CN107903264A - A kind of indole heterocyclic compounds and its organic luminescent device - Google Patents

A kind of indole heterocyclic compounds and its organic luminescent device Download PDF

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CN107903264A
CN107903264A CN201711121896.9A CN201711121896A CN107903264A CN 107903264 A CN107903264 A CN 107903264A CN 201711121896 A CN201711121896 A CN 201711121896A CN 107903264 A CN107903264 A CN 107903264A
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heterocyclic compounds
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刘喜庆
蔡辉
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Changchun Haipurunsi Technology Co Ltd
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains three hetero rings
    • C07D471/14—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms

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  • Organic Chemistry (AREA)
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  • Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Electroluminescent Light Sources (AREA)

Abstract

The present invention provides a kind of indole heterocyclic compounds and its organic luminescent device, is related to organic optoelectronic materials technology.The characteristics of including three nitrogen-atoms that can attract electronics in heterocyclic compound, therefore the heterocyclic compound is easy to shift electronics, and between being stacked on molecule because of its strong flatness, and having indole structure to expand conjugated system, show high electron mobility.When manufacturing organic luminescent device using its, during especially as electron transfer layer, device shows the advantages of driving voltage is low, luminous efficiency is high, long lifespan, better than existing common OLED device.

Description

A kind of indole heterocyclic compounds and its organic luminescent device
Technical field
The present invention relates to organic photoelectrical material technical field, and in particular to a kind of indole heterocyclic compounds and its organic hair Optical device.
Background technology
In recent years, Organic Light Emitting Diode (OLED:Organic Light Emitting Diode) as a kind of new The visual field of people is progressed into promising Display Technique.It is compared with traditional Display Technique, in voltage characteristic, luminance Degree, luminous efficiency, device weight, response speed and appreciative perspective etc. have a significant advantage, and because of its low cost potential, Possess broad mass market prospect.
In the manufacturing process of OLED, the selection of material is very crucial.In terms of the structural point of device, organic electroluminescence Luminescent material can substantially be divided into three types：Electrode material and electrode modified material, carrier transmission material, luminescent material.
The balance injection of carrier is to improve the key factor of OLED element luminous efficiency, therefore, just has to solve such as The problem of He Caineng makes carrier realize balance injection in the devices.It can be divided into according to the difference of carrier：Electron transport material (ETM) and hole mobile material (HTM).
Electron transport material shows as short of electricity subsystem on molecular structure, mostly receives electronic capability with stronger, Electronics, the film forming that also had and stability can be effectively transmitted under certain forward bias.Ideally, electric transmission The electron mobility of material should be suitable with the hole mobility of hole mobile material, and the actually electronics conduction of organic material Speed is much smaller than hole-conductive speed.Electron transport material is all the plane aromatic compound for having big conjugated structure.It is common ETM You oxadiazoles classes (PBD, BND), anthracene azole, ferrosin class (Phen, BCP) and triazines etc..
At present, the research of electroluminescent organic material is carried out extensively in academia and industrial quarters, a large amount of function admirables Electroluminescent organic material be developed successively, but the technological industrialization process still faces many key issues how Design the more preferable electron transport material of new performance to be adjusted, be always those skilled in the art's urgent problem to be solved.
The content of the invention
It is provided by the invention miscellaneous the object of the present invention is to provide a kind of indole heterocyclic compounds and its organic luminescent device Cycle compound thermal stability is high, good film-forming property, and preparation method is simple, the organic luminescent device made of the compound, performance The advantages of going out high efficiency, low driving voltage and long-life, is the luminous organic material of function admirable.
