WO2012056966A1 - アミン含有ホスフィン化合物 - Google Patents

アミン含有ホスフィン化合物 Download PDF

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WO2012056966A1
WO2012056966A1 PCT/JP2011/074029 JP2011074029W WO2012056966A1 WO 2012056966 A1 WO2012056966 A1 WO 2012056966A1 JP 2011074029 W JP2011074029 W JP 2011074029W WO 2012056966 A1 WO2012056966 A1 WO 2012056966A1
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group
substituent
carbon atoms
bis
represented
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French (fr)
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小林　憲史
東村　秀之
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住友化学株式会社
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Definitions

  • the present invention relates to an amine-containing phosphine compound.
  • a shallow HOMO (highest occupied orbit) level material is considered promising.
  • various compounds having an electron-donating strong amine moiety have been studied.
  • the shallow HOMO level is a HOMO level having a small absolute value of energy.
  • phosphine-based ligands are well known as ligands for forming metal complexes.
  • a ligand having two phosphine moieties in the ligand and capable of coordinating in a chelate form with the phosphine moiety can form a stable complex (Non-patent Document 1).
  • bidentate coordination is possible as a ligand capable of forming a metal complex that is excellent in hole injection and / or transportability and excellent in hole injection and / or transportability. It is considered that a compound having an amine moiety in the skeleton having a phosphine moiety is highly useful.
  • the present invention provides the following compounds [1] to [6], a metal complex [7], and a light emitting device [8].
  • [1] A compound represented by the following formula (A).
  • R 1 is a divalent organic group which may have a substituent.
  • Each R 11 is a hydrocarbyl group which may have a substituent.
  • Two R 11 which are attached to the same Q 1 may have taken together with Q 1 to which they are attached form a ring.
  • the four R 11 may be the same or different.
  • At least one group selected from R 1 and four R 11 has a diarylamino group as a substituent.
  • Q 1 is The compound according to [1], wherein [3] R 1 may have a substituent, a group represented by any one of the following formulas r1 ' ⁇ r12', The compound according to [1] or [2].
  • Y 3 is a divalent group represented by — (C (R 53 ) 2 ) n —, —O—, —S—, —N (R 52 ) — or —Si (R 53 ) 2 —. . n is 1 or 2.
  • R 52 is an aryl group having 6 to 18 carbon atoms which may have a substituent.
  • Each R 53 is a hydrogen atom or a hydrocarbyl group having 1 to 18 carbon atoms which may have a substituent.
  • a plurality of R 53 may be the same or different.
  • [4] The compound according to any one of [1] to [3], wherein R 11 is an aryl group which may have a substituent.
  • [5] The compound according to any one of [1] to [4], wherein at least three groups selected from R 1 and four R 11 have a diarylamino group as a substituent.
  • [6] The compound according to any one of [1] to [5], wherein the diarylamino group is a diphenylamino group.
  • a metal complex comprising the compound according to any one of [1] to [6].
  • [8] A light-emitting device containing the compound according to any one of [1] to [6] and / or the metal complex according to [7].
  • the compound of the present invention has a shallow HOMO level and can form a chelate-type coordination with two phosphine sites with respect to a metal, and can form a metal complex with a shallow HOMO level. That is, the compound of the present invention is excellent in hole injecting property and / or transporting property, and by using the compound of the present invention, a metal complex excellent in hole injecting property and / or transporting property can be realized.
  • Me represents a methyl group
  • t-Bu represents a tertiary butyl group
  • Ph represents a phenyl group
  • t-Oct represents a 1,1,3,3-tetramethylbutyl group.
  • the present invention provides a compound represented by the following formula (A).
  • R 1 is a divalent organic group which may have a substituent.
  • Each R 11 is a hydrocarbyl group which may have a substituent.
  • Two R 11 which are attached to the same Q 1 may have taken together with Q 1 to which they are attached form a ring.
  • the four R 11 may be the same or different. At least one group selected from R 1 and four R 11 has a diarylamino group as a substituent.
  • a divalent organic group which may have a substituent is synonymous with “a divalent organic group which may be substituted”, and a part of hydrogen atoms in the divalent organic group. Or all the thing means the divalent organic group which may be substituted by the substituent.
  • the “optionally substituted hydrocarbyl group” has the same meaning as the “optionally substituted hydrocarbyl group”, and a part or all of the hydrogen atoms in the hydrocarbyl group are substituted with the substituent. It refers to a hydrocarbyl group that may be present. The substituent will be described later.
  • the number of carbon atoms of the compound represented by the formula (A) is usually 20 to 350, preferably 25 to 300, more preferably 30 to 250, still more preferably 35 to 200, particularly preferably. 40-150.
  • Q 1 is And preferably And more preferably It is. There are two Q 1 is may be the same or different from each other, but are preferably the same.
  • Examples of the divalent organic group represented by R 1 include a divalent hydrocarbon group, a divalent group formed by combining a divalent hydrocarbon group and —O— and / or —S—, And groups represented by any of formulas r1 to r12.
  • the divalent hydrocarbon group may be linear, branched or cyclic, and usually has 1 to 30 carbon atoms.
  • Examples of the divalent hydrocarbon group include alkanediyl groups having 1 to 30 carbon atoms such as methanediyl group, ethanediyl group, propanediyl group, butanediyl group, pentanediyl group, hexanediyl group, heptanediyl group, and octanediyl group; An alkenediyl group having 2 to 30 carbon atoms such as ethenediyl group, propenediyl group, butenediyl group, pentenediyl group, hexenediyl group, heptenediyl group, octenediyl group; C2-C30 alkynediyl group such as octynediyl group; cyclopropanediyl group
  • a divalent group formed by combining a divalent hydrocarbon group and —O— and / or —S— is a group in which the above divalent hydrocarbon group and —O— and / or —S— are bonded. is there.
  • Examples of such a divalent group include a divalent hydrocarbon oxy group, a divalent hydrocarbon thio group, an oxyhydrocarbon thio group, and a thiohydrocarbon oxy group.
  • the definition, examples, and preferred examples of the hydrocarbon in such a divalent group are the same as those described above for the divalent hydrocarbon group.
