阅读说明：本技术 发光元件和发光元件用组合物 (Light-emitting element and composition for light-emitting element ) 是由 佐佐田敏明 松本龙二 于 2020-03-16 设计创作，主要内容包括：提供在发光效率优异的发光元件的制造中有用的组合物,以及提供含有该组合物的发光元件。一种发光元件,其具备阳极、阴极以及设置于阳极和阴极之间的包含发光元件用组合物的有机层,发光元件用组合物含有式(2)所示的金属络合物、以及具有在环内包含硼原子和选自氧原子、硫原子、硒原子、sp～(3)碳原子和氮原子中的至少1种的稠合杂环骨架(b)的化合物(B)。(Provided are a composition useful for producing a light-emitting element having excellent light-emitting efficiency, and a light-emitting element containing the composition. A light-emitting element comprising an anode, a cathode, and an organic layer containing a composition for light-emitting elements, the composition for light-emitting elements comprising a metal complex represented by formula (2), and having a ring containing a boron atom and a metal atom selected from the group consisting of an oxygen atom, a sulfur atom, a selenium atom, and an sp atom 3 A compound (B) having a condensed heterocyclic skeleton of at least 1 of carbon atoms and nitrogen atoms.)

1. A light-emitting element comprising an anode, a cathode, and an organic layer containing a composition for a light-emitting element, the organic layer being provided between the anode and the cathode,

the composition for a light-emitting element contains:

a metal complex represented by the formula (2), and

having a ring containing boron atoms and atoms selected from oxygen, sulfur, selenium, sp³Carbon atom and nitrogen atomAt least 1 of the compounds B having a condensed heterocyclic skeleton B,

in the formula (I), the compound is shown in the specification,

M²represents a rhodium atom, a palladium atom, an iridium atom or a platinum atom,

n³represents an integer of 1 or more, n⁴Represents an integer of 0 or more, wherein, in M²In the case of a rhodium atom or an iridium atom, n³+n⁴Is 3 at M²In the case of palladium atom or platinum atom, n³+n⁴Is the number of 2, and the number of the second,

E^Lrepresents a carbon atom or a nitrogen atom, E^LWhen a plurality of them are present, they are each optionally the same or different,

ring L¹Represents an aromatic heterocyclic ring comprising a six-membered ring, the ring optionally having a substituent which may be the same or different when plural, and which may be bonded to each other to form a ring together with the atom to which each is bonded, and a ring L¹Where there are plural, they are optionally the same or different,

ring L²Represents an aromatic hydrocarbon ring or an aromatic heterocyclic ring, the rings optionally having a substituent, the substituents, when present in plural, being optionally the same or different and being optionally bonded to each other to form a ring together with the atom to which each is bonded, and a ring L²Where there are plural, they are optionally the same or different,

ring L¹Optionally having substituents and ring L²The substituents optionally having, which are optionally the same or different, are optionally bonded to each other to form a ring together with the atom to which each is bonded,

wherein, the ring L¹And ring L²Wherein at least 1 of the groups has a group represented by the formula (1-T) as a substituent, and when a plurality of the groups represented by the formula (1-T) are present, they may be the same or different,

A³－G²－A⁴represents an anionic bidentate ligand, A³And A⁴Each independently represents a carbon atom, an oxygen atom or a nitrogen atom, these atoms being optionally atoms constituting a ring, G²Represents a single bond, or with A³And A⁴Radicals together forming a bidentate ligand, A³－G²－A⁴Where there are plural, they are optionally the same or different,

-R^1T (1-T)

in the formula, R^1TRepresents an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryloxy group, an aryl group, a monovalent heterocyclic group or a substituted amino group, which groups optionally have a substituent, and when a plurality of these groups are present, they are optionally the same or different, and are optionally bonded to each other to form a ring together with the respective bonded atoms.

2. The light-emitting element according to claim 1,

the ring L¹Is a pyridine ring, a diazaphenzene ring, an azanaphthalene ring or a diazaphalene ring, which rings optionally have a substituent.

3. The light-emitting element according to claim 2,

the ring L¹Is a pyridine ring, a diaza-benzene ring, a quinoline ring or a diaza-naphthalene ring, these rings optionally having a substituent, and

the R is^1TIs an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group or a substituted amino group, and these groups may have a substituent.

4. The light-emitting element according to claim 2,

the ring L¹Is an isoquinoline ring optionally having a substituent, and

the R is^1TIs an aryl group, a monovalent heterocyclic group or a substituted amino group, which may have a substituent.

5. The light-emitting element according to any one of claims 1 to 4,

the ring L²Is a benzene ring, a pyridine ring or a diaza-benzene ring, and these rings may have a substituent.

6. The light-emitting element according to any one of claims 1 to 5,

the R is^1TIs an optionally substituted aryl group or an optionally substituted monovalent heterocyclic group.

7. The light-emitting element according to any one of claims 1 to 6,

the fused heterocyclic skeleton b contains a boron atom and at least 1 selected from an oxygen atom, a sulfur atom and a nitrogen atom in the ring.

8. The light-emitting element according to claim 7,

the fused heterocyclic skeleton b contains a boron atom and a nitrogen atom within the ring.

9. The light-emitting element according to any one of claims 1 to 6,

the compound B is a compound shown as a formula (1-1), a compound shown as a formula (1-2) or a compound shown as a formula (1-3),

in the formula (I), the compound is shown in the specification,

Ar¹、Ar²and Ar³Each independently represents an aromatic hydrocarbon group or a heterocyclic group, which optionally has a substituent, and when a plurality of such substituents are present, they are optionally the same or different, and are optionally bonded to each other to form a ring together with the atom to which each is bonded,

Y¹represents an oxygen atom, a sulfur atom, a selenium atom, a group represented by the formula-N (Ry) -an alkylene group or a cycloalkylene group, these groups optionally having a substituent, and when a plurality of such substituents are present, theyOptionally identical or different, optionally bonded to one another to form a ring together with the atoms to which they are each bonded,

Y²and Y³Each independently represents a single bond, an oxygen atom, a sulfur atom, a selenium atom, -N (Ry) -representing a group, an alkylene group or a cycloalkylene group, which groups optionally have a substituent, which is optionally the same or different in the presence of plural, optionally bonded to each other to form a ring together with each bonded atom, Ry represents a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, which groups optionally have a substituent, which is optionally the same or different in the presence of plural, optionally bonded to each other to form a ring together with each bonded atom, Ry is optionally the same or different in the presence of plural, Ry optionally directly or via a linking group and Ar¹、Ar²Or Ar³And (4) bonding.

10. The light-emitting element according to claim 9,

said Y is¹The Y mentioned²And said Y³Is an oxygen atom, a sulfur atom or a group represented by-N (Ry) -.

11. The light-emitting element according to claim 10,

said Y is¹The Y mentioned²And said Y³Is a group represented by-N (Ry) -or a pharmaceutically acceptable salt thereof.

12. The light-emitting element according to any one of claims 1 to 11,

the absolute value of the difference between the energy level of the lowest triplet excited state of the compound B and the energy level of the lowest singlet excited state of the compound B is 0.50eV or less.

13. The light-emitting element according to any one of claims 1 to 12,

the composition for a light-emitting element further contains a compound represented by the formula (H-1),

in the formula (I), the compound is shown in the specification,

Ar^H1and Ar^H2Each independently represents an aryl group, a monovalent heterocyclic group or a substituted amino group, which groups optionally have a substituent which, when plural, are optionally the same or different, and are optionally bonded to each other to form a ring together with each bonded atom,

n^H1represents an integer of 0 or more and is,

L^H1represents an arylene group, a divalent heterocyclic group, an alkylene group or a cycloalkylene group, these groups optionally having a substituent, which may be the same or different when plural, are optionally bonded to each other to form a ring together with the atom to which each is bonded, L^H1When a plurality of them is present, they are optionally the same or different.

