CN102437290B - A kind of display of organic electroluminescence blue-light device and preparation method thereof - Google Patents
A kind of display of organic electroluminescence blue-light device and preparation method thereof Download PDFInfo
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Abstract
The invention provides a kind of display of organic electroluminescence blue-light device, this device comprises the anode, hole transmission layer, blue light-emitting, electron transfer layer and the negative electrode that stack gradually, blue light-emitting comprises material of main part and luminescent layer dyestuff, the HOMO energy level of wherein said material of main part is not more than-5.7eV, the HOMO energy level of luminescent layer dyestuff is not less than-5.2eV, and the HOMO energy level of hole transport layer material is between material of main part and the HOMO energy level of luminescent layer dyestuff and and poor > 0.3eV between the energy level of the HOMO of luminescent layer dyestuff.The present invention also provide prepare described display of organic electroluminescence blue-light device method, there is the display of organic electroluminescence of this blue-light device and the preparation method of described display of organic electroluminescence.Blue-light device of the present invention compared with prior art has higher luminous efficiency and better colourity.
Description
Technical field
The present invention relates to a kind of display of organic electroluminescence blue-light device, there is the display of organic electroluminescence of this blue-light device and prepare the method for described display of organic electroluminescence blue-light device and described display of organic electroluminescence.
Background technology
Display of organic electroluminescence (OLED) becomes color monitor by the luminescent device of red, green, blue three kinds of colors.Because the better blue light of colourity significantly can reduce the power consumption of display, therefore blue-light device is one of Main way of OLED research always.
For improving the colourity of blue light, usually need the emitting layer material of broad stopband.Such as, the emerging product of Japanese bright dipping discloses the material of a kind of energy gap > 2.8eV in patent application CN1643105A, can obtain the blue light of colourity in (0.12,0.11) to (0.16,0.19).But, use the luminescent material of this broad stopband, easily make electric charge enter transport layer, and then affect luminous efficiency and the life-span of device.
For avoiding the problems referred to above, usually in luminescent layer and charge transport layer, increase electric charge barrier layer, with by charge-limited in luminescent layer.But use electric charge barrier layer to add a bright voltage of device.Meanwhile, increasing by an one functional layer makes the preparation technology of device more complicated.
Summary of the invention
For solving the problem, the invention provides a kind of display of organic electroluminescence blue-light device, so that also good colourity can be obtained when not using electric charge barrier layer, improving the luminous efficiency of device simultaneously.This device comprises the anode, hole transmission layer, blue light-emitting, electron transfer layer and the negative electrode that stack gradually, blue light-emitting comprises material of main part and luminescent layer dyestuff, the HOMO energy level of wherein said material of main part is not more than-5.7eV, the HOMO energy level of luminescent layer dyestuff is not less than-5.2eV, and the HOMO energy level of hole transport layer material is between material of main part and the HOMO energy level of luminescent layer dyestuff and and poor > 0.3eV between the energy level of the HOMO of luminescent layer dyestuff.
The present invention also provides a kind of method preparing display of organic electroluminescence blue-light device, be included in anode substrate depositing successively and is laminated to each other, hole transmission layer, blue light-emitting, electron transfer layer and negative electrode, described blue light-emitting comprises material of main part and luminescent layer dyestuff, the HOMO energy level of wherein said material of main part is not more than-5.7eV, the HOMO energy level of luminescent layer dyestuff is not less than-5.2eV, and the HOMO energy level of hole transport layer material is between material of main part and the HOMO energy level of luminescent layer dyestuff and and poor > 0.3eV between the energy level of the HOMO of luminescent layer dyestuff.
The present invention also provides a kind of display of organic electroluminescence, and it comprises blue-light device, red device and green device, and wherein blue-light device is blue-light device of the present invention.
The present invention also provides a kind of method preparing described display of organic electroluminescence, be included on substrate and deposit stacked anode successively, hole transmission layer, and on hole transmission layer, deposit parallel blue light-emitting, green light emitting layer, red light luminescent layer, deposit stacked electron transfer layer and negative electrode successively afterwards, then encapsulate, described blue light-emitting comprises material of main part and luminescent layer dyestuff, the HOMO energy level of wherein said material of main part is not more than-5.7eV, the HOMO energy level of luminescent layer dyestuff is not less than-5.2eV, and the HOMO energy level of hole transport layer material is between material of main part and the HOMO energy level of luminescent layer dyestuff and and poor > 0.3eV between the energy level of the HOMO of luminescent layer dyestuff.
