CN106478529B - Carrier generation materials and Organic Light Emitting Diode - Google Patents
Carrier generation materials and Organic Light Emitting Diode Download PDFInfo
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- C07—ORGANIC CHEMISTRY
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- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/36—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems
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- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
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Abstract
The present invention provides a kind of carrier generation materials, chemical structure are as follows:Wherein R1For hydrogen or alkyl；R2It is each independently hydrogen, halogen ,-CN ,-CF3、‑NO2Or alkyl；R3It is each independently hydrogen, halogen ,-CN ,-CF3、‑NO2Or alkyl；R4For hydrogen, halogen ,-CN ,-CF3、‑NO2Or alkyl；R5For hydrogen, halogen ,-CN ,-CF3、‑NO2Or alkyl；R6For=O ,=NH or malononitrile group；And R7For hydrogen, halogen ,-CN ,-CF3、‑NO2Or alkyl.
Description
[technical field]
The present invention relates to Organic Light Emitting Diode, relate more specifically to the material composition of its carrier generating layer.
[background technique]
Compared with inorganic compound, the material system of organic compound is more, can synthesize respectively by MOLECULE DESIGN appropriate
The organic material of kind Premium Features.The film that organic compound is formed has great flexibility and superior machinability.
Due to above-mentioned advantage, functional organic material attracts attention in photonics and electronics technologies in recent years.
Since organic compound itself does not have carrier, so substantially having superior insulation performance.It is organic utilizing
In the electronic field of material, the main exercise use of organic compound is insulator such as insulating materials, protection materials and covering material
Material.However electronic field starts using the mechanism that a large amount of electric currents can be allowed to flow in organic material.It for example, can be by total thickness about
The organic film of 100nm is located between electrode, and organic cavity transmission layer and organic electron transport layer group by stacking layer by layer
Body is stacked at organic film, and uses luminescent material (fluorescent material or phosphor material) as electron-hole binder course.By
Apply voltages to device, electron-hole can be allowed to be incorporated into luminous material layer with shine, i.e., so-called Organic Light Emitting Diode
(OLED)。
For the luminous efficiency for further promoting OLED, the Patent Case for having part previous proposes the concept of carrier generating layer.
Sequentially overlapped anode, the first electroluminescence layer, carrier generating layer, the second electroluminescence layer and cathode.It should be noted that
Electroluminescence layer (hereinafter referred to as " EL layers ") refers to containing the organic compound that can be shone by injection carrier
Layer.In addition, carrier generating layer is not attached to external circuit and is floating electrode.
When providing voltage V between the anode and cathode in OLED, carrier generating layer generates electrons and holes, and divides
The first electroluminescence layer is not injected electrons into and injects holes into the second electroluminescence layer.It is above-mentioned that there are double electroluminescence layers
OLED compared with the OLED of the electroluminescence layer only with single layer, twice of light quantity (but needs can be emitted under same current
Twice or more of voltage).
The OLED of such carrier generating layer is introduced, by overlapped several layers of electroluminescence layer, current efficiency be can be improved
Several times.From the point of view of theoretically, with the raising of current efficiency, the extension it can be expected that device lifetime is answered, in particular, tandem element
Used current density is the half of single luminous layer elements under same brightness, so that component life is extended.However
Current carrier generating layer is later because developing due to material selects rareness.It is generated in conclusion needing novel carrier at present
Material is applied to OLED, to further increase feasibility of the carrier generating layer in OLED.
[summary of the invention]
The carrier generation materials that one embodiment of the invention provides, chemical structure are as follows:
Wherein R1For hydrogen or alkyl；R2It is each independently hydrogen, halogen ,-CN ,-CF3、-NO2Or alkyl；R3It is respectively independent
Ground is hydrogen, halogen ,-CN ,-CF3、-NO2Or alkyl；R4For hydrogen, halogen ,-CN ,-CF3、-NO2Or alkyl；R5For hydrogen, halogen
Element ,-CN ,-CF3、-NO2Or alkyl；R6For=O ,=NH or malononitrile group；And R7For hydrogen, halogen ,-CN ,-CF3、-NO2、
Or alkyl.
