CN100567294C - N type organic semiconductor material - Google Patents
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- CN100567294C CN100567294C CN 200510137547 CN200510137547A CN100567294C CN 100567294 C CN100567294 C CN 100567294C CN 200510137547 CN200510137547 CN 200510137547 CN 200510137547 A CN200510137547 A CN 200510137547A CN 100567294 C CN100567294 C CN 100567294C
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- aromatic base
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- alkyl
- cycloalkyl
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
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Abstract
The invention provides a kind of N type organic semiconductor material, be the diimide derivative of line style multi-aromatic ring.The skeleton of described line style multi-aromatic ring has intermolecular π-π reactive force, can make the molecule storehouse neat.And the substituting group on the imide nitrogen-atoms also has same effect.Above-mentioned materials can improve electron transfer rate, uses to comprise the channel region as grid structure, the electron transfer layer of Organic Light Emitting Diode or the n type material of organic solar batteries.
Description
Technical field
The present invention relates to a kind of N type organic semiconductor material, particularly the diimide derivative of line style multi-aromatic ring.
Background technology
The general circuit layout has the advantage of operation power saving for unitary design with CMOS (complementary MOS).Because CMOS comprises two kinds of transistors: pass the PMOS in hole and the NMOS of the son that conducts electricity, therefore need the semiconductor material of P type and N type simultaneously.Organic semiconductor material is owing to being applicable to heat sublimation evaporation or method of spin coating, and is therefore wider in the application that with glass is substrate, particularly in the photovoltaic field.The organic semiconductor material of P type can be used as the channel region of PMOS, and this material often is called P passage (P-channel) on using, and its current carrier (carrier refers to the hole here) mobility is 10
-3-3cm
2/ Vs, (its carrier mobility is similar to 1cm to be better than common amorphous silicon semiconductor
2/ Vs).Such as pentacene (pentacene), its carrier mobility is greater than 2cm
2/ Vs.
Than the organic semiconductor material of P type, N type organic semi-conductor current carrier (referring to electronics here) mobility has only 10
-4-10
-1Cm
2/ Vs differs more than ten times with the P type.The hole is originally just fast than the speed of electronic migration, therefore needs novel materials to overcome this problem.As Appl.Phys.Lett.1995,67, carbon 60 derivatives disclosed in the 121-123 have oxygen sensitive and stable inadequately, are difficult to as device.Deliver De perylene tetracarboxylic acid dianhydride (perylene tetracarboxylicdianhydride as people such as Katz, PTCDA), as Adv.Mater.1996,8, N ' N '-phenylbenzene-3 that 242-244 discloses, 4,9,10-perylene dioctyl phthalate imide (N, N '-diphenyl-3,4,9,10-perylene dicarboxylicdiimide, DP-PTCDI), as Synth.Methods 1994,66, the adulterated four cyano quinolyl bismethane (tetracyanoquinodimethane that 257-261 is disclosed, TCNQ), as Chem.Phys.Lett.1990,167, the N type organic semiconductor material such as rare earth element complex of two phthalocyanine prussiates that 503-506 is disclosed, its carrier mobility is all less than 10
-4Cm
2/ Vs.
As disclosed n type materials of people such as Katz among the US 6387727B1, be dianhydride (dianhydride) derivative or imide (diimide) derivative (being replaced in 1,8,4,5 positions of naphthalene) of naphthalene.As J.Am.Chem.Soc.2000,122, the N disclosed in the 11057-11066, N '-dialkyl group-3,4,9,10-two Er Xian Ya An perylene (N, N '-dialkyl-3,4,9,10-perylenebiscarborboxiimide), the alkyl that is connect on its nitrogen has heptane base, dodecyl, octadecyl.Long alkane chain on the nitrogen has the character of liquid crystal molecule, can improve stability, and induces storehouse to increase carrier mobility.Similarly molecular configuration has also comprised J.Org.Chem.1994,59, and the dianhydride derivative of the anthracene that 6484-6486 is disclosed or diimide derivative (being replaced in 2,3,6,7 positions of naphthalene).But this paper is to synthesize the master, the application of the material of not touching upon.And the n type material that people such as Ong disclose in US 6861664B2 then is naphthalene derivatives (being replaced in 1,8,4,5 positions).Because in this patent, synthesis step is bound to produce cis-trans-isomer, though this patent is mentioned the scope of application between cis: trans is 95: 5-5: 95, along the anti-configuration reguarity of saboteur's storehouse that is bound to, and reduce carrier mobility.
