CN106565711A - 1,3,4-triaza pyrene derivatives used for electroluminescent materials and applications thereof - Google Patents

1,3,4-triaza pyrene derivatives used for electroluminescent materials and applications thereof Download PDF

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CN106565711A
CN106565711A CN201510658636.XA CN201510658636A CN106565711A CN 106565711 A CN106565711 A CN 106565711A CN 201510658636 A CN201510658636 A CN 201510658636A CN 106565711 A CN106565711 A CN 106565711A
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吴凡
龚智豪
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EverDisplay Optronics Shanghai Co Ltd
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    • 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
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    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
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    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
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    • H10K50/14—Carrier transporting layers
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    • H10K50/14—Carrier transporting layers
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    • 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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    • 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
    • H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
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Abstract

1,3,4-triaza pyrene derivatives used for electroluminescent materials are provided. The derivatives are characterized in that the derivatives are compounds shown as the general structure formula (I), wherein any two of R1 to R7 are amido, and the other five are non-amido groups independently, and A1 to A4 are respectively non-amido groups independently. Preferentially, the non-amido groups are hydrogen, halogens, cyano, C1-C10 alkyl, substituted or non-substituted C3-C10 naphthenic bases, C1-C10 alkoxy, C2-C10 alkenyl, substituted or non-substituted C6-C30 aryl, substituted or non-substituted C10-C30 polycyclic aromatic hydrocarbons and C3-C30 heterocyclic aromatic hydrocarbons, substituted or non-substituted C7-C30 aralkyl and C3-C30 propenyloxy. An OLED electron transfer layer material, a luminescent layer material, a hole transfer layer material and an OLED device which contain the compounds shown as the general structure formula (I) and a preparing method of the OLED device are also provided. Hole transfer performance, dissolubility and thermal stability of the OLED material containing the compounds shown as the general structure formula (I) are improved.

