CN115093333A - Organic compounds, mixtures, compositions and organic electronic devices - Google Patents

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

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CN115093333A
CN115093333A CN202210815388.5A CN202210815388A CN115093333A CN 115093333 A CN115093333 A CN 115093333A CN 202210815388 A CN202210815388 A CN 202210815388A CN 115093333 A CN115093333 A CN 115093333A
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organic
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organic compound
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CN115093333B (en
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宋鑫龙
肖志华
何锐锋
宋晶尧
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TCL Huaxing Photoelectric Technology Co Ltd
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TCL Huaxing Photoelectric Technology Co Ltd
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Abstract

The present application provides an organic compound, mixture, composition and organic electronic device. The organic compound has a structure shown as a general formula I:
Figure DDA0003737223720000011
the organic compound provided by the application has good stability, and can improve the luminous efficiency, the service life and the color purity of an organic electronic device.

Description

Organic compound, mixture, composition and organic electronic device
Technical Field
The application relates to the technical field of display, in particular to an organic compound, a mixture, a composition and an organic electronic device.
Background
Organic electronic devices, particularly Organic Light Emitting Diodes (OLEDs), have characteristics such as self-luminescence, high brightness, high efficiency, low driving voltage, wide viewing angle, high contrast, and high responsiveness, and are widely used. The organic electroluminescent device generally includes a positive electrode, a negative electrode, and an organic layer between the positive electrode and the negative electrode, and the organic layer generally includes a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and the like. When a voltage is applied between the anode and the cathode of the organic electroluminescent device, the anode injects holes into the organic layer, the cathode injects electrons into the organic layer, the holes and the electrons meet to form excitons, and the excitons jump back to the ground state to emit light.
The organic electroluminescent device using the blue fluorescent material has high reliability. However, the existing blue light fluorescent material has a wide emission spectrum and poor color purity, and is not beneficial to high-end display. And the existing blue light fluorescent material is complex to synthesize and is not beneficial to large-scale mass production. In addition, the efficiency and lifetime of the existing blue organic electroluminescent device are still to be improved.
The light-emitting layer of the existing blue light organic electroluminescent device adopts a host-guest doped structure. Most blue light host materials adopt anthracene-based fused ring derivatives, most blue light guest compounds adopt aryl vinyl amine compounds, the compounds have poor thermal stability and are easy to decompose, so that the service life of the device is poor, and meanwhile, the compounds have poor color purity and are difficult to realize deep blue light emission. There is therefore a problem in realizing a full-color display.
Disclosure of Invention
In view of the above, the present application provides an organic compound, a mixture, a composition and an organic electronic device, which aim to solve the problems of low light-emitting efficiency, short lifetime and poor color purity of the existing organic electronic device.
The application provides an organic compound having a structure represented by general formula I:
Figure BDA0003737223700000021
wherein the content of the first and second substances,
n1 is any integer from 1 to 8; m1 is any integer of 0-5;
R 1 independently at each occurrence, H, D, or a straight chain alkyl group having 1 to 20C atoms, or a straight chain alkoxy group having 1 to 20C atoms, or a straight chain thioalkoxy group having 1 to 20C atoms, or a branched or cyclic alkyl group having 3 to 20C atoms, or a branched or cyclic alkoxy group having 3 to 20C atoms, or a branched or cyclic thioalkoxy group having 3 to 20C atoms, a silyl group, or a ketone group having 1 to 20C atoms, or an alkoxycarbonyl group having 2 to 20C atoms, or an aryloxycarbonyl group having 7 to 20C atoms, or a substituted or unsubstituted aromatic or heteroaromatic group having 5 to 60 ring atoms, or an aryloxy or heteroaryloxy group having 5 to 60 ring atoms, a cyano group, Carbamoyl, haloformyl, formyl, isocyano, isocyanate, thiocyanate, isothiocyanate, hydroxy, nitro, amino, CF 3 Cl, Br, F, I or combinations of these, wherein adjacent R 1 Can form a ring with each other;
Ar 1 and Ar 2 At each occurrenceEach independently selected from the group consisting of substituted or unsubstituted aromatic groups containing 6 to 60C atoms, substituted or unsubstituted heteroaromatic groups containing 5 to 60 ring atoms, and substituted or unsubstituted non-aromatic ring systems containing 3 to 30 ring atoms;
R 2 each occurrence is independently selected from H, D, or a straight chain alkyl group having 1 to 20C atoms, or a branched alkyl group having 3 to 20C atoms, or a cyclic alkyl group having 3 to 20C atoms, a substituted or unsubstituted aromatic group having 6 to 30 ring atoms, a substituted or unsubstituted heteroaromatic group having 5 to 30 ring atoms.
In an alternative embodiment of the present application, the organic compound is selected from any one of the structures represented by general formulas (II-1) to (II-4):
Figure BDA0003737223700000031
wherein the content of the first and second substances,
r in the general formulae (II-1) to (II-3) 1 Each occurrence is independently selected from D, or a straight chain alkyl group having 1 to 10C atoms, or a branched or cyclic alkyl group having 3 to 10C atoms, or an aryl group having 5 to 20 ring atoms, or a heteroaryl group having 5 to 20 ring atoms, or a combination of these groups.
Ar 1 And Ar 2 Each occurrence is independently selected from the group consisting of substituted or unsubstituted aromatic groups containing 6 to 14C atoms, and substituted or unsubstituted heteroaromatic groups containing 5 to 14 ring atoms.
In an alternative embodiment of the present application, the Ar 1 And Ar 2 At each occurrence, each is independently selected from one of the following groups:
Figure BDA0003737223700000032
wherein each occurrence of X is independently selected from CR 2 Or N; y is selected from NR 3 、CR 3 R 4 、SiR 3 R 4 、O、S、S＝OOr SO 2 ；
R 2 、R 3 And R 4 Each occurrence is independently selected from H, D, or a linear alkyl group having 1 to 20C atoms, or a linear alkoxy group having 1 to 20C atoms, or a linear thioalkoxy group having 1 to 20C atoms, or a branched or cyclic alkyl group having 3 to 20C atoms, or a branched or cyclic alkoxy group having 3 to 20C atoms, or a branched or cyclic thioalkoxy group having 3 to 20C atoms, a silyl group, or a ketone group having 1 to 20C atoms, or an alkoxycarbonyl group having 2 to 20C atoms, or an aryloxycarbonyl group having 7 to 20C atoms, or a substituted or unsubstituted aryl group having 5 to 60 ring atoms, or a substituted or unsubstituted heteroaryl group having 5 to 60 ring atoms, or an aryloxy group having 5 to 60 ring atoms, Or heteroaryloxy having 5 to 60 ring atoms, cyano, amino, carbamoyl, haloformyl, formyl, isocyano, isocyanate, thiocyanate, isothiocyanate, hydroxy, nitro, CF 3 Cl, Br, F, or a combination of these groups.
In an alternative embodiment of the present application, the Ar 1 And Ar 2 Each independently selected from one of the following groups:
Figure BDA0003737223700000041
wherein the content of the first and second substances,
"" indicates a connection site; n is 2 Any integer selected from 0 to 3;
R 2 independently at each occurrence selected from H, D, or a straight chain alkyl group having 1 to 10C atoms, or a branched or cyclic alkyl group having 3 to 10C atoms, or a substituted or unsubstituted aromatic group having 5 to 30 ring atoms, or a substituted or unsubstituted heteroaromatic group having 5 to 30 ring atoms, or a combination of these;
R 3 and R 4 Each occurrence is independently selected from H, D, or a straight chain alkyl group having 1 to 10C atoms, or a branched or cyclic alkane having 3 to 10C atomsA group, or a substituted or unsubstituted aromatic group having 5 to 30 ring atoms, or a substituted or unsubstituted heteroaromatic group having 5 to 30 ring atoms, or a combination of these groups.
In an optional embodiment of the present application, the Ar 1 And Ar 2 Each independently selected from one of the following groups:
Figure BDA0003737223700000051
wherein "+" denotes the attachment site; tAm represents a 2- (2-methyl) butyl group; tBu represents a tert-butyl group.
In an alternative embodiment of the present application, the organic compound is selected from any one of the following structures:
Figure BDA0003737223700000061
Figure BDA0003737223700000071
Figure BDA0003737223700000081
Figure BDA0003737223700000091
Figure BDA0003737223700000101
Figure BDA0003737223700000111
Figure BDA0003737223700000121
Figure BDA0003737223700000131
Figure BDA0003737223700000141
Figure BDA0003737223700000151
Figure BDA0003737223700000161
Figure BDA0003737223700000171
the present application also provides a mixture comprising the organic compound as described above and at least one organic functional material selected from at least one of a hole injection material, a hole transport material, an electron injection material, an electron blocking material, a hole blocking material, a light emitter, a light emitting host material, and an organic dye.
The present application also provides a composition comprising an organic compound as described above or a mixture as described above and at least one organic solvent.
The present application also provides an organic electronic device comprising an organic compound as described above or a mixture as described above.
In an alternative embodiment of the present application, the organic electronic device comprises a light-emitting layer comprising an organic compound as described above.
