CN108658877A - A kind of preparation and its application of electron-transporting type material - Google Patents

A kind of preparation and its application of electron-transporting type material Download PDF

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Publication number
CN108658877A
CN108658877A CN201710212785.2A CN201710212785A CN108658877A CN 108658877 A CN108658877 A CN 108658877A CN 201710212785 A CN201710212785 A CN 201710212785A CN 108658877 A CN108658877 A CN 108658877A
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electron
vacuum evaporation
layer
transporting type
type material
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王启卫
王婷
何卓琳
朱槿
黄晴菲
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Chengdu Organic Chemicals Co Ltd of CAS
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Chengdu Organic Chemicals Co Ltd of CAS
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • 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
    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
    • H10K85/626—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene
    • 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
    • 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
    • C09K2211/1059—Heterocyclic compounds characterised by ligands containing three nitrogen atoms as heteroatoms

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Electroluminescent Light Sources (AREA)

Abstract

The present invention is a kind of preparation and its application of electron-transporting type material, this electron-transporting type material is separately connected the different triazole rings naphthalene nucleus group different with site using anthracene as parent nucleus, at its 9,10.Anthracene nucleus has unique photophysical property and chemical modification is strong, and substitution modification is carried out at its 9,10, has good thermal stability, can effectively reduce intramolecular aggregation, improve efficiency.Triazole ring is the molecular structure of an electron deficient, can be applied to the compound of electron transfer layer.Naphthalene nucleus has big planar conjugate structure, due to the energy barrier for reducing electron injecting layer or electron transfer layer LUMO and preferable electron transport material.The derivative of anthracene is the blue light material of classics, with the advantages of preferable film forming, stability and carrier transmission characteristics appropriate, the material is with the two, it can both be used as electron-transport material, blue emitting material material is can also be used as, electron-transport and luminescent material are can also be used as.

