WO2017170313A1 - 発光素子 - Google Patents
発光素子 Download PDFInfo
- Publication number
- WO2017170313A1 WO2017170313A1 PCT/JP2017/012225 JP2017012225W WO2017170313A1 WO 2017170313 A1 WO2017170313 A1 WO 2017170313A1 JP 2017012225 W JP2017012225 W JP 2017012225W WO 2017170313 A1 WO2017170313 A1 WO 2017170313A1
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- WO
- WIPO (PCT)
- Prior art keywords
- group
- ring
- substituent
- formula
- light emitting
- Prior art date
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- 125000001424 substituent group Chemical group 0.000 claims description 188
- 125000000623 heterocyclic group Chemical group 0.000 claims description 146
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- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000005446 heptyloxy 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])O* 0.000 description 1
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- FHKSXSQHXQEMOK-UHFFFAOYSA-N hexane-1,2-diol Chemical compound CCCCC(O)CO FHKSXSQHXQEMOK-UHFFFAOYSA-N 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 125000003707 hexyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 125000005980 hexynyl group Chemical group 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 1
- LHJOPRPDWDXEIY-UHFFFAOYSA-N indium lithium Chemical compound [Li].[In] LHJOPRPDWDXEIY-UHFFFAOYSA-N 0.000 description 1
- 229910003437 indium oxide Inorganic materials 0.000 description 1
- YZASAXHKAQYPEH-UHFFFAOYSA-N indium silver Chemical compound [Ag].[In] YZASAXHKAQYPEH-UHFFFAOYSA-N 0.000 description 1
- PJXISJQVUVHSOJ-UHFFFAOYSA-N indium(iii) oxide Chemical compound [O-2].[O-2].[O-2].[In+3].[In+3] PJXISJQVUVHSOJ-UHFFFAOYSA-N 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 230000002687 intercalation Effects 0.000 description 1
- 238000009830 intercalation Methods 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 238000007733 ion plating Methods 0.000 description 1
- 229910052741 iridium Inorganic materials 0.000 description 1
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 1
- 125000002510 isobutoxy group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])O* 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 1
- 239000005453 ketone based solvent Substances 0.000 description 1
- 238000010030 laminating Methods 0.000 description 1
- 150000002605 large molecules Chemical class 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 229910001416 lithium ion Inorganic materials 0.000 description 1
- GCICAPWZNUIIDV-UHFFFAOYSA-N lithium magnesium Chemical compound [Li].[Mg] GCICAPWZNUIIDV-UHFFFAOYSA-N 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- SJCKRGFTWFGHGZ-UHFFFAOYSA-N magnesium silver Chemical compound [Mg].[Ag] SJCKRGFTWFGHGZ-UHFFFAOYSA-N 0.000 description 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
- AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 1
- 125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229910001512 metal fluoride Inorganic materials 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- 229940095102 methyl benzoate Drugs 0.000 description 1
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 1
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- 239000011733 molybdenum Substances 0.000 description 1
- 229940094933 n-dodecane Drugs 0.000 description 1
- 150000002791 naphthoquinones Chemical class 0.000 description 1
- 125000006611 nonyloxy group Chemical group 0.000 description 1
- 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 1
- 125000005447 octyloxy 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])O* 0.000 description 1
- 238000007645 offset printing Methods 0.000 description 1
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 1
- 229960003540 oxyquinoline Drugs 0.000 description 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
- 125000004115 pentoxy group Chemical group [*]OC([H])([H])C([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 125000005003 perfluorobutyl group Chemical group FC(F)(F)C(F)(F)C(F)(F)C(F)(F)* 0.000 description 1
- 125000005005 perfluorohexyl group Chemical group FC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)* 0.000 description 1
- 125000005007 perfluorooctyl group Chemical group FC(C(C(C(C(C(C(C(F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)* 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 229940049953 phenylacetate Drugs 0.000 description 1
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 238000000103 photoluminescence spectrum Methods 0.000 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 238000007747 plating Methods 0.000 description 1
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 1
- 229920000553 poly(phenylenevinylene) Polymers 0.000 description 1
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 1
- 229920000767 polyaniline Polymers 0.000 description 1
- 229920000412 polyarylene Polymers 0.000 description 1
- 229920002098 polyfluorene Polymers 0.000 description 1
- 229920000128 polypyrrole Polymers 0.000 description 1
- 239000011970 polystyrene sulfonate Substances 0.000 description 1
- 229960002796 polystyrene sulfonate Drugs 0.000 description 1
- 229920000123 polythiophene Polymers 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011698 potassium fluoride Substances 0.000 description 1
- 235000003270 potassium fluoride Nutrition 0.000 description 1
- 229910001414 potassium ion Inorganic materials 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 238000007348 radical reaction Methods 0.000 description 1
- 238000001226 reprecipitation Methods 0.000 description 1
- 238000012827 research and development Methods 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 229910052701 rubidium Inorganic materials 0.000 description 1
- IGLNJRXAVVLDKE-UHFFFAOYSA-N rubidium atom Chemical compound [Rb] IGLNJRXAVVLDKE-UHFFFAOYSA-N 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 229910001415 sodium ion Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000000956 solid--liquid extraction Methods 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 229910052712 strontium Inorganic materials 0.000 description 1
- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical compound CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 1
- NLDYACGHTUPAQU-UHFFFAOYSA-N tetracyanoethylene Chemical group N#CC(C#N)=C(C#N)C#N NLDYACGHTUPAQU-UHFFFAOYSA-N 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
Classifications
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/10—Organic polymers or oligomers
- H10K85/151—Copolymers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G61/02—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes
- C08G61/10—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes only aromatic carbon atoms, e.g. polyphenylenes
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G61/12—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule
-
- 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
- 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
- H10K85/10—Organic polymers or oligomers
- H10K85/111—Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
- H10K85/115—Polyfluorene; Derivatives thereof
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/14—Carrier transporting layers
- H10K50/15—Hole transporting layers
Definitions
- the present invention relates to a light emitting element.
- Light emitting elements such as organic electroluminescence elements can be suitably used for display and lighting applications, and research and development are being conducted.
- Patent Document 1 discloses an organic layer containing a polymer compound (P0-1) represented by the following formula, and a light emitting layer containing a fluorescent compound (EM0-1) represented by the following formula: A light emitting device having the following is described.
- Patent Document 2 discloses an organic layer containing a polymer compound (P0-2) containing a structural unit (M0) represented by the following formula, and a fluorescent compound (EM0-2) represented by the following formula: And a light-emitting layer containing a light-emitting layer.
- P0-2 polymer compound
- M0 structural unit
- EM0-2 fluorescent compound
- an object of the present invention is to provide a light-emitting element that is excellent in external quantum efficiency.
- the present invention provides the following [1] to [15].
- a light emitting device having two organic layers The first organic layer is a layer containing a fluorescent low molecular weight compound; The maximum peak wavelength of the emission spectrum of the fluorescent low molecular weight compound is 380 nm or more and 750 nm or less,
- the second organic layer is a layer containing a crosslinked product of a polymer compound containing a crosslinked structural unit having a crosslinking group, For each constituent unit constituting the polymer compound, a value x obtained by multiplying the molar ratio C of the constituent unit to the total mole of all constituent units and the molecular weight M of the constituent unit, and the molar ratio C and the constituent unit.
- a light emitting device which is 60 or more.
- the polymer compound is a polymer compound containing a crosslinked structural unit having at least one crosslinking group selected from the group A of crosslinking groups.
- R XL represents a methylene group, an oxygen atom or a sulfur atom
- n XL represents an integer of 0 to 5.
- L A is an alkylene group, a cycloalkylene group, an arylene group, a divalent heterocyclic group, the group represented by -NR'-, an oxygen atom or a sulfur atom, these groups have a substituent Also good.
- R ′ represents a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group, or a monovalent heterocyclic group, and these groups optionally have a substituent.
- X represents a crosslinking group selected from the crosslinking group A group. When two or more X exists, they may be the same or different.
- mA represents an integer of 0 to 5
- m represents an integer of 1 to 4
- c represents an integer of 0 or 1.
- Ar 5 represents an aromatic hydrocarbon group, a heterocyclic group, or a group in which at least one aromatic hydrocarbon ring and at least one heterocyclic ring are directly bonded, and these groups have a substituent. It may be.
- Ar 4 and Ar 6 each independently represent an arylene group or a divalent heterocyclic group, and these groups optionally have a substituent.
- Ar 4 , Ar 5 and Ar 6 are each bonded to a group other than the group bonded to the nitrogen atom to which the group is bonded, directly or via an oxygen atom or a sulfur atom to form a ring. It may be.
- K A is an alkylene group, a cycloalkylene group, an arylene group, a divalent heterocyclic group, the group represented by -NR'-, an oxygen atom or a sulfur atom, these groups have a substituent Also good.
- R ′ represents a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group, or a monovalent heterocyclic group, and these groups optionally have a substituent.
- X ′ represents a bridging group selected from the bridging group A, a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group, or a monovalent heterocyclic group, and these groups may have a substituent. .
- X ′ is a cross-linking group selected from the cross-linking group A group.
- n 1B represents an integer of 0 to 15.
- Ar 1B represents an aromatic hydrocarbon group or an aromatic heterocyclic group, and these groups optionally have a substituent. When a plurality of such substituents are present, they may be the same or different, and may be bonded to each other to form a ring together with the atoms to which each is bonded.
- R 1B represents an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, a monovalent heterocyclic group, a substituted amino group, an alkenyl group, a cycloalkenyl group, an alkynyl group, or a cycloalkynyl group, and The group may have a substituent.
- R 1B When a plurality of R 1B are present, they may be the same or different, and may be bonded to each other to form a ring together with the carbon atoms to which they are bonded.
- the light emitting device according to [4] or [5], wherein the Ar 1B is an aromatic hydrocarbon group which may have a substituent.
- the Ar 1B is a benzene ring, biphenyl ring, naphthalene ring, anthracene ring, phenanthrene ring, dihydrophenanthrene ring, triphenylene ring, naphthacene ring, fluorene ring, spirobifluorene ring, pyrene ring, perylene ring, chrysene ring, A group formed by removing one or more hydrogen atoms directly bonded to the carbon atoms constituting the ring from the indene ring, fluoranthene ring, benzofluoranthene ring or acenaphthofluoranthene ring (the group has a substituent)
- the light-emitting element according to [6].
- [8] A group formed by removing Ar 1B from a pyrene ring, chrysene ring, fluoranthene ring or benzofluoranthene ring by removing one or more hydrogen atoms directly bonded to the carbon atoms constituting the ring (the group is a substituent)
- R 1B is an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group, a substituted amino group, an alkenyl group, or a cycloalkenyl group (these groups may have a substituent).
- the light emitting device according to any one of [4] to [8].
- the first organic layer is a layer containing the fluorescent low molecular weight compound and a host material
- the host material is a compound represented by the formula (FH-1) or a formula (Y)
- the content of the fluorescent light emitting low molecular weight compound is 0.1%
- Ar H1 and Ar H2 each independently represent an aryl group, a monovalent heterocyclic group or a substituted amino group, and these groups optionally have a substituent.
- n H1 represents an integer of 0 to 15.
- L H1 represents an arylene group, a divalent heterocyclic group, or a group represented by — [C (R H11 ) 2 ] n H11 —, and these groups optionally have a substituent. When a plurality of L H1 are present, they may be the same or different.
- n H11 represents an integer of 1 to 10.
- R H11 represents a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, or a monovalent heterocyclic group, and these groups may have a substituent.
- a plurality of R H11 may be the same or different, and may be bonded to each other to form a ring together with the carbon atom to which each is bonded.
- Ar Y1 represents an arylene group, a divalent heterocyclic group, or a divalent group in which at least one arylene group and at least one divalent heterocyclic group are directly bonded, and these This group may have a substituent.
- the group in which the first organic layer is made of a hole transport material, a hole injection material, an electron transport material, an electron injection material, an antioxidant, and a light emitting material different from the fluorescent low molecular weight compound.
- the light emitting device according to any one of [1] to [13], further containing at least one material selected from the above. [15] The light emitting device according to any one of [1] to [14], wherein the second organic layer is a layer provided between the anode and the first organic layer.
- a light emitting device having excellent external quantum efficiency can be provided.
- Me represents a methyl group
- Et represents an ethyl group
- Bu represents a butyl group
- i-Pr represents an isopropyl group
- t-Bu represents a tert-butyl group.
- the hydrogen atom may be a deuterium atom or a light hydrogen atom.
- the solid line representing the bond with the central metal means a covalent bond or a coordinate bond.
- Polymer compound means a polymer having a molecular weight distribution and having a polystyrene-equivalent number average molecular weight of 1 ⁇ 10 3 to 1 ⁇ 10 8 .
- Low molecular weight compound means a compound having no molecular weight distribution and a molecular weight of 1 ⁇ 10 4 or less.
- “Structural unit” means one or more units present in a polymer compound.
- the “alkyl group” may be either linear or branched.
- the number of carbon atoms of the linear alkyl group is usually 1 to 50, preferably 3 to 30, and more preferably 4 to 20, excluding the number of carbon atoms of the substituent.
- the number of carbon atoms of the branched alkyl group is usually 3 to 50, preferably 3 to 30, and more preferably 4 to 20, excluding the number of carbon atoms of the substituent.
- alkyl group examples include methyl group, ethyl group, propyl group, isopropyl group, butyl group, 2-butyl group, isobutyl group, tert-butyl group, pentyl group, isoamyl group, 2-ethylbutyl group, hexyl group, heptyl.
- the alkyl group may have a substituent, for example, a group in which part or all of the hydrogen atoms in the alkyl group are substituted with a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, a fluorine atom, or the like. It may be.
- the alkyl group having a substituent include a trifluoromethyl group, a pentafluoroethyl group, a perfluorobutyl group, a perfluorohexyl group, a perfluorooctyl group, a 3-phenylpropyl group, and 3- (4-methylphenyl).
- a propyl group, a 3- (3,5-di-hexylphenyl) propyl group and a 6-ethyloxyhexyl group can be mentioned.
- the number of carbon atoms of the “cycloalkyl group” is usually 3 to 50, preferably 3 to 30, more preferably 4 to 20, excluding the number of carbon atoms of the substituent.
- Examples of the cycloalkyl group include a cyclopentyl group and a cyclohexyl group.
- the cycloalkyl group may have a substituent.
- part or all of the hydrogen atoms in the cycloalkyl group are alkyl groups, cycloalkyl groups, alkoxy groups, cycloalkoxy groups, aryl groups, fluorine atoms, and the like. It may be a substituted group.
- Examples of the cycloalkyl group having a substituent include a cyclohexylmethyl group and a cyclohexylethyl group.
- Aryl group means an atomic group remaining after removing one hydrogen atom directly bonded to a carbon atom constituting a ring from an aromatic hydrocarbon.
- the number of carbon atoms of the aryl group is usually 6 to 60, preferably 6 to 20, more preferably 6 to 10, not including the number of carbon atoms of the substituent.
- Examples of the aryl group include a phenyl group, 1-naphthyl group, 2-naphthyl group, 1-anthracenyl group, 2-anthracenyl group, 9-anthracenyl group, 1-pyrenyl group, 2-pyrenyl group, 4-pyrenyl group, Examples include 2-fluorenyl group, 3-fluorenyl group, 4-fluorenyl group, 2-phenylphenyl group, 3-phenylphenyl group, and 4-phenylphenyl group.
- the aryl group may have a substituent.
- part or all of the hydrogen atoms in the aryl group are substituted with an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, a fluorine atom, or the like. It may be a radical.
- the “alkoxy group” may be either linear or branched.
- the number of carbon atoms of the straight-chain alkoxy group is usually 1 to 40, preferably 4 to 10, excluding the number of carbon atoms of the substituent.
- the number of carbon atoms of the branched alkoxy group is usually 3 to 40, preferably 4 to 10, excluding the number of carbon atoms of the substituent.
- alkoxy group examples include methoxy group, ethoxy group, propyloxy group, isopropyloxy group, butyloxy group, isobutyloxy group, tert-butyloxy group, pentyloxy group, hexyloxy group, heptyloxy group, octyloxy group, 2 -Ethylhexyloxy group, nonyloxy group, decyloxy group, 3,7-dimethyloctyloxy group and lauryloxy group.
- the alkoxy group may have a substituent, for example, a group in which part or all of the hydrogen atoms in the alkoxy group are substituted with a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, a fluorine atom, or the like. It may be.
- the number of carbon atoms of the “cycloalkoxy group” is usually 3 to 40, preferably 4 to 10, not including the number of carbon atoms of the substituent.
- cycloalkoxy group examples include a cyclopentyloxy group and a cyclohexyloxy group.
- the cycloalkoxy group may have a substituent.
- part or all of the hydrogen atoms in the cycloalkoxy group are alkyl groups, cycloalkyl groups, alkoxy groups, cycloalkoxy groups, aryl groups, fluorine atoms, and the like. It may be a substituted group.
- Aryloxy group means an atomic group in which one aryl group is bonded to an oxygen atom.
- the number of carbon atoms of the aryloxy group is usually 6 to 60, preferably 6 to 48, not including the number of carbon atoms of the substituent.
- aryloxy group examples include a phenoxy group, a 1-naphthyloxy group, a 2-naphthyloxy group, a 1-anthracenyloxy group, a 9-anthracenyloxy group, and a 1-pyrenyloxy group.
- the aryloxy group may have a substituent. For example, part or all of the hydrogen atoms in the aryloxy group are substituted with an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, a fluorine atom, or the like. It may be a group.
- the “p-valent heterocyclic group” (p represents an integer of 1 or more) is p of hydrogen atoms directly bonded to a carbon atom or a hetero atom constituting a ring from a heterocyclic compound. This means the remaining atomic group excluding the hydrogen atom. Among the p-valent heterocyclic groups, it is the remaining atomic group obtained by removing p hydrogen atoms from the hydrogen atoms directly bonded to the carbon atoms or heteroatoms constituting the ring from the aromatic heterocyclic compound. A “p-valent aromatic heterocyclic group” is preferable.
- Aromatic heterocyclic compounds '' are oxadiazole, thiadiazole, thiazole, oxazole, thiophene, pyrrole, phosphole, furan, pyridine, pyrazine, pyrimidine, triazine, pyridazine, quinoline, isoquinoline, carbazole, dibenzophosphole, etc.
- a compound in which the ring itself exhibits aromaticity and a compound in which an aromatic ring is condensed to a heterocyclic ring, even if the heterocyclic ring itself does not exhibit aromaticity, such as phenoxazine, phenothiazine, dibenzoborol, dibenzosilol, and benzopyran Means.
- the number of carbon atoms of the monovalent heterocyclic group is usually 2 to 60, preferably 4 to 20, excluding the number of carbon atoms of the substituent.
- Examples of the monovalent heterocyclic group include thienyl group, pyrrolyl group, furyl group, pyridyl group, piperidinyl group, quinolinyl group, isoquinolinyl group, pyrimidinyl group, and triazinyl group.
- the monovalent heterocyclic group may have a substituent.
- part or all of the hydrogen atoms in the monovalent heterocyclic group are an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, and the like. It may be a substituted group.
- Halogen atom means a fluorine atom, a chlorine atom, a bromine atom or an iodine atom.