Description

A kind of 1,3,4- tri- azepine pyrene derivatives that can be used for electroluminescent material and its application
Technical field
The present invention relates to a kind of compound, more particularly to a kind of can be used for 1, the 3,4- tri- of electroluminescent material Azepine pyrene derivatives and its application.
Background technology
Organic electroluminescent is described as most potential flat panel display of future generation by industrial circle and academia, has Low-power consumption, wide viewing angle, respond it is fast, lighter and thinner and can Flexible Displays the advantages of.
Organic electroluminescent LED (OLEDs) possesses as a kind of brand-new Display Technique in each performance The unmatched advantage of existing Display Technique, such as have it is all solid state, from main light emission, brightness height, high-resolution, Visual angle width (more than 170 degree), fast response time, thickness of thin, small volume, it is lightweight, can using flexible base board, Low-voltage direct-current drives (3-10V), low in energy consumption, operating temperature range width etc. so that its application market is very Extensively, as illuminator, communication system, car-mounted display, portable electric appts, fine definition show even It is military field.
With the development of organic electroluminescent technology, material functional trend is all the more careful, wherein the note of carrier It is physical process most basic in Organic Light Emitting Diode to enter and transmit, the luminescent properties to device, such as quantum effect Rate, power consumption etc. have conclusive impact.Compared with inorganic semiconductor diode, organic semiconductor diodes by The multiformity of randomness, material in its structure and cause carrier physical process seem increasingly complex, be used for The organic material of electron transfer layer and hole blocking layer is most important.
Although in fact, the continuous expansion of OLED ranges of application, but still Shortcomings, more for example show Hole transport ability is not high enough to have OLED material to exist, and luminous efficiency is relatively low, dissolubility and heat stability compared with Low problem, and selection of the good and bad basic factor of OLED performances for material is determined, therefore, design and seek A kind of compound is looked for, is occurred in actual application to overcome the shortcomings of it as OLED new materials, It is the emphasis and Development Trend from now in OLED material research work.
The content of the invention
In order to preferably embody across epoch technical advantages of the OLED relative to TFT-LCD, Er Qieneng OLED material prior art produced problem in actual application is enough solved, it is contemplated that improving existing There are hole transport ability, dissolubility and the heat stability of luminescent material, devise a series of electroluminescent organic materials, Specially blue emitting material.
In a first aspect, the invention provides a kind of 1,3,4- tri- azepine pyrenes that can be used for electroluminescent material spread out It is biological, it is characterised in that its structure is the compound shown in logical formula I：
Wherein, in R1～R7 any 2 be amido, 5 groups for being each independently non-amido in addition；A1～A4 It is each independently the group of non-amido.
Preferably, the group of the non-amido is：Hydrogen, halogen, cyano group, C1～C10 alkyl, replace or not Substituted C3～C10 cycloalkyl, C1～C10 alkoxyls, C2～C10 alkenyls, replace or do not replace C6～C30 aryl radicals, the C10～C30 condensed-nuclei aromatics for replacing or not replacing and C3～C30 heterocyclic arenes, C7～C30 aralkyl, the C3～C30 propenyloxy groups for replacing or not replacing.
It is further preferred that 1,3, the 4- tri- azepine pyrene derivatives that can be used for electroluminescent material are selected from One of following compound：
Second aspect, the invention provides a kind of can be used for 1, the 3,4- tri- of electroluminescent material containing above-mentioned The OLED electron transport layer materials of azepine pyrene derivatives.
The third aspect, the invention provides a kind of can be used for 1, the 3,4- tri- of electroluminescent material containing above-mentioned The OLED emitting layer materials of azepine pyrene derivatives.
Fourth aspect, the invention provides a kind of can be used for 1, the 3,4- tri- of electroluminescent material containing above-mentioned The OLED hole transport layer materials of azepine pyrene derivatives.
5th aspect, the invention provides a kind of can be used for 1, the 3,4- tri- of electroluminescent material containing above-mentioned The OLED of azepine pyrene derivatives.
6th aspect, the invention provides a kind of preparation method of above-mentioned OLED, it is characterised in that The preparation method includes：
1) substrate for being provided with transparent anode electrode ITO is cleaned by ultrasonic into 5-10 minutes in isopropanol, and 20-30 minutes under ultraviolet light are exposed, subsequently 5-10 minutes is processed with plasma；
2) substrate after process is put into into evaporated device, hole transport layer material is deposited with first as hole transport Layer；
