CN104830320B - Phenanthreneopyrazine derivative luminescent material and application thereof in electroluminescent device - Google Patents

Phenanthreneopyrazine derivative luminescent material and application thereof in electroluminescent device Download PDF

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CN104830320B
CN104830320B CN201510267689.9A CN201510267689A CN104830320B CN 104830320 B CN104830320 B CN 104830320B CN 201510267689 A CN201510267689 A CN 201510267689A CN 104830320 B CN104830320 B CN 104830320B
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CN104830320A (en
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王悦
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Jilin Yuanhe Electronic Material Co.,Ltd.
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Jilin University
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Abstract

The invention discloses an organic luminescent material based on a phenanthreneopyrazine derivative and an electroluminescent device thereof, belonging to the technical field of organic electroluminescence. The structural general formula of the luminescent material is shown in the specification, wherein R refers to triphenylamine group or derivatives thereof, diphenylamine group or derivatives thereof, carbazolyl or derivatives thereof, N-phenylcarbazyl or derivatives thereof, phenothiazine or derivatives thereof, or phenoxazine or derivatives thereof. The phenanthreneopyrazine derivative can serve as a luminescent material and is used for preparing a high-performance electroluminescent device. The compound disclosed by the invention has the advantages that the preparation process is simple, and the prepared electroluminescent device is high in efficiency and long in service life, and the like. The device can be applied to the fields of panel display, illumination and light sources.

Description

Phenanthro- pyrazines derivatives luminescent material and its application in terms of electroluminescent device
Technical field
The invention belongs to technical field of organic electroluminescence, and in particular to a class phenanthro- pyrazines derivatives luminescent material and its Application in organic electroluminescence device.
Background technology
Earlier 1960s, Pope et al. report organic electroluminescent phenomenon earliest, and they are in anthracene single crystal two Side apply to observed during the high pressure of four hectovolts blue light that anthracene sends (see M.Pope, H.Kallmann and P.Magnante, J.Chem.Phys.,1963,38,2042).But as monocrystalline is difficult to grow, device drive voltage is very high, what they were adopted Technique almost no practical use.Until 1987, C.W.Tang of U.S.'s Kodak Company et al. adopted ultra-thin membrane technology with sky The preferable aromatic amine of cave laser propagation effect as hole transmission layer, using the aluminum complex of 8-hydroxyquinoline as luminescent layer, to aoxidize Indium stannum (ITO) thin film and metal alloy are prepared for luminescent device respectively as anode and negative electrode.The device is in 10V driving voltages Under obtained brightness and be up to 1000cd/m2Green emission, the efficiency of device is 1.5lm/W (see C.W.Tang and S.A.VanSlyke, Appl.Phys.Lett., 1987,51,913).This breakthrough causes organic electroluminescent research It is worldwide rapid in depth to carry out.
Forrest of Princeton university in 1998 et al. researchs find, using general organic material or using glimmering Organic luminescent device prepared by photoinitiator dye doping techniques, due to the quantum mechanics transition rule constraint by spin conservation, which is maximum Luminous internal quantum efficiency is 25%.They are doped in phosphorescent coloring octaethylporphyrin platinum (PtOEP) in main body luminescent material, system It is standby go out external quantum efficiency be 4%, luminescent device of the internal quantum efficiency up to 23%, so that open the frontier of electrophosphorescence (see M.A.Baldo, D.F.O'Brienetal., Nature, 1998,395,151).But one side phosphor material commonly uses iridium The noble metals such as platinum, expensive, on the other hand for dark blue smooth phosphor material, which there are still chemical instability, device The problems such as efficiency roll-off is larger at higher current densities, thus exploitation it is a kind of using cheap stable organic small molecule material and Can realize that the OLED of high efficiency light-emitting seems particularly important.
Application of the new material in organic electroluminescence device is to promote electroluminescent technology constantly progressive and enter practical The required means in change stage.In recent years, exploitation of the people to new material has put into huge financial resources and energy, a large amount of function admirables Material make organic electroluminescent achieve some breakthroughs (see U.S.Pat.No.5,150,006；5,141,671；5, 073,446；5,061,569；5,059,862；5,059,861；5,047,687；4,950,950；5,104,740；5,227, 252；5,256,945；5,069,975；5,122,711；5,554,450；5,683,823；5,593,788；5,645,948；5, 451,343；5,623,080；5,395,862).
In recent years, with showing huge application prospect, organic electroluminescence in total colouring and solid-state white lighting field Luminescence technology is obtained for extensive research in scientific research circle and industrial circle and pays close attention to.Organic micromolecular photoelectric material is because of its structure Clearly, it is easy to modification, is used for developing as high performance material by substantial amounts of the advantages of purification processing is simple.For at present, pass System luminescent dye molecule often have very high fluorescence quantum yield, but its doping OLED due to be limited to 25% interior amount Sub- efficiency, external quantum efficiency are generally less than 5%, and also there is a big difference with the efficiency of phosphorescent devices.Such as red dye DCM (see C.W.Tang,S.A.VanSlyke,and C.H.Chen,J.Appl.Phys.,1989,65,3610；U.S.Pat.No.5, 908,581), device efficiency<10cd/A；Green glow dyestuff quinacridone is (see U.S.Pat.No.5,227,252；5,593,788； CN1482127A；CN1219778；CN1660844), device efficiency<20cd/A etc..
Can realize that the fluorescence OLED that the internal quantum efficiency for breaking through 25% is limited mainly employs delayed fluorescence machine at present System, the triplet excited state energy in its energy effectively utilizes device.Its mechanism mainly has two classes, and a class is TTA (Triplet- Triplet Annihilation, T-T annihilation) mechanism (see D.Kondakov, T.D.Pawlik, T.K.Hatwar, and J.P.Spindler, J.Appl.Phys., 2009,106,124510).Another kind of is TADF (Thermally Activated Delayed Fluorescence, thermal activation delayed fluorescence) mechanism (see H.Uoyama, K.Goushi, K.Shizu, H.Nomura, C.Adachi, Nature., 2012,492,234).TTA mechanism is using two three The exciton fusion of weight state produces singlet excitons, improves the mechanism that singlet excitons generate ratio, but its device most imperial palace quantum effect Rate only has 40%～62.5%.TADF mechanism is using with poor (the Δ E of less singlet state-triplet energy levelST) organic little point Sub- material, its triplet exciton under environment thermal energy can be converted into singlet state by reverse intersystem crossing (RISC) this process and swash The mechanism of son.Its device internal quantum efficiency can reach 100% in theory.But efficiency roll-off is larger under high illumination for its device, limit Its application in total colouring and white-light illuminating is made.
