WO2018174293A1 - 有機エレクトロルミネッセンス素子及び電子機器 - Google Patents
有機エレクトロルミネッセンス素子及び電子機器 Download PDFInfo
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- WO2018174293A1 WO2018174293A1 PCT/JP2018/011927 JP2018011927W WO2018174293A1 WO 2018174293 A1 WO2018174293 A1 WO 2018174293A1 JP 2018011927 W JP2018011927 W JP 2018011927W WO 2018174293 A1 WO2018174293 A1 WO 2018174293A1
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- BPUBBGLMJRNUCC-UHFFFAOYSA-N oxygen(2-);tantalum(5+) Chemical compound [O-2].[O-2].[O-2].[O-2].[O-2].[Ta+5].[Ta+5] BPUBBGLMJRNUCC-UHFFFAOYSA-N 0.000 description 1
- RVTZCBVAJQQJTK-UHFFFAOYSA-N oxygen(2-);zirconium(4+) Chemical compound [O-2].[O-2].[Zr+4] RVTZCBVAJQQJTK-UHFFFAOYSA-N 0.000 description 1
- 125000005062 perfluorophenyl group Chemical group FC1=C(C(=C(C(=C1F)F)F)F)* 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 125000004934 phenanthridinyl group Chemical group C1(=CC=CC2=NC=C3C=CC=CC3=C12)* 0.000 description 1
- 125000005562 phenanthrylene group Chemical group 0.000 description 1
- 125000001791 phenazinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3N=C12)* 0.000 description 1
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 description 1
- 125000001644 phenoxazinyl group Chemical group C1(=CC=CC=2OC3=CC=CC=C3NC12)* 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920000078 poly(4-vinyltriphenylamine) Polymers 0.000 description 1
- 229920000767 polyaniline Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 230000002250 progressing effect Effects 0.000 description 1
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 description 1
- 125000005412 pyrazyl group Chemical group 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical group C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 229910003449 rhenium oxide Inorganic materials 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 229910001925 ruthenium oxide Inorganic materials 0.000 description 1
- WOCIAKWEIIZHES-UHFFFAOYSA-N ruthenium(iv) oxide Chemical compound O=[Ru]=O WOCIAKWEIIZHES-UHFFFAOYSA-N 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 229910001923 silver oxide Inorganic materials 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 229910052712 strontium Inorganic materials 0.000 description 1
- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 229910001936 tantalum oxide Inorganic materials 0.000 description 1
- 125000006836 terphenylene group Chemical group 0.000 description 1
- 125000001935 tetracenyl group Chemical group C1(=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C12)* 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 125000000025 triisopropylsilyl group Chemical group C(C)(C)[Si](C(C)C)(C(C)C)* 0.000 description 1
- 229910001935 vanadium oxide Inorganic materials 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- OYQCBJZGELKKPM-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O-2].[Zn+2].[O-2].[In+3] OYQCBJZGELKKPM-UHFFFAOYSA-N 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- 229910001928 zirconium oxide Inorganic materials 0.000 description 1
Images
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- H10K85/633—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
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Definitions
- the present invention relates to an organic electroluminescence element and an electronic device.
- organic electroluminescence elements (hereinafter sometimes referred to as “organic EL elements”) are promising for use as solid-state, inexpensive, large-area full-color display elements, and many developments have been made.
- an organic EL element is composed of a light emitting layer and a pair of counter electrodes sandwiching the layer. When an electric field is applied between both electrodes, electrons are injected from the cathode side and holes are injected from the anode side. Further, the electrons recombine with holes in the light emitting layer to generate an excited state, and energy is emitted as light when the excited state returns to the ground state.
- An object of the present invention is to provide an organic EL element having high luminous efficiency and a long lifetime.
- an organic EL element having excellent luminous efficiency and lifetime by using a specific material for the light emitting layer of the organic EL element and the organic layer located between the anode and the light emitting layer.
- the present invention was completed.
- the following organic EL elements and the like are provided.
- An anode, an organic layer, a light emitting layer, and a cathode are provided in this order,
- the organic layer contains a compound represented by the following formula (20),
- the light emitting layer contains a compound represented by the following formula (1):
- Organic electroluminescence device Organic electroluminescence device.
- Ar 21 to Ar 24 are each a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms or a substituted or unsubstituted heteroaryl group having 5 to 50 ring carbon atoms.
- m is an integer from 0 to 4
- L 21 and L 22 are each a single bond, a substituted or unsubstituted arylene group having 6 to 18 ring carbon atoms, or a substituted or unsubstituted heteroarylene group having 5 to 15 ring carbon atoms;
- m is an integer of 2 or more, the plurality of Ar 23 may be the same or different, and the plurality of Ar 24 may be the same or different.
- Ar is a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms
- Each R a is a substituted or unsubstituted alkyl group having 1 to 15 carbon atoms or a substituted or unsubstituted cyclic alkyl group having 3 to 15 carbon atoms
- R b1 to R b4 are each a halogen atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 15 carbon atoms, a substituted or unsubstituted cyclic alkyl group having 3 to 15 carbon atoms, a substituted or unsubstituted carbon
- the plurality of R b1 When x is an integer of 2 or more, the plurality of R b1 may be the same or different, and when y is an integer of 2 or more, the plurality of R b2 may be the same or different, and z is When it is an integer of 2 or more, the plurality of R b3 may be the same or different, and the plurality of R b4 may be the same or different.
- the organic EL element which concerns on 1 aspect of this invention is equipped with an anode, an organic layer, a light emitting layer, and a cathode in this order.
- the organic layer includes a compound represented by Formula (20), and the light emitting layer includes a compound represented by Formula (1).
- the compounds contained in each layer will be described later.
- the organic layer containing the compound represented by the formula (20) is a layer located between the anode and the light emitting layer, and is usually a hole injection layer or a hole transport layer, preferably a hole transport layer.
- the organic layer is preferably adjacent to the light emitting layer.
- the organic EL device may be composed of only each of the above layers, or may be composed of other layers (for example, a hole injection layer, a hole transport layer, an electron injection layer, an electron transport layer, and a barrier layer).
- a hole injection layer for example, a hole injection layer, a hole transport layer, an electron injection layer, an electron transport layer, and a barrier layer.
- the hole transport zone is usually a zone including one or more layers selected from the group consisting of a hole injection layer and a hole transport layer.
- Each of the hole injection layer and the hole transport layer may be composed of one layer or two or more layers.
- Examples of the layer configuration of the hole transport zone include the following configurations (3) to (6). (3) hole transport layer (4) hole injection layer / hole transport layer (5) first hole transport layer / second hole transport layer (6) hole injection layer / first hole Transport layer / second hole transport layer
- one or more layers in each structure contain a compound represented by the formula (20).
- the electron transport band is usually a band including one or more layers selected from the group consisting of an electron injection layer and an electron transport layer.
- Each of the electron injection layer and the electron transport layer may be composed of one layer or two or more layers.
- FIG. 1 shows a schematic configuration of one embodiment of an organic EL element according to one aspect of the present invention.
- the organic EL element 1 includes a translucent substrate 2, an anode 3, a cathode 4, and a light emitting unit 10 disposed between the anode 3 and the cathode 4.
- the light emitting unit 10 includes a hole injection layer 6, a hole transport layer 7, a light emitting layer 5, an electron transport layer 8, and an electron injection layer 9 that are stacked in this order from the anode 3 side.
- the organic EL element 1 is a bottom emission type organic EL element in which light is emitted from the substrate 2 side.
- each layer which comprises an organic EL element is demonstrated.
- the light emitting layer contains a compound represented by the following formula (1).
- Ar is a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms
- Each R a is a substituted or unsubstituted alkyl group having 1 to 15 carbon atoms or a substituted or unsubstituted cyclic alkyl group having 3 to 15 carbon atoms
- R b1 to R b4 are each a halogen atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 15 carbon atoms, a substituted or unsubstituted cyclic alkyl group having 3 to 15 carbon atoms, a substituted or unsubstituted carbon
- the plurality of R b1 When x is an integer of 2 or more, the plurality of R b1 may be the same or different, and when y is an integer of 2 or more, the plurality of R b2 may be the same or different, and z is When it is an integer of 2 or more, the plurality of R b3 may be the same or different, and the plurality of R b4 may be the same or different.
- the compound represented by the formula (1) is preferably represented by the following formula (2).
- Ar, R a , R b1 to R b4 , R c1 to R c10 , x, z, and * are the same as in the formula (1).
- R c1 to R c10 are groups other than arylamino groups, that is, a hydrogen atom, a halogen atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 15 carbon atoms, a substituted or unsubstituted carbon number of 3;
- Substituted or unsubstituted aryloxy groups having 6 to 30 ring carbon atoms substituted or unsubstituted alkylthio groups having 1 to 15 carbon atoms, substituted or unsubstituted arylthio groups having 6 to 30 ring carbon atoms, substituted or Bonded to an unsubstituted aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 ring atoms, or a nitrogen atom
- the compound is a disubstituted product of an arylamino group.
- the compound represented by the formula (1) is preferably represented by the following formula (3), more preferably represented by the following formula (4).
- Ar, R a , R b1 to R b4 , R c2 to R c10 , x, z, and * are the same as those in the formula (1).
- R c2 to R c5 and R c7 to R c10 are each a hydrogen atom, a halogen atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 15 carbon atoms, or a substituted or unsubstituted cyclic group having 3 to 15 carbon atoms.
- Alkyl group substituted or unsubstituted alkylsilyl group having 1 to 45 carbon atoms, substituted or unsubstituted arylsilyl group having 6 to 50 carbon atoms, substituted or unsubstituted alkoxy group having 1 to 15 carbon atoms, substituted or unsubstituted Substituted aryloxy group having 6 to 30 carbon atoms, substituted or unsubstituted alkylthio group having 1 to 15 carbon atoms, substituted or unsubstituted arylthio group having 6 to 30 ring carbon atoms, substituted or unsubstituted ring An arylamino group having 6 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted ring atom number of 3 to 3 30 heteroaryl groups.
- the compound represented by the formula (1) is preferably represented by the following formula (5).
- Ar, R a , R b1 to R b4 , x and z are the same as those in the formula (1).
- R c2 , R c4 to R c10 are each a hydrogen atom, a halogen atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 15 carbon atoms, a substituted or unsubstituted cyclic alkyl group having 3 to 15 carbon atoms, Substituted or unsubstituted alkylsilyl group having 1 to 45 carbon atoms, substituted or unsubstituted arylsilyl group having 6 to 50 carbon atoms, substituted or unsubstituted alkoxy group having 1 to 15 carbon atoms, substituted or unsubstituted ring Aryloxy group having 6 to 30 carbon atoms, substituted or unsubstituted al
- R c7 is preferably a substituted or unsubstituted alkyl group having 1 to 15 carbon atoms or a substituted or unsubstituted cyclic alkyl group having 3 to 15 carbon atoms.
- the benzene ring-containing group to which R b1 is bonded and the benzene ring-containing group to which R b2 are bonded do not have a substituent at the para position relative to the bonding position with the N atom (that is, a hydrogen atom is bonded).
- a substituent at the para position relative to the bonding position with the N atom that is, a hydrogen atom is bonded.
- R b2 is bonded to R b2 is preferably not bonded to the para position with respect to the bonding position with the N atom.
- the compound according to one embodiment of the present invention is used as a light emitting layer dopant material of an organic EL device, the light emission wavelength is increased by having an alkyl group or an aryl group at this position, and the blue chromaticity of the obtained light emission is reduced. There is a risk.
- this position does not have an alkyl group or an aryl group. The above description does not prevent Rb1 and Ar from being substituted at the para position, and these may be substituted at the para position.
- Ar is preferably bonded to the para position relative to Ra .
- a benzene ring-containing group R b1 is attached is represented by the following formula (10)
- a benzene ring-containing group R b2 are bonded is represented by the following formula (11).
- the molecular arrangement in the light emitting layer of the compound represented by the formula (1) is optimized, and when used as a light emitting layer dopant material, energy transfer from the light emitting layer is preferable. Therefore, it is considered that more efficient light emission can be realized.
- Ar, R a , R b1 , R b2 and x are the same as those in the formula (1).
- R b3 and R b4 are preferably not bonded to the para position with respect to the bonding position with the N atom. That is, it is preferably bonded to the meta position or the ortho position with respect to the bonding position with the N atom, and preferably bonded to the ortho position.
- the benzene ring-containing group to which R b3 is bonded is preferably represented by the following formula (12)
- the benzene ring-containing group to which R b4 is bonded is preferably represented by the following formula (13).
- R b3 and R b4 are the same as those in formula (1).
- R b3 ′ and R b4 ′ are each a substituted or unsubstituted alkyl group having 1 to 15 carbon atoms or a substituted or unsubstituted cyclic alkyl group having 3 to 15 carbon atoms, z1 is an integer of 0 to 4, respectively.
- R a is preferably a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms.
- R b1 to R b4 are preferably groups other than electron-withdrawing groups, specifically, substituted or unsubstituted alkyl groups having 1 to 15 carbon atoms, substituted or unsubstituted C 3 to 15 carbon atoms, respectively.
