WO2019216185A1 - 化合物、化合物の製造法及びそれを用いた発光材料の製造法 - Google Patents
化合物、化合物の製造法及びそれを用いた発光材料の製造法 Download PDFInfo
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- WO2019216185A1 WO2019216185A1 PCT/JP2019/017134 JP2019017134W WO2019216185A1 WO 2019216185 A1 WO2019216185 A1 WO 2019216185A1 JP 2019017134 W JP2019017134 W JP 2019017134W WO 2019216185 A1 WO2019216185 A1 WO 2019216185A1
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- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
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- 125000002510 isobutoxy group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])O* 0.000 description 1
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- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
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- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 1
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- 125000005003 perfluorobutyl group Chemical group FC(F)(F)C(F)(F)C(F)(F)C(F)(F)* 0.000 description 1
- 125000005007 perfluorooctyl group Chemical group FC(C(C(C(C(C(C(C(F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)* 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 1
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- IGLNJRXAVVLDKE-UHFFFAOYSA-N rubidium atom Chemical compound [Rb] IGLNJRXAVVLDKE-UHFFFAOYSA-N 0.000 description 1
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- 239000011775 sodium fluoride Substances 0.000 description 1
- 235000013024 sodium fluoride Nutrition 0.000 description 1
- 229910001415 sodium ion Inorganic materials 0.000 description 1
- WWGXHTXOZKVJDN-UHFFFAOYSA-M sodium;n,n-diethylcarbamodithioate;trihydrate Chemical compound O.O.O.[Na+].CCN(CC)C([S-])=S WWGXHTXOZKVJDN-UHFFFAOYSA-M 0.000 description 1
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- 241000894007 species Species 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052712 strontium Inorganic materials 0.000 description 1
- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 description 1
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- DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical compound CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 1
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 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
- 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
- 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
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- 125000004306 triazinyl group Chemical group 0.000 description 1
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- WLPUWLXVBWGYMZ-UHFFFAOYSA-N tricyclohexylphosphine Chemical compound C1CCCCC1P(C1CCCCC1)C1CCCCC1 WLPUWLXVBWGYMZ-UHFFFAOYSA-N 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 229910000404 tripotassium phosphate Inorganic materials 0.000 description 1
- 235000019798 tripotassium phosphate Nutrition 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
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- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- C09D165/00—Coating compositions based on macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain; Coating compositions based on derivatives of such polymers
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- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
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- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N30/00—Investigating or analysing materials by separation into components using adsorption, absorption or similar phenomena or using ion-exchange, e.g. chromatography or field flow fractionation
- G01N30/02—Column chromatography
- G01N30/88—Integrated analysis systems specially adapted therefor, not covered by a single one of the groups G01N30/04 - G01N30/86
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- H10K85/322—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3] comprising boron
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Definitions
- the present invention relates to a compound, a method for producing the compound, and a method for producing a light emitting material using the compound.
- organic EL materials Materials that exhibit the organic EL phenomenon include light emitting materials and charge transport materials. Each of these has a chemical structure in which aromatic rings are linked.
- a raw material for producing the organic EL material for example, an arylene compound represented by the following formula (1) or formula (2) is used.
- the organic EL material has a high purity.
- the raw material (1) or (2) used is also a high purity.
- HPLC method high performance liquid chromatography method
- the gas chromatography method needs to have a certain vapor pressure at a temperature at which the target substance is not decomposed, and the substance having a low vapor pressure is difficult to analyze.
- the HPLC method can analyze even a substance having a low vapor pressure, and is often used for analyzing a raw material of an organic EL light emitting material.
- an aromatic monomer having a boron-containing functional group with a purity of 99% or more is synthesized by HPLC analysis.
- the characteristics required for the organic EL material include that the element has high luminance, high efficiency, low voltage drive, and long life when used in an organic EL element.
- An object of the present invention is to provide a high-purity raw material (1) or (2), a purification method thereof, and a method for producing a luminescent material synthesized using the raw material.
- the performance of the organic EL element is affected by the charge transport property of the organic EL material used for the element. That is, the organic EL element usually has a plurality of layers such as a light emitting layer, a hole transport layer, a hole injection layer, an electron transport layer, and an electron injection layer, and as a whole has high brightness, high efficiency, low voltage drive, and long life.
- the balance should be designed so that the charge transport property of each layer is balanced.
- the charge transport property of each layer depends on the manner in which aromatic rings are linked in the chemical structure of the compound used in the light emitting layer. This is particularly noticeable in the light emitting layer.
- the raw materials (1) or (2) of the organic EL material include compounds having different aromatic ring linking modes as impurities.
- the chemical structure of such impurities is that the aromatic rings of the raw material (1) or (2) are randomly connected, and the molecular weight is considered to be larger than the molecular weight of the compound represented by the formula (1) or (2). It is done. Therefore, as a means for solving the above problems, the content of impurities having a molecular weight larger than the molecular weight of the compound represented by formula (1) or (2) is limited to a specific amount or less. As means for confirming the content of impurities having a molecular weight larger than the molecular weight of the compound represented by the formula (1) or (2), the peak area method of organic solvent-based size exclusion chromatography was employed.
- the present invention is a compound represented by the following formula (1) or (2), and the content of impurities having a molecular weight larger than the molecular weight of the compound represented by formula (1) or (2) is 0. .15% or less, and the content of the impurities is the sum of the areas of peaks having a shorter retention time than the peak identified as the formula (1) or (2) in the chromatogram by organic solvent size exclusion chromatography, Provide a compound that is a percentage of the sum of the total peak areas.
- 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.
- Z 1 represents a leaving group.
- a 1 and a 2 each independently represents an integer of 0 or more.
- Ar X1 and Ar X3 each independently represent an arylene group or a divalent heterocyclic group, and these groups optionally have a substituent.
- Ar X2 and Ar X4 each independently represent an arylene group, a divalent heterocyclic group, or a divalent group in which at least one arylene group and at least one divalent heterocyclic group are directly bonded to each other. And these groups may have a substituent.
- R X1 , R X2 and R X3 each independently represent a hydrogen atom, an alkyl group, an aryl group or a monovalent heterocyclic group, and these groups may have a substituent.
- Z 2 represents a leaving group.
- any one of the above compounds has a purity by the area percentage method exceeding 99% in a chromatogram by high performance liquid chromatography using a reverse phase column.
- the leaving group shown by Z ⁇ 1 >, Z ⁇ 2 > is group chosen from the group which consists of the following substituent A group or B group.
- the substituent group A is a chlorine atom, a bromine atom, an iodine atom, and —O—S ( ⁇ O) 2 R C1 (wherein R C1 represents an alkyl group or an aryl group, and these groups are substituted) Group which may have a group).
- Substituent group B is —B (OR C2 ) 2 (wherein R C2 represents a hydrogen atom, an alkyl group or an aryl group, and these groups may have a substituent.
- C2 may be the same or different, and may be linked to each other to form a ring structure together with the oxygen atom to which each is bonded.
- a group represented by BF 3 Q ′ (wherein Q ′ represents Li, Na, K, Rb or Cs); A group represented by —MgY ′ (wherein Y ′ represents a chlorine atom, a bromine atom or an iodine atom); A group represented by —ZnY ′′ (wherein Y ′′ represents a chlorine atom, a bromine atom or an iodine atom); and —Sn (R C3 ) 3 (wherein R C3 is a hydrogen atom or an alkyl group) Or an aryl group, and these groups may have a substituent, and a plurality of R C3 may be the same or different, and are connected to each other to form a ring structure with the tin atom to which each is bonded. It is a group represented by.
- the leaving group represented by Z 1 or Z 2 is a bromine atom, or —B (OR C2 ) 2 (wherein R C2 represents a hydrogen atom, an alkyl group or an aryl group, and The group may have a substituent, and a plurality of R C2 may be the same or different, and may be linked to each other to form a ring structure together with the oxygen atom to which each is bonded. It is a group represented.
- any of the above compounds is used for the synthesis of a compound by a condensation reaction.
- the compound synthesized is an organic EL material.
- the synthesized compound is a polymer compound.
- this invention provides the manufacturing method of a compound including the process of performing a condensation reaction using the compound shown by any one of said Formula (1), and the compound shown by any said Formula (2). .
- this invention performs a condensation reaction using the compound shown by any one of said Formula (1), the compound shown by any said Formula (2), and the compound shown by the following formula
- a method for producing a compound comprising the steps is provided.
- R X4 represents an aryl group or a monovalent heterocyclic group, and these groups optionally have a substituent.
- Z 3 represents a leaving group.
- the compound produced is an organic EL material.
- the produced compound is a polymer compound.
- 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.
- Z 1 represents a leaving group.
- a 1 and a 2 each independently represents an integer of 0 or more.
- Ar X1 and Ar X3 each independently represent an arylene group or a divalent heterocyclic group, and these groups optionally have a substituent.
- Ar X2 and Ar X4 each independently represent an arylene group, a divalent heterocyclic group, or a divalent group in which at least one arylene group and at least one divalent heterocyclic group are directly bonded to each other. And these groups may have a substituent.
