CN106967065A - Organic electroluminescent compounds and its luminescent device containing two carbazyl phenyl groups - Google Patents

Organic electroluminescent compounds and its luminescent device containing two carbazyl phenyl groups Download PDF

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CN106967065A
CN106967065A CN201710203319.8A CN201710203319A CN106967065A CN 106967065 A CN106967065 A CN 106967065A CN 201710203319 A CN201710203319 A CN 201710203319A CN 106967065 A CN106967065 A CN 106967065A
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黄锦海
苏建华
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Shanghai Taoe Chemical Technology Co Ltd
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Abstract

The invention provides a kind of organic electroluminescent compounds containing two carbazyl phenyl groups, the compound has preferable heat endurance, high-luminous-efficiency, high luminance purity, it can be used for making organic electroluminescence device, applied to organic solar batteries, OTFT or organophotoreceptorswith field.Present invention also offers a kind of organic electroluminescence device, it includes anode, negative electrode and organic layer, organic layer includes at least one layer of compound containing two carbazyl phenyl groups comprising just like structural formula I at least one layer in luminescent layer, hole injection layer, hole transmission layer, hole blocking layer, electron injecting layer, electron transfer layer, organic layer.

Description

Organic electroluminescent compounds and its luminescent device containing two carbazyl phenyl groups
Technical field
The present invention relates to field of organic electroluminescent materials, and in particular to a kind of Organic Electricity containing two carbazyl phenyl groups Electro luminescent compounds and its organic electroluminescence device, belong to organic electroluminescence device display technology field.
Background technology
Organic electroluminescence device (OLEDs) is by spin coating or vacuum evaporation deposition one between two metal electrodes The device that layer organic material is prepared from, a classical three layer organic electroluminescence device includes hole transmission layer, luminescent layer And electron transfer layer.The hole produced by anode through hole transmission layer with the electronics that is produced by negative electrode through combined with electron transfer layer Luminescent layer formation exciton, then lights.Organic electroluminescence device can be adjusted as desired by the material of luminescent layer is changed The light of the various needs of section transmitting.
Organic electroluminescence device is as a kind of new Display Technique, with self-luminous, wide viewing angle, low energy consumption, efficiency High, thin, rich color, fast response time, Applicable temperature scope are wide, low driving voltage, can make flexible with it is transparent Display panel and the particular advantages such as environment-friendly, can be applied on flat-panel monitor and a new generation's illumination, can also conduct LCD backlight.
Since invention at the bottom of 1980s, organic electroluminescence device has industrially been applied, such as As screens such as camera and mobile phones, but current OLED is low due to efficiency, and it is wider that the factor such as service life is short restricts it General application, particularly large screen display, it is therefore desirable to improve the efficiency of device.And restrict one of key factor just It is the performance of the electroluminescent organic material in organic electroluminescence device.Applying voltage-operated additionally, due to OLED When, Joule heat can be produced so that organic material is easily crystallized, have impact on life-span and the efficiency of device, therefore, it is also desirable to Develop the electroluminescent organic material of stability and high efficiency.
Organic electrophosphorescenpolymer phenomenon, breaches theoretical limitation of the organic electroluminescent quantum efficiency less than 25%, and lifting is arrived 100% (Baldo M.A., Forrest S.R.Et al, Nature, 1998,395,151-154), its application is also greatly carried The high efficiency of organic electroluminescence device.Usually, electroluminescent phosphorescence needs to use host-guest system technology, conventional to be used as phosphorus The CBP (4,4'-bis (9-carbazolyl)-biphenyl) of light material of main part has efficient and high triplet energy level, when its work During for material of main part, triplet energy state effectively can be transferred to object phosphorescent light-emitting materials from light emitting host material.But by Easily transmitted and the characteristic of electronics hardly possible flowing in CBP hole so that the charge unbalance of luminescent layer, as a result reduce the effect of device Rate.