Description

A kind of preparation and its application of electron-transporting type material
Technical field
The present invention relates to a kind of preparations and its application of electron-transporting type material, belong to organic photoelectrical material technical field.
Background technology
In recent years, with the development of science and technology, organic electroluminescence device has become very popular emerging tablet Display technology industry.Organic electroluminescence device (Organic light-emitting diodes, OLEDs) and other hairs Optical device is compared, and OLEDs displays have that self-luminous, wide viewing angle, reaction is fast, luminous efficiency is high, low energy consumption, can be fabricated to big ruler The features such as very little and flexible panel and its simple manufacturing process, meets present people to larger display area and smaller accounting for With the demand of the flat-panel display device in space, most ideal and most with prospects next-generation display technology is considered by industry.
The functionization and commercialization of organic electroluminescence device are to the domestic and international great confidence of OLEDs researchers, it is believed that The OLEDs epoch have arrived, although OLEDs has been achieved for prodigious achievement, are not obtained there are many critical issue still Improve.In particular, electron-transport rate is low, the problems such as the short life of luminescent device, efficiency is low.
In OLEDs devices, Organic Electron Transport Material refers to that can control that electronics is oriented and ordered to be moved under electric field action It moves to realize the organic semiconducting materials of electron-transport, the high efficiency of transmission of carrier is to improving the hair of organic electroluminescence device Light efficiency, luminescent lifetime are most important, however the transmission rate of electronics is far below the transmission rate in hole, this is to lead to OLEDs devices One of less efficient key reason.OLEDs device efficiencies are improved, we must break through this difficult point, fundamental way Exactly develop high performance electron transport material.
It is needed to have as a kind of ideal electron transport material：(1) there is reversible electrochemical reduction and sufficiently high Reduction potential；(2) there are suitable highest occupied molecular orbital (HOMO) and minimum non-occupied orbital (LUMO) value, electronics is made to have minimum note Enter energy barrier, starting/operating voltage is made to reduce, and preferably also there is preferable hole blocking ability；(3) higher electronics moves Shifting rate；(4) must have high glass transformation temperature (Tg) and thermal stability；(5) it can be formed via hot dip or rotary coating Uniformly, the film of pore-free；(6) it is noncrystalline film.
Invention content
Present inventor has found that compound anthracene core is good blue light parent, has good thermal stability and film forming Property；And triazole ring is electron deficient heterocycle, and there is certain electron transport ability, naphthalene ring to have big planar conjugate knot Structure, due to the energy barrier for reducing electron injecting layer or electron transfer layer LUMO and preferable electron transport material.By the two In conjunction with will be hopeful to obtain a kind of electron-transporting type blue light material.
Technical problem to be solved by the invention is to provide a kind of electron-transporting type material and its applications, this material is as electricity Sub- transmission material is used in organic electroluminescence device, can significantly improve device efficiency.
The technical solution that the present invention solves above-mentioned technical problem is as follows：A kind of electron-transporting type material, the following institute of structural formula Show：
In formula, R is one kind in having structure
The present invention also provides a kind of preparation methods of above-mentioned electron-transporting type material, which is according to following conjunctions It is realized at route：
It is carried out by 3-triazole compounds and [10- (1- naphthalenes) -9- anthracenes] boric acid or [10-2- naphthalenes) -9- anthracenes] boric acid Suzuki coupling reactions, obtain target compound.In above-mentioned steps, Suzuki coupling reactions carry out under nitrogen protection, instead It is toluene to answer solvent：Ethyl alcohol=0.1-1, catalyst are Pd (PPh3)4Or Pd (OAc)2, reaction temperature is 70-120 DEG C, when reaction Between 12-36 hours.By the above method, the reaction process for preparing electron-transporting type luminescent material I1 and I4 is as follows：
Compound I1-4 set forth below is the representative structure for meeting spirit of that invention and principle, it should be understood that list following Compound structure is intended merely to preferably explain the present invention, is not limitation of the present invention.
The present invention also provides a kind of applications of electron-transporting type luminescent material, and in organic electroluminescence device, electronics passes Defeated layer contains electron-transporting type luminescent material described in claim 1.
The present invention also provides a kind of organic electroluminescence devices, including ITO (tin indium oxide) electro-conductive glass being sequentially overlapped Substrate (anode), hole injection layer (MoO3), hole transmission layer (NPB), luminescent layer (Alq3), electron transfer layer, electron injecting layer (LiF) and cathode layer (Al).Vacuum evaporation or solution film forming technique can be used in all functional layers.Used in the device The molecular structural formula of some organic compounds is as follows：
Certainly, the functional layer of device of the present invention is not limited to use above-mentioned material, these materials that can use other materials generation It replaces, for example hole transmission layer can use the replacements such as BPhen, the molecular structural formula of these materials as follows：
The beneficial effects of the invention are as follows：