- R X1 , R X2 and R X3 each independently represent a hydrogen atom, an alkyl group, an aryl group or a monovalent heterocyclic group, and these groups may have a substituent.
- Z 2 represents a leaving group.
- the content of impurities having a molecular weight greater than the molecular weight of the compound represented by formula (1) or (2) is 0.15% or less by dissolving the compound represented by
- a purification method is provided which is a percentage of the sum of the areas of peaks having a shorter retention time than the peak identified as (2) to the sum of the total peak areas.
- the present invention also provides an organic EL material comprising a polymer obtained by condensation polymerization of any one of the compounds represented by formula (1) and any one of the compounds represented by formula (2).
- the present invention also provides a polymer obtained by condensation polymerization of any one of the compounds represented by the formula (1), any compound represented by any one of the above formulas (2), and any compound represented by the above formula (3).
- the present invention also provides a composition comprising any one of the above organic EL materials and an organic solvent.
- the present invention also provides a thin film containing any one of the above organic EL materials.
- the present invention also provides an organic EL device having the above thin film.
- the present invention it is possible to provide a raw material for producing an organic EL material exhibiting high luminance, high efficiency, low voltage drive, and long life, and a method for purifying the raw material. Further, it is possible to provide a method for manufacturing an organic EL material exhibiting high luminance, high efficiency, low voltage driving, and long life.
- Me represents a methyl group
- Et represents an ethyl group
- i-Pr represents an isopropyl group
- n-Bu represents an n-butyl group
- t-Bu represents a tert-butyl group.
- 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 structural unit contained in the polymer compound is 100 mol% in total.
- 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, branched or cyclic.
- the number of carbon atoms of the linear alkyl group is usually 1 to 50, preferably 3 to 30, more preferably 4 to 20, not including the carbon atoms of the substituent.
- the number of carbon atoms in the branched and cyclic alkyl group is usually 3 to 50, preferably 3 to 30, more preferably 4 to 20, not including the number of carbon atoms of the substituent.
- the alkyl group may have a substituent, for example, methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, tert-butyl group, n-pentyl group, isoamyl 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 does not include the number of carbon atoms of the substituent, and is usually 6 to 60, preferably 6 to 20, and more preferably 6 to 10.
- the aryl group may have a substituent, such as a phenyl group, 1-naphthyl group, 2-naphthyl group, 1-anthracenyl group, 2-anthracenyl group, 9-anthracenyl group, 1-pyrenyl group, 2 -Pyrenyl group, 4-pyrenyl group, 2-fluorenyl group, 3-fluorenyl group, 4-fluorenyl group, 2-phenylphenyl group, 3-phenylphenyl group, 4-phenylphenyl group, and hydrogen atoms in these groups Is a group substituted with an alkyl group, an alkoxy group, an aryl group, a fluorine atom or the like.
- a substituent such as a phenyl group, 1-naphthyl group, 2-naphthyl group, 1-anthracenyl group, 2-anthracenyl group, 9-anthracenyl group,
- the “alkoxy group” may be linear, branched or cyclic.
- the number of carbon atoms of the linear alkoxy group does not include the number of carbon atoms of the substituent, and is usually 1 to 40, preferably 4 to 10.
- the number of carbon atoms of the branched and cyclic alkoxy group does not include the number of carbon atoms of the substituent, and is usually 3 to 40, preferably 4 to 10.
- the alkoxy group may have a substituent, for example, methoxy group, ethoxy group, n-propyloxy group, isopropyloxy group, n-butyloxy group, isobutyloxy group, tert-butyloxy group, n-pentyloxy group.
- a substituent for example, methoxy group, ethoxy group, n-propyloxy group, isopropyloxy group, n-butyloxy group, isobutyloxy group, tert-butyloxy group, n-pentyloxy group.
- An oxy group is
- the “aryloxy group” has 6 to 60 carbon atoms, preferably 7 to 48, not including the carbon atoms of the substituent.
- the aryloxy group may have a substituent, for example, 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, an alkoxy 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” include oxadiazole, thiadiazole, thiazole, oxazole, thiophene, pyrrole, phosphole, furan, pyridine, pyrazine, pyrimidine, triazine, pyridazine, quinoline, isoquinoline, carbazole, dibenzosilole, dibenzophosphole A compound in which the heterocycle itself is aromatic, and a heterocycle itself such as phenoxazine, phenothiazine, dibenzoborol, dibenzosilol, benzopyran does not exhibit aromaticity, but the aromatic ring is condensed to the heterocycle Means a compound that has been
- the number of carbon atoms of the monovalent heterocyclic group does not include the number of carbon atoms of the substituent and is usually 2 to 60, preferably 4 to 20.
- the monovalent heterocyclic group may have a substituent, for example, thienyl group, pyrrolyl group, furyl group, pyridyl group, piperidyl group, quinolyl group, isoquinolyl group, pyrimidinyl group, triazinyl group, and these And a group in which the hydrogen atom in the group is substituted with an alkyl group, an alkoxy group or the like.
- a substituent for example, thienyl group, pyrrolyl group, furyl group, pyridyl group, piperidyl group, quinolyl group, isoquinolyl group, pyrimidinyl group, triazinyl group, and these And a group in which the hydrogen atom in the group is substituted with an alkyl group, an alkoxy 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.
- the substituent that the amino group has is preferably an alkyl group, an aryl group, or a monovalent heterocyclic group.
- Examples of the substituted amino group include a dialkylamino group and a diarylamino group.
- amino group examples include dimethylamino group, diethylamino group, diphenylamino group, bis (4-methylphenyl) amino group, bis (4-tert-butylphenyl) amino group, and bis (3,5-di-tert- Butylphenyl) amino group.
- “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 represent a hydrogen atom, an alkyl group or an aryl group.
- a plurality of R and R a may be the same or different.
- Adjacent R a may be bonded to each other to form a ring together with the carbon 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 without including 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 Are groups represented by formulas (A-21) to (A-52).
- the divalent heterocyclic group includes a group in which a plurality of these groups are bonded.
- R and R a represent the same meaning as described above.
- “Substituent” represents a halogen atom, a cyano group, an alkyl group, an aryl group, a monovalent heterocyclic group, an alkoxy group, an aryloxy group, an amino group, or a substituted amino group.
- crosslinking group refers to formulas (B-1), (B-2), (B-3), (B-4), (B-5), (B-6), (B-7), (B-8), (B-9), (B-10), (B-11), (B-12), (B-13), (B-14), (B-15), (B -16) or a group represented by (B-17).
- these groups may have a substituent.
- the high molecular compound contains the structural unit represented by following formula (X).
- a X1 and a X2 each independently represent an integer of 0 or more.
- Ar X1 and Ar X3 each independently represent an arylene group or a divalent heterocyclic group, and these groups optionally have a substituent.
- Ar X2 and Ar X4 each independently represent an arylene group, a divalent heterocyclic group, or a divalent group in which at least one arylene group and at least one divalent heterocyclic group are directly bonded to each other. And these groups may have a substituent.
- R X1 , R X2 and R X3 each independently represent a hydrogen atom, an alkyl group, an aryl group or a monovalent heterocyclic group, and these groups may have a substituent.
- a X1 is preferably 2 or less, more preferably 1, because the luminance life of a light emitting device using a polymer compound is excellent.
- a X2 is preferably 2 or less, more preferably 0, because the luminance life of a light emitting device using a polymer compound is excellent.
- R X1 , R X2 and R X3 are preferably an alkyl group, an aryl group or a monovalent heterocyclic group, more preferably an aryl group, and these groups may have a substituent.
- the arylene group represented by Ar X1 and Ar X3 is particularly preferably a group represented by the formula (A-1) or (A-9), and particularly preferably represented by the formula (A-1). These groups may have a substituent.
- the divalent heterocyclic group represented by Ar X1 and Ar X3 is particularly preferably represented by formula (A-21), formula (A-22), or formula (A-27) to formula (A-46). 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 particularly preferably formula (A-1), formula (A-6), formula (A-7), formula (A-9) to formula (A-11). ) Or a group represented by the formula (A-19), and these groups optionally have a substituent.
- the particularly preferred range of the divalent heterocyclic group represented by Ar X2 and Ar X4 is the same as the particularly preferred 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, an aryl group, or a monovalent heterocyclic group, and these groups may have a substituent.
- R XX is preferably an alkyl 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 group that may be represented by the groups represented by Ar X1 to Ar X4 and R X1 to R X3 is preferably an alkyl group or an aryl group, and these groups may further have a substituent. Good.
- the structural unit represented by the formula (X) is preferably a structural unit represented by the formulas (X-1) to (X-7), more preferably the formula (X-3) to (X-7).
- the structural unit represented by formulas (X-3) to (X-6) is more preferred.
- R X4 and R X5 each independently represent a hydrogen atom, an alkyl group, an alkoxy group, an aryl group, an aryloxy group, a halogen atom, a monovalent heterocyclic group, or a cyano group, and these groups are substituted. It may have a group.