  • Y 1 represents — (C (R 51 ) 2 ) m —, —O—, —S— , —N (R 50 ) —, —Si (R 51 ) 2 —, —O (C (R 51 ) 2 ) m - or -O (C (R 51) 2 ) is a divalent group represented by m O-.
  • Y 2 is a divalent group represented by — (C (R 51 ) 2 ) m —, —O—, —S— or —Si (R 51 ) 2 —.
  • m is an integer of 1 to 3.
  • R 50 is an aryl group having 6 to 30 carbon atoms which may have a substituent.
  • R 51 is a hydrogen atom or a hydrocarbyl group having 1 to 30 carbon atoms which may have a substituent.
  • a plurality of R 51 may be the same or different.
  • the number of carbon atoms in the “aryl group having 6 to 30 carbon atoms” is preferably 6 to 18; More preferably, it is 6 to 12, and still more preferably 6.
  • Examples of the “aryl group having 6 to 30 carbon atoms” in the aryl group having 6 to 30 carbon atoms which may have a substituent represented by R 50 include, for example, a phenyl group, a 1-naphthyl group, 2 -Naphtyl group, 9-fluorenyl group, 9-anthracenyl group, 2-anthracenyl group.
  • aryl group having 6 to 30 carbon atoms having a substituent in the aryl group having 6 to 30 carbon atoms which may have a substituent represented by R 50 , for example, a 2-methylphenyl group 3-methylphenyl group, 4-methylphenyl group, 2-trifluoromethylmethylphenyl group, 4-trifluoromethylphenyl group, 2,4,6-trimethylphenyl group, 2,6-dimethylphenyl group, 2 -Isopropylphenyl group, 2-methoxyphenyl group, 4-methoxyphenyl group, 4-fluorophenyl group, 4-ethylphenyl group, 4-propylphenyl group, 4-isopropylphenyl group, 4-n-butylphenyl group, 4 -Tert-butylphenyl group, 4-hexylphenyl group, 4- (2-ethylhexyl) phenyl group, 4-cyclohexylsulfate Examples
  • the “hydrocarbyl group having 1 to 30 carbon atoms” in the hydrocarbyl group having 1 to 30 carbon atoms which may have a substituent represented by R 51 may be linear, branched or cyclic, For example, methyl group, ethyl group, propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-butyl group, pentyl group, hexyl group, heptyl group, octyl group, nonyl group, decyl group, C1-C30 alkyl groups such as undecyl, dodecyl, pentadecyl, octadecyl, docosyl, etc .; cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclononyl, cyclododecyl, norbornyl A cyclic saturated
  • hydrocarbyl group having 1 to 30 carbon atoms in the hydrocarbyl group having 1 to 30 carbon atoms represented by R 51 , among the hydrocarbyl groups having 1 to 30 carbon atoms described above, preferably the number of carbon atoms
  • An alkyl group having 1 to 18 carbon atoms and an aryl group having 6 to 18 carbon atoms more preferably an alkyl group having 1 to 12 carbon atoms and an aryl group having 6 to 12 carbon atoms, still more preferably carbon.
  • An alkyl group having 1 to 8 atoms and a phenyl group are preferable, and an alkyl group having 1 to 8 carbon atoms is particularly preferable.
  • Examples of the substituent that the group represented by R 51 may have include a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a trifluoromethyl group, a hydrocarbyl group having 1 to 12 carbon atoms, and a carbon atom.
  • a hydroxy group optionally substituted with a hydrocarbyl group having 1 to 12 ie, hydrocarbyloxy group
  • an amino group optionally mono- or disubstituted with a hydrocarbyl group having 1 to 12 carbon atoms for example, described later
  • Diarylamino group a mercapto group optionally substituted with a hydrocarbyl group having 1 to 12 carbon atoms
  • a formula: —C ( ⁇ O) R 55 (wherein R 55 represents a hydrogen atom or a carbon atom) Represents a hydrocarbyl group having a number of 1 to 12.).
  • hydrocarbyl group having 1 to 12 carbon atoms are the same as those in the description of the hydrocarbyl group having 1 to 30 carbon atoms in R 51 in which the number of carbon atoms is limited to 12 or less. It is.
  • Examples of the group represented by any of the above formulas r1 to r12 include a group represented by any of the following formulas r1 ′ to r12 ′.
  • a hydrogen atom in a group represented by any one of the following formulas r1 ′ to r12 ′ may be substituted.
  • Y 3 is a divalent group represented by — (C (R 53 ) 2 ) n —, —O—, —S—, —N (R 52 ) — or —Si (R 53 ) 2 —. . n is 1 or 2.
  • R 52 is an aryl group having 6 to 18 carbon atoms which may have a substituent.
  • R 53 is a hydrogen atom or a hydrocarbyl group having 1 to 18 carbon atoms which may have a substituent.
  • a plurality of R 53 may be the same or different.
  • Examples of the aryl group having 6 to 18 carbon atoms which may have a substituent represented by R 52 include those having 6 to 30 carbon atoms which may have a substituent represented by R 50 .
  • the aryl group is the same as the group limited to 6 to 18 carbon atoms.
  • the number of carbon atoms of the “aryl group having 6 to 18 carbon atoms” in the aryl group having 6 to 18 carbon atoms which may have a substituent represented by R 52 is preferably 6 to 12, More preferably 6.
  • Examples of the substituent that the group represented by R 52 may have include the same groups as the substituent that the group represented by R 51 described above may have.
  • hydrocarbyl group having 1 to 18 carbon atoms in the hydrocarbyl group having 1 to 18 carbon atoms which may have a substituent represented by R 53 are the carbon atoms represented by R 51 In the hydrocarbyl group having 1-30, it is the same as the group in which the number of carbon atoms is limited to 1-18.
  • the “hydrocarbyl group having 1 to 18 carbon atoms” in the hydrocarbyl group having 1 to 18 carbon atoms which may have a substituent represented by R 53 is preferably an alkyl group having 1 to 18 carbon atoms.
  • An aryl group having 6 to 18 carbon atoms more preferably an alkyl group having 1 to 12 carbon atoms and an aryl group having 6 to 12 carbon atoms, and still more preferably an aryl group having 1 to 8 carbon atoms.