The beneficial effect of this application lies in: the application provides an organic compound, which is an indene-containing arylamine compound, the structure of the organic compound has a better conjugated system, the stability is better, and the organic compound is applied to an organic electronic device, so that the service life of the organic electronic device can be prolonged. Meanwhile, the organic compound has fluorescence emission with the light-emitting wavelength at short wavelength, and the light-emitting spectrum shows narrow half-peak width, so that the organic compound is used as a blue fluorescent light-emitting material, the light-emitting efficiency of an organic electronic device can be improved, and deep blue light emission is realized.
Drawings
In order to illustrate the embodiments or the technical solutions in the prior art more clearly, the drawings needed to be used in the description of the embodiments or the prior art will be briefly described below, and it is obvious that the drawings in the following description are only some embodiments of the invention, and it is obvious for a person skilled in the art that other drawings can be obtained according to these drawings without creative efforts.
Fig. 1 is a schematic structural diagram of an organic electronic device according to an embodiment of the present disclosure.
Description of the drawings: 101-substrate, 102-anode, 103-hole injection layer, 104-hole transport layer, 105-light-emitting layer, 106-electron transport layer, 107-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. It should be apparent that the described embodiments are only a few embodiments of the present application, and not all 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, it is to be understood that the terms "upper", "lower", and the like, indicate orientations or positional relationships based on the orientations or positional relationships shown in the drawings, are only for convenience in describing the present application and simplifying the description, and do not indicate or imply that the referred device or element must have a specific orientation, be constructed in a specific orientation, and be operated, and thus, should not be construed as limiting the present application. Furthermore, the terms "first", "second" and "first" are used for descriptive purposes only and are not to be construed as indicating or implying relative importance or to implicitly indicate the number of technical features indicated. Thus, features defined as "first", "second", may explicitly or implicitly include one or more of the described features. In the description of the present application, "a plurality" means two or more unless explicitly defined otherwise.
The present application may repeat reference numerals and/or letters in the various implementations, such repetition is for the purpose of simplicity and clarity and does not in itself dictate a relationship between the various implementations and/or configurations discussed.
In the present application, the compositions, printing inks, or inks have the same meaning and are interchangeable.
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, the same substituent, when multiple occurrences occur, may be independently selected from different groups. If the formula contains a plurality of R1, then R1 can be independently selected from different groups. For example, in
Figure BDA0003737223700000191
The 6R 1 on the benzene ring may be the same or different from each other.
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 to be optionally substituted with art-acceptable groups including, but not limited to: c 1-30 Alkyl, heterocyclic group containing 3 to 20 ring atoms, aryl group containing 5 to 20 ring atoms, heteroaryl group containing 5 to 20 ring atoms, silane group, carbonyl group, alkoxycarbonyl group, aryloxycarbonyl group, carbamoyl group, haloformyl group, formyl group, -NRR', cyano group, isocyano group, isocyanate group, thiocyanate group, isothiocyanate group, hydroxyl group, trifluoro groupMethyl, nitro or halogen, and the above groups may also be further substituted with art-acceptable substituents; it is understood that R and R 'in-NRR' are each independently substituted with art-acceptable groups including, but not limited to, H, C 1-6 An alkyl group, a cycloalkyl group having 3 to 8 ring atoms, a heterocyclic group having 3 to 8 ring atoms, an aryl group having 5 to 20 ring atoms or a heteroaryl group having 5 to 10 ring atoms; said C is 1-6 Alkyl, cycloalkyl containing 3 to 8 ring atoms, heterocyclyl containing 3 to 8 ring atoms, aryl containing 5 to 20 ring atoms or heteroaryl containing 5 to 10 ring atoms are optionally further substituted by one or more of the following: c 1-6 Alkyl, cycloalkyl having 3 to 8 ring atoms, heterocyclyl having 3 to 8 ring atoms, halogen, hydroxy, nitro or amino.
In the present application, the "number of ring atoms" refers to 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 atoms contained in the substituent are 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.
In the present application, "alkyl" may denote a linear, branched and/or cyclic alkyl group. The carbon number of the alkyl group may be 1-50, 1-30, 1-20, 1-10, or 1-6. 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, 4-methylcyclohexyl, 4-tert-butylcyclohexyl, n-heptyl, 1-methylheptyl, 2-dimethylheptyl, 2-ethylheptyl, 2-butylheptyl, n-octyl, tert-octyl, 2-ethyloctyl, 2-butyloctyl, 2-hexyloctyl, tert-butyl, 2-isobutyl, 2-ethylbutyl, 3-dimethylbutyl, 2-methylhexyl, 2-ethylhexyl, 2-butylhexyl, cyclohexyl, 4-butylcyclohexyl, 2-butylheptyl, 2-methylheptyl, 2-ethylheptyl, 2-ethyloctyl, 2-tert-butylhexyl, 2-butylhexyl, or a, 3, 7-dimethyloctyl, cyclooctyl, n-nonyl, n-decyl, adamantyl, 2-ethyldecyl, 2-butyldecyl, 2-hexyldecyl, 2-octyldecyl, n-undecyl, n-dodecyl, 2-ethyldodecyl, 2-butyldodecyl, 2-hexyldodecyl, 2-octyldodecyl, n-tridecyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, 2-ethylhexadecyl, 2-butylhexadecyl, 2-hexylhexadecyl, 2-octylhexadecyl, n-heptadecyl, n-octadecyl, n-nonadecyl, n-eicosyl, 2-ethyleicosyl, 2-butyleicosyl, 2-hexyleicosyl, 2-octyleicosyl, tert-dodecyl, n-eicosyl, 2-ethyleicosyl, 2-butyleicosyl, 2-hexyleicosyl, 2-octyleicosyl, tert-dodecyl, sec-dodecyl, a, N-heneicosyl, n-docosyl, n-tricosyl, n-tetracosyl, n-pentacosyl, n-hexacosyl, n-heptacosyl, n-octacosyl, n-nonacosyl, n-triacontyl, etc.
In the present application, "aryl, aryl or aromatic group" refers to a hydrocarbon group containing at least one aromatic ring. "heteroaryl or heteroaromatic group" refers to an aromatic hydrocarbon group that contains at least one heteroatom. The heteroatoms are preferably selected from Si, N, P, O, S and/or Ge, particularly preferably from Si, N, P, O and/or S. By fused ring aromatic group is meant that the rings of the aromatic group may have two or more rings in which two carbon atoms are shared by two adjacent rings, i.e., fused rings. The fused heterocyclic aromatic group means a fused ring aromatic hydrocarbon group containing at least one hetero atom. For the purposes of this application, aromatic or heteroaromatic groups include not only aromatic ring systems but also non-aromatic ring systems. Thus, systems such as pyridine, thiophene, pyrrole, pyrazole, triazole, imidazole, oxazole, oxadiazole, thiazole, tetrazole, pyrazine, pyridazine, pyrimidine, triazine, carbene, and the like are also considered for purposes of this application to be aromatic or heterocyclic aromatic groups. For the purposes of this application, fused-ring aromatic or fused-heterocyclic aromatic ring systems include not only systems of aromatic or heteroaromatic groups, but also systems in which a plurality of aromatic or heterocyclic aromatic groups may also be interrupted by short non-aromatic units (< 10% of non-H atoms, preferably less than 5% of non-H atoms, such as C, N or O atoms). Thus, for example, systems such as 9, 9' -spirobifluorene, 9, 9-diarylfluorene, triarylamines, diaryl ethers, etc., are also considered fused ring aromatic ring systems for the purposes of this application.
In the present application, the aromatic group is selected from: benzene, naphthalene, anthracene, fluoranthene, phenanthrene, triphenylene, perylene, tetracene, pyrene, benzopyrene, acenaphthene, fluorene, and derivatives thereof; the heteroaromatic group is selected from the group consisting of triazines, pyridines, pyrimidines, imidazoles, furans, thiophenes, benzothiophenes, indoles, carbazoles, pyrroloimidazoles, pyrrolopyrroles, thienopyrroles, thienothiophenes, furopyrroles, furofurans, thienofurans, benzisoxazoles, benzisothiazoles, benzimidazoles, quinolines, isoquinolines, phthalazines, quinoxalines, phenanthridines, primadines, quinazolines, quinazolinones, dibenzothiophenes, dibenzofurans, carbazoles, and derivatives thereof.
In the present application, when no attachment site is indicated in a group, it means that an optionally attachable site in the group serves as an attachment site.
In the present application, when no fusion site is specified in the group, it means that an optionally annealable site in the group is a fusion site, and preferably two or more sites in the ortho-position in the group are fusion sites.
In this application, a single bond connecting substituents through the corresponding ring means that the substituent may be attached to an optional position of the ring, e.g.
Figure BDA0003737223700000211
Wherein R is connected with any substitutable site of benzene ring,
Figure BDA0003737223700000212
represents a group consisting of 1 or more R 1 Can be connected with any substitutable site of the four benzene rings, and n represents R 1 The number of (2).