Present invention firstly provides a kind of indole heterocyclic compounds, structural formula is：
Wherein, L is selected from the substituted or unsubstituted condensed ring virtue of the substituted or unsubstituted aryl of C6~C25, C10~C20 One kind in base,
A structural formulas are as shown in chemical formula a~chemical formula c：
Wherein, R1、R2、R3、R4The substitution of the independent substituted or unsubstituted alkyl selected from C1-C10, C6~C25 or not One kind in substituted aryl, the substituted or unsubstituted fused ring aryl of C10~C20.
Preferably, the L is selected from such as lower structure：
Wherein, R5、R6、R7The independent alkyl selected from C1~C10, the substituted or unsubstituted aryl of C6~C20, C10~ One kind in the substituted or unsubstituted fused ring aryl of C20.
Preferably, any one of the indole heterocyclic compounds in such as lower structure：
The present invention also provides the application of indole heterocyclic compounds in an organic light emitting device.
Preferably, the organic luminescent device includes anode, cathode and organic matter layer, and organic matter layer is injected comprising hole At least one layer in layer, hole transmission layer, electronic barrier layer, luminescent layer, hole blocking layer, electron transfer layer, electron injecting layer；
At least one layer in the organic matter layer contains the indole heterocyclic compounds.
Preferably, the indole heterocyclic compounds are used to prepare the electron transfer layer of organic luminescent device.
Beneficial effects of the present invention:
Present invention firstly provides a kind of indole heterocyclic compounds, which has knot shown in formula (1) Structure, three nitrogen-atoms that can attract electronics are included in heterocyclic compound, therefore the heterocyclic compound is easy to shift electronics, and Between being stacked on molecule because of its strong flatness, and there is indole structure to expand conjugated system, show high electron mobility The characteristics of.When manufacturing organic luminescent device using its, during especially as electron transfer layer, device show driving voltage it is low, The advantages of luminous efficiency is high, long lifespan, better than existing common OLED device.
Embodiment
For a further understanding of the present invention, the preferred embodiment of the invention is described with reference to embodiment, still It should be appreciated that these descriptions are simply further explanation the features and advantages of the present invention, rather than to the claims in the present invention Limitation.
Alkyl of the present invention refers to minus the alkyl that a hydrogen atom forms in alkane molecule, it can be straight chain alkane Base, branched alkyl, cycloalkyl, example may include methyl, ethyl, propyl group, isopropyl, normal-butyl, isobutyl group, sec-butyl, tertiary fourth Base, amyl group, isopentyl, cyclopenta, cyclohexyl etc., but not limited to this.
Alkoxy of the present invention refer to alkyl and oxygen atom link after group, example may include methoxyl group, ethyoxyl, 2- propoxyl group, 2- cyclohexyloxies etc., but not limited to this.
Aryl of the present invention refers to after removing a hydrogen atom on the aromatic core carbon of phenyl molecule, is left the total of univalent perssad Claiming, example may include phenyl, 4- aminomethyl phenyls, 4- tert-butyl-phenyls, 2- ethylphenyls, xenyl or terphenyl etc., but not It is limited to this.
Thick aryl of the present invention refers to after removing a hydrogen atom on the aromatic core carbon of aromatic hydrocarbon molecule, is left univalent perssad General name, example may include 1- naphthyls, 2- naphthyls, anthryl, phenanthryl or pyrenyl etc., but not limited to this.
Heteroaryl of the present invention refers to the base that one or more of phenyl molecule aromatic core carbon is substituted by hetero atom The general name of group, the hetero atom include but not limited to oxygen, sulphur or nitrogen-atoms, example may include pyridine radicals, pyrrole radicals, thienyl, Furyl, Evil oxazolyls or triazine radical etc., but not limited to this.
Thick heteroaryl of the present invention refers to what one or more of aromatic hydrocarbon molecule aromatic core carbon was substituted by hetero atom The general name of group, the hetero atom include but not limited to oxygen, sulphur or nitrogen-atoms, and example may include indyl, quinolyl, isoquinolin Base, benzothienyl, benzofuranyl, dibenzofuran group, dibenzothiophene or carbazyl etc., but not limited to this.
Present invention firstly provides a kind of indole heterocyclic compounds, structural formula is：
Wherein, L is selected from the substituted or unsubstituted condensed ring virtue of the substituted or unsubstituted aryl of C6~C25, C10~C20 One kind in base,
A structural formulas are as shown in chemical formula a~chemical formula c：