3) and then evaporation luminescent layer, mixing evaporation emitting layer material, and the Ir (ppy) 3 of 5-10%；
4) electron transport layer materials are subsequently adopted, one layer of electron transfer layer is deposited with substrate, be subsequently deposited with again 0.5-2nm thick LiF, is subsequently deposited with the thick metal Al of 100-200nm；
Wherein, one of the hole transport layer material, emitting layer material, electron transport layer materials are formula (I) compound shown in.
Preferably, the thickness of the hole transmission layer is 30-50nm；The thickness of the luminescent layer is 10-120nm；The thickness of the electron transfer layer is 20-40nm.
The invention provides a kind of compound based on structure shown in logical formula I, can be used for electroluminescent blue-light-emitting Material, the OLED material not only can improve hole transport ability, dissolubility, can also improve OLED materials The heat stability of material.Additionally, the compound structure of structure is simple shown in logical formula I, it is easy to synthesize, can be with The preparation cost of OLED material is effectively reduced, with good industrial prospect.Should be containing logical formula I The OLED material of the compound of shown structure, can be used for electron transfer layer, luminescent layer, hole transmission layer Deng so that OLED display screen realizes the effect of high brightness, high efficiency, low-power consumption.
Specific embodiment
With reference to specific embodiment, the present invention is further elaborated, but the present invention is not limited to following enforcement Mode.
In a first aspect, the invention provides a kind of 1,3,4- tri- azepine pyrenes that can be used for electroluminescent material spread out It is biological, it is characterised in that its structure is the compound shown in logical formula I：
Wherein, in R1～R7 any 2 be amido, 5 groups for being each independently non-amido in addition；A1～A4 It is each independently the group of non-amido.
In a preferred embodiment, the group of the non-amido is：Hydrogen, halogen, cyano group, C1～C10 alkane Base, replacement or the C3～C10 cycloalkyl not replaced, C1～C10 alkoxyls, C2～C10 alkenyls, replacement Or C6～C30 aryl radicals, replacement or the C10～C30 condensed-nuclei aromatics not replaced and the C3～C30 not replaced Heterocyclic arene, replacement or the C7～C30 aralkyl not replaced, C3～C30 propenyloxy groups.
In a further preferred embodiment, 1,3,4- tri- nitrogen that can be used for electroluminescent material Miscellaneous pyrene derivatives are selected from one of following compound：
Second aspect, the invention provides a kind of can be used for 1, the 3,4- tri- of electroluminescent material containing above-mentioned The OLED electron transport layer materials of azepine pyrene derivatives.
The third aspect, the invention provides a kind of can be used for 1, the 3,4- tri- of electroluminescent material containing above-mentioned The OLED emitting layer materials of azepine pyrene derivatives.
Fourth aspect, the invention provides a kind of can be used for 1, the 3,4- tri- of electroluminescent material containing above-mentioned The OLED hole transport layer materials of azepine pyrene derivatives.
5th aspect, the invention provides a kind of can be used for 1, the 3,4- tri- of electroluminescent material containing above-mentioned The OLED of azepine pyrene derivatives.
6th aspect, the invention provides a kind of preparation method of above-mentioned OLED, it is characterised in that The preparation method includes：
1) substrate for being provided with transparent anode electrode ITO is cleaned by ultrasonic into 5-10 minutes in isopropanol, and 20-30 minutes under ultraviolet light are exposed, subsequently 5-10 minutes is processed with plasma；
2) substrate after process is put into into evaporated device, hole transport layer material is deposited with first as hole transport Layer；
3) and then evaporation luminescent layer, mixing evaporation emitting layer material, and the Ir (ppy) 3 of 5-10%；
4) electron transport layer materials are subsequently adopted, one layer of electron transfer layer is deposited with substrate, be subsequently deposited with again 0.5-2nm thick LiF, is subsequently deposited with the thick metal Al of 100-200nm；
Wherein, one of the hole transport layer material, emitting layer material, electron transport layer materials are formula (I) compound shown in.
In a preferred embodiment, the thickness of the hole transmission layer is 30-50nm；The luminescent layer Thickness be 10-120nm；The thickness of the electron transfer layer is 20-40nm.
Wherein, with regard to of the present invention 1,3,4- tri- azepine pyrene derivatives synthetic method embodiment, It is as follows：
Embodiment 1
According to prior art literature (Chemistry of Heterocyclic Compounds；vol,45；nb.1； (2009)；P.119-120 method synthetic intermediate A-1-0 described in).
Intermediate A -1-0 (1mol), BPO (0.1mol) and NBS (2.2mol) are dissolved in into carbon tetrachloride In (10 times of volumes), 60 DEG C are stirred 12 hours, and completely, concentration is removed after carbon tetrachloride TLC analytical reactions In being dissolved in dichloromethane, organic faciess anhydrous Na after washing2SO4It is dried, obtains in yellow oil after concentration Mesosome A-1-1 crude products, yield 89%.
