JP5113571B2 - ピリド[3,2−h]キナゾリノン類、および/または、その5,6−ジヒドロ誘導体類、その製造方法、および、これらを含有するドープされた有機半導体材料 - Google Patents
ピリド[3,2−h]キナゾリノン類、および/または、その5,6−ジヒドロ誘導体類、その製造方法、および、これらを含有するドープされた有機半導体材料 Download PDFInfo
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- JP5113571B2 JP5113571B2 JP2008067125A JP2008067125A JP5113571B2 JP 5113571 B2 JP5113571 B2 JP 5113571B2 JP 2008067125 A JP2008067125 A JP 2008067125A JP 2008067125 A JP2008067125 A JP 2008067125A JP 5113571 B2 JP5113571 B2 JP 5113571B2
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- 239000000463 material Substances 0.000 title claims description 40
- 239000004065 semiconductor Substances 0.000 title claims description 37
- 238000000034 method Methods 0.000 title claims description 24
- BWJLRWQWVTZEOD-UHFFFAOYSA-N 1h-pyrido[3,2-h]quinazolin-2-one Chemical class C1=CC=NC2=C(NC(=O)N=C3)C3=CC=C21 BWJLRWQWVTZEOD-UHFFFAOYSA-N 0.000 title claims description 14
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- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 37
- 125000003118 aryl group Chemical group 0.000 claims description 24
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 13
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- 238000004770 highest occupied molecular orbital Methods 0.000 claims description 12
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- 238000004768 lowest unoccupied molecular orbital Methods 0.000 claims description 11
- 125000003342 alkenyl group Chemical group 0.000 claims description 10
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- DHDHJYNTEFLIHY-UHFFFAOYSA-N 4,7-diphenyl-1,10-phenanthroline Chemical compound C1=CC=CC=C1C1=CC=NC2=C1C=CC1=C(C=3C=CC=CC=3)C=CN=C21 DHDHJYNTEFLIHY-UHFFFAOYSA-N 0.000 claims description 7
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- UGNWTBMOAKPKBL-UHFFFAOYSA-N tetrachloro-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(Cl)=C(Cl)C1=O UGNWTBMOAKPKBL-UHFFFAOYSA-N 0.000 claims description 5
- BQVJYQUPRRWNGO-UHFFFAOYSA-N 5,6-dihydropyrido[3,2-h]quinazoline Chemical compound C1=CC=C2CCC3=CN=CN=C3C2=N1 BQVJYQUPRRWNGO-UHFFFAOYSA-N 0.000 claims description 4
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- LDIOUQIXNSSOGU-UHFFFAOYSA-N 8-(3-pentylamino)-2-methyl-3-(2-chloro-4-methoxyphenyl)-6,7-dihydro-5h-cyclopenta[d]pyrazolo[1,5-a]pyrimidine Chemical compound CC1=NN2C(NC(CC)CC)=C3CCCC3=NC2=C1C1=CC=C(OC)C=C1Cl LDIOUQIXNSSOGU-UHFFFAOYSA-N 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- NFNALQOLQWJCNE-UHFFFAOYSA-N [Ir+3].C1=CC=C2C3=NC(C)=CN=C3C3=CC=CC=C3C2=C1.C1=CC=C2C3=NC(C)=CN=C3C3=CC=CC=C3C2=C1 Chemical compound [Ir+3].C1=CC=C2C3=NC(C)=CN=C3C3=CC=CC=C3C2=C1.C1=CC=C2C3=NC(C)=CN=C3C3=CC=CC=C3C2=C1 NFNALQOLQWJCNE-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- BVCZEBOGSOYJJT-UHFFFAOYSA-N ammonium carbamate Chemical compound [NH4+].NC([O-])=O BVCZEBOGSOYJJT-UHFFFAOYSA-N 0.000 description 1
