CN107057680A - A kind of compound as core using anthrone and its application on organic electroluminescence device - Google Patents

A kind of compound as core using anthrone and its application on organic electroluminescence device Download PDF

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CN107057680A
CN107057680A CN201610259287.9A CN201610259287A CN107057680A CN 107057680 A CN107057680 A CN 107057680A CN 201610259287 A CN201610259287 A CN 201610259287A CN 107057680 A CN107057680 A CN 107057680A
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compound
key
formula
anthrone
alkylidene
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李崇
徐凯
张兆超
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Valiant Co Ltd
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Valiant Co Ltd
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Abstract

The invention discloses a kind of compound as core using anthrone and its application on organic electroluminescence device, the compound have it is intermolecular be difficult to crystallize, be difficult to assemble, with good filming the characteristics of, and rigid radical in molecule can improve the heat endurance of material.The compounds of this invention is applied to organic electroluminescence device as emitting layer material, and the organic electroluminescence device produced has good photoelectric properties, disclosure satisfy that the requirement of panel manufacturing enterprise.

Description

A kind of compound using anthrone as core and its on organic electroluminescence device Using
Technical field
The present invention relates to technical field of semiconductors, more particularly, to a kind of compound containing anthrone, and it is used as hair Application of the photosphere material on Organic Light Emitting Diode.
Background technology
Organic electroluminescent (OLED:Organic Light Emission Diodes) device technology both can for system New display product is made, can be used for making novel illumination product, be expected to substitute existing liquid crystal display and fluorescent lighting, Application prospect is quite varied.
OLED luminescent devices just as the structure of sandwich, including electrode material film layer, and be clipped in Different electrodes film layer it Between organic functional material, various difference in functionality materials are overlapped mutually according to purposes collectively constitutes OLED luminescent devices together. As current device, when the two end electrodes to OLED luminescent devices apply voltage, and pass through electric field action organic layer functional material Positive and negative charge in film layer, positive and negative charge is further combined in luminescent layer, that is, produces OLED electroluminescent.
Organic Light Emitting Diode (OLEDs) large-area flat-plate show and illumination in terms of application cause industrial quarters and The extensive concern of art circle.However, traditional organic fluorescence materials can only be lighted using 25% singlet exciton to be formed is electrically excited, device The internal quantum efficiency of part is relatively low (up to 25%).External quantum efficiency is generally less than 5%, also has with the efficiency of phosphorescent devices very big Gap.Although phosphor material enhances intersystem crossing due to the strong SO coupling in heavy atom center, electricity can be effectively utilized The singlet exciton to be formed and Triplet exciton are excited, makes the internal quantum efficiency of device up to 100%.But phosphor material is present Expensive, stability of material is poor, and the problems such as device efficiency tumbles serious limits its application in OLEDs.Hot activation is prolonged Slow fluorescence (TADF) material is the third generation luminous organic material developed after organic fluorescence materials and organic phosphorescent material.Should Class material typically has small poor (the △ E of singlet-tripletST), triplet excitons can be changed by anti-intersystem crossing It is luminous into singlet exciton.This can make full use of the singlet exciton and triplet excitons that are electrically excited lower formation, device it is interior Quantum efficiency can reach 100%.Meanwhile, material structure is controllable, and property is stable, cheap without precious metal, in OLEDs Field has a extensive future.
Although TADF materials can realize 100% exciton utilization rate in theory, following problem there are in fact:(1) T1 the and S1 states of design molecule have strong CT features, very small S1-T1 state energy gaps, although can be realized by TADF processes High T1→S1State exciton conversion ratio, but low S1 state radiation transistion speed is also resulted in, consequently it is difficult to have (or realizing) concurrently simultaneously High exciton utilization rate and high fluorescent radiation efficiency；(2) even if mitigating T exciton concentration quenching effects using doping device, greatly Efficiency roll-off is serious at higher current densities for the device of most TADF materials.
For the actual demand that current OLED shows Lighting Industry, the development of current OLED material is also far from enough, falls After the requirement of panel manufacturing enterprise, it is particularly important as the organic functional material of material enterprise development higher performance.
The content of the invention
In view of the above-mentioned problems existing in the prior art, the applicant provide a kind of compound using anthrone as core and its Application on organic electroluminescence device.The compounds of this invention is based on TADF mechanism, is applied to as emitting layer material organic Electroluminescent device, the organic electroluminescence device produced has good photoelectric properties, disclosure satisfy that panel manufacturing enterprise Requirement.
