the material of the light emitting layer is poor, so that the service life of the device is short. Meanwhile, these materials are difficult to realize deep blue light emission and to satisfy the demand for full color display.
Therefore, a material is needed to improve the performance of the organic electroluminescent device.
Disclosure of Invention
The embodiment of the application provides an organic compound, which can solve the technical problems of low luminous efficiency and short service life of the existing blue-light fluorescent organic electronic device.
In order to achieve the above object, embodiments of the present application provide an organic compound having a structure represented by general formula (1):
Figure BDA0003939242440000021
wherein Ar is 1 Has a structure represented by the general formula (2):
Figure BDA0003939242440000022
Ar 2 、Ar 3 each selected from substituted or unsubstituted aromatic groups containing from 6 to 60 ring atoms, substituted or unsubstituted heteroaromatic groups containing from 5 to 60 ring atoms, or combinations of these groups;
g is selected from: a linear alkyl group having 1 to 20C atoms, a branched alkyl group having 3 to 20C atoms, a cyclic alkyl group having 3 to 20C atoms, a substituted or unsubstituted aromatic group containing 6 to 60 ring atoms, a substituted or unsubstituted heteroaromatic group containing 5 to 60 ring atoms, or a combination of these groups;
L 1 、L 2 independently selected from a single bond, a substituted or unsubstituted aromatic group containing from 6 to 60 ring atoms, or a substituted or unsubstituted heteroaromatic group containing from 5 to 60 ring atoms;
R 1 、R 2 and R 3 Each occurrence is independently selected from: -D, straight-chain alkyl having 1 to 20C atoms, straight-chain alkoxy having 1 to 20C atoms, withA linear thioalkoxy group having 1 to 20C atoms, a branched alkyl group having 3 to 20C atoms, a branched alkoxy group having 3 to 20C atoms, a branched thioalkoxy group having 3 to 20C atoms, a cyclic alkyl group having 3 to 20C atoms, a cyclic alkoxy group having 3 to 20C atoms, a cyclic thioalkoxy group having 3 to 20C atoms, a silyl group, a ketone group having 1 to 20C atoms, an alkoxycarbonyl group having 2 to 20C atoms, an aryloxycarbonyl group having 7 to 20C atoms, a cyano group, a carbamoyl group, a haloformyl group, a formyl group, an isocyano group, an isocyanate group, a thiocyanate group, an isothiocyanate group, a hydroxyl group, a nitro group, a substituted or unsubstituted amine group, -CF 3 -Cl, -Br, -F, -I, a substituted or unsubstituted aromatic group having 6 to 60 ring atoms, a substituted or unsubstituted heteroaromatic group having 5 to 60 ring atoms, a substituted or unsubstituted aryloxy group having 5 to 60 ring atoms, 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, 2,3 or 4;
m3 is 0,1, 2,3 or 4.
Correspondingly, the application also provides a mixture comprising the organic compound and at least one organic functional material, wherein the organic functional material is selected from a hole injection material, a hole transport material, an electron injection material, an electron blocking material, a hole blocking material, a light emitting material, a host material, a guest material or an organic dye.
Accordingly, the present application also provides a composition comprising the above organic compound or the above 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 contains the organic compound or the mixture, or the functional layer is prepared from the composition.
Optionally, in some embodiments of the present application, the organic functional layer includes a light emitting layer including a host material and a guest material, the host material includes the organic compound, and the guest material includes a pyrene-based compound;
the pyrene compound has a structure shown as a general formula (5):
Figure BDA0003939242440000031
wherein the content of the first and second substances,
Ar 4 、Ar 5 、Ar 6 、Ar 7 each independently selected from: a substituted or unsubstituted aromatic group containing 6 to 60 ring atoms, a substituted or unsubstituted heteroaromatic group containing 6 to 60 ring atoms, or a combination of these groups;
R 9 at each occurrence, is independently selected from: -H, -D, straight chain alkyl having 1 to 20C atoms, straight chain alkoxy having 1 to 20C atoms, straight chain thioalkoxy having 1 to 20C atoms, branched alkyl having 3 to 20C atoms, branched alkoxy having 3 to 20C atoms, branched thioalkoxy having 3 to 20C atoms, cyclic alkyl having 3 to 20C atoms, cyclic alkoxy having 3 to 20C atoms, cyclic thioalkoxy having 3 to 20C atoms, silyl, keto having 1 to 20C atoms, alkoxycarbonyl having 2 to 20C atoms, aryloxycarbonyl having 7 to 20C atoms, cyano, carbamoyl, haloformyl, formyl, isocyano, isocyanato, thiocyanate, isothiocyanate, hydroxyl, nitro, amine, CF, amino, hydroxyl, and alkoxy having 2 to 20C atoms 3 Cl, br, F, I, a substituted or unsubstituted aromatic group having 6 to 60 ring atoms, a substituted or unsubstituted heteroaromatic group having 5 to 60 ring atoms, a substituted or unsubstituted aryloxy group having 5 to 60 ring atoms, a substituted or unsubstituted heteroaryloxy group having 5 to 60 ring atoms, or a combination of these groups;
s is selected from 0,1, 2,3,4, 5, 6,7 or 8.
The beneficial effect of this application lies in:
the organic compound provided by the application is an anthracene derivative containing heterocyclic fused rings, and can be used as a host material for a light-emitting layer of an organic electronic device. The organic compounds of the present application have fluorescent emissions at blue wavelengths, and thus can be used in blue organic light emitting electronic devices, and result in devices with higher device luminous efficiency and longer device lifetimes.
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In order to more clearly illustrate the technical solutions in the embodiments of the present application, the drawings needed to be used in the description of the embodiments are briefly introduced below, and it is obvious that the drawings in the following description are only some embodiments of the present application, and it is obvious for those skilled in the art to obtain other drawings based on these drawings without creative efforts.
FIG. 1 is a schematic structural diagram of an OLED device provided in the embodiments of the present application.
The reference numbers in the figures are respectively: 100. an OLED device; 110. a substrate; 120. an anode; 130. a hole injection layer; 140. a hole transport layer; 150. a light emitting layer; 160. an electron transport layer; 170. and a cathode.
Detailed Description
The technical solutions in the embodiments of the present application will be clearly and completely described below with reference to the drawings in the embodiments of the present application, and it is obvious that the described embodiments are only a part of the embodiments of the present application, and not all of the embodiments. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of 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 of forms; it should be understood that the description in range format is merely for convenience and brevity and should not be construed as an inflexible limitation on the scope of the application; accordingly, the described range descriptions should be considered to have specifically disclosed all the possible sub-ranges as well as individual numerical values within that range. For example, it is contemplated that the 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 individual numbers within the stated range, such as 1,2,3,4, 5, and 6, for example, as applicable regardless of the range. In addition, whenever a numerical range is indicated herein, it is meant to include any number (fractional or integer) recited 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 present application is for the purpose of describing particular embodiments only and is not intended to be limiting of the application. As used herein, the term "and/or" includes any and all combinations of one or more of the associated listed items.
In the present application, the compositions, printing inks and inks have the same meaning and can be interchanged.
In the present application, aromatic groups, aromatic ring systems have the same meaning and can be interchanged.
In the present application, heteroaromatic groups, heteroaromatic and heteroaromatic ring systems have the same meaning and can be interchanged.
In the present application, "substituted" means that a hydrogen atom in a substituent is substituted by a substituent.
In the present application, "substituted or unsubstituted" means that the defined group may or may not be substituted. When a defined group is substituted, it is understood that the defined group may be substituted with one or more substituents R selected from, but not limited to, deuterium 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 also be further substituted with art-acceptable substituents; it is understood that R 'and R "in-NR' R" are each independently selected from, but not limited to, H, deuterium atoms, cyano groups, isocyano groups, nitro groups or halogens, alkyl groups containing 1 to 10C atoms, heterocyclic groups containing 3 to 20 ring atoms, aromatic groups containing 6 to 20 ring atoms, heteroaromatic groups containing 5 to 20 ring atoms. Preferably, R is selected from, but not limited to, deuterium atom, cyano group, isocyano group, nitro group or halogen, alkyl group containing 1 to 10C atoms, heterocyclic group containing 3 to 10 ring atoms, aromatic group containing 6 to 20 ring atoms, heteroaromatic group containing 5 to 20 ring atoms, silane group, carbonyl group, alkoxycarbonyl group, aryloxycarbonyl group, carbamoyl group, haloformyl group, formyl group, isocyanate group, thiocyanate group, isothiocyanate group, hydroxyl group and trifluoromethyl group, and the above groups may be further substituted with art-acceptable substituents.
In the present application, the "number of ring atoms" represents 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, and a heterocyclic compound) in which atoms are bonded in a ring shape. When the ring is substituted with a substituent, the atom included in the substituent is not included in the ring-forming atoms. The "number of ring atoms" described below is the same 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" means an aromatic hydrocarbon group derived by removing one hydrogen atom from an aromatic ring compound, and may be a monocyclic aryl group, or a condensed ring aryl group, or a polycyclic aryl group, at least one of which in the polycyclic ring is an aromatic ring system. For example, "substituted or unsubstituted aryl group having 6 to 40 ring atoms" means an aryl group containing 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, fluoranthenyl, triphenylenyl, pyrenyl, perylenyl, tetracenyl, fluorenyl, perylenenyl, acenaphthenyl, and derivatives thereof. It is understood that a plurality of aryl groups may also be interrupted by short non-aromatic units (e.g. <10% of non-H atoms, such as C, N or O atoms), such as in particular acenaphthene, fluorene, 9-diarylfluorene, triarylamine or diarylether systems should also be included in the definition of aryl groups.
"heteroaryl or heteroaromatic group" means that on the basis of an aryl group at least one carbon atom is replaced by a non-carbon atom which may be a N atom, an O atom, an S atom, etc. For example, "substituted or unsubstituted heteroaryl having 5 to 40 ring atoms" means a heteroaryl having 5 to 40 ring atoms, preferably a substituted or unsubstituted heteroaryl having 6 to 30 ring atoms, more preferably a substituted or unsubstituted heteroaryl having 6 to 18 ring atoms, particularly preferably a 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, oxadiazolyl, triazolyl, imidazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, acridinyl, pyridazinyl, pyrazinyl, quinolyl, isoquinolyl, quinazolinyl, quinoxalinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, benzothienyl, benzofuranyl, indolyl, pyrroloimidazolyl, pyrrolopyrrolyl, thienopyrrolyl, thienothienyl, furopyrrolyl, furofuranyl, thienofuranyl, benzisoxazolyl, benzisothiazolyl, benzimidazolyl, o-diazonaphthyl, phenanthridinyl, primary pyridyl, quinazolinyl, dibenzothienyl, dibenzofuranyl, carbazolyl, and derivatives thereof.
In the present application, "alkyl" may mean a linear, branched and/or cyclic alkyl group. The carbon number of the alkyl group may be 1 to 50, 1 to 30, 1 to 20, 1 to 10, or 1 to 6. 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 encompassing 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 connection site.
