WO2017154882A1 - 発光素子 - Google Patents
発光素子 Download PDFInfo
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- WO2017154882A1 WO2017154882A1 PCT/JP2017/008949 JP2017008949W WO2017154882A1 WO 2017154882 A1 WO2017154882 A1 WO 2017154882A1 JP 2017008949 W JP2017008949 W JP 2017008949W WO 2017154882 A1 WO2017154882 A1 WO 2017154882A1
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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
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- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
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- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
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- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 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
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- 238000001226 reprecipitation Methods 0.000 description 1
- 238000012552 review Methods 0.000 description 1
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- 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
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229910001415 sodium ion Inorganic materials 0.000 description 1
- KBXGMZXLKCUSEB-UHFFFAOYSA-M sodium;[ethyl(oxidosulfinothioyl)amino]ethane Chemical compound [Na+].CCN(CC)S([O-])=S KBXGMZXLKCUSEB-UHFFFAOYSA-M 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
- 125000003003 spiro group Chemical group 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
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 125000005346 substituted cycloalkyl group Chemical group 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 150000004763 sulfides Chemical class 0.000 description 1
- DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical compound CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 1
- IFLREYGFSNHWGE-UHFFFAOYSA-N tetracene Chemical compound C1=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C21 IFLREYGFSNHWGE-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
- 125000005323 thioketone group Chemical class 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
- 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
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
- C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table compounds of the platinum group
- C07F15/0033—Iridium compounds
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/10—Organic polymers or oligomers
- H10K85/111—Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/10—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
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/10—Organic polymers or oligomers
- H10K85/151—Copolymers
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/30—Coordination compounds
- H10K85/341—Transition metal complexes, e.g. Ru(II)polypyridine complexes
- H10K85/342—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising iridium
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1007—Non-condensed systems
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1059—Heterocyclic compounds characterised by ligands containing three nitrogen atoms as heteroatoms
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Definitions
- the present invention relates to a light emitting element.
- Patent Document 1 contains an organic layer containing a crosslinked material of a crosslinking material, a compound (H0-1) represented by the following formula, and a phosphorescent compound (G0-1) represented by the following formula: A light emitting element having a light emitting layer is described.
- the compound (H0-1) is a compound having no group represented by the formula (H1-1) described later.
- an object of the present invention is to provide a light-emitting element that has an excellent luminance life.
- the present invention provides the following [1] to [11].
- a light-emitting element having an anode, a cathode, a first organic layer provided between the anode and the cathode, and a second organic layer provided between the anode and the cathode,
- the first organic layer is a layer containing a phosphorescent compound represented by formula (1) and a compound represented by formula (H);
- the light emitting element whose 2nd organic layer is a layer containing the crosslinked body of a crosslinking material.
- M represents a ruthenium atom, a rhodium atom, a palladium atom, an iridium atom or a platinum atom.
- n 1 represents an integer of 1 or more
- n 2 represents an integer of 0 or more
- n 1 + n 2 is 2 or 3.
- E 1 and E 2 each independently represent a carbon atom or a nitrogen atom. However, at least one of E 1 and E 2 is a carbon atom.
- Ring L 1 represents an aromatic heterocyclic ring, and the ring may 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. When a plurality of rings L 1 are present, they may be the same or different.
- the ring L 2 represents an aromatic hydrocarbon ring or an aromatic heterocyclic ring, and these rings may 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.
- a 1 -G 1 -A 2 represents an anionic bidentate ligand.
- a 1 and A 2 each independently represents a carbon atom, an oxygen atom or a nitrogen atom, and these atoms may be atoms constituting a ring.
- G 1 represents a single bond or an atomic group constituting a bidentate ligand together with A 1 and A 2 .
- n H1 represents an integer of 0 or more and 5 or less. When a plurality of n H1 are present, they may be the same or different. n H2 represents an integer of 1 to 10.
- Ar H1 represents a group represented by the formula (H1-1). When a plurality of Ar H1 are present, they may be the same or different.
- L H1 represents an alkylene group, a cycloalkylene group, an arylene group, a divalent heterocyclic group, a group represented by —NR H1 ′ —, an oxygen atom or a sulfur atom, and these groups have a substituent. May be.
- R H1 ′ 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.
- L H1 When a plurality of L H1 are present, they may be the same or different.
- Ar H2 represents an aromatic hydrocarbon group or an aromatic heterocyclic group, and these groups optionally have a substituent.
- Ring R H1 and Ring R H2 each independently represent a monocyclic or condensed aromatic hydrocarbon ring or a monocyclic or condensed aromatic heterocyclic ring, and these rings may have a substituent. Good. 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. However, at least one of the ring R H1 and the ring R H2 represents a condensed aromatic hydrocarbon ring or a condensed aromatic heterocyclic ring, and these rings may have a substituent.
- X H1 represents a single bond, an oxygen atom, a sulfur atom, a group represented by —N (R XH1 ) —, or a group represented by —C (R XH1 ′ ) 2 —.
- R XH1 and R XH1 ′ each independently represents a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, an aryloxy group, a monovalent heterocyclic group, a substituted amino group, or a halogen atom. And these groups may have a substituent.
- a plurality of R XH1 ′ 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.
- a substituent that R XH1 and ring R H1 may have, a substituent that R XH1 and ring R H2 may have, a substituent that R XH1 ′ and ring R H1 may have, and , R XH1 ′ and the substituent which ring R H2 may have may be bonded to each other to form a ring together with the atoms to which they are bonded.
- the cross-linking material is a low molecular compound having at least one cross-linking group selected from the cross-linking group A group, or a polymer compound containing a cross-linking structural unit having at least one cross-linking group selected from the cross-linking group A group.
- the light emitting element according to [1].
- R XL represents a methylene group, an oxygen atom or a sulfur atom
- n XL represents an integer of 0 to 5.
- R XL represents a methylene group, an oxygen atom or a sulfur atom
- n XL represents an integer of 0 to 5.
- * 1 represents a binding position.
- These crosslinking groups may have a substituent.
- the cross-linking material is a polymer compound including a cross-linking structural unit having at least one cross-linking group selected from the cross-linking group A group.
- nA represents an integer of 0 to 5, and n represents 1 or 2.
- Ar 3 represents an aromatic hydrocarbon group or a heterocyclic group, and these groups may have a substituent.
- L 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, and 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.
- 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, and these groups have a substituent.
- 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 group, 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 crosslinking group selected from the crosslinking group A group.
- the crosslinking group of the crosslinking material is represented by the formula (XL-2), formula (XL-3), formula (XL-4), formula (XL-5), formula (XL-6), formula (XL-7).
- X H1 represents the same meaning as described above.
- X H2 and X H3 each independently represent a single bond, an oxygen atom, a sulfur atom, a group represented by —N (R XH2 ) —, or a group represented by —C (R XH2 ′ ) 2 —.
- R XH2 and R XH2 ′ each independently represents a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, an aryloxy group, a monovalent heterocyclic group, a substituted amino group, or a halogen atom. And these groups may have a substituent.
- a plurality of R XH2 ′ 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.
- Z H1, Z H2, Z H3 , Z H4, Z H5, Z H6, Z H7, Z H8, Z H9, Z H10, Z H11 and Z H12 each independently represents a carbon atom or a nitrogen atom.
- R H1 , R H2 , R H3 , R H4 , R H5 , R H6 , R H7 , R H8 , R H9 , R H10 , R H11 and R H12 are each independently a hydrogen atom, an alkyl group or a cycloalkyl group Represents an alkoxy group, a cycloalkoxy group, an aryl group, an aryloxy group, a monovalent heterocyclic group, a substituted amino group, or a halogen atom, and these groups optionally have a substituent.
- Z H1 is a nitrogen atom
- R H1 does not exist.
- Z H2 is a nitrogen atom, R H2 does not exist.
- Z H3 is a nitrogen atom
- R H3 does not exist.
- Z H4 is a nitrogen atom
- R H4 does not exist.
- Z H5 is a nitrogen atom
- R H6 does not exist.
- Z H7 is a nitrogen atom
- R H7 does not exist.
- Z H8 is a nitrogen atom
- Z H9 is a nitrogen atom
- Z H10 is a nitrogen atom
- Z H10 does not exist.
- Z H11 is a nitrogen atom
- R H11 does not exist.
- Z H12 is a nitrogen atom, R H12 does not exist.
- R H1 and R H2 , R H3 and R H4 , R H5 and R H6 , R H6 and R H7 , R H7 and R H8 , R H9 and R H10 , R H10 and R H11 , and R H11 and R H12 are , May be bonded to each other to form a ring together with the carbon atoms to which they are bonded.
- [7] The light emitting device according to any one of [1] to [6], wherein the phosphorescent compound represented by the formula (1) is a phosphorescent compound represented by the formula (1-B).
- E11B , E12B , E13B , E14B , E21B , E22B , E23B and E24B each independently represent a nitrogen atom or a carbon atom.
- E 11B , E 12B , E 13B , E 14B , E 21B , E 22B , E 23B and E 24B they may be the same or different.
- E 11B is a nitrogen atom
- R 11B does not exist.
- E 12B is a nitrogen atom, R 12B does not exist.
- E 13B is a nitrogen atom
- R 13B does not exist.
- E 14B is a nitrogen atom
- R 14B does not exist.
- E 21B is a nitrogen atom
- R 21B does not exist.
- E 22B is a nitrogen atom
- R 23B is a nitrogen atom
- E 24B is a nitrogen atom, R 24B does not exist.
- R 11B , R 12B , R 13B , R 14B , R 21B , R 22B , R 23B and R 24B are each independently a hydrogen atom, alkyl group, cycloalkyl group, alkoxy group, cycloalkoxy group, aryl group, aryl An oxy group, a monovalent heterocyclic group, a substituted amino group, or a halogen atom is represented, and these groups may have a substituent.
- R 11B , R 12B , R 13B , R 14B , R 21B , R 22B , R 23B and R 24B they may be the same or different.
- Ring L 1B represents a pyridine ring or a pyrimidine ring composed of a nitrogen atom, a carbon atom, E 11B , E 12B , E 13B and E 14B .
- Ring L 2B represents a benzene ring, a pyridine ring or a pyrimidine ring composed of two carbon atoms, E 21B , E 22B , E 23B and E 24B .
- the phosphorescent compound represented by the formula (1-B) is a phosphorescent compound represented by the formula (1-B1), a phosphorescent compound represented by the formula (1-B2), the formula (1) The phosphorescent compound represented by -B3), the phosphorescent compound represented by formula (1-B4), or the phosphorescent compound represented by formula (1-B5).
- Light emitting element is a phosphorescent compound represented by the formula (1-B1), a phosphorescent compound represented by the formula (1-B2), the formula (1)
- n 11 and n 12 each independently represents an integer of 1 or more, and n 11 + n 12 is 2 or 3. However, when M is a ruthenium atom, rhodium atom or iridium atom, n 11 + n 12 is 3, and when M is a palladium atom or platinum atom, n 11 + n 12 is 2.
- R 15B , R 16B , R 17B and R 18B are each independently a hydrogen atom, alkyl group, cycloalkyl group, alkoxy group, cycloalkoxy group, aryl group, aryloxy group, monovalent heterocyclic group, substituted amino group Represents a group or a halogen atom, and these groups optionally have a substituent.
- R 15B , R 16B , R 17B and R 18B may be the same or different.
- E 11A , E 12A , E 13A , E 21A , E 22A , E 23A and E 24A each independently represent a nitrogen atom or a carbon atom.
- E 11A , E 12A , E 13A , E 21A , E 22A , E 23A and E 24A they may be the same or different.
- E 11A is a nitrogen atom
- R 11A may or may not be present.
- E 12A is a nitrogen atom
- R 12A may or may not be present.
- E 13A When E 13A is a nitrogen atom, R 13A may or may not be present.
- E 21A When E 22A is a nitrogen atom, R 22A does not exist.
- E 23A When E 23A is a nitrogen atom, R 23A does not exist.
- E 24A When E 24A is a nitrogen atom, R 24A does not exist.
- R 11A , R 12A , R 13A , R 21A , R 22A , R 23A and R 24A are each independently a hydrogen atom, alkyl group, cycloalkyl group, alkoxy group, cycloalkoxy group, aryl group, aryloxy group, It represents a monovalent heterocyclic group, a substituted amino group, or a halogen atom, and these groups may have a substituent.
- R 11A , R 12A , R 13A , R 21A , R 22A , R 23A and R 24A they may be the same or different.
- R 11A and R 12A , R 12A and R 13A , R 11A and R 21A , R 21A and R 22A , R 22A and R 23A , and R 23A and R 24A are bonded to each other together with the atoms to which they are bonded.
- a ring may be formed.
- Ring L 1A represents a triazole ring or a diazole ring composed of a nitrogen atom, E 1 , E 11A , E 12A and E 13A .
- Ring L 2A represents a benzene ring, a pyridine ring or a pyrimidine ring composed of two carbon atoms, E 21A , E 22A , E 23A and E 24A .
- 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.
- the “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 .
- the polymer compound may be any of a block copolymer, a random copolymer, an alternating copolymer, and a graft copolymer, or other embodiments.
- the terminal group of the polymer compound is preferably a stable group because if the polymerization active group remains as it is, there is a possibility that the light emission characteristics or the luminance life may be lowered when the polymer compound is used for the production of a light emitting device. It is.
- the terminal group is preferably a group conjugated to the main chain, and examples thereof include a group bonded to an aryl group or a monovalent heterocyclic group via a carbon-carbon bond.
- 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 linear or branched.
- the number of carbon atoms of the straight chain 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, more preferably 4 to 20, excluding the number of carbon atoms of the substituent.
- the alkyl group may have a substituent, for example, methyl group, ethyl group, propyl group, isopropyl group, butyl group, 2-butyl group, isobutyl group, tert-butyl group, pentyl group, isoamyl group, 2-ethylbutyl, hexyl, heptyl, octyl, 2-ethylhexyl, 3-propylheptyl, decyl, 3,7-dimethyloctyl, 2-ethyloctyl, 2-hexyldecyl, dodecyl And a group in which a hydrogen atom in these groups is substituted with a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, a fluorine atom, etc., for example, a trifluoromethyl group, a pentafluoroethyl group,
- the number of carbon atoms of the “cycloalkyl 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.
- the cycloalkyl group may have a substituent, and examples thereof include a cyclohexyl group, 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.
- the “alkoxy group” may be 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.
- the alkoxy group may have a substituent, for example, 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, lauryloxy group, and the hydrogen atom in these groups is a cycloalkyl group, an alkoxy group, And a group substituted with a cycloalkoxy group, an aryl group, a fluorine atom, or the like.
- a substituent for example, methoxy group, ethoxy group, propyloxy group, isopropyloxy group, butyloxy group, isobutyloxy group, tert-buty
- 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.
- the cycloalkoxy group may have a substituent, and examples thereof include a cyclohexyloxy group.
- 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.
- the aryloxy group may have a substituent, for example, a phenoxy group, 1-naphthyloxy group, 2-naphthyloxy group, 1-anthracenyloxy group, 9-anthracenyloxy group, 1- Examples include a pyrenyloxy group and a group in which a hydrogen atom in these groups is substituted with an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, a fluorine atom, or the like.
- 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 heterocyclic ring such as phenoxazine, phenothiazine, dibenzoborol, dibenzosilol, benzopyran itself does not exhibit aromaticity, but the aromatic ring is condensed to the heterocyclic ring Means a compound.
- 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.
- the monovalent heterocyclic group may have a substituent, for example, thienyl group, pyrrolyl group, furyl group, pyridinyl group, piperidinyl group, quinolinyl group, isoquinolinyl group, pyrimidinyl group, triazinyl group, and these And a group in which the hydrogen atom in the group is substituted with an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, or the like.
- 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.
- the substituted amino group include a dialkylamino group, a dicycloalkylamino group, and a diarylamino group.
- the amino group include dimethylamino group, diethylamino group, diphenylamino group, bis (4-methylphenyl) amino group, bis (4-tert-butylphenyl) amino group, bis (3,5-di-tert- Butylphenyl) amino group.
- the “alkenyl group” may be linear or branched.
- the number of carbon atoms of the straight-chain alkenyl group is usually 2-30, preferably 3-20, excluding the number of 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 number of 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.
- the alkenyl group and the cycloalkenyl group may have a substituent, for example, a vinyl group, a 1-propenyl group, a 2-propenyl group, a 2-butenyl group, a 3-butenyl group, a 3-pentenyl group, a 4-pentenyl group, Examples include a pentenyl group, a 1-hexenyl group, a 5-hexenyl group, a 7-octenyl group, and groups in which these groups have a substituent.
- the “alkynyl group” may be 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.
- the alkynyl group and the cycloalkynyl group may have a substituent, for example, an ethynyl group, a 1-propynyl group, a 2-propynyl group, a 2-butynyl group, a 3-butynyl group, a 3-pentynyl group, 4- Examples include a pentynyl group, 1-hexynyl group, 5-hexynyl group, and groups in which these groups have a substituent.
- the “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.
- the arylene group may have a substituent, for example, phenylene group, naphthalenediyl group, anthracenediyl group, phenanthrene diyl group, dihydrophenanthenediyl group, naphthacene diyl group, fluorenediyl group, pyrenediyl group, perylene diyl group, Examples include chrysenediyl groups and groups in which these groups have substituents, and groups represented by formulas (A-1) to (A-20) are preferable.
- the arylene group includes a group in which a plurality of these groups are bonded.
- R and R a each independently represents a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group.
- a plurality of R and R a may be the same or different, and R a may be bonded to each other to form a ring together with the atoms to which they are bonded.
- the number of carbon atoms of the divalent heterocyclic group is usually 2 to 60, preferably 3 to 20, and more preferably 4 to 15 excluding the number of carbon atoms of the substituent.
- the divalent heterocyclic group may have a substituent, for example, pyridine, diazabenzene, triazine, azanaphthalene, diazanaphthalene, carbazole, dibenzofuran, dibenzothiophene, dibenzosilol, phenoxazine, phenothiazine, acridine, Divalent acridine, furan, thiophene, azole, diazole, and triazole include divalent groups obtained by removing two hydrogen atoms from hydrogen atoms directly bonded to carbon atoms or heteroatoms constituting the ring, and preferably Is 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
- crosslinking group is a group capable of forming a new bond by being subjected to heating, ultraviolet irradiation, near ultraviolet irradiation, visible light irradiation, infrared irradiation, radical reaction, etc.
- “Substituent” means a halogen atom, cyano group, alkyl group, cycloalkyl group, aryl group, monovalent heterocyclic group, alkoxy group, cycloalkoxy group, aryloxy group, amino group, substituted amino group, alkenyl group. Represents a cycloalkenyl group, an alkynyl group or a cycloalkynyl group.
- the substituent may be a crosslinking group.
- the light emitting device of the present invention is a light emitting device having an anode, a cathode, a first organic layer provided between the anode and the cathode, and a second organic layer provided between the anode and the cathode.
- the first organic layer is a layer containing a phosphorescent compound represented by the formula (1) and a compound represented by the formula (H), and the second organic layer is a cross-linking of a cross-linking material.
- a light-emitting element which is a layer containing a body.
- 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.
- a dry method such as a vacuum deposition method
- a wet method such as a spin coating method and an ink jet printing method
- a wet method is preferable.
- the first organic layer is formed by a wet method
- the second organic layer is formed by a wet method, it is preferable to use a second ink described later.
- the crosslinking material contained in the second organic layer can be crosslinked by heating or light irradiation, and the crosslinking contained in the second organic layer by heating. It is preferred to crosslink the material.
- the crosslinked material is contained in the second organic layer in a crosslinked state (crosslinked product of the crosslinked material)
- the second organic layer is substantially insolu
- the heating temperature for crosslinking is usually 25 ° C to 300 ° C, preferably 50 ° C to 250 ° C, more preferably 150 ° C to 200 ° C, and further preferably 170 ° C to 190 ° C. .
- the heating time is usually 0.1 minutes to 1000 minutes, preferably 0.5 minutes to 500 minutes, more preferably 1 minute to 120 minutes, and further preferably 30 minutes 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 phosphorescent compound represented by formula (1) and a compound represented by formula (H).
- the phosphorescent compound represented by the formula (1) is usually a compound that exhibits phosphorescence at room temperature (25 ° C.), and preferably a compound that emits light from a triplet excited state at room temperature.
- the phosphorescent compound represented by the formula (1) has M as a central metal, a ligand whose number is defined by the subscript n 1 , and its number is defined by the subscript n 2 . It consists of a ligand.
- M is preferably an iridium atom or a platinum atom, and more preferably an iridium atom, because the luminance lifetime of the light emitting device according to the embodiment of the present invention is excellent.
- M is a ruthenium atom, a rhodium atom or an iridium atom, n 1 is preferably 2 or 3, and more preferably 3.
- M is a palladium atom or a platinum atom, n 1 is preferably 2.
- E 1 and E 2 are preferably carbon atoms.
- Ring L 1 is preferably a 5-membered aromatic heterocyclic ring or a 6-membered aromatic heterocyclic ring, or a 5-membered aromatic heterocyclic ring having 2 to 4 nitrogen atoms as constituent atoms or one More preferably, it is a 6-membered aromatic heterocycle having 4 or less nitrogen atoms as constituent atoms, and a 5-membered aromatic heterocycle having 2 or more and 3 or less nitrogen atoms as constituent atoms or one More preferably, it is a 6-membered aromatic heterocyclic ring having 2 or less nitrogen atoms as constituent atoms, and these rings may have a substituent.
- E 1 is preferably a carbon atom.
- the ring L 1 include a diazole ring, a triazole ring, a pyridine ring, a diazabenzene ring, a triazine ring, a quinoline ring and an isoquinoline ring, and a diazole ring, a triazole ring, a pyridine ring, a pyrimidine ring, a quinoline ring or an isoquinoline ring.
- a diazole ring, a triazole ring, a pyridine ring, a quinoline ring or an isoquinoline ring is more preferable, a pyridine ring, a quinoline ring or an isoquinoline ring is more preferable, a pyridine ring or an isoquinoline ring is particularly preferable, and these rings have a substituent. May be.
- Ring L 2 is preferably a 5-membered or 6-membered aromatic hydrocarbon ring, or a 5-membered or 6-membered aromatic heterocycle, and a 6-membered aromatic hydrocarbon ring or a 6-membered aromatic heterocycle More preferably, it is a ring, more preferably a 6-membered aromatic hydrocarbon ring, and these rings may have a substituent.
- E 2 is preferably a carbon atom.
- Examples of the ring L 2 include a benzene ring, a naphthalene ring, a fluorene ring, a phenanthrene ring, an indene ring, a pyridine ring, a diazabenzene ring, and a triazine ring, and a benzene ring, a naphthalene ring, a fluorene ring, a pyridine ring, or a pyrimidine ring.
- a benzene ring, a pyridine ring or a pyrimidine ring is more preferable, and a benzene ring is more preferable, and these rings may have a substituent.
- Examples of the substituent that the ring L 1 and the ring L 2 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, and a substituted amino group.
- a halogen atom is preferable, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, a monovalent heterocyclic group or a fluorine atom is more preferable, and an alkyl group, a cycloalkyl group, an aryl group or a monovalent complex is preferable.
