CN106397405B - A kind of organic luminescent compounds containing anthracene and the organic luminescent device containing it - Google Patents

A kind of organic luminescent compounds containing anthracene and the organic luminescent device containing it Download PDF

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CN106397405B
CN106397405B CN201610825572.2A CN201610825572A CN106397405B CN 106397405 B CN106397405 B CN 106397405B CN 201610825572 A CN201610825572 A CN 201610825572A CN 106397405 B CN106397405 B CN 106397405B
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CN106397405A (en
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高春吉
王进政
陈明
胡晓明
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Jilin Optical and Electronic Materials Co Ltd
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
    • C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
    • C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
    • C07D235/18—Benzimidazoles; Hydrogenated benzimidazoles with aryl radicals directly attached in position 2
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • 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
    • H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
    • H10K85/633—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
    • 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
    • H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
    • H10K85/636—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom
    • 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
    • H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
    • 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
    • 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
    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene

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  • Electroluminescent Light Sources (AREA)

Abstract

The present invention provides a kind of materials for electron-transport, and use the organic luminescent device of the organic luminescent compounds.The general formula of molecular structure of the anthracene compound are as follows:Wherein, R1 is selected from substitution or is substituted C1~C60Alkyl, substituted or unsubstituted C6~C60Aryl, substituted or unsubstituted C5~C60Condensed ring radical and substituted or unsubstituted C5~C60Heterocycle.R2 is selected from substitution or is substituted C1~C60Alkyl, substituted or unsubstituted C6~C60Aryl, substituted or unsubstituted C5~C60Condensed ring radical and substituted or unsubstituted C5~C60Heterocycle.The efficiency and excitation purity for having low connection voltage and long-life high using the organic luminescent device that the organic luminescent compounds manufacture.