- a heteroaryl group Preferably a heteroary
- R b1 - R b4 are each a substituted or unsubstituted alkyl group having 1 to 15 carbon atoms, a substituted or unsubstituted C 3-15 cyclic alkyl group, a substituted or unsubstituted C 1 -C 45 carbon atoms It is more preferably an alkylsilyl group, a substituted or unsubstituted arylsilyl group having 6 to 50 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms.
- R c1 to R c10 are a substituted or unsubstituted alkyl group having 1 to 15 carbon atoms, a substituted or unsubstituted cyclic alkyl group having 3 to 15 carbon atoms, and a substituted or unsubstituted alkylsilyl group having 1 to 45 carbon atoms.
- a substituted or unsubstituted arylsilyl group having 6 to 50 carbon atoms is preferred, and a substituted or unsubstituted alkyl group having 1 to 15 carbon atoms and a substituted or unsubstituted cyclic alkyl group having 3 to 15 carbon atoms are more preferred.
- the compound represented by the formula (1) is preferably a compound represented by any one of the following formulas.
- Each group in the formulas (4-2) and (5-2) is as described above.
- the hydrogen atom includes isotopes having different numbers of neutrons, that is, light hydrogen (protium), deuterium (deuterium), and tritium (tritium).
- the number of ring-forming carbon atoms constitutes the ring itself of a compound having a structure in which atoms are bonded cyclically (for example, a monocyclic compound, a condensed ring compound, a bridged compound, a carbocyclic compound, or a heterocyclic compound). Represents the number of carbon atoms in the atom.
- the carbon contained in the substituent is not included in the number of ring-forming carbons.
- the “ring-forming carbon number” described below is the same unless otherwise specified.
- a benzene ring has 6 ring carbon atoms
- a naphthalene ring has 10 ring carbon atoms
- a pyridinyl group has 5 ring carbon atoms
- a furanyl group has 4 ring carbon atoms.
- the carbon number of the alkyl group is not included in the number of ring-forming carbons.
- the carbon number of the fluorene ring as a substituent is not included in the number of ring-forming carbons.
- the number of ring-forming atoms means a compound (for example, a monocyclic compound, a condensed ring compound, a bridging compound, a carbocyclic compound, a heterocycle) having a structure in which atoms are bonded in a cyclic manner (for example, a monocyclic ring, a condensed ring, or a ring assembly).
- a compound for example, a monocyclic compound, a condensed ring compound, a bridging compound, a carbocyclic compound, a heterocycle
- a cyclic manner for example, a monocyclic ring, a condensed ring, or a ring assembly.
- the ring compound represents the number of atoms constituting the ring itself.
- An atom that does not constitute a ring for example, a hydrogen atom that terminates a bond of an atom that constitutes a ring
- an atom contained in a substituent when the ring is substituted by a substituent is not included in the number of ring-forming atoms.
- the “number of ring-forming atoms” described below is the same unless otherwise specified.
- the pyridine ring has 6 ring atoms
- the quinazoline ring has 10 ring atoms
- the furan ring has 5 ring atoms.
- a hydrogen atom bonded to a carbon atom of a pyridine ring or a quinazoline ring or an atom constituting a substituent is not included in the number of ring-forming atoms. Further, when, for example, a fluorene ring is bonded to the fluorene ring as a substituent (including a spirofluorene ring), the number of atoms of the fluorene ring as a substituent is not included in the number of ring-forming atoms.
- the “carbon number XX to YY” in the expression “substituted or unsubstituted ZZ group having XX to YY” represents the number of carbon atoms in the case where the ZZ group is unsubstituted. The carbon number of the substituent in the case where it is present is not included.
- “YY” is larger than “XX”, and “XX” and “YY” each mean an integer of 1 or more.
- atom number XX to YY in the expression “a ZZ group having a substituted or unsubstituted atom number XX to YY” represents the number of atoms when the ZZ group is unsubstituted. In this case, the number of substituent atoms is not included.
- YY is larger than “XX”, and “XX” and “YY” each mean an integer of 1 or more.
- unsubstituted means that a hydrogen atom is bonded without being substituted with the above substituent.
- alkyl group examples include methyl group, ethyl group, propyl group, isopropyl group, n-butyl group, s-butyl group, isobutyl group, t-butyl group, n-pentyl group, n-hexyl group, n-heptyl group, An n-octyl group and the like can be mentioned.
- the alkyl group preferably has 1 to 10 carbon atoms, and more preferably 1 to 6 carbon atoms.
- methyl, ethyl, propyl, isopropyl, n-butyl, s-butyl, isobutyl, t-butyl, n-pentyl and n-hexyl are preferred.
- cyclic alkyl group examples include cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, 4-methylcyclohexyl group, adamantyl group, norbornyl group and the like.
- the number of ring-forming carbon atoms is preferably 3 to 10, more preferably 3 to 8, and still more preferably 5 to 8. Also, it may be 3-6.
- aryl group for example, phenyl group, naphthyl group, anthryl group, phenanthryl group, naphthacenyl group, pyrenyl group, chrysenyl group, benzo [c] phenanthryl group, benzo [g] chrycenyl group, triphenylenyl group, fluorenyl group, benzofuryl group
- aryl group preferably has 6 to 20 ring carbon atoms, more preferably 6 to 12, and among the aryl groups described above, a phenyl group and a biphenyl group are particularly preferable.
- the alkylsilyl group is represented by —SiY 3, and examples of Y include the above examples of alkyl.
- examples of the alkylsilyl group include a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group, and a triisopropylsilyl group.
- the arylsilyl group is a silyl group substituted with 1 to 3 aryl groups, and examples of the aryl group include the above examples of aryl. In addition to the aryl group, the above alkyl group may be substituted. Examples of the arylsilyl group include a triphenylsilyl group and a phenyldimethylsilyl group.
- the alkoxy group is represented as —OY, and examples of Y include the above alkyl examples.
- the alkoxy group is, for example, a methoxy group or an ethoxy group.
- the aryloxy group is represented by —OZ, and examples of Z include the above aryl groups.
- the aryloxy group is, for example, a phenoxy group.
- the alkylthio group is represented by —SY, and examples of Y include the above alkyl examples.
- the arylthio group is represented by —SZ, and examples of Z include the above examples of aryl groups.
- the arylamino group is represented as —NZ 2, and examples of Z include the examples of the aryl group described above.
- heteroaryl groups include pyrrolyl, triazinyl, pyrazinyl, pyrimidinyl, pyridinyl, indolyl, isoindolyl, imidazolyl, furyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, dibenzofuran, Thiophenyl group, quinolyl group, isoquinolyl group, quinoxalinyl group, carbazolyl group, phenanthridinyl group, acridinyl group, phenanthrolinyl group, phenazinyl group, phenothiazinyl group, phenoxazinyl group, oxazolyl group, oxadiazolyl group, flazanyl group, A thienyl group, a benzothiophenyl group, etc. are mentioned.
- the number of ring-forming atoms of the heteroaryl group is preferably 5 to 20, and more preferably 5 to 14.
- the heteroaryl group is preferably a dibenzofuranyl group, a dibenzothiophenyl group, or a carbazolyl group, more preferably a 1-dibenzofuranyl group, a 2-dibenzofuranyl group, a 3-dibenzofuranyl group, 4 -Dibenzofuranyl group, 1-dibenzothiophenyl group, 2-dibenzothiophenyl group, 3-dibenzothiophenyl group, 4-dibenzothiophenyl group.
- X and Y are each an oxygen atom, a sulfur atom or a —NRa— group.
- Ra is a hydrogen atom or a group similar to R b1 to R b4 above.
- halogen atom examples include fluorine, chlorine, bromine, iodine, and the like, preferably a fluorine atom.
- substituents may be further substituted with the above substituents.
- a plurality of these substituents may be bonded to each other to form a ring.
- the compound represented by the formula (1) can be synthesized by a known method. Examples of the compound represented by the formula (1) are shown below.
- the compound represented by the formula (1) is preferably any one selected from the group consisting of the following compounds.
- a light emitting layer may be comprised only from the compound represented by Formula (1), and may contain another compound.
- the content of the compound (1) is not particularly limited, but for example, 0.1 to 70 with respect to the entire light emitting layer.
- the content may be 1% by mass, preferably 1 to 20% by mass, more preferably 1 to 10% by mass, and particularly preferably 1 to 4% by mass.
- the light emitting layer preferably contains a compound represented by the formula (1) and an anthracene derivative represented by the following formula (5).
- the compound represented by Formula (1) is contained as a dopant
- the anthracene derivative represented by Formula (5) is contained as a host.
- Ar 11 and Ar 12 are each a substituted or unsubstituted monocyclic group having 5 to 50 ring atoms, a substituted or unsubstituted condensed ring group having 8 to 50 ring atoms, or It is a group composed of a combination of a monocyclic group and a condensed ring group.
- R 101 to R 108 are each a hydrogen atom, a monocyclic group having 5 to 50 (preferably 5 to 30, more preferably 5 to 20, and still more preferably 5 to 12) ring-substituted or unsubstituted ring atoms;
- R 101 ⁇ R 108 is a hydrogen atom, or one of R 101 and R 108, one of R 104 and R 106, both of R 101 and R 106, or both by R 108 and R 104, Monocyclic group having 5 to 50 ring atoms (preferably phenyl group, biphenylyl group, terphenylyl group), substituted or unsubstituted alkyl group having 1 to 50 carbon atoms (preferably methyl group, ethyl group, n- A group selected from the group consisting of a propyl group, an isopropyl group, an n-butyl group, an isobutyl group, an s-butyl group, a t-butyl group) and a substituted silyl group (preferably a trimethylsilyl group). More preferably, all of 101 to R 108 are hydrogen atoms.
- the monocyclic group in the formula (5) is a group composed only of a ring structure having no fused ring structure.
- Specific examples of the monocyclic group having 5 to 50 ring atoms include aromatic groups such as phenyl group, biphenylyl group, terphenylyl group, quarterphenylyl group, pyridyl group, pyrazyl group, pyrimidyl group, triazinyl group, furyl group.
- heterocyclic groups such as a thienyl group are preferred.
- a phenyl group, a biphenylyl group, and a terphenylyl group are preferable.
- the condensed ring group is a group in which two or more ring structures are condensed.
- the condensed ring group having 8 to 50 ring atoms include naphthyl group, phenanthryl group, anthryl group, chrysenyl group, benzoanthryl group, benzophenanthryl group, triphenylenyl group, benzocrisenyl group, indenyl group, fluorenyl Group, benzofluorenyl group, dibenzofluorenyl group, fluoranthenyl group, benzofluoranthenyl group and other condensed aromatic ring groups, benzofuranyl group, benzothiophenyl group, indolyl group, dibenzofuranyl group, dibenzo A condensed heterocyclic group such as a thiophenyl group, a carbazolyl group, a quinolyl group, or a phenanthrolinyl group is preferred.
- the fluorenyl group may have one or two substituents at the 9-position, and examples of the substituent include an alkyl group, an aryl group, an alkylsilyl group, an arylsilyl group, and an alkoxy group. . Specific examples of such a fluorenyl group include a 9,9-dimethylfluorenyl group and a 9,9-diphenylfluorenyl group.
- a fluorenyl group when it is described as a fluorenyl group, it may have the same substituent unless otherwise specified.
- Examples of the condensed ring group include naphthyl group, phenanthryl group, anthryl group, fluorenyl group (specifically, 9,9-dimethylfluorenyl group, etc.), fluoranthenyl group, benzoanthryl group, dibenzothiol.
- a phenyl group, a dibenzofuranyl group, and a carbazolyl group are preferable.
- an alkyl group, a cycloalkyl group (cyclic alkyl group), an alkoxy group, an alkyl part and an aryl part of an aralkyl group, an aryloxy group, a substituted silyl group (an alkylsilyl group, an arylsilyl group), a halogen atom Specific examples are the same as the specific examples of each group in the above formula (1) and substituents in “substituted or unsubstituted...
- the aralkyl group is represented by —Y—Z.
- Y include alkylene examples corresponding to the above alkyl examples, and examples of Z include the above aryl examples.
- the aralkyl group has 7 to 50 carbon atoms (the aryl moiety has 6 to 49 carbon atoms (preferably 6 to 30, more preferably 6 to 20, particularly preferably 6 to 12), and the alkyl moiety has 1 to 44 carbon atoms. (Preferably 1-30, more preferably 1-20, still more preferably 1-10, particularly preferably 1-6)), for example, benzyl group, phenylethyl group, 2-phenylpropane-2- It is an yl group.
- substituents of “substituted or unsubstituted” for Ar 11 , Ar 12 , R 1 to R 8 monocyclic groups, condensed ring groups, alkyl groups, cycloalkyl groups, silyl groups, alkoxy groups, cyano groups, halogen atoms (Especially fluorine) is preferable, particularly preferably a monocyclic group or a condensed ring group, and preferable specific substituents are as described above.
- the above-mentioned monocyclic group or condensed ring group is preferable as the substituent for Ar 11 and Ar 12 .
- the anthracene derivative represented by the formula (5) is preferably any of the following anthracene derivatives (A), (B), and (C), and is selected depending on the configuration of the organic EL element to be applied and the required characteristics.
- Ar 11 and Ar 12 in the formula (5) are each a substituted or unsubstituted condensed ring group having 8 to 50 ring atoms.