TADF molecules are entrained in the material of main part of broad stopband mainly as guest materials realizes that efficient thermal activation postpones Fluorescence (see Q.Zhang, J.Li, K.Shizu, S.Huang, S.Hirata, H.Miyazaki, C.Adachi, J.Am.Chem.Soc.2012,134,14706；H.Uoyama,K.Goushi,K.Shizu,H.Nomura,C.Adachi, Nature.,2012,492,234；T.Nishimoto,T.Yasuda,S.Y.Lee,R.Kondo,C.Adachi, Mater.Horiz.,2014,1,264)。
Phenanthro- pyrazine compounds can pass through suzuki reaction or ullmann reaction connects as good electron acceptor core Different donor groups.With a series of organic molecule luminescent material that this has synthesized electron donor-acceptor (EDA) types, material has larger Rigid plane skeleton, good heat stability and higher fluorescence quantum yield, while having the simple yield height of synthesis to carry Pure easy the features such as.
The content of the invention
It is an object of the invention to provide the electroluminescent organic material of series of new phenanthro- pyrazines derivatives and its Prepare the application in electroluminescent device.
Compound formula involved in the present invention is as follows：
Wherein R is triphenylamine base and its derivant, hexichol amido and its derivant, carbazyl and its derivant, N- phenyl Card oxazolyl and its derivant, phenothiazine and its derivant, phenoxazine and its derivant etc..
R group is as follows for Phenotype：
Compound synthesis route involved in the present invention is as follows：
Representative phenanthro- pyrazines derivatives (1-48) that the present invention relates to is as follows：
Description of the drawings
Fig. 1：The overall structure diagram of OLED of the present invention；
Fig. 2：Using non-doping electric electroluminescence device spectrogram prepared by material of the present invention 1；
Fig. 3：Using non-doping electric electroluminescence device spectrogram prepared by material of the present invention 6；
Fig. 4：Using adulterated EL part spectrogram prepared by material of the present invention 1；
Fig. 5：Using adulterated EL part spectrogram prepared by material of the present invention 6.
The structure of electroluminescent device prepared by the present invention is as shown in figure 1, each component names are：Clear glass or other are saturating Bright substrate 1, adheres to ITO (indium tin oxide) anode 2 on a transparent substrate, NPB (N, N'- bis- (1- naphthyls)-N, N'- hexichol Base -1,1'- biphenyl -4,4'- diamidogen) hole transmission layer 3, TCTA (4,4', 4 "-three (9- carbazyls) triphenylamine) hole blocking layer 4, (phenanthro- pyrazines derivatives can directly be prepared into luminescent layer and obtain orange light, HONGGUANG, near for the luminescent layer of material of the present invention 5 Infrared electro electroluminescence device, it is also possible to prepare yellow, orange, red, near infrared light electroluminescent device as doping guest materials；Mix Miscellaneous material of main part is TPBi, the mass concentration of doping is 5～30%), TPBI (three (phenylbenzimidazol) benzene) electronics is passed Defeated layer 6, LiF electron injecting layers 7, metal Al is used as negative electrode 8.
Electroluminescent device of the present invention can be used to prepare lighting source, signal lighties, direction board or flat faced display.
NPB, TCTA and TPBi molecular structural formula is as shown below：
Specific embodiment
Embodiment 1：The synthesis of compound 3,6-DBrDCPP：
By 3,6- dibromo phenanthrenequione (12mmol), diaminomaleonitrile (12mmol), during acetic acid (50mL) adds bottle with two necks, N2 Under protection, in oil bath, 125 DEG C are heated to reflux 8h, and stopped reaction is poured reactant mixture in distilled water into, agitation and filtration, gained Lycoperdon polymorphum Vitt filter cake uses water, washing with alcohol to obtain Lycoperdon polymorphum Vitt powder after drying successively, then separates (silica gel, dichloromethane with column chromatography method Alkane) obtain pale yellow powder shape target product.
Embodiment 2：The synthesis of compound 2,7-DBrDCPP：
By 2,7- dibromo phenanthrenequione (12mmol), diaminomaleonitrile (12mmol), during acetic acid (50mL) adds bottle with two necks, N2 Under protection, in oil bath, 125 DEG C are heated to reflux 8h, and stopped reaction is poured reactant mixture in distilled water into, agitation and filtration, gained Lycoperdon polymorphum Vitt filter cake uses water, washing with alcohol to obtain Lycoperdon polymorphum Vitt powder after drying successively, then separates (silica gel, dichloromethane with column chromatography method Alkane) obtain pale yellow powder shape target product.
Embodiment 3：The synthesis of compound 3,6-DBrDCPPP：
3,6- dibromo phenanthrenequione (12mmol), 4,5- diaminourea, two cyanophenyls of neighbour (12mmol), acetic acid (50mL) are added into twoport In bottle, N2Under protection, in oil bath, 125 DEG C are heated to reflux 8h, and stopped reaction pours reactant mixture in distilled water into, stirred Filter, gained Lycoperdon polymorphum Vitt filter cake use water, washing with alcohol to obtain Lycoperdon polymorphum Vitt powder after drying successively, then separate (silicon with column chromatography method Glue, dichloromethane) obtain pale yellow powder shape target product.
Embodiment 4：The synthesis of compound 2,7-DBrDCPPP：
2,7- dibromo phenanthrenequione (12mmol), 4,5- diaminourea, two cyanophenyls of neighbour (12mmol), acetic acid (50mL) are added into twoport In bottle, N2Under protection, in oil bath, 125 DEG C are heated to reflux 8h, and stopped reaction pours reactant mixture in distilled water into, stirred Filter, gained Lycoperdon polymorphum Vitt filter cake use water, washing with alcohol to obtain Lycoperdon polymorphum Vitt powder after drying successively, then separate (silicon with column chromatography method Glue, dichloromethane) obtain pale yellow powder shape target product.