- the “amino group” may have a substituent, and a substituted amino group is preferable.
- a substituent which an amino group has an alkyl group, a cycloalkyl group, an aryl group, or a monovalent heterocyclic group is preferable.
- substituted amino group examples include a dialkylamino group, a dicycloalkylamino group, and a diarylamino group.
- Specific examples of the substituted amino group include dimethylamino group, diethylamino group, diphenylamino group, bis (4-methylphenyl) amino group, bis (4-tert-butylphenyl) amino group, and bis (3,5- A di-tert-butylphenyl) amino group.
- alkenyl group may be either linear or branched.
- the number of carbon atoms of the straight chain alkenyl group is usually 2 to 30, preferably 3 to 20, not including the carbon atoms of the substituent.
- the number of carbon atoms of the branched alkenyl group is usually 3 to 30, preferably 4 to 20, not including the carbon atoms of the substituent.
- the number of carbon atoms of the “cycloalkenyl group” is usually 3 to 30, preferably 4 to 20, not including the number of carbon atoms of the substituent.
- alkenyl group and cycloalkenyl group examples include a vinyl group, 1-propenyl group, 2-propenyl group, 2-butenyl group, 3-butenyl group, 3-pentenyl group, 4-pentenyl group, 1-hexenyl group, 5 -Hexenyl group and 7-octenyl group.
- the alkenyl group may have a substituent, for example, a group in which part or all of the hydrogen atoms in the alkenyl group are substituted with a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, a fluorine atom, or the like. It may be.
- the cycloalkenyl group may have a substituent.
- a part or all of the hydrogen atoms in the cycloalkenyl group are alkyl groups, cycloalkyl groups, alkoxy groups, cycloalkoxy groups, aryl groups, fluorine atoms. It may be a group substituted with or the like.
- alkynyl group may be either linear or branched.
- the number of carbon atoms of the alkynyl group is usually 2 to 20, preferably 3 to 20, not including the carbon atom of the substituent.
- the number of carbon atoms of the branched alkynyl group is usually from 4 to 30, and preferably from 4 to 20, not including the carbon atom of the substituent.
- the number of carbon atoms of the “cycloalkynyl group” is usually 4 to 30, preferably 4 to 20, not including the carbon atom of the substituent.
- alkynyl group and cycloalkynyl group examples include ethynyl group, 1-propynyl group, 2-propynyl group, 2-butynyl group, 3-butynyl group, 3-pentynyl group, 4-pentynyl group, 1-hexynyl group and 5 -A hexynyl group is mentioned.
- the alkynyl group may have a substituent, for example, a group in which some or all of the hydrogen atoms in the alkynyl group are substituted with a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, a fluorine atom, or the like.
- the cycloalkynyl group may have a substituent.
- a part or all of the hydrogen atoms in the cycloalkynyl group are alkyl groups, cycloalkyl groups, alkoxy groups, cycloalkoxy groups, aryl groups, fluorine atoms. It may be a group substituted with or the like.
- “Arylene group” means an atomic group remaining after removing two hydrogen atoms directly bonded to a carbon atom constituting a ring from an aromatic hydrocarbon.
- the number of carbon atoms of the arylene group is usually 6 to 60, preferably 6 to 30, and more preferably 6 to 18, excluding the number of carbon atoms of the substituent.
- arylene group examples include a phenylene group, a naphthalenediyl group, an anthracenediyl group, a phenanthenediyl group, a dihydrophenanthenediyl group, a naphthacenediyl group, a fluorenediyl group, a pyrenediyl group, a perylenediyl group, and a chrysenediyl group.
- the arylene group may have a substituent.
- part or all of the hydrogen atoms in the arylene group are substituted with an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, a fluorine atom, or the like. It may be a radical.
- the arylene group is preferably a group represented by formula (A-1) to formula (A-20).
- the arylene group includes a group in which a plurality of these groups are bonded.
- R and R a each independently represent a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group, or a monovalent heterocyclic group.
- R and R a there are a plurality each may be the same or different, bonded R a each other to each other, may form a ring together with the atoms bonded thereto.
- the number of carbon atoms of the divalent heterocyclic group is usually 2 to 60, preferably 3 to 20, more preferably 4 to 15, excluding the number of carbon atoms of the substituent.
- divalent heterocyclic group examples include pyridine, diazabenzene, triazine, azanaphthalene, diazanaphthalene, carbazole, dibenzofuran, dibenzothiophene, dibenzosilole, phenoxazine, phenothiazine, acridine, dihydroacridine, furan, thiophene, azole, Examples thereof include divalent groups obtained by removing two hydrogen atoms from a hydrogen atom directly bonded to a carbon atom or a hetero atom constituting a ring from a heterocyclic compound such as diazole or triazole.
- the divalent heterocyclic group may have a substituent.
- some or all of the hydrogen atoms in the divalent heterocyclic group are alkyl groups, cycloalkyl groups, alkoxy groups, cycloalkoxy groups, aryls. It may be a group substituted with a group, a fluorine atom or the like.
- the divalent heterocyclic group is preferably a group represented by formula (AA-1) to formula (AA-34).
- the divalent heterocyclic group includes a group in which a plurality of these groups are bonded.
- R and R a represent the same meaning as described above.
- crosslinking group is a group capable of generating a new bond by being subjected to heating, ultraviolet irradiation, near ultraviolet irradiation, visible light irradiation, infrared irradiation, radical reaction, etc. This is a group represented by the formula (XL-1) to (XL-17) of the group A group.
- Examples of the “substituent” include a halogen atom, a cyano group, an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group, an alkoxy group, a cycloalkoxy group, an aryloxy group, an amino group, a substituted amino group, Examples include alkenyl group, cycloalkenyl group, alkynyl group and cycloalkynyl group.
- the substituent may be a crosslinking group.
- the light emitting device includes an anode, a cathode, a first organic layer provided between the anode and the cathode, and a first organic layer provided adjacent to the first organic layer between the anode and the cathode. 2 organic layers.
- the first organic layer is a layer containing a fluorescent light-emitting low molecular compound
- the second organic layer is a layer containing a crosslinked product of a polymer compound containing a crosslinked structural unit having a crosslinking group.
- Examples of the method for forming the first organic layer and the second organic layer include a dry method such as a vacuum deposition method and a wet method such as a spin coating method and an ink jet printing method, and a wet method is preferable.
- first ink an ink for a first organic layer described below
- the second organic layer is formed by a wet method, it is preferable to use an ink for a second organic layer described below (hereinafter also referred to as “second ink”).
- second ink an ink for a second organic layer described below
- the polymer compound of the second organic layer described later contained in the second organic layer can be crosslinked by heating or light irradiation. It is preferable to crosslink the polymer compound of the second organic layer described later contained in the second organic layer.
- the second organic layer is contained in the second organic layer in a state where the polymer compound of the second organic layer described later is crosslinked (crosslinked product of the polymer compound of the second organic layer described later), the second organic layer Is substantially insolubilized in the solvent. Therefore, the second organic layer can be suitably used for stacking light emitting elements.
- the heating temperature for crosslinking is usually 25 to 300 ° C, preferably 50 to 250 ° C, more preferably 150 ° C to 200 ° C, and still more preferably 170 ° C to 190 ° C.
- the heating time for crosslinking is usually 0.1 to 1000 minutes, preferably 0.5 to 500 minutes, more preferably 1 to 120 minutes, and further preferably 30 to 90 minutes. .
- the types of light used for light irradiation are, for example, ultraviolet light, near ultraviolet light, and visible light.
- Examples of the analysis method of the components contained in the first organic layer or the second organic layer include chemical separation analysis methods such as extraction, infrared spectroscopy (IR), nuclear magnetic resonance spectroscopy (NMR), Examples include instrumental analysis methods such as mass spectrometry (MS), and analysis methods combining chemical separation analysis methods and instrumental analysis methods.
- chemical separation analysis methods such as extraction, infrared spectroscopy (IR), nuclear magnetic resonance spectroscopy (NMR)
- Examples include instrumental analysis methods such as mass spectrometry (MS), and analysis methods combining chemical separation analysis methods and instrumental analysis methods.
- insoluble Component components that are substantially insoluble in the organic solvent
- dissolved component components that dissolves in an organic solvent
- insoluble components can be analyzed by infrared spectroscopy or nuclear magnetic resonance spectroscopy, and dissolved components can be analyzed by nuclear magnetic resonance spectroscopy or mass spectrometry.
- the first organic layer is a layer containing a fluorescent light-emitting low molecular compound.
- the first organic layer may contain one kind of fluorescent light-emitting low molecular weight compound, or two or more kinds.
- Fluorescent low molecular weight compound usually means a low molecular weight compound that exhibits fluorescent luminescence at room temperature (25 ° C.), and preferably a low molecular weight compound that emits light from a singlet excited state at room temperature. .
- the maximum peak wavelength of the emission spectrum of the fluorescent low molecular weight compound is usually 380 nm or more and 750 nm or less, preferably 380 nm or more and 570 nm or less, more preferably 390 nm or more and 540 nm or less, and further preferably 400 nm or more and 495 nm or less. Especially preferably, it is 420 nm or more and 480 nm or less.
- the maximum peak wavelength of the emission spectrum of a compound is determined by dissolving the compound in an organic solvent such as xylene, toluene, chloroform, tetrahydrofuran, and preparing a dilute solution (1 ⁇ 10 ⁇ 6 to 1 ⁇ 10 ⁇ 3 It can be evaluated by measuring the PL spectrum of the diluted solution at room temperature.
- an organic solvent such as xylene, toluene, chloroform, tetrahydrofuran
- the fluorescent light-emitting low molecular weight compound is preferably a compound represented by the formula (B).
- n 1B represents an integer of 0 to 15, preferably an integer of 1 to 8, more preferably an integer of 1 to 6, still more preferably an integer of 1 to 4, and particularly preferably 2 to 4 Is an integer.
- Ar 1B represents an aromatic hydrocarbon group or an aromatic heterocyclic group, and these groups optionally have a substituent.
- the number of carbon atoms of the aromatic hydrocarbon group is usually 6 to 60, preferably 6 to 40, more preferably 6 to 30, excluding the number of carbon atoms of the substituent. More preferably, it is 6-20.
- Examples of the aromatic hydrocarbon group in Ar 1B include benzene ring, biphenyl ring, naphthalene ring, anthracene ring, phenanthrene ring, dihydrophenanthrene ring, triphenylene ring, naphthacene ring, fluorene ring, spirobifluorene ring, pyrene ring, perylene. And a group formed by removing one or more hydrogen atoms directly bonded to the carbon atoms constituting the ring from the ring, chrysene ring, indene ring, fluoranthene ring, benzofluoranthene ring or acenaphthofluoranthene ring.
- the aromatic hydrocarbon group is preferably a benzene ring, biphenyl ring, naphthalene ring, anthracene ring, phenanthrene ring, dihydrophenanthrene ring, triphenylene ring, naphthacene ring, fluorene ring, spirobifluorene ring, pyrene ring, perylene ring, chrysene A group formed by removing one or more hydrogen atoms directly bonded to carbon atoms constituting a ring from a ring, a fluoranthene ring, a benzofluoranthene ring or an acenaphthofluoranthene ring, and more preferably a benzene ring or biphenyl Rings from ring, naphthalene ring, anthracene ring, phenanthrene ring, dihydrophenanthrene ring, fluorene ring, spirobiflu
- the number of carbon atoms of the aromatic heterocyclic group is usually 2 to 60, preferably 3 to 30, and more preferably 3 to 20, excluding the number of carbon atoms of the substituent.
- Examples of the aromatic heterocyclic group in Ar 1B include a pyrrole ring, a diazole ring, a triazole ring, a pyridine ring, a diazabenzene ring, a triazine ring, an azanaphthalene ring, a diazanaphthalene ring, a triazanaphthalene ring, an indole ring, and a benzodi ring.
- the aromatic heterocyclic group is preferably a diazole ring, triazole ring, pyridine ring, diazabenzene ring, triazine ring, indole ring, benzodiazole ring, benzotriazole ring, carbazole ring, dibenzofuran ring, dibenzothiophene ring, phenoxazine ring.
- the substituent which Ar 1B may have is preferably a halogen atom, a cyano group, an aryloxy group or an amino group, more preferably a fluorine atom or a cyano group. These groups may further have a substituent.
- Examples and preferred ranges of substituents that Ar 1B may further have are the same as examples and preferred ranges of substituents that R 1B described later may have. .
- Ar 1B is preferably an aromatic hydrocarbon group which may have a substituent.
- R 1B represents an alkyl group, a cycloalkyl group, an alkoxy group, cycloalkoxy group, an aryl group, a monovalent heterocyclic group, a substituted amino group, an alkenyl group, a cycloalkenyl group, an alkynyl group or a cycloalkynyl group, these The group may have a substituent.
- R 1B is preferably an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, a monovalent heterocyclic group, a substituted amino group, an alkenyl group or a cycloalkenyl group, more preferably an alkyl group.
- Cycloalkyl group aryl group, monovalent heterocyclic group, substituted amino group, alkenyl group or cycloalkenyl group, more preferably alkyl group, cycloalkyl group, aryl group, substituted amino group, alkenyl group or cyclo
- An alkenyl group particularly preferably an aryl group, a substituted amino group or an alkenyl group, and particularly preferably an aryl group or a substituted amino group. These groups may have a substituent.
- R 1B is an aryl group
- the number of carbon atoms of the aryl group is usually 6 to 60, preferably 6 to 40, more preferably 6 to 30 excluding the number of carbon atoms of the substituent. More preferably, it is 6-14.
- R 1B is an aryl group
- examples of the aryl group include a benzene ring, naphthalene ring, anthracene ring, phenanthrene ring, triphenylene ring, dihydrophenanthrene ring, naphthacene ring, fluorene ring, spirobifluorene ring, pyrene ring, And a group formed by removing one hydrogen atom directly bonded to the carbon atom constituting the ring from the perylene ring, chrysene ring, indene ring, fluoranthene ring and benzofluoranthene ring.
- the aryl group is preferably a carbon atom that forms a ring from a benzene ring, naphthalene ring, anthracene ring, phenanthrene ring, dihydrophenanthrene ring, fluorene ring, spirobifluorene ring, pyrene ring, fluoranthene ring or benzofluoranthene ring.
- a group formed by removing one hydrogen atom directly bonded to the ring is composed of a benzene ring, naphthalene ring, anthracene ring, fluorene ring, spirobifluorene ring, fluoranthene ring or benzofluoranthene ring
- a group formed by removing one hydrogen atom directly bonded to a carbon atom more preferably, more preferably from a benzene ring, a naphthalene ring, a fluorene ring or a spirobifluorene ring, directly to the carbon atom constituting the ring.
- a group formed by removing one hydrogen atom to be bonded particularly preferably A phenyl group or a naphthyl group. These groups may further have a substituent.
- R 1B is a monovalent heterocyclic group
- the number of carbon atoms of the monovalent heterocyclic group is usually 2 to 60, preferably 3 to 30, not including the number of carbon atoms of the substituent. Yes, more preferably 3-20.
- R 1B is a monovalent heterocyclic group
- examples of the monovalent heterocyclic group include a pyrrole ring, a diazole ring, a triazole ring, a pyridine ring, a diazabenzene ring, a triazine ring, an azanaphthalene ring, and a diazanaphthalene.
- Ring triazanaphthalene ring, indole ring, carbazole ring, azacarbazole ring, diazacarbazole ring, dibenzofuran ring, dibenzothiophene ring, phenoxazine ring, phenothiazine ring, acridine ring, 9,10-dihydroacridine ring, acridone ring, Examples thereof include a group formed by removing one hydrogen atom directly bonded to a carbon atom or a hetero atom constituting a ring from a phenazine ring and a 5,10-dihydrophenazine ring.
- the monovalent heterocyclic group is preferably a pyridine ring, diazabenzene ring, triazine ring, azanaphthalene ring, diazanaphthalene ring, carbazole ring, azacarbazole ring, diazacarbazole ring, dibenzofuran ring, dibenzothiophene ring, phenoxazine.
- These groups may further have a substituent.
- R 1B is a substituted amino group
- the amino group preferably has an aryl group or a monovalent heterocyclic group, more preferably an aryl group, and these groups may further have a substituent.
- Examples and preferred ranges of the aryl group in the substituent that the amino group has are the same as examples and preferred ranges of the aryl group in R 1B .
- Examples and preferred ranges of the monovalent heterocyclic group in the substituent that the amino group has are the same as examples and preferred ranges of the monovalent heterocyclic group in R 1B .
- R 1B may have, an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group, an alkoxy group, a cycloalkoxy group, an aryloxy group, a substituted amino group, or a halogen is preferable.
- An atom more preferably an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, a monovalent heterocyclic group or a substituted amino group, still more preferably an alkyl group, a cycloalkyl group, an aryl Group or a monovalent heterocyclic group, particularly preferably an alkyl group, a cycloalkyl group or an aryl group, and particularly preferably an alkyl group or a cycloalkyl group.
- These groups may further have a substituent.
- aryl group, monovalent heterocyclic group and substituted amino group in the substituent that R 1B may have and preferred ranges thereof are the aryl group, monovalent heterocyclic group and substituted amino group in R 1B , respectively. The same as the examples and preferred ranges.
- the substituent which R 1B may have may further have, preferably an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group, an alkoxy group, a cycloalkoxy group , An aryloxy group, a substituted amino group or a halogen atom, more preferably an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, and still more preferably an alkyl group or a cycloalkyl group. These groups may further have a substituent.
- Examples and preferred ranges of the aryl group, monovalent heterocyclic group and substituted amino group in the substituent that the substituent which R 1B may have may further have, respectively, are the aryl group in R 1B , Examples of the monovalent heterocyclic group and substituted amino group are the same as the preferred range.
- the maximum peak wavelength of the emission spectrum of the compound represented by the formula (B) is a short wavelength, when there are a plurality of R 1B , it is preferable that they are bonded to each other and do not form a ring with the atoms to which they are bonded.
- Examples of the fluorescent light-emitting low-molecular compound include compounds represented by the following formula.
- Fluorescent low molecular weight compounds are available from Aldrich, Luminescence Technology Corp. , AK Scientific, etc.
- International Publication No. 2007/100010, International Publication No. 2008/059713, International Publication No. 2011/012212, International Publication No. 2012/096263, International Publication No. 2006/025273, International Publication No. 2006 / 030527 can be synthesized according to the method described in US Pat.
- the first organic layer is composed of a fluorescent light emitting low molecular weight compound, a hole injection property, a hole transport property, an electron injection property, and an electron transport property.
- a layer containing a host material having at least one function selected from the group is preferable.
- the host material may be contained singly or in combination of two or more.
- the content of the fluorescent light-emitting low molecular compound is 100 as the total of the fluorescent light-emitting low molecular compound and the host material.
- mass parts it is usually 0.05 to 80 parts by mass, preferably 0.1 to 50 parts by mass, more preferably 1 to 30 parts by mass, and further preferably 5 to 15 parts by mass. is there.
- the lowest excited singlet state (S 1 ) of the host material is the external quantum of the light emitting device according to this embodiment.
- S 1 equivalent energy level possessed by the fluorescing low molecular compound or is preferably a higher energy level. That is, the maximum peak wavelength of the emission spectrum of the host material is excellent in the external quantum efficiency of the light emitting device according to the present embodiment. Preferably there is.
