WO2010067893A1 - Novel pyrene compound - Google Patents
Novel pyrene compound Download PDFInfo
- Publication number
- WO2010067893A1 WO2010067893A1 PCT/JP2009/070941 JP2009070941W WO2010067893A1 WO 2010067893 A1 WO2010067893 A1 WO 2010067893A1 JP 2009070941 W JP2009070941 W JP 2009070941W WO 2010067893 A1 WO2010067893 A1 WO 2010067893A1
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- BBEAQIROQSPTKN-UHFFFAOYSA-N antipyrene Natural products C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 title claims abstract description 27
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 title claims abstract description 27
- -1 pyrene compound Chemical class 0.000 title claims abstract description 27
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims abstract description 21
- 125000003118 aryl group Chemical group 0.000 claims abstract description 17
- 125000001624 naphthyl group Chemical group 0.000 claims abstract description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 9
- 150000002894 organic compounds Chemical class 0.000 claims description 18
- 239000010410 layer Substances 0.000 description 67
- 150000001875 compounds Chemical class 0.000 description 63
- 239000000758 substrate Substances 0.000 description 23
- 239000000463 material Substances 0.000 description 18
- 230000005525 hole transport Effects 0.000 description 12
- 125000001424 substituent group Chemical group 0.000 description 12
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 9
- 239000010408 film Substances 0.000 description 9
- 239000000543 intermediate Substances 0.000 description 9
- 125000005581 pyrene group Chemical group 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 125000006267 biphenyl group Chemical group 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- 238000002347 injection Methods 0.000 description 5
- 239000007924 injection Substances 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 238000005259 measurement Methods 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- 125000000753 cycloalkyl group Chemical group 0.000 description 3
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 3
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- 125000002704 decyl 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])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 238000000151 deposition Methods 0.000 description 3
- 125000003438 dodecyl 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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 230000009477 glass transition Effects 0.000 description 3
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 239000011159 matrix material Substances 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 125000001421 myristyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 239000012044 organic layer Substances 0.000 description 3
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 125000002958 pentadecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 3
- 125000005561 phenanthryl group Chemical group 0.000 description 3
- 150000003220 pyrenes Chemical class 0.000 description 3
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- 125000003944 tolyl group Chemical group 0.000 description 3
- 125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 230000021615 conjugation Effects 0.000 description 2
- 238000001840 matrix-assisted laser desorption--ionisation time-of-flight mass spectrometry Methods 0.000 description 2
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 2
- 238000001771 vacuum deposition Methods 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- MEKOFIRRDATTAG-UHFFFAOYSA-N 2,2,5,8-tetramethyl-3,4-dihydrochromen-6-ol Chemical compound C1CC(C)(C)OC2=C1C(C)=C(O)C=C2C MEKOFIRRDATTAG-UHFFFAOYSA-N 0.000 description 1
- 101150067539 AMBP gene Proteins 0.000 description 1
- 239000004925 Acrylic resin Substances 0.000 description 1
- 229920000178 Acrylic resin Polymers 0.000 description 1
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 125000002619 bicyclic group Chemical group 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 230000005587 bubbling Effects 0.000 description 1
- 239000003990 capacitor Substances 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000000919 ceramic Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 239000002274 desiccant Substances 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000004770 highest occupied molecular orbital Methods 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 150000002484 inorganic compounds Chemical class 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 238000009413 insulation Methods 0.000 description 1
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000002985 plastic film Substances 0.000 description 1
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 239000012780 transparent material Substances 0.000 description 1
- 238000004506 ultrasonic cleaning Methods 0.000 description 1
- 238000007738 vacuum evaporation Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C13/00—Cyclic hydrocarbons containing rings other than, or in addition to, six-membered aromatic rings
- C07C13/28—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof
- C07C13/32—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings
- C07C13/54—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with three condensed rings
- C07C13/547—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with three condensed rings at least one ring not being six-membered, the other rings being at the most six-membered
- C07C13/567—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with three condensed rings at least one ring not being six-membered, the other rings being at the most six-membered with a fluorene or hydrogenated fluorene ring system
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
- H05B33/00—Electroluminescent light sources
- H05B33/10—Apparatus or processes specially adapted to the manufacture of electroluminescent light sources
-
- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
- H05B33/00—Electroluminescent light sources
- H05B33/12—Light sources with substantially two-dimensional radiating surfaces
- H05B33/14—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of the electroluminescent material, or by the simultaneous addition of the electroluminescent material in or onto the light source
-
- 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
- H10K85/622—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing four rings, e.g. pyrene
-
- 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
-
- 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
- C07C2603/22—Ortho- or ortho- and peri-condensed systems containing three rings containing only six-membered rings
- C07C2603/26—Phenanthrenes; Hydrogenated phenanthrenes
-
- 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
- C07C2603/50—Pyrenes; Hydrogenated pyrenes
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1011—Condensed systems
-
- 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
Definitions
- the present invention relates to a novel pyrene compound and an organic electroluminescent (EL) device including an organic compound layer containing such a novel pyrene compound.
