WO2007029798A1 - 発光素子材料および発光素子 - Google Patents
発光素子材料および発光素子 Download PDFInfo
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- WO2007029798A1 WO2007029798A1 PCT/JP2006/317810 JP2006317810W WO2007029798A1 WO 2007029798 A1 WO2007029798 A1 WO 2007029798A1 JP 2006317810 W JP2006317810 W JP 2006317810W WO 2007029798 A1 WO2007029798 A1 WO 2007029798A1
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- WIPO (PCT)
- Prior art keywords
- group
- light emitting
- emitting device
- compound
- aryl
- Prior art date
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- 239000000463 material Substances 0.000 title claims abstract description 139
- -1 pyrene compound Chemical class 0.000 claims abstract description 69
- BBEAQIROQSPTKN-UHFFFAOYSA-N antipyrene Natural products C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 claims abstract description 63
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 claims abstract description 45
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 38
- 125000003118 aryl group Chemical group 0.000 claims abstract description 33
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 31
- 125000001424 substituent group Chemical group 0.000 claims abstract description 31
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 23
- 125000000732 arylene group Chemical group 0.000 claims abstract description 12
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 12
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- 239000001257 hydrogen Substances 0.000 claims abstract description 12
- 125000005013 aryl ether group Chemical group 0.000 claims abstract description 11
- 125000005549 heteroarylene group Chemical group 0.000 claims abstract description 11
- 125000003277 amino group Chemical group 0.000 claims abstract description 10
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 9
- 125000004414 alkyl thio group Chemical group 0.000 claims abstract description 9
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 8
- 125000000392 cycloalkenyl group Chemical group 0.000 claims abstract description 8
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims abstract description 8
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 6
- 150000002367 halogens Chemical class 0.000 claims abstract description 6
- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical group [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 claims abstract description 6
- 150000004832 aryl thioethers Chemical group 0.000 claims abstract description 5
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract 6
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims abstract 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 136
- 150000001875 compounds Chemical class 0.000 claims description 121
- 229910052757 nitrogen Inorganic materials 0.000 claims description 76
- 239000010410 layer Substances 0.000 claims description 48
- 239000012044 organic layer Substances 0.000 claims description 41
- 239000000126 substance Substances 0.000 claims description 24
- 239000002019 doping agent Substances 0.000 claims description 22
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 13
- 229910052799 carbon Inorganic materials 0.000 claims description 13
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 6
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 5
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 4
- 229910052698 phosphorus Inorganic materials 0.000 claims description 4
- 239000011574 phosphorus Substances 0.000 claims description 4
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- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 239000001301 oxygen Substances 0.000 claims description 3
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- 239000010703 silicon Substances 0.000 claims description 2
- IARLISDOOLYUNK-UHFFFAOYSA-N O[PH2]=N Chemical compound O[PH2]=N IARLISDOOLYUNK-UHFFFAOYSA-N 0.000 claims 1
- 125000000304 alkynyl group Chemical group 0.000 abstract description 3
- 125000003342 alkenyl group Chemical group 0.000 abstract 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 abstract 1
- 125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 159
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- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 96
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- 238000000746 purification Methods 0.000 description 86
- 238000000859 sublimation Methods 0.000 description 84
- 230000008022 sublimation Effects 0.000 description 84
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 76
- 239000011259 mixed solution Substances 0.000 description 64
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- 239000007787 solid Substances 0.000 description 54
- 239000013078 crystal Substances 0.000 description 53
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 52
- 238000005160 1H NMR spectroscopy Methods 0.000 description 47
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- 235000019341 magnesium sulphate Nutrition 0.000 description 38
- 230000015572 biosynthetic process Effects 0.000 description 37
- 238000003786 synthesis reaction Methods 0.000 description 37
- 239000000843 powder Substances 0.000 description 35
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- 238000000034 method Methods 0.000 description 25
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 24
- 239000012141 concentrate Substances 0.000 description 22
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- 230000005525 hole transport Effects 0.000 description 14
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- 125000004432 carbon atom Chemical group C* 0.000 description 11
- 238000001914 filtration Methods 0.000 description 11
- 229910052751 metal Inorganic materials 0.000 description 11
- 239000002184 metal Substances 0.000 description 11
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 11
- 238000003756 stirring Methods 0.000 description 11
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 10
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 10
- 239000012043 crude product Substances 0.000 description 10
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- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
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- HYCYKHYFIWHGEX-UHFFFAOYSA-N (2-phenylphenyl)boronic acid Chemical compound OB(O)C1=CC=CC=C1C1=CC=CC=C1 HYCYKHYFIWHGEX-UHFFFAOYSA-N 0.000 description 6
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- 229910052782 aluminium Inorganic materials 0.000 description 6
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 6
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- BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 description 6
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- MYKQKWIPLZEVOW-UHFFFAOYSA-N 11h-benzo[a]carbazole Chemical compound C1=CC2=CC=CC=C2C2=C1C1=CC=CC=C1N2 MYKQKWIPLZEVOW-UHFFFAOYSA-N 0.000 description 4
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- RQGPLDBZHMVWCH-UHFFFAOYSA-N pyrrolo[3,2-b]pyrrole Chemical class C1=NC2=CC=NC2=C1 RQGPLDBZHMVWCH-UHFFFAOYSA-N 0.000 description 1
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- HFFLGKNGCAIQMO-UHFFFAOYSA-N trichloroacetaldehyde Chemical compound ClC(Cl)(Cl)C=O HFFLGKNGCAIQMO-UHFFFAOYSA-N 0.000 description 1
- PWYVVBKROXXHEB-UHFFFAOYSA-M trimethyl-[3-(1-methyl-2,3,4,5-tetraphenylsilol-1-yl)propyl]azanium;iodide Chemical compound [I-].C[N+](C)(C)CCC[Si]1(C)C(C=2C=CC=CC=2)=C(C=2C=CC=CC=2)C(C=2C=CC=CC=2)=C1C1=CC=CC=C1 PWYVVBKROXXHEB-UHFFFAOYSA-M 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
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Classifications
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/622—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing four rings, e.g. pyrene
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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
- 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
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- 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
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
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- 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
- H10K50/12—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers comprising dopants
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- 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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- 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
- H10K85/626—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene
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- H—ELECTRICITY
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- 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
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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
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
- H10K85/633—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
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- H—ELECTRICITY
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- 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
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- 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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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
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Definitions
- Light emitting device material and light emitting device are Light emitting device material and light emitting device
- the present invention relates to a light emitting device material useful as a fluorescent dye or a charge transport material, and a light emitting device using the same.
- the light emitting device of the present invention can be used in the fields of display devices, flat panel displays, knock lights, lighting, interiors, signs, signboards, electrophotographic machines and optical signal generators.
- organic thin-film light-emitting elements are capable of obtaining various emission colors by using various fluorescent materials in the light-emitting layer.
- Research on green light emitting materials is the most advanced among the three primary color light emitting materials. Currently, red light emitting materials and blue light emitting materials are being studied with the aim of improving their characteristics.