The Organic Light Emitting Diode that one embodiment of the invention provides, comprising: anode；Cathode；Carrier generation materials layer, packet
Above-mentioned carrier generation materials are included, and between anode and cathode；First luminescent layer is located at anode and carrier generation materials
Between layer；And second luminescent layer, between cathode and carrier generation materials layer.
[Detailed description of the invention]
Fig. 1 is the schematic diagram of the Organic Light Emitting Diode in one embodiment of the invention.
[description of symbols]
11 anodes
13 first luminescent layers
15 carrier generation materials layers
17 second luminescent layers
19 cathodes
100 Organic Light Emitting Diodes
[specific embodiment]
The carrier generation materials that one embodiment of the invention provides are as shown in Equation 1.In formula 1, R1For hydrogen or alkyl.R2Respectively
From independently being hydrogen, halogen ,-CN ,-CF3、-NO2Or alkyl.R3It is each independently hydrogen, halogen ,-CN ,-CF3、-NO2Or alkane
Base.
The synthesis mode of the carrier generation materials of above-mentioned formula 1 is as follows.Firstly, compound such as formula 2 need to be synthesized first.In formula 2
In, R1Type can be reacted and be changed by the selection of commercial goods or general chemical, this will not be repeated here.
Then 2 product of modus ponens is reacted with acetylene compound such as formula 3.In formula 3, R2Type can be by the selection of commercial goods
Or general chemical reacts and changes, this will not be repeated here.
Then 3 product of modus ponens is reacted with diamine compound such as formula 4, that is, forms product such as formula 1.In formula 4, R3Type can
Changed by the selection of commercial goods or general chemical reaction, this will not be repeated here.
The carrier generation materials that one embodiment of the invention provides are as shown in Equation 5.In formula 5, R1For hydrogen or alkyl.R2Respectively
From independently being hydrogen, halogen ,-CN ,-CF3、-NO2Or alkyl.R4For hydrogen, halogen ,-CN ,-CF3、-NO2Or alkyl.
The synthesis mode of the carrier generation materials of above-mentioned formula 5 is as follows.3 product of modus ponens is reacted with diamine compound such as formula 6,
Form product such as formula 5.In formula 6, R4Type can be reacted and be changed by the selection of commercial goods or general chemical, herein not
It repeats.
The carrier generation materials that one embodiment of the invention provides are as shown in Equation 7.In formula 7, R5For hydrogen, halogen ,-CN ,-
CF3、-NO2Or alkyl.
The synthesis mode of the carrier generation materials of above-mentioned formula 7 is as follows.Second dione compounds are taken to react with tetramine compound
Such as formula 8, that is, form product such as formula 7.In formula 8, R5Type can be reacted and be changed by the selection of commercial goods or general chemical,
This will not be repeated here.
The carrier generation materials that one embodiment of the invention provides are as shown in Equation 9.In formula 9, R6For=O ,=NH or third
Dinitrile.R7For hydrogen, halogen ,-CN ,-CF3、-NO2Or alkyl.
The synthesis mode of the carrier generation materials of above-mentioned formula 9 is as follows.Firstly, 2 are taken, the chloro- 1,4-naphthoquinone of 3- bis- and adjacent benzene
Dicarboximide reactant salt such as formula 10.
Then the product of modus ponens 10 is reacted with diamine monohydrate such as formula 11.
Then the product of modus ponens 11 is reacted with second dione compounds such as formula 12.In formula 12, R7Type can be by commercially available quotient
The selection of product or general chemical react and change, and this will not be repeated here.