In the present application, the energy level structure of the organic material, the triplet energy level ET1, the highest occupied orbital energy level HOMO, and the lowest unoccupied orbital energy level LUMO play a key role. The determination of these energy levels is described below. The HOMO and LUMO energy levels can be measured by the photoelectric effect, for example XPS (X-ray photoelectron spectroscopy) and UPS (ultraviolet photoelectron spectroscopy) or by cyclic voltammetry (hereinafter referred to as CV). Recently, quantum chemical methods such as density functional theory (hereinafter abbreviated as DFT) have become effective methods for calculating the molecular orbital level. The triplet energy level ET1 of the organic material can be measured by low temperature Time resolved luminescence spectroscopy, or obtained by quantum simulation calculations (e.g. by Time-dependent, DFT), such as by the commercial software Gaussian 09W (Gaussian Inc.). It should be noted that the absolute values of HOMO, LUMO, ET1 depend on the measurement or calculation method used, and even for the same method, different methods of evaluation, e.g. starting point and peak point on the CV curve, may give different HOMO/LUMO values. Thus, a reasonably meaningful comparison should be made with the same measurement method and the same evaluation method. In the description of the embodiments of the present application, the values of HOMO, LUMO, ET1 are based on a Time-dependent DFT simulation, but do not affect the application of other measurement or calculation methods.
The technical solution provided by the present application will be described in detail below.
The application provides an organic compound having a structure shown in general formula I:
Figure BDA0003737223700000221
wherein, the first and the second end of the pipe are connected with each other,
n1 is any integer from 1 to 8; m1 is any integer of 0-5;
R 1 independently at each occurrence, H, D, or a straight chain alkyl group having 1 to 20C atoms, or a straight chain alkoxy group having 1 to 20C atoms, or a straight chain thioalkoxy group having 1 to 20C atoms, or a branched or cyclic alkyl group having 3 to 20C atoms, or a branched or cyclic alkoxy group having 3 to 20C atoms, or a branched or cyclic thioalkoxy group having 3 to 20C atoms, a silyl group, or a ketone group having 1 to 20C atoms, or an alkoxycarbonyl group having 2 to 20C atoms, or an aryloxycarbonyl group having 7 to 20C atoms, or a substituted or unsubstituted aromatic or heteroaromatic group having 5 to 60 ring atoms, or an aryloxy or heteroaryloxy group having 5 to 60 ring atoms, a cyano group, Carbamoyl, haloformyl, formylRadical, isocyano radical, isocyanate radical, thiocyanate radical, isothiocyanate radical, hydroxyl radical, nitro radical, amino radical, CF 3 Cl, Br, F, I or combinations of these, wherein adjacent R 1 Can form a ring with each other;
Ar 1 and Ar 2 Each occurrence is independently selected from the group consisting of substituted or unsubstituted aromatic groups containing 6 to 60C atoms, substituted or unsubstituted heteroaromatic groups containing 5 to 60 ring atoms, substituted or unsubstituted non-aromatic ring systems containing 3 to 30 ring atoms;
R 2 each occurrence is independently selected from H, D, or a straight chain alkyl group having 1 to 20C atoms, or a branched alkyl group having 3 to 20C atoms, or a cyclic alkyl group having 3 to 20C atoms, a substituted or unsubstituted aromatic group having 6 to 30 ring atoms, a substituted or unsubstituted heteroaromatic group having 5 to 30 ring atoms.
In some embodiments, R 1 Independently for each occurrence, H, D, or a straight chain alkyl group having 1 to 10C atoms, or a branched or cyclic alkyl group having 3 to 10C atoms, or an aryl group having 5 to 20 ring atoms, or a heteroaryl group having 5 to 20 ring atoms, or a combination of these groups.
In some embodiments, R 1 Selected from H, D, or a straight chain alkyl group having 1 to 8C atoms, or a branched or cyclic alkyl group having 3 to 8C atoms for each occurrence.
In some embodiments, R 1 Selected from the group consisting of H, 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, 4-methylcyclohexyl, 4-tert-butylcyclohexyl, n-heptyl, 1-methylheptyl, 2-dimethylheptyl, 2-ethylheptyl, 2-butylheptyl, n-octyl, tert-octyl, 2-ethyloctyl, 2-butyloctyl, 2-hexyloctyl, n-butyl, sec-butyl, tert-butyl, isobutyl, 2-ethylbutyl, 3-dimethylbutyl, 2-ethylhexyl, 2-butylhexyl, 2-ethylhexyl, 2-pentyl, 4-pentyl, 2-methylpentyl, 4-methylpentyl, 2-methylpentyl, 4-methylheptyl, 2-methylheptyl, 2-ethylheptyl, 2-octyl, 2-ethylheptyl, 2-ethyloctyl, 2-tert-octyl, 2-ethyloctyl, 2-tert-pentyl, 2-pentyl, or a-pentyl, 2-pentyl, or a-pentyl, 2-pentyl, or a-pentyl, 2-pentyl, or a-pentyl, 2-pentyl, or a-pentyl, 2-pentyl, or a-pentyl, or-hexyl, or-pentyl, or a, 3, 7-dimethyloctyl, cyclooctyl, n-nonylOne of n-decyl, adamantyl, or 2- (2-methyl) butyl.
In some embodiments, n1 is any integer from 1 to 4; further, n1 is 2.
In an alternative embodiment of the present application, the organic compound is selected from the group consisting of structures represented by general formulas (II-1) to (II-4):
Figure BDA0003737223700000241
wherein the content of the first and second substances,
r in the general formulae (II-1) to (II-3) 1 Each occurrence is independently selected from D, or a straight chain alkyl group having 1 to 10C atoms, or a branched or cyclic alkyl group having 3 to 10C atoms, or an aryl group having 5 to 20 ring atoms, or a heteroaryl group having 5 to 20 ring atoms, or a combination of these groups.
Ar 1 And Ar 2 Each occurrence is independently selected from the group consisting of substituted or unsubstituted aromatic groups containing 6 to 14C atoms, and substituted or unsubstituted heteroaromatic groups containing 5 to 14 ring atoms.
In some embodiments, R in formulas (II-1) - (II-3) 1 Independently for each occurrence, is selected from D, or a straight chain alkyl group having 1 to 8C atoms, or a branched or cyclic alkyl group having 3 to 8C atoms.
In some embodiments, R is described in general formulas (II-1) - (II-3) 1 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, 4-methylcyclohexyl, 4-tert-butylcyclohexyl, n-heptyl, 1-methylheptyl, 2-dimethylheptyl, 2-ethylheptyl, 2-butylheptyl, n-octyl, tert-octyl, 2-ethyloctyl, 2-butyloctyl, 2-hexyloctyl, n-butyl, sec-butyl, tert-butyl, isobutyl, 2-ethylbutyl, 3-dimethylpentyl, 4-methyl-2-pentyl, 2-methylhexyl, 2-ethylhexyl, 2-methylheptyl, 2-ethylheptyl, 2-ethyloctyl, 2-tert-octyl, 2-pentyl, or 2-pentyl, or a, 2-pentyl, or a, 3, 7-dimethyloctyl, cyclooctyl, n-nonyl, n-decylAdamantyl or 2- (2-methyl) butyl.
In some embodiments, R 1 And, in multiple occurrences, are selected from the same group.
In an alternative embodiment of the present application, the Ar 1 And Ar 2 At each occurrence, each is independently selected from one of the following groups:
Figure BDA0003737223700000251
wherein, each occurrence of X is independently selected from CR 2 Or N; y is selected from NR 3 、CR 3 R 4 、SiR 3 R 4 O, S, S ═ O or SO 2 ；
R 2 、R 3 And R 4 Each occurrence is independently selected from H, D, or a straight chain alkyl group having 1 to 20C atoms, or a straight chain alkoxy group having 1 to 20C atoms, or a straight chain thioalkoxy group having 1 to 20C atoms, or a branched or cyclic alkyl group having 3 to 20C atoms, or a branched or cyclic alkoxy group having 3 to 20C atoms, or a branched or cyclic thioalkoxy group having 3 to 20C atoms, a silyl group, or a ketone group having 1 to 20C atoms, or an alkoxycarbonyl group having 2 to 20C atoms, or an aryloxycarbonyl group having 7 to 20C atoms, or a substituted or unsubstituted aromatic group having 5 to 60 ring atoms, or a substituted or unsubstituted heteroaromatic group having 5 to 60 ring atoms, or an aryloxycarbonyl group having 5 to 60 ring atoms, Or heteroaryloxy having 5 to 60 ring atoms, cyano, amino, carbamoyl, haloformyl, formyl, isocyano, isocyanate, thiocyanate, isothiocyanate, hydroxy, nitro, CF 3 Cl, Br, F, or a combination of these groups.
When X is a linking site, X is a C atom.
In an alternative embodiment of the present application, the Ar 1 And Ar 2 Each independently selected from one of the following groups:
Figure BDA0003737223700000252
wherein, the first and the second end of the pipe are connected with each other,
"" indicates a connection site; n is 2 Any integer selected from 0 to 3;
R 2 independently at each occurrence selected from H, D, or a straight chain alkyl group having 1 to 10C atoms, or a branched or cyclic alkyl group having 3 to 10C atoms, or a substituted or unsubstituted aromatic group having 5 to 30 ring atoms, or a substituted or unsubstituted heteroaromatic group having 5 to 30 ring atoms, or a combination of these;
R 3 and R 4 Each occurrence is independently selected from H, D, or a straight chain alkyl group having 1 to 10C atoms, or a branched or cyclic alkyl group having 3 to 10C atoms, or a substituted or unsubstituted aryl group having 5 to 30 ring atoms, or a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms, or a combination of these groups.
