EP1896388A2 - Oligo-tetracene, ihre herstellung und ihre anwendung - Google Patents
Oligo-tetracene, ihre herstellung und ihre anwendungInfo
- Publication number
- EP1896388A2 EP1896388A2 EP06762105A EP06762105A EP1896388A2 EP 1896388 A2 EP1896388 A2 EP 1896388A2 EP 06762105 A EP06762105 A EP 06762105A EP 06762105 A EP06762105 A EP 06762105A EP 1896388 A2 EP1896388 A2 EP 1896388A2
- Authority
- EP
- European Patent Office
- Prior art keywords
- oligo
- tetracene
- carbon atoms
- tetracenes
- organic
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
Links
- 238000004519 manufacturing process Methods 0.000 title abstract description 5
- 230000005669 field effect Effects 0.000 claims abstract description 19
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 14
- 125000003118 aryl group Chemical group 0.000 claims abstract description 13
- 239000004065 semiconductor Substances 0.000 claims abstract description 10
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 8
- -1 alkoxy radicals Chemical class 0.000 claims abstract description 6
- 150000005840 aryl radicals Chemical class 0.000 claims abstract description 3
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 3
- 150000002367 halogens Chemical class 0.000 claims abstract description 3
- 125000001424 substituent group Chemical group 0.000 claims abstract description 3
- XBDYBAVJXHJMNQ-UHFFFAOYSA-N Tetrahydroanthracene Natural products C1=CC=C2C=C(CCCC3)C3=CC2=C1 XBDYBAVJXHJMNQ-UHFFFAOYSA-N 0.000 claims description 17
- IFLREYGFSNHWGE-UHFFFAOYSA-N tetracene Chemical compound C1=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C21 IFLREYGFSNHWGE-UHFFFAOYSA-N 0.000 claims description 17
- 238000000034 method Methods 0.000 claims description 9
- 150000003518 tetracenes Chemical class 0.000 claims description 9
- 230000008569 process Effects 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- XUXDOWHYARJFFA-UHFFFAOYSA-N 2-tetracen-2-yltetracene Chemical compound C1=CC=CC2=CC3=CC4=CC(C5=CC6=CC7=CC8=CC=CC=C8C=C7C=C6C=C5)=CC=C4C=C3C=C21 XUXDOWHYARJFFA-UHFFFAOYSA-N 0.000 claims description 3
- 238000006619 Stille reaction Methods 0.000 claims description 3
- 238000006069 Suzuki reaction reaction Methods 0.000 claims description 3
- 238000006880 cross-coupling reaction Methods 0.000 claims description 3
- 150000002430 hydrocarbons Chemical group 0.000 claims description 3
- 238000002061 vacuum sublimation Methods 0.000 claims description 3
- 125000002947 alkylene group Chemical group 0.000 claims description 2
- 150000002902 organometallic compounds Chemical class 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 5
- 230000009977 dual effect Effects 0.000 abstract 1
- 125000001183 hydrocarbyl group Chemical group 0.000 abstract 1
- 230000037230 mobility Effects 0.000 description 11
- SLIUAWYAILUBJU-UHFFFAOYSA-N pentacene Chemical compound C1=CC=CC2=CC3=CC4=CC5=CC=CC=C5C=C4C=C3C=C21 SLIUAWYAILUBJU-UHFFFAOYSA-N 0.000 description 9
- 239000000126 substance Substances 0.000 description 6
- 238000004770 highest occupied molecular orbital Methods 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 239000011368 organic material Substances 0.000 description 5
- HZNVUJQVZSTENZ-UHFFFAOYSA-N 2,3-dichloro-5,6-dicyano-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(C#N)=C(C#N)C1=O HZNVUJQVZSTENZ-UHFFFAOYSA-N 0.000 description 4
- 238000005859 coupling reaction Methods 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 229910004298 SiO 2 Inorganic materials 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000002800 charge carrier Substances 0.000 description 3
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 3
- 239000010931 gold Substances 0.000 description 3
- 229910052737 gold Inorganic materials 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 229920001296 polysiloxane Polymers 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical group CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- UMIVXZPTRXBADB-UHFFFAOYSA-N benzocyclobutene Chemical compound C1=CC=C2CCC2=C1 UMIVXZPTRXBADB-UHFFFAOYSA-N 0.000 description 2
- 230000031709 bromination Effects 0.000 description 2
- 238000005893 bromination reaction Methods 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 230000008878 coupling Effects 0.000 description 2
- 238000010168 coupling process Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 238000006471 dimerization reaction Methods 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 239000010408 film Substances 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- 229910010272 inorganic material Inorganic materials 0.000 description 2
- 239000011147 inorganic material Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 238000006384 oligomerization reaction Methods 0.000 description 2