Description

A kind of organic luminescent compounds containing anthracene and the organic luminescent device containing it
Technical field
The present invention relates to organic photoelectrical material technical field, more particularly to it is a kind of containing anthracene compound and preparation method thereof with And a kind of organic luminescent device.
Background technique
Organic electroluminescent (EL) is generally by two opposed electrodes and at least one layer being inserted between two electrodes Organic luminescent compounds composition.Charge is injected into the organic layer formed between the anode and cathode, to form electronics and sky Cave pair makes the organic compound with fluorescence or phosphorescent characteristics produce light emitting.
Research for organic EL Material is to apply height to the macromolecule membrane containing organic pigment from nineteen fifty Bernose What Current Voltage observed.Nineteen sixty-five, Pope et al. have found the Electroluminescence Properties of anthracene single crystal for the first time, this is organic compound The first electro optical phenomenon.
For the high organic luminescent device of producing efficiency, researcher gradually becomes the structure of organic matter layer in device from single layer For multilayered structure.It is the movement speed difference due to hole with electronics that El element, which is designed as multilayered structure, appropriate to design Hole injection layer, hole transmission layer, electron transfer layer and electron injecting layer improve the efficiency of transmission of hole and electronics, make device Hole and electronics reach balanced in part, to improve luminous efficiency.
Tang of Kodak in 1987 et al. discovery, by using ITO as anode, Mg-Ag alloy is as cathode, and three (8-hydroxyquinoline conjunction) aluminium (Alq3) it is used as electron transport material and luminescent material, triphenylamine derivative is as hole transport material Material, the separation function type organic luminescent device (OLED) with double-layer structure emit about 1000cd/ under the voltage that about 10V applies m2The light of intensity.The OLED has a stacked structure of electron transport material and hole mobile material, and with conventional monolayers type device Part, which is compared, has the improved characteristics of luminescence.This develops whole world height studies have shown that can use organic film light emitting diode The efficient display of brightness, cause it is worldwide attract attention, the research later to OLED plays significant role.
After the 1980's, the basic structure of OLED device is anode (ITO), hole transmission layer (HTL), luminescent layer (EML), the simple structure of cathode (Mg:Ag).It then joined hole injection layer, such as copper phthalocyanine CuPc.Electron injecting layer (LiF) and the research of cathode Al:Li.Due to the insertion of a large amount of organic layer, the structure of OLED device becomes complicated, technically Increased difficulty；For producing in order to reduce production stage quantity, it is desirable to reduce the quantity of layer, improve power efficiency.
Summary of the invention
For the deficiency of remedy technology, we have studied a kind of Novel asymmetric anthracene inductor and electronic transmission performance are good Imidazoles material is connected, and can be used as electron transport material.Luminous efficiency and luminous brightness are improved, to greatly improve The various aspects of performance of organic electroluminescence devices.
The present invention provides a kind of following formula of anthracene compound (1) compounds:
Formula (1)
Wherein, R1, which is selected from, replaces or is substituted C1 ~ C60 alkyl, substituted or unsubstituted C6 ~ C60 aryl, replaces or not Substituted C5 ~ C60 condensed ring radical and substituted or unsubstituted C5 ~ C60 heterocycle；R2 is selected from substitution or is substituted C1 ~ C60 alkane Base, substituted or unsubstituted C6 ~ C60 aryl, substituted or unsubstituted C5 ~ C60 condensed ring radical and substituted or unsubstituted C5 ~ C60 Heterocycle.
Preferably, the general formula of molecular structure of the anthracene compound is chemical formula 2-1 ~ chemical formula 2-4,
Chemical formula 2-1
Chemical formula 2-2
Chemical formula 2-3
Chemical formula 2-4
Wherein, R2 is selected from substitution or is substituted C1~C60Alkyl, substituted or unsubstituted C6~C60Aryl replaces or does not take The C in generation5~C60Condensed ring radical and substituted or unsubstituted C5~C60Heterocycle, X are H or N.
Preferably, the R2Substituent group is selected from、、、、、、、, and can be in any position of the substituent group, preferably in substituent group The contraposition of connecting key.
Preferably, the anthracene compound is shown in chemical formula 001-010:
001,002,003,004,005,006,007,008,
009,010。
The present invention also provides a kind of preparation methods of formula (1) anthracene compound electroluminescent organic material, comprising:
By aminated compounds shown in formula (B), substitution reaction is carried out with halides shown in formula (A), is obtained shown in formula (1) Contain anthracene compound；
(A),(B),
(1)；
Wherein, R1, which is selected from, replaces or is substituted C1 ~ C60 alkyl, substituted or unsubstituted C6 ~ C60 aryl, replaces or not Substituted C5 ~ C60 condensed ring radical and substituted or unsubstituted C5 ~ C60 heterocycle；R2 is selected from substitution or is substituted C1 ~ C60 alkane Base, substituted or unsubstituted C6 ~ C60 aryl, substituted or unsubstituted C5 ~ C60 condensed ring radical and substituted or unsubstituted C5 ~ C60 Heterocycle.X is I, Br or Cl.It is preferred that X is Br.
The present invention also provides a kind of organic luminescent device, including above-mentioned prepared containing anthracene compound or above-mentioned preparation method Contain anthracene compound.
The organic luminescent device preferably includes first electrode, second electrode and is set to the first electrode and second Organic compound layer between electrode；The organic compound layer includes above-mentioned preparing containing anthracene compound or above-mentioned preparation method Contain anthracene compound.