In addition, with the n type material that the oligomer (US 6608323) of thiophene (thiophene) is formed, because the compound like multi-aromatic ring is not neat on the storehouse, the carrier mobility after forming device is also not good.Last above-mentioned N-type semiconductor organic materials with high mobility often has thermolability and aqueous vapor, oxygen sensitive, reduces the operation lifetime of device.
Summary of the invention
The invention provides a kind of N type organic semiconductor material, be the derivative (poly-aromatic tetracarboxylic diimide derivatices) of multi-aromatic ring tetracarboxylic acid diimide.This derivative has imide as electrophilic functional group, in order to improving the mobility of electronics, and modifies imide to improve the stability of this n type material with multiple substituting group.
The invention provides a kind of N type organic semiconductor material, its structure is as follows:
M, n are selected from 0 or positive integer independently of one another; R
1, R
2Be selected from hydrogen atom, C independently of one another
1-C
20Alkyl, C
1-C
20Fluorinated alkyl, C
1-C
20Cycloalkyl, C
1-C
20Fluoridize cycloalkyl, C
1-C
20Aromatic base, C
1-C
20Fluoridize aromatic base, C
1-C
20Heterocyclic aromatic base, C
1-C
20Fluoridize heterocyclic aromatic base, C
1-C
20Alkaryl or C
1-C
20The alkyl fluoride aryl; And each R
3Be selected from hydrogen atom, fluorine, chlorine, bromine, C independently of one another
1-C
20Alkyl, C
1-C
20Fluorinated alkyl, C
1-C
20Cycloalkyl, C
1-C
20Fluoridize cycloalkyl, C
1-C
20Aromatic base, C
1-C
20Fluoridize aromatic base, C
1-C
20Heterocyclic aromatic base, C
1-C
20Fluoridize heterocyclic aromatic base, C
1-C
20Alkaryl or C
1-C
20The alkyl fluoride aryl.
The present invention also provides another kind of N type organic semiconductor material, and its structure is as follows:
During n=1, R
1, R
2Be selected from hydrogen atom, C independently of one another
1-C
20Alkyl, C
1-C
20Fluorinated alkyl, C
1-C
20Cycloalkyl, C
1-C
20Fluoridize cycloalkyl, C
1-C
20Fluoridize aromatic base, C
1-C
20Heterocyclic aromatic base, C
1-C
20Fluoridize heterocyclic aromatic base, C
1-C
20Alkaryl or C
1-C
20The alkyl fluoride aryl;
N is during greater than 1 positive integer, R
1, R
2Be selected from hydrogen atom, C independently of one another
1-C
20Alkyl, C
1-C
20Fluorinated alkyl, C
1-C
20Cycloalkyl, C
1-C
20Fluoridize cycloalkyl, C
1-C
20Aromatic base, C
1-C
20Fluoridize aromatic base, C
1-C
20Heterocyclic aromatic base, C
1-C
20Fluoridize heterocyclic aromatic base, C
1-C
20Alkaryl or C
1-C
20The alkyl fluoride aryl; And each R
3Be selected from hydrogen atom, fluorine, chlorine, bromine, C independently of one another
1-C
20Alkyl, C
1-C
20Fluorinated alkyl, C
1-C
20Cycloalkyl, C
1-C
20Fluoridize cycloalkyl, C
1-C
20Aromatic base, C
1-C
20Fluoridize aromatic base, C
1-C
20Heterocyclic aromatic base, C
1-C
20Fluoridize heterocyclic aromatic base, C
1-C
20Alkaryl or C
1-C
20The alkyl fluoride aryl.
Description of drawings
Fig. 1 is applied to the synoptic diagram of the grid structure of upper current conducting cap (top contact) for N type organic semiconductor material of the present invention.
Fig. 2 is applied to the synoptic diagram of the grid structure of bottom electrode (bottom contact) for N type organic semiconductor material of the present invention.