- Ar 11 and Ar 12 may be the same or different.
- Anthracene derivatives which are substituted or unsubstituted condensed ring groups in which Ar 11 and Ar 12 in formula (5) are different (including the difference in the position to which the anthracene ring is bonded) are particularly preferred.
- Preferred examples of the condensed ring are as described above. It is. Of these, a naphthyl group, a phenanthryl group, a benzanthryl group, a fluorenyl group (specifically, 9,9-dimethylfluorenyl group, etc.) and a dibenzofuranyl group are preferable.
- Ar 11 and Ar 12 in Formula (5) is a substituted or unsubstituted monocyclic group having 5 to 50 ring atoms, and the other of Ar 11 and Ar 12 is substituted or unsubstituted.
- Ar 12 is a naphthyl group, phenanthryl group, benzoanthryl group, fluorenyl group (specifically, 9,9-dimethylfluorenyl group, etc.), or dibenzofuranyl group
- Ar 11 is an unsubstituted phenyl group, a monocyclic group or a condensed ring group (for example, a phenyl group, a biphenyl group, a naphthyl group, a phenanthryl group, a fluorenyl group (specifically, 9,9-dimethylfluorene group).
- anthracene derivative (B) is a derivative in which Ar 12 is a substituted or unsubstituted condensed ring group having 8 to 50 ring-forming atoms, and Ar 11 is an unsubstituted phenyl group.
- the condensed ring group is particularly preferably a phenanthryl group, a fluorenyl group (specifically, 9,9-dimethylfluorenyl group, etc.), a dibenzofuranyl group, or a benzoanthryl group.
- Ar 11 and Ar 12 in the formula (5) are each a substituted or unsubstituted monocyclic group having 5 to 50 ring atoms.
- Preferable forms of the anthracene derivative (C) include derivatives in which both Ar 11 and Ar 12 are substituted or unsubstituted phenyl groups.
- Ar 11 is an unsubstituted phenyl group
- Ar 12 is a phenyl group substituted with a monocyclic group or a condensed ring group
- Ar 11 and Ar 12 are each a monocyclic group or a condensed ring.
- Specific examples of the preferred monocyclic group and condensed ring group as the substituent are as described above. More preferable monocyclic groups as a substituent are a phenyl group and a biphenyl group, and more preferable condensed ring groups as a substituent are a naphthyl group, a phenanthryl group, a fluorenyl group (specifically, 9,9-dimethylfluorine). An oleenyl group), a dibenzofuranyl group, and a benzoanthryl group.
- anthracene derivative represented by the formula (5) include the following.
- the organic layer (usually one or more organic layers constituting the hole transport zone) located between the anode and the light-emitting layer is represented by the following formula (20).
- the compound represented by these is included.
- Ar 21 to Ar 24 are each a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms or a substituted or unsubstituted heteroaryl group having 5 to 50 ring carbon atoms.
- m is an integer from 0 to 4
- L 21 and L 22 are each a single bond, a substituted or unsubstituted arylene group having 6 to 18 ring carbon atoms, or a substituted or unsubstituted heteroarylene group having 5 to 15 ring carbon atoms;
- m is an integer of 2 or more
- the plurality of Ar 23 may be the same or different
- the plurality of Ar 24 may be the same or different.
- adjacent Ar 21 to Ar 24 may form a ring. That is, Ar 21 and Ar 22 adjacent to each other may be bonded to form a ring. Adjacent Ar 23 and Ar 24 may be bonded to each other to form a ring.
- Ar 21 to Ar 24 include phenyl, biphenyl, terphenyl, naphthyl, anthryl, phenanthryl, fluorenyl, indenyl, pyrenyl, acetonaphthenyl, fluoranthenyl, triphenylenyl, Pyridyl group, pyranyl group, quinolyl group, isoquinolyl group, benzofuranyl group, benzothienyl group, indolyl group, carbazolyl group, benzoxazolyl group, benzothiazolyl group, quinoxalyl group, benzoimidazolyl group, dibenzofuranyl group, dibenzothienyl group, etc. Can be mentioned.
- Preferable examples include a phenyl group, a biphenyl group, a terphenyl group, a fluorenyl group, a carbazolyl group, and a dibenzofuranyl group.
- L 21 and L 22 in addition to a single bond, specifically, a phenylene group, a biphenylylene group, a terphenylylene group, a naphthylene group, an anthrylene group, a phenanthrylene group, a fluorylene group, an indandiyl group, a pyrenediyl group, an acenaphthenediyl group, Fluoranthene diyl group, triphenylene diyl group, pyridine diyl group, pyrandiyl group, quinoline diyl group, isoquinoline diyl group, benzofurandiyl group, benzothiophene diyl group, indole diyl group, carbazole diyl group, benzoxazole diyl group, benzothiazole diyl group Quinoxaline diyl group, benzimidazole diyl group, dibenzofurandiyl group and the like.
- substituents in “substituted or unsubstituted...” include the groups listed in the above formula (1). These substituents may be further substituted with similar substituents. A plurality of these substituents may be bonded to each other to form a ring.
- the compound represented by the formula (20) can be synthesized by a known method.
- Examples of the compound represented by the formula (20) include the following compounds. However, it is not necessarily limited to the following compounds.
- the compound represented by the formula (20) is preferably any one selected from the group consisting of the following compounds.
- anode It is preferable to use a metal, an alloy, an electrically conductive compound, a mixture thereof, or the like having a high work function (specifically, 4.0 eV or more) for the anode.
- a metal, an alloy, an electrically conductive compound, a mixture thereof, or the like having a high work function (specifically, 4.0 eV or more) for the anode.
- ITO indium tin oxide
- ITO indium oxide-tin oxide containing silicon or silicon oxide
- indium oxide-zinc oxide silicon oxide
- tungsten oxide tungsten oxide
- indium oxide containing zinc oxide and graphene.
- gold (Au) platinum (Pt), a nitride of a metal material (for example, titanium nitride), or the like can be given.
- the hole injection layer is a layer containing a material having a high hole injection property (hole injection material).
- Hole injection materials include molybdenum oxide, titanium oxide, vanadium oxide, rhenium oxide, ruthenium oxide, chromium oxide, zirconium oxide, hafnium oxide, tantalum oxide, silver oxide, tungsten oxide Products, manganese oxides, and the like can be used.
- Polymer compounds (oligomers, dendrimers, polymers, etc.) can also be used.
- poly (N-vinylcarbazole) (abbreviation: PVK)
- poly (4-vinyltriphenylamine) (abbreviation: PVTPA)
- PVTPA poly (4-vinyltriphenylamine)
- PTPDMA poly [N- (4- ⁇ N ′-[4- (4-diphenylamino)] Phenyl] phenyl-N′-phenylamino ⁇ phenyl) methacrylamide]
- PTPDMA poly [N, N′-bis (4-butylphenyl) -N, N′-bis (phenyl) benzidine]
- Polymer compounds such as Poly-TPD).
- a polymer compound to which an acid such as poly (3,4-ethylenedioxythiophene) / poly (styrene sulfonic acid) (PEDOT / PSS), polyaniline / poly (styrene sulfonic acid) (PAni / PSS) is added is properly used. It can also be used as a hole injecting material.
- acceptor materials such as a hexaazatriphenylene (HAT) compound represented by the following formula (K) can also be used as the hole injecting material.
- HAT hexaazatriphenylene
- R 31 to R 36 are each a cyano group, —CONH 2 , a carboxyl group, or —COOR 37 (R 37 is an alkyl group having 1 to 20 carbon atoms or a cyclohexane having 3 to 20 carbon atoms).
- R 31 and R 32 , R 33 and R 34 , and R 35 and R 36 two adjacent groups are bonded to each other and represented by —CO—O—CO—.
- R 37 examples include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a t-butyl group, a cyclopentyl group, and a cyclohexyl group.
- hole injecting material examples include a compound represented by the following (2-1) and a compound represented by (2-2).
- Ar 31 represents a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 30 ring carbon atoms or a substituted or unsubstituted ring atom having 5 to 30 ring atoms.
- the aromatic hydrocarbon ring is preferably a benzene ring.
- the aromatic heterocyclic ring is preferably a ring having 6 ring atoms, for example, a pyridine ring, a pyrazine ring, or a pyridazine ring.
- X 23 to X 28 are each C (R) or a nitrogen atom.
- R is a hydrogen atom, halogen atom, hydroxyl group, cyano group, substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, substituted or unsubstituted A mono-, di- or tri-substituted silyl group having one or more substituents selected from the group consisting of an alkyl group having 1 to 30 carbon atoms and a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, An alkoxy group having a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having an aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstitute
- alkyl group aryl group, alkoxy group, aryloxy group, alkylthio group, arylthio group, and heteroaryl group
- silyl group examples include groups substituted with one or more groups selected from the group consisting of the above alkyl groups and aryl groups.
- amino group examples include groups substituted with one or more groups selected from the group consisting of the above alkyl groups and aryl groups.
- substituents in “substituted or unsubstituted...” include the groups listed in the above formula (1). These substituents may be further substituted with similar substituents. A plurality of these substituents may be bonded to each other to form a ring.
- a 21 to a 23 are ring structures represented by the following formula (2b).
- X 20 in the formula (2b) is represented by any of the following formulas (2b-1) to (2b-12). (In the formulas (2b-1) to (2b-12), R 20 has the same meaning as R.)
- R 23 to R 28 have the same meanings as R.
- the hole injection layer may further include a compound composed of 2 to 6 aromatic 6-membered rings and a connecting portion that includes the structure represented by the formula (2a) and connects the aromatic 6-membered rings. it can.
- each X is a group represented by the following formula.
- R 200 -C * -CN (In the above formula, C * is a carbon atom bonded to the cyclopropane of formula (2) by a double bond.
- R 200 is an aromatic 6-membered ring, a halogen atom, a substituted or unsubstituted fluoroalkyl group, respectively. And an aromatic 6-membered ring substituted with one or more selected from a substituted or unsubstituted fluoroalkoxy group and a cyano group.
- each group quoted by said Formula (1) is mentioned.
- the aromatic 6-membered ring include 6-membered rings among the aryl groups and heteroaryl groups mentioned in the above formula (1).
- a fluoroalkyl group the group which combined the alkyl group quoted by the said Formula (1), and the fluorine atom is mentioned.
- the fluoroalkoxy group include groups obtained by combining the alkoxy group exemplified in the above formula (1) and a fluorine atom.
- substituents in “substituted or unsubstituted...” include the groups listed in the above formula (1). These substituents may be further substituted with similar substituents. A plurality of these substituents may be bonded to each other to form a ring.
- R 200 in formula (2) is preferably perfluoropyridin-4-yl, tetrafluoro-4- (trifluoromethyl) phenyl group, 4-cyanoperfluorophenyl, dichloro-3,5-difluoro-4- (tri Fluoromethyl) phenyl or perfluorophenyl.
- the single hole injection layer may contain a compound represented by the formula (20), or the single hole injection layer is the above-mentioned And a compound represented by the formula (20) may be included, or a hole injection layer containing the above compound and a hole injection layer containing a compound represented by the formula (20) may be provided separately. Good.
- an aromatic amine compound for example, an aromatic amine derivative represented by the following formula (H) is preferably used.
- Ar 211 to Ar 214 each represents a substituted or unsubstituted aryl having 6 to 50 ring carbon atoms (preferably 6 to 30, more preferably 6 to 20, more preferably 6 to 12).
- Ar 211 and Ar 212 , Ar 213 and Ar 214 may combine with each other to form a saturated or unsaturated ring structure.
- L 211 represents an arylene group having a substituted or unsubstituted ring-forming carbon number of 6 to 50 (preferably 6 to 30, more preferably 6 to 20, more preferably 6 to 12), a substituted or unsubstituted ring forming carbon number.
- 10 to 50 (preferably 10 to 30, more preferably 10 to 20) fused arylene group, substituted or unsubstituted 5 to 50 ring atoms (preferably 5 to 30, more preferably 5 to 20, more preferably)
- the aryl group quoted by the said Formula (1) and the bivalent group corresponding to it are mentioned.
- the condensed aryl group and the condensed arylene group include a condensed aryl group and a corresponding divalent group among the condensed rings mentioned in the above formula (5).
- the heteroaryl group and the heteroarylene group include the heteroaryl group exemplified in the above formula (1) and the corresponding divalent group.
- Examples of the condensed heteroaryl group and the condensed heteroarylene group include a condensed heteroaryl group and a corresponding divalent group among the condensed rings mentioned in the above formula (5).
- substituents in “substituted or unsubstituted...” include the groups listed in the above formula (1). These substituents may be further substituted with similar substituents. A plurality of these substituents may be bonded to each other to form a ring.
- aromatic amines of the following formula (J) are also suitably used for forming the hole transport layer.
- Ar 221 to Ar 223 each represents a substituted or unsubstituted aryl having 6 to 50 ring carbon atoms (preferably 6 to 30, more preferably 6 to 20, more preferably 6 to 12).
- the single hole transport layer may contain a compound represented by the formula (20), or the single hole transport layer is the above-mentioned Or a compound represented by formula (20) may be included, or a hole transport layer containing the above compound and a hole transport layer containing a compound represented by formula (20) may be provided separately.