Embodiment 5：The synthesis of compound 1：
By 3,6-DBrDCPP (0.88g, 2mmol), 4- triphenylamine boric acid (1.27g, 4.4mmol), sodium carbonate (1.70g, 16mmol), tetra-triphenylphosphine palladium (1.16g, 0.1mmol), tetrahydrofuran (40mL) H2During O (10mL) adds there-necked flask, N2Protection Under, in oil bath, 100 DEG C are heated to reflux 12h stopped reaction, and reactant mixture is poured in distilled water, are extracted with dichloromethane, dense Dark red powder shape target product is obtained with column chromatography method separation (silica gel, dichloromethane) after contracting, and (1.22g, yield is 80%).Matter Analysis of spectrum determine molecular ion quality be：766.80 (value of calculation is：766.91)；Theoretical elemental content (%) C54H34N6：C, 84.57；H, 4.47；N, 10.96, actual measurement constituent content (%)：C, 84.49；H, 4.49；N, 10.83.Above-mentioned analysis result table Bright, the product of acquisition is estimated product.
Embodiment 6：The synthesis of compound 2：
According to the synthesis of compound 1, step is identical, replaces compound with compound 4- (9H- carbazole -9- phenyl) phenylboric acid 4- triphenylamine boric acid, obtain red powder compound 2 (1.12g, yield 73%), the molecular ion quality that mass spectral analyses determine For：762.30 (value of calculation is：762.88)；Theoretical elemental content (%) C54H30N6：C,85.02；H,3.96；N,11.02；Actual measurement Constituent content (%)：C,85.12；H,3.88；N,11.13.Above-mentioned analysis result shows that the product of acquisition is estimated product.
Embodiment 7：The synthesis of compound 3：
According to the synthesis of compound 1, step is identical, is replaced with compound 4- (3,6- dimethyl -9H- carbazyls) phenylboric acid Compound 4- triphenylamine boric acid, obtain dark red powder shape compound 3 (1.02g, yield 67%), the molecule that mass spectral analyses determine Mass of ion is：818.32 (value of calculation is：818.98)；Theoretical elemental content (%) C58H38N6：C,85.06；H,4.68；N, 10.26；；Actual measurement constituent content (%)：C,85.15；H,4.75；N,10.36.Above-mentioned analysis result shows that the product of acquisition is Estimated product.
Embodiment 8：The synthesis of compound 4：
According to the synthesis of compound 1, step is identical, with compound 4- (4,4 '-accelerine base) phenylboric acid replacementization Compound 4- triphenylamine boric acid, obtain dark red powder shape compound 4 (1.42g, yield 85%), the molecule that mass spectral analyses determine from Protonatomic mass is：822.35 (value of calculation is：823.02)；Theoretical elemental content (%) C58H42N6：C,84.64；H,5.14；N, 10.21；Actual measurement constituent content (%)：C, 84.75；H, 5.08；N, 10.16.Above-mentioned analysis result shows that the product of acquisition is pre- The product of meter.
Embodiment 9：The synthesis of compound 5：
By 3,6-DBrDCPP (0.88g, 2mmol), diphenylamines (0.74g, 4.4mmol), cesium carbonate (2.68g, 16mmol), three (dibenzalacetone) two palladium (0.10g, 0.1mmol), tri-butyl phosphine (0.20g, 0.1mmol), adjacent diformazan During benzene (80mL) adds there-necked flask, N2Under protection, in oil bath, 130 DEG C are heated to reflux 24h stopped reaction, and reactant mixture is poured into In distilled water, extracted with dichloromethane, (silica gel, dichloromethane) is separated with column chromatography method after concentration and obtain red powder target (0.80g, yield is 65%) for product.Mass spectral analyses determine molecular ion quality be：614.62 (value of calculation is：614.71)；Reason Argument cellulose content (%) C42H26N6：C,82.06；H,4.26；N,13.67；Actual measurement constituent content (%)：C,82.12；H,4.33； N,13.65.Above-mentioned analysis result shows that the product of acquisition is estimated product.
Embodiment 10：The synthesis of compound 6：
According to the synthesis of compound 5, step is identical, replaces compound diphenylamines with compound carbazole, obtains orange red toner (0.92g, 75%), the molecular ion quality that mass spectral analyses determine is yield last shape compound 6：610.95 (value of calculation is： 610.68)；Theoretical elemental content (%) C42H22N6：C,82.61；H,3.63；N,13.76；Actual measurement constituent content (%)：C, 82.56；H,3.45；N,13.64.Above-mentioned analysis result shows that the product of acquisition is estimated product.
Embodiment 11：The synthesis of compound 7：
According to the synthesis of compound 5, step is identical, replaces compound diphenylamines with compound phenoxazine, obtains orange red (1.08g, 84%), the molecular ion quality that mass spectral analyses determine is yield powdered compounds 7：642.19 (value of calculation is： 642.68)；Theoretical elemental content (%) C42H22N6O2：C,78.49；H,3.45；N,13.08；Actual measurement constituent content (%)：C, 78.49；H,3.45；N,13.08.Above-mentioned analysis result shows that the product of acquisition is estimated product.
Embodiment 12：The synthesis of compound 8：
According to the synthesis of compound 5, step is identical, replaces compound diphenylamines with compound phenothiazine, obtains orange powder (0.81g, 80%), the molecular ion quality that mass spectral analyses determine is yield last shape compound 3：674.92 (value of calculation is： 674.80)；Theoretical elemental content (%) C42H22N6S2：C,74.76；H,3.29；N,12.45；Actual measurement constituent content (%)：C, 74.82；H,3.33；N,12.52.Above-mentioned analysis result shows that the product of acquisition is estimated product.
Embodiment 13：The synthesis of compound 9：
According to the synthesis of compound 5, step is identical, with compound 3,6- Dimethylcarbazoles replacement compound diphenylamines, obtains To orange red powdered compounds 9, (1.19g, 88%), the molecular ion quality that mass spectral analyses determine is yield：666.85 (meters Calculation value is：666.79)；Theoretical elemental content (%) C46H30N6：C,82.86；H,4.54；N,12.60；Actual measurement constituent content (%)：C,82.82；H,4.49；N,12.51.Above-mentioned analysis result shows that the product of acquisition is estimated product.