Fig. 3 is applied to the synoptic diagram of the electron transfer layer of Organic Light Emitting Diode for N type organic semiconductor material of the present invention.
Main description of reference numerals
10,20,30～substrate; 12,22～grid; 14,24～insulation layer; 16,26～channel region; 17,27～source electrode; 18,28～drain; 31～anode; 32～hole injection layer; 33～hole transmission layer; 34～luminescent layer; 35～electron transfer layer; 36～electron injecting layer; 37～negative electrode.
Embodiment
For improving the carrier mobility speed of N type organic semiconductor material, the invention provides a kind of N type organic semiconductor material, its structure is as follows:
M, n are selected from 0 or positive integer independently of one another; R
1, R
2Be selected from hydrogen atom, C independently of one another
1-C
20Alkyl, C
1-C
20Fluorinated alkyl, C
1-C
20Cycloalkyl, C
1-C
20Fluoridize cycloalkyl, C
1-C
20Aromatic base, C
1-C
20Fluoridize aromatic base, C
1-C
20Heterocyclic aromatic base, C
1-C
20Fluoridize heterocyclic aromatic base, C
1-C
20Alkaryl or C
1-C
20The alkyl fluoride aryl; And each R
3Be selected from hydrogen atom, fluorine, chlorine, bromine, C independently of one another
1-C
20Alkyl, C
1-C
20Fluorinated alkyl, C
1-C
20Cycloalkyl, C
1-C
20Fluoridize cycloalkyl, C
1-C
20Aromatic base, C
1-C
20Fluoridize aromatic base, C
1-C
20Heterocyclic aromatic base, C
1-C
20Fluoridize heterocyclic aromatic base, C
1-C
20Alkaryl or C
1-C
20The alkyl fluoride aryl.
Said structure mainly is to encircle as molecular skeleton with line style more, and the π of many interannulars-the π reactive force can help the molecule storehouse, and the quality that molecule stacks will influence carrier mobility.Both sides respectively have the imide of one or six rings as the Electron Affinities of electron withdrawing group with the raising molecule, and on the nitrogen-atoms of imide, modify substituting group, be preferably chain alkyl, make intermolecular generation misfit effect (interdigitation), the stability of this molecule can be improved, this molecule proper alignment can be induced simultaneously.This substituting group is preferably fluoridizes substituting group, and fluorine atom is the strongest element of electronegativity, and volume is also quite little, can not cause sterically hindered and influences whole molecular configuration.Fluoro substituents can increase the thermostability of material and to the barriering effect of air, aqueous vapor, and improves the stability of material under air.Here use " fluoridizing " need not " perfluorination " reason (perfluorinated) to be that (fluorinated) the present invention does not fluoridize the carbon atom of this substituting group in abutting connection with nitrogen-atoms.In brief, promptly substituent alpha position does not replace with fluorine atom, competes with strong electronegativity and the imide electron withdrawing group of avoiding fluorine atom, reduces the electronegativity of nitrogen-atoms on the contrary and reduces carrier mobility.
N type organic semi-conductor carrier mobility is subjected to many parameter influences, as drain in the device and source interpolar distance, or the thickness of channel region, material.Commaterial may cause different carrier mobilities because form the technology of device.Therefore, in the research and development of material, we use the less interferential electronic migration energy level that is subjected to replace current carrier (electronics) mobility.Find that through experiment of the present invention get over for a long time when the polycyclic number, the electronic migration energy level is low more, experimental result such as following table:
Table 1
Can understand by above-mentioned comparison, increase the polycyclic number and can reduce the electronic migration energy level of molecule, and the carrier mobility when further increasing it as material.Along with many number of rings purpose increases, the electronic migration energy level will reduce at leisure, and therefore material behavior of the present invention is that its electronic migration energy level is less than 1.2kcal/mol.Because being reduced to a limit promptly might no longer descend, and because of many cyclizations become technical complexity, the number of ring is preferably integer 4-14.
