CN103936653A - Benzo carbazoles OLED material, its preparation method and its application - Google Patents

Benzo carbazoles OLED material, its preparation method and its application Download PDF

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CN103936653A
CN103936653A CN201310680508.6A CN201310680508A CN103936653A CN 103936653 A CN103936653 A CN 103936653A CN 201310680508 A CN201310680508 A CN 201310680508A CN 103936653 A CN103936653 A CN 103936653A
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condensed ring
formula
base
specially
aromatic
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曹建华
郭剑
李雅敏
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Shijiazhuang Chengzhi Yonghua Display Material Co Ltd
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Shijiazhuang Chengzhi Yonghua Display Material Co Ltd
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Abstract

The invention discloses a benzo carbazoles OLED material, its preparation method and its application. A structural general formula of the benzo carbazoles OLED material is disclosed as a formula (I). The OLED material can increase the carrier transmission efficiency and enhance the luminescence efficiency of a device. Introduction of R1 and R2 substituents in the compound molecule is capable of reducing HOMO value of the OLED material molecule, and is capable of increasing the molecule stability and material glass transition temperature, and is in favor of cavity injection, the invention provides the OLED material with excellent performance. The preparation method has the advantages of simple synthesis route, easy operation, high reaction yield, and reduced preparation cost of the OLED material, and the preparation method has good industrial prospect.

Description

Benzo carbazoles OLED material and preparation method thereof and application
Technical field
The invention belongs to ORGANIC ELECTROLUMINESCENCE DISPLAYS technical field, relate to a kind of benzo carbazoles OLED material and preparation method thereof and application.
Background technology
First organic electroluminescent (being called for short OLED) and relevant research have found the electro optical phenomenon of organic compound single-crystal anthracene as far back as people such as pope in 1963.A kind of amorphous membranous type device has been made by the method for evaporation organic molecule by the Kodak of the U.S. in 1987, and driving voltage has been dropped in 20V.This class device owing to thering is ultra-thin, complete solidify, luminous, brightness is high, visual angle is wide, fast response time, driving voltage is low, power consumption is little, bright in luster, contrast gradient is high, technological process is simple, good temp characteristic, can realize the advantages such as softness demonstration, can be widely used in flat-panel monitor and area source, therefore obtain studying widely, develop and used.
Organic electroluminescent is mainly divided into fluorescence and phosphorescence, but according to spin quantum statistical theory, the probability of singlet state exciton and triplet exciton is 1:3, and the theoretical limit of the fluorescence of white singlet state exciton radiative transition is 25, and the theoretical limit of the fluorescence of triplet exciton radiative transition is 75.How to utilize the energy of 75% triplet excitons to become the task of top priority.The discovery electrophosphorescence phenomenons such as Forrest in 1997 have broken through the restriction of electroluminescent organic material quantum yield 25% efficiency, cause the extensive concern of people to metal complexes phosphor material.From then on, people carry out a large amount of research to phosphor material.
Summary of the invention
The object of this invention is to provide a kind of benzo carbazoles OLED material and preparation method thereof and application.
Benzo carbazoles OLED material provided by the invention, its general structure is suc as formula shown in I,
In described formula I, R 1be selected from following group a or b:
Any one in the heterocyclic radical of condensed ring aromatic ethylene base, the aryl amine of C2-C60, the condensed ring radical of the nitrogen atom of C2-C60, the condensed ring radical of the sulfur-bearing of C6-C60 or Sauerstoffatom and the nitrogen atom of C2-C60 of the aromatic ethylene base of a, the aromatic base that is selected from C2-C60, C2-C60, the condensed ring aromatic base of C2-C60, C2-C60;
B, contain substituent group a;
R 2be selected from following group c or d:
The condensed ring aromatic ethylene base of the aromatic ethylene base of c, the aromatic base that is selected from hydrogen, halogen, methyl, methoxyl group, C2-C60, C2-C60, the condensed ring aromatic base of C2-C60, C2-C60, the aryl amine of C2-C60, any one in the heterocyclic radical of the phosphorous or silicon of the condensed ring radical of the nitrogen atom of C2-C60, C6-C60 or the condensed ring radical of boron atom and the nitrogen atom of C2-C60;
D, contain substituent group c;
In described group b and group d, substituting group is all selected from least one in aliphatic group, halogen and the cyano group of deuterium, C1-C20;
N is the integer of 1-5.
