JP6570834B2 - 電子素子のための化合物 - Google Patents
電子素子のための化合物 Download PDFInfo
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- JP6570834B2 JP6570834B2 JP2014546340A JP2014546340A JP6570834B2 JP 6570834 B2 JP6570834 B2 JP 6570834B2 JP 2014546340 A JP2014546340 A JP 2014546340A JP 2014546340 A JP2014546340 A JP 2014546340A JP 6570834 B2 JP6570834 B2 JP 6570834B2
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- 150000001875 compounds Chemical class 0.000 title claims description 104
- 125000003118 aryl group Chemical group 0.000 claims description 72
- -1 aryl compound Chemical class 0.000 claims description 39
- 239000000463 material Substances 0.000 claims description 32
- 230000005525 hole transport Effects 0.000 claims description 29
- 125000001072 heteroaryl group Chemical group 0.000 claims description 23
- 125000004432 carbon atom Chemical group C* 0.000 claims description 20
- 239000000203 mixture Substances 0.000 claims description 17
- 239000002019 doping agent Substances 0.000 claims description 14
- 229910052757 nitrogen Inorganic materials 0.000 claims description 14
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 12
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 230000000903 blocking effect Effects 0.000 claims description 8
- 238000009472 formulation Methods 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 6
- 125000004122 cyclic group Chemical group 0.000 claims description 3
- 238000005401 electroluminescence Methods 0.000 claims description 3
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 3
- 238000007832 transition metal-catalyzed coupling reaction Methods 0.000 claims description 3
- 125000003277 amino group Chemical group 0.000 claims description 2
- DEFLNOSTNCSZRB-IDTAVKCVSA-N 9-[(2r,3r,4r,5r)-3,4-dimethoxy-5-(methoxymethyl)oxolan-2-yl]-n-methoxypurin-6-amine Chemical compound CO[C@@H]1[C@H](OC)[C@@H](COC)O[C@H]1N1C2=NC=NC(NOC)=C2N=C1 DEFLNOSTNCSZRB-IDTAVKCVSA-N 0.000 claims 1
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- 238000000034 method Methods 0.000 description 14
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- 229920000736 dendritic polymer Polymers 0.000 description 13
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- 125000000304 alkynyl group Chemical group 0.000 description 5
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- 229910052740 iodine Inorganic materials 0.000 description 5
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- 125000004001 thioalkyl group Chemical group 0.000 description 5
- DXBHBZVCASKNBY-UHFFFAOYSA-N 1,2-Benz(a)anthracene Chemical compound C1=CC=C2C3=CC4=CC=CC=C4C=C3C=CC2=C1 DXBHBZVCASKNBY-UHFFFAOYSA-N 0.000 description 4
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- KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
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- DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical compound C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 description 4
- 150000004982 aromatic amines Chemical class 0.000 description 4
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 239000004305 biphenyl Substances 0.000 description 4
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 4
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical compound C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 description 4
- 230000014509 gene expression Effects 0.000 description 4
- 125000000623 heterocyclic group Chemical group 0.000 description 4