The present invention also provides another kind of N type organic semiconductor material, and its structure is as follows:
During n=1, R
1, R
2Be selected from hydrogen atom, C independently of one another
1-C
20Alkyl, C
1-C
20Fluorinated alkyl, C
1-C
20Cycloalkyl, C
1-C
20Fluoridize cycloalkyl, C
1-C
20Fluoridize aromatic base, C
1-C
20Heterocyclic aromatic base, C
1-C
20Fluoridize heterocyclic aromatic base, C
1-C
20Alkaryl or C
1-C
20The alkyl fluoride aryl.N is during greater than 1 positive integer, R
1, R
2Be selected from hydrogen atom, C independently of one another
1-C
20Alkyl, C
1-C
20Fluorinated alkyl, C
1-C
20Cycloalkyl, C
1-C
20Fluoridize cycloalkyl, C
1-C
20Aromatic base, C
1-C
20Fluoridize aromatic base, C
1-C
20Heterocyclic aromatic base, C
1-C
20Fluoridize heterocyclic aromatic base, C
1-C
20Alkaryl or C
1-C
20The alkyl fluoride aryl.Identical with the molecular designing of preceding a kind of material, use line style to encircle as molecular skeleton more, the π of many interannulars-π reactive force can help the molecule storehouse.The polycyclic end respectively has the imide at five rings as the electronics nucleophilicity of electron withdrawing group with the raising molecule, and on the nitrogen-atoms of imide, modify substituting group, be preferably chain alkyl, make intermolecular generation misfit effect, the stability of this molecule can be improved, this molecule proper alignment can be induced simultaneously.This substituting group is preferably fluoridizes substituting group, and fluorine atom is the strongest element of electronegativity, and volume is also quite little, can not cause sterically hindered and influences whole molecular configuration.Fluoro substituents can increase the thermostability of material and to the barriering effect of air, aqueous vapor, and improves the stability of material under air.Here use " fluoridizing " and reason that need not " perfluorination " is that the present invention does not fluoridize the carbon atom of this substituting group in abutting connection with nitrogen-atoms.As preceding a kind of material, substituent alpha position does not replace with fluorine atom, competes with strong electronegativity and the imide electron withdrawing group of avoiding fluorine atom, reduces the electronegativity of nitrogen-atoms on the contrary and reduces carrier mobility.With preceding a kind of similar, many number of rings order of this structure is many more, and its electronic migration energy level is low more, as described in Table 2:
Table 2
Can understand by above-mentioned comparison, increase the polycyclic number and can reduce the electronic migration energy level of molecule, and the carrier mobility when further increasing it as material.Along with many number of rings purpose increases, the electronic migration energy level will reduce at leisure, and therefore material behavior of the present invention is that its electronic migration energy level is less than 1.25kcal/mol.Because being reduced to a limit promptly might no longer descend, and because of many cyclizations become technical complexity, the polycyclic number is preferably integer 3-12.
Above-mentioned two kinds of structures all can be used as the channel region that connects source electrode and drain in the grid structure.Be illustrated in figure 1 as a upper current conducting cap (top contact) structure, on substrate 10, form grid 12, after the blanket property covered ground forms insulation layer 14, form channel region 16, form drain 17 and source electrode 18 at last again with N type organic semiconductor material of the present invention.Perhaps bottom electrode as shown in Figure 2 (bottom contact) structure forms grid 22 on substrate 20, after the blanket property covered ground forms insulation layer 24, forms drain 27 and source electrode 28, forms channel region 26 with N type organic semiconductor material of the present invention more at last.These two kinds of structures are widely used in thin film transistor, particularly on the glass substrate of liquid-crystal display.Certainly, organic materials of the present invention is used the grid structure that further comprises silicon base.The material of source electrode, drain can be Au, Cr, Al, Mo, Cu, ITO, Si or organic materials poly-(3,4-vinyl dioxy base thiophene/sodium polystyrene sulfonate (PEDOT/PSS, (Poly (3,4-Ethylenedioxythiophene)/Poly (styrenesulfonate)).Substrate comprises glass, organic polymer material polyethylene naphthalenedicarboxylate dicarboxylic acid esters (PEN, poly (ethylenenaphthalate)), polyethylene terephthalate (PET, polyethylene terephthalate), polypropylene (PP, polypropylene), and polyimide (PI, polyimide) or tinsel.Insulation layer comprise silicon-dioxide, silicon nitride, aluminum oxide or polymethylmethacrylate (PMMA, PolymethylMethacrylate).