Embodiment 14：The synthesis of compound 10：
According to the synthesis of compound 5, step is identical, and with compound 3,6- di-t-butyls carbazole replaces compound diphenylamines, (1.15g, 69%), the molecular ion quality that mass spectral analyses determine is yield to obtain red powder compound 10：835.34 (meters Calculation value is：835.11)；Theoretical elemental content (%) C58H54N6：C,83.42；H,6.52；N,10.06；Actual measurement constituent content (%)：C,83.52；H,6.45；N,10.12.Above-mentioned analysis result shows that the product of acquisition is estimated product.
Embodiment 15：The synthesis of compound 11：
According to the synthesis of compound 5, step is identical, with compound 4,4 '-dimethylaniline replacement compound diphenylamines, obtains To red powder compound 11, (1.16g, 87%), the molecular ion quality that mass spectral analyses determine is yield：670.75 (calculate It is worth and is：670.82)；Theoretical elemental content (%) C46H34N6：C,82.36；H,5.11；N,12.53；Actual measurement constituent content (%)： C,82.44；H,5.23；N,12.47.Above-mentioned analysis result shows that the product of acquisition is estimated product.
Embodiment 16：The synthesis of compound 12：
According to the synthesis of compound 5, step is identical, and with compound 4,4 '-tri-tert aniline replaces compound diphenylamines, (1.13g, 80%), the molecular ion quality that mass spectral analyses determine is yield to obtain red powder compound 12：839.53 (meters Calculation value is：839.14)；Theoretical elemental content (%) C58H58N6：C,83.02；H,6.97；N,10.02；Actual measurement constituent content (%)：C,83.21；H,6.86；N,10.13.Above-mentioned analysis result shows that the product of acquisition is estimated product.
Embodiment 17：The synthesis of compound 13：
According to the synthesis of compound 1, step is identical, and with compound 2,7-DBrDCPP replaces compound 3,6-DBrDCPP, (1.15g, 75%), the molecular ion quality that mass spectral analyses determine is yield to obtain red powder compound 13：766.82 (meters Calculation value is：766.91)；Theoretical elemental content (%) C52H38N4：C,84.57；H,4.47；N,10.96；Actual measurement constituent content (%)：C,84.46；H,4.36；N,10.91.Above-mentioned analysis result shows that the product of acquisition is estimated product.
Embodiment 18：The synthesis of compound 14：
According to the synthesis of compound 1, step is identical, and with compound 2,7-DBrDCPP replaces compound 3,6-DBrDCPP, Replace compound 4- triphenylamine boric acid with compound 4- (9H- carbazole -9- bases) phenylboric acid, obtain red powder compound 2 (1.12g, 73%), the molecular ion quality that mass spectral analyses determine is yield：762.30 (value of calculation is：762.88)；Theoretical unit Cellulose content (%) C54H30N6：C,85.02；H,3.96；N,11.02；Actual measurement constituent content (%)：C,85.12；H,3.88；N, 11.13.Above-mentioned analysis result shows that the product of acquisition is estimated product.
Embodiment 19：The synthesis of compound 15：
According to the synthesis of compound 5, step is identical, and with compound 2,7-DBrDCPP replaces compound 3,6-DBrDCPP, Replace compound diphenylamines with compound phenoxazine, (0.75g, 59%), mass spectrum divides yield to obtain red powder compound 15 Analysing the molecular ion quality for determining is：642.38 (value of calculation is：642.68)；Theoretical elemental content (%) C42H22N6O2：C, 78.49；H,3.45；N,13.08；Actual measurement constituent content (%)：C,78.43；H,3.38；N,13.14.Above-mentioned analysis result table Bright, the product of acquisition is estimated product.
Embodiment 20：The synthesis of compound 16：
According to the synthesis of compound 1, step is identical, and with compound 2,7-DBrDCPP replaces compound 3,6-DBrDCPP, Replace compound 4- triphenylamine boric acid with compound 4- (4,4 '-accelerine base) phenylboric acid, obtain dark red powder shape (1.42g, 85%), the molecular ion quality that mass spectral analyses determine is yield compound 4：822.35 (value of calculation is：823.02)；Reason Argument cellulose content (%) C58H42N6：C,84.64；H,5.14；N,10.21；Actual measurement constituent content (%)：C, 84.75；H, 5.08； N, 10.16.Above-mentioned analysis result shows that the product of acquisition is estimated product.
Embodiment 21：The synthesis of compound 17：
According to the synthesis of compound 1, step is identical, and with compound 2,7-DBrDCPP replaces compound 3,6-DBrDCPP, Replace compound 4- triphenylamine boric acid with compound 4- (3,6- dimethyl -9H- carbazyls) phenylboric acid, obtain dark red powder shape (1.02g, 67%), the molecular ion quality that mass spectral analyses determine is yield compound 3：818.32 (value of calculation is：818.98)； Theoretical elemental content (%) C58H38N6：C,85.06；H,4.68；N,10.26；；Actual measurement constituent content (%)：C,85.15；H, 4.75；N,10.36.Above-mentioned analysis result shows that the product of acquisition is estimated product.
Embodiment 22：The synthesis of compound 18：
According to the synthesis of compound 5, step is identical, and with compound 2,7-DBrDCPP replaces compound 3,6-DBrDCPP, Replace compound diphenylamines with compound phenothiazine, (0.81g, 80%), mass spectrum divides yield to obtain orange powder shape compound 18 Analysing the molecular ion quality for determining is：674.92 (value of calculation is：674.80)；Theoretical elemental content (%) C42H22N6S2：C, 74.76；H,3.29；N,12.45；Actual measurement constituent content (%)：C,74.82；H,3.33；N,12.52.Above-mentioned analysis result table Bright, the product of acquisition is estimated product.
Embodiment 23：The synthesis of compound 19：
According to the synthesis of compound 5, step is identical, and with compound 2,7-DBrDCPP replaces compound 3,6-DBrDCPP, (0.97g, 65%), the molecular ion quality that mass spectral analyses determine is yield to obtain red powder compound 19：614.62 (meters Calculation value is：614.71)；Theoretical elemental content (%) C42H26N6：C,82.06；H,4.26；N,13.67；Actual measurement constituent content (%)：C,82.12；H,4.33；N,13.65.Above-mentioned analysis result shows that the product of acquisition is estimated product.
