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WO2016186012A1 - Composition et élément électroluminescent utilisant une telle composition - Google Patents

Composition et élément électroluminescent utilisant une telle composition Download PDF

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Publication number
WO2016186012A1
WO2016186012A1 PCT/JP2016/064221 JP2016064221W WO2016186012A1 WO 2016186012 A1 WO2016186012 A1 WO 2016186012A1 JP 2016064221 W JP2016064221 W JP 2016064221W WO 2016186012 A1 WO2016186012 A1 WO 2016186012A1
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group
composition
weight
substituent
minutes
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Japanese (ja)
Inventor
正剛 岩▲崎▼
寛幸 齊藤
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Sumitomo Chemical Co Ltd
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Sumitomo Chemical Co Ltd
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    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/14—Carrier transporting layers
    • H10K50/15—Hole transporting layers

Definitions

  • the present invention relates to a composition and a light emitting device using the composition.
  • a light-emitting element such as an organic electroluminescence element has high luminous efficiency and low driving voltage, and thus can be suitably used for display and lighting applications.
  • a composition containing a soluble functional compound used for a light-emitting element and a solvent an organic functional layer can be formed using a discharge-type coating method typified by an ink jet printing method.
  • a composition containing a soluble polymer organic EL material, cyclohexylbenzene, and 4-methylanisole has been proposed (Patent Document 1).
  • an object of the present invention is to provide a composition having excellent flatness of a film obtained when used in a discharge-type coating method.
  • Another object of the present invention is to provide a light-emitting device obtained using the composition.
  • the present invention is as follows. [1] A composition comprising at least one hole transporting material and at least two solvents, in which 1 g of the composition is placed in a borosilicate glass container having an outer diameter of 50 mm and heated to 80 ° C. under 1 atm.
  • the weight loss curve of the composition over time (horizontal axis: heating time at 80 ° C. (min), vertical axis: composition weight retention (% by weight)) has at least one inflection point.
  • the slope of weight change per unit time from 0 minutes to 30 minutes (wt% / min) is smaller than -1 and the slope of weight change per unit time from 80 minutes to 120 minutes of heating time (wt% / min) (Composition) greater than -0.3 and less than 0.
  • FIG. 6 is a view showing the shape of a film produced in Example 2.
  • FIG. 6 is a view showing the shape of a film produced in Comparative Example 1.
  • FIG. 6 is a view showing the shape of a film produced in Comparative Example 1.
  • 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, isobutyl group, tert-butyl group, pentyl group, isoamyl group, 2-ethylbutyl group, Hexyl group, heptyl group, octyl group, 2-butyl group, 2-ethylhexyl group, 3-propylheptyl group, decyl group, 3,7-dimethyloctyl group, 2-ethyloctyl group, 2-hexyldecyl group, dodecyl group 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 penta
  • 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, pyridyl 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 to 30, preferably 3 to 20, not including the carbon atoms of the substituent.
  • the number of carbon atoms of the branched alkenyl group is usually 3 to 30, preferably 4 to 20, not including the carbon atoms of the substituent.
  • the number of carbon atoms in the “cycloalkenyl group” is usually 3 to 30, preferably 4 to 20, not including the 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, dibenzosilole, 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 generating a new bond by being subjected to heat treatment, ultraviolet irradiation treatment, near ultraviolet irradiation treatment, visible light irradiation treatment, infrared irradiation treatment, radical reaction, etc.
  • it is a group represented by any one of formulas (B-1)-(B-17). These groups may have a substituent.
  • “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 composition of the present invention is a composition containing at least one kind of hole transporting material and at least two kinds of solvents, and 1 g of the composition is placed in a borosilicate glass container having an outer diameter of 50 mm under 1 atm.
  • the weight loss curve of the composition over time has at least one inflection point, and the slope of weight change per unit time from 0 to 30 minutes is less than ⁇ 1, from 80 minutes.
  • the composition has a weight change gradient per unit time up to 120 minutes which is greater than ⁇ 0.3 and less than 0.
  • the composition of the present invention is a composition containing at least one hole transport material and at least two solvents, and 1 g of the composition is put in a borosilicate glass container having an outer diameter of 50 mm.
  • the weight loss curve of the composition over time horizontal axis: heating time at 80 ° C. (min), vertical axis: composition weight retention rate (% by weight)
  • the slope of weight change per unit time from 0 minutes to 30 minutes is less than -1
  • per unit time from 80 minutes to 120 minutes of heating time The composition has a weight change gradient (wt% / min) of more than ⁇ 0.3 and less than 0.