Technical scheme is as follows：
A kind of compound using anthrone as core, shown in the structure such as formula (1) of the compound：
In formula (1), D1、D2Selection C independently1-10Straight or branched alkyl, phenyl, xenyl, terphenyl, Naphthyl or anthryl, D1、D2Can be with identical or different；N takes 1 or 2；
Described-(R)nExpression is connected on any carbon atom on the phenyl ring of formula (1) both sides；
In formula (1), R is represented using formula (2) or formula (3)：
Wherein, Ar represents C6-30Aromatic radical, furyl, thienyl, pyrrole radicals, quinolyl or isoquinolyl；X1It is former for oxygen Son, sulphur atom, selenium atom, C1-10Alkylidene, alkylidene, the alkyl or aryl of aryl substitution of straight or branched alkyl substitution take One kind in the amido in generation；
Wherein, R1、R2Structure shown in selection hydrogen or formula (4) independently：
A isX2、X3It is expressed as oxygen atom, sulphur atom, selenium atom, C1-10Straight or branched One kind in alkyl-substituted alkylidene, the alkylidene of aryl substitution, the amido of alkyl or aryl substitution；A and CL1-CL2Key, CL2-CL3Key, CL3-CL4Key, CL4-CL5Key, CL‘1-CL’2Key, CL‘2-CL’3Key, CL‘3-CL’4Key or CL‘4-CL’5Key is connected.
When a is represented in the compoundAnd and CL4-CL5Key or CL‘4-CL’5When key is connected, X1And X2Position weight It is folded, only take X1Or X2；X3It is expressed as oxygen atom, sulphur atom, selenium atom, C1-10Alkylidene, the virtue of straight or branched alkyl substitution One kind in the amido that alkylidene, the alkyl or aryl of base substitution replace；A passes through CL4-CL5Key or CL‘4-CL’5Key is connected to logical On the middle phenyl ring of formula (2) or formula (3).
The general structure of the compound is：
R is in the formula (1)：
Any of.
The concrete structure formula of the compound is：
A kind of luminescent device containing the compound, the compound as luminescent layer material of main part, applied to having Organic electroluminescence devices.
A kind of luminescent device containing the compound, the compound as luminescent layer dopant material, applied to having Organic electroluminescence devices.
A kind of method for preparing the compound, reaction equation is：
Reaction equation 1：
Reaction equation 2：
Course of reaction is：
Bromo anthrone and secondary amine heterocyclic compounds are weighed, is dissolved with toluene；Add Pd2(dba)3, tri-butyl phosphine, Sodium tert-butoxide；Under an inert atmosphere, by the mixed solution of above-mentioned reactant in 95~110 DEG C of reaction temperature, reaction 10~24 is small When, cool down and filtering reacting solution, filtrate revolving crosses silicagel column, obtains target product；The bromo anthrone and secondary amine class heterocycle The mol ratio of compound is 1:2.0~4.0, Pd2(dba)3Mol ratio with bromo anthrone is 0.006~0.02:1, tri-tert The mol ratio of phosphine and bromo anthrone is 0.006~0.02:1, the mol ratio of sodium tert-butoxide and bromo anthrone is 1.0~3.0:1.
The present invention is beneficial to be had technical effect that：
The compounds of this invention connects one or two aromatic heterocycle group using anthrone as parent nucleus, the crystallinity of saboteur, It is generally rigid radical to avoid in intermolecular aggtegation, molecule, with good film forming and fluorescence quantum efficiency；It can make Used for luminescent layer dopant material；The compound structure intramolecular includes electron donor (donor, D) and electron acceptor The combination of (acceptor, A) can increase Orbital Overlap, improve luminous efficiency, while connecting aromatic heterocycle group to obtain The charge transfer state material that HOMO, LUMO are spatially separating, realizes the energy level difference of small S1 states and T1 states, so that in thermostimulation condition Under realize reverse intersystem crossing, be suitable as luminescent layer material of main part and use.
Compound of the present invention can make as emitting layer material applied to OLED luminescent devices, and respectively as hair Photosphere material of main part and dopant material, can obtain good device performance, the current efficiency of device, power efficiency and outer amount Sub- efficiency is greatly improved；Simultaneously for device lifetime lifting clearly.
Compound of the present invention has good application effect in OLED luminescent devices, before good industrialization Scape.