- a plurality of R X4 may be the same or different.
- a plurality of R X5 may be the same or different, and adjacent R X5 may be bonded to each other to form a ring together with the carbon atom to which each is bonded.
- the structural unit represented by the formula (X) has excellent hole transportability, it is preferably 0.1 to 50 mol%, more preferably based on the total amount of structural units contained in the polymer compound. It is 1 to 40 mol%, and more preferably 5 to 30 mol%.
- Examples of the structural unit represented by the formula (X) include structural units represented by the formulas (X1-1) to (X1-19), preferably the formulas (X1-6) to (X1-14). ).
- the structural unit represented by the formula (X) may be included alone or in combination of two or more.
- the polymer compound has excellent hole transport properties, it is preferable that the polymer compound further includes a structural unit represented by the formula (Y).
- the polymer compound preferably contains a structural unit represented by the formula (X) or a structural unit represented by the formula (Y) from the viewpoint of light emission efficiency when used in the production of a light emitting device.
- 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.
- the group may have a substituent.
- the arylene group represented by Ar Y1 is particularly preferably formula (A-1), formula (A-6), formula (A-7), formula (A-9) to formula (A-11), formula A group represented by formula (A-13) or formula (A-19), particularly preferably formula (A-1), formula (A-7), formula (A-9) or formula (A-19) These groups may have a substituent.
- the divalent heterocyclic group represented by Ar Y1 is particularly preferably formula (A-24), formula (A-30), formula (A-33), formula (A-35), formula (A- 38) or a group represented by formula (A-40), particularly preferably represented by formula (A-24), formula (A-30), formula (A-38) or formula (A-40). These groups may have a substituent.
- a particularly preferred range of the arylene group and the divalent heterocyclic group in the divalent group in which at least one arylene group represented by Ar Y1 and at least one divalent heterocyclic group are directly bonded particularly preferred.
- the ranges are the same as the particularly preferred ranges, particularly preferred ranges, of the arylene group and divalent heterocyclic group represented by Ar Y1 described above, respectively.
- the substituent that the group represented by Ar Y1 may have is preferably an alkyl 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 formulas (Y-1) to (Y-7). From the viewpoint of the luminance life of the light-emitting element using the polymer compound. Is preferably a structural unit represented by formula (Y-1) or (Y-2), and from the viewpoint of electron transport properties, it is preferably represented by formula (Y-3) or (Y-4). From the viewpoint of hole transportability, structural units represented by formulas (Y-5) to (Y-7) are preferable.
- R Y1 represents a hydrogen atom, an alkyl group, an alkoxy group, an aryl group, or a monovalent heterocyclic group, and these groups may have a substituent.
- a plurality of R Y1 may be the same or different, and adjacent R Y1 may be bonded to each other to form a ring together with the carbon atom to which each is bonded.
- R Y1 is preferably a hydrogen atom, an alkyl group, or an aryl 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, an alkoxy 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, an aryl group, or a monovalent heterocyclic group, more preferably an alkyl group or an aryl group, and these groups optionally have a substituent.
- the combination of two R Y2 in the group represented by —C (R Y2 ) 2 — in X Y1 is preferably both an alkyl group, both an aryl group, both a monovalent heterocyclic group, or , One is an alkyl group and the other is an aryl group or a monovalent heterocyclic group, more preferably one is an alkyl group and the other is an aryl group, and these groups may have a substituent.
- R Y2 s may be bonded to each other to form a ring together with the atoms to which they are bonded, and when R Y2 forms a ring, the group represented by —C (R Y2 ) 2 — Is preferably a group represented by formulas (Y-A1) to (Y-A5), more preferably a group represented by formula (Y-A4), and these groups have a substituent. It may be.
- the combination of two R Y2 in the group represented by —C (R Y2 ) ⁇ C (R Y2 ) — is preferably both an alkyl group, or one is an alkyl group and the other is an aryl group. These groups may have a substituent.
- R Y2 in the group represented by —C (R Y2 ) 2 —C (R Y2 ) 2 — are preferably an alkyl group which may have a substituent.
- a plurality of R Y2 may be bonded to each other to form a ring together with the atoms to which each is bonded.
- R Y2 forms a ring —C (R Y2 ) 2 —C (R Y2 ) 2 —
- the group represented is preferably a group represented by the formulas (Y-B1) to (Y-B5), more preferably a group represented by the formula (Y-B3). These groups are substituted It may have a group.
- R Y2 represents the same meaning as described above.
- R Y1 represents the same meaning as described above.
- R Y3 represents a hydrogen atom, an alkyl group, an alkoxy group, an aryl group, or a monovalent heterocyclic group, and these groups optionally have a substituent.
- R Y3 is preferably an alkyl group, an alkoxy group, an aryl group, or a monovalent heterocyclic group, more preferably an aryl group, and these groups optionally have a substituent.
- R Y1 represents the same meaning as described above.
- R Y4 represents a hydrogen atom, an alkyl group, an alkoxy group, an aryl group, or a monovalent heterocyclic group, and these groups optionally have a substituent.
- R Y4 is preferably an alkyl group, an alkoxy group, an aryl group or a monovalent heterocyclic group, more preferably an aryl group, and these groups optionally have a substituent.
- Examples of the structural unit represented by the formula (Y) include structural units represented by the formulas (Y-11) to (Y-55).
- the structural unit represented by the formula (Y), in which Ar Y1 is an arylene group, has excellent luminance life of a light-emitting element using the polymer compound, and thus the total of the structural units contained in the polymer compound
- the amount is preferably 0.5 to 80 mol%, more preferably 30 to 60 mol%, based on the amount.
- the structural unit which is a group is preferably 0.5 to 30 mol% with respect to the total amount of the structural units contained in the polymer compound, since the charge transport property of the light emitting device using the polymer compound is excellent. More preferably, it is 3 to 40 mol%.
- the structural unit represented by the formula (Y) may be included in the polymer compound alone or in combination of two or more.
- the raw material as used herein refers to a compound that is a raw material for synthesizing an organic EL material.
- a high molecular weight impurity means an impurity having a molecular weight larger than the molecular weight of a compound as a raw material.
- the high molecular weight impurity has a chemical structure in which aromatic rings derived from raw materials are randomly connected, and when present in an organic EL material, the charge transportability balance in each layer in the organic EL element is balanced. Breaking down and lowering the performance when an organic EL element is obtained. In order to improve the performance of the organic EL element, it is necessary to remove high molecular weight impurities from the raw material.
- the content of high molecular weight impurities in the raw material is 0.15% or less, preferably 0.10% or less, more preferably 0.05% or less.
- High molecular weight impurities are components having a shorter elution time than the compound when the compound as a raw material is analyzed by organic solvent-based size exclusion chromatography.
- the column used for organic solvent-based size exclusion chromatography is not particularly limited, but a column that can favorably separate a polystyrene-equivalent molecular weight of 500 to 10,000 in a calibration curve using standard polystyrene is preferable.
- Preferred columns include TSK gel G1000-G4000H series, GMH-L series, Super HZ1000-4000, Super HZM (Tosoh), KF-801-803, 803L series, KF-401-403 series (Shoudex), etc.
- PLGEL MIXED-A ⁇ E Algilent
- the mobile phase in the organic solvent-based size exclusion chromatography is not particularly limited as long as the raw material monomer is a solvent that guarantees performance by the column manufacturer, but usually tetrahydrofuran, chloroform, dichloromethane, dichloroethane, DMF, DMSO, dioxane, hexane, cyclohexane, NMP, methyl ethyl ketone, acetone, methanol, ethanol, or a mixed solvent thereof is used, and tetrahydrofuran, chloroform, DMF, and acetone are preferable, and tetrahydrofuran is more preferable.
- the chromatography detector is not particularly limited, but a UV-vis detector and a differential refractive index detector are preferably used, and a UV-vis detector is preferably used.
- the content of high molecular weight impurities in the raw material is obtained from the chromatogram obtained by organic solvent size exclusion chromatography using the following formula.
- JP-T-2002-536492 As a method for synthesizing a raw material compound, for example, there is a method shown in JP-T-2002-536492.
- This raw material is disclosed to have a content of 99% or more in high performance liquid chromatography, but some high molecular weight impurities in the raw material are not detected by high performance liquid chromatography and are not sufficiently removed.
- the raw material needs to be purified until the high molecular weight impurities are sufficiently removed.
- the raw material of the present invention preferably has a high purity by high performance liquid chromatography. Purity by high performance liquid chromatography is determined based on the peak area percentage of the high performance liquid chromatogram using a reverse phase column.
- the raw material of the present invention has a purity by high-performance liquid chromatography of more than 99%, preferably 99.5% or more, more preferably 99.8% or more.
- the type of the reverse phase column is not particularly limited as long as the compound as a raw material can be analyzed with high resolution, but usually an octadecyl group (C18), an octyl group (C8), a butyl group (C4), a trimethyl group (C3 ),
- a silica gel column to which a phenyl group, a cyanopropyl group or the like is bonded is preferable.