The content of the invention
Present invention firstly provides a kind of organic electroluminescent compounds containing two carbazyl phenyl groups, it is with as follows Structural formula I compound：
Wherein, R1-R4Separately selected from hydrogen, deuterium, halogen, cyano group, containing straight chain or with side chain C1-C12 alkane Base, straight chain or with side chain C1-C8 alkoxyl, C6-C30 substitution or unsubstituted aryl, C3-C30 substitution or Unsubstituted heteroaryl, triaromatic amine base, carbazyl, triaryl phosphinyl；
Cz1-Cz5Two of which is selected from carbazyl, and other are hydrogen or D-atom.
Preferably, R1-R4Separately selected from hydrogen, deuterium, methyl, ethyl, propyl group, butyl, amyl group, hexyl, octyl group, different Propyl group, isobutyl group, the tert-butyl group, cyclohexyl, phenyl, xenyl, terphenyl, diphenyl benzene, naphthyl, phenanthryl, fluorenyl, anthryl, Dibenzofuran group, dibenzothiophenes base, benzo phenanthryl, Qu Ji, fluoranthene base, pyrenyl, perylene base, carbazyl, triaromatic amine base, with Upper aryl can be further by straight chain or with side chain C1-C12 alkyl replace.
It is further preferred that the organic electroluminescent compounds containing two carbazyl phenyl groups of the present invention are having structure Formula 1-52 compound：
The organic electroluminescent compounds containing two carbazyl phenyl groups of the present invention can be applied in organic electroluminescent Device, organic solar batteries, OTFT or organophotoreceptorswith field.
Present invention also offers a kind of organic electroluminescence device, the device includes anode, negative electrode and organic layer, organic layer Include at least one in luminescent layer, hole injection layer, hole transmission layer, hole blocking layer, electron injecting layer, electron transfer layer Layer, wherein the compound containing two carbazyl phenyl groups that at least one layer contains as described in structural formula I in the organic layer：
Wherein R1-R4And Cz1-Cz5It is defined as described above.
Wherein organic layer is luminescent layer；
Or organic layer is luminescent layer and electron transfer layer；
Or organic layer is luminescent layer, electron transfer layer and electron injecting layer；
Or organic layer is hole transmission layer and luminescent layer；
Or organic layer is hole injection layer, hole transmission layer and luminescent layer；
Or organic layer is hole transmission layer, luminescent layer and electron transfer layer；
Or organic layer is hole injection layer, hole transmission layer, luminescent layer and electron transfer layer；
Or organic layer is hole injection layer, hole transmission layer, luminescent layer, electron transfer layer and electron injecting layer；
Or organic layer is hole injection layer, hole transmission layer, barrier layer, luminescent layer, electron transfer layer and electron injection Layer；
Or organic layer is hole transmission layer, luminescent layer, electron transfer layer, electron injecting layer and hole blocking layer；
Or organic layer is hole transmission layer, luminescent layer, electron injecting layer and hole blocking layer.
Preferably, wherein the layer where compound as described in structural formula I be luminescent layer, hole transmission layer, hole injection At least one layer in layer.
Preferably, the hole transmission layer compound wherein described in structural formula I is structural formula 1-52 compound.
, can be independent when the compound containing two carbazyl phenyl groups as described in structural formula I is used for luminescent device preparation Use, can also be used in mixed way with other compounds；The electroluminescent containing two carbazyl phenyl groups as described in structural formula I Compound can be used alone a kind of compound therein, and the two or more compounds in structural formula I can also be used simultaneously.
The organic electroluminescence device of the present invention, further preferred mode is that the organic electroluminescence device includes sun Contain in pole, hole injection layer, hole transmission layer, luminescent layer, electron transfer layer, electron injecting layer and negative electrode, wherein luminescent layer At least one structural formula I compound；It is further preferred that containing at least one structural formula 1-52 compound in luminescent layer.