- the light-emitting element according to the present embodiment can be manufactured by a solution coating process, so that the host material has solubility in a solvent capable of dissolving the fluorescent light-emitting low-molecular compound contained in the first organic layer. It is preferable that it is shown.
- Host materials are classified into low molecular compounds and high molecular compounds.
- the below-mentioned hole transport material and the below-mentioned electron transport material are mentioned, for example.
- Low molecular host A low molecular compound (hereinafter also referred to as “low molecular host”) that is preferable as a host material will be described.
- the low molecular host is preferably a compound represented by the formula (FH-1).
- Ar H1 and Ar H2 are preferably an aryl group or a monovalent heterocyclic group, and more preferably an aryl group. These groups may have a substituent.
- the number of carbon atoms of the aryl group is usually 6 to 60, preferably 6 to 30, and more preferably not including the number of carbon atoms of the substituent. 6 to 20, more preferably 6 to 14.
- Ar H1 and Ar H2 are aryl groups
- examples of the aryl group include benzene ring, naphthalene ring, anthracene ring, phenanthrene ring, triphenylene ring, dihydrophenanthrene ring, naphthacene ring, fluorene ring, spirobifluorene ring, Examples thereof include a group formed by removing one hydrogen atom directly bonded to a carbon atom constituting a ring from a pyrene ring, a perylene ring, a chrysene ring, an indene ring, a fluoranthene ring or a benzofluoranthene ring.
- the aryl group is preferably a hydrogen atom directly bonded to a carbon atom constituting the ring from a benzene ring, naphthalene ring, anthracene ring, phenanthrene ring, dihydrophenanthrene ring, fluorene ring, spirobifluorene ring, pyrene ring or chrysene ring. More preferably, one hydrogen atom directly bonded to the carbon atom constituting the ring is selected from a benzene ring, naphthalene ring, anthracene ring, pyrene ring, fluorene ring or spirobifluorene ring.
- a group to be excluded more preferably a phenyl group, a naphthyl group or an anthracenyl group, and particularly preferably a phenyl group or a naphthyl group. These groups may further have a substituent.
- the number of carbon atoms of the monovalent heterocyclic group is usually 2 to 60, preferably 3 to 60, not including the number of carbon atoms of the substituent. -30, more preferably 3-20.
- examples of the monovalent heterocyclic group include a pyrrole ring, diazole ring, triazole ring, pyridine ring, diazabenzene ring, triazine ring, azanaphthalene ring, Diazanaphthalene ring, triazanaphthalene ring, indole ring, benzodiazole ring, benzotriazole ring, carbazole ring, azacarbazole ring, diazacarbazole ring, dibenzofuran ring, dibenzothiophene ring, phenoxazine ring, phenothiazine ring, acridine ring , 9,10-dihydroacridine ring, acridone ring, phenazine ring and 5,10-dihydrophenazine ring, a group obtained by removing one hydrogen atom directly bonded to a carbon atom
- the monovalent heterocyclic group is preferably a diazole ring, a triazole ring, a pyridine ring, a diazabenzene ring, a triazine ring, an indole ring, a benzodiazole ring, a benzotriazole ring, a carbazole ring, a dibenzofuran ring, a dibenzothiophene ring, or a phenoxazine.
- the substituent that the amino group has is preferably an aryl group or a monovalent heterocyclic group, more preferably an aryl group, and these groups further have a substituent. It may be. Examples and preferred ranges of the aryl group in the substituent that the amino group has are the same as examples and preferred ranges of the aryl group in Ar H1 and Ar H2 . Examples and preferred ranges of the monovalent heterocyclic group in the substituent that the amino group has are the same as examples and preferred ranges of the monovalent heterocyclic group in Ar H1 and Ar H2 .
- Ar H1 and Ar H2 may have is preferably an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group, an alkoxy group, a cycloalkoxy group, an aryloxy group, or a substituted amino group.
- halogen atom more preferably an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, a monovalent heterocyclic group or a substituted amino group, and still more preferably an alkyl group or a cycloalkyl group A group, an aryl group or a monovalent heterocyclic group, particularly preferably an alkyl group, a cycloalkyl group or an aryl group. These groups may further have a substituent.
- Examples of the aryl group, monovalent heterocyclic group and substituted amino group in the substituent that Ar H1 and Ar H2 may have are the aryl group and monovalent complex in Ar H1 and Ar H2 , respectively.
- the examples and preferred ranges of the cyclic group and the substituted amino group are the same.
- substituent that the substituent that Ar H1 and Ar H2 may have further may preferably have, an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group, an alkoxy group, A cycloalkoxy group, an aryloxy group, a substituted amino group or a halogen atom, more preferably an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, a monovalent heterocyclic group or a substituted amino group.
- it is an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, particularly preferably an alkyl group or a cycloalkyl group, and these groups may further have a substituent.
- alkyl group preferably a cycloalkyl group, an aryl group or a monovalent heterocyclic group, particularly preferably an alkyl group or a cycloalkyl group, and these groups may further have a substituent.
- Examples of the aryl group, monovalent heterocyclic group and substituted amino group in the substituent that the substituent that Ar H1 and Ar H2 may further have may further have Ar H1 and Examples of the aryl group, monovalent heterocyclic group and substituted amino group in Ar H2 are the same as the preferred range.
- n H1 is preferably an integer of 0 to 10, more preferably an integer of 1 to 5, and still more preferably an integer of 1 to 3.
- L H1 is preferably an arylene group or a divalent heterocyclic group, and more preferably an arylene group.
- Examples and preferred ranges of the substituent that L H1 may have are the same as examples and preferred ranges of the substituent that Ar H1 and Ar H2 may have.
- the arylene group in L H1 is preferably a group represented by the formula (A-1) to the formula (A-14) or the formula (A-17) to the formula (A-20), more preferably the formula A group represented by formula (A-1) to formula (A-9), formula (A-11) to formula (A-14), formula (A-19) or formula (A-20), more preferably Is a group represented by formula (A-1) to formula (A-7), formula (A-9), formula (A-11) to formula (A-14), or formula (A-19) Particularly preferred are groups represented by formula (A-1) to formula (A-6), formula (A-11) or formula (A-12).
- Divalent heterocyclic groups in L H1 are preferably of the formula (AA-1) ⁇ formula (AA-6), formula (AA-10) ⁇ formula (AA-22) or formula (AA-24) ⁇ Formula And more preferably a group represented by formula (AA-1) to formula (AA-4), formula (AA-10) to formula (AA-15), formula (AA-18) ) To formula (AA-21) or formula (AA-27) to formula (AA-34), more preferably formula (AA-1) to formula (AA-4), formula (AA) It is a group represented by AA-10) to formula (AA-15) or formula (AA-27) to formula (AA-32).
- n H11 is preferably an integer of 1 to 5, more preferably an integer of 1 to 3, and even more preferably 1.
- R H11 is preferably a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, more preferably a hydrogen atom, an alkyl group or a cycloalkyl group, and a hydrogen atom or an alkyl group. More preferably. These groups may have a substituent.
- Examples and preferred ranges of the substituent that R H11 may have are the same as examples and preferred ranges of the substituent that Ar H1 and Ar H2 may have.
- Examples of the compound represented by the formula (FH-1) include compounds represented by the following formula.
- Polymer host A polymer compound (hereinafter also referred to as “polymer host”) preferable as a host material will be described.
- the polymer host is preferably a polymer compound containing a structural unit represented by the formula (Y).
- the arylene group represented by Ar Y1 is preferably formula (A-1), formula (A-6), formula (A-7), formula (A-9) to formula (A-11), formula (A-11), -13) or a group represented by formula (A-19), more preferably formula (A-1), formula (A-7), formula (A-9), formula (A-11) or formula A group represented by (A-19); These groups may have a substituent.
- the divalent heterocyclic group represented by Ar Y1 is preferably the formula (AA-4), formula (AA-10), formula (AA-13), formula (AA-15), formula (AA-18) Or a group represented by formula (AA-20), more preferably a group represented by formula (AA-4), formula (AA-10), formula (AA-18) or formula (AA-20) It is. These groups may have a substituent.
- Preferred range and more preferred range of arylene group and divalent heterocyclic group in a divalent group in which at least one arylene group represented by Ar Y1 and at least one divalent heterocyclic group are directly bonded. are respectively the same as the preferred range and more preferred range of the arylene group and divalent heterocyclic group represented by Ar Y1 described above.
- the divalent group in which at least one arylene group represented by Ar Y1 and at least one divalent heterocyclic group are directly bonded at least represented by Ar X2 and Ar X4 in the formula (X) Examples thereof include the same divalent groups in which one kind of arylene group and at least one kind of divalent heterocyclic group are directly bonded.
- the substituent that the group represented by Ar Y1 may have is preferably an alkyl group, a cycloalkyl group, or an aryl group. These groups may further have a substituent.
- Examples of the structural unit represented by the formula (Y) include structural units represented by the formulas (Y-1) to (Y-7), and the external quantum efficiency of the light emitting device according to the present embodiment. From the viewpoint, it is preferably a structural unit represented by the formula (Y-1) or the formula (Y-2). From the viewpoint of the electron transport property of the polymer host, the formula (Y-3) or the formula From the viewpoint of the hole transport property of the polymer host, it is preferably a structural unit represented by formula (Y-5) to formula (Y-7). .
- R Y1 represents a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, or a monovalent heterocyclic group, and these groups may have a substituent.
- a plurality of R Y1 may be the same or different, and adjacent R Y1 may be bonded to each other to form a ring together with the carbon atom to which each is bonded.
- R Y1 is preferably a hydrogen atom, an alkyl group, a cycloalkyl group, or an aryl group. These groups may have a substituent.
- the structural unit represented by the formula (Y-1) is preferably a structural unit represented by the formula (Y-1 ′).
- R Y11 represents an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, or a monovalent heterocyclic group, and these groups may have a substituent.
- a plurality of R Y11 may be the same or different.
- R Y11 is preferably an alkyl group, a cycloalkyl group, or an aryl group, and more preferably an alkyl group or a cycloalkyl group. These groups may have a substituent.
- R Y1 represents the same meaning as described above.
- X Y1 is, -C (R Y2) 2 -
- R Y2 represents a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, or a monovalent heterocyclic group, and these groups may have a substituent.
- a plurality of R Y2 may be the same or different, and R Y2 may be bonded to each other to form a ring together with the carbon atom to which each is bonded.
- R Y2 is preferably an alkyl group, a cycloalkyl group, an aryl group, or a monovalent heterocyclic group, more preferably an alkyl group, a cycloalkyl group, or an aryl group, and these groups have a substituent. May be.
- the combination of two R Y2 in the group represented by —C (R Y2 ) 2 — in X Y1 is preferably both an alkyl group or a cycloalkyl group, both an aryl group, and both monovalent complex
- One is an alkyl group or a cycloalkyl group and the other is an aryl group or a monovalent heterocyclic group, more preferably one is an alkyl group or a cycloalkyl group and the other is an aryl group.
- These groups may have a substituent.
- R Y2 s may be bonded to each other to form a ring together with the atoms to which they are bonded, and when R Y2 forms a ring, the group represented by —C (R Y2 ) 2 — Is preferably a group represented by the formula (Y-A1) to the formula (Y-A5), more preferably a group represented by the formula (Y-A4). These groups may have a substituent.
- R Y2 C (R Y2) - 2 pieces of combinations of R Y2 in the group represented by is preferably both an alkyl group or a cycloalkyl group, or, one is an alkyl group Alternatively, a cycloalkyl group and the other is an aryl group, and these groups optionally have a substituent.
- R Y2 in the group represented by —C (R Y2 ) 2 —C (R Y2 ) 2 — are preferably an alkyl group or a substituent which may have a substituent. It is a cycloalkyl group that may have.
- a plurality of R Y2 may be bonded to each other to form a ring together with the atoms to which each is bonded.
- R Y2 forms a ring —C (R Y2 ) 2 —C (R Y2 ) 2 —
- the group represented is preferably a group represented by the formula (Y-B1) to the formula (Y-B5), and more preferably a group represented by the formula (Y-B3). These groups may have a substituent.
- R Y2 represents the same meaning as described above.
- the structural unit represented by the formula (Y-2) is preferably a structural unit represented by the formula (Y-2 ′).
- R Y1 and X Y1 represent the same meaning as described above.
- R Y1 represents the same meaning as described above.
- R Y3 represents a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, or a monovalent heterocyclic group, and these groups may have a substituent.
- R Y3 is preferably an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group or a monovalent heterocyclic group, more preferably an aryl group. These groups may have a substituent.
- R Y1 represents the same meaning as described above.
- R Y4 represents a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, or a monovalent heterocyclic group, and these groups optionally have a substituent.
- R Y4 is preferably an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group or a monovalent heterocyclic group, and more preferably an aryl group. These groups may have a substituent.
- Examples of the structural unit represented by the formula (Y) include structural units represented by the formula (Y-11) to the formula (Y-56), and preferably the formula (Y-11) to the formula (Y Y-55).
- the structural unit represented by the formula (Y), in which Ar Y1 is an arylene group, is more excellent in the external quantum efficiency of the light emitting device according to the present embodiment.
- the amount is preferably 10 to 100 mol%, more preferably 50 to 100 mol%, based on the total amount.
- the structural unit which is a group is preferably 0.5 to 40 mol%, more preferably 3%, based on the total amount of the structural units contained in the polymer host, since the charge transport property of the polymer host is excellent. ⁇ 30 mol%.
- the polymer host is excellent in hole transportability, it is preferable that the polymer host further includes a structural unit represented by the formula (X).
- a X1 and a X2 each independently represent an integer of 0 or more.
- Ar X1 and Ar X3 each independently represent an arylene group or a divalent heterocyclic group, and these groups optionally have a substituent.
- Ar X2 and Ar X4 each independently represent an arylene group, a divalent heterocyclic group, or a divalent group in which at least one arylene group and at least one divalent heterocyclic group are directly bonded to each other. And these groups may have a substituent.
- Ar X2 and Ar X4 When a plurality of Ar X2 and Ar X4 are present, they may be the same or different.
- R X1 , R X2 and R X3 each independently represent a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, and these groups may have a substituent.
- R X2 and R X3 may be the same or different.
- a X1 is preferably an integer of 2 or less, more preferably 1, since the external quantum efficiency of the light emitting device according to this embodiment is more excellent.
- a X2 is preferably an integer of 2 or less, more preferably 0, because the external quantum efficiency of the light emitting device according to this embodiment is more excellent.
- R X1 , R X2 and R X3 are preferably an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, and more preferably an aryl group. These groups may have a substituent.
- the arylene group represented by Ar X1 and Ar X3 is preferably a group represented by the formula (A-1) or the formula (A-9), more preferably a group represented by the formula (A-1). It is. These groups may have a substituent.
- the divalent heterocyclic group represented by Ar X1 and Ar X3 is preferably represented by Formula (AA-1), Formula (AA-2), or Formula (AA-7) to Formula (AA-26). It is a group. These groups may have a substituent.
- Ar X1 and Ar X3 are preferably an arylene group which may have a substituent.
- the arylene group represented by Ar X2 and Ar X4 is preferably represented by formula (A-1), formula (A-6), formula (A-7), formula (A-9) to formula (A-11) or A group represented by formula (A-19); These groups may have a substituent.
- the preferred range of the divalent heterocyclic group represented by Ar X2 and Ar X4 is the same as the preferred range of the divalent heterocyclic group represented by Ar X1 and Ar X3 .
- Preferred ranges of the arylene group and the divalent heterocyclic group in the divalent group in which at least one arylene group represented by Ar X2 and Ar X4 and the at least one divalent heterocyclic group are directly bonded More preferable ranges are the same as the preferable range and the more preferable range of the arylene group and divalent heterocyclic group represented by Ar X1 and Ar X3 , respectively.
- Examples of the divalent group in which at least one arylene group represented by Ar X2 and Ar X4 and at least one divalent heterocyclic group are directly bonded include groups represented by the following formulae: These may have a substituent.
- R XX represents a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group, or a monovalent heterocyclic group, and these groups may have a substituent.
- Ar X2 and Ar X4 are preferably an arylene group which may have a substituent.
- the substituent that the group represented by Ar X1 to Ar X4 and R X1 to R X3 may have is preferably an alkyl group, a cycloalkyl group, or an aryl group. These groups may further have a substituent.
- the structural unit represented by the formula (X) is preferably a structural unit represented by the formula (X-1) to the formula (X-7), more preferably the formula (X-3) to the formula (X -7), more preferably structural units represented by formulas (X-3) to (X-6).
- R X4 and R X5 each independently represent a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, an aryloxy group, a halogen atom, a monovalent heterocyclic group, or a cyano group. These groups may have a substituent.
- a plurality of R X4 may be the same or different.
- a plurality of R X5 may be the same or different, and adjacent R X5 may be bonded to each other to form a ring together with the carbon atom to which each is bonded.
- the structural unit represented by the formula (X) has excellent hole transportability, it is preferably 0.1 to 50 mol%, more preferably based on the total amount of the structural units contained in the polymer host. It is 1 to 40 mol%, and more preferably 5 to 30 mol%.
- Examples of the structural unit represented by the formula (X) include structural units represented by the formula (X1-1) to the formula (X1-19), preferably the formula (X1-6) to the formula (X1 -14).
- polymer host examples include polymer compounds (P-1) to (P-6) shown in Table 1.
- the “other structural unit” means a structural unit other than the structural unit represented by the formula (Y) and the structural unit represented by the formula (X).
- p, q, r, s, and t represent the molar ratio of each structural unit.
- p + q + r + s + t 100 and 100 ⁇ p + q + r + s ⁇ 70.
- the polymer host may be any of a block copolymer, a random copolymer, an alternating copolymer, and a graft copolymer, and may be in other modes.
- a copolymer obtained by polymerization is preferred.
- the number average molecular weight in terms of polystyrene of the polymer host is preferably 5 ⁇ 10 3 to 1 ⁇ 10 6 , more preferably 1 ⁇ 10 4 to 5 ⁇ 10 5 , and even more preferably 1.5 ⁇ 10 4. ⁇ 2 ⁇ 10 5 .
- the polymer host can be produced by using a known polymerization method described in Chemical Review (Chem. Rev.), Vol. 109, pages 897-1091 (2009), etc., and the Suzuki reaction, Buchwald reaction, Stille Examples thereof include a polymerization method by a coupling reaction using a transition metal catalyst such as a reaction, a Negishi reaction and a Kumada reaction.
- a method of charging the monomer a method in which the entire amount of the monomer is charged all at once into the reaction system, after a part of the monomer is charged and reacted, the remaining monomers are batched, Examples thereof include a method of charging continuously or divided, a method of charging monomer continuously or divided, and the like.
- transition metal catalysts examples include palladium catalysts and nickel catalysts.
- Post-treatment of the polymerization reaction is a known method, for example, a method of removing water-soluble impurities by liquid separation, adding the reaction solution after polymerization reaction to a lower alcohol such as methanol, filtering the deposited precipitate, and then drying. These methods are performed alone or in combination.
- a lower alcohol such as methanol
- filtering the deposited precipitate and then drying.
- These methods are performed alone or in combination.
- the purity of the polymer host is low, it can be purified by usual methods such as crystallization, reprecipitation, continuous extraction with a Soxhlet extractor, column chromatography, and the like.