- Patent Document 1 Japanese Unexamined Patent Publication No. 2000-273056 (Claims 1 and 2)
- Patent Document 2 JP 2002-63988 A (Claim 1)
- Patent Document 3 International Publication No. 2004Z096945 Pamphlet (Claims)
- Patent Document 4 JP-A-2004-75567 (Claims 1 to 4)
- Patent Document 5 Japanese Unexamined Patent Application Publication No. 2004-139957 (Claim 1)
- Patent Document 6 Japanese Patent Laid-Open No. 2003-272864 (Claim 1)
- Non-Patent Document 1 Applied Physics Letters (USA) 1987, 51 ⁇ , 12, 913-915
- an object of the present invention is to solve the problems of the prior art, and to provide a light emitting element material that enables a blue light emitting element with high luminous efficiency and excellent durability, and a light emitting element using the same. .
- the present invention is a light emitting device material containing a pyrene compound represented by the general formula (1).
- R 18 may be the same or different from each other, hydrogen, alkyl group, cycloalkyl group, heterocyclic group, alkyl group, cycloalkyl group, alkyl group, alkoxy group, alkylthio group, Aryl ether group, aryl ether ether group, aryl group, heteroaryl group, halogen, carbo group, carboxyl group, oxy group, carbon It is a group selected from among a vamoyl group, an amino group, a phosphine oxide group and a silyl group. 1-8, may form a ring adjacent substituents. n is an integer from 1 to 3.
- X is a group chosen for the medium power of —O—, —S— and —NR 19 —.
- R 19 is a selected group of hydrogen, alkyl group, cycloalkyl group, heterocyclic group, alkyl group, cycloalkenyl group, alkyl group, aryl group, heteroaryl group and amino group.
- R 1 9 may form a ring with R 11 or R 18.
- Y is a single bond, an arylene group or a heteroarylene group. 1 ⁇ to 1 ⁇ one of the one force of n and R U to R 19 of the
- the present invention is a light emitting device having at least an anode, a cathode and a light emitting layer, wherein the light emitting layer exists between the anode and the cathode, and the light emitting layer emits light by electric energy
- the layer is a light emitting device containing a pyrene compound represented by the general formula (1).
- the light emitting device material of the present invention can be used for a light emitting device and the like, and can provide a light emitting device material having excellent thin film stability. According to the present invention, a light emitting device having high luminous efficiency and excellent durability can be obtained.
- the pyrene compound represented by the general formula (1) is selected from among a pyrene skeleton and an electron-donating fused aromatic dibenzofuran group, dibenzothiophene group and force rubazole group in the molecule. 1 to 3 groups, both of which are connected by a linking group Y. By having such a structure, the pyrene compound has high thin film stability and excellent heat resistance. In the general formula (1), if n is 4 or more, the stability and heat resistance of the thin film are lowered.
- General formula (1 ) is preferably in the range of 1 to 2 because the thin film stability and heat resistance are more excellent.
- the linking group Y is a single bond, an arylene group or a heteroarylene group.
- the linking group Y is preferably an arylene group or a heteroarylene group.
- the arylene group is a divalent group derived from an aromatic hydrocarbon group such as a phenyl group, a naphthyl group, a biphenyl group, a phenanthryl group, a terfel group, or a pyrel group, This may or may not have a substituent.
- the number of carbon atoms of the arylene group is not particularly limited, but is usually in the range of 6-40.
- the arylene group preferably has a carbon number in the range of 6 to 12 including the substituent.
- the heteroarylene group is an aromatic group having one or more atoms other than carbon, such as a pyridyl group, a quinolinyl group, a birazinyl group, a naphthyridyl group, a dibenzofuryl group, a dibenzothiophenyl group, and a carbazolyl group.
- the number of carbon atoms of the heteroarylene group is not particularly limited, but is usually in the range of 2 to 30, and more preferably in the range of 2 to 12 including the substituent.
- At least one of 1 ⁇ to 1 ⁇ is preferably an aryl group or a heteroaryl group.
- X is a group in which medium forces of —O—, —S—, and —NR 19 — are also selected.
- R 19 is a selected group of hydrogen, alkyl group, cycloalkyl group, heterocyclic group, alkyl group, cycloalkenyl group, alkyl group, aryl group, heteroaryl group and amino group.
- R 1 9 may form a ring with R 11 or R 18.
- an alkyl group is, for example, a saturated fat such as a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n -butyl group, a sec-butyl group, or a tert-butyl group.
- the additional substituent when it is substituted and examples thereof include an alkyl group, aryl group, heteroaryl group, etc., and this point is common to the following description.
- the number of carbon atoms of the alkyl group is not particularly limited, but is usually in the range of 1 to 20 and more preferably 1 to 8 in view of availability and cost.
- the cycloalkyl group refers to a saturated alicyclic hydrocarbon group such as cyclopropyl, cyclohexyl, norbornyl, adamantyl, and the like, which has a substituent. It does not have to be.
- the number of carbon atoms of the cycloalkyl group is not particularly limited, but is usually in the range of 3 or more and 20 or less.
- the heterocyclic group refers to an aliphatic ring having atoms other than carbon, such as a pyran ring, piperidine ring, and cyclic amide, in the ring, which has a substituent! / Have it! / You don't have to go ⁇ .
- the number of carbon atoms of the heterocyclic group is not particularly limited, but is usually in the range of 2 or more and 20 or less.
- the alkell group refers to, for example, an unsaturated aliphatic hydrocarbon group containing a double bond such as a bur group, a allyl group, or a butagel group, which has a substituent. It is not necessary to have it.
- the carbon number of the alkaryl group is not particularly limited, but is usually in the range of 2-20.
- the cycloalkenyl group refers to an unsaturated alicyclic hydrocarbon group containing a double bond such as a cyclopentyl group, a cyclopentagel group, a cyclohexenyl group, and the like. Even if you have a substituent, you don't have it.
- the number of carbon atoms of the cycloalkenyl group is not particularly limited, but is usually in the range of 3 or more and 20 or less.
- the alkynyl group refers to, for example, an unsaturated aliphatic hydrocarbon group containing a triple bond such as an ethynyl group, which may or may not have a substituent.
- the number of carbon atoms of the alkyl group is not particularly limited, but is usually in the range of 2-20.
- the alkoxy group refers to a functional group to which an aliphatic hydrocarbon group is bonded via an ether bond such as a methoxy group, an ethoxy group, or a propoxy group. With or without substituents.
- the number of carbon atoms of the alkoxy group is not particularly limited, but is usually in the range of 1 or more and 20 or less.
- the alkylthio group is a group in which an oxygen atom of an ether bond of an alkoxy group is substituted with a sulfur atom.
- the hydrocarbon group of the alkylthio group has a substituent and may or may not have a substituent.
- the number of carbon atoms of the alkylthio group is not particularly limited, but is usually in the range of 1 or more and 20 or less.
- the aryl ether group refers to a functional group to which an aromatic hydrocarbon group is bonded via an ether bond, such as a phenoxy group, and the aromatic hydrocarbon group has a substituent! It does not have to be present.
- the carbon number of the aryl ether group is not particularly limited, but is usually in the range of 6 to 40.
- the arylthioether group is a group in which the oxygen atom of the ether bond of the aryl ether group is substituted with a sulfur atom.
- the aromatic hydrocarbon group in the aryl ether group may have a substituent or not.
