CN108359445A - A kind of bipolarity electroluminescent organic material and its organic luminescent device - Google Patents

A kind of bipolarity electroluminescent organic material and its organic luminescent device Download PDF

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CN108359445A
CN108359445A CN201810422781.1A CN201810422781A CN108359445A CN 108359445 A CN108359445 A CN 108359445A CN 201810422781 A CN201810422781 A CN 201810422781A CN 108359445 A CN108359445 A CN 108359445A
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substituted
unsubstituted
base
bipolarity
organic material
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孙可
孙可一
蔡辉
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Changchun Haipurunsi Technology Co Ltd
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Changchun Haipurunsi Technology Co Ltd
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Abstract

A kind of bipolarity electroluminescent organic material of present invention offer and its organic luminescent device, belong to organic photoelectrical material technical field.Structure containing sulfone and carbazole in electroluminescent organic material structure provided by the invention has bipolar transmission ability so that carrier transport balances, and electronics is happened at luminescent layer with hole-recombination so that the luminous efficiency of device improves.Compared with prior art, it is applied to organic luminescent device, is used especially as the blue emitting material in luminescent layer, there is relatively high luminous efficiency and lower driving voltage.

Description

A kind of bipolarity electroluminescent organic material and its organic luminescent device
Technical field
The present invention relates to organic photoelectrical material technical fields, and in particular to a kind of bipolarity electroluminescent organic material and its Organic luminescent device.
Background technology
Organic electroluminescent refers to organic material under electric field action, luminous by the excitation of electric current and electric field to show As.Organic electroluminescent LED (OLED) is the display technology of new generation that display is realized using this phenomenon.From U.S. in 1987 State Kodak Company Tang C.W. and Vanslyke S.A. made the organic electroluminescence device of first function admirable with Come, ORGANIC ELECTROLUMINESCENCE DISPLAYS causes the great interest of people since it has the advantage that.
At present, the luminescent material of feux rouges and green light is commercially applied due to its excellent performance, and blue The wide energy gap and high thermal stability of luminescent material, are conflicts, therefore the blue light material haveing excellent performance more lacks.For common Anthracene class fluorescence blue light material, luminous efficiency is relatively low；And for the phosphorescence blue light material such as Firpic, the service life is again relatively low.
On the other hand, as material of main part, in addition to triplet is higher than guest materials, prevent exciton transition from discharging Other than the inverse transmission of energy, it is often more important that the mobility of balance electronic and hole so that carrier transport balances, electronics and hole Compound to be happened at luminescent layer, this is particularly significant for the luminous efficiency for improving device.Therefore, it is better how to design new performance Blue light material is always those skilled in the art's urgent problem to be solved.
Invention content
In view of this, the purpose of the present invention is to provide a kind of bipolarity electroluminescent organic material and its organic illuminators Part, the organic luminescent device prepared using bipolarity electroluminescent organic material of the present invention have higher luminous efficiency.
Present invention firstly provides a kind of bipolarity electroluminescent organic materials, and general structure is as shown in I：
L1-L9It is independent selected from hydrogen, it is C1-C30 alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted One kind in C6-C30 arylamine, substituted or unsubstituted C3-C30 heteroaryls.
L, L10It is independent to be selected from C1-C30 alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6- One kind in C30 arylamine, substituted or unsubstituted C3-C30 heteroaryls.
Preferably, L1-L9Independent one kind in hydrogen, substituted or unsubstituted C6-C30 aryl；L, L10It is independent It is miscellaneous selected from substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 arylamine, substituted or unsubstituted C3-C30 One kind in aryl.
Preferably, general structure is as shown in II：
L, L10It is independent to be selected from substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 arylamine, substitution Or one kind in unsubstituted C3-C30 heteroaryls.