The present inventor finds, when the HOMO energy level of material of main part, luminescent layer dyestuff and hole transport layer material meets above-mentioned relation, the comparatively deep energy level that the HOMO that hole is more prone to be injected into luminescent layer dyestuff can be with, and then form the exciton of more macro-energy with the electronics of lumo energy, thus obtain the better blue light of colourity.And the probability that electric charge enters transport layer greatly reduces, thus improve the luminous efficiency of device.Therefore, blue-light device of the present invention has higher luminous efficiency and better colourity, and the life-span also improves.
Accompanying drawing explanation
Fig. 1 is the single pixel schematic diagram of organic light emitting display of the present invention.
Wherein,
1 is substrate;
2 is anode
3 is hole injection layer
4 is hole transmission layer
5R is red light luminescent layer
5G is green light emitting layer
5B is blue light-emitting
6 is electron transfer layer
7 is electron injecting layer
8 is negative electrode.
Embodiment
Display of organic electroluminescence blue-light device of the present invention comprises the anode, hole transmission layer, blue light-emitting, electron transfer layer and the negative electrode that stack gradually, blue light-emitting comprises material of main part and luminescent layer dyestuff, the HOMO energy level of wherein said material of main part is not more than-5.7eV, the HOMO energy level of luminescent layer dyestuff is not less than-5.2eV, and the HOMO energy level of hole transport layer material is between material of main part and the HOMO energy level of luminescent layer dyestuff and and poor > 0.3eV between the energy level of the HOMO of luminescent layer dyestuff.
The difference > 0.4eV of the HOMO energy level of preferred luminescent layer dyestuff and the HOMO energy level of hole transport layer material, now, the exciton that luminescent layer dyestuff is formed can more effectively be limited in luminescent layer, and then add exciton transition probability, thus improve the luminous efficiency of blue-light device.
The energy gap of preferably described hole mobile material is greater than the energy gap of luminescent layer dyestuff; Further, the energy gap of preferably described hole mobile material is also greater than the energy gap of luminescent layer material of main part.
Preferred described hole mobile material has the triplet being greater than 2.45eV, thus, display of organic electroluminescence except described blue light organic emissive device also comprise ruddiness organic luminescent device and green glow organic luminescent device and ruddiness, green glow, blue light organic emissive device use same hole mobile material time, improve the luminous efficiency of ruddiness and green glow organic luminescent device, make described display of organic electroluminescence obtain higher brightness.
Preferably, described hole transport layer material has lower conjugate property, thus is conducive to obtaining wider energy gap and lower HOMO energy level, improves colourity and the luminous efficiency of device thus.Preferred hole transport layer material is the compound with following general formula:
Wherein, R
1-R
4, R
5-R
8, R
5'-R
8' be selected from protium, halogen, CN, NO
2, amino, sub-fused ring aryl, sub-condensed hetero ring aryl, alkyl and alcohol radical, described sub-fused ring aryl is preferably the sub-fused ring aryl that carbon number is 6 to 30, described sub-condensed hetero ring aryl is preferably the sub-condensed hetero ring aryl that carbon number is 6 to 30, described alkyl is preferably the alkyl that carbon number is 6 to 20, and described alcohol radical is preferably the alcohol radical that carbon number is 6 to 30.A and B is selected from phenyl, naphthyl and anilino-respectively.R
9, R
10, R
9' and R
10' be aryl respectively, being preferably carbon number is the aryl of 6 to 30.
Also preferred is indenofluorene derivative as hole transport layer material, more preferably has the indenofluorene derivative of following structure:
Wherein, A and B is selected from phenyl, naphthyl and anilino-respectively.R
1and R
2, R
1' and R
2' being selected from aryl respectively, preferred carbon number is the aryl of 6 to 30.R
3for carbon number is from the alkyl of 1-6, especially methyl, ethyl, propyl group, isopropyl, butyl, isobutyl group, n-pentyl or n-hexyl.
Also preferred is the compound of following general formula as hole transport layer material:
Wherein, A and B is selected from phenyl, naphthyl and anilino-respectively.R
1and R
2, R
1' and R
2' be aryl respectively, preferred carbon number is the aryl of 6 to 30.
