CN106928188A - A kind of electroluminescent organic material and its application - Google Patents

A kind of electroluminescent organic material and its application Download PDF

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CN106928188A
CN106928188A CN201710112579.4A CN201710112579A CN106928188A CN 106928188 A CN106928188 A CN 106928188A CN 201710112579 A CN201710112579 A CN 201710112579A CN 106928188 A CN106928188 A CN 106928188A
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organic material
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张成新
高自良
李庆
慈振华
孟凡民
胡葆华
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Valiant Co Ltd
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    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
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    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
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    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
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    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
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    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
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Abstract

The invention belongs to field of organic electroluminescence, and in particular to a kind of electroluminescent organic material and its application, the electroluminescent organic material, including with the molecular structure shown in meeting formula (1), formula (2) or formula (3)：Be difficult to crystallize between material molecule of the present invention, be difficult to assemble, with good film forming and heat endurance, when the material is used as the emitting layer material of OLED luminescent devices, the device of making has good photoelectric properties, with good industrialization prospect.

Description

A kind of electroluminescent organic material and its application
Technical field
The invention belongs to field of organic electroluminescence, and in particular to a kind of electroluminescent organic material and its application.
Background technology
Since 1987, and organic electroluminescence device (Organic Light-Emitting Diodes, referred to as OLEDs) it is increasingly becoming the generally acknowledged flat panel display of future generation of industry.OLEDs belongs to selfluminous element, when electric charge (electronics and Hole) be injected between anode and negative electrode organic film when, electronics and hole-recombination form exciton and transfer energy to hair Optical molecule, and then excite electronics from ground state transition to excitation state, excited energy lights by Radiation-induced deactivation.OLEDs has Low, frivolous, the luminous visual angle of self-luminous, driving voltage is wide, fast response time, flexible folding, energy consumption is low, can carry out large area life The advantages of product, thus had broad application prospects in presentation of information and solid-state illumination field.
However, traditional organic fluorescence materials can only be lighted using 25% singlet exciton to be formed is electrically excited, device it is interior Quantum efficiency is relatively low (up to 25%).External quantum efficiency is generally less than 5%, and also there is a big difference with the efficiency of phosphorescent devices. Although phosphor material enhances intersystem crossing due to the strong SO coupling in heavy atom center, can effectively using being electrically excited The singlet exciton and Triplet exciton of formation, make the internal quantum efficiency of device up to 100%.But there is price in phosphor material Costliness, stability of material is poor, limits its application in OLEDs the problems such as device efficiency tumbles serious.Hot activation postpones glimmering Light (TADF) material is the third generation luminous organic material developed after organic fluorescence materials and organic phosphorescent material.Such material Material typically has small poor (the △ E of singlet-tripletST), triplet excitons can be transformed into list by anti-intersystem crossing Line state excitonic luminescence.This can make full use of the singlet exciton and triplet excitons for being electrically excited lower formation, the interior quantum of device Efficiency can reach 100%.Meanwhile, material structure is controllable, stable in properties, cheap without precious metal, in OLEDs fields Have a extensive future.
Although TADF materials can realize 100% exciton utilization rate in theory, following problem is there are in fact:(1) Design the T of molecule1And S1State has strong CT features, very small S1-T1State energy gap, although can be realized by TADF processes T high1→S1State exciton conversion ratio, but also result in low S1State radiation transistion speed, consequently it is difficult to have (or realizing) concurrently simultaneously Exciton utilization rate high and fluorescent radiation efficiency high；(2) even if having used doping device to mitigate T exciton concentration quenching effects, greatly Efficiency roll-off is serious at higher current densities for the device of most TADF materials.
For the actual demand of current OLED display Lighting Industries, the development of current OLED material is also far from enough, falls After the requirement of panel manufacturing enterprise, there is excellent photoelectric characteristic, good stability organic electroluminescent as material enterprise development Material is particularly important.
The content of the invention
The technical problems to be solved by the invention are to provide a kind of electroluminescent organic material and its application.The present invention is with pyrrole Pyridine ketone or cyano group substituted pyridines or pyrimidines are electrophilic unit, with carbazole, 9.9- dimethyl acridinium Huo phenoxazines It is electron unit, constructs a series of new electroluminescent organic material for obtaining and be applied on Organic Light Emitting Diode, has Good photoelectric properties, good stability disclosure satisfy that the requirement of panel manufacturing enterprise.
