CN106608828A - Benzoperylene derivative for organic light-emitting material - Google Patents
Benzoperylene derivative for organic light-emitting material Download PDFInfo
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- CN106608828A CN106608828A CN201510695392.2A CN201510695392A CN106608828A CN 106608828 A CN106608828 A CN 106608828A CN 201510695392 A CN201510695392 A CN 201510695392A CN 106608828 A CN106608828 A CN 106608828A
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Abstract
The invention provides a benzoperylene derivative for an organic light-emitting material. The structure of the benzoperylene derivative is shown in the general formula 1 (as shown in the description), wherein two positions in R1-R12 are substituted for amino, and other positions are independently selected from hydrogen atom, halogen atom, cyano, substituted or unsubstituted alkyl, substituted or unsubstituted naphthenic base, substituted or unsubstituted alkoxy, substituted or unsubstituted alkenyl, substituted or unsubstituted aromatic base, substituted or unsubstituted aromatic condensed ring, substituted or unsubstituted aralkyl and substituted or unsubstituted acryloyloxy. The benzoperylene derivative is used in an organic light-emitting device (OLED), and particularly as an organic light-emitting material, used in an OLED luminous layer, an OLED electronic transmission layer or an OLED hole blocking layer, and has excellent performance mainly manifested in such aspects as solubility and heat stability.
Description
Technical field
The present invention relates to Material Field, more particularly to a kind of Ben Bing perylenes for electroluminescent organic material are derivative
Thing.
Background technology
Organic electroluminescent refers to that the thin-film device being prepared into by organic photoelectric functional material excites work in electric field
With lower luminous phenomenon, most potential flat panel display of future generation is described as by industrial circle and academia, is had
Low-power consumption, wide viewing angle, respond it is fast, lighter and thinner and can Flexible Displays the advantages of.
Organic electroluminescence device is also called Organic Light Emitting Diode (OLED), by transparent anode ITO, metal
Negative electrode and organic thin film layer are constituted.Under direct voltage drive, negative electrode injected electrons and anode injected holes
Move to organic luminous layer, finally meet in luminescent layer and recombination luminescence.Compared with inorganic semiconductor diode,
Organic semiconductor diodes due to the randomness of its structure, the diversity of material and cause carrier physical process
Seem increasingly complex, the organic material for electron transfer layer and hole blocking layer is most important.
Electroluminescent organic material as organic electroluminescence device core component, its heat endurance, light
Chemical stability, quantum efficiency, film forming and crystallinity etc. all have a great impact to making devices.Wherein,
CN104650040A discloses a kind of organic electroluminescent compounds of azophenlyene analog derivative, and its structural formula is：Wherein, the organic electroluminescent compounds are used at least luminescent layer, hole note
Enter one layer in layer, hole transmission layer, hole blocking layer, electron injecting layer or electron transfer layer or which floor in,
Have the advantages that electroluminescent efficiency is good and excitation is excellent and life-span length；CN104744369A is disclosed
A kind of electroluminescent organic material, it contains structural formula and isDerivative；Wherein,
The derivative defines the material of class spiro-compound due to having introduced 2 phenyl ring, increased molecular structure
Planar conjugate, improve the dissolubility of such electroluminescent organic material so as to easily prepare, meanwhile,
Such electroluminescent organic material can change the transition of electronics so as to glow peak due to the introducing of different substituents
Position can adjust, for the preparation of blue-light device in, can have the needs for meeting industrialized production.
The content of the invention
Present inventor has found a kind of Ben Bing perylene derivatives for electroluminescent organic material, can be used as having
The blue material of organic electro luminescent, also can be used for luminescent layer material of main part or alloy, electron transfer layer, hole
In barrier layer, with good dissolubility and heat endurance.
Technical scheme includes a kind of Ben Bing perylene derivatives for electroluminescent organic material, its feature
It is that its structure is shown in formula 1：
Wherein, have two positions to be replaced by amino in R1-R12, other positions separately selected from hydrogen atom,
Halogen atom, cyano group, replacement or the alkyl not replaced, the cycloalkyl for replacing or not replacing, replacement or not
Alkoxyl, replace or do not replace alkenyl, replace or do not replace aryl radical, replace or do not replace
Aromatic fused ring base, the aralkyl for replacing or not replacing, the propenyloxy group for replacing or not replacing；
A1-A4 is separately selected from hydrogen atom, halogen atom, cyano group, replacement or the alkyl not replaced, takes
Generation or do not replace cycloalkyl, replace or do not replace alkoxyl, replace or do not replace alkenyl, replace or
The aryl radical that do not replace, the aromatic heterocycle for replacing or not replacing, the aralkyl for replacing or not replacing, take
Generation or the propenyloxy group not replaced.