- the first organic layer is composed of a fluorescent low molecular weight compound, the above-described host material, hole transport material, hole injection material, electron transport material, electron injection material, antioxidant, and light emitting material (fluorescent light emitting material). It may be a layer containing a composition (hereinafter also referred to as “first composition”) containing at least one material selected from the group consisting of:
- the hole transport material is classified into a low molecular compound and a high molecular compound, and is preferably a high molecular compound.
- the hole transport material may have a crosslinking group.
- polymer compound examples include polyvinyl carbazole and derivatives thereof; polyarylene having an aromatic amine structure in the side chain or main chain and derivatives thereof.
- the polymer compound may be a compound to which an electron accepting site is bonded. Examples of the electron accepting site include fullerene, tetrafluorotetracyanoquinodimethane, tetracyanoethylene, trinitrofluorenone, and fullerene is preferable.
- the compounding amount of the hole transport material is usually 1 to 400 parts by mass, preferably 5 to 150 parts by mass when the fluorescent light emitting low molecular weight compound is 100 parts by mass.
- the hole transport material may be used alone or in combination of two or more.
- Electron transport materials are classified into low molecular compounds and high molecular compounds.
- the electron transport material may have a crosslinking group.
- low molecular weight compounds examples include phosphorescent compounds having 8-hydroxyquinoline as a ligand, oxadiazole, anthraquinodimethane, benzoquinone, naphthoquinone, anthraquinone, tetracyanoanthraquinodimethane, fluorenone, diphenyldicyanoethylene. And diphenoquinone, and derivatives thereof.
- polymer compound examples include polyphenylene, polyfluorene, and derivatives thereof.
- the polymer compound may be doped with a metal.
- the compounding amount of the electron transport material is usually 1 to 400 parts by mass, preferably 5 to 150 parts by mass, with 100 parts by mass of the fluorescent light-emitting low-molecular compound.
- the electron transport material may be used alone or in combination of two or more.
- the hole injection material and the electron injection material are classified into a low molecular compound and a high molecular compound, respectively.
- the hole injection material and the electron injection material may have a crosslinking group.
- low molecular weight compounds include metal phthalocyanines such as copper phthalocyanine; carbon; metal oxides such as molybdenum and tungsten; and metal fluorides such as lithium fluoride, sodium fluoride, cesium fluoride, and potassium fluoride.
- metal phthalocyanines such as copper phthalocyanine
- carbon such as carbon
- metal oxides such as molybdenum and tungsten
- metal fluorides such as lithium fluoride, sodium fluoride, cesium fluoride, and potassium fluoride.
- polymer compound examples include polyaniline, polythiophene, polypyrrole, polyphenylene vinylene, polythienylene vinylene, polyquinoline and polyquinoxaline, and derivatives thereof; conductive polymers such as polymers containing an aromatic amine structure in the main chain or side chain. A functional polymer.
- the compounding amounts of the hole injecting material and the electron injecting material are each usually 1 to 400 parts by mass, preferably 5 to 5 parts per 100 parts by mass of the fluorescent light-emitting low molecular weight compound. 150 parts by mass.
- the electron injection material and the hole injection material may be used alone or in combination of two or more.
- the electrical conductivity of the conductive polymer is preferably 1 ⁇ 10 ⁇ 5 S / cm to 1 ⁇ 10 3 S / cm.
- the conductive polymer can be doped with an appropriate amount of ions.
- the kind of ions to be doped is an anion for a hole injection material and a cation for an electron injection material.
- the anion include polystyrene sulfonate ion, alkylbenzene sulfonate ion, and camphor sulfonate ion.
- the cation include lithium ion, sodium ion, potassium ion, and tetrabutylammonium ion.
- the ions to be doped may be used alone or in combination of two or more.
- Luminescent materials are classified into low molecular compounds and high molecular compounds.
- the light emitting material may have a crosslinking group.
- low molecular weight compound examples include naphthalene and derivatives thereof, anthracene and derivatives thereof, perylene and derivatives thereof, and triplet light-emitting complexes having iridium, platinum, or europium as a central metal.
- Examples of the polymer compound include a phenylene group, a naphthalenediyl group, a fluorenediyl group, a phenanthrene diyl group, a dihydrophenanthrene diyl group, a structural unit represented by the formula (X), a carbazole diyl group, a phenoxazine diyl group, and a phenothiazine.
- Examples thereof include polymer compounds containing a diyl group, an anthracene diyl group, a pyrenediyl group, and the like.
- the light emitting material preferably contains a triplet light emitting complex and / or a polymer compound.
- triplet light-emitting complex examples include the metal complexes shown below.
- the amount of the luminescent material is usually 1 to 400 parts by mass, preferably 5 to 150 parts by mass, with 100 parts by mass of the fluorescent low-molecular compound.
- Fluorescent materials may be used alone or in combination of two or more.
- the antioxidant may be any compound that is soluble in the same solvent as the fluorescent light-emitting low-molecular compound and does not inhibit light emission and charge transport. Examples thereof include phenol-based antioxidants and phosphorus-based antioxidants.
- the blending amount of the antioxidant is usually 0.001 to 10 parts by mass when the fluorescent low-molecular compound is 100 parts by mass.
- Antioxidants may be used alone or in combination of two or more.
- first ink As the first ink for forming the first organic layer, a composition containing a fluorescent light-emitting low molecular compound and a solvent can be used.
- the first ink is spin coating method, casting method, micro gravure coating method, gravure coating method, bar coating method, roll coating method, wire bar coating method, dip coating method, spray coating method, screen printing method, flexographic printing method.
- wet methods such as offset printing, ink jet printing, capillary coating, and nozzle coating.
- the viscosity of the first ink may be adjusted according to the type of wet method. However, when a solution such as an ink jet printing method is applied to a printing method that passes through a discharge device, clogging at the time of discharge and flight bending occur. Since it is difficult, it is preferably 1 to 20 mPa ⁇ s at 25 ° C.
- the solvent contained in the first ink is preferably a solvent that can dissolve or uniformly disperse the solid content in the ink.
- the solvent include chlorine solvents such as 1,2-dichloroethane, 1,1,2-trichloroethane, chlorobenzene and o-dichlorobenzene; ether solvents such as THF, dioxane, anisole and 4-methylanisole; Aromatic hydrocarbon solvents such as xylene, mesitylene, ethylbenzene, n-hexylbenzene, cyclohexylbenzene; cyclohexane, methylcyclohexane, n-pentane, n-hexane, n-heptane, n-octane, n-nonane, n- Aliphatic hydrocarbon solvents such as decane, n-dodecane, and bicyclohexyl; ketone solvents such as acetone,
- the blending amount of the solvent is usually 1000 to 100,000 parts by mass, preferably 2000 to 20000 parts by mass, with 100 parts by mass of the fluorescent low-molecular compound.
- the first organic layer is preferably a layer that does not contain the above-described triplet light-emitting complex.
- the second organic layer is a layer containing a crosslinked product of a polymer compound containing a crosslinked structural unit having a crosslinking group (hereinafter also referred to as “polymer compound of the second organic layer”).
- the crosslinked polymer compound of the second organic layer may be contained singly or in combination of two or more.
- the crosslinked product of the polymer compound of the second organic layer can be obtained by bringing the polymer compound of the second organic layer into a crosslinked state by the above-described method and conditions.
- the second organic layer is a layer containing a crosslinked product obtained by crosslinking a polymer compound of a kind of second organic layer
- a value x obtained by multiplying the molar ratio C of the structural unit with respect to the total moles of all the structural units constituting one kind of polymer compound and the molecular weight M of the structural unit, and the crosslinking ratio of the molar ratio C and the structural unit
- a value y obtained by multiplying the number n is obtained, the value of (Y 1 ⁇ 1000) / X 1 calculated from the sum X 1 of x and the sum Y 1 of y is 0.60 or more.
- the polymer compound of each second organic layer was determined (Y 1 ⁇ 1000) / X 1 value (average value based on the blend ratio of the polymer compounds of the two or more second organic layers) is 0.60 or more.
- the second organic layer is a layer containing a crosslinked product obtained by crosslinking one or more polymer compounds of the second organic layer and a polymer compound that does not include a crosslinked structural unit having a crosslinking group
- the weighted average average value from the blending ratio of the polymer compound of one or more second organic layers and the polymer compound not including the crosslinking structural unit having one or more crosslinking groups) is 0.60 or more It becomes.
- examples of the polymer compound that does not include a cross-linking structural unit having a cross-linking group include a structural unit represented by the formula (Y) and a structural unit represented by the formula (X). Examples thereof include a polymer compound containing at least one selected structural unit.
- the polymer compound of the second organic layer Since the polymer compound of the second organic layer is excellent in the external quantum efficiency of the light emitting device according to this embodiment, the polymer compound includes a crosslinked structural unit having at least one kind of crosslinking group selected from the above-mentioned crosslinking group A group. It is preferable that
- the external quantum efficiency of the light emitting device is more excellent, and therefore, preferably the formula (XL-1) to the formula (XL-4) and the formula (XL- 7) to a crosslinking group represented by formula (XL-10) or formula (XL-14) to formula (XL-17), more preferably formula (XL-1), formula (XL-3), A crosslinking group represented by formula (XL-9), formula (XL-10), formula (XL-16) or formula (XL-17), more preferably formula (XL-1), formula (XL -16) or a crosslinking group represented by formula (XL-17), particularly preferably a crosslinking group represented by formula (XL-1) or formula (XL-17), and particularly preferred It is a crosslinking group represented by (XL-17).
- the structural unit having at least one cross-linking group selected from the cross-linking group A group contained in the polymer compound of the second organic layer is a structural unit represented by formula (2) described later, formula (2 ′).
- the structural unit represented may be a structural unit represented by the following formula or a structural unit represented by the formula (2) or a structural unit represented by the formula (2 ′).
- nA represents an integer of 0 to 5, and is preferably an integer of 0 to 3, more preferably an integer of 0 to 2, even more preferably, since the external quantum efficiency of the light emitting device according to this embodiment is more excellent. Is 1 or 2.
- N represents 1 or 2, and is preferably 2 because the external quantum efficiency of the light emitting device according to this embodiment is more excellent.
- Ar 3 represents an aromatic hydrocarbon group or a heterocyclic group, and since the external quantum efficiency of the light-emitting device according to this embodiment is more excellent, it is preferably an aromatic hydrocarbon group that may have a substituent. .
- the number of carbon atoms of the aromatic hydrocarbon group represented by Ar 3 is usually 6 to 60, preferably 6 to 30, and more preferably 6 to 18, excluding the number of carbon atoms of the substituent. is there.
- the arylene group portion excluding n substituents of the aromatic hydrocarbon group represented by Ar 3 is preferably represented by groups represented by formulas (A-1) to (A-20). More preferably, the group is more preferably the formula (A-1), the formula (A-2), the formula (A-6) to the formula (A-10), the formula (A-19) or the formula (A-20). And more preferably represented by formula (A-1), formula (A-2), formula (A-7), formula (A-9) or formula (A-19). It is a group. These groups may have a substituent.
- the number of carbon atoms of the heterocyclic group represented by Ar 3 is usually 2 to 60, preferably 3 to 30, and more preferably 4 to 18, excluding the number of carbon atoms of the substituent.
- the divalent heterocyclic group moiety excluding n substituents of the heterocyclic group represented by Ar 3 is preferably a group represented by the formula (AA-1) to the formula (AA-34). is there.
- the aromatic hydrocarbon group and heterocyclic group represented by Ar 3 may have a substituent, such as an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, an aryl group.
- a substituent such as an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, an aryl group.
- An oxy group, a halogen atom, a monovalent heterocyclic group and a cyano group are preferred.
- L A is an alkylene group, a cycloalkylene group, an arylene group, a divalent heterocyclic group, the group represented by -NR'-, an oxygen atom or a sulfur atom, these groups have a substituent Also good.
- R ′ represents a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group.
- L A number of carbon atoms of the alkylene group represented by the not including the carbon atom number of substituent is usually 1 to 20, preferably 1 to 15, more preferably 1 to 10.
- the number of carbon atoms a cycloalkylene group represented by L A is not including the carbon atom number of substituent is usually 3 to 20.
- alkylene group represented by L A for example, methylene group, ethylene group, propylene group, butylene group, hexylene group, and octylene group.
- Alkylene group represented by L A may have a substituent, and examples of the substituent, a cycloalkyl group, an alkoxy group, cycloalkoxy group, a halogen atom and a cyano group. These groups may further have a substituent.
- the cycloalkylene group represented by L A for example, cyclopentylene group, cyclohexylene group and the like.
- Cycloalkylene group represented by L A may have a substituent, examples of the substituent include an alkyl group, a cycloalkyl group, an alkoxy group, cycloalkoxy group, a halogen atom and a cyano group. These groups may further have a substituent.
- Arylene group represented by L A may have a substituent.
- the arylene group is preferably a phenylene group or a fluorenediyl group, more preferably an m-phenylene group, a p-phenylene group, a fluorene-2,7-diyl group, or a fluorene-9,9-diyl group.
- the substituent that the arylene group may have include an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, an aryloxy group, a monovalent heterocyclic group, a halogen atom, a cyano group, and the above-described bridging group.
- a crosslinking group selected from Group A is preferred. These groups may further have a substituent.
- the divalent heterocyclic group represented by L A is preferably a group represented by the formula (AA-1) ⁇ formula (AA-34).
- an arylene group or an alkylene group preferably a phenylene group, fluorenediyl group or an alkylene group. These groups may have a substituent.
- X represents a crosslinking group selected from the crosslinking group A group.
- the bridging group represented by X since the external quantum efficiency of the light emitting device according to this embodiment is more excellent, preferably, the formula (XL-1) to the formula (XL-4) and the formula (XL-7) to A crosslinking group represented by formula (XL-10) or formula (XL-14) to formula (XL-17), more preferably formula (XL-1), formula (XL-3), formula (XL) -9), a crosslinking group represented by formula (XL-10), formula (XL-16) or formula (XL-17), more preferably formula (XL-1) or formula (XL-16) Or a crosslinking group represented by the formula (XL-17), particularly preferably a crosslinking group represented by the formula (XL-1) or the formula (XL-17), particularly preferably a formula (XL- It is a crosslinking group represented by 17).
- the structural unit represented by the formula (2) may be included in the high molecular compound of the second organic layer, or may be included in two or more types.
- mA represents an integer of 0 to 5, and since the external quantum efficiency of the light emitting device according to this embodiment is more excellent, it is preferably an integer of 0 to 3, more preferably an integer of 0 to 2, and still more preferably. Is 0 or 1, particularly preferably 0.
- M represents an integer of 1 to 4, and is preferably 1 or 2 and more preferably 2 because the external quantum efficiency of the light emitting device according to the present embodiment is more excellent.
- c represents an integer of 0 or 1, and is preferably 0 because the production of the polymer compound of the second organic layer is facilitated and the external quantum efficiency of the light-emitting device according to this embodiment is more excellent.
- Ar 5 represents an aromatic hydrocarbon group, a heterocyclic group, or a group in which at least one aromatic hydrocarbon ring and at least one heterocyclic ring are directly bonded.
- Ar 5 is preferably an aromatic hydrocarbon group which may have a substituent since the external quantum efficiency of the light emitting device according to this embodiment is more excellent.
- the definition and example of the arylene group part excluding m substituents of the aromatic hydrocarbon group represented by Ar 5 are the same as the definition and example of the arylene group represented by Ar X2 in formula (X). .
- divalent heterocyclic group part excluding m substituents of the heterocyclic group represented by Ar 5 are the same as those of the divalent heterocyclic group part represented by Ar X2 in formula (X). Definitions and examples are the same.
- Ar 4 and Ar 6 each independently represent an arylene group or a divalent heterocyclic group, and since the external quantum efficiency of the light-emitting device according to this embodiment is more excellent, it may preferably have a substituent.
- An arylene group An arylene group.
- the definitions and examples of the arylene group represented by Ar 4 and Ar 6 are the same as the definitions and examples of the arylene group represented by Ar X1 and Ar X3 in the formula (X).
- the definitions and examples of the divalent heterocyclic group represented by Ar 4 and Ar 6 are the same as the definitions and examples of the divalent heterocyclic group represented by Ar X1 and Ar X3 in Formula (X).
- Ar 4 , Ar 5 and Ar 6 are each bonded to a group other than the group bonded to the nitrogen atom to which the group is bonded, directly or via an oxygen atom or a sulfur atom to form a ring. It may be.
- the groups represented by Ar 4 , Ar 5 and Ar 6 may have a substituent, and examples of the substituent include an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, an aryloxy group, A halogen atom, a monovalent heterocyclic group and a cyano group are preferred.
- K A represents an alkylene group, a cycloalkylene group, an arylene group, a divalent heterocyclic group, a group represented by —NR′—, an oxygen atom or a sulfur atom.
- the definition and examples of the cyclic group are the same.
- X ′ represents a bridging group selected from the above bridging group A group, a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group, or a monovalent heterocyclic group.
- the definition and examples of the crosslinking group represented by X ′ are the same as the definition and examples of the crosslinking group represented by X described above.
- the structural unit represented by the formula (2 ′) may be included in the high molecular compound of the second organic layer, or may be included in two or more types.
- Examples of the structural unit represented by the formula (2) include structural units represented by the formulas (2-1) to (2-30).
- Examples of the structural unit represented by the formula (2 ′) include structural units represented by the formulas (2′-1) to (2′-9).
- it is preferably a structural unit represented by the formula (2-1) to the formula (2-30), more preferably the formula (2).
- the second organic layer further includes a structural unit represented by the formula (X).
- the polymer compound further contains the structural unit represented by Formula (Y).
- the structural unit and formula represented by the formula (X) are further included. It is preferable that the structural unit represented by (Y) is included.
- the definitions, examples and preferred ranges of the structural unit represented by the formula (X) and the structural unit represented by the formula (Y) that may be contained in the polymer compound of the second organic layer are the above-mentioned high
- the definition, examples, and preferred ranges of the structural unit represented by the formula (X) and the structural unit represented by the formula (Y) that may be contained in the molecular host are the same.
- each of the structural unit represented by the formula (X) and the structural unit represented by the formula (Y) may be included alone or in combination of two or more. It may be.
- Examples of the polymer compound in the second organic layer include polymer compounds (P-7) to (P-14) shown in Table 2.
- the “other structural unit” means a structural unit other than the structural units represented by Formula (2), Formula (2 ′), Formula (X), and Formula (Y).
- p ′, q ′, r ′, s ′, and t ′ represent the molar ratio of each structural unit.
- p ′ + q ′ + r ′ + s ′ + t ′ 100 and 70 ⁇ p ′ + q ′ + r ′ + s ′ ⁇ 100.
- the polymer compound of the second organic layer may be any of a block copolymer, a random copolymer, an alternating copolymer, and a graft copolymer, and may be in other modes.
- a copolymer obtained by copolymerizing seed raw material monomers is preferable.
- the number average molecular weight in terms of polystyrene of the polymer compound of the second organic layer is preferably 5 ⁇ 10 3 to 1 ⁇ 10 6 , more preferably 1 ⁇ 10 4 to 5 ⁇ 10 5 , and still more preferably. 1.5 ⁇ 10 4 to 1 ⁇ 10 5 .