Under nitrogen protection, by intermediate A -1-1 (1mol), diphenylamines (2.2mol), 1,2- cyclohexanediamine (4mol), Hydro-Giene (Water Science). (0.1mol) is dissolved in Isosorbide-5-Nitrae-dioxane, and 100 DEG C are stirred 6 hours, LC-MS Show that reaction is complete, MS measures C42H39N5(M+1=582.4).Room temperature is cooled to, and is slowly dropped into and is stirred In the water mixed (10 volume ratio), extracted 3 times with ethyl acetate (3 volume), after merging organic faciess, done Dry, silicagel column (ethyl acetate/petroleum ether=1 is crossed in concentration：10) compound as white solid A-1 (50% is obtained Yield).
Compound A-1：1HNMR(400MHz,DMSO)9.1(s,1H),7.40(d,1H),7.24(s,1H), 6.7-7.1(m,21H),3.1(td,1H),1.3(d,6H)。
Embodiment 2
According to prior art literature (Chemistry of Heterocyclic Compounds；vol,45；nb.1； (2009)；P.119-120 method synthetic intermediate A-1-0 described in).
Intermediate A -1-0 (1mol), BPO (0.1mol) and NBS (2.2mol) are dissolved in into carbon tetrachloride In (10 times of volumes), 60 DEG C are stirred 12 hours, and completely, concentration is removed after carbon tetrachloride TLC analytical reactions In being dissolved in dichloromethane, organic faciess anhydrous Na after washing2SO4It is dried, obtains in yellow oil after concentration Mesosome A-1-1 crude products, yield 89%.
Under nitrogen protection, by intermediate A -1-1 (1mol), 4- isopropyl diphenyl amine (2.2mol), 1,2- Cyclohexanediamine (4mol), Hydro-Giene (Water Science). (0.1mol) is dissolved in Isosorbide-5-Nitrae-dioxane, 100 DEG C of stirrings 6 Hour, LC-MS shows that reaction is complete, and MS measures C46H43N5(M+1=666.4).It is cooled to room temperature, And be slowly dropped in the water that stirred (10 volume ratio), extracted 3 times with ethyl acetate (3 volume), close And after organic faciess, be dried, silicagel column (ethyl acetate/petroleum ether=1 is crossed in concentration：10) white solid is obtained Compound A-2 (58% yield).
Compound A-2：1H NMR(400MHz,DMSO)9.17(s,1H),7.45(d,1H),7.3(s,1H), 6.7-7.2(m,19H),3.1(td,3H),1.3(d,18H)。
Embodiment 3
According to prior art literature (Chemistry of Heterocyclic Compounds；vol,45；nb.1； (2009)；P.119-120 method synthetic intermediate A-1-0 described in).
Intermediate A -1-0 (1mol), BPO (0.1mol) and NBS (2.2mol) are dissolved in into carbon tetrachloride In (10 times of volumes), 60 DEG C are stirred 12 hours, and completely, concentration is removed after carbon tetrachloride TLC analytical reactions In being dissolved in dichloromethane, organic faciess anhydrous Na after washing2SO4It is dried, obtains in yellow oil after concentration Mesosome A-1-1 crude products, yield 89%.
Under nitrogen protection, by intermediate A -1-1 (1mol), A-3-0 (2.2mol), 1,2- cyclohexanediamine (4 Mol), Hydro-Giene (Water Science). (0.1mol) is dissolved in Isosorbide-5-Nitrae-dioxane, and 100 DEG C are stirred 6 hours, LC-MS Show that reaction is complete, MS measures C58H47N5O2(M+1=846.4).Room temperature is cooled to, and is slowly dropped into To in the water that stirred (10 volume ratio), extracted 3 times with ethyl acetate (3 volume), after merging organic faciess, It is dried, silicagel column (ethyl acetate/petroleum ether=1 is crossed in concentration：10) compound as white solid A-3 (53% is obtained Yield).
Compound A-3：1H NMR(400MHz,DMSO)9.17(s,1H),7.45(d,1H),6.7-7.3(m,24 H),3.1(td,3H),1.3(d,18H)。
Additionally, device architecture embodiment is as follows：
ITO(50nm)/HIL(40nm)/HTL(45nm)/BH:BD (alloy 5%) (25nm)/TB (5 nm)/ET(20nm)/LiF(1nm)/Al(100nm)；Wherein, described HIL, HTL, ET, TB, BH are respectively following compound：
The blue-light device characteristic of compound A-1, A-2 and the A-3 as Dopant (alloy) is detected, such as Shown in table 1 below:
Table 1
As can be seen that compound A-1, A-2 and A-3 are showed on emission wavelength and colour code from upper table 1 Go out excellent blue light characteristic, blue light service life preferably, from data above compound A-1, A-2 and A-3 is proved All it is blue light Dopant (alloy) material for having good prospect.
The physicochemical properties of compound A-1, A-2 and A-3 are as shown in table 2：
Compound Vitrification point (DEG C) IP(eV) Mobility (cm2.V-1.s-1) Electric field intensity (V.cm-1)
A-1 132 5.60 3.5*10-2 4.0*105
A-2 145 5.23 3.8*10-2 4.0*105
A-3 180 5.21 3.8*10-2 4.0*105
Table 2
From Table 2, it can be seen that the glass transition temperature of compound A-1, A-2 and A-3 is high, mobility is good, so as to Beneficial to evaporation, it is seen that compound A-1, A-2 and A-3 are blue light Dopant (alloy) materials for having good prospect.
The specific embodiment of the present invention has been described in detail above, but it is intended only as example, and the present invention is simultaneously It is not restricted to particular embodiments described above.To those skilled in the art, it is any that the present invention is carried out Equivalent modifications and substitute also all among scope of the invention.Therefore, in the spirit and model without departing from the present invention Enclose lower made impartial conversion and change, all should cover within the scope of the invention.

