CN103936722B - Azophenlyene compounds that a kind of carbazole replaces and its production and use - Google Patents

Azophenlyene compounds that a kind of carbazole replaces and its production and use Download PDF

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CN103936722B
CN103936722B CN201410145155.4A CN201410145155A CN103936722B CN 103936722 B CN103936722 B CN 103936722B CN 201410145155 A CN201410145155 A CN 201410145155A CN 103936722 B CN103936722 B CN 103936722B
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azophenlyene
general structure
electroluminescence device
organic electroluminescence
compounds
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CN103936722A (en
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董清晨
黄锦海
苏建华
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Taiyuan University of Technology
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    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains three hetero rings
    • C07D471/14—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
    • C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
    • C07D495/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
    • C07D495/12—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains three hetero rings
    • C07D495/14—Ortho-condensed systems
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    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
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    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1092—Heterocyclic compounds characterised by ligands containing sulfur as the only heteroatom

Abstract

The invention discloses azophenlyene compounds of a kind of carbazole replacement and preparation method thereof, described azophenlyene compounds is for having the compound of formula (I) described general structure.Described azophenlyene compounds has good thermostability, as organic electroluminescent hole transport or injecting material, can be applied on organic electroluminescence device.The organic electroluminescence device prepared by material of the present invention has the advantage that electroluminescent efficiency is good and purity of color is excellent and the life-span is long.