In one embodiment of the invention, the other positions in the R1-R12 are separately former selected from hydrogen
Son, halogen atom, cyano group, replacement or the C1-C10 alkyl not replaced, the C1-C10 for replacing or not replacing
Cycloalkyl, replacement or the C1-C10 alkoxyls not replaced, the C1-C10 alkenyls for replacing or not replacing, take
Generation or the C6-C30 aryl radicals not replaced, the C6-C30 aromatic fused ring bases for replacing or not replacing, replacement
Or do not replace C6-C30 aralkyl, replace or the C1-C10 propenyloxy groups that do not replace.
Preferably, the A1-A4 is separately selected from hydrogen atom, halogen atom, cyano group, replacement or not
Substituted C1-C10 alkyl, the C1-C10 cycloalkyl for replacing or not replacing, the C1-C10 for replacing or not replacing
Alkoxyl, replacement or the C1-C10 alkenyls not replaced, the C6-C30 aryl radicals for replacing or not replacing,
The C6-C30 aromatic heterocycles for replacing or not replacing, the C6-C30 aralkyl, the replacement that replace or do not replace
Or the C1-C10 propenyloxy groups not replaced.
In one embodiment of the invention, R5 and R10 are replaced by amino.
In another embodiment of the present invention, the other positions in R1-R12 are replaced by hydrogen atom.
In another embodiment of the presently claimed invention, A1-A4 is separately selected from the fragrance for replacing or do not replace
Alkyl, replacement or the aromatic heterocycle not replaced, the aralkyl for replacing or not replacing.
Ben Bing perylene derivatives of the present invention preferably are selected from following structure：
Technical scheme also includes a kind of OLED luminescent layers containing Ben Bing perylene derivatives described above.
Further, benzo described above is contained in the material of main part or alloy in the OLED luminescent layers
Perylene derivative.
Technical scheme also includes that a kind of OLED electronics containing Ben Bing perylene derivatives described above is passed
Defeated layer.
Technical scheme also includes a kind of resistance of the OLED holes containing Ben Bing perylene derivatives described above
Interlayer.
Technical scheme also includes a kind of organic electroluminescent containing Ben Bing perylene derivatives described above
Device.
The structure shown in formula 1 that the present invention is provided, therein defining and have in R1-R12 two positions by amino
Replace, and further specify that the classification of other substituents, the benzene for finally giving and perylene derivative are used for organic
In electroluminescent device, especially as a kind of electroluminescent organic material, for OLED luminescent layers, OLED
In electron transfer layer or OLED hole blocking layers, with good performance, be mainly manifested in hole transport ability,
The aspect such as dissolubility and heat endurance.
Specific embodiment
The invention provides a kind of Ben Bing perylene derivatives for electroluminescent organic material, it is characterised in that its
Structure is shown in formula 1：
Wherein, have two positions to be replaced by amino in R1-R12, other positions separately selected from hydrogen atom,
Halogen atom, cyano group, replacement or the alkyl not replaced, the cycloalkyl for replacing or not replacing, replacement or not
Alkoxyl, replace or do not replace alkenyl, replace or do not replace aryl radical, replace or do not replace
Aromatic fused ring base, the aralkyl for replacing or not replacing, the propenyloxy group for replacing or not replacing；
A1-A4 is separately selected from hydrogen atom, halogen atom, cyano group, replacement or the alkyl not replaced, takes
Generation or do not replace cycloalkyl, replace or do not replace alkoxyl, replace or do not replace alkenyl, replace or
The aryl radical that do not replace, the aromatic heterocycle for replacing or not replacing, the aralkyl for replacing or not replacing, take
Generation or the propenyloxy group not replaced.