  • An alkyl group and a phenyl group are preferable, and an alkyl group having 1 to 8 carbon atoms is particularly preferable.
  • Examples of the substituent that the group represented by R 53 may have include the same groups as the substituent that the group represented by R 51 described above may have.
  • R 1 is a group represented by any one of the above formulas r1 to r12 which may have a substituent. More preferably, R 1 is a group represented by any one of the above formulas r1, r2, r5, r6, r8, and r9 which may have a substituent; and the above formula that may have a substituent.
  • a group represented by r10 wherein Y 1 in the formula is —O—; a group represented by formula r11 that may have a substituent, wherein Y 1 in the formula is A group represented by —O— or —S—; a group represented by the above formula r12 which may have a substituent, wherein Y 1 is —O— and Y 2 is —CH 2; Or a group represented by the above formula r12 which may have a substituent, wherein Y 1 is —O— and Y 2 is —Si (R 51 ) 2 —. Is a group.
  • R 1 is a group represented by any one of the above formulas r1 ′, r5 ′, and r10 ′ that may have a substituent; in the above formula r12 ′ that may have a substituent.
  • Y 3 in the formula is —CH 2 —; a group represented by the above formula r12 ′ which may have a substituent, wherein Y 3 is It is a group that is —Si (CH 3 ) 2 —.
  • R 1 is a group represented by the above formula r12 ′, which may have a substituent, wherein Y 3 is —CH 2 —; And a group represented by the above formula r12 ′, wherein Y 3 is —Si (CH 3 ) 2 —.
  • Examples of the substituent that the group represented by R 1 may have include, for example, a halogen atom (for example, fluorine atom, chlorine atom, bromine atom, iodine atom), hydrocarbyl group having 1 to 30 carbon atoms, carbon A hydroxy group optionally substituted with a hydrocarbyl group having 1 to 30 atoms (ie, a hydrocarbyloxy group), an amino group optionally monosubstituted or disubstituted with a hydrocarbyl group having 1 to 30 carbon atoms (for example, A diarylamino group described later), a mercapto group optionally substituted with a hydrocarbyl group having 1 to 30 carbon atoms, a formula: —C ( ⁇ O) R 56 (wherein R 56 represents a hydrogen atom or a carbon atom) Represents a hydrocarbyl group having 1 to 30 atoms).
  • a halogen atom for example, fluorine atom, chlorine atom, bromine atom
  • hydrocarbyl group having 1 to 30 carbon atoms are the same as those described for R 51 .
  • a substituent is a diarylamino group, fluorine atom, chlorine atom, bromine atom, trifluoromethyl group, methyl group, ethyl group, propyl group, n-butyl group, isobutyl group, tert-butyl, which will be described later.
  • such a substituent is a fluorine atom, chlorine atom, trifluoromethyl group, methyl group, ethyl group, propyl group, n-butyl group, tert-butyl group, hexyl group, octyl group, cyclohexyl group.
  • a substituent is a fluorine atom, chlorine atom, trifluoromethyl group, methyl group, ethyl group, propyl group, n-butyl group, tert-butyl group, hexyl group, octyl group, cyclohexyl group.
  • substituents are fluorine atom, trifluoromethyl group, methyl group, n-butyl group, tert-butyl group, phenyl group, 4-methylphenyl group, 4-methoxyphenyl group, 4-tert. -A butylphenyl group and a methoxy group.
  • a substituent is a fluorine atom, a methyl group, or a tert-butyl group.
  • the number of substituents that the group represented by R 1 may have is preferably 0 to 4, more preferably 0 to 3, and still more preferably 0 to 2.
  • R 1 is a divalent group represented by any one of the above formulas r1 ′ to r12 ′, the substituent is preferably in the following positions.
  • a diarylamino group may be substituted at the position shown below.
  • Formula r1 ′ Preferably, at least one position selected from the 2′-position and the 3′-position;
  • Formula r2 ′ Preferably, at least one position selected from the 2 ′ position, the 3 ′ position, the 4 ′ position, and the 5 ′ position, more preferably the two positions of the 2 ′ position and the 5 ′ position, or the 3 ′ position and 2 places in 4 'position;
  • Formula r3 ′ Preferably, at least one position selected from the 2′-position, 3′-position, 4′-position, 5′-position, 6′-position and 8′-position, more preferably one-position only at the 4′-position, 2 2 positions of 'position and 6' position, 2 positions of 3 'position and 5' position, 3 positions of 2 'position, 4' position and 6 'position, or 3 positions of 3', 4 'position and 5'Location;
  • Formula r4 ′ Preferably, at least one position selected from the 2 ′ position, the 3
  • Formula r5 ′ Preferably, at least one position selected from the 2 ′ position, the 3 ′ position, the 4 ′ position, the 5 ′ position, the 6 ′ position and the 7 ′ position, more preferably 2 at the 2 ′ position and the 7 ′ position.
  • Formula r6 ′ Preferably, at least one position selected from the 2′-position, 3′-position, 4′-position, 5′-position, 8′-position, 9′-position, 10′-position and 11′-position, more preferably 2 2 places of 'position and 11' position, 2 places of 3 'position and 10' position, or 2 places of 4 'position and 9'position;
  • Formula r7 ′ Preferably, at least one position selected from the 2 ′ position, the 3 ′ position, the 4 ′ position, the 5 ′ position, the 6 ′ position and the 7 ′ position, more preferably 2 at the 2 ′ position and the 7 ′ position.
  • Formula r8 ′ Preferably, at least one position selected from the 2′-position, 3′-position, 5′-position, 6′-position, 7′-position, 8′-position, 9′-position and 10′-position, more preferably 2 2 places, 'position and 6' position, or 2 places, 3 'position and 5'position;
  • Formula r9 ′ Preferably, at least one position selected from the 2 ′ position and the 5 ′ position;
  • Formula r10 ′ Preferably, at least one position selected from the 2′-position, 3′-position, 4′-position, 5′-position, 6′-position and 7′-position, more preferably 2 at the 2′-position and 7′-position Or two locations at the 3 ′ and 6 ′ positions, more preferably two locations at the 2 ′ and 7 ′ positions;
  • Formula r11 ′ Preferably, at least one position selected from the 2 ′ position, the 3 ′ position, the 4 ′ position, and the 5 ′ position, more
  • the “hydrocarbyl group” in the hydrocarbyl group which may have a substituent represented by R 11 may be linear, branched or cyclic, and usually has 1 to 30 carbon atoms.