- a cyclic group is more preferable, an aryl group or a monovalent heterocyclic group is particularly preferable, and these groups may further have a substituent.
- the aryl group in the substituent which the ring L 1 and the ring L 2 may have is preferably a phenyl group, a naphthyl group, an anthracenyl group, a phenanthrenyl group, a dihydrophenanthrenyl group, a fluorenyl group or a pyrenyl group.
- a group, a naphthyl group or a fluorenyl group is more preferable, a phenyl group is more preferable, and these groups may further have a substituent.
- Examples of the monovalent heterocyclic group in the substituent that the ring L 1 and the ring L 2 may have include a pyridyl group, a pyrimidinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, a dibenzofuranyl group, a dibenzothienyl group, A carbazolyl group, azacarbazolyl group, diazacarbazolyl group, phenoxazinyl group or phenothiazinyl group is preferable, pyridyl group, pyrimidinyl group, triazinyl group, carbazolyl group, azacarbazolyl group or diazacarbazolyl group is more preferable, pyridyl group, A pyrimidinyl group or a triazinyl group is more preferable, a triazinyl group is particularly preferable, and these groups may further have a substituent.
- the amino group preferably has an aryl group or a monovalent heterocyclic group, more preferably an aryl group, 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 the substituent that the ring L 1 and the ring L 2 may have.
- 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 the substituent that the ring L 1 and the ring L 2 may have. It is.
- Examples of the substituent that the ring L 1 and the ring L 2 may have further include an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, an aryloxy group, A monovalent heterocyclic group, a substituted amino group or a halogen atom is preferable, and an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, a monovalent heterocyclic group or a fluorine atom is more preferable, an alkyl group, a cyclo An alkyl group, an aryl group or a monovalent heterocyclic group is more preferred, an alkyl group, a cycloalkyl group or an aryl group is particularly preferred, and these groups may further have a substituent.
- the aryl group, monovalent heterocyclic group or substituted amino group in the substituent that the ring L 1 and the ring L 2 may have is preferable because the luminance lifetime of the light emitting device according to the embodiment of the present invention is more excellent.
- m DA1 , m DA2 and m DA3 each independently represent an integer of 0 or more.
- GDA represents a nitrogen atom, an aromatic hydrocarbon group, or a heterocyclic group, and these groups may have a substituent.
- Ar DA1 , Ar DA2 and Ar DA3 each independently represent an arylene group or a divalent heterocyclic group, and these groups optionally have a substituent.
- T DA represents an aryl group or a monovalent heterocyclic group, and these groups optionally have a substituent.
- the plurality of TDAs may be the same or different.
- m DA1 , m DA2 , m DA3 , m DA4 , m DA5 , m DA6 and m DA7 each independently represent an integer of 0 or more.
- GDA represents a nitrogen atom, an aromatic hydrocarbon group, or a heterocyclic group, and these groups may have a substituent.
- a plurality of GDAs may be the same or different.
- Ar DA1 , Ar DA2 , Ar DA3 , Ar DA4 , Ar DA5 , Ar DA6 and Ar DA7 each independently represent an arylene group or a divalent heterocyclic group, and these groups may have a substituent. Good.
- T DA represents an aryl group or a monovalent heterocyclic group, and these groups optionally have a substituent.
- the plurality of TDAs may be the same or different.
- m DA1 represents an integer of 0 or more.
- Ar DA1 represents an arylene group or a divalent heterocyclic group, and these groups optionally have a substituent.
- T DA represents an aryl group or a monovalent heterocyclic group, and these groups optionally have a substituent.
- m DA1 , m DA2 , m DA3 , m DA4 , m DA5 , m DA6 and m DA7 are usually an integer of 10 or less, preferably an integer of 5 or less, more preferably an integer of 2 or less, Preferably 0 or 1.
- m DA2 , m DA3 , m DA4 , m DA5 , m DA6 and m DA7 are preferably the same integer.
- GDA is preferably an aromatic hydrocarbon group or a heterocyclic group, more preferably hydrogen bonded directly to a carbon atom or a nitrogen atom constituting the ring from a benzene ring, a pyridine ring, a pyrimidine ring, a triazine ring or a carbazole ring. It is a group formed by removing three atoms, and these groups may have a substituent.
- the substituent that GDA may have 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 alkyl group, It is a cycloalkyl group, an alkoxy group or a cycloalkoxy group, more preferably an alkyl group or a cycloalkyl group, and these groups optionally have a substituent.
- G DA is preferably a group represented by the formula (GDA-11) ⁇ formula (GDA-15), more preferably a group represented by the formula (GDA-11) ⁇ formula (GDA-14) And more preferably a group represented by the formula (GDA-11) or the formula (GDA-14).
- R DA 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 further have a substituent. When there are a plurality of RDA , they may be the same or different. ]
- R DA is preferably a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group or a cycloalkoxy group, more preferably a hydrogen atom, an alkyl group or a cycloalkyl group, and these groups have a substituent. May be.
- Ar DA1 , Ar DA2 , Ar DA3 , Ar DA4 , Ar DA5 , Ar DA6 and Ar DA7 are preferably a phenylene group, a fluorenediyl group or a carbazolediyl group, more preferably a formula (ArDA-1) to a formula A group represented by formula (ArDA-5), more preferably a group represented by formula (ArDA-1) to formula (ArDA-3), particularly preferably formula (ArDA-1) or formula (ArDA -2), particularly preferably a group represented by the formula (ArDA-2), and these groups may have a substituent.
- R DA represents the same meaning as described above.
- R DB 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. When there are a plurality of RDBs , they may be the same or different. ]
- R DB is preferably an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, more preferably an aryl group or a monovalent heterocyclic group, still more preferably an aryl group, The group may have a substituent.
- Ar DA1, Ar DA2, Ar DA3 , Ar DA4, Ar DA5, Ar DA6 and examples and preferred ranges of the substituent which may be possessed by Ar DA7 are examples of the substituent which may be possessed by G DA and It is the same as a preferable range.
- T DA is preferably a group represented by the formula (TDA-1) ⁇ formula (TDA-3), more preferably a group represented by the formula (TDA-1).
- R DA and R DB are as defined above.
- the group represented by the formula (DA) is preferably a group represented by the formula (D-A1) to the formula (D-A5), more preferably the formula (D-A1) or the formula (D-A3).
- a group represented by the formula (D-A5) more preferably a group represented by the formula (D-A1), the formula (D-A3) or the formula (D-A5).
- R p1 , R p2 , R p3 and R p4 each independently represents an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group or a halogen atom.
- R p1 , R p2 and R p4 may be the same or different.
- np1 represents an integer of 0 to 5
- np2 represents an integer of 0 to 3
- np3 represents 0 or 1
- np4 represents an integer of 0 to 4.
- a plurality of np1 may be the same or different.
- the group represented by the formula (DB) is preferably a group represented by the formula (D-B1) to the formula (D-B6), more preferably the formula (D-B1) to the formula (D-B3).
- a group represented by formula (D-B5) or formula (D-B6), more preferably a group represented by formula (D-B1), formula (D-B3) or formula (D-B5) And particularly preferably a group represented by the formula (D-B1).
- R p1 , R p2 , R p3 and R p4 each independently represents an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group or a halogen atom.
- R p1 , R p2 and R p4 they may be the same or different.
- np1 represents an integer of 0 to 5
- np2 represents an integer of 0 to 3
- np3 represents 0 or 1
- np4 represents an integer of 0 to 4.
- a plurality of np1 may be the same or different.
- a plurality of np2 may be the same or different.
- the group represented by the formula (DC) is preferably a group represented by the formula (D-C1) to the formula (D-C4), more preferably the formula (D-C1) to the formula (D-C3). More preferably a group represented by the formula (D-C1) or the formula (D-C2), particularly preferably a group represented by the formula (D-C1).
- R p4 , R p5 and R p6 each independently represents an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group or a halogen atom. When there are a plurality of R p4 , R p5 and R p6 , they may be the same or different.
- np4 represents an integer of 0 to 4
- np5 represents an integer of 0 to 5
- np6 represents an integer of 0 to 5.
- Np1 is preferably an integer of 0 to 2, more preferably 0 or 1.
- np2 is preferably 0 or 1
- np3 is preferably 0.
- np4 is preferably an integer of 0 to 2
- np5 is preferably an integer of 0 to 3, more preferably 0 or 1.
- np6 is preferably an integer of 0 to 2, more preferably 0 or 1.
- the alkyl group or cycloalkyl group in R p1 , R p2 , R p3 , R p4 , R p5 and R p6 is preferably a methyl group, an ethyl group, an isopropyl group, a tert-butyl group, a hexyl group, 2-ethylhexyl. Group, cyclohexyl group or tert-octyl group.
- the alkoxy group or cycloalkoxy group in R p1 , R p2 , R p3 , R p4 , R p5 and R p6 is preferably a methoxy group, a 2-ethylhexyloxy group or a cyclohexyloxy group.
- R p1 , R p2 , R p3 , R p4 , R p5 and R p6 are preferably an optionally substituted alkyl group or an optionally substituted cycloalkyl group, and more An alkyl group which may have a substituent is preferable, and a methyl group, an ethyl group, an isopropyl group, a tert-butyl group, a hexyl group, a 2-ethylhexyl group or a tert-octyl group is more preferable.
- Examples of the group represented by the formula (D-A) include groups represented by the formula (DA-1) to the formula (DA-12).
- R D represents a hydrogen atom, a methyl group, an ethyl group, an isopropyl group, a tert-butyl group, a hexyl group, a 2-ethylhexyl group, a tert-octyl group, a cyclohexyl group, a methoxy group, a 2-ethylhexyloxy group, or Represents a cyclohexyloxy group.
- two or more RD exists, they may be the same or different.
- Examples of the group represented by the formula (D-B) include groups represented by the formula (DB-1) to the formula (DB-7).
- R D represents the same meaning as described above.
- Examples of the group represented by the formula (D-C) include groups represented by the formula (DC-1) to the formula (DC-13).
- R D represents the same meaning as described above.
- R D is preferably a hydrogen atom, a methyl group, an ethyl group, an isopropyl group, a tert-butyl group, a hexyl group, a 2-ethylhexyl group or a tert-octyl group, and is preferably a hydrogen atom, a tert-butyl group or a tert-octyl group. More preferably, it is a group.
- substituents that the ring L 1 may have they may be the same or different and may be bonded to each other to form a ring together with the atoms to which they are bonded.
- substituents that the ring L 2 may have they may be the same or different and may be bonded to each other to form a ring together with the atoms to which they are bonded.
- the substituent that the ring L 1 may have and the substituent that the ring L 2 may have may be bonded to each other to form a ring together with the atoms to which they are bonded.
- anionic bidentate ligand examples include a ligand represented by the following formula. However, the anionic bidentate ligand represented by A 1 -G 1 -A 2 is different from the ligand whose number is defined by the subscript n 1 .
- R L1 represents a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group, or a halogen atom, and these groups optionally have a substituent.
- a plurality of R L1 may be the same or different.
- R L2 represents an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group, or a halogen atom, and these groups optionally have a substituent.
- R L1 is preferably a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group or a fluorine atom, more preferably a hydrogen atom or an alkyl group, and these groups optionally have a substituent. .
- R L2 is preferably an alkyl group or an aryl group, and these groups optionally have a substituent.
- the phosphorescent compound represented by the formula (1) has excellent luminance life of the light emitting device according to the embodiment of the present invention
- the phosphorescent compound represented by the formula (1-A) or the formula (1-B) The phosphorescent compound represented by formula (1-B) is preferred, and the phosphorescent compound represented by formula (1-B) is more preferred.
- ring L 1A is a diazole ring
- an imidazole ring in which E 11A is a nitrogen atom or an imidazole ring in which E 12A is a nitrogen atom is preferable
- an imidazole ring in which E 11A is a nitrogen atom is more preferable.
- ring L 1A is a triazole ring
- a triazole ring in which E 11A and E 12A are nitrogen atoms, or a triazole ring in which E 11A and E 13A are nitrogen atoms is preferable, and E 11A and E 12A are nitrogen atoms.
- a triazole ring is more preferred.
- Examples and preferred ranges of the aryl group, monovalent heterocyclic group and substituted amino group in R 11A , R 12A , R 13A , R 21A , R 22A , R 23A and R 24A are ring L 1 and ring L 2 , respectively.
- R 11A , R 12A , R 13A , R 21A , R 22A , R 23A and R 24A may have and preferred ranges thereof may have ring L 1 and ring L 2. It is the same as the example and preferable range of the substituent which the substituent may further have.
- R 11A is preferably an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, and an aryl group or a monovalent heterocyclic ring It is more preferably a group, and further preferably an aryl group, and these groups may have a substituent.
- R 11A is preferably a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group or a substituted amino group, and a hydrogen atom, an alkyl group, a cycloalkyl group Or it is more preferably an aryl group, more preferably a hydrogen atom, an alkyl group or a cycloalkyl group, and particularly preferably a hydrogen atom, and these groups optionally have a substituent.
- R 12A is preferably an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, and an aryl group or a monovalent heterocyclic ring It is more preferably a group, and further preferably an aryl group, and these groups may have a substituent.
- R 12A is preferably a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group or a substituted amino group, a hydrogen atom, an alkyl group, a cycloalkyl group Or it is more preferably an aryl group, more preferably a hydrogen atom, an alkyl group or a cycloalkyl group, and particularly preferably a hydrogen atom, and these groups optionally have a substituent.
- R 13A is preferably an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, and an aryl group or a monovalent heterocyclic ring It is more preferably a group, and further preferably an aryl group, and these groups may have a substituent.
- R 13A is preferably a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group or a substituted amino group, a hydrogen atom, an alkyl group, a cycloalkyl group Or it is more preferably an aryl group, more preferably a hydrogen atom, an alkyl group or a cycloalkyl group, and particularly preferably a hydrogen atom, and these groups optionally have a substituent.
- ring L 2A is a pyridine ring
- a pyridine ring in which E 23A is a nitrogen atom is preferable
- E 22A is a nitrogen atom
- Ring L 2A is preferably a benzene ring.
- R 21A , R 22A , R 23A and R 24A are preferably a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, a monovalent heterocyclic group, a fluorine atom or a substituted amino group, An atom, an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group or a substituted amino group is more preferable, and a hydrogen atom, an alkyl group, a cycloalkyl group, a formula (DA), a formula (D- B) or a group represented by formula (DC) is more preferred, and a hydrogen atom or a group represented by formula (DA), formula (DB) or formula (DC) It is particularly preferable that a hydrogen atom or a group represented by the formula (DA) is particularly preferable, and these groups may have a substituent.
- R 22A or R 23A is preferably an aryl group, monovalent heterocyclic group or substituted amino group, and R 22A is aryl. It is more preferably a group, a monovalent heterocyclic group or a substituted amino group.
- the phosphorescent compound represented by the formula (1-A) has a further excellent luminance life of the light emitting device according to the embodiment of the present invention
- the phosphorescent compound represented by the formula (1-A1), A phosphorescent compound represented by 1-A2), a phosphorescent compound represented by formula (1-A3), or a phosphorescent compound represented by formula (1-A4) is preferred.
- the phosphorescent compound represented by 1-A1) or the phosphorescent compound represented by formula (1-A3) is more preferred, and the phosphorescent compound represented by formula (1-A1). More preferably.
- Examples and preferred ranges of the aryl group, monovalent heterocyclic group and substituted amino group in R 11B , R 12B , R 13B , R 14B , R 21B , R 22B , R 23B and R 24B are the ring L 1 and Examples of the aryl group, monovalent heterocyclic group and substituted amino group in the substituent which the ring L 2 may have are the same as the preferred range.
- R 11B , R 12B , R 13B , R 14B , R 21B , R 22B , R 23B and R 24B may have and preferred ranges thereof include ring L 1 and ring L 2. It is the same as the example and preferable range of the substituent which the substituent which may be further may have.
- R 11B , R 12B , R 13B , R 14B , R 21B , R 22B , R 23B and R 24B are a hydrogen atom, alkyl group, cycloalkyl group, alkoxy group, cycloalkoxy group, fluorine atom, aryl group, monovalent Are preferably a heterocyclic group or a substituted amino group, more preferably a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group or a substituted amino group, a hydrogen atom, an alkyl group, It is more preferably a cycloalkyl group, or a group represented by the formula (DA), formula (DB), or formula (DC), a hydrogen atom, or a formula (DA), A group represented by formula (DB) or formula (DC) is particularly preferred, and these groups may have a substituent.
- R 11B , R 12B or R 13B is preferably an aryl group, a monovalent heterocyclic group or a substituted amino group, 12B or R 13B is more preferably an aryl group, monovalent heterocyclic group or substituted amino group, and R 13B is more preferably an aryl group, monovalent heterocyclic group or substituted amino group.
- R 22B or R 23B is preferably an aryl group, monovalent heterocyclic group or substituted amino group, and R 22B is aryl. It is more preferably a group, a monovalent heterocyclic group or a substituted amino group.
- the phosphorescent compound represented by the formula (1-B) has a further excellent luminance lifetime of the light emitting device according to the embodiment of the present invention
- the phosphorescent compound represented by formula (1-B1), the phosphorescent compound represented by formula (1-B2) or the formula (1-B3) is preferred. More preferably, it is a phosphorescent compound represented by the formula (1-B1) or a phosphorescent compound represented by the formula (1-B3), A phosphorescent compound represented by the formula (1-B1) is particularly preferable.
- aryl groups, monovalent heterocyclic groups and substituted amino groups in R 15B , R 16B , R 17B and R 18B and preferred ranges thereof are the substituents that the ring L 1 and the ring L 2 may have, respectively.
- R 15B , R 16B , R 17B and R 18B may have and preferred ranges thereof may be further included in the substituents which ring L 1 and ring L 2 may have. Examples of good substituents and preferred ranges are the same.
- R 15B , R 16B , R 17B and R 18B may be a hydrogen atom, alkyl group, cycloalkyl group, alkoxy group, cycloalkoxy group, fluorine atom, aryl group, monovalent heterocyclic group or substituted amino group.
- they are a hydrogen atom, 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 a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl More preferably a monovalent heterocyclic group or a substituted amino group, particularly preferably a hydrogen atom, an alkyl group or a cycloalkyl group, particularly preferably a hydrogen atom, these groups being a substituent. You may have.
- Examples of the phosphorescent compound represented by the formula (1) include a phosphorescent compound represented by the following formula.
- Examples of the phosphorescent compound represented by the formula (1) include “Journal of the American Chemical Society, Vol. 107, 1431-1432 (1985)”, “Journal of the American Chemical, 47”. 6653 (1984) ", Japanese translations of PCT publication No. 2004-530254, Japanese Unexamined Patent Publication No. 2008-179617, Japanese Unexamined Patent Publication No. 2011-105701, Japanese translations of PCT publication No. 2007-504272, International Publication No. 2006/121811, and Japanese Unexamined Patent Publication No. 2013-201311. It can be synthesized according to the methods described in JP-A-147450 and JP-A-2014-224101.
- the molecular weight of the compound represented by the formula (H) is usually 1 ⁇ 10 2 to 5 ⁇ 10 4 , preferably 2 ⁇ 10 2 to 1 ⁇ 10 4 , more preferably 3 ⁇ 10 2. ⁇ a 5 ⁇ 10 3, more preferably from 4 ⁇ 10 2 ⁇ 2.5 ⁇ 10 3, particularly preferably from 5 ⁇ 10 2 ⁇ 1.5 ⁇ 10 3.
- n H1 is preferably an integer of 0 or more, 3 or less, more preferably an integer of 0 or more, 2 or less, still more preferably 0 or 1, and particularly preferably 0 because synthesis is easy.
- n H2 is preferably an integer of 1 or more and 7 or less, more preferably an integer of 1 or more and 5 or less, and further preferably 1 or more and 3 or less, because the luminance life of the light emitting device according to the embodiment of the present invention is excellent. , Particularly preferably 1 or 2, particularly preferably 1.
- the number of carbon atoms of the monocyclic aromatic hydrocarbon ring does not include the number of carbon atoms of the substituent, and is preferably 6.
- the monocyclic aromatic hydrocarbon ring is preferably a benzene ring which may have a substituent.
- the number of carbon atoms of the aromatic hydrocarbon ring of the condensed ring is usually 7 to 60, preferably 9 to 30, not including the number of carbon atoms of the substituent. Preferably, it is 10-18.
- the condensed aromatic hydrocarbon ring in ring R H1 and ring R H2 include a naphthalene ring, anthracene ring, phenanthrene ring, dihydrophenanthrene ring, naphthacene ring, fluorene ring, spirobifluorene ring, indene ring, and pyrene ring.
- Perylene ring and chrysene ring preferably naphthalene ring, anthracene ring, phenanthrene ring, dihydrophenanthrene ring, fluorene ring or spirobifluorene ring, more preferably naphthalene ring, fluorene ring or spirobifluorene ring More preferably, it is a fluorene ring or a spirobifluorene ring, and particularly preferably a fluorene ring, and these rings optionally have a substituent.
- the number of carbon atoms of the monocyclic aromatic heterocyclic ring does not include the number of carbon atoms of the substituent, and is preferably 2 to 5, more preferably 3 to 5.
- the monocyclic aromatic heterocycle in the ring R H1 and the ring R H2 include a pyrrole ring, a diazole ring, a triazole ring, a pyridine ring, a diazabenzene ring, and a triazine ring, and preferably a pyridine ring or a diazabenzene ring. Yes, these rings may have a substituent.
- the number of carbon atoms of the condensed aromatic heterocyclic ring is usually 2 to 60, preferably 4 to 30, excluding the number of carbon atoms of the substituent. Preferably, it is 6-20.
- Examples of the condensed aromatic heterocycle in the ring R H1 and the ring R H2 include, for example, an azanaphthalene ring, 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, phenazine ring and 5,10-dihydrophenazine ring, preferably azanaphthalene ring, diaza ring Naphthalene ring, carbazole ring, azacarbazole ring, diazacarbazole ring, dibenzofuran ring, dibenzothiophene ring, phenoxazine ring,
- Examples of the substituent that the ring R H1 and the ring R H2 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, and a substituted amino group.
- an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, a monovalent heterocyclic group or a substituted amino group is more preferred, and an alkyl group, a cycloalkyl group, an aryl group, a monovalent group
- a heterocyclic group or a substituted amino group is more preferred, an alkyl group, a cycloalkyl group, or a group represented by the formula (DA), formula (DB) or formula (DC) is particularly preferred, and an alkyl group or a cycloalkyl group is preferred. Particularly preferred, these groups may further have a substituent.
- Examples of the aryl group, monovalent heterocyclic group and substituted amino group in the substituents that the ring R H1 and the ring R H2 may have include and the preferred ranges of the ring L 1 and the ring L 2 , respectively.
- Examples of the aryl group, monovalent heterocyclic group and substituted amino group in the substituent which may be the same as the preferred range are the same.
- Examples and preferred ranges of the aryl group, monovalent heterocyclic group and substituted amino group in the substituent which the substituent which the ring R H1 and the ring R H2 may have further have are respectively Examples of the aryl group, monovalent heterocyclic group, and substituted amino group in the substituent that L 1 and ring L 2 may have are the same as the preferred range.