- the thickness of the hole transport layer in contact with the light emitting layer is not particularly limited, but may be 0.1 to 20 nm, for example. Yes, 20 nm or less, preferably 10 nm or less, more preferably 5 nm or less.
- the organic layer containing the compound represented by formula (20) is preferably a hole transport layer.
- it is preferable that the organic layer containing the compound represented by Formula (20) is adjacent to the light emitting layer.
- the electron transport layer is a layer containing a material having a high electron transport property (electron transport material).
- electron transport material include the following compounds (1) to (3).
- Metal complexes such as aluminum complexes, beryllium complexes, zinc complexes
- Heteroaromatic compounds such as imidazole derivatives, benzimidazole derivatives, azine (nitrogen-containing six-membered ring) derivatives, carbazole derivatives, phenanthroline derivatives (3)
- Molecular compound (1) such as aluminum complexes, beryllium complexes, zinc complexes
- Heteroaromatic compounds such as imidazole derivatives, benzimidazole derivatives, azine (nitrogen-containing six-membered ring) derivatives, carbazole derivatives, phenanthroline derivatives
- the electron transport layer preferably contains a carbazole derivative
- the carbazole derivative is preferably a compound containing a carbazole ring and a nitrogen-containing six-membered ring.
- the nitrogen-containing 6-membered ring in the compound containing a carbazole ring and a nitrogen-containing 6-membered ring include a pyrimidine ring, a triazine ring, and a pyridine ring, and a pyrimidine ring is particularly preferable.
- an electron carrying layer contains the compound represented by a following formula (M).
- Ar 231 and Ar 232 are each a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms or a substituted or unsubstituted heteroaryl group having 5 to 50 ring carbon atoms. is there.
- R 231 and R 232 are each a substituent. When two or more R 231 are present, the two or more R 231 may be the same or different. When two or more R 232 are present, the two or more R 232 may be the same or different.
- X 1 to X 3 are each N, CH or C (R 233 ), and at least two of X 1 to X 3 are N.
- R 233 is a substituent, and when two or more R 233 are present, two or more R 233 may be the same or different.
- L 231 is a substituted or unsubstituted arylene group having 6 to 18 ring carbon atoms or a substituted or unsubstituted heteroarylene group having 5 to 15 ring carbon atoms, and when L 231 is 2 or more, 2 The above L 231 may be the same or different.
- m1 is an integer of 0 to 3.
- m2 is an integer of 1 to 5.
- m3 and m4 are each an integer of 0 to 4. )
- the aryl group having 6 to 50 ring carbon atoms and the heteroaryl group having 5 to 50 ring carbon atoms of Ar 231 and Ar 232 include an aryl group having 6 to 50 ring carbon atoms of Ar 21 to Ar 24 and ring formation. Examples thereof include those similar to heteroaryl groups having 5 to 50 carbon atoms. Examples of the arylene group having 6 to 18 ring carbon atoms and the heteroarylene group having 5 to 15 ring carbon atoms of L 231 include an arylene group having 6 to 18 ring carbon atoms and a ring carbon number of 5 to L 21 and L 22 Examples are the same as those described above for the heteroarylene group of ⁇ 15. When two or more R 231 are present, adjacent R 231 may be bonded to each other to form a ring. If R 232 is present 2 or more, each other R 232 adjacent may be bonded to each other to form a ring.
- R 231 to R 233 examples include the groups exemplified in the above formula (1). These substituents may be further substituted with similar substituents.
- substituents in “substituted or unsubstituted...” include the groups listed in the above formula (1). These substituents may be further substituted with similar substituents. A plurality of these substituents may be bonded to each other to form a ring.
- the compound represented by the formula (M) can be synthesized by a known method.
- the electron transporting material is a material mainly having an electron mobility of 10 ⁇ 6 cm 2 / Vs or higher. Note that any material having a higher electron transporting property than a hole transporting property may be used for the electron transporting layer.
- the electron transport layer is not limited to a single layer, and two or more layers may be stacked.
- the electron injection layer is a layer containing a material having a high electron injection property.
- a material having a high electron injection property lithium (Li), cesium (Cs), calcium (Ca), lithium fluoride (LiF), cesium fluoride (CsF), calcium fluoride (CaF 2 ), lithium oxide (LiOx), etc.
- Alkali metals, alkaline earth metals, or compounds thereof can be used.
- a material containing an electron transporting property containing an alkali metal, an alkaline earth metal, or a compound thereof, specifically, a material containing magnesium (Mg) in Alq may be used. In this case, electron injection from the cathode can be performed more efficiently.
- a composite material obtained by mixing an organic compound and an electron donor (donor) may be used for the electron injection layer.
- Such a composite material is excellent in electron injecting property and electron transporting property because the organic compound receives electrons from the electron donor.
- the organic compound is preferably a material that is excellent in transporting received electrons.
- a material a metal complex, a heteroaromatic compound, or the like
- the electron donor may be any material that exhibits an electron donating property with respect to the organic compound.
- alkali metals, alkaline earth metals, and rare earth metals are preferable, and lithium, cesium, magnesium, calcium, erbium, ytterbium, and the like can be given.
- Alkali metal oxides and alkaline earth metal oxides are preferable, and lithium oxide, calcium oxide, barium oxide, and the like can be given.
- a Lewis base such as magnesium oxide can also be used.
- an organic compound such as tetrathiafulvalene (abbreviation: TTF) can be used.
- cathode For the cathode, it is preferable to use a metal, an alloy, an electrically conductive compound, a mixture thereof, or the like having a small work function (specifically, 3.8 eV or less).
- a cathode material include elements belonging to Group 1 or Group 2 of the periodic table of elements, that is, alkali metals such as lithium (Li) and cesium (Cs), and magnesium (Mg), calcium ( Examples thereof include alkaline earth metals such as Ca) and strontium (Sr), and alloys containing these (for example, rare earth metals such as MgAg and AlLi), europium (Eu) and ytterbium (Yb), and alloys containing these.
- a vacuum evaporation method or a sputtering method can be used.
- coating method, the inkjet method, etc. can be used.
- a cathode is formed using various conductive materials such as indium oxide-tin oxide containing Al, Ag, ITO, graphene, silicon, or silicon oxide regardless of the work function. can do. These conductive materials can be formed by a sputtering method, an inkjet method, a spin coating method, or the like.
- the substrate is also preferably transparent.
- the transparent electrode is set using the above-described conductive material so that predetermined translucency is ensured by a method such as vapor deposition or sputtering.
- the electrode on the light emitting surface preferably has a light transmittance of 10% or more.
- the substrate for example, glass, quartz, plastic, or the like can be used.
- a flexible substrate may be used.
- the flexible substrate is a substrate that can be bent (flexible), and examples thereof include a plastic substrate made of polycarbonate or polyvinyl chloride.
- Each layer of the organic EL element can be formed by any of dry film forming methods such as vacuum deposition, sputtering, plasma, and ion plating, and wet film forming methods such as spin coating, dipping, and flow coating.
- the thickness of each layer is not particularly limited, but must be set to an appropriate thickness. If the film thickness is too thick, a large applied voltage is required to obtain a constant light output, and the efficiency may deteriorate. If the film thickness is too thin, pinholes and the like are generated, and there is a possibility that sufficient light emission luminance cannot be obtained even when an electric field is applied.
- the film thickness is usually preferably 1 nm to 10 ⁇ m, and may be 5 nm to 0.2 ⁇ m.
- an appropriate resin or additive may be used for improving the film formability and preventing pinholes in the film.
- the organic EL element according to one embodiment of the present invention may be a bottom emission type (FIG. 1) in which light is extracted from the substrate side, or may be a top emission type in which light is extracted from the cathode side.
- FOG. 1 bottom emission type
- top emission type in which light is extracted from the cathode side.
- the light emitting unit portion (the light emitting unit 10 in FIG. 1) sandwiched between the anode and the cathode can have the same configuration as the bottom emission type.
- the anode and cathode are as follows.
- the anode material is preferably a metal such as Ag, Al, or Au, or a metal alloy such as APC (Ag—Pd—Cu). These metal materials and metal alloys may be laminated. Further, a transparent electrode layer such as indium tin oxide (ITO) or indium zinc oxide may be formed on the upper surface and / or the lower surface of the metal, metal alloy, or laminated structure thereof.
- a metal such as Ag, Al, or Au
- APC Au—Pd—Cu
- a transparent electrode layer such as indium tin oxide (ITO) or indium zinc oxide may be formed on the upper surface and / or the lower surface of the metal, metal alloy, or laminated structure thereof.
- a metallic material can be used as the cathode.
- the metallic material means a material having a negative real part of dielectric constant. Such materials include not only metals but also organic transparent electrode materials and inorganic transparent electrode materials that exhibit a metallic luster other than metal.
- the metal those formed of Ag, Mg, Al, Ca and the like and alloys thereof are preferable.
- the transmissivity in the front direction is preferably 20% or more and translucent.
- the film thickness is preferably 30 nm or less in order to exhibit sufficient light transmittance.
- a capping layer may be provided on the top of the cathode. By providing the capping layer, it is possible to adjust the peak intensity and peak wavelength of light emission.
- the compound that can be used for the capping layer is a compound whose molecular formula includes a carbon atom and a hydrogen atom as constituent elements, and includes an oxygen atom, a nitrogen atom, a fluorine atom, a silicon atom, a chlorine atom, a bromine atom, and an iodine atom. It is also a compound that may have a substituent.
- Examples of preferable materials include the following compounds.
- (I) A compound whose molecular formula contains carbon atoms and hydrogen atoms as constituent elements, which may contain oxygen atoms, nitrogen atoms, fluorine atoms, silicon atoms, chlorine atoms, bromine atoms, iodine atoms, and have substituents
- Aromatic hydrocarbon compound (ii) The compound whose molecular formula contains a carbon atom and a hydrogen atom as constituent elements, wherein an oxygen atom, nitrogen atom, fluorine atom, silicon atom, chlorine atom, bromine atom, iodine atom
- An aromatic heterocyclic compound which may contain and may have a substituent (iii) is a compound in which the molecular formula includes a carbon atom and a hydrogen atom as constituent elements, and includes an oxygen atom, a nitrogen atom, a fluorine atom, a silicon atom,
- An amine compound which may contain a chlorine atom, a bro
- the film thickness of the capping layer is preferably 200 nm or less, more preferably 20 nm or more and 200 nm or less, and further preferably 40 nm or more and 140 nm or less.
- FIG. 2 shows a schematic configuration of an example of an organic EL element provided with a capping layer.
- the organic EL element 100 includes an anode 3, a light emitting unit 10, a cathode 4, and a capping layer 20 in this order on a substrate 2, and is configured to extract light from the capping layer 20 side.
- the light emitting unit 10 is as described in FIG.
- the organic EL device can be used for a flat light emitter such as a flat panel display of a wall-mounted television, a light source such as a copying machine, a printer, a backlight of a liquid crystal display or instruments, a display board, a marker lamp, and the like.
- the compound according to one embodiment of the present invention can be used not only in an organic EL element but also in fields such as an electrophotographic photosensitive member, a photoelectric conversion element, a solar cell, and an image sensor.
- Example 1 Manufacture of bottom emission type organic EL devices
- a 25 mm ⁇ 75 mm ⁇ 1.1 mm thick glass substrate with ITO transparent electrode (anode) (manufactured by Geomatic) was subjected to ultrasonic cleaning in isopropyl alcohol for 5 minutes and then UV (ultraviolet) ozone cleaning for 30 minutes. .
- the film thickness of the ITO transparent electrode was 130 nm.
- a glass substrate with a transparent electrode line after washing is mounted on a substrate holder of a vacuum vapor deposition apparatus, and first, compound HI-1 is vapor-deposited so as to cover the transparent electrode on the surface where the transparent electrode line is formed.
- a hole injection layer having a thickness of 5 nm was formed.
- Compound 1 was deposited to form a first hole transport layer having a thickness of 90 nm.
- Compound 4 was deposited to form a second hole transport layer having a thickness of 10 nm.
- Compound BH-1 (host material) and compound BD-1 (dopant material) are co-evaporated on the second hole transport layer so that the ratio of BD-1 is 4% by mass, and light emission with a film thickness of 20 nm is achieved. Layers were deposited.
- Compound 6 was deposited on the light emitting layer to form a first electron transport layer having a thickness of 5 nm.
- Compound 7 was deposited on the first electron transport layer to form a second electron transport layer having a thickness of 20 nm.
- LiF was vapor-deposited on the second electron transport layer to form an electron injection layer having a thickness of 1 nm.
- a metal Al was vapor-deposited on the electron injection layer to form a cathode having a thickness of 80 nm.
- An organic EL device was manufactured as described above. The compounds used in Example 1 and Examples and Comparative Examples described below are shown below.
- Examples 2-7 Comparative Example 1 [Manufacture and evaluation of bottom emission type organic EL elements]
- Table 1 Materials of the hole injection layer, the first hole transport layer, the second hole transport layer, the light emitting layer, the first electron transport layer and the second electron transport layer as shown in Table 1
- Example 2 Compound 7 and 8-hydroxyquinolinolato-lithium (Liq) were co-evaporated so that the Liq ratio was 50% by mass to form a second electron transport layer having a thickness of 20 nm. .