In the present application, when a plurality of substituents of the same symbol are contained on the same group, the substituents may be the same as or different from each other. For example
Figure BDA0003939242440000061
6R in the benzene ring 1 May be the same as or different from each other.
In this 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 of the ring. For example
Figure BDA0003939242440000062
Wherein R is connected with any substitutable site of the benzene ring; such as
Figure BDA0003939242440000063
To represent
Figure BDA0003939242440000067
Can be combined with
Figure BDA0003939242440000064
The optional position on the middle benzene ring forms a combined ring.
The cyclic alkyl and cycloalkyl groups described herein have the same meaning and are interchangeable.
The embodiment of the application provides an organic compound, a mixture, a composition and an organic electronic device. The following are detailed below. It should be noted that the following description of the embodiments is not intended to limit the preferred order of the embodiments.
The embodiment of the application provides an organic compound, which has a structure shown as a general formula (1):
Figure BDA0003939242440000065
wherein Ar is 1 Selected from the structures represented by the general formula (2):
Figure BDA0003939242440000066
Ar 2 、Ar 3 each independently selected from substituted or unsubstituted aromatic groups containing from 6 to 60 ring atoms, substituted or unsubstituted heteroaromatic groups containing from 5 to 60 ring atoms, or combinations of these groups;
g is selected from a linear alkyl group having 1 to 20C atoms, a branched alkyl group having 3 to 20C atoms, a cyclic alkyl group having 3 to 20C atoms, a substituted or unsubstituted aromatic group containing 6 to 60 ring atoms, a substituted or unsubstituted heteroaromatic group containing 5 to 60 ring atoms, or a combination of these groups;
L 1 、L 2 each independently selected from a single bond, a substituted or unsubstituted aromatic group containing from 6 to 60 ring atoms, a substituted or unsubstituted heteroaromatic group containing from 5 to 60 ring atoms;
R 1 、R 2 and R 3 Each occurrence is independently selected from: -D (deuterium), straight-chain alkyl having 1 to 20C atoms, straight-chain alkoxy having 1 to 20C atoms, straight-chain thioalkoxy having 1 to 20C atoms, branched alkyl having 3 to 20C atoms, branched alkoxy having 3 to 20C atoms, branched thioalkoxy having 3 to 20C atoms, cyclic alkyl having 3 to 20C atoms, cyclic alkoxy having 3 to 20C atoms, cyclic thioalkoxy having 3 to 20C atoms, silyl, keto having 1 to 20C atoms, keto having 2C atomsAlkoxycarbonyl of up to 20C atoms, aryloxycarbonyl of 7 to 20C atoms, cyano, carbamoyl, haloformyl, formyl, isocyano, isocyanate, thiocyanate, isothiocyanate, hydroxy, nitro, substituted or unsubstituted amine, -CF 3 -Cl, -Br, -F, -I, a substituted or unsubstituted aromatic group having 6 to 60 ring atoms, a substituted or unsubstituted heteroaromatic group having 5 to 60 ring atoms, a substituted or unsubstituted aryloxy group having 5 to 60 ring atoms, 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, 2,3 or 4;
m3 is 0,1, 2,3 or 4.
In some embodiments, R 1 、R 2 And R 3 Each occurrence is independently selected from: -D, a straight-chain alkyl group having 1 to 10C atoms, a straight-chain alkoxy group having 1 to 10C atoms, a straight-chain thioalkoxy group having 1 to 10C atoms, a branched-chain alkyl group having 3 to 10C atoms branched alkoxy having 3 to 10C atoms, branched thioalkoxy having 3 to 10C atoms, cyclic alkyl having 3 to 20C atoms, cyclic alkoxy having 3 to 10C atoms cyclic thioalkoxy having 3 to 10C atoms, silyl, keto having 1 to 10C atoms, alkoxycarbonyl having 2 to 10C atoms, aryloxycarbonyl having 7 to 10C atoms, cyano, carbamoyl, haloformyl, formyl, isocyano, isocyanate, thiocyanate, isothiocyanate, hydroxyl, nitro, amine, -CF 3 -Cl, -Br, -F, -I, a substituted or unsubstituted aromatic group having 6 to 30 ring atoms, a substituted or unsubstituted heteroaromatic group having 6 to 30 ring atoms, a substituted or unsubstituted aryloxy group having 6 to 30 ring atoms, a substituted or unsubstituted heteroaryloxy group having 6 to 30 ring atoms, or a combination of these groups.
In some embodiments, R 1 、R 2 And R 3 Each time goes outAt each occurrence, is independently selected from-D, straight chain alkyl of 1 to 8C atoms, branched alkyl of 3 to 8C atoms, cyclic alkyl of 3 to 8C atoms, silyl, cyano, isocyano, hydroxy, nitro, -CF 3 -Cl, -Br, -F, an aromatic group having 6 to 10 ring atoms which is substituted or unsubstituted, a heteroaromatic group having 5 to 10 ring atoms which is substituted or unsubstituted, or a combination of these groups.
In some embodiments, R 1 、R 2 And R 3 Each occurrence is independently selected from-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, a substituted or unsubstituted aromatic group having 6 to 10 ring atoms, a substituted or unsubstituted heteroaromatic group having 6 to 10 ring atoms, or a combination of these groups.
In some specific embodiments, R 1 、R 2 And R 3 At each of the time of the occurrence of the event, each 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, 1-methylhexyl, 2-ethylhexyl, 2-butylhexyl, cyclohexyl, adamantyl, phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthryl, triazinyl, pyridyl, pyrimidinyl, imidazolyl, furyl, thienyl, benzofuryl, benzothienyl, indolyl, carbazolyl, dibenzothienyl, dibenzofuryl, phenyl-substituted carbazolyl, fluorenyl substituted fluorenyl with alkyl having 1 to 6C atoms, phenyl substituted with alkyl having 1 to 6C atoms, naphthyl substituted with alkyl having 1 to 6C atoms, phenyl substituted with one or more D, naphthyl substituted with one or more D, phenyl, or a combination of these groups.
In some embodiments, m1 is selected from 0;
in some embodiments, m2 is 0 or 1.R 2 Each occurrence is independently selected from-D, methyl, isopropyl, t-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 alkyl groups having 1-6C atoms, naphthyl substituted with alkyl groups having 1-6C atoms, phenyl substituted with one or more D, naphthyl substituted with phenyl, or a combination of these groups.
In one embodiment, m3 is 0 or 1.R 3 Each occurrence is independently selected from-D, methyl, isopropyl, tert-butyl, phenyl, biphenyl, naphthyl, phenyl-substituted carbazolyl, dibenzofuranyl, dibenzothiophenyl, fluorenyl substituted with one or more methyl groups, phenanthryl, pyrenyl, fluoranthenyl, pyridyl, pyrimidyl, phenyl substituted with alkyl groups having 1-6C atoms, naphthyl substituted with alkyl groups having 1-6C atoms, phenyl substituted with one or more D, naphthyl substituted with phenyl, or a combination of these groups.
In one embodiment, the organic compound has at least one of the structures shown in formula (3-1) or formula (3-2):
Figure BDA0003939242440000091
in some embodiments, ar 2 Selected from substituted or unsubstituted aromatic groups containing 6 to 30 ring atoms, substituted or unsubstituted heteroaromatic groups containing 6 to 30 ring atoms.
In some embodiments, ar 2 Selected from substituted or unsubstituted aromatic groups containing 6 to 16 ring atoms, substituted or unsubstituted heteroaromatic groups containing 6 to 16 ring atoms.
In some embodiments, the Ar is 2 Selected from the structures shown in any one of:
Figure BDA0003939242440000092
wherein:
x is independently selected from CR at each occurrence 4 Or N;
y is selected from NR 5 、CR 6 R 7 、SiR 6 R 7 O, S = O or SO 2 ；
R 4 、R 5 、R 6 、R 7 Independently at each occurrence selected from-H, -D, straight chain alkyl having 1 to 20C atoms, straight chain alkoxy having 1 to 20C atoms, straight chain thioalkoxy having 1 to 20C atoms, or branched alkyl having 3 to 20C atoms, branched alkoxy having 3 to 20C atoms, branched thioalkoxy having 3 to 20C atoms, cyclic alkyl having 3 to 20C atoms, cyclic alkoxy having 3 to 20C atoms, cyclic thioalkoxy having 3 to 20C atoms, silyl, keto having 1 to 20C atoms, alkoxycarbonyl having 2 to 20C atoms, aryloxycarbonyl having 7 to 20C atoms, cyano, carbamoyl, haloformyl, formyl, isocyano, isocyanate, thiocyanate, isothiocyanate, hydroxyl, nitro, amine, -CF 3 -Cl, -Br, -F, -I, a substituted or unsubstituted aromatic group having 6 to 60 ring atoms, a substituted or unsubstituted heteroaromatic group having 5 to 60 ring atoms, a substituted or unsubstituted aryloxy group having 5 to 60 ring atoms, a substituted or unsubstituted heteroaryloxy group having 5 to 60 ring atoms, or a combination of these groups; r is 6 And R 7 With or without rings.
Understandably, in the present application, when X is the attachment site, X is C; when Y is the attachment site, Y is N.
In some embodiments, the structure of the organic compound is selected from the group consisting of structures represented by any of general formulas (4-1) to (4-14):
Figure BDA0003939242440000101
Figure BDA0003939242440000111
in some specific examples, R 4 At each occurrence, is independently selected from: -H, -D, linear 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 4 At 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.
The substituents are as defined above. Preferably, the substituents are selected from: -D, a straight chain alkyl group having 1 to 4C atoms, a branched alkyl group having 3 to 4C atoms, a phenyl or a pyridyl group.
In one embodiment, X in each of formulas (4-1) - (4-14) is selected from CR 4 ；R 4 Each occurrence is independently selected from: -H, -D, straight chain alkyl having 1 to 6C atoms, branched alkyl having 3 to 6C atoms, cyclic alkyl having 3 to 6C atoms.
In one embodiment, R 5 At 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 5 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 these groups; further, R 5 Each occurrence is independently selected from: methyl, ethyl, isopropyl, tert-butyl, phenyl, pyridyl, pyrimidinyl, triazinyl, biphenyl, terphenyl, or naphthyl.
In some specific examples, R 6 、R 7 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 6 、R 7 Each occurrence is independently selected from: -H, -D, methyl, ethyl, isopropyl, phenyl, pyridyl, pyrimidinyl, triazinyl, biphenyl, terphenyl, or naphthyl.
In a specific embodiment, ar 2 Any one selected from the structures shown below:
Figure BDA0003939242440000121
wherein: * Indicates the attachment site.
In one embodiment, G is 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 containing 6 to 30 ring atoms, a substituted or unsubstituted heteroaromatic group containing 6 to 30 ring atoms, or a combination of these groups.
