CN105237520B - A kind of compound-material containing pyrazoline structure and its application - Google Patents

A kind of compound-material containing pyrazoline structure and its application Download PDF

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CN105237520B
CN105237520B CN201510753518.7A CN201510753518A CN105237520B CN 105237520 B CN105237520 B CN 105237520B CN 201510753518 A CN201510753518 A CN 201510753518A CN 105237520 B CN105237520 B CN 105237520B
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fluorenes
amine
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CN105237520A (en
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李崇
张兆超
王立春
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Jiangsu Sunera Technology Co Ltd
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Jiangsu Sanyue Optoelectronic Technology Co Ltd
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    • H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
    • H10K85/633—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
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Abstract

The invention provides a kind of compound-material containing pyrazoline structure and its application.Compound of the invention containing pyrazoline structure has higher glass transition temperature and molecule heat endurance, easily form good amorphous thin film, efficiency and life-span can be improved, so that the driving life-span of device obtains larger lifting, and prepare easily, cost is relatively low, can be applied well in electroluminescent device technical field.

Description

A kind of compound-material containing pyrazoline structure and its application
Technical field
The present invention relates to organic photoelectrical material technical field, more particularly, to skeleton centered on a kind of structure by pyrazoline Compound-material and its application for injecting/transmitting layer material or CPL layer materials as hole in OLED.
Background technology
The correlative study of organic electroluminescence device is initiated at the sixties in 19th century, until the end of the eighties OLED just vigorously send out Exhibition is got up.There is OLED all solid state, low-voltage driving, active to light, response quickly, wide viewing angle, light-emitting area are big, emission wavelength covers Cover whole visible region and it is rich in color the advantages that, realizing that panchromatic large-area displays field has very big advantage, turning into The flat-panel display device of great prospect.The luminosity of organic electroluminescence device is proportional to the concentration and exciton of hole and electronics The probability of recombination product, it is desirable to obtain higher luminous efficiency, not only need hole and electronics can be efficiently injected into, transmit and It is compound and require that hole and electron injection reach balance.Therefore, in organic electroluminescence device, between organic layer and organic layer Matched with the energy band of two electrodes extremely important to device recombination luminescence.
In order to optimize the properties with balancing device, people introduce the functional layer of a variety of not same-actions, such as hole Implanted layer, hole blocking layer etc..The effect that hole injection layer is added between ito anode and hole transmission layer is mainly manifested in drop Low interface potential barrier, the Adhering capacity for increasing hole transmission layer and ITO electrode, improve its stability and balance electronic and hole note Enter etc..
Electron transport material and hole-injecting material or hole mobile material be stop OLED technology comprehensively it is practical compared with Big obstacle, it directly limit the luminous efficiency of device and service life and operating voltage etc..At present except triarylamine derivative or Beyond carbazole derivates, it can be used as hole injection predominantly six azepine Sanya benzene derivatives, especially cyano group substituent (HAT- CN, WO 01/049806), but its service life, efficiency and operating voltage etc. also need to improve always.
Therefore, it is vital that efficient and the long-life hole-injecting material is found in organic electroluminescence device.
The content of the invention
In view of the above-mentioned problems existing in the prior art, the applicant provides a kind of compound material containing pyrazoline structure Material and its application.Compound of the invention containing pyrazoline structure has higher glass transition temperature and molecule heat endurance, holds Good amorphous thin film is easily formed, efficiency and life-span can be improved so that the driving life-span of device obtains larger lifting, and makes Standby easy, cost is relatively low, can be applied well in electroluminescent device technical field.
Technical scheme is as follows：
A kind of compound-material containing pyrazoline structure, compound skeleton centered on pyrazoline, its molecular structure Formula such as formula (1) shown in：
In formula (1), R1、R2Respectively hydrogen or phenyl；R1、R2Can be with identical or different；
In formula (1), R3Represented using formula (2)：
Ar1—R
Formula (2)
In formula (2), Ar1Pass through C-C key connections, Ar with formula (1)1Represent benzene, biphenyl, naphthalene, 1- phenylnaphthalenes, 9,9- bis- Methyl fluorenes；
In formula (2), R be dibenzofurans, benzo aphthofurans, N- phenyl carbazoles, the fluorenes of spiral shell two, phenanthrene, dibiphenylyl amine, 9,9- dimethyl fluorenes-xenylamine or phenyl-terphenyl amine；
In formula (2), the preferred dibenzofurans of R, benzo [b] naphtho- [1,2-d] furans, N- phenyl carbazoles, 9,9 ' spiral shells two Fluorenes, phenanthrene, two (4- xenylamines), N- [1,1'- biphenyl -4- bases] -9,9- dimethyl -9H- fluorenes -2- amine or N- phenyl-[1,1': 4', 1 "-terphenyl] -4- amine.