The technical scheme that the present invention solves above-mentioned technical problem is as follows：A kind of electroluminescent organic material, it is characterised in that Including with the molecular structure shown in meeting formula (1), formula (2) or formula (3)：
Wherein, Ar is selected from any one in following structures：
Further, formula (1), formula (2) are with Ar is identical described in formula (3) or differs.
A kind of above-mentioned electroluminescent organic material of the present invention as organic electroluminescent LED material application.
The present invention also provides a kind of organic electroluminescence device, and the organic electroluminescence device includes luminescent layer, described Luminescent layer contains a kind of above-mentioned electroluminescent organic material.
The beneficial effects of the invention are as follows：
1. the compounds of this invention it is intermolecular be difficult to crystallize, be difficult to assemble, with good film forming and heat endurance；Have Suitable HOMO and lumo energy, electron cloud efficiently separate achievable less S1-T1State energy gap, can effectively improve exciton profit high With rate and fluorescent radiation efficiency high, the efficiency roll-off under high current density is reduced, reduce device voltage, it is special with good photoelectricity Property.
2. compound of the present invention can be applied to the making of OLED luminescent devices, and can obtain good device table Existing, when the compound is used as the emitting layer material of OLED luminescent devices, the device of making has good photoelectric properties. Compound of the present invention has good application effect in OLED luminescent devices, with good industrialization prospect.
Compound A1 set forth below to compound A45, is the representative structure for meeting spirit of the invention and principle, should be managed Solution, lists following compound structure, is intended merely to preferably explain the present invention, is not limitation of the present invention：
Brief description of the drawings
Fig. 1 is the structural representation of organic electroluminescence device prepared by the present invention.
In accompanying drawing, the list of parts representated by each label is as follows：
101st, ITO Conducting Glass, 102, hole injection layer, 103, hole transmission layer, 104, luminescent layer, 105, electronics Transport layer, 106, electron injecting layer, 107, cathode layer.
Specific embodiment
Principle of the invention and feature are described below, example is served only for explaining the present invention, is not intended to limit Determine the scope of the present invention.
Material of the present invention is used to make organic electroluminescence device, and the device includes the ITO electro-conductive glass lining being sequentially overlapped Bottom (anode), hole injection layer, hole transmission layer (TAPC-mCP), luminescent layer (organic electroluminescence material of the present invention Material), electron transfer layer (3TPYMB), electron injecting layer (LiF) and cathode layer (Al), as shown in Figure 1.All functional layers are used Vacuum evaporation process is made.The molecular structural formula of some used organic compounds is as follows in such device.
The preparation of the compound A4 of embodiment 1
Under nitrogen protection, by raw material A 4-a (2.13g, 5.0mmol), raw material A 4-b (2.31g, 5.0mmol), 80mL first Benzene and 20mL water are added in 250mL there-necked flasks, then put into catalyst tetrakis triphenylphosphine palladium (0.029g, 0.025mmol), are tied up Sour agent potassium carbonate (1.04g, 7.5mmol).System is warming up to back flow reaction 8 hours, is naturally cooling to 20~25 DEG C, point liquid, removes Solvent is removed, by crude product toluene crystallization, 1.71g object A4, yield 71.2% is obtained.
High resolution mass spectrum, ESI sources, positive ion mode, molecular formula C34H28N2O, theoretical value 480.220, test value 480.221.Elementary analysis (C34H28N2O), theoretical value C：84.97, H：8.87, N：5.83, O：3.33, measured value C：84.97, H： 8.86, N：5.84, O：3.33.
The preparation of the compound A11 of embodiment 2
Under nitrogen protection, by raw material A 11-a (1.57g, 5mmol), raw material bromobenzene (1.56g, 10mmol) and 120mL first Benzene is added in 250mL there-necked flasks, then puts into catalyst acetic acid palladium (0.011g, 0.05mmol), catalyst ligand tri-tert Phosphine tetrafluoroborate (0.026g, 0.1mmol), acid binding agent sodium tert-butoxide (1.44g, 15mmol).System is warming up to back flow reaction 10 hours, 50mL water quenchings are added to go out reaction after being naturally cooling to 20~25 DEG C, point liquid, removing solvent, by crude product toluene crystallization, Obtain 1.63g object A11, yield 83.6%.
High resolution mass spectrum, ESI sources, positive ion mode, molecular formula C27H22N2O, theoretical value 390.173, test value 390.173.Elementary analysis (C27H22N2O), theoretical value C：83.05, H：5.68, N：7.17, O：4.10, measured value C：83.06, H： 5.69, N：7.17, O：4.10.
The preparation of the compound A18 of embodiment 3
Under nitrogen protection, by raw material M1 (2.06g, 5.0mmol), raw material A 18-a (1.82g, 10mmol), 80mL toluene Add in 250mL there-necked flasks, then put into catalyst tetrakis triphenylphosphine palladium (0.058g, 0.05mmol), acid binding agent potassium carbonate (1.38g, 10mmol).System is warming up to back flow reaction 6 hours, is naturally cooling to 20~25 DEG C, removes solvent, crude product toluene Crystallization, obtains 1.68g object A18, yield 86.8%.