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 4
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- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 4
- 150000002576 ketones Chemical class 0.000 description 4
- RDOWQLZANAYVLL-UHFFFAOYSA-N phenanthridine Chemical compound C1=CC=C2C3=CC=CC=C3C=NC2=C1 RDOWQLZANAYVLL-UHFFFAOYSA-N 0.000 description 4
- 229910052697 platinum Inorganic materials 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 4
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- 238000006467 substitution reaction Methods 0.000 description 4
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- BPMFPOGUJAAYHL-UHFFFAOYSA-N 9H-Pyrido[2,3-b]indole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=N1 BPMFPOGUJAAYHL-UHFFFAOYSA-N 0.000 description 3
- 0 C*(*)C([C@]1C(C)****1)=**=C(*)C(C)(C)* Chemical compound C*(*)C([C@]1C(C)****1)=**=C(*)C(C)(C)* 0.000 description 3
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 3
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- 230000008878 coupling Effects 0.000 description 3
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- 239000002346 layers by function Substances 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- IMKMFBIYHXBKRX-UHFFFAOYSA-M lithium;quinoline-2-carboxylate Chemical compound [Li+].C1=CC=CC2=NC(C(=O)[O-])=CC=C21 IMKMFBIYHXBKRX-UHFFFAOYSA-M 0.000 description 1
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 1
- 229910001092 metal group alloy Inorganic materials 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- 229940095102 methyl benzoate Drugs 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 229910003455 mixed metal oxide Inorganic materials 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- 239000011733 molybdenum Substances 0.000 description 1
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000005244 neohexyl group Chemical group [H]C([H])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000004365 octenyl group Chemical group C(=CCCCCCC)* 0.000 description 1
- 125000005069 octynyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C#C* 0.000 description 1
- 238000007645 offset printing Methods 0.000 description 1
- 125000000962 organic group Chemical group 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229910052762 osmium Inorganic materials 0.000 description 1
- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 description 1
- 150000002921 oxetanes Chemical class 0.000 description 1
- 150000002924 oxiranes Chemical class 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
- 125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 1
- 125000005981 pentynyl group Chemical group 0.000 description 1
- 238000001126 phototherapy Methods 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 150000003142 primary aromatic amines Chemical class 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- BUAWIRPPAOOHKD-UHFFFAOYSA-N pyrene-1,2-diamine Chemical class C1=CC=C2C=CC3=C(N)C(N)=CC4=CC=C1C2=C43 BUAWIRPPAOOHKD-UHFFFAOYSA-N 0.000 description 1
- GDISDVBCNPLSDU-UHFFFAOYSA-N pyrido[2,3-g]quinoline Chemical compound C1=CC=NC2=CC3=CC=CN=C3C=C21 GDISDVBCNPLSDU-UHFFFAOYSA-N 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 229920013730 reactive polymer Polymers 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 229910052702 rhenium Inorganic materials 0.000 description 1