Preferably, L, L10It is independent to be selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthalene, substitution or do not take It is the anthryl in generation, substituted or unsubstituted phenanthryl, substituted or unsubstituted benzo phenanthryl, substituted or unsubstitutedBase, substitution or One kind in unsubstituted pyrene or group as described below：
R1, R2It is independent to be selected from hydrogen, methyl, ethyl, isopropyl, tertiary butyl, phenyl, naphthalene, anthryl, phenanthryl, pyrenyl, bend Base, fluoranthene base, base, hexichol amido, triphenylamine base, carbazyl, dicarbazyl, benzo carbazole base, indyl, phenothiazinyl, Phenoxazine group, dimethyl acridinium base, diphenylacridine base, dimethyl fluorenyl, diphenyl fluorenyl, dibenzothiophene, dibenzo Furyl, diphenyl ether base, diphenyl sulfide ether, diphenyl sulfone, pyridyl group, pyrimidine radicals, triazine radical or phenanthroline base；
N is selected from the integer of 0-5；
M is selected from the integer of 0-4；
P is selected from the integer of 0-3；
Y is selected from O, S, N (Ph) or C (CH3)2；
* binding site is indicated.
Preferably, L1-L9It is independent selected from hydrogen, substituted or unsubstituted phenyl, substituted or unsubstituted naphthalene, substitution or It is unsubstituted anthryl, substituted or unsubstituted phenanthryl, substituted or unsubstituted benzo phenanthryl, substituted or unsubstitutedBase takes Generation or unsubstituted pyrene.
Preferably, a kind of bipolarity electroluminescent organic material, any one in such as lower structure：
The present invention also provides a kind of bipolarity organic luminescent device, including first electrode, second electrode and it is placed in described One or more organic compound layers between one electrode and the second electrode, at least one organic compound layer contain described Electroluminescent organic material.
Preferably, the organic compound layer includes luminescent layer, and the organic electroluminescence material is contained in the luminescent layer Material.
Beneficial effects of the present invention：
Structure containing sulfone and carbazole in electroluminescent organic material structure provided by the invention has bipolar transmission energy Power so that carrier transport balances, and electronics is happened at luminescent layer with hole-recombination so that the luminous efficiency of device improves.With it is existing There is technology to compare, be applied to organic luminescent device, used especially as the blue emitting material in luminescent layer, there is phase To higher luminous efficiency and lower driving voltage.
Specific implementation mode
It is clearly and completely described below in conjunction with the technical solution of the embodiment of the present invention, it is clear that described implementation Example is only a part of the embodiment of the present invention, instead of all the embodiments.Based on the embodiments of the present invention, the common skill in this field The every other embodiment that art personnel are obtained without making creative work belongs to the model that the present invention protects It encloses.
Present invention firstly provides a kind of bipolarity electroluminescent organic materials, and general structure is as shown in I：
L1-L9It is independent selected from hydrogen, it is C1-C30 alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted One kind in C6-C30 arylamine, substituted or unsubstituted C3-C30 heteroaryls.
L, L10It is independent to be selected from C1-C30 alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6- One kind in C30 arylamine, substituted or unsubstituted C3-C30 heteroaryls.
According to the present invention, the alkyl refers to alkyl made of minusing a hydrogen atom in alkane molecule.Such as it can be selected from Methyl, ethyl, isopropyl etc., but not limited to this.
The aryl refer to aromatic hydrocarbon molecule aromatic core carbon on remove a hydrogen atom after, be left univalent perssad general name, It can be monocyclic aryl or fused ring aryl, such as can be selected from phenyl, xenyl, naphthalene, anthryl, phenanthryl or pyrenyl etc., but is unlimited In this.
The arylamine refers to the amine for having armaticity substituent, i.e.-NH2,-NH- or nitrogen-containing group be connected on aromatic hydrocarbon, Such as can be selected from aniline, naphthylamines, triphenylamine etc., but not limited to this.