- Preferred columns include the L-column series (Chemical Substance Evaluation Research Organization), C18M, C18P, 5C8, 5CN series (Shoudex), and ZORBAX®RP series (Aglient).
- the mobile phase used in high performance liquid chromatography using a reverse phase column water, methanol, acetonitrile, tetrahydrofuran, etc. are used, and these may be used as a mixture, or the gradient method changes the mixing ratio over time. May be used. Antioxidants and pH adjusters may be added.
- adsorption with an adsorbent As the raw material purification method, adsorption with an adsorbent, recrystallization, and a combination of adsorption and recrystallization are preferable.
- Adsorption by the adsorbent is performed by dissolving the raw material monomer in an organic solvent, adding the adsorbent and stirring with heating as necessary, followed by filtration.
- Organic solvents include aromatic hydrocarbons such as benzene, toluene, ethylbenzene, xylene, mesitylene, 1,2,4-trimethylbenzene, and halogenated aromatics such as chlorobenzene, o-dichlorobenzene, m-dichlorobenzene, and bromobenzene.
- Hydrocarbons such as aromatic hydrocarbons, ethers such as diethyl ether, diisopropyl ether and anisole, cyclic ethers such as tetrahydrofuran and dioxane, aliphatic hydrocarbons such as pentane, hexane, heptane and octane, halogenated hydrocarbons such as dichloromethane, dichloroethane and chloroform , Alcohols such as methanol, ethanol and 2-propanol, ketones such as acetone and methyl ethyl ketone, acetonitrile, dimethylformamide, dimethyl sulfoxide, N-methylpyrrolide And the like, it may be used by mixing these solvents, if necessary. Of these, toluene, hexane, dichloromethane and chloroform are preferred.
- the amount of the organic solvent used is usually 0.5 to 100 times by weight, preferably 1 to 50 times by weight with respect to the raw material monomer.
- Examples of the adsorbent include activated carbon, silica gel, activated alumina, zeolite, activated clay, or a mixture thereof, and activated carbon is particularly preferable.
- the amount of adsorbent is usually 0.05 to 5 times by weight, preferably 0.1 to 1 times by weight with respect to the raw material monomer.
- the temperature at the time of stirring is usually from ⁇ 20 ° C. to the boiling point of the solvent, preferably from 20 ° C. to the boiling point of the solvent.
- the stirring time is usually 5 minutes to 48 hours, preferably 30 minutes to 3 hours.
- the adsorbent is usually separated by filtration, but a filter aid may be used in combination.
- Adsorption by the adsorbent may be performed by using a packed tower of adsorbent and circulating the raw material monomer solution through the packed tower. In this case, it may be circulated as necessary.
- the solution of the raw material monomer treated with the adsorbent may be adjusted to an appropriate concentration by concentration or dilution and then subjected to the reaction, or the recrystallization operation may be subsequently performed to take out the raw material monomer crystals.
- Purification by recrystallization is a method in which the raw material monomer is heated and dissolved in a soluble organic solvent, and then cooled and separated from the precipitated crystals. After the raw material monomer is dissolved in the soluble organic solvent, a poor solvent for the raw material monomer is added dropwise. There are a method of filtering out the precipitated crystals and a method of combining cooling and dropping of a poor solvent.
- Soluble organic solvents include benzene, toluene, ethyl benzene, xylene, mesitylene, 1,2,4-trimethylbenzene and other aromatic hydrocarbons, chlorobenzene, o-dichlorobenzene, m-dichlorobenzene and bromobenzene
- Aromatic hydrocarbons such as diethyl ether, diisopropyl ether and anisole, cyclic ethers such as tetrahydrofuran and dioxane, aliphatic hydrocarbons such as pentane, hexane, heptane and octane, halogenated carbonization such as dichloromethane, dichloroethane and chloroform Hydrogen etc. are mentioned, You may mix and use these solvents as needed. Of these, toluene, hexane, dichloromethane and chloroform are preferred.
- the amount of the soluble organic solvent used is usually 0.5 to 100 times by weight, preferably 1 to 50 times by weight with respect to the raw material monomer.
- an organic solvent having a relatively high polarity is preferable, and alcohols such as methanol, ethanol and 2-propanol, ketones such as acetone and methyl ethyl ketone, acetonitrile, dimethylformamide, dimethyl sulfoxide, N-methylpyrrolidone and the like can be mentioned. These solvents may be mixed and used as necessary. Of these, methanol, ethanol, 2-propanol, acetone, and acetonitrile are preferable.
- the amount of the poor solvent used is usually 0.05 to 100 times by weight, preferably 0.1 to 50 times by weight with respect to the raw material monomer.
- a solvent in which a soluble organic solvent and a poor solvent are mixed in advance can also be used.
- the dissolution temperature is usually from room temperature to the boiling point of the solvent, and preferably from 30 ° C. to the boiling point of the solvent.
- the cooling rate is usually 2 to 50 ° C./hr, preferably 5 to 30 ° C./hr.
- seed crystals may be added during cooling, and at the stage where the crystals are precipitated, the temperature is raised by about 2 to 15 ° C., and the temperature is kept for about 5 minutes to 5 hours. It may be cooled again.
- Cooling is usually -50 ° C to 80 ° C, preferably -20 ° C to 30 ° C. After keeping at the final cooling temperature for usually 0 to 24 hours, preferably 0.5 to 8 hours, filtration is performed, and the crystals are washed with a soluble organic solvent, a poor solvent, or a mixed solvent thereof, and then dried. To do.
- the poor solvent is usually dropped over 0.5 to 24 hours, preferably 1 to 8 hours.
- the temperature when dropping the poor solvent is usually from ⁇ 50 ° C. to the boiling point of the solvent, preferably from ⁇ 20 ° C. to the boiling point of the solvent.
- the poor solvent dropping may be performed before the cooling operation, or may be performed during the cooling operation or after the cooling operation.
- R C2 represents a hydrogen atom, an alkyl group or an aryl group, and these groups may have a substituent.
- a plurality of R C2 s may be the same or different. Or may be linked to each other to form a ring structure together with the oxygen atoms to which they are bonded.
- a group represented by BF 3 Q ′ (wherein Q ′ represents Li, Na, K, Rb or Cs);
- Q ′ represents Li, Na, K, Rb or Cs);
- a group represented by —MgY ′ (wherein Y ′ represents a chlorine atom, a bromine atom or an iodine atom);
- a group represented by —ZnY ′′ (wherein Y ′′ represents a chlorine atom, a bromine atom or an iodine atom);
- R C3 represents a hydrogen atom, an alkyl group or an aryl group, and these groups may have a substituent.
- a plurality of R C3 may be the same or different. And may be linked to each other to form a ring structure together with the tin atoms to which they are bonded.
- Examples of the group represented by —B (OR C2 ) 2 include groups represented by the following formulae.
- a compound having a group selected from Substituent Group A and a compound having a group selected from Substituent Group B are subjected to condensation polymerization by a known coupling reaction, and a group selected from Substituent Group A and Substituent Group B Carbon atoms bonded to a group selected from are bonded to each other. Therefore, if a compound having two groups selected from Substituent Group A and a compound having two groups selected from Substituent Group B are subjected to a known coupling reaction, condensation of these compounds by condensation polymerization A polymer can be obtained.
- the condensation polymerization is usually performed in the presence of a catalyst, a base, and a solvent, but may be performed in the presence of a phase transfer catalyst, if necessary.
- the catalyst examples include dichlorobis (triphenylphosphine) palladium, dichlorobis (tris-o-methoxyphenylphosphine) palladium, palladium [tetrakis (triphenylphosphine)], [tris (dibenzylideneacetone)] dipalladium, palladium acetate and the like.
- Nickel complexes such as palladium complexes of nickel, nickel [tetrakis (triphenylphosphine)], [1,3-bis (diphenylphosphino) propane] dichloronickel, [bis (1,4-cyclooctadiene)] nickel Metal complexes; these transition metal complexes may further include triphenylphosphine, tri-o-tolylphosphine, tri-tert-butylphosphine, tricyclohexylphosphine, diphenylphosphinopropane, bipyridyl, etc.
- a catalyst may be used individually by 1 type, or may use 2 or more types together.
- the amount of catalyst used is usually 0.00001 to 3 molar equivalents as the amount of transition metal relative to the total number of moles of raw material monomers.
- Examples of the base and phase transfer catalyst include inorganic bases such as sodium carbonate, potassium carbonate, cesium carbonate, potassium fluoride, cesium fluoride, and tripotassium phosphate; organics such as tetrabutylammonium fluoride and tetrabutylammonium hydroxide.
- Bases Phase transfer catalysts such as tetrabutylammonium chloride, tetrabutylammonium bromide, tricaprylmethylammonium chloride (Aliquat 336) and the like can be mentioned. Each of the base and the phase transfer catalyst may be used alone or in combination of two or more.
- the amount of base and phase transfer catalyst used is usually 0.001 to 100 molar equivalents relative to the total number of moles of raw material monomers.