  • composition weight retention is when the weight of the composition before the start of heating is 100% by weight, It refers to the ratio indicating how many weight percent of the composition is retained (on the container) after heating at each time.
  • Composition weight retention ratio (% by weight) (weight of composition held on container after heating at each time / weight of composition before starting heating at 80 ° C.) ⁇ 100
  • the composition of the present invention is as described above, since the flatness of the film is excellent, when 1 g of the composition is placed in a borosilicate glass container having an outer diameter of 50 mm and heated to 80 ° C. under 1 atmosphere, the time The weight loss curve of the composition over time has 1 to 3 inflection points, the slope of weight change per unit time from 0 minutes to 30 minutes is -1 to -3, and from 80 minutes to 120 minutes
  • the composition is preferably a composition having an inclination of weight change per unit time of ⁇ 0.01 to ⁇ 0.3, and 1 g of the composition is placed in a borosilicate glass container having an outer diameter of 50 mm at 80 ° C. under 1 atm.
  • the weight loss curve of the composition over time has 1 to 2 inflection points, and the slope of the weight change per unit time from 0 to 30 minutes is ⁇ 1 to ⁇ 2, The slope of weight change per unit time from 80 minutes to 120 minutes- And more preferably .05 ⁇ -0.2 For a composition.
  • a borosilicate glass container having an outer diameter of 50 mm is an open container made of borosilicate glass having an outer diameter of 50 mm.
  • a petri dish is usually used as the borosilicate glass container.
  • the weight of the composition placed in the borosilicate glass container is 1 g, usually 1.0 g to 1.2 g.
  • the environment for heating the composition to 80 ° C. is usually 1 atm, temperature 23 to 26 ° C., humidity 40 to 60%.
  • the content of the hole transport material is usually 0.1 to 20 parts by weight when the total content of the hole transport material and the solvent is 100 parts by weight. Is preferably 0.2 to 10 parts by weight, more preferably 0.3 to 5 parts by weight, and still more preferably 0.5 to 3 parts by weight.
  • solvent contained in the composition of the present invention examples include hydrocarbon solvents, monohydric alcohol solvents, polyhydric alcohol solvents, ester solvents, ketone solvents, ether solvents, solvents containing nitrogen atoms, sulfur Examples thereof include solvents containing atoms, preferably hydrocarbon solvents, ester solvents, ketone solvents, and ether solvents, more preferably hydrocarbon solvents, ester solvents, and ether solvents. More preferred are hydrocarbon solvents and ether solvents, and particularly preferred are aromatic hydrocarbon solvents and aromatic ether solvents.
  • hydrocarbon solvent examples include aromatic hydrocarbon solvents. Decylbenzene is preferable, and n-decylbenzene (boiling point: 293 ° C.) is more preferable.
  • ether solvents include aromatic ether solvents, preferably methylanisole and phenoxytoluene, and more preferably 4-methylanisole (boiling point: 175 ° C.) and 3-phenoxytoluene (boiling point: 272 ° C.).
  • the boiling point of at least one kind of solvent is less than 200 ° C., and the boiling point of at least one kind of solvent is 250 ° C. The above is preferable.
  • Preferred solvent combinations include, for example, 3-phenoxytoluene and 4-methylanisole, 4-methylanisole, n-decylbenzene, and cyclohexylbenzene.
  • the content of the solvent having a boiling point of 250 ° C. or higher is preferably 10% by weight or more and 50% by weight or less.
  • the hole transport material contained in the composition of the present invention is classified into a low molecular compound and a high molecular compound.
  • the hole transport material is a low molecular compound, it is preferably a compound represented by the formula (H-1).
  • Ar H1 and Ar H2 each independently represent an aryl group or a monovalent heterocyclic group, and these groups optionally have a substituent.
  • n H1 and n H2 each independently represent 0 or 1. When a plurality of n H1 are present, they may be the same or different. A plurality of n H2 may be the same or different.
  • n H3 represents an integer of 0 or more and 10 or less.
  • L H1 represents an arylene group, a divalent heterocyclic group, or a group represented by — [C (R H11 ) 2 ] n H11 —, and these groups optionally have a substituent. When a plurality of L H1 are present, they may be the same or different.
  • n H11 represents an integer of 1 or more and 10 or less.
  • R H11 represents a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, or a monovalent heterocyclic group, and these groups may have a substituent.