In some embodiments, R 2 Each occurrence is independently selected from H, D, or a straight chain alkyl group having 1 to 8C atoms, or a branched or cyclic alkyl group having 3 to 8C atoms, or a phenyl, pyridyl, pyrimidinyl, or naphthyl group.
In some embodiments, R 2 Each occurrence is independently selected from the group consisting of H, 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, 4-methylcyclohexyl, 4-tert-butylcyclohexyl, n-heptyl, 1-methylheptyl, 2-dimethylheptyl, 2-ethylheptyl, 2-butylheptyl, n-octyl, tert-octyl, 2-ethyloctyl, 2-butyloctyl, 2-hexyloctyl, n-butyl, sec-butyl, tert-butyl, 2-methyl-pentyl, 4-methylpentyl, 2-methylpentyl, 4-methylheptyl, 2-ethylpentyl, 2-ethylheptyl, 2-ethyloctyl, tert-octyl, 2-ethyloctyl, 2-hexyloctyl, 2-octyloctyl, n-butylheptyl, n-butyl, tert-octyl, 2-pentyl, tert-pentyl, 2, or a, 2, or a, L, or a, L, or a, L, or a, L, or a, L, 3, 7-dimethyloctyl, cyclooctyl, n-nonyl, n-decyl, adamantyl or one of 2- (2-methyl) butyl, phenyl, pyridyl, pyrimidinyl or naphthyl.
In some embodiments, R 3 And R 4 Each independently selected from H, D, or a straight chain alkyl group having 1 to 8C atoms, or a branched or cyclic alkyl group having 3 to 8C atoms, or a phenyl, pyridyl, pyrimidinyl or naphthyl group.
In some embodiments, R 3 And R 4 Each independently selected from H, D, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, phenyl, pyridyl, pyrimidyl or naphthyl.
In an alternative embodiment of the present application, the Ar 1 And Ar 2 Each independently selected from one of the following groups:
Figure BDA0003737223700000271
wherein "+" attached to a single bond represents a connection site; tAm represents a 2- (2-methyl) butyl group; tBu represents a tert-butyl group.
In some embodiments, Ar 1 And Ar 2 And, when occurring, are selected from the same group.
In some embodiments, Ar 1 And Ar 2 And, when present, are selected from different groups.
In an alternative embodiment of the present application, the organic compound is selected from any one of the following structures:
Figure BDA0003737223700000281
Figure BDA0003737223700000291
Figure BDA0003737223700000301
Figure BDA0003737223700000311
Figure BDA0003737223700000321
Figure BDA0003737223700000331
Figure BDA0003737223700000341
Figure BDA0003737223700000351
Figure BDA0003737223700000361
Figure BDA0003737223700000371
Figure BDA0003737223700000381
Figure BDA0003737223700000391
Figure BDA0003737223700000401
the organic compound can be used as a functional material in organic electronic devices, especially Organic Light Emitting Diodes (OLEDs).
In some embodiments, the organic compound may serve as a blue light emitting material.
Specifically, the organic compound can be used as a blue fluorescent luminescent material and applied to a luminescent material of an organic electronic device. The organic compound has a stable conjugated system structure, so that the thermal stability of the organic compound is better, the organic compound is applied to a luminescent material of an organic electronic device, the service life of the organic electronic device can be effectively prolonged, the organic compound has fluorescence emission with the luminescent wavelength positioned at short wavelength, and the luminescent spectrum shows that the luminescent wavelength has narrow half-peak width, so that the organic compound is used as a blue luminescent material, the luminescent efficiency of the organic electronic device can be improved, and deep blue luminescence is realized.
The present application also provides a mixture comprising the organic compound and at least one organic functional material selected from at least one of 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), an organic dye, and the like. Various organic functional materials are described in detail, for example, in patents WO2010135519a1, US20090134784a1 and WO2011110277a1, the entire contents of these 3 patent documents being incorporated herein by reference.
The present application also provides a composition comprising the organic compound or the mixture and at least one organic solvent.
Wherein the composition is used as a printing ink or coating for the preparation of the organic electronic device.
In the preparation of the organic electronic device by printing or coating, suitable printing or coating techniques include, but are not limited to, ink jet printing, letterpress printing, screen printing, dip coating, spin coating, knife coating, roll printing, twist roll printing, offset printing, flexographic printing, rotary printing, spray coating, brush or pad printing, slot die coating, and the like. Gravure printing, jet printing and ink jet printing are preferred. The composition may additionally include one or more components such as surface active compounds, lubricants, wetting agents, dispersants, hydrophobing agents, binders, and the like, for adjusting viscosity, film forming properties, enhancing adhesion, and the like.
In some embodiments, the organic solvent is selected from at least one of an aromatic or heteroaromatic, ester, aromatic ketone or ether, aliphatic ketone or ether, cycloaliphatic or olefinic compound, borate, or phosphate-based compound.
In some embodiments, the organic solvent is selected from aromatic or heteroaromatic-based solvents.
In particular, the aromatic or heteroaromatic-based solvents include, but are not limited to: p-diisopropylbenzene, pentylbenzene, tetrahydronaphthalene, cyclohexylbenzene, chloronaphthalene, 1, 4-dimethylnaphthalene, 3-isopropylbiphenyl, p-methylisopropylbenzene, dipentylbenzene, tripentylbenzene, 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, diphenylbenzene, phenylpyridine, and phenylpyridine, N-methyldiphenylamine, 4-isopropylbiphenyl, α -dichlorodiphenylmethane, 4- (3-phenylpropyl) pyridine, benzyl benzoate, 1-bis (3, 4-dimethylphenyl) ethane, 2-isopropylnaphthalene, quinoline, isoquinoline, methyl 2-furancarboxylate, ethyl 2-furancarboxylate, and the like.
In particular, the aromatic ketone-based solvent includes, but is not limited to: 1-tetralone, 2- (phenylepoxy) tetralone, 6- (methoxy) tetralone, acetophenone, propiophenone, benzophenone, and derivatives thereof, such as 4-methylacetophenone, 3-methylacetophenone, 2-methylacetophenone, 4-methylpropiophenone, 3-methylpropiophenone, 2-methylpropiophenone, and the like.
In particular, the aromatic ether-based solvent includes, but is not limited to: 3-phenoxytoluene, butoxybenzene, p-anisaldehyde dimethylacetal, tetrahydro-2-phenoxy-2H-pyran, 1, 2-dimethoxy-4- (1-propenyl) benzene, 1, 4-benzodioxan, 1, 3-dipropylbenzene, 2, 5-dimethoxytoluene, 4-ethylphenetole, 1, 3-dipropoxybenzene, 1,2, 4-trimethoxybenzene, 4- (1-propenyl) -1, 2-dimethoxybenzene, 1, 3-dimethoxybenzene, glycidylphenyl ether, dibenzyl ether, 4-t-butylanisole, trans-p-propenylanisole, 1, 2-dimethoxybenzene, 1-methoxynaphthalene, diphenyl ether, 2-phenoxymethyl ether, methyl ether, 2-phenoxytetrahydrofuran, ethyl-2-naphthyl ether, and the like.
In some embodiments, the organic solvent may preferably be selected from: aliphatic ketones such as 2-nonanone, 3-nonanone, 5-nonanone, 2-decanone, 2, 5-hexanedione, 2,6, 8-trimethyl-4-nonanone, fenchylone, phorone, isophorone, di-n-amyl ketone, etc.; or aliphatic ethers such as amyl ether, hexyl ether, dioctyl ether, ethylene glycol dibutyl ether, diethylene glycol diethyl ether, diethylene glycol butyl methyl ether, diethylene glycol dibutyl ether, triethylene glycol dimethyl ether, triethylene glycol ethyl methyl ether, triethylene glycol butyl methyl ether, tripropylene glycol dimethyl ether, tetraethylene glycol dimethyl ether, and the like.
In some embodiments, the organic solvent may be selected from ester-based solvents: alkyl octanoates, alkyl sebacates, alkyl stearates, alkyl benzoates, alkyl phenylacetates, alkyl cinnamates, alkyl oxalates, alkyl maleates, alkyl lactones, alkyl oleates, and the like. Particularly preferred are octyl octanoate, diethyl sebacate, diallyl phthalate, isononyl isononanoate and the like.
The organic solvent may contain one kind of the above-mentioned organic solvent, or may be a mixture containing two or more kinds of the above-mentioned organic solvents.
In some embodiments, preferably, the organic solvent includes, but is not limited to: methanol, ethanol, 2-methoxyethanol, methylene chloride, chloroform, chlorobenzene, o-dichlorobenzene, tetrahydrofuran, anisole, morpholine, toluene, o-xylene, m-xylene, p-xylene, 1, 4-dioxane, acetone, methyl ethyl ketone, 1, 2-dichloroethane, 3-phenoxytoluene, 1,1, 1-trichloroethane, 1,1,2, 2-tetrachloroethane, ethyl acetate, butyl acetate, dimethylformamide, dimethylacetamide, dimethyl sulfoxide, tetrahydronaphthalene, decalin, indene, and/or mixtures thereof.