- the solvent examples include organic solvents such as toluene, xylene, mesitylene, tetrahydrofuran, 1,4-dioxane, dimethoxyethane, N, N-dimethylacetamide, N, N-dimethylformamide, and water.
- organic solvents such as toluene, xylene, mesitylene, tetrahydrofuran, 1,4-dioxane, dimethoxyethane, N, N-dimethylacetamide, N, N-dimethylformamide, and water.
- a solvent may be used individually by 1 type, or may use 2 or more types together.
- the amount of the solvent used is usually 10 to 100,000 parts by weight with respect to 100 parts by weight as a total of the raw material monomers.
- the reaction temperature of the condensation polymerization is usually ⁇ 100 to 200 ° C.
- the reaction time of the condensation polymerization is usually 1 hour or more.
- 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 carried out alone or in combination.
- a lower alcohol such as methanol
- filtering the deposited precipitate and then drying.
- these methods are carried out alone or in combination.
- the purity of the polymer compound is low, it can be purified by a usual method such as recrystallization, reprecipitation, continuous extraction with a Soxhlet extractor, column chromatography, or the like.
- composition contains 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, an antioxidant and a solvent, and a polymer compound. .
- a composition containing a polymer compound and a solvent (hereinafter sometimes referred to as “ink”) is suitable for manufacturing a light-emitting element using a printing method such as an inkjet printing method or a nozzle printing method.
- the viscosity of the ink may be adjusted according to the type of printing method, but when applying a printing method such as an inkjet printing method to a printing method that passes through a discharge device, in order to prevent clogging and flight bending at the time of discharge. It is preferably 1 to 20 mPa ⁇ s at 25 ° C.
- the solvent contained in the 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 tetrahydrofuran, dioxane, anisole and 4-methylanisole; toluene, 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-decane, bicyclohexyl; ketone
- the compounding amount of the solvent is usually 1000 to 100,000 parts by weight, preferably 2000 to 20000 parts by weight with respect to 100 parts by weight of the polymer compound.
- the hole transport material is classified into a low molecular compound and a high molecular compound, and a high molecular compound is preferable, and a high molecular compound having a crosslinking group is more preferable.
- polymer compound examples include polyvinyl carbazole and derivatives thereof; polyarylene having an aromatic amine structure in the side chain or main chain and derivatives thereof.
- the polymer compound may be a compound to which an electron accepting site is bonded. Examples of the electron accepting site include fullerene, tetrafluorotetracyanoquinodimethane, tetracyanoethylene, trinitrofluorenone, and fullerene is preferable.
- the compounding amount of the hole transport material is usually 1 to 400 parts by weight, preferably 5 to 150 parts by weight with respect to 100 parts by weight of the polymer compound.
- the hole transport material may be used alone or in combination of two or more.
- Electron transport materials are classified into low molecular compounds and high molecular compounds.
- the electron transport material may have a crosslinking group.
- low molecular weight compound examples include metal complexes having 8-hydroxyquinoline as a ligand, oxadiazole, anthraquinodimethane, benzoquinone, naphthoquinone, anthraquinone, tetracyanoanthraquinodimethane, fluorenone, diphenyldicyanoethylene, and , Diphenoquinone, and derivatives thereof.
- polymer compound examples include polyphenylene, polyfluorene, and derivatives thereof.
- the polymer compound may be doped with a metal.
- the compounding amount of the electron transport material is usually 1 to 400 parts by weight, preferably 5 to 150 parts by weight with respect to 100 parts by weight of the polymer compound.
- the electron transport material may be used alone or in combination of two or more.
- the hole injection material and the electron injection material are each classified into a low molecular compound and a high molecular compound.
- 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, polyquinoxaline, and derivatives thereof; a group represented by the formula (X) is a main chain or a side chain And conductive polymers such as polymers contained in.
- the compounding amounts of the hole injection material and the electron injection material are usually 1 to 400 parts by weight, preferably 5 to 150 parts by weight, with respect to 100 parts by weight of the polymer compound.
- the hole injection material and the electron injection material may be used alone or in combination of two or more.
- the electrical conductivity of the conductive polymer is preferably 1 ⁇ 10 ⁇ 5 S / cm to 1 ⁇ 10 3 S / cm.
- the conductive polymer can be doped with an appropriate amount of ions.
- the kind of ions to be doped is an anion for a hole injection material and a cation for an electron injection material.
- the anion include polystyrene sulfonate ion, alkylbenzene sulfonate ion, and camphor sulfonate ion.
- the cation include lithium ion, sodium ion, potassium ion, and tetrabutylammonium ion.
- the ion to be doped may be one kind or two or more kinds.
- the polymer compound obtained by the condensation reaction using the raw material compound of the present invention can be used as a light emitting material. You may use together issuing materials other than this high molecular compound. 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.
- polymer compound examples include phenylene group, naphthalenediyl group, anthracenediyl group, fluorenediyl diyl group, phenanthrene diyl group, dihydrophenanthenediyl group, group represented by formula (X), carbazole diyl group, phenoxazine High molecular compounds containing a diyl group, a phenothiazinediyl group, an anthracene diyl group, a pyrenediyl group, and the like can be given.
- the light emitting material may contain a low molecular compound and a high molecular compound, and preferably contains a triplet light emitting complex and a high molecular compound.
- iridium complexes such as metal complexes represented by the formulas Ir-1 to Ir-3 are preferable.
- R D1 to R D8 and R D11 to R D20 each independently represent a hydrogen atom, an alkyl group, an alkoxy group, an aryl group, an aryloxy group, a monovalent heterocyclic group or a halogen atom, The group may have a substituent.
- a D1 ——— A D2 — represents an anionic bidentate ligand, and A D1 and A D2 each independently represent a carbon atom, an oxygen atom or a nitrogen atom bonded to an iridium atom.
- n D1 represents 1, 2 or 3
- n D2 represents 1 or 2.
- At least one of R D1 to R D8 is preferably a group represented by the formula (Dend-A).
- m DA1 , m DA2 and m DA3 each independently represent an integer of 0 or more.
- G DA1 represents a nitrogen atom, an aromatic hydrocarbon group or a heterocyclic group, and these groups optionally 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 DA2 and T DA3 each independently represent an aryl group or a monovalent heterocyclic group, and these groups optionally have a substituent.
- m DA1 , m DA2 and m DA3 are usually 10 or less. m DA1 , m DA2 and m DA3 are preferably the same.
- G DA1 is preferably a group represented by formulas (GDA-11) to (GDA-15), and these groups may have a substituent.
- R DA represents a hydrogen atom, an alkyl group, an alkoxy 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 or an alkoxy group, more preferably a hydrogen atom or an alkyl group, and these groups optionally have a substituent.
- Ar DA1 , Ar DA2 and Ar DA3 are preferably groups represented by the formulas (ArDA-1) to (ArDA-3).
- R DA represents the same meaning as described above.
- R DB represents a hydrogen atom, an alkyl 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.
- T DA2 and T DA3 are preferably groups represented by the formulas (TDA-1) to (TDA-3).
- R DA and R DB represent the same meaning as described above.
- R D11 to R D20 is a group represented by the formula (Dend-A).
- R D1 to R D8 and R D11 to R D20 is a group represented by formula (Dend-A).
- the group represented by the formula (Dend-A) is preferably a group represented by the formulas (Dend-A1) to (Dend-A3).
- R p1 , R p2 and R p3 each independently represents an alkyl group, an alkoxy group or a halogen atom. When a plurality of R p1 and R p2 are present, they may be the same or different. np1 represents an integer of 0 to 5, np2 represents an integer of 0 to 3, and np3 represents 0 or 1. A plurality of np1 may be the same or different.
- Np1 is preferably 0 or 1, more preferably 1.
- np2 is preferably 0 or 1, more preferably 0.
- np3 is preferably 0.
- Examples of the anionic bidentate ligand represented by —A D1 ——A D2 — include a ligand represented by the following formula.
- * represents a site that binds to Ir.
- the metal complex represented by the formula Ir-1 is preferably a metal complex represented by the formulas Ir-11 to Ir-13.
- the metal complex represented by the formula Ir-2 is preferably a metal complex represented by the formula Ir-21.
- the metal complex represented by the formula Ir-3 is preferably a metal complex represented by the formula Ir-31 to Ir-33.
- Dend represents a group represented by the formula (Dend-A).
- n D2 represents 1 or 2.
- triplet light-emitting complex examples include the metal complexes shown below.
- the content of the light emitting material is usually 0.1 to 400 parts by weight with respect to 100 parts by weight of the polymer compound.
- the antioxidant may be any compound that is soluble in the same solvent as the polymer compound and does not inhibit light emission and charge transport. Examples thereof include phenol-based antioxidants and phosphorus-based antioxidants.
- the blending amount of the antioxidant is usually 0.001 to 10 parts by weight with respect to 100 parts by weight of the polymer compound.
- Antioxidants may be used alone or in combination of two or more.
- the membrane contains a polymer compound.