In a certain 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 a specific embodiment, G is selected from the structures shown in any one of:
Figure BDA0003939242440000122
wherein the content of the first and second substances,
x is independently selected from CR at each occurrence 4 Or N;
y is selected from NR 5 、CR 6 R 7 、SiR 6 R 7 O, S = O or SO 2 ；
R 4 、R 5 、R 6 、R 7 At each occurrence, is independently selected from: -H, -D, straight chain alkyl having 1 to 20C atoms, straight chain alkoxy having 1 to 20C atoms, straight chain thioalkoxy having 1 to 20C atoms, branched alkyl having 3 to 20C atoms, branched alkoxy having 3 to 20C atoms, branched thioalkoxy having 3 to 20C atoms, cyclic alkyl having 3 to 20C atoms, cyclic alkoxy having 3 to 20C atoms, cyclic thioalkoxy having 3 to 20C atoms, silyl, keto having 1 to 20C atoms, alkoxycarbonyl having 2 to 20C atoms, aryloxycarbonyl having 7 to 20C atoms, cyano, carbamoyl, haloformyl, formyl, isocyano, isocyanate, thiocyanate, isothiocyanate, hydroxyl, nitro, amine, -CF 3 -Cl, -Br, -F, -I, a substituted or unsubstituted aromatic group having 6 to 60 ring atoms, a substituted or unsubstituted heteroaromatic group having 5 to 60 ring atoms, a substituted or unsubstituted aryloxy group having 5 to 60 ring atoms, a substituted or unsubstituted heteroaryloxy group having 5 to 60 ring atoms, or a combination of these groups. R 6 And R 7 With or without rings.
Understandably, in the present application, when X is the attachment site, X is C; when Y is the attachment site, Y is N.
In one embodiment, in formula (3-1), formula (4-1) - (4-7), G is independently selected from the group consisting of groups represented by formulas (A-1) - (A-7):
Figure BDA0003939242440000131
wherein denotes a ligation site.
In another embodiment, in formulae (3-2), formulae (4-8) - (4-14), G is independently selected from the group consisting of those represented by formulae (B-1) - (B-4):
Figure BDA0003939242440000132
wherein denotes the attachment site.
Preferably, X, at each occurrence in (A-1) - (A-7) and/or (B-1) - (B-4), is independently selected from CR 4 Or N; r 4 At 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.
The substituents are as defined above. Preferably, the substituents are selected from-D, straight chain alkyl having 1 to 4C atoms, branched alkyl having 3 to 4C atoms, phenyl, pyridyl.
In a certain embodiment, R in (A-1) - (A-7) and/or (B-1) - (B-4) 4 At each occurrence, is independently selected from: -H, -D, straight chain alkyl having 1 to 6C atoms, branched alkyl having 3 to 6C atoms, cyclic alkyl having 3 to 6C atoms, phenyl. In one embodiment, L 1 、L 2 Independently selected from a single bond, a substituted or unsubstituted aromatic group containing from 6 to 20 ring atoms, a substituted or unsubstituted heteroaromatic group containing from 6 to 20 ring atoms. Further, L 1 、L 2 Independently selected from a single bond, a substituted or unsubstituted aromatic group containing from 6 to 14 ring atoms, a substituted or unsubstituted heteroaromatic group containing from 6 to 14 ring atoms.
Further, in some embodiments, L 1 、L 2 Each independently selected from a single bond orA structure as shown in any one of:
Figure BDA0003939242440000141
wherein:
X 1 at each occurrence, independently selected from CR 8 Or N;
R 8 at each occurrence, is independently selected from: -H, -D, straight chain alkyl having 1 to 20C atoms, straight chain alkoxy having 1 to 20C atoms, straight chain thioalkoxy having 1 to 20C atoms, branched alkyl having 3 to 20C atoms, branched alkoxy having 3 to 20C atoms, branched thioalkoxy having 3 to 20C atoms, cyclic alkyl having 3 to 20C atoms, cyclic alkoxy having 3 to 20C atoms, cyclic thioalkoxy having 3 to 20C atoms, silyl, keto having 1 to 20C atoms, alkoxycarbonyl having 2 to 20C atoms, aryloxycarbonyl having 7 to 20C atoms, cyano, carbamoyl, haloformyl, formyl, isocyano, isocyanate, thiocyanate, isothiocyanate, hydroxyl, nitro, amine, -CF 3 -Cl, -Br, -F, -I, a substituted or unsubstituted aromatic group having 6 to 60 ring atoms, a substituted or unsubstituted heteroaromatic group having 5 to 60 ring atoms, a substituted or unsubstituted aryloxy group having 5 to 60 ring atoms, a substituted or unsubstituted heteroaryloxy group having 5 to 60 ring atoms, or a combination of these groups.
Understandably, in this application, when X is 1 When it is a linking site, X 1 Is C.
In some specific examples, R 8 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, an aromatic group having 6 to 14 ring atoms substituted with a linear alkyl group having 1 to 4C atomsA linear alkyl group of (a) or a branched alkyl group of 3 to 6C atoms substituted heteroaromatic group of 6 to 14 ring atoms.
In some embodiments, L 1 And L 2 Each independently selected from a single bond or at least one of the following groups (but not limited thereto):
Figure BDA0003939242440000142
Figure BDA0003939242440000151
by way of example, the organic compound may include, but is not limited to, at least one of the following structures:
Figure BDA0003939242440000152
Figure BDA0003939242440000161
Figure BDA0003939242440000171
Figure BDA0003939242440000181
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), an Emitter (Emitter), a Host material (Host), or an organic dye.
In some embodiments, the organic compounds of the present application can be used as light emitting materials in the light emitting layer of organic electronic devices. In some preferred embodiments, the organic compounds of the present application are used as host materials in the emissive layer of organic electronic devices.
The application also relates to a mixture comprising at least one of the organic compounds and at least one further organic functional material. The other organic functional material may be, but is not limited to, a hole injection material, a hole transport material, an electron injection 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 organic electronic devices.
In some embodiments, the further organic functional material is selected from guest materials. Further, the another organic functional material is selected from a blue light guest material. Further, the blue light guest is a pyrene compound 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.
In particular, the at least one organic solvent is selected from aromatic or heteroaromatic-based solvents, ester-based solvents, aromatic ketone-based solvents, aromatic ether-based solvents, aliphatic ketones, aliphatic ethers, cycloaliphatic compounds, olefinic compounds, borate compounds or phosphate compounds.
The aromatic or heteroaromatic-based solvent may be selected from, but not limited to, at least one selected from the group consisting of p-diisopropylbenzene, pentylbenzene, tetrahydronaphthalene, cyclohexylbenzene, chloronaphthalene, 1, 4-dimethylnaphthalene, 3-isopropylbiphenyl, p-methylisopropylbenzene, dipentylbenzene, tripentylbenzene, pentyltoluene, o-diethylbenzene, m-diethylbenzene, p-diethylbenzene, 1,2,3, 4-tetramethylbenzene, 1,2,3, 5-tetramethylbenzene, 1,2,4, 5-tetramethylbenzene, butylbenzene, dodecylbenzene, dihexylbenzene, dibutylbenzene, p-diisopropylbenzene, cyclohexylbenzene, benzylbutylbenzene, dimethylnaphthalene, 3-isopropylbiphenyl, 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-phenylpropyl) pyridine, 1, benzyl (1, 1-dimethyl-2-phenyl) benzene, 2-ethyl benzoate, 2-dimethylquinoline, and 2-isopropylfuran.
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. Particularly, at least one of octyl octanoate, diethyl sebacate, diallyl phthalate and isononyl isononanoate is preferable.
The aromatic ketone-based solvent may be selected from, but not limited to: 1-tetralone, 2- (phenylepoxy) tetralone, 6- (methoxy) tetralone, acetophenone, propiophenone, benzophenone, and derivatives thereof, such as at least one of 4-methylacetophenone, 3-methylacetophenone, 2-methylacetophenone, 4-methylacetophenone, 3-methylacetophenone, and 2-methylacetophenone.
The aromatic ether-based solvent may be selected from, but not limited to, at least one of 3-phenoxytoluene, butoxybenzene, p-anisaldehyde dimethylacetal, tetrahydro-2-phenoxy-2H-pyran, 1, 2-dimethoxy-4- (1-propenyl) benzene, 1, 4-benzodioxane, 1, 3-dipropylbenzene, 2, 5-dimethoxytoluene, 4-ethylphenethyl ether, 1, 3-dipropoxybenzene, 1,2, 4-trimethoxybenzene, 4- (1-propenyl) -1, 2-dimethoxybenzene, 1, 3-dimethoxybenzene, glycidylphenyl ether, dibenzyl ether, 4-tert-butylanisole, trans-p-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-nonanone, 3-nonanone, 5-nonanone, 2-decanone, 2, 5-hexanedione, 2,6, 8-trimethyl-4-nonanone, fenchone, phorone, isophorone, di-n-amyl ketone, and the like; or an aliphatic ether, for example, 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 to be understood that the organic solvent may be used alone or as a mixed solvent of two or more organic solvents.
In some embodiments, the compositions herein 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 another organic solvent may be selected from, but not limited to, at least one of methanol, ethanol, 2-methoxyethanol, dichloromethane, chloroform, chlorobenzene, o-dichlorobenzene, tetrahydrofuran, anisole, morpholine, toluene, o-xylene, m-xylene, p-xylene, 1, 4-dioxane, acetone, methyl ethyl ketone, 1, 2-dichloroethane, 3-phenoxytoluene, 1-trichloroethane, 1, 2-tetrachloroethane, ethyl acetate, butyl acetate, dimethylformamide, dimethylacetamide, dimethyl sulfoxide (DMSO), tetrahydronaphthalene, decalin, and indene.
In some preferred embodiments, the organic solvent suitable for the present application is a solvent having Hansen (Hansen) solubility parameters in the following ranges:
δ d (dispersion force) in the range of 17.0 to 23.2MPa1/2, particularly in the range of 18.5 to 21.0MPa1/2;
δ p (polar force) is in the range of 0.2 to 12.5MPa1/2, particularly in the range of 2.0 to 6.0 MPa1/2;
δ h (hydrogen bonding force) is in the range of 0.9 to 14.2MPa1/2, particularly in the range of 2.0 to 6.0 MPa1/2.
In some embodiments, the organic solvent is selected with a boiling point in mind in the compositions herein. In at least some embodiments, the organic solvent has a boiling point of 150 ℃ or higher; preferably equal to or more than 180 ℃; more preferably more than or equal to 200 ℃; more preferably more than or equal to 250 ℃; most preferably greater than or equal to 300 ℃. Boiling points in these ranges are beneficial for preventing nozzle clogging in inkjet print heads.
It is understood that the organic solvent may be evaporated from the composition system to form a thin 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 the mixture in the composition may be 0.01 to 10wt%, preferably 0.1 to 8wt%, more preferably 0.2 to 5wt%, and still more preferably 0.25 to 3wt%.
