CN115093333B - Organic compounds, mixtures, compositions and organic electronic devices - Google Patents

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

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CN115093333B
CN115093333B CN202210815388.5A CN202210815388A CN115093333B CN 115093333 B CN115093333 B CN 115093333B CN 202210815388 A CN202210815388 A CN 202210815388A CN 115093333 B CN115093333 B CN 115093333B
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organic
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atoms
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CN115093333A (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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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C211/00—Compounds containing amino groups bound to a carbon skeleton
    • C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
    • C07C211/57—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton
    • C07C211/61—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton with at least one of the condensed ring systems formed by three or more rings
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    • C07D209/88—Carbazoles; Hydrogenated carbazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the ring system
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    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
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Abstract

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

Description

Organic compounds, mixtures, compositions and organic electronic devices
Technical Field
The present application relates to the field of display technology, and in particular, to an organic compound, a mixture, a composition, and an organic electronic device.
Background
Organic electronic devices, particularly organic electroluminescent devices (Organic Light Emitting Diode, OLED), have been widely used because of their self-luminescence, high brightness, high efficiency, low driving voltage, wide viewing angle, high contrast, high responsiveness, and the like. 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 positive electrode and the negative electrode of the organic electroluminescent device, holes are injected into the organic layer by the positive electrode, electrons are injected into the organic layer by the negative electrode, excitons are formed after the holes meet the electrons, and light is emitted when the excitons transition back to the ground state.
The organic electroluminescent device using the blue light fluorescent material has higher reliability. However, the existing blue light fluorescent material has wider emission spectrum and poorer color purity, and is unfavorable for high-end display. And the existing blue light fluorescent material is complex to synthesize, which is not beneficial to large-scale mass production. In addition, the efficiency and lifetime of the existing blue-light organic electroluminescent device are also to be improved.
The existing blue light organic electroluminescent device luminescent layer adopts a host-guest doped structure. The blue light host material adopts condensed ring derivatives based on anthracene, the blue light guest compound adopts aryl vinyl amine compounds, the compounds have poor thermal stability and are easy to decompose, thus 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 are problems 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 luminous efficiency and lifetime, and poor color purity of the existing organic electronic devices.
The application provides an organic compound, which has a structure shown in a general formula I:
Wherein,
n1 is any integer from 1 to 8; m1 is any integer from 0 to 5;
R 1 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 keto group having 1 to 20C atoms, or an alkoxycarbonyl group having 2 to 20C atoms, or an aryloxycarbonyl group having 7 to 20C atoms, 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, cyano, carbamoyl, haloformyl, formyl, isocyano, thiocyanate, isothiocyanate, hydroxy, nitro, amino, CF 3 Cl, br, F, I or combinations of these groups, wherein adjacent R' s 1 Can form a ring with each other;
Ar 1 and Ar is a group 2 Each occurrence is independently selected from a substituted or unsubstituted aromatic group containing 6 to 60C atoms, a substituted or unsubstituted heteroaromatic group containing 5 to 60 ring atoms, a substituted or unsubstituted non-aromatic ring system containing 3 to 30 ring atoms;
R 2 Each occurrence is independently selected from H, D, or a linear alkyl group having 1 to 20C atoms, or a branched alkyl group having 3 to 20C atoms, or a cyclic alkyl group having 3 to 20C atoms, a substituted or unsubstituted aromatic group having 6 to 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 structures shown in general formulas (II-1) - (II-4):
wherein,
r in the general formulae (II-1) to (II-3) 1 Independently at each occurrence, 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 aromatic group having 5 to 20 ring atoms, or a heteroaromatic group having 5 to 20 ring atoms, or a combination of such groups.
Ar 1 And Ar is a group 2 Each occurrence is independently selected from a substituted or unsubstituted aromatic group containing 6 to 14C atoms, a substituted or unsubstituted heteroaromatic group containing 5 to 14 ring atoms.
In an alternative embodiment of the present application, the Ar 1 And Ar is a group 2 Each occurrence is independently selected from one of the following groups:
wherein X is independently selected from CR for each occurrence 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 R is 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 alkoxycarbonyl group having 7 to 20C atomsAryloxycarbonyl of C atom, or substituted or unsubstituted aryl group having 5 to 60 ring atoms, or substituted or unsubstituted heteroaryl group having 5 to 60 ring atoms, or aryloxy group having 5 to 60 ring atoms, or heteroaryloxy group having 5 to 60 ring atoms, cyano group, amino group, carbamoyl group, haloformyl group, formyl group, isocyano group, isocyanate group, thiocyanate group, isothiocyanate group, hydroxyl group, nitro group, CF 3 Cl, br, F, or a combination of these groups.
In an alternative embodiment of the present application, the Ar 1 And Ar is a group 2 Each independently selected from one of the following groups:
Wherein,
". Times" represent the site of attachment; n is n 2 Any integer selected from 0-3;
R 2 independently at each occurrence, selected from H, D, or a linear 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;
R 3 r is R 4 Each occurrence is independently selected from H, D, or a linear 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 an alternative embodiment of the present application, the Ar 1 And Ar is a group 2 Each independently selected from one of the following groups:
wherein "×" denotes a ligation site; tAm represents 2- (2-methyl) butyl; tBu represents tert-butyl.
In an alternative embodiment of the present application, the organic compound is selected from any one of the following structures:
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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 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 luminophore, a luminescent 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 effects of this application lie in: the organic compound is an indene-containing arylamine compound, has a better conjugated system and better stability, and can be applied to an organic electronic device to improve the service life of the organic electronic device. Meanwhile, the organic compound has fluorescence emission with the luminescence wavelength at a short wavelength, and the luminescence spectrum is shown to have a narrow half-peak width, so that the organic compound is used as a blue fluorescence luminescent material, the luminescence efficiency of an organic electronic device can be improved, and deep blue luminescence can be realized.
Drawings
In order to more clearly illustrate the embodiments or the technical solutions in the prior art, the following description will briefly introduce the drawings that are needed in the embodiments or the description of the prior art, it is obvious that the drawings in the following description are only some embodiments of the invention, and that other drawings can be obtained according to these drawings without inventive effort for a person skilled in the art.
Fig. 1 is a schematic structural diagram of an organic electronic device according to an embodiment of the present application.