Brief description of the drawings
Fig. 1 is the device architecture schematic diagram that the compounds of this invention is applied；
Wherein, 1 is transparent substrate layer, and 2 be ito anode layer, and 3 be hole injection layer, and 4 be hole transmission layer, and 5 be luminous Layer, 6 be electron transfer layer, and 7 be electron injecting layer, and 8 be negative electrode reflection electrode layer.
Embodiment
With reference to the accompanying drawings and examples, the present invention is specifically described.
The compound 1 of embodiment 1
The specific synthetic route of the compound is now provided：
250ml four-hole bottle, under the atmosphere for being passed through nitrogen, adds 0.01mol 3- (4- bromophenyls) -10,10- diformazans Base -10H- anthrones, 0.03mol 9,9- dimethyl acridiniums, 0.03mol sodium tert-butoxides, 1 × 10-4molPd2(dba)3, 1 × 10- 4Mol tri-butyl phosphines, 150ml toluene is heated to reflux 24 hours, sample point plate, and reaction is complete；Natural cooling, filtering, filtrate Revolving, crosses silicagel column, obtains target product, purity 95.2%, yield 77.00%.
HPLC-MS：Material molecule amount is 505.24, surveys molecular weight 505.29.
The compound 2 of embodiment 2
The specific synthetic route of the compound is now provided：
250ml four-hole bottle, under the atmosphere for being passed through nitrogen, adds 0.01mol 3- (3- bromophenyls) -10,10- diformazans Base -10H- anthrones, 0.03mol phenoxazines, 0.03mol sodium tert-butoxides, 1 × 10-4mol Pd2(dba)3, 1 × 10-4The tertiary fourths of mol tri- Base phosphine, 150ml toluene is heated to reflux 24 hours, sample point plate, and reaction is complete；Natural cooling, filtering, filtrate revolving crosses silica gel Post, obtains target product, purity 99.20%, yield 73.50%.
HPLC-MS：Material molecule amount is 479.19, surveys molecular weight 479.46.
The compound 4 of embodiment 3
The specific synthetic route of the compound is now provided：
250ml four-hole bottle, under the atmosphere for being passed through nitrogen, addition 0.01mol 3, bromo- 10, the 10- diphenyl of 6- bis-- 10H- anthrones, 0.03mol 5- phenyl azophenlyene, 0.03mol sodium tert-butoxides, 1 × 10-4mol Pd2(dba)3, 1 × 10-4The uncles of mol tri- Butyl phosphine, 150ml toluene is heated to reflux 24 hours, sample point plate, and reaction is complete；Natural cooling, filtering, filtrate revolving crosses silicon Glue post, obtains target product, purity 99.1%, yield 73.60%.
HPLC-MS：Material molecule amount is 858.34, surveys molecular weight 858.52.
The compound 5 of embodiment 4
The specific synthetic route of the compound is now provided：
250ml four-hole bottle, under the atmosphere for being passed through nitrogen, adds bromo- 10, the 10- dimethyl -10H- anthracenes of 0.01mol 2- Ketone, 0.03mol 9,9- diphenylacridines, 0.03mol sodium tert-butoxides, 01 × 10-4mol Pd2(dba)3, 1 × 10-4The uncles of mol tri- Butyl phosphine, 150ml toluene is heated to reflux 24 hours, sample point plate, and reaction is complete；Natural cooling, filtering, filtrate revolving crosses silicon Glue post, obtains target product, purity 99.325%, yield 63.56%.
HPLC-MS：Material molecule amount is 553.24, surveys molecular weight 553.53.
The compound 7 of embodiment 5
The specific synthetic route of the compound is now provided：
250ml four-hole bottle, under the atmosphere for being passed through nitrogen, adds 0.01mol 3- (4- bromophenyls) -10,10- diformazans Base -10H- anthrones, 0.03mol acridine spiral shell anthrones, 0.03mol sodium tert-butoxides, 1 × 10-4mol Pd2(dba)3, 1 × 10-4Mol tri- Tert-butyl group phosphine, 150ml toluene is heated to reflux 24 hours, sample point plate, and reaction is complete；Natural cooling, filtering, filtrate revolving, mistake Silicagel column, obtains target product, purity 98.50%, yield 63.25%.
HPLC-MS：Material molecule amount is 655.25, surveys molecular weight 655.66.