Also preferred is the compound of following general formula as hole transport layer material:
Wherein, A and B is selected from phenyl, naphthyl and anilino-respectively.R
1and R
2, R
1' and R
2' be aryl respectively, preferred carbon number is the aryl of 6 to 30.
The particularly preferred hole transport layer material of one class is following compound H TL-1 ~ HTL-5:
Another kind of particularly preferred hole transport layer material is following compound H TL-6 ~ HTL-10:
The particularly preferred hole transport layer material of a class is following compound H TL-11 ~ HTL-15 again:
The particularly preferred hole transport layer material of a class is following compound H TL-16 ~ HTL-20 again:
Described material of main part is preferably anthracene derivant, especially asymmetric anthracene derivant or phenylanthracene derivative, or general formula is the compound of (Cz) nMm, wherein Cz represents substituted or unsubstituted carbazyl, M represents the substituted or unsubstituted assorted aromatic group with 2-40 carbon atom and nitrogen-atoms, n represents the integer of 2 to 3, and m represents the integer of 1 to 3.
As described material of main part, preferred following anthracene derivant compound:
As described material of main part, the especially preferred compd B H-1 as phenylanthracene derivative, compd B H-2, the compd B H-3 as asymmetric anthracene derivant, compd B H-4, and compd B H-5.
Described luminescent layer dyestuff preferably adopts indeno benzfluorene derivative, wherein, and preferred following compd B D-1 ~ BD-11:
Also preferred following compd B D-12 ~ BD-22:
The ratio of described material of main part and luminescent layer dyestuff is preferably, and luminescent layer dyestuff counts 2 % by weight-8 % by weight relative to material of main part.
Electron transfer layer can adopt in prior art the material being commonly used for electron transfer layer in organic electroluminescence device, can use such as metal organic complex, aromatic condensed ring class or o-phenanthroline class etc.
In addition, between anode and hole transmission layer, also can have hole injection layer, and also can have electron injecting layer between negative electrode and electron transfer layer.Hole injection layer and electron injecting layer all can adopt in prior art the material being usually used in hole injection layer or electron injecting layer.
Negative electrode can adopt metal or metal mixture to make, as the Ca etc. of Mg, Ag doping of Ag doping.Also electron injecting layer can be combined with negative electrode, form electron injecting layer/metal-layer structure, as LiF/Al, Li
2the common structures such as O/Al.
Anode can be in prior art the anode be usually used in organic electroluminescence device, such as ito anode.
Between hole transmission layer and hole injection layer, also preferably have the second hole transmission layer, this second hole transmission layer has the hole mobility higher than described hole transmission layer.By increasing by the second hole transmission layer, higher brightness can be obtained.As the material of this second hole transmission layer, preferably use arylamine derivatives, such as N, N '-diphenyl-N, N '-two (1,1 '-biphenyl)-4,4 '-diamines (NPB).
The thickness of each layer all can be the general thickness of these material layers used in prior art.Wherein, preferred described thickness of hole transport layer is 5nm-50nm, is more preferably 5nm-15nm.
The present invention also provides a kind of method preparing display of organic electroluminescence blue-light device, be included in anode substrate depositing successively and is laminated to each other, hole transmission layer, blue light-emitting, electron transfer layer and negative electrode, described blue light-emitting comprises material of main part and luminescent layer dyestuff, the HOMO energy level of wherein said material of main part is not more than-5.7eV, the HOMO energy level of luminescent layer dyestuff is not less than-5.2eV, and the HOMO energy level of hole transport layer material is between luminescent layer main body and the HOMO energy level of luminescent layer dyestuff and and poor > 0.3eV between the energy level of the HOMO of luminescent layer dyestuff.
Described deposition by realizing for the formation of the conventional deposition method of these material layers in prior art, such as, passes through physical vapor deposition, chemical vapor deposition method etc.
Preferred also deposition of hole implanted layer between anode and hole transmission layer, and/or electron injecting layer is deposited between negative electrode and electron transfer layer.If deposited hole injection layer, preferably between hole transmission layer and hole injection layer, also deposit the second hole transmission layer, described second hole transmission layer definition as above.