The gross thickness of the organic electroluminescence device organic layer of the present invention is 1-1000nm, preferably 50-500nm.
The organic electroluminescence device of the present invention is when having structural formula I compound using the present invention, and can arrange in pairs or groups makes With other materials, such as in hole injection layer, hole transmission layer, luminescent layer, electron transfer layer, electron injecting layer and barrier layer Deng, and obtain blue and green light, gold-tinted, feux rouges or white light.
The hole transmission layer and hole injection layer of organic electroluminescence device of the present invention, material requested have good hole Transmission performance, can effectively be transferred to hole on luminescent layer from anode.There is compound described in structural formula I except above-mentioned Outside, other small molecules and macromolecular organic compound, including but not limited to carbazole compound, triaromatic amine can also be included Compound, benzidine compound, compound of fluorene class, phthalocyanine-like compound, the miscellaneous triphen of six cyano group six (hexanitrilehexaazatriphenylene), the cyanogen dimethyl-parabenzoquinone (F4- of 2,3,5,6- tetra- fluoro- 7,7', 8,8'- tetra- TCNQ), PVK, polythiophene, polyethylene or polyphenyl sulfonic acid.
The luminescent layer of the organic electroluminescence device of the present invention, with the good characteristics of luminescence, can be adjusted as needed The scope of visible ray.In addition to the present invention is with Compounds of structural formula I, following compound can also be contained, including but not limit In naphthalene compounds, pyrene compound, compound of fluorene class, luxuriant and rich with fragrance class compound, class compound in the wrong, glimmering anthracene compound, anthracene class Compound, pentacene class compound, perylene classes compound, two aromatic ethylene class compounds, triphenylamine ethylene compounds, amine chemical combination Thing, benzimidazoles compound, furfuran compound, organic metal chelate complex.
The Organic Electron Transport Material requirement of organic electroluminescence device of the present invention has good electronic transmission performance, energy It is enough effectively electronics from cathode transport to luminescent layer in, with very big electron mobility.Following compound can be selected, but It is not limited to this：Oxa- oxazole, thiazole compound, triazole compound, three nitrogen piperazine class compounds, triazine class chemical combination Thing, quinoline class compound, phenodiazine anthracene compound, siliceous heterocycle compound, quinolines, ferrosin class compound, Metallo-chelate (such as Alq3), fluorine substituted benzene compound, benzimidazoles compound.
Electronics, effectively can be injected into organic layer by the electron injecting layer of organic electroluminescence device of the present invention from negative electrode In, it is mainly selected from the compound of alkali metal or alkali metal, or compound or alkali selected from alkaline-earth metal or alkaline-earth metal Metal complex, can select following compound, but not limited to this：Alkali metal, alkaline-earth metal, rare earth metal, alkali metal Oxide or halide, the oxide of alkaline-earth metal or halide, the oxide of rare earth metal or halide, alkali metal Or the organic complex of alkaline-earth metal；Preferably lithium, lithium fluoride, lithia, lithium nitride, 8-hydroxyquinoline lithium, caesium, carbonic acid Caesium, 8-hydroxyquinoline caesium, calcium, calcirm-fluoride, calcium oxide, magnesium, magnesium fluoride, magnesium carbonate, magnesia, these compounds can individually make With can also mixture use, can also be used cooperatively with other electroluminescent organic materials.
Each layer of organic layer in the organic electroluminescence device of the present invention, can be steamed by vacuum vapour deposition, molecular beam It is prepared by the modes such as plating method, the dip coating for being dissolved in solvent, spin-coating method, stick coating method or inkjet printing.It can make for metal motor Prepared with vapour deposition method or sputtering method.
Device experimental shows that compound containing two carbazyl phenyl groups of the present invention as described in structural formula I has preferable Heat endurance, high-luminous-efficiency, high luminance purity.Contain the organic electroluminescent compounds system of two carbazyl phenyl groups using this The organic electroluminescence device of work has the advantages that electroluminescent efficiency is good and excitation is excellent and long lifespan.