  • Examples of the hydrocarbyl group optionally having a substituent represented by R 11 include a methyl group, an ethyl group, a propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, and a tert-butyl group.
  • phenyl group 1-naphthyl group, 2-naphthyl group, 2-methylphenyl group, 3-methylphenyl group, 4-methylphenyl group, 2-ethylphenyl group, 2-propylphenyl group, 2-isopropylphenyl group 2-n-butylphenyl group, 2-isobutylphenyl group, 2-tert-butylphenyl group, 2-hexylphenyl group, 2-cyclohexylphenyl group, 4-adamantylphenyl group, 4-phenylphenyl group, 9-fluorenyl
  • Aryl groups having 6 to 30 carbon atoms such as a phenyl group, 1-phenylethyl group, 2-phenylethyl group, 1-phenyl-1-propyl group, 1-phenyl-2-propyl group, 2-phenyl -2-propyl group, 3-phenyl-1-propyl group, 4-phenyl-1-n-buty
  • Hydrocarbyl group in a hydrocarbyl group that may have a substituent represented by R 11, among the “hydrocarbyl group” in the hydrocarbyl group optionally substituted as described above, preferably, carbon atoms
  • R 11 substituent represented by R 11
  • Examples of the substituent that the group represented by R 11 may have include a halogen atom (for example, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom), and a hydrocarbyl group having 1 to 30 carbon atoms.
  • a halogen atom for example, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom
  • a hydrocarbyl group having 1 to 30 carbon atoms for example, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom
  • An optionally substituted hydroxy group that is, a hydrocarbyloxy group
  • an amino group that may be mono- or disubstituted with a hydrocarbyl group having 1 to 30 carbon atoms for example, a diarylamino group described later
  • the number of carbon atoms examples thereof include a mercapto group optionally substituted with 1 to 30 hydrocarbyl groups, a group represented by the formula: —C ( ⁇ O) R 56 (wherein R 56 is the same as defined above).
  • R 56 is the same as defined above.
  • the definition, examples and preferred examples of the hydrocarbyl group having 1 to 30 carbon atoms are the same as those described for R 51 .
  • Preferred examples of the substituent that the hydrocarbyl group represented by R 11 may have are the same as the substituent that the divalent organic group represented by R 1 may have.
  • the number of substituents that the group represented by R 11 may have is preferably 0 to 4, more preferably 0 to 3, and still more preferably 0 to 2.
  • the “hydrocarbyl group” in the optionally substituted hydrocarbyl group represented by R 11 is an aryl group.
  • aryl groups include phenyl, 1-naphthyl, 2-methyl-1-naphthyl, 2-naphthyl, 2-methylphenyl, 3-methylphenyl, 4-methylphenyl, 2,4 -Dimethylphenyl group, 3,5-dimethylphenyl group, 2,6-dimethylphenyl group, 2,4,6-trimethylphenyl group, 2-ethylphenyl group, 4-ethylphenyl group, 2,6-diethylphenyl group 4-propylphenyl group, 2-isopropylphenyl group, 4-isopropylphenyl group, 2,6-diisopropylphenyl group, 2-n-butylphenyl group, 4-n-butylphenyl group, 2-tert-butylphenyl group 4-tert-butylbuty
  • the aryl group is a phenyl group, 2-methylphenyl group, 3-methylphenyl group, 4-methylphenyl group, 2,4-dimethylphenyl group, 3,5-dimethylphenyl group, 2,6-dimethylphenyl.
  • the aryl group is a phenyl group, 2-methylphenyl group, 3-methylphenyl group, 4-methylphenyl group, 2,4-dimethylphenyl group, 3,5-dimethylphenyl group, 2,6-dimethyl group.
  • the aryl group is a phenyl group.
  • At least one group selected from R 1 and four R 11 has a diarylamino group as a substituent.
  • the group represented by R 1 may have one or more diarylamino groups as a substituent, and at least one group selected from four R 11 replaces one or more diarylamino groups.
  • You may have as a group.
  • at least one group selected from four R 11 has one or more diarylamino groups as substituents, more preferably at least two groups have one or more diarylamino groups,
  • at least three groups have one or more diarylamino groups, particularly preferably each of the four groups has one or more diarylamino groups.
  • the number of diarylamino groups that each of the group represented by R 1 and / or the four groups represented by four R 11 may have as a substituent is, for example, 1, 2, or 3. It is. At least two, three, or four groups selected from four R 11 may have the same number of diarylamino groups as substituents, or have different numbers of diarylamino groups as substituents. You may do it. Examples of the compound represented by the above formula (A), also a hydrogen atom in the four groups represented by the four R 11 are each, also compounds are substituted with one or two same number of diarylamino groups preferable.
  • the diarylamino group is an amino group in which two hydrogen atoms in the amino group are substituted with two aryl groups.
  • Two aryl groups in a diarylamino group may be the same or different, examples and preferred examples are the same as the aryl group having 6 to 30 carbon atoms described in R 11.
  • examples of the diarylamino group include a diphenylamino group, a bis (1-naphthyl) amino group, a bis (2-methyl-1-naphthyl) amino group, a bis (2-naphthyl) amino group, and a bis ( 2-methylphenyl) amino group, bis (3-methylphenyl) amino group, bis (4-methylphenyl) amino group, bis (2,4-dimethylphenyl) amino group, bis (3,5-dimethylphenyl) amino Group, bis (2,6-dimethylphenyl) amino group, bis (2,4,6-trimethylphenyl) amino group, bis (2-ethylphenyl) amino group, bis (4-ethylphenyl) amino group, bis ( 2,6-diethylphenyl) amino group, bis (4-propylphenyl) amino group, bis (2-isopropylphenyl) amino group, bis (4-isopropylpropylene) Phen
  • the diarylamino group is a diphenylamino group, a bis (1-naphthyl) amino group, a bis (2-naphthyl) amino group, a bis (2-methylphenyl) amino group, a bis (3-methylphenyl) amino group, Bis (4-methylphenyl) amino group, bis (3,5-dimethylphenyl) amino group, bis (4-propylphenyl) amino group, bis (4-n-butylphenyl) amino group, bis (4-tert- Butylphenyl) amino group, bis (4-hexylphenyl) amino group, bis (4-cyclohexylphenyl) amino group, bis (4-methoxyphenyl) amino group, bis (4-fluorophenyl) amino group, or bis (4 -Trifluoromethylmethylphenyl) amino group.