The compound 8 of embodiment 6
The specific synthetic route of the compound is now provided：
250ml four-hole bottle, under the atmosphere for being passed through nitrogen, adds 0.01mol2- (4- bromophenyls) -10,10- diformazans Base -10H- anthrones, 0.03mol 6,6- dimethyl -6,11- dihydro -13- oxa-s -11- azepines-indoles and anthracene, the tertiary fourths of 0.03mol Sodium alkoxide, 1 × 10-4mol Pd2(dba)3, 1 × 10-4Mol tri-butyl phosphines, 150ml toluene is heated to reflux 24 hours, sample point Plate, reaction is complete；Natural cooling, filtering, filtrate revolving crosses silicagel column, obtains target product, purity 99.33%, yield 72.50%.
HPLC-MS：Material molecule amount is 595.25, surveys molecular weight 595.32.
The compound 9 of embodiment 7
The specific synthetic route of the compound is now provided：
250ml four-hole bottle, under the atmosphere for being passed through nitrogen, addition 0.01mol3, bromo- 10, the 10- dimethyl of 6- bis-- 10H- anthrones, 0.03mol 6,6- dimethyl -6,11- dihydro -13- oxa-s -11- azepines-indoles and anthracene, the 0.03mol tert-butyl alcohols Sodium, 1 × 10-4mol Pd2(dba)3, 1 × 10-4Mol tri-butyl phosphines, 150ml toluene is heated to reflux 24 hours, sample point plate, Reaction is complete；Natural cooling, filtering, filtrate revolving crosses silicagel column, obtains target product, purity 99..20%, yield 68.20%.
HPLC-MS：Material molecule amount is 816.34, surveys molecular weight 816.56.
The compound 15 of embodiment 8
The specific synthetic route of the compound is now provided：
250ml four-hole bottle, under the atmosphere for being passed through nitrogen, adds 0.01mol 1- (3- bromophenyls) -10,10- diformazans Base -10H- anthrones, 0.03mol 11,11- dimethyl -5- phenyl -11,13- dihydro -5H- indoles [1,2-b] azophenlyene, 0.03mol Sodium tert-butoxide, 1 × 10-4mol Pd2(dba)3, 1 × 10-4Mol tri-butyl phosphines, 150ml toluene is heated to reflux 24 hours, taken Sampling point plate, reaction is complete；Natural cooling, filtering, filtrate revolving crosses silicagel column, obtains target product, purity 99.55%, yield 63.50%.
HPLC-MS：Material molecule amount is 670.30, surveys molecular weight 670.61.
The compound 17 of embodiment 9
The specific synthetic route of the compound is now provided：
250ml four-hole bottle, under the atmosphere for being passed through nitrogen, adds 0.01mol 2,7- bis- (4- bromophenyls) -10,10- Dimethyl -10H- anthrones, 0.03mol 11,11- dimethyl -6,11- dihydro -13- oxa-s -6- azepines-indoles [1,2-b] anthracene, 0.03mol sodium tert-butoxides, 1 × 10-4mol Pd2(dba)3, 1 × 10-4Mol tri-butyl phosphines, 150ml toluene, are heated to reflux 24 Hour, sample point plate, reaction is complete；Natural cooling, filtering, filtrate revolving crosses silicagel column, obtains target product, purity 98.62%, yield 72.3%.
HPLC-MS：Material molecule amount is 968.40, surveys molecular weight 968.94.
The compound 19 of embodiment 10
The specific synthetic route of the compound is now provided：
250ml four-hole bottle, under the atmosphere for being passed through nitrogen, adds 0.01mol2- (5- bromine furans -2- bases) -10,10- Dimethyl -10H- anthrones, 0.03mol 6H-11- oxa- -13- thias -6- azepines-indoles [1,2-b] anthracene, the 0.03mol tert-butyl alcohols Sodium, 1 × 10-4mol Pd2(dba)3, 1 × 10-4Mol tri-butyl phosphines, 150ml toluene is heated to reflux 24 hours, sample point plate, Reaction is complete；Natural cooling, filtering, filtrate revolving crosses silicagel column, obtains target product, purity 99.20%, yield 62.3%.
HPLC-MS：Material molecule amount is 575.16, surveys molecular weight 575.33.