- WUAPFZMCVAUBPE-UHFFFAOYSA-N rhenium atom Chemical compound [Re] WUAPFZMCVAUBPE-UHFFFAOYSA-N 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000003336 secondary aromatic amines Chemical class 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 239000010944 silver (metal) Substances 0.000 description 1
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical compound C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
- 235000021286 stilbenes Nutrition 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 125000006836 terphenylene group Chemical group 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000001931 thermography Methods 0.000 description 1
- 238000010023 transfer printing Methods 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 238000002061 vacuum sublimation Methods 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/60—Preparation of compounds containing amino groups bound to a carbon skeleton by condensation or addition reactions, e.g. Mannich reaction, addition of ammonia or amines to alkenes or to alkynes or addition of compounds containing an active hydrogen atom to Schiff's bases, quinone imines, or aziranes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C211/54—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to two or three six-membered aromatic rings
-
- 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]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
-
- 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
- H10K50/15—Hole transporting layers
-
- 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
- H10K85/341—Transition metal complexes, e.g. Ru(II)polypyridine complexes
- H10K85/342—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising iridium
-
- 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
- H10K85/341—Transition metal complexes, e.g. Ru(II)polypyridine complexes
- H10K85/346—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising platinum
-
- 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
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
-
- 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
- C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
- C07C2603/06—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members
- C07C2603/10—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings
- C07C2603/12—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings only one five-membered ring
- C07C2603/18—Fluorenes; Hydrogenated fluorenes
-
- 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
- H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
-
- 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
Description
Wは、CHまたはNであり;
Ar1は、出現毎に同一であるか異なり、1以上の基R1により置換されてよい6〜30個の芳香族環原子を有する芳香族もしくは複素環式芳香族環構造であり;
Ar2は、出現毎に同一であるか異なり、1以上の基R1により置換されてよい6〜24個の芳香族環原子を有する芳香族もしくは複素環式芳香族環構造であり;
R1は、出現毎に同一であるか異なり、H、D、F、Cl、Br、I、C(=O)R2、CN、Si(R2)3、NO2、P(=O)(R2)2、S(=O)R2、S(=O)2R2、1〜20個のC原子を有する直鎖アルキル、アルコキシもしくはチオアルキル基、3〜20個のC原子を有する分岐あるいは環状アルキル、アルコキシもしくはチオアルキル基、2〜20個のC原子を有するアルケニルもしくはアルキニル基(上記言及した基は、夫々1以上の基R2により置換されてよく、上記言及した基中の1以上のCH2基は、-R2C=CR2-、-C≡C-、Si(R2)2、C=O、C=S、C=NR2、-C(=O)O-、-C(=O)NR2-、NR2、P(=O)(R2)、-O-、-S-、SOもしくはSO2で置き代えられてよく、ここで、上記言及した基中の1以上のH原子は、D、F、Cl、Br、I、CNもしくはNO2で置き代えられてよい。)または、各場合に、1以上の基R2により置換されてよい5〜30個の芳香族環原子を有する芳香族もしくは複素環式芳香族環構造であり;ここで、2個以上の基R1は、たがいに結合してよく、および環を形成してよく;
R2は、出現毎に同一であるか異なり、H、D、F、Cl、Br、I、C(=O)R3、CN、Si(R3)3、NO2、P(=O)(R3)2、S(=O)R3、S(=O)2R3、1〜20個のC原子を有する直鎖アルキル、アルコキシもしくはチオアルキル基、3〜20個のC原子を有する分岐あるいは環状アルキル、アルコキシもしくはチオアルキル基、2〜20個のC原子を有するアルケニルもしくはアルキニル基(上記言及した基は、夫々1以上の基R3により置換されてよく、上記言及した基中の1以上のCH2基は、-R3C=CR3-、-C≡C-、Si(R3)2、C=O、C=S、C=NR3、-C(=O)O-、-C(=O)NR3-、NR3、P(=O)(R3)、-O-、-S-、SOもしくはSO2で置き代えられてよく、ここで、上記言及した基中の1以上のH原子は、D、F、Cl、Br、I、CNもしくはNO2で置き代えられてよい。)または、各場合に、1以上の基R3により置換されてよい5〜30個の芳香族環原子を有する芳香族もしくは複素環式芳香族環構造であり;ここで、2個以上の基R2は、たがいに結合してよく、および環を形成してよく;