- 150000002964 pentacenes Chemical class 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 230000035945 sensitivity Effects 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 239000010409 thin film Substances 0.000 description 2
- JWCGDNHAPBZVHD-UHFFFAOYSA-N 1,4-epoxy-1,4-dihydronaphthalene Chemical compound C12=CC=CC=C2C2OC1C=C2 JWCGDNHAPBZVHD-UHFFFAOYSA-N 0.000 description 1
- VQRBXYBBGHOGFT-UHFFFAOYSA-N 1-(chloromethyl)-2-methylbenzene Chemical group CC1=CC=CC=C1CCl VQRBXYBBGHOGFT-UHFFFAOYSA-N 0.000 description 1
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- LJQDHTNTYYEGHX-UHFFFAOYSA-N 2-(5,12-dihydrotetracen-2-yl)-5,12-dihydrotetracene Chemical compound C1=CC=C2C=C(CC=3C(=CC=C(C=3)C3=CC=C4CC5=CC6=CC=CC=C6C=C5CC4=C3)C3)C3=CC2=C1 LJQDHTNTYYEGHX-UHFFFAOYSA-N 0.000 description 1
- VCZOGKXIRNIUDC-UHFFFAOYSA-N 2-bromo-5,12-dihydrotetracene Chemical compound C1=CC=C2C=C(CC=3C(=CC=C(C=3)Br)C3)C3=CC2=C1 VCZOGKXIRNIUDC-UHFFFAOYSA-N 0.000 description 1
- VUQQEZHVXFHPMR-UHFFFAOYSA-N 2-bromotetracene Chemical compound C1=CC=CC2=CC3=CC4=CC(Br)=CC=C4C=C3C=C21 VUQQEZHVXFHPMR-UHFFFAOYSA-N 0.000 description 1
- GMHHTGYHERDNLO-UHFFFAOYSA-N 4-bromobicyclo[4.2.0]octa-1(6),2,4-triene Chemical compound BrC1=CC=C2CCC2=C1 GMHHTGYHERDNLO-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- QDZGLKRYQGDOFS-UHFFFAOYSA-N C1=CCCCCC([Ni]C=2CCCCC=CC=2)=C1 Chemical compound C1=CCCCCC([Ni]C=2CCCCC=CC=2)=C1 QDZGLKRYQGDOFS-UHFFFAOYSA-N 0.000 description 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- 238000005698 Diels-Alder reaction Methods 0.000 description 1
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 1
- 239000012080 ambient air Substances 0.000 description 1
- 238000007080 aromatic substitution reaction Methods 0.000 description 1
- 238000003491 array Methods 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 239000002178 crystalline material Substances 0.000 description 1
- 238000006352 cycloaddition reaction Methods 0.000 description 1
- 238000006356 dehydrogenation reaction Methods 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 238000001212 derivatisation Methods 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 230000000447 dimerizing effect Effects 0.000 description 1
- 230000005670 electromagnetic radiation Effects 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 229920002457 flexible plastic Polymers 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 239000012212 insulator Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 229940078552 o-xylene Drugs 0.000 description 1
- 230000003606 oligomerizing effect Effects 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 238000005457 optimization Methods 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 125000005582 pentacene group Chemical group 0.000 description 1
- 238000000103 photoluminescence spectrum Methods 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 238000000197 pyrolysis Methods 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 230000009897 systematic effect Effects 0.000 description 1
- 125000001935 tetracenyl group Chemical group C1(=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C12)* 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 238000000870 ultraviolet spectroscopy Methods 0.000 description 1
- 238000012800 visualization Methods 0.000 description 1
Classifications
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C15/00—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts
- C07C15/20—Polycyclic condensed hydrocarbons
- C07C15/38—Polycyclic condensed hydrocarbons containing four rings
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K10/00—Organic devices specially adapted for rectifying, amplifying, oscillating or switching; Organic capacitors or resistors having potential barriers
- H10K10/40—Organic transistors
- H10K10/46—Field-effect transistors, e.g. organic thin-film transistors [OTFT]
- H10K10/462—Insulated gate field-effect transistors [IGFETs]
- H10K10/464—Lateral top-gate IGFETs comprising only a single gate
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/14—Carrier transporting layers
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/40—Ortho- or ortho- and peri-condensed systems containing four condensed rings
- C07C2603/42—Ortho- or ortho- and peri-condensed systems containing four condensed rings containing only six-membered rings
- C07C2603/44—Naphthacenes; Hydrogenated naphthacenes
-
- 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
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E10/00—Energy generation through renewable energy sources
- Y02E10/50—Photovoltaic [PV] energy
- Y02E10/549—Organic PV cells
Definitions
- the invention relates to substituted and unsubstituted oligo-tetracenes, their preparation and their use as semiconductors in organic field-effect transistors (OFETS), organic light-emitting diodes (OLEDs), sensors, organic solar cells and in other fields of optics and electronics.