The compound 20 of embodiment 11
The specific synthetic route of the compound is now provided：
250ml four-hole bottle, under the atmosphere for being passed through nitrogen, adds 0.01mol3- (the bromo- 1- methyl isophthalic acids H- pyrroles -2- of 5- Base) -10,10- dimethyl -10H- anthrones, 0.03mol 13,13- dimethyl -6,13- dihydro -11- oxa-s -6- azepines-indoles [1,2-b] anthracene, 0.03mol sodium tert-butoxides, 1 × 10-4mol Pd2(dba)3, 1 × 10-4Mol tri-butyl phosphines, 150ml toluene, It is heated to reflux 24 hours, sample point plate, reaction is complete；Natural cooling, filtering, filtrate revolving crosses silicagel column, obtains target production Thing, purity 99.6%, yield 68.00%.
HPLC-MS：Material molecule amount is 598.26, surveys molecular weight 598.35.
The compound 21 of embodiment 12
The specific synthetic route of the compound is now provided：
250ml four-hole bottle, under the atmosphere for being passed through nitrogen, adds 0.01mol3- (8- bromoquinoline -5- bases) -10,10- Dimethyl -10H- anthrones, 0.03mol 11,11- dimethyl -13- phenyl -11,13- dihydro -5H- indoles [1,2-b] azophenlyene, 0.03mol sodium tert-butoxides, 1 × 10-4mol Pd2(dba)3, 1 × 10-4Mol tri-butyl phosphines, 150ml toluene, are heated to reflux 24 Hour, sample point plate, reaction is complete；Natural cooling, filtering, filtrate revolving crosses silicagel column, obtains target product, purity 99.8%, yield 63.51%.
HPLC-MS：Material molecule amount is 721.31, surveys molecular weight 721.36.
The compound 23 of embodiment 13
The specific synthetic route of the compound is now provided：
250ml four-hole bottle, under the atmosphere for being passed through nitrogen, adds 0.01mol3- (4- bromophenyls) -10,10- hexichol Base -10H- anthrones, 0.03mol 13,13- dimethyl -5,13- dihydro -8- oxa-s -5- azepines-indoles [1,2-a] anthracene, 0.03mol sodium tert-butoxides, 1 × 10-4mol Pd2(dba)3, 1 × 10-4Mol tri-butyl phosphines, 150ml toluene, are heated to reflux 24 Hour, sample point plate, reaction is complete；Natural cooling, filtering, filtrate revolving crosses silicagel column, obtains target product, purity 99.8%, yield 63.51%.
HPLC-MS：Material molecule amount is 719.28, surveys molecular weight 719.38.
The compound 31 of embodiment 14
The specific synthetic route of the compound is now provided：
The preparation method be the same as Example 1 of compound 31, difference is raw material 5,5- diphenyl -5,8a, 12a, 13- tetra- Hydrogen -8- oxa-s -13- azepines-indoles [1,2-a] anthracene replaces acridine and anthrone.
The compound 35 of embodiment 15
The specific synthetic route of the compound is now provided：
The preparation method be the same as Example 1 of compound 35, difference is raw material 14,14- dimethyl -5,14- dihydro-naphthalene And [2,3-b] acridine replaces 9,9- dimethyl acridiniums.
The compound 38 of embodiment 16
The specific synthetic route of the compound is now provided：
The preparation method be the same as Example 13 of compound 38, difference is raw material 14,14- dimethyl -7,14- dihydro - 5,12- dioxas -7- azepines-pentacene replaces 13,13- dimethyl -5,13- dihydro -8- oxa-s -5- azepines-indoles [1,2-a] Anthracene.
The compound 40 of embodiment 17
The specific synthetic route of the compound is now provided：
The preparation method be the same as Example 7 of compound 40, difference is raw material 14,14- dimethyl -7,14- dihydro -5, 12- dioxas -7- azepines-pentacene replaces 6,6- dimethyl -6,11- dihydro -13- oxa-s -11- azepines-indoles and anthracene.
The compound 41 of embodiment 18
The specific synthetic route of the compound is now provided：
The preparation method be the same as Example 13 of compound 38, difference is that raw material A replaces 13,13- dimethyl -5,13- Dihydro -8- oxa-s -5- azepines-indoles [1,2-a] anthracene.
The compound 45 of embodiment 19
The specific synthetic route of the compound is now provided：
250ml four-hole bottle, under the atmosphere for being passed through nitrogen, addition 0.01mol3, bromo- 10, the 10- dimethyl of 6- bis-- 10H- anthrones, 0.03mol 9H-5- oxa-s -9,13b- diaza-naphthalene [3,2,1-de] anthracene, 0.03mol sodium tert-butoxides, 1 × 10- 4mol Pd2(dba)3, 1 × 10-4Mol tri-butyl phosphines, 150ml toluene is heated to reflux 24 hours, sample point plate, and reaction is complete； Natural cooling, filtering, filtrate revolving crosses silicagel column, obtains target product, purity 99.8%, yield 63.51%.