The organic solvent is a solvent with Hansen (Hansen) solubility parameters in the following range:
δ d (dispersion force) of 17.0 to 23.2MPa 1/2 In particular in the range of 18.5 to 21.0MPa 1/2 A range of (d);
δ p (polar force) is 0.2 to 12.5MPa 1/2 In particular in the range of 2.0 to 6.0MPa 1/2 A range of (d);
δ h (hydrogen bonding force) of 0.9 to 14.2MPa 1/2 In particular in the range of 2.0 to 6.0MPa 1/2 In (c) is used.
The organic solvent is selected by considering the boiling point parameter. In the application, the boiling point of the organic solvent is more than or equal to 150 ℃; 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 more than or equal to 275 ℃ or more than or equal to 300 ℃. Boiling points in these ranges are beneficial for preventing nozzle clogging in inkjet print heads. The organic solvent may be evaporated from the solvent system to form a thin film comprising the functional material.
In some embodiments, the composition may be a solution or a suspension.
In some embodiments, the mass percentage of the organic compound or the mixture in the composition is 0.01 wt% to 20 wt%.
Preferably, the mass percentage of the organic compound or the mixture in the composition is 0.1 wt% to 15 wt%.
More preferably, the mass percentage of the organic compound or the mixture in the composition is 0.2 wt% to 5 wt%.
More preferably, the mass percentage of the organic compound or the mixture in the composition is 0.25 wt% to 3 wt%.
In the present application, the organic compound, the mixture, and the composition may be applied to the organic electronic device. Such organic electronic devices include, but are not limited to: organic Light Emitting Diodes (OLEDs), Organic photovoltaic cells (OPVs), Organic light Emitting cells (OLEECs), Organic Field Effect Transistors (OFETs), Organic light Emitting field effect transistors (efets), Organic lasers, Organic spintronic devices, Organic sensors, and Organic Plasmon Emitting diodes (Organic plasma Emitting diodes), among others.
In the present application, the organic electronic device comprises at least one organic functional layer selected from at least one of a hole injection layer, a hole transport layer, an electron injection layer, an electron blocking layer, and a hole blocking layer, the organic functional layer comprising the organic compound or the mixture.
In an alternative embodiment of the present application, the organic electronic device includes a light emitting layer including the organic compound.
The organic compound is an indene-containing arylamine compound, has a better conjugated system and better stability, can effectively prolong the service life of an organic electronic device when applied to a luminescent layer material of the organic electronic device, and has fluorescence emission with a luminescent wavelength at a short wavelength, and a luminescent spectrum shows narrow half-peak width, so that the luminescent efficiency can be effectively improved.
Referring to fig. 1, an embodiment of an organic electronic device is provided.
Such organic electronic devices include, but are not limited to: OLED, OLEEC or organic light emitting field effect transistor. In the present embodiment, an OLED device is taken as an example.
The OLED device 100 includes a substrate 101, an anode 102, a hole injection layer 103, a hole transport layer 104, an emission layer 105, an electron transport layer 106, and a cathode 107. The light-emitting layer 105 contains at least one of the organic compounds.
Specifically, the substrate 101 may be a transparent substrate or an opaque substrate. The substrate 101 may be a rigid substrate or an elastic substrate. The substrate 101 may be made of plastic, metal, semiconductor wafer or glass. Preferably, the substrate 101 has a smooth surface. Preferably, the substrate 101 is a flexible substrate, the material of the flexible substrate is a polymer film or plastic, and the glass transition temperature Tg is greater than or equal to 150 ℃; preferably, the glass transition temperature of the substrate 101 is greater than or equal to 200 ℃; preferably, the glass transition temperature of the substrate 101 is greater than or equal to 250 ℃; most preferably, the glass transition temperature of the substrate 101 is 300 ℃ or higher. The flexible substrate may be polyethylene terephthalate (PET) or polyethylene glycol (2, 6-naphthalene) (PEN).
Specifically, the material of the anode 102 is a conductive metal, a conductive metal oxide, a conductive polymer, or the like. The anode 102 can easily inject holes into the hole injection layer 103, the hole transport layer 104, or the light emitting layer 105. The absolute value of the difference between the work function of the anode 102 and the HOMO level or the valence band level of the emitter in the light emitting layer 105 or the hole injection layer 103, the hole transport layer 104, or the p-type semiconductor material in the electron blocking layer is less than 0.5eV, preferably less than 0.3eV, and more preferably less than 0.2 eV. The material of the anode 102 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). The anode material may be formed into the anode 102 using methods known in the art for forming anodes, such as radio frequency magnetron sputtering, vacuum thermal evaporation, electron beam (e-beam), and the like in physical vapor deposition methods.
The material of the cathode 107 is a conductive metal or a conductive metal oxide. The cathode 107 can easily inject electrons into the electron injection layer, the electron transport layer 106, or the light emitting layer 105. The absolute value of the difference between the work function of the cathode 107 and the LUMO level or the conduction band level of the light emitter or the electron injection layer in the light-emitting layer 105, the electron transport layer 106, or the n-type semiconductor material in the hole-blocking layer is less than 0.5eV, preferably less than 0.3eV, and more preferably less than 0.2 eV. The cathode 107 material may be selected from, but is not limited to, Al, Au, Ag, Ca, Ba, Mg, LiF/Al, MgAg alloy, BaF 2 At least one of Al, Cu, Fe, Co, Ni, Mn, Pd, Pt and ITO. The cathode material may be formed using a method known in the art for forming a cathode, such as radio frequency magnetron sputtering in a physical vapor deposition method, vacuum thermal evaporation, electron beam (e-beam), and the like, to form the cathode 107.
In other embodiments, the OLED device may further include other functional layers, such as an electron blocking layer, an electron injection layer, an electron transport layer, and the like.
The materials of the hole injection layer, the hole transport layer, the electron blocking layer, the electron injection layer, the electron transport layer, and the hole blocking layer of the OLED device 100 are known in the art to be applied to the hole injection layer, the hole transport layer, the electron blocking layer, the electron injection layer, the electron transport layer, and the hole blocking layer.
In this embodiment, the light emitting wavelength range of the OLED device 100 is 300-1000nm, preferably 350-900nm, and more preferably 400-800 nm.
The present application also relates to the use of the organic electronic device in an electronic device, which may be, but is not limited to, a display device, a lighting device, a light source, a sensor, etc., and an electronic device comprising the organic electronic device.
The following are examples of the organic compounds and synthesis methods of the present application, and the following examples are only preferred examples of the present application and are not intended to limit the present application.
Example 1
The synthetic route for organic compound 1 is as follows:
Figure BDA0003737223700000461
1. synthesis of intermediate Compounds 1-3
Mixing compound 1-1(10mmol), compound 1-2(10mmol), palladium catalyst Pd (dba) 2 (0.1mmol), TTBP (tri-tert-butylphosphine) (0.2mmol) and sodium tert-butoxide (30mmol) are dissolved in toluene solvent, stirred at 100 ℃ for 6h under nitrogen atmosphere, cooled, evaporated to remove solvent, extracted, washed with water, and separated by organic phase column chromatography to obtain 7.69mmol of intermediate compound 1-3. The yield of intermediate compound 1-3 was 76.9%, and ms (asap) 207.3.
2. Synthesis of organic Compound 1
Mixing intermediate compound 1-3(20mmol), compound 1-4(10mmol), palladium catalyst Pd (dba) 2 (0.1mmol), TTBP (0.2mmol) and sodium tert-butoxide (30mmol) were dissolved in toluene solvent, stirred at 100 ℃ for 6h under nitrogen atmosphere,and (3) cooling, performing rotary evaporation to remove the solvent, extracting, washing the separated liquid with water, and performing organic phase column chromatography to separate to obtain the organic compound 1. The yield of organic compound 1 was 78.8%, and ms (asap) was 612.4.
Example 2
The synthetic route of organic compound 2 is as follows:
Figure BDA0003737223700000462
1. synthesis of intermediate Compounds 1-3
Mixing compound 1-1(10mmol), compound 1-2(10mmol), palladium catalyst Pd (dba) 2 (0.1mmol), TTBP (tri-tert-butylphosphine) (0.2mmol) and sodium tert-butoxide (30mmol) are dissolved in toluene solvent, stirred at 100 ℃ for 6h under nitrogen atmosphere, cooled, evaporated to remove solvent, extracted, washed with water, and separated by organic phase column chromatography to obtain 7.69mmol of intermediate compound 1-3. The yield of intermediate compound 1-3 was 76.9%, and ms (asap) 207.3.
2. Synthesis of organic compound 2:
mixing compound 1-3(20mmol), compound 2-1(10mmol), Pd (dba) 2 (0.1mmol), TTBP (0.2mmol) and sodium tert-butoxide (30mmol) were dissolved in toluene and stirred at 100 ℃ for 6h under a nitrogen atmosphere. And (3) cooling, performing rotary evaporation to remove the solvent, extracting, washing the separated liquid with water, and performing organic phase column chromatography to obtain the organic compound 2. The yield of organic compound 2 was 67.9%, and ms (asap) 696.3.
Example 3
The synthetic route of organic compound 3 is as follows:
Figure BDA0003737223700000471
1. synthesis of intermediate 3-2:
mixing compound 3-3(10mmol), compound 3-1(10mmol), Pd (dba) 2 (0.1mmol), TTBP (0.2mmol) and sodium tert-butoxide (30mmol) were dissolved in toluene and stirred at 100 ℃ for 6h under a nitrogen atmosphere. Cooling, rotary evaporating to remove solvent, extracting, washing with water, and separating liquidAnd carrying out organic phase column chromatography to obtain the intermediate compound 3-2 with the molar weight of the intermediate 3-2 being 7.07 mmol. The yield of intermediate compound 3-2 was 70.7%, and ms (asap) was 283.3.