Preferably, in described formula I, R 1, R 2all be selected from any one in following group:
In above-mentioned group, described A, B and C are independently carbon atom or nitrogen-atoms respectively, but A, B and C can not be nitrogen-atoms simultaneously,, represent substituent position;
R 3be selected from the aromatic base of hydrogen, C2-C60, any one in the heterocyclic radical of condensed ring aromatic ethylene base, the aryl amine of C2-C60, the condensed ring radical of the nitrogen atom of C2-C60 and the nitrogen atom of C2-C60 of the condensed ring aromatic base of the aromatic ethylene base of C2-C60, C2-C60, C2-C60;
R 4and R 5all be selected from the aliphatic group of C1-C18, the condensed ring aromatic base of the aromatic base of C2-C60, C2-C60, the aryl amine of C2-C60, be connected with heterocycle C2-C60 aromatic base and be connected with any one in the aromatic base of C2-C60 of alkyl of C1-C18;
R 6be selected from any one in the condensed ring aromatic base of the aliphatic group of C1-C18, the aromatic base of C2-C60 and C2-C60;
R 7be selected from the aliphatic group of hydrogen, C1-C18, the aromatic ethylene base of the aromatic base of C2-C60, C2-C60, any one in the condensed ring aromatic ethylene base of the condensed ring aromatic base of C2-C60 and C2-C60;
D and E independently represent respectively the aromatic base of C2-C60, any one in the heterocyclic radical of condensed ring aromatic ethylene base, the condensed ring radical of C2-C60 and the nitrogen atom of C2-C60 of the condensed ring aromatic base of the aromatic ethylene base of C2-C60, C2-C60, C2-C60;
F and G independently represent respectively carbon atom or nitrogen-atoms.
Concrete, compound shown in described formula I is any one in following compound:
Shown in preparation formula I provided by the invention, the method for compound, comprises the steps:
1) will catalyzer, part and alkali mix and carry out ring closure reaction in solvent, react complete and obtain
2) by step 1) gained consider to be worth doing to mix in solvent with potassium and carry out after linked reaction, use the mixed solution cancellation being formed by tetrahydrofuran (THF) and water to react, obtain
3) by step 2) gained mix to reflux with catalyzer, phosphorus part and alkali and react, obtain compound shown in described formula I;
Described step 1)-3) in, the R in each reaction materil structure general formula 1, R 2all identical with the definition in aforementioned formula I with the definition of n.
In the step 1) of aforesaid method, catalyzer is palladium or Pd (PPh 3) 4, Pd (PPh 3) 2cl 2or Pd (dba) 2;
Part is tri-butyl phosphine, triphenyl phosphorus or thricyclohexyl phosphorus;
Alkali is salt of wormwood, sodium carbonate, potassium acetate or sodium acetate;
Described the mole dosage that feeds intake of catalyzer, part and alkali is 1.0:1.0-1.5:0.01-0.05:0.02-0.10:2.0-3.0, is specially 1.0:1.2:0.02:0.05:2.5;
In described ring closure reaction, temperature is 100-150 ℃, and the time is 8-16 hour, is specially 12 hours;
Described step 2) in, the mole dosage that feeds intake of considering to be worth doing with potassium is 1.0:1.0-5.0, is specially 1.0:4.0;
In the described mixed solution being comprised of tetrahydrofuran (THF) and water, the volume ratio of tetrahydrofuran (THF) and water is 1.0:1.0;
In described linked reaction step, temperature is room temperature, and the time is 12-48 hour, is specially 24 hours;
In described step 3), catalyzer is three (dibenzalacetone) two palladiums, palladium, Pd (PPh 3) 4or Pd (PPh 3) 2cl 2or Pd (dba) 2;
Phosphorus part be 2-dicyclohexylphosphontetrafluoroborate-2 ', 6 '-dimethoxy-biphenyl, tri-butyl phosphine, triphenyl phosphorus or thricyclohexyl phosphorus;
Alkali is sodium tert-butoxide, potassium tert.-butoxide, sodium hydroxide or potassium hydroxide;
than for 2.0-2.5:1.0:0.005-0.02:0.01-0.05:2.0-3.0, be specially 2.2:1.0:0.01:0.04:2.5,2.25:1.0:0.01:0.04:2.5,2.2-2.25:1.0:0.01:0.04:2.5,3.1:1.0:0.01:0.04:2.5,2.25-3.1:1.0:0.01:0.04:2.5 or 2.2-3.1:1.0:0.01:0.04:2.5 with the mole dosage that feeds intake of catalyzer, phosphorus part and alkali;
In described reactions steps, the time is 24-56 hour, is specially 48 hours;
Described step 1)-3) all in inert atmosphere, carry out; Described inert atmosphere is specially nitrogen or argon gas atmosphere;
Described step 1)-3), in, described solvent is all selected from least one in N-Methyl pyrrolidone, tetrahydrofuran (THF), toluene, DMF and dimethylbenzene.