HPLC-MS：Material molecule amount is 762.26, surveys molecular weight 762.36.
The compound 49 of embodiment 20
The specific synthetic route of the compound is now provided：
250ml four-hole bottle, under the atmosphere for being passed through nitrogen, adds 0.01mol2- (3- bromophenyls) -10,10- hexichol Base -10H- anthrones, 0.03mol 9,9- dimethyl -5H, 9H-5,13b- diaza-naphthalene [3,2,1-de] anthracene, the tertiary fourths of 0.03mol Sodium alkoxide, 1 × 10-4mol Pd2(dba)3, 1 × 10-4Mol tri-butyl phosphines, 150ml toluene is heated to reflux 24 hours, sample point Plate, reaction is complete；Natural cooling, filtering, filtrate revolving crosses silicagel column, obtains target product, purity 99.8%, yield 63.51%.
HPLC-MS：Material molecule amount is 718.30, surveys molecular weight 718.37.
The compound 50 of embodiment 21
The specific synthetic route of the compound is now provided：
250ml four-hole bottle, under the atmosphere for being passed through nitrogen, adds 0.01mol2- (3- bromophenyls) -10,10- diformazans Base -10H- anthrones, 0.03mol 9,9- diphenyl -5H, 9H-5,13b- diaza-naphthalene [3,2,1-de] anthracene, the tertiary fourths of 0.03mol Sodium alkoxide, 1 × 10-4mol Pd2(dba)3, 1 × 10-4Mol tri-butyl phosphines, 150ml toluene is heated to reflux 24 hours, sample point Plate, reaction is complete；Natural cooling, filtering, filtrate revolving crosses silicagel column, obtains target product, purity 99.8%, yield 63.51%.
HPLC-MS：Material molecule amount is 718.30, surveys molecular weight 719.03.
The compound 51 of embodiment 22
The specific synthetic route of the compound is now provided：
The preparation method be the same as Example 20 of compound 51, difference is raw material 3,6- bis- (4- bromophenyls) -10,10- Dimethyl -10H- anthrones replace 2- (3- bromophenyls) -10,10- diphenyl -10H- anthrones.
The compounds of this invention can be used as emitting layer material, to the compounds of this invention 8, compound 23, current material CBP carries out the test of hot property, luminescent spectrum, fluorescence quantum efficiency and cyclic voltammetric stability, testing result such as table 1 respectively It is shown.
Table 1
Note：Thermal weight loss temperature Td is the temperature of the weightlessness 1% in nitrogen atmosphere, in the TGA-50H heat of Japanese Shimadzu Corporation It is measured on weight analysis instrument, nitrogen flow is 20mL/min；λPLIt is sample solution fluorescence emission wavelengths, Pu Kang is opened up using Japan SR-3 spectroradiometers are determined；Φ f are that solid powder fluorescence quantum efficiency (utilizes the Maya2000Pro of U.S.'s marine optics Fiber spectrometer, the test solid fluorescence amount of C-701 integrating spheres and marine optics LLS-LED the light sources composition of Lan Fei companies of the U.S. Sub- efficiency test system, reference literature Adv.Mater.1997,9,230-232 method is measured)；Cyclic voltammetric stability It is to observe the redox characteristic of material to be identified by cyclic voltammetry；Test condition：Test sample is dissolved in volume ratio For 2:1 dichloromethane and acetonitrile mixed solvent, concentration 1mg/mL, electrolyte is 0.1M tetrabutyl ammonium tetrafluoroborate or hexafluoro The organic solution of phosphoric acid tetrabutylammonium.Reference electrode is Ag/Ag+ electrodes, is titanium plate to electrode, working electrode is ITO electrode, is followed Ring number of times is 20 times.
Hot annealing conditions：WithEvaporation rate compound is deposited on quartz glass, 100 DEG C are added to after encapsulation Baking oven in dry 72 hours, take out, be cooled to room temperature, its crystal habit observed with AFM.