Above-mentioned materials also can be used as the electron transfer layer of organic luminescent device (OLED).OLED structure has as shown in Figure 3 generally included substrate 30, the anode 31 that forms in substrate in regular turn, hole injection layer 32, hole transmission layer 33, luminescent layer 34, electron transfer layer 35, electron injecting layer 36, negative electrode 37.Thickness of each layer and material are from making electronics arrive luminescent layer 35 apace from negative electrode 37 but N-type semiconductor material of the present invention can be applicable to electron transfer layer 35 by the prior art adjustment.
Preferred embodiment
Comparing embodiment 1
Enchashment has 1 of technology, 4,5,8-naphthalenetetracarbacidic acidic dianhydride (1,4,5,8-naphthalene tetracarboxylicdianhydride, 5.00g, 18.64mmol) and N-octyl amine (5.3g, 41.01mmol) in the mixing solutions of acetic acid/methylpyrrole pyridine 90 ℃ the reaction 20 hours, get final product product, its reaction as shown in the formula:
Embodiment 1
With 1 (3.00g, 22.35mmol) with the carbon tetrachloride solution of 11.48mL bromine (223.5mmol) under the UV-irradiation of 3000 dusts, reflux and obtain 1,2,4 after 6 hours, 5-dibrominated methylbenzene (5.13g, 6.70mmol).Get along the butyryl dicarboxylic anhydride (2.00g, 20.40mmol) with the N-octyl amine (3.16g, 24.48mmol) in the mixing solutions of acetic acid/methylpyrrole pyridine in 90 ℃ the reaction 20 hours, obtain N-octyl group-2,4-diketo-3-pyrrolin (3.88g, 18.56mmol).Get 1,2,4, (5.13g, 7.70mmol) with N-octyl group-2, (3.08g 14.74mmol) is dissolved under the DMF 4-diketo-3-pyrrolin 5-dibrominated methylbenzene, and (0.75g 5.00mmol), stirs and promptly gets product after 24 hours to add sodium iodide.Above-mentioned chemical equation is as follows:
Embodiment 2
Get 2, and the 3-benzanthrene (2,3-benzanthracene, 5.00mL, 21.90mmol) be dissolved in methylene dichloride (40mL) back logical bromine gas under room temperature, after 8 hours, drain purifying, obtain 1,4,9, the 10-tetrabromobisphenol, the 3-benzanthrene is dissolved in it after 45mL THF, slowly splash into n-Butyl Lithium (2.5N in-78 ℃, 43.8mL, 4.2eq), add 3.29g formaldehyde after 30 minutes, after 12 hours to drain behind the dichloromethane extraction, obtain 1,4,9,10-tetrakis hydroxymethyl phosphonium-2, the 3-benzanthrene is dissolved in methylene dichloride (60mL) back with it and adds potassium permanganate, with the ring reaction of contracting under phenylate behind the hydroxyl oxidize acid-forming group.The intermediate product of above-mentioned reaction and N-octyl amine (3.47g, 9.42mmol) in the mixing solutions of acetic acid/methylpyrrole pyridine 90 ℃ the reaction 20 hours, get final product product, its reaction as shown in the formula:
Embodiment 3
The comparison of carrier mobility (μ) and critical voltage (VT)
1. when VDS is small voltage (linear section):
I wherein
DSBe the drain electric current, μ is a carrier mobility, and W, L are respectively width and the length (being generally 10: 1) in the transistor channels, C
iBe the capacitance of unit surface insulation layer, V
GBe grid voltage, V
TBe critical voltage (threshold voltage).