The present invention also provides a kind of organic photoelectrical materials, including above-mentioned heteroaromatic compounds or the preparation of above-mentioned preparation method Heteroaromatic compounds；The organic photoelectrical material includes organic photovoltaic cell, Electronic Paper, Organophotoreceptor or organic crystal Pipe.
Compared with prior art, the present invention provides one kind to contain anthracene compound, has structure shown in formula (1).The present invention By modifying structure containing anthracene compound, to make comprising the organic electroluminescence hair shown in formula (1) containing anthracene compound Optical device has the features such as higher brightness, preferable heat resistance, long-life and high efficiency.
Specific embodiment
The present invention provides a kind of following formula of anthracene compound (1) compounds:
Formula (1)
Wherein, R1, which is selected from, replaces or is substituted C1 ~ C60 alkyl, substituted or unsubstituted C6 ~ C60 aryl, replaces or not Substituted C5 ~ C60 condensed ring radical and substituted or unsubstituted C5 ~ C60 heterocycle；R2 is selected from substitution or is substituted C1 ~ C60 alkane Base, substituted or unsubstituted C6 ~ C60 aryl, substituted or unsubstituted C5 ~ C60 condensed ring radical and substituted or unsubstituted C5 ~ C60 Heterocycle.
Preferably, the general formula of molecular structure of the anthracene compound is chemical formula 2-1 ~ chemical formula 2-4,
Chemical formula 2-1
Chemical formula 2-2
Chemical formula 2-3
Chemical formula 2-4
Wherein, R2 is selected from substitution or is substituted C1~C60Alkyl, substituted or unsubstituted C6~C60Aryl replaces or does not take The C in generation5~C60Condensed ring radical and substituted or unsubstituted C5~C60Heterocycle, X are H or N.
Preferably, the R2Substituent group is selected from、、、、、、、, and can be in any position of the substituent group, preferably in substituent group The contraposition of connecting key.
Preferably, the anthracene compound is shown in chemical formula 001-010:
001,002,003,004,005,006,007,008,
009,010。
The present invention also provides a kind of preparation methods of formula (1) anthracene compound electroluminescent organic material, comprising:
By aminated compounds shown in formula (B), substitution reaction is carried out with halides shown in formula (A), is obtained shown in formula (1) Contain anthracene compound；
(A),(B),
(1)；
Wherein, R1, which is selected from, replaces or is substituted C1 ~ C60 alkyl, substituted or unsubstituted C6 ~ C60 aryl, replaces or not Substituted C5 ~ C60 condensed ring radical and substituted or unsubstituted C5 ~ C60 heterocycle；R2 is selected from substitution or is substituted C1 ~ C60 alkane Base, substituted or unsubstituted C6 ~ C60 aryl, substituted or unsubstituted C5 ~ C60 condensed ring radical and substituted or unsubstituted C5 ~ C60 Heterocycle.X is I, Br or Cl.It is preferred that X is Br.
Two palladium of the catalysts preferably three (dibenzylideneacetone), tri-tert-butylphosphine；The preferred tertiary fourth of reaction base Sodium alkoxide；The preferred toluene of reaction dissolvent；Preferably 50 ~ 90 DEG C of the reaction temperature；After reaction, it is preferred to use petroleum ether: Methylene chloride=3:1(volume ratio) column chromatography post-processing approach.
Those skilled in the art can deduce preparation method according to product structure and above-mentioned reaction method.
Above-mentioned reaction condition is same as above, and details are not described herein.
In above-mentioned reaction raw materials and product structure, the range of R is same as above, and details are not described herein.
Preparation method containing anthracene compound provided by the invention is simple, is easy to industrialization.
The present invention also provides a kind of organic luminescent devices, including containing anthracene compound shown in above-mentioned formula (I).
The organic luminescent device is organic luminescent device well known to those skilled in the art, present invention preferably comprises First electrode, second electrode and the organic matter layer being set between the first electrode and second electrode；The organic matter layer packet Contain anthracene compound containing above-mentioned.It is described to can be single form containing anthracene compound, or with other material mixings, be contained in It states in organic matter layer.
When the organic matter layer includes electron transfer layer, the electron transfer layer may include class containing anthracene shown in formula (1) Compound and/or metallic compound.The metallic compound is the substance well known to those skilled in the art for electron-transport , have no special limitation.
When the organic matter layer includes simultaneously luminescent layer and electron transfer layer, the luminescent layer can divide with electron transfer layer Not Bao Kuo structure is identical or different formula (1) shown in contain anthracene compound.
Organic electroluminescence device provided by the invention, using shown in formula (1) contain anthracene compound and conventional material system It to the preparation method of the organic electroluminescence device and is not limited, conventional method in that art, this hair at, the present invention It is bright preferably by the methods of film vapor deposition, electron beam evaporation or physical vapour deposition (PVD) on substrate evaporation metal and conductive Oxide and they alloy formed anode, be then formed on organic matter layer and evaporation cathode, obtain organic electroluminescence hair Optical device.
Cathode substance layer on outer substrate is deposited in organic matter layer, anode material by the present invention in order, makes organic light emission Device.