From upper table data, the compounds of this invention has preferable oxidation-reduction stability, and higher heat endurance is fitted Cooperate the material of main part for luminescent layer；Meanwhile, the compounds of this invention has suitable luminescent spectrum, higher Φ f so that application The compounds of this invention gets a promotion as the OLED efficiency of dopant material and life-span.
23-44 and comparative example 1 describe the OLED material conduct in the devices that the present invention is synthesized in detail by the following examples The application effect of luminescent layer material of main part.24-44 of the present invention, the device compared with embodiment 23 of comparative example 1 making Technique is identical, and employed identical baseplate material and electrode material, and the thickness of electrode material is also consistent, institute The difference is that being converted to the material of main part of the luminescent layer 5 in device, the structure composition of obtained device is as shown in table 2.Each device The performance test results of part are as shown in table 3.
Embodiment 23
Ito anode layer 2/ hole injection layer 3 (molybdenum trioxide MoO3, thickness 10nm) and/hole transmission layer 4 (TAPC, thickness (compound 1 and GD-19 are according to 100 for 80nm)/luminescent layer 5：5 weight is than blending, thickness 30nm)/electron transfer layer 6 (TPBI, Thickness 40nm)/electron injecting layer 7 (LiF, thickness 1nm)/Al
Specific preparation process is as follows：
Ito anode 2 (thickness is 150nm) of layer are washed, i.e., carried out successively after neutralizing treatment, pure water, drying again Ultraviolet-ozone washing is carried out to remove the organic residue on transparent ITO surfaces.
On the ito anode layer 2 after having carried out above-mentioned washing, using vacuum deposition apparatus, evaporation thickness is 10nm's Molybdenum trioxide MoO3Used as hole injection layer 3.And then the TAPC of evaporation 80nm thickness is used as hole transmission layer 4.
After above-mentioned hole mobile material evaporation terminates, the luminescent layer 5 of OLED luminescent devices is made, its structure is sent out including OLED Photosphere 5 uses material compound 1 as material of main part, and GD-19 is as dopant material, and dopant material doping ratio is 5% weight Amount ratio, luminescent layer thickness is 30nm.
After above-mentioned luminescent layer 5, it is TPBI to continue vacuum evaporation electron transport layer materials.The vacuum evaporation coating of the material Thickness is 40nm, and this layer is electron transfer layer 6.
On electron transfer layer 6, by vacuum deposition apparatus, lithium fluoride (LiF) layer that thickness is 1nm is made, this layer is Electron injecting layer 7.
On electron injecting layer 7, by vacuum deposition apparatus, aluminium (Al) layer that thickness is 80nm is made, this layer is negative electrode Reflection electrode layer 8 is used.
Complete after OLED luminescent devices, connected anode and negative electrode as described above with known drive circuit, survey The I-E characteristic of the luminous efficiency of metering device, luminescent spectrum and device.The test result of obtained device is shown in Table 3.
Table 2
Table 3
Explanation:Device detection performance is using comparative example 1 as reference, and the device property indices of comparative example 1 are set to 1.0.Than Current efficiency compared with example 1 is 6.5cd/A (@10mA/cm2)；CIE chromaticity coordinates is (0.32,0.61)；The LT95 life-spans under 5000 brightness Decay to 3.8Hr.Life-span test system is owner of the present invention and the OLED life test of Shanghai University's joint research Instrument.
45-52 and comparative example 2 illustrate the compound of the invention synthesized in the devices as luminescent layer by the following examples The application effect of dopant material.45-52 of the present invention, the device compared with embodiment 23 of comparative example 2 manufacture craft it is complete It is exactly the same, and employed identical baseplate material and electrode material, the thickness of electrode material is also consistent, different It is that the dopant material of the luminescent layer 5 in device is converted, doping concentration is changed into 7%.The structure of each embodiment obtained device Composition is as shown in table 4.The performance test results of each device are as shown in table 5.
Table 4
Table 5
Explanation:Device detection performance is using comparative example 2 as reference, and the device property indices of comparative example 2 are set to 1.0.Than Current efficiency compared with example 2 is 9.5cd/A (@10mA/cm2)；CIE chromaticity coordinates is (0.27,0.65)；The LT95 life-spans under 5000 brightness Decay to 8.2Hr.Life-span test system is owner of the present invention and the OLED life test of Shanghai University's joint research Instrument.
The result of table 3 can be seen that compound of the present invention can be applied and OLED photophores as luminescent layer material of main part Part makes, and compared with comparative example 1, either efficiency or life-span change more larger than the acquisition of known OLED material, especially It is the larger lifting of the driving life-span acquisition of device.
