CN109053739A - A kind of pyrrolotriazine derivatives and its application in OLED device - Google Patents

A kind of pyrrolotriazine derivatives and its application in OLED device Download PDF

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CN109053739A
CN109053739A CN201811094524.6A CN201811094524A CN109053739A CN 109053739 A CN109053739 A CN 109053739A CN 201811094524 A CN201811094524 A CN 201811094524A CN 109053739 A CN109053739 A CN 109053739A
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pyrrolotriazine derivatives
aryl
phenyl
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刘凯鹏
孙军
张宏科
王小伟
刘骞峰
高仁孝
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Xi'an Ruilian New Material Co Ltd
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Xi'an Ruilian New Material Co Ltd
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Abstract

A kind of application the invention discloses pyrrolotriazine derivatives and its in OLED device, pyrrolotriazine derivatives of the invention, it is with D-A structure, using triazine and its modification group as electron acceptor (A), using carbazole and its modification group as electron donor (D), the structure of the derivative is with shown in the general formula (1), general formula (2), general formula (3) structure.Pyrrolotriazine derivatives of the invention are a kind of ambipolar TADF materials, have the charge transport ability for comparing balance, and be not easy to crystallize, and have good film forming and thermal stability.Pyrrolotriazine derivatives of the invention can be used as the functional material of OLED luminescent device, especially a kind of material of main part and dopant material with TADF property, pyrrolotriazine derivatives of the invention are used to be greatly improved as the brightness of device made by material of main part or dopant material, efficiency roll-off, and driving voltage reduce, simultaneously for device lifetime promotion clearly.

Description

A kind of pyrrolotriazine derivatives and its application in OLED device
Technical field
The present invention relates to organic electroluminescent field of functional materials more particularly to a kind of triazines with TADF luminosity Derivative and its application in organic electroluminescence device.
Background technique
The basic structure of OLED is to be connected by the indium tin oxide (ITO) of a thin and transparent tool characteristic of semiconductor with anode, Along with another metallic cathode, it is bundled into the structure such as sandwich.Include hole transmission layer (HTL) in total layer, shine Layer (EL) and electron transfer layer (ETL).When supplying power to appropriate voltage, positive hole will be tied with cathode charge in luminescent layer It closes, generates bright.
Since OLED display technology has many advantages, such as that self-luminous, wide viewing angle, low energy consumption reaction speed are fast, and this technology Make it possible the display screen of portable highly collapsible, in mobile phone, DV, laptop, TV, automobile It is used widely in equal fields.But compared with the requirement of product in practical application, there is also certain differences for its performance at present Away from especially luminous efficiency and service life are improved there is still a need for further.Mainly improved in terms of two: first is that device architecture Optimization and innovation, second is that the research and development of performance function material.
In order to make high performance OLED luminescent device, Recent study personnel constantly propose new luminous mechanism and function Material.Qiu Yong seminar of Tsinghua University proposes thermal activation sensitized luminescence mechanism within 2014, uses TADF material as OLED device The material of main part of part is sensitized conventional fluorescent/phosphor material by TADF material to realize the promotion of device performance.Almost simultaneously, Adachi seminar of Kyushu University also proposed similar luminous mechanism.With the continuous research to the type material, grind Study carefully personnel and constantly design new OLED functional material, but there is presently no superior performance and can satisfy large-scale production and want The TADF material of main part asked occurs.The charge transport properties for focusing on balancing material of such TADF design of material exploitation, and And keep high charge mobility and triplet.
It must just be selected according to the industry application requirement of current OLED device to meet the photoelectric characteristic demand of device OLED functional material or combination of materials with high performance are just able to achieve high efficiency, the synthesis of long-life and low-voltage of device Characteristic.The development of OLED material at present also lags significantly behind the requirement of panel manufacturing enterprise and the demand of practical application, and exploitation is more High performance organic functional material is particularly important and urgently in face of the current market demand.