The application also relates to the use of said composition as a coating or printing ink for the production of organic electronic devices. In some embodiments, the composition is used to prepare organic electronic devices by a printing or coating preparation method. The printing or coating may be prepared by, but is not limited to, ink jet printing, gravure printing, jet printing, letterpress printing, screen printing, dip coating, spin coating, doctor blade coating, roll printing, twist roll printing, offset printing, flexographic printing, rotary printing, spraying, brushing, pad printing, slot die coating, and the like. Gravure printing, jet printing and ink-jet printing are preferred.
The solution or suspension may additionally include additives for adjusting viscosity, adjusting film-forming properties, improving adhesion, and the like. The additive may be selected from, but is not limited to, at least one of a surface active compound, a lubricant, a wetting agent, a dispersant, a hydrophobic agent, and a binder. The requirements for the coating or printing ink may differ 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 scheme is as follows:
the present application provides an organic electronic device comprising an organic compound or mixture as described above, or prepared from said composition.
Further, the organic electronic device comprises an anode, a cathode, and one or more organic functional layers positioned between the anode and the cathode; the organic functional layer comprises the organic compound, the mixture or the composition.
The organic functional layer is selected from a Hole Injection Layer (HIL), a Hole Transport Layer (HTL), an emission 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 (oelt), an Organic laser, an Organic spintronic device, an Organic sensor, an Organic Plasmon Emitting Diode (Organic plasma Emitting Diode), and the like. The organic electronic device is preferably an OLED device. Further, in one embodiment, the organic compound is used in a light emitting layer of an OLED device, the light emitting layer comprising an organic compound or mixture as described above, or prepared from the composition.
In some embodiments, the one or more organic functional layers of the organic electronic device comprise at least a light-emitting layer. The material of the light-emitting layer comprises a host material and a guest material. The host material comprises the organic compound and the guest material comprises a pyrene organic compound.
The present application further relates to an organic electronic device comprising: the organic light-emitting diode 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, the light-emitting layer material comprises a host material and a guest material, the host material comprises an organic compound shown in a general formula (1), and the guest material comprises a pyrene compound;
the pyrene compound (pyrene organic compound) has a structure as described in general formula (5):
Figure BDA0003939242440000211
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, a substituted or unsubstituted heteroaromatic group containing 6 to 60 ring atoms, or a combination of these groups;
R 9 at each occurrence, is independently selected from: -H, -D, straight chain alkyl having 1 to 20C atoms, straight chain alkoxy having 1 to 20C atoms, straight chain thioalkoxy having 1 to 20C atoms, branched alkyl having 3 to 20C atoms, branched alkoxy having 3 to 20C atoms, branched thioalkoxy having 3 to 20C atoms, cyclic alkyl having 3 to 20C atoms, cyclic alkoxy having 3 to 20C atoms, cyclic thioalkoxy having 3 to 20C atoms, silyl, keto having 1 to 20C atoms, alkoxycarbonyl having 2 to 20C atoms, aryloxycarbonyl having 7 to 20C atoms, cyano, carbamoyl, haloformyl, formyl, isocyano, isocyanato, thiocyanate, isothiocyanate, hydroxyl, nitro, amine, CF, amino, hydroxyl, and alkoxy having 2 to 20C atoms 3 Cl, br, F, I, a substituted or unsubstituted aromatic group having 6 to 60 ring atoms, a substituted or unsubstituted heteroaromatic group having 5 to 60 ring atoms, a substituted or unsubstituted aryloxy group having 5 to 60 ring atoms, a substituted or unsubstituted heteroaryloxy group having 5 to 60 ring atoms, or a combination of these groups;
s is selected from 0,1, 2,3,4, 5, 6,7 or 8.
The organic compound is shown as a general formula (1), and further description is given in the foregoing, and is not repeated here.
In some embodiments, ar 4 、Ar 5 、Ar 6 、Ar 7 Each independently selected from: substituted or unsubstituted aromatic groups containing 6 to 14 ring atoms, substituted or unsubstituted heteroaromatic groups containing 6 to 14 ring atoms, or combinations of these groups.
Further, in some embodiments, ar is 4 、Ar 5 、Ar 6 、Ar 7 Each independently comprises the structure shown in any one of the following:
Figure BDA0003939242440000221
wherein:
v is independently selected from CR at each occurrence 10 Or N;
w is selected from NR 11 、CR 11 R 12 、SiR 11 R 12 O, S = O or SO 2 ；
R 10 、R 11 、R 12 At each occurrence, is independently selected from: -H, -D, straight chain alkyl having 1 to 20C atoms, straight chain alkoxy having 1 to 20C atoms, straight chain thioalkoxy having 1 to 20C atoms, branched alkyl having 3 to 20C atoms, branched alkoxy having 3 to 20C atoms, branched thioalkoxy having 3 to 20C atoms, cyclic alkyl having 3 to 20C atoms, cyclic alkoxy having 3 to 20C atoms, cyclic thioalkoxy having 3 to 20C atoms, silyl, keto having 1 to 20C atoms, alkoxycarbonyl having 2 to 20C atoms, aryloxycarbonyl having 7 to 20C atoms, cyano, carbamoyl, haloformyl, formyl, isocyano, isocyanate, thiocyanate, isothiocyanate, hydroxyl, nitro, amine, -CF 3 -Cl, -Br, -F, -I, a substituted or unsubstituted aromatic group having 6 to 60 ring atoms, a substituted or unsubstituted heteroaromatic group having 5 to 60 ring atoms, a substituted or unsubstituted aryloxy group having 5 to 60 ring atoms, a substituted or unsubstituted heteroaryloxy group having 5 to 60 ring atoms, or a combination of these groups.
Further, in some embodiments, R 9 、R 10 、R 11 、R 12 Each occurrence is independently selected from: -H, -D, straight chain alkyl having 1 to 10C atoms, branched or cyclic alkyl having 3 to 10C atoms or phenyl.
In some embodiments, the pyrene-based organic compound is selected from the following general structural formulas:
Figure BDA0003939242440000231
wherein R is 10 Each occurrence is independently selected from-H, -D, a straight chain alkyl group having 1 to 10C atoms, a branched chain alkyl group having 3 to 10C atoms, a cyclic alkyl group, or a phenyl group.
Further, in some embodiments, the pyrene-based organic compound is selected from the following general formulas:
Figure BDA0003939242440000232
wherein R is 10 Each occurrence is independently selected from-H, -D, a straight chain alkyl group having 1 to 10C atoms, a branched chain alkyl group having 3 to 10C atoms, a cyclic alkyl group, or a phenyl group; w is as described above.
As an example, the pyrene compound described herein may be selected from, but not limited to, any one of the following structural formulas (BD-1) to (BD-24):
Figure BDA0003939242440000233
Figure BDA0003939242440000241
it is understood that the organic electronic device may further add some functional layers that are conventionally used in organic electronic devices and contribute to the performance of the device, such as an electron transport layer, an electron injection layer, an electron blocking layer, a hole transport layer, a hole injection layer, a hole blocking layer, a light extraction layer, and the like.
In one embodiment, the organic electronic device comprises a cathode, an electron transport layer, a light emitting layer, a hole transport layer, and an anode.
In one embodiment, the organic electronic device comprises a cathode, an electron transport layer, a light emitting layer, a hole transport layer, a hole injection layer, and an anode.
In one embodiment, the organic electronic device comprises a cathode, an electron transport layer, a light emitting layer, an electron blocking layer, a hole transport layer, a hole injection layer and an anode.
Suitable materials for use in these functional layers are described in detail above and in WO2010135519A1, US20090134784A1 and WO2011110277A1, the entire contents of these 3 patent documents being 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 flexible, for example the material of the substrate may be plastic, metal, semiconductor wafer or glass. Preferably, the substrate has a smooth surface, and a substrate free of surface defects is particularly desirable. In a preferred embodiment, the substrate is a flexible substrate. The material of the flexible substrate may be a polymer film or plastic. The glass transition temperature Tg of the flexible substrate is 150 ℃ or higher, preferably more than 200 ℃, more preferably more than 250 ℃, and most preferably more than 300 ℃. As an example, the material of the flexible substrate may be poly (ethylene terephthalate) (PET) or polyethylene glycol (2, 6-naphthalene) (PEN).
The material of the anode is an anode material known in the art for organic electronic devices, such as a conductive metal, a conductive metal oxide, or a conductive polymer. In some embodiments, the absolute value of the difference between the work function of the material of the anode and the HOMO level or valence band level of the emitter in the light emitting layer or the p-type semiconductor material acting as a hole injection layer or hole transport layer or electron blocking layer is less than 0.5eV, preferably less than 0.3eV, most preferably less than 0.2eV. As an example, the material of the anode may be selected from, but not limited to, at least one of Al, cu, au, ag, mg, fe, co, ni, mn, pd, pt, ITO, and aluminum-doped zinc oxide (AZO). Other suitable anode materials are known and 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 pattern structured. 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 organic electronic devices, such as a conductive metal or a conductive metal oxide. In some embodiments, the absolute value of the difference between the work function of the material of the cathode and the LUMO level or conduction band level of the emitter 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 cathodes for OLEDs are possible as cathode materials for the devices of the present application. As an example, the material of the cathode may be selected from, but not limited to, at least one of Al, au, ag, ca, ba, mg, liF/Al, mgAg alloy, baF2/Al, cu, fe, co, ni, mn, pd, pt, and ITO. The cathode material 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 known in the art for hole transport layer materials, for example, at least one selected from 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), polytriphenylamine (polytriphenylamine), poly (3, 4-ethylene-thiophene) (tcpss), and polythenylene-triphenylamine (tcpss) 4 ″ -triphenylamine (tcpss, 9, 4' -triphenylene).
The material of the electron transport layer is a material known in the art for electron transport layers, and may be selected from, for example, but not limited to, ET and Liq, PBD (2- (4-biphenyl) -5-phenyl oxadiazole), 8-hydroxyquinoline aluminum (Xlq) 3 ) And graphene.
Wherein the chemical structural formulas of ET and Liq are as follows:
Figure BDA0003939242440000261
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-hexaazatriphenylene (HXT-CN), PEDOT (polyethylenedioxythiophene), PEDOT: PSS, and s-MoO doped therewith 3 (PEDOT: PSS: s-MoO) 3 ) At least one of (1).
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 light-emitting wavelength of the organic electronic device is between 300nm and 1000nm, preferably between 350nm and 900nm, and more preferably between 400nm and 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, and the like.
The present application has been carried out several times in sequence, and the present invention will now be described in further detail with reference to some test results, which are described in detail below with reference to specific examples.
Example 1
This example provides an organic compound (compound 1).