14. The light-emitting element according to any one of claims 1 to 13,

the composition for a light-emitting element further contains at least 1 selected from a hole-transporting material, a hole-injecting material, an electron-transporting material, an electron-injecting material, a light-emitting material, an antioxidant, and a solvent.

15. A composition for a light-emitting element, comprising:

a metal complex represented by the formula (2), and

having a ring containing boron atoms and atoms selected from oxygen, sulfur, selenium, sp³A compound B having a condensed heterocyclic skeleton B of at least 1 of carbon atoms and nitrogen atoms,

in the formula (I), the compound is shown in the specification,

M²represents a rhodium atom or a palladium atomAn iridium atom or a platinum atom,

n³represents an integer of 1 or more, n⁴Represents an integer of 0 or more, wherein, in M²In the case of a rhodium atom or an iridium atom, n³+n⁴Is 3 at M²In the case of palladium atom or platinum atom, n³+n⁴Is the number of 2, and the number of the second,

E^Lrepresents a carbon atom or a nitrogen atom, E^LWhen a plurality of them are present, they are each optionally the same or different,

ring L¹Represents an aromatic heterocyclic ring comprising a six-membered ring, the ring optionally having a substituent which may be the same or different when plural, and which may be bonded to each other to form a ring together with the atom to which each is bonded, and a ring L¹Where there are plural, they are optionally the same or different,

ring L²Represents an aromatic hydrocarbon ring or an aromatic heterocyclic ring, the rings optionally having a substituent, the substituents, when present in plural, being optionally the same or different and being optionally bonded to each other to form a ring together with the atom to which each is bonded, and a ring L²Where there are plural, they are optionally the same or different,

ring L¹Optionally having substituents and ring L²The substituents optionally having, which are optionally the same or different, are optionally bonded to each other to form a ring together with the atom to which each is bonded,

wherein, the ring L¹And ring L²Wherein at least 1 of the groups has a group represented by the formula (1-T) as a substituent, and when a plurality of the groups represented by the formula (1-T) are present, they may be the same or different,

A³－G²－A⁴represents an anionic bidentate ligand, A³And A⁴Each independently represents a carbon atom, an oxygen atom or a nitrogen atom, these atoms being optionally atoms constituting a ring, G²Represents a single bond, or with A³And A⁴Radicals together forming a bidentate ligand, A³－G²－A⁴In case of plural, they are optionally in phaseEither the same or different from each other,

-R^1T (1-T)

in the formula, R^1TRepresents an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryloxy group, an aryl group, a monovalent heterocyclic group or a substituted amino group, which groups optionally have a substituent, and when a plurality of these groups are present, they are optionally the same or different, and are optionally bonded to each other to form a ring together with the respective bonded atoms.

16. The composition for a light-emitting element according to claim 15,

the ring L¹Is a pyridine ring, a diaza-benzene ring, a quinoline ring or a diaza-naphthalene ring, these rings optionally having a substituent, and

the R is^1TIs an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group or a substituted amino group, and these groups may have a substituent.

17. The composition for a light-emitting element according to claim 15,

the ring L¹Is an isoquinoline ring optionally having a substituent, and R is^1TIs an aryl group, a monovalent heterocyclic group or a substituted amino group, which may have a substituent.

18. The composition for a light-emitting element according to any one of claims 15 to 17,

the fused heterocyclic skeleton b contains a boron atom and a nitrogen atom within the ring.

19. The composition for a light-emitting element according to any one of claims 15 to 18,

further comprises a compound represented by the formula (H-1),

in the formula (I), the compound is shown in the specification,

Ar^H1and Ar^H2Each independently represents an aryl group, a monovalent heterocyclic group or a substituted amino group, which groups optionally have a substituent which, when plural, are optionally the same or different, and are optionally bonded to each other to form a ring together with each bonded atom,

n^H1represents an integer of 0 or more and is,

L^H1represents an arylene group, a divalent heterocyclic group, an alkylene group or a cycloalkylene group, these groups optionally having a substituent, which may be the same or different when plural, are optionally bonded to each other to form a ring together with the atom to which each is bonded, L^H1When a plurality of them is present, they are optionally the same or different.

20. The composition for a light-emitting element according to any one of claims 15 to 19,

further contains at least 1 selected from the group consisting of a hole transporting material, a hole injecting material, an electron transporting material, an electron injecting material, a light emitting material, an antioxidant and a solvent.

Technical Field

The present invention relates to a light-emitting element and a composition for a light-emitting element.

Background

Light-emitting elements such as organic electroluminescent elements can be suitably used for displays and lighting, for example. As a light-emitting material used in a light-emitting layer of a light-emitting element, for example, patent document 1 proposes a composition containing compound B0 and metal complex G1 or metal complex Firpic.

[ chemical formula 1]

As a light-emitting material used in a light-emitting layer of a light-emitting element, for example, patent document 2 proposes a composition containing a Thermally Activated Delayed Fluorescence (TADF) compound T0 and a metal complex G3.

[ chemical formula 2]

Documents of the prior art

Patent document

Patent document 1: japanese patent laid-open publication No. 2018-043984

Patent document 2: international publication No. 2017/154884

Disclosure of Invention

Problems to be solved by the invention

However, the light-emitting element produced using the above composition does not necessarily have sufficient light-emitting efficiency.

Accordingly, an object of the present invention is to provide a composition useful for producing a light-emitting element having excellent luminous efficiency, and to provide a light-emitting element containing the composition.

Means for solving the problems

The present inventors have conducted extensive studies to solve the above problems, and as a result, have found that a light-emitting element having excellent light-emitting efficiency can be formed by a combination of a specific metal complex and a specific compound (B), and have completed the present invention. The metal complex G1 of patent document 1 is a metal complex having no group represented by the formula (1-T) described later. Further, the compound T0 of patent document 2 is a compound having no fused heterocyclic skeleton (b) described later.

Namely, the present invention provides the following [1] to [20 ].

[1] A light-emitting element comprising an anode, a cathode, and an organic layer containing a light-emitting element composition provided between the anode and the cathode,

the composition for a light-emitting element contains

A metal complex represented by the formula (2), and

having a ring containing boron atoms and atoms selected from oxygen, sulfur, selenium, sp³A compound (B) having a condensed heterocyclic skeleton of at least 1 of carbon atoms and nitrogen atoms.

[ chemical formula 3]

[ in the formula,

M²represents a rhodium atom, a palladium atom, an iridium atom or a platinum atom.

n³Represents an integer of 1 or more, n⁴Represents an integer of 0 or more. Wherein, at M²In the case of a rhodium atom or an iridium atom, n³+n⁴Is 3 at M²In the case of palladium atom or platinum atom, n³+n⁴Is 2.

E^LRepresents a carbon atom or a nitrogen atom. E^LWhen there are a plurality of them, they may be the same or different.

Ring L¹Represents an aromatic heterocyclic ring comprising a six-membered ring, which ring may have a substituent. When a plurality of such substituents are present, they may be the same or different, and may be bonded to each other to form a ring together with the atom to which they are bonded. Ring L¹When a plurality of the compounds exist, they may be the same or different.

Ring L²Representing an aromatic hydrocarbon ring or an aromatic hydrocarbonAromatic heterocyclic rings, which may have a substituent. When a plurality of such substituents are present, they may be the same or different, and may be bonded to each other to form a ring together with the atom to which they are bonded. Ring L²When a plurality of the compounds exist, they may be the same or different.

Ring L¹Substituent which may be present with the ring L²The substituents which may be present may be the same or different and may be bonded to each other to form a ring together with the atoms to which they are bonded.

Wherein, the ring L¹And ring L²At least 1 of them having a group represented by the formula (1-T) as a substituent. When a plurality of groups represented by the formula (1-T) are present, they may be the same or different.