Another formula of the compound structure is formula (3)：
In formula (3), R1、R2Respectively hydrogen or phenyl；R1、R2Can be with identical or different；R is dibenzofurans, benzo Aphthofurans, N- phenyl carbazoles, the fluorenes of spiral shell two, phenanthrene, dibiphenylyl amine, 9,9- dimethyl fluorenes-xenylamine or phenyl-terphenyl Amine；The preferred dibenzofurans of R, benzo [b] naphtho- [1,2-d] furans, N- phenyl carbazoles, 9,9 ' fluorenes of spiral shell two, phenanthrene, two (4- biphenyl Base amine), N- [1,1'- biphenyl -4- bases] -9,9- dimethyl -9H- fluorenes -2- amine or N- phenyl-[1,1':4', 1 "-terphenyl] -4- Amine.
Another formula of the compound structure is formula (4)：
In formula (4), R1、R2Respectively hydrogen or phenyl；R1、R2Can be with identical or different；R is dibenzofurans, benzo Aphthofurans, N- phenyl carbazoles, the fluorenes of spiral shell two, phenanthrene, dibiphenylyl amine, 9,9- dimethyl fluorenes-xenylamine or phenyl-terphenyl Amine；The preferred dibenzofurans of R, benzo [b] naphtho- [1,2-d] furans, N- phenyl carbazoles, 9,9 ' fluorenes of spiral shell two, phenanthrene, two (4- biphenyl Base amine), N- [1,1'- biphenyl -4- bases] -9,9- dimethyl -9H- fluorenes -2- amine or N- phenyl-[1,1':4', 1 "-terphenyl] -4- Amine.
Another formula of the compound structure is formula (5)：
In formula (5), R1、R2Respectively hydrogen or phenyl；R1、R2Can be with identical or different；R is dibenzofurans, benzo Aphthofurans, N- phenyl carbazoles, the fluorenes of spiral shell two, phenanthrene, dibiphenylyl amine, 9,9- dimethyl fluorenes-xenylamine or phenyl-terphenyl Amine；The preferred dibenzofurans of R, benzo [b] naphtho- [1,2-d] furans, N- phenyl carbazoles, 9,9 ' fluorenes of spiral shell two, phenanthrene, two (4- biphenyl Base amine), N- [1,1'- biphenyl -4- bases] -9,9- dimethyl -9H- fluorenes -2- amine or N- phenyl-[1,1':4', 1 "-terphenyl] -4- Amine.
Another formula of the compound structure is formula (6)：
In formula (6), R1、R2Respectively hydrogen or phenyl；R1、R2Can be with identical or different；R is dibenzofurans, benzo Aphthofurans, N- phenyl carbazoles, the fluorenes of spiral shell two, phenanthrene, dibiphenylyl amine, 9,9- dimethyl fluorenes-xenylamine or phenyl-terphenyl Amine；The preferred dibenzofurans of R, benzo [b] naphtho- [1,2-d] furans, N- phenyl carbazoles, 9,9 ' fluorenes of spiral shell two, phenanthrene, two (4- biphenyl Base amine), N- [1,1'- biphenyl -4- bases] -9,9- dimethyl -9H- fluorenes -2- amine or N- phenyl-[1,1':4', 1 "-terphenyl] -4- Amine.
Another formula of the compound structure is formula (7)：
In formula (7), R1、R2Respectively hydrogen or phenyl；R1、R2Can be with identical or different；R is dibenzofurans, benzo Aphthofurans, N- phenyl carbazoles, the fluorenes of spiral shell two, phenanthrene, dibiphenylyl amine, 9,9- dimethyl fluorenes-xenylamine or phenyl-terphenyl Amine；The preferred dibenzofurans of R, benzo [b] naphtho- [1,2-d] furans, N- phenyl carbazoles, 9,9 ' fluorenes of spiral shell two, phenanthrene, two (4- biphenyl Base amine), N- [1,1'- biphenyl -4- bases] -9,9- dimethyl -9H- fluorenes -2- amine or N- phenyl-[1,1':4', 1 "-terphenyl] -4- Amine.