The present invention also provides a kind of display of organic electroluminescence, and it comprises blue-light device, red device and green device, and wherein blue-light device is blue-light device of the present invention.At least one in preferred described ruddiness, green glow organic luminescent device is Phosphorescent luminescent device.
The present invention also provides the preparation method of described display of organic electroluminescence, be included on substrate and deposit stacked anode successively, hole transmission layer, and on hole transmission layer, deposit parallel blue light-emitting, green light emitting layer, red light luminescent layer, deposit stacked electron transfer layer and negative electrode successively afterwards, then encapsulate, described blue light-emitting comprises material of main part and luminescent layer dyestuff, the HOMO energy level of wherein said material of main part is not more than-5.7eV, the HOMO energy level of luminescent layer dyestuff is not less than-5.2eV, and the HOMO energy level of hole transport layer material is between material of main part and the HOMO energy level of luminescent layer dyestuff and and poor > 0.3eV between the energy level of the HOMO of luminescent layer dyestuff.
Described encapsulation is undertaken by the method for packing being usually used in organic electroluminescence device in prior art.
Further illustrate the present invention by the following examples, but the invention is not restricted to these specific embodiments.
In following embodiment, the HOMO energy level of material adopts cyclic voltammetry.
Embodiment 1:
Deposit the anode of ITO as OLED blue-light device on the glass substrate, and etch required figure, use O
2plasma treatment 3 minutes.Gained substrate is placed in vacuum, and deposit the mixture of MTDATA and F4TCNQ of 50nm as hole injection layer by common steaming, wherein F4TCNQ counts 4 % by weight relative to MTDATA.Then the HTL-1 of 20nm is deposited as hole transmission layer.Steam the mixture of BH-3 and BD-1 of deposition 40nm more altogether as luminescent layer, wherein BD-1 counts 5 % by weight relative to BH-3.Then the Bphen of 20nm is deposited as electron transfer layer.Keep the vacuum constant, the LiF of deposition 0.5nm is as electron injecting layer.Finally deposit the Al of 150nm as negative electrode.Substrate is passed to pure N
2encapsulate in environment.Thus obtained OLED blue-light device.
The structural formula of MTDATA, F4TCNQ, BPhen is as follows:
HOMO energy level and the energy gap of selected material HTL-1, BH-3, BD-1 are as shown in table 1 below.
Table 1
Material | HTL-1 | BH-3 | BD-1 |
HOMO | -5.52eV | -5.8eV | -5.1eV |
Energy gap | 3.2eV | 3.0eV | 2.8eV |
Embodiment 2
OLED blue-light device is prepared according to the method described in embodiment 1.Difference is to replace HTL-1 with HTL-2, and BH-1 replaces BH-3, BD-2 to replace BD-1.
HOMO energy level and the energy gap of selected HTL-2, BH-1, BD-2 are as shown in table 2 below.
Table 2
Material | HTL-2 | BH-1 | BD-2 |
HOMO | -5.45eV | -5.75eV | -5.1eV |
Energy gap | 3.2eV | 3eV | 2.8eV |
Embodiment 3
OLED blue-light device is prepared according to the method described in embodiment 1.Difference is, hole transport layer material is HTL-3, and thickness is 10nm, and between hole injection layer and hole transmission layer, increase the second hole transmission layer that thickness is 10nm, material is NPB.
Table 3
Material | HTL-3 | BH-3 | BD-1 | NPB |
HOMO | -5.51eV | -5.8eV | -5.1eV | -5.4eV |
Energy gap | 3.2eV | 3eV | 2.8eV | 3.0eV |
Embodiment 4
OLED blue-light device is prepared according to the method described in embodiment 1.Difference is to replace BH-3 with BH-4.
HOMO energy level and the energy gap of selected HTL-1, BH-4, BD-1 are as shown in table 4 below.
Table 4
Material | HTL-1 | BH-4 | BD-1 |
HOMO | -5.52eV | -5.8eV | -5.1eV |
Energy gap | 3.2eV | 3.1eV | 2.8eV |
Embodiment 5
OLED blue-light device is prepared according to the method described in embodiment 1.Difference is to replace BH-3 with BH-5.
HOMO energy level and the energy gap of selected HTL-1, BH-5, BD-1 are as shown in table 5 below.