- the number of carbon atoms of the arylthioether group is not particularly limited, but is usually in the range of 6 to 40.
- the aryl group refers to, for example, an aromatic hydrocarbon group such as a phenyl group, a naphthyl group, a biphenyl group, a phenanthryl group, a terphenyl group, and a pyrenyl group.
- the aryl group may or may not have a substituent.
- the carbon number of the aryl group is not particularly limited, but is usually in the range of 6-40.
- the heteroaryl group is a 6-membered aromatic group having one or more atoms other than carbon, such as a pyridyl group, a quinolinyl group, a birazinyl group, or a naphthyridyl group, a dibenzofuranyl group, a dibenzothiophenyl group, A strong rubazolyl group, which may be unsubstituted or substituted;
- the number of carbon atoms of the heteroaryl group is not particularly limited, but is usually in the range of 2-30.
- the halogen atom represents fluorine, chlorine, bromine and iodine.
- the carbo group, carboxyl group, oxycarbol group, strong rubamoyl group, amino group and phosphine oxide group may or may not have a substituent.
- substituent include an alkyl group, a cycloalkyl group, an aryl group, and a heteroaryl group as described above.
- the silyl group refers to, for example, a functional group having a bond to a silicon atom such as a trimethylsilyl group, which may or may not have a substituent.
- the carbon number of the silyl group is not particularly limited, but is usually in the range of 3-20. The key number is usually 1-6.
- adjacent substituents form a ring
- two adjacent adjacent substituents are bonded to each other to form a conjugated or non-conjugated condensed ring.
- a conjugated or non-conjugated condensed ring it can.
- an element selected from nitrogen, oxygen, sulfur, phosphorus, and key strength may be included.
- the condensed ring may be further condensed with another ring.
- R 3 , R 6 , and R 8 are a group different from R 1 in the pyrene compound represented by the general formula (1), the symmetry of the molecule is lowered, and a high-quality amorphous It is preferable because a thin film can be formed.
- the pyrene compound represented by the general formula (1) is a pyrene compound in which R 1 is an aryl group or a heteroaryl group, and at least one of Y is linked at the position of R 6 or R 8 . It is preferable because the interaction between the members is suppressed and high luminous efficiency is possible. More preferably, R 1 is an aryl group. Further, R 2 is an alkyl group or a cycloalkyl group, and at least one of Y is connected at the position of R 6 or R 8 , which is preferable because the amorphous nature of the molecule is improved and a stable thin film can be formed.
- X is —NR 19 —, that is, the electron donating condensed aromatic is a strong rubazole group, and at least one of Y is a position of R 6 or R 8 And R 19 are preferably connected. That is, the pyrene compound represented by the general formula (1) is preferably a compound represented by the general formula (2).
- R u to R db may be the same as or different from each other, and may be hydrogen, an alkyl group, or cycloal. Kill group, heterocyclic group, alkyl group, cycloalkenyl group, alkyl group, alkoxy group, alkylthio group, aryl ether group, aryl thioether group, aryl group, heteroaryl group, halogen, carbon A group selected from among a group, a carboxyl group, an oxycarbol group, a force rubamoyl group, an amino group, a phosphine oxide group and a silyl group.
- R 2G to R 36 may form a ring with adjacent substituents.
- Ar is a single bond, an arylene group or a heteroarylene group.
- Ar is preferably an arylene group or a heteroarylene group.
- R 22 and R 24 when at least one of R 22 and R 24 is an aryl group or a heteroaryl group, the intermolecular interaction between the pyrene skeletons is suppressed, High efficiency light emission is possible, and at the same time a stable thin film can be formed, which is preferable.
- R 24 is more preferably an aryl group or a heteroaryl group because the synthesis process becomes easy and the cost can be reduced.
- R 23 is an alkyl group or a cycloalkyl group.
- R 27 is preferably an aryl group or a heteroaryl group, since intermolecular interaction is suppressed and high-efficiency light emission is possible.
- At least one R U to R 18 in the general formula (1), or the general formula in (2) at least one alkyl group R 2 9 to R 36, a cycloalkyl group, Ariru group and to A preferred form is a group selected from reel groups.
- the pyrene compound as described above is not particularly limited, but specific examples include the following.
- a known method can be used for the synthesis of the pyrene compound represented by the general formula (1).
- Examples of the method for introducing a force rubazolyl group into the pyrene skeleton include, for example, a method using a coupling reaction of a halogenated pyrene derivative with force rubazole or force rubazolylaryl metal complex under a radium or nickel catalyst, or radium. Or a force using a coupling reaction between a pyrenyl metal complex and a halogenated power rubazole derivative in the presence of a nickel catalyst, but is not limited thereto.
- the method for introducing a dibenzofuran group or dibenzothiophenyl group into the pyrene skeleton is, for example, coupling of a halogenated pyrene derivative with a dibenzofuranyl metal complex or a dibenzothiophenyl metal complex under a radium or nickel catalyst.
- Powers including a method using a reaction, a method using a coupling reaction between a pyrenyl metal complex and a halogenated dibenzofuran derivative or a halogenated dibenzothiophene derivative under a palladium or nickel catalyst are not limited thereto.
- the light-emitting element of the present invention includes an anode, a cathode, and an organic layer present between the anode and the cathode.
- the organic layer includes at least a light-emitting layer, and the light-emitting layer emits light by electric energy.
- the organic layer includes 1) a hole transport layer, a Z light emitting layer, a Z electron transport layer, and 2) a light emitting layer, a Z electron transport layer, and 3) a hole transport layer, a Z light emitting layer. And the like.
- Each of the layers may be a single layer or a plurality of layers.
- the layers in contact with the electrodes may be referred to as the hole injection layer and the electron injection layer, respectively.
- the electron injection material is included in the electron transport material.
- the light emitting device of the present invention is formed of the light emitting device material of the present invention in which the organic layer contains a pyrene compound represented by the general formula (1).
- the light emitting element material corresponds to either a compound that emits light by itself or a substance that assists the light emission, and refers to a compound that participates in light emission. Specifically, a hole transport material, a light emitting material, and This includes electron transport materials.
- the light emitting device material of the present invention may be used as a hole transport material or an electron transport material, but is preferably used as a light emitting material because of its high light emission performance.
- the light emitting element material of the present invention exhibits strong light emission in the blue region, and thus is suitably used as a blue light emitting material, but can also be used as a material for green to red light emitting elements and white light emitting elements. wear.
- the anode is not particularly limited as long as it can efficiently inject holes into the organic layer, but it is preferable to use a material having a relatively high work function.
- the anode material include conductive metal oxides such as tin oxide, indium oxide, indium oxide zinc indium, and indium oxide tin indium (ITO), or metals such as gold, silver, and chromium, copper iodide, Inorganic conductive materials such as copper sulfide, and conductive polymers such as polythiophene, polypyrrole, and polyarine. These electrode materials may be used alone, or a plurality of materials may be laminated or mixed.
- the resistance of the anode is preferably low from the viewpoint of power consumption of the light-emitting element as long as a current sufficient for light emission of the light-emitting element can be supplied. For example, if the resistance is 300 ⁇ or less The ability to function as an electrode if possible Since it is now possible to supply ⁇ substrates of about 10 ⁇ Z ports, it is particularly desirable to use low resistance products of 100 ⁇ / port or less.