- One combination of the ring R H1 and the ring R H2 is a condensed aromatic hydrocarbon ring or a condensed aromatic heterocyclic ring, and the other is a monocyclic aromatic hydrocarbon ring or a monocyclic aromatic heterocyclic ring. More preferably, one is a condensed aromatic hydrocarbon ring or condensed aromatic heterocycle, the other is a monocyclic aromatic hydrocarbon ring, and one is a condensed aromatic ring More preferably, it is an aromatic hydrocarbon ring, and the other is a monocyclic aromatic hydrocarbon ring.
- X H1 is preferably a single bond, an oxygen atom or a sulfur atom, and more preferably a single bond.
- R XH1 is preferably an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, more preferably an aryl group or a monovalent heterocyclic group, still more preferably an aryl group. These groups may have a substituent.
- R XH1 ′ is preferably an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group or a substituted amino group, more preferably an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic ring.
- a group more preferably an alkyl group, a cycloalkyl group or an aryl group, and particularly preferably an alkyl group or a cycloalkyl group, and these groups optionally have a substituent.
- R XH1 and R XH1 ′ may have are examples of the substituent that the ring R H1 and the ring R H2 may further have. And the same as the preferred range.
- the group represented by the formula (H1-1) is preferably a group represented by the formula (H1-1B), a group represented by the formula (H1-1C), or a formula (H1-1D).
- X H2 and X H3 are preferably a single bond, a group represented by —N (R XH2 ) —, or a group represented by —C (R XH2 ′ ) 2 —, more preferably a single group.
- At least one of X H2 and X H3 is preferably a single bond, and X H3 is more preferably a single bond.
- X H2 and X H3 are a single bond
- the other is an oxygen atom, a sulfur atom, a group represented by —N (R XH2 ) —, or —C (R XH2 ′ ) 2 —.
- R XH2 and preferred ranges are the same as examples of R XH1 and preferred ranges.
- R XH2 'examples and preferred ranges, R XH1' is the same as the examples and preferable range.
- Examples of the substituent that R XH2 and R XH2 ′ may have and preferred ranges thereof are examples of the substituent that the ring R H1 and the ring R H2 may further have. And the same as the preferred range.
- Z H1 , Z H2 , Z H3 , Z H4 , Z H5 , Z H6 , Z H7 , Z H8 , Z H9 , Z H10 , Z H11 and Z H12 are preferably carbon atoms.
- R H1 , R H2 , R H3 , R H4 , R H5 , R H6 , R H7 , R H8 , R H9 , R H10 , R H11 and R H12 are a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, A cycloalkoxy group, an aryl group, a monovalent heterocyclic group or a substituted amino group is preferred, and a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group or a substituted amino group is preferred.
- a hydrogen atom, an alkyl group, a cycloalkyl group, or a group represented by the formula (DA), formula (DB), or formula (DC) is more preferable, and a hydrogen atom, an alkyl group, or a cycloalkyl group is particularly preferable.
- a hydrogen atom is particularly preferable, and these groups may further have a substituent. Examples of substituents that R H1 , R H2 , R H3 , R H4 , R H5 , R H6 , R H7 , R H8 , R H9 , R H10 , R H11, and R H12 may have are as follows.
- the examples of the substituent which the ring R H1 and the ring R H2 may have and the substituent which the ring R H2 may further have are the same as the preferred range.
- R H1 and R H2 , R H3 and R H4 , R H5 and R H6 , R H6 and R H7 , R H7 and R H8 , R H9 and R H10 , R H10 and R H11 , and R H11 and R H12 are These may be bonded to each other to form a ring together with the carbon atoms to which they are bonded, but it is preferable not to form a ring.
- L H1 is preferably an alkylene group, a cycloalkylene group, an arylene group or a divalent heterocyclic group, more preferably an arylene group or a divalent heterocyclic group, and even more preferably an arylene group. These groups may have a substituent.
- the arylene group represented by L H1 is preferably a phenylene group, a naphthalene diyl group, a fluorenediyl group, a phenanthrene diyl group or a dihydrophenanthrene diyl group, and more preferably a formula (A-1) to a formula ( A-9), a group represented by formula (A-19) or formula (A-20), more preferably a group represented by formula (A-1) to formula (A-3). Particularly preferred is a group represented by the formula (A-1) or (A-2), and particularly preferred is a group represented by the formula (A-2). These groups have substituents. You may have.
- the divalent heterocyclic group represented by L H1 is preferably a group represented by the formula (AA-1) to the formula (AA-34), more preferably a formula (AA-1) to Groups represented by formula (AA-6), formula (AA-10) to formula (AA-21), or formula (AA-24) to formula (AA-34), more preferably formula (AA- 1) to groups represented by formula (AA-4), formula (AA-10) to formula (AA-15), or formula (AA-29) to formula (AA-34), particularly preferably A group represented by formula (AA-2), formula (AA-4), formula (AA-10), formula (AA-12) or formula (AA-14).
- Examples and preferred ranges of the substituent that L H1 may have are the same as examples and preferred ranges of the substituent that the ring R H1 and ring R H2 may have. Examples and preferred ranges of the substituent that the substituent which L H1 may have may further have a substituent which the ring R H1 and ring R H2 may have further include. Examples of the preferred substituents and the preferred ranges are the same.
- R H1 ′ is preferably an aryl group or a monovalent heterocyclic group, more preferably an aryl group, and these groups optionally have a substituent. Examples and preferred ranges of the substituent that R H1 ′ may have are examples and preferred ranges of the substituent that the ring R H1 and ring R H2 may further have. Is the same.
- the number of carbon atoms of the aromatic hydrocarbon group does not include the number of carbon atoms of the substituent, and is usually 6 to 60, preferably 6 to 30, and more preferably 6 to 18.
- the aromatic hydrocarbon group include a benzene ring, a naphthalene ring, anthracene ring, phenanthrene ring, dihydrophenanthrene ring, a naphthacene ring, a fluorene ring, spirobifluorene ring, indene ring, a pyrene ring, a perylene ring, a chrysene ring Or a group formed by removing one or more hydrogen atoms directly bonded to the carbon atoms constituting the ring from a condensed ring of these rings, preferably a benzene ring, naphthalene ring, phenanthrene ring, dihydro A phenanthrene ring,
- a group formed by removing one or more hydrogen atoms directly bonded particularly preferably a group formed by removing one or more hydrogen atoms directly bonded to a carbon atom constituting the ring from a benzene ring, and these groups May have a substituent.
- the number of carbon atoms of the aromatic heterocyclic group is usually 1 to 60, preferably 2 to 40, more preferably 3 to 20, excluding the number of carbon atoms of the substituent. More preferably, it is 3-10.
- the aromatic heterocyclic group includes pyrrole ring, furan ring, thiophene ring, oxadiazole ring, thiadiazole ring, thiazole ring, oxazole ring, isothiazole ring, isoxazole ring, benzooxadiazole ring, benzo Thiadiazole ring, benzothiazole ring, benzoxazole ring, pyridine ring, diazabenzene ring, triazine ring, azanaphthalene ring, diazanaphthalene ring, triazanaphthalene ring, tetraazanaphthalene ring, azaanthracene ring, diazaanthracene ring, diazaan
- a group formed by removing one or more elementary atoms is preferred), more preferably a pyridine ring, a diazabenzene ring, a triazine ring, a quinoline ring, an isoquinoline ring, a quinazoline ring, a quinoxaline ring, an acridine ring, a phenazine ring, a phenanthroline ring, or a dibenzofuran ring.
- Ar H2 has an excellent luminance life of the light emitting device according to the embodiment of the present invention, preferably, a benzene ring, a fluorene ring, a spirobifluorene ring, a pyridine ring, a diazabenzene ring, a triazine ring, a quinoline ring, an isoquinoline ring, a quinazoline.
- a group formed by removing one or more atoms More preferably a group formed by removing one or more hydrogen atoms directly bonded to the carbon atoms constituting the ring from a benzene ring,
- Ar H2 may have a substituent (different from the group represented by the formula (1H ′) described later. The same shall apply hereinafter) as an alkyl group, cycloalkyl group, alkoxy group, cycloalkoxy.
- Group, aryl group, aryloxy group, monovalent heterocyclic group, substituted amino group or halogen atom are preferred, alkyl group, cycloalkyl group, alkoxy group, cycloalkoxy group, aryl group, monovalent heterocyclic group or substituted group
- An amino group is more preferable, an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group or a substituted amino group is more preferable, and an alkyl group, a cycloalkyl group, a formula (DA), a formula (D- B) or a group represented by formula (DC) is particularly preferred, and a group represented by formula (DA), formula (DB) or formula (DC) is
- aryl group, monovalent heterocyclic group and substituted amino group in the substituent that Ar H2 may have and preferred ranges thereof are the substituents that ring L 1 and ring L 2 may have, respectively. Are the same as the examples and preferred ranges of the aryl group, monovalent heterocyclic group and substituted amino group.
- Examples of aryl groups, monovalent heterocyclic groups, and substituted amino groups in the substituents that the substituent that Ar H2 may have further may further have the ring L 1 and the ring L, respectively.
- Examples of the aryl group, monovalent heterocyclic group and substituted amino group in the substituent that 2 may have are the same as the preferred range.
- the compound represented by the formula (H) is preferably represented by the formula (H′-1) to the formula (H′-14) because the luminance lifetime of the light emitting device according to the embodiment of the present invention is more excellent.
- a compound represented by the formula (H′-4) is particularly preferable.
- R 1H represents a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, an aryloxy group, a monovalent heterocyclic group, a substituted amino group, a halogen atom, or a compound represented by the formula (1H ′ ), And these groups optionally have a substituent.
- a plurality of R 1H may be the same or different. However, at least one of a plurality of R 1H is a group represented by the formula (1H ′).
- n H2 are preferably groups represented by the formula (1H ′).
- R 1H is preferably a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, a monovalent heterocyclic group, a substituted amino group, or a group represented by the formula (1H ′).
- Examples and preferred ranges of the aryl group, monovalent heterocyclic group and substituted amino group in R 1H are the aryl group and monovalent heterocyclic ring in the substituent that the ring L 1 and ring L 2 may have, respectively.
- Examples and preferred ranges of the group and substituted amino group are the same.
- Examples and preferred ranges of the substituent that R 1H may have include examples and preferred ranges of the substituent that the ring R H1 and ring R H2 may further have. The same.
- Examples of the compounds represented by formula (H′-1) to formula (H′-14) include compounds represented by formula (H ′′ -1) to formula (H ′′ -33). Preferably, it is a compound represented by the formula (H ′′ -1) to the formula (H ′′ -21), more preferably the formula (H ′′ -1) to the formula (H ′′ -11). More preferably, it is a compound represented by formula (H ′′ -1) to formula (H ′′ -8), and particularly preferred is a compound represented by formula (H ′′ -8). It is a compound represented.
- R 2H represents an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group, a substituted amino group, or a group represented by the formula (1H ′), and these groups have a substituent. You may do it.
- a plurality of R 2H may be the same or different. However, at least one of a plurality of R 2H is a group represented by the formula (1H ′).
- n H2 are preferably groups represented by the formula (1H ′).
- R 2H is preferably an alkyl group, a cycloalkyl group, a group represented by the formula (DA), formula (DB), formula (DC) or formula (1H ′), more preferably Is a group represented by the formula (DA), formula (DB), formula (DC) or formula (1H ′), more preferably the formula (DA) or formula (1H ′).
- R 2H is preferably an alkyl group, a cycloalkyl group, a group represented by the formula (DA), formula (DB), formula (DC) or formula (1H ′), more preferably Is a group represented by the formula (DA), formula (DB), formula (DC) or formula (1H ′), more preferably the formula (DA) or formula (1H ′).
- R 2H is preferably an alkyl group, a cycloalkyl group, a group represented by the formula (DA), formula (DB), formula (DC) or formula (1H ′), more preferably Is a group represented by the formula (DA), formula (DB),
- Examples and preferred ranges of the aryl group, monovalent heterocyclic group and substituted amino group in R 2H are the aryl group and monovalent heterocyclic ring in the substituent which ring L 1 and ring L 2 may have, respectively.
- Examples and preferred ranges of the group and substituted amino group are the same.
- Examples and preferred ranges of the substituent that R 2H may have include examples and preferred ranges of the substituent that the ring R H1 and ring R H2 may further have. The same.
- Examples of the compound represented by the formula (H) include a compound represented by the following formula. *
- the compound represented by the formula (H) is Aldrich, Luminescence Technologymin Corp. Etc. are available.
- the first organic layer is a layer containing a phosphorescent compound represented by the formula (1) and a compound represented by the formula (H).
- the first organic layer may contain a single phosphorescent compound represented by the formula (1), and the emission color of the light emitting device according to the embodiment of the present invention can be adjusted. Therefore, 2 or more types may be contained.
- the 1st organic layer may contain the compound represented by Formula (H) individually by 1 type, and may contain 2 or more types.
- the content of the phosphorescent compound represented by formula (1) is the sum of the phosphorescent compound represented by formula (1) and the compound represented by formula (H).
- it is usually 0.01 to 95 parts by weight, and since the luminance life of the light emitting device according to the embodiment of the present invention is more excellent, it is preferably 0.1 to 80 parts by weight.
- the amount is more preferably from 65 to 65 parts by weight, further preferably from 3 to 50 parts by weight, particularly preferably from 5 to 40 parts by weight.
- the first organic layer includes a phosphorescent compound represented by the formula (1), a compound represented by the formula (H), a hole transport material, a hole injection material, an electron transport material, an electron injection material, It may be a layer containing a composition containing at least one material selected from the group consisting of a light emitting material and an antioxidant (hereinafter also referred to as “first composition”). However, in the first composition, the light emitting material is different from the phosphorescent compound represented by the formula (1). In the first composition, the hole transport material, the hole injection material, the light emitting material, the electron transport material, and the electron injection material are different from the compound represented by the formula (H).
- 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 when the total of the phosphorescent compound represented by the formula (1) and the compound represented by the formula (H) is 100 parts by weight. 1 to 400 parts by weight, preferably 5 to 150 parts by weight.
- a hole transport material may be used individually by 1 type, or may use 2 or more types together.
- 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 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 total amount of the phosphorescent compound represented by the formula (1) and the compound represented by the formula (H) is 100 parts by weight, 1 to 400 parts by weight, preferably 5 to 150 parts by weight.
- An electron transport material may be used individually by 1 type, or may use 2 or more types together.
- 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 injection material and the electron injection material are each 100 weights of the total of the phosphorescent compound represented by the formula (1) and the compound represented by the formula (H).
- the amount is usually 1 to 400 parts by weight, preferably 5 to 150 parts by weight.
- Each of 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 type 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. Doping ions 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 group represented by the formula (X), a carbazole diyl group, a phenoxazine diyl group, and a phenothiazine diyl.
- the light emitting material preferably comprises a triplet light emitting complex.
- the triplet luminescent complex include the metal complexes shown below.
- the amount of the luminescent material is usually 1 when the total of the phosphorescent compound represented by the formula (1) and the compound represented by the formula (H) is 100 parts by weight. Up to 400 parts by weight, preferably 5 to 150 parts by weight.
- a luminescent material may be used individually by 1 type, or may use 2 or more types together.
- the antioxidant may be any compound that is soluble in the same solvent as the phosphorescent compound represented by formula (1) and the compound represented by formula (H) and does not inhibit light emission and charge transport. , Phenolic antioxidants and phosphorus antioxidants.
- the total amount of the phosphorescent compound represented by the formula (1) and the compound represented by the formula (H) is 100 parts by weight, 0.001 to 10 parts by weight.
- Antioxidants may be used alone or in combination of two or more.
- a composition containing a phosphorescent compound represented by the formula (1), a compound represented by the formula (H), and a solvent (hereinafter also referred to as “first ink”) is prepared by a spin coating method.
- 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 amount of the solvent is usually 1000 to 100,000 when the total of the phosphorescent compound represented by the formula (1) and the compound represented by the formula (H) is 100 parts by weight. Parts by weight, preferably 2000 to 20000 parts by weight.
- the second organic layer is a layer containing a crosslinked material of a crosslinking material.
- a cross-linked body of the cross-linking material can be obtained by cross-linking the cross-linking material by the above-described method and conditions.
- the cross-linking material may be a low molecular compound or a high molecular compound, but since the luminance life of the light emitting device according to the embodiment of the present invention is more excellent, at least one cross-link selected from the cross-linking group A group is used.
- a low molecular compound having a group hereinafter also referred to as “low molecular compound of the second organic layer” or a polymer compound containing a cross-linking structural unit having at least one cross-linking group selected from the cross-linking group A group (Hereinafter also referred to as “polymer compound of the second organic layer”), and is a polymer compound containing a cross-linking structural unit having at least one cross-linking group selected from the cross-linking group A group. Is more preferable.
- the crosslinkable group selected from the crosslinkable group A is preferably a group represented by the formula (XL-2) to the formula (XL-15) or the formula (XL-17) because the crosslinkability of the crosslinkable material is more excellent. More preferably, the formula (XL-2) to the formula (XL-4), the formula (XL-7) to the formula (XL-10), the formula (XL-14), the formula (XL-15) or the formula A crosslinking group represented by (XL-17), more preferably a crosslinking group represented by formula (XL-3), formula (XL-9), formula (XL-10) or formula (XL-17) And particularly preferably a crosslinking group represented by the formula (XL-17).
- the structural unit having at least one crosslinking group selected from the crosslinking group A group contained in the polymer compound of the second organic layer is represented by the structural unit represented by the formula (2) or the formula (2 ′). However, it may be a structural unit represented by the following formula.
- nA is preferably an integer of 0 to 3, more preferably an integer of 0 to 2, more preferably 0 or 1, since the luminance lifetime of the light emitting device according to the embodiment of the present invention is more excellent. Particularly preferred is 0. n is preferably 2 because the luminance lifetime of the light emitting device according to the embodiment of the present invention is more excellent.
- Ar 3 is preferably an aromatic hydrocarbon group which may have a substituent since the luminance lifetime of the light emitting device according to the embodiment of the present invention is more excellent.
- 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 a group represented by the formula (A-1) to the formula (A-20), More preferably, groups represented by formula (A-1), formula (A-2), formula (A-6) to formula (A-10), formula (A-19) or formula (A-20) And more preferably a group represented by formula (A-1), formula (A-2), formula (A-7), formula (A-9) or formula (A-19), This group 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 part 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.
- substituents include an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, and an aryloxy group.
- Group, halogen atom, monovalent heterocyclic group and cyano group are preferred.
- the alkylene group represented by L A is usually 1 to 20, preferably 1 to 15, more preferably 1 to 10, not including the number of carbon atoms of the substituent. Cycloalkylene group represented by L A is not including the carbon atom number of substituent is usually 3 to 20.
- the alkylene group and the cycloalkylene group may have a substituent, and examples thereof include a methylene group, an ethylene group, a propylene group, a butylene group, a hexylene group, a cyclohexylene group, and an octylene group.
- Alkylene group and cycloalkylene group represented by L A may have a substituent.
- the substituent that the alkylene group and the cycloalkylene group may have is preferably an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, a halogen atom or a cyano group, and these groups further have a substituent. It may be.
- the 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, or a bridging group A.
- a crosslinking group selected from the group is preferred, and these groups may further have a substituent.
- the divalent heterocyclic group represented by L A is preferably a group represented by formula (AA-1) to formula (AA-34).
- L A is preferably an arylene group or an alkylene group, more preferably a phenylene group, a fluorenediyl group, or an alkylene group, because production of the polymer compound of the second organic layer is facilitated.
- This group may have a substituent.
- the crosslinking group represented by X is represented by the formula (XL-2) to the formula (XL-15) or the formula (XL-17) because the crosslinkability of the polymer compound of the second organic layer is excellent. And more preferably a formula (XL-2) to a formula (XL-4), a formula (XL-7) to a formula (XL-10), a formula (XL-14), a formula (XL-15) or A crosslinking group represented by the formula (XL-17), more preferably represented by the formula (XL-3), the formula (XL-9), the formula (XL-10) or the formula (XL-17).
- the formula (XL-1) to the formula (XL-4) and the formula (XL-7) are preferable.
- a bridging group represented by formula (XL-10) or formula (XL-14) to formula (XL-17) more preferably formula (XL-1), formula (XL-3), formula (XL) XL-9), a formula (XL-10), a formula (XL-16) or a crosslinking group represented by formula (XL-17), and more preferably a formula (XL-1), a formula (XL-16).
- the structural unit represented by the formula (2) is excellent in the stability and crosslinkability of the polymer compound of the second organic layer, it is based on the total amount of the structural units contained in the polymer compound of the second organic layer. Thus, it is preferably 0.5 to 80 mol%, more preferably 3 to 50 mol%, still more preferably 5 to 20 mol%.
- One type of structural unit represented by the formula (2) may be contained in the polymer compound of the second organic layer, or two or more types may be contained.
- mA is preferably an integer of 0 to 3, more preferably an integer of 0 to 2, and even more preferably 0 or 1, since the luminance lifetime of the light emitting device according to the embodiment of the present invention is more excellent. Particularly preferred is 0. m is preferably 1 or 2 and more preferably 2 because the luminance lifetime of the light emitting device according to the embodiment of the present invention is more excellent. c is preferably 0 because it facilitates the production of the polymer compound of the second organic layer and the luminance lifetime of the light emitting device according to the embodiment of the present invention is more excellent.
- Ar 5 is preferably an aromatic hydrocarbon group which may have a substituent since the luminance lifetime of the light emitting device according to the embodiment of the present invention is more excellent.
- the definition and examples of the arylene group portion excluding m substituents of the aromatic hydrocarbon group represented by Ar 5 are the same as the definitions and examples of the arylene group represented by Ar X2 in formula (X) described later. It is.
- the definition and examples of the divalent heterocyclic group part excluding m substituents of the heterocyclic group represented by Ar 5 are the divalent heterocyclic group represented by Ar X2 in formula (X) described later. Same as definition and example of part.
- divalent groups excluding m substituents of a group in which at least one aromatic hydrocarbon ring represented by Ar 5 and at least one heterocyclic ring are directly bonded are shown in the formula ( The definition and examples of the divalent group in which at least one arylene group represented by Ar X2 in X) and at least one divalent heterocyclic group are directly bonded are the same.
- Ar 4 and Ar 6 are preferably an arylene group which may have a substituent since the luminance lifetime of the light emitting device according to the embodiment of the present invention is more excellent.
- 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) described later.
- 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) described later. is there.
- 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, Examples thereof include a halogen atom, a monovalent heterocyclic group, and a cyano group.
- K A since production of the polymer compound of the second organic layer becomes easy, it is preferable that a phenylene group or a methylene group.
- crosslinking group represented by X ′ are the same as the definition and example of the crosslinking group represented by X described above.
- the structural unit represented by the formula (2 ′) is excellent in the stability of the polymer compound in the second organic layer and in the crosslinking property of the polymer compound in the second organic layer.
- the amount is preferably 0.5 to 50 mol%, more preferably 3 to 30 mol%, still more preferably 5 to 20 mol%, based on the total amount of structural units contained in the polymer compound in the layer.