- the polymer compound of the second organic layer can be produced by the same method as the polymer host production method described above.
- the value of (Y 1 ⁇ 1000) / X 1 is substantially equal to the average number of crosslinking groups per 1000 molecular weight of the polymer compound of the second organic layer, and the polymer compound of the second organic layer It can be effectively used as an index indicating the average number of cross-linking groups.
- the polymer compound HTL-5 has structural units derived from the compound M3, the compound M4, and the compound M5.
- the ratio of all the structural units to the total mole is 0.45 for the structural unit derived from the compound M3, 0.05 for the structural unit derived from the compound M4, and 0.50 for the structural unit derived from the compound M5. .
- the molecular weight of the structural unit derived from the compound M3 is 776.45
- the molecular weight of the structural unit derived from the compound M4 is 240.20
- the molecular weight of the structural unit derived from the compound M5 is 750.51.
- the number of cross-linking groups included in the structural unit derived from the compound M3 is 2
- the number of cross-linking groups included in the structural unit derived from the compound M4 is 2
- the number of cross-linking groups included in the structural unit derived from the compound M5. Is 0.
- the value of (Y 1 ⁇ 1000) / X 1 is obtained based on the structural unit constituting each polymer compound. Also, determine the value of (Y 1 ⁇ 1000) / X 1 for each polymer compound, from the amount ratio of each polymer compound, obtaining the value of (Y 1 ⁇ 1000) / X 1.
- the polymer compound HTL-2 has structural units derived from the compound M3, the compound M4, the compound M6, and the compound M5.
- the ratio of all the structural units to the total mole is 0.05 for the structural unit derived from the compound M3, 0.05 for the structural unit derived from the compound M4, and derived from the compound M6.
- the structural unit is 0.40, and the structural unit derived from the compound M5 is 0.05.
- the molecular weight of the structural unit derived from the compound M3 is 776.45
- the molecular weight of the structural unit derived from the compound M4 is 240.20
- the molecular weight of the structural unit derived from the compound M6 is 244.23, and from the compound M5.
- the molecular weight of the derived structural unit is 750.51.
- the number of cross-linking groups possessed by the structural unit derived from the compound M3 is 2, the number of cross-linking groups possessed by the structural unit derived from the compound M4 is 2, and the number of cross-linking groups possessed by the monomer derived from the compound M6.
- the number is 0, and the number of crosslinking groups in the structural unit derived from the compound M5 is 0. Therefore, for the high molecular compound HTL-2, the value of (Y 1 ⁇ 1000) / X 1 calculated by the method described above is 0.38.
- the polymer compound HTL-1 has structural units derived from the compound M6 and the compound M5.
- the ratio of all the structural units to the total mole is 0.50 for the structural unit derived from the compound M6 and 0.50 for the structural unit derived from the compound M5.
- the molecular weight of the structural unit derived from compound M6 is 244.23, and the molecular weight of the structural unit derived from compound M5 is 750.51.
- the number of crosslinking groups included in the structural unit derived from the compound M6 is 0, and the number of crosslinking groups included in the structural unit derived from the compound M5 is 0. Therefore, the value of (Y 1 ⁇ 1000) / X 1 calculated by the above method is 0 for the polymer compound HTL-1.
- the value of (Y 1 ⁇ 1000) / X 1 is preferably 0.69 or more, more preferably 0.85 or more, because the external quantum efficiency of the light emitting device according to this embodiment is more excellent. More preferably, it is 0.95 or more, particularly preferably 1.10 or more, and particularly preferably 1.20 or more. As the value of (Y 1 ⁇ 1000) / X 1 increases, the second organic layer becomes a dense film, and the charge transport property of the second organic layer and / or the second organic layer to the first organic layer It is thought that the charge injection into is improved.
- the value of (Y 1 ⁇ 1000) / X 1 is usually 5.0 or less, preferably 4.0 or less, more preferably 3.0 or less, and still more preferably 2. 0 or less, particularly preferably 1.50 or less.
- the value of (Y 1 ⁇ 1000) / X 1 is more excellent in the external quantum efficiency of the light emitting device according to this embodiment, and more excellent in the luminance life of the light emitting device according to this embodiment. Therefore, Preferably it is 0.85 or more and 4.0 or less, More preferably, it is 0.95 or more and 3.0 or less, More preferably, it is 1.10 or more and 2.0 or less, Especially preferably, it is 1.20 or more 1.50 or less.
- the second organic layer is a group consisting of a crosslinked polymer of the second organic layer, a hole transport material, a hole injection material, an electron transport material, an electron injection material, an antioxidant, and a light emitting material. It may be a layer containing a composition containing at least one material selected from (hereinafter also referred to as “second composition”).
- Examples and preferred ranges of the hole transport material, electron transport material, hole injection material, electron injection material and light-emitting material contained in the second composition are the hole transport material contained in the first composition, The examples and preferred ranges of the electron transport material, hole injection material, electron injection material, and light emitting material are the same.
- the compounding amounts of the hole transport material, the electron transport material, the hole injection material, the electron injection material, and the light emitting material are each 100 parts by mass of the crosslinked polymer of the second organic layer. In general, it is 1 to 400 parts by mass, preferably 5 to 150 parts by mass.
- the blending amount of the antioxidant is usually 0.001 to 10 parts by mass when the crosslinked polymer of the polymer compound of the second organic layer is 100 parts by mass.
- the second ink for forming the second organic layer a second composition containing the polymer compound of the second organic layer and a solvent can be used.
- the second ink can be suitably used in the wet method described in the first ink section.
- the preferable range of the viscosity of the second ink is the same as the preferable range of the viscosity of the first ink.
- Examples and preferred ranges of the solvent contained in the second ink are the same as examples and preferred ranges of the solvent contained in the first ink.
- the blending amount of the solvent is usually 1000 to 100,000 parts by mass, preferably 2000 to 20000 parts by mass, when the polymer compound of the second organic layer is 100 parts by mass.
- the light emitting device includes an anode, a cathode, a first organic layer provided between the anode and the cathode, and adjacent to the first organic layer between the anode and the cathode. And a second organic layer provided.
- the light emitting device may have a layer other than the anode, the cathode, the first organic layer, and the second organic layer.
- the first organic layer is usually a light emitting layer (hereinafter, also referred to as “first light emitting layer”).
- the second organic layer is usually a hole transport layer, a light emitting layer (hereinafter also referred to as “second light emitting layer”) or an electron transport layer, preferably a hole. It is a transport layer or a second light emitting layer, more preferably a hole transport layer.
- the second organic layer is preferably a layer provided between the anode and the first organic layer because the external quantum efficiency of the light emitting device is more excellent. More preferably, it is a hole transport layer or a second light emitting layer provided between one organic layer, and more preferably a hole transport layer provided between an anode and a first organic layer. .
- the second organic layer when the second organic layer is a hole transport layer provided between the anode and the first organic layer, the external quantum efficiency of the light emitting device is more excellent. It is preferable to further have a hole injection layer between the two organic layers. In addition, when the second organic layer is a hole transport layer provided between the anode and the first organic layer, the external quantum efficiency of the light-emitting element is more excellent, and therefore, between the cathode and the first organic layer. In addition, it is preferable to further include at least one of an electron injection layer and an electron transport layer.
- the external quantum efficiency of the light emitting device when the second organic layer is the second light emitting layer provided between the anode and the first organic layer, the external quantum efficiency of the light emitting device is more excellent. It is preferable to further include at least one of a hole injection layer and a hole transport layer between the second organic layer. In addition, when the second organic layer is the second light emitting layer provided between the anode and the first organic layer, the external quantum efficiency of the light emitting element is more excellent, so that the cathode and the first organic layer It is preferable to further have at least one of an electron injection layer and an electron transport layer in between.
- the second organic layer is a second light emitting layer provided between the cathode and the first organic layer
- the external quantum efficiency of the light emitting device is more excellent
- the second organic layer is a second light emitting layer provided between the cathode and the first organic layer
- the external quantum efficiency of the light emitting element is more excellent, so that the cathode and the second organic layer
- the second organic layer is an electron transport layer provided between the cathode and the first organic layer
- the external quantum efficiency of the light emitting device is more excellent, so the anode and the first
- the second organic layer is an electron transport layer provided between the cathode and the first organic layer
- the external quantum efficiency of the light-emitting element is more excellent, so that the gap between the cathode and the second organic layer is higher. It is preferable to further have an electron injection layer.
- the layer configuration of the light emitting device includes the layer configurations represented by the following (D1) to (D14).
- the light-emitting element usually has a substrate, but may be laminated from the anode on the substrate, or may be laminated from the cathode on the substrate.
- “/” means that the layers before and after are stacked adjacent to each other.
- “second light emitting layer (second organic layer) / first light emitting layer (first organic layer)” means the second light emitting layer (second organic layer) and the first light emitting layer (second organic layer). The light emitting layer (first organic layer) is adjacently laminated.
- the layer configuration represented by (D3) to (D12) is preferable, and the layer configuration represented by (D7) to (D10) is more preferable.
- the anode, the hole injection layer, the hole transport layer, the second light emitting layer, the electron transport layer, the electron injection layer, and the cathode are each provided in two or more layers as necessary. It may be.
- hole injection layers When there are a plurality of anodes, hole injection layers, hole transport layers, second light emitting layers, electron transport layers, electron injection layers, and cathodes, they may be the same or different.
- the thickness of the anode, hole injection layer, hole transport layer, first light emitting layer, second light emitting layer, electron transport layer, electron injection layer and cathode is usually 1 nm to 1 ⁇ m, preferably 2 nm to It is 500 nm, more preferably 5 nm to 150 nm.
- the order, the number, and the thickness of the stacked layers may be adjusted in consideration of the external quantum efficiency and the device life of the light emitting device.
- the second light emitting layer is usually a layer containing a second organic layer or a light emitting material.
- the second light emitting layer is a layer containing a light emitting material
- examples of the light emitting material contained in the second light emitting layer include the light emitting material that may be contained in the first composition. It is done.
- the light emitting material contained in the second light emitting layer may be contained singly or in combination of two or more.
- the second light-emitting layer is the second light-emitting layer.
- An organic layer is preferred.
- the hole transport layer is usually a layer containing a second organic layer or a hole transport material.
- the hole transport layer is a layer containing a hole transport material
- examples of the hole transport material include a hole transport material that may be contained in the first composition described above.
- the hole transport material contained in the hole transport layer may be contained singly or in combination of two or more.
- the hole-transport layer is the second organic layer.
- a layer is preferred.
- the electron transport layer is usually the second organic layer or a layer containing an electron transport material, and preferably a layer containing an electron transport material.
- the electron transport layer is a layer containing an electron transport material
- examples of the electron transport material contained in the electron transport layer include the electron transport material that may be contained in the first composition described above. .
- the electron transport material contained in the electron transport layer may be contained singly or in combination of two or more.
- the hole injection layer is a layer containing a hole injection material.
- a hole injection material contained in a hole injection layer the hole injection material which the above-mentioned 1st composition may contain is mentioned, for example.
- the hole injection material contained in the hole injection layer may be contained singly or in combination of two or more.
- the electron injection layer is a layer containing an electron injection material.
- an electron injection material contained in an electron injection layer the electron injection material which the above-mentioned 1st composition may contain is mentioned, for example.
- the electron injection material contained in the electron injection layer may be contained singly or in combination of two or more.
- the substrate in the light-emitting element may be any substrate that can form electrodes and does not change chemically when the organic layer is formed.
- the substrate is made of a material such as glass, plastic, or silicon.
- the electrode farthest from the substrate is transparent or translucent.
- Examples of the material for the anode include conductive metal oxides and translucent metals, preferably indium oxide, zinc oxide, tin oxide; indium tin oxide (ITO), indium zinc oxide, etc.
- conductive metal oxides and translucent metals preferably indium oxide, zinc oxide, tin oxide; indium tin oxide (ITO), indium zinc oxide, etc.
- ITO indium tin oxide
- Examples of the material of the cathode include metals such as lithium, sodium, potassium, rubidium, cesium, beryllium, magnesium, calcium, strontium, barium, aluminum, zinc, indium; two or more kinds of alloys thereof; Alloys of at least one species and at least one of silver, copper, manganese, titanium, cobalt, nickel, tungsten, and tin; and graphite and graphite intercalation compounds.
- Examples of the alloy include a magnesium-silver alloy, a magnesium-indium alloy, a magnesium-aluminum alloy, an indium-silver alloy, a lithium-aluminum alloy, a lithium-magnesium alloy, a lithium-indium alloy, and a calcium-aluminum alloy.
- At least one of the anode and the cathode is usually transparent or translucent, but the anode is preferably transparent or translucent.
- Examples of the method for forming the anode and the cathode include a vacuum deposition method, a sputtering method, an ion plating method, a plating method, and a laminating method.
- a method for forming each layer such as the first light emitting layer, the second light emitting layer, the hole transporting layer, the electron transporting layer, the hole injecting layer, and the electron injecting layer is a low molecular compound.
- a vacuum deposition method from a powder a method by film formation from a solution or a molten state
- a polymer compound for example, a method by film formation from a solution or a molten state can be mentioned.
- the first light-emitting layer, the second light-emitting layer, the hole transport layer, the electron transport layer, the hole injection layer, and the electron injection layer are the first ink, the second ink, and the above-described light-emitting material and hole. It can be formed by a wet method such as a spin coating method or an ink jet printing method using inks each containing a transport material, an electron transport material, a hole injection material, and an electron injection material.
- planar anode and the cathode may be arranged so as to overlap each other.
- pattern-like light emission a method in which a mask having a pattern-like window is provided on the surface of a planar light-emitting element, a layer that is desired to be a non-light-emitting portion is formed extremely thick and substantially non-light-emitting. There is a method, a method of forming an anode or a cathode, or both electrodes in a pattern.
- a segment type display device capable of displaying numbers, characters, and the like can be obtained.
- both the anode and the cathode may be formed in stripes and arranged orthogonally. Partial color display and multicolor display are possible by a method of separately coating a plurality of types of polymer compounds having different emission colors, or a method using a color filter or a fluorescence conversion filter.
- the dot matrix display device can be driven passively or can be driven actively in combination with TFTs. These display devices can be used for displays of computers, televisions, portable terminals and the like.
- the planar light emitting element can be suitably used as a planar light source for backlight of a liquid crystal display device or a planar illumination light source. If a flexible substrate is used, it can be used as a curved light source and display device.
- the polystyrene-equivalent number average molecular weight (Mn) and polystyrene-equivalent weight average molecular weight (Mw) of the polymer compound were determined by size exclusion chromatography (SEC) (manufactured by Shimadzu Corporation, trade name: LC-10Avp). Determined by The SEC measurement conditions are as follows. [Measurement condition] The polymer compound to be measured was dissolved in tetrahydrofuran (THF) at a concentration of about 0.05% by mass, and 10 ⁇ L was injected into SEC. THF was used as the mobile phase of SEC, and flowed at a flow rate of 2.0 mL / min. As the column, PLgel MIXED-B (manufactured by Polymer Laboratories) was used. A UV-VIS detector (manufactured by Shimadzu Corporation, trade name: SPD-10Avp) was used as the detector.
- SEC size exclusion chromatography
- the maximum peak wavelength of the emission spectrum of the compound was measured at room temperature with a spectrophotometer (trade name: FP-6500, manufactured by JASCO Corporation).
- a spectrophotometer (trade name: FP-6500, manufactured by JASCO Corporation).
- a toluene solution in which the compound was dissolved in xylene at a concentration of about 0.8 ⁇ 10 ⁇ 4 mass% was used as a sample.
- excitation light UV light having a wavelength of 325 nm was used.
- Compound EM-1 was synthesized according to the method described in International Publication No. 2008/059713.
- Compound EM-2 was synthesized according to the method described in JP-A-2006-176491.
- Compound EM-3 was synthesized according to the method described in International Publication No. 2005/033051.
- Compound EM-4 and Compound EM-5 were purchased from Tokyo Chemical Industry Co., Ltd.
- Compound EM-6 was synthesized according to the method described in International Publication No. 2010/013006.
- Compound EM-7 was purchased from Aldrich.
- Compound EM-A1 was synthesized according to the method described in JP2011-105643A.
- Compound EM-A2 was synthesized according to the method described in WO2007 / 058368.
- the maximum peak wavelength of the emission spectrum of Compound EM-1 was 441 nm.
- the maximum peak wavelength of the emission spectrum of Compound EM-2 was 446 nm.
- the maximum peak wavelength of the emission spectrum of Compound EM-3 was 453 nm.
- the maximum peak wavelength of the emission spectrum of Compound EM-4 was 446 nm.
- the maximum peak wavelength of the emission spectrum of Compound EM-5 was 404 nm.
- the maximum peak wavelength of the emission spectrum of Compound EM-6 was 453 nm.
- the maximum peak wavelength of the emission spectrum of Compound EM-7 was 448 nm.
- the maximum peak wavelength of the emission spectrum of compound EM-A1 was 454 nm.
- the maximum peak wavelength of the emission spectrum of compound EM-A2 was 521 nm.
- Compound HM-1 was purchased from AK Scientific.
- Compound HM-2 was synthesized according to the methods described in JP2011-10000942 and International Publication No. 2011-137922.
- the maximum peak wavelength of the emission spectrum of Compound HM-1 was 425 nm.
- the maximum peak wavelength of the emission spectrum of Compound HM-2 was 430 nm.
- Compound M1 was synthesized according to the method described in JP2012-144721A. A commercially available product was used as Compound M2.
- Compound M3 was synthesized according to the method described in International Publication No. 2015/145871.
- Compound M4 was synthesized according to the method described in International Publication No. 2013/146806.
- Compound M5 was synthesized according to the method described in WO2005 / 049546.
- Compound M6 was synthesized according to the method described in JP 2010-189630 A.
- Step 1 Synthesis of Polymer Compound HP-1 (Step 1) After the inside of the reaction vessel was set to an inert gas atmosphere, Compound M1 (1.73 g), Compound M2 (0.843 g), dichlorobis [Tris (2 -Methoxyphenyl) phosphine] palladium (2.2 mg) and toluene (40 ml) were added and heated to 105.degree. (Step 2) A 20% by mass tetraethylammonium hydroxide aqueous solution (8.7 g) was added dropwise to the resulting reaction solution and refluxed for 3 hours.
- Step 3 Thereafter, 9-bromoanthracene (64.1 mg), 20 mass% tetraethylammonium hydroxide aqueous solution (8.8 g) and dichlorobis [tris (2-methoxyphenyl) phosphine] palladium (2.2 mg) And refluxed for 16 hours.
- Step 4 Thereafter, an aqueous sodium diethyldithiacarbamate solution was added thereto, and the mixture was stirred at 80 ° C. for 2 hours. The obtained reaction solution was cooled, washed twice with water, twice with a 3% by mass aqueous acetic acid solution and twice with water, and the resulting solution was added dropwise to methanol, resulting in precipitation.
- the precipitate was dissolved in toluene and purified by passing through an alumina column and a silica gel column in this order. When the obtained solution was added dropwise to methanol and stirred, precipitation occurred. The precipitate was collected by filtration and dried to obtain 0.91 g of polymer compound HP-1.
- the Mn of the polymer compound HP-1 was 1.2 ⁇ 10 5 and the Mw was 4.8 ⁇ 10 5 .