High resolution mass spectrum, ESI sources, positive ion mode, molecular formula C27H21N3, theoretical value 387.174, test value 387.173. Elementary analysis (C27H21N3), theoretical value C：83.69, H：5.46, N：10.84, measured value C：83.70, H：5.45, N：10.84.
The preparation of the compound A23 of embodiment 4
The preparation method of synthetic method reference A4, total recovery 72.2%.
High resolution mass spectrum, ESI sources, positive ion mode, molecular formula C33H26N2O, theoretical value 466.205, test value 466.205.Elementary analysis (C33H26N2O), theoretical value C：84.95, H：5.62, N：6.00,0：3.43, measured value C：84.95, H： 5.64, N：6.02, O:3.43.
The preparation of the compound A29 of embodiment 5
The preparation method of synthetic method reference A18, total recovery 78.6%.
High resolution mass spectrum, ESI sources, positive ion mode, molecular formula C32H24N4, theoretical value 464.200, test value 464.201. Elementary analysis (C32H24N4), theoretical value C：82.73, H：5.21, N：12.06, measured value C：82.73, H：5.21, N：12.06.
The preparation of the compound A-13 6 of embodiment 6
The preparation method of synthetic method reference A18, total recovery 77.6%.
High resolution mass spectrum, ESI sources, positive ion mode, molecular formula C23H14N4O, theoretical value 362.117, test value 362.118.Elementary analysis (C23H14N4O), theoretical value C：76.23, H：3.89, N：15.46, O:4.42, measured value C：76.23, H：3.60, N：15.46, O:4.41.
The preparation of the compound A40 of embodiment 7
The preparation method of synthetic method reference C03, total recovery 78.3%.
High resolution mass spectrum, ESI sources, positive ion mode, molecular formula C31H20N2O, theoretical value 436.158, test value 436.158.Elementary analysis (C31H20N2O), theoretical value C：85.30, H：4.62, N：6.42, O:3.67, measured value C：85.31, H： 4.61, N：6.42, O:3.67.
Organic electroluminescence device makes embodiment：
The present invention chooses compound A4, compound A18 and makes organic electroluminescence device, and selects what is had been commercialized to light Material Ir (ppy)3As a comparison case, described with reference to Fig. 1, organic electroluminescence device is sequentially consisted of as ITO leads Electric glass substrate (101), hole injection layer (102), hole transmission layer (103) luminescent layer (104), electron transfer layer (105), electricity Sub- implanted layer (106) and cathode layer (107).It should be appreciated that device implementation process and result, are intended merely to preferably explain this hair It is bright, not limitation of the present invention.
Applications of the compound A4 of embodiment 8 in organic electroluminescence device
The present embodiment prepares organic electroluminescence device one by the following method：
A) ITO (tin indium oxide) glass is cleaned：Each 30 points of ito glass is cleaned with deionized water, acetone, EtOH Sonicate respectively Clock, is then processed 5 minutes in plasma cleaner；
B) vacuum evaporation hole injection layer (MoO3) successively on anode ito glass, thickness is 10nm；, evaporation rate 0.1nm/s；
C) the vacuum evaporation hole transmission layer on hole injection layer, is deposited with TAPC, and thickness is 10nm, is deposited with mCP, thickness 10nm, evaporation rate is 0.1nm/s, and evaporation total film thickness is 20nm；
D) vacuum evaporation luminescent layer (the compound A4 that the present invention is provided on hole transmission layer：MCPCN=8：100 (wt:Wt), evaporation rate 0.1nm/s, thickness is 20nm；
E) on luminescent layer vacuum evaporation as electron transfer layer 3TPYMB, thickness is 50nm；
F) on electron transfer layer, vacuum evaporation electron injecting layer LiF, thickness is 1nm；
G) on electron injecting layer, vacuum evaporation negative electrode Al, thickness is 100nm.
The structure of device is ITO/Mo03(10nm)/TAPC (10nm), mCP (10nm)/mCPCN:8%wt compounds A4 (20nm)/3TPYMB (50nm)/LiF (1nm)/Al (100nm), during vacuum evaporation, pressure<4.0×10-4Pa, with chemical combination Thing A4 as device one luminescent material, the test result of obtained device is shown in Table 1.
Embodiment 9：Applications of the compound A18 in organic electroluminescence device
Organic electroluminescence device two is made according to method same as Example 8, difference is to use A18 as luminous The luminescent material of layer replaces as synthesis compound A4 in the embodiment 1 of luminescent layer luminescent material.The test result of obtained device It is shown in Table 1.
Comparative example 1：Organic electroluminescence device three is made according to method same as Example 8, difference is using Commercialized Ir (ppy)3As the luminescent material of luminescent layer instead of synthesis in the embodiment 1 as luminescent layer luminescent material A4.The test result of obtained device is shown in Table 1.
The device photoelectric tables of data of table 1
As known from Table 1, the luminescent device that the material protected with the present invention makes has preferable current efficiency, power efficiency And relatively low driving voltage.
Compound A11, compound A23, compound A29, compound A-13 6, compound A40 is chosen to make respectively and embodiment 8 mutually isostructural organic electroluminescence devices four differ only in the luminescent material species of luminescent layer to device eight.Device performance Test result is as shown in table 2.
The device photoelectric tables of data of table 2
As known from Table 2, the present invention use TADF materials as luminescent dye with current efficiency higher, power efficiency with And relatively low driving voltage, device performance stabilization, with good industrialization prospect.
The foregoing is only presently preferred embodiments of the present invention, be not intended to limit the invention, it is all it is of the invention spirit and Within principle, any modification, equivalent substitution and improvements made etc. should be included within the scope of the present invention.