  • the diarylamino group is a diphenylamino group, bis (4-methylphenyl) amino group, bis (4-n-butylphenyl) amino group, bis (4-tert-butylphenyl) amino group, bis (4 -Hexylphenyl) amino group, bis (4-methoxyphenyl) amino group, or bis (4-fluorophenyl) amino group. More preferably, the diarylamino group is a diphenylamino group, a bis (4-methylphenyl) amino group, a bis (4-n-butylphenyl) amino group, a bis (4-tert-butylphenyl) amino group, or a bis ( 4-hexylphenyl) amino group. Particularly preferably, the diarylamino group is a diphenylamino group.
  • Examples of the compound represented by the above formula (A) include compounds represented by the following formulas a1 to a26.
  • the formula is preferably the formulas a1 to a22, more preferably the formulas a1, a6, a7, a9, a11 to a22, and still more preferably the formulas a1, a6, a7, a9, and a11 to a19. Particularly preferred are the formulas a1, a6, a7, a9.
  • the compound of the present invention can be produced according to a conventional method for synthesizing a phosphine compound having a substituent.
  • the compound represented by the formula a12 will be described as an example. Under an argon gas atmosphere, 1 mmol of 1,2-bis (dichlorophosphino) benzene and 5 mmol of (4-diphenylaminophenyl) magnesium bromide are obtained. Mix in tetrahydrofuran (10 mL) at ⁇ 78 ° C. and stir for 12 hours while gradually warming to room temperature. The reaction solution can be extracted with water and chloroform, and the organic layer can be concentrated and then purified by silica gel column chromatography.
  • the present invention also provides a metal complex containing a compound represented by the above formula (A).
  • the metal complex of the present invention may be a mononuclear complex, a binuclear complex, or a complex having three or more nuclei, but a mononuclear complex or a binuclear complex is preferable, and a mononuclear complex is more preferable.
  • the metal complex of the present invention is preferably a metal complex represented by the following composition formula (1).
  • M (L 1 ) a (L 2 ) b (X 1 ) c (1)
  • M is a metal that may be charged.
  • L 1 is a compound represented by the above formula (A).
  • L 2 is a ligand different from L 1.
  • X 1 is an anion, a is a positive number, b and c are each independently a number of 0 or more, and a plurality of L 1 , L 2 and X 1 are the same or different. May be.
  • M is preferably Mg, V, Cr, Mn, Fe, Co, Ni, Cu, Zn, Ga, Ge, Zr, Ru, Rh, Pd, Ag, Sn, Hf, W , Re, Os, Ir, Pt, Au, Eu, Tb, more preferably Fe, Ni, Cu, Zn, Ge, Ru, Rh, Pd, Ag, W, Pt, Au, and more preferably Cu.
  • Pd, Ag, Pt, and Au particularly preferably Cu, Ag, and Au.
  • L 1 may be monodentate or bidentate to M, but is preferably bidentate.
  • L 1 is preferably such that the atom coordinated to M is C, N, O, P or S, more preferably N, O, P or S, and N, O or P More preferably, N or P is particularly preferable.
  • the atom (element) coordinated to M may be neutral or charged, but is preferably neutral.
  • L 2 may be a monodentate ligand, a bidentate ligand, or a tridentate or higher ligand.
  • a ligand is more preferred.
  • L 2 examples include a ligand having a structure in which the diarylamino group in the compound represented by the above formula (A) is substituted with a hydrogen atom, triphenylphosphine which may have a substituent, and a substituent.
  • the diarylamino group in the compound represented by the formula (A) is a ligand having a structure in which a hydrogen atom is substituted, a biquinoline which may have a substituent, or a substituent.
  • Bipyridine phenanthroline optionally having a substituent, pyridinylimidazole optionally having a substituent, pyridinylbenzimidazole optionally having a substituent, More preferably, the biquinoline which may have a substituent, the bipyridine which may have a substituent, the phenanthroline which may have a substituent, the pyridinylimidazole which may have a substituent , Pyridinylbenzimidazole optionally having a substituent, More preferred are bipyridine which may have a substituent and phenanthroline which may have a substituent.
  • Examples of the substituent that the group exemplified as L 2 may have include a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a trifluoromethyl group, a hydrocarbyl group having 1 to 18 carbon atoms, A hydroxy group optionally substituted with a hydrocarbyl group having 1 to 18 carbon atoms (ie, a hydrocarbyloxy group), a mercapto group optionally substituted with a hydrocarbyl group having 1 to 18 carbon atoms, a formula: —C ( ⁇ O) R 57 (wherein R 57 represents a hydrogen atom or a hydrocarbyl group having 1 to 12 carbon atoms).
  • hydrocarbyl group having 1 to 18 carbon atoms are the same as those in the description of the hydrocarbyl group having 1 to 30 carbon atoms in R 51 in which the number of carbon atoms is limited to 18 or less. It is.
  • examples of the anion represented by X 1 include halide ions such as fluoride ion, chloride ion, bromide ion and iodide ion; sulfate ion, nitrate ion, carbonate ion and acetate ion.
  • X 1 is also an anion obtained by removing a hydrogen atom of a hydroxyl group from an organic group having a hydroxyl group, such as phenol and parafluorophenol; an organic group having a mercapto group, such as thiophenol and triphenylmethanethiol An anion formed by removing a hydrogen atom of the mercapto group; an anion formed by removing a hydrogen atom of the carboxylic acid from an organic group having a carboxylic acid such as para-tert-butylbenzoic acid and triphenylacetic acid; Anions obtained by removing hydrogen atoms of sulfonic acid from organic groups having sulfonic acid such as acid and para-n-butylbenzenesulfonic acid; phosphines such as diphenylphosphinic acid and bis (4-methoxyphenyl) phosphinic acid The hydrogen atom of the phosphinic acid is removed from the organic group having an acid.