Specifically, the structural formula of compound is：
A kind of preparation method of the compound-material, synthetic route are：
Wherein, R1、R2Respectively hydrogen or phenyl；R1、R2Can be with identical or different；Ar1Represent benzene, biphenyl, naphthalene, 1- phenyl Naphthalene, 9,9- dimethyl fluorenes；R be dibenzofurans, benzo aphthofurans, N- phenyl carbazoles, the fluorenes of spiral shell two, phenanthrene, dibiphenylyl amine, 9, 9- dimethyl fluorenes-xenylamine or phenyl-terphenyl amine；The preferred dibenzofurans of R, benzo [b] naphtho- [1,2-d] furans, N- phenyl carbazoles, 9,9 ' fluorenes of spiral shell two, phenanthrene, two (4- xenylamines), N- [1,1'- biphenyl -4- bases] -9,9- dimethyl -9H- fluorenes - 2- amine or N- phenyl-[1,1':4', 1 "-terphenyl] -4- amine；
The preparation method is initiation material with raw material 1 and raw material 2, and (hydrazine spreads out after Aldol condensation reaction, then with raw material 3 Biology) ring-closure reaction is carried out, the compound-material is made.
A kind of organic electroluminescence device, inject/transmit layer material or CPL layer materials using described compound as hole Material, for organic electroluminescent LED.
The present invention is beneficial to be had technical effect that：
Centered on pyrazoline group, polyaromatic conjugated structure group, experimental result are introduced at the 1 of pyrazoline, 3,5 Show, the material has high thermal stability and glass transition temperature, easily forms good amorphous thin film；As OLED Hole-injecting material, high brightness, high efficiency, the effect of low-voltage can be realized using such material；And the material has high roll over Rate feature is penetrated, after CPL layers (Cap layer, light extraction coating) material as OLED, the light of device can be effectively improved Extraction efficiency.
Further, relatively low voltage is set in the course of the work and the high thermal stability having in itself and vitrifying turn Temperature, apply in electroluminescent device, more stable effect and longer service life can be obtained.
Because the preparation method of pyrazolines derivative provided by the invention is simpler, therefore there is relatively low cost, It is easier to prepare and obtain in industrial production, it is relatively low as material cost.
Brief description of the drawings
Fig. 1 is the structural representation of electroluminescent device of the present invention.
In figure：1st, OLED substrate, 2, anode layer, 3, hole injection/transport layer, 4, luminescent layer, 5, electron transfer layer, 6th, electron injecting layer, 7, cathode layer, 8, CPL layers.
Embodiment
With reference to the accompanying drawings and examples, the present invention is specifically described.
The compound C1 of embodiment 1 synthesis
34.7g (0.1mol) 4- (base of 9- phenyl -9H- carbazoles -3) benzaldehydes and 10.6g are added into there-necked flask successively (0.1mol) Benzophenone, in 80ml alcohol sodium solutions, under room temperature condition, stir 12 hours, until reaction solution is changed into orange-yellow； Then, reactant mixture is filtered, and the filter cake of gained is washed with 3% hydrochloric acid solution, products therefrom alcohol crystal, obtained Yellow crystal intermediate bright 22.5g (0.05mol)；The centre of 22.5g (0.05mol) above-mentioned preparation is added in there-necked flask Body, 5.4g (0.05mol) phenylhydrazine is added, add the acetic acid of 100ml dryings, stirring, be heated to 90 DEG C, back flow reaction 10 is small When, terminate to ring-closure reaction；Separating acetic acid is evaporated under reduced pressure in reactant mixture, residue ethyl alcohol recrystallization, obtains compound C1 (18.6g, yield 34.5%).
The compound, molecular formula C are identified using DEI-MS39H29N3, detected value [M+1]+=540.5, calculated value 539.67。
The compound C4 of embodiment 2 synthesis
Prepared by the synthetic method of compound C1 in embodiment 1, difference is to replace benzene with 1- biphenyl -4- bases-ketone Ketone, [1,1'- biphenyl] -4- hydrazines replace phenylhydrazine.The compound, molecular formula C are identified using DEI-MS51H37N3, detected value [M+ 1]+=692.47, calculated value 691.86.