A³－G²－A⁴Represents an anionic bidentate ligand. A. the³And A⁴Each independently represents a carbon atom, an oxygen atom or a nitrogen atom, and these atoms may be atoms constituting a ring. G²Represents a single bond, or with A³And A⁴Together forming the radical of a bidentate ligand. A. the³－G²－A⁴When a plurality of the compounds exist, they may be the same or different.]

[ chemical formula 4]

-R^1T(1-T)

[ in the formula, R^1TRepresents an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryloxy group, an aryl group, a monovalent heterocyclic group or a substituted amino group, and these groups may have a substituent. When a plurality of such substituents are present, they may be the same or different, and may be bonded to each other to form a ring together with the atom to which they are bonded.]

[2] The light-emitting element according to [1], wherein,

the above-mentioned ring L¹Is a pyridine ring, a diazaphenzene ring, an azanaphthalene ring or a diazaphalene ring, and these rings may have a substituent.

[3] The light-emitting element according to [2], wherein,

the above-mentioned ring L¹Is pyridine ring, diazabenzeneA ring, a quinoline ring or a naphthyridine ring, which may have a substituent, and

r is as defined above^1TIs an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group or a substituted amino group, and these groups may have a substituent.

[4] The light-emitting element according to [2], wherein,

the above-mentioned ring L¹Is an isoquinoline ring which may have a substituent, and

r is as defined above^1TIs an aryl group, a monovalent heterocyclic group or a substituted amino group, and these groups may have a substituent.

[5] The light-emitting element according to any one of [1] to [4], wherein,

the above-mentioned ring L²Is a benzene ring, a pyridine ring or a diaza-benzene ring, and these rings may have a substituent.

[6] The light-emitting element according to any one of [1] to [5],

r is as defined above^1TIs an aryl group which may have a substituent or a monovalent heterocyclic group which may have a substituent.

[7] The light-emitting element according to any one of [1] to [6],

the fused heterocyclic skeleton (b) contains a boron atom and at least 1 selected from an oxygen atom, a sulfur atom and a nitrogen atom in the ring.

[8] The light-emitting element according to [7], wherein,

the fused heterocyclic skeleton (b) contains a boron atom and a nitrogen atom in the ring.

[9] The light-emitting element according to any one of [1] to [6],

the compound (B) is a compound represented by the formula (1-1), a compound represented by the formula (1-2) or a compound represented by the formula (1-3).

[ chemical formula 5]

[ in the formula,

Ar¹、Ar²and Ar³Each independently represents an aromatic hydrocarbon group or a heterocyclic group, and these groups may have a substituent. When a plurality of such substituents are present, they may be the same or different, and may be bonded to each other to form a ring together with the atom to which they are bonded.

Y¹Represents an oxygen atom, a sulfur atom, a selenium atom, a group represented by the formula-N (Ry) -or an alkylene group or a cycloalkylene group, and these groups may have a substituent. When a plurality of such substituents are present, they may be the same or different, and may be bonded to each other to form a ring together with the atom to which they are bonded.

Y²And Y³Each independently represents a single bond, an oxygen atom, a sulfur atom, a selenium atom, a group represented by-N (Ry) -, an alkylene group or a cycloalkylene group, and these groups may have a substituent. When a plurality of such substituents are present, they may be the same or different, and may be bonded to each other to form a ring together with the atom to which they are bonded. Ry represents a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, and these groups may have a substituent. When a plurality of such substituents are present, they may be the same or different, and may be bonded to each other to form a ring together with the atom to which they are bonded. When there are a plurality of Ry, they may be the same or different. Ry may be bonded to Ar directly or via a linking group¹、Ar²Or Ar³And (4) bonding.]

[10] The light-emitting element according to [9], wherein,

y is above¹Y is as defined above²And the above Y³Is an oxygen atom, a sulfur atom or a group represented by-N (Ry) -.

[11] The light-emitting element according to [10], wherein,

y is above¹Y is as defined above²And the above Y³Is a group represented by-N (Ry) -or a pharmaceutically acceptable salt thereof.

[12] The light-emitting element according to any one of [1] to [11], wherein,

the absolute value of the difference between the energy level of the lowest triplet excited state of the compound (B) and the energy level of the lowest singlet excited state of the compound (B) is 0.50eV or less.

[13] The light-emitting element according to any one of [1] to [12],

the composition for a light-emitting element further contains a compound represented by the formula (H-1).

[ chemical formula 6]

[ in the formula,

Ar^H1and Ar^H2Each independently represents an aryl group, a monovalent heterocyclic group or a substituted amino group, and these groups may have a substituent. When a plurality of such substituents are present, they may be the same or different, and may be bonded to each other to form a ring together with the atom to which they are bonded.

n^H1Represents an integer of 0 or more.

L^H1Represents an arylene group, a divalent heterocyclic group, an alkylene group or a cycloalkylene group, and these groups may have a substituent. When a plurality of such substituents are present, they may be the same or different, and may be bonded to each other to form a ring together with the atom to which they are bonded. L is^H1When a plurality of the compounds exist, they may be the same or different.]

[14] The light-emitting element according to any one of [1] to [13],

the composition for a light-emitting element further contains at least 1 selected from a hole-transporting material, a hole-injecting material, an electron-transporting material, an electron-injecting material, a light-emitting material, an antioxidant and a solvent.

[15] A composition for a light-emitting element comprising

A metal complex represented by the formula (2), and

having a ring containing boron atoms and atoms selected from oxygen, sulfur, selenium, sp³A compound (B) having a condensed heterocyclic skeleton of at least 1 of carbon atoms and nitrogen atoms.

[ chemical formula 7]

[ in the formula,

M²represents a rhodium atom, a palladium atom, an iridium atom or a platinum atom.

n³Represents an integer of 1 or more, n⁴Represents an integer of 0 or more. Wherein, at M²In the case of a rhodium atom or an iridium atom, n³+n⁴Is 3 at M²In the case of palladium atom or platinum atom, n³+n⁴Is 2.

E^LRepresents a carbon atom or a nitrogen atom. E^LWhen there are a plurality of them, they may be the same or different.

Ring L¹Represents an aromatic heterocyclic ring comprising a six-membered ring, which ring may have a substituent. When a plurality of such substituents are present, they may be the same or different, and may be bonded to each other to form a ring together with the atom to which they are bonded. Ring L¹When a plurality of the compounds exist, they may be the same or different.

Ring L²Represents an aromatic hydrocarbon ring or an aromatic heterocyclic ring, and these rings may have a substituent. When a plurality of such substituents are present, they may be the same or different, and may be bonded to each other to form a ring together with the atom to which they are bonded. Ring L²When a plurality of the compounds exist, they may be the same or different.

Ring L¹Substituent which may be present with the ring L²The substituents which may be present may be the same or different and may be bonded to each other to form a ring together with the atoms to which they are bonded.

Wherein, the ring L¹And ring L²At least 1 of them having a group represented by the formula (1-T) as a substituent. When a plurality of groups represented by the formula (1-T) are present, they may be the same or different.

A³－G²－A⁴Represents an anionic bidentate ligand.A³And A⁴Each independently represents a carbon atom, an oxygen atom or a nitrogen atom, and these atoms may be atoms constituting a ring. G²Represents a single bond, or with A³And A⁴Together forming the radical of a bidentate ligand. A. the³－G²－A⁴When a plurality of the compounds exist, they may be the same or different.]

[ chemical formula 8]

-R^1T (1-T)

[ in the formula, R^1TRepresents an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryloxy group, an aryl group, a monovalent heterocyclic group or a substituted amino group, and these groups may have a substituent. When a plurality of such substituents are present, they may be the same or different, and may be bonded to each other to form a ring together with the atom to which they are bonded.]