Summary of the invention
It is not able to satisfy the application in actual production for current OLED functional material, the present invention provides one kind to have TADF The bipolarity pyrrolotriazine derivatives of property and its application in OLED device.Pyrrolotriazine derivatives of the invention have the charge of balance Transmission performance and higher triplet, and be not easy to crystallize, there is good thermal stability and film forming.Of the invention Pyrrolotriazine derivatives are used as material of main part and dopant material is applied in OLED device, can effectively improve the luminous efficiency of device And service life.
Technical scheme is as follows: a kind of pyrrolotriazine derivatives, with D-A structure, with triazine and its modification group For electron acceptor (A), using carbazole and its modification group as electron donor (D), the structure of the derivative has as described below logical Formula (1), general formula (2), shown in general formula (3) structure:
Z is independently expressed as N or C in formula, and Z is not C or N simultaneously in formula；
R in above-mentioned general formula0It is expressed as one of F, Cl, Br, cyano, trifluoromethyl；
R1Alkyl, alkoxy for C1-C6；
R2Indicate the alkyl of H or C1-C20, the alkylamine of C2-C6, the aryl of C6-C20；
W is expressed as singly-bound, N, O, S, CR3R4, wherein R3、R4For one of methyl, phenyl；
M=0,1 or 2；
N=0,1,2；
Q=1 or 2；
X and Y is separately expressed as singly-bound, N, O, S, CR5R6, wherein R5、R6For one of methyl, phenyl；X and Y is different When be singly-bound；When X or Y be the N atomic time, be connected with the aryl of C6-C20.
In general formula (2) and general formula (3), when X or Y is the N atomic time, it is connected with the aryl of C6-C20, the aryl is benzene One of base, naphthalene, anthryl, xenyl, pyrenyl, dibenzofuran group, two phenylpropyl alcohol thienyls, carbazyl.
In general formula (1), general formula (2) and general formula (3), when Z is N, m=0, aryl containing Z is pyridine, pyrimidine, pyrazine, rattles away One of piperazine, triazine.
In general formula (1), general formula (2) and general formula (3), R1For one of methyl, isopropyl, tert-butyl, methoxyl group.
In general formula (1), general formula (2) and general formula (3), R2For methyl, isopropyl, tert-butyl, methoxyl group, C2-C6 alkyl One of amine and phenyl, naphthalene, anthryl, xenyl, base, pyrenyl, dibenzofuran group, two phenylpropyl alcohol thienyls, carbazyl it One.
In general formula (2) and general formula (3), when X or Y is the N atomic time, the aryl group of connection be phenyl, xenyl, naphthalene, One of anthryl, dibenzofuran group, dibenzothiophene, N- phenyl carbazole base, and selected aryl is connected with substituent group, replaces Base is selectable any position on aromatic ring, and substituent group is methyl, isopropyl, tert-butyl, methoxyl group, alkylamine, phenyl, biphenyl One of base, dibenzofurans, carbazole, hexichol amido.
In general formula (1), work as R2When for aryl, the aryl is connected with substituent group, and substituent group is selectable on aromatic ring Anticipate position, substituent group be methyl, isopropyl, tert-butyl, methoxyl group, the alkylamine of C2-C6, phenyl, dibenzofurans, carbazole, One of hexichol amido.
Electron acceptor in general formula (1), general formula (2) and general formula (3) one of comprises the following structure:
Electron donor in general formula (1), general formula (2) and general formula (3) one of comprises the following structure:
General formula (1), general formula (2) and general formula (3) include any one in following compound:
Application of the pyrrolotriazine derivatives in organic electroluminescence device, especially as the main body of organic electroluminescence device The application of material and dopant material.
Pyrrolotriazine derivatives of the present invention are a kind of ambipolar TADF material, thermal stability with higher and film forming Performance can be applied to organic electroluminescence device luminescent layer as material of main part or dopant material.