  • a plurality of R H11 may be the same or different, and may be bonded to each other to form a ring together with the carbon atom to which each is bonded.
  • L H2 represents a group represented by —N (—L H21 —R H21 ) —. When a plurality of L H2 are present, they may be the same or different.
  • L H21 represents a single bond, an arylene group or a divalent heterocyclic group, and these groups may have a substituent.
  • R H21 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.
  • the polymer includes at least one structural unit selected from the group consisting of the structural unit represented by the formula (X) and the structural unit represented by the formula (Y). It is preferably a compound (hereinafter also referred to as “polymer compound XY”), and a polymer compound containing a structural unit represented by formula (X), or a structural unit and formula represented by formula (X)
  • a polymer compound containing the structural unit represented by (Y) hereinafter, the polymer compound containing the structural unit represented by formula (X) is generically referred to as “aromatic amine polymer compound”). It is more preferable that
  • 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, since the light emitting device obtained using the composition of the present invention has excellent luminous efficiency.
  • a X2 is preferably an integer of 2 or less, and more preferably 0, because the light emitting device obtained using the composition of the present invention has excellent light emission efficiency.
  • R X1 , R X2 and R X3 are preferably an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, and these groups optionally have a substituent.
  • 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 these groups may have a substituent. .
  • the divalent heterocyclic group represented by Ar X1 and Ar X3 is more preferably represented by the formula (AA-1), the formula (AA-2), or the formula (AA-7)-(AA-26). These groups may have a substituent.
  • Ar X1 and Ar X3 are preferably an arylene group which 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 .
  • More preferable range of the arylene group and the divalent heterocyclic group in the divalent group in which at least one kind of arylene group represented by Ar X2 and Ar X4 and at least one kind of divalent heterocyclic group are directly bonded. are the same as the preferred ranges of the arylene group and divalent heterocyclic group represented by Ar X1 and Ar X3 , respectively.
  • Examples of the divalent group in which at least one arylene group represented by Ar X2 and Ar X4 and at least one divalent heterocyclic group are directly bonded include groups represented by the following formulae. These may have a substituent.
  • R XX represents a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, and these groups 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)-(X-7).
  • 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) is excellent in the hole transportability of the light-emitting device obtained using the composition of the present invention, and therefore, with respect to the total amount of the structural units contained in the polymer compound XY, The amount is preferably 0.1 to 50 mol%, 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)-(X1-11).
  • the structural unit represented by the formula (X) may be included in the polymer compound XY only in one kind or in two or more kinds.
  • 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 more preferably a formula (A-1), a formula (A-2), a formula (A-6)-(A-10), a formula (A-19) or a formula (A A-20), and these groups may have a substituent.
  • the divalent heterocyclic group represented by Ar Y1 is more preferably a formula (AA-1)-(AA-4), a formula (AA-10)-(AA-15), a formula (AA-18) -(AA-21), a group represented by formula (AA-33) or formula (AA-34), and these groups may have a substituent.
  • More preferable ranges 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 to each other are as follows: These are the same as the more 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 formulas (Y-1)-(Y-10), and the light emitting device obtained by using the composition of the present invention. From the viewpoint of luminous efficiency, it is preferably a structural unit represented by the formula (Y-1)-(Y-3), from the viewpoint of electron transport properties of a light-emitting device obtained using the composition of the present invention. Preferably, it is a structural unit represented by the formula (Y-4)-(Y-7), and from the viewpoint of hole transportability of the light-emitting device obtained by using the composition of the present invention, preferably the formula (Y Y-8) is a structural unit represented by (Y-10). Further, as the structural unit represented by the formula (Y), since the luminance life of the light-emitting element obtained using the composition of the present invention is excellent, preferably the formula (Y-1)-(Y-4) It is a structural unit that is represented.
  • 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, and these groups optionally have a substituent.
  • the combination of two R Y2 in the group represented by —C (R Y2 ) 2 — is preferably an alkyl group or a cycloalkyl group, both are aryl groups, and both are monovalent complex A cyclic group, or one is an alkyl group or a cycloalkyl group and the other is an aryl group or a monovalent heterocyclic group, and these groups may have a substituent.
  • Two R Y2 s may be bonded to each other to form a ring together with the atoms to which they are bonded.
  • the group represented by —C (R Y2 ) 2 — Is preferably a group represented by the formula (Y-A1)-(Y-A5), and these groups may have a substituent.
  • 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 may 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)-(Y-B5), and these groups may have a substituent.