[16] The composition for a light-emitting element according to [15], wherein,

the above-mentioned ring L¹Is a pyridine ring, a diaza-benzene ring, a quinoline ring or a diaza-naphthalene ring, which rings may have a substituent, and

r is as defined above^1TIs an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group or a substituted amino group, and these groups may have a substituent.

[17] The composition for a light-emitting element according to [15], wherein,

the above-mentioned ring L¹Is an isoquinoline ring which may have a substituent, and the above R^1TIs an aryl group, a monovalent heterocyclic group or a substituted amino group, and these groups may have a substituent.

[18] The composition for a light-emitting element according to any one of [15] to [17], wherein,

the fused heterocyclic skeleton (b) contains a boron atom and a nitrogen atom in the ring.

[19] The composition for a light-emitting element according to any one of [15] to [18], wherein,

also contains a compound represented by the formula (H-1).

[ chemical formula 9]

[ in the formula,

Ar^H1and Ar^H2Each independently represents an aryl group, a monovalent heterocyclic group or a substituted amino group, and these groups may have a substituent. When a plurality of such substituents are present, they may be the same or different, and may be bonded to each other to form a ring together with the atom to which they are bonded.

n^H1Represents an integer of 0 or more.

L^H1Represents an arylene group, a divalent heterocyclic group, an alkylene group or a cycloalkylene group, and these groups may have a substituent. When a plurality of such substituents are present, they may be the same or different, and may be bonded to each other to form a ring together with the atom to which they are bonded. L is^H1When a plurality of the compounds exist, they may be the same or different.]

[20] The composition for a light-emitting element according to any one of [15] to [19], wherein,

further contains at least 1 selected from the group consisting of a hole transporting material, a hole injecting material, an electron transporting material, an electron injecting material, a light emitting material, an antioxidant and a solvent.

ADVANTAGEOUS EFFECTS OF INVENTION

According to the present invention, a composition useful for producing a light-emitting element having excellent light-emitting efficiency can be provided. Further, according to the present invention, a light-emitting element containing the composition can be provided.

Detailed Description

Hereinafter, preferred embodiments of the present invention will be described in detail.

Description of common terms

Terms commonly used in the present specification have the following meanings unless otherwise specified.

"Room temperature" means 25 ℃.

Me represents a methyl group, Et represents an ethyl group, Bu represents a butyl group, i-Pr represents an isopropyl group, and t-Bu represents a tert-butyl group.

The hydrogen atom may be a deuterium atom or a protium atom.

"Low molecular weight compound" means a compound having no molecular weight distribution and a molecular weight of 1X 10⁴The following compounds.

The term "polymer compound" means a compound having a molecular weight distribution and a number average molecular weight of 1X 10 in terms of polystyrene³Above (e.g., 1 × 10)³～1×10⁸) The polymer of (1).

The term "structural unit" means that 1 or more units are present in the polymer compound.

The polymer compound may be any of a block copolymer, a random copolymer, an alternating copolymer, and a graft copolymer, or may be in other forms.

The end groups of the polymer compound are preferably stable groups since the polymerizable groups remain as they are, and when the polymer compound is used for manufacturing a light-emitting element, the light-emitting characteristics or the luminance lifetime may be reduced. The terminal group of the polymer compound is preferably a group conjugated to the main chain, and examples thereof include a group bonded to an aryl group or a monovalent heterocyclic group bonded to the main chain of the polymer compound via a carbon-carbon bond.

The "alkyl group" may be any of a straight chain and a branched chain. The number of carbon atoms of the linear alkyl group excluding the number of carbon atoms of the substituent is usually 1 to 50, preferably 1 to 20, and more preferably 1 to 10. The number of carbon atoms of the branched alkyl group excluding the number of carbon atoms of the substituent is usually 3 to 50, preferably 3 to 20, and more preferably 4 to 10.

The alkyl group may have a substituent. Examples of the alkyl group include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, a 2-butyl group, an isobutyl group, a tert-butyl group, a pentyl group, an isopentyl group, a 2-ethylbutyl group, a hexyl group, a heptyl group, an octyl group, a 2-ethylhexyl group, a 3-propylheptyl group, a decyl group, a 3, 7-dimethyloctyl group, a 2-ethyloctyl group, a 2-hexyldecyl group and a dodecyl group. The alkyl group may be a group in which some or all of the hydrogen atoms in these groups are substituted with a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, a fluorine atom, or the like. Examples of such an alkyl group include a trifluoromethyl group, a pentafluoroethyl group, a perfluorobutyl group, a perfluorohexyl group, a perfluorooctyl group, a 3-phenylpropyl group, a 3- (4-methylphenyl) propyl group, a 3- (3, 5-dihexylphenyl) propyl group and a 6-ethoxyhexyl group.

The number of carbon atoms of the "cycloalkyl group" is usually 3 to 50, preferably 4 to 10, excluding the number of carbon atoms of the substituent. The cycloalkyl group may have a substituent. Examples of the cycloalkyl group include cyclohexyl and methylcyclohexyl.

The number of carbon atoms of the "alkylene group" is usually 1 to 20, preferably 1 to 15, and more preferably 1 to 10, excluding the number of carbon atoms of the substituent. The alkylene group may have a substituent. Examples of the alkylene group include a methylene group, an ethylene group, a propylene group, a butylene group, a hexylene group and an octylene group.

The number of carbon atoms of the "cycloalkylene group" is usually 3 to 20, preferably 4 to 10, excluding the number of carbon atoms of the substituent. The cycloalkylene group may have a substituent. Examples of the cycloalkylene group include cyclohexylene group.

The "aromatic hydrocarbon group" refers to a group obtained by removing 1 or more hydrogen atoms directly bonded to atoms constituting a ring from an aromatic hydrocarbon. A group obtained by removing 1 hydrogen atom directly bonded to an atom constituting a ring from an aromatic hydrocarbon is also referred to as an "aryl group". A group obtained by removing 2 hydrogen atoms directly bonded to atoms constituting a ring from an aromatic hydrocarbon is also referred to as "arylene".

The number of carbon atoms of the aromatic hydrocarbon group excluding the number of carbon atoms of the substituent is usually 6 to 60, preferably 6 to 40, and more preferably 6 to 20.

Examples of the "aromatic hydrocarbon group" include groups obtained by removing 1 or more hydrogen atoms directly bonded to atoms constituting a ring from monocyclic aromatic hydrocarbons (for example, benzene) or polycyclic aromatic hydrocarbons (for example, bicyclic aromatic hydrocarbons such as naphthalene and indene, tricyclic aromatic hydrocarbons such as anthracene, phenanthrene, dihydrophenanthrene, and fluorene, tetracyclic aromatic hydrocarbons such as benzanthracene, benzophenanthrene, benzofluorene, pyrene, and fluoranthene, pentacyclic aromatic hydrocarbons such as dibenzoanthracene, dibenzophenanthrene, dibenzofluorene, perylene, and benzofluoranthene, hexacyclic aromatic hydrocarbons such as spirobifluorene, and heptacyclic aromatic hydrocarbons such as benzospirobifluorene and acenaphthofluorene). The aromatic hydrocarbon group includes a group in which a plurality of these groups are bonded. The aromatic hydrocarbon group may have a substituent.

The "alkoxy group" may be any of a straight chain and a branched chain. The number of carbon atoms of the linear alkoxy group is usually 1 to 40, preferably 1 to 10, excluding the number of carbon atoms of the substituent. The number of carbon atoms of the branched alkoxy group excluding the number of carbon atoms of the substituent is usually 3 to 40, preferably 4 to 10.

The alkoxy group may have a substituent. Examples of the alkoxy group include a methoxy group, an ethoxy group, an isopropoxy group, a butoxy group, a hexyloxy group, a 2-ethylhexyloxy group, a 3, 7-dimethyloctyloxy group and a lauryloxy group.