- Example 4 Compound 9 and Compound HI-2 were co-evaporated so that the ratio of Compound HI-2 was 3% by mass to form a 5 nm-thick hole injection layer.
- Example 5 Compound 10 and Compound HI-2 were co-evaporated so that the ratio of Compound HI-2 was 3% by mass to form a 5 nm-thick hole injection layer.
- Example 6 Compound 11 and Compound HI-2 were co-evaporated so that the ratio of Compound HI-2 was 3% by mass to form a 5 nm thick hole injection layer.
- Example 7 the compound BH-2 (host material) and the compound BD-2 (dopant material) are co-evaporated so that the ratio of BD-2 is 4% by mass to form a light-emitting layer having a thickness of 20 nm. did.
- Examples 8-28, Comparative Examples 2-3 Manufacture and evaluation of bottom emission type organic EL elements
- Table 1 Materials of the hole injection layer, the first hole transport layer, the second hole transport layer, the light emitting layer, the first electron transport layer and the second electron transport layer as shown in Table 1
- Example 1 Were produced and evaluated in the same manner as in Example 1. The results are shown in Table 1.
- the host material and the dopant material were co-deposited so that the proportion of the dopant material was 4% by mass.
- Example 8 Compound 1 and Compound HI-2 were co-evaporated so that the ratio of Compound HI-2 was 3% by mass to form a 5 nm thick hole injection layer.
- Example 9 Compound 2 and Compound HI-2 were co-evaporated so that the ratio of Compound HI-2 was 3% by mass to form a hole injection layer having a thickness of 5 nm.
- Example 7 and 8-hydroxyquinolinolato-lithium (Liq) were co-evaporated so that the Liq ratio was 50% by mass to form a second electron transport layer having a thickness of 20 nm.
- Example 10 Compound 2 and Compound HI-2 were co-evaporated so that the ratio of Compound HI-2 was 3% by mass to form a 5 nm-thick hole injection layer.
- Example 11 Compound 3 and Compound HI-2 were co-evaporated so that the ratio of Compound HI-2 was 3% by mass to form a 5 nm thick hole injection layer.
- Example 12 Compound 1 and Compound HI-2 were co-evaporated so that the ratio of Compound HI-2 was 3% by mass to form a 5 nm thick hole injection layer.
- Example 13 Compound 2 and Compound HI-2 were co-evaporated so that the ratio of Compound HI-2 was 3% by mass to form a 5 nm-thick hole injection layer.
- Example 14 Compound 3 and Compound HI-2 were co-evaporated so that the ratio of Compound HI-2 was 3% by mass to form a 5 nm-thick hole injection layer.
- Example 15 Compound 3 and Compound HI-2 were co-evaporated so that the ratio of Compound HI-2 was 3% by mass to form a 5 nm-thick hole injection layer.
- Example 16 Compound 3 and Compound HI-2 were co-evaporated so that the ratio of Compound HI-2 was 3% by mass to form a 5 nm-thick hole injection layer.
- Example 17 Compound 3 and Compound HI-2 were co-evaporated so that the ratio of Compound HI-2 was 3% by mass to form a hole injection layer having a thickness of 5 nm.
- Example 18 Compound 1 and Compound HI-2 were co-evaporated so that the ratio of Compound HI-2 was 3% by mass to form a 5 nm-thick hole injection layer. Further, Compound 17 and Liq were co-evaporated so that the Liq ratio was 50% by mass to form a second electron transport layer having a thickness of 20 nm. In Example 19, Compound 2 and Compound HI-2 were co-evaporated so that the ratio of Compound HI-2 was 3% by mass to form a 5 nm thick hole injection layer. Further, Compound 17 and Liq were co-evaporated so that the Liq ratio was 50% by mass to form a second electron transport layer having a thickness of 20 nm.
- Example 20 Compound 10 and Compound HI-2 were co-evaporated so that the ratio of Compound HI-2 was 3% by mass to form a 5 nm thick hole injection layer. Further, Compound 17 and Liq were co-evaporated so that the Liq ratio was 50% by mass to form a second electron transport layer having a thickness of 20 nm.
- Example 21 Compound 1 and Compound HI-2 were co-evaporated so that the ratio of Compound HI-2 was 3% by mass to form a 5 nm-thick hole injection layer. Further, Compound 17 and Liq were co-evaporated so that the Liq ratio was 50% by mass to form a second electron transport layer having a thickness of 20 nm. In Example 22, Compound 2 and Compound HI-2 were co-evaporated so that the ratio of Compound HI-2 was 3% by mass to form a 5 nm thick hole injection layer. Further, Compound 17 and Liq were co-evaporated so that the Liq ratio was 50% by mass to form a second electron transport layer having a thickness of 20 nm.
- Example 23 Compound 10 and Compound HI-2 were co-evaporated so that the ratio of Compound HI-2 was 3% by mass to form a 5 nm-thick hole injection layer. Further, Compound 17 and Liq were co-evaporated so that the Liq ratio was 50% by mass to form a second electron transport layer having a thickness of 20 nm.
- Example 24 Compound 1 and Compound HI-2 were co-evaporated so that the ratio of Compound HI-2 was 3% by mass to form a 5 nm-thick hole injection layer. Further, Compound 17 and Liq were co-evaporated so that the Liq ratio was 50% by mass to form a second electron transport layer having a thickness of 20 nm. In Example 25, Compound 2 and Compound HI-2 were co-evaporated so that the ratio of Compound HI-2 was 3% by mass to form a 5 nm-thick hole injection layer. Further, Compound 17 and Liq were co-evaporated so that the Liq ratio was 50% by mass to form a second electron transport layer having a thickness of 20 nm.
- Example 26 Compound 10 and Compound HI-2 were co-evaporated so that the ratio of Compound HI-2 was 3% by mass to form a 5 nm-thick hole injection layer. Further, Compound 17 and Liq were co-evaporated so that the Liq ratio was 50% by mass to form a second electron transport layer having a thickness of 20 nm.
- Example 27 Compound 3 and Compound HI-2 were co-evaporated so that the ratio of Compound HI-2 was 3% by mass to form a 5 nm-thick hole injection layer.
- the film thickness of the second hole transport layer was 5 nm.
- Example 28 Compound 1 and Compound HI-2 were co-evaporated so that the ratio of Compound HI-2 was 3% by mass to form a 5 nm-thick hole injection layer.
- the film thickness of the second hole transport layer was 5 nm.
- Compound 17 and Liq were co-evaporated so that the Liq ratio was 50% by mass to form a second electron transport layer having a thickness of 20 nm.
- Examples 11, 21, 27, and 28 the voltage (unit: V) when a voltage was applied to the obtained organic EL elements was measured so that the current density was 10 mA / cm 2 .
- the results are shown in Table 1.
- the organic EL elements of Examples 11, 21, 27 and 28 (particularly Examples 27 and 28) had a low drive voltage.
- Table 1 shows that the organic EL device according to one embodiment of the present invention has high efficiency and a long lifetime.