- OFETS organic field-effect transistors
- OLEDs organic light-emitting diodes
- sensors organic solar cells and in other fields of optics and electronics.
- Organic field-effect transistors allow the use of inexpensive, lightweight and flexible plastic materials as an alternative to glass in liquid crystal displays and displays equipped with light emitting diodes.
- the best-studied and semiconductive organic material in organic field-effect transistors is ⁇ -sexithienyl.
- Pentacene-containing organic field-effect transistors have been reported to achieve field-effect mobility above 0.5 cm 2 / V xs and an on / off ratio greater than 10 8 (FIG. 1). Both results are comparable to those of hydrogenated amorphous silicones and are the best currently available for organic field-effect transistors.
- pentacenes have the considerable disadvantage that they are chemically unstable, readily oxidize and disproportionate, and undergo cycloaddition reactions (2-4). Pentacene must therefore be cleaned and handled with great care under inert conditions.
- the chemical derivatization of pentacene is very difficult because of its sensitivity and does not allow the use of conventional aromatic substitution reactions. Therefore, every derivative, if it is accessible at all, requires an individual synthesis. Systematic investigations and optimizations of pentacene derivatives for organic field effect transistors (OFETs) are therefore hardly possible.
- HOMO occupied molecular orbital
- tetracene which consists of four rather than five condensed benzene rings, is much more chemically stable, but exhibits much worse semiconductor properties.
- OFETs based on polycrystalline tetracenes generally have field effect mobilities of 0.05 cm 2 / V xs and an on / off ratio of about 10 6 .
- tetracene has an equally well delocalized ⁇ -electron system that is very similar to that of the pentacene.
- One way to achieve this goal might be to extend the tetracene, because one crucial difference between the tetracene and the pentacene is that the tetracene is shorter. This could be the cause of lower order and less favorable transistor properties. If this assumption is correct, one solution to the problem might be to increase the length of the tetracene molecule increase without impairing its chemical and semiconducting properties. The attachment of hydrocarbons or simple aromatic groups to the longitudinal axis of the tetracenes is probably not the best way to do so because it may result in a reduction of the conductive properties and disturbances of the advantageous arrangement of the tetracene molecules associated with an increase in the sensitivity of the molecules to oxidation.
- Alkyl or alkoxy radicals having 1 to 18 carbon atoms Alkyl or alkoxy radicals having 1 to 18 carbon atoms
- Aryl radicals with up to 10 carbon atoms which are also one or more
- n is an integer from 1 to 20, preferably from 1 to 6, very particularly preferably 1 or 2
- X is a single bond, an alkylene group having 1-6 carbon atoms, a hydrocarbon chain having one or more conjugated double bonds, an aryl group or a system consisting of a plurality of fused, aromatic rings.
- one or more of the six-atom condensed aromatic rings may be replaced by a five-atom ring which may also contain a heteroatom.
- the bridging aryl group may be one or more phenyl rings unsubstituted or containing 1-18 carbon atoms, or a double unsaturated heteroatom containing five-membered ring or a ferrocenylene unit.