2. Synthesis of organic compound 3:
mixing compound 3-2(20mmol), compound 2-1(10mmol), Pd (dba) 2 (0.1mmol), TTBP (0.2mmol) and sodium tert-butoxide (30mmol) were dissolved in toluene and stirred at 100 ℃ under a nitrogen atmosphere for 6 h. And (3) cooling, performing rotary evaporation to remove the solvent, extracting, washing the separated liquid with water, and performing organic phase column chromatography to obtain the organic compound 3. The yield of organic compound 3 was 55.4%, and ms (asap) was 848.4.
Example 4
The synthetic route of organic compound 4 is as follows:
Figure BDA0003737223700000481
1. synthesis of intermediate 4-2:
mixing compound 3-3(10mmol), compound 4-1(10mmol), Pd (dba) 2 (0.1mmol), TTBP (0.2mmol) and sodium tert-butoxide (30mmol) were dissolved in toluene and stirred at 100 ℃ for 6h under a nitrogen atmosphere. And (3) cooling, performing rotary evaporation to remove the solvent, extracting, washing the separated liquid with water, and performing organic phase column chromatography to obtain an intermediate compound 4-2 of which the molar weight is 6.63 mmol. The yield of intermediate compound 4-2 was 66.3%, and ms (asap) was 283.3.
2. Synthesis of organic compound 4:
mixing compound 4-2(20mmol), compound 2-1(10mmol), Pd (dba) 2 (0.1mmol), TTBP (0.2mmol) and sodium tert-butoxide (30mmol) were dissolved in toluene and stirred at 100 ℃ for 6h under a nitrogen atmosphere. And (3) cooling, performing rotary evaporation to remove the solvent, extracting, washing the separated liquid with water, and performing organic phase column chromatography to obtain an organic compound 4. The yield of organic compound 4 was 69.3%, and ms (asap) was 848.4.
Example 5
The synthetic route for organic compound 5 is as follows:
Figure BDA0003737223700000482
1. synthesis of intermediate 5-2:
mixing compound 1-2(10mmol), compound 5-1(10mmol), Pd (dba) 2 (0.1mmol), TTBP (0.2mmol) and sodium tert-butoxide (30mmol) were dissolved in toluene and stirred at 100 ℃ for 6h under a nitrogen atmosphere. And (3) cooling, performing rotary evaporation to remove the solvent, extracting, washing the separated liquid with water, and performing organic phase column chromatography to obtain an intermediate compound 5-2 of which the molar weight is 7.34 mmol. The yield of intermediate compound 5-2 was 73.4%, and ms (asap) was 297.1.
2. Synthesis of organic compound 5:
mixing compound 5-2(20mmol), compound 2-1(10mmol), Pd (dba) 2 (0.1mmol), TTBP (0.2mmol) and sodium tert-butoxide (30mmol) were dissolved in toluene and stirred at 100 ℃ under a nitrogen atmosphere for 6 h. And (3) cooling, performing rotary evaporation to remove the solvent, extracting, washing the separated liquid with water, and performing organic phase column chromatography to obtain the organic compound 5. The yield of organic compound 5 was 67.1%, and ms (asap) was 876.3.
Example 6
The synthetic route for organic compound 6 is as follows:
Figure BDA0003737223700000491
1. synthesis of intermediate 6-2:
mixing the compound 6-3(10mmol), the compound 6-1(10mmol), Pd (dba) 2 (0.1mmol), TTBP (0.2mmol) and sodium tert-butoxide (30mmol) were dissolved in toluene and stirred at 100 ℃ for 6h under a nitrogen atmosphere. And (3) cooling, performing rotary evaporation to remove the solvent, extracting, washing the separated liquid with water, and performing organic phase column chromatography to obtain an intermediate compound 6-2 of which the molar weight is 6.32 mmol. The yield of intermediate compound 6-2 was 63.2%, and ms (asap) was 297.1.
2. Synthesis of organic compound 6:
mixing compound 6-2(20mmol), compound 2-1(10mmol), Pd (dba) 2 (0.1mmol), TTBP (0.2mmol) and sodium tert-butoxide (30mmol) were dissolved in toluene at 100 ℃ under a nitrogen atmosphereStirring for 6 h. And (3) cooling, performing rotary evaporation to remove the solvent, extracting, washing the separated liquid with water, and performing organic phase column chromatography to obtain the organic compound 6. The yield of organic compound 6 was 75.3%, and ms (asap) was 876.3.
Example 7
The synthetic route for organic compound 7 is as follows:
Figure BDA0003737223700000501
1. synthesis of intermediate 7-2:
mixing the compound 6-3(10mmol), the compound 7-1(10mmol), Pd (dba) 2 (0.1mmol), TTBP (0.2mmol) and sodium tert-butoxide (30mmol) were dissolved in toluene and stirred at 100 ℃ under a nitrogen atmosphere for 6 h. And (3) cooling, performing rotary evaporation to remove the solvent, extracting, washing the separated liquid with water, and performing organic phase column chromatography to obtain an intermediate compound 7-2 with the molar weight of 7.35mmol of the intermediate compound 7-2. The yield of intermediate compound 7-2 was 73.5%, and ms (asap) was 313.6.
2. Synthesis of organic compound 7:
mixing the compound 7-2(20mmol), the compound 2-1(10mmol), Pd (dba) 2 (0.1mmol), TTBP (0.2mmol) and sodium tert-butoxide (30mmol) were dissolved in toluene and stirred at 100 ℃ for 6h under a nitrogen atmosphere. And (3) cooling, removing the solvent by rotary evaporation, extracting, washing the separated liquid with water, and performing organic phase column chromatography to obtain the organic compound 7. The yield of organic compound 7 was 61.3%, and ms (asap) was 908.7.
Example 8
The synthetic route for compound 8 is as follows:
Figure BDA0003737223700000511
1. synthesis of intermediate 8-2:
mixing compound 8-3(10mmol), compound 8-1(10mmol), Pd (dba) 2 (0.1mmol), TTBP (0.2mmol) and sodium tert-butoxide (30mmol) were dissolved in toluene and stirred at 100 ℃ for 6h under a nitrogen atmosphere. Cooling, removing solvent by rotary evaporation, extracting, washing with water, separating, and performing organic phase column chromatography to obtainTo the intermediate 8-2 molar amount of 5.79mmol of intermediate compound 8-2. The yield of intermediate compound 8-2 was 57.9%, and ms (asap) 323.6.
2. Synthesis of organic compound 8:
mixing compound 8-2(20mmol), compound 2-1(10mmol), Pd (dba) 2 (0.1mmol), TTBP (0.2mmol) and sodium tert-butoxide (30mmol) were dissolved in toluene and stirred at 100 ℃ under a nitrogen atmosphere for 6 h. And (3) cooling, removing the solvent by rotary evaporation, extracting, washing the separated liquid with water, and performing organic phase column chromatography to obtain an organic compound 8. The yield of organic compound 8 was 66.9%, and ms (asap) was 928.4.
Example 9
The synthetic route for organic compound 9 is as follows:
Figure BDA0003737223700000512
1. synthesis of intermediate 9-2:
mixing compound 9-3(10mmol), compound 9-1(10mmol), Pd (dba) 2 (0.1mmol), TTBP (0.2mmol) and sodium tert-butoxide (30mmol) were dissolved in toluene and stirred at 100 ℃ for 6h under a nitrogen atmosphere. And (3) after cooling, removing the solvent by rotary evaporation, extracting, washing and separating liquid, and performing organic phase column chromatography to obtain an intermediate compound 9-2 of which the molar weight of the intermediate 9-2 is 8.32 mmol. The yield of intermediate compound 9-2 was 83.2%, and ms (asap) was 310.5.
2. Synthesis of organic compound 9:
mixing compound 9-2(20mmol), compound 2-1(10mmol), Pd (dba) 2 (0.1mmol), TTBP (0.2mmol) and sodium tert-butoxide (30mmol) were dissolved in toluene and stirred at 100 ℃ for 6h under a nitrogen atmosphere. And (3) cooling, performing rotary evaporation to remove the solvent, extracting, washing the separated liquid with water, and performing organic phase column chromatography to obtain the compound 9. The yield of organic compound 9 was 68.4%, and ms (asap) was 902.2.
Example 10
The synthetic route for compound 10 is shown below:
Figure BDA0003737223700000521
1. synthesis of intermediate 10-2:
mixing the compound 10-3(10mmol), the compound 10-1(10mmol), Pd (dba) 2 (0.1mmol), TTBP (0.2mmol) and sodium tert-butoxide (30mmol) were dissolved in toluene and stirred at 100 ℃ for 6h under a nitrogen atmosphere. And (3) cooling, performing rotary evaporation to remove the solvent, extracting, washing the separated liquid with water, and performing organic phase column chromatography to obtain an intermediate compound 10-2 of which the molar weight is 6.97 mmol. The yield of intermediate compound 10-2 was 69.7%, and ms (asap) was 386.2.