- EL organic electroluminescent
- the present invention provides a novel pyrene compound having high thermal stability.
- the present invention also provides a highly durable organic EL device with such a novel pyrene compound having high thermal stability.
- the present invention provides a pyrene compound represented by general formula (1) . [ 0005 ]
- the present invention also provides an organic electroluminescent device including an anode, a cathode, and an organic compound layer disposed between the anode and the cathode, wherein the organic compound layer contains the above-described pyrene compound.
- the present invention can provide a novel pyrene compound having high thermal stability. Use of such a novel pyrene compound having high thermal stability can provide a highly durable organic EL device.
- a pyrene compound according to the present invention is represented by general formula (1) below. This compound includes an aryl group in the 1 position of the pyrene ring; and a fluorenyl group in the 7 position of the pyrene ring.
- the 7 position of a pyrene ring is electronically unique and such introduction of a fluorenyl group negligibly causes an increase in the emission wavelength. For this reason, introduction of a fluorenyl group into the 7 position of a pyrene ring is advantageous for providing organic EL materials having short emission wavelengths (for example, blue light or green light) .
- a fluorenyl group represented as FL in general formula (1) may be unsubstituted or include a substituent.
- substituents include: linear alkyl groups such as a methyl group, an ethyl group, an isopropyl group, a n-butyl group, a tert-butyl group, a pentyl group, a hexyl group, an octyl group, a decyl group, a dodecyl group, a tridecyl group, a tetradecyl group, a pentadecyl group, a hexadecyl group, and an octadecyl group; cycloalkyl groups such as a cyclopentyl group and a cyclohexyl group; and aryl groups such as a phenyl group, a tolyl group, a biphenyl group, a nap
- Al has a large influence over the HOMO of the molecule.
- the resultant compound has degraded stability against oxidation and relatively long emission wavelengths .
- Al is preferably any one of a benzene ring, a naphthalene ring, and a fluorene ring, which have short conjugation length.
- An organic EL device at least includes an anode, a cathode, and an organic compound layer disposed between the anode and the cathode.
- An organic EL device emits light means that such an organic compound layer of the EL device emits light.
- Such an organic compound emitting light is referred to as a light-emitting material in this specification.
- An organic compound layer containing such a light-emitting material functions as a light-emitting layer.
- the organic compound layer may contain a host material and a guest material.
- a host material is a main component of an organic light-emitting layer, and a guest material is an accessory component of the organic light-emitting layer.
- such a benzene ring, a naphthalene ring, or a fluorene ring that is represented by Al may be unsubstituted or include a substituent.
- substituents include: linear alkyl groups such as a methyl group, an ethyl group, an isopropyl group, a n-butyl group, a tert-butyl group, a pentyl group, a hexyl group, an octyl group, a decyl group, a dodecyl group, a tridecyl group, a tetradecyl group, a pentadecyl group, a hexadecyl group, and an octadecyl group; cycloalkyl groups such as a cyclopentyl group and a cyclohexyl group; and aryl groups such as a phenyl group, a tolyl group, a biphenyl group, a naphthyl group, and a fluorenyl group.
- linear alkyl groups such as a methyl group, an ethyl
- an aryl group represented by A2 can be selected in accordance with a desired emission wavelength.
- an aryl group represented by A2 is preferably a mono- to tricyclic aryl group.
- an aryl group represented by A2 is a mono- to tricyclic aryl group
- the resultant compound is suitable as a material emitting short-wavelength light such as blue light or green light, particularly as a host material.
- examples of a mono- to tricyclic aryl group include a phenyl group, a biphenyl group, a naphthyl group, a fluorenyl group, a phenanthryl group, and an anthryl group.
- a biphenyl group, a naphthyl group, and a fluorenyl group are classified as bicyclic aryl groups.
- a phenanthryl group and an anthryl group are classified as tricyclic aryl groups. Of these examples, more preferred are a naphthyl group, a fluorenyl group, and a phenanthryl group.
- A2 may be unsubstituted or include a substituent.