- 238000005899 aromatization reaction Methods 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- 238000005452 bending Methods 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- UFVXQDWNSAGPHN-UHFFFAOYSA-K bis[(2-methylquinolin-8-yl)oxy]-(4-phenylphenoxy)alumane Chemical compound [Al+3].C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC([O-])=CC=C1C1=CC=CC=C1 UFVXQDWNSAGPHN-UHFFFAOYSA-K 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-N carbonic acid monoamide Natural products NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000004020 conductor Substances 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000002484 cyclic voltammetry Methods 0.000 description 1
- 125000005044 dihydroquinolinyl group Chemical group N1(CC=CC2=CC=CC=C12)* 0.000 description 1
- 238000002848 electrochemical method Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 230000005693 optoelectronics Effects 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 125000000962 organic group Chemical group 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 229920000620 organic polymer Polymers 0.000 description 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical class OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 1
- 229920001197 polyacetylene Polymers 0.000 description 1
- XCILQFXEZGRNRO-UHFFFAOYSA-N pyrido[2,3-f]phthalazine Chemical class N1=NC=C2C3=NC=CC=C3C=CC2=C1 XCILQFXEZGRNRO-UHFFFAOYSA-N 0.000 description 1
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 1
- 229930185107 quinolinone Natural products 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 125000003003 spiro group Chemical group 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- 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
- C07D487/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/20—Oxygen atoms
- C07D215/24—Oxygen atoms attached in position 8
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B57/00—Other synthetic dyes of known constitution
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- 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
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
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- 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
- H10K50/16—Electron transporting layers
- H10K50/165—Electron transporting layers comprising dopants