Embodiment 24：The synthesis of compound 20：
According to the synthesis of compound 5, step is identical, and with compound 2,7-DBrDCPP replaces compound 3,6-DBrDCPP, With compound 4,4 '-dimethylaniline replacement compound diphenylamines, red powder compound 20 (1.16g, yield is obtained 87%), the molecular ion quality of mass spectral analyses determination is：670.75 (value of calculation is：670.82)；Theoretical elemental content (%) C46H34N6：C,82.36；H,5.11；N,12.53；Actual measurement constituent content (%)：C,82.44；H,5.23；N,12.47.Above-mentioned point Analysis result shows that the product of acquisition is estimated product.
Embodiment 25：The synthesis of compound 21：
According to the synthesis of compound 5, step is identical, and with compound 2,7-DBrDCPP replaces compound 3,6-DBrDCPP, With compound 4,4 '-tri-tert aniline replacement compound diphenylamines, red powder compound 21 (1.13g, yield is obtained 80%), the molecular ion quality of mass spectral analyses determination is：839.53 (value of calculation is：839.14)；Theoretical elemental content (%) C58H58N6：C,83.02；H,6.97；N,10.02；Actual measurement constituent content (%)：C,83.21；H,6.86；N,10.13.Above-mentioned point Analysis result shows that the product of acquisition is estimated product.
Embodiment 26：The synthesis of compound 22：
According to the synthesis of compound 5, step is identical, and with compound 2,7-DBrDCPP replaces compound 3,6-DBrDCPP, Replace compound diphenylamines with compound carbazole, (0.92g, 75%), mass spectrum divides yield to obtain orange red powdered compounds 22 Analysing the molecular ion quality for determining is：610.95 (value of calculation is：610.68)；Theoretical elemental content (%) C42H22N6：C, 82.61；H,3.63；N,13.76；Actual measurement constituent content (%)：C,82.56；H,3.45；N,13.64.Above-mentioned analysis result table Bright, the product of acquisition is estimated product.
Embodiment 27：The synthesis of compound 23：
According to the synthesis of compound 5, step is identical, and with compound 2,7-DBrDCPP replaces compound 3,6-DBrDCPP, With compound 3,6- Dimethylcarbazoles replacement compound diphenylamines, orange red powdered compounds 23 (1.19g, yield is obtained 88%), the molecular ion quality of mass spectral analyses determination is：666.85 (value of calculation is：666.79)；Theoretical elemental content (%) C46H30N6：C,82.86；H,4.54；N,12.60；Actual measurement constituent content (%)：C,82.82；H,4.49；N,12.51.Above-mentioned point Analysis result shows that the product of acquisition is estimated product.
Embodiment 28：The synthesis of compound 24：
According to the synthesis of compound 5, step is identical, and with compound 2,7-DBrDCPP replaces compound 3,6-DBrDCPP, With compound 3,6- di-t-butyls carbazole replacement compound diphenylamines, red powder compound 24 (1.15g, yield is obtained 69%), the molecular ion quality of mass spectral analyses determination is：835.34 (value of calculation is：835.11)；Theoretical elemental content (%) C58H54N6：C,83.42；H,6.52；N,10.06；Actual measurement constituent content (%)：C,83.52；H,6.45；N,10.12.Above-mentioned point Analysis result shows that the product of acquisition is estimated product.
Embodiment 29：The synthesis of compound 25：
According to the synthesis of compound 1, step is identical, and with compound 3,6-DBrDCPPP replaces compound 3,6-DBrDCPP, (1.20g, 74%), the molecular ion quality that mass spectral analyses determine is yield to obtain dark red powder shape compound 25：817.07 (value of calculation is：816.97)；Theoretical elemental content (%) C51H36N4：C,85.27；H,4.44；N,10.29；Actual measurement constituent content (%)：C,85.23；H,4.38；N,10.25.Above-mentioned analysis result shows that the product of acquisition is estimated product.
Embodiment 30：The synthesis of compound 26：
According to the synthesis of compound 1, step is identical, and with compound 3,6-DBrDCPPP replaces compound 3,6-DBrDCPP, Replace compound 4- triphenylamine boric acid with compound 4- (9H- carbazole -9- bases) phenylboric acid, obtain dark red powder shape compound 26 (1.20g, 75%), the molecular ion quality that mass spectral analyses determine is yield：812.88 (value of calculation is：812.94)；Theoretical unit Cellulose content (%) C58H32N6：C,85.69；H,3.97；N,10.34；Actual measurement constituent content (%)：C, 85.63；H, 4.01；N, 10.38.Above-mentioned analysis result shows that the product of acquisition is estimated product.
Embodiment 31：The synthesis of compound 27：
According to the synthesis of compound 1, step is identical, and with compound 3,6-DBrDCPPP replaces compound 3,6-DBrDCPP, Replace compound 4- triphenylamine boric acid with compound 4- (4,4 '-accelerine base) phenylboric acid, obtain dark red powder shape (1.18g, 72%), the molecular ion quality that mass spectral analyses determine is yield compound 27：872.36 (value of calculation is：873.08)； Theoretical elemental content (%) C62H44N6：C,85.29；H,5.08；N,9.63；Actual measurement constituent content (%)：C,85.32；H,5.12； N,9.55.Above-mentioned analysis result shows that the product of acquisition is estimated product.
Embodiment 32：The synthesis of compound 28：
According to the synthesis of compound 1, step is identical, and with compound 3,6-DBrDCPPP replaces compound 3,6-DBrDCPP, Replace compound 4- triphenylamine boric acid with compound 4- (3,6- dimethyl -9H- carbazyls) phenylboric acid, obtain dark red powder shape (1.15g, 70%), the molecular ion quality that mass spectral analyses determine is yield compound 28：868.33 (value of calculation is： 869.04)；Theoretical elemental content (%) C62H40N6：C,85.69；H,4.64；N,9.67；Actual measurement constituent content (%)：C, 85.56；H,4.56；N,9.58.Above-mentioned analysis result shows that the product of acquisition is estimated product.