Organic electroluminescence device provided by the invention according to the material used can also be divided into front shine, back side illuminated or Lighting at two sides；And the organic electroluminescence device can be applied with same principle in organic luminescent device (OLED), organic sun In battery (OSC), Electronic Paper (e-paper), Organophotoreceptor (OPC) or Organic Thin Film Transistors (OTFT).
Containing anthracene compound in organic photovoltaic cell, illumination OLED, flexibility shown in formula (I) provided by the invention It can also be applicable according to the principle for being applicable in organic luminescent device in the organic assemblies such as OLED, Organophotoreceptor and organic transistor.
The present invention also provides a kind of organic photoelectrical materials, including contain anthracene compound shown in above-mentioned formula (1)；It is described to have Machine photoelectric material includes organic photovoltaic cell, Electronic Paper, Organophotoreceptor or organic transistor.
In order to further illustrate the present invention, contain anthracene compound and its preparation to provided by the invention below with reference to embodiment Method and a kind of organic luminescent device are described in detail.
Example 1
The synthesis of compound [001]
It under the conditions of nitrogen protection, is added 0.10mol compound [1-1], sodium tert-butoxide 0.30mol, toluene 400mL are added It into reaction flask, stirs 30 minutes, nitrogen protection, 0.12mol compound [1-2], three (dibenzylideneacetones) two is then added Palladium 1.5g is eventually adding tri-tert-butylphosphine 4g, is warming up to 100 DEG C and reacts 24 hours, after reaction, water is added in system cooling Reaction, filtering are terminated, filtrate liquid separation is spin-dried for toluene, a small amount of methylene chloride dissolved solid is added, petroleum ether: methylene chloride=3:1 (volume ratio) column separation obtains solid (001) (0.05mol, y=50%), MS/FAB (M+): 766.93.
Embodiment 2
The change of 002-010 described in table 1 is prepared using raw material as shown in table 1 according to the preparation method of above compound 001 Close object.
1 embodiment of table, 2 reactive material, generation substance and yield summarize
The preparation of 3 luminescent device of embodiment
The ito glass substrate that Fisher Co., Ltd's coating layer thickness is 1500 is placed in distilled water and is cleaned 2 times, ultrasonic wave Washing 30 minutes, is then cleaned 2 times, ultrasonic washing 10 minutes repeatedly with distilled water, after distilled water cleans, using isopropyl Alcohol, acetone, methanol ultrasonic washing in order, then dry, are transferred in plasma washing machine, and aforesaid substrate is washed 5 Minute, it is sent in evaporator.Organic luminescent device includes anode, hole injection layer, hole transmission layer, organic luminous layer, electronics Transport layer, layer of auxiliary material and cathode.Wherein, anode is indium tin oxide；Hole injection layer be 60nm Isosorbide-5-Nitrae, 5,8,9, 11-hexaazatriphenylene-hexacarbonitrile(HAT-CN) ；Hole transmission layer is the [two-[4- of 30nm (N, N- xylyl-amino)-phenyl] hexamethylene (TAPC)；Organic luminous layer is 10nm comprising 90%4,4′-It is double (carbazole-9-Base)-Biphenyl, CBP) and it is used as light emitting host material, and doped with 10% 2 (1- phenyl-isoquinolin) (levulinic Ketone) close iridium (III) (Ir (ppy) 2 (acac)) luminescent material；Electron transfer layer is the compound 001 ~ 010 of 50nm；Assist material The bed of material is the LIF of 1nm；And cathode is aluminium.Above process organic matter vaporization plating speed keeps 1/sec, the evaporation rate of LiF For 0.2/sec, the evaporation rate of Al is 3 ~ 7/sec.
The electron luminescence characteristic of organic luminescent device obtained by the above method is shown in Table 2, and table 2 is the preparation of the embodiment of the present invention 3 Luminescent device characteristics of luminescence test result.
The characteristics of luminescence test result of the luminescent device of 2 embodiment of the present invention 3 of table preparation
As shown in Table 2, use the compound of the present invention 001 ~ 010 as the organic illuminating element of electron transfer layer have compared with Good luminous efficiency.
In conclusion electron transport material of the invention includes the compound of formula (1), the compound of formula (1) is to be with anthracene Core element and electron group is haled in the imidazoles for introducing different substituents.Therefore, the compound of formula (1) remains anthracene institute The high triplet energy rank having and good thermal stability, and have lower LUMO can rank, such as between -2.6eV to - 3.0eV, and then reduce the energy barrier of electron injection.Therefore, had using the organic illuminating element of electron transport material of the invention Preferable luminous efficiency.
The present invention be using new anthracene biology the available luminous efficiency of organic luminescent device and the service life it is good as a result, So the present invention is useful in the high OLED industry of practicability.Organic luminescent device of the invention is that flat panel shows, is flat Planar luminous body, illumination face illuminating OLED illuminator, flexible illuminator, duplicator, printer, LCD backlight lamp or dosing machine class The suitable use such as light source, display board, mark.

Claims (3)

1. one kind contains anthracene compound, which is characterized in that the anthracene compound is shown in chemical formula 001-010:
001,002,003,004,005,006,007,008,
009,010。
2. a kind of organic luminescent device, including first electrode, second electrode and the one or more being placed between two electrode Organic compound layer, wherein at least one organic compound layer include at least one such as claim 1 defined by any oneization Close object.
3. described in any item applications containing anthracene compound in organic electroluminescence device according to claim 1, feature It is, described is used as electron transport material in the organic electroluminescence device containing anthracene compound.
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