  • R Y2 represents the same meaning as described above.
  • the structural unit represented by the formula (Y-2) is preferably a structural unit represented by the formula (Y-2 ′).
  • the structural unit represented by the formula (Y-3) is preferably a structural unit represented by the formula (Y-3 ′).
  • 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, and these groups may have a substituent.
  • the structural unit represented by the formula (Y-4) is preferably a structural unit represented by the formula (Y-4 ′), and the structural unit represented by the formula (Y-6) is represented by the formula (Y -6 ′) is preferred.
  • R Y1 represents the same meaning as described above.
  • R Y4 represents a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, or a monovalent heterocyclic group, and these groups optionally have a substituent.
  • R Y4 is preferably an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, or a monovalent heterocyclic group, and these groups optionally have a substituent.
  • a structural unit represented by the formula (Y) for example, a structural unit comprising an arylene group represented by the formula (Y-101)-(Y-121), a formula (Y-201)-(Y-206)
  • the structural unit represented by the formula (Y), in which Ar Y1 is an arylene group, is included in the polymer compound XY because the light-emitting element obtained using the composition of the present invention has excellent luminous efficiency.
  • the amount is preferably 0.5 to 90 mol%, more preferably 30 to 80 mol%, based on the total amount of the structural units.
  • % More preferably 3 to 30 mol%.
  • the structural unit represented by the formula (Y) may be included in the polymer compound XY only in one kind, or in two or more kinds.
  • Examples of the polymer compound XY include polymer compounds (P-101) to (P-107) shown in Table 1.
  • p, q, r, s and t represent the molar ratio of each constituent unit.
  • p + q + r + s + t 100 and 100 ⁇ p + q + r + s ⁇ 70.
  • the other structural unit means a structural unit that is neither the structural unit represented by the formula (Y) nor the structural unit represented by the formula (X). ]
  • the polymer compound XY preferably has a polystyrene equivalent weight average molecular weight of 5 ⁇ 10 3 to 1 ⁇ 10 6 and a polystyrene equivalent number average molecular weight of 5 ⁇ 10 3 to 1 ⁇ 10 6 .
  • the polymer compound XY when the polymer compound XY is a copolymer, the polymer compound XY may be any of a block copolymer, a random copolymer, an alternating copolymer, and a graft copolymer. A copolymer obtained by copolymerizing a plurality of types of raw material monomers is preferable.
  • the polymer compound XY can be synthesized, for example, according to the description in WO11 / 078387.
  • composition of the present invention may further contain at least one material selected from the group consisting of a hole injection material, an electron transport material, an electron injection material, a light emitting material, and an antioxidant.
  • 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, for example, metal complexes having 8-hydroxyquinoline as a ligand, oxadiazole, anthraquinodimethane, benzoquinone, naphthoquinone, anthraquinone, tetracyanoanthraquinodimethane, fluorenone, diphenyldicyanoethylene and diphenoquinone. As well as these derivatives.
  • polymer compound examples include polyphenylene, polyfluorene, and derivatives thereof.
  • the polymer compound may be doped with a metal.
  • the content of the electron transport material is usually 1 to 100 parts by weight, preferably 5 to 100 parts by weight with respect to 100 parts by weight of the hole transport material.
  • the electron transport material may be used alone or in combination of two or more.
  • the hole injection material and the electron injection material are classified into a low molecular compound and a high molecular compound, respectively.
  • the hole injection material and the electron injection material may have a crosslinking group.
  • low molecular weight compounds include metal phthalocyanines such as copper phthalocyanine; carbon; metal oxides such as molybdenum and tungsten; and metal fluorides such as lithium fluoride, sodium fluoride, cesium fluoride, and potassium fluoride.
  • metal phthalocyanines such as copper phthalocyanine
  • carbon such as carbon
  • metal oxides such as molybdenum and tungsten
  • metal fluorides such as lithium fluoride, sodium fluoride, cesium fluoride, and potassium fluoride.
  • polymer compound examples include polyaniline, polythiophene, polypyrrole, polyphenylene vinylene, polythienylene vinylene, polyquinoline and polyquinoxaline, and derivatives thereof; conductive polymers such as polymers containing an aromatic amine structure in the main chain or side chain. A functional polymer.
  • the content of the hole injection material and the electron injection material is usually 1 to 100 parts by weight, preferably 5 to 100 parts by weight, with respect to 100 parts by weight of the hole transport material. It is.