In addition, the application of compound in preparing luminescent material shown in the luminescent material that contains compound shown in the formula I that the invention described above provides and this formula I, also belongs to protection scope of the present invention; Wherein, the fluorescent emission wavelength of described luminescent material is specially 370-420nm.Be specially 378,407,414,418,378-414 or 407-418nm;
The application of compound shown in the formula I that the invention described above provides in preparing electroluminescent device and the electroluminescent device that contains compound shown in formula I, also belong to protection scope of the present invention.Wherein, in described electroluminescent device, compound shown in formula I is for forming the material of organic luminous layer;
Described electroluminescent device specifically can be following structure:
By transparent substrate, anode, hole transmission layer, organic luminous layer, electron transfer layer and cathode layer, formed successively from the bottom to top;
Wherein, the material that forms described transparent substrate is glass or flexible substrate;
The material that forms described anode layer is inorganic materials or organic conductive polymkeric substance; Wherein, described inorganic materials is tin indium oxide, zinc oxide, stannic oxide, gold and silver or copper; Described organic conductive polymkeric substance is selected from least one in Polythiophene, polyvinylbenzenesulfonic acid sodium and polyaniline;
The material that forms described hole transmission layer is selected from least one in TDATA and NPB;
The structural formula of described NPB and TDATA is as follows:
The material that forms described organic luminous layer for by compound shown in formula I and the mixture forming; Compound shown in described formula I and mass ratio be 1:0.001-0.2, be specially 1:0.08;
The material that forms described electron transfer layer is Alq3, Gaq3 or BPhen;
Wherein, the structural formula of Alq3, BPhen and Gaq3 is as follows successively:
The material that forms described cathode layer is selected from any one or the alloy of any two kinds of compositions or the fluorochemical of following element in following element: lithium, magnesium, silver, calcium, strontium, aluminium, indium, copper, Jin Heyin.
The thickness of described hole transmission layer is 5-15nm, is specially 10nm;
The thickness of described organic luminous layer is 10-100nm, is specially 80nm;
The thickness of described electron transfer layer is 40-60nm, is specially 50nm;
The thickness of described cathode layer is 90-110nm, is specially 100nm.
The invention provides a kind of OLED material that comprises carbazole structure unit.This OLED material not only can improve carrier transport efficiency, can also improve the luminous efficiency of device.R in compound molecule 1, R 2substituent introducing, has reduced the HOMO value of this OLED material molecule, has improved the stability of molecule and the second-order transition temperature of material, is more conducive to the injection in hole, is a kind of OLED material of excellent performance.The synthetic route of this material is simple to operation, and reaction yield is higher, can reduce the preparation cost of OLED material, has good industrial prospect.This OLED material can be used in any one deck in hole transmission layer in organic electroluminescent LED, luminescent layer, electron transfer layer, electron injecting layer, or uses in organic electroluminescence device as hotchpotch or the material of main part of luminescent layer.The organic electroluminescent LED that uses this OLED material to prepare, can realize the effect of high brightness, high-level efficiency, low voltage, can effectively avoid screen dim spot, and performance is more excellent.
Embodiment
Below in conjunction with specific embodiment, the present invention is further elaborated, but the present invention is not limited to following examples.Described method is ordinary method if no special instructions.Described starting material all can obtain from open commercial sources if no special instructions.