In another embodiment, retrievable 12 product is reacted with malononitrile such as formula 13.The product of formula 12 and the production of formula 13
Object belongs to the compound of formula 9, and difference is R6For=O or malononitrile group.
Above-mentioned carrier generation materials can be applied to Organic Light Emitting Diode.As shown in Figure 1, Organic Light Emitting Diode 100
It may include anode 11, cathode 19 and the carrier generation materials layer 15 being located between anode 11 and cathode 19.Above-mentioned organic hair
Optical diode 100 also includes the first luminescent layer 13, and between anode 11 and carrier generation materials layer 15 and second shines
Layer 17, between cathode 19 and carrier generation materials layer 15.
In an embodiment of the present invention, the thickness of anode 11 is about 15 nanometers, material can for indium tin oxide (ITO),
Indium-zinc oxide (IZO), aluminium zinc oxide (AZO), cadmium tin-oxide (CTO), tin oxide (SnO2) or zinc oxide (ZnO) etc.
Transparent conductive material.For the thickness of cathode 19 about between 75 to 100 nanometers, material can be magnesium alloy, magnesium silver alloy, magnesium
Indium alloy, aluminium lithium alloy or aluminium.About between 120 nanometers to 140 nanometers, material can be the thickness of first luminescent layer 13
N, N'- diphenyl-N, N'- (1- naphthalene) -1,1'- biphenyl -4,4'- diamines, 4,4', 4 "-three (carbazole -9- base) triphenylamines, 9,
Two -9H- carbazole of 9'- (1,3- phenyl), three (2- phenylpyridines) close iridium, Ir (piq) 3, bis- (4,6- difluorophenyl pyridinato-N, C2)
Pyridinecarboxylic closes iridium, 1,3,5- tri- (1- phenyl -1H- benzimidazolyl-2 radicals-yl) benzene, 3,3'- [5'- [3- (3- pyridyl group) phenyl]
[1,1':3', 1 "-terphenyl] -3,3 "-diyl] two pyridines, lithium fluoride and electron transfer layer be deposited altogether, aluminium.Second luminescent layer 17
Thickness about between 120 nanometers to 140 nanometers, material can be N, N'- diphenyl-N, N'- (1- naphthalene) -1,1'- connection
Benzene -4,4'- diamines, 4,4', 4 "-three (carbazole -9- base) triphenylamines, two -9H- carbazole of 9,9'- (1,3- phenyl), three (2- phenyl
Pyridine) close iridium, Ir (piq) 3, bis- (4,6- difluorophenyl pyridinato-N, C2) pyridinecarboxylics conjunction the iridium, (1- phenyl -1H- of 1,3,5- tri-
Benzimidazolyl-2 radicals-yl) benzene, 3,3'- [5'- [3- (3- pyridyl group) phenyl] [1,1':3', 1 "-terphenyl] -3,3 "-diyl] two
Pyridine.The thickness of carrier generation materials layer 15 about between 1 nanometer to 5 nanometers, material can for formula 1, formula 5, formula 7 or
9 compound represented of formula.
Above-mentioned Organic Light Emitting Diode 100 can further include other common stratified materials, as electron injecting layer, hole are infused
Enter layer, electron transfer layer, hole transmission layer, hole blocking layer, other function layer or combinations of the above, should depend on the needs.?
In another embodiment of the present invention, Organic Light Emitting Diode 100 may include multiple carrier generating layers, and the number of luminescent layer is to carry
The number+1 of sub- generating layer is flowed, the material of wherein at least one carrier generating layer is to change shown in formula 1, formula 5, formula 7 or formula 9
Close object.