Pyrrolotriazine derivatives of the invention have the charge transport ability for comparing balance, and are not easy to crystallize, and have good Film forming and thermal stability.Pyrrolotriazine derivatives of the invention can be used as the functional material of OLED luminescent device, especially a kind of tool There are the material of main part and dopant material of TADF property, uses pyrrolotriazine derivatives of the invention as material of main part or dopant material institute The brightness of making devices, efficiency roll-off are greatly improved, and driving voltage reduces, simultaneously for the promotion of device lifetime Clearly.
Specific embodiment
With reference to embodiments to the present invention it is further elucidated above, it should be appreciated that listed embodiment only for ease of understanding this The core methed and application field of invention, but the scope of the present invention is not limited to this.
A kind of pyrrolotriazine derivatives, with D-A structure, using triazine and its modification group as electron acceptor (A), with carbazole and Its modification group is electron donor (D), and the structure of the derivative has general formula as described below (1), general formula (2), general formula (3) knot Shown in structure:
Z is independently expressed as N or C in formula, and Z is not C or N simultaneously in formula；
R in above-mentioned general formula0It is expressed as one of F, Cl, Br, cyano, trifluoromethyl；
R1Alkyl, alkoxy for C1-C6；
R2Indicate the alkyl of H or C1-C20, the alkylamine of C2-C6, the aryl of C6-C20；
W is expressed as singly-bound, N, O, S, CR3R4, wherein R3、R4For one of methyl, phenyl；
M=0,1 or 2；
N=0,1,2；
Q=1 or 2；
X and Y is separately expressed as singly-bound, N, O, S, CR5R6, wherein R5、R6For one of methyl, phenyl；X and Y is different When be singly-bound；When X or Y be the N atomic time, be connected with the aryl of C6-C20.
In general formula (2) and general formula (3), when X or Y is the N atomic time, it is connected with the aryl of C6-C20, the aryl is benzene One of base, naphthalene, anthryl, xenyl, pyrenyl, dibenzofuran group, two phenylpropyl alcohol thienyls, carbazyl.
In general formula (1), general formula (2) and general formula (3), when Z is N, m=0, aryl containing Z is pyridine, pyrimidine, pyrazine, rattles away One of piperazine, triazine.
In general formula (1), general formula (2) and general formula (3), R1For one of methyl, isopropyl, tert-butyl, methoxyl group.
In general formula (1), general formula (2) and general formula (3), R2For methyl, isopropyl, tert-butyl, methoxyl group, C2-C6 alkyl One of amine and phenyl, naphthalene, anthryl, xenyl, base, pyrenyl, dibenzofuran group, two phenylpropyl alcohol thienyls, carbazyl it One.
In general formula (2) and general formula (3), when X or Y is the N atomic time, the aryl group of connection be phenyl, xenyl, naphthalene, One of anthryl, dibenzofuran group, dibenzothiophene, N- phenyl carbazole base, and selected aryl is connected with substituent group, replaces Base is selectable any position on aromatic ring, and substituent group is methyl, isopropyl, tert-butyl, methoxyl group, alkylamine, phenyl, biphenyl One of base, dibenzofurans, carbazole, hexichol amido.
In general formula (1), work as R2When for aryl, the aryl is connected with substituent group, and substituent group is selectable on aromatic ring Anticipate position, substituent group be methyl, isopropyl, tert-butyl, methoxyl group, the alkylamine of C2-C6, phenyl, dibenzofurans, carbazole, One of hexichol amido.