- One type of structural unit represented by the formula (2 ′) may be contained in the polymer compound of the second organic layer, or two or more types may be contained.
- Examples of the structural unit represented by the formula (2) include structural units represented by the formula (2-1) to the formula (2-30), and the structural unit represented by the formula (2 ′) Examples 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 -1) to Formula (2-15), Formula (2-19), Formula (2-20), Formula (2-23), Formula (2-25), or Formula (2-30)
- the second organic layer further contains a structural unit represented by the formula (X).
- the polymer compound of the second organic layer preferably further includes a structural unit represented by the formula (Y) because the luminance life of the light emitting device according to the embodiment of the present invention is more excellent.
- 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. And these groups may have a substituent.
- Ar X2 and Ar X4 When there are a plurality of Ar X2 and Ar X4 , 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. When there are a plurality of R X2 and R X3 , they may be the same or different. ]
- a X1 is preferably an integer of 2 or less, more preferably 1, because the luminance lifetime of the light emitting device according to the embodiment of the present invention is more excellent.
- a X2 is preferably an integer of 2 or less, more preferably 0, because the luminance lifetime of the light emitting device according to the embodiment of the present invention 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, more preferably an aryl group, and these groups have a substituent. Also good.
- the arylene group represented by Ar X1 and Ar X3 is more preferably a group represented by the formula (A-1) or the formula (A-9), and more preferably a formula (A-1). These groups may have a substituent.
- the divalent heterocyclic group represented by Ar X1 and Ar X3 is more preferably represented by Formula (AA-1), Formula (AA-2), or Formula (AA-7) to Formula (AA-26). 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 represented by formula (A-1), formula (A-6), formula (A-7), formula (A-9) to formula (A-11). Or it is group represented by a formula (A-19), and these groups may have a substituent.
- the more preferable range of the divalent heterocyclic group represented by Ar X2 and Ar X4 is the same as the more preferable range of the divalent heterocyclic group represented by Ar X1 and Ar X3 .
- 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 optionally have a substituent.
- R XX is preferably an alkyl group, a cycloalkyl group, or an aryl group, and these groups optionally have a substituent.
- Ar X2 and Ar X4 are preferably an arylene group which may have a substituent.
- the substituent which the groups 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, and these groups further have a substituent. You may do it.
- 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 formula (X-3) to formula (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 cyano. Represents a group, and 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 90 mol% based on the total amount of the structural units contained in the polymer compound of the second organic layer. More preferably, it is 1 to 70 mol%, and still more preferably 10 to 50 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).
- the structural unit represented by the formula (X) may be included alone or in combination of two or more.
- 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 arylene group represented by Ar Y1 is represented by formula (A-1), formula (A-6), formula (A-7), formula (A-9) to formula (A-11), formula (A) A-13) or a group represented by formula (A-19), more preferably in formula (A-1), formula (A-7), formula (A-9) or formula (A-19). And these groups may have a substituent.
- the divalent heterocyclic group represented by Ar Y1 is represented by 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 represented by formula (AA-4), formula (AA-10), formula (AA-18) or formula (AA-20) These groups may have a substituent.
- the ranges are the same as the more preferable ranges and further preferable ranges 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 to each other is 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, and these groups may further have a substituent.
- Examples of the structural unit represented by the formula (Y) include structural units represented by the formula (Y-1) to the formula (Y-7), and the luminance lifetime of the light-emitting element according to the embodiment of the present invention. From the viewpoint of the above, it is preferably a structural unit represented by the formula (Y-1) or the formula (Y-2), and from the viewpoint of the electron transport property of the polymer compound of the second organic layer, preferably the formula (Y-3) or a structural unit represented by the formula (Y-4), and from the viewpoint of the hole transport property of the polymer compound of the second organic layer, preferably the formula (Y-5) to the formula It is a structural unit represented by (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 optionally 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, and these groups optionally 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 optionally 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, more preferably an alkyl group or a cycloalkyl group, and these groups optionally 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.
- R Y2 in the group represented by —C (R Y2 ) 2 — in X Y1 is preferably an alkyl group or a cycloalkyl group, both are aryl groups, and both are monovalent complex
- 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 formula (Y-A1) to formula (Y-A5), more preferably a group represented by formula (Y-A4), and these groups have a substituent. You may do it.
- the combination of two R Y2 in the group represented by —C (R Y2 ) ⁇ C (R Y2 ) — is preferably such that both are alkyl groups or cycloalkyl groups, 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 cycloalkyl group which may have a substituent. It is. A plurality of R Y2 may be bonded to each other to form a ring together with the atoms to which each is bonded. When 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), more preferably a group represented by the formula (Y-B3). It 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 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, and these groups have a substituent. May be.
- 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, more preferably an aryl group, and these groups have a substituent. May be.
- 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, has a higher luminance life of the light emitting device according to the embodiment of the present invention, and therefore the second organic layer polymer.
- the amount is preferably 0.5 to 80 mol%, more preferably 30 to 60 mol%, based on the total amount of structural units contained in the compound.
- the structural unit that is a group of the organic compound is preferably 0.5 to a total amount of the structural units contained in the polymer compound of the second organic layer because the polymer compound of the second organic layer is excellent in charge transportability. It is 40 mol%, more preferably 3 to 30 mol%.
- One type of structural unit represented by the formula (Y) may be contained in the polymer compound of the second organic layer, or two or more types may be contained.
- Examples of the polymer compound in the second organic layer include polymer compounds P-1 to P-8 shown in Table 1.
- the “other structural unit” means a structural unit other than the structural units represented by Formula (2), Formula (2 ′), Formula (X), and Formula (Y).
- 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 , more preferably 1.5 ⁇ 10 4 to 1 ⁇ 10 5 .
- the polymer compound of the second organic layer can be produced using a known polymerization method described in Chemical Review (Chem. Rev.), Vol. 109, pages 897-1091 (2009), etc. Examples thereof include a polymerization method by a coupling reaction using a transition metal catalyst such as a reaction, a Yamamoto reaction, a Buchwald reaction, a Stille reaction, a Negishi reaction, and a Kumada reaction.
- a transition metal catalyst such as a reaction, a Yamamoto reaction, a Buchwald reaction, a Stille reaction, a Negishi reaction, and a Kumada reaction.
- a method of charging the monomer a method of charging the entire amount of the monomer into the reaction system at once, a part of the monomer is charged and reacted, and then the remaining monomer is 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 low molecular compound of the second organic layer is preferably a low molecular compound represented by the formula (3).
- m B1 , m B2 and m B3 each independently represent an integer of 0 or more.
- a plurality of m B1 may be the same or different.
- a plurality of m B3 are present, they may be the same or different.
- Ar 7 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. When a plurality of Ar 7 are present, they may be the same or different.
- L B1 represents an alkylene group, a cycloalkylene group, an arylene group, a divalent heterocyclic group, a group represented by —N (R ′ ′′) —, an oxygen atom or a sulfur atom, and these groups are substituent groups. You may have.
- 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.
- a plurality of L B1 When a plurality of L B1 are present, they may be the same or different.
- X ′′ represents a bridging group, a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, and these groups may have a substituent.
- a plurality of X ′′ may be the same or different. However, at least one of a plurality of X ′′ is a crosslinking group.
- m B1 is generally an integer of 0 to 10, and is preferably an integer of 0 to 5, more preferably an integer of 0 to 2, and even more preferably 0 or 0, because synthesis of the crosslinking material is facilitated.
- m B2 is usually an integer of 0 to 10, and is preferably an integer of 0 to 5 because the synthesis of the crosslinking material is facilitated and the luminance life of the light emitting device according to the embodiment of the present invention is more excellent. More preferably, it is an integer of 0 to 3, more preferably 1 or 2, and particularly preferably 1.
- m B3 is usually an integer of 0 to 5, for the synthesis of cross-linked material is facilitated, and preferably is an integer of from 0 to 4, more preferably an integer of 0 to 2, more preferably at 0 is there.
- the definition and examples of the arylene group part excluding m B3 substituents of the aromatic hydrocarbon group represented by Ar 7 are the definitions and examples of the arylene group represented by Ar X2 in the aforementioned formula (X). The same.
- the definition and examples of the divalent heterocyclic group part excluding m B3 substituents of the heterocyclic group represented by Ar 7 are the divalent heterocyclic ring represented by Ar X2 in the above formula (X). Same as definition and example of base part.
- the definition and examples of the divalent group excluding m B3 substituents of the group in which at least one aromatic hydrocarbon ring represented by Ar 7 and at least one heterocycle are directly bonded are as described above.
- the definition and example of the divalent group in which at least one kind of arylene group represented by Ar X2 and at least one kind of divalent heterocyclic group in (X) are directly bonded are the same.
- the definition and example of the substituent that the group represented by Ar 7 may have are the same as the definition and example of the substituent that the group represented by Ar X2 in Formula (X) may have. is there.
- Ar 7 is preferably an aromatic hydrocarbon group because the luminance lifetime of the light emitting device according to the embodiment of the present invention is excellent, and this aromatic hydrocarbon group may have a substituent.
- alkylene group, cycloalkylene group, arylene group and divalent heterocyclic group represented by L B1 are respectively the alkylene group, cycloalkylene group, arylene group and divalent represented by L A described above. This is the same as the definition and example of the heterocyclic group of
- L B1 is preferably an alkylene group, an arylene group or an oxygen atom, more preferably an alkylene group or an arylene group, still more preferably a phenylene group, a fluorenediyl group or An alkylene group, particularly preferably a phenylene group or an alkylene group, and these groups optionally have a substituent.
- X ′′ is preferably a bridging group, an aryl group or a monovalent heterocyclic group represented by any one of the formulas (XL-1) to (XL-17), more preferably the formula (XL -1), a crosslinking group represented by formula (XL-3), formula (XL-7) to formula (XL-10), formula (XL-16) or formula (XL-17), or an aryl group More preferably a crosslinking group represented by the formula (XL-1), the formula (XL-16) or the formula (XL-17), a phenyl group, a naphthyl group or a fluorenyl group.
- XL-16 or a crosslinking group represented by the formula (XL-17), a phenyl group or a naphthyl group, particularly preferably a crosslinking group represented by the formula (XL-16) or a naphthyl group, These groups may have a substituent.
- cross-linking material examples include low molecular compounds represented by formulas (3-1) to (3-16), and preferably represented by formulas (3-1) to (3-10). Low molecular compounds, more preferably low molecular compounds represented by formulas (3-5) to (3-9).
- the low molecular weight compound of the second organic layer is available from Aldrich, Luminescence Technology Corp. Available from the American Dye Source. In addition, it is compoundable according to the method described in the international publication 1997/033193, the international publication 2005/035221, and the international publication 2005/049548, for example.
- the crosslinked material of the crosslinking material may be contained singly or in combination of two or more.
- the second organic layer includes a crosslinked material of a crosslinking material and at least one material selected from the group consisting of a hole transport material, a hole injection material, an electron transport material, an electron injection material, a light emitting material, and an antioxidant. May be a layer containing a composition (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 luminescent material contained in the second composition are the hole transport material contained in the first composition.
- the examples of the electron transport material, the hole injection material, the electron injection material, and the light emitting material are the same as the preferred range.
- 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 usually 1 when the crosslinked material is 100 parts by weight. Up to 400 parts by weight, preferably 5 to 150 parts by weight.
- the blending amount of the antioxidant is usually 0.001 to 10 parts by weight when the crosslinked material of the crosslinking material is 100 parts by weight.
- the second composition containing the crosslinking material and the solvent (hereinafter also referred to as “second ink”) can be suitably used in the wet method described in the section of the first ink.
- 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 compounding amount of the solvent is usually 1000 to 100,000 parts by weight, preferably 2000 to 20000 parts by weight when the crosslinking material is 100 parts by weight.
- the light emitting element according to the embodiment of the present invention 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 referred to as “first light emitting layer”).
- the second organic layer is usually a hole transport layer, a second light emitting layer or an electron transport layer, preferably a hole transport layer or a second light emitting layer. Yes, more preferably a hole transport layer.
- the first organic layer and the second organic layer are preferably adjacent to each other because the luminance life of the light emitting device according to the embodiment of the present invention is more excellent.
- the second organic layer is a layer provided between the anode and the first organic layer because the luminance life of the light emitting device according to the embodiment of the present invention is more excellent.
- the second organic layer is a hole transport layer provided between the anode and the first organic layer
- the luminance lifetime of the light emitting device according to the embodiment of the present invention Therefore, it is preferable to further have a hole injection layer between the anode and the second organic layer.
- the second organic layer is a hole transport layer provided between the anode and the first organic layer
- the luminance life of the light emitting device according to the embodiment of the present invention is more excellent. It is preferable to further include at least one of an electron injection layer and an electron transport layer between the organic layer and the organic layer.
- the luminance of the light emitting device according to the embodiment of the present invention since the lifetime is more excellent, it is preferable to further include at least one of a hole injection layer and a hole transport layer between the anode and the second organic layer.
- the second organic layer is a second light emitting layer provided between the anode and the first organic layer, the luminance life of the light emitting device according to the embodiment of the present invention is more excellent. It is preferable to further include at least one of an electron injection layer and an electron transport layer between one organic layer.
- the luminance of the light emitting device according to the embodiment of the present invention since the lifetime is more excellent, it is preferable to further include at least one of a hole injection layer and a hole transport layer between the anode and the first organic layer.
- the second organic layer is a second light emitting layer provided between the cathode and the first organic layer, the luminance life of the light emitting device according to the embodiment of the present invention is more excellent. It is preferable to further include at least one of an electron injection layer and an electron transport layer between the two organic layers.
- the luminance lifetime of the light emitting device according to the embodiment of the present invention is Since it is more excellent, it is preferable to further include at least one of a hole injection layer and a hole transport layer between the anode and the first organic layer.
- the second organic layer is an electron transport layer provided between the cathode and the first organic layer, the luminance life of the light emitting device according to the embodiment of the present invention is more excellent. It is preferable to further have an electron injection layer between the organic layer.
- the layer structure of the light emitting device according to the embodiment of the present invention include layer structures represented by the following (D1) to (D15).
- the light-emitting element according to the embodiment of the present invention usually includes a substrate, but may be stacked on the substrate from the anode, or may be stacked on the substrate from the cathode.
- “/” means that the previous and subsequent layers are adjacently stacked.
- “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. Since the luminance lifetime of the light emitting device according to the embodiment of the present invention is more excellent, 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 each have two or more layers as necessary. It may be provided.
- 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 light-emitting efficiency and the element life of the light-emitting element.
- 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 first light-emitting layer. 2 organic layers are 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 layer.
- the organic layer is preferable.
- 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 is represented by the formula (ET-1).
- a polymer compound containing at least one structural unit selected from the group consisting of a structural unit represented by formula (ET-2) and a structural unit represented by formula (ET-2) (hereinafter, also referred to as “electron transport layer polymer compound”). ) Is preferable.
- nE1 represents an integer of 1 or more.
- Ar E1 represents an aromatic hydrocarbon group or a heterocyclic group, and these groups may have a substituent other than R E1 .
- R E1 represents a group represented by the formula (ES-1). When a plurality of R E1 are present, they may be the same or different. ]
- nE3 represents an integer of 0 or more
- aE1 represents an integer of 1 or more
- bE1 represents an integer of 0 or more
- mE1 represents an integer of 1 or more.
- nE3, aE1, and bE1 may be the same or different.
- mE1 is 1 when R E3 is a single bond.
- aE1 and bE1 are selected so that the charge of the group represented by the formula (ES-1) becomes zero.
- R E3 represents a single bond, a hydrocarbon group, a heterocyclic group or —O—R E3 ′ (R E3 ′ represents a hydrocarbon group or a heterocyclic group), and these groups have a substituent. It may be.
- Q E1 represents an alkylene group, a cycloalkylene group, an arylene group, an oxygen atom or a sulfur atom, and these groups optionally have a substituent. When a plurality of Q E1 are present, they may be the same or different.
- Y E1 represents CO 2 ⁇ , SO 3 ⁇ , SO 2 — or PO 3 2 ⁇ . When a plurality of Y E1 are present, they may be the same or different.
- M E1 represents an alkali metal cation, an alkaline earth metal cation or an ammonium cation, and this ammonium cation may have a substituent. When a plurality of M E1 are present, they may be the same or different.
- Z E1 is F ⁇ , Cl ⁇ , Br ⁇ , I ⁇ , OH ⁇ , B (R E4 ) 4 ⁇ , R E4 SO 3 ⁇ , R E4 COO ⁇ , NO 3 ⁇ , SO 4 2 ⁇ , HSO 4 ⁇ . , PO 4 3 ⁇ , HPO 4 2 ⁇ , H 2 PO 4 ⁇ , BF 4 ⁇ or PF 6 ⁇ .
- R E4 represents an alkyl group, a cycloalkyl group, or an aryl group, and these groups optionally have a substituent. When a plurality of Z E1 are present, they may be the same or different. ]
- NE1 is usually an integer of 1 to 4, preferably 1 or 2.
- Examples of the aromatic hydrocarbon group or heterocyclic group represented by Ar E1 include 1,4-phenylene group, 1,3-phenylene group, 1,2-phenylene group, 2,6-naphthalenediyl group, 1,4 Hydrogen bonded directly to the atoms constituting the ring from a naphthalenediyl group, a 2,7-fluorenediyl group, a 3,6-fluorenediyl group, a 2,7-phenanthenediyl group or a 2,7-carbazolediyl group
- a group excluding one atom nE1 is preferable, and may have a substituent other than R E1 .
- Examples of the substituent other than R E1 that Ar E1 may have 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, and an aryloxy group.
- 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 aryloxy group.
- n ′, m ′ and nx each independently represents an integer of 1 or more.
- nE3 is usually an integer of 0 to 10, preferably an integer of 0 to 8, and more preferably an integer of 0 to 2.
- aE1 is usually an integer of 1 to 10, preferably an integer of 1 to 5, and more preferably 1 or 2.
- bE1 is generally an integer of 0 to 10, preferably an integer of 0 to 4, more preferably 0 or 1.
- mE1 is usually an integer of 1 to 5, preferably 1 or 2, and more preferably 1.
- R E3 is —O—R E3 ′
- the group represented by the formula (ES-1) is a group represented by the following formula. -O-R E3 '- ⁇ (Q E1 ) nE3 -Y E1 (M E1 ) aE1 (Z E1 ) bE1 ⁇ mE1
- R E3 is preferably a hydrocarbon group or a heterocyclic group, more preferably an aromatic hydrocarbon group or an aromatic heterocyclic group, and still more preferably an aromatic hydrocarbon group.
- R E3 may have include an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group, and a group represented by the formula (ES-3).
- the group represented by 3) is preferred.
- Q E1 is preferably an alkylene group, an arylene group or an oxygen atom, more preferably an alkylene group or an oxygen atom.
- Y E1 is preferably CO 2 ⁇ , SO 2 ⁇ or PO 3 2 ⁇ , more preferably CO 2 ⁇ .
- Examples of the alkali metal cation represented by M E1 include Li + , Na + , K + , Rb + , and Cs + . K + , Rb +, and Cs + are preferable, and Cs + is more preferable.
- Examples of the alkaline earth metal cation represented by M E1 include Be 2+ , Mg 2+ , Ca 2+ , Sr 2+ and Ba 2+ , and Mg 2+ , Ca 2+ and Sr 2+. Or Ba ⁇ 2+> is preferable and Ba ⁇ 2+> is more preferable.
- M E1 is preferably an alkali metal cation or alkaline earth metal cation, more preferably an alkali metal cation.
- Z E1 is preferably F ⁇ , Cl ⁇ , Br ⁇ , I ⁇ , OH ⁇ , B (R E4 ) 4 ⁇ , R E4 SO 3 ⁇ , R E4 COO ⁇ or NO 3 ⁇ , and F ⁇ , Cl ⁇ . , Br -, I -, OH -, R E4 SO 3 - or R E4 COO - are preferred.
- R E4 is preferably an alkyl group.
- Examples of the group represented by the formula (ES-1) include a group represented by the following formula.
- M + represents Li + , Na + , K + , Cs + or N (CH 3 ) 4 + .
- M + represents Li + , Na + , K + , Cs + or N (CH 3 ) 4 + .
- M + may be the same or different.
- nE2 represents an integer of 1 or more.
- Ar E2 represents an aromatic hydrocarbon group or a heterocyclic group, and these groups may have a substituent other than R E2 .
- R E2 represents a group represented by the formula (ES-2). When a plurality of R E2 are present, they may be the same or different. ]
- nE4 represents an integer of 0 or more
- aE2 represents an integer of 1 or more
- bE2 represents an integer of 0 or more
- mE2 represents an integer of 1 or more.
- nE4 represents an integer of 0 or more
- aE2 represents an integer of 1 or more
- bE2 represents an integer of 0 or more
- mE2 represents an integer of 1 or more.
- R E5 represents a single bond, a hydrocarbon group, a heterocyclic group or —O—R E5 ′ (R E5 ′ represents a hydrocarbon group or a heterocyclic group), and these groups have a substituent. It may be.
- Q E2 represents an alkylene group, a cycloalkylene group, an arylene group, an oxygen atom or a sulfur atom, and these groups optionally have a substituent. When a plurality of Q E2 are present, they may be the same or different.
- Y E2 represents -C + R E6 2 , -N + R E6 3 , -P + R E6 3 , -S + R E6 2 or -I + R E6 2 .
- R E6 represents a hydrogen atom, an alkyl group, a cycloalkyl group, or an aryl group, and these groups optionally have a substituent.
- a plurality of R E6 may be the same or different.
- Y E2 When a plurality of Y E2 are present, they may be the same or different.
- M E2 represents F ⁇ , Cl ⁇ , Br ⁇ , I ⁇ , OH ⁇ , B (R E7 ) 4 ⁇ , R E7 SO 3 ⁇ , R E7 COO ⁇ , BF 4 ⁇ , SbCl 6 ⁇ or SbF 6 ⁇ .
- R E7 represents an alkyl group, a cycloalkyl group, or an aryl group, and these groups optionally have a substituent.
- M E2 represents an alkali metal cation or an alkaline earth metal cation.
- Z E2 represents an alkali metal cation or an alkaline earth metal cation.
- NE2 is usually an integer of 1 to 4, preferably 1 or 2.
- Examples of the aromatic hydrocarbon group or heterocyclic group represented by Ar E2 include 1,4-phenylene group, 1,3-phenylene group, 1,2-phenylene group, 2,6-naphthalenediyl group, 1,4 Hydrogen bonded directly to the atoms constituting the ring from a naphthalenediyl group, a 2,7-fluorenediyl group, a 3,6-fluorenediyl group, a 2,7-phenanthenediyl group or a 2,7-carbazolediyl group
- a group excluding n2 atoms is preferable, and may have a substituent other than R E2 .
- the substituent group other than Ar E2 is may have R E2, is the same as the substituent other than optionally Ar E1 is have R E1.
- nE4 is generally an integer of 0 to 10, preferably an integer of 0 to 8, and more preferably an integer of 0 to 2.
- aE2 is usually an integer of 1 to 10, preferably an integer of 1 to 5, and more preferably 1 or 2.