Wherein, R1、R2、R3、R4The substitution of the independent substituted or unsubstituted alkyl selected from C1-C10, C6~C25 or not One kind in substituted aryl, the substituted or unsubstituted fused ring aryl of C10~C20.
Preferably, the L is selected from such as lower structure：
Wherein, R5、R6、R7The independent alkyl selected from C1~C10, the substituted or unsubstituted aryl of C6~C20, C10~ One kind in the substituted or unsubstituted fused ring aryl of C20.
According to the present invention, the substituted aryl, substitution five-ring heterocycles, substitution hexa-member heterocycle, substitution it is thick miscellaneous In ring, substituent independence is selected from alkyl, alkoxy, amino, halogen, cyano group, nitro, hydroxyl or sulfydryl.
Preferably, any one of the indole heterocyclic compounds in such as lower structure：
The preparation method of the indole heterocyclic compounds of the present invention is as follows：
Wherein, L is selected from the substituted or unsubstituted condensed ring virtue of the substituted or unsubstituted aryl of C6~C25, C10~C20 One kind in base,
A structural formulas are as shown in chemical formula a~chemical formula c：
Wherein, R1、R2、R3、R4The substitution of the independent substituted or unsubstituted alkyl selected from C1-C10, C6~C25 or not One kind in substituted aryl, the substituted or unsubstituted fused ring aryl of C10~C20.
According to the present invention, the compound shown in intermediate A is prepared according to method as follows：
Under nitrogen protection, halides obtain intermediate A with triisopropyl borate ester reaction.
According to the present invention, the compound shown in intermediate B is prepared according to method as follows：
2-aminopyridine obtains intermediate B via a series of condensation ring closure reactions.
According to the present invention, the compound shown in structural formula (1) is prepared according to method as follows：
Under nitrogen protection, tetra-triphenylphosphine palladium is catalyst, in the case that potassium carbonate is alkali, intermediate B and intermediate A Compound shown in structural formula (1) is obtained through Suzuki coupling reactions.
Alternatively, intermediate B and the indoles of substitution are obtained shown in structural formula (1) via Buchwald-Hartwig coupling reactions Compound.
The indole heterocyclic compounds of the present invention are prepared via coupling reaction, do not have special limit to the coupling reaction System, using coupling reaction condition well-known to those skilled in the art, the preparation method is simple, and raw material is easy to get.
The present invention also provides the application of the indole heterocyclic compounds in an organic light emitting device, the organic illuminator Part includes anode, cathode and organic matter layer, and organic matter layer includes hole injection layer, hole transmission layer, electronic barrier layer, shines At least one layer in layer, hole blocking layer, electron transfer layer, electron injecting layer；At least one layer in the organic matter layer contains The indole heterocyclic compounds.The indole heterocyclic compounds specifically can be as the electronics for preparing organic luminescent device Transport layer.The device architecture of use is preferably specially：The ITO on transparent glass is attached to as anode, 2-TNATA is as hole Implanted layer, NPB is as hole transmission layer, and mixing evaporation H1/D1 is miscellaneous as luminescent layer, indoles of the present invention on hole transmission layer Cycle compound is electron transfer layer, and LiF is as electron injecting layer, and metal Al is as cathode.The organic luminescent device can be used for The application fields such as flat-panel monitor, lighting source, direction board, signal lamp.
The present invention has no particular limits the raw material employed in following embodiments, can be for commercial product or using this Preparation method known to field technology personnel is prepared.
Embodiment 1：
The preparation of intermediate B 1
Ethanol (1100ml) is put into compound 2-aminopyridine (27.0g, 286.6mmol) and 2 bromo- 2 '-nitrobenzene second In ketone (70.0g, 286.6mmol), and gained mixture is flowed back.After termination of the reaction, products therefrom is cooled to room temperature simultaneously Extracted with ethyl acetate/water, organic layer is dried with anhydrous magnesium sulfate, then remove solvent by using Rotary Evaporators.Through Target compound a (30.3g, yield 44%) is obtained by column chromatography.
Compound a (30.3g, 126.7mmol) and stannous chloride (II) dihydrate (142.9g, 633.3mmol) is molten Solution in ethanol, and flows back resulting solution under the injection of nitrogen.After termination of the reaction, solution is cooled to room temperature, Xiang Qi Middle addition ice, is then adjusted pH to about 8 by being slowly added sodium acid carbonate thereto.Be laid with bed of diatomaceous earth, with ethyl acetate/ Water extracts filtered filtrate, and organic layer is dried with anhydrous magnesium sulfate, then removes solvent by using Rotary Evaporators.Through Target compound b (213.75g, yield 52%) is obtained by column chromatography.