Description

Azophenlyene compounds that a kind of carbazole replaces and its production and use
Technical field
The present invention relates to a kind of azophenlyene compounds, particularly a kind of azophenlyene compounds with carbazole group, and the preparation method of this azophenlyene compounds and purposes.
Background technology
Organic electroluminescence device, as a kind of novel technique of display, has the particular advantages such as luminous, wide viewing angle, less energy-consumption, efficiency is high, thin, rich color, fast response time, Applicable temperature scope wide, low driving voltage.Since the Tang etc. of Kodak in 1987 utilizes vacuum evaporation ultrathin membrane technology, with oxine aluminium (Alq 3) as luminescent layer, triphenylamine derivative is as hole transmission layer, low voltage drive organic electroluminescence device (the TangC.W. with bilayer film sandwich type structural is made with metal electrode, VanslykeS.A.Organicelectroluminescentdiodes.Appl.Phys.Le tt.1987,51:913-916), people have carried out a lot of research to organic electroluminescence device.
The principle of luminosity of organic electroluminescence device is when a field is applied, and positive and negative charge is injected into hole transmission layer and electron transfer layer by anode and negative electrode respectively, then compound make luminophore luminous in luminescent layer.Therefore, the efficiency of device be improved, need the efficiency improving charge injection hole transmission layer and electron transfer layer.These years, people have studied various hole mobile material and electron transport material, and electroluminescent organic material and device have been widely used on the display panel of mobile phone and the small screen.But the stability of electroluminescent organic material and the life-span of device remain its important factor applied of restriction, and hole mobile material remains the important factor affecting device.
NPB (N, N '-two (1-naphthyl)-N, N '-phenylbenzene-1,1 '-biphenyl-4-4 '-diamines) as a kind of hole mobile material, from invention till now, applied by large quantifier elimination, but its stability and conductive capability still need to improve always.
Azophenlyene compounds has good hole transport performance, and Su Jianhua etc. report the synthetic method of new azophenlyene compounds, as the compound of structure following in CN102491950, has greatly promoted the industrialization process of phenol piperazine.The present invention is exactly on the basis of its synthesis technique, azophenlyene introduces a carbazole group, offers compare with original text, and the stability of compound is improved and hole transport performance strengthens.
Summary of the invention
Azophenlyene compounds that the object of the present invention is to provide a series of carbazole with better thermostability to replace and preparation method thereof.
To the present invention also aims to described azophenlyene compounds, as organic electroluminescent hole transport or injecting material, be applied on organic electroluminescence device.The organic electroluminescence device prepared by material of the present invention has the advantage that electroluminescent efficiency is good and purity of color is excellent and the life-span is long.
The azophenlyene compounds that carbazole of the present invention replaces is for having the compound of formula (I) described general structure:
Wherein, Ar1, Ar2 are expressed as C independently of one another 1~ C 4substituted or unsubstituted benzene, naphthalene, pyridine, thiophene or quinoline.
Azophenlyene compounds described in general structure of the present invention (I) is that raw material prepares by the halo azophenlyene described in general structure (II) and the carbazoles derivative described in general structure (III):
Wherein X is expressed as Cl, Br or I;
Wherein, Ar1, Ar2 are expressed as C independently of one another 1~ C 4substituted or unsubstituted benzene, naphthalene, pyridine, thiophene or quinoline.
The concrete preparation method of general structure of the present invention (I) described azophenlyene compounds is:
With the halo azophenlyene described in general structure (II) and the carbazoles derivative described in general structure (III) for raw material, under palladium chtalyst and alkali exist, carry out Buchwald-Hartwig reaction 8 ~ 10 hours in 80 ~ 120 DEG C, obtain the azophenlyene compounds described in general structure (I).
Wherein, the amount of substance ratio of the halo azophenlyene described in described general structure (II), carbazoles derivative, palladium catalyst and alkali described in general structure (III) is 1 ︰ 1 ︰ 0.01 ︰ 1.5.
Described alkali is selected from alkaline carbonate, alkali metal phosphate, alkali metal hydroxide or trimethyl carbinol an alkali metal salt.
Described palladium catalyst is selected from the one in palladium, palladium chloride, four (triphenyl phosphorus) palladium, [1,1 '-bis-(diphenylphosphine) ferrocene] palladium chloride (II).
General structure of the present invention (I) described azophenlyene compounds can also be prepared by following method:
With the halo azophenlyene described in general structure (II) and the carbazoles derivative described in general structure (III) for raw material, under copper catalysis and alkali exist, carry out Ullmman reaction 8 ~ 10 hours in 120 ~ 200 DEG C, obtain the azophenlyene compounds described in general structure (I).
Wherein, the amount of substance ratio of the halo azophenlyene described in described general structure (II), carbazoles derivative, copper catalyst and alkali described in general structure (III) is 1 ︰ 1 ︰ 0.01 ︰ 1.5.
Described alkali is selected from alkaline carbonate, alkali metal phosphate, alkali metal hydroxide or trimethyl carbinol an alkali metal salt.
Described copper catalyst is selected from the one in cuprous halide, copper halide, copper sulfate, venus crystals, copper powder or cupric oxide.
The reaction formula of general structure of the present invention (I) azophenlyene compounds preparation method is as follows:
X is expressed as Cl or Br or I.Ar1, Ar2 are expressed as C independently of one another 1~ C 4substituted or unsubstituted benzene, naphthalene, pyridine, thiophene or quinoline.
(1) ~ (11) list the concrete structure formula that part meets the azophenlyene compounds of general structure (I) below, but it should be noted that, the following structural formula enumerated does not form the restriction to azophenlyene compounds of the present invention:
。
The azophenlyene compounds that the present invention prepares has good thermostability, as organic electroluminescent hole mobile material or hole-injecting material, can be applied on organic electroluminescence device.
Equally, the azophenlyene compounds that the present invention prepares also as emitting layer material, can be applied on organic electroluminescence device.
Present invention also offers the organic electroluminescence device including above-mentioned azophenlyene compounds.
Described organic electroluminescence device is made up of substrate, anodic-cathodic and the organic layer be arranged between anodic-cathodic, wherein organic layer comprises luminescent layer, electron transfer layer, hole transmission layer, hole injection layer, electron injecting layer etc., it needs to be noted, above-mentioned organic layer can be selected as required, need not every layer all exist.
Particularly, organic electroluminescence device of the present invention is between the anodic-cathodic of device, at least include the organic layer that one deck contains the described azophenlyene compounds of general structure (I).
And then organic electroluminescence device of the present invention at least includes hole transmission layer or the hole injection layer that one deck contains the described azophenlyene compounds of general structure (I).
Azophenlyene compounds described in general structure of the present invention (I) can also be included in the luminescent layer of organic electroluminescence device.
In the present invention, the organic layer thickness of described organic electroluminescence device is 50 ~ 1000nm, is preferably 100 ~ 500nm.
Described hole transmission layer and the thickness of hole injection layer are 10 ~ 1000nm, are preferably 30 ~ 200nm.
The described organic layer containing the described azophenlyene compounds of general structure (I) can be deposited on electrode by vacuum evaporation or spin coating mode.
Carry out experiment test to described organic electroluminescence device to show, general structure of the present invention (I) described azophenlyene compounds has good thermostability, high-luminous-efficiency and high luminance purity as electroluminescent organic material.The organic electroluminescence device using described electroluminescent organic material to make has the advantage that electroluminescent efficiency is good and purity of color is excellent and the life-span is long.
Accompanying drawing explanation
Fig. 1 is the device architecture figure of the embodiment of the present invention 2 organic electroluminescence device, and in figure, 10 is glass substrate, and 20 is anode, and 30 is hole transmission layer, and 40 is luminescent layer, and 50 is electron transfer layer, and 60 is electron injecting layer, and 70 is negative electrode.
Fig. 2 is the utilizing emitted light spectrogram of embodiment 2 organic electroluminescence device under 7V voltage.
Embodiment
Embodiment 1
Raw material 1
0.0045g palladium and 0.0058g tri-tert phosphorus is added in the 50mL single port flask being added with 20mL toluene; after dissolving; 0.5g is added again successively purchased from the Shanghai Road also raw material 1 of Chemical Industry Science Co., Ltd, 0.3g carbazole and 0.22g potassium tert.-butoxide, heated overnight at reflux under nitrogen protection.After reacting completely, filter, washing, filtrate is revolved and is steamed except desolventizing, and silica gel column chromatography is separated, and obtains 280mg azophenlyene compounds white solid, productive rate 47%.
1HNMR(400MHz,CDCl 3)δ8.84–8.77(m,2H),8.39–8.34(m,1H),8.21(d,J=8.1Hz,1H),8.10(d,J=7.6Hz,2H),7.84(m,2H),7.73(m,3H),7.61(t,J=7.6Hz,1H),7.46–7.41(m,2H),7.35(t,J=7.7Hz,2H),7.23(t,J=7.5Hz,2H),7.16–6.99(m,10H),6.86(t,J=7.2Hz,1H)。HRMS (ESI, m/z): calculated value [M+H] +c 44h 29n 3, 600.2440; Measured value 600.2443.
Embodiment 2
Present embodiments provide a kind of organic electroluminescence device containing embodiment 1 azophenlyene compounds, described azophenlyene compounds uses as hole transport layer material in this device, and its device architecture is:
ITO/ embodiment 1 azophenlyene compounds (60nm)/Alq 3(30nm)/Alq 3(10nm)/LiF (1nm)/Al (100nm).
First, electrically conducting transparent ito glass substrate 10 (above with anode 20) is cleaned through washing composition, deionized water, ethanol, acetone and deionized water successively, then uses oxygen plasma treatment 30 seconds, then with the CFx process of plasma treatment; Then evaporation embodiment 1 azophenlyene compounds on ito glass substrate, forms the hole transmission layer 30 that 60nm is thick; The order Alq that evaporation 30nm is thick on hole transmission layer 3as luminescent layer 40, the Alq that evaporation 10nm is thick on luminescent layer 3as electron transfer layer 50, the thick LiF of evaporation 1nm is as electron injecting layer 60, and finally, the thick Al of evaporation 100nm is as device cathodes 70.
The efficiency of organic electroluminescence device under 7V voltage of above-mentioned preparation is 2.06cd/A, green light, and Fig. 2 is its emmission spectrum under 7V voltage.
Comparative example 1
Using NPB as hole transport layer material, prepare organic electroluminescence device, its device architecture is:
ITO/NPB(60nm)/Alq 3(30nm)/Alq 3(10nm)/LiF(1nm)/Al(100nm)。Preparation method is embodiment 2 simultaneously.
The prepared efficiency of organic electroluminescence device under 7V voltage is 1.87cd/A, green light.
As can be seen here, under the same conditions, the luminous efficiency of organic electroluminescence device prepared by the present invention is higher than comparative example, and electroluminescent organic material of the present invention has high stability, and the organic electroluminescence device prepared with it has high efficiency and optical purity.