The synthetic route for compound 1 of this example is as follows:
Figure BDA0003939242440000262
synthesis of intermediate 1-1:
indole (23.4 g, 200mmol) was dissolved in DMF (100 ml), bromine (32g, 200mmol) was dissolved in DMF (50 ml) and slowly added dropwise to the indole solution. Stir at room temperature for 2h. After the reaction was completed, sodium thiosulfate aqueous solution was added to remove the remaining bromine, most of the solvent was removed by rotary evaporation, and then the solution was extracted and washed with water, separated by organic phase column chromatography (eluent PE: DCM = 5) and recrystallized to give intermediate 1-1, yield: 94 percent. MS (ASAP) =195.0.
Synthesis of intermediates 1-2:
the intermediate 1-1 (10g, 51mmol) and 2-nitro-5-chlorobenzeneboronic acid (12.4g, 61mmol) were dissolved in a mixed solvent of 1, 4-dioxane and water (100 ml/10 ml), and Pd (PPh) was added 3 ) 4 (2.9g, 2.5mmol) and potassium carbonate (27.6g, 200mmol). Stirring was carried out at 100 ℃ for 12h under a nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation, and the separated liquid was extracted and washed with water, subjected to organic phase column chromatography (eluent PE: DCM = 3) and recrystallized to give intermediates 1-2, yield: and 63 percent. MS (ASAP) =272.0.
Synthesis of intermediates 1 to 3:
the intermediates 1-2 (8g, 29mmol) were placed in a 100ml two-necked flask, 30ml of dichlorobenzene was added until complete dissolution, triethyl phosphite (16.6 g, 100mmol) was added, and stirring was carried out at 180 ℃ for 12 hours under a nitrogen atmosphere. After cooling, the solvent was distilled off under reduced pressure, and dichloromethane was then added, and the liquid was washed with water, subjected to organic phase column chromatography (eluent PE: DCM = 5) and recrystallized to give intermediates 1 to 3 in a yield of 53%. MS (ASAP) =240.1.
Synthesis of intermediates 1 to 4:
intermediate 1-3 (10g, 41.7mmol), iodobenzene (20.4g, 100mmol) and Pd were weighed 2 (dba) 3 (2.9g，3.2mmol)，t-Bu 3 P (0.78g, 3.9mmol) and sodium tert-butoxide (15.5g, 162mmol) were put in a 500mL three-necked flask, 200mL of toluene was added, nitrogen was replaced, and the mixture was reacted at 80 ℃ for 12 hours. Spin-dry, water-wash, and column-chromatographically (eluent PE: DCM = 6. Yield: 82 percent. MS (ASAP) =392.1.
Synthesis of Compound 1:
the intermediate 1-4 (3.9g, 10mmol) and 10- (1-naphthyl) -9-anthraceneboronic acid (5.4g, 14mmol) are dissolved in a mixed solvent of 1, 4-dioxane and water (100 ml/10 ml), and Pd is added 2 (dba) 3 (0.18g, 0.2mmol), s-phos (0.16g, 0.4mmol), and potassium carbonate (6.9g, 50mmol). Stirring at 100 ℃ for 12h under nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation, then the separated liquid was extracted and washed with water, and organic phase column chromatography (eluent PE: DCM = 5) and recrystallized to give compound 1, yield: 58 percent. MS (ASAP) =660.3.
Example 2
This example provides an organic compound (compound 2).
The synthetic route for compound 2 of this example is as follows:
Figure BDA0003939242440000281
synthesis of intermediate 2-1:
intermediate 1-1 (10g, 41.7mmol), iodobenzene (8.6g, 42mmol) and Pd were weighed 2 (dba) 3 (1.9g，2.1mmol)，t-Bu 3 P (0.51g, 2.5 mmol) and sodium t-butoxide (20g, 209mmol) were placed in a 500mL three-necked flask, and 200mL of toluene was added thereto under nitrogen exchange and reacted at 80 ℃ for 12 hours. Spin-drying, washing with water, and performing column chromatography (eluent PE: DCM = 8). Yield: and 72 percent. MS (ASAP) =271.0.
Synthesis of intermediate 2-2:
the intermediate 2-1 (10g, 37mmol) and 2-nitro-5-chlorobenzeneboronic acid (7.4g, 37mmol) were dissolved in a mixed solvent of 1, 4-dioxane and water (100 ml/10 ml), and Pd (PPh) was added 3 ) 4 (0.86g, 0.74mmol) and potassium carbonate (25.5g, 185mmol). Stirring at 100 ℃ for 12h under nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation, then the separated liquid was extracted and washed with water, and organic phase column chromatography (eluent PE: DCM = 3) and recrystallized to give intermediate 2-2, yield: 81 percent. MS (ASAP) =348.1.
And (3) synthesis of intermediates 2-3:
intermediate 2-2 (8g, 23mmol) was added to a 100ml two-necked flask, 30ml of dichlorobenzene was added to complete dissolution, triethyl phosphite (19.1g, 115mmol) was added, and the mixture was stirred at 180 ℃ for 12h under nitrogen. After cooling, the solvent was distilled off under reduced pressure, dichloromethane was then added and the layers were washed with water, the organic phase was purified by column chromatography (eluent PE: DCM = 4) and recrystallized to give intermediates 2-3, yield: 57 percent. MS (ASAP) =316.1.
Synthesis of intermediates 2 to 4:
intermediate 2-3 (6.3g, 20mmol), 2-iodonaphthalene (5.1g, 20mmol) and Pd were weighed 2 (dba) 3 (0.92g，1mmol)，t-Bu 3 P (0.24g, 1.2mmol) and sodium tert-butoxide (20g, 209mmol) were put in a 500mL three-necked flask, and 200mL of toluene was added thereto, and the mixture was reacted at 80 ℃ for 12 hours while replacing nitrogen. Spin-drying, washing with water, and performing column chromatography (eluent PE: DCM = 8). Yield: and 78 percent. MS (ASAP) =442.1.
Synthesis of Compound 2:
the intermediate 2-4 (4.4g, 10mmol) and 10-phenyl-9-anthraceneboronic acid (4.2g, 14mmol) were dissolved in a mixed solvent of 1, 4-dioxane and water (100 ml/10 ml), and Pd was added 2 (dba) 3 (0.18g, 0.2mmol), s-phos (0.16g, 0.4mmol) and potassium carbonate (6.9g, 50mmol). Stirring was carried out at 100 ℃ for 12h under a nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation, then the separated liquid was extracted and washed with water, and organic phase column chromatography (eluent PE: DCM = 5) and recrystallized to give compound 2, yield: and 64 percent. MS (ASAP) =660.3.
Example 3
This example provides an organic compound (compound 3).
The synthetic route for compound 3 of this example is as follows:
Figure BDA0003939242440000291
synthesis of intermediate 3-1:
intermediate 2-3 (6.3g, 20mmol), 2-bromodibenzofuran (4.9g, 20mmol) and Pd are weighed 2 (dba) 3 (0.92g，1mmol)，t-Bu 3 P (0.24g, 1.2mmol), tert-butylSodium butoxide (19g, 200mmol) was placed in a 500mL three-necked flask, 200mL of toluene was added, nitrogen was replaced, and the reaction was carried out at 80 ℃ for 12 hours. Spin-drying, washing with water, and performing column chromatography (eluent PE: DCM = 8). Yield: 72 percent. MS (ASAP) =482.1.
Synthesis of Compound 3:
the intermediate 3-1 (4.8g, 10mmol) and 10-deuterated phenyl-9-anthraceneboronic acid (4.2g, 14mmol) were dissolved in a mixed solvent of 1, 4-dioxane and water (100 ml/10 ml), and Pd was added 2 (dba) 3 (0.18g, 0.2mmol), s-phos (0.16g, 0.4mmol), and potassium carbonate (6.9g, 50mmol). Stirring at 100 ℃ for 12h under nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation, and the separated liquid was extracted and washed with water, and subjected to organic phase column chromatography (eluent PE: DCM = 5) and recrystallized to give compound 3 in yield: 66 percent. MS (ASAP) =705.3.
Example 4
This example provides an organic compound (compound 4).
The synthetic route for compound 4 of this example is as follows:
Figure BDA0003939242440000292
synthesis of intermediate 4-1:
intermediate 2-3 (6.3g, 20mmol), 2-bromobiphenyl (4.6g, 20mmol) and Pd were weighed 2 (dba) 3 (0.92g，1mmol)，t-Bu 3 P (0.24g, 1.2 mmol) and sodium tert-butoxide (19g, 200mmol) were placed in a 500mL three-necked flask, and 200mL of toluene was added thereto, and the mixture was purged with nitrogen and reacted at 80 ℃ for 12 hours. Spin-drying, washing with water, and performing column chromatography (eluent PE: DCM = 8). Yield: 77 percent. MS (ASAP) =468.1.
Synthesis of Compound 4:
the intermediate 4-1 (4.7g, 10mmol) and 10- (2-deuterated naphthyl) -9-anthracene boric acid (5.0g, 14mmol) were dissolved in a mixed solvent of 1, 4-dioxane and water (100 ml/10 ml), and Pd was added 2 (dba) 3 (0.18g, 0.2mmol), s-phos (0.16g, 0.4mmol) and potassium carbonate (6.9g, 50mmol). In a nitrogen atmosphereThen, the mixture was stirred at 100 ℃ for 12 hours. After cooling, most of the solvent was removed by rotary evaporation, and the separated liquid was extracted and washed with water, subjected to organic phase column chromatography (eluent PE: DCM = 5) and recrystallized to give compound 4 in yield: 71 percent. MS (ASAP) =743.3.
Example 5
This example provides an organic compound (compound 5).
The synthetic route for compound 5 of this example is as follows:
Figure BDA0003939242440000301
synthesis of intermediate 5-1:
9, 10-dibromoanthracene (6.8g, 20mmol) and 2-biphenylboronic acid (4.0g, 20mmol) were dissolved in a mixed solvent of 1, 4-dioxane and water (100/10 ml), and Pd (PPh) was added 3 ) 4 (1.2g, 1mmol) and potassium carbonate (6.9g, 50mmol). Stirring was carried out at 100 ℃ for 12h under a nitrogen atmosphere. After cooling, most of the solvent is removed by rotary evaporation, then liquid is extracted and washed by water, and the intermediate 5-1 is obtained by organic phase column chromatography and recrystallization, and the yield is as follows: 76 percent. MS (ASAP) =408.1.
Synthesis of intermediate 5-2:
preparing a dry 250mL three-neck flask, building a reaction device, vacuumizing, and introducing nitrogen; keeping nitrogen circulation in a reaction bottle, weighing the intermediate 5-1 (5.0 g, 12mmol), adding THF (100 ml), vacuumizing, introducing nitrogen, circulating for three times, and cooling to-78 ℃; an n-butyllithium solution (4.9ml, 12mmol) was slowly dropped into the reaction flask, and after the reaction at-78 ℃ for 60min, triethyl borate (1.8g, 12mmol) was slowly dropped. The reaction was allowed to slowly warm to room temperature and allowed to react for 12h. Adding dilute hydrochloric acid, stirring for 30 min, extracting with EA, spin-drying the solvent, and pulping with PE to obtain white solid. The yield thereof was found to be 82%. MS (ASAP) =374.2.