- a particularly preferred oligotetracene is the 2- (tetracen-2-yl) tetracene of formula II
- R and R ' can be hydrogen or have the meanings given for formula I.
- Another preferred dietetracen corresponds to the formula III
- R and R ' may have hydrogen or the meanings given for formula I.
- oligo-tetracenes and ditetracenes are prepared by an oligomerization or dimerization of the corresponding tetracenes by, for example, a coupling reaction controlled by transition metals.
- these processes require halogenated starting materials.
- a tetracene derivative containing a chlorine or bromine atom in the 2-position was needed. Direct selective bromination of the tetracene leading to such a derivative is not possible. Therefore, a new process for the preparation of 2-bromotetracene has been developed.
- one in any position, in particular in the 1-, 2- or 4-position, mono- or poly-substituted, preferably halogenated, in particular brominated tetracene oligomerized is particularly preferred.
- a cross Coupling reaction eg Suzuki or Stille reaction.
- the product obtained is then purified by vacuum sublimation.
- ⁇ -chloro-o-xylene 1 was subjected to pyrolysis at about 800 ° C. and 0.5 mbar.
- Benzocyclobutene 2 was obtained in 45% yield. Its selective bromination was carried out by treating benzocyclobutene dissolved in acetic acid with a mixture of bromine and iodine at room temperature. This gave 4-bromobenzocyclobutene 3.
- the coupling reaction was carried out with about 80% yield in a mixture of Dimethylformamide and Tolyol carried out at 80 0 C, with bis (cyclooctadienyl) nickel (O) in stoichiometric. Quantities was used. After recrystallization from o-dichlorobenzene, dehydrogenation of 7 was achieved by treatment with 2,3-dichloro-5,6-dicyano-p-benzoquinone (DDQ) in boiling o-xylene. After purification by repeated vacuum sublimation, orange-red crystals of 2- (tetracen-2-yl) tetracene 8 were recovered in 75% yield. All intermediates were characterized by 1 H and 13 C NMR spectroscopy and mass spectroscopy. Compound 8 was characterized by UV-vis spectroscopy.
- FIG. 1A shows a representative spectrum taken in a thin layer of 8 on a quartz wafer.
- the synthesis of the oligo- and ditetracenes according to the invention can be carried out in particular successfully, when oligomerizing or dimerizing a two-position halogenated, preferably brominated tetracene.
- a two-position halogenated, preferably brominated tetracene Particularly suitable for this purpose are the dimerizations, e.g. with the help of organoboron compounds in a cross-coupling reaction, which is widely known as the Suzuki or Stille reaction in chemistry.
- OFETs organic field-effect transistors
- the SiO 2 surface was treated with a silane coupling reagent to improve the homogeneity of the organic film and substrate coverage.
- the substrates thus prepared were introduced directly into a vacuum chamber and the influence of ambient air was avoided.
- the ditetracene 8 was x 10 -6 mbar thermally deposited at a pressure of 1 to structures with prepared at room temperature or at 140 0 C. Electrical characterization was performed using an HP 4155 A semiconductor inert property analyzer. On standard devices with an untreated SiO 2 surface, the organic field-effect transistors produced with ditetracene as semiconductors were tested for their characteristic properties. The representative properties are shown in FIG.
- the curves show the characteristic properties of monopolar field effect transistors with good saturation property.
- the method according to the invention thus demonstrates an efficient synthesis method which can be used in a very general manner, according to which bis- (tetracenyl aromatics) can be prepared.