- the thickness of the anode can be arbitrarily selected according to the resistance value, but is usually used in the range of 100 to 300 nm.
- the light-emitting element In order to maintain the mechanical strength of the light-emitting element, it is preferable to form the light-emitting element on a substrate.
- a glass substrate such as soda glass or non-alkali glass is preferably used.
- the thickness of the glass substrate it is sufficient that the thickness is sufficient to maintain the mechanical strength.
- the glass material is preferably alkali-free glass because it is better to have less ions eluted from the glass, but a barrier coat such as SiO is applied.
- soda lime glass is also commercially available, it can be used. Furthermore, if the anode functions stably, the substrate need not be glass.
- an anode may be formed on a plastic substrate.
- the method for forming the anode is not particularly limited, and for example, an electron beam method, a sputtering method, an electrochemical reaction method, or the like can be used.
- the material used for the cathode is not particularly limited as long as it can efficiently inject electrons into the organic layer.
- Platinum, gold, silver, copper, iron, tin, zinc, aluminum, indium, chromium, lithium examples thereof include sodium, potassium, cesium, calcium and magnesium, and alloys thereof.
- Lithium, sodium, potassium, cesium, calcium, magnesium, or alloys containing these low work function metals are effective for increasing the electron injection efficiency and improving device characteristics.
- these low work function metals are generally unstable in the atmosphere. Therefore, the organic layer is doped with a small amount of lithium or magnesium (less than 1 nm on the vacuum deposition film thickness display).
- a preferable example is a method of obtaining an electrode having high stability.
- inorganic salts such as lithium fluoride can be used.
- metals such as platinum, gold, silver, copper, iron, tin, aluminum and indium, or alloys using these metals, inorganic substances such as silica, titania and nitrided nitride, polyvinyl alcohol Preferred examples include laminating organic polymer compounds such as polyvinyl chloride and hydrocarbon polymer compounds.
- the method for forming these electrodes is not particularly limited, and for example, resistance heating, electron beam, spottering, ion plating and coating can be used.
- the hole transport layer is formed by a method of laminating or mixing one kind or two or more kinds of hole transport materials, or a method using a mixture of a hole transport material and a polymer binder. Further, the hole transport layer may be formed by adding an inorganic salt such as iron (III) chloride to the hole transport material.
- the hole transport material is not particularly limited as long as it is a compound that can form a thin film, can inject holes with an anodic force, and can further transport holes.
- the light emitting layer may be a mixture of a host material and a dopant material, or a host material alone.
- the host material and dopant material may be one type or a combination of two or more.
- the dopant material may be included in the entire host material or may be included partially.
- the dopant material may be either laminated with the host material or dispersed in the host material. If the amount of the dopant material is too large, a concentration quenching phenomenon occurs, and therefore it is preferable to use it at 20 wt% or less, more preferably 10 wt% or less, based on the total of the host material and the dopant material.
- the dopant material may be formed by a co-evaporation method with the host material, or the host material and the dopant material may be mixed in advance and force may be deposited.
- the pyrene compound of the present invention may be used as a dopant material, it is preferably used as a host material because of its excellent thin film stability.
- the ionization potential of the pyrene compound of the present invention is not particularly limited, but is preferably 4.6 eV or more and 6.2 eV or less, more preferably 4.8 eV or more and 6. OeV or less.
- the absolute value of the ion potential may vary depending on the measurement method.
- the present invention The ON potential is 30 ⁇ on an ITO glass substrate using an atmospheric-type ultraviolet photoelectron analyzer (AC-1, manufactured by Riken Kikai Co., Ltd.). ⁇ Measured value of thin film deposited to a thickness of lOOnm.
- the host material used in the present invention need not be limited to only one kind of pyrene compound represented by the general formula (1), and a mixture of a plurality of pyrene compounds may be used. One or more types may be mixed with the pyrene compound represented by the general formula (1).
- the host materials that can be mixed include condensed ring derivatives such as anthracene and perylene, which are light emitters, and aromatics such as N, N, -dinaphthyl N, N, -diphenyl 4, 4'-diphenyl 2, 1'-diamine Metal derivatives, tris (8-quinolinato) aluminum (III) and other metal chelate oxinoid compounds, bisstyryl derivatives such as distyrylbenzene derivatives, tetraphenylbutadiene derivatives, indene derivatives, coumarin derivatives, oxadiazole Derivatives, Pyroguchi Pyridine Derivatives, Perinone Derivatives, Cyclopentagen Derivatives, Oxadiazole Derivatives, Forced Rubazole Derivatives, Pyrrolopyrrole Derivatives Derivative Porichiofen derivative is preferably used.
- condensed ring derivatives such as anthracene and perylene,
- the dopant material contained in the light-emitting material is not particularly limited, but is a compound having an aryl ring such as naphthalene, anthracene, phenanthrene, pyrene, triphenylene, perylene, fluorene, indene or a derivative thereof (for example, 2- (Benzothiazol-2-yl) —9, 10-diphenylanthracene, 5, 6, 11, 12-tetraphenyl-naphthacene, etc.), furan, pyrrole, thiophene, silole, 9-silaffnoleolene, 9, 9'— Spirovicirafluorene, benzothiophene, benzofuran, indole, dibenzothiophene, dibenzazofuran, imidazopyridine, phenanthorin, pyrazine, naphthyridine, quinoxaline, pyrrolopyridine, thioxanthen
- pyrene compounds having a benzoazole group represented by 1 (benzoxazole-2-yl) 3,8-bis (4 methylphenol) pyrene are particularly preferred dopants. .
- the electron transport layer is a layer into which cathode-power electrons are injected and further transports electrons. It is desired that the electron transport layer efficiently transports the injected electrons with high electron injection efficiency. Therefore, it is desirable that the electron transport layer is made of a material having a high electron affinity and a high electron mobility, and excellent stability, and impurities that become traps are less likely to be generated during manufacture and use.
- the electron transport layer mainly plays a role of effectively preventing the positive holes from flowing toward the cathode without recombination. If so, even if the material is not so high in the electron transport capability, the effect of improving the light emission efficiency is equivalent to that in the case of the material having a high electron transport capability.
- the electron transport material used for the electron transport layer is not particularly limited, but is represented by a compound having a condensed aryl ring such as naphthalene or anthracene or a derivative thereof, 4, 4 'bis (diphenyl-) phenyl.
- Styryl aromatic ring derivatives include quinolinol complexes such as III), hydroxyazole complexes such as hydroxyphenol-luoxazole complexes, azomethine complexes, trobolone metal complexes and flavonol metal complexes, and compounds having a heteroaryl ring.
- a compound having a heteroaryl ring having electron-accepting nitrogen is preferable because it has a high electron transporting ability.
- the electron-accepting nitrogen represents a nitrogen atom that forms a multiple bond with an adjacent atom.
- heteroaryl rings containing electron-accepting nitrogen have a high electron affinity.
- heteroaryl ring containing an electron-accepting nitrogen include a pyridine ring, a pyridine ring, a pyrimidine ring, a quinoline ring, a quinoxaline ring, a naphthyridine ring, a pyrimidopyrimidine ring, a benzoquinoline ring, a phenanthorin ring, an imidazole ring, and an oxazole.