Electron acceptor in general formula (1), general formula (2) and general formula (3) one of comprises the following structure:
Electron donor in general formula (1), general formula (2) and general formula (3) one of comprises the following structure:
General formula (1), general formula (2) and general formula (3) include any one in following compound:
Intermediate synthetic example 1, the synthesis of intermediate 1
The synthesis of intermediate 1: addition 30g intermediate 1-1, the 8.1g sodium hydroxide in 500ml there-necked flask, 350ml ethyl alcohol, 25.2g intermediate 1-2 is added after stirring 2h under the conditions of 40 DEG C, is warming up to 80 DEG C and is stirred to react 10h, is down to room temperature and white is precipitated admittedly Body, filtering gained crude product obtain the total 13.2g of intermediate 1, yield 29.6% through re crystallization from toluene；
Intermediate synthetic example 2, the synthesis of intermediate 2
The synthesis of intermediate 2: addition 30g intermediate 1-1, the 8.1g sodium hydroxide in 500ml there-necked flask, 350ml ethyl alcohol, 28.5g intermediate 2-1 is added after stirring 2h under the conditions of 40 DEG C, is warming up to 80 DEG C and is stirred to react 10h, is down to room temperature and white is precipitated admittedly Body, filtering gained crude product obtain the total 16.9g of intermediate 2, yield 35.2% through re crystallization from toluene；
Intermediate synthetic example 3, the synthesis of intermediate 3
The synthesis of intermediate 3-2: 30g intermediate 3-1,25.7g potassium carbonate, 240ml first are added in 500ml there-necked flask Benzene, 60ml water, 60ml ethyl alcohol, 29.2g 4,6- diphenyl -1,3,5-triazines -2- boric acid replace nitrogen protection, and 0.6g tetra- is added (triphenylphosphine) palladium is warming up to 80 DEG C and is stirred to react 8h, and TLC monitoring raw material is down to room temperature after reacting completely, filters, separate organic Phase is washed to neutrality, and silicagel column is crossed after anhydrous sodium sulfate is dry, and gained crude product obtains intermediate 3-2 through re crystallization from toluene and is total to 32.9g, yield 72.6%；
The synthesis of intermediate 3: 30g intermediate 3-2,300ml methylene chloride, 18.5ml tri- are added in 500ml there-necked flask Ethamine replaces nitrogen protection, and 12.3ml trifluoromethanesulfanhydride anhydride is added dropwise after being cooled to 0 DEG C, continues normal-temperature reaction 6h after being added dropwise After be washed to neutrality, cross column after anhydrous sodium sulfate is dry, gained crude product re crystallization from toluene obtains the total 33.5g of intermediate 3, yield 86.3%；
Compound synthesis embodiment 1, the synthesis of compound 1
The synthesis of compound 1: 10g intermediate 1,7.8g compound 1-1, potassium carbonate are sequentially added in 250ml there-necked flask 6.0g, toluene 150ml lead to nitrogen 5min, and 1,10- Féraud beautiful jade 0.2g, cuprous bromide 0.15g is added, and are heated to 110-120 DEG C instead It answers, sample detection is down to 40 DEG C of filterings after raw material reacts completely after reacting 7h, and organic phase is washed to neutrality, anhydrous sodium sulfate Column is crossed after dry 2h, eluent concentration recrystallization obtains the total 11.6g of compound 1, yield 75.3%.1H NMR(400MHz, CDCl3) δ 8.84 (s, 2H), 7.48-7.55 (m, 9H), 7.40 (d, J=7.2,2H), 7.28-7.32 (m, 11H), 7.22 (t, J =7.2,2H), 7.08 (t, J=7.2,2H), 7.00 (t, J=7.2,3H)；
Compound synthesis embodiment 2, the synthesis of compound 2
The synthesis of compound 2: 10g intermediate 2,7.0g compound 1-1, potassium carbonate are sequentially added in 250ml there-necked flask 5.4g, toluene 150ml lead to nitrogen 5min, and 1,10- Féraud beautiful jade 0.19g is added, and cuprous bromide 0.14g is heated to 110-120 DEG C Reaction, sample detection is down to 40 DEG C of filterings after raw material reacts completely after reacting 7h, and organic phase is washed to neutrality, anhydrous slufuric acid Column is crossed after the dry 2h of sodium, eluent concentration recrystallization obtains the total 10.9g of compound 2, yield 72.8%.1H NMR(400MHz, CDCl3) δ 7.55 (d, J=7.2,3H), 7.46-7.50 (m, 6H), 7.40 (d, J=7.2,2H), 7.27-7.32 (m, 11H), 7.22 (d, J=7.2,2H), 7.08 (t, J=7.2,2H), 7.00-7.02 (m, 5H)；