Brief description of the drawings
Fig. 1 is a kind of organic electroluminescence device structural representation of the invention；
Wherein, 110 glass substrate is represented as, 120 are represented as anode, and 130 are represented as hole injection layer, and 140 are represented as sky Cave transport layer, 150 are represented as barrier layer, and 160 are represented as luminescent layer, and 170 are represented as electron transfer layer, and 180 are represented as electronics note Enter layer, 190 are represented as negative electrode.
Embodiment
In order to describe the present invention in more detail, especially exemplified by example below, but not limited to this.
Embodiment
Intermediate 1a synthesis
In 500mL three-necked flasks, add carbazole (10g, 60mmol) be dissolved in 100mL DMF, by potassium tert-butoxide (6.72g, 60mmol) be dissolved in 70mL DMF, be slowly dropped under nitrogen protection, 3h is stirred at room temperature after completion of dropping, after by 2,6- difluoros Cyanophenyl (4.17g, 30mmol) is dissolved in 50mL DMF, is slowly dropped into, after completion of dropping, is warming up to 80 DEG C, stirs 8h.Reaction knot Shu Hou, is cooled to room temperature, and reaction solution is poured into water, and suction filtration goes out solid, and crude product is further purified using column chromatography, obtains white Color solid 11g, yield 88%.
Intermediate 1b synthesis
Synthetic method is with intermediate 1a, except being replaced with 3,5- difluorobenzonilyiles outside 2,6- difluorobenzonilyiles, yield 70%.
Intermediate 1c synthesis
Synthetic method is with intermediate 1a, except being replaced with 2,4- difluorobenzonilyiles outside 2,6- difluorobenzonilyiles, yield 70%.
Embodiment 1
The synthesis of compound 1
Intermediate 1a (4.3g, 10mmol), PA (1.13g, 12mmol), bromine are added in 100mL single port bottles Change cuprous (0.54mmol, 80mg), 1-10 ferrosins (0.54mmol, 100mg), zinc iodide (1.11mmol, 354mg) and neighbour two Chlorobenzene 30mL, 130 DEG C of reaction 24h of blowing air, is cooled to after room temperature and is diluted with EA, is filtered to remove inorganic salts, makes after filtrate concentration Use column chromatography (PE:EA=3:1).Obtain white solid 3.1g, yield 60%.
Embodiment 2-7
Following compound is prepared with similar method：
Embodiment 8-14
The preparation of organic electroluminescence device
OLED is prepared using the compound in the embodiment of the present invention.
First, by electrically conducting transparent ito glass substrate 110 (carrying anode 120 above) (the limited public affairs of South China glass group share Department) pass through successively：Deionized water, ethanol, acetone and deionized water are cleaned, then with oxygen plasma treatment 30 seconds.
Then, PEDOT thick spin coating 35nm on ITO:PSS (Polyglycolic acid fibre-poly- (styrene sulfonate)) is 130,150 degree of hole injection layer is lower to be dried 30 minutes；
Then, it is hole mobile material 140 that the thick TAPC of 45nm are deposited on hole injection layer.
Then, TCTA is deposited, the thick electronic barrier layers 150 of 5nm are formed.
Then, the thick luminescent layers 160 of 20nm are deposited on electronic barrier layer, wherein, the compounds of this invention is luminous for main body Material, and with 8% weight than Ir (ppy)3It is used as phosphorescence doping guest materials.
Then, the thick BmPYPB of 55nm are deposited on luminescent layer and are used as electron transfer layer 170.
Finally, evaporation 1nm LiF are that electron injecting layer 180 and 80nm Al are used as device cathodes 190.
Prepared device (structural representation is shown in Fig. 1) measured with Photo Research PR650 spectrometers 5000cd/m2Brightness under current efficiency be such as table 1.
Comparative example
Device prepared by comparative example is with embodiment 8-14 device preparation method, except replacing the present inventionization with CBP Compound as material of main part outside.