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 will be apparent that the described embodiments are only some, but not all, of the embodiments of the present application. All other embodiments, which can be made by those skilled in the art based on the embodiments herein without making any inventive effort, are intended to be within the scope of the present application.
In the description of the present application, it should be understood that the azimuth or positional relationship indicated by the terms "upper", "lower", etc. are based on the azimuth or positional relationship shown in the drawings, and are merely for convenience of description of the present application and to simplify the description, and do not indicate or imply that the apparatus or element referred to must have a specific azimuth, be configured and operated in a specific azimuth, and thus should not be construed as limiting the present application. Furthermore, the terms "first," "second," and the like, are used for descriptive purposes only and are not to be construed as indicating or implying a relative importance or implicitly indicating the number of technical features indicated. Thus, a feature defining "a first" or "a second" may explicitly or implicitly include one or more of the described features. In the description of the present application, the meaning of "a plurality" is two or more, unless specifically defined otherwise.
The present application may repeat reference numerals and/or letters in the various examples, and such repetition is for the purpose of simplicity and clarity and does not in itself dictate a relationship between the various embodiments and/or configurations discussed.
In this application, 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 are interchangeable.
In the present application, heteroaromatic groups, heteroaromatic ring systems have the same meaning and can be interchanged.
In the present application, "substituted" means that a hydrogen atom in a substituted group is substituted with a substituent.
In this application, the same substituent, when present multiple times, may be independently selected from different groups. If the general formula contains a plurality of R1, R1 can be independently selected from different groups. For exampleThe 6R 1 groups 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 groups acceptable in the art, including but not limited to: c (C) 1-30 Alkyl, heterocyclyl having 3 to 20 ring atoms, aryl having 5 to 20 ring atoms, heteroaryl having 5 to 20 ring atoms, silyl, carbonyl, alkoxycarbonyl, aryloxycarbonyl, carbamoyl, haloformyl, formyl, -NRR', cyano, isocyano, thiocyanate, isothiocyanate, hydroxy, trifluoromethyl, nitro or halogen, and which may be further substituted with substituents acceptable in the art; it is understood that R and R 'in-NRR' are each independently substituted with a group acceptable in the art, including but not limited to H, C 1-6 Alkyl, cycloalkyl having 3 to 8 ring atoms, heterocyclyl having 3 to 8 ring atoms, aryl having 5 to 20 ring atoms or heteroaryl having 5 to 10 ring atoms; the C is 1-6 Optionally 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 atomsOne step is substituted with one or more of the following groups: c (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" means the number of atoms among atoms constituting the ring itself of a structural compound (for example, a monocyclic compound, a condensed ring compound, a crosslinked compound, a carbocyclic compound, a heterocyclic compound) in which atoms are bonded to form a ring. When the ring is substituted with a substituent, the atoms contained in the substituent are not included in the ring-forming atoms. The same applies to the "number of ring atoms" described below, unless otherwise specified. For example, the number of ring atoms of the benzene ring is 6, the number of ring atoms of the naphthalene ring is 10, and the number of ring atoms of the thienyl group is 5.
In this application, "alkyl" may mean straight, branched, and/or cyclic alkyl. The carbon number of the alkyl group may be 1 to 50, 1 to 30, 1 to 20, 1 to 10 or 1 to 6. Non-limiting examples of alkyl groups include methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, isobutyl, 2-ethylbutyl, 3-dimethylbutyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, cyclopentyl, 1-methylpentyl, 3-methylpentyl, 2-ethylpentyl, 4-methyl-2-pentyl, n-hexyl, 1-methylhexyl, 2-ethylhexyl, 2-butylhexyl, cyclohexyl, 4-methylcyclohexyl, 4-tert-butylcyclohexyl, n-heptyl, 1-methylheptyl, 2-dimethylheptyl, 2-ethylheptyl, 2-butylheptyl, n-octyl, tert-octyl, 2-ethyloctyl, 2-hexyloctyl, 3, 7-dimethyloctyl cyclooctyl, n-nonyl, n-decyl, adamantyl, 2-ethyldecyl, 2-butyldecyl, 2-hexyldecyl, 2-octyldecyl, n-undecyl, n-dodecyl, 2-ethyldodecyl, 2-butyldodecyl, 2-hexyldodecyl, 2-octyldodecyl, n-tridecyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, 2-ethylhexadecyl, 2-butylhexadecyl, 2-hexylhexadecyl, 2-octylhexadecyl, n-heptadecyl, n-octadecyl, n-nonadecyl, n-eicosyl, 2-ethyleicosyl, 2-hexyleicosyl, 2-octyleicosyl, n-eicosyl, N-docosanyl, n-tricosyl, n-tetracosyl, n-pentacosyl, n-hexacosyl, n-heptacosyl, n-octacosyl, n-nonacosyl, n-triacontyl, etc.
In the present application, "aryl, or aryl" refers to a hydrocarbon group containing at least one aromatic ring. "heteroaryl" or "heteroaromatic" refers to an aromatic hydrocarbon group containing 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. Fused ring aromatic group means that the ring 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. Fused heterocyclic aromatic groups refer to fused ring aromatic hydrocarbon groups containing at least one heteroatom. For purposes of this application, an aromatic or heteroaromatic group includes not only an aromatic ring system but also a non-aromatic ring system. 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 aromatic or heterocyclic aromatic groups for purposes of this application. For the purposes of this application, fused ring aromatic or fused heterocyclic aromatic ring systems include not only aromatic or heteroaromatic systems, but also systems in which multiple 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-diaryl fluorene, triarylamine, diaryl ether, and the like 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, benzophenanthrene, perylene, naphthacene, pyrene, benzopyrene, acenaphthene, fluorene, and derivatives thereof; the heteroaromatic group is selected from the group consisting of triazines, pyridines, pyrimidines, imidazoles, furans, thiophenes, benzofurans, benzothiophenes, indoles, carbazoles, pyrroloimidazoles, pyrrolopyrroles, thienopyrroles, thienothiothiophenes, furopyrroles, furofurans, thienofurans, benzisoxazoles, benzisothiazoles, benzimidazoles, quinolines, isoquinolines, phthalazines, quinoxalines, phenanthridines, primary pyridines, quinazolines, quinazolinones, dibenzothiophenes, dibenzofurans, carbazoles, and derivatives thereof.