The heteroaryl refers to the group that one or more of aromatic hydrocarbyl aromatic core carbon is substituted by hetero atom General name, the hetero atom include but not limited to oxygen, sulphur and nitrogen-atoms, and the aromatic heterocycle can be monocycle or condensed ring, such as can Selected from carbazyl, carbazole diindyl base, dibenzofuran group, dibenzothiophene, dibenzo-thiophene dioxide base, phenthazine Base, titanium dioxide phenothiazinyl, phenoxazine groups, acridinyl, dimethyl acridinium base, diphenylacridine base, dibenzo piperidyl, pyridine Base, pyrimidine radicals, pyridazinyl, pyrazinyl, quinolyl, triazine radical, oxadiazolyl, thiadiazolyl group, triazol radical, indyl, Qu Luo Quinoline base, isoquinolyl etc., but not limited to this.
The substituent group refers to that organic compound group removes one or several-H and the group that is formed, as methyl, ethyl, Isopropyl, tertiary butyl, phenyl, naphthalene, anthryl, Qu Ji, benzo bend base, phenanthryl, benzo phenanthryl, fluoranthene base, base, tolyl, Methoxyl group, methyl mercapto, phenoxy group, thiophenyl, fluorenyl, 9,9- dimethyl fluorenyl, 9,9- diphenyl fluorenyl, hexichol amido, diformazan Amido, carbazyl, carbazole diindyl base, phenyl substituted carbazole base, dibenzofuran group, dibenzothiophene, dibenzo dioxy Thienyl, cyano, fluorine-based, deuterium base, two phenenyl phosphinyl, phenyl sulfuryl, phenylsulfone base, triphenyl silicon substrate, trimethyl silicon substrate, Phenothiazinyl, phenoxazine groups, dimethyl acridinium, diphenylacridine, dibenzo piperidyl, pyridyl group, pyrimidine radicals, are rattled away at acridinyl Piperazine base, pyrazinyl, triazine radical, oxazolyls, thiazolyl, oxadiazolyls, thiadiazolyl group, triazol radical, xenyl, terphenyl, Indyl, indenyl, phenanthroline base, quinolyl, isoquinolyl, nitro etc., but not limited to this.
Preferably, L1-L9It is independent to be selected from hydrogen, substituted or unsubstituted C6-C30 aryl；L, L10It is independent to be selected from substitution Or in unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 arylamine, substituted or unsubstituted C3-C30 heteroaryls It is a kind of.
Preferably, which is characterized in that its general structure is as shown in II：
L, L10It is independent to be selected from substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 arylamine, substitution Or one kind in unsubstituted C3-C30 heteroaryls.
Preferably, L, L10It is independent to be selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthalene, substitution or do not take It is the anthryl in generation, substituted or unsubstituted phenanthryl, substituted or unsubstituted benzo phenanthryl, substituted or unsubstitutedBase, substitution or One kind in unsubstituted pyrene or group as described below.
R1, R2It is independent to be selected from hydrogen, methyl, ethyl, isopropyl, tertiary butyl, phenyl, naphthalene, anthryl, phenanthryl, pyrenyl, bend Base, fluoranthene base, base, hexichol amido, triphenylamine base, carbazyl, dicarbazyl, benzo carbazole base, indyl, phenothiazinyl, Phenoxazine group, dimethyl acridinium base, diphenylacridine base, dimethyl fluorenyl, diphenyl fluorenyl, dibenzothiophene, dibenzo Furyl, diphenyl ether base, diphenyl sulfide ether, diphenyl sulfone, pyridyl group, pyrimidine radicals, triazine radical or phenanthroline base；
N is selected from the integer of 0-5；
M is selected from the integer of 0-4；
P is selected from the integer of 0-3；
Y is selected from O, S, N (Ph) or C (CH3)2；
* binding site is indicated.
Preferably, L1-L9It is independent selected from hydrogen, substituted or unsubstituted phenyl, substituted or unsubstituted naphthalene, substitution or It is unsubstituted anthryl, substituted or unsubstituted phenanthryl, substituted or unsubstituted benzo phenanthryl, substituted or unsubstitutedBase takes Generation or unsubstituted pyrene.