The electron-transporting type luminescent material of the present invention is applied in organic electroluminescent, significantly improves the efficiency of device, It above has potential foreground, the major advantage of the material to be in the application of organic electroluminescence device：
1. the material uses anthracene nucleus for core, the different triazole rings naphthalene different with site is separately connected at its 9,10- Cyclic group, entire molecule avoid intermolecular aggregation and interaction at nonplanar structure；
2. having preferable electronic transmission performance, 2.2-3.02cd/ is reached with the device maximum current efficiency of the material preparation A；
3. the device prepared with the material preparation electron transfer layer, CIE (0.30-0.31,0.56--0.57).
Specific implementation mode
The principles and features of the present invention are described below, and example is only applied to explain the present invention, is not intended to Limit the scope of the present invention.
The preparation of 1 electron-transport of embodiment and luminescent material I1
Potassium carbonate (2.76g, 0.02mmol) is dissolved in toluene: ethyl alcohol: water volume ratio 3: 3: 1 (50mL) mixed solution In, N2Protection is lower to be added 4- (4- bromophenyls) -3,5- diphenyl -4H-1,2,4- triazoles (1.13g, 3mmol), 10- (1- naphthalenes Base)-anthracene -9- boric acid (1.25g, 3.6mmol), tetra-triphenylphosphine palladium (0.35g, 0.3mmol), be heated to 90 DEG C of back flow reactions, TLC is monitored to the reaction was complete.Reaction solution is extracted with dichloromethane, and organic layer is washed with water and saturated common salt water washing, drying.Through two The column chromatography of chloromethanes/methanol=30/1, obtains 1.01g gray solids product I 1.Yield：56%.
1H NMR (300MHz, CDCl3)δ：8.11 (d, J=8.1Hz, 1H), 8.05 (d, J=8.1Hz, 1H), 7.75 (d, J =7.0Hz, 1H), 7.57-7.71 (m, 9H), 7.38-7.54 (m, 13H), 7.28-7.31 (m, 2H), 7.23-7.25 (m, 1H), 7.15 (d, J=8.5Hz, 1H)；13C NMR (75MHz, CDCl3)δ：136.26,135.97,134.98,134.64,133.63, 133.40,133.06,130.53,129.85,129.50,129.10,128.95,128.48,128.26,128.11,127.34, 126.99,126.40,126.32,126.01,125.63,125.55,125.28.
High resolution mass spectrum, the sources ESI, cation [M+H]+, molecular formula C44H31N3, theoretical value 600.2440, test value is 600.2444。
The preparation of 2 electron-transport of embodiment and luminescent material I4
Potassium carbonate (2.76g, 0.02mmol) is dissolved in toluene: ethyl alcohol: water volume ratio 3: 3: 1 (50mL) mixed solution In, N2Protection is lower to be added 3- (4- bromophenyls) -4,5- diphenyl -4H-1,2,4- triazoles (1.13g, 3mmol), 10- (2- naphthalenes Base)-anthracene -9- boric acid (1.25g, 3.6mmol), tetra-triphenylphosphine palladium (0.35g, 0.3mmol), be heated to 90 DEG C of back flow reactions, TLC is monitored to the reaction was complete.Reaction solution is extracted with dichloromethane, and organic layer is washed with water and saturated common salt water washing, drying.Through two The column chromatography of chloromethanes/methanol=30/1, obtains 1.06g light yellow solids product I 4.Yield：59%.
1H NMR (300MHz, CDCl3)δ：8.07 (d, J=8.4Hz), 8.03-8.04 (m, 1H), 7.96 (m, 1H), 7.90-7.93 (m, 1H), 7.65-7.73 (m, 4H), 7.57-7.65 (m, 5H), 7.52-7.54 (m, 5H), 7.44-7.46 (m, 2H), 7.28-7.40 (m, 9H)；13C NMR (75MHz, CDCl3)δ：137.34,136.41,136.01,135.42,133.40, 132.78,131.55,130.20,130.09,130.00,129.81,129.68,129.66,129.46,128.84,128.75, 128.46,128.08,127.98,127.90,127.2,127.00,126.62,126.47,126.33,126.26,125.26, 125.14.
High resolution mass spectrum, the sources ESI, cation [M+H]+, molecular formula C44H31N3, theoretical value 600.2440, test value is 600.2437。
Organic electroluminescence device embodiment：
The present invention chooses compound I1 prepared by embodiment 1, and compound I4 prepared by embodiment 2 makes organic electroluminescent Device, it should be understood that the implementation process of device with as a result, be intended merely to be better understood from the present invention, not to the limit of the present invention System.ITO/MoO3(3nm)/NPB (60nm)/Alq3 (30nm)/electron transfer layer I (20nm)/LiF (1nm)/Al
Applications of the 3 electron transport material C1 of embodiment in organic electroluminescence device
A) ITO (tin indium oxide) electro-conductive glass is cleaned：Deionized water, acetone, absolute ethyl alcohol is used to be cleaned by ultrasonic ITO glass respectively Then each 15 minutes of glass is handled 2 minutes in plasma cleaner；
B) vacuum evaporation or solution film forming hole injection layer MoO on anode ito glass3, thickness 3nm；
C) in hole injection layer MoO3Upper vacuum evaporation or solution film forming hole transmission layer NPB, thickness 60nm；
D) on hole transmission layer NPB, vacuum evaporation luminescent layer Alq3, thickness 30nm；
E) in Alq3On, vacuum evaporation electron transfer layer I1, thickness 20nm
F) on C1, vacuum evaporation electron injecting layer LiF, thickness 1nm
G) on electron injecting layer LiF, vacuum evaporation cathode Al.
Device one opens bright voltage, maximum current efficiency, and the photooptical datas such as power efficiency and coloration are listed in Table 1 below.
Applications of the 4 electron transport material I4 of embodiment in organic electroluminescence device
A) ITO (tin indium oxide) electro-conductive glass is cleaned：Deionized water, acetone, absolute ethyl alcohol is used to be cleaned by ultrasonic ITO glass respectively Then each 15 minutes of glass is handled 2 minutes in plasma cleaner；
B) vacuum evaporation or solution film forming hole injection layer MoO3, thickness 3nm on anode ito glass；
C) vacuum evaporation or solution film forming hole transmission layer NPB, thickness 60nm on hole injection layer MoO3；
D) on hole transmission layer NPB, vacuum evaporation luminescent layer Alq3, thickness 30nm；
E) on Alq3, vacuum evaporation electron transfer layer I4, thickness 20nm
F) on I4, vacuum evaporation electron injecting layer LiF, thickness 1nm
G) on electron injecting layer LiF, vacuum evaporation cathode A1.
Device two opens bright voltage, maximum current efficiency, and the photooptical datas such as power efficiency and coloration are listed in Table 1 below.
Two photooptical data table of 1 device one of table and device
aBrightness is that current density is 20mA/cm2When estimated value.