Claims (10)

1. an azophenlyene compounds for carbazole derivative replacement, for having the compound of formula (I) described general structure:
Wherein, Ar1, Ar2 are expressed as C independently of one another 1~ C 4substituted or unsubstituted benzene, naphthalene, pyridine, thiophene or quinoline.
2. the preparation method of azophenlyene compounds described in claim 1 is raw material by the halo azophenlyene described in general structure (II) and the carbazoles derivative described in general structure (III),
Wherein X is expressed as Cl, Br or I;
Wherein, Ar1, Ar2 are expressed as C independently of one another 1~ C 4substituted or unsubstituted benzene, naphthalene, pyridine, thiophene or quinoline;
Under palladium chtalyst and alkali exist, Buchwald-Hartwig reaction 8 ~ 10 hours is carried out in 80 ~ 120 DEG C, obtain the azophenlyene compounds described in general structure (I), wherein, the amount of substance ratio of the halo azophenlyene described in described general structure (II), carbazoles derivative, palladium catalyst and alkali described in general structure (III) is 1 ︰ 1 ︰ 0.01 ︰ 1.5.
3. the preparation method of azophenlyene compounds described in claim 1 is raw material by the halo azophenlyene described in general structure (II) and the carbazoles derivative described in general structure (III),
Wherein X is expressed as Cl, Br or I;
Wherein, Ar1, Ar2 are expressed as C independently of one another 1~ C 4substituted or unsubstituted benzene, naphthalene, pyridine, thiophene or quinoline;
Under copper catalysis and alkali exist, Ullmman reaction 8 ~ 10 hours is carried out in 120 ~ 200 DEG C, obtain the azophenlyene compounds described in general structure (I), wherein, the amount of substance ratio of the halo azophenlyene described in described general structure (II), carbazoles derivative, copper catalyst and alkali described in general structure (III) is 1 ︰ 1 ︰ 0.01 ︰ 1.5.
4. the preparation method according to Claims 2 or 3, is characterized in that described alkali is selected from alkaline carbonate, alkali metal phosphate, alkali metal hydroxide or trimethyl carbinol an alkali metal salt.
5. claim 1 azophenlyene compounds is as the purposes of hole mobile material in organic electroluminescence device.
6. claim 1 azophenlyene compounds is as the purposes of hole-injecting material in organic electroluminescence device.
7. claim 1 azophenlyene compounds is as the purposes of emitting layer material in organic electroluminescence device.
8. an organic electroluminescence device, described organic electroluminescence device is made up of substrate, anodic-cathodic and the organic layer be arranged between anodic-cathodic, at least includes the organic layer that one deck contains azophenlyene compounds described in claim 1 between anodic-cathodic.
9. organic electroluminescence device according to claim 8, is characterized in that described azophenlyene compounds is included in hole transmission layer or hole injection layer.
10. organic electroluminescence device according to claim 8, is characterized in that described azophenlyene compounds is included in luminescent layer.
CN201410145155.4A 2014-04-14 2014-04-14 Azophenlyene compounds that a kind of carbazole replaces and its production and use Expired - Fee Related CN103936722B (en)

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CN102491950A (en) * 2011-12-09 2012-06-13 华东理工大学 Quinoxaline derivative and preparation method thereof

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