R3は、出現毎に同一であるか異なり、H、D、F、1〜20個のC原子を有する脂肪族、芳香族もしくは複素環式芳香族有機基であって、さらに、1以上のH原子は、DもしくはFで置き代えられてよく;ここで、2個以上の置換基R3は、たがいに結合してよく、および環を形成してよく;
nは、出現毎に同一であるか異なり、0、1、2、3、4または5であり;
mは、0、1、2または3であり;
ここで、中央の窒素原子に結合する三個の基は、全体として、全て同一ではなく、および
以下の化合物は、除外される。
aおよびbは、互いに、同一か異なり、0または1であってよく、および
基は、破線を介して式(I)の親構造に結合するか、または
式(Ar1-2)の基である。
cおよびdは、互いに、同一か異なり、0または1であってよく、および
基は、破線を介して式(I)の親構造に結合する
基Ar1の、非常に、特に、好ましい態様は、以下の式(Ar1-a)〜(Ar1-d)である。
基は、破線を介して式(I)の親構造に結合する。
eは、各場合に、同一か異なり、0または1であってよく、および
基は、破線を介して式(I)の親構造に結合する。
(A)スズキ重合;
(B)ヤマモト重合;
(C)スチル重合および
(D)ハートウイッグ-ブッフバルト重合
重合をこれらの方法により実行することができる方法と次いでポリマーを反応媒体から分離し、精製することができる方法は、当業者に知られており、文献、たとえば、WO 2003/048225、WO 2004/037887およびWO 2004/037887に詳細に記載されている。
本発明の有機エレクトロルミネセンス素子の正孔注入もしくは正孔輸送層中で、または電子輸送層中で使用することができる適切な電荷輸送材料は、たとえば、Y. Shirota et al., Chem. Rev. 2007, 107(4), 953-1010に開示された化合物または先行技術によりこれらの層に使用される他の材料である。
A)合成例
以下の合成は、他に断らない限り、保護ガス雰囲気下、無水溶媒中で行われる。出発物質は、たとえば、アルドリッチ(ALDRICH)またはABCRから購入することができる。括弧内の番号は、CAS番号に関する。
本発明によるOLEDと先行技術にしたがうOLEDが、WO 04/058911にしたがう一般的プロセスにより製造されるが、ここに記載される状況(層の厚さの変化、材料)に適合される。
厚さ150nmの構造化されたITO(インジウム錫酸化物)で被覆されたガラス板が、改善された加工のために、20nmのPEDOT(ポリ(3,4-エチレンジオキシ-2,5-チオフェン)ポリ(スチレンスホネート、水からのスピンコートにより適用、H. C. Starck, Goslar,独から購入。)で被覆される。これらの被覆されたガラス板は、OLEDが適用される基板を形成する。OLEDは、基本的に、次の層構造を有する:基板/正孔注入層(HIL)/正孔輸送層(HTL)/中間層(IL)/随意に正孔輸送層(HTL2)、電子ブロック層(EBL)/発光層(EML)/電子輸送層(ETL)および最後にカソード。カソードは、100nm厚のアルミニウム層により形成される。OLEDの正確な構造は、表1と2に示される。OLEDの製造のために必要とされる材料は、表5に示される。
Claims (12)
- 以下が、出現する記号と添え字に適用される式(I)の化合物;
Wは、CHであり;
Ar1は、出現毎に同一であるか異なり、夫々、1以上の基R1により置換されてよいフェニルまたはフルオレニルであり;
Ar2は、出現毎に同一であるか異なり、1以上の基R1により置換されてよいフェニルであり;
R1は、出現毎に同一であるか異なり、H、1〜10個のC原子を有する直鎖アルキル基、3〜10個のC原子を有する分岐あるいは環状アルキル基または、各場合に、5〜20個の芳香族環原子を有する芳香族もしくは複素環式芳香族環構造であり;
nは、出現毎に同一であるか異なり、0または1であり;
ただし、添え字nの合計は少なくとも2であり;
mは、出現毎に同一であるか異なり、0または1であり;
ここで、中央の窒素原子に結合する三個の基は、全体として、全て同一ではなく、および
以下の化合物は、除外される。
- 複素環式芳香族環を含まないことを特徴とする、請求項1または2記載の化合物。
- Ar1は、1以上の基R1により置換されてよいフェニルであることを特徴とする、請求項1または2記載の化合物。
- 式(I)の化合物中の少なくとも一つの基Ar1は、中央の窒素原子への結合に対して、メタ位で六員環に結合することを特徴とする、請求項1〜3何れか1項記載の化合物。
- nは、出現毎に同一であるか異なり、1であることを特徴とする、請求項1〜4何れか1項記載の化合物。
- mは、0であることを特徴とする、請求項1〜5何れか1項記載の化合物。
- Ar1は、中央の窒素原子への結合に対して、オルト位で六員環に結合しないことを特徴とする、請求項1〜6何れか1項記載の化合物。
- Ar1は、フェニルおよび9,9'-ジメチルフルオレニルから選ばれ、Ar2はフェニルであり、R1ではHである、請求項1記載の化合物。
- アミノ基を含むアリール化合物と、脱離基を含むアリール化合物が、遷移金属触媒カップリング反応で互いに結合することを特徴とする、請求項1〜8何れか1項記載の化合物の製造方法。
- 請求項1〜8何れか1項記載の少なくとも一つの化合物と少なくとも一つの溶媒を含む調合物。
- 請求項1〜8何れか1項記載の少なくとも一つの化合物を含むことを特徴とする有機エレクトロルミネッセンス素子(OLED)。
- 請求項1〜8何れか1項記載の化合物が、正孔輸送層もしくは電子ブロック層の一以上の層中で正孔輸送材料として、または一以上の燐光ドーパントと組み合わせて発光層中でのマトリックス材料として使用されることを特徴とする、請求項11記載の有機エレクトロルミッセンス素子。
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CN103998415A (zh) | 2014-08-20 |
KR20170083154A (ko) | 2017-07-17 |
US20180269399A1 (en) | 2018-09-20 |
CN105742499A (zh) | 2016-07-06 |
CN103998415B (zh) | 2016-10-12 |
US10424739B2 (en) | 2019-09-24 |
EP2791105B1 (de) | 2020-03-18 |
JP2015502960A (ja) | 2015-01-29 |
KR101961613B1 (ko) | 2019-03-25 |
KR20140103146A (ko) | 2014-08-25 |
US20140312287A1 (en) | 2014-10-23 |
JP2018035169A (ja) | 2018-03-08 |
EP2791105A1 (de) | 2014-10-22 |
US10665787B2 (en) | 2020-05-26 |
KR20180126629A (ko) | 2018-11-27 |
US10008672B2 (en) | 2018-06-26 |
WO2013087142A1 (de) | 2013-06-20 |
US20180269398A1 (en) | 2018-09-20 |
CN105742499B (zh) | 2018-02-13 |
KR101921896B1 (ko) | 2018-11-26 |
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