Preferably, a kind of bipolarity electroluminescent organic material, any one in such as lower structure：
A kind of preparation method of bipolarity electroluminescent organic material of the present invention, including shown in raw material pass through it is as follows A kind of electroluminescent organic material shown in route reaction production I：
L1-L9It is independent selected from hydrogen, it is C1-C30 alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted One kind in C6-C30 arylamine, substituted or unsubstituted C3-C30 heteroaryls.
L, L10It is independent to be selected from C1-C30 alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6- One kind in C30 arylamine, substituted or unsubstituted C3-C30 heteroaryls.
1,3- bis- bromo- 2- iodobenzenes pass through suzuki and react successively, more cyclizations of card, oxidation reaction, buchward ammonifications life At target product.
The present invention also provides a kind of organic luminescent device, what the organic luminescent device was well known to those skilled in the art Organic luminescent device.Organic luminescent device of the present invention includes first electrode, second electrode and is placed between two electrodes One or more organic compound layers, at least one organic compound layer includes at least one organic electroluminescence of the present invention Luminescent material.The organic compound layer preferably includes hole injection layer, hole transmission layer, luminescent layer, hole blocking layer, electronics Transport layer and at least one layer in electron injecting layer, preferably containing of the present invention in the luminescent layer or electron transfer layer Electroluminescent organic material.
Embodiment 1：The preparation of compound 1
Step1. 1-7 100mmol are taken, the phenyl boric acid of 1 equivalent, sodium carbonate 300mmol, four triphenyl phosphorus palladiums are added 1mmol, toluene, ethyl alcohol, the mixed solvent of water, argon gas are replaced three times, 5h are reacted under reflux temperature, after reaction, addition is gone Ionized water separates organic phase, and three times, concentration, obtained crude product crosses silicagel column, obtains product 1-6 80mmol for washing.
Step2. 1-6 80mmol are taken, the 1-8, sodium carbonate 240mmol, four triphenyl phosphorus palladium 0.8mmol of 1 equivalent is added, Toluene, ethyl alcohol, the mixed solvent of water, argon gas are replaced three times, and 5h is reacted under reflux temperature, after reaction, deionized water are added, Organic phase is separated, three times, concentration, obtained crude product crosses silicagel column, obtains product 1-5 70mmol for washing.
Step3. 70mmol products 1-5 is dissolved in trifluoromethanesulfonic acid, is stirred at room temperature for 24 hours.Water is added after the completion of reaction It is 8 with pyridine volume ratio:1 in the mixed solvent.Mixed solvent is heated to flowing back, reaction is overnight.Crude product crosses silicagel column, is produced Product 1-4,50mmol.
Step4. 1-4 50mmol are taken, the ortho-nitrophenyl boric acid of 1 equivalent, sodium carbonate 150mmol, four triphenyl phosphorus palladiums are added 0.5mmol, toluene, ethyl alcohol, the mixed solvent of water, argon gas are replaced three times, and 5h is reacted under reflux temperature, after reaction, are added Deionized water separates organic phase, and three times, concentration, obtained crude product crosses silicagel column, obtains product 1-3 40mmol for washing.
Step5. the addition 1-3 40mmol in 250ml there-necked flasks, solvent o-dichlorohenzene, triethyl phosphite 120mmol, Solution is heated to 150 DEG C of holding 15h.Solvent and extra triethyl phosphite are removed in vacuum distillation, and crude product passes through column chromatography. To white solid.Obtain product 1-2 40mmol.
Step6. product 1-2 40mmol are taken, are dissolved in DCM, are cooled to 0 degree Celsius, the m-CPBA of 2 equivalents is added, by It is gradually warming up to room temperature, is stirred to react 6 hours, after the completion of reaction, is washed with anhydrous sodium hydrogensulfite is saturated, organic phase drying, rotation Dry, obtained product crosses silicagel column, obtains target product 1-1,30mmol.