  • Each of 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 ions to be doped may be used alone or in combination of two or more.
  • Luminescent materials are classified into low molecular compounds and high molecular compounds.
  • the light emitting material may have a crosslinking group.
  • Examples of the low molecular weight compound include naphthalene and derivatives thereof, anthracene and derivatives thereof, and perylene and derivatives thereof.
  • 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 content of the light emitting material is usually 0.1 to 100 parts by weight with respect to 100 parts by weight of the hole transport material.
  • the antioxidant may be any compound that is soluble in a solvent 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 10 ⁇ 6 to 10 1 parts by weight when the composition is 100 parts by weight.
  • Antioxidants may be used alone or in combination of two or more.
  • the light emitting device of the present invention has an anode, a cathode, a light emitting layer provided between the anode and the cathode, and a layer obtained using the composition of the present invention provided between the anode and the cathode.
  • the layer obtained by using the composition of the present invention is usually a hole transport layer.
  • the light emitting device of the present invention 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 injection property and electron transport property, 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.
  • hole transport layer As the material of the hole transport layer, electron transport layer, light emitting layer, hole injection layer and electron injection layer, the above-described hole transport material, electron transport material, light emitting material, hole injection material and electron injection material, respectively, etc. Is mentioned.
  • the solvent In order to avoid dissolution of the material, it is preferable that the material has a crosslinking group. After forming each layer using a material having a crosslinking group, the layer can be insolubilized by crosslinking the crosslinking group.
  • Crosslinking can be performed by heating, light irradiation, or the like.
  • the heating temperature for crosslinking is usually 25 to 300 ° C.
  • Types of light used for light irradiation for crosslinking are, for example, ultraviolet light, near ultraviolet light, and visible light.
  • 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 compound for example, vacuum deposition from powder
  • a method using film formation from a solution or a molten state may be used.
  • Each layer of the light emitting device of the present invention is formed using the composition of the present invention, 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. It can be produced by a coating method, a spray coating method, a screen printing method, a flexographic printing method, an offset printing method, an ink jet printing method, a capillary coating method, or a nozzle coating method.
  • the order, number and thickness of the layers to be laminated are adjusted in consideration of luminous efficiency and luminance life.
  • 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.
  • 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.
  • Each of the anode and the cathode may 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 active in combination with a TFT or the like.
  • 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 weight of the composition was measured with an analytical electronic balance (manufactured by ASONE, model number: GR202).
  • Example 1 1.0 part by weight of an aromatic amine polymer (hole transport material), 49.5 parts by weight of 3-phenoxytoluene (boiling point: 272 ° C.), and 4-methylanisole (boiling point: 175 ° C.) 49.
  • Composition 1 was prepared by mixing 5 parts by weight and stirring.
  • the weight change of the composition with the passage of heating time was measured by the following procedure.
  • (I) 1.0295 g of the composition 1 was put in a petri dish (model number: 3160065) made of ASONE having an outer diameter of 50 mm ⁇ . The weight of Composition 1 at this time was 100%.
  • the petri dish had an inner diameter of 47 mm ⁇ , a height of 17 mm, and a depth of 15.5 mm.
  • a weight reduction curve (horizontal axis: heating time (minutes), vertical axis: weight retention (% by weight)) of the composition with the passage of heating time was prepared.
  • the weight loss curve of the composition over the course of the heating time had an inflection point (one) at the heating time of 30 minutes.
  • the slope of the weight change per unit time from 0 minutes to 30 minutes of heating time is -1.508 (wt% / min), and the slope of the weight change per unit time from 80 minutes to 120 minutes is -0.065 ( % By weight).
  • the slope of weight change per unit time from 0 minutes to 30 minutes (% by weight) is the slope of the regression line obtained by the least square method using data within the range from 0 minutes to 30 minutes. .
  • the slope of weight change per unit time from 80 minutes to 120 minutes (wt% / minute) is the slope of the regression line obtained by the least square method using data within the range from 80 minutes to 120 minutes of heating time.
  • Example 2 1.0 part by weight of an aromatic amine polymer (hole transport material), 39.6 parts by weight of cyclohexylbenzene (boiling point: 236 ° C.), 39.6 parts by weight of 4-methylanisole (boiling point: 175 ° C.), Then, 19.8 parts by weight of n-decylbenzene (boiling point: 293 ° C.) was mixed and stirred to prepare composition 2.
  • the weight change of the composition with the passage of heating time was measured by the following procedure.