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K71/00—Manufacture or treatment specially adapted for the organic devices covered by this subclass
- H10K71/30—Doping active layers, e.g. electron transporting layers
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- 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
- H10K85/30—Coordination compounds
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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
- 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
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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
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
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- Chemical & Material Sciences (AREA)
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- Spectroscopy & Molecular Physics (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Electroluminescent Light Sources (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Description
1.上記電荷キャリアの移動度を、
a)複数の有機基から成る電子伝達層を用いることによって(米国特許第5,811,833号公報)、
b)上記各分子のπ軌道の最適なオーバーラップを可能にする、高度に配置された各層を生成することによって、増大させる手段。
2.可動性電荷キャリアの濃度を、
a)上記材料を清浄して丁寧に処理して、電荷キャリアの付着した各サイトの形成を回避することによって、
b)各有機層を、
aa)無機材料(アルカリ金属:J. Kido et al., 米国特許第6,013,384号公報; J.Kido et al., Appl. Phys. Lett. 73, 2866頁 (1998年)、ヨウ素、SbCl5などのような酸化剤)、
bb)有機材料(TNCQ:M. Maitrot et al., J. Appl. Phys. 60(7), 2396−2400頁(1986年)、F4TCNQ:M. Pfeiffer et al., Appl. Phys. Lett., 73(22) 3202頁(1998年)、BEDT−TTF:A. Nollau et al., J. Appl. Phys., 87(9), 4340頁(2000年)、ナフタレンジカルボン酸アミド:M. Thomson et al., 国際公開第03088271号公報、陽イオン色素:A. G. Werner, Appl. Phys. Lett. 82, 4495頁(2003年))、
cc)有機金属化合物類(メタロセン:M. Thomson et al., 国際公開第03088271号公報)、
dd)金属錯体類(Ru0(terpy)3:K. Harada et al., Phys. Rev. Lett. 94, 036601(2005年))によりドーピングすることによって増大させる手段。
上記各構造成分a−fは、a=−CR9R10−、b=−CR11R12−、c=−CR13R14−、d=−CR15R16−、e=−CR17R18−、および、f=−CR19R20−であることを意味することが可能であり、この場合、R9−R20は、独立して、水素、C1−C20のアルキル基、C1−C20のシクロアルキル基、C1−C20のアルケニル基、C1−C20のアルキニル基、アリール基、ヘテロアリール基、−NRR、または、−ORであり、R=C1−C20のアルキル基、C1−C20のシクロアルキル基、C1−C20のアルケニル基、C1−C20のアルキニル基、アリール基、または、ヘテロアリール基であり、この場合、好ましくは、R9、R11、R13、R15、R17、R19はH、および、好ましくは、R10、R12、R14、R16、R18、R20はC1−C20のアルキル基、C1−C20のシクロアルキル基、C1−C20のアルケニル基、C1−C20のアルキニル基、アリール基、ヘテロアリール基、−NRR、または、−ORであり、または、上記構造成分cおよび/またはdにおいて、Cを、Siに置き換えることが可能であり、または、必要に応じて、aまたはbまたはeまたはfは、NR(R=C1−C20のアルキル基、C1−C20のシクロアルキル基、C1−C20のアルケニル基、C1−C20のアルキニル基、アリール基、ヘテロアリール基)であるか、または、必要に応じて、aおよびfまたはbおよびcは、NR(R=C1−C20のアルキル基、C1−C20のシクロアルキル基、C1−C20のアルケニル基、C1−C20のアルキニル基、アリール基、ヘテロアリール基)であり、上記構造式Iでは、各化学結合a−c、b−d、c−e、および、d−fの少なくとも何れかはは、不飽和であるが、a−cとc−eとが、共に不飽和になることはなく、b−dとd−fとが、共に不飽和になることはなく、上記構造式Iの場合、上記各化学結合a−c、b−d、c−e、および、d−fは、ヘテロ元素O、S、Se、N、P、Ge、Snを含み得る、飽和または不飽和の環形の一部であることが可能であり、または、上記各化学結合a−c、b−d、c−e、および、d−fは、ヘテロ元素O、S、Si、Nを含み得る、芳香族環形、または、縮合芳香族環形の一部であり、原子Eは、好ましくはC、N、P、As、Sbの群から選択された典型元素であり、上記構造成分a−E−bは、必要に応じて、ヘテロ元素O、S、Se、N、P、Si、Ge、Snを含み得る、飽和または不飽和の環形の構成要素であり、または、上記構造成分a−E−bは、必要に応じて、ヘテロ元素O、S、Se、Nを含み得る、芳香族環形の構成要素である。