Following embodiment 3 initial reactant three used (4-bromophenyl) amine is be prepared as follows and obtain:
Step 1: triphenylamine synthetic
In 100mL reaction flask; drop into the aniline of 5g (55mmol), 2-dicyclohexylphosphontetrafluoroborate-2 of the bromobenzene of 21g (121mmol), 250mg (0.275mmol) three (dibenzalacetone) two palladiums, 450mg (1.1mmol) '; 6 '-dimethoxy-biphenyl; 16g (176mmol) sodium tert-butoxide and 50ml toluene; nitrogen protection reflux, reaction 24h.System is to entering to fill in the beaker of 100ml water, and adds the ethyl acetate of 100mL, stirs separatory, and 50mL ethyl acetate extraction 2 times for water, merges organic phase, crosses silicagel column, and sherwood oil/eluent methylene chloride obtains white solid product.Yield: 96%.
Step 2: three (4-bromophenyl) amine synthetic
In 100mL reaction flask, drop into step 1 product triphenylamine and the 25ml DMF of 2.45g (10mmol), stir triphenylamine is dissolved completely, the NBS of 5.9g (33mmol) is dissolved in 10ml DMF in constant pressure funnel, slowly be added drop-wise in system stirred overnight at room temperature.System, to entering to fill in the beaker of 300ml water, fully stirs suction filtration.White powder is with ethyl acetate: ethanol=1:1 recrystallization is to white crystal.Yield: 87.1%.
Following embodiment 4 initial reactant 2 used, 8-dibromo dibenzo [b, d] thiophene is be prepared as follows and obtain:
In 250mL reaction flask, drop into dibenzo [b, d] thiophene and the 150ml chloroform of 18.4 (0.1mol), system is placed in ice-water bath and is cooled to 0 ℃, the Br of 33.6g (0.21mol) 2be dissolved in 50ml chloroform in constant pressure funnel, be slowly added drop-wise in system, dropwise the rear stirred overnight at room temperature that naturally rises to.System adds 20% hypo solution to remove excessive Br 2, suction filtration, 2 bodies of filter cake washing, aqueous sodium carbonate washing 2 times, Gossypol recrystallized from chloroform yield: 43.9%.
The Performance Detection condition of embodiment 5 and 6 obtained device OD-1 to OD-4 is as follows:
Brightness and tristimulus coordinates: use spectrum scanner PhotoResearch PR-715 test;
Current density and a bright voltage: use digital sourcemeter Keithley 2420 tests;
Power efficiency: use NEWPORT 1931-C test.
Embodiment 1,1,3-bis-(9H-dibenzo [a, c] carbazole-9-yl) benzene synthetic
Step 1: compound 2,3-diphenyl indole synthetic
In 500mL reaction flask, drop into 20g(116.3mmol) o-bromoaniline, tolane, the 0.52g(2.3mmol of 24.8g (139.5mmol)) catalyst acetic acid palladium, 1.3g(5.8mmol) and part tri-butyl phosphine; 37.2g (290.3mmol) alkali salt of wormwood and 400ml solvent N-Methyl pyrrolidone (NMP); nitrogen protection is heated to 110 ℃, carries out ring closure reaction 12h.System is to entering to fill in the beaker of 500ml water, and add the ethyl acetate of 200mL, stir separatory, 200mL ethyl acetate extraction 2 times for water, 100mL saturated common salt washing 2 times for organic phase, merges organic phase, crosses silicagel column, sherwood oil/eluent methylene chloride obtains white solid product 2,3-diphenyl indole yield: 80%.
Step 2: compound 9H-dibenzo [a, c] carbazole synthetic
In 500mL reaction flask; drop into 2g (7.4mmol) step 1 product 2,3-diphenyl indole, 1g (29.7mmol) potassium metal bits, 300ml THF nitrogen protection, under room temperature, vigorous stirring is carried out linked reaction; system becomes atropurpureus, adds 10ml by isopyknic THF and H after 24h 2the mixed solution cancellation reaction that O forms, system is become orange by atropurpureus.Decompression is spin-dried for THF, adds the ethyl acetate of 100ml water and 100mL, stirs separatory, and 50mL ethyl acetate extraction 2 times for water, merges organic phase, crosses silicagel column, and sherwood oil/eluent methylene chloride obtains white solid product.Yield: 50%.