- These compounds are suitable for highly efficient organic field-effect transistors with increased charge mobility.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Optics & Photonics (AREA)
- Thin Film Transistor (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Electroluminescent Light Sources (AREA)
- Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)
- Photovoltaic Devices (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102005029574A DE102005029574A1 (de) | 2005-06-25 | 2005-06-25 | Oligo-Tetracene, ihre Herstellung und ihre Anwendung |
| PCT/EP2006/005926 WO2007000268A2 (de) | 2005-06-25 | 2006-06-21 | Oligo-tetracene, ihre herstellung und ihre anwendung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| EP1896388A2 true EP1896388A2 (de) | 2008-03-12 |
Family
ID=37461419
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP06762105A Withdrawn EP1896388A2 (de) | 2005-06-25 | 2006-06-21 | Oligo-tetracene, ihre herstellung und ihre anwendung |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US8293957B2 (ja) |
| EP (1) | EP1896388A2 (ja) |
| JP (1) | JP5171617B2 (ja) |
| KR (2) | KR101156239B1 (ja) |
| CN (1) | CN101203471A (ja) |
| CA (1) | CA2610816C (ja) |
| DE (1) | DE102005029574A1 (ja) |
| WO (1) | WO2007000268A2 (ja) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2007238565A (ja) * | 2006-03-10 | 2007-09-20 | Hokkaido Univ | ポリアセン二量体 |
Family Cites Families (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP3591226B2 (ja) * | 1997-06-18 | 2004-11-17 | 東洋インキ製造株式会社 | 有機エレクトロルミネッセンス素子材料およびそれを使用した有機エレクトロルミネッセンス素子 |
| JPH11111458A (ja) * | 1997-09-29 | 1999-04-23 | Toyo Ink Mfg Co Ltd | 有機エレクトロルミネッセンス素子材料およびそれを使用した有機エレクトロルミネッセンス素子 |
| WO2000003565A1 (en) * | 1998-07-10 | 2000-01-20 | Fed Corporation | Amorphous molecular materials for optoelectronic devices and process for producing the same |
| US6284562B1 (en) * | 1999-11-17 | 2001-09-04 | Agere Systems Guardian Corp. | Thin film transistors |
| EP1182183B1 (en) * | 2000-03-29 | 2009-12-09 | Idemitsu Kosan Co., Ltd. | Anthracene derivatives and organic electroluminescent devices made by using the same |
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| US20030097010A1 (en) * | 2001-09-27 | 2003-05-22 | Vogel Dennis E. | Process for preparing pentacene derivatives |
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| US7109519B2 (en) * | 2003-07-15 | 2006-09-19 | 3M Innovative Properties Company | Bis(2-acenyl)acetylene semiconductors |
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| US20060105199A1 (en) * | 2004-11-18 | 2006-05-18 | 3M Innovative Properties Company | Electroluminescent devices containing trans-1,2-bis(acenyl)ethylene compounds |
| KR20080024136A (ko) * | 2005-05-21 | 2008-03-17 | 메르크 파텐트 게엠베하 | 올리고머 폴리아센 및 반도체 배합물 |
-
2005
- 2005-06-25 DE DE102005029574A patent/DE102005029574A1/de not_active Withdrawn
-
2006
- 2006-06-21 KR KR1020077030180A patent/KR101156239B1/ko not_active IP Right Cessation
- 2006-06-21 EP EP06762105A patent/EP1896388A2/de not_active Withdrawn
- 2006-06-21 CN CNA200680022499XA patent/CN101203471A/zh active Pending
- 2006-06-21 US US11/922,963 patent/US8293957B2/en not_active Expired - Fee Related
- 2006-06-21 KR KR1020127005071A patent/KR20120036376A/ko not_active Application Discontinuation
- 2006-06-21 JP JP2008517401A patent/JP5171617B2/ja not_active Expired - Fee Related
- 2006-06-21 CA CA2610816A patent/CA2610816C/en not_active Expired - Fee Related
- 2006-06-21 WO PCT/EP2006/005926 patent/WO2007000268A2/de active Application Filing
Non-Patent Citations (1)
| Title |
|---|
| See references of WO2007000268A2 * |
Also Published As
| Publication number | Publication date |
|---|---|
| US20080214838A1 (en) | 2008-09-04 |
| CA2610816A1 (en) | 2007-01-04 |
| KR20120036376A (ko) | 2012-04-17 |
| JP5171617B2 (ja) | 2013-03-27 |
| KR101156239B1 (ko) | 2012-06-13 |
| CA2610816C (en) | 2012-09-11 |
| WO2007000268A2 (de) | 2007-01-04 |
| DE102005029574A1 (de) | 2006-12-28 |
| JP2008546728A (ja) | 2008-12-25 |
| WO2007000268A3 (de) | 2007-04-19 |
| KR20080027274A (ko) | 2008-03-26 |
| WO2007000268B1 (de) | 2007-05-31 |
| US8293957B2 (en) | 2012-10-23 |
| CN101203471A (zh) | 2008-06-18 |
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