2. Synthesis of compound 10:
mixing compound 10-2(20mmol), compound 2-1(10mmol), Pd (dba) 2 (0.1mmol), TTBP (0.2mmol) and sodium tert-butoxide (30mmol) were dissolved in toluene and stirred at 100 ℃ for 6h under a nitrogen atmosphere. And (3) cooling, performing rotary evaporation to remove the solvent, extracting, washing the separated liquid with water, and performing organic phase column chromatography to obtain the compound 10. The yield of organic compound 10 was 78.5%, and ms (asap) 1054.5.
Example 11
The synthetic route for compound 11 is shown below:
Figure BDA0003737223700000531
1. synthesis of intermediate 10-2:
mixing compound 10-3(10mmol), compound 10-1(10mmol), Pd (dba) 2 (0.1mmol), TTBP (0.2mmol) and sodium tert-butoxide (30mmol) were dissolved in toluene and stirred at 100 ℃ for 6h under a nitrogen atmosphere. And (3) cooling, removing the solvent by rotary evaporation, extracting, washing and separating liquid, and performing organic phase column chromatography to separate to obtain 80.3mmol of the intermediate compound 10-2. The yield of the intermediate compound 10-2 was 80.3%, and ms (asap) was 386.2.
2. Synthesis of compound 11:
mixing compound 10-2(20mmol), compound 11-1(10mmol), Pd (dba) 2 (0.1mmol), TTBP (0.2mmol) and sodium tert-butoxide (30mmol) were dissolved in toluene and stirred at 100 ℃ for 6h under a nitrogen atmosphere. Cooling, rotary evaporating to remove solvent, extracting, and washingLiquid and organic phase column chromatography to obtain the compound 11. The yield of organic compound 11 was 75.9%, and ms (asap) was 998.2.
Example 12
The synthetic route for compound 12 is as follows:
Figure BDA0003737223700000541
1. synthesis of intermediate 7-2:
mixing compound 6-3(10mmol), compound 7-1(10mmol), Pd (dba) 2 (0.1mmol), TTBP (0.2mmol) and sodium tert-butoxide (30mmol) were dissolved in toluene and stirred at 100 ℃ for 6h under a nitrogen atmosphere. And (3) cooling, performing rotary evaporation to remove the solvent, extracting, washing the separated liquid with water, and performing organic phase column chromatography to separate to obtain 7.35mmol of an intermediate compound 7-2. The yield of intermediate compound 7-2 was 73.5%, and ms (asap) was 313.6.
2. Synthesis of compound 12:
mixing compound 7-2(20mmol), compound 11-1(10mmol), Pd (dba) 2 (0.1mmol), TTBP (0.2mmol) and sodium tert-butoxide (30mmol) were dissolved in toluene and stirred at 100 ℃ for 6h under a nitrogen atmosphere. And (3) cooling, performing rotary evaporation to remove the solvent, extracting, washing the separated liquid with water, and performing organic phase column chromatography to obtain the compound 12. The yield of organic compound 12 was 71.7%, and ms (asap) was 852.2.
Example 13
The synthetic route for compound 13 is as follows:
Figure BDA0003737223700000542
1. synthesis of intermediate 6-2:
mixing compound 6-3(10mmol), compound 6-1(10mmol), Pd (dba) 2 (0.1mmol), TTBP (0.2mmol) and sodium tert-butoxide (30mmol) were dissolved in toluene and stirred at 100 ℃ under a nitrogen atmosphere for 6 h. And (3) cooling, performing rotary evaporation to remove the solvent, extracting, washing the separated liquid with water, and performing organic phase column chromatography to separate to obtain 6.32mmol of intermediate compound 6-2. Wherein the yield of the intermediate compound 6-2 is 63.2 percent,MS(ASAP)＝297.1。
2. synthesis of compound 13:
mixing compound 6-2(20mmol), compound 11-1(10mmol), Pd (dba) 2 (0.1mmol), TTBP (0.2mmol) and sodium tert-butoxide (30mmol) were dissolved in toluene and stirred at 100 ℃ for 6h under a nitrogen atmosphere. And (3) cooling, performing rotary evaporation to remove the solvent, extracting, washing the separated liquid with water, and performing organic phase column chromatography to obtain a compound 13. The yield of organic compound 13 was 76.9%, and ms (asap) was 820.6.
Example 14
The synthetic route for compound 14 is as follows:
Figure BDA0003737223700000551
1. synthesis of intermediate 8-2:
mixing compound 8-3(10mmol), compound 8-1(10mmol), Pd (dba) 2 (0.1mmol), TTBP (0.2mmol) and sodium tert-butoxide (30mmol) were dissolved in toluene and stirred at 100 ℃ for 6h under a nitrogen atmosphere. And (3) cooling, performing rotary evaporation to remove the solvent, extracting, washing the separated liquid with water, and performing organic phase column chromatography to separate to obtain 5.79mmol of the intermediate compound 8-2. The yield of intermediate compound 8-2 was 57.9%, and ms (asap) 323.6.
2. Synthesis of compound 14:
mixing compound 8-2(20mmol), compound 11-1(10mmol), Pd (dba) 2 (0.1mmol), TTBP (0.2mmol) and sodium tert-butoxide (30mmol) were dissolved in toluene and stirred at 100 ℃ under a nitrogen atmosphere for 6 h. And after cooling, removing the solvent by rotary evaporation, extracting, washing the separated liquid by water, and performing organic phase column chromatography to obtain the compound 14. Wherein the yield of organic compound 14 is 87.6%, and ms (asap) 872.4.
Comparative example:
the chemical structures of comparative compound 1 and comparative compound 2 are as follows:
Figure BDA0003737223700000561
organic compound energy level calculation:
the energy levels HOMO, LUMO, T1 and S1 were calculated for the organic compounds of examples 1-14 and comparative compound 1, comparative compound 1.
The calculation method comprises the following steps: by using TD-DFT (including time density functional theory) through Gaussian 09W (Gaussian Inc.), firstly, a Semi-empirical method of 'group State/Semi-empirical/Default Spin/AM 1' (Charge0/Spin Singlet) is used for optimizing the molecular geometrical structure, and then the energy structure of the organic molecule is calculated by the TD-DFT (including time density functional theory) method to obtain 'TD-SCF/DFT/Default Spin/B3PW 91' and a base group of '6-31G (d)' (Charge0/Spin Singlet). The HOMO and LUMO energy levels were calculated according to the following calibration formula, and S1, T1 and resonance factor f (S1) were used directly.
HOMO(eV)＝((HOMO(G)×27.212)-0.9899)/1.1206；
LUMO(eV)＝((LUMO(G)×27.212)-2.0041)/1.385。
Where HOMO, LUMO, T1, and S1 are direct calculations of Gaussian 09W, given in Hartree. The results are shown in table 1 below.
Table 1:
Figure BDA0003737223700000562
Figure BDA0003737223700000571
preparing and detecting a device:
OLED devices were prepared using the organic compounds 1-14 prepared in examples 1-14 above and comparative compound 1 and comparative compound 2, respectively. The OLED device is prepared by the following steps:
a. providing an ITO (indium tin oxide) conductive glass substrate, cleaning the substrate by using a cleaning agent, and then carrying out ultraviolet ozone treatment, wherein the cleaning agent can be one or more of but not limited to chloroform, acetone or isopropanol;
b. spin-coating PEDOT (polyethylene dioxythiophene, Clevios) on the ITO conductive glass substrate in an ultra-clean room TM AI4083) Then processing the mixture for 10 minutes on a hot plate at 180 ℃ to obtain a hole injection layer with the thickness of 40 nm;
c. a TFB or PVK (Sigma Aldrich, average Mn 25,000-50,000) solution with toluene as a solvent at a concentration of 5mg/ml was spin-coated on the hole injection layer in a nitrogen glove box, followed by treatment on a hot plate at 180 ℃ for 60 minutes to obtain a hole transport layer having a thickness of 20 nm;
d. in a nitrogen glove box, an organic luminescent material mixture is spin-coated on the hole transport layer, and then treated on a hot plate at 140 ℃ for 10 minutes to obtain an organic luminescent layer with a thickness of 40nm, wherein in the organic luminescent material mixture, a solvent is methyl benzoate, a host material is BH, and guest materials are organic compounds 1 to 14 prepared in examples 1 to 14, comparative compound 1 and comparative compound 2, respectively, and a weight ratio of the host material to the guest material is 95: 5;
e. transferring the substrate into a vacuum cavity, placing ET and Liq into different evaporation units, co-depositing the ET and the Liq respectively in a proportion of 50 wt% in high vacuum (1 x 10 < -6 > mbar), forming an electron transport layer with the thickness of 20nm on the organic light-emitting layer, and then depositing an Al cathode with the thickness of 100nm to respectively obtain OLED devices;
f. and packaging the OLED device by using ultraviolet curing resin in a nitrogen glove box.