1H?NMR(CDCl 3,300MHz)：δ=7.89-7.91(s,1H),8.84-8.88(t,2H),8.77-8.80(d,1H),8.53-8.59(t,2H),7.68-7.78(m,4H),7.55-7.57(t,1H),7.42-7.44(t,1H),7.7.37-7.39(t,1H)。As from the foregoing, this white solid product structure is correct, is 9H-dibenzo [a, c] carbazole
Step 3: compound 1,3-bis-(9H-dibenzo [a, c] carbazole-9-yl) benzene synthetic
In 25mL reaction flask, drop into the m-dibromobenzene of 0.2g (0.8mmol), 0.47g (1.8mmol) step 2) gained 9H-dibenzo [a, c] carbazole, 8.3mg (0.008mmol) catalyzer three (dibenzalacetone) two palladiums, phosphorus part 2-dicyclohexylphosphontetrafluoroborate-2 of 13.1mg (0.032mmol) ', 6 '-dimethoxy-biphenyl, 0.192g (2mmol) alkali sodium tert-butoxide and 3ml solvent xylene, nitrogen protection reflux is reacted after 48h, reaction system is poured in the beaker that fills 50ml water, and add the ethyl acetate of 50mL, stir separatory, 20mL ethyl acetate extraction 2 times for water, merge organic phase, cross silicagel column, sherwood oil/eluent methylene chloride obtains white solid product.Yield: 30%.
Structure and the performance test results of this product are as follows:
（1） 1H?NMR(CDCl 3,300MHz)：δ=7.89-7.91(d,2H),6.82-6.85(d,2H),5.35(b,1H)。As from the foregoing, this white solid product structure is correct, is Compound C JH1,1,3-bis-(9H-dibenzo [a, c] carbazole-9-yl) benzene.
(2) second-order transition temperature Tg:227.62 ℃;
(3) uv-absorbing wavelength: 295nm, 325nm, 338nm;
(4) fluorescent emission wavelength: 418nm.
Embodiment 2, compound 4,4`-bis-(9H-dibenzo [a, c] carbazole-9-yl) biphenyl synthetic
According to the step of embodiment 1, only m-dibromobenzene used in step 3) is replaced with to 4,4`-'-dibromobiphenyl, obtain target compound 4,4`-bis-(9H-dibenzo [a, c] carbazole-9-yl) biphenyl, yield: 25%.
Structure and the performance test results of this product are as follows:
（1） 1H?NMR(CDCl 3,300MHz)：δ=9.13-9.15(d,1H),8.91-9.03(m,6H)，8.69-8.74(d,1H)，6.98-8.04(m,23H)，6.68-6.73(d,1H)。As from the foregoing, this white solid product structure is correct, is Compound C JH11,4,4`-bis-(9H-dibenzo [a, c] carbazole-9-yl) biphenyl.
(2) second-order transition temperature Tg:265.49 ℃;
(3) uv-absorbing wavelength: 295nm, 315nm, 338nm;
(4) fluorescent emission wavelength: 378nm.
Synthesizing of embodiment 3, compound three (4-(9H-dibenzo [a, c] carbazole-9-yl) phenyl) amine
Step 1) and 2) with embodiment 1;
3) in 25mL reaction flask, drop into three (4-bromophenyl) amine of 0.39g (0.8mmol), 9H-dibenzo [a of 0.67g (2.5mmol), c] carbazole, 8.3mg (0.008mmol) three (dibenzalacetone) two palladiums, 2-dicyclohexylphosphontetrafluoroborate-2 of 13.1mg (0.032mmol) ', 6 '-dimethoxy-biphenyl, 0.307g (3.2mmol) sodium tert-butoxide and 3ml dimethylbenzene, nitrogen protection reflux is reacted after 48h, reaction system is poured in the beaker that fills 50ml water, and add the ethyl acetate of 50mL, stir separatory, 20mL ethyl acetate extraction 2 times for water, merge organic phase, cross silicagel column, sherwood oil/eluent methylene chloride obtains white solid product.Yield: 23%.
Structure and the performance test results of this product are as follows:
（1） 1H?NMR(CDCl 3,300MHz)：δ=8.96-8.99(d,3H),8.81-8.85(q,6H),8.69-8.72(q,3H),7.50-7.85(m,24H),7.39-7.49(m,12H)。As from the foregoing, this white solid product structure is correct, is Compound C JH21, three (4-(9H-dibenzo [a, c] carbazole-9-yl) phenyl) amine.