  • Anions
  • X 1 is preferably fluoride ion, chloride ion, bromide ion, iodide ion, nitrate ion, perchlorate ion, tetrafluoroborate ion, hexafluorophosphate ion, trifluoromethanesulfonate ion, tetraphenylborate ion, Tetrakis (pentafluorophenyl) borate ion and tetrakis (3,5-bis (trifluoromethyl) phenyl) borate ion, more preferably tetrafluoroborate ion, hexafluorophosphate ion, trifluoromethanesulfonate ion, tetraphenyl Borate ion, tetrakis (pentafluorophenyl) borate ion.
  • X 1 may be a monovalent anion or a divalent or higher anion, but is preferably a monovalent anion.
  • composition formula (1) a, b and c are determined so that the charge of the metal complex becomes neutral as a whole. a, b, and c are relative values with the coefficient of M set to 1. In the complex represented by the composition formula (1), for one M, there are a L 1 , b L 2 , and c X 1 .
  • A is preferably a number of 0.5 to 3.0, more preferably a number of 0.7 to 2.0, and even more preferably a number of 0.9 to 1.1.
  • b and c are each independently preferably a number of 0.0 to 4.0, more preferably a number of 0.0 to 3.0, and still more preferably a number of 0.5 to 2.0.
  • the number is particularly preferably 0.9 to 1.1.
  • Examples of the metal complex of the present invention include metal complexes represented by the following formulas b1 to b20.
  • the formulas are preferably b3 to b5, b11 to b13, b17 to b20, more preferably the formulas b3 to b5, b11 to b13, and still more preferably the formulas b11 to b13.
  • the compound and / or metal complex of the present invention can be used, for example, as a reaction catalyst or cocatalyst, or as a luminescent material, but is preferably used as a luminescent material.
  • the present invention also contains a compound represented by the above formula (A) and / or a metal complex containing a compound represented by the above formula (A) (hereinafter referred to as “material of the present invention”).
  • a light emitting device is provided.
  • the light-emitting element of the present invention is usually a light-emitting element in which a pair of electrodes composed of an anode and a cathode and a thin film layer composed of one or more layers having a light-emitting layer provided between the electrodes are sandwiched between the thin film At least one of the layers comprises the material of the present invention.
  • the content of the material of the present invention in the layer containing the material of the present invention is usually 0.01 to 100% by weight, preferably 0. It is 1 to 99% by weight, more preferably 1 to 90% by weight, still more preferably 5 to 85% by weight, and particularly preferably 10 to 80% by weight.
  • Examples of the light emitting device of the present invention include a single layer type light emitting device (anode / light emitting layer / cathode).
  • a layer structure of the multilayer light emitting element for example, (A) anode / hole injection layer / (hole transport layer) / light emitting layer / cathode (b) anode / light emitting layer / electron injection layer / (electron transport layer) / cathode (c) anode / hole injection layer / (Hole transport layer) / light emitting layer / electron injection layer / (electron transport layer) / cathode (d) anode / light emitting layer / (electron transport layer) / electron injection layer / cathode (e) anode / hole injection layer / (Hole transport layer) / light emitting layer / (electron transport layer) / electron injection layer / cathode.
  • the light emitting device of the present invention is not limited
  • (hole transport layer) and (electron transport layer) represent arbitrary layers that may or may not exist at each position.
  • the material of the present invention may be contained in any layer, but is preferably contained in at least one of the hole injection layer, the hole transport layer, and the light emitting layer, and at least one of the hole transport layer and the light emitting layer. It is more preferable that it is contained in at least the light emitting layer.
  • the anode supplies holes to a hole injection layer, a hole transport layer, a light emitting layer, and the like, and preferably has a work function of 4.5 eV or more.
  • a material of the anode metals, alloys, metal oxides, electrically conductive compounds and combinations thereof can be used. Specifically, tin oxide, zinc oxide, indium oxide, indium tin oxide (ITO), etc.
  • Conductive metal oxides metals such as gold, silver, chromium and nickel, mixtures and laminates of these conductive metal oxides and metals, inorganic conductive materials such as copper iodide and copper sulfide, polyaniline , Polythiophenes [poly (3,4) ethylenedioxythiophene, etc.], organic conductive materials such as polypyrrole, and combinations thereof with ITO can be used.
  • the cathode supplies electrons to an electron injection layer, an electron transport layer, a light emitting layer, and the like.
  • As the material for the cathode metals, alloys, metal halides, metal oxides, electrically conductive compounds, and combinations thereof can be used.
  • alkali metals Li, Na, K, Cs, etc.
  • alkaline earth metals Mg, Ca, Ba, etc.
  • gold, silver, lead, aluminum, alloys and mixed metals [sodium-potassium alloys, sodium-potassium Mixed metal, lithium-aluminum alloy, lithium-aluminum mixed metal, magnesium-silver alloy, magnesium-silver mixed metal, etc.], rare earth metal [ytterbium, etc.] can be used.
  • the hole injection layer and the hole transport layer have a function of injecting holes from the anode, a function of transporting holes, or a function of blocking electrons injected from the cathode.
  • materials used for these layers include carbazole derivatives, triazole derivatives, oxazole derivatives, oxadiazole derivatives, imidazole derivatives, polyarylalkane derivatives, pyrazoline derivatives, pyrazolone derivatives, phenylenediamine derivatives, arylamine derivatives, amino-substituted Chalcone derivatives, styrylanthracene derivatives, fluorenone derivatives, hydrazone derivatives, stilbene derivatives, silazane derivatives, aromatic tertiary amine derivatives, styrylamine derivatives, aromatic dimethylidine derivatives, porphyrin derivatives, polysilane derivatives, poly (N-vinylcarbazole) derivatives , Organosilane derivatives, and polymers
  • the electron injection layer and the electron transport layer have a function of injecting electrons from the cathode, a function of transporting electrons, or a function of blocking holes injected from the anode.