Synthetic example 3, the synthesis of compound 3
The synthesis of compound 3: 10g intermediate 3,6.0g compound 1-1, potassium carbonate are sequentially added in 250ml there-necked flask 4.6g, toluene 150ml lead to nitrogen 5min, and 1,10- Féraud beautiful jade 0.15g is added, and cuprous bromide 0.12g is heated to 110-120 DEG C Reaction, sample detection is down to 40 DEG C of filterings after raw material reacts completely after reacting 7h, and organic phase is washed to neutrality, anhydrous slufuric acid Column is crossed after the dry 2h of sodium, eluent concentration recrystallization obtains the total 7.5g of compound 3, yield 76.2%.1H NMR(400MHz, CDCl3) δ 7.55 (d, J=7.2,3H), 7.46-7.50 (m, 6H), 7.40 (d, J=7.2,2H), 7.27-7.32 (m, 11H), 7.22 (d, J=7.2,2H), 7.08 (t, J=7.2,2H), 7.00-7.02 (m, 5H)；
Pyrrolotriazine derivatives in the present invention may be used as the material of main part of OLED device and dopant material uses, this hair of part Compound and the hot property of common OLED material and orbital energy level parameter (glass transition temperature Tg, 5% decomposition at present in bright Temperature Td, energy level of frontier orbital HOMO/LUMO) as shown in table 1.
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 20ml/min；DSC-60 heat differential scanning point of the Tg temperature in Japanese Shimadzu Corporation It is measured in analyzer, nitrogen flow 10ml/min；HOMO/LUOMO energy level is to carry out simulation meter in 09 software of Gaussian The data obtained is calculated, calculation method uses B3LYP hydridization functional, base group 6-31g (d).
By upper table data it is found that pyrrolotriazine derivatives of the invention thermal stability with higher, thus have preferably at Film properties, so that the made OLED device life-span upgrading containing material of the present invention；Pyrrolotriazine derivatives of the invention also have Different HOMO energy levels, can be applied to different functional layers.
It is suitable in OLED device as main body (Host) material and dopant material preferably to evaluate the compounds of this invention With property, below by way of the device comparative example for using current material and the device embodiments for using material of the present invention relatively this hair in detail Application effect of the material of bright synthesis in OLED device.The embodiment is compared with comparative example, the manufacture craft of the device It is identical, and identical baseplate material and electrode material are used, the film thickness of electrode material is also consistent, unlike Some adjustment have been carried out to some materials used in device.
Organic film carries out double source by ANS evaporated device and steams altogether, and vapor deposition substrate is high saturating quartz glass, guest materials doping Mass concentration is 2%, and after vapor deposition, being packaged in glove box (is ar gas environment in glove box, water content and oxygen are dense Degree is less than 1ppm)
Comparative example 1
Transparent substrate layer/ito anode layer/hole transmission layer (TAPC, with a thickness of 60nm)/luminescent layer (light emitting host material CBP and Ir (mphmq)2(tmd) according to the quality of 98:2 than blending, with a thickness of 30nm)/electron transfer layer (TPBi, with a thickness of 40nm)/electron injecting layer (LiF, thickness 1nm)/cathode reflection electrode layer Al.
Comparative example 2
Transparent substrate layer/ito anode layer/hole transmission layer (TAPC, with a thickness of 60nm)/luminescent layer (light emitting host material CBP and DPAVBi according to the quality of 98:2 than blending, with a thickness of 30nm)/electron transfer layer (TPBi, with a thickness of 40nm)/electronics Implanted layer (LiF, thickness 1nm)/cathode reflection electrode layer Al.
The molecular structural formula of associated materials is as follows:
Some materials structure used in device:
Specific preparation process is as follows:
Transparent substrate layer is transparent substrate, such as transparent PI film, glass.