- the film includes an insolubilized film in which a polymer compound is insolubilized in a solvent by crosslinking.
- the insolubilized film is a film obtained by crosslinking a polymer compound by an external stimulus such as heating or light irradiation. Since the insolubilized film is substantially insoluble in a solvent, the insolubilized film can be suitably used for stacking light emitting elements.
- the heating temperature for crosslinking the film is usually 25 to 300 ° C., and the light emission efficiency is improved. Therefore, the heating temperature is preferably 50 to 250 ° C., more preferably 150 to 200 ° C.
- the type of light used for light irradiation for crosslinking the film is, for example, ultraviolet light, near ultraviolet light, or visible light.
- the film is suitable as a hole transport layer or a hole injection layer in the light emitting element.
- the film is made of ink, for example, spin coating method, casting method, micro gravure coating method, gravure coating method, bar coating method, roll coating method, wire bar coating method, dip coating method, spray coating method, screen printing method. , Flexographic printing, offset printing, ink jet printing, capillary coating, and nozzle coating.
- the thickness of the film is usually 1 nm to 10 ⁇ m.
- the light-emitting element is a light-emitting element such as organic electroluminescence obtained by using a polymer compound, and the light-emitting element includes, for example, a light-emitting element containing a polymer compound, a polymer compound is intramolecular, intermolecular, or There are light-emitting elements that are cross-linked with both.
- the structure of the light-emitting element includes, for example, an electrode composed of an anode and a cathode, and a layer obtained using a polymer compound provided between the electrodes.
- the layer obtained using the polymer compound is usually one or more of a light emitting layer, a hole transport layer, a hole injection layer, an electron transport layer, and an electron injection layer, and is preferably a light emitting layer.
- Each of these layers includes a light emitting material, a hole transport material, a hole injection material, an electron transport material, and an electron injection material.
- Each of these layers is the same as the above-described film production, in which a light-emitting material, a hole transport material, a hole injection material, an electron transport material, and an electron injection material are dissolved in the above-described solvent and ink is prepared and used. It can be formed using a method.
- the light emitting element has a light emitting layer between the anode and the cathode.
- the light-emitting element preferably has at least one of a hole injection layer and a hole transport layer between the anode and the light-emitting layer from the viewpoint of hole injection and hole transport. From the viewpoint of electron transport properties, it is preferable to have at least one of an electron injection layer and an electron transport layer between the cathode and the light emitting layer.
- the above-described hole transport material, electron transport material, light emitting material, hole injection layer, and electron injection layer in addition to the polymer compound, the above-described hole transport material, electron transport material, light emitting material, positive Examples thereof include a hole injection material and an electron injection material.
- the material of the hole transport layer, the material of the electron transport layer, and the material of the light emitting layer are used when forming the hole transport layer, the electron transport layer, and the layer adjacent to the light emitting layer, respectively, in the production of the light emitting device.
- the material When dissolved in a solvent, it is preferable that the material has a crosslinking group in order to avoid dissolution of the material in the solvent. After forming each layer using a material having a crosslinking group, the layer can be insolubilized by crosslinking the crosslinking group.
- each layer such as a light emitting layer, a hole transport layer, an electron transport layer, a hole injection layer, and an electron injection layer
- a low molecular weight compound for example, vacuum deposition from powder
- solution or the method by the film-forming from a molten state is mentioned, for example.
- a high molecular compound the method by the film-forming from a solution or a molten state is mentioned, for example.
- the order, number, and thickness of the layers to be stacked may be adjusted in consideration of light emission efficiency and element lifetime.
- 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 preferably 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 these alloys; 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.
- the anode and the cathode may each have a laminated structure of two or more layers.
- 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 also be used as a curved light source and a display device.
- F8BE synthesized using high performance liquid chromatography and organic solvent size exclusion chromatography was analyzed.
- the analysis conditions are as follows.
- the content of F8BE according to the high performance liquid chromatogram was 99.8%, and the impurity content with a retention time shorter than the retention time of F8BE in the organic solvent size exclusion chromatogram was 0.16%.
- a 3 L separable flask equipped with a thermometer, a stirring blade and a cooling tube was charged with 1100 g of the concentrate and acetonitrile, and the temperature was raised to 50 ° C. and it was confirmed that the crystals were dissolved, and then cooled to 20 ° C. over 3 hours. . Crystals purified after being kept at 20 ° C. for 1 hour were filtered, washed with acetonitrile, and then dried in a vacuum dryer at 50 ° C. to obtain 160 g of high-purity F8BE.
- the content of F8BE according to the high performance liquid chromatogram was 100%, and the impurity content with a retention time shorter than the retention time of F8BE was 0.09% in the organic solvent size exclusion chromatograph chromatogram.
- Example 1 0.05 g of high-purity F8BE obtained in Example 1 was added as a seed crystal and kept at 40 ° C. for 1 hour. The solution was cooled to 0 ° C. at a cooling rate of 10 ° C./hr, and kept at 0 ° C. for 1 hour. The precipitated crystals were filtered, washed with 100 g of hexane cooled to 5 ° C., and then dried with a vacuum dryer at 50 ° C. to obtain 180 g of high purity F8BE.
- the content of F8BE according to the high performance liquid chromatogram was 99.9%, and the impurity content with a retention time shorter than the retention time of F8BE in the organic solvent size exclusion chromatogram was 0.06%.
- the content of F6BE according to the high performance liquid chromatogram was 99.9%, and the impurity content with a retention time shorter than the retention time of F6BE in the organic solvent size exclusion chromatogram was 0.23%.
- the content of F6BE in the high performance liquid chromatogram was 99.9%, and the impurity content in the retention time shorter than the retention time of F6BE in the organic solvent size exclusion chromatogram was 0.04%.
- Example 4 In a separable flask equipped with a stirring blade, baffle, condenser, and thermometer, 3.30 g of F8BE obtained in Example 1, 2.68 g of 2,7-dibromo-2,1,3-benzothiadiazole, 4,7- Bis (5-bromo-2-thienyl) -2,1,3-benzothiadiazole 0.56 g, tricaprylmethylammonium chloride (Aliquat 336) 1.1 g and toluene 48.6 g were charged and heated to 90 ° C. with stirring.
- Aliquat 336 tricaprylmethylammonium chloride
- reaction solution was transferred to a separable flask with a bottomed cock, diluted with toluene and allowed to stand, and the aqueous layer was removed.
- the toluene solution was washed with a 3% aqueous acetic acid solution and ion-exchanged water, and 2.3 g of sodium N, N-diethyldithiocarbamate trihydrate was added and stirred for 5 hours.
- a toluene solution was passed through a column premixed with 142 g of silica gel and 142 g of activated alumina, and then dropped into 1600 g of methanol.
- the generated red precipitate was filtered, washed with methanol, and dried under reduced pressure to obtain 10 g of a red polymer.
- the polystyrene-reduced weight average molecular weight of the obtained red polymer by an organic solvent-based size exclusion chromatography analysis method was 469,000.
- Example 4 F8BE obtained in Synthesis Example 1 was used instead of F8BE obtained in Example 1, and F6BE obtained in Synthesis Example 2 was used instead of F6BE obtained in Example 3.
- the obtained red polymer had a weight-average molecular weight in terms of polystyrene of 511,000 as determined by organic solvent-based size exclusion chromatography.
- the subsequent operations were performed in the same manner as in Example 4.
- the obtained polymer had a weight-average molecular weight in terms of polystyrene of 289,000 as determined by organic solvent-based size exclusion chromatography.
- Example 5 A suspension of poly (3,4) ethylenedioxythiophene / polystyrene sulfonic acid (manufactured by Bayer) is applied to a glass substrate with an ITO film having a thickness of 150 nm by a sputtering method to a thickness of about 65 nm by spin coating. And then dried on a hot plate at 200 ° C. for 15 minutes. Next, the polymer obtained in Synthesis Example 3 was dissolved in mixed xylene at a concentration of 0.5% by weight. After the film was formed to about 10 nm by spin coating using the obtained xylene solution, the oxygen concentration, And dried at 180 ° C.
- Example 4 the polymer obtained in Example 4 was dissolved in mixed xylene at a concentration of 1.6% by weight, and a film was formed to about 100 nm by spin coating using the obtained xylene solution. And it dried at 130 degreeC for 30 minutes in nitrogen atmosphere whose oxygen concentration and water concentration are 10 ppm or less (weight basis). After reducing the pressure to 1.0 ⁇ 10 ⁇ 4 Pa or less, barium was vapor-deposited at about 5 nm and aluminum was then vapor-deposited at about 80 nm as a cathode. After vapor deposition, a polymer light emitting device was produced by sealing using a glass substrate.
- the element configuration is as follows.