Table 5
Material | HTL-1 | BH-5 | BD-1 |
HOMO | -5.52eV | -5.75eV | -5.1eV |
Energy gap | 3.2eV | 3.0eV | 2.8eV |
Comparative example 1:
Except use NPB substitutes except HTL-1, prepare OLED according to the method described in embodiment 1.
Comparative example 2:
Except use NPB substitutes except HTL-1, prepare OLED according to the method described in embodiment 2.
OLED blue-light device Performance comparision prepared by embodiment 1-5 and comparative example 1-2 is as following table.Wherein, brightness and colourity are measured by photometric and chromatric meter PR655, and the ratio of the current density that luminous efficiency is measured by brightness and current voltmeter Keithley obtains, and the life-span is the time that brightness partly declines, and continues observation obtain by luminance meter.
Table 6
As can be seen from Table 6, the device of embodiment 1-5, compared with comparative example 1-2, can obtain more excellent colourity, higher luminous efficiency and/or longer life-span.
Claims (26)
1. a display of organic electroluminescence blue-light device, this device comprises the anode, hole transmission layer, blue light-emitting, electron transfer layer and the negative electrode that stack gradually, blue light-emitting comprises material of main part and luminescent layer dyestuff, the HOMO energy level of wherein said material of main part is not more than-5.7eV, the HOMO energy level of luminescent layer dyestuff is not less than-5.2eV, and the HOMO energy level of hole transport layer material is between material of main part and the HOMO energy level of luminescent layer dyestuff and and poor >0.3eV between the energy level of the HOMO of luminescent layer dyestuff.
2. the display of organic electroluminescence blue-light device of claim 1, is characterized in that, the difference >0.4eV of the HOMO energy level of luminescent layer dyestuff and the HOMO energy level of hole transport layer material.
3. the display of organic electroluminescence blue-light device of claim 1, is characterized in that, the energy gap of described hole transport layer material is greater than the energy gap of luminescent layer dyestuff.
4. the display of organic electroluminescence blue-light device of claim 3, is characterized in that, the energy gap of described hole transport layer material is also greater than the energy gap of luminescent layer material of main part.
5. the display of organic electroluminescence blue-light device of claim 1, is characterized in that, described hole transport layer material has the triplet being greater than 2.45eV.
6. the display of organic electroluminescence blue-light device of claim 1, is characterized in that, hole transport layer material is the compound with following general formula:
Wherein, R
1-R
4, R
5-R
8, R
5'-R
8' be selected from protium, halogen, CN, NO
2, amino, sub-fused ring aryl, sub-condensed hetero ring aryl, alkyl and alcohol radical; A and B is selected from phenyl, naphthyl and anilino-respectively; R
9, R
10, R
9' and R
10' be aryl respectively;
Or indenofluorene derivative;
Or the compound of following general formula:
Wherein, A and B is selected from phenyl, naphthyl and anilino-respectively; R
1and R
2, R
1' and R
2' be aryl respectively;
Or the compound of following general formula:
Wherein, A and B is selected from phenyl, naphthyl and anilino-respectively; R
1and R
2, R
1' and R
2' be aryl respectively.
7. the display of organic electroluminescence blue-light device of claim 6, is characterized in that, the radicals R in following general formula
1-R
4, R
5-R
8, R
5'-R
8' definition in
Described sub-fused ring aryl to be carbon number be 6 to 30 sub-fused ring aryl, described sub-condensed hetero ring aryl to be carbon number be 6 to 30 sub-condensed hetero ring aryl, described alkyl to be carbon number be 6 to 20 alkyl, described alcohol radical to be carbon number be 6 to 30 alcohol radical.
8. the display of organic electroluminescence blue-light device of claim 6, is characterized in that, R
9, R
10, R
9' and R
10' to be carbon number be respectively 6 to 30 aryl.
9. the display of organic electroluminescence blue-light device of claim 6, is characterized in that, described indenofluorene derivative has following structure:
Wherein, A and B is selected from phenyl, naphthyl and anilino-respectively; R
1and R
2, R
1' and R
2' be selected from aryl respectively; R
3for carbon number is from the alkyl of 1-6.
10. the display of organic electroluminescence blue-light device of claim 9, is characterized in that, the R in described indenofluorene derivative
1and R
2, R
1' and R
2' be selected from the aryl that carbon number is 6 to 30 respectively.