(2) second-order transition temperature Tg: nothing;
(3) uv-absorbing wavelength: 293nm, 328nm, 335nm;
(4) fluorescent emission wavelength: 407nm.
Embodiment 4, compound 2,8-bis-(9H-dibenzo [a, c] carbazole-9-yl) dibenzo [b, d] thiophene synthetic
Step 1) and 2) with embodiment 1;
3) in 25mL reaction flask, drop into 2 of 0.27g (0.8mmol), 8-dibromo dibenzo [b, d] thiophene, 9H-dibenzo [a of 0.47g (1.76mmol), c] carbazole, 8.3mg (0.008mmol) three (dibenzalacetone) two palladiums, 2-dicyclohexylphosphontetrafluoroborate-2 of 13.1mg (0.032mmol) ', 6 '-dimethoxy-biphenyl, 0.2g (2.0mmol) sodium tert-butoxide and 3ml dimethylbenzene, nitrogen protection reflux is reacted after 48h, reaction system is poured in the beaker that fills 50ml water, and add the ethyl acetate of 50mL, stir separatory, 20mL ethyl acetate extraction 2 times for water, merge organic phase, cross silicagel column, sherwood oil/eluent methylene chloride obtains yellow solid product.Yield: 30%.
Structure and the performance test results of this product are as follows:
（1） 1H?NMR(CDCl 3,300MHz)：δ=8.86-8.96(d,2H),8.78-8.84(q,4H),8.68-8.73(d,2H),8.28-8.34(d,2H),8.11-8.14(d,2H),7.68-7.79(m,2H),7.37-7.65(m,12H),7.15-7.28(m,4H)。As from the foregoing, this yellow solid product structure is correct, is Compound C JH41,2,8-bis-(9H-dibenzo [a, c] carbazole-9-yl) dibenzo [b, d] thiophene.
(2) second-order transition temperature Tg:163.82 ℃;
(3) uv-absorbing wavelength: 290nm, 315nm, 325nm;
(4) fluorescent emission wavelength: 414nm.
By above-described embodiment 1～4, can be found out, provided by the invention have a compound shown in formula I, has very high second-order transition temperature, and carrier transport ability and luminous power preferably, therefore in OLED field, has a good application prospect.On the preparation process basis of above-described embodiment, reactant consumption is expanded on year-on-year basis or dwindled, all do not affect the quality of gained OLED material.
Embodiment 5, prepare electroluminescent device OD-1, OD-2
1) by the glass substrate that has been coated with ITO conductive layer supersound process 30 minutes in clean-out system, in deionized water, rinse, in acetone/ethanol mixed solvent ultrasonic 30 minutes, under clean environment, be baked to complete drying, with UV-light cleaning machine, irradiate 10 minutes, and with low energy positively charged ion bundle bombarded surface.
2) the above-mentioned ito glass substrate of handling well is placed in vacuum chamber, is evacuated to 1 * 10 -5～9 * 10 -3pa continues difference evaporation compound N PB as hole transmission layer on above-mentioned anode tunic, and evaporation speed is 0.1nm/s, and evaporation thickness is 10nm;
Wherein, the structural formula of NPB is as follows:
3) on hole transmission layer, continue evaporation one deck by embodiment 1 gained formula I Compound C JH1 and phosphor material the mixture forming is as the organic luminous layer of device, and evaporation speed is 0.1nm/s, and evaporation thickness is 80nm; Wherein, FIrpic is 8% of CJH1 quality;
4) on organic luminous layer, continue evaporation one deck BPhen material as the electron transfer layer of device, evaporation speed is 0.1nm/s, and evaporation thickness is 50nm;
Wherein, the structural formula of BPhen is as follows:
5) on electron transfer layer, evaporation magnesium/ag alloy layer is as the cathode layer of device successively, and wherein the evaporation speed of magnesium/ag alloy layer is 2.0～3.0nm/s, and evaporation thickness is 100nm, and magnesium and silver-colored mass ratio are 1:9, obtain device OD-1 provided by the invention.
According to upper identical step, only step 3) CJH1 used is replaced with to embodiment 2 gained formula I Compound C JH11, obtain device O-2 provided by the invention;
Reference examples 1, fabricate devices OD-3 and OD-4
According to the step of embodiment 5, only step 3) CJH1 used is replaced with to mCP or CBP, obtain device OD-3 and OD-4.