- ITO / BaytronP (about 65 nm) / polymer of synthesis example 3 (10 nm) / polymer of example 4 (about 100 nm) / Ba / Al
- ⁇ Comparative example 2> A suspension of poly (3,4) ethylenedioxythiophene / polystyrene sulfonic acid (manufactured by Bayer) is applied to a glass substrate with an ITO film having a thickness of 150 nm by a sputtering method to a thickness of about 65 nm by spin coating. And then dried on a hot plate at 200 ° C. for 15 minutes. Next, the polymer obtained in Synthesis Example 3 was dissolved in mixed xylene at a concentration of 0.5% by weight. After the film was formed to about 10 nm by spin coating using the obtained xylene solution, the oxygen concentration, And dried at 180 ° C.
- ITO / BaytronP (about 65 nm) / polymer of synthesis example 3 (10 nm) / polymer of comparison example 1 (about 100 nm) / Ba / Al
- Example 5 The comparison of the elements obtained in Example 5 and Comparative Example 2 is summarized as follows.
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Abstract
Description
-BF3Q’(式中、Q’は、Li、Na、K、Rb又はCsを示す。)で表される基;
-MgY’(式中、Y’は、塩素原子、臭素原子又はヨウ素原子を示す。)で表される基;
-ZnY”(式中、Y”は、塩素原子、臭素原子又はヨウ素原子を示す。)で表される基;及び
-Sn(RC3)3(式中、RC3は、水素原子、アルキル基又はアリール基を示し、これらの基は置換基を有していてもよい。複数存在するRC3は同一でも異なっていてもよく、互いに連結して、それぞれが結合するスズ原子とともに環構造を形成していてもよい。)で表される基である。
以下、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。
Meはメチル基、Etはエチル基、i-Prはイソプロピル基、n-Buはn-ブチル基、t-Buはtert-ブチル基を表す。
「アルコキシ基」は、直鎖、分岐及び環状のいずれでもよい。直鎖のアルコキシ基の炭素原子数は、置換基の炭素原子数を含まないで、通常1~40であり、好ましくは4~10である。分岐及び環状のアルコキシ基の炭素原子数は、置換基の炭素原子数を含まないで、通常3~40であり、好ましくは4~10である。
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、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。
高分子化合物は、正孔輸送性が優れるので、下記式(X)で表される構成単位を含むことが好ましい。
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。
本明細書でいう原料とは有機EL材料を合成する原料になる化合物をいう。高分子量不純物とは原料である化合物の分子量よりも大きい分子量を有する不純物をいう。高分子量不純物は原料由来の芳香族環が無作為に連結した化学構造を有しており、有機EL材料中に存在することになった場合、有機EL素子中の各層における電荷輸送性のバランスを崩し、有機EL素子としたときの性能を低下させる。有機EL素子の性能を向上させるためには、高分子量不純物は原料から除去する必要がある。
次に、本発明の高分子化合物の製造方法について説明する。
本明細書において、本発明の高分子化合物の製造に使用される化合物を総称して、「原料モノマー」ということがある。
化合物(1) 又は(2)は、高分子化合物の製造においては、いずれも原料モノマーであり、Z1、Z2はそれぞれ独立に、置換基A群及び置換基B群からなる群から選ばれる基を示す。]
塩素原子、臭素原子、ヨウ素原子、-O-S(=O)2RC1(式中、RC1は、アルキル基又はアリール基を示し、これらの基は置換基を有していてもよい。)で表される基。
-B(ORC2)2(式中、RC2は、水素原子、アルキル基又はアリール基を示し、これらの基は置換基を有していてもよい。複数存在するRC2は同一でも異なっていてもよく、互いに連結して、それぞれが結合する酸素原子とともに環構造を形成していてもよい。)で表される基;
-MgY’(式中、Y’は、塩素原子、臭素原子又はヨウ素原子を示す。)で表される基;
組成物は、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、酸化防止剤及び溶媒からなる群から選ばれる少なくとも1種の材料と、高分子化合物とを含有する。
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、高分子化合物が好ましく、架橋基を有する高分子化合物がより好ましい。
電子輸送材料は、低分子化合物と高分子化合物とに分類される。電子輸送材料は、架橋基を有していてもよい。
正孔注入材料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。
本発明の原料化合物を使用した縮合反応により得られる高分子化合物は発光材料として用いることが出来る。該高分子化合物以外の発行材料を併用してもよい。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。
酸化防止剤は、高分子化合物と同じ溶媒に可溶であり、発光及び電荷輸送を阻害しない化合物であればよく、例えば、フェノール系酸化防止剤、リン系酸化防止剤が挙げられる。
膜は、高分子化合物を含有する。
発光素子は、高分子化合物を用いて得られる有機エレクトロルミネッセンス等の発光素子であり、該発光素子には、例えば、高分子化合物を含む発光素子、高分子化合物が分子内、分子間、又は、それらの両方で架橋した発光素子がある。
高分子化合物を用いて得られる層は、通常、発光層、正孔輸送層、正孔注入層、電子輸送層、電子注入層の1種以上の層であり、好ましくは、発光層である。これらの層は、各々、発光材料、正孔輸送材料、正孔注入材料、電子輸送材料、電子注入材料を含む。これらの層は、各々、発光材料、正孔輸送材料、正孔注入材料、電子輸送材料、電子注入材料を、上述した溶媒に溶解させ、インクを調製して用い、上述した膜の作製と同じ方法を用いて形成することができる。
発光素子における基板は、電極を形成することができ、かつ、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。不透明な基板の場合には、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。
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、陽極もしくは陰極、又は両方の電極をパターン状に形成する方法がある。これらのいずれかの方法でパターンを形成し、いくつかの電極を独立にON/OFFできるように配置することにより、数字、文字等を表示できるセグメントタイプの表示装置が得られる。ドットマトリックス表示装置とするためには、陽極と陰極を共にストライプ状に形成して直交するように配置すればよい。複数の種類の発光色の異なる高分子化合物を塗り分ける方法、カラーフィルター又は蛍光変換フィルターを用いる方法により、部分カラー表示、マルチカラー表示が可能となる。ドットマトリックス表示装置は、パッシブ駆動も可能であるし、TFT等と組み合わせてアクティブ駆動も可能である。これらの表示装置は、コンピュータ、テレビ、携帯端末等のディスプレイに用いることができる。面状の発光素子は、液晶表示装置のバックライト用の面状光源、又は、面状の照明用光源として好適に用いることができる。フレキシブルな基板を用いれば、曲面状の光源、及び、表示装置としても使用できる。
2,7-ビス(1,3,2-ジオキサボロラン-2-イル)-9,9-ジオクチルフルオレン(以下F8BEと略す)は特表2002-536492の実施例に従い合成した。
機器:島津製作所LC-10AT (LC-Solution データ処理)
カラム:Zorbax XDB-C8(Agilent製)
移動相:水:アセトニトリル(20:80)一定、1.0mL/分
検出器: UV-Vis(280nm)
機器:島津製作所LC-10AT (LC-Solution データ処理)
カラム:TSKgel G2000HHR(東ソー製)
移動相:THF 1.0mL/分
検出器: VU-Vis 228nm
高純度F8BE
温度計、攪拌翼、冷却管をつけた1Lセパラブルフラスコに合成例1で得られたF8BE200g、ジクロロメタン800gを仕込み、40℃で溶解した。この溶液に活性炭(関東化学、粉末)20gを加え、還流下2時間攪拌した。30℃まで冷却した後、セライト545(関東化学)をプレコートした濾過器で活性炭を濾過し、ジクロロメタン50gで洗浄した。濾液をロータリーエバポレータで400gまで濃縮した。温度計、攪拌翼、冷却管をつけた3Lセパラブルフラスコに濃縮物及びアセトニトリル1100gを仕込み、50℃まで昇温して結晶が溶解したことを確認した後、20℃まで3時間かけて冷却した。20℃で1時間保温した後精製した結晶を濾過、アセトニトリルで洗浄した後、50℃の真空乾燥機で乾燥して高純度F8BE160gを得た。