In one embodiment of the invention, the other positions in the R1-R12 are separately former selected from hydrogen
Son, halogen atom, cyano group, replacement or the C1-C10 alkyl not replaced, the C1-C10 for replacing or not replacing
Cycloalkyl, replacement or the C1-C10 alkoxyls not replaced, the C1-C10 alkenyls for replacing or not replacing, take
Generation or the C6-C30 aryl radicals not replaced, the C6-C30 aromatic fused ring bases for replacing or not replacing, replacement
Or do not replace C6-C30 aralkyl, replace or the C1-C10 propenyloxy groups that do not replace.
Preferably, the A1-A4 is separately selected from hydrogen atom, halogen atom, cyano group, replacement or not
Substituted C1-C10 alkyl, the C1-C10 cycloalkyl for replacing or not replacing, the C1-C10 for replacing or not replacing
Alkoxyl, replacement or the C1-C10 alkenyls not replaced, the C6-C30 aryl radicals for replacing or not replacing,
The C6-C30 aromatic heterocycles for replacing or not replacing, the C6-C30 aralkyl, the replacement that replace or do not replace
Or the C1-C10 propenyloxy groups not replaced.
In one embodiment of the invention, R5 and R10 are replaced by amino.
In another embodiment of the present invention, the other positions in R1-R12 are replaced by hydrogen atom.
In another embodiment of the presently claimed invention, A1-A4 is separately selected from the fragrance for replacing or do not replace
Alkyl, replacement or the aromatic heterocycle not replaced, the aralkyl for replacing or not replacing.Benzo of the present invention
Perylene derivative preferably is selected from following structure：
Present invention also offers a kind of OLED luminescent layers containing Ben Bing perylene derivatives described above.Further
Ground, contains Ben Bing perylene derivatives described above in the material of main part or alloy in the OLED luminescent layers.
Present invention also offers a kind of OLED electron transfer layers containing Ben Bing perylene derivatives described above.
Present invention also offers a kind of OLED hole blocking layers containing Ben Bing perylene derivatives described above.
Present invention also offers a kind of organic electroluminescence device containing Ben Bing perylene derivatives described above.
Embodiment 1
1st, a kind of Ben Bing perylene derivatives for electroluminescent organic material, its structure is shown in formula 1-1：
2nd, the preparation method of the Ben Bing perylene derivatives (1-1)：
Under nitrogen protection, by 2,7- bis- it is bromo- (1,12) benzene and perylene (1mol), 7- quinazoline aniline (2.2mol),
1,2- cyclohexanediamine (4mol) and cuprous iodide (0.1mol) are dissolved in Isosorbide-5-Nitrae-dioxane, 100 DEG C of bars
Stir 6 hours under part, LC-MS shows that reaction is complete, and C50H30N6 (M+1=715.4) is cooled to room
Temperature, and be slowly dropped in the water of stirring (10 volume ratio), extracted 3 times with ethyl acetate (3 volume), close
And after organic phase, be dried, silicagel column (ethyl acetate/petroleum ether=1 is crossed in concentration：10) white solid is obtained
The Ben Bing perylene derivatives (1-1) (70% yield).
3rd, structural characterization：
1HNMR(400MHz,DMSO)9.30(s,2H),9.23(s,2H),8.1-7.8(m,3H),7.4-7.6(m,6
H),7.2(d,3H),7.0-6.9(m,6H),6.6-6.5(m,8H)。
Embodiment 2
1st, a kind of Ben Bing perylene derivatives for electroluminescent organic material, its structure is shown in formula 1-2：
2nd, the preparation method of the Ben Bing perylene derivatives (1-2)：
WillReplace withLC-MS shows
Show C54H34N2 (M+1=711.4), other raw materials and operating procedure obtain white solid with embodiment 1
The Ben Bing perylene derivatives (1-2) (65% yield).
3rd, structural characterization：
1HNMR(400MHz,DMSO)8.1-7.9(m,3H),7.6-7.4(m,11H),7.1-6.9(m,12H),6.
6-6.4(m,8H)。
Embodiment 3
1st, a kind of Ben Bing perylene derivatives for electroluminescent organic material, its structure is shown in formula 1-3：
2nd, the preparation method of the Ben Bing perylene derivatives (1-3)：
WillReplace with
LC-MS displays C50H38N2 (M+1=667.4), other raw materials and operating procedure are obtained with embodiment 1
Ben Bing perylene derivatives (1-3) (73% yield) described in white solid.