Claims (9)

1. a kind of 1,3,4- tri- azepine pyrene derivatives that can be used for electroluminescent material, it is characterised in that its structure To lead to the compound shown in formula I：
Wherein, in R1～R7 any 2 be amido, 5 groups for being each independently non-amido in addition；A1～A4 It is each independently the group of non-amido.
2. 1,3,4- tri- azepine pyrene derivatives that can be used for electroluminescent material according to claim 1, its It is characterised by, the group of the non-amido is：Hydrogen, halogen, cyano group, C1～C10 alkyl, replacement do not take C3～C10 cycloalkyl in generation, C1～C10 alkoxyls, C2～C10 alkenyls, replace or do not replace C6～C30 aryl radicals, the C10～C30 condensed-nuclei aromatics for replacing or not replacing and C3～C30 heterocyclic arenes, C7～C30 aralkyl, the C3～C30 propenyloxy groups for replacing or not replacing.
3. 1,3,4- tri- azepine pyrene derivatives that can be used for electroluminescent material according to claim 2, its It is characterised by, it is selected from one of following compound：
4. a kind of 1,3,4- tri- azepines that can be used for electroluminescent material containing any one of claim 1-3 The OLED electron transport layer materials of pyrene derivatives.
5. a kind of 1,3,4- tri- azepines that can be used for electroluminescent material containing any one of claim 1-3 The OLED emitting layer materials of pyrene derivatives.
6. a kind of 1,3,4- tri- nitrogen that can be used for electroluminescent material containing any one of claim 1-3 The OLED hole transport layer materials of miscellaneous pyrene derivatives.
7. a kind of 1,3,4- tri- azepines that can be used for electroluminescent material containing any one of claim 1-3 The OLED of pyrene derivatives.
8. a kind of preparation method of OLED as claimed in claim 7, it is characterised in that the preparation method bag Include：
1) substrate for being provided with transparent anode electrode ITO is cleaned by ultrasonic into 5-10 minutes in isopropanol, and 20-30 minutes under ultraviolet light are exposed, subsequently 5-10 minutes is processed with plasma；
2) substrate after process is put into into evaporated device, hole transport layer material is deposited with first as hole transport Layer；
3) and then evaporation luminescent layer, mixing evaporation emitting layer material, and the Ir (ppy) 3 of 5-10%；
4) electron transport layer materials are subsequently adopted, one layer of electron transfer layer is deposited with substrate, be subsequently deposited with again 0.5-2nm thick LiF, is subsequently deposited with the thick metal Al of 100-200nm；
Wherein, one of the hole transport layer material, emitting layer material, electron transport layer materials are formula (I) compound shown in.
9. the preparation method of OLED according to claim 8, it is characterised in that
The thickness of the hole transmission layer is 30-50nm；
The thickness of the luminescent layer is 10-120nm；
The thickness of the electron transfer layer is 20-40nm.
CN201510658636.XA 2015-10-12 2015-10-12 1,3,4-triaza pyrene derivatives used for electroluminescent materials and applications thereof Pending CN106565711A (en)

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KR20140134884A (en) * 2013-05-15 2014-11-25 에스에프씨 주식회사 An electroluminescent compound and an electroluminescent device comprising the same

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* Cited by examiner, † Cited by third party
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Application publication date: 20170419