Embodiment 33：The synthesis of compound 29：
According to the synthesis of compound 5, step is identical, and with compound 3,6-DBrDCPPP replaces compound 3,6-DBrDCPP, (1.11g, 82%), the molecular ion quality that mass spectral analyses determine is yield to obtain red powder compound 29：664.85 (meters Calculation value is：664.77)；Theoretical elemental content (%) C46H28N6：C,83.11；H,4.25；N,12.64；Actual measurement constituent content (%)：C,83.20；H,4.32；N,12.70.Above-mentioned analysis result shows that the product of acquisition is estimated product.
Embodiment 34：The synthesis of compound 30：
According to the synthesis of compound 5, step is identical, and with compound 3,6-DBrDCPPP replaces compound 3,6-DBrDCPP, Replace compound diphenylamines with compound carbazole, (1.10g, 80%), mass spectrum divides yield to obtain orange red powdered compounds 30 Analysing the molecular ion quality for determining is：660.34 (value of calculation is：660.74)；Theoretical elemental content (%) C46H24N6：C, 83.62；H,3.66；N,12.72；Actual measurement constituent content (%)：C,83.58；H,3.63；N,12.68.Above-mentioned analysis result table Bright, the product of acquisition is estimated product.
Embodiment 35：The synthesis of compound 31：
According to the synthesis of compound 5, step is identical, and with compound 3,6-DBrDCPPP replaces compound 3,6-DBrDCPP, Replace compound diphenylamines with compound phenoxazine, obtain orange red powdered compounds 31 (1.20g, yield 85%), mass spectrum Analyzing the molecular ion quality for determining is：692.53 (value of calculation is：692.74)；Theoretical elemental content (%) C46H24N6O2：C, 79.76；H,3.49；N,12.13；Actual measurement constituent content (%)：C,79.76；H,3.49；N,12.13.Above-mentioned analysis result table Bright, the product of acquisition is estimated product.
Embodiment 36：The synthesis of compound 32：
According to the synthesis of compound 5, step is identical, and with compound 3,6-DBrDCPPP replaces compound 3,6-DBrDCPP, Replace compound diphenylamines with compound phenothiazine, obtain orange red powdered compounds 32 (1.11g, yield 79%), mass spectrum Analyzing the molecular ion quality for determining is：724.66 (value of calculation is：724.86)；Theoretical elemental content (%) C46H24N6S2：C, 76.22；H,3.34；N,11.59；Actual measurement constituent content (%)：C,76.18；H,3.31；N,11.55.Above-mentioned analysis result table Bright, the product of acquisition is estimated product.
Embodiment 37：The synthesis of compound 33：
According to the synthesis of compound 5, step is identical, and with compound 3,6-DBrDCPPP replaces compound 3,6-DBrDCPP, With compound 4,4 '-dimethylaniline replacement compound diphenylamines, red powder compound 33 (1.15g, yield is obtained 80%), the molecular ion quality of mass spectral analyses determination is：720.62 (value of calculation is：720.88)；Theoretical elemental content (%) C50H36N6：C,83.31；H,5.03；N,11.66；Actual measurement constituent content (%)：C,83.25；H,5.11；N,11.62.Above-mentioned point Analysis result shows that the product of acquisition is estimated product.
Embodiment 38：The synthesis of compound 34：
According to the synthesis of compound 5, step is identical, and with compound 3,6-DBrDCPPP replaces compound 3,6-DBrDCPP, With compound 3,6- Dimethylcarbazoles replacement compound diphenylamines, orange red powdered compounds 34 (1.12g, yield is obtained 78%), the molecular ion quality of mass spectral analyses determination is：716.76 (value of calculation is：716.85)；Theoretical elemental content (%) C50H36N6：C,83.31；H,5.03；N,11.66；Actual measurement constituent content (%)：C,83.22；H,5.11；N,11.62.Above-mentioned point Analysis result shows that the product of acquisition is estimated product.
Embodiment 39：The synthesis of compound 35：
According to the synthesis of compound 5, step is identical, and with compound 3,6-DBrDCPPP replaces compound 3,6-DBrDCPP, With compound 3,6- di-t-butyls carbazole replacement compound diphenylamines, red powder compound 35 (1.15g, yield is obtained 72%), the molecular ion quality of mass spectral analyses determination is：885.32 (value of calculation is：885.17)；Theoretical elemental content (%) C62H56N6：C,84.13；H,6.38；N,9.49；Actual measurement constituent content (%)：C,84.13；H,6.38；N,9.49.Above-mentioned analysis As a result show, the product of acquisition is estimated product.
Embodiment 40：The synthesis of compound 36：
According to the synthesis of compound 5, step is identical, and with compound 3,6-DBrDCPPP replaces compound 3,6-DBrDCPP, With compound 4,4 '-tri-tert aniline replacement compound diphenylamines, red powder compound 36 (1.13g, yield is obtained 70%), the molecular ion quality of mass spectral analyses determination is：889.40 (value of calculation is：889.20)；Theoretical elemental content (%) C62H60N6：C,83.75；H,6.80；N,9.45；Actual measurement constituent content (%)：C,83.69；H,6.77；N,9.42.Above-mentioned analysis As a result show, the product of acquisition is estimated product.
Embodiment 41：The synthesis of compound 37：
According to the synthesis of compound 1, step is identical, and with compound 2,7-DBrDCPPP replaces compound 3,6-DBrDCPP, (1.08g, 75%), the molecular ion quality that mass spectral analyses determine is yield to obtain dark red powder shape compound 37：816.73 (value of calculation is：816.97)；Theoretical elemental content (%) C58H36N6：C,85.27；H,4.44；N,10.29；Actual measurement constituent content (%)：C,85.32；H,4.40；N,10.34.Above-mentioned analysis result shows that the product of acquisition is estimated product.
Embodiment 42：The synthesis of compound 38：
According to the synthesis of compound 1, step is identical, and with compound 2,7-DBrDCPPP replaces compound 3,6-DBrDCPP, Replace compound 4- triphenylamine boric acid with compound 4- (9H- carbazole -9- bases) phenylboric acid, obtain dark red powder shape compound 38 (1.20g, 75%), the molecular ion quality that mass spectral analyses determine is yield：812.88 (value of calculation is：812.94)；Theoretical unit Cellulose content (%) C58H32N6：C,85.69；H,3.97；N,10.34；Actual measurement constituent content (%)：C, 85.63；H, 4.01；N, 10.38.Above-mentioned analysis result shows that the product of acquisition is estimated product.