Wherein, the structural formula of mCP and CBP is as follows:
The performance test results of obtained device OD-1 to OD-4 is as shown in table 1.
The performance test results of table 1, OD-1 to OD-4

Claims (9)

1. compound shown in formula I,
In described formula I, R 1be selected from following group a or b:
Any one in the heterocyclic radical of condensed ring aromatic ethylene base, the aryl amine of C2-C60, the condensed ring radical of the nitrogen atom of C2-C60, the condensed ring radical of the sulfur-bearing of C6-C60 or Sauerstoffatom and the nitrogen atom of C2-C60 of the aromatic ethylene base of a, the aromatic base that is selected from C2-C60, C2-C60, the condensed ring aromatic base of C2-C60, C2-C60;
B, contain substituent group a;
R 2be selected from following group c or d:
The condensed ring aromatic ethylene base of the aromatic ethylene base of c, the aromatic base that is selected from hydrogen, halogen, methyl, methoxyl group, C2-C60, C2-C60, the condensed ring aromatic base of C2-C60, C2-C60, the aryl amine of C2-C60, any one in the heterocyclic radical of the phosphorous or silicon of the condensed ring radical of the nitrogen atom of C2-C60, C6-C60 or the condensed ring radical of boron atom and the nitrogen atom of C2-C60;
D, contain substituent group c;
In described group b and group d, substituting group is all selected from least one in aliphatic group, halogen and the cyano group of deuterium, C1-C20;
N is the integer of 1-5.
2. compound according to claim 1, is characterized in that: in described formula I, and R 1and R 2all be selected from any one in following group:
In above-mentioned group, described A, B and C are independently carbon atom or nitrogen-atoms respectively, but A, B and C can not be nitrogen-atoms simultaneously,, represent substituent position;
R 3be selected from the aromatic base of hydrogen, C2-C60, any one in the heterocyclic radical of condensed ring aromatic ethylene base, the aryl amine of C2-C60, the condensed ring radical of the nitrogen atom of C2-C60 and the nitrogen atom of C2-C60 of the condensed ring aromatic base of the aromatic ethylene base of C2-C60, C2-C60, C2-C60;
R 4and R 5all be selected from the aliphatic group of C1-C18, the condensed ring aromatic base of the aromatic base of C2-C60, C2-C60, the aryl amine of C2-C60, be connected with heterocycle C2-C60 aromatic base and be connected with any one in the aromatic base of C2-C60 of alkyl of C1-C18;
R 6be selected from any one in the condensed ring aromatic base of the aliphatic group of C1-C18, the aromatic base of C2-C60 and C2-C60;
R 7be selected from the aliphatic group of hydrogen, C1-C18, the aromatic ethylene base of the aromatic base of C2-C60, C2-C60, any one in the condensed ring aromatic ethylene base of the condensed ring aromatic base of C2-C60 and C2-C60;
D and E independently represent respectively the aromatic base of C2-C60, any one in the heterocyclic radical of condensed ring aromatic ethylene base, the condensed ring radical of C2-C60 and the nitrogen atom of C2-C60 of the condensed ring aromatic base of the aromatic ethylene base of C2-C60, C2-C60, C2-C60;
F and G independently represent respectively carbon atom or nitrogen-atoms.
3. according to the arbitrary described compound of claim 1-2, it is characterized in that: compound shown in described formula I is any one in following compound:
4. a method of preparing compound shown in the arbitrary described formula I of claim 1-3, comprises the steps:
1) will catalyzer, part and alkali mix and carry out ring closure reaction in solvent, react complete and obtain
2) by step 1) gained consider to be worth doing to mix in solvent with potassium and carry out after linked reaction, use the mixed solution cancellation being formed by tetrahydrofuran (THF) and water to react, obtain
3) by step 2) gained mix to reflux with catalyzer, phosphorus part and alkali and react, obtain compound shown in described formula I;
Described step 1)-3) in, the R in each reaction materil structure general formula 1, R 2all identical with claim 1 with the definition of n.