The compound F1 of embodiment 3 synthesis
Prepared by the synthetic method of compound C1 in embodiment 1, difference is with 4 '-(biphenyl -4- bases-amino) - Biphenyl -4- formaldehyde replaces 4- (base of 9- phenyl -9H- carbazoles -3) benzaldehyde.The compound, molecular formula are identified using DEI-MS C51H39N3, detected value [M+1]+=694.52, calculated value 693.88.
The compound G1 of embodiment 4 synthesis
Prepared by the synthetic method of compound C1 in embodiment 1, difference be with 4 '-(phenyl-[1 ', 4 ', 1 '] three Benzene -4- bases-amino)-biphenyl -4- formaldehyde replaces 4- (base of 9- phenyl -9H- carbazoles -3) benzaldehyde.This is identified using DEI-MS Compound, molecular formula C51H39N3, detected value [M+1]+=694.65, calculated value 693.88.
The compound E1 of embodiment 5 synthesis
Prepared by the synthetic method of compound C1 in embodiment 1, difference is with 4 '-[biphenyl -4- bases-(9,9- diformazans Base -9H- fluorenes -2- bases)-amino]-biphenyl -4- formaldehyde replaces 4- (base of 9- phenyl -9H- carbazoles -3) benzaldehyde.Come using DEI-MS Identify the compound, molecular formula C44H43N3Detected value [M+1]+=734.55, calculated value 733.94.
The compound E5 of embodiment 6 synthesis
Prepared by the synthetic method of compound C1 in embodiment 1, difference is with 4 '-[biphenyl -4- bases-(9,9- diformazans Base -9H- fluorenes -2- bases)-amino]-biphenyl -4- formaldehyde replaces 4- (base of 9- phenyl -9H- carbazoles -3) benzaldehyde, biphenyl -2- bases-hydrazine Instead of phenylhydrazine.The compound, molecular formula C are identified using DEI-MS60H47N3Detected value [M+1]+=810.82, calculated value 810.04。
The compound I1 of embodiment 7 synthesis
Prepared by the synthetic method of compound C1 in embodiment 1, difference is to use 4- dibenzofurans -4- bases-naphthalene -1- Formaldehyde replaces 4- (base of 9- phenyl -9H- carbazoles -3) benzaldehyde.The compound, molecular formula C are identified using DEI-MS37H26N2O, Detected value [M+1]+=515.11, calculated value 514.26.
The compound I8 of embodiment 8 synthesis
By in embodiment 1 compound C1 synthetic method prepare, difference be with 4- (4- phenanthrene -9- bases-phenyl)-naphthalene - 1- formaldehyde replaces 4- (base of 9- phenyl -9H- carbazoles -3) benzaldehyde.The compound, molecular formula C are identified using DEI-MS45H32N2, Detected value [M+1]+=601.21, calculated value 600.75.
The compound J2 of embodiment 9 synthesis
Prepared by the synthetic method of compound C1 in embodiment 1, difference is to use 7- benzos [b] naphtho- [1,2-d] furan - 6- base -9,9- dimethyl -9H- fluorenes -2- formaldehyde of muttering replaces 4- (base of 9- phenyl -9H- carbazoles -3) benzaldehyde.Come using DEI-MS Identify the compound, molecular formula C46H34N2O, detected value [M+1]+=631.56, calculated value 630.77.
The compounds of this invention uses in luminescent device, can be injected as hole/layer material is transmitted, can also conduct CPL materials.
Hereinafter, compound provided by the present invention is described in detail in electroluminescent hair by device embodiments 1~7 and comparative example 1 Application and its effect on optical device；Wherein, in device embodiments 1~6 using the compounds of this invention as hole injection/transport layer Material, device embodiments 7 prove its advantage using the compounds of this invention as CPL materials and with comparative example 1.
Fig. 1 is the structural representation of electroluminescent device of the present invention, wherein：1st, OLED substrate, 2, anode layer, 3, empty Cave injection/transport layer, 4, luminescent layer, 5, electron transfer layer, 6, electron injecting layer, 7, cathode layer, 8, CPL layers.