Embodiment 43：The synthesis of compound 39：
According to the synthesis of compound 5, step is identical, and with compound 2,7-DBrDCPPP replaces compound 3,6-DBrDCPP, Replace compound diphenylamines with compound phenoxazine, obtain orange red powdered compounds 39 (1.20g, yield 85%), mass spectrum Analyzing the molecular ion quality for determining is：692.53 (value of calculation is：692.74)；Theoretical elemental content (%) C46H24N6O2：C, 79.76；H,3.49；N,12.13；Actual measurement constituent content (%)：C,79.76；H,3.49；N,12.13.Above-mentioned analysis result table Bright, the product of acquisition is estimated product.
Embodiment 44：The synthesis of compound 40：
According to the synthesis of compound 1, step is identical, and with compound 2,7-DBrDCPPP replaces compound 3,6-DBrDCPP, Replace compound 4- triphenylamine boric acid with compound 4- (4,4 '-accelerine base) phenylboric acid, obtain dark red powder shape (1.18g, 72%), the molecular ion quality that mass spectral analyses determine is yield compound 27：872.36 (value of calculation is：873.08)； Theoretical elemental content (%) C62H44N6：C,85.29；H,5.08；N,9.63；Actual measurement constituent content (%)：C,85.32；H,5.12； N,9.55.Above-mentioned analysis result shows that the product of acquisition is estimated product.
Embodiment 45：The synthesis of compound 41：
According to the synthesis of compound 1, step is identical, and with compound 2,7-DBrDCPPP replaces compound 3,6-DBrDCPP, Replace compound 4- triphenylamine boric acid with compound 4- (3,6- dimethyl -9H- carbazyls) phenylboric acid, obtain dark red powder shape (1.15g, 70%), the molecular ion quality that mass spectral analyses determine is yield compound 28：868.33 (value of calculation is： 869.04)；Theoretical elemental content (%) C62H40N6：C,85.69；H,4.64；N,9.67；Actual measurement constituent content (%)：C, 85.56；H,4.56；N,9.58.Above-mentioned analysis result shows that the product of acquisition is estimated product.
Embodiment 44：The synthesis of compound 42：
According to the synthesis of compound 5, step is identical, and with compound 2,7-DBrDCPPP replaces compound 3,6-DBrDCPP, Replace compound diphenylamines with compound phenothiazine, obtain orange red powdered compounds 42 (1.11g, yield 79%), mass spectrum Analyzing the molecular ion quality for determining is：724.66 (value of calculation is：724.86)；Theoretical elemental content (%) C46H24N6S2：C, 76.22；H,3.34；N,11.59；Actual measurement constituent content (%)：C,76.18；H,3.31；N,11.55.Above-mentioned analysis result table Bright, the product of acquisition is estimated product.
Embodiment 47：The synthesis of compound 43：
According to the synthesis of compound 5, step is identical, and with compound 2,7-DBrDCPPP replaces compound 3,6-DBrDCPP, (1.11g, 82%), the molecular ion quality that mass spectral analyses determine is yield to obtain red powder compound 43：664.85 (meters Calculation value is：664.77)；Theoretical elemental content (%) C46H28N6：C,83.11；H,4.25；N,12.64；Actual measurement constituent content (%)：C,83.20；H,4.32；N,12.70.Above-mentioned analysis result shows that the product of acquisition is estimated product.
Embodiment 48：The synthesis of compound 44：
According to the synthesis of compound 5, step is identical, and with compound 2,7-DBrDCPPP replaces compound 3,6-DBrDCPP, With compound 4,4 '-dimethylaniline replacement compound diphenylamines, red powder compound 44 (1.15g, yield is obtained 80%), the molecular ion quality of mass spectral analyses determination is：720.62 (value of calculation is：720.88)；Theoretical elemental content (%) C50H36N6：C,83.31；H,5.03；N,11.66；Actual measurement constituent content (%)：C,83.25；H,5.11；N,11.62.Above-mentioned point Analysis result shows that the product of acquisition is estimated product.
Embodiment 49：The synthesis of compound 45：
According to the synthesis of compound 5, step is identical, and with compound 2,7-DBrDCPPP replaces compound 3,6-DBrDCPP, With compound 4,4 '-tri-tert aniline replacement compound diphenylamines, red powder compound 45 (1.13g, yield is obtained 70%), the molecular ion quality of mass spectral analyses determination is：889.40 (value of calculation is：889.20)；Theoretical elemental content (%) C62H60N6：C,83.75；H,6.80；N,9.45；Actual measurement constituent content (%)：C,83.69；H,6.77；N,9.42.Above-mentioned analysis As a result show, the product of acquisition is estimated product.
Embodiment 50：The synthesis of compound 46：
According to the synthesis of compound 5, step is identical, and with compound 2,7-DBrDCPPP replaces compound 3,6-DBrDCPP, Replace compound diphenylamines with compound carbazole, (1.10g, 80%), mass spectrum divides yield to obtain orange red powdered compounds 46 Analysing the molecular ion quality for determining is：660.34 (value of calculation is：660.74)；Theoretical elemental content (%) C46H24N6：C, 83.62；H,3.66；N,12.72；Actual measurement constituent content (%)：C,83.58；H,3.63；N,12.68.Above-mentioned analysis result table Bright, the product of acquisition is estimated product.
Embodiment 51：The synthesis of compound 47：
According to the synthesis of compound 5, the identical use compound 2 of step, 7-DBrDCPPP replace compound 3,6-DBrDCPP, With compound 3,6- Dimethylcarbazoles replacement compound diphenylamines, orange red powdered compounds 47 (1.12g, yield is obtained 78%), the molecular ion quality of mass spectral analyses determination is：716.76 (value of calculation is：716.85)；Theoretical elemental content (%) C50H36N6：C,83.31；H,5.03；N,11.66；Actual measurement constituent content (%)：C,83.22；H,5.11；N,11.62.Above-mentioned point Analysis result shows that the product of acquisition is estimated product.