高純度F8BE
温度計、3枚後退攪拌翼、フィンガーバッフル、冷却管をつけた1Lジャケット付セパラブルフラスコに合成例1で得られたF8BE200g、ヘキサン750gを仕込んだ。プログラム温度調節器を備えた温水循環装置を用いてセパラブルフラスコのジャケットに温水を循環させた。ジャケット温度を60℃に設定して昇温し、結晶が溶解したことを確認した後、攪拌回転数を500rpmとして、10℃/hrの冷却速度で40℃まで冷却した。実施例1で得られた高純度F8BE0.05gを種晶として加え、40℃で1時間保温した。10℃/hrの冷却速度で0℃まで冷却し、0℃で1時間保温した。析出した結晶を濾過、5℃に冷却したヘキサン100gで洗浄した後、50℃の真空乾燥機で乾燥して、高純度F8BE180gを得た。
2,7-ビス(1,3,2-ジオキサボロラン-2-イル)-9,9-ジヘキシルフルオレン(以下F6BEと略す)は特表2002-536492の実施例に従い合成した。
高純度F6BE
温度計、3枚後退攪拌翼、フィンガーバッフル、冷却管をつけた1Lジャケット付セパラブルフラスコに合成例2で得られたF6BE300g、トルエン450gを仕込んだ。プログラム温度調節器を備えた温水循環装置を用いてセパラブルフラスコのジャケットに温水を循環させた。ジャケット温度を80℃に設定して昇温し、結晶が溶解したことを確認した後、攪拌回転数を450rpmとして、10℃/hrの冷却速度で60℃まで冷却した。合成例2で得られたF6BE0.15gを種晶として加え、60℃で1時間保温した。10℃/hrの冷却速度で0℃まで冷却し、0℃で1時間保温した。析出した結晶を濾過、5℃に冷却したトルエン30g及びヘキサン150gで洗浄した後、50℃の真空乾燥機で乾燥して、高純度F6BE240gを得た。
攪拌翼、バッフル、冷却管、温度計をつけたセパラブルフラスコに実施例1で得られたF8BE3.30g、2,7-ジブロモ-2,1,3-ベンゾチアジアゾール1.68g、4,7-ビス(5-ブロモ-2-チエニル)-2,1,3-ベンゾチアジアゾール0.56g、トリカプリルメチルアンモニウムクロリド(Aliquat336)1.1g、トルエン48.6gを仕込み攪拌下90℃まで昇温した。ビストリフェニルホスフィンパラジウム(II)ジクロリド0.005gを仕込み、17.5%炭酸ナトリウム水溶液13gを滴下した。滴下終了後還流下3時間保温した後、室温まで冷却した。
実施例4において、実施例1で得られたF8BEの代わりに合成例1で得られたF8BEを用い、実施例3で得られたF6BEの代わりに合成例2で得られたF6BEを用いた以外は、実施例4と同様に実施し、重合体10gを得た。
得られた赤色重合体の有機溶媒系サイズ排除クロマトグラフ分析法によるポリスチレン換算重量平均分子量は511,000であった。
攪拌翼、バッフル、冷却管、温度計をつけたセパラブルフラスコに合成例1で得られたF8BE10.49g、ビス-(4-ブロモフェニル)-4-(1-メチルプロピル)-ベンゼンアミン9.07gを仕込み、トリカプリルメチルアンモニウムクロリド(Aliquat336)1.8g、トルエン120gを仕込み、攪拌下90℃まで加熱した。酢酸パラジウム(II)0.0044g、トリ(o-トルイル)ホスフィン0.030gを加えた後、17.5%炭酸ナトリウム水溶液36.3gを1時間かけて滴下した。滴下終了後還流下3時間保温した後フェニルホウ酸0.28gを加え、14時間還流下保温した後、室温まで冷却した。
スパッタ法により150nmの厚みでITO膜をつけたガラス基板に、ポリ(3,4)エチレンジオキシチオフェン/ポリスチレンスルフォン酸(Bayer製)の懸濁液をスピンコート法により、約65nmの厚みと成るように製膜し、ホットプレート上で200℃、15分間乾燥した。次に、合成例3で得られた重合体を混合キシレンに0.5重量%の濃度で溶解させ、得られたキシレン溶液を用いてスピンコート法により約10nm程度に製膜後、酸素濃度、及び水分濃度が10ppm以下(重量基準)の窒素雰囲気下で、180℃、15分間乾燥した。次に、実施例4で得られた重合体を混合キシレンに1.6重量%の濃度で溶解させ、得られたキシレン溶液を用いてスピンコート法により約100nmに製膜した。そして、酸素濃度、及び水分濃度が10ppm以下(重量基準)の窒素雰囲気下で、130℃、30分間乾燥した。1.0×10-4Pa以下にまで減圧した後、陰極として、バリウムを約5nm、次いでアルミニウムを約80nm蒸着した。蒸着後、ガラス基板を用いて封止を行うことで、高分子発光素子を作製した。素子構成は次の通りである。
スパッタ法により150nmの厚みでITO膜をつけたガラス基板に、ポリ(3,4)エチレンジオキシチオフェン/ポリスチレンスルフォン酸(Bayer製)の懸濁液をスピンコート法により、約65nmの厚みと成るように製膜し、ホットプレート上で200℃、15分間乾燥した。次に、合成例3で得られた重合体を混合キシレンに0.5重量%の濃度で溶解させ、得られたキシレン溶液を用いてスピンコート法により約10nm程度に製膜後、酸素濃度、及び水分濃度が10ppm以下(重量基準)の窒素雰囲気下で、180℃、15分間乾燥した。次に、比較例1で得られた重合体を混合キシレンに1.6重量%の濃度で溶解させ、得られたキシレン溶液を用いてスピンコート法により約100nmに製膜した。そして、酸素濃度、及び水分濃度が10ppm以下(重量基準)の窒素雰囲気下で、130℃、30分間乾燥した。1.0×10-4Pa以下にまで減圧した後、陰極として、バリウムを約5nm、次いでアルミニウムを約80nm蒸着した。蒸着後、ガラス基板を用いて封止を行うことで、高分子発光素子を作製した。素子構成は次の通りである。
Claims (17)
- 以下の式(1)又は(2)で表される化合物であって、式(1)又は(2)で表される化合物の分子量よりも大きい分子量を有する不純物の含有量が0.15%以下であり、該不純物の含有量は有機溶媒系サイズ排除クロマトグラフ法によるクロマトグラムにおいて式(1)又は(2)と同定されるピークよりも保持時間の短いピークの面積の和の、全ピーク面積の和に対する百分率である化合物。
- 逆相カラムを使用する高速液体クロマトグラフィーによるクロマトグラムにおいて、面積百分率法による純度が99%を超えるものである請求項1の化合物。
- Z1、Z2で示される脱離基が、次の置換基A群、又はB群からなる群から選ばれる基である請求項1又は2に記載の化合物。
[ここで、置換基A群は、塩素原子、臭素原子、ヨウ素原子、及び-O-S(=O)2RC1(式中、RC1は、アルキル基又はアリール基を示し、これらの基は置換基を有していてもよい。)で表される基であり;
置換基B群は、-B(ORC2)2(式中、RC2は、水素原子、アルキル基又はアリール基を示し、これらの基は置換基を有していてもよい。複数存在するRC2は同一でも異なっていてもよく、互いに連結して、それぞれが結合する酸素原子とともに環構造を形成していてもよい。)で表される基;
-BF3Q’(式中、Q’は、Li、Na、K、Rb又はCsを示す。)で表される基;
-MgY’(式中、Y’は、塩素原子、臭素原子又はヨウ素原子を示す。)で表される基;
-ZnY”(式中、Y”は、塩素原子、臭素原子又はヨウ素原子を示す。)で表される基;及び
-Sn(RC3)3(式中、RC3は、水素原子、アルキル基又はアリール基を示し、これらの基は置換基を有していてもよい。複数存在するRC3は同一でも異なっていてもよく、互いに連結して、それぞれが結合するスズ原子とともに環構造を形成していてもよい。)で表される基である。] - Z1、Z2で示される脱離基が臭素原子、又は-B(ORC2)2(式中、RC2は、水素原子、アルキル基又はアリール基を示し、これらの基は置換基を有していてもよい。複数存在するRC2は同一でも異なっていてもよく、互いに連結して、それぞれが結合する酸素原子とともに環構造を形成していてもよい。)で表される基である請求項1~3のいずれか一項に記載の化合物。
- 縮合反応による化合物の合成に使用される請求項1~4のいずれか一項に記載の化合物。
- 合成される化合物が有機EL材料である請求項5に記載の化合物。
- 合成される化合物が高分子化合物である請求項5又は6に記載の化合物。
- 請求項1~4のいずれか一項に記載の式(1)で示される化合物、及び請求項1~4のいずれか一項に記載の式(2)で示される化合物を用いて縮合反応を行う工程を包含する化合物の製造方法。
- 製造される化合物が有機EL材料である請求項8又は9に記載の化合物の製造方法。
- 製造される化合物が高分子化合物である請求項8~10のいずれか一項に記載の化合物の製造方法。
- 式(1)又は(2)
で表される化合物を溶媒に溶解した後、活性炭に接触させることで、式(1)又は(2)で表される化合物の分子量よりも大きい分子量を有する不純物の含有量を0.15%以下に低減する工程を包含する、式(1)又は(2)で表される化合物の精製方法であって、該不純物の含有量は有機溶媒系サイズ排除クロマトグラフィーによるクロマトグラムにおいて式(1)又は(2)と同定されるピークよりも保持時間の短いピークの面積の和の、全ピーク面積の和に対する百分率である精製方法。 - 請求項1~4のいずれか一項に記載の式(1)で示される化合物、及び請求項1~4のいずれか一項に記載の式(2)で示される化合物を縮合重合させて成る重合体を含む有機EL材料。
- 請求項1~4のいずれか一項に記載の式(1)で示される化合物、請求項1~4のいずれか一項に記載の式(2)で示される化合物、及び上記式(3)で示される化合物を縮合重合させて成る重合体を含む有機EL材料。
- 請求項13又は14に記載の有機EL材料と有機溶媒を含む組成物。
- 請求項13又は14に記載の有機EL材料を含む薄膜。
- 請求項16に記載の薄膜を有する有機EL素子。
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