3rd, structural characterization：
1HNMR(400MHz,DMSO)8.1-7.9(m,3H),7.4(dd,4H),7.2(d,1H),6.8-6.6(m,10
H),6.4(d,8H),2.4(s,12H)。
Application Example
Device architecture is as follows：
ITO(50nm)/HIL(40nm)/HTL(45nm)/BH:BD (5%) (25nm)/TB (5nm)
/ET(20nm)/LiF(1nm)/Al(100nm)；
Wherein,
The Ben Bing perylene derivatives (1-1), (1-2) and (1-3) that embodiment 1-3 is obtained, make respectively
It is used in the preparation of blue-light device for blue light alloy, the characteristic value for obtaining device is as shown in the table：
Can obtain from table：The Ben Bing perylene derivatives (1-1), (1-2) and (1-3) in emission wavelength and
The blue light characteristic all shown on colour code, and blue lifetime is preferably, may with material of main part collocation on need into
One step is improved.At present, the Ben Bing perylene derivatives (1-1), (1-2) and (1-3) are illustrated from available data
All it is promising blue light dopant material.
Further, the physical property of the Ben Bing perylene derivatives (1-1), (1-2) and (1-3) is as follows
Shown in table：
Can obtain from table：The gamma transition temperature of the Ben Bing perylene derivatives (1-1), (1-2) and (1-3)
Degree is high, and mobility is good, particularly (1-1), may be relevant with the electron deficient of its side chain.
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 (10)
1. a kind of Ben Bing perylene derivatives for electroluminescent organic material, it is characterised in that its structure is formula 1
It is shown：
Wherein, have two positions to be replaced by amino in R1-R12, other positions separately selected from hydrogen atom,
Halogen atom, cyano group, replacement or the alkyl not replaced, the cycloalkyl for replacing or not replacing, replacement or not
Alkoxyl, replace or do not replace alkenyl, replace or do not replace aryl radical, replace or do not replace
Aromatic fused ring base, the aralkyl for replacing or not replacing, the propenyloxy group for replacing or not replacing；
A1-A4 is separately selected from hydrogen atom, halogen atom, cyano group, replacement or the alkyl not replaced, takes
Generation or do not replace cycloalkyl, replace or do not replace alkoxyl, replace or do not replace alkenyl, replace or
The aryl radical that do not replace, the aromatic heterocycle for replacing or not replacing, the aralkyl for replacing or not replacing, take
Generation or the propenyloxy group not replaced.
2. Ben Bing perylene derivatives according to claim 1, it is characterised in that R5 and R10 are replaced by amino.
3. Ben Bing perylene derivatives according to claim 1, it is characterised in that the other positions in R1-R12
Replaced by hydrogen atom.
4. Ben Bing perylene derivatives according to claim 1, it is characterised in that A1-A4 is separately selected from
The aryl radical, replacement or the aromatic heterocycle not replaced, the replacement that replace or do not replace or the aralkyl not replaced
Base.
5. Ben Bing perylene derivatives according to claim 1, it is characterised in that the Ben Bing perylene derivatives are preferred
From following structure：
6. a kind of OLED luminescent layers of the Ben Bing perylene derivatives containing described in any one in claim 1-5.
7. OLED luminescent layers according to claim 6, it is characterised in that in the OLED luminescent layers
Contain the Ben Bing perylene derivatives in material of main part or alloy.
8. a kind of OLED electron transfer layers of the Ben Bing perylene derivatives containing described in any one in claim 1-5.
9. a kind of OLED hole blocking layers of the Ben Bing perylene derivatives containing described in any one in claim 1-5.
10. a kind of organic electroluminescence of the Ben Bing perylene derivatives containing described in any one in claim 1-5
Part.
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| Application Number | Priority Date | Filing Date | Title |
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| CN201510695392.2A CN106608828A (en) | 2015-10-22 | 2015-10-22 | Benzoperylene derivative for organic light-emitting material |
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| CN201510695392.2A CN106608828A (en) | 2015-10-22 | 2015-10-22 | Benzoperylene derivative for organic light-emitting material |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111153810A (en) * | 2020-01-15 | 2020-05-15 | 合肥鼎材科技有限公司 | Compound, application thereof and organic electroluminescent device containing compound |
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