In order to which above and other purpose, feature and advantage of the invention can be clearer and more comprehensible, multiple implementations are cited below particularly
The appended diagram of example cooperation, is described in detail below:
Embodiment
Embodiment 1
Selenium dioxide (8g, 72mmol) and water (1g, 55mmol) is placed in 100ml two-neck bottle, and 40ml 1 is added,
4- dioxanes, reaction are warming up to reflux, and the 4- methyl acetophenone bought by Alfa Aesar is added after selenium dioxide dissolution
(5.37g, 40mmol), and react 6 hours.Filtering and with ethyl acetate rinse filter cake after reaction, and spin concentration filtrate
It to remove organic solvent, then is recrystallized with hot water, obtains white solid 5.88g, yield 88%.Above-mentioned reaction can refer to
P.Wang,W.-J.Tao,X.-L.Sun,S.Liao,Y.Tang,J.Am.Chem.Soc.,2013,135,16849–16852.On
State reaction equation such as formula 14.The spectrum of product is as follows:1H NMR (400MHz, CDCl3): δ 9.65 (s, 1H), 8.09 (d, J=
8.4Hz, 2H), 7.31 (d, J=8.0Hz, 2H), 2.43 (s, 3H).
The product (33.3mg, 0.2mmol) of formula 14 and dibenzenyl (42.8mg, 0.24mmol) and molecular sieve are placed in
In high-voltage tube, and 0.5ml 1 is added, 1.5ml is added under nitrogen in 2- dichloroethanes, ferric trichloride (97.4mg, 0.6mmol)
1,2- dichloroethanes is dissolved and is added into reaction, is taken out filling nitrogen and is placed on room temperature reaction 1 hour.1ml is added after reaction
Water neutralizes, and with ethyl acetate rinse after filtering, and spin concentration filtrate is worked as with removing organic solvent with ethyl acetate and n-hexane
Make eluent (1:4, v/v), carries out col-umn chromatography separation, obtain red solid 39mg, yield 60%.Above-mentioned reaction such as formula 15,
The spectrum of product is as follows:1H NMR(400MHz,CDCl3):δ8.00(s,1H),7.30-7.24(m,4H),7.12-7.06(m,
5H),6.95-6.89(m,3H),2.40(s,3H)；13C NMR(100MHz,CDCl3):δ180.6(CO),179.3(CO),
152.9(C),140.9(C),137.5(C),135.9(CH),135.7(C),134.1(C),133.5(C),130.9(C),
130.8(CH),130.3(2CH),130.2(CH),129.0(2CH),128.1(2CH),128.1(CH),127.4(2CH),
127.2(CH),21.0(CH3)。
Embodiment 2
The product (324.4mg, 1mmol) and o-phenylenediamine (108.2mg, 1mmol) of modus ponens 15 are placed in 100ml round-bottomed bottle
In, and 40ml toluene is added, refluxed under nitrogen, which is installed on, using Dean-Stark reacts.Spin concentration removal after reaction has
Solvent, and to be recrystallized after the dissolution of a small amount of ethyl acetate with n-hexane, obtain faint yellow solid 361mg, yield 91%.
Above-mentioned reaction such as formula 16, the spectrum of product are as follows:1H NMR(400MHz,CDCl3):δ9.38(s,1H),8.38
(d, J=8.4Hz, 1H), 8.13 (d, J=8.4Hz, 1H), 7.83 (t, J=8.4Hz, 1H), 7.75 (t, J=8.4Hz, 1H),
7.52-7.47(m,2H),7.33-7.22(m,10H),2.70(s,3H)；13C NMR(100MHz,CDCl3):δ143.4(C),
142.7(2C),141.8(C),141.3(C),138.6(C),137.7(C),137.7(C),136.4(C),131.7(2CH),
131.5(C),131.0(CH),130.8(C),130.7(2CH),130.0(CH),129.7(CH),129.3(CH),129.2
(CH),127.7(2CH),127.7(CH),127.0(2CH),126.9(CH),126.3(CH),125.1(CH),21.7(CH3)。
The product of modus ponens 16 is dissolved in methylene chloride, and being configured to concentration is 10-5The solution of M.The ultraviolet light for measuring solution is inhaled
After receiving spectrum (UV-abs) and photoluminescence luminescent spectrum (PL), the intersection numerical value of the two is 2.7eV to get Eg divided by 1241.