13.51gの2,4,6−トリフェニルピリリウムテトラフルオロホウ酸(34.1mmol)と、4.78gのシクロヘキサン−1,2−ジオン(42.6mmol)との懸濁液を、メタノール中において、沸点まで加熱し、その後、4.56gの酢酸(75.9mmol)と7.68gのトリエチルアミン(75.9mmol)とを少しのメタノールに溶かした溶液を、滴下して加えた。還流において7時間加熱した後に、上記反応溶液を室温まで冷却した。吸引によって淡黄色の沈殿物を分取し、100mlの氷冷メタノールによって少しずつ洗浄して、恒量まで乾燥させた。融点が178℃−179℃(文献:182−184℃)の、11.37gの淡黄色の粉末(79.3%)を得た。
15mlの蒸留水中の1.5gの水酸化カリウムの溶液(36.7mmol)を、5gの6,7−ジヒドロ−2,4−ジフェニルキノリン−8(5H)−オン(16.7mmol)の懸濁液に加えた。結果として生じる懸濁液を、室温において、密封された丸底フラスコの中で1日間攪拌し、氷酢酸によって中和させて、室温における攪拌工程を30分間続ける。この沈殿物を吸引によって分取し、蒸留水で洗浄して、乾燥させた。
3gの7−トルイデン−6,7−ジヒドロ−2,4−ジフェニルキノリン−8(5H)−オン(7.5mmol)、および、1.6gのベンズアミジニウム塩化物一水和物(8.2mmol)を50mlのエタノールにおいて懸濁し、沸点まで加熱した。上記沈殿物が徐々に溶解する間に、該懸濁液に、20mlのエタノール中の1.2gのカリウムtert−ブトキシド(10mmol)の溶液を滴下した。還流状態において24時間沸騰させた後に、上記懸濁液を室温において冷却した。この沈殿物を吸引によって分取し、蒸留水およびエタノールで洗浄し、高真空の下で恒量まで乾燥させた。128℃−133℃の融点を有する、2.6gの生成物(57%)を得た。
2.5gの2,4,7,9−テトラフェニル−1,4,5,6−テトラヒドロピリド[3,2−h]キナゾリン(4.96mmol)を、70mlのクロロホルムにおいて溶解した。その後、1.46gのクロルアニル(5.95mmol)を一度に加えた。結果として生じた茶色がかった懸濁液を室温において攪拌する工程を続けた。30分後に、この上澄み液のDC検査(アルミニウム酸化物;溶離液:二塩化メチレン)は、上記反応が完了したことを示した。この懸濁液をD4ガラス濾過器によって濾過した。
2gの5,6−ジヒドロ−2,7,9−トリフェニル−4−p−トルイルピリド[3,2−h]キナゾリン(3.98mmol)を、100mlのジエチレングリコールにて懸濁し、加熱しながら溶液とした後、500mgのPd/C(10%)を少しずつ加えた。この懸濁液を沸点まで加熱し、DC検査によって決定されるように、還流状態において、上記出発材料を検出することが不可能になるまで沸騰状態にて加熱した。
Claims (27)
- 下記の構造式8であり、
R3は、H、C1−C20のアルキル基およびアリール基から選択されており、
R4は、H、C1−C20のアルキル基およびアリール基、NH 2 、NHR(R=C1−C20のアルキル基)、NR2(R=C1−C20のアルキル基)、N−アルキルアリール基、N−(アリール基)2、カルバゾリル基、ジベンザゼピニル基、並びに、CN基から選択されている、ピリド[3,2−h]キナゾリノン、および/または、その5,6−ジヒドロ誘導体。 - ピリド[3,2−h]キナゾリノン、および/または、その5,6−ジヒドロ誘導体の製造方法であって、
上記方法は、
(i)以下の反応スキームに従って、
(ii)以下の反応スキームに従って、
(iii) 必要に応じて、以下の反応スキームに従って、
R1、R2、R3およびR4は、請求項1に記載のものである、ピリド[3,2−h]キナゾリノン、および/または、その5,6−ジヒドロ誘導体の製造方法。 - 上記塩基として、水酸化カリウム、および/または、カリウムtert−ブトキシドを用いることを特徴とする、請求項2に記載の製造方法。
- 1,4,5,6−テトラヒドロピリド[3,2−h]キナゾリン6を酸化させるためにクロルアニルを用いることを特徴とする、請求項2または3に記載の製造方法。
- Pd触媒された脱水素反応による芳香族化する工程は、Pd/Cで行われることを特徴とする請求項2〜4のいずれか1項に記載の製造方法。
- 少なくとも1つのドーパントでドープされた、少なくとも1つの有機マトリクス材を含み、
上記有機マトリクス材は、請求項1に記載の、ピリド[3,2−h]キナゾリン、および/または、その5,6−ジヒドロ誘導体である、ドープされた有機半導体材料。 - 上記有機マトリクス材は、可逆的に還元可能であることを特徴とする、請求項6に記載の有機半導体材料。
- 上記有機マトリクス材は、還元中に、安定した酸化還元の各活性成分を生じるものであることを特徴とする、請求項6に記載の有機半導体材料。
- 上記ドーパントは、金属錯体であることを特徴とする、請求項6〜8のいずれか1項に記載の有機半導体材料。
- 上記金属錯体は、下記の構造式Iのものであり、
上記各構造成分a−fは、a=−CR9R10−、b=−CR11R12−、c=−CR13R14−、d=−CR15R16−、e=−CR17R18−、および、f=−CR19R20−であり、R9−R20は、独立して、水素、C1−C20のアルキル基、C 3 −C 20 のシクロアルキル基、C 2 −C 20 のアルケニル基、C 2 −C 20 のアルキニル基、アリール基、−NRR、または、−ORであり、上記Rは、R=C1−C20のアルキル基、C 3 −C 20 のシクロアルキル基、C 2 −C 20 のアルケニル基、C 2 −C 20 のアルキニル基またはアリール基であり、