By compound b (13.75g, 65.71mmol), 3- bromobenzaldehydes (18.24g, 98.57mmol) and p-methyl benzenesulfonic acid (11.3g, 65.71mmol) is dissolved in toluene, and then resulting solution flows back.After termination of the reaction, solution is cooled to often Temperature, first removes toluene, extracts products therefrom with ethyl acetate/water, organic layer is dried with anhydrous magnesium sulfate, then by using Rotary Evaporators remove solvent.Intermediate B 1 (9.34g, yield 38%) is obtained via column chromatography.
The preparation of compound 1
By tri-butyl phosphine (toluene solution of the 1.0M of 4.4mL, 1.48g, 0.05mmol), palladium (0.4g, 1.83mmol) and sodium tert-butoxide (22.8g, 238mmol) is added to intermediate B 1 (68.4g, 183mmol) and 2- phenyl -1H- Yin Solution of the diindyl (35.7g, 185mmol) in degassed toluene (1L), and by the mixture heat under reflux 2 it is small when.Should Reaction mixture is cooled to room temperature, and is filtered with dilution with toluene and via diatomite.The filtrate water is diluted, and is carried with toluene Take, and merge organic phase, it is evaporated under vacuo.The residue is filtered via silica gel, and is recrystallized. To target product compound 1 (62.2g, theoretical value 70%).Mass spectrum m/z：486.53 (calculated values：486.57).Theoretical elemental contains Measure (%) C34H22N4：C,83.93；H,4.56；N, 11.51 actual measurement constituent contents (%)：C,83.91；H,4.57；N,11.52.On Stating result confirms that it is target product to obtain product.
Embodiment 2：
Change 3- bromobenzaldehydes in embodiment 1 into equimolar p-bromobenzaldehyde, 2- phenyl -1H- indoles changes equimolar into 2,3- diphenyl -1H- indoles, other steps are identical, obtain compound 4.Mass spectrum m/z：562.67 (calculated values：562.66). Theoretical elemental content (%) C40H26N4：C,85.38；H,4.66；N, 9.96 actual measurement constituent contents (%)：C,85.37；H,4.65； N,9.98.The above results confirm that it is target product to obtain product.
Embodiment 3：
Change 3- bromobenzaldehydes in embodiment 1 into equimolar 5- bromo- 2- naphthaldehydes, other steps are identical, obtain chemical combination Thing 14.Mass spectrum m/z：612.78 (calculated values：612.72).Theoretical elemental content (%) C44H28N4：C,86.25；H,4.61；N, 9.14 actual measurement constituent contents (%)：C,86.24；H,4.63；N,9.13.The above results confirm that it is target product to obtain product.
Embodiment 4：
The preparation of intermediate A 1
By tri-butyl phosphine (toluene solution of the 1.0M of 4.4mL, 1.48g, 0.05mmol), palladium (0.4g, 1.83mmol) and sodium tert-butoxide (40.4g, 420mmol) added to the bromo- 3- phenyl -1H- indoles (49.7g, 183mmol) of 2- and Solution of the 4- iodine biphenyl (51.8g, 185mmol) in degassed toluene (1L), and it is small that the mixture is heated 2 under reflux When.The reaction mixture is cooled to room temperature, is filtered with dilution with toluene and via diatomite.The filtrate water is diluted, and Extracted with toluene, and merge organic phase, it is evaporated under vacuo.The residue is filtered via silica gel, and Recrystallization.To adding THF 100mL in obtained product (18.0,42.4mmol), nitrogen protection, -78 DEG C are stirred 30 minutes, so N-BuLi (2.5M) 21mL is added afterwards, when reaction 1 is small, adds triisopropyl borate ester 14g, it is gradually extensive when low-temp reaction 1 is small Multiple room temperature.Last handling process, 2M hydrochloric acid is added in system makes solution pH value be 4-5, stands liquid separation, and aqueous layer with ethyl acetate extracts Take, merge organic layer, be spin-dried for, obtain intermediate A 1 (13.2g, yield 80%).
The preparation of compound 24
By tri-butyl phosphine (toluene solution of the 1.0M of 4.4mL, 1.48g, 0.05mmol), palladium (0.4g, 1.83mmol) and sodium tert-butoxide (22.8g, 238mmol) is added to intermediate B 2 (68.4g, 183mmol) and intermediate A 1 The solution of (72.0g, 185mmol) in degassed toluene (1L), and by the mixture heat under reflux 2 it is small when.This is anti- Answer mixture to be cooled to room temperature, filtered with dilution with toluene and via diatomite.The filtrate water is diluted, and is carried with toluene Take, and merge organic phase, it is evaporated under vacuo.The residue is filtered via silica gel, and is recrystallized. To target product compound 24 (70.0g, theoretical value 60%).Mass spectrum m/z：638.83 (calculated values：638.76).Theoretical elemental contains Measure (%) C46H30N4：C,86.49；H,4.73；N, 8.77 actual measurement constituent contents (%)：C,86.48；H,4.76；N,8.76.It is above-mentioned As a result confirm that it is target product to obtain product.
Embodiment 5：