Embodiment 52：The synthesis of compound 48：
According to the synthesis of compound 5, step is identical, and with compound 2,7-DBrDCPPP replaces compound 3,6-DBrDCPP, With compound 3,6- di-t-butyls carbazole replacement compound diphenylamines, red powder compound 48 (1.15g, yield is obtained 72%), the molecular ion quality of mass spectral analyses determination is：885.32 (value of calculation is：885.17)；Theoretical elemental content (%) C62H56N6：C,84.13；H,6.38；N,9.49；Actual measurement constituent content (%)：C,84.13；H,6.38；N,9.49.Above-mentioned analysis As a result show, the product of acquisition is estimated product.
Embodiment 53：Luminescent device [ITO/NPB/TCTA/ compound 1/TPBI/LiF/Al]
It is deposited with hole transmission layer NPB (thickness is 80nm), hole blocking layer in the glass substrate for be coated with ito anode successively TCTA (thickness is 10nm), the compound 1 (20nm) that luminescent layer is prepared for embodiment 3, electron transfer layer TPBI (30nm), electronics Injection material LiFAl negative electrodesDuring evaporation, keep pressure to be 5 × 10-6Pa.The device cut-in voltage 4.0V, maximum current efficiency 0.24cd/A, power efficiency 0.19lm/W.The device sends out near infrared light, and peak position 710nm is most light Degree 590cd/m2。
Embodiment 54：Luminescent device [ITO/NPB/TCTA/ compound 6/TPBI/LiF/Al]
It is deposited with hole transmission layer NPB (thickness is 60nm), hole blocking layer in the glass substrate for be coated with ito anode successively TCTA (thickness is 10nm), the compound 6 (20nm) that luminescent layer is prepared for embodiment 10, electron transfer layer TPBI (30nm), electricity Sub- injection material LiFAl negative electrodesDuring evaporation, keep pressure to be 5 × 10-6Pa.The device opens electricity Pressure 3.0V, maximum current efficiency 3.80cd/A, power efficiency 4.48lm/W.The device glows, peak position 620nm, high-high brightness 7680cd/m2。
Embodiment 55：Luminescent device [ITO/NPB/TCTA/ compound 25/TPBI/LiF/Al]
It is deposited with hole transmission layer NPB (thickness is 80nm), hole blocking layer in the glass substrate for be coated with ito anode successively TCTA (thickness is 10nm), the compound 25 (20nm) that luminescent layer is prepared for embodiment 29, electron transfer layer TPBI (30nm), electricity Sub- injection material LiFAl negative electrodesDuring evaporation, keep pressure to be 5 × 10-6Pa.The device opens electricity Pressure 4.2V, maximum current efficiency 0.18cd/A, power efficiency 0.16lm/W.The device sends out near infrared light, and peak position 730nm is maximum Brightness 680cd/m2。
Embodiment 56：Luminescent device [ITO/NPB/TCTA/TPBi:1 (20%)/TPBI/LiF/Al of compound]
It is deposited with hole transmission layer NPB (thickness is 60nm), hole blocking layer in the glass substrate for be coated with ito anode successively TCTA (thickness is 10nm), luminescent layer are that compound 1 prepared by embodiment 5 is doped in TPBi with 20% mass concentration (20nm), electron transfer layer TPBI (30nm), electron injection material LiFAl negative electrodesLuminescent layer doping is dense Spend for weight percentage.During evaporation, keep pressure to be 5 × 10-6Pa.Device cut-in voltage 3.1V, maximum current effect Rate 5.0cd/A, power efficiency 5.0lm/W.The device sends out light dark red, peak position 668nm, high-high brightness 3805cd/m2。
Embodiment 57：Luminescent device [ITO/NPB/TCTA/TPBi:6 (20%)/TPBI/LiF/Al of compound]
It is deposited with hole transmission layer NPB (thickness is 60nm), hole blocking layer in the glass substrate for be coated with ito anode successively TCTA (thickness is 10nm), luminescent layer are that compound 25 prepared by embodiment 10 is doped in TPBi with 20% mass concentration (20nm), electron transfer layer TPBI (30nm), electron injection material LiFAl negative electrodesLuminescent layer doping content For weight percentage.During evaporation, keep pressure to be 5 × 10-6Pa.Device cut-in voltage 3.6V, maximum current efficiency 40.5cd/A, power efficiency 38.6lm/W.The device Yellow light-emitting low temperature, peak position 560nm, high-high brightness 10610cd/m2。
Embodiment 58：Luminescent device [ITO/NPB/TCTA/TPBi:25 (20%)/TPBI/LiF/Al of compound]
It is deposited with hole transmission layer NPB (thickness is 60nm), hole blocking layer in the glass substrate for be coated with ito anode successively TCTA (thickness is 10nm), luminescent layer are that compound 25 prepared by embodiment 29 is doped in TPBi with 20% mass concentration (20nm), electron transfer layer TPBI (30nm), electron injection material LiFAl negative electrodesLuminescent layer doping content For weight percentage.During evaporation, keep pressure to be 5 × 10-6Pa.Device cut-in voltage 3.4V, maximum current efficiency 3.7cd/A, power efficiency 2.8lm/W.The device sends out light dark red, peak position 680nm, high-high brightness 1805cd/m2。

Claims (5)

1. a kind of phenanthro- pyrazines derivatives luminescent material, it is characterised in that：Shown in its structural formula is one of following,
Wherein, R group structure it is one of following shown in,
2. a kind of phenanthro- pyrazines derivatives luminescent material, it is characterised in that：Shown in its structural formula is one of following,
3. application of the phenanthro- pyrazines derivatives luminescent material described in claim 1 or 2 in organic electroluminescence device.
4. application of the phenanthro- pyrazines derivatives luminescent material as claimed in claim 3 in organic electroluminescence device, which is special Levy and be：Organic electroluminescence device carries one or more luminescent layers, and in luminescent layer, at least one or more right will Seek the phenanthro- pyrazines derivatives luminescent material described in 1 or 2.
5. application of the phenanthro- pyrazines derivatives luminescent material as claimed in claim 4 in organic electroluminescence device, which is special Levy and be：Organic electroluminescence device is used for preparing flat faced display or light source.
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