In this application, where no attachment site is specified in a group, an optionally attachable site in the group is meant as an attachment site.
In this application, where no fused site is indicated in a group, it is meant that an optionally fused site in the group is taken as a fused site, preferably two or more sites in the group that are ortho to each other are fused sites.
In the present application, a single bond to which a substituent is attached extends through the corresponding ring, meaning that the substituent may be attached to an optional position on the ring, e.g R in (2) is linked to any substitutable site of the benzene ring, -, or a combination thereof>Represented by 1 or more R 1 Can be connected with any substitutable site of the four benzene rings, n represents R 1 Is a number of (3).
In the present application, the energy level structure of the organic material, the triplet energy level ET1, the highest occupied orbital energy level HOMO, the lowest unoccupied orbital energy level LUMO play a key role. The determination of these energy levels is described below. HOMO and LUMO energy levels can be measured by photoelectric effects such as XPS (X-ray photoelectron spectroscopy) and UPS (ultraviolet electron spectroscopy) or by cyclic voltammetry (hereinafter referred to as CV). Recently, quantum chemical methods, such as density functional theory (hereinafter abbreviated as DFT), have also become effective methods for calculating molecular orbital energy levels. The triplet energy level ET1 of the organic material can be measured by low temperature Time resolved luminescence spectroscopy, or obtained by quantum analog calculations (e.g. by Time-dependent, DFT), such as by commercial software Gaussian 09W (Gaussian inc.). It should be noted that the absolute value of HOMO, LUMO, ET1 depends on the measurement or calculation method used, and even for the same method, different evaluation methods, e.g. starting and peak points on the CV curve, may give different HOMO/LUMO values. Thus, a reasonable and 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 value of HOMO, LUMO, ET1 is based on a simulation of the Time-dependent DFT, but does not affect the application of other measurement or calculation methods.
The technical solutions provided in the present application will be described in detail below.
The application provides an organic compound, which has a structure shown as a general formula I:
wherein,
n1 is any integer from 1 to 8; m1 is any integer from 0 to 5;
R 1 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 keto group having 1 to 20C atoms, or an alkoxycarbonyl group having 2 to 20C atoms, or an aryloxycarbonyl group having 7 to 20C atoms, 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, cyano, carbamoyl, haloformyl, formyl, isocyano, thiocyanate, isothiocyanate, hydroxy, nitro, amino, CF 3 Cl, br, F, I or combinations of these groups, wherein adjacent R' s 1 Can form a ring with each other;
Ar 1 and Ar is a group 2 Each occurrence is independently selected from a substituted or unsubstituted aromatic group containing 6 to 60C atoms, a substituted or unsubstituted heteroaromatic group containing 5 to 60 ring atoms, a substituted or unsubstituted non-aromatic ring system containing 3 to 30 ring atoms;
R 2 each occurrence is independently selected from H, D, or a linear alkyl group having 1 to 20C atoms, or a branched alkyl group having 3 to 20C atoms, or a cyclic alkyl group having 3 to 20C atoms, a substituted or unsubstituted aromatic group having 6 to 30 ring atoms, a substituted or unsubstituted heteroaromatic group having 5 to 30 ring atoms.
In some embodiments, R 1 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 an aromatic group having 5 to 20 ring atoms, or a heteroaromatic group having 5 to 20 ring atoms, or a combination of such groups.
In some embodiments, R 1 Each occurrence is 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.
In some embodiments, R 1 Each occurrence is selected from one 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, 3, 7-dimethyloctyl, cyclooctyl, n-nonyl, 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 structures represented by general formulas (II-1) - (II-4):
wherein,
r in the general formulae (II-1) to (II-3) 1 Independently at each occurrence, 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 aromatic group having 5 to 20 ring atoms, or a heteroaromatic group having 5 to 20 ring atoms, or a combination of such groups.
Ar 1 And Ar is a group 2 Each occurrence is independently selected from a substituted or unsubstituted aromatic group containing 6 to 14C atoms, a substituted or unsubstituted heteroaromatic group containing 5 to 14 ring atoms.
In some embodiments, R in formulas (II-1) - (II-3) 1 Each occurrence is independently 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 as described in formulas (II-1) - (II-3) 1 Each occurrence is independently selected from the group consisting of D, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, isobutyl, 2-ethylbutyl, 3-dimethylbutyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, cyclopentyl, 1-methylpentyl, 3-methylpentyl, 2-ethylpentyl, 4-methyl-2-pentyl, n-hexyl, 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, 3, 7-dimethyloctyl, cyclooctyl, n-nonyl, n-decyl, adamantyl, and 2- (2-methyl) butyl.
In some embodiments, R 1 And at multiple occurrences, are selected from the same group.
In an alternative embodiment of the present application, the Ar 1 And Ar is a group 2 Each occurrence is independently selected from one of the following groups:
wherein X is independently selected from CR for each occurrence 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 R is 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 a heteroaryloxy group having 5 to 60 ring atoms, cyano, amine, carbamoyl, haloformyl, formyl, isocyano, isocyanate, thiocyanate, isothiocyanate, hydroxy, nitro, CF 3 Cl, br, F, or a combination of these groups.
When X is a bonding site, X is a C atom.
In an alternative embodiment of the present application, the Ar 1 And Ar is a group 2 Each independently selected from one of the following groups:
wherein,
". Times" represent the site of attachment; n is n 2 Any integer selected from 0-3;
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 aryl group having 5 to 30 ring atoms, or a substitution having 5 to 30 ring atomsOr an unsubstituted heteroaryl group, or a combination of these groups;
R 3 r is R 4 Each occurrence is independently selected from H, D, or a linear 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 one 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, 3, 7-dimethyloctyl, cyclooctyl, n-nonyl, n-decyl, adamantyl or 2- (2-methyl) butyl, phenyl, pyridyl, pyrimidinyl or naphthyl.
In some embodiments, R 3 R is 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, pyridinyl, pyrimidinyl, or naphthyl group.
In some embodiments, R 3 R is R 4 Each independently selected from H, D, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, phenyl, pyridinyl, pyrimidinyl or naphthyl.
In an alternative embodiment of the present application, the Ar 1 And Ar is a group 2 Each independently selected from one of the following groups:
wherein "×" attached to a single bond represents the site of attachment; tAm represents 2- (2-methyl) butyl; tBu represents tert-butyl.