- Example 31 [Manufacture and evaluation of top emission organic EL elements] A layer of APC (Ag—Pd—Cu) (reflective layer) (film thickness: 100 nm) and a layer of indium zinc oxide (IZO) (film thickness: 10 nm), which are silver alloys, are sputtered in this order on a glass substrate. Was formed. Subsequently, the conductive material layer was patterned by etching using a resist pattern as a mask by using a normal lithography technique to form an anode. The substrate on which the lower electrode was formed was subjected to ultrasonic cleaning in isopropyl alcohol for 5 minutes and then UV ozone cleaning for 30 minutes.
- APC Al—Pd—Cu
- IZO indium zinc oxide
- the compound HI-1 was vapor-deposited using a vacuum vapor deposition method to form a 5 nm-thick hole injection layer.
- Compound 1 was deposited to form a first hole transport layer having a thickness of 130 nm.
- Compound 4 was deposited to form a second hole transport layer having a thickness of 10 nm.
- Compound BH-1 (host material) and compound BD-1 (dopant material) are co-evaporated on the second hole transport layer so that the ratio of BD-1 is 4% by mass, and light emission with a film thickness of 20 nm is achieved. Layers were deposited.
- Compound 6 was deposited on the light emitting layer to form a first electron transport layer having a thickness of 5 nm.
- Compound 7 was deposited on the first electron transport layer to form a second electron transport layer having a thickness of 20 nm.
- LiF was vapor-deposited on the second electron transport layer to form an electron injection layer having a thickness of 1 nm.
- Mg and Ag were deposited on the electron injection layer in a film thickness ratio of 1: 9 to form a 15 nm-thick cathode made of a semi-permeable MgAg alloy.
- Compound 13 was deposited on the cathode by vacuum deposition to form a 65 nm thick capping layer.
- An organic EL device was manufactured as described above. The compound 13 used for the capping layer is shown below.
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Abstract
Description
本発明の一態様によれば、以下の有機EL素子等が提供される。
陽極と、有機層と、発光層と、陰極と、をこの順で備え、
前記有機層は下記式(20)で表される化合物を含み、
前記発光層は下記式(1)で表される化合物を含む、
有機エレクトロルミネッセンス素子。
mは0~4の整数であり、
L21及びL22は、それぞれ、単結合、置換もしくは無置換の環形成炭素数6~18のアリーレン基、又は置換もしくは無置換の環形成炭素数5~15のヘテロアリーレン基であり、
mが2以上の整数である場合、複数のAr23はそれぞれ同一でもよく異なってもよく、複数のAr24はそれぞれ同一でもよく異なってもよい。)
Raは、それぞれ、置換もしくは無置換の炭素数1~15のアルキル基又は置換もしくは無置換の炭素数3~15の環状アルキル基であり、
Rb1~Rb4は、それぞれ、ハロゲン原子、シアノ基、置換もしくは無置換の炭素数1~15のアルキル基、置換もしくは無置換の炭素数3~15の環状アルキル基、置換もしくは無置換の炭素数1~45のアルキルシリル基、置換もしくは無置換の炭素数6~50のアリールシリル基、置換もしくは無置換の炭素数1~15のアルコキシ基、置換もしくは無置換の環形成炭素数6~30のアリールオキシ基、置換もしくは無置換の炭素数1~15のアルキルチオ基、置換もしくは無置換の環形成炭素数6~30のアリールチオ基、置換もしくは無置換の環形成炭素数6~30のアリールアミノ基、置換もしくは無置換の環形成炭素数6~30のアリール基、又は置換もしくは無置換の環形成原子数3~30のヘテロアリール基であり、
Rc1~Rc10は、それぞれ、水素原子、ハロゲン原子、シアノ基、置換もしくは無置換の炭素数1~15のアルキル基、置換もしくは無置換の炭素数3~15の環状アルキル基、置換もしくは無置換の炭素数1~45のアルキルシリル基、置換もしくは無置換の炭素数6~50のアリールシリル基、置換もしくは無置換の炭素数1~15のアルコキシ基、置換もしくは無置換の環形成炭素数6~30のアリールオキシ基、置換もしくは無置換の炭素数1~15のアルキルチオ基、置換もしくは無置換の環形成炭素数6~30のアリールチオ基、置換もしくは無置換の環形成炭素数6~30のアリールアミノ基、置換もしくは無置換の環形成炭素数6~30のアリール基、置換もしくは無置換の環形成原子数3~30のヘテロアリール基、又は窒素原子と結合する単結合であり、
*は、Rc1~Rc10のいずれかと窒素原子との結合位置を示し、
xは、0~3の整数であり、
yは、0~4の整数であり、
zは、それぞれ0~5の整数であり、
xが2以上の整数である場合、複数のRb1はそれぞれ同一でもよく異なってもよく、yが2以上の整数である場合、複数のRb2はそれぞれ同一でもよく異なってもよく、zが2以上の整数である場合、複数のRb3はそれぞれ同一でもよく異なってもよく、複数のRb4はそれぞれ同一でもよく異なってもよい。)
本発明の一態様に係る有機EL素子は、陽極と、有機層と、発光層と、陰極とをこの順序で備える。有機層は式(20)で表される化合物を含み、発光層は式(1)で表される化合物を含む。各層に含まれる化合物については後述する。
式(20)で表される化合物を含む有機層は陽極と発光層の間に位置する層であり、通常、正孔注入層又は正孔輸送層であり、好ましくは正孔輸送層である。また、当該有機層は好ましくは発光層と隣接する。
(1)陽極/正孔輸送帯域/発光層/陰極
(2)陽極/正孔輸送帯域/発光層/電子輸送帯域/陰極
(「/」は各層が隣接して積層されていることを示す。)
(3)正孔輸送層
(4)正孔注入層/正孔輸送層
(5)第1の正孔輸送層/第2の正孔輸送層
(6)正孔注入層/第1の正孔輸送層/第2の正孔輸送層
有機EL素子1は、透光性の基板2、陽極3、陰極4、及び陽極3と陰極4との間に配置された発光ユニット10を含む。発光ユニット10は、陽極3側から順に、正孔注入層6、正孔輸送層7、発光層5、電子輸送層8、及び電子注入層9がこの順番で積層されて構成される。有機EL素子1は、光が基板2側から放出されるボトムエミッション型の有機EL素子である。
以下、有機EL素子を構成する各層について説明する。
発光層は下記式(1)で表される化合物を含む。
Raは、それぞれ、置換もしくは無置換の炭素数1~15のアルキル基又は置換もしくは無置換の炭素数3~15の環状アルキル基であり、
Rb1~Rb4は、それぞれ、ハロゲン原子、シアノ基、置換もしくは無置換の炭素数1~15のアルキル基、置換もしくは無置換の炭素数3~15の環状アルキル基、置換もしくは無置換の炭素数1~45のアルキルシリル基、置換もしくは無置換の炭素数6~50のアリールシリル基、置換もしくは無置換の炭素数1~15のアルコキシ基、置換もしくは無置換の環形成炭素数6~30のアリールオキシ基、置換もしくは無置換の炭素数1~15のアルキルチオ基、置換もしくは無置換の環形成炭素数6~30のアリールチオ基、置換もしくは無置換の環形成炭素数6~30のアリールアミノ基、置換もしくは無置換の環形成炭素数6~30のアリール基、又は置換もしくは無置換の環形成原子数3~30のヘテロアリール基であり、
Rc1~Rc10は、それぞれ、水素原子、ハロゲン原子、シアノ基、置換もしくは無置換の炭素数1~15のアルキル基、置換もしくは無置換の炭素数3~15の環状アルキル基、置換もしくは無置換の炭素数1~45のアルキルシリル基、置換もしくは無置換の炭素数6~50のアリールシリル基、置換もしくは無置換の炭素数1~15のアルコキシ基、置換もしくは無置換の環形成炭素数6~30のアリールオキシ基、置換もしくは無置換の炭素数1~15のアルキルチオ基、置換もしくは無置換の環形成炭素数6~30のアリールチオ基、置換もしくは無置換の環形成炭素数6~30のアリールアミノ基、置換もしくは無置換の環形成炭素数6~30のアリール基、置換もしくは無置換の環形成原子数3~30のヘテロアリール基、又は窒素原子と結合する単結合であり、
*は、Rc1~Rc10のいずれかと窒素原子との結合位置を示し、
xは、0~3の整数であり、
yは、0~4の整数であり、
zは、それぞれ0~5の整数であり、
xが2以上の整数である場合、複数のRb1はそれぞれ同一でもよく異なってもよく、yが2以上の整数である場合、複数のRb2はそれぞれ同一でもよく異なってもよく、zが2以上の整数である場合、複数のRb3はそれぞれ同一でもよく異なってもよく、複数のRb4はそれぞれ同一でもよく異なってもよい。)
この場合、上記化合物はアリールアミノ基の2置換体となる。
Rc2~Rc5、Rc7~Rc10は、それぞれ、水素原子、ハロゲン原子、シアノ基、置換もしくは無置換の炭素数1~15のアルキル基、置換もしくは無置換の炭素数3~15の環状アルキル基、置換もしくは無置換の炭素数1~45のアルキルシリル基、置換もしくは無置換の炭素数6~50のアリールシリル基、置換もしくは無置換の炭素数1~15のアルコキシ基、置換もしくは無置換の環形成炭素数6~30のアリールオキシ基、置換もしくは無置換の炭素数1~15のアルキルチオ基、置換もしくは無置換の環形成炭素数6~30のアリールチオ基、置換もしくは無置換の環形成炭素数6~30のアリールアミノ基、置換もしくは無置換の環形成炭素数6~30のアリール基、又は置換もしくは無置換の環形成原子数3~30のヘテロアリール基である。
Rc3及びRc8は、好ましくは、それぞれ水素原子、炭素数1~6のアルキル基又は炭素数1~6の環状アルキル基である。
Rc2、Rc4~Rc10は、それぞれ、水素原子、ハロゲン原子、シアノ基、置換もしくは無置換の炭素数1~15のアルキル基、置換もしくは無置換の炭素数3~15の環状アルキル基、置換もしくは無置換の炭素数1~45のアルキルシリル基、置換もしくは無置換の炭素数6~50のアリールシリル基、置換もしくは無置換の炭素数1~15のアルコキシ基、置換もしくは無置換の環形成炭素数6~30のアリールオキシ基、置換もしくは無置換の炭素数1~15のアルキルチオ基、置換もしくは無置換の環形成炭素数6~30のアリールチオ基、置換もしくは無置換の環形成炭素数6~30のアリールアミノ基、置換もしくは無置換の環形成炭素数6~30のアリール基、又は置換もしくは無置換の環形成原子数3~30のヘテロアリール基である。
Rc7は、好ましくは、置換もしくは無置換の炭素数1~15のアルキル基又は置換もしくは無置換の炭素数3~15の環状アルキル基である。
尚、上記記載はRb1とArがパラ位に置換することを妨げるものではなく、これらがパラ位に置換していてもよい。
Rb3’及びRb4’は、それぞれ、置換もしくは無置換の炭素数1~15のアルキル基又は置換もしくは無置換の炭素数3~15の環状アルキル基であり、
z1は、それぞれ、0~4の整数である。
アルキル基の炭素数は、1~10が好ましく、1~6がさらに好ましい。中でもメチル基、エチル基、プロピル基、イソプロピル基、n-ブチル基、s-ブチル基、イソブチル基、t-ブチル基、n-ペンチル基、n-ヘキシル基が好ましい。
アリール基は、環形成炭素数が6~20であることが好ましく、より好ましくは6~12であり、上述したアリール基の中でもフェニル基、ビフェニル基、が特に好ましい。
アリールチオ基は、-SZと表され、Zの例として上記のアリール基の例が挙げられる。
ヘテロアリール基は、好ましくは、ジベンゾフラニル基、ジベンゾチオフェニル基、又はカルバゾリル基であり、より好ましくは、1-ジベンゾフラニル基、2-ジベンゾフラニル基、3-ジベンゾフラニル基、4-ジベンゾフラニル基、1-ジベンゾチオフェニル基、2-ジベンゾチオフェニル基、3-ジベンゾチオフェニル基、4-ジベンゾチオフェニル基である。
発光層が、式(1)で表される化合物と、他の化合物とを含む場合、化合物(1)の含有量は特に制限されないが、例えば、発光層全体に対して、0.1~70質量%とすることができ、好ましくは1~20質量%であり、より好ましくは1~10質量%であり、特に好ましくは1~4質量%である。
発光層は、好ましくは式(1)で表される化合物と下記式(5)で表されるアントラセン誘導体とを含有する。好ましくは、式(1)で表される化合物をドーパントとして、式(5)で表されるアントラセン誘導体をホストとして含有する。
R101~R108は、それぞれ、水素原子、置換もしくは無置換の環形成原子数5~50(好ましくは5~30、より好ましくは5~20、さらに好ましくは5~12)の単環基、置換もしくは無置換の環形成原子数8~50(好ましくは8~30、より好ましくは8~20、さらに好ましくは8~14)の縮合環基、前記単環基と前記縮合環基との組合せから構成される基、置換もしくは無置換の炭素数1~50(好ましくは1~20、より好ましくは1~10、さらに好ましくは1~6)のアルキル基、置換もしくは無置換の環形成炭素数3~50(好ましくは3~20、より好ましくは3~10、さらに好ましくは5~8)のシクロアルキル基、置換もしくは無置換の炭素数1~50(好ましくは1~20、より好ましくは1~10、さらに好ましくは1~6)のアルコキシ基、置換もしくは無置換の炭素数7~50(好ましくは7~20、より好ましくは7~14)のアラルキル基、置換もしくは無置換の環形成炭素数6~50(好ましくは6~20、より好ましくは6~12)のアリールオキシ基、置換もしくは無置換のシリル基、ハロゲン原子、及びシアノ基からなる群から選ばれる基である。