- substituents include: linear alkyl groups such as a methyl group, an ethyl group, an isopropyl group, a n-butyl group, a tert-butyl group, a pentyl group, a hexyl group, an octyl group, a decyl group, a dodecyl group, a tridecyl group, a tetradecyl group, a pentadecyl group, a hexadecyl group, and an octadecyl group; cycloalkyl groups such as a cyclopentyl group and a cyclohexyl group; and aryl groups such as a phenyl group, a tolyl group, a biphenyl group, a naphthyl group, and a fluorenyl group.
- linear alkyl groups such as a methyl group, an ethyl
- Compound (11) Compound (15) [0029]
- These compounds shown as examples include a fluorenyl group in the 7 position of the pyrene ring and hence the stacking of pyrenes is hindered due to steric hindrance.
- a highly amorphous pyrene compound is provided.
- Such a compound has high thermal stability and hence use of such a compound can provide devices having long lives.
- a method for producing a novel pyrene compound represented by general formula (1) is not particularly restricted.
- such a pyrene compound can be produced by the following method.
- an organic EL device at least includes a pair of electrodes constituted by an anode and a cathode, and an organic compound layer held between the pair of electrodes.
- the organic EL device may further include another compound layer other than the organic compound layer (for example, an inorganic compound layer or another organic compound layer) between the electrodes.
- the organic compound layer contains a pyrene compound represented by general formula (1) .
- a preferred embodiment of such an organic EL device is described below.
- An organic compound layer disposed between the anode and the cathode of an organic light-emitting device may be a monolayer or a multilayer.
- a first layer configuration includes, in sequence, a substrate, an anode, a light-emitting layer, and a cathode.
- a second layer configuration includes, in sequence, a substrate, an anode, a hole transport layer, an electron transport layer, and a cathode.
- the hole transport layer and the electron transport layer may serve as a light-emitting layer in which light is emitted from the interface between the hole transport layer and the electron transport layer.
- a third layer configuration includes, in sequence, a substrate, an anode, a hole transport layer, a light-emitting layer, an electron transport layer, and a cathode.
- a fourth layer configuration includes, in sequence, a substrate, an anode, a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, and a cathode.
- a fifth layer configuration includes, in sequence, a substrate, an anode, a hole transport layer, a light-emitting layer, a hole/exciton blocking layer, an electron transport layer, and a cathode.
- An organic compound layer containing a pyrene compound represented by general formula (1) may be any layer among the layers of the layer configurations.
- an organic EL device containing a pyrene compound according to the present invention is not restricted to the above-described first to fifth layer configurations.
- Various layer configurations other than these examples may be employed.
- an insulation layer may be provided at the interface between an electrode and an organic layer; an adhesion layer or an interference layer may be provided; or a hole transport layer may include two layers having different ionization potentials.
- an organic compound layer that contains a compound according to the present invention and is formed by vacuum evaporation, solution coating, or the like, the occurrence of disadvantages such as crystallization is reduced and hence such an organic compound layer has excellent stability over time.
- An organic EL device contains a compound represented by general formula (1), the compound particularly serving as a component for a light-emitting layer.
- the compound may be used together with, for example, known compounds such as low-molecular-weight hole transport compounds, polymeric hole transport compounds, light-emitting compounds, and electron transport compounds.
- a substrate for an organic EL device is not particularly restricted.
- a substrate is, for example, an opaque substrate such as a metal substrate or a ceramic substrate; or a transparent substrate such as a glass substrate, a quartz substrate, or a plastic sheet.
- Color light to be emitted can be controlled with a color filter film, fluorescent color conversion filter film, a dielectric reflection film, or the like on a substrate. It is also possible to form a thin-film transistor (TFT) on a substrate and produce a device connected to the transistor.
- TFT thin-film transistor
- either of the following device configurations may be used: a bottom emission configuration where light is output from the substrate side, and a top emission configuration where light is output from the side opposite the substrate.
- the anode and the cathode of a device should be formed with appropriate materials.
- An electrode disposed on the side on which light is output to the outside of a device is semitransparent or transparent to the light.
- Such an electrode is preferably formed of, for example, ITO.
- an electrode is preferably formed of a highly reflective material such as silver or aluminum.
- an electrode formed of a semitransparent or transparent material is disposed on a side where light is reflected and a reflective member that does not serve as an electrode is disposed on the side.
- An organic EL device may be operated in the manner of the active matrix operation or the passive matrix operation.
- a driving circuit for driving an organic EL device includes TFT, a capacitor, and the like.
- a plurality of organic EL devices may be used as a unit serving as a light-emitting point.
- a light-emitting point can be used as a lighting apparatus.
- a light-emitting point can be used as a pixel in the display portion of a display unit.
- Such a display unit can be used for a display for PC, a television receiver, or an image pickup apparatus.