Claims (9)

1. the noval chemical compound with formula (I) structure：
In formula, R is one kind in having structure
2. a kind of structure described in claim 1, which is characterized in that including preparing synthesis 3- (4- bromophenyls) -4,5- diphenyl - 4H-1,2,4- triazole compounds and 4- (4- bromophenyls) -3,5- diphenyl -4H-1,2,4- triazole compounds.
3. a kind of preparation method of the new compound of claim 1-2 any one of them, it is characterised in that include the following steps：
A) 3- (4- bromophenyls) -4,5- diphenyl -4H-1,2,4- triazole compounds and 4- (4- bromophenyls) -3,5- diphenyl - 4H-1, the synthesis of 2,4- triazole compounds；
B) triazole class compounds are carried out with [10- (1- naphthalenes) -9- anthracenes] boric acid or [10-2- naphthalenes) -9- anthracenes] boric acid respectively Suzuki coupling reactions.
4. applications of the claim 1-2 any one of them noval chemical compound I in preparing electron-transporting type material.
5. a kind of electron-transporting type material, which is characterized in that it includes that claim 1-3 any one of them is newly changed that it, which prepares raw material, Close object I.
6. application of the electron-transporting type material in preparing organic electroluminescence device described in claim 5.
7. a kind of organic electroluminescence device, including electron transfer layer, which is characterized in that the electron transfer layer, which contains, has the right to want Seek the electron-transporting type material described in 5.
8. organic electroluminescence device according to claim 7, which is characterized in that including compound I1-4 set forth below：
9. a kind of preparation method of organic electroluminescence device according to any one of claims 8, which is characterized in that include the following steps：
A) vacuum evaporation or solution film forming technique can be used in all functional layers；
B) ITO (tin indium oxide) electro-conductive glass is cleaned：Use deionized water, acetone, absolute ethyl alcohol ultrasonic cleaning ito glass each respectively It 15 minutes, is then handled 2 minutes in plasma cleaner；
C) vacuum evaporation or solution film forming hole injection layer MoO3, thickness 3nm on anode ito glass；
D) vacuum evaporation or solution film forming hole transmission layer NPB, thickness 60nm on hole injection layer MoO3；
E) on hole transmission layer NPB, vacuum evaporation luminescent layer Alq3, thickness 30nm；
F) on Alq3, vacuum evaporation electron transport layer materials I, thickness 20nm；
G) on electron transport layer materials I, vacuum evaporation electron injecting layer LiF, thickness 1nm；
H) on electron injecting layer LiF, vacuum evaporation cathode Al.
CN201710212785.2A 2017-04-01 2017-04-01 A kind of preparation and its application of electron-transporting type material Pending CN108658877A (en)

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Cited By (3)

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CN111187267A (en) * 2018-11-15 2020-05-22 北京鼎材科技有限公司 Luminescent material and application thereof
CN111377932A (en) * 2018-12-30 2020-07-07 北京鼎材科技有限公司 Compound, application thereof and organic electroluminescent device
CN115583941A (en) * 2022-12-09 2023-01-10 华南理工大学 Anthracene-based blue light organic semiconductor material containing triazole and preparation method and application thereof

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Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN111187267A (en) * 2018-11-15 2020-05-22 北京鼎材科技有限公司 Luminescent material and application thereof
CN111187267B (en) * 2018-11-15 2022-10-21 北京鼎材科技有限公司 Luminescent material and application thereof
CN111377932A (en) * 2018-12-30 2020-07-07 北京鼎材科技有限公司 Compound, application thereof and organic electroluminescent device
CN111377932B (en) * 2018-12-30 2023-08-22 北京鼎材科技有限公司 Compound, application thereof and organic electroluminescent device
CN115583941A (en) * 2022-12-09 2023-01-10 华南理工大学 Anthracene-based blue light organic semiconductor material containing triazole and preparation method and application thereof

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Application publication date: 20181016