In some embodiments, ar 1 And Ar is a group 2 And when present, are selected from the same groups.
In some embodiments, ar 1 And Ar is a group 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:
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wherein, the organic compound can be used as a functional material in organic electronic devices, especially organic light emitting diode (organic light emitting diodes, OLED) devices.
In some embodiments, the organic compound may serve as a blue light emitting material.
In particular, 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 organic compound has better thermal stability, can be applied to a luminescent material of an organic electronic device, can effectively prolong the service life of the organic electronic device, has fluorescence emission with a luminescent wavelength at a short wavelength, and has a narrow half-peak width, so that the organic compound is used as a blue luminescent material, can improve the luminescent efficiency of the organic electronic device, and can realize deep blue luminescence.
The application also provides a mixture comprising the organic compound and at least one organic functional material, wherein the organic functional material is at least one selected from a Hole Injection Material (HIM), a Hole Transport Material (HTM), an Electron Transport Material (ETM), an Electron Injection Material (EIM), an Electron Blocking Material (EBM), a Hole Blocking Material (HBM), a light Emitter (Emitter), a Host material (Host), an organic dye, and the like. Various organic functional materials are described in detail, for example, in patent WO2010135519A1, US20090134784A1 and WO2011110277A1, the entire contents of which 3 patent documents are 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 preparing the organic electronic device.
In preparing 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, doctor blade coating, roller printing, twist roller printing, lithographic printing, flexography, rotary printing, spray coating, brush or pad printing, slot die coating, and the like. Gravure printing, inkjet printing and inkjet printing are preferred. One or more components may be additionally included in the composition, such as surface active compounds, lubricants, wetting agents, dispersants, hydrophobing agents, binders, and the like, for adjusting viscosity, film forming properties, improving adhesion, and the like.
In some embodiments, the organic solvent is selected from at least one of an aromatic or heteroaromatic, an ester, an aromatic ketone or aromatic ether, an aliphatic ketone or aliphatic ether, a cycloaliphatic or olefinic compound, a borate or phosphate 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, pentyltoluenes, o-diethylbenzene, m-diethylbenzene, p-diethylbenzene, 1,2,3, 4-tetramethylbenzene, 1,2,3, 5-tetramethylbenzene, 1,2,4, 5-tetramethylbenzene, butylbenzene, dodecylbenzene, dihexylbenzene, dibutylbenzene, p-diisopropylbenzene, cyclohexylbenzene, benzylbutylbenzene, dimethylnaphthalene, 3-isopropylbiphenyl, p-methylisopropylbenzene, 1-methylnaphthalene, 1,2, 4-trichlorobenzene, 4-difluorodiphenyl methane, 1, 2-dimethoxy-4- (1-propenyl) benzene, diphenyl methane, 2-phenylpyridine, 3-phenylpyridine, N-methyldiphenylamine, 4-isopropylbiphenyl, α -dichlorodiphenyl methane, 4- (3-phenylpropyl) pyridine, benzyl benzoate, 1-bis (3, 4-dimethylphenyl) ethane, 2-isopropylnaphthalene, 2-quinolinecarboxylic acid, ethyl ester, 2-methylfuran, etc.
In particular, the aromatic ketone-based solvents include, but are 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-methylpropionophenone, 3-methylpropionophenone, 2-methylpropionophenone, and the like.
In particular, the aromatic ether-based solvents include, but are not limited to: 3-phenoxytoluene, butoxybenzene, p-anisaldehyde dimethyl acetal, tetrahydro-2-phenoxy-2H-pyran, 1, 2-dimethoxy-4- (1-propenyl) benzene, 1, 4-benzodioxane, 1, 3-dipropylbenzene, 2, 5-dimethoxytoluene, 4-ethylben-ther, 1, 3-dipropoxybenzene, 1,2, 4-trimethoxybenzene, 4- (1-propenyl) -1, 2-dimethoxybenzene, 1, 3-dimethoxybenzene, glycidyl phenyl ether, dibenzyl ether, 4-t-butyl anisole, trans-p-propenyl anisole, 1, 2-dimethoxybenzene, 1-methoxynaphthalene, diphenyl ether, 2-phenoxymethyl ether, 2-phenoxytetrahydrofuran, ethyl-2-naphthyl ether, and the like.
In some embodiments, the organic solvent may preferably be selected from: aliphatic ketones such as 2-nonene, 3-nonene, 5-nonene, 2-decanone, 2, 5-adipone, 2,6, 8-trimethyl-4-nonene, fenchyl ketone, phorone, isophorone, di-n-amyl ketone and the like; or aliphatic ethers such as amyl ether, hexyl ether, dioctyl ether, ethylene glycol dibutyl ether, diethylene glycol diethyl ether, diethylene glycol butyl methyl ether, diethylene glycol dibutyl ether, triethylene glycol dimethyl ether, triethylene glycol ethyl methyl ether, triethylene glycol butyl methyl ether, tripropylene glycol dimethyl ether, tetraethylene glycol dimethyl ether, and the like.
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. Particular preference is given to 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-trichloroethane, 1, 2-tetrachloroethane, ethyl acetate, butyl acetate, dimethylformamide, dimethylacetamide, dimethylsulfoxide, tetrahydronaphthalene, decalin, indene and/or mixtures thereof.
The organic solvent is a solvent with Hansen (Hansen) solubility parameters in the following ranges:
δ d (dispersion force) of 17.0-23.2 MPa 1/2 In particular in the range from 18.5 to 21.0MPa 1/2 Is defined by the range of (2);
δ p (polar force) is 0.2-12.5 MPa 1/2 In particular in the range of 2.0 to 6.0MPa 1/2 Is defined by the range of (2);
δ h the (hydrogen bond force) is between 0.9 and 14.2MPa 1/2 In particular in the range of 2.0 to 6.0MPa 1/2 Is not limited in terms of the range of (a).
The organic solvent is selected by taking the boiling point parameter into consideration. In the application, the boiling point of the organic solvent is more than or equal to 150 ℃; preferably not less than 180 ℃; more preferably not less than 200 ℃; more preferably not less than 250 ℃; and most preferably at a temperature of 275 ℃ or more or 300 ℃ or more. Boiling points in these ranges are beneficial in preventing nozzle clogging of inkjet printheads. The organic solvent may be evaporated from the solvent system to form a film comprising the functional material.