Then the ultraviolet light photoelectron spectroscopy (UPS) of the product of formula 16 is measured to obtain its HOMO value as -7.5eV.It is above-mentioned with
UPS spectrum convert HOMO value method see Adv.Funct.Mater.2012,22,600-608 and J.Mater.Chem.C,
2014,2,1982–1989.HOMO value is subtracted into Eg up to LUMO value (- 4.8eV).
Embodiment 3
4, the 4'- dibromo benzil (2g, 5.4mmol) bought by Alfa Aesar is placed in high-voltage tube, cyaniding is added
Cuprous (1.07g, 12mmol) after vacuumizing logical nitrogen, is added DMF (30mL), is warming up to 160 DEG C and stirs 20 hours.Reaction knot
Used saturated salt solution and ether extraction after beam, collected organic layer, with magnesium sulfate water removal, spin concentration, then with methylene chloride and
N-hexane carries out col-umn chromatography separation, obtains yellow solid 0.8g, yield 40% as eluent (5:1, v/v).Above-mentioned reaction
Formula such as formula 17, the spectrum of product are as follows:1H NMR(400MHz,CDCl3): δ 8.09 (d, J=8Hz, 4H), 7.83 (d, J=8Hz,
4H).13C NMR(100MHz,CDCl3,δ):190.8,135.3,132.9,130.4,118.4,117.4。
By Alfa Aesar four hydrochloride (0.5g, 1.76mmol) of 1,2,4,5- benzene tetramine bought and the product of formula 17
(1g, 3.85mmol) is placed in reaction flask, and sodium acetate (0.576g, 7.02mmol) and n-butanol (50mL) is added, is warming up to 120
DEG C reaction 20 hours.After reaction, yellow mercury oxide is generated in solution at this time, is then separated by filtration sediment, and with just
Hexane and ether clean this yellow solid, then this yellow solid can be obtained glassy yellow powder 0.8g via heat sublimation after purification, produce
Rate 25%.Above-mentioned reaction equation such as formula 18, the spectrum of product are as follows: 1H NMR (400MHz, CDCl3): δ 9.08 (s, 2H),
7.72 (s, 16H) .HRMS (EI, m/z): calculated value (C38H18N8): 586.1654, measured value: 586.1649 (M+).
It is similar with calculation with the measurement of embodiment 2, it is known that the Eg of the product of formula 18 is 2.8eV, and HOMO is -7.2eV,
And LUMO is -4.4eV.
Embodiment 4
The 2,3 dichlro 1,4 naphtho quinone (4.54g, 20mmol) and phthalimide potassium that will be bought by Alfa Aesar
(15.54g, 84mmol) is placed in reaction flask, is added acetonitrile (100mL), is warming up to 85 DEG C and is reacted 3 hours.After reaction, this
When solution in have yellow mercury oxide, then sediment is separated by filtration, and with water and methanol cleaning this yellow solid, yellow powder can be obtained
Last product, yield 97%.Above-mentioned reaction equation such as formula 19, the spectrum of product are as follows: 1H NMR (400MHz, CDCl3): δ 8.21
(m,2H),7.86(m,4H),7.83(m,2H),7.75(m,4H)。
Will in product (2.24g, 5mmol) the merging reaction flask of formula 19, be added hydrazine hydrate (that is, diamine monohydrate,
20mL) with water (150mL), it is warming up to 70 DEG C and reacts 3 hours.After reaction, there is violet precipitate in solution, it then will precipitating
Object filtering, and violet precipitate is cleaned with ether with water, violet solid, yield 70% can be obtained.Above-mentioned reaction equation such as formula 20 produces
The spectrum of object is as follows: 1H NMR (400MHz, CDCl3): δ 8.21 (m, 2H), 7.86 (m, 4H), 7.83 (m, 2H), 7.75 (m,
4H)。
The product (0.1g, 0.5mmol) of formula 20 and the product (0.138g, 0.53mmol) of formula 17 are placed in high-voltage tube,
Acetic acid is added, is warming up to 75 DEG C and reacts 20 hours.After reaction, there is yellow mercury oxide in solution at this time, then by sediment
It is separated by filtration, and cleans sediment with water and ether, then this yellow solid can be obtained into yellow powder via heat sublimation after purification
0.15g, yield 35%.Above-mentioned reaction equation such as formula 21, the spectrum of product are as follows:1H NMR(400MHz,CDCl3):δ8.45(m,
2H), 7.93 (m, 2H), 7.71 (dd, J=8.4,18Hz, 8H)13C NMR(100MHz,CDCl3,δ):180.5,154.9,
142.7,140.5,135.4,133.1,132.6,130.7,128.1,117.8,114.4.HR MS (EI, m/z): calculated value
(C26H12N4O2): 412.0960, measured value: 412.0961 (M+).