- the image pickup apparatus is a digital camcorder, a digital still camera, or the like.
- Such an image pickup apparatus includes an image display part referred to as a finder.
- Such an image display part may include a display unit including organic EL devices.
- a display unit including organic EL devices is also used in control panel sections or the like of various electric apparatuses .
- An organic EL device may also be used as a light source for exposing a photosensitive member to light in an electrophotographic image formation apparatus such as a laser printer or a copying machine.
- the light source is constituted by a plurality of organic EL devices arranged in the longitudinal direction of the photosensitive member.
- a reaction vessel purged with nitrogen was charged with 60 mL of toluene, 30 itiL of ethanol, 30 mL of a 10 wt% aqueous solution of sodium carbonate, 35.7 mg of tetrakis (triphenyl phosphine) palladium, 403.1 mg of Compound (16) prepared above, and 350.2 mg of Compound (17) prepared above.
- Oxygen remaining in the system was purged by bubbling argon gas into the system for a few minutes.
- This reaction mixture was heated with a temperature regulated heat medium to reflux for 12 hours.
- the resultant solution was cooled to room temperature and subsequently neutralized with an aqueous solution of ammonium chloride and subjected to extraction with chloroform.
- a transparent conductive support substrate was produced by forming a film of indium tin oxide (ITO) by sputtering so as to have a thickness of 120 nm on a glass substrate serving as a substrate 1, the film serving as an anode 2.
- the resultant substrate was subjected to ultrasonic cleaning with acetone and subsequently isopropyl alcohol (IPA), cleaned by boiling with IPA, and subsequently dried.
- the resultant substrate was further subjected to UV/ozone cleaning to provide a transparent conductive support substrate.
- This solution was dropped and spin-coated on the ITO electrode to form a film.
- the resultant hole injection layer 7 had a thickness of 11 nm.
- a hole transport layer 5 was formed on the hole injection layer 7 by vapor depositing Compound (19) represented by the following structural formula.
- the hole transport layer 5 had a thickness of 15 nm.
- a light-emitting layer 3 was subsequently formed on the hole transport layer 5 by vapor depositing both Compound (20) having the following structure and above-described Compound (2) (the ratio of the weight of Compound (20) to the weight of Compound (2) was 5:95) .
- the light-emitting layer 3 had a thickness of 30 nm.
- An electron transport layer 6 was further formed by vacuum depositing
- a lithium fluoride (LiF) film was formed on the electron transport layer 6 (organic layer) by vacuum deposition so as to have a thickness of 0.5 nm.
- An aluminum film serving as an electron injection electrode (cathode 4) was formed by vacuum deposition so as to have a thickness of 150 nm. Thus, an organic EL device was produced.
- the organic HL ⁇ evice was covered with a protection glass plate in dry air atmosphere and sealed with an acrylic resin-based adhesive.
- the thus-obtained device produced good emission of blue light where the ITO electrode (anode 2) served as a positive electrode and the Al electrode (cathode 4) served as a negative electrode.
- Compound (18) of Comparative Example 1 does not include ⁇ a fluorene ring in the 7 position of the pyrene ring. As a result, Compound (18) had a low glass transition temperature, crystallized, and had a low melting point and a low decomposition temperature, compared with Compound (2) of Example 1.
- a pyrene compound according to the present invention can be presumably used as a material suitable for an organic EL device.
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Abstract
A novel pyrene compound is provided that is represented by general formula (1) where FL represents a substituted or unsubstituted fluorenyl group; A1 represents a substituted or unsubstituted benzene ring, a substituted or unsubstituted naphthalene ring, or a substituted or unsubstituted fluorene ring; and A2 represents a substituted or unsubstituted aryl group.
Description
DESCRIPTION
NOVEL PYRENE COMPOUND
Technical Field
[0001] The present invention relates to a novel pyrene compound and an organic electroluminescent (EL) device including an organic compound layer containing such a novel pyrene compound. Background Art
[0002] Many compounds having a pyrene structure have been synthesized as organic EL materials and such pyrene compounds have been disclosed as materials providing excellent durability when used for organic EL devices (see Patent Citation 1) . However, higher durability is necessary for practical use and hence there is presently a need for a material exhibiting higher stability when used for organic EL devices.
Patent Citation 1
WO 2005/123634
Disclosure of Invention Technical Problem
[0003] The present invention provides a novel pyrene compound having high thermal stability. The present invention also provides a highly durable organic EL device with such a novel pyrene compound having high thermal stability.
Solution to Problem
[0004] The present invention provides a pyrene compound represented by general formula (1) .