The display of organic electroluminescence blue-light device of 11. claims 9, is characterized in that, the R in described indenofluorene derivative
3for methyl, ethyl, propyl group, isopropyl, butyl, isobutyl group, n-pentyl or n-hexyl.
The display of organic electroluminescence blue-light device of 12. claims 6, is characterized in that, in the compound of following general formula
R
1and R
2, R
1' and R
2' to be carbon number be respectively 6 to 30 aryl.
The display of organic electroluminescence blue-light device of 13. claims 6, is characterized in that, in the compound of following general formula
R
1and R
2, R
1' and R
2' to be carbon number be respectively 6 to 30 aryl.
The display of organic electroluminescence blue-light device of 14. claims 6, is characterized in that, described thickness of hole transport layer is 5nm-50nm.
The display of organic electroluminescence blue-light device of 15. claims 6, is characterized in that, described thickness of hole transport layer is 5nm-15nm.
The display of organic electroluminescence blue-light device of 16. claims 6, is characterized in that, hole transport layer material is selected from following compound H TL-1 ~ HTL-5:
Or be selected from following compound H TL-6 ~ HTL-10:
Or be selected from following compound H TL-11 ~ HTL-15:
Or be selected from following compound H TL-16 ~ HTL-20:
The display of organic electroluminescence blue-light device of 17. claims 1, it is characterized in that, described material of main part is anthracene derivant, or general formula is the compound of (Cz) nMm, wherein Cz represents substituted or unsubstituted carbazyl, M represents the substituted or unsubstituted assorted aromatic group with 2-40 carbon atom and nitrogen-atoms, and n represents the integer of 2 to 3, and m represents the integer of 1 to 3.
The display of organic electroluminescence blue-light device of 18. claims 17, is characterized in that, described material of main part is asymmetric anthracene derivant or phenylanthracene derivative.
The display of organic electroluminescence blue-light device of 19. claims 17, is characterized in that, described material of main part is selected from following anthracene derivant compound:
The display of organic electroluminescence blue-light device of 20. claims 19, it is characterized in that, described material of main part is selected from as compd B H-1, the compd B H-2 of phenylanthracene derivative, the compd B H-3 as asymmetric anthracene derivant, compd B H-4, and compd B H-5.
The display of organic electroluminescence blue-light device of 21. claims 1, is characterized in that, described luminescent layer dyestuff is indeno benzfluorene derivative.
The display of organic electroluminescence blue-light device of 22. claims 21, is characterized in that, described luminescent layer dyestuff is selected from following compd B D-1 ~ BD-11:
And following compd B D-12 ~ BD-22:
The display of organic electroluminescence blue-light device of 23. claims 1, is characterized in that, the ratio of described material of main part and luminescent layer dyestuff is that luminescent layer dyestuff counts 2 % by weight-8 % by weight relative to material of main part.
24. 1 kinds of methods preparing display of organic electroluminescence blue-light device, be included in anode substrate depositing successively and is laminated to each other, hole transmission layer, blue light-emitting, electron transfer layer and negative electrode, described blue light-emitting comprises material of main part and luminescent layer dyestuff, the HOMO energy level of wherein said material of main part is not more than-5.7eV, the HOMO energy level of luminescent layer dyestuff is not less than-5.2eV, and the HOMO energy level of hole transport layer material is between material of main part and the HOMO energy level of luminescent layer dyestuff and and poor >0.3eV between the energy level of the HOMO of luminescent layer dyestuff.
25. 1 kinds of display of organic electroluminescence, comprise blue-light device, red device and green device, the blue-light device of wherein said blue-light device any one of claim 1-23.
26. 1 kinds of methods preparing display of organic electroluminescence, be included on substrate and deposit stacked anode successively, hole transmission layer, and on hole transmission layer, deposit parallel blue light-emitting, green light emitting layer, red light luminescent layer, deposit stacked electron transfer layer and negative electrode successively afterwards, then encapsulate, described blue light-emitting comprises material of main part and luminescent layer dyestuff, the HOMO energy level of wherein said material of main part is not more than-5.7eV, the HOMO energy level of luminescent layer dyestuff is not less than-5.2eV, and the HOMO energy level of hole transport layer material is between material of main part and the HOMO energy level of luminescent layer dyestuff and and poor >0.3eV between the energy level of the HOMO of luminescent layer dyestuff.
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