- the compound having a heteroaryl ring structure containing electron-accepting nitrogen is preferably composed of an element selected from carbon, hydrogen, nitrogen, oxygen, silicon, and phosphorus.
- a compound having a heteroaryl ring structure containing an electron-accepting nitrogen composed of an element selected from these medium strengths has a high electron transporting ability and can significantly reduce the driving voltage of the light-emitting element.
- Examples of such compounds include benzimidazole derivatives, benzoxazole derivatives, benzthiazole derivatives, oxadiazole derivatives, thiadiazol derivatives, triazole derivatives, pyrazine derivatives, phenanthorin derivatives, quinoxaline derivatives, quinoline derivatives, benzoquinoline derivatives.
- Oligopyridine derivatives such as biviridine and terpyridine, quinoxaline derivatives, naphthyridine derivatives, and the like are preferable, and examples thereof include compounds.
- imidazole derivatives such as tris (N-phenol benzimidazole-2-yl) benzene, oxadiazole derivatives such as 1,3 bis [(4-tert butylphenol) 1,3,4 oxadiazolyl] phenol, N—Naphthyl 2, 5 diphenyl— Triazole derivatives such as 1, 3, 4 triazole, phenant mouth phosphorus derivatives such as bathocuproine and 1, 3 bis (1, 10 phenantine 9-9) benzene, 2, 2 , 1 bis (benzo [h] quinoline 2-yl) 9, 9, benzoquinoline derivatives such as spirobifluorene, 2, 5 bis (6,-(2, 2, 2, -bibilidyl))-1 , 1-dimethyl-3,4-diphenyl
- the electron transport material may be used alone, but two or more of the electron transport materials may be mixed and used, or one or more of the other electron transport materials may be mixed and used in the electron transport material. I do not care. It can also be used by mixing with metals such as alkali metals and alkaline earth metals.
- the ionic potential of the electron transport layer is not particularly limited. Preferably, it is 5.8 eV or more and 8. OeV or less, and more preferably 6. OeV or more and 7.5 eV or less.
- the method for forming each of the layers constituting the light emitting element is not particularly limited, such as resistance heating vapor deposition, electron beam vapor deposition, sputtering, molecular lamination method, coating method, ink jet method, printing method, laser induced thermal transfer method, etc.
- resistance heating vapor deposition or electron beam vapor deposition is preferable from the viewpoint of device characteristics.
- the thickness of the layer cannot be limited because it depends on the resistance value of the luminescent material, but is selected from 1-1000 nm.
- the film thicknesses of the light-emitting layer, the electron transport layer, and the hole transport layer are each preferably 1 nm or more and 200 nm or less, and more preferably 5 nm or more and lOO nm or less.
- the light-emitting element of the present invention has a function of converting electrical energy into light.
- the electric energy it is possible to use a force S in which a direct current is mainly used, a pulse current or an alternating current.
- the current value and voltage value are not particularly limited, but should be selected so that the maximum brightness can be obtained with as low energy as possible in consideration of the power consumption and lifetime of the device.
- the light-emitting device of the present invention is suitably used as a display for displaying in a matrix and Z or segment system, for example.
- pixels for display are arranged two-dimensionally, such as a grid or mosaic.
- a character and an image are displayed with a set of pixels.
- the shape and size of the pixel are determined by the application. For example, rectangular pixels with a side of 300 ⁇ m or less are usually used for images and text display on computers, monitors, and televisions. Also, for large displays such as display panels, one side is on the order of mm. Pixels are used.
- monochrome display pixels of the same color may be arranged, but in color display, red, green, and blue pixels are displayed side by side. In the case of color display, there are typically delta type and stripe type.
- the matrix driving method may be either line sequential driving or active matrix. In the case of line sequential driving, the structure of the light emitting element is simple, but the active matrix may be superior in consideration of operating characteristics. Use different driving methods depending on the application.
- the segment system is a system in which a pattern is formed so as to display predetermined information and an area determined by the arrangement of the pattern is emitted. Examples include time and temperature displays on digital and thermometers, operating status displays for audio equipment and electromagnetic cookers, and car panel displays. And the matrix display and the segment display can coexist in the same panel.
- the light-emitting device of the present invention is also preferably used as a backlight for various devices. Knocklights are mainly used for the purpose of improving the visibility of non-self-luminous display devices, and are used for liquid crystal display devices, watches, audio devices, automobile panels, display boards and signs.
- the light-emitting element of the present invention is preferably used for a backlight for a liquid crystal display device, especially a personal computer application for which a reduction in thickness is being studied.
- the light-emitting element of the present invention can provide a backlight that is thinner and lighter than conventional ones.
- H-NMR was measured using a superconducting FTNMR-270 (manufactured by JEOL Ltd.) in a deuterated chloroform solution.
- HPLC purity was determined using a high performance liquid chromatograph 1 ⁇ -10 (manufactured by Shimadzu Corporation). The measurement was performed with a lgZL black mouth form solution. As a developing solvent for the column, a mixed solution of 0.1% aqueous phosphoric acid solution and acetonitrile was used.
- the obtained solid was washed with 30 ml of ethanol, purified by silica gel column chromatography, recrystallized from dimethylformamide, and dried under vacuum to obtain 0.69 g of white crystals.
- the results of 1 H-NMR analysis of the obtained powder are as follows, and it was confirmed that the white crystals obtained above were a compound [30].
- This compound [30] was subjected to sublimation purification at about 240 ° C under a pressure of 1 X 10_3 Pa using an oil diffusion pump and used as a force light emitting device material.
- the HPLC purity (area% at a measurement wavelength of 254 ⁇ m) was 99.6% before sublimation purification and 99.7% after sublimation purification.
- 1-Bromopyrene 45 Og, 4-Methylphenolic acid 21.7 g, Tripotassium phosphate 34.
- a mixed solution of 0 g, tetraptyl ammonium bromide 10.3 g, palladium acetate 0.71 g and dimethylformamide 1.6 L was heated and stirred at 120 ° C. for 5 hours under a nitrogen stream. After the solution was cooled to room temperature, 1.6 L of water was injected and stirred at room temperature for 0.5 h. The precipitated solid was collected by filtration and washed twice with 200 ml of water. The obtained solid was dissolved in 500 ml of dichloromethane, dried over magnesium sulfate, and filtered through celite. The filtrate was evaporated, the residue was washed twice with 200 ml of methanol, and the precipitated solid was collected by filtration and dried under vacuum to obtain 1- (4-methylphenol) pyrene 40.
- This compound [69] was subjected to sublimation purification at about 240 ° C under a pressure of 1 X 10_3 Pa using an oil diffusion pump and used as a force light emitting device material.
- the HPLC purity (area% at a measurement wavelength of 254 ⁇ m) was 99.4% before sublimation purification and 99.5% after sublimation purification.
- This compound [47] was subjected to sublimation purification at about 260 ° C under a pressure of 1 X 10 _3 Pa using an oil diffusion pump and used as a force light emitting device material.
- the HPLC purity (area% at a measurement wavelength of 254 ⁇ m) was 99.7% before sublimation purification and 99.8% after sublimation purification.