環形成原子数5~50の単環基の具体例としては、フェニル基、ビフェニリル基、ターフェニリル基、クォーターフェニリル基等の芳香族基と、ピリジル基、ピラジル基、ピリミジル基、トリアジニル基、フリル基、チエニル基等の複素環基が好ましい。
上記単環基としては、中でも、フェニル基、ビフェニリル基、ターフェニリル基が好ましい。
環形成原子数8~50の縮合環基の具体例としては、ナフチル基、フェナントリル基、アントリル基、クリセニル基、ベンゾアントリル基、ベンゾフェナントリル基、トリフェニレニル基、ベンゾクリセニル基、インデニル基、フルオレニル基、ベンゾフルオレニル基、ジベンゾフルオレニル基、フルオランテニル基、ベンゾフルオランテニル基等の縮合芳香族環基や、ベンゾフラニル基、ベンゾチオフェニル基、インドリル基、ジベンゾフラニル基、ジベンゾチオフェニル基、カルバゾリル基、キノリル基、フェナントロリニル基等の縮合複素環基が好ましい。
上記フルオレニル基は、9位に置換基を1つ又は2つ有していてもよく、置換基としては、例えば、アルキル基、アリール基、アルキルシリル基、アリールシリル基、アルコキシ基等が挙げられる。このようなフルオレニル基の具体例としては、例えば、9,9-ジメチルフルオレニル基や9,9-ジフェニルフルオレニル基等が挙げられる。以後、フルオレニル基と記載した場合には、特筆しない限り同様の置換基を有していてもよいものとする。
尚、Ar11及びAr12の置換基は、上述の単環基又は縮合環基が好ましい。
アントラセン誘導体(A)は、式(5)におけるAr11及びAr12が、それぞれ、置換もしくは無置換の環形成原子数8~50の縮合環基である。当該アントラセン誘導体としては、Ar11及びAr12は同一でもよく異なってもよい。
アントラセン誘導体(B)は、式(5)におけるAr11及びAr12の一方が置換もしくは無置換の環形成原子数5~50の単環基であり、Ar11及びAr12の他方が置換もしくは無置換の環形成原子数8~50の縮合環基である。
アントラセン誘導体(B)の好ましい形態としては、Ar12がナフチル基、フェナントリル基、ベンゾアントリル基、フルオレニル基(具体的には、9,9-ジメチルフルオレニル基等)、又はジベンゾフラニル基であり、Ar11が無置換フェニル基、又は、単環基又は縮合環基(例えば、フェニル基、ビフェニル基、ナフチル基、フェナントリル基、フルオレニル基(具体的には、9,9-ジメチルフルオレニル基等)、ジベンゾフラニル基)で置換されたフェニル基である誘導体が挙げられる。好ましい単環基、縮合環基の具体的な基は上述した通りである。
アントラセン誘導体(B)の別の好ましい形態としては、Ar12が置換もしくは無置換の環形成原子数8~50の縮合環基であり、Ar11が無置換のフェニル基である誘導体が挙げられる。この場合、縮合環基としては、フェナントリル基、フルオレニル基(具体的には、9,9-ジメチルフルオレニル基等)、ジベンゾフラニル基、ベンゾアントリル基が特に好ましい。
アントラセン誘導体(C)は、式(5)におけるAr11及びAr12が、それぞれ、置換もしくは無置換の環形成原子数5~50の単環基である。
アントラセン誘導体(C)の好ましい形態としては、Ar11、Ar12ともに置換もしくは無置換のフェニル基である誘導体が挙げられる。さらに好ましい形態として、Ar11が無置換のフェニル基であり、Ar12が単環基又は縮合環基で置換されたフェニル基である場合と、Ar11、Ar12がそれぞれ単環基又は縮合環基で置換されたフェニル基である場合がある。
前記置換基としての好ましい単環基、縮合環基の具体例は上述した通りである。置換基としてのさらに好ましい単環基は、フェニル基、ビフェニル基であり、置換基としてのさらに好ましい縮合環基は、ナフチル基、フェナントリル基、フルオレニル基(具体的には、9,9-ジメチルフルオレニル基等)、ジベンゾフラニル基、ベンゾアントリル基である。
上述したように、本発明の一態様に係る有機EL素子は、陽極と発光層の間に位置する有機層(通常、正孔輸送帯域を構成する1以上の有機層)が下記式(20)で表される化合物を含む。
mは0~4の整数であり、
L21及びL22は、それぞれ、単結合、置換もしくは無置換の環形成炭素数6~18のアリーレン基、又は置換もしくは無置換の環形成炭素数5~15のヘテロアリーレン基であり、
mが2以上の整数である場合、複数のAr23はそれぞれ同一でもよく異なってもよく、複数のAr24はそれぞれ同一でもよく異なってもよい。)
陽極には、仕事関数の大きい(具体的には4.0eV以上)金属、合金、電気伝導性化合物、及びこれらの混合物等を用いることが好ましい。具体的には、例えば、酸化インジウム-酸化スズ(ITO:Indium Tin Oxide)、珪素又は酸化珪素を含有した酸化インジウム-酸化スズ、酸化インジウム-酸化亜鉛、酸化タングステン、及び酸化亜鉛を含有した酸化インジウム、グラフェン等が挙げられる。この他、金(Au)、白金(Pt)、又は金属材料の窒化物(例えば、窒化チタン)等が挙げられる。
正孔注入層は、正孔注入性の高い材料(正孔注入性材料)を含む層である。
R37としては、メチル基、エチル基、n-プロピル基、イソプロピル基、n-ブチル基、イソブチル基、t-ブチル基、シクロペンチル基、シクロヘキシル基等が挙げられる。
Rは、水素原子、ハロゲン原子、ヒドロキシル基、シアノ基、置換もしくは無置換の炭素数1~30のアルキル基、置換もしくは無置換の環形成炭素数6~30のアリール基、置換もしくは無置換の炭素数1~30のアルキル基及び置換もしくは無置換の環形成炭素数6~30のアリール基からなる群から選択される1以上の置換基を有する、モノ置換、ジ置換もしくはトリ置換シリル基、置換もしくは無置換の炭素数1~30のアルキル基を有するアルコキシ基、置換もしくは無置換の環形成炭素数6~30のアリール基を有するアリールオキシ基、置換もしくは無置換の炭素数1~30のアルキル基及び置換もしくは無置換の環形成炭素数6~30のアリール基からなる群から選択される1以上の置換基を有するモノ置換もしくはジ置換アミノ基、置換もしくは無置換の炭素数1~30のアルキル基を有するアルキルチオ基、置換もしくは無置換の環形成炭素数6~30のアリール基を有するアリールチオ基、又は置換もしくは無置換の環形成原子数5~30のヘテロアリール基である。
上記アルキル基、アリール基、アルコキシ基、アリールオキシ基、アルキルチオ基、アリールチオ基及びヘテロアリール基としては、上記式(1)で挙げた各基が挙げられる。
シリル基は、上記のアルキル基及びアリール基からなる群から選択される1以上の基で置換された基が挙げられる。
アミノ基は、上記のアルキル基及びアリール基からなる群から選択される1以上の基で置換された基が挙げられる。
R200-C*-CN
(上記式中、C*は二重結合で式(2)のシクロプロパンに結合する炭素原子である。R200は、それぞれ、芳香族6員環、ハロゲン原子、置換もしくは無置換のフルオロアルキル基、置換もしくは無置換のフルオロアルコキシ基及びシアノ基から選択される1以上で置換されている芳香族6員環である。)
芳香族6員環としては、上記式(1)で挙げたアリール基及びヘテロアリール基のうち6員環のものが挙げられる。
フルオロアルキル基としては、上記式(1)で挙げたアルキル基とフッ素原子を組み合わせた基が挙げられる。
フルオロアルコキシ基としては、上記式(1)で挙げたアルコキシ基とフッ素原子を組み合わせた基が挙げられる。
L211は、置換もしくは無置換の環形成炭素数6~50(好ましくは6~30、より好ましくは6~20、さらに好ましくは6~12)のアリーレン基、置換もしくは無置換の環形成炭素数10~50(好ましくは10~30、より好ましくは10~20)の縮合アリーレン基、置換もしくは無置換の環形成原子数5~50(好ましくは5~30、より好ましくは5~20、さらに好ましくは5~12)のヘテロアリーレン基、又は置換もしくは無置換の環形成原子数8~50(好ましくは8~30、より好ましくは8~20)の縮合ヘテロアリーレン基を表す。
縮合アリール基及び縮合アリーレン基としては、上記式(5)で挙げた縮合環のうち縮合アリール基及びそれに対応する2価の基が挙げられる。
ヘテロアリール基及びヘテロアリーレン基としては、上記式(1)で挙げたヘテロアリール基及びそれに対応する2価の基が挙げられる。
縮合ヘテロアリール基及び縮合ヘテロアリーレン基としては、上記式(5)で挙げた縮合環のうち縮合ヘテロアリール基及びそれに対応する2価の基が挙げられる。
本発明の一態様における有機EL素子が2以上の正孔輸送層を含む場合、発光層に接する正孔輸送層の膜厚は、特に制限されるものではないが、例えば0.1~20nmであり、20nm以下が好ましく、10nm以下がより好ましく、5nm以下がさらに好ましい。
式(20)で表される化合物を含む有機層は、正孔輸送層であることが好ましい。また、式(20)で表される化合物を含む有機層は発光層と隣接することが好ましい。
電子輸送層は電子輸送性の高い材料(電子輸送性材料)を含む層である。電子輸送層材料としては、例えば、下記(1)~(3)の化合物が挙げられる。
(1)アルミニウム錯体、ベリリウム錯体、亜鉛錯体等の金属錯体
(2)イミダゾール誘導体、ベンゾイミダゾール誘導体、アジン(含窒素六員環)誘導体、カルバゾール誘導体、フェナントロリン誘導体等の複素芳香族化合物
(3)高分子化合物
カルバゾール環と含窒素六員環を含む化合物における含窒素六員環としては、例えば、ピリミジン環、トリアジン環、ピリジン環が挙げられ、ピリミジン環が特に好ましい。
R231及びR232は、それぞれ、置換基である。R231が2以上存在する場合、2以上のR231は同一でもよく、異なっていてもよい。R232が2以上存在する場合、2以上のR232は同一でもよく、異なっていてもよい。
X1~X3は、それぞれ、N、CH又はC(R233)であり、X1~X3の少なくとも2つはNである。
R233は置換基であり、R233が2以上存在する場合、2以上のR233は同一でもよく、異なっていてもよい。
L231は、置換もしくは無置換の環形成炭素数6~18のアリーレン基、又は置換もしくは無置換の環形成炭素数5~15のヘテロアリーレン基であり、L231が2以上存在する場合、2以上のL231は同一でもよく、異なっていてもよい。
m1は、0~3の整数である。
m2は、1~5の整数である。
m3及びm4は、それぞれ、0~4の整数である。)
L231の環形成炭素数6~18のアリーレン基及び環形成炭素数5~15のヘテロアリーレン基としては、L21及びL22の環形成炭素数6~18のアリーレン基及び環形成炭素数5~15のヘテロアリーレン基と同様のものが挙げられる。
R231が2以上存在する場合、隣り合うR231同士は互いに結合して環を形成してもよい。R232が2以上存在する場合、隣り合うR232同士は互いに結合して環を形成してもよい。
電子注入層は、電子注入性の高い材料を含む層である。電子注入層には、リチウム(Li)、セシウム(Cs)、カルシウム(Ca)、フッ化リチウム(LiF)、フッ化セシウム(CsF)、フッ化カルシウム(CaF2)、リチウム酸化物(LiOx)等のアルカリ金属、アルカリ土類金属、又はそれらの化合物を用いることができる。その他、電子輸送性を有する材料にアルカリ金属、アルカリ土類金属、又はそれらの化合物を含有させたもの、具体的にはAlq中にマグネシウム(Mg)を含有させたもの等を用いてもよい。尚、この場合には、陰極からの電子注入をより効率良く行うことができる。
陰極には、仕事関数の小さい(具体的には3.8eV以下)金属、合金、電気伝導性化合物、及びこれらの混合物等を用いることが好ましい。このような陰極材料の具体例としては、元素周期表の第1族又は第2族に属する元素、即ち、リチウム(Li)やセシウム(Cs)等のアルカリ金属、及びマグネシウム(Mg)、カルシウム(Ca)、ストロンチウム(Sr)等のアルカリ土類金属、及びこれらを含む合金(例えば、MgAg、AlLi)、ユーロピウム(Eu)、イッテルビウム(Yb)等の希土類金属及びこれらを含む合金等が挙げられる。
尚、アルカリ金属、アルカリ土類金属、これらを含む合金を用いて陰極を形成する場合には、真空蒸着法やスパッタリング法を用いることができる。また、銀ペースト等を用いる場合には、塗布法やインクジェット法等を用いることができる。
尚、電子注入層を設けることにより、仕事関数の大小に関わらず、Al、Ag、ITO、グラフェン、珪素もしくは酸化珪素を含有した酸化インジウム-酸化スズ等様々な導電性材料を用いて陰極を形成することができる。これらの導電性材料は、スパッタリング法やインクジェット法、スピンコート法等を用いて成膜することができる。
有機EL素子は、効率良く発光させるために、少なくとも一方の面は素子の発光波長領域において十分透明にすることが望ましい。また、基板も透明であることが望ましい。透明電極は、上記の導電性材料を使用して、蒸着やスパッタリング等の方法で所定の透光性が確保されるように設定する。発光面の電極は、光透過率を10%以上にすることが望ましい。
基板としては、例えば、ガラス、石英、プラスチック等を用いることができる。また、可撓性基板を用いてもよい。可撓性基板とは、折り曲げることができる(フレキシブル)基板のことであり、例えば、ポリカーボネート、ポリ塩化ビニルからなるプラスチック基板等が挙げられる。
有機EL素子の各層の形成は、真空蒸着、スパッタリング、プラズマ、イオンプレーティング等の乾式成膜法やスピンコーティング、ディッピング、フローコーティング等の湿式成膜法のいずれの方法を適用することができる。
各層の膜厚は特に限定されるものではないが、適切な膜厚に設定する必要がある。膜厚が厚すぎると、一定の光出力を得るために大きな印加電圧が必要になり効率が悪くなる恐れがある。膜厚が薄すぎるとピンホール等が発生して、電界を印加しても充分な発光輝度が得られない恐れがある。膜厚は、通常、1nm~10μmが好ましく、5nm~0.2μmのとしてもよい。いずれの有機層においても、成膜性向上、膜のピンホール防止等のため適切な樹脂や添加剤を使用してもよい。
本発明の一態様に係る有機EL素子は、基板側から光を取り出すボトムエミッション型(図1)であってもよいし、陰極側から取り出すトップエミッション型であってもよい。本発明の一態様に係る有機EL素子をトップエミッション型とする場合について、以下説明する。
陽極と陰極については下記の通りである。
陽極の材料としては、Ag、Al、Au等の金属やAPC(Ag-Pd-Cu)等の金属合金が好ましい。これらの金属材料や金属合金を積層してもよい。また金属、金属合金又はこれらの積層構造の上面及び/又は下面にインジウム錫酸化物(ITO)やインジウム亜鉛酸化物といった透明電極層を成膜してもよい。
陰極としては金属性の材料を用いることができる。金属性の材料とは、誘電率の実部が負の値であるものをいう。このような材料には、金属だけでなく金属以外の金属光沢を示す有機透明電極材料や無機透明電極材料が含まれる。
金属としては、Ag,Mg,Al,Ca等、及びこれらの合金により形成されるものが好ましい。また、正面方向の透過率が20%以上で半透明であることが好ましい。Ag,Mg,Al,Ca又はこれらの合金を陰極として用いた場合、十分な光の透過性を示すために、膜厚は30nm以下であることが好ましい。