  • a petri dish containing the composition 2 was placed on an ASONE hot plate (model number: HP-1SA) heated to 80 ° C. in an atmosphere of 1 atm, an air temperature of 23 to 26 ° C., and a humidity of 40 to 60%.
  • One minute after placing the petri dish heating time: 1 minute
  • the petri dish was removed from the hot plate and the weight was measured with an electronic balance.
  • the weight of the composition 2 was 1.1101 g. At this time, the weight retention rate of the composition 2 was 98.975%. Moreover, the time required for the weight measurement with an electronic balance was about 10 seconds.
  • the petri dish was again placed on a hot plate heated to 80 ° C., and after 2 minutes (heating time: 3 minutes), the petri dish was removed from the hot plate and the weight was measured with an electronic balance. The weight of the composition 2 was 1.0701 g. At this time, the weight retention rate of the composition 2 was 95.408%.
  • V The same operation was performed several times, and the weight change up to 120 minutes of heating time was measured. The results are shown in Table 3.
  • a weight loss curve of the composition over time (horizontal axis: time (minutes), vertical axis: weight retention (% by weight)) was prepared.
  • the weight loss curve of the composition over the course of the heating time had an inflection point (one) at the heating time of 30 minutes.
  • the slope of the weight change per unit time from 0 minutes to 30 minutes of heating time is -1.237 (% by weight / min), and the slope of the weight change per unit time from 80 minutes to 120 minutes of heating time is -0. 151 (wt% / min).
  • the film 2 had a flat shape.
  • the film thickness of the thinnest part of the film 2 was 55 nm, and the film thickness of the thickest part was 70 nm.
  • the value of “(thickness of the thickest part) / (thickness of the thinnest part)” (which is a measure of flatness) of the film 2 was 1.27.
  • the shape of the membrane 2 is shown in FIG. The film shape measurement was performed using NewView 5000 (OMP-0423F) manufactured by Zygo.
  • the weight change of the composition with the passage of heating time was measured by the following procedure.
  • a petri dish containing the composition C1 was placed on an ASONE hot plate (model number: HP-1SA) heated to 80 ° C. in an atmosphere of 1 atm, an air temperature of 23 to 26 ° C., and a humidity of 40 to 60%.
  • the weight of the composition C1 was 1.0024 g. At this time, the weight retention rate of the composition C1 was 99.208%. Moreover, the time required for the weight measurement with an electronic balance was about 10 seconds.
  • the petri dish was again placed on a hot plate heated to 80 ° C., and after 2 minutes (heating time: 3 minutes), the petri dish was removed from the hot plate and the weight was measured with an electronic balance. The weight of the composition C1 was 0.9797 g. At this time, the weight retention rate of the composition C1 was 96.962%.
  • V The same operation was performed several times, and the weight change up to 120 minutes of heating time was measured. The results are shown in Table 4.
  • the film C1 was an extremely concave shape.
  • the film thickness of the thinnest part of the film C1 was 52 nm, and the film thickness of the thickest part was 115 nm.
  • the value of “(thickness of the thickest part) / (thickness of the thinnest part)” (which is a measure of flatness) of the film C1 was 2.21.
  • the shape of the film C1 is shown in FIG. The film shape measurement was performed using NewView 5000 (OMP-0423F) manufactured by Zygo.
  • a composition having excellent flatness of the resulting film can be provided when used in a discharge-type coating method. Moreover, according to this invention, the light emitting element obtained using this composition can be provided.

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  • Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)
  • Electroluminescent Light Sources (AREA)

Abstract

La présente invention concerne une composition dans laquelle, dont lorsque 1 g est introduit dans un récipient en verre de borosilicate de 50-mm et chauffé à 80 °C sous 1 atmosphère: la courbe décrivant la perte de poids de la composition pendant la durée de chauffage (axe horizontal: temps (minutes) de chauffage à 80°C; axe vertical: rétention de poids de la composition (% en poids)) présente au moins un point d'inflexion; la pente de la variation de poids par unité de temps (% en poids/minute) à partir d'une durée de chauffage de 0 minute à 30 minutes est inférieure à –1; et la pente de la variation de poids par unité de temps (% en poids/minute) à partir d'une durée de chauffage de 80 minutes à 120 minutes est supérieure à – 0,3 et inférieur à 0.
PCT/JP2016/064221 2015-05-19 2016-05-13 Composition et élément électroluminescent utilisant une telle composition Ceased WO2016186012A1 (fr)

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