- This compound [29] was subjected to sublimation purification at about 250 ° C under a pressure of 1 X 10 _3 Pa using an oil diffusion pump and used as a force light emitting device material.
- the HPLC purity (area% at a measurement wavelength of 254 ⁇ m) was 99.6% before sublimation purification and 99.8% after sublimation purification.
- This compound [33] was subjected to sublimation purification at about 260 ° C under a pressure of 1 X 10 _3 Pa using an oil diffusion pump and used as a force light emitting device material.
- the HPLC purity (area% at a measurement wavelength of 254 ⁇ m) was 99.8% before sublimation purification and 99.9% after sublimation purification.
- the compound was synthesized in the same manner as in Example 4 except that phenylboronic acid was used instead of 2-biphenylboronic acid to obtain 322 mg of white crystals.
- the results of 1 H-NMR analysis of the obtained powder are as follows, and it was confirmed that the white crystals obtained above were the compound [28].
- This compound [28] was subjected to sublimation purification at about 240 ° C under a pressure of 1 X 10_3 Pa using an oil diffusion pump, and used as a force light emitting device material.
- HPLC purity (measurement wavelength 254 ⁇ The area% in m) was 99.5% before sublimation purification and 99.6% after sublimation purification.
- This compound [35] was subjected to sublimation purification at about 280 ° C under a pressure of 1 X 10_3 Pa using an oil diffusion pump and used as a force light emitting device material.
- the HPLC purity (area% at a measurement wavelength of 254 ⁇ m) was 99.1% before sublimation purification and 99.8% after sublimation purification.
- This compound [45] was subjected to sublimation purification at about 300 ° C under a pressure of 1 X 10_3 Pa using an oil diffusion pump and used as a force light emitting device material.
- the HPLC purity (area% at a measurement wavelength of 254 ⁇ m) was 99.5% before sublimation purification and 99.6% after sublimation purification.
- This compound [49] is about 270 ° C under the pressure of 1 X 10 _3 Pa using an oil diffusion pump.
- Sublimation purification was carried out using a force light emitting device material.
- the HPLC purity (area% at a measurement wavelength of 254 ⁇ m) was 99.7% before sublimation purification and 99.8% after sublimation purification.
- 1-bromo 6- (4-methylphenol) pyrene 8 Og, 3,5 dichlorophenolic acid 4.5 g, tripotassium phosphate 9.2 g, tetraptyl ammonium bromide 1.4 g, paradium acetate 97 mg
- a mixed solution of 215 ml of dimethylformamide was heated and stirred at 120 ° C for 5 hours under a nitrogen stream. After the solution was cooled to room temperature, water 1.OL was injected and extracted with 600 ml of dichloromethane. The organic layer was washed twice with 200 ml of water, dried over magnesium sulfate, and filtered through celite.
- This compound [81] was subjected to sublimation purification at about 280 ° C under a pressure of 1 X 10 _3 Pa using an oil diffusion pump and used as a force light emitting device material.
- the HPLC purity (area% at a measurement wavelength of 254 ⁇ m) was 99.2% before sublimation purification and 99.3% after sublimation purification.
- the solution was cooled to room temperature, filtered, and the obtained solid was washed with 30 ml of dioxane, 50 ml of water, and 50 ml of ethanol.
- the obtained solid was recrystallized from 100 ml of xylene and vacuum-dried to obtain 0.15 g of yellowish white crystals.
- the results of 1 H-NMR analysis of the obtained powder are as follows, and it was confirmed that the yellowish white crystals obtained above were the compound [99].
- the HPLC purity (area% at a measurement wavelength of 254 nm) was 99.1%.
- This compound [104] was subjected to sublimation purification at about 280 ° C. under a pressure of 1 ⁇ 10_3 Pa using an oil diffusion pump and used as a force light emitting device material.
- the HPLC purity (area% at a measurement wavelength of 25 4 nm) was 99.5% before sublimation purification and 99.7% after sublimation purification.
- This compound [117] was subjected to sublimation purification at about 230 ° C under a pressure of 1 X 10 _3 Pa using an oil diffusion pump and used as a force light emitting device material.
- the HPLC purity (area% at a measurement wavelength of 25 4 nm) was 99.7% before sublimation purification and 99.9% after sublimation purification.
- This compound [120] was subjected to sublimation purification at about 270 ° C. under a pressure of 1 ⁇ 10_3 Pa using an oil diffusion pump and used as a force light emitting device material.
- the HPLC purity (area% at a measurement wavelength of 25 4 nm) was 99.7% before sublimation purification and 99.9% after sublimation purification.
- the compound was synthesized in the same manner as in Example 13 except that 4 t-butylphenol boronic acid was used in place of 4 methylphenol boronic acid to obtain 569 mg of white crystals.
- the results of 1 H NMR analysis of the obtained powder are as follows, and it was confirmed that the white crystals obtained above were the compound [127].
- This compound [127] was subjected to sublimation purification at about 260 ° C. under a pressure of 1 ⁇ 10 — 3 Pa using an oil diffusion pump, and used as a force light emitting device material.
- the HPLC purity (area% at a measurement wavelength of 25 4 nm) was 99.5% before sublimation purification and 99.6% after sublimation purification.
- Example 13 except that 9 [4- (4, 4, 5, 5-tetramethyl- [1, 3, 2,2] oxaborolane-2-yl) phenol] rubazole was used in place of 4 methylphenol boronic acid.
- milky white crystals were obtained.
- the results of 1 H-NMR analysis of the obtained powder are as follows, and it was confirmed that the milky white crystals obtained above were the compound [128].
- This compound [128] was subjected to sublimation purification at about 300 ° C. under a pressure of 1 ⁇ 10 3 Pa using an oil diffusion pump and used as a force light emitting device material.
- the HPLC purity (area% at a measurement wavelength of 25 4 nm) was 99.8% before sublimation purification and 99.9% after sublimation purification.
- This compound [129] was subjected to sublimation purification at about 280 ° C under a pressure of 1 X 10 _3 Pa using an oil diffusion pump and used as a force light emitting device material.
- HPLC purity (measurement wavelength 25 The area% at 4 nm) was 99.7% before sublimation purification and 99.9% after sublimation purification.
- This compound [131] was subjected to sublimation purification at about 250 ° C under a pressure of 1 X 10 _3 Pa using an oil diffusion pump and used as a force light emitting device material.
- the HPLC purity (area% at a measurement wavelength of 25 4 nm) was 99.8% before sublimation purification and 99.9% after sublimation purification.
- This compound [135] was subjected to sublimation purification at about 310 ° C. under a pressure of 1 ⁇ 10_3 Pa using an oil diffusion pump and used as a force light emitting device material.
- the HPLC purity (area% at a measurement wavelength of 25 4 nm) was 99.5% before sublimation purification and 99.9% after sublimation purification.
- This compound [141] was subjected to sublimation purification at about 280 ° C under a pressure of 1 X 10 _3 Pa using an oil diffusion pump, and used as a force light emitting device material.
- the HPLC purity (area% at a measurement wavelength of 25 4 nm) was 99.7% before sublimation purification and 99.9% after sublimation purification.