- bE2 is usually an integer of 0 to 10, preferably an integer of 0 to 4, more preferably 0 or 1.
- mE2 is usually an integer of 1 to 5, preferably 1 or 2, and more preferably 1.
- R E5 is —O—R E5 ′
- the group represented by the formula (ES-2) is a group represented by the following formula. -O-R E5 '- ⁇ (Q E1 ) nE3 -Y E1 (M E1 ) aE1 (Z E1 ) bE1 ⁇ mE1
- R E5 is preferably a hydrocarbon group or a heterocyclic group, more preferably an aromatic hydrocarbon group or an aromatic heterocyclic group, and still more preferably an aromatic hydrocarbon group.
- R E5 may have include an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group, and a group represented by the formula (ES-3).
- the group represented by 3) is preferred.
- Q E2 is preferably an alkylene group, an arylene group or an oxygen atom, more preferably an alkylene group or an oxygen atom.
- R E6 is preferably a hydrogen atom, an alkyl group or an aryl group, more preferably a hydrogen atom or an alkyl group.
- M E2 is preferably F ⁇ , Cl ⁇ , Br ⁇ , I ⁇ , B (R E7 ) 4 ⁇ , R E7 SO 3 ⁇ , R E7 COO ⁇ , BF 4 ⁇ or SbF 6 ⁇ , and Br ⁇ , I -, B (R E7) 4 -, R E7 COO - or SbF 6- is more preferable.
- R E7 is preferably an alkyl group.
- Examples of the alkali metal cation represented by Z E2 include Li + , Na + , K + , Rb + and Cs + , and Li + , Na + or K + is preferable.
- Examples of the alkaline earth metal cation represented by Z E2 include Be 2+ , Mg 2+ , Ca 2+ , Sr 2+ and Ba 2+ , with Mg 2+ or Ca 2+ being preferred.
- Z E2 is preferably an alkali metal cation.
- Examples of the group represented by the formula (ES-2) include a group represented by the following formula.
- X ⁇ represents F ⁇ , Cl ⁇ , Br ⁇ , I ⁇ , B (C 6 H 5 ) 4 ⁇ , CH 3 COO ⁇ or CF 3 SO 3 ⁇ .
- X ⁇ represents F ⁇ , Cl ⁇ , Br ⁇ , I ⁇ , B (C 6 H 5 ) 4 ⁇ , CH 3 COO ⁇ or CF 3 SO 3 ⁇ .
- X ⁇ represents F ⁇ , Cl ⁇ , Br ⁇ , I ⁇ , B (C 6 H 5 ) 4 ⁇ , CH 3 COO ⁇ or CF 3 SO 3 ⁇ .
- X ⁇ represents F ⁇ , Cl ⁇ , Br ⁇ , I ⁇ , B (C 6 H 5 ) 4 ⁇ , CH 3 COO ⁇ or CF 3 SO 3 ⁇ .
- Examples of the structural units represented by formula (ET-1) and formula (ET-2) include structural units represented by the following formula (ET-31) to formula (ET-38).
- Examples of the polymer compound for the electron transport layer include, for example, JP2009-239279A, JP2012-033845A, JP2012-216281A, JP2012-216822A, and JP2012-216815A. It can be synthesized according to the method described in 1.
- a material used for forming a hole injection layer a material used for forming a hole transport layer, a material used for forming a first light emitting layer, a material used for forming a second light emitting layer, and a material for forming an electron transport layer.
- the materials used and the materials used to form the electron injection layer are a hole injection layer, a hole transport layer, a first light emitting layer, a second light emitting layer, an electron transport layer, and an electron, respectively, in manufacturing a light emitting element.
- a method for avoiding dissolution of the material i) a method using a material having a crosslinking group, or ii) a method of providing a difference in solubility between adjacent layers is preferable.
- the layer after forming a layer using a material having a crosslinking group, the layer can be insolubilized by crosslinking the crosslinking group.
- the electron-emitting layer when an electron transport layer is stacked on a first light-emitting layer or a second light-emitting layer using a difference in solubility, the electron-emitting layer is soluble in the first light-emitting layer or the second light-emitting layer.
- the electron transport layer can be stacked by using a low solution.
- a solvent used when an electron transport layer is laminated on the first light-emitting layer or the second light-emitting layer using a difference in solubility water, alcohol, ether, ester, nitrile compound, nitro compound, Fluorinated alcohol, thiol, sulfide, sulfoxide, thioketone, amide, carboxylic acid and the like are preferable.
- the solvent examples include methanol, ethanol, 2-propanol, 1-butanol, tert-butyl alcohol, acetonitrile, 1,2-ethanediol, N, N-dimethylformamide, dimethyl sulfoxide, acetic acid, nitromethane, propylene carbonate , Pyridine, carbon disulfide, and a mixed solvent of these solvents.
- a mixed solvent one or more solvents selected from water, alcohols, ethers, esters, nitrile compounds, nitro compounds, fluorinated alcohols, thiols, sulfides, sulfoxides, thioketones, amides, carboxylic acids, and the like, and chlorinated solvents Further, it may be a mixed solvent with one or more of an aromatic hydrocarbon solvent, an aliphatic hydrocarbon solvent, and a ketone solvent.
- 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.
- 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 transport layer, the electron transport layer, the hole injection layer, and the electron injection layer is low.
- a molecular compound for example, a vacuum deposition method from a powder
- a method by film formation from a solution or a molten state is exemplified
- a polymer compound for example, a method by a film formation from a solution or a molten state is mentioned. It is done.
- 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 the following size exclusion chromatography (SEC) using tetrahydrofuran as the mobile phase. .
- SEC size exclusion chromatography
- the polymer compound to be measured was dissolved in tetrahydrofuran at a concentration of about 0.05% by weight, and 10 ⁇ L was injected into SEC. The mobile phase was run at a flow rate of 2.0 mL / min.
- PLgel MIXED-B manufactured by Polymer Laboratories
- a UV-VIS detector manufactured by Shimadzu Corporation, trade name: SPD-10Avp was used as the detector.
- the phosphorescent compound G1 was synthesized according to the method described in International Publication No. 2004/026886.
- the phosphorescent compound G2 was synthesized according to the method described in International Publication No. 2011/032626.
- the phosphorescent compound G3 was synthesized according to the method described in International Publication No. 2009/131255.
- the phosphorescent compound G4 was synthesized according to the method described in JP 2014-224101 A.
- the phosphorescent compound G5 was synthesized according to the method described in JP 2014-224101 A.
- Step 3 After the reaction, phenylboronic acid (36.8 mg) and dichlorobis (triphenylphosphine) palladium (2.1 mg) were added thereto and refluxed for 16.5 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 weight aqueous acetic acid solution and twice with water, and the resulting solution was added dropwise to methanol, resulting in precipitation.
- 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 3.12 g of a polymer compound HTL-2.
- the polymer compound HTL-2 had an Mn of 7.8 ⁇ 10 4 and an Mw of 2.6 ⁇ 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 M1, a structural unit derived from the compound M2, a structural unit derived from the compound M3, and a compound.
- the structural unit derived from M4 is a copolymer composed of a molar ratio of 50: 12.5: 30: 7.5.
- Step 1-1 After making the inside of the reaction vessel an inert gas atmosphere, Compound M5 (1.74 g), Compound M3 (3.19 g), dichlorobis (triphenylphosphine) palladium (2.5 mg) and toluene (40 mL) ) And heated to 80 ° C.
- Step 2-1 A 20 wt% tetraethylammonium hydroxide aqueous solution (12 mL) was added dropwise to the resulting reaction solution, and the mixture was refluxed for 8 hours.
- Step 3-1 After the reaction, phenylboronic acid (0.427 g) and dichlorobis (triphenylphosphine) palladium (2.5 mg) were added thereto and refluxed for 17 hours.
- the polymer compound HTL-3 had an Mn of 4.5 ⁇ 10 4 and an Mw of 1.5 ⁇ 10 5 .
- the polymer compound HTL-3 is composed of a structural unit derived from the compound M5 and a structural unit derived from the compound M3 in a molar ratio of 50:50 according to the theoretical value obtained from the amount of the raw materials. It is a copolymer.
- 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.
- AQ-1200 manufactured by Plextronics
- the hole injection layer was formed by heating for 15 minutes.
- the polymer compound HTL-1 was dissolved in xylene at a concentration of 0.6% by weight. Using the obtained xylene solution, a film having a thickness of 20 nm is 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-1 became a crosslinked product.
- Example D3 Production and Evaluation of Light-Emitting Element D3
- a light emitting device D3 was manufactured.
- Example D4 Production and Evaluation of Light-Emitting Element D4
- a light emitting device D4 was manufactured.
- Example D5 Production and Evaluation of Light-Emitting Element D5
- Example D1 Formation of First Organic Layer
- / 30 wt%) was dissolved at a concentration of 2.2 wt%, and a light emitting device D5 was produced in the same manner as in Example D1.
- Example D6 Production and Evaluation of Light-Emitting Element D6
- compound H5 and phosphorescent compound G2 70 wt% in chlorobenzene.
- 30 wt%) was dissolved at a concentration of 2.2 wt%, and a light emitting device D6 was produced in the same manner as in Example D1.
- Example D7 Production and Evaluation of Light-Emitting Element D7
- polymer compound HTL-1 in (formation of second organic layer) in example D1
- polymer compound HTL-2 was used.
- Example D1 Formation of first organic layer
- a light-emitting element D7 was produced in the same manner as in Example D1, except that it was dissolved at a concentration of%.
- Example D1 Formation of First Organic Layer
- Example D1 Formation of the second organic layer
- Polymer compound HTL-1 in xylene was 0.6 wt%.
- a light emitting device CD1 was prepared in the same manner as in Example D1, except that “the polymer compound HTL-1 was dissolved in xylene at a concentration of 0.7 wt%”.
- the polymer compound HTL-1 was dissolved in xylene at a concentration of 0.7 wt%”.
- Example D1 Formation of First Organic Layer
- Example D1 Formation of First Organic Layer
- Table 2 shows the results obtained in Examples D1 to D7 and Comparative Examples CD1 to CD4.
- Example D8 Production and Evaluation of Light-Emitting Element D8
- polymer compound HTL-1 in (formation of second organic layer) in example D1
- polymer compound HTL-4 was used.
- Example D1 Formation of first organic layer
- a light-emitting element D8 was produced in the same manner as in Example D1, except that it was dissolved at a concentration of%.
- Example D1 Formation of first organic layer
- a light emitting device CD5 was produced in the same manner as in Example D1 except that the composition was dissolved at a concentration of%.
- EL light emission was observed by applying a voltage to the light emitting device CD5.
- the chromaticity coordinates (x, y) at 1000 cd / m 2 were (0.33, 0.63).
- the current value was set so that the initial luminance was 4000 cd / m 2 , the device was then driven at a constant current, and the time until the luminance became 75% of the initial luminance was measured and found to be 52.5 hours.
- Table 3 shows the results obtained in Example D8 and Comparative Example CD5.
- Example D9 Fabrication and evaluation of light-emitting element D9 (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.
- AQ-1200 manufactured by Plextronics
- the hole injection layer was formed by heating for 15 minutes.
- the polymer compound HTL-1 was dissolved in xylene at a concentration of 0.7% by weight. Using the obtained xylene solution, a film having a thickness of 20 nm is 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-1 became a crosslinked product.
- a light emitting device D10 was manufactured.
- Example D12 Production and Evaluation of Light-Emitting Element D12
- Example D9 Formation of First Organic Layer
- “Chlorobenzene, Compound H1 and Phosphorescent Compound R1 90
- a light emitting device D12 was produced in the same manner as in Example D9, except that the content was dissolved.
- Example D13 Production and Evaluation of Light-Emitting Element D13
- polymer compound HTL-1 in (formation of second organic layer) in example D9
- polymer compound HTL-2 was used.
- Example D9 Formation of first organic layer
- Example D9 Formation of First Organic Layer
- a light emitting device CD6 was produced.
- EL light emission was observed by applying a voltage to the light emitting device CD6.
- the chromaticity coordinates (x, y) at 1000 cd / m 2 were (0.67, 0.33).
- the current value was set so that the initial luminance was 4000 cd / m 2 , the device was then driven at a constant current, and the time until the luminance became 50% of the initial luminance was measured to be 10.4 hours.
- Table 4 shows the results obtained in Examples D9 to D13 and Comparative Examples CD6 to CD8.
- Embodiment of this invention aims at providing the light emitting element which is excellent in a luminance lifetime.
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Abstract
Description
そこで、本発明は、輝度寿命に優れる発光素子を提供することを目的とする。
陽極と、陰極と、陽極及び陰極の間に設けられた第1の有機層と、陽極及び陰極の間に設けられた第2の有機層とを有する発光素子であって、
第1の有機層が、式(1)で表される燐光発光性化合物と式(H)で表される化合物とを含有する層であり、
第2の有機層が、架橋材料の架橋体を含有する層である、発光素子。
Mは、ルテニウム原子、ロジウム原子、パラジウム原子、イリジウム原子又は白金原子を表す。
n1は1以上の整数を表し、n2は0以上の整数を表し、n1+n2は2又は3である。但し、Mがルテニウム原子、ロジウム原子又はイリジウム原子の場合、n1+n2は3であり、Mがパラジウム原子又は白金原子の場合、n1+n2は2である。
E1及びE2は、それぞれ独立に、炭素原子又は窒素原子を表す。但し、E1及びE2の少なくとも一方は炭素原子である。E1及びE2が複数存在する場合、それらはそれぞれ同一でも異なっていてもよい。
環L1は、芳香族複素環を表し、該環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。環L1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。
環L2は、芳香族炭化水素環又は芳香族複素環を表し、これらの環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。環L2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。
環L1が有していてもよい置換基と、環L2が有していてもよい置換基とは、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。
A1-G1-A2は、アニオン性の2座配位子を表す。A1及びA2は、それぞれ独立に、炭素原子、酸素原子又は窒素原子を表し、これらの原子は環を構成する原子であってもよい。G1は、単結合、又は、A1及びA2とともに2座配位子を構成する原子団を表す。A1-G1-A2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。]
nH1は、0以上5以下の整数を表す。nH1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。
nH2は、1以上10以下の整数を表す。
ArH1は、式(H1-1)で表される基を表す。ArH1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。
LH1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、-NRH1’-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。RH1’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。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。