The result of table 5 can be seen that compound of the present invention can be applied and OLED photophores as luminescent layer dopant material Part makes, and compared with comparative example 2, either efficiency or life-span change more larger than the acquisition of known OLED material, especially It is the larger lifting of the driving life-span acquisition of device.
From the point of view of data above application, the compounds of this invention has well as emitting layer material in OLED luminescent devices Application effect, with good industrialization prospect.
Although disclosing the present invention by embodiment and preferred embodiment, it should be appreciated that public the invention is not restricted to institute The embodiment opened.On the contrary, it will be understood by those skilled in the art that it is intended to various modifications and similar arrangement.Therefore, institute The scope of attached claim should be consistent with most wide explanation to cover all such modifications and similar arrangement.

Claims (8)

1. a kind of compound using anthrone as core, it is characterised in that shown in the structure of the compound such as formula (1)：
In formula (1), D1、D2Selection C independently1-10Straight or branched alkyl, phenyl, xenyl, terphenyl, naphthyl Or anthryl, D1、D2Can be with identical or different；N takes 1 or 2；
Described-(R)nExpression is connected on any carbon atom on the phenyl ring of formula (1) both sides；
In formula (1), R is represented using formula (2) or formula (3)：
Wherein, Ar represents C6-30Aromatic radical, furyl, thienyl, pyrrole radicals, quinolyl or isoquinolyl；X1For oxygen atom, Sulphur atom, selenium atom, C1-10The alkylidene of straight or branched alkyl substitution, the alkylidene of aryl substitution, alkyl or aryl substitution Amido in one kind；
Wherein, R1、R2Structure shown in selection hydrogen or formula (4) independently：
A isX2、X3It is expressed as oxygen atom, sulphur atom, selenium atom, C1-10Straight or branched alkyl One kind in substituted alkylidene, the alkylidene of aryl substitution, the amido of alkyl or aryl substitution；A and CL1-CL2Key, CL2-CL3 Key, CL3-CL4Key, CL4-CL5Key, CL‘1-CL’2Key, CL‘2-CL’3Key, CL‘3-CL’4Key or CL‘4-CL’5Key is connected.
2. compound according to claim 1, it is characterised in that when a is represented in the compoundAnd and CL4-CL5 Key or CL‘4-CL’5When key is connected, X1And X2Location overlap, only take X1Or X2；X3Be expressed as oxygen atom, sulphur atom, selenium atom, C1-10One kind in the amido that alkylidene, the alkylidene of aryl substitution, the alkyl or aryl of straight or branched alkyl substitution replace.
3. compound according to claim 1, it is characterised in that the general structure of the compound is：
4. compound according to claim 1, it is characterised in that R is in the formula (1)：
Any of.
5. compound according to claim 1, it is characterised in that the concrete structure formula of the compound is：
6. a kind of luminescent device for including any one of the Claims 1 to 5 compound, it is characterised in that the compound conduct The material of main part of luminescent layer, for making organic electroluminescence device.
7. a kind of luminescent device for including any one of the Claims 1 to 5 compound, it is characterised in that the compound conduct The dopant material of luminescent layer, for making organic electroluminescence device.
8. a kind of method for preparing any one of Claims 1 to 5 compound, it is characterised in that reaction equation is：
Reaction equation 1：
Reaction equation 2：
Course of reaction is：
Bromo anthrone and secondary amine heterocyclic compounds are weighed, is dissolved with toluene；Add Pd2(dba)3, tri-butyl phosphine, tertiary fourth Sodium alkoxide；Under an inert atmosphere, by the mixed solution of above-mentioned reactant in 95~110 DEG C of reaction temperature, react 10~24 hours, it is cold But and filtering reacting solution, filtrate revolving, crosses silicagel column, obtains target product；The bromo anthrone and secondary amine class heterocyclic compound The mol ratio of thing is 1:2.0~4.0, Pd2(dba)3Mol ratio with bromo anthrone is 0.006~0.02:1, tri-butyl phosphine with The mol ratio of bromo anthrone is 0.006~0.02:1, the mol ratio of sodium tert-butoxide and bromo anthrone is 1.0~3.0:1.
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CN111848589A (en) * 2019-04-30 2020-10-30 江苏三月科技股份有限公司 Xanthone derivative, preparation method and application thereof, and light-emitting device comprising xanthone derivative
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