- 1-bromopyrene 7g trimethylboroxine 6g, cesium carbonate 12g, PdCl (dppf) -C
- the organic layer was washed twice with 20 ml of water, dried over magnesium sulfate and evaporated.
- the concentrate was purified by silica force gel column chromatography and dried in vacuo to obtain 3 g of 7 t-Pitreux 1-methinorepyrene.
- the obtained solid was washed with 30 ml of ethanol, purified by silica gel chromatography, and vacuum-dried to obtain 1.2 g of white crystals.
- the results of 1 H-NMR analysis of the obtained powder are as follows, and it was confirmed that the white crystals obtained above were the compound [183].
- This compound [183] was subjected to sublimation purification at about 230 ° C. under a pressure of 1 ⁇ 10 3 Pa using an oil diffusion pump and used as a force light emitting device material.
- the HPLC purity (area% at a measurement wavelength of 25 4 nm) was 99.1% before sublimation purification and 99.3% after sublimation purification.
- the obtained solid was washed with 40 ml of methanol and then purified by silica gel chromatography, followed by vacuum drying to obtain 2.5 g of yellowish white crystals.
- the results of 1 H-NMR analysis of the obtained powder are as follows, and it was confirmed that the yellowish white crystals obtained above are the compound [185].
- This compound [185] was subjected to sublimation purification at about 250 ° C. under a pressure of 1 ⁇ 10_3 Pa using an oil diffusion pump and used as a force light emitting device material.
- the HPLC purity (area% at a measurement wavelength of 25 4 nm) was 99.4% before sublimation purification and 99.6% after sublimation purification.
- This compound [174] was subjected to sublimation purification at about 260 ° C. under a pressure of 1 ⁇ 10 3 Pa using an oil diffusion pump, and used as a force light emitting device material.
- the HPLC purity (area% at a measurement wavelength of 25 4 nm) was 99.4% before sublimation purification and 99.6% after sublimation purification.
- the obtained solid was washed with 40 ml of methanol and then purified by silica gel chromatography, followed by vacuum drying to obtain 2.3 g of yellowish white crystals.
- the results of 1 H-NMR analysis of the obtained powder are as follows, and it was confirmed that the yellowish white crystal obtained above was Compound [199].
- This compound [199] was subjected to sublimation purification at about 230 ° C under a pressure of 1 X 10_3 Pa using an oil diffusion pump and used as a force light emitting device material.
- the HPLC purity (area% at a measurement wavelength of 25 4 nm) was 99.4% before sublimation purification and 99.6% after sublimation purification.
- This compound [245] was subjected to sublimation purification at about 270 ° C. under a pressure of 1 ⁇ 10 3 Pa using an oil diffusion pump and used as a force light emitting device material.
- the HPLC purity (area% at a measurement wavelength of 25 4 nm) was 99.5% before sublimation purification and 99.6% after sublimation purification.
- 1-bromopyrene 2. Og, 4-t-butylphenol boronic acid 1.9 g, tripotassium phosphate 3. lg, tetraptyl ammonium bromide 0.46 g, mixed solution of palladium acetate 70 mg and dimethylformamide 70 mL under nitrogen stream The mixture was stirred at 130 ° C for 2 hours. Solution at room temperature The solution was poured into 350 mL of water, and the precipitated solid was collected by filtration. The obtained solid was dissolved in dichloromethane, washed with water, dried over magnesium sulfate, and concentrated. The resulting crude product was purified by column chromatography and vacuum dried to obtain 1.9 g of 1- (4-t-butylphenol) pyrene.
- the obtained solid was dissolved in diclonal methane, washed with water, dried over magnesium sulfate, and concentrated.
- the obtained crude product was purified by column chromatography and vacuum-dried to obtain 0.49 g of 1- (4-t-butylphenol) 7 vinylene.
- the obtained solid was dissolved in dichloromethane, washed with water, dried over magnesium sulfate, and concentrated.
- the resulting crude product was purified by column chromatography and vacuum dried to obtain 0.54 g of a white solid.
- Ethyl acetate 2 OmL was added to the obtained solid, and this suspension was heated and stirred. After cooling to room temperature, filtration and vacuum drying, 0.21 g of a white solid was obtained.
- the results of 1 H-NMR analysis of the obtained powder are as follows, and it was confirmed that the white crystals obtained above were the compound [267].
- the HPLC purity (area% at a measurement wavelength of 254 nm) was 99.8%.
- This compound [283] was subjected to sublimation purification at about 270 ° C. under a pressure of 1 ⁇ 10 _3 Pa using an oil diffusion pump and used as a force light emitting device material.
- the HPLC purity (area% at a measurement wavelength of 25 4 nm) was 99.5% before sublimation purification and 99.8% after sublimation purification.
- a mixed solution of 5 g of 1-bromopyrene, 7.9 g of N-bromosuccinimide, and 140 ml of dimethylformamide was stirred at 80 ° C. for 10 hours under a nitrogen stream. After cooling the solution to room temperature, 40 Oml of water was injected, and the precipitate was filtered. The filtered solid was washed with 50 ml of water, 100 ml of methanol, and 200 ml of dichloromethane, and then vacuum-dried at 70 ° C. to obtain 6.1 g of 1,3,6 tribromopyrene as a light ocher powder.
- This compound [49] was subjected to sublimation purification at about 300 ° C under a pressure of 1 X 10_3 Pa using an oil diffusion pump and used as a force light emitting device material.
- the HPLC purity (area% at a measurement wavelength of 254 ⁇ m) was 99.3% before sublimation purification and 99.4% after sublimation purification.
- a mixed solution of 100 g of pyrene, 55.4 g of t-butyl chloride and 400 ml of dichloromethane was cooled to 0 ° C. under an argon stream to obtain 70.4 g of salt aluminum.
- the mixed solution was stirred at room temperature for 5 hours, poured into 500 g of ice, and stirred at room temperature for 30 minutes.
- the mixed solution was suction filtered, and the filtrate was extracted twice with 300 ml of dichloromethane.
- the organic layer was washed with 300 ml of water, dried over magnesium sulfate and evaporated. To the concentrated residue, 300 ml of methanol was added and stirred at 80 ° C., followed by filtration.
- Hexane Z dichloromethane (15 ml of 30ZD) was added to the resulting crude product, stirred, filtered and dried under reduced pressure. Hexane Z dichloromethane (10 ml of 30ZD was added to the resulting solid for 30 minutes. After stirring, the mixture was filtered and dried under reduced pressure to obtain 435 mg of white powder, and the result of 1 H-NMR analysis of the obtained powder is as follows, and the obtained white powder was compound [338]. It was confirmed that.
- a light emitting device using the compound [29] was produced as follows.
- a glass substrate manufactured by Asahi Glass Co., Ltd., 15 ⁇ well, electron beam evaporated product
- the ITO film was patterned by photolithography to produce a light emitting portion and an electrode lead portion.
- the obtained substrate was ultrasonically cleaned with acetone, “Semicocrine (registered trademark) 56” (manufactured by Fruch Chemical Co., Ltd.) for 15 minutes and then with ultrapure water. Subsequently, the substrate was ultrasonically cleaned with isopropyl alcohol for 15 minutes and then immersed in hot methanol for 15 minutes to dry. Immediately before the device was fabricated, this substrate was subjected to UV-ozone treatment for 1 hour, and then placed in a vacuum deposition apparatus, and evacuated until the degree of vacuum in the apparatus was 5 X 10_4 Pa or less.