ArH2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。]
環RH1及び環RH2は、それぞれ独立に、単環若しくは縮合環の芳香族炭化水素環又は単環若しくは縮合環の芳香族複素環を表し、これらの環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。
但し、環RH1及び環RH2のうちの少なくとも一つは、縮合環の芳香族炭化水素環又は縮合環の芳香族複素環を表し、これらの環は置換基を有していてもよい。
XH1は、単結合、酸素原子、硫黄原子、-N(RXH1)-で表される基、又は、-C(RXH1’)2-で表される基を表す。RXH1及びRXH1’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、アルコキシ基、シクロアルコキシ基、アリール基、アリールオキシ基、1価の複素環基、置換アミノ基又はハロゲン原子を表し、これらの基は置換基を有していてもよい。複数存在するRXH1’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。
RXH1と環RH1が有していてもよい置換基、RXH1と環RH2が有していてもよい置換基、RXH1’と環RH1が有していてもよい置換基、及び、RXH1’と環RH2が有していてもよい置換基は、それぞれ結合して、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。]
[2]
前記架橋材料が、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低分子化合物、又は、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。
(架橋基A群)
[3]
前記架橋材料が、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、[2]に記載の発光素子。
[4]
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、[3]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、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、直接又は酸素原子も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、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、架橋基A群から選ばれる架橋基である。]
[5]
前記架橋材料が有する架橋基が、式(XL-2)、式(XL-3)、式(XL-4)、式(XL-5)、式(XL-6)、式(XL-7)、式(XL-8)、式(XL-9)、式(XL-10)、式(XL-11)、式(XL-12)、式(XL-13)、式(XL-14)、式(XL-15)又は式(XL-17)で表される基である、[2]~[4]のいずれかに記載の発光素子。
[6]
前記式(H1-1)で表される基が、式(H1-1B)で表される基、式(H1-1C)で表される基又は式(H1-1D)で表される基である、[1]~[5]のいずれかに記載の発光素子。
XH1は、前記と同じ意味を表す。
XH2及びXH3は、それぞれ独立に、単結合、酸素原子、硫黄原子、-N(RXH2)-で表される基、又は、-C(RXH2’)2-で表される基を表す。RXH2及びRXH2’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、アルコキシ基、シクロアルコキシ基、アリール基、アリールオキシ基、1価の複素環基、置換アミノ基又はハロゲン原子を表し、これらの基は置換基を有していてもよい。複数存在するRXH2’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。
ZH1、ZH2、ZH3、ZH4、ZH5、ZH6、ZH7、ZH8、ZH9、ZH10、ZH11及びZH12は、それぞれ独立に、炭素原子又は窒素原子を表す。
RH1、RH2、RH3、RH4、RH5、RH6、RH7、RH8、RH9、RH10、RH11及びRH12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、アルコキシ基、シクロアルコキシ基、アリール基、アリールオキシ基、1価の複素環基、置換アミノ基又はハロゲン原子を表し、これらの基は置換基を有していてもよい。
ZH1が窒素原子の場合、RH1は存在しない。ZH2が窒素原子の場合、RH2は存在しない。ZH3が窒素原子の場合、RH3は存在しない。ZH4が窒素原子の場合、RH4は存在しない。ZH5が窒素原子の場合、RH5は存在しない。ZH6が窒素原子の場合、RH6は存在しない。ZH7が窒素原子の場合、RH7は存在しない。ZH8が窒素原子の場合、RH8は存在しない。ZH9が窒素原子の場合、RH9は存在しない。ZH10が窒素原子の場合、RH10は存在しない。ZH11が窒素原子の場合、RH11は存在しない。ZH12が窒素原子の場合、RH12は存在しない。
RH1とRH2、RH3とRH4、RH5とRH6、RH6とRH7、RH7とRH8、RH9とRH10、RH10とRH11、及び、RH11とRH12は、それぞれ結合して、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。]
[7]
前記式(1)で表される燐光発光性化合物が、式(1-B)で表される燐光発光性化合物である、[1]~[6]のいずれかに記載の発光素子。
M、n1、n2及びA1-G1-A2は、前記と同じ意味を表す。
E11B、E12B、E13B、E14B、E21B、E22B、E23B及びE24Bは、それぞれ独立に、窒素原子又は炭素原子を表す。E11B、E12B、E13B、E14B、E21B、E22B、E23B及びE24Bが複数存在する場合、それらはそれぞれ同一でも異なっていてもよい。E11Bが窒素原子の場合、R11Bは存在しない。E12Bが窒素原子の場合、R12Bは存在しない。E13Bが窒素原子の場合、R13Bは存在しない。E14Bが窒素原子の場合、R14Bは存在しない。E21Bが窒素原子の場合、R21Bは存在しない。E22Bが窒素原子の場合、R22Bは存在しない。E23Bが窒素原子の場合、R23Bは存在しない。E24Bが窒素原子の場合、R24Bは存在しない。
R11B、R12B、R13B、R14B、R21B、R22B、R23B及びR24B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、アルコキシ基、シクロアルコキシ基、アリール基、アリールオキシ基、1価の複素環基、置換アミノ基又はハロゲン原子を表し、これらの基は置換基を有していてもよい。R11B、R12B、R13B、R14B、R21B、R22B、R23B及びR24Bが複数存在する場合、それらはそれぞれ同一でも異なっていてもよい。R11BとR12B、R12BとR13B、R13BとR14B、R11BとR21B、R21BとR22B、R22BとR23B、及び、R23BとR24Bは、それぞれ結合して、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。
環L1Bは、窒素原子、炭素原子、E11B、E12B、E13B及びE14Bとで構成されるピリジン環又はピリミジン環を表す。
環L2Bは、2つの炭素原子、E21B、E22B、E23B及びE24Bとで構成されるベンゼン環、ピリジン環又はピリミジン環を表す。]
[8]
前記式(1-B)で表される燐光発光性化合物が、式(1-B1)で表される燐光発光性化合物、式(1-B2)で表される燐光発光性化合物、式(1-B3)で表される燐光発光性化合物、式(1-B4)で表される燐光発光性化合物又は式(1-B5)で表される燐光発光性化合物である、[7]に記載の発光素子。
M、n1、n2、A1-G1-A2、R11B、R12B、R13B、R14B、R21B、R22B、R23B及びR24Bは、前記と同じ意味を表す。
n11及びn12は、それぞれ独立に、1以上の整数を表し、n11+n12は2又は3である。但し、Mがルテニウム原子、ロジウム原子又はイリジウム原子の場合、n11+n12は3であり、Mがパラジウム原子又は白金原子の場合、n11+n12は2である。
R15B、R16B、R17B及びR18B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、アルコキシ基、シクロアルコキシ基、アリール基、アリールオキシ基、1価の複素環基、置換アミノ基又はハロゲン原子を表し、これらの基は置換基を有していてもよい。R15B、R16B、R17B及びR18Bが複数存在する場合、それらはそれぞれ同一でも異なっていてもよい。R13BとR15B、R15BとR16B、R16BとR17B、R17BとR18B、及び、R18BとR21Bは、それぞれ結合して、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。]
[9]
前記式(1)で表される燐光発光性化合物が、式(1-A)で表される燐光発光性化合物である、[1]~[6]のいずれかに記載の発光素子。
M、n1、n2、E1及びA1-G1-A2は、前記と同じ意味を表す。
E11A、E12A、E13A、E21A、E22A、E23A及びE24Aは、それぞれ独立に、窒素原子又は炭素原子を表す。E11A、E12A、E13A、E21A、E22A、E23A及びE24Aが複数存在する場合、それらはそれぞれ同一でも異なっていてもよい。E11Aが窒素原子の場合、R11Aは存在しても存在しなくてもよい。E12Aが窒素原子の場合、R12Aは存在しても存在しなくてもよい。E13Aが窒素原子の場合、R13Aは存在しても存在しなくてもよい。E21Aが窒素原子の場合、R21Aは存在しない。E22Aが窒素原子の場合、R22Aは存在しない。E23Aが窒素原子の場合、R23Aは存在しない。E24Aが窒素原子の場合、R24Aは存在しない。
R11A、R12A、R13A、R21A、R22A、R23A及びR24A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、アルコキシ基、シクロアルコキシ基、アリール基、アリールオキシ基、1価の複素環基、置換アミノ基又はハロゲン原子を表し、これらの基は置換基を有していてもよい。R11A、R12A、R13A、R21A、R22A、R23A及びR24Aが複数存在する場合、それらはそれぞれ同一でも異なっていてもよい。R11AとR12A、R12AとR13A、R11AとR21A、R21AとR22A、R22AとR23A、及び、R23AとR24Aは、それぞれ結合して、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。
環L1Aは、窒素原子、E1、E11A、E12A及びE13Aとで構成されるトリアゾール環又はジアゾール環を表す。
環L2Aは、2つの炭素原子、E21A、E22A、E23A及びE24Aとで構成されるベンゼン環、ピリジン環又はピリミジン環を表す。]
[10]
前記第1の有機層と、前記第2の有機層とが、隣接している、[1]~[9]のいずれかに記載の発光素子。
[11]
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]~[10]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。
金属錯体を表す式中、中心金属との結合を表す実線は、共有結合又は配位結合を意味する。
高分子化合物は、ブロック共重合体、ランダム共重合体、交互共重合体、グラフト共重合体のいずれであってもよいし、その他の態様であってもよい。
高分子化合物の末端基は、重合活性基がそのまま残っていると、高分子化合物を発光素子の作製に用いた場合に発光特性又は輝度寿命が低下する可能性があるので、好ましくは安定な基である。この末端基としては、好ましくは主鎖と共役結合している基であり、例えば、炭素-炭素結合を介してアリール基又は1価の複素環基と結合している基が挙げられる。
アルキル基は、置換基を有していてもよく、例えば、メチル基、エチル基、プロピル基、イソプロピル基、ブチル基、2-ブチル基、イソブチル基、tert-ブチル基、ペンチル基、イソアミル基、2-エチルブチル基、ヘキシル基、ヘプチル基、オクチル基、2-エチルヘキシル基、3-プロピルヘプチル基、デシル基、3,7-ジメチルオクチル基、2-エチルオクチル基、2-ヘキシルデシル基、ドデシル基、及び、これらの基における水素原子が、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、フッ素原子等で置換された基が挙げられ、例えば、トリフルオロメチル基、ペンタフルオロエチル基、パーフルオロブチル基、パーフルオロヘキシル基、パーフルオロオクチル基、3-フェニルプロピル基、3-(4-メチルフェニル)プロピル基、3-(3,5-ジ-ヘキシルフェニル)プロピル基、6-エチルオキシヘキシル基が挙げられる。
「シクロアルキル基」の炭素原子数は、置換基の炭素原子数を含めないで、通常3~50であり、好ましくは3~30であり、より好ましくは4~20である。
シクロアルキル基は、置換基を有していてもよく、例えば、シクロヘキシル基、シクロヘキシルメチル基、シクロヘキシルエチル基が挙げられる。
アリール基は、置換基を有していてもよく、例えば、フェニル基、1-ナフチル基、2-ナフチル基、1-アントラセニル基、2-アントラセニル基、9-アントラセニル基、1-ピレニル基、2-ピレニル基、4-ピレニル基、2-フルオレニル基、3-フルオレニル基、4-フルオレニル基、2-フェニルフェニル基、3-フェニルフェニル基、4-フェニルフェニル基、及び、これらの基における水素原子が、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、フッ素原子等で置換された基が挙げられる。
アルコキシ基は、置換基を有していてもよく、例えば、メトキシ基、エトキシ基、プロピルオキシ基、イソプロピルオキシ基、ブチルオキシ基、イソブチルオキシ基、tert-ブチルオキシ基、ペンチルオキシ基、ヘキシルオキシ基、ヘプチルオキシ基、オクチルオキシ基、2-エチルヘキシルオキシ基、ノニルオキシ基、デシルオキシ基、3,7-ジメチルオクチルオキシ基、ラウリルオキシ基、及び、これらの基における水素原子が、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、フッ素原子等で置換された基が挙げられる。
「シクロアルコキシ基」の炭素原子数は、置換基の炭素原子数を含めないで、通常3~40であり、好ましくは4~10である。
シクロアルコキシ基は、置換基を有していてもよく、例えば、シクロヘキシルオキシ基が挙げられる。
アリールオキシ基は、置換基を有していてもよく、例えば、フェノキシ基、1-ナフチルオキシ基、2-ナフチルオキシ基、1-アントラセニルオキシ基、9-アントラセニルオキシ基、1-ピレニルオキシ基、及び、これらの基における水素原子が、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、フッ素原子等で置換された基が挙げられる。
「芳香族複素環式化合物」は、オキサジアゾール、チアジアゾール、チアゾール、オキサゾール、チオフェン、ピロール、ホスホール、フラン、ピリジン、ピラジン、ピリミジン、トリアジン、ピリダジン、キノリン、イソキノリン、カルバゾール、ジベンゾホスホール等の複素環自体が芳香族性を示す化合物、及び、フェノキサジン、フェノチアジン、ジベンゾボロール、ジベンゾシロール、ベンゾピラン等の複素環自体は芳香族性を示さなくとも、複素環に芳香環が縮環されている化合物を意味する。
1価の複素環基は、置換基を有していてもよく、例えば、チエニル基、ピロリル基、フリル基、ピリジニル基、ピペリジニル基、キノリニル基、イソキノリニル基、ピリミジニル基、トリアジニル基、及び、これらの基における水素原子が、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等で置換された基が挙げられる。
置換アミノ基としては、例えば、ジアルキルアミノ基、ジシクロアルキルアミノ基及びジアリールアミノ基が挙げられる。
アミノ基としては、例えば、ジメチルアミノ基、ジエチルアミノ基、ジフェニルアミノ基、ビス(4-メチルフェニル)アミノ基、ビス(4-tert-ブチルフェニル)アミノ基、ビス(3,5-ジ-tert-ブチルフェニル)アミノ基が挙げられる。
「シクロアルケニル基」の炭素原子数は、置換基の炭素原子数を含めないで、通常3~30であり、好ましくは4~20である。
アルケニル基及びシクロアルケニル基は、置換基を有していてもよく、例えば、ビニル基、1-プロペニル基、2-プロペニル基、2-ブテニル基、3-ブテニル基、3-ペンテニル基、4-ペンテニル基、1-ヘキセニル基、5-ヘキセニル基、7-オクテニル基、及び、これらの基が置換基を有する基が挙げられる。
「シクロアルキニル基」の炭素原子数は、置換基の炭素原子を含めないで、通常4~30であり、好ましくは4~20である。
アルキニル基及びシクロアルキニル基は、置換基を有していてもよく、例えば、エチニル基、1-プロピニル基、2-プロピニル基、2-ブチニル基、3-ブチニル基、3-ペンチニル基、4-ペンチニル基、1-ヘキシニル基、5-ヘキシニル基、及び、これらの基が置換基を有する基が挙げられる。
アリーレン基は、置換基を有していてもよく、例えば、フェニレン基、ナフタレンジイル基、アントラセンジイル基、フェナントレンジイル基、ジヒドロフェナントレンジイル基、ナフタセンジイル基、フルオレンジイル基、ピレンジイル基、ペリレンジイル基、クリセンジイル基、及び、これらの基が置換基を有する基が挙げられ、好ましくは、式(A-1)~式(A-20)で表される基である。アリーレン基は、これらの基が複数結合した基を含む。
2価の複素環基は、置換基を有していてもよく、例えば、ピリジン、ジアザベンゼン、トリアジン、アザナフタレン、ジアザナフタレン、カルバゾール、ジベンゾフラン、ジベンゾチオフェン、ジベンゾシロール、フェノキサジン、フェノチアジン、アクリジン、ジヒドロアクリジン、フラン、チオフェン、アゾール、ジアゾール、トリアゾールから、環を構成する炭素原子又はヘテロ原子に直接結合している水素原子のうち2個の水素原子を除いた2価の基が挙げられ、好ましくは、式(AA-1)~式(AA-34)で表される基である。2価の複素環基は、これらの基が複数結合した基を含む。
本発明の発光素子は、陽極と、陰極と、陽極及び陰極の間に設けられた第1の有機層と、陽極及び陰極の間に設けられた第2の有機層とを有する発光素子であって、第1の有機層が、式(1)で表される燐光発光性化合物と式(H)で表される化合物とを含有する層であり、第2の有機層が、架橋材料の架橋体を含有する層である、発光素子である。
第1の有機層を湿式法により形成する場合、後述する第1のインクを用いることが好ましい。
第2の有機層を湿式法により形成する場合、後述する第2のインクを用いることが好ましい。第2の有機層を形成後、加熱又は光照射することで、第2の有機層に含有される架橋材料を架橋させることができ、加熱することで、第2の有機層に含有される架橋材料を架橋させることが好ましい。架橋材料が架橋した状態(架橋材料の架橋体)で、第2の有機層に含有されている場合、第2の有機層は溶媒に対して実質的に不溶化されている。そのため、第2の有機層は、発光素子の積層化に好適に使用することができる。
加熱の時間は、通常、0.1分~1000分であり、好ましくは0.5分~500分であり、より好ましくは1分~120分であり、更に好ましくは30分~90分である。
光照射に用いられる光の種類は、例えば、紫外光、近紫外光、可視光である。
第1の有機層は、式(1)で表される燐光発光性化合物と式(H)で表される化合物とを含有する層である。
式(1)で表される燐光発光性化合物は、通常、室温(25℃)で燐光発光性を示す化合物であり、好ましくは、室温で三重項励起状態からの発光を示す化合物である。
式(1)で表される燐光発光性化合物は、中心金属であるMと、添え字n1でその数を規定されている配位子と、添え字n2でその数を規定されている配位子とから構成されている。
Mがルテニウム原子、ロジウム原子又はイリジウム原子の場合、n1は2又は3であることが好ましく、3であることがより好ましい。
Mがパラジウム原子又は白金原子の場合、n1は2であることが好ましい。
環L1としては、例えば、ジアゾール環、トリアゾール環、ピリジン環、ジアザベンゼン環、トリアジン環、キノリン環及びイソキノリン環が挙げられ、ジアゾール環、トリアゾール環、ピリジン環、ピリミジン環、キノリン環又はイソキノリン環が好ましく、ジアゾール環、トリアゾール環、ピリジン環、キノリン環又はイソキノリン環がより好ましくピリジン環、キノリン環又はイソキノリン環が更に好ましく、ピリジン環又はイソキノリン環が特に好ましく、これらの環は置換基を有していてもよい。
環L2としては、例えば、ベンゼン環、ナフタレン環、フルオレン環、フェナントレン環、インデン環、ピリジン環、ジアザベンゼン環及びトリアジン環が挙げられ、ベンゼン環、ナフタレン環、フルオレン環、ピリジン環又はピリミジン環が好ましく、ベンゼン環、ピリジン環又はピリミジン環がより好ましく、ベンゼン環が更に好ましく、これらの環は置換基を有していてもよい。
mDA1、mDA2及びmDA3は、それぞれ独立に、0以上の整数を表す。
GDAは、窒素原子、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。
ArDA1、ArDA2及びArDA3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。ArDA1、ArDA2及びArDA3が複数ある場合、それらはそれぞれ同一でも異なっていてもよい。
TDAは、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。複数あるTDAは、同一でも異なっていてもよい。]
mDA1、mDA2、mDA3、mDA4、mDA5、mDA6及びmDA7は、それぞれ独立に、0以上の整数を表す。
GDAは、窒素原子、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。複数あるGDAは、同一でも異なっていてもよい。
ArDA1、ArDA2、ArDA3、ArDA4、ArDA5、ArDA6及びArDA7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。ArDA1、ArDA2、ArDA3、ArDA4、ArDA5、ArDA6及びArDA7が複数ある場合、それらはそれぞれ同一でも異なっていてもよい。
TDAは、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。複数あるTDAは、同一でも異なっていてもよい。]
mDA1は、0以上の整数を表す。
ArDA1は、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。ArDA1が複数ある場合、それらは同一でも異なっていてもよい。
TDAは、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。]
*は、式(D-A)におけるArDA1、式(D-B)におけるArDA1、式(D-B)におけるArDA2、又は、式(D-B)におけるArDA3との結合を表す。
**は、式(D-A)におけるArDA2、式(D-B)におけるArDA2、式(D-B)におけるArDA4、又は、式(D-B)におけるArDA6との結合を表す。
***は、式(D-A)におけるArDA3、式(D-B)におけるArDA3、式(D-B)におけるArDA5、又は、式(D-B)におけるArDA7との結合を表す。
RDA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、これらの基は更に置換基を有していてもよい。RDAが複数ある場合、それらは同一でも異なっていてもよい。]
RDAは、前記と同じ意味を表す。
RDB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。RDBが複数ある場合、それらは同一でも異なっていてもよい。]
Rp1、Rp2、Rp3及びRp4は、それぞれ独立に、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又はハロゲン原子を表す。Rp1、Rp2及びRp4が複数ある場合、それらはそれぞれ同一であっても異なっていてもよい。
np1は、0~5の整数を表し、np2は0~3の整数を表し、np3は0又は1を表し、np4は0~4の整数を表す。複数あるnp1は、同一でも異なっていてもよい。]
Rp1、Rp2、Rp3及びRp4は、それぞれ独立に、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又はハロゲン原子を表す。Rp1、Rp2及びRp4が複数ある場合、それらはそれぞれ同一でも異なっていてもよい。
np1は0~5の整数を表し、np2は0~3の整数を表し、np3は0又は1を表し、np4は0~4の整数を表す。複数あるnp1は同一でも異なっていてもよい。複数あるnp2は、それらは同一でも異なっていてもよい。]
Rp4、Rp5及びRp6は、それぞれ独立に、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又はハロゲン原子を表す。Rp4、Rp5及びRp6が複数ある場合、それらはそれぞれ同一であっても異なっていてもよい。
np4は0~4の整数を表し、np5は0~5の整数を表し、np6は0~5の整数を表す。]
環L2が有していてもよい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。
環L1が有していてもよい置換基と、環L2が有していてもよい置換基とは、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。
A1-G1-A2で表されるアニオン性の2座配位子としては、例えば、下記式で表される配位子が挙げられる。但し、A1-G1-A2で表されるアニオン性の2座配位子は、添え字n1でその数を定義されている配位子とは異なる。
*は、Mと結合する部位を表す。
RL1は、水素原子、アルキル基、シクロアルキル基、アリール基、1価の複素環基又はハロゲン原子を表し、これらの基は置換基を有していてもよい。複数存在するRL1は、同一でも異なっていてもよい。
RL2は、アルキル基、シクロアルキル基、アリール基、1価の複素環基又はハロゲン原子を表し、これらの基は置換基を有していてもよい。]
環L1Aがジアゾール環である場合、E11Aが窒素原子であるイミダゾール環、又は、E12Aが窒素原子であるイミダゾール環が好ましく、E11Aが窒素原子であるイミダゾール環がより好ましい。
環L1Aがトリアゾール環である場合、E11A及びE12Aが窒素原子であるトリアゾール環、又は、E11A及びE13Aが窒素原子であるトリアゾール環が好ましく、E11A及びE12Aが窒素原子であるトリアゾール環がより好ましい。
E11Aが炭素原子である場合、R11Aは水素原子、アルキル基、シクロアルキル基、アリール基、1価の複素環基又は置換アミノ基であることが好ましく、水素原子、アルキル基、シクロアルキル基又はアリール基であることがより好ましく、水素原子、アルキル基又はシクロアルキル基であることが更に好ましく、水素原子であることが特に好ましく、これらの基は置換基を有していてもよい。
E12Aが炭素原子である場合、R12Aは水素原子、アルキル基、シクロアルキル基、アリール基、1価の複素環基又は置換アミノ基であることが好ましく、水素原子、アルキル基、シクロアルキル基又はアリール基であることがより好ましく、水素原子、アルキル基又はシクロアルキル基であることが更に好ましく、水素原子であることが特に好ましく、これらの基は置換基を有していてもよい。
E13Aが炭素原子である場合、R13Aは水素原子、アルキル基、シクロアルキル基、アリール基、1価の複素環基又は置換アミノ基であることが好ましく、水素原子、アルキル基、シクロアルキル基又はアリール基であることがより好ましく、水素原子、アルキル基又はシクロアルキル基であることが更に好ましく、水素原子であることが特に好ましく、これらの基は置換基を有していてもよい。
環L2Aがピリミジン環である場合、E22A及びE24Aが窒素原子であるピリミジン環が好ましい。
環L2Aは、ベンゼン環であることが好ましい。
環L1Bがピリミジン環である場合、E11Bが窒素原子であるピリミジン環が好ましい。
環L2Bがピリジン環である場合、E21Bが窒素原子であるピリジン環、E22Bが窒素原子であるピリジン環、又は、E23Bが窒素原子であるピリジン環が好ましく、E22Bが窒素原子であるであるピリジン環がより好ましい。
環L2Bがピリミジン環である場合、E22B及びE24Bが窒素原子であるピリミジン環が好ましい。
環L2Bは、ベンゼン環であることが好ましい。
式(H)で表される化合物の分子量は、通常、1×102~5×104であり、好ましくは、2×102~1×104であり、より好ましくは、3×102~5×103であり、更に好ましくは、4×102~2.5×103であり、特に好ましくは、5×102~1.5×103である。
環RH1及び環RH2において、単環の芳香族炭化水素環の炭素原子数は、置換基の炭素原子数を含めないで、好ましくは6である。
環RH1及び環RH2において、単環の芳香族炭化水素環は、好ましくは、置換基を有していてもよいベンゼン環である。
環RH1及び環RH2における縮合環の芳香族炭化水素環としては、例えば、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、ナフタセン環、フルオレン環、スピロビフルオレン環、インデン環、ピレン環、ペリレン環及びクリセン環が挙げられ、好ましくは、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、フルオレン環又はスピロビフルオレン環であり、より好ましくは、ナフタレン環、フルオレン環又はスピロビフルオレン環であり、更に好ましくは、フルオレン環又はスピロビフルオレン環であり、特に好ましくは、フルオレン環であり、これらの環は置換基を有していてもよい。
環RH1及び環RH2における単環の芳香族複素環としては、例えば、ピロール環、ジアゾール環、トリアゾール環、ピリジン環、ジアザベンゼン環及びトリアジン環が挙げられ、好ましくは、ピリジン環又はジアザベンゼン環であり、これらの環は置換基を有していてもよい。
環RH1及び環RH2における縮合環の芳香族複素環としては、例えば、アザナフタレン環、ジアザナフタレン環、トリアザナフタレン環、インドール環、カルバゾール環、アザカルバゾール環、ジアザカルバゾール環、ジベンゾフラン環、ジベンゾチオフェン環、フェノキサジン環、フェノチアジン環、アクリジン環、9,10-ジヒドロアクリジン環、アクリドン環、フェナジン環及び5,10-ジヒドロフェナジン環が挙げられ、好ましくは、アザナフタレン環、ジアザナフタレン環、カルバゾール環、アザカルバゾール環、ジアザカルバゾール環、ジベンゾフラン環、ジベンゾチオフェン環、フェノキサジン環、フェノチアジン環、9,10-ジヒドロアクリジン環又は5,10-ジヒドロフェナジン環であり、より好ましくは、カルバゾール環、アザカルバゾール環、ジアザカルバゾール環、ジベンゾフラン環、ジベンゾチオフェン環、フェノキサジン環、フェノチアジン環、9,10-ジヒドロアクリジン環又は5,10-ジヒドロフェナジン環であり、更に好ましくは、カルバゾール環、ジベンゾフラン環又はジベンゾチオフェン環であり、特に好ましくは、カルバゾール環であり、これらの環は置換基を有していてもよい。
RXH1’は、好ましくは、アルキル基、シクロアルキル基、アリール基、1価の複素環基又は置換アミノ基であり、より好ましくは、アルキル基、シクロアルキル基、アリール基又は1価の複素環基であり、更に好ましくは、アルキル基、シクロアルキル基又はアリール基であり、特に好ましくは、アルキル基又はシクロアルキル基であり、これらの基は置換基を有していてもよい。
RXH1及びRXH1’が有していてもよい置換基の例及び好ましい範囲は、環RH1及び環RH2が有していてもよい置換基が更に有していてもよい置換基の例及び好ましい範囲と同じである。