5. method according to claim 4, is characterized in that: in described step 1), catalyzer is palladium or Pd (PPh 3) 4, Pd (PPh 3) 2cl 2or Pd (dba) 2;
Part is tri-butyl phosphine, triphenyl phosphorus or thricyclohexyl phosphorus;
Alkali is salt of wormwood, sodium carbonate, potassium acetate or sodium acetate;
Described the mole dosage that feeds intake of catalyzer, part and alkali is 1.0:1.0-1.5:0.01-0.05:0.02-0.10:2.0-3.0, is specially 1.0:1.2:0.02:0.05:2.5;
In described ring closure reaction, temperature is 100-150 ℃, and the time is 8-16 hour;
Described step 2) in, the mole dosage that feeds intake of considering to be worth doing with potassium is 1.0:1.0-5.0, is specially 1.0:4.0;
In the described mixed solution being comprised of tetrahydrofuran (THF) and water, the volume ratio of tetrahydrofuran (THF) and water is 1.0:1.0;
In described linked reaction step, temperature is room temperature, and the time is 12-48 hour;
In described step 3), catalyzer is three (dibenzalacetone) two palladiums, palladium, Pd (PPh 3) 4or Pd (PPh 3) 2cl 2or Pd (dba) 2;
Phosphorus part be 2-dicyclohexylphosphontetrafluoroborate-2 ', 6 '-dimethoxy-biphenyl, tri-butyl phosphine, triphenyl phosphorus or thricyclohexyl phosphorus;
Alkali is sodium tert-butoxide, potassium tert.-butoxide, sodium hydroxide or potassium hydroxide;
than for 2.0-2.5:1.0:0.005-0.02:0.01-0.05:2.0-3.0, be specially 2.25:1.0:0.01:0.04:2.5 with the mole dosage that feeds intake of catalyzer, phosphorus part and alkali;
In described reactions steps, the time is 24-56 hour;
Described step 1)-3) all in inert atmosphere, carry out; Described inert atmosphere is specially nitrogen or argon gas atmosphere;
Described step 1)-3), in, described solvent is all selected from least one in N-Methyl pyrrolidone, tetrahydrofuran (THF), toluene, DMF and dimethylbenzene.
6. the luminescent material that contains compound shown in the arbitrary described formula I of claim 1-3; Or,
The application of compound in preparing luminescent material shown in the arbitrary described formula I of claim 1-3;
The fluorescent emission wavelength of described luminescent material is specially 370-420nm.
7. the electroluminescent device that contains compound shown in the arbitrary described formula I of claim 1-3;
The application of compound in preparing electroluminescent device shown in the arbitrary described formula I of claim 1-3.
8. device according to claim 7 or application, is characterized in that: in described electroluminescent device, compound shown in formula I is for forming the material of organic luminous layer;
Described electroluminescent device is comprised of transparent substrate, anode, hole transmission layer, organic luminous layer, electron transfer layer and cathode layer from the bottom to top successively;
Wherein, the material that forms described transparent substrate is glass or flexible substrate;
The material that forms described anode layer is inorganic materials or organic conductive polymkeric substance; Wherein, described inorganic materials is tin indium oxide, zinc oxide, stannic oxide, gold and silver or copper; Described organic conductive polymkeric substance is selected from least one in Polythiophene, polyvinylbenzenesulfonic acid sodium and polyaniline;
The material that forms described hole transmission layer is selected from least one in TDATA and NPB;
The structural formula of described NPB is as follows:
The structural formula of described TDATA is as follows:
The material that forms described organic luminous layer for by compound shown in formula I described in claim 1 and the mixture forming; Compound shown in described formula I and mass ratio be 1:0.001-0.2, be specially 1:0.08;
The material that forms described electron transfer layer is Alq3, Gaq3 or BPhen;
Wherein, the structural formula of Alq3, BPhen and Gaq3 is as follows successively:
The material that forms described cathode layer is selected from any one or the alloy of any two kinds of compositions or the fluorochemical of following element in following element: lithium, magnesium, silver, calcium, strontium, aluminium, indium, copper, Jin Heyin.
9. application according to claim 8 or organic electroluminescence device claimed in claim 7, is characterized in that:
The thickness of described hole transmission layer is 5-15nm, is specially 10nm;
The thickness of described organic luminous layer is 10-100nm, is specially 80nm;
The thickness of described electron transfer layer is 40-60nm, is specially 50nm;
The thickness of described cathode layer is 90-110nm, is specially 100nm.
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Application publication date: 20140723