- lithium fluoride was vapor-deposited to a thickness of 0.5 nm, and then aluminum was lOOOnm vapor-deposited as a cathode to produce a 5 ⁇ 5 mm square device.
- the film thickness referred to here is a display value of a crystal oscillation type film thickness monitor.
- a light emitting device was fabricated in the same manner as in Example 31 except that the materials listed in Tables 1 to 3 were used as the host material. The results of each example are shown in Tables 1-3.
- H- :! to H-6 are compounds represented by the following formulae.
- a light emitting device was produced in the same manner as in Example 31 except that the materials listed in Table 4 were used as the dopant material so that the doping concentration was 2%.
- the results of each example are shown in Table 4 [Table 4]
- D-2 to D-10 are compounds represented by the following formulae:
- a light emitting device was fabricated in the same manner as in Example 31 except that the materials listed in Table 5 were used as the electron transporting material. The results of each example are shown in Table 5.
- E-2 to E-8 are compounds represented by the following formulas,
- a light emitting device was produced in the same manner as in Example 31 except that D-11 shown by the following formula was used as a dopant material so that the doping concentration was 2%.
- this light emitting device was DC driven with lOmAZcm 2 , high efficiency green light emission with a luminous efficiency of 5.21 mZW was obtained.
- this light emitting device was continuously driven with a direct current of lOmAZcm 2 , the luminance half-life was 4000 hours.
- a light emitting device was produced in the same manner as in Example 31 except that D-12 represented by the following formula was used as a dopant material so that the doping concentration was 5%.
- this light emitting device was DC driven with lOmAZcm 2 , high efficiency yellow light emission with a luminous efficiency of 5.81 mZW was obtained.
- this light-emitting device was driven continuously with a direct current of lOmAZcm 2 , the luminance half-life was 10,000 hours.
- the compound [29] as the host material and the compound [29] as the dopant material and D-12 as the dopant material were deposited to a thickness of 5 nm so that the dopant concentration was 5%, and then the compound [29] as the host material as the luminescent material.
- a light emitting device was produced in the same manner as in Example 31 except that D-1 was laminated as a dopant material to a thickness of 30 nm so that the doping concentration was 2%.
- this light-emitting device was DC-driven with lOmAZcm 2 , a high-efficiency white with a luminous efficiency of 6.51 mZW was obtained. Color emission was obtained.
- this light emitting device was continuously driven with a direct current of lOmAZcm 2 , the luminance half time was 10,000 hours.
- a glass substrate manufactured by Asahi Glass Co., Ltd., 15 ⁇ well, electron beam evaporated product
- an ITO transparent conductive film was deposited to 150 nm was cut into 30 ⁇ 40 mm.
- the ITO film was patterned into a stripe shape of 300 ⁇ m pitch (remaining width 270 m) ⁇ 32 stripes by photolithography.
- One side of the ITO stripe in the long side direction is extended to 1.27mm pitch (opening width 800 / zm) to facilitate electrical connection to the outside.
- the obtained substrate was ultrasonically cleaned with acetone and “Semicocrine (registered trademark) 56” (manufactured by Furuuchi Chemical Co., Ltd.) for 15 minutes, respectively, and then with ultrapure water. Subsequently, the substrate was ultrasonically cleaned with isopropyl alcohol for 15 minutes, and then immersed in hot methanol for 15 minutes and dried. This substrate was subjected to UV-ozone treatment for 1 hour immediately before the device was fabricated, and further placed in a vacuum deposition apparatus, and evacuated until the degree of vacuum in the apparatus was 5 ⁇ 10 -4 Pa or less.
- a 4,4'-bis (N— (m-tolyl) -N-phenolamino) bi-layer was first deposited as a hole transport material by resistance heating method at 150 nm. did.
- compound [29] was deposited as a host material and D-1 was deposited as a dopant material to a thickness of 35 nm so that the doping concentration was 2%.
- E-1 was laminated to a thickness of 20 nm as an electron transport material.
- the film thickness referred to here is a display value of a crystal oscillation type film thickness monitor.
- a mask with 16 250 ⁇ m openings (remaining width 50 ⁇ m, equivalent to 300 m pitch) formed by wet etching on a 50 ⁇ m thick Kovar plate is perpendicular to the ITO stripe in a vacuum.
- the magnet was applied from the back of the substrate and fixed so that the mask and the ITO substrate were in close contact.
- the organic layer was doped with 0.5 nm of lithium and then evaporated with 200 nm of aluminum to produce a 32 ⁇ 16 dot matrix device. When this device was driven in matrix, characters could be displayed without crosstalk.
- the light emitting device material of the present invention can be used for a light emitting device or the like, and can provide a light emitting device material having excellent thin film stability. According to the present invention, a light emitting device having high luminous efficiency and excellent durability can be obtained.
- the light-emitting element of the present invention includes a display element, a flat panel display, and a bar. It can be used for fields such as lighting, lighting, interiors, signs, signboards, electronic cameras and optical signal generators.
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Abstract
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EP06797666.2A EP1942171B1 (en) | 2005-09-08 | 2006-09-08 | Light-emitting device material and light-emitting device |
US11/991,461 US8610345B2 (en) | 2005-09-08 | 2006-09-08 | Light-emitting device material and light-emitting device |
KR1020137015484A KR20130079658A (ko) | 2005-09-08 | 2006-09-08 | 발광 소자 재료 및 발광 소자 |
US14/073,651 US20140061629A1 (en) | 2005-09-08 | 2013-11-06 | Light-emitting device material and light-emitting device |
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WO2008108256A1 (ja) * | 2007-03-07 | 2008-09-12 | Toray Industries, Inc. | 発光素子材料および発光素子 |
JP2009010181A (ja) * | 2007-06-28 | 2009-01-15 | Toray Ind Inc | 発光素子 |
JP2009246354A (ja) * | 2008-03-10 | 2009-10-22 | Toray Ind Inc | 発光素子 |
JP2009267378A (ja) * | 2008-04-01 | 2009-11-12 | Canon Inc | 有機発光素子 |
WO2010001817A1 (ja) | 2008-07-01 | 2010-01-07 | 東レ株式会社 | 発光素子 |
WO2010067893A1 (en) * | 2008-12-10 | 2010-06-17 | Canon Kabushiki Kaisha | Novel pyrene compound |
JP2010150168A (ja) * | 2008-12-24 | 2010-07-08 | Tosoh Corp | アミン誘導体及びその用途 |
US20100244676A1 (en) * | 2009-03-31 | 2010-09-30 | Fujifilm Corporation | Organic electroluminescent device |
EP2100941A3 (en) * | 2008-03-14 | 2010-10-06 | Gracel Display Inc. | Novel organic electroluminescent compounds and organic electroluminescent device using the same |
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KR20130079657A (ko) | 2013-07-10 |
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EP2463351A2 (en) | 2012-06-13 |
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CN103193697B (zh) | 2015-11-18 |
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EP2463351A3 (en) | 2012-06-27 |
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EP1942171A1 (en) | 2008-07-09 |
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