[ 0005 ]
General formula (1)
Description of Embodiments
[0008] A pyrene compound according to the present invention is represented by general formula (1) below. This compound includes an aryl group in the 1 position of the pyrene ring; and a fluorenyl group in the 7 position of the pyrene ring.
[0009] As a result of introduction of a fluorenyl group into the 7 position of the pyrene ring, the stacking of pyrenes is hindered due to steric hindrance. Thus, a highly amorphous pyrene compound is provided. Such a compound
has high thermal stability and hence use of such a compound can provide devices having long lives. [0010]
General formula (1)
[0011] The 7 position of a pyrene ring is electronically unique and such introduction of a fluorenyl group negligibly causes an increase in the emission wavelength. For this reason, introduction of a fluorenyl group into the 7 position of a pyrene ring is advantageous for providing organic EL materials having short emission wavelengths (for example, blue light or green light) .
[0012] A fluorenyl group represented as FL in general formula (1) may be unsubstituted or include a substituent. Specific examples of such a substituent include: linear alkyl groups such as a methyl group, an ethyl group, an isopropyl group, a n-butyl group, a tert-butyl group, a pentyl group, a hexyl group, an octyl group, a decyl group, a dodecyl group, a tridecyl group, a tetradecyl group, a pentadecyl group, a hexadecyl group, and an octadecyl group; cycloalkyl groups such as a cyclopentyl group and a cyclohexyl group; and aryl groups such as a phenyl group, a tolyl group, a biphenyl group, a naphthyl group, and a fluorenyl group.
[0013] These examples of the substituent may themselves be substituted with such a substituent.
[0014] In general formula (1) , Al has a large influence over the HOMO of the molecule. When Al includes conjugation that is too long, the resultant compound has degraded stability
against oxidation and relatively long emission wavelengths .
[0015] For this reason, when the compound is used as a material emitting short-wavelength light such as blue light or green light, particularly as a host material, Al is preferably any one of a benzene ring, a naphthalene ring, and a fluorene ring, which have short conjugation length.
[0016] An organic EL device at least includes an anode, a cathode, and an organic compound layer disposed between the anode and the cathode. "An organic EL device emits light" means that such an organic compound layer of the EL device emits light. Such an organic compound emitting light is referred to as a light-emitting material in this specification. An organic compound layer containing such a light-emitting material functions as a light-emitting layer.
[0017] The organic compound layer may contain a host material and a guest material. A host material is a main component of an organic light-emitting layer, and a guest material is an accessory component of the organic light-emitting layer.
[0018] In general formula (1), such a benzene ring, a naphthalene ring, or a fluorene ring that is represented by Al may be unsubstituted or include a substituent.
[0019] Specific examples of such a substituent include: linear alkyl groups such as a methyl group, an ethyl group, an isopropyl group, a n-butyl group, a tert-butyl group, a pentyl group, a hexyl group, an octyl group, a decyl group, a dodecyl group, a tridecyl group, a tetradecyl group, a pentadecyl group, a hexadecyl group, and an octadecyl group; cycloalkyl groups such as a cyclopentyl group and a cyclohexyl group; and aryl groups such as a phenyl group, a tolyl group, a biphenyl group, a naphthyl group, and a fluorenyl group.
[0020] These examples of the substituent may themselves be substituted with, for example, such a substituent.
[002i] In general formula (1), an aryl group represented by A2 can be selected in accordance with a desired emission wavelength. In particular, an aryl group represented by A2 is preferably a mono- to tricyclic aryl group.
[0022] When an aryl group represented by A2 is a mono- to tricyclic aryl group, the resultant compound is suitable as a material emitting short-wavelength light such as blue light or green light, particularly as a host material.
[0023] Herein, examples of a mono- to tricyclic aryl group include a phenyl group, a biphenyl group, a naphthyl group, a fluorenyl group, a phenanthryl group, and an anthryl group. A biphenyl group, a naphthyl group, and a fluorenyl group are classified as bicyclic aryl groups. A phenanthryl group and an anthryl group are classified as tricyclic aryl groups. Of these examples, more preferred are a naphthyl group, a fluorenyl group, and a phenanthryl group. When an aryl group represented by A2 is one of these groups, use of the resultant compound provides films having good properties.
[0024] A2 may be unsubstituted or include a substituent.
Specific examples of such a substituent include: linear alkyl groups such as a methyl group, an ethyl group, an isopropyl group, a n-butyl group, a tert-butyl group, a pentyl group, a hexyl group, an octyl group, a decyl group, a dodecyl group, a tridecyl group, a tetradecyl group, a pentadecyl group, a hexadecyl group, and an octadecyl group; cycloalkyl groups such as a cyclopentyl group and a cyclohexyl group; and aryl groups such as a phenyl group, a tolyl group, a biphenyl group, a naphthyl group, and a fluorenyl group.