XH2及びXH3のうち、少なくとも一方は単結合であることが好ましく、XH3が単結合であることがより好ましい。
XH2及びXH3のうち、少なくとも一方が単結合である場合、もう一方は酸素原子、硫黄原子、-N(RXH2)-で表される基、又は、-C(RXH2’)2-で表される基であることが好ましく、-N(RXH2)-で表される基、又は、-C(RXH2’)2-で表される基であることがより好ましく、-C(RXH2’)2-で表される基であることが更に好ましい。
RXH2’の例及び好ましい範囲は、RXH1’の例及び好ましい範囲と同じである。
RXH2及びRXH2’が有していてもよい置換基の例及び好ましい範囲は、環RH1及び環RH2が有していてもよい置換基が更に有していてもよい置換基の例及び好ましい範囲と同じである。
RH1、RH2、RH3、RH4、RH5、RH6、RH7、RH8、RH9、RH10、RH11及びRH12が有していてもよい置換基の例及び好ましい範囲は、環RH1及び環RH2が有していてもよい置換基が更に有していてもよい置換基の例及び好ましい範囲と同じである。
LH1が有していてもよい置換基が更に有していてもよい置換基の例及び好ましい範囲は、環RH1及び環RH2が有していてもよい置換基が更に有していてもよい置換基の例及び好ましい範囲と同じである。
RH1’が有していてもよい置換基の例及び好ましい範囲は、環RH1及び環RH2が有していてもよい置換基が更に有していてもよい置換基の例及び好ましい範囲と同じである。
ArH2において、芳香族炭化水素基としては、ベンゼン環、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、ナフタセン環、フルオレン環、スピロビフルオレン環、インデン環、ピレン環、ペリレン環、クリセン環、又は、これらの環が縮環した環から、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が挙げられ、好ましくは、ベンゼン環、ナフタレン環、フェナントレン環、ジヒドロフェナントレン環、フルオレン環、スピロビフルオレン環、又は、これらの環が縮環した環から、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であり、より好ましくは、ベンゼン環、ナフタレン環、フェナントレン環、ジヒドロフェナントレン環、フルオレン環又はスピロビフルオレン環から、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であり、更に好ましくは、ベンゼン環、フルオレン環又はスピロビフルオレン環から、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であり、特に好ましくは、ベンゼン環から、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であり、これらの基は置換基を有していてもよい。
ArH2において、芳香族複素環基としては、ピロール環、フラン環、チオフェン環、オキサジアゾール環、チアジアゾール環、チアゾール環、オキサゾール環、イソチアゾール環、イソオキサゾール環、ベンゾオキサジアゾール環、ベンゾチアジアゾール環、ベンゾチアゾール環、ベンゾオキサゾール環、ピリジン環、ジアザベンゼン環、トリアジン環、アザナフタレン環、ジアザナフタレン環、トリアザナフタレン環、テトラアザナフタレン環、アザアントラセン環、ジアザアントラセン環、トリアザアントラセン環、テトラアザアントラセン環、アザフェナントレン環、ジアザフェナントレン環、トリアザフェナントレン環、テトラアザフェナントレン環、ジベンゾフラン環、ジベンゾチオフェン環、ジベンゾシロール環、ジベンゾホスホール環、カルバゾール環、アザカルバゾール環、ジアザカルバゾール環、フェノキサジン環、フェノチアジン環、又は、これらの複素環に芳香環が縮環した環から、環を構成する炭素原子又はヘテロ原子に直接結合する水素原子1個以上を除いてなる基が挙げられ、好ましくは、ピリジン環、ジアザベンゼン環、トリアジン環、アザナフタレン環、ジアザナフタレン環、アザアントラセン環、ジアザアントラセン環、アザフェナントレン環、ジアザフェナントレン環、ジベンゾフラン環、ジベンゾチオフェン環、カルバゾール環、アザカルバゾール環又はジアザカルバゾール環から、環を構成する炭素原子又はヘテロ原子に直接結合する水素原子1個以上を除いてなる基であり(これらの基の中でも、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が好ましい)、より好ましくは、ピリジン環、ジアザベンゼン環、トリアジン環、キノリン環、イソキノリン環、キナゾリン環、キノキサリン環、アクリジン環、フェナジン環、フェナントロリン環、ジベンゾフラン環、ジベンゾチオフェン環、カルバゾール環、アザカルバゾール環又はジアザカルバゾール環から、環を構成する炭素原子又はヘテロ原子に直接結合する水素原子1個以上を除いてなる基であり(これらの基の中でも、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が好ましい)、更に好ましくは、ピリジン環、ジアザベンゼン環、トリアジン環、キノリン環、イソキノリン環、キナゾリン環、キノキサリン環、ジベンゾフラン環、ジベンゾチオフェン環又はカルバゾール環から、環を構成する炭素原子又はヘテロ原子に直接結合する水素原子1個以上を除いてなる基であり(これらの基の中でも、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が好ましい)、特に好ましくは、ピリジン環、ピリミジン環又はトリアジン環から、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であり、とりわけ好ましくは、トリアジン環から、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であり、これらの基は置換基を有していてもよい。
R1Hが有していてもよい置換基の例及び好ましい範囲は、環RH1及び環RH2が有していてもよい置換基が更に有していてもよい置換基の例及び好ましい範囲と同じである。
R2Hが有していてもよい置換基の例及び好ましい範囲は、環RH1及び環RH2が有していてもよい置換基が更に有していてもよい置換基の例及び好ましい範囲と同じである。
第1の有機層は、式(1)で表される燐光発光性化合物と、式(H)で表される化合物とを含有する層である。
第1の有機層には、式(1)で表される燐光発光性化合物が1種単独で含有されていてもよく、本発明の実施形態に係る発光素子の発光色を調整することができるので、2種以上含有されていてもよい。また、第1の有機層には、式(H)で表される化合物が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。
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。
正孔輸送材料は、一種単独で用いても二種以上を併用してもよい。
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。
電子輸送材料は、一種単独で用いても二種以上を併用してもよい。
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。
電子注入材料及び正孔注入材料は、各々、一種単独で用いても二種以上を併用してもよい。
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。
ドープするイオンは、一種単独で用いても二種以上を併用してもよい。
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。
三重項発光錯体としては、例えば、以下に示す金属錯体が挙げられる。
発光材料は、一種単独で用いても二種以上を併用してもよい。
酸化防止剤は、式(1)で表される燐光発光性化合物と式(H)で表される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。
酸化防止剤は、一種単独で用いても二種以上を併用してもよい。
式(1)で表される燐光発光性化合物と、式(H)で表される化合物と、溶媒とを含有する組成物(以下、「第1のインク」ともいう。)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-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。
溶媒は、一種単独で用いても二種以上を併用してもよい。
第2の有機層は、架橋材料の架橋体を含有する層である。
架橋材料の架橋体は、架橋材料を上述した方法及び条件等により架橋した状態にすることで得られる。
第2の有機層の高分子化合物に含まれる、架橋基A群から選ばれる少なくとも一種の架橋基を有する構成単位は、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ことが好ましいが、下記式で表される構成単位であってもよい。
nAは、本発明の実施形態に係る発光素子の輝度寿命がより優れるので、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。
nは、本発明の実施形態に係る発光素子の輝度寿命がより優れるので、好ましくは2である。
Ar3で表される芳香族炭化水素基のn個の置換基を除いたアリーレン基部分としては、好ましくは、式(A-1)~式(A-20)で表される基であり、より好ましくは、式(A-1)、式(A-2)、式(A-6)~式(A-10)、式(A-19)又は式(A-20)で表される基であり、さらに好ましくは、式(A-1)、式(A-2)、式(A-7)、式(A-9)又は式(A-19)で表される基であり、これらの基は置換基を有していてもよい。
Ar3で表される複素環基のn個の置換基を除いた2価の複素環基部分としては、好ましくは、式(AA-1)~式(AA-34)で表される基である。
アルキレン基及びシクロアルキレン基は、置換基を有していてもよく、例えば、メチレン基、エチレン基、プロピレン基、ブチレン基、ヘキシレン基、シクロヘキシレン基、オクチレン基が挙げられる。
式(2)で表される構成単位は、第2の有機層の高分子化合物中に、1種のみ含まれていてもよく、2種以上含まれていてもよい。
mAは、本発明の実施形態に係る発光素子の輝度寿命がより優れるので、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。
mは、本発明の実施形態に係る発光素子の輝度寿命がより優れるので、好ましくは1又は2であり、より好ましくは2である。
cは、第2の有機層の高分子化合物の製造が容易になり、且つ、本発明の実施形態に係る発光素子の輝度寿命がより優れるので、好ましくは0である。
Ar5で表される芳香族炭化水素基のm個の置換基を除いたアリーレン基部分の定義や例は、後述する式(X)におけるArX2で表されるアリーレン基の定義や例と同じである。
Ar5で表される複素環基のm個の置換基を除いた2価の複素環基部分の定義や例は、後述する式(X)におけるArX2で表される2価の複素環基部分の定義や例と同じである。
Ar5で表される少なくとも1種の芳香族炭化水素環と少なくとも1種の複素環が直接結合した基のm個の置換基を除いた2価の基の定義や例は、後述する式(X)におけるArX2で表される少なくとも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価の基の定義や例と同じである。
Ar4及びAr6で表されるアリーレン基の定義や例は、後述する式(X)におけるArX1及びArX3で表されるアリーレン基の定義や例と同じである。
Ar4及びAr6で表される2価の複素環基の定義や例は、後述する式(X)におけるArX1及びArX3で表される2価の複素環基の定義や例と同じである。
Ar4、Ar5及びAr6で表される基は置換基を有していてもよく、置換基としては、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、アリールオキシ基、ハロゲン原子、1価の複素環基及びシアノ基が挙げられる。
KAは、第2の有機層の高分子化合物の製造が容易になるので、フェニレン基又はメチレン基であることが好ましい。
式(2')で表される構成単位は、第2の有機層の高分子化合物中に、1種のみ含まれていてもよく、2種以上含まれていてもよい。
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)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、本発明の実施形態に係る発光素子の輝度寿命がより優れるので、更に、式(Y)で表される構成単位を含むことが好ましい。
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。]
aX2は、本発明の実施形態に係る発光素子の輝度寿命がより優れるので、好ましくは2以下の整数であり、より好ましくは0である。
ArX1及びArX3で表される2価の複素環基は、より好ましくは式(AA-1)、式(AA-2)又は式(AA-7)~式(AA-26)で表される基であり、これらの基は置換基を有していてもよい。
ArX1及びArX3は、好ましくは置換基を有していてもよいアリーレン基である。
ArX2及びArX4で表される2価の複素環基のより好ましい範囲は、ArX1及びArX3で表される2価の複素環基のより好ましい範囲と同じである。
ArX2及びArX4で表される少なくとも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価の基としては、例えば、下記式で表される基が挙げられ、これらは置換基を有していてもよい。
RY1は前記と同じ意味を表す。
XY1は、-C(RY2)2-、-C(RY2)=C(RY2)-又は-C(RY2)2-C(RY2)2-で表される基を表す。RY2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RY2は、同一でも異なっていてもよく、RY2同士は互いに結合して、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。]
RY1は前記と同じ意味を表す。
RY3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。]
RY1は前記を同じ意味を表す。
RY4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。]
式(Y)で表される構成単位は、第2の有機層の高分子化合物中に、1種のみ含まれていてもよく、2種以上含まれていてもよい。
第2の有機層の高分子化合物は、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、Yamamoto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2の有機層の低分子化合物は、式(3)で表される低分子化合物が好ましい。
mB1、mB2及びmB3は、それぞれ独立に、0以上の整数を表す。複数存在するmB1は、同一でも異なっていてもよい。mB3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。
Ar7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。Ar7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。
LB1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、-N(R’’’)-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。LB1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、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。複数存在するX’’は、同一でも異なっていてもよい。但し、複数存在するX’’のうち、少なくとも1つは、架橋基である。]
mB2は、通常、0~10の整数であり、架橋材料の合成が容易となり、且つ、本発明の実施形態に係る発光素子の輝度寿命がより優れるため、好ましくは0~5の整数であり、より好ましくは0~3の整数であり、更に好ましくは1又は2であり、特に好ましくは1である。
mB3は、通常、0~5の整数であり、架橋材料の合成が容易になるため、好ましくは0~4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である。
Ar7で表される複素環基のmB3個の置換基を除いた2価の複素環基部分の定義や例は、前述の式(X)におけるArX2で表される2価の複素環基部分の定義や例と同じである。
Ar7で表される少なくとも1種の芳香族炭化水素環と少なくとも1種の複素環が直接結合した基のmB3個の置換基を除いた2価の基の定義や例は、前述の式(X)におけるArX2で表される少なくとも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価の基の定義や例と同じである。
Ar7で表される基が有してもよい置換基の定義や例は、前述の式(X)におけるArX2で表される基が有してもよい置換基の定義や例と同じである。
Ar7は、本発明の実施形態に係る発光素子の輝度寿命が優れるので、好ましくは芳香族炭化水素基であり、この芳香族炭化水素基は置換基を有していてもよい。
第2の有機層は、架橋材料の架橋体と、正孔輸送材料、正孔注入材料、電子輸送材料、電子注入材料、発光材料及び酸化防止剤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。
架橋材料と、溶媒とを含有する第2の組成物(以下、「第2のインク」ともいう。)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。
本発明の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。
本発明の実施形態に係る発光素子において、第1の有機層は、通常、発光層(以下、「第1の発光層」と言う。)である。
本発明の実施形態に係る発光素子において、第2の有機層は、通常、正孔輸送層、第2の発光層又は電子輸送層であり、好ましくは正孔輸送層又は第2の発光層であり、より好ましくは正孔輸送層である。
(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
(D15)陽極/正孔注入層/正孔輸送層(第2の有機層)/第2の発光層/第1の発光層(第1の有機層)/電子輸送層/電子注入層/陰極
本発明の実施形態に係る発光素子の輝度寿命がより優れるので、(D3)~(D12)で表される層構成が好ましく、(D7)~(D10)で表される層構成がより好ましい。
陽極、正孔注入層、正孔輸送層、第2の発光層、電子輸送層、電子注入層及び陰極が複数存在する場合、それらはそれぞれ同一でも異なっていてもよい。
本発明の実施形態に係る発光素子において、積層する層の順番、数、及び厚さは、発光素子の発光効率及び素子寿命を勘案して調整すればよい。
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。
本発明の実施形態に係る発光素子が第2の発光層を有し、且つ、後述の正孔輸送層及び後述の電子輸送層が第2の有機層ではない場合、第2の発光層は第2の有機層であることが好ましい。
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。
本発明の実施形態に係る発光素子が正孔輸送層を有し、且つ、前述の第2の発光層及び後述の電子輸送層が第2の有機層ではない場合、正孔輸送層は第2の有機層であることが好ましい。
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。
nE1は、1以上の整数を表す。
ArE1は、芳香族炭化水素基又は複素環基を表し、これらの基はRE1以外の置換基を有していてもよい。
RE1は、式(ES-1)で表される基を表す。RE1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。]
(ES-1)
[式中、
nE3は0以上の整数を表し、aE1は1以上の整数を表し、bE1は0以上の整数を表し、mE1は1以上の整数を表す。nE3、aE1及びbE1が複数存在する場合、それらはそれぞれ同一でも異なっていてもよい。但し、RE3が単結合である場合、mE1は1である。また、aE1及びbE1は、式(ES-1)で表される基の電荷が0となるように選択される。
RE3は、単結合、炭化水素基、複素環基又は-O-RE3’を表し(RE3’は、炭化水素基又は複素環基を表す。)、これらの基は置換基を有していてもよい。
QE1は、アルキレン基、シクロアルキレン基、アリーレン基、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。QE1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。
YE1は、CO2 -、SO3 -、SO2 -又はPO3 2-を表す。YE1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。
ME1は、アルカリ金属カチオン、アルカリ土類金属カチオン又はアンモニウムカチオンを表し、このアンモニウムカチオンは置換基を有していてもよい。ME1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。
ZE1は、F-、Cl-、Br-、I-、OH-、B(RE4)4 -、RE4SO3 -、RE4COO-、NO3 -、SO4 2-、HSO4 -、PO4 3-、HPO4 2-、H2PO4 -、BF4 -又はPF6 -を表す。RE4は、アルキル基、シクロアルキル基又はアリール基を表し、これらの基は置換基を有していてもよい。ZE1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。]
[式中、n’、m’及びnxは、それぞれ独立に、1以上の整数を表す。]
aE1は、通常1~10の整数であり、好ましくは1~5の整数であり、より好ましくは1又は2である。
bE1は、通常0~10の整数であり、好ましくは0~4の整数であり、より好ましくは0又は1である。
mE1は、通常1~5の整数であり、好ましくは1又は2であり、より好ましくは1である。
-O-RE3’-{(QE1)nE3-YE1(ME1)aE1(ZE1)bE1}mE1
YE1としては、CO2 -、SO2 -又はPO3 2-が好ましく、CO2 -がより好ましい。
ME1で表されるアルカリ土類金属カチオンとしては、例えば、Be2+、Mg2+、Ca2+、Sr2+、Ba2+が挙げられ、Mg2+、Ca2+、Sr2+又はBa2+が好ましく、Ba2+がより好ましい。
ME1としては、アルカリ金属カチオン又はアルカリ土類金属カチオンが好ましく、アルカリ金属カチオンがより好ましい。
nE2は、1以上の整数を表す。
ArE2は、芳香族炭化水素基又は複素環基を表し、これらの基はRE2以外の置換基を有していてもよい。
RE2は、式(ES-2)で表される基を表す。RE2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。]
(ES-2)
[式中、
nE4は0以上の整数を表し、aE2は1以上の整数を表し、bE2は0以上の整数を表し、mE2は1以上の整数を表す。nE4、aE2及びbE2が複数存在する場合、それらはそれぞれ同一でも異なっていてもよい。但し、RE5が単結合である場合、mE2は1である。また、aE2及びbE2は、式(ES-2)で表される基の電荷が0となるように選択される。
RE5は、単結合、炭化水素基、複素環基又は-O-RE5’を表し(RE5’は、炭化水素基又は複素環基を表す。)、これらの基は置換基を有していてもよい。
QE2は、アルキレン基、シクロアルキレン基、アリーレン基、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。QE2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。
YE2は、-C+RE6 2、-N+RE6 3、-P+RE6 3、-S+RE6 2又は-I+RE6 2を表す。RE6は、水素原子、アルキル基、シクロアルキル基又はアリール基を表し、これらの基は置換基を有していてもよい。複数存在するRE6は、同一でも異なっていてもよい。YE2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。
ME2は、F-、Cl-、Br-、I-、OH-、B(RE7)4 -、RE7SO3 -、RE7COO-、BF4 -、SbCl6 -又はSbF6 -を表す。RE7は、アルキル基、シクロアルキル基又はアリール基を表し、これらの基は置換基を有していてもよい。ME2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。
ZE2は、アルカリ金属カチオン又はアルカリ土類金属カチオンを表す。ZE2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。]
aE2は、通常1~10の整数であり、好ましくは1~5の整数であり、より好ましくは1又は2である。
bE2は、通常0~10の整数であり、好ましくは0~4の整数であり、より好ましくは0又は1である。
mE2は、通常1~5の整数であり、好ましくは1又は2であり、より好ましくは1である。
-O-RE5’-{(QE1)nE3-YE1(ME1)aE1(ZE1)bE1}mE1
ZE2で表されるアルカリ土類金属カチオンとしては、例えば、Be2+、Mg2+、Ca2+、Sr2+、Ba2+が挙げられ、Mg2+又はCa2+が好ましい。
ZE2としては、アルカリ金属カチオンが好ましい。
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。
陽極及び陰極の形成方法としては、例えば、真空蒸着法、スパッタリング法、イオンプレーティング法、メッキ法及びラミネート法が挙げられる。
本発明の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。
第1の発光層、第2の発光層、正孔輸送層、電子輸送層、正孔注入層及び電子注入層は、第1のインク、第2のインク、並びに、上述した発光材料、正孔輸送材料、電子輸送材料、正孔注入材料及び電子注入材料をそれぞれ含有するインクを用いて、スピンコート法、インクジェット印刷法等の湿式法により形成することができる。
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、陽極と陰極をとも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。
燐光発光性化合物G1は、国際公開第2004/026886号に記載の方法に準じて合成した。
燐光発光性化合物G2は、国際公開第2011/032626号に記載の方法に準じて合成した。
燐光発光性化合物G3は、国際公開第2009/131255号に記載の方法に従って合成した。
燐光発光性化合物G4は、特開2014-224101号公報に記載の方法に準じて合成した。
燐光発光性化合物G5は、特開2014-224101号公報に記載の方法に従って合成した。
燐光発光性化合物R1は、特開2006-188673号公報に記載の方法に準じて合成した。
燐光発光性化合物R2は、特開2008-179617号公報に記載の方法に従って合成した。
燐光発光性化合物R3は、特開2011-105701号公報に記載の方法に従って合成した。
化合物H1は、国際公開第2010/136109号に記載の方法に準じて合成した。
化合物H2及びH3は、Luminescense Technology社より購入した。
化合物H4は、特開2010-189630号公報に記載の方法に従って合成した。
化合物H5は、国際公開第2011/070963号に記載の方法に準じて合成した。
化合物H6は、特開2015-110751号公報に記載の方法に従って合成した。
化合物M1は、特開2011―174062号公報に記載の方法に従って合成した。
化合物M2、化合物M7及び化合物M8は、国際公開第2002/045184号に記載の方法に従って合成した。
化合物M3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M4は、特開2008-106241号公報に記載の方法に従って合成した
化合物M5は、特開2010-189630号公報に記載の方法に従って合成した。
化合物M6は、国際公開第2011/049241号に記載の方法に従って合成した。
高分子化合物HTL-1は、化合物M5、化合物M3、及び、化合物M6を用いて、国際公開第2013/146806号に記載の方法に従ってSuzukiカップリング反応により合成した。高分子化合物HTL-1のMnは1.9×104であり、Mwは9.9×104であった。
高分子化合物HTL-1は、仕込み原料の量から求めた理論値では、化合物M5から誘導される構成単位と、化合物M3から誘導される構成単位と、化合物M6から誘導される構成単位とが、50:42.5:7.5のモル比で構成されてなる共重合体である。
(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(2.69g)、化合物M2(0.425g)、化合物M3(1.64g)、化合物M4(0.238g)、ジクロロビス(トリフェニルホスフィン)パラジウム(2.1mg)及びトルエン(62ml)を加え、105℃に加熱した。
(工程2)得られた反応液に、20重量%水酸化テトラエチルアンモニウム水溶液(10ml)を滴下し、4.5時間還流させた。
(工程3)反応後、そこに、フェニルボロン酸(36.8mg)及びジクロロビス(トリフェニルホスフィン)パラジウム(2.1mg)を加え、16.5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重量%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。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3.12g得た。高分子化合物HTL-2のMnは7.8×104であり、Mwは2.6×105であった。
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、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3.00g得た。
(工程2-1)得られた反応液に、20重量%水酸化テトラエチルアンモニウム水溶液(12mL)を滴下し、8時間還流させた。
(工程3-1)反応後、そこに、フェニルボロン酸(0.427g)及びジクロロビス(トリフェニルホスフィン)パラジウム(2.5mg)を加え、17時間還流させた。
高分子化合物HTL-3のMnは4.5×104であり、Mwは1.5×105であった。
高分子化合物HTL-4は、化合物M7、化合物M8及び化合物M6を用いて、国際公開第2011/049241号に記載の方法に従って合成した。高分子化合物HTL-4のMnは8.9×104であり、Mwは4.2×105であった。
高分子化合物HTL-4は、仕込み原料の量から求めた理論値では、化合物M7から誘導される構成単位と、化合物M8から誘導される構成単位と、化合物M6から誘導される構成単位とが、50:42.5:7.5のモル比で構成された共重合体である。
高分子化合物HTL-5は、化合物M7及び化合物M8を用いて、特開2012-36381号公報に記載の方法に従って合成した。高分子化合物HTL-5のMnは8.1×104であり、Mwは3.4×105であった。
高分子化合物HTL-5は、仕込み原料の量から求めた理論値では、化合物M7から誘導される構成単位と、化合物M8から誘導される構成単位とが、50:50のモル比で構成された共重合体である。