(i)分子式が炭素原子と水素原子を構成元素として含む化合物であって、酸素原子、窒素原子、フッ素原子、珪素原子、塩素原子、臭素原子、ヨウ素原子を含んでもよく、また置換基を有してもよい芳香族炭化水素化合物
(ii)分子式が炭素原子と水素原子を構成元素として含む化合物であって、酸素原子、窒素原子、フッ素原子、珪素原子、塩素原子、臭素原子、ヨウ素原子を含んでもよく、また置換基を有してもよい芳香族複素環化合物
(iii)分子式が炭素原子と水素原子を構成元素として含む化合物であって、酸素原子、窒素原子、フッ素原子、珪素原子、塩素原子、臭素原子、ヨウ素原子を含んでもよく、また置換基を有してもよいアミン化合物
有機EL素子100は、基板2上に、陽極3、発光ユニット10、陰極4及びキャッピング層20をこの順に備え、キャッピング層20側から光を取り出す構成となっている。発光ユニット10は図1で説明した通りである。
本発明の一態様における有機EL素子は、壁掛けテレビのフラットパネルディスプレイ等の平面発光体、複写機、プリンター、液晶ディスプレイのバックライト又は計器類等の光源、表示板、標識灯等に利用できる。また、本発明の一態様における化合物は、有機EL素子だけでなく、電子写真感光体、光電変換素子、太陽電池、イメージセンサー等の分野においても使用できる。
[ボトムエミッション型有機EL素子の製造]
25mm×75mm×1.1mm厚のITO透明電極(陽極)付きガラス基板(ジオマティック社製)をイソプロピルアルコール中で超音波洗浄を5分間行なった後、UV(紫外線)オゾン洗浄を30分間行なった。ITO透明電極の膜厚は、130nmとした。洗浄後の透明電極ライン付きガラス基板を真空蒸着装置の基板ホルダーに装着し、まず透明電極ラインが形成されている側の面上に透明電極を覆うようにして化合物HI-1を蒸着し、膜厚5nmの正孔注入層を形成した。正孔注入層の成膜に続けて化合物1を蒸着し、膜厚90nmの第1の正孔輸送層を成膜した。第1の正孔輸送層の成膜に続けて化合物4を蒸着し、膜厚10nmの第2の正孔輸送層を成膜した。第2の正孔輸送層上に化合物BH-1(ホスト材料)及び化合物BD-1(ドーパント材料)を、BD-1の割合が4質量%となるように共蒸着し、膜厚20nmの発光層を成膜した。発光層上に化合物6を蒸着し、膜厚5nmの第1の電子輸送層を形成した。第1の電子輸送層上に化合物7を蒸着し、膜厚20nmの第2の電子輸送層を形成した。第2の電子輸送層上にLiFを蒸着して膜厚1nmの電子注入層を形成した。電子注入層上に金属Alを蒸着して膜厚80nmの陰極を形成した。
以上のようにして有機EL素子を製造した。
実施例1及び後述する実施例及び比較例で用いた化合物を以下に示す。
得られた有機EL素子について、以下のように電流効率及び素子寿命(LT95)を測定した。結果を表1に示す。
電流密度が10mA/cm2となるように有機EL素子に電圧を印加した時の分光放射輝度スペクトルを分光放射輝度計(コニカミノルタ株式会社製「CS-1000」)で計測し、得られた分光放射輝度スペクトルから電流効率(単位:cd/A)を算出した。
電流密度が50mA/cm2となるように有機EL素子に電圧を印加し、初期輝度に対して輝度が95%となるまでの時間(単位:h)を測定した。
[ボトムエミッション型有機EL素子の製造及び評価]
正孔注入層、第1の正孔輸送層、第2の正孔輸送層、発光層、第1の電子輸送層及び第2の電子輸送層の材料を表1に記載のように変更した他は実施例1と同様にして有機EL素子を作製し、評価した。結果を表1に示す。
実施例2では、化合物7と8-ヒドロキシキノリノラト-リチウム(Liq)を、Liqの割合が50質量%となるように共蒸着して、膜厚20nmの第2の電子輸送層を形成した。
実施例4では、化合物9と化合物HI-2を、化合物HI-2の割合が3質量%となるように共蒸着して、膜厚5nmの正孔注入層を形成した。
実施例5では、化合物10と化合物HI-2を、化合物HI-2の割合が3質量%となるように共蒸着して、膜厚5nmの正孔注入層を形成した。
実施例6では、化合物11と化合物HI-2を、化合物HI-2の割合が3質量%となるように共蒸着して、膜厚5nmの正孔注入層を形成した。
実施例7では、化合物BH-2(ホスト材料)及び化合物BD-2(ドーパント材料)を、BD-2の割合が4質量%となるように共蒸着し、膜厚20nmの発光層を成膜した。
[ボトムエミッション型有機EL素子の製造及び評価]
正孔注入層、第1の正孔輸送層、第2の正孔輸送層、発光層、第1の電子輸送層及び第2の電子輸送層の材料を表1に記載のように変更した他は実施例1と同様にして有機EL素子を作製し、評価した。結果を表1に示す。
尚、実施例8~28及び比較例2~3では、ホスト材料及びドーパント材料を、ドーパント材料の割合が4質量%となるように共蒸着した。
実施例9では、化合物2と化合物HI-2を、化合物HI-2の割合が3質量%となるように共蒸着して、膜厚5nmの正孔注入層を形成した。また、化合物7と8-ヒドロキシキノリノラト-リチウム(Liq)を、Liqの割合が50質量%となるように共蒸着して、膜厚20nmの第2の電子輸送層を形成した。
実施例10では、化合物2と化合物HI-2を、化合物HI-2の割合が3質量%となるように共蒸着して、膜厚5nmの正孔注入層を形成した。
実施例11では、化合物3と化合物HI-2を、化合物HI-2の割合が3質量%となるように共蒸着して、膜厚5nmの正孔注入層を形成した。
実施例13では、化合物2と化合物HI-2を、化合物HI-2の割合が3質量%となるように共蒸着して、膜厚5nmの正孔注入層を形成した。
実施例14では、化合物3と化合物HI-2を、化合物HI-2の割合が3質量%となるように共蒸着して、膜厚5nmの正孔注入層を形成した。
実施例16では、化合物3と化合物HI-2を、化合物HI-2の割合が3質量%となるように共蒸着して、膜厚5nmの正孔注入層を形成した。
実施例17では、化合物3と化合物HI-2を、化合物HI-2の割合が3質量%となるように共蒸着して、膜厚5nmの正孔注入層を形成した。
実施例19では、化合物2と化合物HI-2を、化合物HI-2の割合が3質量%となるように共蒸着して、膜厚5nmの正孔注入層を形成した。また、化合物17とLiqを、Liqの割合が50質量%となるように共蒸着して、膜厚20nmの第2の電子輸送層を形成した。
実施例20では、化合物10と化合物HI-2を、化合物HI-2の割合が3質量%となるように共蒸着して、膜厚5nmの正孔注入層を形成した。また、化合物17とLiqを、Liqの割合が50質量%となるように共蒸着して、膜厚20nmの第2の電子輸送層を形成した。
実施例22では、化合物2と化合物HI-2を、化合物HI-2の割合が3質量%となるように共蒸着して、膜厚5nmの正孔注入層を形成した。また、化合物17とLiqを、Liqの割合が50質量%となるように共蒸着して、膜厚20nmの第2の電子輸送層を形成した。
実施例23では、化合物10と化合物HI-2を、化合物HI-2の割合が3質量%となるように共蒸着して、膜厚5nmの正孔注入層を形成した。また、化合物17とLiqを、Liqの割合が50質量%となるように共蒸着して、膜厚20nmの第2の電子輸送層を形成した。
実施例25では、化合物2と化合物HI-2を、化合物HI-2の割合が3質量%となるように共蒸着して、膜厚5nmの正孔注入層を形成した。また、化合物17とLiqを、Liqの割合が50質量%となるように共蒸着して、膜厚20nmの第2の電子輸送層を形成した。
実施例26では、化合物10と化合物HI-2を、化合物HI-2の割合が3質量%となるように共蒸着して、膜厚5nmの正孔注入層を形成した。また、化合物17とLiqを、Liqの割合が50質量%となるように共蒸着して、膜厚20nmの第2の電子輸送層を形成した。
実施例28では、化合物1と化合物HI-2を、化合物HI-2の割合が3質量%となるように共蒸着して、膜厚5nmの正孔注入層を形成した。また、第2の正孔輸送層の膜厚5nmとした。また、化合物17とLiqを、Liqの割合が50質量%となるように共蒸着して、膜厚20nmの第2の電子輸送層を形成した。
実施例11,21,27及び28(特に実施例27及び28)の有機EL素子は、低駆動電圧であった。
[トップエミッション型有機EL素子の製造及び評価]
ガラス基板の上に、銀合金であるAPC(Ag-Pd-Cu)の層(反射層)(膜厚100nm)、及び酸化インジウム亜鉛(IZO)の層(膜厚10nm)を、この順にスパッタリング法により成膜した。続いて、通常のリソグラフィ技術を用いて、レジストパターンをマスクに用いたエッチングにより、この導電材料層をパターニングし、陽極を形成した。下部電極が形成した基板をイソプロピルアルコール中で超音波洗浄を5分間行なった後、UVオゾン洗浄を30分間行なった。その後、真空蒸着法を用いて化合物HI-1を蒸着し、膜厚5nmの正孔注入層を成膜した。正孔注入層の成膜に続けて化合物1を蒸着し、膜厚130nmの第1の正孔輸送層を成膜した。第1の正孔輸送層の成膜に続けて化合物4を蒸着し、膜厚10nmの第2の正孔輸送層を成膜した。第2の正孔輸送層上に化合物BH-1(ホスト材料)及び化合物BD-1(ドーパント材料)を、BD-1の割合が4質量%となるように共蒸着し、膜厚20nmの発光層を成膜した。発光層上に化合物6を蒸着し、膜厚5nmの第1の電子輸送層を形成した。第1の電子輸送層上に化合物7を蒸着し、膜厚20nmの第2の電子輸送層を形成した。第2の電子輸送層上にLiFを蒸着して膜厚1nmの電子注入層を形成した。電子注入層上にMgとAgを1:9の膜厚比で蒸着成膜し、半透過性のMgAg合金からなる膜厚15nmの陰極を形成した。陰極の上に化合物13を真空蒸着法によって成膜し、膜厚65nmのキャッピング層を形成した。
以上のようにして有機EL素子を製造した。キャッピング層に用いた化合物13を以下に示す。
本願のパリ優先の基礎となる日本出願明細書の内容を全てここに援用する。
Claims (11)
- 陽極と、有機層と、発光層と、陰極と、をこの順で備え、
前記有機層は下記式(20)で表される化合物を含み、
前記発光層は下記式(1)で表される化合物を含む、
有機エレクトロルミネッセンス素子。
mは0~4の整数であり、
L21及びL22は、それぞれ、単結合、置換もしくは無置換の環形成炭素数6~18のアリーレン基、又は置換もしくは無置換の環形成炭素数5~15のヘテロアリーレン基であり、
mが2以上の整数である場合、複数のAr23はそれぞれ同一でもよく異なってもよく、複数のAr24はそれぞれ同一でもよく異なってもよい。)
Raは、それぞれ、置換もしくは無置換の炭素数1~15のアルキル基又は置換もしくは無置換の炭素数3~15の環状アルキル基であり、
Rb1~Rb4は、それぞれ、ハロゲン原子、シアノ基、置換もしくは無置換の炭素数1~15のアルキル基、置換もしくは無置換の炭素数3~15の環状アルキル基、置換もしくは無置換の炭素数1~45のアルキルシリル基、置換もしくは無置換の炭素数6~50のアリールシリル基、置換もしくは無置換の炭素数1~15のアルコキシ基、置換もしくは無置換の環形成炭素数6~30のアリールオキシ基、置換もしくは無置換の炭素数1~15のアルキルチオ基、置換もしくは無置換の環形成炭素数6~30のアリールチオ基、置換もしくは無置換の環形成炭素数6~30のアリールアミノ基、置換もしくは無置換の環形成炭素数6~30のアリール基、又は置換もしくは無置換の環形成原子数3~30のヘテロアリール基であり、
Rc1~Rc10は、それぞれ、水素原子、ハロゲン原子、シアノ基、置換もしくは無置換の炭素数1~15のアルキル基、置換もしくは無置換の炭素数3~15の環状アルキル基、置換もしくは無置換の炭素数1~45のアルキルシリル基、置換もしくは無置換の炭素数6~50のアリールシリル基、置換もしくは無置換の炭素数1~15のアルコキシ基、置換もしくは無置換の環形成炭素数6~30のアリールオキシ基、置換もしくは無置換の炭素数1~15のアルキルチオ基、置換もしくは無置換の環形成炭素数6~30のアリールチオ基、置換もしくは無置換の環形成炭素数6~30のアリールアミノ基、置換もしくは無置換の環形成炭素数6~30のアリール基、置換もしくは無置換の環形成原子数3~30のヘテロアリール基、又は窒素原子と結合する単結合であり、
*は、Rc1~Rc10のいずれかと窒素原子との結合位置を示し、
xは、0~3の整数であり、
yは、0~4の整数であり、
zは、それぞれ0~5の整数であり、
xが2以上の整数である場合、複数のRb1はそれぞれ同一でもよく異なってもよく、yが2以上の整数である場合、複数のRb2はそれぞれ同一でもよく異なってもよく、zが2以上の整数である場合、複数のRb3はそれぞれ同一でもよく異なってもよく、複数のRb4はそれぞれ同一でもよく異なってもよい。) - 前記有機層が、前記発光層と隣接している請求項1に記載の有機エレクトロルミネッセンス素子。
- 前記有機層と前記陽極との間に正孔注入層を備え、前記正孔注入層が下記式(2-1)で表される化合物を含む請求項1又は2に記載の有機エレクトロルミネッセンス素子。
X23~X26は、それぞれ、C(R)又は窒素原子である。
a21及びa22は、それぞれ、下記式(2b)で表される環構造である。
- 前記発光層と前記陰極との間に電子輸送層を備え、前記電子輸送層が、イミダゾール誘導体、ベンゾイミダゾール誘導体、アジン誘導体、カルバゾール誘導体及びフェナントロリン誘導体からなる群から選択される1以上の化合物を含む請求項1~3のいずれかに記載の有機エレクトロルミネッセンス素子。
- 前記発光層と前記陰極との間に2以上の電子輸送層を備える請求項1~4のいずれかに記載の有機エレクトロルミネッセンス素子。
- 前記電子輸送層がカルバゾール誘導体を含み、
前記カルバゾール誘導体が、カルバゾール環及び含窒素六員環を含む化合物である請求項4又は5に記載の有機エレクトロルミネッセンス素子。 - 前記電子輸送層が、下記式(M)で表される化合物を含む請求項4~6のいずれかに記載の有機エレクトロルミネッセンス素子。
R231及びR232は、それぞれ、置換基である。R231が2以上存在する場合、2以上のR231は同一でもよく、異なっていてもよい。R232が2以上存在する場合、2以上のR232は同一でもよく、異なっていてもよい。
X1~X3は、それぞれ、N、CH又はC(R233)であり、X1~X3の少なくとも2つはNである。
R233は置換基であり、R233が2以上存在する場合、2以上のR233は同一でもよく、異なっていてもよい。
L231は、置換もしくは無置換の環形成炭素数6~18のアリーレン基、又は置換もしくは無置換の環形成炭素数5~15のヘテロアリーレン基であり、L231が2以上存在する場合、2以上のL231は同一でもよく、異なっていてもよい。
m1は、0~3の整数である。
m2は、1~5の整数である。
m3及びm4は、それぞれ、0~4の整数である。) - 前記有機層と前記陽極との間に正孔輸送層を備え、前記正孔輸送層が下記式(J)で表される化合物を含む請求項1~7のいずれかに記載の有機エレクトロルミネッセンス素子。
- 請求項1~10のいずれかに記載の有機エレクトロルミネッセンス素子を搭載した電子機器。
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CN110431682A (zh) | 2019-11-08 |
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