または、上記構造成分cおよび/またはdにおいて、Cを、Siに置き換えることが可能であり、
または、必要に応じて、aまたはbまたはeまたはfは、NR(R=C1−C20のアルキル基、C 3 −C 20 のシクロアルキル基、C 2 −C 20 のアルケニル基、C 2 −C 20 のアルキニル基、アリール基)であり、
または、必要に応じて、aおよびfまたはbおよびcは、NR(R=C1−C20のアルキル基、C 3 −C 20 のシクロアルキル基、C 2 −C 20 のアルケニル基、C 2 −C 20 のアルキニル基、アリール基)であり、
各化学結合a−c、b−d、c−e、および、d−fの少なくとも何れかは、不飽和であるが、a−cとc−eとが、共に不飽和になることはなく、b−dとd−fとが、共に不飽和になることはなく、
上記各化学結合a−c、b−d、c−e、および、d−fは、ヘテロ元素O、S、N、P、Se、Ge、Snを含み得る、飽和または不飽和の環形の一部であってもよく、
または、上記各化学結合a−c、b−d、c−e、および、d−fは、ヘテロ元素O、S、Si、Nを含み得る、芳香族環形、または、縮合芳香族環形の一部であり、
原子Eは、典型元素であり、
上記構造成分a−E−bは、必要に応じて、ヘテロ元素O、S、Se、N、P、Si、Ge、Snを含み得る、飽和または不飽和の環形の構成要素であるか、または、
上記構造成分a−E−bは、必要に応じて、ヘテロ元素O、S、Se、Nを含み得る、芳香族環形の構成要素であることを特徴とする、請求項9に記載の有機半導体材料。 - Mは、MoまたはWであることを特徴とする、請求項10に記載の有機半導体材料。
- R9、R11、R13、R15、R17、R19はHであり、および、R10、R12、R14、R16、R18、R20はC1−C20のアルキル基、C 3 −C 20 のシクロアルキル基、C 2 −C 20 のアルケニル基、C 2 −C 20 のアルキニル基、アリール基、−NRR、または、−ORであることを特徴とする、請求項10に記載の有機半導体材料。
- Eは、C、N、P、As、Sbの群から選択されていることを特徴とする、請求項10に記載の有機半導体材料。
- 上記ドーパントは、アルカリ、および/または、アルカリ土類金属であることを特徴とする、請求項6〜8のいずれか1項に記載の有機半導体材料。
- 上記ドーパントは、セシウムであることを特徴とする、請求項15に記載の有機半導体材料。
- 上記有機マトリクス材は、上記ドーパントのイオン化電位(HOMO)から0〜0.5Vにて異なる最低空軌道(LUMO)のエネルギー準位を有することを特徴とする、請求項6〜16のいずれか1項に記載の有機半導体材料。
- 上記有機マトリクス材のエネルギー準位は、上記ドーパントのイオン化電位から0〜0.3Vにて異なることを特徴とする、請求項17に記載の有機半導体材料。
- 上記有機マトリクス材のエネルギー準位は、上記ドーパントのイオン化電位から0〜0.15Vにて異なることを特徴とする、請求項17に記載の有機半導体材料。
- 上記有機マトリクス材は、上記ドーパントのイオン化電位(HOMO)よりも低いLUMOエネルギー準位を有することを特徴とする、請求項6〜19のいずれか1項に記載の有機半導体材料。
- 上記ドーパントの濃度は、0.5重量パーセント〜25重量パーセントであることを特徴とする、請求項6〜20のいずれか1項に記載の有機半導体材料。
- 上記ドーパントの濃度は、1重量パーセント〜10重量パーセントであることを特徴とする、請求項21に記載の有機半導体材料。
- 上記ドーパントの濃度は、2.5重量パーセント〜5重量パーセントであることを特徴とする、請求項21に記載の有機半導体材料。
- 上記有機マトリクス材のガラス転移温度Tgは、4,7−ジフェニル−1,10−フェナントロリンの転移温度よりも高いことを特徴とする、請求項6〜23のいずれか1項に記載の有機半導体材料。
- 上記有機マトリクス材は、少なくとも200℃の昇華温度を有していることを特徴とする、請求項6〜24のいずれか1項に記載の有機半導体材料。
- 請求項6〜25のいずれか1項に記載の有機半導体材料を含む、有機発光ダイオード。
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KR101104552B1 (ko) | 2012-01-11 |
US7807687B2 (en) | 2010-10-05 |
KR20080084762A (ko) | 2008-09-19 |
ES2350409T3 (es) | 2011-01-21 |
US20110046374A1 (en) | 2011-02-24 |
TWI387596B (zh) | 2013-03-01 |
JP2009001544A (ja) | 2009-01-08 |
EP1970371A1 (de) | 2008-09-17 |
CN101348484A (zh) | 2009-01-21 |
CN101348484B (zh) | 2013-10-02 |
EP1970371B1 (de) | 2010-08-25 |
US20120041197A1 (en) | 2012-02-16 |
DE502008001180D1 (de) | 2010-10-07 |
US20080227979A1 (en) | 2008-09-18 |
DE102007012794B3 (de) | 2008-06-19 |
TW200846349A (en) | 2008-12-01 |
US8115003B2 (en) | 2012-02-14 |
US8329898B2 (en) | 2012-12-11 |
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