Step6. product product 1-1,30mmol are added in the reaction vessel；Iodobenzene 30mmol, potassium tert-butoxide 90mmol, Three times, ligand tri-tert phosphorus is added in 3 0.3mol of Pd2 (dba), the dimethylbenzene of ultrasonic deoxygenation, stirring and dissolving, displaced air 4%, 1.2mmol, again displaced air three times, back flow reaction 6h.It is cooled to room temperature, enough dichloromethane is added and so that product is complete Fully dissolved, excessively a small amount of silica gel funnel, removes catalyst and salt.Filtrate be concentrated into it is thick, cross column chromatography, obtain product 1, 20mmol。
Embodiment 2：The preparation of compound 2
With embodiment 1.Phenyl boric acid in step1. is changed to anthracene boric acid.
Embodiment 3：The preparation of compound 14
With embodiment 1, the iodobenzene of Step6 is changed to the bromo- 9- phenyl carbazoles of 3-.
Embodiment 4：The preparation of compound 33
With embodiment 1, the phenyl boric acid in Step1 is changed to 4- pyridine boronic acids.
Embodiment 5：The preparation of compound 42
With embodiment 1, the iodobenzene in Step6 is changed to bromo- 9, the 9- dimethyl fluorenes of 3-.
Compound FD-MS values prepared by 1 embodiment of the present invention of table
Compound FD-MS
1 M/z:457.12, C30H19NO2S (457.11)
2 M/z:557.34, C38H23NO2S (557.14)
14 M/z:622.09, C42H26N2O2S (622.17)
33 M/z:458.18, C29H18N2O2S (458.11)
42 M/z：573.08, C39H27NO2S (573.18)
Compare Application Example 1：
Ito glass substrate is placed in distilled water and is cleaned 2 times, ultrasonic washing 30 minutes is different after distilled water cleans Ultrasonic washing is later dry in order for propyl alcohol, acetone, methanol equal solvent, is transferred in plasma washing machine, by above-mentioned base Plate washs 5 minutes, is sent in evaporator.
Hole injection layer TPT-1 is deposited successively on the ito transparent electrode being already prepared toHole is deposited to pass Defeated layer NPBEmitting layer material ADN is deposited：5%DPAP-DPPAThen vapor deposition electron transfer layer Alq3 CathodeAbove process organic matter vaporization plating speed is to maintainLiF isAl is
Application example 1：
Hole injection layer TPT-1 is deposited successively on the ito transparent electrode being already prepared toHole transport is deposited Layer NPBCompound 1 is deposited：5%DPAP-DPPAThen vapor deposition electron transfer layer Alq3 It is cloudy PoleAbove process organic matter vaporization plating speed is to maintainLiF isAl is
Application example 2：
Compound 5 in embodiment 1 is changed to compound 2.
Application example 3：
Compound 5 in embodiment 1 is changed to compound 14.
Application example 4：
Compound 5 in embodiment 1 is changed to compound 33.
Application example 5：
Compound 5 in embodiment 1 is changed to compound 42.
Measure embodiment 1：The luminescent properties of contrast sample and sample
Contrast sample and sample are using Keithley SMU235, and the results are shown in Table 2 for PR650 evaluations luminous efficiency：
The characteristics of luminescence of luminescent device prepared by 2 embodiment of the present invention of table
Although the present invention has carried out special description with exemplary embodiment, but it is understood that without departing from claim Defined by the case of spirit and scope of the invention, those of ordinary skill in the art can carry out various forms and details to it On change.

Claims (8)

1. a kind of bipolarity electroluminescent organic material, general structure is as shown in I：
L1-L9It is independent to be selected from hydrogen, C1-C30 alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 One kind in arylamine, substituted or unsubstituted C3-C30 heteroaryls；
L, L10It is independent fragrant selected from C1-C30 alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 One kind in amine, substituted or unsubstituted C3-C30 heteroaryls.
2. a kind of electroluminescent organic material of bipolarity electroluminescent organic material according to claim 1, feature It is,
L1-L9Independent one kind in hydrogen, substituted or unsubstituted C6-C30 aryl；
L, L10It is independent selected from substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 arylamine, substitution or not One kind in substituted C3-C30 heteroaryls.