In some embodiments, the composition may be a solution or a suspension.
In some embodiments, the mass percent of the organic compound or the mixture in the composition is from 0.01wt% to 20wt%.
Preferably, the mass percentage of the organic compound or the mixture in the composition is 0.1wt% to 15wt%.
More preferably, the mass percentage of the organic compound or the mixture in the composition is 0.2wt% to 5wt%.
More preferably, the mass percentage of the organic compound or the mixture in the composition is 0.25wt% to 3wt%.
In the present application, the organic compound, the mixture and the composition are applicable to the organic electronic device. The organic electronic device includes, but is not limited to: organic Light Emitting Diodes (OLEDs), organic photovoltaic cells (OPVs), organic light emitting cells (OLEEC), organic Field Effect Transistors (OFET), organic light emitting field effect transistors, organic lasers, organic spintronics devices, organic sensors, and organic plasmon emitting diodes (Organic Plasmon Emitting Diode), and the like.
In the present application, the organic electronic device includes at least one organic functional layer, the organic functional layer is 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, and the organic functional layer includes the organic compound or the mixture.
In an alternative embodiment of the present application, the organic electronic device comprises a light emitting layer comprising the organic compound.
Specifically, the organic compound is an indene-containing arylamine compound, the structure of the organic compound has a better conjugated system and better stability, and the organic compound can be applied to a luminescent layer material of an organic electronic device to effectively prolong the service life of the organic electronic device, and meanwhile, the organic compound has fluorescence emission with a luminescent wavelength at a short wavelength, and a luminescent spectrum is shown to have a 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.
The organic electronic device includes, but is not limited to: an OLED, OLEEC or organic light emitting field effect transistor. In this 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, a light emitting layer 105, an electron transport layer 106, and a cathode 107. The light emitting layer 105 includes 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, and the material of the 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 ℃; more preferably, the glass transition temperature of the substrate 101 is greater than or equal to 250 ℃; optimally, 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 anode 102 is made of conductive metal, conductive metal oxide, 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 valence band level of the light-emitting or hole-injecting layer 103, the hole-transporting layer 104, and the p-type semiconductor material in the electron blocking layer 105 is less than 0.5eV, preferably less than 0.3eV, more preferably less than 0.2eV. 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 in physical vapor deposition, vacuum thermal evaporation, electron beam (e-beam), and the like.
The material of the cathode 107 is conductive metal or 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 conduction band level of the light-emitting or electron-injecting layer, the electron-transporting layer 106, and the n-type semiconductor material in the hole-blocking layer 105 is less than 0.5eV, preferably less than 0.3eV, more preferably less than 0.2eV. The cathode 107 material may be selected from, but 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 into the cathode 107 using methods known in the art for forming cathodes, such as radio frequency magnetron sputtering in physical vapor deposition, vacuum thermal evaporation, electron beam (e-beam), and the like.
In other embodiments, the OLED device may also include other functional layers, such as electron blocking layers, electron injection layers, electron transport layers, 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 materials 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 of the OLED device 100 ranges from 300 nm to 1000nm, preferably from 350 nm to 900nm, and more preferably from 400 nm to 800nm.
The application also relates to the application of the organic electronic device in electronic equipment and the electronic equipment comprising the organic electronic device, wherein the electronic equipment can be, but is not limited to, display equipment, lighting equipment, light sources, sensors and the like.
The following are examples of the organic compounds and synthetic methods of the present application, which are only preferred examples of the present application, and are not limiting of the present application.
Example 1
The synthetic route for organic compound 1 is as follows:
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1. synthesis of intermediate Compounds 1-3
Compounds 1-1 (10 mmol), 1-2 (10 mmol), palladium catalyst Pd (dba) 2 (0.1 mmol), TTBP (tri-tert-butylphosphine) (0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene solvent, stirred for 6h at 100℃under nitrogen atmosphere, cooled, distilled off, extracted and separated by water, and the organic phase column chromatography gave 7.69mmol of intermediate compound 1-3. Wherein the yield of intermediate compound 1-3 was 76.9%, MS (ASAP) =207.3.
2. Synthesis of organic Compound 1
Intermediate Compounds 1-3 (20 mmol), compounds 1-4 (10 mmol), palladium catalyst Pd (dba) 2 (0.1 mmol), TTBP (0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene solvent, stirred for 6h at 100deg.C under nitrogen atmosphere, cooled, distilled off, extracted and washed with water to separate the liquid, and the organic phase was separated by column chromatography to give organic compound 1. Wherein the yield of organic compound 1 was 78.8%, MS (ASAP) =612.4.
Example 2
The synthetic route for organic compound 2 is as follows:
1. synthesis of intermediate Compounds 1-3
Compounds 1-1 (10 mmol), 1-2 (10 mmol), palladium catalyst Pd (dba) 2 (0.1 mmol), TTBP (tri-tert-butylphosphine) (0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene solvent, stirred for 6h at 100℃under nitrogen atmosphere, cooled, distilled off, extracted and separated by water, and the organic phase column chromatography gave 7.69mmol of intermediate compound 1-3. Wherein the yield of intermediate compound 1-3 was 76.9%, MS (ASAP) =207.3.
2. Synthesis of organic compound 2:
compounds 1-3 (20 mmol), 2-1 (10 mmol), pd (dba) 2 (0.1 mmol), TTBP (0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred under nitrogen at 100deg.C for 6h. Cooling, rotary evaporating to remove solvent, extracting, washing with water, separating liquid, and performing organic phase column chromatography to obtain organic compound 2. Wherein the yield of organic compound 2 was 67.9%, MS (ASAP) = 696.3.
Example 3
The synthetic route for organic compound 3 is as follows:
1. synthesis of intermediate 3-2:
compound 3-3 (10 mmol), compound 3-1 (10 mmol), pd (dba) 2 (0.1 mmol), TTBP (0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred under nitrogen at 100deg.C for 6h. After cooling, the solvent was removed by rotary evaporation, extraction and water washing were carried out, and the organic phase column chromatography gave intermediate 3-2 in a molar amount of 7.07mmol of intermediate compound 3-2. Wherein the yield of intermediate compound 3-2 was 70.7%, MS (ASAP) =283.3.