- the theoretical value obtained from the amount of charged raw material for polymer compound HP-1 is that the structural unit derived from compound M1 and the structural unit derived from compound M2 are formed in a molar ratio of 50:50. It is a copolymer.
- the polymer compound HTL-1 had an Mn of 4.5 ⁇ 10 4 and an Mw of 1.5 ⁇ 10 5 .
- the high molecular weight compound HTL-1 has a theoretical value obtained from the amount of the raw materials charged, and the structural unit derived from the compound M5 and the structural unit derived from the compound M6 are configured in a molar ratio of 50:50. It is a copolymer. With respect to the polymer compound HTL-1, the value of (Y 1 ⁇ 1000) / X 1 was calculated by the above-described method, and was 0.
- Step 3 phenylboronic acid (61.0 mg) and dichlorobis (tris-o-methoxyphenylphosphine) palladium (1.1 mg) were added thereto and refluxed for 14.5 hours.
- Step 4 Thereafter, an aqueous sodium diethyldithiacarbamate solution was added thereto, and the mixture was stirred at 80 ° C. for 2 hours. After cooling, the resulting reaction solution was washed twice with water, twice with a 3% by mass aqueous acetic acid solution and twice with water, and when the resulting solution was added dropwise to methanol, precipitation occurred.
- the obtained precipitate was dissolved in toluene and purified by passing through an alumina column and a silica gel column in this order.
- the obtained solution was added dropwise to methanol and stirred, and then the resulting precipitate was collected by filtration and dried to obtain 1.05 g of a polymer compound HTL-2.
- the polymer compound HTL-2 had a Mn of 2.4 ⁇ 10 4 and a Mw of 1.8 ⁇ 10 5 .
- the polymer compound HTL-2 has a theoretical value determined from the amount of raw materials charged, a structural unit derived from the compound M3, a structural unit derived from the compound M4, a structural unit derived from the compound M6, and a compound.
- the structural unit derived from M5 is a copolymer composed of a molar ratio of 5: 5: 40: 50.
- the value of (Y 1 ⁇ 1000) / X 1 was calculated by the method described above, and it was 0.38.
- Step 1-1 After making the inside of the reaction vessel an inert gas atmosphere, Compound M3 (0.311 g), Compound M4 (0.0496 g), Compound M6 (0.295 g), Compound M5 (0.917 g), Dichlorobis (tris-o-methoxyphenylphosphine) palladium (1.76 mg) and toluene (30 mL) were added and heated to 105 ° C.
- Step 2-1 A 20% by mass aqueous tetraethylammonium hydroxide solution (6.7 mL) was added dropwise to the reaction solution, and the mixture was refluxed for 6 hours.
- Step 3-1 Thereafter, phenylboronic acid (48.8 mg) and dichlorobis (tris-o-methoxyphenylphosphine) palladium (0.88 mg) were added thereto and refluxed for 14.5 hours.
- the polymer compound HTL-3 had Mn of 2.5 ⁇ 10 4 and Mw of 1.3 ⁇ 10 5 .
- the high molecular compound HTL-3 has a structural value derived from the compound M3, a structural unit derived from the compound M4, a structural unit derived from the compound M6,
- the structural unit derived from M5 is a copolymer composed of a molar ratio of 15: 5: 30: 50.
- the value of (Y 1 ⁇ 1000) / X 1 was calculated by the above-described method, and was 0.69.
- Step 1-2 After making the inside of the reaction vessel an inert gas atmosphere, Compound M3 (0.518 g), Compound M4 (0.0496 g), Compound M6 (0.195 g), Compound M5 (0.917 g), Dichlorobis (tris-o-methoxyphenylphosphine) palladium (1.76 mg) and toluene (30 mL) were added and heated to 105 ° C.
- the polymer compound HTL-4 had an Mn of 2.5 ⁇ 10 4 and an Mw of 3.0 ⁇ 10 5 .
- the high molecular compound HTL-4 has a theoretical value determined from the amount of raw materials charged, a structural unit derived from the compound M3, a structural unit derived from the compound M4, a structural unit derived from the compound M6, and a compound.
- the structural unit derived from M5 is a copolymer composed of a molar ratio of 25: 5: 20: 50.
- the value of (Y 1 ⁇ 1000) / X 1 was calculated by the above-described method, and was 0.95.
- the polymer compound HTL-5 had Mn of 2.3 ⁇ 10 4 and Mw of 1.2 ⁇ 10 5 .
- the theoretical value obtained from the amount of charged raw materials for polymer compound HTL-5 is that the structural unit derived from compound M3, the structural unit derived from compound M4, and the structural unit derived from compound M5 are: It is a copolymer formed by a molar ratio of 45: 5: 50.
- the value of (Y 1 ⁇ 1000) / X 1 was calculated by the method described above, and it was 1.36.
- Example D1 Fabrication and evaluation of light-emitting element D1 (formation of anode and hole injection layer)
- An anode was formed by attaching an ITO film with a thickness of 45 nm to the glass substrate by sputtering.
- a hole injection material ND-3202 manufactured by Nissan Chemical Industries
- the hole injection layer was formed by heating at 50 ° C. for 3 minutes and further heating at 230 ° C. for 15 minutes.
- the polymer compound HTL-5 was dissolved in xylene at a concentration of 0.6% by mass. Using the obtained xylene solution, a film having a thickness of 20 nm was formed on the hole injection layer by spin coating, and heated in a nitrogen gas atmosphere on a hot plate at 180 ° C. for 60 minutes to form a second film. An organic layer of was formed. By this heating, the polymer compound HTL-5 became a crosslinked product.
- the substrate on which the first organic layer is formed is depressurized to 1 ⁇ 10 ⁇ 4 Pa or less in a vapor deposition machine, and then, as a cathode, sodium fluoride is about 4 nm on the first organic layer, and then fluorinated. About 80 nm of aluminum was deposited on the sodium layer. After vapor deposition, the light emitting element D1 was produced by sealing using a glass substrate.
- Example D2 Production and evaluation of light-emitting device D2 Light-emitting device D2 was prepared in the same manner as in Example D1, except that polymer compound HTL-4 was used instead of polymer compound HTL-5 in Example D1. Was made.
- Example D3 Production and evaluation of light-emitting device D3 Light-emitting device D3 was prepared in the same manner as in Example D1, except that polymer compound HTL-3 was used instead of polymer compound HTL-5 in Example D1. Was made.
- Table 3 shows the results of Examples and Comparative Examples.
- Example D4 Fabrication and evaluation of light-emitting element D4 (formation of anode and hole injection layer)
- An anode was formed by attaching an ITO film with a thickness of 45 nm to the glass substrate by sputtering.
- a hole injection material ND-3202 manufactured by Nissan Chemical Industries
- the hole injection layer was formed by heating at 50 ° C. for 3 minutes and further heating at 230 ° C. for 15 minutes.
- the polymer compound HTL-5 was dissolved in xylene at a concentration of 0.6% by mass. Using the obtained xylene solution, a film having a thickness of 20 nm was formed on the hole injection layer by spin coating, and heated in a nitrogen gas atmosphere on a hot plate at 180 ° C. for 60 minutes to form a second film. An organic layer of was formed. By this heating, the polymer compound HTL-5 became a crosslinked product.
- the substrate on which the first organic layer is formed is depressurized to 1.0 ⁇ 10 ⁇ 4 Pa or less in a vapor deposition machine, and then, as a cathode, sodium fluoride is about 4 nm on the first organic layer, and then About 80 nm of aluminum was deposited on the sodium fluoride layer. After vapor deposition, the light emitting element D4 was produced by sealing using a glass substrate.
- Example D5 Production and evaluation of light-emitting device D5 Light-emitting device D5 was prepared in the same manner as in Example D4, except that polymer compound HTL-4 was used instead of polymer compound HTL-5 in Example D4. Was made.
- Example D6 Production and evaluation of light-emitting device D6
- Light-emitting device D6 was prepared in the same manner as in Example D4, except that polymer compound HTL-3 was used instead of polymer compound HTL-5 in Example D4. Was made.
- Example D7 Production and evaluation of light-emitting device D7 A light-emitting device D7 was produced in the same manner as in Example D4, except that Compound EM-2 was used instead of Compound EM-1 in Example D4.
- Example D8 Fabrication and evaluation of light-emitting device D8 A light-emitting device D8 was fabricated in the same manner as in Example D4 except that Compound EM-3 was used instead of Compound EM-1 in Example D4.
- Example D9 Production and evaluation of light-emitting device D9 A light-emitting device D9 was produced in the same manner as in Example D4, except that Compound EM-4 was used instead of Compound EM-1 in Example D4.
- Example D10 Production and evaluation of light-emitting device D10 Light-emitting device D10 was produced in the same manner as in Example D4, except that polymer compound HP-1 was used instead of compound HM-1 in Example D4. did.
- Example D11 Production and evaluation of light-emitting device D11 A light-emitting device D11 was produced in the same manner as in Example D4, except that compound HM-2 was used instead of compound HM-1 in Example D4.
- Table 4 shows the results of Examples and Comparative Examples.
- Example D12 Production and evaluation of light-emitting device D12 A light-emitting device D12 was produced in the same manner as in Example D1, except that compound EM-A2 was used instead of compound EM-A1 in Example D1.
- Example D13 Production and evaluation of light-emitting device D13 Light-emitting device D13 was prepared in the same manner as in Example D12, except that polymer compound HTL-4 was used instead of polymer compound HTL-5 in Example D12. Was made.
- Example D14 Production and evaluation of light-emitting device D14 A light-emitting device D14 was produced in the same manner as in Example D1, except that Compound EM-5 was used instead of Compound EM-A1 in Example D1.
- Example D15 Production and evaluation of light-emitting device D15 Light-emitting device D15 was prepared in the same manner as in Example D14, except that polymer compound HTL-3 was used instead of polymer compound HTL-5 in Example D14. Was made.
- Table 5 shows the results of Examples and Comparative Examples.
- Example D16 Production and evaluation of light-emitting element D16 A light-emitting element D16 was produced in the same manner as in Example D4.
- Example D17 Production and evaluation of light-emitting device D17 A light-emitting device D17 was produced in the same manner as in Example D4 except that Compound EM-6 was used instead of Compound EM-1 in Example D4.