[0025] These examples of the substituent may themselves be substituted with, for example, such a substituent.
[0026] Specific examples of a pyrene compound according to the present invention are described below as structural formulae. However, the present invention is not restricted to these examples.
Compound (1 )
Compound (2)
Compound (3) Compound (6)
Compound (7)
Compound (8)
Compound (9) Compound (13)
Compound (10) Compound (14)
Compound (11) Compound (15)
[0029] These compounds shown as examples include a fluorenyl group in the 7 position of the pyrene ring and hence the stacking of pyrenes is hindered due to steric hindrance. Thus, a highly amorphous pyrene compound is provided. Such a compound has high thermal stability and hence use of such a compound can provide devices having long lives.
[0030] A method for producing a novel pyrene compound represented by general formula (1) is not particularly restricted. For example, such a pyrene compound can be produced by the following method.
[0031] An example of the synthesis of intermediate A is shown below.
[ 0032 ;
[lrOMe(COD)]2 Cyclohexane
Intermediate A
[0033] An example of the synthesis of intermediate B is shown below.
[ 0034 ]
Tf2Q TfO
\
Pyridine A1-A2
Intermediate B
[0035] An example of the synthesis of a novel pyrene compound from intermediate A and intermediate B is shown below. [0036]
Intermediate A + Intermediate B
[0037] An organic EL device containing a pyrene compound according to the present invention is described in detail below.
[0038] As described above, an organic EL device according to this embodiment at least includes a pair of electrodes constituted by an anode and a cathode, and an organic compound layer held between the pair of electrodes. The organic EL device may further include another compound
layer other than the organic compound layer (for example, an inorganic compound layer or another organic compound layer) between the electrodes.
[0039] The organic compound layer contains a pyrene compound represented by general formula (1) . A preferred embodiment of such an organic EL device is described below.
[0040] The configuration of the layers of an organic light-emitting device is described below.
[0041] An organic compound layer disposed between the anode and the cathode of an organic light-emitting device may be a monolayer or a multilayer.
[0042] Specific examples of such a layer configuration are described below. A first layer configuration includes, in sequence, a substrate, an anode, a light-emitting layer, and a cathode.
[0043] A second layer configuration includes, in sequence, a substrate, an anode, a hole transport layer, an electron transport layer, and a cathode. In this case, the hole transport layer and the electron transport layer may serve as a light-emitting layer in which light is emitted from the interface between the hole transport layer and the electron transport layer.
[0044] A third layer configuration includes, in sequence, a substrate, an anode, a hole transport layer, a light-emitting layer, an electron transport layer, and a cathode.
[0045] A fourth layer configuration includes, in sequence, a substrate, an anode, a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, and a cathode.
[0046] A fifth layer configuration includes, in sequence, a substrate, an anode, a hole transport layer, a light-emitting layer, a hole/exciton blocking layer, an electron transport layer, and a cathode.
[0047] An organic compound layer containing a pyrene compound
represented by general formula (1) may be any layer among the layers of the layer configurations.
[0048] Note that the configuration of an organic EL device containing a pyrene compound according to the present invention is not restricted to the above-described first to fifth layer configurations. Various layer configurations other than these examples may be employed. For example, an insulation layer may be provided at the interface between an electrode and an organic layer; an adhesion layer or an interference layer may be provided; or a hole transport layer may include two layers having different ionization potentials.
[0049] In an organic compound layer that contains a compound according to the present invention and is formed by vacuum evaporation, solution coating, or the like, the occurrence of disadvantages such as crystallization is reduced and hence such an organic compound layer has excellent stability over time.
[0050] An organic EL device according to the present embodiment contains a compound represented by general formula (1), the compound particularly serving as a component for a light-emitting layer. The compound may be used together with, for example, known compounds such as low-molecular-weight hole transport compounds, polymeric hole transport compounds, light-emitting compounds, and electron transport compounds.
[0051] A substrate for an organic EL device according to the present embodiment is not particularly restricted. Such a substrate is, for example, an opaque substrate such as a metal substrate or a ceramic substrate; or a transparent substrate such as a glass substrate, a quartz substrate, or a plastic sheet.
[0052] Color light to be emitted can be controlled with a color filter film, fluorescent color conversion filter film, a dielectric reflection film, or the like on a substrate. It is also possible to form a thin-film transistor (TFT)
on a substrate and produce a device connected to the transistor.