3. a kind of electroluminescent organic material of bipolarity electroluminescent organic material according to claim 1, feature It is, general structure is as shown in II：
L, L10It is independent selected from substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 arylamine, substitution or not One kind in substituted C3-C30 heteroaryls.
4. a kind of electroluminescent organic material of bipolarity electroluminescent organic material according to claim 1, feature It is, L, L10It is independent selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthalene, substituted or unsubstituted anthryl, It is substituted or unsubstituted phenanthryl, substituted or unsubstituted benzo phenanthryl, substituted or unsubstitutedBase, substituted or unsubstituted pyrene Or group as described below：
R1, R2It is independent selected from hydrogen, it is methyl, ethyl, isopropyl, tertiary butyl, phenyl, naphthalene, anthryl, phenanthryl, pyrenyl, Qu Ji, glimmering Anthryl, base, hexichol amido, triphenylamine base, carbazyl, dicarbazyl, benzo carbazole base, indyl, phenothiazinyl, phenoxazine Base, dimethyl acridinium base, diphenylacridine base, dimethyl fluorenyl, diphenyl fluorenyl, dibenzothiophene, dibenzofuran group, Diphenyl ether base, diphenyl sulfide ether, diphenyl sulfone, pyridyl group, pyrimidine radicals, triazine radical or phenanthroline base；
N is selected from the integer of 0-5；
M is selected from the integer of 0-4；
P is selected from the integer of 0-3；
Y is selected from O, S, N (Ph) or C (CH3)2；
* binding site is indicated.
5. a kind of electroluminescent organic material of bipolarity electroluminescent organic material according to claim 1, feature It is, L1-L9It is independent to be selected from hydrogen, substituted or unsubstituted phenyl, substituted or unsubstituted naphthalene, substituted or unsubstituted anthracene It is base, substituted or unsubstituted phenanthryl, substituted or unsubstituted benzo phenanthryl, substituted or unsubstitutedBase, substitution or unsubstituted Pyrene in one kind.
6. a kind of bipolarity electroluminescent organic material according to claim 1, which is characterized in that in such as lower structure One kind：
7. a kind of bipolarity organic luminescent device, including first electrode, second electrode and it is placed in the first electrode and described the One or more organic compound layers between two electrodes, which is characterized in that at least one organic compound layer contains such as right It is required that a kind of bipolarity electroluminescent organic material described in 1 to 6 any one.
8. according to a kind of bipolarity organic luminescent device described in claim 7, which is characterized in that the organic compound layer Including luminescent layer, a kind of bipolarity organic electroluminescent as described in any one of claim 1 to 6 is contained in the luminescent layer Material.
CN201810422781.1A 2018-05-05 2018-05-05 A kind of bipolarity electroluminescent organic material and its organic luminescent device Withdrawn CN108359445A (en)

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CN111217832A (en) * 2018-11-23 2020-06-02 北京夏禾科技有限公司 Organic compound, electroluminescent device containing organic compound and application of electroluminescent device
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WO2023152063A1 (en) * 2022-02-09 2023-08-17 Merck Patent Gmbh Materials for organic electroluminescent devices
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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN111217832A (en) * 2018-11-23 2020-06-02 北京夏禾科技有限公司 Organic compound, electroluminescent device containing organic compound and application of electroluminescent device
CN111217832B (en) * 2018-11-23 2023-04-18 北京夏禾科技有限公司 Organic compound, electroluminescent device containing organic compound and application of organic compound
WO2021145429A1 (en) * 2020-01-15 2021-07-22 出光興産株式会社 Compound, material for organic electroluminescent elements, organic electroluminescent element, and electronic device
CN113354661A (en) * 2021-05-18 2021-09-07 陕西莱特光电材料股份有限公司 Organic compound, electronic element containing organic compound and electronic device
WO2023152063A1 (en) * 2022-02-09 2023-08-17 Merck Patent Gmbh Materials for organic electroluminescent devices
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