Ito anode layer is washed, successively carries out neutralizing treatment, milli-Q water, drying, then carry out ultraviolet-ozone It washs to remove the organic residue on the transparent surface ITO.
On above-mentioned ito anode layer, using vacuum deposition apparatus, it is the TAPC of 80nm as hole transmission layer that film thickness, which is deposited, It uses.
After above-mentioned hole mobile material vapor deposition, make the luminescent layer of OLED luminescent device, use compound CBP as Material of main part, compound Ir (mphmq)2It (tmd) is dopant material, dopant material doping ratio is 2% weight ratio, and shine tunic Thickness is 30nm.
After above-mentioned luminescent layer, continue vacuum evaporation electron transport material TPBI, as electron transfer layer, film thickness is 40nm。
It on the electron transport layer, is the layer of lithium fluoride of 1nm as electron injecting layer by vacuum evaporation production film thickness.
It is the aluminium layer of 80nm as negative electrode layer by vacuum evaporation production film thickness on electron injecting layer.
After the production of above-mentioned OLED device, anode and cathode is connected with driving circuit, the electricity of measurement device Flow efficiency, the service life of light emission luminance and device.
Device embodiments 1~12
Embodiment 1
Transparent substrate layer/ito anode layer/hole transmission layer (TAPC, with a thickness of 80nm)/luminescent layer (light emitting host material Compound 1 and Ir (mphmq)2(tmd) according to the quality of 98:2 than blending, with a thickness of 30nm)/electron transfer layer (TPBi, thickness For 40nm)/electron injecting layer (LiF, thickness 1nm)/cathode reflection electrode layer Al；
Embodiment 2
Transparent substrate layer/ito anode layer/hole transmission layer (TAPC, with a thickness of 80nm)/luminescent layer (light emitting host material Compound 2 and Ir (mphmq)2(tmd) according to the quality of 98:2 than blending, with a thickness of 30nm)/electron transfer layer (TPBi, thickness For 40nm)/electron injecting layer (LiF, thickness 1nm)/cathode reflection electrode layer Al；
Embodiment 3
Transparent substrate layer/ito anode layer/hole transmission layer (TAPC, with a thickness of 80nm)/luminescent layer (light emitting host material Compound 3 and Ir (mphmq)2(tmd) according to the quality of 98:2 than blending, with a thickness of 30nm)/electron transfer layer (TPBi, thickness For 40nm)/electron injecting layer (LiF, thickness 1nm)/cathode reflection electrode layer Al；
Embodiment 4
Transparent substrate layer/ito anode layer/hole transmission layer (TAPC, with a thickness of 80nm)/luminescent layer (light emitting host material Compound 4 and Ir (mphmq)2(tmd) according to the quality of 98:2 than blending, with a thickness of 30nm)/electron transfer layer (TPBi, thickness For 40nm)/electron injecting layer (LiF, thickness 1nm)/cathode reflection electrode layer Al；
Embodiment 5
Transparent substrate layer/ito anode layer/hole transmission layer (TAPC, with a thickness of 80nm)/luminescent layer (light emitting host material Compound 8 and Ir (mphmq)2(tmd) according to the quality of 98:2 than blending, with a thickness of 30nm)/electron transfer layer (TPBi, thickness For 40nm)/electron injecting layer (LiF, thickness 1nm)/cathode reflection electrode layer Al；
Embodiment 6
Transparent substrate layer/ito anode layer/hole transmission layer (TAPC, with a thickness of 80nm)/luminescent layer (light emitting host material Compound 9 and Ir (mphmq)2(tmd) according to the quality of 98:2 than blending, with a thickness of 30nm)/electron transfer layer (TPBi, thickness For 40nm)/electron injecting layer (LiF, thickness 1nm)/cathode reflection electrode layer Al；
Embodiment 7
Transparent substrate layer/ito anode layer/hole transmission layer (TAPC, with a thickness of 80nm)/luminescent layer (light emitting host material Compound 10 and Ir (mphmq)2(tmd) according to the quality of 98:2 than blending, with a thickness of 30nm) and/electron transfer layer (TPBi, it is thick Degree is 40nm)/electron injecting layer (LiF, thickness 1nm)/cathode reflection electrode layer Al；
Embodiment 8