Table 1
Embodiment Compound Current efficiency (cd/A) Glow color
8 1 67 Green glow
9 6 65 Green glow
10 13 68 Green glow
11 15 69 Green glow
12 23 63 Green glow
13 24 64 Green glow
14 41 65 Green glow
Comparative example CBP 45 Green glow
Structural formula is as follows described in device：
As can be seen from the table, new organic materials of the invention are used for organic electroluminescence device, can reduce work Voltage, improves device efficiency, is the phosphorescent light body material with premium properties.As described above, the compound of the present invention has height Stability, the organic electroluminescence device of preparation has high efficiency and optical purity.

Claims (9)

1. a kind of organic electroluminescent compounds containing two carbazyl phenyl groups, it is characterised in that it is with following structural formula I compound：
Wherein, R1-R4Separately selected from hydrogen, deuterium, halogen, cyano group, containing straight chain or with side chain C1-C12 alkyl, straight Chain or with side chain C1-C8 alkoxyl, C6-C30 substitution or unsubstituted aryl, C3-C30 substitution or unsubstituted Heteroaryl, triaromatic amine base, carbazyl, triaryl phosphinyl；
Cz1-Cz5Two of which is selected from carbazyl, and other are hydrogen or D-atom.
2. the organic electroluminescent compounds according to claim 1 containing two carbazyl phenyl groups, it is characterised in that R1- R4Separately it is selected from hydrogen, deuterium, methyl, ethyl, propyl group, butyl, amyl group, hexyl, octyl group, isopropyl, isobutyl group, tertiary fourth Base, cyclohexyl, phenyl, xenyl, terphenyl, diphenyl benzene, naphthyl, phenanthryl, fluorenyl, anthryl, dibenzofuran group, hexichol Bithiophene base, benzo phenanthryl, Qu Ji, fluoranthene base, pyrenyl, perylene base, carbazyl, triaromatic amine base, above aryl can be further C1-C12 alkyl by straight chain or with side chain replaces.
3. the organic electroluminescent compounds according to claim 1 containing two carbazyl phenyl groups, it is characterised in that its For following structural 1-52 compound：
4. a kind of organic electroluminescence device, it includes anode, negative electrode and organic layer, and organic layer injects comprising luminescent layer, hole At least one layer in layer, hole transmission layer, hole blocking layer, electron injecting layer, electron transfer layer, it is characterised in that in organic layer At least one layer includes the compound as claimed in claim 1 containing two carbazyl phenyl groups.
5. organic electroluminescence device according to claim 4, it is characterised in that contain two carbazoles as described in structural formula I Layer where the compound of base phenyl group is at least one layer in luminescent layer, hole transmission layer, hole injection layer.
6. organic electroluminescence device according to claim 4, it is characterised in that contain two carbazoles as described in structural formula I The compound of base phenyl group is used alone, or is used in mixed way with other compounds.
7. organic electroluminescence device according to claim 4, it is characterised in that contain two carbazoles as described in structural formula I A kind of compound therein is used alone in the compound of base phenyl group, or uses the two or more chemical combination in structural formula I simultaneously Thing.
8. organic electroluminescence device according to claim 4, it includes anode, hole injection layer, hole transmission layer, hair Photosphere, electron transfer layer, electron injecting layer and negative electrode, it is characterised in that contain at least one structural formula I chemical combination in luminescent layer Thing.
9. organic electroluminescence device according to claim 4, it includes anode, hole injection layer, hole transmission layer, hair Photosphere, electron transfer layer, electron injecting layer and negative electrode, it is characterised in that contain at least one structural formula 1-52 in hole transmission layer Compound.
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CN112300152B (en) * 2019-07-25 2021-11-19 南京高光半导体材料有限公司 Novel bipolar green phosphorescent host material and OLED (organic light emitting diode) light emitting device containing same
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Application publication date: 20170721