It is similar with calculation with the measurement of embodiment 2, it is known that the Eg of the product of formula 21 is 3.4eV, and HOMO is -7.5eV,
And LUMO is -4.1eV.
Embodiment 5
By in product (0.15g, 0.24mmol) the merging reaction flask of formula 21, after vacuum pumping nitrogen filling, anhydrous dichloro is added
Methane (5mL) and malononitrile (0.063mL) are slowly added into anhydrous titanium tetrachloride (0.22mL), then slowly beat then under ice bath
Enter anhydrous pyridine (0.66mL), stirring is back to room temperature after 15 minutes, react 24 hours.After reaction, be added dilute hydrochloric acid until
Solution is neutrality, methylene chloride extraction is recycled, after collected organic layer is with magnesium sulfate water removal and spin concentration, then with methylene chloride
As eluent, carry out col-umn chromatography separation, yellow solid can be obtained, then by this yellow solid via heat sublimation after purification, can obtain
Blackish green powdered product 0.035g, yield 24.3%.Above-mentioned reaction equation such as formula 22, the spectrum of product are as follows:1H NMR
(400MHz,CDCl3): δ 8.57 (m, 2H), 7.88 (m, 2H), 7.76 (dd, J=8.8,42Hz, 8H) .HRMS (EI, m/z): meter
Calculation value (C32H12N8): 508.1185, measured value: 508.1187 (M+).
It is similar with calculation with the measurement of embodiment 2, it is known that the Eg of the product of formula 22 is 3.0eV, and HOMO is -7.2eV,
And LUMO is -4.2eV.
Although the present invention is disclosed above with multiple embodiments, however, it is not to limit the invention, any this technology neck
Without departing from the spirit and scope of the present invention, Ying Kezuo is arbitrarily changed and is retouched technical staff in domain, therefore the present invention
Protection scope should be subject to the appended claims limited range.
Claims (2)
1. a kind of carrier generation materials, chemical structure are as follows:
2. a kind of Organic Light Emitting Diode, comprising:
Anode；
Cathode；
Carrier generation materials layer, including carrier generation materials described in claim 1, and be located at the anode and the cathode it
Between；
First luminescent layer, between the anode and the carrier generation materials layer；And
Second luminescent layer, between the cathode and the carrier generation materials layer.
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| Synthesis and Photovoltaic Performance of Pyrazinoquinoxaline Containing Conjugated Thiophene-Based Dendrimers and Polymers;Gisela L. Schulz 等;《Macromolecules》;20130308;第46卷(第6期);第2141-2151页，尤其是第2143页化合物2以及第2144页化合物8 * |
| The Reaction between Diphenylketene and Phenylacetylenel;Lee Irvin Smith 等;《Journal of the American Chemical Society》;19391031;第61卷;第2619-2614页，尤其是第2620页化合物VIII * |
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