Transparent substrate layer/ito anode layer/hole transmission layer (TAPC, with a thickness of 80nm)/luminescent layer (light emitting host material Compound 29 and Ir (mphmq)2(tmd) according to the quality of 98:2 than blending, with a thickness of 30nm) and/electron transfer layer (TPBi, it is thick Degree is 40nm)/electron injecting layer (LiF, thickness 1nm)/cathode reflection electrode layer Al；
Embodiment 9
Transparent substrate layer/ito anode layer/hole transmission layer (TAPC, with a thickness of 80nm)/luminescent layer (light emitting host material Compound CBP and compound 38 according to the quality of 98:2 than blending, with a thickness of 30nm)/electron transfer layer (TPBi, with a thickness of 40nm)/electron injecting layer (LiF, thickness 1nm)/cathode reflection electrode layer Al；
Embodiment 10
Transparent substrate layer/ito anode layer/hole transmission layer (TAPC, with a thickness of 80nm)/luminescent layer (light emitting host material Compound CBP and compound 39 according to the quality of 98:2 than blending, with a thickness of 30nm)/electron transfer layer (TPBi, with a thickness of 40nm)/electron injecting layer (LiF, thickness 1nm)/cathode reflection electrode layer Al；
Embodiment 11
Transparent substrate layer/ito anode layer/hole transmission layer (TAPC, with a thickness of 80nm)/luminescent layer (light emitting host material Compound CBP and compound 50 according to the quality of 98:2 than blending, with a thickness of 30nm)/electron transfer layer (TPBi, with a thickness of 40nm)/electron injecting layer (LiF, thickness 1nm)/cathode reflection electrode layer Al；
Embodiment 12
Transparent substrate layer/ito anode layer/hole transmission layer (TAPC, with a thickness of 80nm)/luminescent layer (light emitting host material Compound CBP and compound 51 according to the quality of 98:2 than blending, with a thickness of 30nm)/electron transfer layer (TPBi, with a thickness of 40nm)/electron injecting layer (LiF, thickness 1nm)/cathode reflection electrode layer Al；
Embodiment 1~12 of the present invention is using present invention synthesis compound as the layer main body material that shines in OLED device Material and the application of luminescent layer dopant material, compared with comparative example, the manufacture craft of the device of embodiment 1~12 is identical, and And used baseplate material is also identical with electrode material, the film thickness of electrode material is also consistent, device performance test Method is identical as comparative example.The test result of obtained device is as shown in table 2.
Table 2
Note: half-life test is device in 1000cd/m in table2Brightness lower die-away time.
It can be seen that compared with using device of the current material CBP as Host material by 2 data of table, in device reality Apply used in a 1-8 material of the present invention as Host material after, the driving voltage of device reduces about 25%, and the half-life improves about 85%, and current efficiency and light emission luminance increase, therefore material of the present invention can be applied to conduct in OLED device Host material improves device performance；
It can be seen that by 2 data of table compared with using device of the current material DPAVBi as Dopant material, in device Used in part embodiment 9-12 material of the present invention as Dopant material after, the driving voltage of device reduces about 25%, the half-life About 2 times are improved, and current efficiency and light emission luminance increase, therefore material of the present invention can be applied in OLED device Improve device performance as Dopant material；
In conclusion compared with current material, material of the present invention be applied to OLED device, especially Host material and When Dopant material, device performance can be improved by a relatively large margin, be a kind of more promising novel organic OLED function Material.
Above embodiments only section Example cited by the synthesis of material of the present invention and application method for ease of understanding, and It is not used in the limitation present invention.It is appreciated that related practitioner is easy to carry out modification appropriate in this structure, thus it is all Made any modifications, equivalent replacements, and improvements etc. within the spirit and principles in the present invention, should be included in protection of the invention Within the scope of.