2. Synthesis of organic compound 3:
compound 3-2 (20 mmol), compound 2-1 (10 mmol), pd (dba) 2 (0.1 mmol), TTBP (0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred under nitrogen at 100deg.C for 6h. Cooling, rotary evaporating to remove solvent, extracting, washing with water, separating liquid, and performing organic phase column chromatography to obtain organic compound 3. Wherein the yield of organic compound 3 was 55.4%, MS (AS AP)＝848.4。
Example 4
The synthetic route for organic compound 4 is as follows:
1. synthesis of intermediate 4-2:
compound 3-3 (10 mmol), compound 4-1 (10 mmol), pd (dba) 2 (0.1 mmol), TTBP (0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred under nitrogen at 100deg.C for 6h. After cooling, the solvent was removed by rotary evaporation, extraction and water washing were carried out, and the organic phase column chromatography gave intermediate compound 4-2 having a molar mass of 6.63 mmol. Wherein the yield of intermediate compound 4-2 was 66.3%, MS (ASAP) =283.3.
2. Synthesis of organic compound 4:
compound 4-2 (20 mmol), compound 2-1 (10 mmol), pd (dba) 2 (0.1 mmol), TTBP (0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred under nitrogen at 100deg.C for 6h. Cooling, rotary evaporating to remove solvent, extracting, washing with water, separating liquid, and performing organic phase column chromatography to obtain organic compound 4. Wherein the yield of organic compound 4 was 69.3%, MS (ASAP) = 848.4.
Example 5
The synthetic route for organic compound 5 is as follows:
1. synthesis of intermediate 5-2:
compounds 1-2 (10 mmol), 5-1 (10 mmol), pd (dba) 2 (0.1 mmol), TTBP (0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred under nitrogen at 100deg.C for 6h. After cooling, the solvent was removed by rotary evaporation, extraction and water washing were carried out, and the organic phase column chromatography gave intermediate 5-2 in a molar amount of 7.34mmol of intermediate compound 5-2. Wherein the yield of intermediate compound 5-2 was 73.4%, MS (ASAP) =297.1.
2. Synthesis of organic compound 5:
compound 5-2 (20 mmol), compound 2-1 (10 mmol), pd (dba) 2 (0.1 mmol), TTBP (0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred under nitrogen at 100deg.C for 6h. Cooling, rotary evaporating to remove solvent, extracting, washing with water, separating liquid, and performing organic phase column chromatography to obtain organic compound 5. Wherein the yield of organic compound 5 was 67.1%, MS (ASAP) = 876.3.
Example 6
The synthetic route for organic compound 6 is as follows:
1. synthesis of intermediate 6-2:
compound 6-3 (10 mmol), compound 6-1 (10 mmol), pd (dba) 2 (0.1 mmol), TTBP (0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred under nitrogen at 100deg.C for 6h. After cooling, the solvent was removed by rotary evaporation, extraction and water washing were carried out, and the organic phase column chromatography gave intermediate 6-2 in a molar amount of 6.32mmol of intermediate compound 6-2. Wherein the yield of intermediate compound 6-2 was 63.2%, MS (ASAP) =297.1.
2. Synthesis of organic compound 6:
compound 6-2 (20 mmol), compound 2-1 (10 mmol), pd (dba) 2 (0.1 mmol), TTBP (0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred under nitrogen at 100deg.C for 6h. Cooling, rotary evaporating to remove solvent, extracting, washing with water, separating liquid, and performing organic phase column chromatography to obtain organic compound 6. Wherein the yield of organic compound 6 was 75.3%, MS (ASAP) = 876.3.
Example 7
The synthetic route for organic compound 7 is as follows:
1. synthesis of intermediate 7-2:
compound 6-3 (10 mmol), compound 7-1 (10 mmol), pd (dba) 2 (0.1 mmol), TTBP (0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred under nitrogen at 100deg.C for 6h. After cooling, the solvent was removed by rotary evaporation, extraction and water washing were carried out, and the organic phase column chromatography gave intermediate 7-2 in a molar amount of 7.35mmol of intermediate compound 7-2. Wherein the yield of intermediate compound 7-2 was 73.5%, MS (ASAP) =313.6.
2. Synthesis of organic compound 7:
compound 7-2 (20 mmol), compound 2-1 (10 mmol), pd (dba) 2 (0.1 mmol), TTBP (0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred under nitrogen at 100deg.C for 6h. After cooling, the solvent is removed by rotary evaporation, extraction and water washing are carried out, and the organic phase column chromatography is carried out to obtain the organic compound 7. Wherein the yield of organic compound 7 was 61.3%, MS (ASAP) = 908.7.
Example 8
The synthetic route for compound 8 is as follows:
1. synthesis of intermediate 8-2:
compound 8-3 (10 mmol), compound 8-1 (10 mmol), pd (dba) 2 (0.1 mmol), TTBP (0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred under nitrogen at 100deg.C for 6h. After cooling, the solvent was removed by rotary evaporation, extraction and water washing were carried out, and the organic phase column chromatography gave intermediate 8-2 in a molar amount of 5.79mmol of intermediate compound 8-2. Wherein the yield of intermediate compound 8-2 was 57.9%, MS (ASAP) =323.6.
2. Synthesis of organic compound 8:
compound 8-2 (20 mmol), compound 2-1 (10 mmol), pd (dba) 2 (0.1 mmol), TTBP (0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred under nitrogen at 100deg.C for 6h. Cooling, rotary evaporating to remove solvent, extracting, washing with water, separating liquid, and performing organic phase column chromatography to obtain organic compound 8. Wherein the yield of organic compound 8 was 66.9%, MS (ASAP) = 928.4.
Example 9
The synthetic route for organic compound 9 is as follows:
1. synthesis of intermediate 9-2:
compound 9-3 (10 mmol), compound 9-1 (10 mmol), pd (dba) 2 (0.1 mmol), TTBP (0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred under nitrogen at 100deg.C for 6h. After cooling, the solvent was removed by rotary evaporation, extraction and water washing were carried out, and the organic phase column chromatography gave intermediate 9-2 in a molar amount of 8.32mmol of intermediate compound 9-2. Wherein the yield of intermediate compound 9-2 was 83.2%, MS (ASAP) = 310.5.