The number of carbon atoms of the "cycloalkoxy group" is usually 3 to 40, preferably 4 to 10, excluding the number of carbon atoms of the substituent. The cycloalkoxy group may have a substituent. Examples of the cycloalkoxy group include a cyclohexyloxy group.

The number of carbon atoms of the "aryloxy group" is usually 6 to 60, preferably 6 to 40, and more preferably 6 to 20, excluding the number of carbon atoms of the substituent. The aryloxy group may have a substituent. Examples of the aryloxy group include a phenoxy group, a naphthoxy group, an anthracenoxy group, and a pyreneoxy group.

The "heterocyclic group" refers to a group obtained by removing 1 or more hydrogen atoms directly bonded to atoms constituting a ring from a heterocyclic compound. Among the heterocyclic groups, a "aromatic heterocyclic group" is preferred, which is a group obtained by removing 1 or more hydrogen atoms directly bonded to atoms constituting a ring from an aromatic heterocyclic compound. A group obtained by removing p (p represents an integer of 1 or more) hydrogen atoms directly bonded to atoms constituting a ring from a heterocyclic compound is also referred to as a "p-valent heterocyclic group". A group obtained by removing p hydrogen atoms directly bonded to the ring-constituting atoms from an aromatic heterocyclic compound is also referred to as a "p-valent aromatic heterocyclic group".

Examples of the "aromatic heterocyclic compound" include compounds in which a heterocyclic ring itself such as oxazole, thiophene, furan, pyridine, diazabenzene, triazine, azanaphthalene, naphthyridine and carbazole exhibits aromaticity, and compounds in which an aromatic ring is fused to a heterocyclic ring itself such as phenoxazine, phenothiazine and benzopyran even if the heterocyclic ring itself does not exhibit aromaticity.

The number of carbon atoms of the heterocyclic group excluding the number of carbon atoms of the substituent is usually 1 to 60, preferably 2 to 40, and more preferably 3 to 20. The number of hetero atoms of the aromatic heterocyclic group is usually 1 to 30, preferably 1 to 10, more preferably 1 to 5, and further preferably 1 to 3, excluding the number of hetero atoms of the substituent.

Examples of the heterocyclic group include: from monocyclic heterocyclic compounds (for example, furan, thiophene, oxadiazole, pyrrole, oxadiazole, triazole, tetrazole, pyridine, diazabenzene and triazine) or polycyclic heterocyclic compounds (for example, bicyclic heterocyclic compounds such as azanaphthalene, naphthyridine, benzofuran, benzothiophene, indole, benzodiazole and benzothiadiazole; dibenzofuran, dibenzothiophene, dibenzoborole, dibenzothiaole, dibenzophosphole, dibenzoselenophene, carbazole, azacarbazole, diazacazole, phenoxazine, phenothiazine, 9, 10-dihydroacridine, 5, 10-dihydrophenazine, 9-aza-10-boranthracene (Japanese: フェナザボリン), 9-aza-10-phosphahanthrene (phenophosphosphazine), Phenoselenazine (Phenoselenazine), Tricyclic heterocyclic compounds such as 9-aza-10-silaanthracene (phenoazasine), azaanthracene, diazaanthracene, azaphenanthrene and phenanthroline; tetracyclic heterocyclic compounds such as hexaazatriphenylene, benzocarbazole, benzonaphthofuran, benzonaphthothiophene and the like; pentacyclic heterocyclic compounds such as dibenzocarbazole, indolocarbazole, and indenocarbazole; hexacyclic heterocyclic compounds such as carbazolocarbazole, benzindolocarbazole and benzindenocarbazole; and a heptacyclic heterocyclic compound such as dibenzoindolocarbazole) from which 1 or more hydrogen atoms directly bonded to atoms constituting the ring have been removed. The heterocyclic group includes a group in which a plurality of these groups are bonded. The heterocyclic group may have a substituent.

"halogen atom" means a fluorine atom, chlorine atom, bromine atom or iodine atom.

The "amino group" may have a substituent, preferably a substituted amino group (i.e., a secondary or tertiary amino group, more preferably a tertiary amino group). The substituent of the amino group is preferably an alkyl group, a cycloalkyl group, an aryl group, or a monovalent heterocyclic group. When a plurality of substituents are present, the substituents may be the same or different, and may be bonded to each other to form a ring together with the nitrogen atom to which each substituent is bonded.

Examples of the substituted amino group include a dialkylamino group, a bicycloalkylamino group, and a diarylamino group.

Examples of the amino group include a dimethylamino group, a diethylamino group, a diphenylamino group, a bis (methylphenyl) amino group, and a bis (3, 5-di-t-butylphenyl) amino group.

The "alkenyl group" may be any of a straight chain and a branched chain. The number of carbon atoms of the linear alkenyl group excluding the number of carbon atoms of the substituent is usually 2 to 30, preferably 3 to 20. The number of carbon atoms of the branched alkenyl group excluding the number of carbon atoms of the substituent is usually 3 to 30, preferably 4 to 20.

The number of carbon atoms of the "cycloalkenyl group" is usually 3 to 30, preferably 4 to 20, excluding the number of carbon atoms of the substituent.

The alkenyl group and the cycloalkenyl group may have a substituent. Examples of the alkenyl group include a vinyl group, a 1-propenyl group, a 2-butenyl group, a 3-pentenyl group, a 4-pentenyl group, a 1-hexenyl group, a 5-hexenyl group, a 7-octenyl group, and groups in which some or all of the hydrogen atoms in these groups are substituted with a substituent. Examples of the cycloalkenyl group include a cyclohexenyl group, a cyclohexadienyl group, a cyclooctatrienyl group, a norbornenyl group, and groups in which some or all of hydrogen atoms in these groups are substituted with a substituent.

The "alkynyl group" may be any of a straight chain and a branched chain. The number of carbon atoms of the alkynyl group excluding the carbon atoms of the substituent is usually 2 to 20, preferably 3 to 20. The number of carbon atoms of the branched alkynyl group excluding the carbon atoms of the substituent is usually 4 to 30, preferably 4 to 20.

The number of carbon atoms of the "cycloalkynyl group" is usually 4 to 30, preferably 4 to 20, excluding the carbon atoms of the substituent.

The alkynyl group and the cycloalkynyl group may have a substituent. Examples of the alkynyl group include an ethynyl group, a 1-propynyl group, a 2-butynyl group, a 3-pentynyl group, a 4-pentynyl group, a 1-hexynyl group, a 5-hexynyl group, and groups in which some or all of the hydrogen atoms in these groups are substituted with a substituent. Examples of the cycloalkynyl group include cyclooctynyl.

The "crosslinking group" is a group capable of generating a new bond by being subjected to heat, ultraviolet irradiation, near ultraviolet irradiation, visible light irradiation, infrared irradiation, radical reaction, or the like. The crosslinking group is preferably a crosslinking group selected from the group A of crosslinking groups (i.e., a group represented by any one of the formulae (XL-1) to (XL-19)).

(Cross-linking group A group)

[ chemical formula 10]

[ in the formula, R^XLRepresents a methylene group, an oxygen atom or a sulfur atom, n^XLRepresents an integer of 0 to 5. R^XLWhen a plurality of the compounds exist, they may be the same or different. A plurality of n present^XLMay be the same or different. And x 1 represents a bonding site. These crosslinking groups may have a substituent. When a plurality of such substituents are present, they may be the same or different, and may be bonded to each other to form a ring together with the carbon atom to which each substituent is bonded.]

Examples of the "substituent" include a halogen atom, a cyano group, an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group, an alkoxy group, a cycloalkoxy group, an aryloxy group, an amino group, a substituted amino group, an alkenyl group, a cycloalkenyl group, an alkynyl group, and a cycloalkynyl group. The substituent may be a crosslinking group. When a plurality of substituents are present, they may be bonded to each other to form a ring together with the atoms to which they are bonded, but preferably do not form a ring.