Claims (11)

1. a kind of pyrrolotriazine derivatives, with D-A structure, using triazine and its modification group as electron acceptor (A), with carbazole and its Modification group be electron donor (D), it is characterised in that: the structure of the derivative have general formula as described below (1), general formula (2), Shown in general formula (3) structure:
Z is independently expressed as N or C in formula, and Z is not C or N simultaneously in formula；
R in above-mentioned general formula0It is expressed as one of F, Cl, Br, cyano, trifluoromethyl；
R1Alkyl, alkoxy for C1-C6；
R2Indicate the alkyl of H or C1-C20, the alkylamine of C2-C6, the aryl of C6-C20；
W is expressed as singly-bound, N, O, S, CR3R4, wherein R3、R4For one of methyl, phenyl；
M=0,1 or 2；
N=0,1,2；
Q=1 or 2；
X and Y is separately expressed as singly-bound, N, O, S, CR5R6, wherein R5、R6For one of methyl, phenyl；X and Y is not simultaneously Singly-bound；When X or Y be the N atomic time, be connected with the aryl of C6-C20.
2. pyrrolotriazine derivatives according to claim 1, it is characterised in that: in general formula (2) and general formula (3), when X or Y is N Atomic time, it is connected with the aryl of C6-C20, the aryl is phenyl, naphthalene, anthryl, xenyl, pyrenyl, base, dibenzo One of furyl, two phenylpropyl alcohol thienyls, carbazyl.
3. pyrrolotriazine derivatives according to claim 1, it is characterised in that: in general formula (1), general formula (2) and general formula (3), When Z is N, m=0, aryl containing Z is one of pyridine, pyrimidine, pyrazine, pyridazine, triazine.
4. pyrrolotriazine derivatives according to claim 1, it is characterised in that: in general formula (1), general formula (2) and general formula (3), R1 For one of methyl, isopropyl, tert-butyl, methoxyl group.
5. pyrrolotriazine derivatives according to claim 1, it is characterised in that: in general formula (1), general formula (2) and general formula (3), R2 For methyl, isopropyl, tert-butyl, methoxyl group, one of the alkylamine of C2-C6 and phenyl, naphthalene, anthryl, xenyl, base, One of pyrenyl, dibenzofuran group, two phenylpropyl alcohol thienyls, carbazyl.
6. pyrrolotriazine derivatives according to claim 1, it is characterised in that: in general formula (2) and general formula (3), when X or Y is N Atomic time, the aryl group of connection are phenyl, xenyl, naphthalene, anthryl, dibenzofuran group, dibenzothiophene, N- phenyl One of carbazyl, and selected aryl is connected with substituent group, substituent group is selectable any position on aromatic ring, and substituent group is first One of base, isopropyl, tert-butyl, methoxyl group, alkylamine, phenyl, xenyl, dibenzofurans, carbazole, hexichol amido.
7. pyrrolotriazine derivatives according to claim 1, it is characterised in that: in general formula (1), work as R2When for aryl, the virtue Base is connected with substituent group, and substituent group is selectable any position on aromatic ring, and substituent group is methyl, isopropyl, tert-butyl, methoxy One of base, the alkylamine of C2-C6, phenyl, dibenzofurans, carbazole, hexichol amido.
8. pyrrolotriazine derivatives according to claim 1, it is characterised in that: in general formula (1), general formula (2) and general formula (3) Electron acceptor one of comprises the following structure:
9. pyrrolotriazine derivatives according to claim 1, it is characterised in that: in general formula (1), general formula (2) and general formula (3) Electron donor one of comprises the following structure:
10. pyrrolotriazine derivatives according to claim 1, it is characterised in that: general formula (1), general formula (2) and general formula (3) include Any one in following compound:
11. application of the pyrrolotriazine derivatives according to claim 1 to 9 in organic electroluminescence device, especially It is the application of the material of main part and dopant material as organic electroluminescence device.
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