- Example D18 Production and evaluation of light-emitting device D18 A light-emitting device D18 was produced in the same manner as in Example D4 except that Compound EM-7 was used instead of Compound EM-1 in Example D4.
- a light emitting device having excellent external quantum efficiency can be provided.
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Abstract
Description
前記第1の有機層が、蛍光発光性低分子化合物を含有する層であり、
前記蛍光発光性低分子化合物の発光スペクトルの最大ピーク波長が380nm以上750nm以下であり、
前記第2の有機層が、架橋基を有する架橋構成単位を含む高分子化合物の架橋体を含有する層であり、
前記高分子化合物を構成する各構成単位について、全構成単位の総モルに対するその構成単位のモル比Cとその構成単位の分子量Mとを乗じた値x、及び、前記モル比Cとその構成単位が有する前記架橋基の数nとを乗じた値yを求めたとき、前記xの総和X1及び前記yの総和Y1から計算される(Y1×1000)/X1の値が、0.60以上である、発光素子。
[2]前記高分子化合物が、架橋基A群から選ばれる少なくとも1種の架橋基を有する架橋構成単位を含む高分子化合物である、[1]に記載の発光素子。
[3]前記架橋構成単位が、式(2)で表される構成単位又は式(2’)で表される構成単位である、[2]に記載の発光素子。
nAは0~5の整数を表し、nは1又は2を表す。nAが複数存在する場合、それらは同一でも異なっていてもよい。
Ar3は、芳香族炭化水素基又は複素環基を表し、これらの基は置換基を有していてもよい。
LAは、アルキレン基、シクロアルキレン基、アリーレン基、2価の複素環基、-NR’-で表される基、酸素原子又は硫黄原子を表し、これらの基は置換基を有していてもよい。R’は、水素原子、アルキル基、シクロアルキル基、アリール基又は1価の複素環基を表し、これらの基は置換基を有していてもよい。LAが複数存在する場合、それらは同一でも異なっていてもよい。
Xは、前記架橋基A群から選ばれる架橋基を表す。Xが複数存在する場合、それらは同一でも異なっていてもよい。]
mAは0~5の整数を表し、mは1~4の整数を表し、cは0又は1の整数を表す。mAが複数存在する場合、それらは同一でも異なっていてもよい。
Ar5は、芳香族炭化水素基、複素環基、又は、少なくとも1種の芳香族炭化水素環と少なくとも1種の複素環とが直接結合した基を表し、これらの基は置換基を有していてもよい。
Ar4及びAr6は、それぞれ独立に、アリーレン基又は2価の複素環基を表し、これらの基は置換基を有していてもよい。
Ar4、Ar5及びAr6はそれぞれ、当該基が結合している窒素原子に結合している当該基以外の基と、直接又は酸素原子若しくは硫黄原子を介して結合して、環を形成していてもよい。
KAは、アルキレン基、シクロアルキレン基、アリーレン基、2価の複素環基、-NR’-で表される基、酸素原子又は硫黄原子を表し、これらの基は置換基を有していてもよい。R’は、水素原子、アルキル基、シクロアルキル基、アリール基又は1価の複素環基を表し、これらの基は置換基を有していてもよい。KAが複数存在する場合、それらは同一でも異なっていてもよい。
X’は、前記架橋基A群から選ばれる架橋基、水素原子、アルキル基、シクロアルキル基、アリール基又は1価の複素環基を表し、これらの基は置換基を有していてもよい。X’が複数存在する場合、それらは同一でも異なっていてもよい。但し、少なくとも1つのX’は、前記架橋基A群から選ばれる架橋基である。]
[4]前記蛍光発光性低分子化合物が、式(B)で表される化合物である、[1]~[3]のいずれかに記載の発光素子。
n1Bは、0~15の整数を表す。
Ar1Bは、芳香族炭化水素基又は芳香族複素環基を表し、これらの基は置換基を有していてもよい。該置換基が複数存在する場合、それらは同一でも異なっていてもよく、互いに結合して、それぞれが結合する原子とともに環を形成していてもよい。
R1Bは、アルキル基、シクロアルキル基、アルコキシ基、シクロアルコキシ基、アリール基、1価の複素環基、置換アミノ基、アルケニル基、シクロアルケニル基、アルキニル基又はシクロアルキニル基を表し、これらの基は置換基を有していてもよい。R1Bが複数存在する場合、同一でも異なっていてもよく、互いに結合して、それぞれが結合する炭素原子とともに環を形成していてもよい。]
[5]前記n1Bが、1~8の整数である、[4]に記載の発光素子。
[6]前記Ar1Bが、置換基を有していてもよい芳香族炭化水素基である、[4]又は[5]に記載の発光素子。
[7]前記Ar1Bが、ベンゼン環、ビフェニル環、ナフタレン環、アントラセン環、フェナントレン環、ジヒドロフェナントレン環、トリフェニレン環、ナフタセン環、フルオレン環、スピロビフルオレン環、ピレン環、ペリレン環、クリセン環、インデン環、フルオランテン環、ベンゾフルオランテン環又はアセナフトフルオランテン環から、環を構成する炭素原子に直接結合する水素原子1個以上を除いてなる基(該基は置換基を有していてもよい)である、[6]に記載の発光素子。
[8]前記Ar1Bが、ピレン環、クリセン環、フルオランテン環又はベンゾフルオランテン環から、環を構成する炭素原子に直接結合する水素原子1個以上を除いてなる基(該基は置換基を有していてもよい)である、[7]に記載の発光素子。
[9]前記R1Bが、アルキル基、シクロアルキル基、アリール基、1価の複素環基、置換アミノ基、アルケニル基又はシクロアルケニル基(これらの基は置換基を有していてもよい)である、[4]~[8]のいずれかに記載の発光素子。
[10]前記R1Bが、アリール基、置換アミノ基又はアルケニル基(これらの基は置換基を有していてもよい)である、[9]に記載の発光素子。
[11]前記蛍光発光性低分子化合物の発光スペクトルの最大ピーク波長が380nm以上570nm以下である、[1]~[10]のいずれかに記載の発光素子。
[12]前記(Y1×1000)/X1の値が、0.85以上4.0以下である、[1]~[11]のいずれかに記載の発光素子。
[13]前記第1の有機層が、前記蛍光発光性低分子化合物とホスト材料とを含有する層であり、前記ホスト材料が式(FH-1)で表される化合物又は式(Y)で表される構成単位を含む高分子化合物であり、前記蛍光発光性低分子化合物の含有量が、前記蛍光発光性低分子化合物と前記ホスト材料との合計を100質量部とした場合、0.1~50質量部である、[1]~[12]のいずれかに記載の発光素子。
ArH1及びArH2は、それぞれ独立に、アリール基、1価の複素環基又は置換アミノ基を表し、これらの基は置換基を有していてもよい。
nH1は、0~15の整数を表す。
LH1は、アリーレン基、2価の複素環基、又は、-[C(RH11)2]nH11-で表される基を表し、これらの基は置換基を有していてもよい。LH1が複数存在する場合、それらは同一でも異なっていてもよい。nH11は、1~10の整数を表す。RH11は、水素原子、アルキル基、シクロアルキル基、アルコキシ基、シクロアルコキシ基、アリール基又は1価の複素環基を表し、これらの基は置換基を有していてもよい。複数存在するRH11は、同一でも異なっていてもよく、互いに結合して、それぞれが結合する炭素原子とともに環を形成していてもよい。]
[14]前記第1の有機層が、正孔輸送材料、正孔注入材料、電子輸送材料、電子注入材料、酸化防止剤、及び、前記蛍光発光性低分子化合物とは異なる発光材料からなる群より選ばれる少なくとも1種の材料を更に含有する、[1]~[13]のいずれかに記載の発光素子。
[15]前記第2の有機層が、前記陽極及び前記第1の有機層との間に設けられた層である、[1]~[14]のいずれかに記載の発光素子。
本明細書で共通して用いられる用語は、特記しない限り、以下の意味である。
次に、本発明の一実施形態に係る発光素子について説明する。
第1の有機層は、蛍光発光性低分子化合物を含有する層である。第1の有機層には、蛍光発光性低分子化合物が1種単独で含有されていてもよく、2種以上含有されていてもよい。
「蛍光発光性低分子化合物」は、通常、室温(25℃)で蛍光発光性を示す低分子化合物を意味するが、好ましくは、室温で一重項励起状態からの発光を示す低分子化合物である。
n1Bは、0~15の整数を表し、好ましくは1~8の整数であり、より好ましくは1~6の整数であり、更に好ましくは1~4の整数であり、特に好ましくは2~4の整数である。
本実施形態に係る発光素子の外部量子効率がより優れるので、第1の有機層は、蛍光発光性低分子化合物と、正孔注入性、正孔輸送性、電子注入性及び電子輸送性からなる群から選ばれる少なくとも1つの機能を有するホスト材料とを含有する層であることが好ましい。第1の有機層が、蛍光発光性低分子化合物とホスト材料とを含有する層である場合、ホスト材料は、1種単独で含有されていても、2種以上含有されていてもよい。
ホスト材料として好ましい低分子化合物(以下、「低分子ホスト」ともいう。)に関して説明する。
ホスト材料として好ましい高分子化合物(以下、「高分子ホスト」ともいう。)に関して説明する。
aX1及びaX2は、それぞれ独立に、0以上の整数を表す。
ArX1及びArX3は、それぞれ独立に、アリーレン基又は2価の複素環基を表し、これらの基は置換基を有していてもよい。
ArX2及びArX4は、それぞれ独立に、アリーレン基、2価の複素環基、又は、少なくとも1種のアリーレン基と少なくとも1種の2価の複素環基とが直接結合した2価の基を表し、これらの基は置換基を有していてもよい。ArX2及びArX4が複数存在する場合、それらは同一でも異なっていてもよい。
RX1、RX2及びRX3は、それぞれ独立に、水素原子、アルキル基、シクロアルキル基、アリール基又は1価の複素環基を表し、これらの基は置換基を有していてもよい。
RX2及びRX3が複数存在する場合、それらは同一でも異なっていてもよい。
高分子ホストは、ケミカルレビュー(Chem. Rev.),第109巻,897-1091頁(2009年)等に記載の公知の重合方法を用いて製造することができ、Suzuki反応、Buchwald反応、Stille反応、Negishi反応及びKumada反応等の遷移金属触媒を用いるカップリング反応により重合させる方法が例示される。
第1の有機層は、蛍光発光性低分子化合物と、前述のホスト材料、正孔輸送材料、正孔注入材料、電子輸送材料、電子注入材料、酸化防止剤、及び、発光材料(蛍光発光性低分子化合物とは異なる。)からなる群から選ばれる少なくとも1種の材料とを含む組成物(以下、「第1の組成物」ともいう。)を含有する層であってもよい。
正孔輸送材料は、低分子化合物と高分子化合物とに分類され、好ましくは高分子化合物である。正孔輸送材料は、架橋基を有していてもよい。
電子輸送材料は、低分子化合物と高分子化合物とに分類される。電子輸送材料は、架橋基を有していてもよい。
正孔注入材料及び電子注入材料は、各々、低分子化合物と高分子化合物とに分類される。正孔注入材料及び電子注入材料は、架橋基を有していてもよい。
正孔注入材料又は電子注入材料が導電性高分子を含む場合、導電性高分子の電気伝導度は、好ましくは、1×10-5S/cm~1×103S/cmである。導電性高分子の電気伝導度をかかる範囲とするために、導電性高分子に適量のイオンをドープすることができる。
発光材料は、低分子化合物と高分子化合物とに分類される。発光材料は、架橋基を有していてもよい。
酸化防止剤は、蛍光発光性低分子化合物と同じ溶媒に可溶であり、発光及び電荷輸送を阻害しない化合物であればよく、例えば、フェノール系酸化防止剤、リン系酸化防止剤が挙げられる。
第1の有機層を形成するための第1のインクとして、蛍光発光性低分子化合物と、溶媒とを含有する組成物を用いることができる。第1のインクは、スピンコート法、キャスティング法、マイクログラビアコート法、グラビアコート法、バーコート法、ロールコート法、ワイヤーバーコート法、ディップコート法、スプレーコート法、スクリーン印刷法、フレキソ印刷法、オフセット印刷法、インクジェット印刷法、キャピラリーコート法、ノズルコート法等の湿式法に好適に使用することができる。
第2の有機層は、架橋基を有する架橋構成単位を含む高分子化合物(以下、「第2の有機層の高分子化合物」ともいう。)の架橋体を含有する層である。
第2の有機層の高分子化合物は、本実施形態に係る発光素子の外部量子効率が優れるので、上記架橋基A群から選ばれる少なくとも1種の架橋基を有する架橋構成単位を含む高分子化合物であることが好ましい。
nAは、0~5の整数を表し、本実施形態に係る発光素子の外部量子効率がより優れるので、好ましくは0~3の整数であり、より好ましくは0~2の整数であり、更に好ましくは1又は2である。
mAは、0~5の整数を表し、本実施形態に係る発光素子の外部量子効率がより優れるので、好ましくは0~3の整数であり、より好ましくは0~2の整数であり、更に好ましくは0又は1であり、特に好ましくは0である。
式(2)で表される構成単位としては、例えば、式(2-1)~式(2-30)で表される構成単位が挙げられ、式(2’)で表される構成単位としては、例えば、式(2’-1)~式(2’-9)で表される構成単位が挙げられる。これらの中でも、第2の有機層の高分子化合物の架橋性が優れるので、好ましくは式(2-1)~式(2-30)で表される構成単位であり、より好ましくは式(2-1)~式(2-15)、式(2-19)、式(2-20)、式(2-23)、式(2-25)又は式(2-30)で表される構成単位であり、更に好ましくは式(2-1)~式(2-9)、式(2-20)、式(2-22)又は式(2-30)で表される構成単位である。
第2の有機層の高分子化合物は、正孔輸送性が優れるので、更に、式(X)で表される構成単位を含むことが好ましい。また、第2の有機層の高分子化合物は、本実施形態に係る発光素子の外部量子効率がより優れるので、更に、式(Y)で表される構成単位を含むことが好ましい。
第2の有機層の高分子化合物は、前述の高分子ホストの製造方法と同様の方法で製造することができる。
第2の有機層の高分子化合物における(Y1×1000)/X1の値は、以下の方法で求めることができる。
(0.45×776.45)+(0.05×240.20)+(0.50×750.51)=736.67
(0.45×2)+(0.05×2)+(0.50×0)=1.00
(1.00×1000)/736.67=1.36
0.38×0.5+0×0.5=0.19
第2の有機層は、第2の有機層の高分子化合物の架橋体と、正孔輸送材料、正孔注入材料、電子輸送材料、電子注入材料、酸化防止剤、及び、発光材料からなる群から選ばれる少なくとも1種の材料とを含む組成物(以下、「第2の組成物」ともいう。)を含有する層であってもよい。
第2の組成物において、正孔輸送材料、電子輸送材料、正孔注入材料、電子注入材料及び発光材料の配合量は、各々、第2の有機層の高分子化合物の架橋体を100質量部とした場合、通常、1~400質量部であり、好ましくは5~150質量部である。
第2の有機層を形成するための第2のインクとして、第2の有機層の高分子化合物と、溶媒とを含有する第2の組成物を用いることができる。第2のインクは、第1のインクの項で説明した湿式法に好適に使用することができる。第2のインクの粘度の好ましい範囲は、第1のインクの粘度の好ましい範囲と同じである。第2のインクに含有される溶媒の例及び好ましい範囲は、第1のインクに含有される溶媒の例及び好ましい範囲と同じである。
本実施形態に係る発光素子は、陽極と、陰極と、前記陽極及び前記陰極の間に設けられた第1の有機層と、前記陽極及び前記陰極の間に、前記第1の有機層に隣接して設けられた第2の有機層と、を有する。本実施形態に係る発光素子は、陽極、陰極、第1の有機層及び第2の有機層以外の層を有していてもよい。
(D2)陽極/正孔輸送層(第2の有機層)/第1の発光層(第1の有機層)/陰極
(D3)陽極/正孔注入層/第2の発光層(第2の有機層)/第1の発光層(第1の有機層)/陰極
(D4)陽極/正孔注入層/第2の発光層(第2の有機層)/第1の発光層(第1の有機層)/電子輸送層/陰極
(D5)陽極/正孔注入層/第2の発光層(第2の有機層)/第1の発光層(第1の有機層)/電子注入層/陰極
(D6)陽極/正孔注入層/第2の発光層(第2の有機層)/第1の発光層(第1の有機層)/電子輸送層/電子注入層/陰極
(D7)陽極/正孔注入層/正孔輸送層(第2の有機層)/第1の発光層(第1の有機層)/陰極
(D8)陽極/正孔注入層/正孔輸送層(第2の有機層)/第1の発光層(第1の有機層)/電子輸送層/陰極
(D9)陽極/正孔注入層/正孔輸送層(第2の有機層)/第1の発光層(第1の有機層)/電子注入層/陰極
(D10)陽極/正孔注入層/正孔輸送層(第2の有機層)/第1の発光層(第1の有機層)/電子輸送層/電子注入層/陰極
(D11)陽極/正孔注入層/正孔輸送層/第2の発光層(第2の有機層)/第1の発光層(第1の有機層)/電子輸送層/電子注入層/陰極
(D12)陽極/正孔注入層/正孔輸送層(第2の有機層)/第1の発光層(第1の有機層)/第2の発光層/電子輸送層/電子注入層/陰極
(D13)陽極/正孔注入層/正孔輸送層/第1の発光層(第1の有機層)/第2の発光層(第2の有機層)/電子輸送層/電子注入層/陰極
(D14)陽極/正孔注入層/正孔輸送層/第1の発光層(第1の有機層)/電子輸送層(第2の有機層)/電子注入層/陰極
第2の発光層は、通常、第2の有機層又は発光材料を含有する層である。第2の発光層が発光材料を含有する層である場合、第2の発光層に含有される発光材料としては、例えば、前述の第1の組成物が含有していてもよい発光材料が挙げられる。第2の発光層に含有される発光材料は、1種単独で含有されていても、2種以上が含有されていてもよい。
正孔輸送層は、通常、第2の有機層又は正孔輸送材料を含有する層である。正孔輸送層が正孔輸送材料を含有する層である場合、正孔輸送材料としては、例えば、前述の第1の組成物が含有していてもよい正孔輸送材料が挙げられる。正孔輸送層に含有される正孔輸送材料は、1種単独で含有されていても、2種以上が含有されていてもよい。
電子輸送層は、通常、第2の有機層であるか、又は、電子輸送材料を含有する層であり、好ましくは、電子輸送材料を含有する層である。電子輸送層が電子輸送材料を含有する層である場合、電子輸送層に含有される電子輸送材料としては、例えば、前述の第1の組成物が含有していてもよい電子輸送材料が挙げられる。電子輸送層に含有される電子輸送材料は、1種単独で含有されていても、2種以上が含有されていてもよい。
正孔注入層は、正孔注入材料を含有する層である。正孔注入層に含有される正孔注入材料としては、例えば、前述の第1の組成物が含有していてもよい正孔注入材料が挙げられる。正孔注入層に含有される正孔注入材料は、1種単独で含有されていても、2種以上が含有されていてもよい。
発光素子における基板は、電極を形成することができ、且つ、有機層を形成する際に化学的に変化しない基板であればよく、例えば、ガラス、プラスチック、シリコン等の材料からなる基板である。不透明な基板を使用する場合には、基板から最も遠くにある電極が透明又は半透明であることが好ましい。
本実施形態に係る発光素子において、第1の発光層、第2の発光層、正孔輸送層、電子輸送層、正孔注入層、電子注入層等の各層の形成方法としては、低分子化合物を用いる場合、例えば、粉末からの真空蒸着法、溶液又は溶融状態からの成膜による方法が挙げられ、高分子化合物を用いる場合、例えば、溶液又は溶融状態からの成膜による方法が挙げられる。
発光素子を用いて面状の発光を得るためには、面状の陽極と陰極が重なり合うように配置すればよい。パターン状の発光を得るためには、面状の発光素子の表面にパターン状の窓を設けたマスクを設置する方法、非発光部にしたい層を極端に厚く形成し実質的に非発光とする方法、陽極若しくは陰極、又は両方の電極をパターン状に形成する方法がある。これらのいずれかの方法でパターンを形成し、いくつかの電極を独立にON/OFFできるように配置することにより、数字、文字等を表示できるセグメントタイプの表示装置が得られる。ドットマトリックス表示装置とするためには、陽極と陰極を共にストライプ状に形成して直交するように配置すればよい。複数の種類の発光色の異なる高分子化合物を塗り分ける方法、カラーフィルター又は蛍光変換フィルターを用いる方法により、部分カラー表示、マルチカラー表示が可能となる。ドットマトリックス表示装置は、パッシブ駆動も可能であるし、TFT等と組み合わせてアクティブ駆動も可能である。これらの表示装置は、コンピュータ、テレビ、携帯端末等のディスプレイに用いることができる。面状の発光素子は、液晶表示装置のバックライト用の面状光源、又は、面状の照明用光源として好適に用いることができる。フレキシブルな基板を用いれば、曲面状の光源及び表示装置としても使用できる。
[測定条件]
測定する高分子化合物を約0.05質量%の濃度でテトラヒドロフラン(THF)に溶解させ、SECに10μL注入した。SECの移動相としてTHFを用い、2.0mL/分の流量で流した。カラムとして、PLgel MIXED-B(ポリマーラボラトリーズ製)を用いた。検出器にはUV-VIS検出器(島津製作所製、商品名:SPD-10Avp)を用いた。
化合物EM-1は、国際公開第2008/059713号に記載の方法に準じて合成した。
化合物EM-2は、特開2006-176491号公報に記載の方法に準じて合成した。
化合物EM-3は、国際公開第2005/033051号に記載の方法に準じて合成した。
化合物EM-4及び化合物EM-5は、東京化成工業株式会社より購入した。
化合物EM-6は、国際公開第2010/013006号に記載の方法に準じて合成した。
化合物EM-7は、Aldrich社より購入した。
化合物EM-A1は、特開2011-105643号公報に記載の方法に準じて合成した。
化合物EM-A2は、国際公開第2007/058368号に記載の方法に従って合成した。
化合物EM-2の発光スペクトルの最大ピーク波長は、446nmであった。
化合物EM-3の発光スペクトルの最大ピーク波長は、453nmであった。
化合物EM-4の発光スペクトルの最大ピーク波長は、446nmであった。
化合物EM-5の発光スペクトルの最大ピーク波長は、404nmであった。
化合物EM-6の発光スペクトルの最大ピーク波長は、453nmであった。
化合物EM-7の発光スペクトルの最大ピーク波長は、448nmであった。
化合物EM-A1の発光スペクトルの最大ピーク波長は、454nmであった。
化合物EM-A2の発光スペクトルの最大ピーク波長は、521nmであった。
化合物HM-1は、AK Scientific社より購入した。
化合物HM-2は、特開2011-100942号公報及び国際公開第2011/137922号に記載の方法に準じて合成した。
化合物HM-2の発光スペクトルの最大ピーク波長は、430nmであった。
化合物M1は、特開2012-144721号公報に記載の方法に従って合成した。
化合物M2は、市販品を用いた。
化合物M3は、国際公開第2015/145871号に記載の方法に従って合成した。
化合物M4は、国際公開第2013/146806号に記載の方法に従って合成した。
化合物M5は、国際公開第2005/049546号に記載の方法に従って合成した。
化合物M6は、特開2010-189630号公報に記載の方法に従って合成した。
(工程1)反応容器内を不活性ガス雰囲気とした後、化合物M1(1.73g)、化合物M2(0.843g)、ジクロロビス〔トリス(2-メトキシフェニル)ホスフィン〕パラジウム(2.2mg)及びトルエン(40ml)を加え、105℃に加熱した。
(工程2)得られた反応液に、20質量%水酸化テトラエチルアンモニウム水溶液(8.7g)を滴下し、3時間還流させた。