[0053] As for the direction of light output from a device, either of the following device configurations may be used: a bottom emission configuration where light is output from the substrate side, and a top emission configuration where light is output from the side opposite the substrate.
[0054] The anode and the cathode of a device should be formed with appropriate materials. An electrode disposed on the side on which light is output to the outside of a device is semitransparent or transparent to the light. Such an electrode is preferably formed of, for example, ITO.
[0055] When light needs to be reflected in a device, an electrode is preferably formed of a highly reflective material such as silver or aluminum.
[0056] Alternatively, when light needs to be reflected in a device, the following configuration may also be used: an electrode formed of a semitransparent or transparent material is disposed on a side where light is reflected and a reflective member that does not serve as an electrode is disposed on the side.
[0057] An organic EL device may be operated in the manner of the active matrix operation or the passive matrix operation. When the active matrix operation is employed, a driving circuit for driving an organic EL device includes TFT, a capacitor, and the like.
[0058] A plurality of organic EL devices may be used as a unit serving as a light-emitting point. For example, such a light-emitting point can be used as a lighting apparatus. Alternatively, such a light-emitting point can be used as a pixel in the display portion of a display unit. Such a display unit can be used for a display for PC, a television receiver, or an image pickup apparatus.
[0059] The image pickup apparatus is a digital camcorder, a digital still camera, or the like. Such an image pickup apparatus includes an image display part referred to as
a finder. Such an image display part may include a display unit including organic EL devices.
[0060] A display unit including organic EL devices is also used in control panel sections or the like of various electric apparatuses .
[0061] An organic EL device may also be used as a light source for exposing a photosensitive member to light in an electrophotographic image formation apparatus such as a laser printer or a copying machine. In this case, the light source is constituted by a plurality of organic EL devices arranged in the longitudinal direction of the photosensitive member.
EXAMPLES
EXAMPLE 1: Synthesis of Compound (2)
[0062] Compounds (16) and (17) were synthesized in the manners described below and were subsequently subjected to coupling described below.
[0063]
[IrOMe(COD)J2 Cyclohexane
Compound (16)
[0064]
Compound (17)
[ 0065 ]
Compound (16) + Compound (17)
Compound (2)
[0066] A reaction vessel purged with nitrogen was charged with 60 mL of toluene, 30 itiL of ethanol, 30 mL of a 10 wt% aqueous solution of sodium carbonate, 35.7 mg of tetrakis (triphenyl phosphine) palladium, 403.1 mg of Compound (16) prepared above, and 350.2 mg of Compound (17) prepared above. Oxygen remaining in the system was purged by bubbling argon gas into the system for a few minutes. This reaction mixture was heated with a temperature regulated heat medium to reflux for 12 hours. The resultant solution was cooled to room temperature and subsequently neutralized with an aqueous solution of ammonium chloride and subjected to extraction with chloroform. The resultant solution was separated and an organic layer was subsequently dried with anhydrous magnesium sulfate and this drying agent was removed by filtration. A crude product obtained as a result of concentration of the dried substance was purified by column chromatography and GPC to provide 230 mg of Compound (2) . Compound (2) was identified by NMR and MALDI-TOF.
1H-NMR (CDCl3, 400 MHz) δ = 1.61 ppm (s, 6H) , 1.63 ppm (s, 6H) , 7.34-7.41 ppm (m, 4H), 7.49-7.50 ppm (m, 2H), 7.77-7.96 ppm (m, 10H), 8.05-8.30 ppm (m, 10H), 8.49 (dd, 2H). MALDI-TOF m/z = 712.16 (calc. m/z = 712.31)
[0067] The resultant Compound (2) was subjected to DSC measurement and TG-DTA measurement. The glass transition temperature was 149.9°C. The melting point was 256.70C. The temperature at which decomposition started was 454.50C. The temperature at which crystallization occurred was not clearly measured. These results are summarized in Table 2 below.
[0068] Compounds (1) and (3) to (15) can also be synthesized as in Example 1 except that the intermediates are replaced with the compounds shown in Table 1 below.
[0069]
Table 1 (continued)
[0071]
Table 1 (continued)
EXAMPLE 2
[0072] An organic EL device having the above-described fourth layer configuration was produced in the following manner.
[0073] A transparent conductive support substrate was produced by forming a film of indium tin oxide (ITO) by sputtering so as to have a thickness of 120 nm on a glass substrate serving as a substrate 1, the film serving as an anode 2. The resultant substrate was subjected to ultrasonic cleaning with acetone and subsequently isopropyl alcohol (IPA), cleaned by boiling with IPA, and subsequently dried. The resultant substrate was further subjected to UV/ozone cleaning to provide a transparent conductive support substrate.