Claims (4)

1. a kind of electroluminescent organic material, it is characterised in that including with shown in meeting formula (1), formula (2) or formula (3) point Minor structure：
Wherein, Ar is selected from any one in following structures：
2. a kind of electroluminescent organic material according to claim 1, it is characterised in that formula (1), formula (2) and institute in formula (3) State Ar identical or differ.
3. a kind of a kind of electroluminescent organic material as claimed in claim 1 or 2 is used as organic electroluminescent LED material Using.
4. a kind of organic electroluminescence device, it is characterised in that the organic electroluminescence device includes luminescent layer, described luminous Layer contains a kind of electroluminescent organic material described in claim 1 or 2.
CN201710112579.4A 2017-02-28 2017-02-28 A kind of electroluminescent organic material and its application Pending CN106928188A (en)

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Cited By (1)

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CN102491968A (en) * 2011-12-08 2012-06-13 大连理工大学 Method for preparing carbazolyl biaryl compound in aqueous phase
WO2014054263A1 (en) * 2012-10-05 2014-04-10 出光興産株式会社 Material for organic electroluminescent element, and organic electroluminescent element produced using same
JP2014183226A (en) * 2013-03-19 2014-09-29 Toyo Ink Sc Holdings Co Ltd Material for organic electroluminescent element and organic electroluminescent element using the same
CN105254562A (en) * 2015-09-01 2016-01-20 华南理工大学 Organic small molecule luminescent material and organic electroluminescent device prepared from same
CN106083825A (en) * 2016-06-07 2016-11-09 石家庄诚志永华显示材料有限公司 Pyrazines derivatives and the application in organic electroluminescence device thereof

Cited By (1)

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CN110183426A (en) * 2019-05-29 2019-08-30 武汉华星光电半导体显示技术有限公司 A kind of thermal activation delayed fluorescence material, preparation method and electroluminescent device

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Application publication date: 20170707