Synthesis of Compound 5:
dissolving intermediate 5-2 (3.7g, 10mmol) and intermediate 3-1 (4.8g, 10mmol) in a mixed solvent of 1, 4-dioxane and water (100/10 ml), and adding Pd 2 (dba) 3 (0.18g，0.2mmol)、s-phos(0.16g,0.4 mmol) and potassium carbonate (6.2g, 45mmol). Stirring was carried out at 100 ℃ for 12h under a nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation, followed by extraction and water washing of the separated liquid, organic phase column chromatography and recrystallization to give compound 5, yield: 48 percent. MS (ASAP) =776.3.
Example 6
This example provides an organic compound (compound 6).
The synthetic route for compound 6 of this example is as follows:
Figure BDA0003939242440000311
synthesis of intermediate 6-1:
9, 10-dibromoanthracene (6.7g, 20mmol) and dibenzo [ b, d ] were added]Furan-2-boronic acid (4.3g, 20mmol) was dissolved in a mixed solvent of 1, 4-dioxane and water (100/10 ml), and Pd (PPh) was added 3 ) 4 (1.2g, 1mmol) and potassium carbonate (14g, 100mmol). Stirring was carried out at 100 ℃ for 12h under a nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation, followed by extraction and water washing for liquid separation, organic phase column chromatography and recrystallization to give intermediate 6-1, yield: 58 percent. MS (ASAP) =422.0.
Synthesis of intermediate 6-2:
preparing a dry 250mL three-neck flask, building a reaction device, vacuumizing, and introducing nitrogen; keeping nitrogen circulation in a reaction bottle, weighing intermediate 6-1 (5.0g, 11.8mmol), adding THF (100 ml), vacuumizing, introducing nitrogen, circulating for three times, and cooling to-78 ℃; an n-butyl lithium solution (4.7ml, 11.8mmol) was slowly dropped into the reaction flask, and after a reaction at-78 ℃ for 60min, triethyl borate (1.7g, 11.8mmol) was slowly dropped. The reaction was allowed to slowly warm to room temperature and allowed to react for 12h. Adding dilute hydrochloric acid, stirring for 30 minutes, extracting with EA, spin-drying the solvent, and pulping with PE to obtain a white solid. The yield thereof was found to be 88%. MS (ASAP) =388.1.
Synthesis of Compound 6:
the intermediate 6-2 (3.9g, 10mmol) and the intermediate 4-1 (4.7g, 10mmol) were dissolved in a mixed solvent of 1, 4-dioxane and water (100/10 ml), and Pd was added 2 (dba) 3 (0.18g, 0.2mmol), s-phos (0.16g, 0.4mmol), and potassium carbonate (4.1g, 30mmol). Stirring was carried out at 100 ℃ for 12h under a nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation, followed by extraction and water washing of the separated liquid, organic phase column chromatography and recrystallization to give compound 6, yield: and 69 percent. MS (ASAP) =776.3.
Example 7
This example provides an organic compound (compound 7).
The synthetic route for compound 7 of this example is as follows:
Figure BDA0003939242440000321
synthesis of intermediate 7-1:
the intermediate 2-1 (10 g, 37mmol) and 2-nitrophenylboronic acid (6.2g, 37mmol) were dissolved in a mixed solvent of 1, 4-dioxane and water (100 ml/10 ml), and Pd (PPh) was added 3 ) 4 (0.86g, 0.74mmol) and potassium carbonate (25.5g, 185mmol). Stirring was carried out at 100 ℃ for 12h under a nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation, then the separated liquid was extracted and washed with water, and organic phase column chromatography (eluent PE: DCM = 3) and recrystallized to give intermediate 7-1, yield: 72 percent. MS (ASAP) =314.1.
Synthesis of intermediate 7-2:
intermediate 7-1 (10g, 32mmol) was added to a 100ml two-necked flask, 30ml of dichlorobenzene was added until complete dissolution, and triethyl phosphite (26g, 159mmol) was added and stirred at 180 ℃ for 12 hours under a nitrogen atmosphere. After cooling, the solvent was distilled off under reduced pressure, dichloromethane was then added and the liquid was washed with water, and the organic phase was purified by column chromatography (eluent PE: DCM = 3) and recrystallized to give intermediate 7-2, yield: 59 percent. MS (ASAP) =282.1.
Synthesis of compound 7:
intermediate 7-2 (5.6 g, 20mmol), 10- (1-naphthyl) -9-bromoanthracene (11.5g, 30mmol) and Pd were weighed 2 (dba) 3 (0.92g，1mmol)，t-Bu 3 P (0.24g, 1.2mmol), sodium tert-butoxide (20g, 209mmol) in a 500mL three-necked flask, 200mL of toluene was added,the nitrogen was replaced and the reaction was carried out at 80 ℃ for 12 hours. Spin-dry, water-wash, and column-chromatographe (eluent PE: DCM = 8). Yield: 67 percent. MS (ASAP) =584.2.
Example 8
This example provides an organic compound (compound 8).
The synthetic route for compound 8 of this example is as follows:
Figure BDA0003939242440000322
synthesis of intermediate 8-1:
9, 10-dibromoanthracene (3.4g, 10mmol) and fluoranthene-3-boric acid (2.5g, 10mmol) were dissolved in a mixed solvent of 1, 4-dioxane and water (100 ml/10 ml), and Pd (PPh) was added 3 ) 4 (1.15g, 1mmol) and potassium carbonate (8.3g, 60mmol). Stirring was carried out at 100 ℃ for 12h under a nitrogen atmosphere. After cooling, most of the solvent is removed by rotary evaporation, then liquid is extracted and washed by water, and the intermediate 8-1 is obtained by organic phase column chromatography and recrystallization, and the yield is as follows: and 64 percent. MS (ASAP) =456.1.
Synthesis of intermediate 8-2:
the intermediate 8-1 (4.6g, 10mmol) and 4-chlorophenylboronic acid (1.6g, 10mmol) were dissolved in a mixed solvent of 1, 4-dioxane and water (100 ml/10 ml), and Pd (PPh) was added 3 ) 4 (1.15g, 1mmol) and potassium carbonate (4.1g, 30mmol). Stirring was carried out at 100 ℃ for 12h under a nitrogen atmosphere. After cooling, most of the solvent is removed by rotary evaporation, then liquid is extracted and washed by water, and the intermediate 8-2 is obtained by organic phase column chromatography and recrystallization, and the yield is as follows: and 55 percent. MS (ASAP) =488.1.
Synthesis of compound 8:
weighing 8-2 (9.8g, 20mmol) of intermediate, 7-2 (5.6g, 20mmol) of intermediate and Pd 2 (dba) 3 (0.92g，1mmol)，t-Bu 3 P (0.24g, 1.2mmol) and sodium tert-butoxide (20g, 209mmol) were put in a 500mL three-necked flask, and 200mL of toluene was added thereto, and the mixture was reacted at 80 ℃ for 12 hours while replacing nitrogen. Spin-drying, washing with water, and performing column chromatography (eluent PE: DCM = 8). Yield: 73 percent. MS (ASAP) =734.3。
Example 9
This example provides an organic compound (compound 9).
The synthetic route for compound 9 of this example is as follows:
Figure BDA0003939242440000331
synthesis of intermediate 9-1:
9-bromo-10- (4-tert-butylphenyl) anthracene (3.9g, 10mmol) and 6-bromo-2-naphthaleneboronic acid (2.5g, 10mmol) were dissolved in a mixed solvent of 1, 4-dioxane and water (100 ml/10 ml), and Pd (PPh) was added 3 ) 4 (1.15g, 1mmol) and potassium carbonate (4.1g, 30mmol). Stirring was carried out at 100 ℃ for 12h under a nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation, followed by extraction and water washing for liquid separation, organic phase column chromatography and recrystallization to give intermediate 9-1, yield: 71 percent. MS (ASAP) =514.1.
Synthesis of compound 9:
intermediate 9-1 (10.3g, 20mmol), intermediate 7-2 (5.6g, 20mmol) and Pd were weighed 2 (dba) 3 (1.8g，2.0mmol)，t-Bu 3 P (0.51g, 2.5 mmol) and sodium t-butoxide (9.6 g, 100mmol) were placed in a 500mL three-necked flask, 200mL of toluene was added, nitrogen was replaced, and the reaction was carried out at 80 ℃ for 12 hours. Spin-drying, washing with water, and column chromatography (eluent PE: DCM = 4). MS (ASAP) =716.3.
Example 10
This example provides an organic compound (compound 10).
The synthetic route for compound 10 of this example is as follows:
Figure BDA0003939242440000341
synthesis of intermediate 10-1:
intermediate 1-1 (10g, 41.7mmol), 2-iodonaphthalene (10.7g, 42mmol) and Pd were weighed 2 (dba) 3 (1.9g，2.1mmol)，t-Bu 3 P(0.51g,2.5 mmol), sodium t-butoxide (20g, 209mmol) in a 500mL three-necked flask, 200mL of toluene was added, nitrogen gas was replaced, and the reaction was carried out at 80 ℃ for 12 hours. Spin-drying, washing with water, and performing column chromatography (eluent PE: DCM = 8). Yield: and 64 percent. MS (ASAP) =321.0.
Synthesis of intermediate 10-2:
the intermediate 10-1 (10g, 31mmol) and 2-nitrophenylboronic acid (5.2g, 31mmol) are dissolved in a mixed solvent of 1, 4-dioxane and water (100 ml/10 ml), and Pd (PPh) is added 3 ) 4 (0.86g, 0.74mmol) and potassium carbonate (25.5g, 185mmol). Stirring at 100 ℃ for 12h under nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation, and the separated liquid was extracted and washed with water, subjected to organic phase column chromatography (eluent PE: DCM = 3) and recrystallized to give intermediate 10-2, yield: 79 percent. MS (ASAP) =364.1.
Synthesis of intermediate 10-3:
intermediate 10-2 (10g, 27mmol) was added to a 100ml two-necked flask, 30ml of dichlorobenzene was added until complete dissolution, triethyl phosphite (23g, 137mmol) was added, and the mixture was stirred at 180 ℃ for 12 hours under a nitrogen atmosphere. After cooling, the solvent was distilled off under reduced pressure, dichloromethane was then added and the layers were washed with water, the organic phase was purified by column chromatography (eluent PE: DCM = 4) and recrystallized to give intermediate 10-3, yield: 46 percent. MS (ASAP) =332.1.