Change p-bromobenzaldehyde in embodiment 4 into equimolar 4 '-bromo- [1,1 '-biphenyl] -4- formaldehyde, other step phases Together, compound 36 is obtained.Mass spectrum m/z：638.78 (calculated values：638.76).Theoretical elemental content (%) C46H30N4：C,86.49； H,4.73；N, 8.77 actual measurement constituent contents (%)：C,86.48；H,4.75；N,8.77.The above results confirm that it is mesh to obtain product Mark product.
Embodiment 6：
Change 4- iodine biphenyl in embodiment 4 into equimolar 2- iodine naphthalene, p-bromobenzaldehyde changes the bromo- 1- naphthalenes of equimolar 4- into Formaldehyde, other steps are identical, obtain compound 64.Mass spectrum m/z：662.80 (calculated values：662.78).Theoretical elemental content (%) C48H30N4：C,86.98；H,4.56；N, 8.45 actual measurement constituent contents (%)：C,86.99；H,4.57；N,8.44.The above results are demonstrate,proved The real product that obtains is target product.
Embodiment 7：
Change 4- iodine biphenyl in embodiment 4 into equimolar 1- iodine naphthalene, p-bromobenzaldehyde changes the bromo- 1- naphthalenes of equimolar 6- into Formaldehyde, other steps are identical, obtain compound 76.Mass spectrum m/z：662.80 (calculated values：662.78).Theoretical elemental content (%) C48H30N4：C,86.98；H,4.56；N, 8.45 actual measurement constituent contents (%)：C,86.97；H,4.57；N,8.46.The above results are demonstrate,proved The real product that obtains is target product.
Embodiment 8：
Change 4- iodine biphenyl in embodiment 4 into equimolar iodobenzene, p-bromobenzaldehyde changes the bromo- 2- naphthalenes first of equimolar 6- into Aldehyde, other steps are identical, obtain compound 114.Mass spectrum m/z：688.80 (calculated values：688.82).Theoretical elemental content (%) C50H32N4：C,87.18；H,4.68；N, 8.13 actual measurement constituent contents (%)：C,87.19；H,4.69；N,8.12.The above results are demonstrate,proved The real product that obtains is target product.
Embodiment 9：
Change 4- iodine biphenyl in embodiment 4 into equimolar iodobenzene, p-bromobenzaldehyde changes the bromo- 2- naphthalenes first of equimolar 6- into Aldehyde, other steps are identical, obtain compound 114.Mass spectrum m/z：688.80 (calculated values：688.82).Theoretical elemental content (%) C50H32N4：C,87.18；H,4.68；N, 8.13 actual measurement constituent contents (%)：C,87.19；H,4.69；N,8.12.The above results are demonstrate,proved The real product that obtains is target product.
Comparative example 1
Anode is 15 Ω/cm of healthy and free from worry (Corning) company2 Ito glass substrate cuts into 50mm*50mm* 0.7mm sizes, and each ultrasonic cleaning for carrying out 15 minutes, UV ozone of 30 minutes in water, acetone, isopropanol successively by it Reused after cleaning.On the glass substrate, 2-TNATA is carried out to the hole injection layer of formation 80nm thickness after vacuum evaporation. NPB is subjected to vacuum evaporation on hole injection layer, forms the hole transmission layer of 30nm thickness.Will on hole transmission layer above H1/D1 (doping level 5%) carries out the luminescent layer of formation 25nm after vacuum evaporation.Then, on the light-emitting layer by the compound of E1 with The thickness of 30nm carries out vacuum evaporation, forms electron transfer layer.By LiF 0.5nm (electron injecting layer) and Al on electron transfer layer The carry out vacuum evaporations of 600nm (cathode) successively.Organic luminescent device is made, is known as comparative sample 1
Organic luminescent device is prepared by the aromatic amine analog derivative：
The indole heterocyclic compounds of the invention are replaced into E1 as the compound in electron transfer layer, with and on State the same method of comparative example 1 and manufacture organic luminescent device.
The device of comparative example 1 is surveyed with preparing the parameter of organic luminescent device by the indole heterocyclic compounds Examination, it is beautiful using US business Keithley instrument limited company Taiwan branch company Keithley2400 series digits source table, Konica It can be evaluated up to konica minolta CS-2000, CS-2000A photometer evaluation driving voltage, luminous efficiency, to result The form of table 1 below shows.
Table 1
Result above shows that the indole heterocyclic compounds in the present invention are applied in organic luminescent device, especially make For electron transport material, the advantages of showing high efficiency, low driving voltage, be luminous organic material of good performance.
Obviously, the explanation of above example is only intended to help to understand method and its core concept of the invention.It should refer to Go out, without departing from the principle of the present invention, can also be to this hair for the those of ordinary skill of the technical field Bright to carry out some improvement and modification, these are improved and modification is also fallen into the protection domain of the claims in the present invention.