Device embodiments 1
A kind of electroluminescent device, its preparation process include：
A) anode layer 2 cleaned on transparent substrate layer 1, cleans each 15 points with deionized water, acetone, EtOH Sonicate respectively Clock, then handled 2 minutes in plasma cleaner；
B) on the anode layer be deposited hole injection layer 3, compound C1 made from the embodiment of the present invention 1 as hole injection/ Transmit layer material, thickness 40nm；
C) the co-evaporation luminescent layer 4 on hole injection/transmitting layer 3, CBP is as material of main part, Ir (ppy)3As Phosphorescence dopant material, phosphor material doping ratio are 5%, thickness 30nm；
D) on doping type luminescent layer compound, electron transport material TPBI, thickness are deposited by vacuum evaporation mode For 30nm, this layer of organic material uses as electron transfer layer 5；
E) on electron transfer layer 5, vacuum evaporation electron injecting layer LiF, thickness 0.5nm, the layer is electron injection Layer 6；
F) on electron injecting layer 6, vacuum evaporation negative electrode Mg：Ag/Ag layers, Mg:Ag doping ratios are 9:1, thickness 15nm, Ag thickness 3nm, the layer are cathode layer 7；
G) without CPL layers on cathode layer 7.
After the making that electroluminescent device is completed according to above-mentioned steps, the driving voltage of measurement device, quantum efficiency, electric current Efficiency, power efficiency and life-span, it the results are shown in Table shown in 1.
Device embodiments 2
The difference of the present embodiment and device embodiments 1 is：The hole of electroluminescent device injects/transmit layer material It is changed into compound C4 made from the embodiment of the present invention 2.The detection data of gained electroluminescent device are shown in Table 1.
Device embodiments 3
The difference of the present embodiment and device embodiments 1 is：The hole of electroluminescent device injects/transmit layer material It is changed into compound F1 made from the embodiment of the present invention 3.The detection data of gained electroluminescent device are shown in Table 1.
Device embodiments 4
The difference of the present embodiment and device embodiments 1 is：The hole of electroluminescent device injects/transmit layer material It is changed into compound G1 made from the embodiment of the present invention 4.The detection data of gained electroluminescent device are shown in Table 1.
Device embodiments 5
The difference of the present embodiment and device embodiments 1 is：The hole of electroluminescent device injects/transmit layer material It is changed into compound E1 made from the embodiment of the present invention 5.The detection data of gained electroluminescent device are shown in Table 1.
Device embodiments 6
The difference of the present embodiment and device embodiments 1 is：The hole of electroluminescent device injects/transmit layer material It is changed into compound E5 made from the embodiment of the present invention 6.The detection data of gained electroluminescent device are shown in Table 1.
Device embodiments 7
The difference of the present embodiment and device embodiments 1 is：Hole injection/transmitting layer 3 of electroluminescent device Material is NPB, and the CPL layers 8 of electroluminescent device are using compound C1, thickness 60nm made from the embodiment of the present invention 1.Gained The detection data of electroluminescent device are shown in Table 1.
Device comparative example 1
The difference of this device comparative example 1 and device embodiments 1 is：Hole injection/transmission of electroluminescent device The material of layer 3 is NPB.The detection data of gained electroluminescent device are shown in Table 1.
Table 1
From the point of view of result by table 1, photoelectric material of the present invention can be applied to electroluminescent device making, and can obtain Obtain performance well.Used using material of the present invention as the hole of electroluminescent device injection/transmission material, with device Comparative example 1 is compared, and external quantum efficiency, current efficiency, power efficiency and the life-span of embodiment 1 to 6 are obviously improved, voltage Reduce 20-25%；Device embodiments 7 lift 25% compared to the device efficiency of device comparative example 1.
To sum up, presently preferred embodiments of the present invention is the foregoing is only, is not intended to limit the invention, all essences in the present invention God any modification, equivalent substitution and improvements made etc., should be included in the scope of the protection with principle.