In this specification, the most important isThe absolute value of the difference between the energy level of the low triplet excited state and the energy level of the lowest singlet excited state (hereinafter also referred to as "Δ E_ST") was calculated by the following method. First, the ground state of the compound was structurally optimized using the density functional method at the B3LYP level. In this case, 6-31 G.ANG.is used as the basis function. Then, using the structure optimized by the obtained structure, the time-dependent density functional method of B3LYP level was used to calculate the Δ E of the compound_ST. When an atom which cannot be used is included in the range of 6 to 31G, LANL2DZ is used for the atom. Note that, as a quantum chemical calculation program, calculation was performed using Gaussian 09.

< composition for light-emitting element >

The composition for a light-emitting element of the present embodiment contains a metal complex represented by formula (2) and a compound (B) having a condensed heterocyclic skeleton (B).

In the composition for a light-emitting element of the present embodiment, each of the metal complex represented by the formula (2) and the compound (B) may contain only 1 species, or may contain 2 or more species.

In the composition for a light-emitting element of the present embodiment, the metal complex represented by the formula (2) and the compound (B) preferably interact physically, chemically, or electrically. By this interaction, for example, the light-emitting characteristics, the charge transport characteristics, or the charge injection characteristics of the light-emitting element composition of the present embodiment can be improved or adjusted.

In the composition for a light-emitting element of the present embodiment, a light-emitting material is exemplified, and in this case, the metal complex represented by the formula (2) and the compound (B) electrically interact with each other, and electric energy is efficiently transmitted from the compound (B) to the metal complex represented by the formula (2), whereby the metal complex represented by the formula (2) can emit light more efficiently, and the light-emitting element of the present embodiment has more excellent light-emitting efficiency.

From the above viewpoint, the lowest excited triplet state (T) of the compound (B) is more excellent in the light-emitting efficiency of the light-emitting element of the present embodiment₁) Preferably, the lowest excited triplet state of the metal complex represented by the formula (2)(T₁) A higher energy level.

In the composition for a light-emitting element of the present embodiment, the content of the metal complex represented by formula (2) is usually 0.1 to 99.9 parts by mass when the total of the compound (B) and the metal complex represented by formula (2) is 100 parts by mass, but is preferably 1 to 99 parts by mass, more preferably 10 to 97 parts by mass, further preferably 30 to 95 parts by mass, particularly preferably 50 to 90 parts by mass, and particularly preferably 70 to 90 parts by mass, because the light-emitting element of the present embodiment has more excellent light-emitting efficiency.

[ Compound (B) ]

The compound (B) is a compound having a ring containing a boron atom and a sulfur atom, a selenium atom, sp³A compound having a condensed heterocyclic skeleton of at least 1 of carbon atoms and nitrogen atoms.

In the compound (B), when the condensed heterocyclic skeleton (B) contains a nitrogen atom, at least 1 of the nitrogen atoms contained in the condensed heterocyclic skeleton (B) is preferably a nitrogen atom which does not form a double bond, and more preferably all of the nitrogen atoms contained in the condensed heterocyclic skeleton (B) are nitrogen atoms which do not form a double bond.

The number of carbon atoms of the condensed heterocyclic skeleton (b) is usually 1 to 60, preferably 5 to 40, and more preferably 10 to 25, excluding the number of carbon atoms of the substituent.

The number of hetero atoms of the condensed heterocyclic skeleton (b) is usually 2 to 30, preferably 2 to 15, more preferably 2 to 10, further preferably 2 to 5, particularly preferably 2 or 3, excluding the number of hetero atoms of the substituent.

The number of boron atoms of the condensed heterocyclic skeleton (b) is usually 1 to 10, preferably 1 to 5, more preferably 1 to 3, and still more preferably 1, excluding the number of boron atoms of the substituent.

Oxygen atom, sulfur atom, selenium atom, sp of condensed heterocyclic skeleton (b)³The total number of carbon atoms and nitrogen atoms is usually 1 to 20, preferably 1 to 10, more preferably 1 to 5, further preferably 1 to 3, and particularly preferably 2, excluding the number of atoms of the substituent.

The condensed heterocyclic skeleton (b) preferably contains a boron atom and at least 1 selected from an oxygen atom, a sulfur atom, and a nitrogen atom in the ring, more preferably contains a boron atom and a nitrogen atom in the ring, and still more preferably contains a boron atom and a nitrogen atom not forming a double bond in the ring, from the viewpoint that the light-emitting element of the present embodiment is more excellent in light-emitting efficiency.

The condensed heterocyclic skeleton (b) is preferably a three-to twelve-ring condensed heterocyclic skeleton, more preferably a three-to six-ring condensed heterocyclic skeleton, and still more preferably a five-ring condensed heterocyclic skeleton, because the light-emitting element of the present embodiment has more excellent light-emitting efficiency.

The fused heterocyclic skeleton (b) may also be referred to as a compound having a heterocyclic group (b') including the fused heterocyclic skeleton (b).

The heterocyclic group (b') may be a heterocyclic group consisting of a ring containing a boron atom and a nitrogen atom selected from the group consisting of an oxygen atom, a sulfur atom, a selenium atom, and sp³The polycyclic heterocyclic compound having at least 1 of carbon atoms and nitrogen atoms may have a substituent except for a group in which 1 or more hydrogen atoms directly bonded to the ring-constituting atoms are removed. Among the heterocyclic groups (b'), the polycyclic heterocyclic compound is preferably a polycyclic heterocyclic compound containing a boron atom and at least 1 selected from an oxygen atom, a sulfur atom and a nitrogen atom in the ring, more preferably a polycyclic heterocyclic compound containing a boron atom and a nitrogen atom in the ring, and still more preferably a polycyclic heterocyclic compound containing a boron atom and a nitrogen atom which does not form a double bond in the ring. Among the heterocyclic groups (b'), the polycyclic heterocyclic compound is preferably a tricyclic to dodecacyclic heterocyclic compound, more preferably a tricyclic to hexacyclic heterocyclic compound, and still more preferably a pentacyclic heterocyclic compound.

The substituent which the heterocyclic group (b') may have is preferably a halogen atom, a cyano group, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, a monovalent heterocyclic group or a substituted amino group, more preferably an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, a monovalent heterocyclic group or a substituted amino group, and further preferably an alkyl group, an aryl group or a substituted amino group, and these groups may further have a substituent.

Among the substituents which the heterocyclic group (b') may have, the aryl group is preferably a group obtained by removing 1 hydrogen atom directly bonded to a ring-constituting atom from a monocyclic or bicyclic to hexacyclic aromatic hydrocarbon, more preferably a group obtained by removing 1 hydrogen atom directly bonded to a ring-constituting atom from a monocyclic, bicyclic or tricyclic aromatic hydrocarbon, still more preferably a group obtained by removing 1 hydrogen atom directly bonded to a ring-constituting atom from benzene, naphthalene, anthracene, phenanthrene or fluorene, particularly preferably a phenyl group, and these groups may have a substituent.

Among the substituents that the heterocyclic group (b') may have, a monovalent heterocyclic group is preferably a group obtained by removing 1 hydrogen atom directly bonded to a ring-constituting atom from a monocyclic or bicyclic to hexacyclic heterocyclic compound, more preferably a group obtained by removing 1 hydrogen atom directly bonded to a ring-constituting atom from a monocyclic, bicyclic or tricyclic heterocyclic compound, still more preferably a group obtained by removing 1 hydrogen atom directly bonded to a ring-constituting atom from pyridine, diazabenzene, triazine, azanaphthalene, naphthyridine, carbazole, dibenzofuran, dibenzothiophene, phenoxazine or phenothiazine, particularly preferably a group obtained by removing 1 hydrogen atom directly bonded to a ring-constituting atom from pyridine, diazabenzene or triazine, and these groups may have a substituent.