2. Synthesis of organic compound 9:
compound 9-2 (20 mmol), compound 2-1 (10 mmol), pd (dba) 2 (0.1 mmol), TTBP (0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred under nitrogen at 100deg.C for 6h. Cooling, rotary evaporating to remove solvent, extracting, washing with water, separating liquid, and performing organic phase column chromatography to obtain the compound 9. Wherein the yield of organic compound 9 was 68.4%, MS (ASAP) =902.2.
Example 10
The synthetic route for compound 10 is shown in the following figure:
1. synthesis of intermediate 10-2:
compound 10-3 (10 mmol), compound 10-1 (10 mmol), pd (dba) 2 (0.1 mmol), TTBP (0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred under nitrogen at 100deg.C for 6h. After cooling, the solvent was removed by rotary evaporation, extraction and water washing were carried out, and the organic phase column chromatography gave intermediate 10-2 in a molar amount of 6.97mmol of intermediate compound 10-2. Wherein the yield of intermediate compound 10-2 was 69.7%, MS (ASAP) = 386.2.
2. Synthesis of Compound 10:
compound 10-2 (20 mmol), compound 2-1 (10 mmol), pd (dba) 2 (0.1 mmol), TTBP (0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred under nitrogen at 100deg.C for 6h. Cooling, rotary evaporating to remove solvent, extracting, washing with water, separating liquid, and performing organic phase column chromatography to obtain compound 10. The yield of the organic compound 10 was 78.5%, MS (ASAP) = 1054.5.
Example 11
The synthetic route for compound 11 is shown in the following figure:
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1. synthesis of intermediate 10-2:
compound 10-3 (10 mmol), compound 10-1 (10 mmol), pd (dba) 2 (0.1 mmol), TTBP (0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred under nitrogen at 100deg.C for 6h. After cooling, the solvent was removed by rotary evaporation, extraction and water washing were performed, and 80.3mmol of intermediate compound 10-2 was obtained by column chromatography of the organic phase. Wherein the yield of intermediate compound 10-2 was 80.3%, MS (ASAP) = 386.2.
2. Synthesis of Compound 11:
compound 10-2 (20 mmol), compound 11-1 (10 mmol), pd (dba) 2 (0.1 mmol), TTBP (0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred under nitrogen at 100deg.C for 6h. After cooling, the solvent is removed by rotary evaporation, extraction and water washing are carried out, and the organic phase column chromatography is carried out to obtain the compound 11. Wherein the yield of organic compound 11 was 75.9%, MS (ASAP) = 998.2.
Example 12
The synthetic route for compound 12 is as follows:
1. synthesis of intermediate 7-2:
compound 6-3 (10 mmol), compound 7-1 (10 mmol), pd (dba) 2 (0.1 mmol), TTBP (0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred under nitrogen at 100deg.C for 6h. After cooling, the solvent was removed by rotary evaporation, extraction and water washing were carried out, and the organic phase was separated by column chromatography to obtain 7.35mmol of intermediate compound 7-2. Wherein the yield of intermediate compound 7-2 was 73.5%, MS (ASAP) =313.6.
2. Synthesis of Compound 12:
compound 7-2 (20 mmol), compound 11-1 (10 mmol), pd (dba) 2 (0.1 mmol), TTBP (0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred under nitrogen at 100deg.C for 6h. Cooling, rotary evaporating to remove solvent, extracting, washing with water, separating liquid, and performing organic phase column chromatography to obtain compound 12. Wherein the yield of organic compound 12 was 71.7%, MS (ASAP) = 852.2.
Example 13
The synthetic route for compound 13 is as follows:
1. synthesis of intermediate 6-2:
compound 6-3 (10 mmol), compound 6-1 (10 mmol), pd (dba) 2 (0.1 mmol), TTBP (0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred under nitrogen at 100deg.C for 6h. After cooling, the solvent was removed by rotary evaporation, extraction and water washing were carried out, and the organic phase was separated by column chromatography to obtain 6.32mmol of intermediate compound 6-2. Wherein the yield of intermediate compound 6-2 was 63.2%, MS (ASAP) =297.1.
2. Synthesis of Compound 13:
compound 6-2 (20 mmol), compound 11-1 (10 mmol), pd (dba) 2 (0.1 mmol), TTBP (0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred under nitrogen at 100deg.C for 6h. Cooling, rotary evaporating to remove solvent, extracting, washing with water, separating liquid, and performing organic phase column chromatography to obtain the compound 13. The yield of the organic compound 13 was 76.9%, MS (ASAP) = 820.6.
Example 14
The synthetic route for compound 14 is as follows:
1. synthesis of intermediate 8-2:
compound 8-3 (10 mmol), compound 8-1 (10 mmol), pd (dba) 2 (0.1 mmol), TTBP (0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred under nitrogen at 100deg.C for 6h. After cooling, the solvent was removed by rotary evaporation, extraction and water washing were carried out, and the organic phase was separated by column chromatography to obtain 5.79mmol of intermediate compound 8-2. Wherein the yield of intermediate compound 8-2 was 57.9%, MS (ASAP) =323.6.
2. Synthesis of Compound 14:
compound 8-2 (20 mmol), compound 11-1 (10 mmol), pd (dba) 2 (0.1 mmol), TTBP (0.2 mmol) and sodium tert-butoxide (30 mmol) were dissolved in toluene and stirred under nitrogen at 100deg.C for 6h. Cooling, rotary evaporating to remove solvent, extracting, washing with water, separating liquid, and performing organic phase column chromatography to obtain compound 14. The yield of organic compound 14 was 87.6%, MS (ASAP) =872.4.
Comparative example:
the chemical structural formulas of the comparative compound 1 and the comparative compound 2 are as follows:
energy level calculation of organic compound:
the energy levels HOMO, LUMO, T1 and S1 of the organic compounds of examples 1-14 and comparative compound 1 were calculated.
The calculation method comprises the following steps: the molecular geometry is optimized by using TD-DFT (time-Density functional theory) through Gaussian 09W (Gaussian Inc.), first using a Semi-empirical method "group State/Semi-empirical/Default Spin/AM1" (Charge 0/Spin single), and then the energy structure of the organic molecule is calculated by TD-DFT (time-Density functional theory) method as "TD-SCF/DFT/Default Spin/B3PW91" and the basis set "6-31G (d)" (Charge 0/Spin single). The HOMO and LUMO energy levels are calculated according to the following calibration formula, and S1, T1 and resonance factor f (S1) are directly used.