Synthesis of compound 10:
intermediate 10-3 (6.6g, 20mmol), 10-phenyl-9- (4-bromophenyl) anthracene (8.2g, 20mmol) and Pd were weighed 2 (dba) 3 (0.92g，1mmol)，t-Bu 3 P (0.24g, 1.2mmol) and sodium tert-butoxide (20g, 209mmol) were put in a 500mL three-necked flask, and 200mL of toluene was added thereto, and the mixture was reacted at 80 ℃ for 12 hours while replacing nitrogen. Spin-dry, water-wash, and column-chromatographe (eluent PE: DCM = 8). Yield: and 72 percent. MS (ASAP) =660.3.
Example 11
This example provides an organic compound (compound 11).
The synthetic route for compound 11 of this example is as follows:
Figure BDA0003939242440000351
synthesis of intermediate 11-1:
9, 10-dibromoanthracene (3.4g, 10mmol), 1-pyreneboronic acid (2.5g, 10mmol) was dissolved in a mixed solvent of 1, 4-dioxane and water (100 ml/10 ml), and Pd (PPh) was added 3 ) 4 (1.15g, 1mmol) and potassium carbonate (8.3g, 60mmol). Stirring was carried out at 100 ℃ for 12h under a nitrogen atmosphere. After cooling, most of the solvent is removed by rotary evaporation, then liquid is extracted and washed by water, and the intermediate 11-1 is obtained by organic phase column chromatography and recrystallization, and the yield is as follows: 73 percent. MS (ASAP) =456.1.
Synthesis of intermediate 11-2:
the intermediate 11-1 (4.6g, 10mmol) and 4-chlorobenzeneboronic acid (1.6g, 10mmol) were dissolved in a mixed solvent of 1, 4-dioxane and water (100 ml/10 ml), and Pd (PPh) was added 3 ) 4 (1.15g, 1mmol) and potassium carbonate (4.1g, 30mmol). Stirring was carried out at 100 ℃ for 12h under a nitrogen atmosphere. After cooling, most of the solvent is removed by rotary evaporation, then liquid is extracted and washed by water, and the intermediate 11-2 is obtained by organic phase column chromatography and recrystallization, and the yield is as follows: 59 percent. MS (ASAP) =488.1.
Synthesis of compound 11:
intermediate 11-2 (9.8g, 20mmol), intermediate 10-3 (6.6g, 20mmol) and Pd were weighed 2 (dba) 3 (0.92g，1mmol)，t-Bu 3 P (0.24g, 1.2mmol) and sodium tert-butoxide (20g, 209mmol) were put in a 500mL three-necked flask, and 200mL of toluene was added thereto, and the mixture was reacted at 80 ℃ for 12 hours while replacing nitrogen. Spin-dry, water-wash, and column-chromatographe (eluent PE: DCM = 8). Yield: 77 percent. MS (ASAP) =784.3.
Example 12
This example provides an organic compound (compound 12).
The synthetic route for compound 12 of this example is as follows:
Figure BDA0003939242440000352
synthesis of intermediate 12-1:
9, 10-dibromoanthracene (6.8g, 20mmol), 9-dimethylfluorene-2-boronic acid (4.8g, 20mmol) were dissolved in a mixed solvent of 1, 4-dioxane and water (100 ml/10 ml), and Pd (PPh) was added 3 ) 4 (2.3g, 2mmol) and potassium carbonate (14g, 100mmol). Stirring was carried out at 100 ℃ for 12h under a nitrogen atmosphere. After cooling, most of the solvent was removed by rotary evaporation, followed by extraction and water washing of the separated liquid, organic phase column chromatography and recrystallization to give intermediate 12-1, yield: 65 percent. MS (ASAP) =448.1
Synthesis of compound 12:
intermediate 12-1 (9.0g, 20mmol), intermediate 10-3 (6.6g, 20mmol) and Pd were weighed 2 (dba) 3 (1.8g，2.0mmol)、t-Bu 3 P (0.51g, 2.5 mmol) and sodium tert-butoxide (9.6 g, 100mmol) were placed in a 500mL three-necked flask, and 200mL of toluene was added to replace nitrogen and reacted at 80 ℃ for 12 hours. Spin-drying, washing with water, and column chromatography (eluent PE: DCM = 5) to give a white solid with 83% yield. MS (ASAP) =700.3.
Comparative example 1
The organic compound of this comparative example was BH-Ref, which has the following chemical formula:
Figure BDA0003939242440000361
the process for the preparation of organic electronic devices (OLED devices) comprising the above compounds is described in detail below by means of specific examples. The OLED device has the structure that: ITO/HIL/HTL/EML/ETL/cathode. Referring to fig. 1, fig. 1 shows a structure of an OLED device, and the OLED device 100 includes an anode (ITO) 120, a Hole Injection Layer (HIL) 130, a Hole Transport Layer (HTL) 140, an emission layer (EML) 150, an Electron Transport Layer (ETL) 160, and a cathode 170, which are stacked on a substrate 110.
Preparing an OLED device:
the structural formulas of Liq, ET and BD-1 of compounds that may be involved in the OLED preparation are as follows:
Figure BDA0003939242440000362
device example 1
The embodiment provides an OLED device, which is prepared by the following steps:
a. cleaning an ITO (indium tin oxide) conductive glass substrate: washing with various solvents (such as one or more of chloroform, acetone or isopropanol), and then performing ultraviolet ozone treatment.
b. HIL (hole injection layer, 40 nm): 40nm PEDOT (polyethylenedioxythiophene, clevios) TM AI 4083) was spin coated as HIL in a clean room and treated on a hot plate at 180 ℃ for 10 minutes.
c. HTL (hole transport layer, 20 nm): 20nm PVK (Sigma Aldrich, average Mn25,000-50,000) was made by spin coating in a nitrogen glove box using a solution of PVK added to toluene solvent at a solution solubility of 5mg/ml followed by treatment on a hotplate 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 and guests (95 weight ratio of host to guest: 5), with a solubility of 15mg/ml, followed by treatment on a hotplate at 140 ℃ for 10 minutes, the host using compound 1 of example 1 and the guest material selected from BD-1.
e. Electron transport layer and cathode: the heat treated substrate was transferred to a vacuum chamber followed by ET and Liq placed in different evaporation units under high vacuum (1 × 10) -6 Mbar) were co-deposited at a ratio of 50 wt%, respectively, to form an electron transport layer of 20nm on the light-emitting layer, followed by deposition of an Al cathode having a thickness of 100 nm.
f. And (3) packaging: the devices were encapsulated with ultraviolet curable resin in a nitrogen glove box.
Device examples 2 to 12
Compared with device example 1, the technical solutions of the OLED devices of device examples 2 to 12 are different in that: the host material in example 1 was replaced from compound 1 with the corresponding compound in table 1; other conditions were the same as in device example 1.
Comparative device example 1
Device the embodiment of the OLED device of comparative example 1 differs from device example 1 in that: compound 1 in example 1 was replaced with the corresponding compound (BH-ref) in table 1.
Test example 1
The current-voltage (J-V) characteristics of each OLED device were characterized by characterization equipment, while recording important parameters such as luminous efficiency (CE @ 1knits) and lifetime (LT90 @ 1knits), etc., and the results are detailed in Table 1.
TABLE 1
Figure BDA0003939242440000371
As can be seen from Table 1: the OELD devices 1 to 12 prepared using the organic compounds 1 to 12 of examples 1 to 12 as host materials in the emission layer according to the present application have higher emission efficiency and longer life than the blue OELD device (device comparative example 1) prepared using the organic compound of comparative example 1 as host material in the emission layer. Specifically, the blue OELD devices prepared by using the compounds 1 to 12 of examples 1 to 12 as host materials in the light emitting layer all had light emitting efficiencies in the range of 5 to 8cd/a, and had more excellent light emitting efficiencies.
In conclusion, the organic compound provided by the application is an anthracene derivative containing heterocyclic fused rings, has fluorescence emission at blue light wavelength, can be used as a main material for a light emitting layer of an organic electronic device, and can enable the organic electronic device to have high light emitting efficiency and long device life by using the organic compound.
In the foregoing embodiments, the descriptions of the respective embodiments have respective emphasis, and for parts that are not described in detail in a certain embodiment, reference may be made to the related descriptions of other embodiments.
All possible combinations of the technical features of the above embodiments may not be described for the sake of brevity, but should be considered as within the scope of the present disclosure as long as there is no contradiction between the combinations of the technical features.
The organic compounds, mixtures, compositions and organic electronic devices provided in the examples of the present application are described in detail, and the principles and embodiments of the present application are described herein using specific examples, which are provided only to help understand the method and the core concept of the present application; meanwhile, for those skilled in the art, according to the idea of the present application, there may be variations in the specific embodiments and the application scope, and in summary, the content of the present specification should not be construed as a limitation to the present application.

Claims (18)

1. An organic compound having a structure represented by general formula (1):
Figure FDA0003939242430000011
wherein Ar is 1 Has a structure shown as a general formula (2):
Figure FDA0003939242430000012
Ar 2 、Ar 3 each independently selected from substituted or unsubstituted aromatic groups containing from 6 to 60 ring atoms, substituted or unsubstituted heteroaromatic groups containing from 5 to 60 ring atoms, or combinations of these groups;
g is selected from a linear alkyl group having 1 to 20C atoms, a branched alkyl group having 3 to 20C atoms, a cyclic alkyl group having 3 to 20C atoms, a substituted or unsubstituted aromatic group containing 6 to 60 ring atoms, a substituted or unsubstituted heteroaromatic group containing 5 to 60 ring atoms, or a combination of these groups;
L 1 、L 2 each independently selected from the group consisting of a single bond, a substituted or unsubstituted aromatic group containing from 6 to 60 ring atoms, a substituted or unsubstituted heteroaromatic group containing from 5 to 60 ring atoms;
R 1 、R 2 and R 3 Each occurrence is independently selected from: -D, straight chain alkyl having 1 to 20C atoms, straight chain alkoxy having 1 to 20C atoms, straight chain thioalkoxy having 1 to 20C atoms, branched chain alkyl having 3 to 20C atoms, branched chain alkoxy having 3 to 20C atoms, branched chain thioalkoxy having 3 to 20C atoms, cyclic alkyl having 3 to 20C atoms, cyclic alkoxy having 3 to 20C atoms, cyclic thioalkoxy having 3 to 20C atoms, silyl, keto having 1 to 20C atoms, alkoxycarbonyl having 2 to 20C atoms, aryloxycarbonyl having 7 to 20C atoms, cyano, carbamoyl, haloformyl, formyl, isocyano, isocyanate, thiocyanate, isothiocyanate, hydroxyl, nitro, substituted or unsubstituted amine, -CF 3 -Cl, -Br, -F, -I, a substituted or unsubstituted aromatic group having 6 to 60 ring atoms, a substituted or unsubstituted heteroaromatic group having 5 to 60 ring atoms, a substituted or unsubstituted aryloxy group having 5 to 60 ring atoms, 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, 2,3 or 4;
m3 is 0,1, 2,3 or 4.