[0074] A 0.1 wt% solution of chloroform was prepared with
Compound (18) that served as a positive hole injection material 'and is represented by the following structural formula.
[0075]
Compound (18)
[0076] This solution was dropped and spin-coated on the ITO electrode to form a film. The resultant hole injection layer 7 had a thickness of 11 nm.
[0077] A hole transport layer 5 was formed on the hole injection layer 7 by vapor depositing Compound (19) represented by the following structural formula. The hole transport layer 5 had a thickness of 15 nm.
[0078]
Compound (19)
[0079] A light-emitting layer 3 was subsequently formed on the hole transport layer 5 by vapor depositing both Compound (20) having the following structure and above-described Compound (2) (the ratio of the weight of Compound (20) to the weight of Compound (2) was 5:95) . The light-emitting layer 3 had a thickness of 30 nm.
[0080]
Compound (20)
[0081] An electron transport layer 6 was further formed by vacuum depositing
2, 9- [2- (9,9' -dimethylfluorenyl) ] -1, 10-phenanthroline so as to have a thickness of 30 nm.
[0082] A lithium fluoride (LiF) film was formed on the electron transport layer 6 (organic layer) by vacuum deposition so as to have a thickness of 0.5 nm. An aluminum film serving as an electron injection electrode (cathode 4) was formed by vacuum deposition so as to have a thickness of 150 nm. Thus, an organic EL device was produced.
[0083] To prevent degradation due to absorption of water, the
organic HL αevice was covered with a protection glass plate in dry air atmosphere and sealed with an acrylic resin-based adhesive.
[0084] The thus-obtained device produced good emission of blue light where the ITO electrode (anode 2) served as a positive electrode and the Al electrode (cathode 4) served as a negative electrode.
COMPARATIVE EXAMPLE 1: Synthesis of Comparative Compound
[0085] Compound (18) that has the following structure and served as a comparative example was synthesized in the following manner.
[0086]
Compound (18)
[0087] The resultant Compound (18) was subjected to DSC measurement and TG-DTA measurement. The glass transition temperature was 109.30C. The temperature at which crystallization occurred was 186.2°C. The melting point was 247.9°C. The temperature at which decomposition started was 400.60C. These results are summarized in Table 2 below.
[0088] Table 2
[0089] Compound (18) of Comparative Example 1 does not include ■ a fluorene ring in the 7 position of the pyrene ring. As a result, Compound (18) had a low glass transition temperature, crystallized, and had a low melting point and a low decomposition temperature, compared with Compound (2) of Example 1.
[0090] In summary, Compound (18) of Comparative Example 1 is presumably susceptible to thermal influences. In contrast, a pyrene compound according to the present invention has excellent stability against thermal influences .
[0091] Therefore, a pyrene compound according to the present invention can be presumably used as a material suitable for an organic EL device.
[0092] While the present invention has been described with reference to exemplary embodiments, it is to be understood that the invention is not limited to the disclosed exemplary embodiments. The scope of the following claims is to be accorded the broadest interpretation so as to encompass all such modifications and equivalent structures and functions.
[0093] This application claims the benefit of Japanese Patent Application No. 2008-314611, filed December 10, 2008, which is hereby incorporated by reference herein in its entirety.
Claims
[1] A pyrene compound represented by general formula (I]
General formula (1)
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| JP2004043349A (en) * | 2002-07-11 | 2004-02-12 | Mitsui Chemicals Inc | Hydrocarbon compound, material for organic electroluminescent element and organic electroluminescent element |
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| JP2004043349A (en) * | 2002-07-11 | 2004-02-12 | Mitsui Chemicals Inc | Hydrocarbon compound, material for organic electroluminescent element and organic electroluminescent element |
| WO2005115950A1 (en) * | 2004-05-27 | 2005-12-08 | Idemitsu Kosan Co., Ltd. | Asymmetric pyrene derivative and organic electroluminescent device using same |
| WO2007029798A1 (en) * | 2005-09-08 | 2007-03-15 | Toray Industries, Inc. | Light-emitting device material and light-emitting device |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2018095385A1 (en) * | 2016-11-23 | 2018-05-31 | 广州华睿光电材料有限公司 | Fused ring compound, high polymer, mixture, composition, and organic electronic component |
| US11518723B2 (en) | 2016-11-23 | 2022-12-06 | Guangzhou Chinaray Optoelectronic Materials Ltd. | Fused ring compound, high polymer, mixture, composition and organic electronic component |
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| Publication number | Publication date |
|---|---|
| JP2010138090A (en) | 2010-06-24 |
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