  • materials used for these layers include triazole derivatives, oxazole derivatives, oxadiazole derivatives, imidazole derivatives, fluorene derivatives, fluorenone derivatives, anthraquinodimethane derivatives, anthrone derivatives, diphenylquinone derivatives, thiopyran dioxide derivatives.
  • the electron injection layer and the electron transport layer may have a single-layer structure composed of one or more of these, or a multilayer structure composed of a plurality of layers having the same composition or different compositions.
  • the electron injection layer and the electron transport layer may contain fullerene or a derivative thereof, carbon nanotube or a derivative thereof.
  • An insulator or a semiconductor inorganic compound can also be used as the material for the electron injection layer and the electron transport layer. If the electron injection layer and the electron transport layer are made of an insulator or a semiconductor, current leakage can be effectively prevented and the electron injection property can be improved.
  • Examples of such an insulator include at least one metal compound selected from the group consisting of alkali metal chalcogenides, alkaline earth metal chalcogenides, alkali metal halides, and alkaline earth metal halides, such as CaO, BaO, SrO, BeO, BaS and CaSe are preferred.
  • a semiconductor which comprises an electron injection layer and an electron carrying layer the group which consists of Ba, Ca, Sr, Yb, Al, Ga, In, Li, Na, Cd, Mg, Si, Ta, Sb, and Zn, for example And oxides, nitrides, and oxynitrides of at least one element selected from
  • a reducing dopant may be added to the interface region between the cathode and the thin film in contact with the cathode.
  • the reducing dopant include alkali metals, alkaline earth metals, rare earth metals, alkali metal oxides, alkali metal halides, alkaline earth metal oxides, alkaline earth metal halides, rare earth metals. And oxides or rare earth metal halides, alkali metal complexes, alkaline earth metal complexes, and rare earth metal complexes.
  • the light-emitting layer can inject holes from the anode, hole injection layer or hole transport layer when an electric field is applied, and can inject electrons from the cathode, electron injection layer or electron transport layer, injected charge It has either a function of moving (electrons and holes) by the force of an electric field or a function of providing a field for recombination of electrons and holes and connecting this to light emission. You may make the light emitting layer contain the host material which uses the material of this invention contained in a light emitting layer as a guest material.
  • Examples of the host material include a compound having a fluorene skeleton, a compound having a carbazole skeleton, a compound having a diarylamine skeleton, a compound having a pyridine skeleton, a compound having a pyrazine skeleton, a compound having a triazine skeleton, and a compound having an arylsilane skeleton Is mentioned.
  • the energy (T1) of the lowest excited triplet state of the host material is preferably larger than that of the guest material.
  • the host material may be a low molecular compound or a high molecular compound.
  • the host material may further contain an electrolyte, such as a supporting salt (lithium trifluoromethanesulfonate, lithium perchlorate, tetra-n-butylammonium perchlorate, potassium hexafluorophosphate, tetrafluoro Solvents that may contain tetra-n-butylammonium borate (propylene carbonate, acetonitrile, 2-methyltetrahydrofuran, 1,3-dioxofuran, nitrobenzene, N, N-dimethylformamide, dimethyl sulfoxide, glycerin, propyl alcohol , Water, etc.) or a gel-like polymer (polyethylene oxide, polyacrylonitrile, a copolymer of vinylidene fluoride and propylene hexafluoride, etc.) swollen with the solvent.
  • a supporting salt lithium trifluoromethanesulfonate, lithium perchlorate,
  • a light-emitting layer in which a light-emitting material is doped in the host material can be formed by applying a mixture of the host material and the material of the present invention or by co-evaporation.
  • guest materials include metal complexes using platinum group elements (for example, iridium complexes coordinated with phenylpyridine derivatives), metal complexes using rare earth elements (for example, europium complexes coordinated with phenanthroline derivatives), 8 -Aluminum complex coordinated with a quinolinol derivative, a compound having a naphthacene skeleton, a compound having a dicyanoethylene skeleton, a compound having a coumarin skeleton, a compound having a quinacridone skeleton, a compound having an anthracene skeleton, a compound having a perylene skeleton, a phenylene vinylene skeleton , A compound having a fluorene skeleton, and a compound having a naphthalene skeleton.
  • platinum group elements for example, iridium complexes coordinated with phenylpyridine derivatives
  • rare earth elements for example, europium complexes coordinated with phenanthroline
  • each layer may be formed by, for example, a vacuum deposition method (resistance heating deposition method, electron beam method, etc.), sputtering method, LB method, molecular lamination method, coating method (casting method, spin coating method). , Bar coating method, blade coating method, roll coating method, gravure printing method, screen printing method, ink jet method and the like], but the coating method is preferable because the manufacturing process can be simplified.
  • the material of the present invention can be formed by mixing a material with a solvent to prepare a coating solution, and coating and / or drying the coating solution on a desired layer (or electrode).
  • the coating solution may contain a resin as a host material and / or a binder. This resin can be dissolved in a solvent to form a solution, or can be dispersed to form a dispersion.
  • a non-conjugated polymer such as polyvinyl carbazole and a conjugated polymer such as poly (phenylene vinylene)
  • a non-conjugated polymer such as polyvinyl carbazole and a conjugated polymer such as poly (phenylene vinylene)
  • examples thereof include polyvinyl chloride, polycarbonate, polystyrene, polymethyl methacrylate, Polybutyl methacrylate, polyester, polysulfone, polyphenylene oxide, polybutadiene, poly (N-vinylcarbazole), hydrocarbon resin, ketone resin, phenoxy resin, polyamide, ethyl cellulose, vinyl acetate, ABS resin, polyurethane, melamine resin, unsaturated polyester resin , Alkyd resin, epoxy resin, and silicon resin.
  • the solution and dispersion containing the resin may further contain an antioxidant, a viscosity modifier and the like.
  • the solvent is preferably a solvent that uniformly dissolves the components of the thin film or a solvent that gives a stable dispersion.
  • alcohol methanol, ethanol, isopropyl alcohol, etc.
  • ketone acetone, methyl ethyl ketone, etc.
  • chlorinated hydrocarbon Chloroform, 1,2-dichloroethane, etc.]