HOMO(eV)＝((HOMO(G)×27.212)-0.9899)/1.1206；
LUMO(eV)＝((LUMO(G)×27.212)-2.0041)/1.385。
HOMO, LUMO, T1 and S1 are direct calculations of Gaussian 09W in Hartree. The results are shown in Table 1 below.
Table 1:
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preparing and detecting a device:
OLED devices were prepared using organic compounds 1-14 and comparative compound 1, comparative compound 2 prepared in examples 1-14, respectively. The OLED device was prepared as follows:
a. providing an ITO (indium tin oxide) conductive glass substrate, cleaning the substrate by using a cleaning agent, and then performing ultraviolet ozone treatment, wherein the cleaning agent can be one or more of chloroform, acetone or isopropanol;
b. spin-coating PEDOT (polyethylene dioxythiophene, clevelos) on the ITO conductive glass substrate in an ultra clean room TM AI 4083), and then treating on a hot plate at 180 ℃ for 10 minutes to obtain a hole injection layer with a thickness of 40 nm;
c. a solution of toluene as solvent TFB or PVK (Sigma Aldrich, average Mn 25,000-50,000) was spin-coated on the hole injection layer at a concentration of 5mg/ml in a nitrogen glove box, followed by treatment on a hot plate at 180 ℃ for 60 minutes to give a hole transport layer with a thickness of 20 nm;
d. in a nitrogen glove box, spin-coating an organic luminescent material mixture on the hole transport layer, and then treating the mixture 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 the guest materials are respectively organic compounds 1-14 and comparative compounds 1 and 2 prepared in the above examples 1-14, and the weight ratio of the host material to the guest material is 95:5, a step of;
e. Transferring the substrate into a vacuum cavity, placing ET and Liq into different evaporation units, respectively performing codeposition at a proportion of 50wt% in high vacuum (1X 10-6 mbar), forming a 20nm electron transport layer on the organic light-emitting layer, and then depositing Al cathodes with a thickness of 100nm to obtain OLED devices respectively;
f. the OLED device was encapsulated with an ultraviolet curable resin in a nitrogen glove box.
The organic compounds 1-14, the comparison compounds 1 and the comparison compounds 2 respectively correspond to the 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;
wherein, the chemical structural formula of BH in the step d is as follows:
wherein, the chemical structural formulas of the comparison compound 1 and the comparison compound 2 in the step d are as follows:
wherein, the chemical structural formula of ET in the step e is as follows:
wherein, the chemical structural formula of the Liq in the step e is as follows:
the current-voltage (J-V) characteristics of each OLED device prepared were characterized by the characterization apparatus while recording important parameters such as luminous efficacy (CE@1knits) and lifetime (LT90@1knits), the results of which are shown in Table 2.
Table 2:
as can be seen from Table 2, the color coordinates of the OELD device fabricated with organic compounds 1-14 as the emitters in the organic light-emitting layer are better than those of the OELD device fabricated with comparative compounds 1-2 as the emitters. According to the color coordinate graph, the lower the X, Y values of the color coordinates, the more toward deep blue the organic compounds 1-14 of the present application than the comparative compounds 1-2.
In addition, the organic compounds 1 to 14 are adopted as the luminous bodies in the organic luminous layers, so that the luminous efficiency of the OELD device is in the range of 8 to 9cd/A, and the OELD device has more excellent luminous efficiency. This is because the organic compound of the present application introduces a cyclopentenyl group as compared to comparative compound 1, and the indenyl group in the organic compound of the present application is superior to the biphenyl group in comparative compound 1 in terms of stability after film formation as compared to comparative compounds 1-2, and is superior to the dibenzofuran structure in comparative compound 2. Accordingly, the lifetime of an OLED device fabricated using organic compounds 1-14 as emitters in the organic light-emitting layer is much better than that of an OELD device fabricated using comparative compounds 1-2 as emitters in terms of OELD device lifetime.
In summary, the organic compound provided by the application is an indene-containing arylamine compound, has a better conjugated system and better stability, and can be applied to an organic electronic device to prolong the service life of the organic electronic device. Meanwhile, the organic compound has fluorescence emission with the luminescence wavelength at a short wavelength, and the luminescence spectrum is shown to have a narrow half-peak width, so that the organic compound is used as a blue fluorescence luminescent material, the luminescence efficiency of an organic electronic device can be improved, and deep blue luminescence can be realized.
In summary, although the present application has been described with reference to the preferred embodiments, the preferred embodiments are not intended to limit the application, and those skilled in the art can make various modifications and adaptations without departing from the spirit and scope of the application, and the scope of the application is therefore defined by the claims.

Claims (7)

1. An organic compound characterized by having a structure represented by the general formula I:
（I）
wherein,
n1 is 1 or 2; m1 is any integer from 0 to 5;
R 1 independently at each occurrence, selected from H, or a straight chain alkyl group having 1 to 20C atoms, or a branched alkyl group having 3 to 20C atoms;
R 2 independently at each occurrence, selected from H, or a straight chain alkyl group having 1 to 20C atoms, or a branched alkyl group having 3 to 20C atoms;
Ar 1 and Ar is a group 2 Each occurrence is independently selected from one of the following groups:
wherein,
". Times" represent the site of attachment;
tAm represents 2- (2-methyl) butyl; tBu represents tert-butyl.
2. The organic compound according to claim 1, wherein the organic compound is selected from any one of structures represented by general formulas (II-1) to (II-4):
wherein,
r in the general formula (II-1) 1 Independently at each occurrence, selected from a straight chain alkyl group having 1 to 10C atoms, or a branched alkyl group having 3 to 10C atoms.
3. An organic compound, characterized in that the organic compound is selected from any one of the following structures:
/>
/>
。
4. a mixture comprising an organic compound according to any one of claims 1 to 3 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 emitting host material.
5. A composition comprising an organic compound according to any one of claims 1 to 3 or a mixture according to claim 4 and at least one organic solvent.
6. An organic electronic device comprising the organic compound according to any one of claims 1 to 3 or the mixture according to claim 4.
7. The organic electronic device of claim 6, wherein the organic electronic device comprises a light-emitting layer comprising the organic compound of any one of claims 1-3.
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