2. The organic compound of claim 1, wherein R is 1 、R 2 And R 3 Each occurrence is independently selected from: -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, 1-methylhexyl, 2-ethylhexyl, 2-butylhexyl, cyclohexyl, adamantyl, phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthryl, triazinyl, pyridyl, pyrimidinyl, imidazolyl, furyl, thienyl, benzofuryl, benzothienyl, indolinylIndole, carbazolyl, dibenzothienyl, dibenzofuranyl, phenyl-substituted carbazolyl, fluorenyl substituted with alkyl having 1-6C atoms, phenyl substituted with alkyl having 1-6C atoms, naphthyl substituted with alkyl having 1-6C atoms, phenyl substituted with one or more D, naphthyl substituted with phenyl.
3. The organic compound according to claim 1, wherein the organic compound has at least one of the structures represented by general formulas (3-1) to (3-2):
Figure FDA0003939242430000021
4. the organic compound according to any one of claims 1 to 3, wherein Ar is Ar 2 And G are respectively and independently selected from one of the structures shown as follows:
Figure FDA0003939242430000022
wherein, the first and the second end of the pipe are connected with each other,
x is, at each occurrence, independently selected from CR 4 Or N;
y is selected from NR 5 、CR 6 R 7 、SiR 6 R 7 O, S = O or SO 2 ；
R 4 、R 5 、R 6 、R 7 At each occurrence, is independently selected from: -H, -D, linear alkyl having 1 to 20C atoms, linear alkoxy having 1 to 20C atoms, linear thioalkoxy having 1 to 20C atoms, branched alkyl having 3 to 20C atoms, branched alkoxy having 3 to 20C atoms, branched thioalkoxy having 3 to 20C atoms, cyclic alkyl having 3 to 20C atoms, cyclic alkoxy having 3 to 20C atoms, cyclic ring having 3 to 20C atomsThioalkoxy, silyl, keto with 1 to 20C atoms, alkoxycarbonyl with 2 to 20C atoms, aryloxycarbonyl with 7 to 20C atoms, cyano, carbamoyl, haloformyl, formyl, isocyano, isocyanate, thiocyanate, isothiocyanate, hydroxy, nitro, amine, -CF 3 -Cl, -Br, -F, -I, a substituted or unsubstituted aromatic group having 6 to 60 ring atoms, a substituted or unsubstituted heteroaromatic group having 5 to 60 ring atoms, a substituted or unsubstituted aryloxy group having 5 to 60 ring atoms, a substituted or unsubstituted heteroaryloxy group having 5 to 60 ring atoms, or a combination of these groups;
R 6 and R 7 With or without rings formed therebetween.
5. The organic compound of claim 4, wherein Ar is Ar 2 Any one selected from the structures shown below:
Figure FDA0003939242430000031
wherein denotes the attachment site.
6. The organic compound according to claim 3, wherein the organic compound has at least one of the structures represented by general formulae (4-1) to (4-14):
Figure FDA0003939242430000032
Figure FDA0003939242430000041
7. the organic compound according to claim 3 or 6, wherein in the formula (3-1), the formulae (4-1) to (4-5), G is independently selected from the group consisting of the groups represented by the formulae (A-1) to (A-7):
Figure FDA0003939242430000051
wherein denotes a ligation site;
and/or the presence of a gas in the gas,
in the formulas (3-2) and (4-8) to (4-14), G is independently selected from the group consisting of the formulas (B-1) to (B-4):
Figure FDA0003939242430000052
wherein denotes a ligation site.
8. The organic compound of claim 1, wherein L is 1 、L 2 Independently selected from a single bond or at least one of the structures shown below:
Figure FDA0003939242430000053
wherein the content of the first and second substances,
X 1 at each occurrence, is independently selected from CR 8 Or N;
R 8 at each occurrence, is independently selected from: -H, -D, straight chain alkyl having 1 to 20C atoms, straight chain alkoxy having 1 to 20C atoms, straight chain thioalkoxy having 1 to 20C atoms, branched alkyl having 3 to 20C atoms, branched alkoxy having 3 to 20C atoms, branched thioalkoxy having 3 to 20C atoms, cyclic alkyl having 3 to 20C atoms, cyclic alkoxy having 3 to 20C atoms, cyclic thioalkoxy having 3 to 20C atoms, silyl, keto having 1 to 20C atoms, alkoxycarbonyl having 2 to 20C atoms, aryloxycarbonyl having 7 to 20C atoms, cyano, carbamoyl, haloformyl, formyl, isocyanatoRadicals, isocyanate, thiocyanate, isothiocyanate, hydroxyl, nitro, amine, -CF 3 -Cl, -Br, -F, -I, a substituted or unsubstituted aromatic group having 6 to 60 ring atoms, a substituted or unsubstituted heteroaromatic group having 5 to 60 ring atoms, a substituted or unsubstituted aryloxy group having 5 to 60 ring atoms, a substituted or unsubstituted heteroaryloxy group having 5 to 60 ring atoms, or a combination of these groups.
9. The organic compound of claim 1, wherein L is 1 And L 2 Each independently selected from a single bond or at least one of the following groups:
Figure FDA0003939242430000061
10. the organic compound of claim 1, wherein the organic compound comprises at least one of the following structures:
Figure FDA0003939242430000062
Figure FDA0003939242430000071
Figure FDA0003939242430000081
Figure FDA0003939242430000091
Figure FDA0003939242430000101
11. a mixture comprising an organic compound according to any one of claims 1 to 10, and further comprising an organic functional material; the organic functional material is at least one selected from a hole injection material, a hole transport material, an electron injection material, an electron blocking material, a hole blocking material, a light emitting material, a host material and an organic dye.
12. A composition comprising the organic compound according to any one of claims 1 to 10 or the mixture according to claim 11, and further comprising an organic solvent.
13. An organic electronic device comprising an anode, a cathode and an organic functional layer between the anode and the cathode; the organic functional layer comprises an organic compound according to any one of claims 1 to 10 or a mixture according to claim 11, or is prepared from a composition according to claim 12.
14. The organic electronic device according to claim 13, wherein the organic functional layer comprises a light emitting layer comprising a host material and a guest material, the host material comprising the organic compound, the guest material comprising a pyrene-based compound;
the pyrene compound has a structure shown as a general formula (5):
Figure FDA0003939242430000102
wherein the content of the first and second substances,
Ar 4 、Ar 5 、Ar 6 、Ar 7 each independently selected from: substituted or unsubstituted aromatic groups containing 6 to 60 ring atoms, substituted or unsubstitutedHeteroaromatic groups containing 6 to 60 ring atoms, or combinations of these groups;
R 9 at each occurrence, is independently selected from: -H, -D, linear alkyl having 1 to 20C atoms, linear alkoxy having 1 to 20C atoms, linear thioalkoxy having 1 to 20C atoms, branched alkyl having 3 to 20C atoms, branched alkoxy having 3 to 20C atoms, branched thioalkoxy having 3 to 20C atoms, cyclic alkyl having 3 to 20C atoms, cyclic alkoxy having 3 to 20C atoms, cyclic thioalkoxy having 3 to 20C atoms, silyl, keto having 1 to 20C atoms, alkoxycarbonyl having 2 to 20C atoms, aryloxycarbonyl having 7 to 20C atoms, cyano, carbamoyl, haloformyl, formyl, isocyano, isocyanato, thiocyanate, isothiocyanate, hydroxyl, nitro, amine, CF, hydroxyl, nitro, carboalkoxy, alkoxy, and thioalkoxy having 3 to 20C atoms 3 Cl, br, F, I, a substituted or unsubstituted aromatic group having 6 to 60 ring atoms, a substituted or unsubstituted heteroaromatic group having 5 to 60 ring atoms, a substituted or unsubstituted aryloxy group having 5 to 60 ring atoms, a substituted or unsubstituted heteroaryloxy group having 5 to 60 ring atoms, or a combination of these groups;
s is selected from 0,1, 2,3,4, 5, 6,7 or 8.
15. The organic electronic device of claim 13, wherein Ar is 4 、Ar 5 、Ar 6 、Ar 7 Each independently selected from at least one of the structures shown below:
Figure FDA0003939242430000111
wherein the content of the first and second substances,
v is independently selected from CR at each occurrence 10 Or N;
w is selected from NR 11 、CR 11 R 12 、SiR 11 R 12 O, S = O or SO 2 ；
R 10 、R 11 、R 12 At each occurrence, is independently selected from: -H, -D, straight chain alkyl having 1 to 20C atoms, straight chain alkoxy having 1 to 20C atoms, straight chain thioalkoxy having 1 to 20C atoms, branched alkyl having 3 to 20C atoms, branched alkoxy having 3 to 20C atoms, branched thioalkoxy having 3 to 20C atoms, cyclic alkyl having 3 to 20C atoms, cyclic alkoxy having 3 to 20C atoms, cyclic thioalkoxy having 3 to 20C atoms, silyl, keto having 1 to 20C atoms, alkoxycarbonyl having 2 to 20C atoms, aryloxycarbonyl having 7 to 20C atoms, cyano, carbamoyl, haloformyl, formyl, isocyano, isocyanate, thiocyanate, isothiocyanate, hydroxyl, nitro, amine, -CF 3 -Cl, -Br, -F, -I, a substituted or unsubstituted aromatic group having 6 to 60 ring atoms, a substituted or unsubstituted heteroaromatic group having 5 to 60 ring atoms, a substituted or unsubstituted aryloxy group having 5 to 60 ring atoms, a substituted or unsubstituted heteroaryloxy group having 5 to 60 ring atoms, or a combination of these groups.
16. The organic electronic device of claim 14, wherein the pyrene-based compound comprises the structure shown below:
Figure FDA0003939242430000112
17. the organic electronic device of claim 14, wherein the pyrene-based compound comprises at least one of the following structures:
Figure FDA0003939242430000113
18. the organic electronic device of claim 14, wherein the pyrene based compound comprises at least one of the structures represented by formulas (BD-1) - (BD-24):
Figure FDA0003939242430000121
CN202211414584.8A 2022-11-11 2022-11-11 Organic compounds, mixtures, compositions and organic electronic devices Pending CN115677709A (en)

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN114206875A (en) * 2020-05-29 2022-03-18 株式会社Lg化学 Compound and organic light emitting device including the same
CN114605425A (en) * 2022-04-08 2022-06-10 华南师范大学 Organic compound, and mixture, composition and organic electronic device comprising the same
CN115093333A (en) * 2022-07-08 2022-09-23 Tcl华星光电技术有限公司 Organic compounds, mixtures, compositions and organic electronic devices

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN114206875A (en) * 2020-05-29 2022-03-18 株式会社Lg化学 Compound and organic light emitting device including the same
CN114605425A (en) * 2022-04-08 2022-06-10 华南师范大学 Organic compound, and mixture, composition and organic electronic device comprising the same
CN115093333A (en) * 2022-07-08 2022-09-23 Tcl华星光电技术有限公司 Organic compounds, mixtures, compositions and organic electronic devices

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