2. work as VDS increasing (saturation region), and make drain electric current (I
DS) when reaching capacity:
Therefore can utilize (I
DS .sat.) 1/2 couple of V
GLinear regression is done in mapping, and the slope of the tropic is extrapolated carrier mobility (μ) thus, and tries to achieve V by the intercept of the tropic and X-axis
T
Table 3
| Comparing embodiment 1 | Embodiment 1 | Embodiment 2 | |
| The carrier mobility of upper current conducting cap passage | 1*10 -3cm 2/V-s | 0.015cm 2/V-s | 0.025cm 2/V-s |
| The carrier mobility of bottom electrode passage | 1*10 -4cm 2/V-s | 0.002cm 2/V-s | 0.007cm 2/V-s |
| ON/OFF current ratio (ION/IOFF) | Ion/Ioff＝2*10 4 | Ion/Ioff ＝1*10 5 | Ion/Ioff ＝2*10 5 |
By above-mentioned comparison, N-type semiconductor material of the present invention as can be known is in the application of upper current conducting cap or bottom electrode, and the N-type semiconductor material compared with prior art has preferable carrier mobility and switch current ratio.Upper current conducting cap with Fig. 1 is an example, and embodiment 1, the 2 relatively carrier mobility of embodiment 1 exceeds 15 times to 20 times; Bottom electrode with Fig. 2 is an example, and embodiment 1, the 2 relatively carrier mobility of embodiment 1 exceeds 20 times to 70 times.No matter and be which kind of structure, embodiment 1,2 all exceeds 50-100 doubly than the switch current ratio of embodiment 1 relatively.Therefore no matter be devices such as the electronic conductive layer of channel region, OLED of grid electrode of semiconductor or solar cell, the present invention is more suitable for as n type material than prior art.
Though the present invention discloses as above with a plurality of preferred embodiments; right its is not in order to limit the present invention; any those skilled in the art; without departing from the spirit and scope of the present invention; should change arbitrarily and retouching, so protection scope of the present invention is when being as the criterion of limiting with appended claims.
Claims (1)
1. N type organic semiconductor material, its structure is as follows:
M, n are the integer of 0-5;
R
1, R
2Be selected from hydrogen atom, C independently of one another
1-C
20Alkyl, C
1-C
20Fluorinated alkyl, C
1-C
20Cycloalkyl, C
1-C
20Fluoridize cycloalkyl, C
1-C
20Aromatic base, C
1-C
20Fluoridize aromatic base, C
1-C
20Heterocyclic aromatic base, C
1-C
20Fluoridize heterocyclic aromatic base, C
1-C
20Alkaryl or C
1-C
20The alkyl fluoride aryl; And
Each R
3Be selected from hydrogen atom, fluorine, chlorine, bromine, C independently of one another
1-C
20Alkyl, C
1-C
20Fluorinated alkyl, C
1-C
20Cycloalkyl, C
1-C
20Fluoridize cycloalkyl, C
1-C
20Aromatic base, C
1-C
20Fluoridize aromatic base, C
1-C
20Heterocyclic aromatic base, C
1-C
20Fluoridize heterocyclic aromatic base, C
1-C
20Alkaryl or C
1-C
20The alkyl fluoride aryl;
Wherein said C
1-C
20Fluorinated alkyl is not replaced by fluorine atom in abutting connection with the hydrogen atom on the carbon atom of nitrogen-atoms;
Described C
1-C
20Fluoridizing cycloalkyl is not replaced by fluorine atom in abutting connection with the hydrogen atom on the carbon atom of nitrogen-atoms;
Described C
1-C
20The alkyl fluoride aryl is not replaced by fluorine atom in abutting connection with the hydrogen atom on the carbon atom of nitrogen-atoms.
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| WO2008063583A1 (en) * | 2006-11-17 | 2008-05-29 | Polyera Corporation | Acene-based organic semiconductor materials and methods of preparing and using the same |
| KR101496931B1 (en) * | 2009-10-23 | 2015-02-27 | 상하이 인스티튜트 오브 오가닉 케미스트리, 차이니즈 아카데미 오브 사이언시스 | Sulfur Containing Heterocycle-Fused Naphthalene tetracarboxylic Acid Diimide Derivatives, Preparation Method and Use Thereof |
| EP2390253A1 (en) * | 2010-05-28 | 2011-11-30 | Universität des Saarlandes | Morylenes, a new class of modified rylenes |
| CN102617572A (en) * | 2011-01-31 | 2012-08-01 | 中国科学院化学研究所 | Tetracene-5,6:11,12-tetrabasic carboxylic acid diimide compound and preparation method thereof |
| WO2013024409A1 (en) * | 2011-08-12 | 2013-02-21 | Basf Se | Carbazolocarbazol-bis(dicarboximides) and their use as semiconductors |
| WO2014185408A1 (en) * | 2013-05-13 | 2014-11-20 | 国立大学法人九州大学 | Compound, luminescent material, and organic luminescent element |
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