(工程3)その後、そこに、9-ブロモアントラセン(64.1mg)、20質量%水酸化テトラエチルアンモニウム水溶液(8.8g)及びジクロロビス〔トリス(2-メトキシフェニル)ホスフィン〕パラジウム(2.2mg)を加え、16時間還流させた。
(工程4)その後、そこに、ジエチルジチアカルバミン酸ナトリウム水溶液を加え、80℃で2時間撹拌した。得られた反応液を冷却後、水で2回、3質量%酢酸水溶液で2回、水で2回洗浄し、得られた溶液をメタノールに滴下したところ、沈殿が生じた。沈殿物をトルエンに溶解させ、アルミナカラム、シリカゲルカラムの順番で通液することにより精製した。得られた溶液をメタノールに滴下し、撹拌したところ、沈殿が生じた。沈殿物をろ取し、乾燥させることにより、高分子化合物HP-1を0.91g得た。高分子化合物HP-1のMnは1.2×105であり、Mwは4.8×105であった。
高分子化合物HTL-1は、化合物M5及び化合物M6を用いて、国際公開第2015/194448号に記載の方法に従って合成した。
(工程1)反応容器内を不活性ガス雰囲気とした後、化合物M3(0.130g)、化合物M4(0.0620g)、化合物M6(0.493g)、化合物M5(1.15g)、ジクロロビス(トリス-o-メトキシフェニルホスフィン)パラジウム(2.2mg)及びトルエン(30mL)を加え、105℃に加熱した。
(工程2)反応液に、20質量%水酸化テトラエチルアンモニウム水溶液(8.3mL)を滴下し、6時間還流させた。
(工程3)その後、そこに、フェニルボロン酸(61.0mg)及びジクロロビス(トリス-o-メトキシフェニルホスフィン)パラジウム(1.1mg)を加え、14.5時間還流させた。
(工程4)その後、そこに、ジエチルジチアカルバミン酸ナトリウム水溶液を加え、80℃で2時間撹拌した。冷却後、得られた反応液を、水で2回、3質量%酢酸水溶液で2回、水で2回洗浄し、得られた溶液をメタノールに滴下したところ、沈澱が生じた。得られた沈殿物をトルエンに溶解させ、アルミナカラム、シリカゲルカラムの順番で通すことにより精製した。得られた溶液をメタノールに滴下し、撹拌した後、得られた沈殿物をろ取し、乾燥させることにより、高分子化合物HTL-2を1.05g得た。
高分子化合物HTL-2の合成における(工程1)を下記(工程1-1)に変更し、(工程2)を下記(工程2-1)に変更し、(工程3)を下記(工程3-1)に変更したこと以外は、上記高分子化合物HTL-2の合成と同様の方法により、高分子化合物HTL-3を0.92g得た。
(工程2-1)反応液に、20質量%水酸化テトラエチルアンモニウム水溶液(6.7mL)を滴下し、6時間還流させた。
(工程3-1)その後、そこに、フェニルボロン酸(48.8mg)及びジクロロビス(トリス-o-メトキシフェニルホスフィン)パラジウム(0.88mg)を加え、14.5時間還流させた。
高分子化合物HTL-3の合成における(工程1-1)を下記(工程1-2)に変更したこと以外は、上記高分子化合物HTL-3の合成と同様の方法により、高分子化合物HTL-4を0.92g得た。
高分子化合物HTL-5は、化合物M3、化合物M4及び化合物M5を用いて、国際公開第2015/145871号に記載の方法に従って合成した。
(陽極及び正孔注入層の形成)
ガラス基板にスパッタ法により45nmの厚みでITO膜を付けることにより陽極を形成した。該陽極上に、正孔注入材料であるND-3202(日産化学工業製)をスピンコート法により35nmの厚さで成膜した。大気雰囲気下において、50℃、3分間加熱し、更に230℃、15分間加熱することにより正孔注入層を形成した。
キシレンに、高分子化合物HTL-5を0.6質量%の濃度で溶解させた。得られたキシレン溶液を用いて、正孔注入層の上にスピンコート法により20nmの厚さで成膜し、窒素ガス雰囲気下において、ホットプレート上で180℃、60分間加熱することにより第2の有機層を形成した。この加熱により、高分子化合物HTL-5は、架橋体となった。
トルエンに、化合物HM-1及び化合物EM-A1(化合物HM-1/化合物EM-A1=91.5質量%/8.5質量%)を2質量%の濃度で溶解させた。得られたトルエン溶液を用いて、第2の有機層の上にスピンコート法により60nmの厚さで成膜し、窒素ガス雰囲気下において、ホットプレート上で150℃、10分間加熱することにより第1の有機層を形成した。
第1の有機層を形成した基板を蒸着機内において、1×10-4Pa以下にまで減圧した後、陰極として、第1の有機層の上に、フッ化ナトリウムを約4nm、次いで、フッ化ナトリウム層の上に、アルミニウムを約80nm蒸着した。蒸着後、ガラス基板を用いて封止することにより、発光素子D1を作製した。
発光素子D1に電圧を印加することによりEL発光が観測された。200cd/m2における外部量子効率は2.99%であり、CIE色度座標(x,y)は(0.14,0.18)であった。
実施例D1における高分子化合物HTL-5に代えて、高分子化合物HTL-4を用いたこと以外は、実施例D1と同様にして、発光素子D2を作製した。
発光素子D2に電圧を印加することによりEL発光が観測された。200cd/m2における外部量子効率は2.87%であり、CIE色度座標(x,y)は(0.14,0.18)であった。
実施例D1における高分子化合物HTL-5に代えて、高分子化合物HTL-3を用いたこと以外は、実施例D1と同様にして、発光素子D3を作製した。
発光素子D3に電圧を印加することによりEL発光が観測された。200cd/m2における外部量子効率は2.32%であり、CIE色度座標(x,y)は(0.14,0.17)であった。
実施例D1における高分子化合物HTL-5に代えて、高分子化合物HTL-2及び高分子化合物HTL-3(高分子化合物HTL-2/高分子化合物HTL-3=45質量%/55質量%)を用いたこと以外は、実施例D1と同様にして、発光素子CD1を作製した。なお、上記高分子化合物HTL-2及び高分子化合物HTL-3を45:55の比で配合したものについて、上述の方法で(Y1×1000)/X1の値を算出すると、0.55であった。
発光素子CD1に電圧を印加することによりEL発光が観測された。200cd/m2における外部量子効率は1.77%であり、CIE色度座標(x,y)は(0.14,0.17)であった。
実施例D1における高分子化合物HTL-5に代えて、高分子化合物HTL-2を用いたこと以外は、実施例D1と同様にして、発光素子CD2を作製した。
発光素子CD2に電圧を印加することによりEL発光が観測された。200cd/m2における外部量子効率は1.38%であり、CIE色度座標(x,y)は(0.14,0.16)であった。
実施例D1における高分子化合物HTL-5に代えて、高分子化合物HTL-1及び高分子化合物HTL-2(高分子化合物HTL-1/高分子化合物HTL-2=50質量%/50質量%)を用いたこと以外は、実施例D1と同様にして、発光素子CD3を作製した。なお、上記高分子化合物HTL-1及び高分子化合物HTL-2を50:50の比で配合したものについて、上述の方法で(Y1×1000)/X1の値を算出すると、0.19であった。
発光素子CD3に電圧を印加することによりEL発光が観測された。200cd/m2における外部量子効率は0.89%であり、CIE色度座標(x,y)は(0.14,0.17)であった。
実施例D1における高分子化合物HTL-5に代えて、高分子化合物HTL-1を用いたこと以外は、実施例D1と同様にして、発光素子CD4を作製した。
発光素子CD4に電圧を印加することによりEL発光が観測された。200cd/m2における外部量子効率は0.75%であり、CIE色度座標(x,y)は(0.14,0.17)であった。
(陽極及び正孔注入層の形成)
ガラス基板にスパッタ法により45nmの厚みでITO膜を付けることにより陽極を形成した。該陽極上に、正孔注入材料であるND-3202(日産化学工業製)をスピンコート法により35nmの厚さで成膜した。大気雰囲気下において、50℃、3分間加熱し、更に230℃、15分間加熱することにより正孔注入層を形成した。
キシレンに、高分子化合物HTL-5を0.6質量%の濃度で溶解させた。得られたキシレン溶液を用いて、正孔注入層の上にスピンコート法により20nmの厚さで成膜し、窒素ガス雰囲気下において、ホットプレート上で180℃、60分間加熱することにより第2の有機層を形成した。この加熱により、高分子化合物HTL-5は、架橋体となった。
トルエンに、化合物HM-1及び化合物EM-1(化合物HM-1/化合物EM-1=91.5質量%/8.5質量%)を2質量%の濃度で溶解させた。得られたトルエン溶液を用いて、第2の有機層の上にスピンコート法により60nmの厚さで成膜し、窒素ガス雰囲気下において、ホットプレート上で150℃、10分間加熱することにより第1の有機層を形成した。
第1の有機層を形成した基板を蒸着機内において、1.0×10-4Pa以下にまで減圧した後、陰極として、第1の有機層の上に、フッ化ナトリウムを約4nm、次いで、フッ化ナトリウム層の上に、アルミニウムを約80nm蒸着した。蒸着後、ガラス基板を用いて封止することにより、発光素子D4を作製した。
発光素子D4に電圧を印加することによりEL発光が観測された。50cd/m2における外部量子効率は2.33%であり、CIE色度座標(x,y)は(0.16,0.22)であった。
実施例D4における高分子化合物HTL-5に代えて、高分子化合物HTL-4を用いたこと以外は、実施例D4と同様にして、発光素子D5を作製した。
発光素子D5に電圧を印加することによりEL発光が観測された。50cd/m2における外部量子効率は2.28%であり、CIE色度座標(x,y)は(0.16,0.23)であった。
実施例D4における高分子化合物HTL-5に代えて、高分子化合物HTL-3を用いたこと以外は、実施例D4と同様にして、発光素子D6を作製した。
発光素子D6に電圧を印加することによりEL発光が観測された。50cd/m2における外部量子効率は2.06%であり、CIE色度座標(x,y)は(0.16,0.21)であった。
実施例D4における化合物EM-1に代えて、化合物EM-2を用いたこと以外は、実施例D4と同様にして、発光素子D7を作製した。
発光素子D7に電圧を印加することによりEL発光が観測された。50cd/m2における外部量子効率は2.03%であり、CIE色度座標(x,y)は(0.16,0.22)であった。
実施例D4における化合物EM-1に代えて、化合物EM-3を用いたこと以外は、実施例D4と同様にして、発光素子D8を作製した。
発光素子D8に電圧を印加することによりEL発光が観測された。50cd/m2における外部量子効率は1.63%であり、CIE色度座標(x,y)は(0.18,0.28)であった。
実施例D4における化合物EM-1に代えて、化合物EM-4を用いたこと以外は、実施例D4と同様にして、発光素子D9を作製した。
発光素子D9に電圧を印加することによりEL発光が観測された。50cd/m2における外部量子効率は1.53%であり、CIE色度座標(x,y)は(0.17,0.24)であった。
実施例D4における化合物HM-1に代えて、高分子化合物HP-1を用いたこと以外は、実施例D4と同様にして、発光素子D10を作製した。
発光素子D10に電圧を印加することによりEL発光が観測された。50cd/m2における外部量子効率は3.74%であり、CIE色度座標(x,y)は(0.15,0.16)であった。
実施例D4における化合物HM-1に代えて、化合物HM-2を用いたこと以外は、実施例D4と同様にして、発光素子D11を作製した。
発光素子D11に電圧を印加することによりEL発光が観測された。50cd/m2における外部量子効率は2.69%であり、CIE色度座標(x,y)は(0.16,0.22)であった。
実施例D4における高分子化合物HTL-5に代えて、高分子化合物HTL-1を用いたこと以外は、実施例D4と同様にして、発光素子CD5を作製した。
発光素子CD5に電圧を印加することによりEL発光が観測された。50cd/m2における外部量子効率は0.33%であり、CIE色度座標(x,y)は(0.16,0.19)であった。
実施例D1における化合物EM-A1に代えて、化合物EM-A2を用いたこと以外は、実施例D1と同様にして、発光素子D12を作製した。
発光素子D12に電圧を印加することによりEL発光が観測された。400cd/m2における外部量子効率は2.00%であり、CIE色度座標(x,y)は(0.27,0.64)であった。
実施例D12における高分子化合物HTL-5に代えて、高分子化合物HTL-4を用いたこと以外は、実施例D12と同様にして、発光素子D13を作製した。
発光素子D13に電圧を印加することによりEL発光が観測された。400cd/m2における外部量子効率は1.69%であり、CIE色度座標(x,y)は(0.27,0.64)であった。
実施例D12における高分子化合物HTL-5に代えて、高分子化合物HTL-2及び高分子化合物HTL-3(高分子化合物HTL-2/高分子化合物HTL-3=45質量%/55質量%)を用いたこと以外は、実施例D12と同様にして、発光素子CD6を作製した。
発光素子CD6に電圧を印加することによりEL発光が観測された。400cd/m2における外部量子効率は0.45%であり、CIE色度座標(x,y)は(0.27,0.64)であった。
実施例D12における高分子化合物HTL-5に代えて、高分子化合物HTL-2を用いたこと以外は、実施例D12と同様にして、発光素子CD7を作製した。
発光素子CD7に電圧を印加することによりEL発光が観測された。400cd/m2における外部量子効率は0.59%であり、CIE色度座標(x,y)は(0.27,0.64)であった。
実施例D12における高分子化合物HTL-5に代えて、高分子化合物HTL-1を用いたこと以外は、実施例D12と同様にして、発光素子CD8を作製した。
発光素子CD8に電圧を印加することによりEL発光が観測された。400cd/m2における外部量子効率は0.62%であり、CIE色度座標(x,y)は(0.27,0.64)であった。
実施例D1における化合物EM-A1に代えて、化合物EM-5を用いたこと以外は、実施例D1と同様にして、発光素子D14を作製した。
発光素子D14に電圧を印加することによりEL発光が観測された。400cd/m2における外部量子効率は1.24%であり、CIE色度座標(x,y)は(0.16,0.22)であった。
実施例D14における高分子化合物HTL-5に代えて、高分子化合物HTL-3を用いたこと以外は、実施例D14と同様にして、発光素子D15を作製した。
発光素子D15に電圧を印加することによりEL発光が観測された。400cd/m2における外部量子効率は1.07%であり、CIE色度座標(x,y)は(0.16,0.23)であった。
実施例D14における高分子化合物HTL-5に代えて、高分子化合物HTL-1を用いたこと以外は、実施例D14と同様にして、発光素子CD9を作製した。
発光素子CD9に電圧を印加することによりEL発光が観測された。400cd/m2における外部量子効率は0.60%であり、CIE色度座標(x,y)は(0.16,0.24)であった。
実施例D4と同様にして、発光素子D16を作製した。
発光素子D16に電圧を印加することによりEL発光が観測された。1000cd/m2における外部量子効率は2.30%であり、CIE色度座標(x,y)は(0.16,0.22)であった。
実施例D4における化合物EM-1に代えて、化合物EM-6を用いたこと以外は、実施例D4と同様にして、発光素子D17を作製した。
発光素子D17に電圧を印加することによりEL発光が観測された。1000cd/m2における外部量子効率は1.78%であり、CIE色度座標(x,y)は(0.14,0.18)であった。
実施例D4における化合物EM-1に代えて、化合物EM-7を用いたこと以外は、実施例D4と同様にして、発光素子D18を作製した。
発光素子D18に電圧を印加することによりEL発光が観測された。1000cd/m2における外部量子効率は1.37%であり、CIE色度座標(x,y)は(0.16,0.19)であった。
Claims (15)
- 陽極と、
陰極と、
前記陽極及び前記陰極の間に設けられた第1の有機層と、
前記陽極及び前記陰極の間に、前記第1の有機層に隣接して設けられた第2の有機層と、を有する発光素子であって、
前記第1の有機層が、蛍光発光性低分子化合物を含有する層であり、
前記蛍光発光性低分子化合物の発光スペクトルの最大ピーク波長が380nm以上750nm以下であり、
前記第2の有機層が、架橋基を有する架橋構成単位を含む高分子化合物の架橋体を含有する層であり、
前記高分子化合物を構成する各構成単位について、全構成単位の総モルに対するその構成単位のモル比Cとその構成単位の分子量Mとを乗じた値x、及び、前記モル比Cとその構成単位が有する前記架橋基の数nとを乗じた値yを求めたとき、前記xの総和X1及び前記yの総和Y1から計算される(Y1×1000)/X1の値が、0.60以上である、発光素子。 - 前記架橋構成単位が、式(2)で表される構成単位又は式(2’)で表される構成単位である、請求項2に記載の発光素子。
nAは0~5の整数を表し、nは1又は2を表す。nAが複数存在する場合、それらは同一でも異なっていてもよい。
Ar3は、芳香族炭化水素基又は複素環基を表し、これらの基は置換基を有していてもよい。
LAは、アルキレン基、シクロアルキレン基、アリーレン基、2価の複素環基、-NR’-で表される基、酸素原子又は硫黄原子を表し、これらの基は置換基を有していてもよい。R’は、水素原子、アルキル基、シクロアルキル基、アリール基又は1価の複素環基を表し、これらの基は置換基を有していてもよい。LAが複数存在する場合、それらは同一でも異なっていてもよい。
Xは、前記架橋基A群から選ばれる架橋基を表す。Xが複数存在する場合、それらは同一でも異なっていてもよい。]
mAは0~5の整数を表し、mは1~4の整数を表し、cは0又は1の整数を表す。mAが複数存在する場合、それらは同一でも異なっていてもよい。
Ar5は、芳香族炭化水素基、複素環基、又は、少なくとも1種の芳香族炭化水素環と少なくとも1種の複素環とが直接結合した基を表し、これらの基は置換基を有していてもよい。
Ar4及びAr6は、それぞれ独立に、アリーレン基又は2価の複素環基を表し、これらの基は置換基を有していてもよい。
Ar4、Ar5及びAr6はそれぞれ、当該基が結合している窒素原子に結合している当該基以外の基と、直接又は酸素原子若しくは硫黄原子を介して結合して、環を形成していてもよい。
KAは、アルキレン基、シクロアルキレン基、アリーレン基、2価の複素環基、-NR’-で表される基、酸素原子又は硫黄原子を表し、これらの基は置換基を有していてもよい。R’は、水素原子、アルキル基、シクロアルキル基、アリール基又は1価の複素環基を表し、これらの基は置換基を有していてもよい。KAが複数存在する場合、それらは同一でも異なっていてもよい。
X’は、前記架橋基A群から選ばれる架橋基、水素原子、アルキル基、シクロアルキル基、アリール基又は1価の複素環基を表し、これらの基は置換基を有していてもよい。X’が複数存在する場合、それらは同一でも異なっていてもよい。但し、少なくとも1つのX’は、前記架橋基A群から選ばれる架橋基である。] - 前記蛍光発光性低分子化合物が、式(B)で表される化合物である、請求項1~3のいずれか一項に記載の発光素子。
n1Bは、0~15の整数を表す。
Ar1Bは、芳香族炭化水素基又は芳香族複素環基を表し、これらの基は置換基を有していてもよい。該置換基が複数存在する場合、それらは同一でも異なっていてもよく、互いに結合して、それぞれが結合する原子とともに環を形成していてもよい。
R1Bは、アルキル基、シクロアルキル基、アルコキシ基、シクロアルコキシ基、アリール基、1価の複素環基、置換アミノ基、アルケニル基、シクロアルケニル基、アルキニル基又はシクロアルキニル基を表し、これらの基は置換基を有していてもよい。R1Bが複数存在する場合、同一でも異なっていてもよく、互いに結合して、それぞれが結合する炭素原子とともに環を形成していてもよい。] - 前記n1Bが、1~8の整数である、請求項4に記載の発光素子。
- 前記Ar1Bが、置換基を有していてもよい芳香族炭化水素基である、請求項4又は5に記載の発光素子。
- 前記Ar1Bが、ベンゼン環、ビフェニル環、ナフタレン環、アントラセン環、フェナントレン環、ジヒドロフェナントレン環、トリフェニレン環、ナフタセン環、フルオレン環、スピロビフルオレン環、ピレン環、ペリレン環、クリセン環、インデン環、フルオランテン環、ベンゾフルオランテン環又はアセナフトフルオランテン環から、環を構成する炭素原子に直接結合する水素原子1個以上を除いてなる基(該基は置換基を有していてもよい)である、請求項6に記載の発光素子。
- 前記Ar1Bが、ビフェニル環、ピレン環、クリセン環、フルオランテン環又はベンゾフルオランテン環から、環を構成する炭素原子に直接結合する水素原子1個以上を除いてなる基(該基は置換基を有していてもよい)である、請求項7に記載の発光素子。
- 前記R1Bが、アルキル基、シクロアルキル基、アリール基、1価の複素環基、置換アミノ基、アルケニル基又はシクロアルケニル基(これらの基は置換基を有していてもよい)である、請求項4~8のいずれか一項に記載の発光素子。
- 前記R1Bが、アリール基、置換アミノ基又はアルケニル基(これらの基は置換基を有していてもよい)である、請求項9に記載の発光素子。
- 前記蛍光発光性低分子化合物の発光スペクトルの最大ピーク波長が380nm以上570nm以下である、請求項1~10のいずれか一項に記載の発光素子。
- 前記(Y1×1000)/X1の値が、0.85以上4.0以下である、請求項1~11のいずれか一項に記載の発光素子。
- 前記第1の有機層が、前記蛍光発光性低分子化合物とホスト材料とを含有する層であり、
前記ホスト材料が式(FH-1)で表される化合物又は式(Y)で表される構成単位を含む高分子化合物であり、
前記蛍光発光性低分子化合物の含有量が、前記蛍光発光性低分子化合物と前記ホスト材料との合計を100質量部とした場合、0.1~50質量部である、請求項1~12のいずれか一項に記載の発光素子。
ArH1及びArH2は、それぞれ独立に、アリール基、1価の複素環基又は置換アミノ基を表し、これらの基は置換基を有していてもよい。
nH1は、0~15の整数を表す。
LH1は、アリーレン基、2価の複素環基、又は、-[C(RH11)2]nH11-で表される基を表し、これらの基は置換基を有していてもよい。LH1が複数存在する場合、それらは同一でも異なっていてもよい。nH11は、1~10の整数を表す。RH11は、水素原子、アルキル基、シクロアルキル基、アルコキシ基、シクロアルコキシ基、アリール基又は1価の複素環基を表し、これらの基は置換基を有していてもよい。複数存在するRH11は、同一でも異なっていてもよく、互いに結合して、それぞれが結合する炭素原子とともに環を形成していてもよい。]
- 前記第1の有機層が、正孔輸送材料、正孔注入材料、電子輸送材料、電子注入材料、酸化防止剤、及び、前記蛍光発光性低分子化合物とは異なる発光材料からなる群より選ばれる少なくとも1種の材料を更に含有する、請求項1~13のいずれか一項に記載の発光素子。
- 前記第2の有機層が、前記陽極及び前記第1の有機層との間に設けられた層である、請求項1~14のいずれか一項に記載の発光素子。
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EP3439061A4 (en) | 2019-10-30 |
CN108780850B (zh) | 2020-08-18 |
JPWO2017170313A1 (ja) | 2019-02-14 |
CN108780850A (zh) | 2018-11-09 |
EP3439061B1 (en) | 2021-07-21 |
US20200203615A1 (en) | 2020-06-25 |
JP6913079B2 (ja) | 2021-08-04 |
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