Claims (10)

  1. A kind of 1. compound-material containing pyrazoline structure, it is characterised in that compound skeleton centered on pyrazoline, its Shown in the formula of molecular structure such as formula (1)：
    In formula (1), R1、R2Respectively hydrogen or phenyl；R1、R2Can be with identical or different；
    In formula (1), R3Represented using formula (2)：
    Ar1—R
    Formula (2)
    In formula (2), Ar1Pass through C-C key connections, Ar with formula (1)1Represent benzene, biphenyl, naphthalene, 1- phenylnaphthalenes, 9,9- dimethyl Fluorenes；
    In formula (2), R is dibenzofurans, benzo aphthofurans, N- phenyl carbazoles, the fluorenes of spiral shell two, phenanthrene, dibiphenylyl amine, 9,9- Dimethyl fluorene-xenylamine or phenyl-terphenyl amine.
  2. 2. compound-material according to claim 1, it is characterised in that the formula of the compound structure is formula (3)：
    In formula (3), R1、R2Respectively hydrogen or phenyl；R1、R2Can be with identical or different；R is dibenzofurans, benzo naphtho- Furans, N- phenyl carbazoles, the fluorenes of spiral shell two, phenanthrene, dibiphenylyl amine, 9,9- dimethyl fluorenes-xenylamine or phenyl-terphenyl amine.
  3. 3. compound-material according to claim 1, it is characterised in that the formula of the compound structure is formula (4)：
    In formula (4), R1、R2Respectively hydrogen or phenyl；R1、R2Can be with identical or different；R is dibenzofurans, benzo naphtho- Furans, N- phenyl carbazoles, the fluorenes of spiral shell two, phenanthrene, dibiphenylyl amine, 9,9- dimethyl fluorenes-xenylamine or phenyl-terphenyl amine.
  4. 4. compound-material according to claim 1, it is characterised in that the formula of the compound structure is formula (5)：
    In formula (5), R1、R2Respectively hydrogen or phenyl；R1、R2Can be with identical or different；R is dibenzofurans, benzo naphtho- Furans, N- phenyl carbazoles, the fluorenes of spiral shell two, phenanthrene, dibiphenylyl amine, 9,9- dimethyl fluorenes-xenylamine or phenyl-terphenyl amine.
  5. 5. compound-material according to claim 1, it is characterised in that the formula of the compound structure is formula (6)：
    In formula (6), R1、R2Respectively hydrogen or phenyl；R1、R2Can be with identical or different；R is dibenzofurans, benzo naphtho- Furans, N- phenyl carbazoles, the fluorenes of spiral shell two, phenanthrene, dibiphenylyl amine, 9,9- dimethyl fluorenes-xenylamine or phenyl-terphenyl amine.
  6. 6. compound-material according to claim 1, it is characterised in that the formula of the compound structure is formula (7)：
    In formula (7), R1、R2Respectively hydrogen or phenyl；R1、R2Can be with identical or different；R is dibenzofurans, benzo naphtho- Furans, N- phenyl carbazoles, the fluorenes of spiral shell two, phenanthrene, dibiphenylyl amine, 9,9- dimethyl fluorenes-xenylamine or phenyl-terphenyl amine.
  7. 7. according to the compound-material described in any one of claim 1~6, it is characterised in that in the compound, R is dibenzo Furans, benzo [b] naphtho- [1,2-d] furans, N- phenyl carbazoles, the fluorenes of 9,9' spiral shells two, phenanthrene, two (4- xenylamines), N- [1,1'- Biphenyl -4- bases] -9,9- dimethyl -9H- fluorenes -2- amine or N- phenyl-[1,1':4', 1 "-terphenyl] -4- amine.
  8. 8. compound-material according to claim 1, it is characterised in that the structural formula of compound is：
  9. 9. the preparation method of the compound-material described in a kind of claim 1, it is characterised in that synthetic route is：
    Wherein, R1、R2Respectively hydrogen or phenyl；R1、R2Can be with identical or different；Ar1Represent benzene, biphenyl, naphthalene, 1- phenylnaphthalenes, 9,9- dimethyl fluorenes；R is dibenzofurans, benzo aphthofurans, N- phenyl carbazoles, the fluorenes of spiral shell two, phenanthrene, xenylamine, fluorenes-biphenyl Base amine or phenyl-xenylamine；
    The preparation method is initiation material with raw material 1 and raw material 2, after Aldol condensation reaction, then with raw material 3 (hydrazine derivate) Ring-closure reaction is carried out, the compound-material is made.
  10. 10. a kind of organic electroluminescence device, it is characterised in that using the compound described in claim 1 as hole injection/biography Defeated material or CPL layer material, for organic electroluminescent LED.
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