Devices OLED-1, OLED-2, OLED-3, OLED-4, OLED-5, OLED-6, OLED-7, OLED-8, OLED-9, OLED-10, OLED-11, OLED-12, OLED-13, OLED-14, OLED-Ref1 and OLED-Ref2 are respectively and correspondingly prepared from the organic compounds 1-14, the comparative compound 1 and the comparative compound 2;
wherein, the chemical structural formula of BH in step d is as follows:
Figure BDA0003737223700000581
wherein, the chemical structural formulas of the comparative compound 1 and the comparative compound 2 in the step d are as follows:
Figure BDA0003737223700000582
wherein the chemical structural formula of ET in the step e is as follows:
Figure BDA0003737223700000583
wherein the chemical structural formula of Liq in the step e is as follows:
Figure BDA0003737223700000591
the current-voltage (J-V) characteristics of each of the prepared OLED devices were characterized by characterization equipment, while recording important parameters such as luminous efficiency (CE @1knits) and lifetime (LT90@1knits), and the results are shown in table 2.
Table 2:
Figure BDA0003737223700000592
as can be seen from Table 2, the color coordinates of the OELD devices prepared using the organic compounds 1-14 as the light-emitting bodies in the organic light-emitting layer are better than those of the OELD devices prepared using the comparative compounds 1-2 as the light-emitting bodies. According to the color coordinate graph, the lower the X, Y values of the color coordinates, the more toward deep blue, the organic compounds 1 to 14 of the present application are more toward deep blue than the comparative compounds 1 to 2.
In addition, the OELD devices prepared by using the organic compounds 1-14 as the light-emitting bodies in the organic light-emitting layer have light-emitting efficiencies in the range of 8-9cd/A, and have more excellent light-emitting efficiencies. This is because the organic compound of the present application introduces cyclopentenyl groups as compared with comparative compound 1, and the indene groups in the organic compound of the present application are superior to the biphenyl groups in comparative compound 1 and the dibenzofuran structure in comparative compound 2 in the stability after film formation as compared with comparative compounds 1-2. Therefore, the lifetime of the OLED device prepared using the organic compounds 1 to 14 as the light-emitting body in the organic light-emitting layer is more superior to that of the OELD device prepared using the comparative compounds 1 to 2 as the light-emitting body in terms of the lifetime of the OELD device.
In summary, the organic compound provided by the application is an indene-containing arylamine compound, the structure of the organic compound has a better conjugated system, the stability is better, and the organic compound is applied to an organic electronic device, so that the service life of the organic electronic device can be prolonged. Meanwhile, the organic compound has fluorescence emission with the light-emitting wavelength at a short wavelength, and the light-emitting spectrum shows that the light-emitting wavelength has narrow half-peak width, so that the organic compound is used as a blue fluorescent light-emitting material, the light-emitting efficiency of an organic electronic device can be improved, and deep blue light emission is realized.
In summary, although the present application has been described with reference to the preferred embodiments, the above-described preferred embodiments are not intended to limit the present application, and those skilled in the art can make various changes and modifications without departing from the spirit and scope of the present application, so that the scope of the present application shall be determined by the scope of the appended claims.

Claims (10)

1. An organic compound having a structure represented by formula I:
Figure FDA0003737223690000011
wherein the content of the first and second substances,
n1 is any integer from 1 to 8; m1 is any integer of 0 to 5;
R 1 each occurrence is independently selected from H, D, or a straight chain alkyl group having 1 to 20C atoms, or a straight chain alkoxy group having 1 to 20C atoms, or a straight chain thioalkoxy group having 1 to 20C atoms, or a branched or cyclic alkyl group having 3 to 20C atoms, or a branched or cyclic alkoxy group having 3 to 20C atoms, or a branched or cyclic thioalkoxy group having 3 to 20C atoms, a silyl group, or a ketone group having 1 to 20C atoms, or an alkoxycarbonyl group having 2 to 20C atoms, or an aryloxycarbonyl group having 7 to 20C atoms, or an aryloxycarbonyl group having 5 to 60C atomsSubstituted or unsubstituted aromatic or heteroaromatic groups of ring atoms, or aryloxy or heteroaryloxy having 5 to 60 ring atoms, cyano, carbamoyl, haloformyl, formyl, isocyano, isocyanate, thiocyanate, isothiocyanate, hydroxyl, nitro, amine, CF 3 Cl, Br, F, I or combinations of these, wherein adjacent R 1 Can form a ring with each other;
Ar 1 and Ar 2 Each occurrence is independently selected from the group consisting of substituted or unsubstituted aromatic groups containing 6 to 60C atoms, substituted or unsubstituted heteroaromatic groups containing 5 to 60 ring atoms, and substituted or unsubstituted non-aromatic ring systems containing 3 to 30 ring atoms;
R 2 each occurrence is independently selected from H, D, or a straight chain alkyl group having 1 to 20C atoms, or a branched alkyl group having 3 to 20C atoms, or a cyclic alkyl group having 3 to 20C atoms, a substituted or unsubstituted aromatic group having 6 to 30 ring atoms, a substituted or unsubstituted heteroaromatic group having 5 to 30 ring atoms.
2. The organic compound according to claim 1, wherein the organic compound is selected from any one of the structures represented by general formulas (II-1) to (II-4):
Figure FDA0003737223690000021
wherein the content of the first and second substances,
r in the general formulae (II-1) to (II-3) 1 Each occurrence is independently selected from D, or a straight chain alkyl group having 1 to 10C atoms, or a branched or cyclic alkyl group having 3 to 10C atoms, or an aryl group having 5 to 20 ring atoms, or a heteroaryl group having 5 to 20 ring atoms, or a combination of these groups.
Ar 1 And Ar 2 Each occurrence is independently selected from the group consisting of substituted or unsubstituted aromatic groups containing 6 to 14C atoms, and substituted or unsubstituted heteroaromatic groups containing 5 to 14 ring atoms.
3. The organic compound of claim 1 or 2, wherein Ar is 1 And Ar 2 At each occurrence, each is independently selected from one of the following groups:
Figure FDA0003737223690000022
wherein each occurrence of X is independently selected from CR 2 Or N; y is selected from NR 3 、CR 3 R 4 、SiR 3 R 4 O, S, S ═ O or SO 2 ；
R 2 、R 3 And R 4 Each occurrence is independently selected from H, D, or a straight chain alkyl group having 1 to 20C atoms, or a straight chain alkoxy group having 1 to 20C atoms, or a straight chain thioalkoxy group having 1 to 20C atoms, or a branched or cyclic alkyl group having 3 to 20C atoms, or a branched or cyclic alkoxy group having 3 to 20C atoms, or a branched or cyclic thioalkoxy group having 3 to 20C atoms, a silyl group, or a ketone group having 1 to 20C atoms, or an alkoxycarbonyl group having 2 to 20C atoms, or an aryloxycarbonyl group having 7 to 20C atoms, or a substituted or unsubstituted aromatic group having 5 to 60 ring atoms, or a substituted or unsubstituted heteroaromatic group having 5 to 60 ring atoms, or an aryloxycarbonyl group having 5 to 60 ring atoms, Or heteroaryloxy having 5 to 60 ring atoms, cyano, amino, carbamoyl, haloformyl, formyl, isocyano, isocyanate, thiocyanate, isothiocyanate, hydroxy, nitro, CF 3 Cl, Br, F, or a combination of these groups.
4. The organic compound of claim 3, wherein Ar is Ar 1 And Ar 2 Each independently selected from one of the following groups:
Figure FDA0003737223690000031
wherein the content of the first and second substances,
"" indicates a connection site; n is a radical of an alkyl radical 2 Any integer selected from 0 to 3;
R 2 independently at each occurrence selected from H, D, or a straight chain alkyl group having 1 to 10C atoms, or a branched or cyclic alkyl group having 3 to 10C atoms, or a substituted or unsubstituted aromatic group having 5 to 30 ring atoms, or a substituted or unsubstituted heteroaromatic group having 5 to 30 ring atoms, or a combination of these;
R 3 and R 4 Each occurrence is independently selected from H, D, or a straight chain alkyl group having 1 to 10C atoms, or a branched or cyclic alkyl group having 3 to 10C atoms, or a substituted or unsubstituted aryl group having 5 to 30 ring atoms, or a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms, or a combination of these groups.
5. The organic compound of claim 4, wherein Ar is Ar 1 And Ar 2 Each independently selected from one of the following groups:
Figure FDA0003737223690000041
wherein the content of the first and second substances,
"" indicates a connection site;
tAm represents a 2- (2-methyl) butyl group; tBu represents a tert-butyl group.
6. The organic compound of claim 1, wherein the organic compound is selected from any one of the following structures:
Figure FDA0003737223690000051
Figure FDA0003737223690000061
Figure FDA0003737223690000071
Figure FDA0003737223690000081
Figure FDA0003737223690000091
Figure FDA0003737223690000101
Figure FDA0003737223690000111
Figure FDA0003737223690000121
Figure FDA0003737223690000131
Figure FDA0003737223690000141
Figure FDA0003737223690000151
Figure FDA0003737223690000161
7. a mixture comprising an organic compound according to any one of claims 1 to 6 and at least one organic functional material selected from at least one of a hole injecting material, a hole transporting material, an electron injecting material, an electron blocking material, a hole blocking material, a light emitter, a light emitting host material and an organic dye.
8. A composition comprising an organic compound according to any one of claims 1 to 6 or a mixture according to claim 7 and at least one organic solvent.
9. An organic electronic device comprising an organic compound according to any one of claims 1 to 6 or a mixture according to claim 7.
10. The organic electronic device according to claim 9, comprising a light-emitting layer comprising the organic compound according to any one of claims 1 to 6.
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