(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、ポリチオフェン・スルホン酸系の正孔注入剤であるAQ-1200(Plextronics社製)をスピンコート法により35nmの厚さで成膜し、大気雰囲気下において、ホットプレート上で170℃、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-1を0.6重量%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分間加熱させることにより第2の有機層を形成した。この加熱により、高分子化合物HTL-1は、架橋体となった。
キシレンに、化合物H1及び燐光発光性化合物G2(化合物H1/燐光発光性化合物G2=70重量%/30重量%)を3.3重量%の濃度で溶解させた。得られたキシレン溶液を用いて、第2の有機層の上にスピンコート法により80nmの厚さで成膜し、窒素ガス雰囲気下において、130℃、10分間加熱させることにより第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。1000cd/m2における色度座標(x,y)は、(0.32,0.63)であった。初期輝度が4000cd/m2となるように電流値を設定後、定電流で駆動させ、輝度が初期輝度の80%となるまでの時間を測定したところ、75.9時間であった。
実施例D1の(第1の有機層の形成)における、「化合物H1及び燐光発光性化合物G2(化合物H1/燐光発光性化合物G2=70重量%/30重量%)」に代えて、「化合物H1及び燐光発光性化合物G4(化合物H1/燐光発光性化合物G4=70重量%/30重量%)」を用いた以外は、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。1000cd/m2における色度座標(x,y)は、(0.30,0.62)であった。初期輝度が4000cd/m2となるように電流値を設定後、定電流で駆動させ、輝度が初期輝度の80%となるまでの時間を測定したところ、12.1時間であった。
実施例D1の(第1の有機層の形成)における、「化合物H1及び燐光発光性化合物G2(化合物H1/燐光発光性化合物G2=70重量%/30重量%)」に代えて、「化合物H1及び燐光発光性化合物G5(化合物H1/燐光発光性化合物G5=70重量%/30重量%)」を用いた以外は、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。1000cd/m2における色度座標(x,y)は、(0.32,0.62)であった。初期輝度が4000cd/m2となるように電流値を設定後、定電流で駆動させ、輝度が初期輝度の80%となるまでの時間を測定したところ、88.3時間であった。
実施例D1の(第1の有機層の形成)における、「化合物H1及び燐光発光性化合物G2(化合物H1/燐光発光性化合物G2=70重量%/30重量%)」に代えて、「化合物H1及び燐光発光性化合物G3(化合物H1/燐光発光性化合物G3=70重量%/30重量%)」を用いた以外は、実施例D1と同様にして、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。1000cd/m2における色度座標(x,y)は、(0.32,0.63)であった。初期輝度が4000cd/m2となるように電流値を設定後、定電流で駆動させ、輝度が初期輝度の80%となるまでの時間を測定したところ、63.9時間であった。
実施例D1の(第1の有機層の形成)における、「キシレンに、化合物H1及び燐光発光性化合物G2(化合物H1/燐光発光性化合物G2=70重量%/30重量%)を3.3重量%の濃度で溶解させた。」に代えて、「クロロベンゼンに、化合物H5及び燐光発光性化合物G3(化合物H5/燐光発光性化合物G3=70重量%/30重量%)を2.2重量%の濃度で溶解させた。」とする以外は、実施例D1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。1000cd/m2における色度座標(x,y)は、(0.31,0.64)であった。初期輝度が4000cd/m2となるように電流値を設定後、定電流で駆動させ、輝度が初期輝度の80%となるまでの時間を測定したところ、44.9時間であった。
実施例D1の(第1の有機層の形成)における、「キシレンに、化合物H1及び燐光発光性化合物G2(化合物H1/燐光発光性化合物G2=70重量%/30重量%)を3.3重量%の濃度で溶解させた。」に代えて、「クロロベンゼンに、化合物H5及び燐光発光性化合物G2(化合物H5/燐光発光性化合物G2=70重量%/30重量%)を2.2重量%の濃度で溶解させた。」とする以外は、実施例D1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。1000cd/m2における色度座標(x,y)は、(0.32,0.63)であった。初期輝度が4000cd/m2となるように電流値を設定後、定電流で駆動させ、輝度が初期輝度の80%となるまでの時間を測定したところ、63.9時間であった。
実施例D1の(第2の有機層の形成)における、「高分子化合物HTL-1」に代えて、「高分子化合物HTL-2」を用い、更に、実施例D1の(第1の有機層の形成)における、「キシレンに、化合物H1及び燐光発光性化合物G2(化合物H1/燐光発光性化合物G2=70重量%/30重量%)を3.3重量%の濃度で溶解させた。」に代えて、「クロロベンゼンに、化合物H1及び燐光発光性化合物G2(化合物H1/燐光発光性化合物G2=70重量%/30重量%)を2.2重量%の濃度で溶解させた。」とする以外は、実施例D1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。1000cd/m2における色度座標(x,y)は、(0.33,0.63)であった。初期輝度が4000cd/m2となるように電流値を設定後、定電流で駆動させ、輝度が初期輝度の80%となるまでの時間を測定したところ、118.1時間であった。
実施例D1の(第1の有機層の形成)における、「キシレンに、化合物H1及び燐光発光性化合物G2(化合物H1/燐光発光性化合物G2=70重量%/30重量%)を3.3重量%の濃度で溶解させた。」に代えて、「クロロベンゼンに、化合物H2及び燐光発光性化合物G1(化合物H2/燐光発光性化合物G1=70重量%/30重量%)を2重量%の濃度で溶解させた。」とし、実施例D1の(第2の有機層の形成)における、「キシレンに高分子化合物HTL-1を0.6重量%の濃度で溶解させた。」に代えて、「キシレンに高分子化合物HTL-1を0.7重量%の濃度で溶解させた。」とする以外は、実施例D1と同様にして、発光素子CD1を作製した。
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。1000cd/m2における色度座標(x,y)は、(0.32,0.63)であった。初期輝度が4000cd/m2となるように電流値を設定後、定電流で駆動させ、輝度が初期輝度の80%となるまでの時間を測定したところ、0.3時間であった。
実施例D1の(第1の有機層の形成)における、「化合物H1及び燐光発光性化合物G2(化合物H1/燐光発光性化合物G2=70重量%/30重量%)」に代えて、「化合物H6及び燐光発光性化合物G4(化合物H6/燐光発光性化合物G4=70重量%/30重量%)」を用いた以外は、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。1000cd/m2における色度座標(x,y)は、(0.29,0.63)であった。初期輝度が4000cd/m2となるように電流値を設定後、定電流で駆動させ、輝度が初期輝度の80%となるまでの時間を測定したところ、1.4時間であった。
実施例D1の(第1の有機層の形成)における、「キシレンに、化合物H1及び燐光発光性化合物G2(化合物H1/燐光発光性化合物G2=70重量%/30重量%)を3.3重量%の濃度で溶解させた。」に代えて、「クロロベンゼンに、化合物H2及び燐光発光性化合物G3(化合物H2/燐光発光性化合物G3=70重量%/30重量%)を2重量%の濃度で溶解させた。」とする以外は、実施例D1と同様にして、発光素子CD3を作製した。
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。1000cd/m2における色度座標(x,y)は、(0.31,0.64)であった。初期輝度が4000cd/m2となるように電流値を設定後、定電流で駆動させ、輝度が初期輝度の80%となるまでの時間を測定したところ、4.6時間であった。
実施例D1の(第1の有機層の形成)における、「キシレンに、化合物H1及び燐光発光性化合物G2(化合物H1/燐光発光性化合物G2=70重量%/30重量%)を3.3重量%の濃度で溶解させた。」に代えて、「クロロベンゼンに、化合物H2及び燐光発光性化合物G4(化合物H2/燐光発光性化合物G4=70重量%/30重量%)を2重量%の濃度で溶解させた。」とする以外は、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。1000cd/m2における色度座標(x,y)は、(0.29,0.64)であった。初期輝度が4000cd/m2となるように電流値を設定後、定電流で駆動させ、輝度が初期輝度の80%となるまでの時間を測定したところ、2.5時間であった。
実施例D1の(第2の有機層の形成)における、「高分子化合物HTL-1」に代えて、「高分子化合物HTL-4」を用い、更に、実施例D1の(第1の有機層の形成)における、「キシレンに、化合物H1及び燐光発光性化合物G2(化合物H1/燐光発光性化合物G2=70重量%/30重量%)を3.3重量%の濃度で溶解させた。」に代えて、「クロロベンゼンに、化合物H1及び燐光発光性化合物G2(化合物H1/燐光発光性化合物G2=70重量%/30重量%)を2.2重量%の濃度で溶解させた。」とする以外は、実施例D1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。1000cd/m2における色度座標(x,y)は、(0.33,0.63)であった。初期輝度が4000cd/m2となるように電流値を設定後、定電流で駆動させ、輝度が初期輝度の75%となるまでの時間を測定したところ、78.4時間であった。
実施例D1の(第2の有機層の形成)における、「高分子化合物HTL-1」に代えて、「高分子化合物HTL-5」を用い、更に、実施例D1の(第1の有機層の形成)における、「キシレンに、化合物H1及び燐光発光性化合物G2(化合物H1/燐光発光性化合物G2=70重量%/30重量%)を3.3重量%の濃度で溶解させた。」に代えて、「クロロベンゼンに、化合物H1及び燐光発光性化合物G2(化合物H1/燐光発光性化合物G2=70重量%/30重量%)を2.2重量%の濃度で溶解させた。」とする以外は、実施例D1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。1000cd/m2における色度座標(x,y)は、(0.33,0.63)であった。初期輝度が4000cd/m2となるように電流値を設定後、定電流で駆動させ、輝度が初期輝度の75%となるまでの時間を測定したところ、52.5時間であった。
(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、ポリチオフェン・スルホン酸系の正孔注入剤であるAQ-1200(Plextronics社製)をスピンコート法により65nmの厚さで成膜し、大気雰囲気下において、ホットプレート上で170℃、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-1を0.7重量%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分間加熱させることにより第2の有機層を形成した。この加熱により、高分子化合物HTL-1は、架橋体となった。
クロロベンゼンに、化合物H1及び燐光発光性化合物R1(化合物H1/燐光発光性化合物R1=90重量%/10重量%)を2.5重量%の濃度で溶解させた。得られたクロロベンゼン溶液を用いて、第2の有機層の上にスピンコート法により80nmの厚さで成膜し、窒素ガス雰囲気下において、130℃、10分間加熱させることにより第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。1000cd/m2における色度座標(x,y)は、(0.62,0.33)であった。初期輝度が4000cd/m2となるように電流値を設定後、定電流で駆動させ、輝度が初期輝度の50%となるまでの時間を測定したところ、15.4時間であった。
実施例D9の(第1の有機層の形成)における、「化合物H1及び燐光発光性化合物R1(化合物H1/燐光発光性化合物R1=90重量%/10重量%)」に代えて、「化合物H1及び燐光発光性化合物R2(化合物H1/燐光発光性化合物R2=90重量%/10重量%)」を用いた以外は、実施例D9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。1000cd/m2における色度座標(x,y)は、(0.59,0.40)であった。初期輝度が4000cd/m2となるように電流値を設定後、定電流で駆動させ、輝度が初期輝度の50%となるまでの時間を測定したところ、75.4時間であった。
実施例D9の(第1の有機層の形成)における、「化合物H1及び燐光発光性化合物R1(化合物H1/燐光発光性化合物R1=90重量%/10重量%)」に代えて、「化合物H1及び燐光発光性化合物R3(化合物H1/燐光発光性化合物R3=90重量%/10重量%)」を用いた以外は、実施例D9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。1000cd/m2における色度座標(x,y)は、(0.62,0.36)であった。初期輝度が4000cd/m2となるように電流値を設定後、定電流で駆動させ、輝度が初期輝度の50%となるまでの時間を測定したところ、34.3時間であった。
実施例D9の(第1の有機層の形成)における、「クロロベンゼンに、化合物H1及び燐光発光性化合物R1(化合物H1/燐光発光性化合物R1=90重量%/10重量%)を2.5重量%の濃度で溶解させた。」に代えて、「クロロベンゼンに、化合物H5及び燐光発光性化合物R1(化合物H5/燐光発光性化合物R1=90重量%/10重量%)を2.2重量%の濃度で溶解させた。」とする以外は、実施例D9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。1000cd/m2における色度座標(x,y)は、(0.68,0.32)であった。初期輝度が4000cd/m2となるように電流値を設定後、定電流で駆動させ、輝度が初期輝度の50%となるまでの時間を測定したところ、20.0時間であった。
実施例D9の(第2の有機層の形成)における、「高分子化合物HTL-1」に代えて、「高分子化合物HTL-2」を用い、更に、実施例D9の(第1の有機層の形成)における、「クロロベンゼンに、化合物H1及び燐光発光性化合物R1(化合物H1/燐光発光性化合物R1=90重量%/10重量%)を2.5重量%の濃度で溶解させた。」に代えて、「トルエンに、化合物H1及び燐光発光性化合物R1(化合物H1/燐光発光性化合物R1=90重量%/10重量%)を2.2重量%の濃度で溶解させた。」とする以外は、実施例D9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。1000cd/m2における色度座標(x,y)は、(0.67,0.33)であった。初期輝度が4000cd/m2となるように電流値を設定後、定電流で駆動させ、輝度が初期輝度の50%となるまでの時間を測定したところ、12.9時間であった。
実施例D9の(第1の有機層の形成)における、「化合物H1及び燐光発光性化合物R1(化合物H1/燐光発光性化合物R1=90重量%/10重量%)」に代えて、「化合物H3及び燐光発光性化合物R1(化合物H3/燐光発光性化合物R1=90重量%/10重量%)」を用いた以外は、実施例D9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。1000cd/m2における色度座標(x,y)は、(0.67,0.33)であった。初期輝度が4000cd/m2となるように電流値を設定後、定電流で駆動させ、輝度が初期輝度の50%となるまでの時間を測定したところ、10.4時間であった。
実施例D9の(第1の有機層の形成)における、「化合物H1及び燐光発光性化合物R1(化合物H1/燐光発光性化合物R1=90重量%/10重量%)」に代えて、「化合物H4及び燐光発光性化合物R1(化合物H4/燐光発光性化合物R1=90重量%/10重量%)」を用いた以外は、実施例D9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。1000cd/m2における色度座標(x,y)は、(0.66,0.34)であった。初期輝度が4000cd/m2となるように電流値を設定後、定電流で駆動させ、輝度が初期輝度の50%となるまでの時間を測定したところ、2.0時間であった。
実施例D9の(第2の有機層の形成)における、「高分子化合物HTL-1」に代えて、「高分子化合物HTL-3」を用い、更に、実施例D9の(第1の有機層の形成)における、「クロロベンゼンに、化合物H1及び燐光発光性化合物R1(化合物H1/燐光発光性化合物R1=90重量%/10重量%)を2.5重量%の濃度で溶解させた。」に代えて、「トルエンに、化合物H1及び燐光発光性化合物R1(化合物H1/燐光発光性化合物R1=90重量%/10重量%)を2.2重量%の濃度で溶解させた。」とする以外は、実施例D9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。1000cd/m2における色度座標(x,y)は、(0.67,0.32)であった。初期輝度が4000cd/m2となるように電流値を設定後、定電流で駆動させ、輝度が初期輝度の50%となるまでの時間を測定したところ、4.9時間であった。
Claims (11)
- 陽極と、陰極と、陽極及び陰極の間に設けられた第1の有機層と、陽極及び陰極の間に設けられた第2の有機層とを有する発光素子であって、
第1の有機層が、式(1)で表される燐光発光性化合物と式(H)で表される化合物とを含有する層であり、
第2の有機層が、架橋材料の架橋体を含有する層である、発光素子。
Mは、ルテニウム原子、ロジウム原子、パラジウム原子、イリジウム原子又は白金原子を表す。
n1は1以上の整数を表し、n2は0以上の整数を表し、n1+n2は2又は3である。但し、Mがルテニウム原子、ロジウム原子又はイリジウム原子の場合、n1+n2は3であり、Mがパラジウム原子又は白金原子の場合、n1+n2は2である。
E1及びE2は、それぞれ独立に、炭素原子又は窒素原子を表す。但し、E1及びE2の少なくとも一方は炭素原子である。E1及びE2が複数存在する場合、それらはそれぞれ同一でも異なっていてもよい。
環L1は、芳香族複素環を表し、該環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。環L1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。
環L2は、芳香族炭化水素環又は芳香族複素環を表し、これらの環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。環L2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。
環L1が有していてもよい置換基と、環L2が有していてもよい置換基とは、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。
A1-G1-A2は、アニオン性の2座配位子を表す。A1及びA2は、それぞれ独立に、炭素原子、酸素原子又は窒素原子を表し、これらの原子は環を構成する原子であってもよい。G1は、単結合、又は、A1及びA2とともに2座配位子を構成する原子団を表す。A1-G1-A2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。]
nH1は、0以上5以下の整数を表す。nH1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。
nH2は、1以上10以下の整数を表す。
ArH1は、式(H1-1)で表される基を表す。ArH1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。
LH1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、-NRH1’-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。RH1’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。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。
ArH2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。]
環RH1及び環RH2は、それぞれ独立に、単環若しくは縮合環の芳香族炭化水素環又は単環若しくは縮合環の芳香族複素環を表し、これらの環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。
但し、環RH1及び環RH2のうちの少なくとも一つは、縮合環の芳香族炭化水素環又は縮合環の芳香族複素環を表し、これらの環は置換基を有していてもよい。
XH1は、単結合、酸素原子、硫黄原子、-N(RXH1)-で表される基、又は、-C(RXH1’)2-で表される基を表す。RXH1及びRXH1’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、アルコキシ基、シクロアルコキシ基、アリール基、アリールオキシ基、1価の複素環基、置換アミノ基又はハロゲン原子を表し、これらの基は置換基を有していてもよい。複数存在するRXH1’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。
RXH1と環RH1が有していてもよい置換基、RXH1と環RH2が有していてもよい置換基、RXH1’と環RH1が有していてもよい置換基、及び、RXH1’と環RH2が有していてもよい置換基は、それぞれ結合して、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。] - 前記架橋材料が、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、請求項2に記載の発光素子。
- 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3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、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、直接又は酸素原子も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、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、架橋基A群から選ばれる架橋基である。] - 前記架橋材料が有する架橋基が、式(XL-2)、式(XL-3)、式(XL-4)、式(XL-5)、式(XL-6)、式(XL-7)、式(XL-8)、式(XL-9)、式(XL-10)、式(XL-11)、式(XL-12)、式(XL-13)、式(XL-14)、式(XL-15)又は式(XL-17)で表される基である、請求項2~4のいずれか一項に記載の発光素子。
- 前記式(H1-1)で表される基が、式(H1-1B)で表される基、式(H1-1C)で表される基又は式(H1-1D)で表される基である、請求項1~5のいずれか一項に記載の発光素子。
XH1は、前記と同じ意味を表す。
XH2及びXH3は、それぞれ独立に、単結合、酸素原子、硫黄原子、-N(RXH2)-で表される基、又は、-C(RXH2’)2-で表される基を表す。RXH2及びRXH2’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、アルコキシ基、シクロアルコキシ基、アリール基、アリールオキシ基、1価の複素環基、置換アミノ基又はハロゲン原子を表し、これらの基は置換基を有していてもよい。複数存在するRXH2’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。
ZH1、ZH2、ZH3、ZH4、ZH5、ZH6、ZH7、ZH8、ZH9、ZH10、ZH11及びZH12は、それぞれ独立に、炭素原子又は窒素原子を表す。
RH1、RH2、RH3、RH4、RH5、RH6、RH7、RH8、RH9、RH10、RH11及びRH12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、アルコキシ基、シクロアルコキシ基、アリール基、アリールオキシ基、1価の複素環基、置換アミノ基又はハロゲン原子を表し、これらの基は置換基を有していてもよい。
ZH1が窒素原子の場合、RH1は存在しない。ZH2が窒素原子の場合、RH2は存在しない。ZH3が窒素原子の場合、RH3は存在しない。ZH4が窒素原子の場合、RH4は存在しない。ZH5が窒素原子の場合、RH5は存在しない。ZH6が窒素原子の場合、RH6は存在しない。ZH7が窒素原子の場合、RH7は存在しない。ZH8が窒素原子の場合、RH8は存在しない。ZH9が窒素原子の場合、RH9は存在しない。ZH10が窒素原子の場合、RH10は存在しない。ZH11が窒素原子の場合、RH11は存在しない。ZH12が窒素原子の場合、RH12は存在しない。
RH1とRH2、RH3とRH4、RH5とRH6、RH6とRH7、RH7とRH8、RH9とRH10、RH10とRH11、及び、RH11とRH12は、それぞれ結合して、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。] - 前記式(1)で表される燐光発光性化合物が、式(1-B)で表される燐光発光性化合物である、請求項1~6のいずれか一項に記載の発光素子。
M、n1、n2及びA1-G1-A2は、前記と同じ意味を表す。
E11B、E12B、E13B、E14B、E21B、E22B、E23B及びE24Bは、それぞれ独立に、窒素原子又は炭素原子を表す。E11B、E12B、E13B、E14B、E21B、E22B、E23B及びE24Bが複数存在する場合、それらはそれぞれ同一でも異なっていてもよい。E11Bが窒素原子の場合、R11Bは存在しない。E12Bが窒素原子の場合、R12Bは存在しない。E13Bが窒素原子の場合、R13Bは存在しない。E14Bが窒素原子の場合、R14Bは存在しない。E21Bが窒素原子の場合、R21Bは存在しない。E22Bが窒素原子の場合、R22Bは存在しない。E23Bが窒素原子の場合、R23Bは存在しない。E24Bが窒素原子の場合、R24Bは存在しない。
R11B、R12B、R13B、R14B、R21B、R22B、R23B及びR24B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、アルコキシ基、シクロアルコキシ基、アリール基、アリールオキシ基、1価の複素環基、置換アミノ基又はハロゲン原子を表し、これらの基は置換基を有していてもよい。R11B、R12B、R13B、R14B、R21B、R22B、R23B及びR24Bが複数存在する場合、それらはそれぞれ同一でも異なっていてもよい。R11BとR12B、R12BとR13B、R13BとR14B、R11BとR21B、R21BとR22B、R22BとR23B、及び、R23BとR24Bは、それぞれ結合して、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。
環L1Bは、窒素原子、炭素原子、E11B、E12B、E13B及びE14Bとで構成されるピリジン環又はピリミジン環を表す。
環L2Bは、2つの炭素原子、E21B、E22B、E23B及びE24Bとで構成されるベンゼン環、ピリジン環又はピリミジン環を表す。] - 前記式(1-B)で表される燐光発光性化合物が、式(1-B1)で表される燐光発光性化合物、式(1-B2)で表される燐光発光性化合物、式(1-B3)で表される燐光発光性化合物、式(1-B4)で表される燐光発光性化合物又は式(1-B5)で表される燐光発光性化合物である、請求項7に記載の発光素子。
M、n1、n2、A1-G1-A2、R11B、R12B、R13B、R14B、R21B、R22B、R23B及びR24Bは、前記と同じ意味を表す。
n11及びn12は、それぞれ独立に、1以上の整数を表し、n11+n12は2又は3である。但し、Mがルテニウム原子、ロジウム原子又はイリジウム原子の場合、n11+n12は3であり、Mがパラジウム原子又は白金原子の場合、n11+n12は2である。
R15B、R16B、R17B及びR18B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、アルコキシ基、シクロアルコキシ基、アリール基、アリールオキシ基、1価の複素環基、置換アミノ基又はハロゲン原子を表し、これらの基は置換基を有していてもよい。R15B、R16B、R17B及びR18Bが複数存在する場合、それらはそれぞれ同一でも異なっていてもよい。R13BとR15B、R15BとR16B、R16BとR17B、R17BとR18B、及び、R18BとR21Bは、それぞれ結合して、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。] - 前記式(1)で表される燐光発光性化合物が、式(1-A)で表される燐光発光性化合物である、請求項1~6のいずれか一項に記載の発光素子。
M、n1、n2、E1及びA1-G1-A2は、前記と同じ意味を表す。
E11A、E12A、E13A、E21A、E22A、E23A及びE24Aは、それぞれ独立に、窒素原子又は炭素原子を表す。E11A、E12A、E13A、E21A、E22A、E23A及びE24Aが複数存在する場合、それらはそれぞれ同一でも異なっていてもよい。E11Aが窒素原子の場合、R11Aは存在しても存在しなくてもよい。E12Aが窒素原子の場合、R12Aは存在しても存在しなくてもよい。E13Aが窒素原子の場合、R13Aは存在しても存在しなくてもよい。E21Aが窒素原子の場合、R21Aは存在しない。E22Aが窒素原子の場合、R22Aは存在しない。E23Aが窒素原子の場合、R23Aは存在しない。E24Aが窒素原子の場合、R24Aは存在しない。
R11A、R12A、R13A、R21A、R22A、R23A及びR24A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、アルコキシ基、シクロアルコキシ基、アリール基、アリールオキシ基、1価の複素環基、置換アミノ基又はハロゲン原子を表し、これらの基は置換基を有していてもよい。R11A、R12A、R13A、R21A、R22A、R23A及びR24Aが複数存在する場合、それらはそれぞれ同一でも異なっていてもよい。R11AとR12A、R12AとR13A、R11AとR21A、R21AとR22A、R22AとR23A、及び、R23AとR24Aは、それぞれ結合して、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。
環L1Aは、窒素原子、E1、E11A、E12A及びE13Aとで構成されるトリアゾール環又はジアゾール環を表す。
環L2Aは、2つの炭素原子、E21A、E22A、E23A及びE24Aとで構成されるベンゼン環、ピリジン環又はピリミジン環を表す。] - 前記第1の有機層と、前記第2の有機層とが、隣接している、請求項1~9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1~10のいずれか一項に記載の発光素子。
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