Claims (5)

1. a kind of indole heterocyclic compounds, it is characterised in that shown in structural formula such as formula (1)：
Wherein, in the substituted or unsubstituted fused ring aryl of substituted or unsubstituted aryl of the L selected from C6~C25, C10~C20 One kind,
A structural formulas are as shown in chemical formula a~chemical formula c：
Wherein, R1、R2、R3、R4The substitution or unsubstituted of the independent substituted or unsubstituted alkyl selected from C1-C10, C6~C25 Aryl, C10~C20 substituted or unsubstituted fused ring aryl in one kind.
2. a kind of indole heterocyclic compounds according to claim 1, it is characterised in that L is selected from such as lower structure：
Wherein, R5、R6、R7The independent alkyl selected from C1~C10, substituted or unsubstituted aryl, the C10~C20 of C6~C20 Substituted or unsubstituted fused ring aryl in one kind.
3. a kind of indole heterocyclic compounds according to claim 1, it is characterised in that the derivative is selected from following knot Any one in structure：
4. a kind of organic luminescent device, it is characterised in that the organic luminescent device includes cathode, anode and is placed in two electricity Organic compound layer between pole, the organic compound layer include hole injection layer, hole transmission layer, electronic barrier layer, hair At least one layer in photosphere, hole blocking layer, electron transfer layer, electron injecting layer；It is at least one layer of in the organic compound layer Contain a kind of indole heterocyclic compounds of claim 1-3 any one of them.
5. according to a kind of organic luminescent device described in claim 4, it is characterised in that wanted in electron transfer layer containing having the right Seek a kind of indole heterocyclic compounds described in book 1-3.
CN201711121896.9A 2017-11-14 2017-11-14 A kind of indole heterocyclic compounds and its organic luminescent device Withdrawn CN107903264A (en)

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Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2016160208A (en) * 2015-03-02 2016-09-05 東レ株式会社 Chemical compound, luminous element containing the same, photoelectric conversion element and image sensor
CN106632327A (en) * 2015-11-04 2017-05-10 三星显示有限公司 Compound and organic light emitting device comprising same
CN107001370A (en) * 2014-10-31 2017-08-01 喜星素材株式会社 Heterocyclic compound and use its organic luminescent device

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN107001370A (en) * 2014-10-31 2017-08-01 喜星素材株式会社 Heterocyclic compound and use its organic luminescent device
JP2016160208A (en) * 2015-03-02 2016-09-05 東レ株式会社 Chemical compound, luminous element containing the same, photoelectric conversion element and image sensor
CN106632327A (en) * 2015-11-04 2017-05-10 三星显示有限公司 Compound and organic light emitting device comprising same

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Application publication date: 20180413