Among the substituted amino groups that the heterocyclic group (b') may have, as the substituent group that the amino group has, preferably an aryl group or a monovalent heterocyclic group, more preferably an aryl group, and these groups may further have a substituent group. Examples and preferable ranges of the aryl group and the monovalent heterocyclic group in the substituent which the amino group has are the same as those of the aryl group and the monovalent heterocyclic group in the substituent which the heterocyclic group (b') may have, respectively.

The substituent which the heterocyclic group (b') may have is preferably a halogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, a monovalent heterocyclic group or a substituted amino group, more preferably an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group or a substituted amino group, and further preferably an alkyl group or a cycloalkyl group, and these groups may further have a substituent, but preferably do not further have a substituent.

Examples and preferable ranges of the aryl group, the monovalent heterocyclic group and the substituted amino group in the substituents which the heterocyclic group (b ') may have may further be the same as examples and preferable ranges of the aryl group, the monovalent heterocyclic group and the substituted amino group in the substituents which the heterocyclic group (b') may have, respectively.

The "nitrogen atom not forming a double bond" means a nitrogen atom bonded to the other 3 atoms by single bonds, respectively.

"containing a nitrogen atom having no double bond formed in a ring" means that-N (-R) is contained in the ring^N) - (in the formula, R^NRepresents a hydrogen atom or a substituent. ) Or a group of the formula.

[ chemical formula 11]

The compound (B) is preferably a Thermally Active Delayed Fluorescence (TADF) compound for the reason that the light-emitting element of the present embodiment has more excellent light-emitting efficiency.

Delta E of Compound (B)_STThe thickness may be 2.0eV or less, may be 1.5eV or less, may be 1.0eV or less, may be 0.80eV or less, and may be 0.60eV or less, and is preferably 0.50eV or less for the reason that the light-emitting element of the present embodiment is more excellent in light-emitting efficiency. In addition,. DELTA.E of Compound (B)_STThe dielectric constant may be 0.001eV or more, may be 0.01eV or more, may be 0.10eV or more, may be 0.20eV or more, may be 0.30eV or more, or may be 0.40eV or more.

The compound (B) is preferably a low-molecular compound.

The molecular weight of the compound (B) is preferably 1X 10²～5×10³More preferably 2X 10²～3×10³More preferably 3X 10²～1.5×10³Particularly preferably 4X 10²～1×10³。

The compound (B) is preferably a compound represented by formula (1-1), formula (1-2), or formula (1-3), more preferably a compound represented by formula (1-2) or formula (1-3), and still more preferably a compound represented by formula (1-2), because the light-emitting element of the present embodiment has more excellent light-emitting efficiency.

Ar¹、Ar²And Ar³For the reason that the light-emitting element of the present embodiment has more excellent light-emitting efficiency, a group obtained by removing 1 or more hydrogen atoms directly bonded to atoms constituting a ring from a monocyclic, bicyclic, or tricyclic aromatic hydrocarbon or a monocyclic, bicyclic, or tricyclic heterocyclic compound is preferable, a group obtained by removing 1 or more hydrogen atoms directly bonded to atoms constituting a ring from a monocyclic aromatic hydrocarbon or monocyclic heterocyclic compound is more preferable, a group obtained by removing 1 or more hydrogen atoms directly bonded to atoms constituting a ring from benzene, pyridine, or diazepine is even more preferable, a group obtained by removing 1 or more hydrogen atoms directly bonded to atoms constituting a ring from benzene is particularly preferable, and these groups may have a substituent.

Ar¹、Ar²And Ar³Examples and preferred ranges of substituents which may be present are the same as those of substituents which may be present in the heterocyclic group (b').

Y¹Preferably an oxygen atom, a sulfur atom, -N (Ry) -or a methylene group, more preferably an oxygen atom, a sulfur atom or a group-N (Ry) -, and still more preferably a group-N (Ry) -, which may have a substituent.

Y²And Y³Preferably a single bond, an oxygen atom, a sulfur atom, a group represented by-N (Ry) -or a methylene group, more preferably a single bond, an oxygen atom, a sulfur atom or a group represented by-N (Ry) -and still more preferably an oxygen atom, a sulfur atom or a group represented by-N (Ry) -and particularly preferably a group represented by-N (Ry) -which may have a substituent.

Y is preferable for the reason that the light-emitting element of this embodiment mode has more excellent light-emitting efficiency¹、Y²And Y³All of which are oxygen atoms, sulfur atoms or groups represented by-N (Ry) -, more preferably Y¹、Y²And Y³Are all groups represented by-N (Ry) -or a salt thereof.

Y¹、Y²And Y³Examples and preferred ranges of substituents which may be present are the same as those of substituents which may be present in the heterocyclic group (b').

Ry is preferably an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, more preferably an aryl group or a monovalent heterocyclic group, and further preferably an aryl group, and these groups may have a substituent.

Examples and preferable ranges of the aryl group and the monovalent heterocyclic group in Ry are the same as those of the aryl group and the monovalent heterocyclic group, respectively, among the substituents which the heterocyclic group (b') may have.

Examples and preferred ranges of substituents that Ry may have are the same as those of substituents that heterocyclic group (b') may have.

Ry may be bonded to Ar directly or via a linking group¹、Ar²Or Ar³Bonded, but preferably not bonded. Examples of the linking group include: a group represented by-O-, a group represented by-S-, a group represented by-N (Ry) -, an alkylene group, a cycloalkylene group, an arylene group and a divalent heterocyclic group, preferably a group represented by-O-, a group represented by-S-, a group represented by-N (Ry) -, or a methylene group, and these groups may have a substituent.

Examples of the compound (B) include compounds represented by the following formulae and compounds B1 to B3 described later.

[ chemical formula 12]

[ chemical formula 13]

In the formula, Z¹Represents an oxygen atom or a sulfur atom.

[ Metal Complex represented by formula (2) ]

The metal complex represented by the formula (2) is usually a metal complex that exhibits phosphorescence at room temperature, and is preferably a metal complex that exhibits luminescence from a triplet excited state at room temperature.

The maximum peak wavelength of the emission spectrum of the metal complex represented by formula (2) is preferably 495nm or more and 750nm or less, more preferably 500nm or more and 680nm or less, still more preferably 505nm or more and 660nm or less, and particularly preferably 510nm or more and 640nm or less.

The maximum peak wavelength of the emission spectrum of the metal complex can be made into a dilute solution (1 × 10) by dissolving the metal complex in an organic solvent such as xylene, toluene, chloroform, tetrahydrofuran, or the like^-6～1×10^-3Mass%), the PL spectrum of the diluted solution was measured at room temperature to evaluate. As the organic solvent for dissolving the metal complex, xylene is preferable.

M²For the reason that the light-emitting element of the present embodiment has more excellent light-emitting efficiency, an iridium atom or a platinum atom is preferable, and an iridium atom is more preferable.

At M²In the case of a rhodium atom or an iridium atom, n³Preferably 2 or 3, more preferably 3.

At M²In the case of palladium atom or platinum atom, n³Preferably 2.

E^LPreferably a carbon atom. E^LWhen there are plural, they are preferably the same.

Ring L¹The number of carbon atoms of the six-membered aromatic heterocycle in (2) is usually 1 to 60, preferably 2 to 30, and more preferably 3 to 15, excluding the number of carbon atoms of the substituent. As a ring L¹Examples of the six-membered aromatic heterocyclic ring in (b) include aromatic heterocyclic rings having a six-membered ring and a nitrogen atom in the ring among the aromatic heterocyclic rings of the aromatic heterocyclic compounds exemplified in the above heterocyclic group.

Ring L¹The light-emitting element of the present embodiment preferably has 1 to 4 nitrogen atoms as a constituent for the reason that the light-emitting element has more excellent light-emitting efficiencyThe aromatic heterocyclic ring containing a six-membered ring of atoms is more preferably a pyridine ring, a diazaphenzene ring, an azanaphthalene ring or a diazaphalene ring, further preferably a pyridine ring, a quinoline ring or an isoquinoline ring, particularly preferably a pyridine ring or a quinoline ring, and particularly preferably a pyridine ring, and these rings may have a substituent.