  • aromatic hydrocarbons benzene, toluene, xylene, etc.
  • aliphatic hydrocarbons normal hexane, cyclohexane, etc.
  • amides dimethylformamide, etc.
  • sulfoxides dimethylsulfoxide, etc.
  • a mixture thereof may be mentioned.
  • a high-boiling solvent anisole, bicyclohexylbenzene, etc.
  • anisole bicyclohexylbenzene, etc.
  • the viscosity of the solution is preferably 1 to 100 mPa ⁇ s at 25 ° C.
  • each layer of the light emitting device of the present invention is usually 1 nm to 100 ⁇ m, preferably 2 nm to 1 ⁇ m, more preferably 5 nm to 200 nm.
  • the light-emitting element of the present invention can be used for, for example, an illumination light source, a sign light source, a backlight light source, a display device, and a printer head.
  • the display device can be configured in a segment type, a dot matrix type, or the like using a known driving technique, driving circuit, or the like.
  • NMR measurement a 300 MHz NMR spectrometer manufactured by Varian was used.
  • DART-MS measurement The AccuTOF TLC (JMS-T100TD) manufactured by JEOL Ltd. was used.
  • a photoelectron spectrometer (manufactured by Riken Keiki Co., Ltd .: AC-2) was used for measurement of the HOMO level.
  • Example 1 (Synthesis of 2,7-di-tert-butyl-4,5-bis [di [m- (N, N-diphenylamino) phenyl] phosphino] -9,9-dimethylxanthene (a1)) Dissolve 4,5-dibromo-2,7-di-tert-butyl-9,9-dimethylxanthene (250 mg, 0.520 mmol) in dehydrated THF (4 mL) at room temperature under a nitrogen atmosphere and cool to -78 ° C.
  • the energy level of the HOMO level of the obtained compound (a1) was measured and found to be ⁇ 5.40 eV.
  • the energy level of the HOMO level of the obtained complex (b11) was measured and found to be ⁇ 5.50 eV.
  • Example 3 (Production of Light-Emitting Element 1) A suspension of poly (3,4-ethylenedioxythiophene) / polystyrene sulfonic acid (manufactured by Bayer, trade name Bytron P AI4083) on a glass substrate on which a 60 nm ITO film was adhered was 60 rpm at 1500 rpm for 60 seconds at 1500 rpm. The film was formed to a thickness of 70 nm by spin coating for 2 seconds, and dried on a hot plate at 200 ° C. for 10 minutes. Thereafter, the substrate was naturally cooled to room temperature to obtain a substrate on which a hole injection layer was formed.
  • poly (3,4-ethylenedioxythiophene) / polystyrene sulfonic acid manufactured by Bayer, trade name Bytron P AI4083
  • a 0.6 wt% xylene solution of a hole transporting polymer material was prepared.
  • the hole transporting polymer material was synthesized by the following method.
  • methyl trioctyl ammonium chloride manufactured by Aldrich, trade name Aliquat 336 (registered trademark) (2.29 g) was added, followed by 50 mL of toluene.
  • PdCl 2 (PPh 3 ) 2 4.90 mg
  • the mixture was stirred in an oil bath at 105 ° C. for 15 minutes.
  • Aqueous sodium carbonate 2.0 M, 14 mL was added and the resulting mixture was stirred in an oil bath at 105 ° C. for 16.5 hours.
  • Phenylboronic acid 500 mg was then added and the resulting mixture was stirred for 7 hours.
  • the aqueous layer was removed from the reaction solution, and the organic layer was washed with 50 mL of water.
  • the organic layer thus obtained was returned to the reaction flask, and 0.750 g of sodium diethyldithiocarbamate and 50 mL of water were added.
  • the resulting mixture was stirred in an 85 ° C. oil bath for 16 hours.
  • the aqueous layer was removed from the reaction solution, and the organic layer was washed 3 times with 100 mL of water and then passed through a column of silica gel and basic alumina. Using toluene as an eluent, a toluene solution containing the eluted polymer was recovered.
  • the recovered toluene solution was poured into methanol to precipitate a polymer.
  • the precipitated polymer was dissolved again in toluene, and the obtained toluene solution was poured into methanol to precipitate the polymer again.
  • the precipitated polymer was vacuum dried at 60 ° C. to obtain 4.20 g of a hole transporting polymer material.
  • the obtained hole transporting polymer material has a polystyrene equivalent weight average molecular weight of 1.24 ⁇ 10 5 and a molecular weight distribution index [weight average molecular weight (Mw) / number average molecular weight. (Mn)] was 2.8.
  • a 0.6 wt% xylene solution of a hole transporting polymer material was applied by spin coating for 15 seconds at 1000 rpm and 60 seconds at 1500 rpm, A coating film having a thickness of 25 nm was obtained.
  • the substrate provided with this coating film was heated at 200 ° C. for 15 minutes and allowed to cool naturally to room temperature to obtain a substrate on which a hole transport layer was formed.
  • a light-emitting element 2 was produced in the same manner as the light-emitting element 1 except that the solution prepared as described above was used, and by applying a voltage of 10 V to the light-emitting element 2, light emission with a light emission efficiency of 1.6 cd / A was exhibited. It was.
  • the compound of the present invention has a shallow HOMO level, can be coordinated in a chelate form at the phosphine site, and can form a metal complex with a shallow HOMO level. Therefore, the compound of the present invention is excellent in hole injection and / or transportability, and the metal complex of the present invention using the compound of the present invention is excellent in hole injection and / or transportability. It is recognized that

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US10777753B2 (en) 2017-07-12 2020-09-15 Samsung Display Co., Ltd. Heterocyclic compound and organic electroluminescence device including the same

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JP2015185829A (ja) 2014-03-26 2015-10-22 三星ディスプレイ株式會社Ｓａｍｓｕｎｇ Ｄｉｓｐｌａｙ Ｃｏ．，Ｌｔｄ． 有機エレクトロルミネッセンス素子用発光材料、および有機エレクトロルミネッセンス素子
KR102603864B1 (ko) * 2016-05-13 2023-11-21 삼성디스플레이 주식회사 화합물 및 이를 포함하는 유기 발광 소자

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