The ring L is a metal complex represented by the formula (2) because the metal complex can be easily synthesized¹In the case where there are plural, there are plural rings L¹Of these, preferably at least 2 identical, more preferably a plurality of rings L are present¹Are all the same.

Ring L²The number of carbon atoms of the aromatic hydrocarbon ring in (1) is usually 6 to 60, preferably 6 to 30, and more preferably 6 to 18, excluding the number of carbon atoms of the substituent.

As a ring L²The aromatic hydrocarbon ring in (b) includes, for example, aromatic hydrocarbon rings of the aromatic hydrocarbons exemplified in the above aromatic hydrocarbon group.

Ring L²The aromatic hydrocarbon ring in (3) is preferably a monocyclic, bicyclic or tricyclic aromatic hydrocarbon ring, more preferably a benzene ring, a naphthalene ring, a fluorene ring, a phenanthrene ring or a dihydrophenanthrene ring, still more preferably a benzene ring, a fluorene ring or a dihydrophenanthrene ring, and particularly preferably a benzene ring, and these rings may have a substituent.

Ring L²The number of carbon atoms of the aromatic heterocycle in (2) is usually 1 to 60, preferably 2 to 30, and more preferably 3 to 15, excluding the number of carbon atoms of the substituent. Ring L²The number of hetero atoms of the aromatic heterocycle in (1) is usually 1 to 30, preferably 1 to 10, and more preferably 1 to 3, excluding the number of hetero atoms of the substituent.

As a ring L²Examples of the aromatic heterocyclic ring in (b) include aromatic heterocyclic rings of the aromatic heterocyclic compounds exemplified in the above items of heterocyclic groups.

Ring L²The aromatic heterocyclic ring in (1) is preferably a monocyclic, bicyclic or tricyclic aromatic heterocyclic ring, more preferably a pyridine ring, a diazepine ring, an azanaphthalene ring, a diazepine ring, an indole ring, a benzofuran ring, a benzothiophene ring, a carbazole ring, an azacarbazole ringA diazacarbazole ring, a dibenzofuran ring or a dibenzothiophene ring, more preferably a pyridine ring, a diazabenzene ring, a carbazole ring, a dibenzofuran ring or a dibenzothiophene ring, and particularly preferably a pyridine ring or a diazabenzene ring, and these rings may have a substituent.

Ring L²For the reason that the light-emitting element of this embodiment mode has more excellent light-emitting efficiency, a benzene ring, a pyridine ring, or a diaza-benzene ring is preferable, and a benzene ring is more preferable, and these rings may have a substituent.

The ring L is a metal complex represented by the formula (2) because the metal complex can be easily synthesized²In the case where there are plural, there are plural rings L²Of these, preferably at least 2 identical, more preferably a plurality of rings L are present²Are all the same.

The ring L is preferable for the reason that the light-emitting element of this embodiment mode has more excellent light-emitting efficiency¹Is a pyridine ring, a diazepine ring, an azanaphthalene ring or a diazepine ring, and ring L²Is a benzene ring, pyridine ring or diazepine ring, more preferably a ring L¹Is a pyridine ring, a quinoline ring or an isoquinoline ring and a ring L²As the benzene ring, further preferred is ring L¹Is a pyridine ring or a quinoline ring and a ring L²Being a benzene ring, particular preference is given to ring L¹Is a pyridine ring and a ring L²Is a benzene ring. These rings may have a substituent.

"Ring L¹And ring L²Wherein at least 1 of the groups represented by the formula (1-T) has as a substituent "means that a ring L is constituted¹And ring L²At least 1 of the atoms (preferably carbon atoms or nitrogen atoms) of (A) is directly bonded with a group represented by the formula (1-T).

In the metal complex represented by the formula (2), in the ring L¹And ring L²In the case where there are plural rings, there are plural rings L¹And ring L²Among them, at least 1 ring may have a group represented by the formula (1-T), and the presence of a plurality of rings L is preferable for the reason that the light-emitting element of the present embodiment has more excellent light-emitting efficiency¹Each having a group represented by the formula (1-T), a plurality of rings L being present²All have the formula (1-T)Radicals shown, or multiple rings L present¹And ring L²Each having a group represented by the formula (1-T), more preferably a plurality of rings L¹Each having a group represented by the formula (1-T), or a plurality of rings L present²All have a group represented by the formula (1-T).

In the metal complex represented by the formula (2), the ring L¹And ring L²The number of groups represented by the formula (1-T) in (1) is usually 1 to 5, but is preferably 1 to 3, more preferably 1 or 2, and still more preferably 1, for the reason that the metal complex represented by the formula (2) can be easily synthesized.

In the metal complex represented by the formula (2), M is²In the case of a rhodium atom or an iridium atom, the ring L¹And ring L²The total number of groups represented by the formula (1-T) is usually 1 to 30, but is preferably 1 to 18, more preferably 2 to 12, and even more preferably 3 to 6, for the reason that the light-emitting element of the present embodiment has more excellent light-emitting efficiency.

In the metal complex represented by the formula (2), M is²In the case of a palladium atom or a platinum atom, the ring L¹And ring L²The total number of groups represented by the formula (1-T) is usually 1 to 20, but is preferably 1 to 12, more preferably 1 to 8, and even more preferably 2 to 4, for the reason that the light-emitting element of the present embodiment has more excellent light-emitting efficiency.

Ring L¹And ring L²The substituent which can be provided is preferably a group represented by the formula (1-T) because the light-emitting element of this embodiment mode is more excellent in light-emitting efficiency.

Ring L¹And ring L²Among the substituents which may be present, a cyano group, an alkenyl group or a cycloalkenyl group is preferable as a substituent other than the group represented by the formula (1-T), and these groups may further have a substituent. Examples and preferable ranges of substituents which may further have a substituent other than the group represented by the formula (1-T) are as defined below for R^1TExamples and preferred ranges of substituents which may be present are the same.

[ group represented by the formula (1-T) ]

As R^1TThe aryl group in (1) is preferably a group obtained by removing 1 hydrogen atom directly bonded to a ring-constituting atom from a monocyclic, bicyclic or tricyclic aromatic hydrocarbon, more preferably a phenyl group, a naphthyl group or a fluorenyl group, and still more preferably a phenyl group, and these groups may have a substituent.

As R^1TThe monovalent heterocyclic group in (b) is preferably a group obtained by removing 1 hydrogen atom directly bonded to a ring-constituting atom from a monocyclic, bicyclic or tricyclic heterocyclic compound, more preferably a group obtained by removing 1 hydrogen atom directly bonded to a ring-constituting atom from pyridine, diazabenzene, triazine, azanaphthalene, naphthyridine, carbazole, dibenzofuran or dibenzothiophene, and still more preferably a group obtained by removing 1 hydrogen atom directly bonded to a ring-constituting atom from pyridine, diazabenzene or triazine, and these groups may have a substituent.

R^1TAmong the substituted amino groups in (1), the substituent of the amino group is preferably an aryl group or a monovalent heterocyclic group, more preferably an aryl group, and these groups may further have a substituent. Examples and preferred ranges of aryl groups as substituents of amino groups with R^1TExamples and preferred ranges of aryl in (1) are the same. Examples and preferred ranges of the monovalent heterocyclic group as a substituent having an amino group are as follows^1TExamples and preferred ranges of the monovalent heterocyclic group in (1) are the same.

In at least 1 of the groups represented by the formula (1-T), R is preferable for the reason that the light-emitting element of the present embodiment has more excellent light-emitting efficiency^1TIs alkyl, cycloalkyl, aryl, monovalent heterocyclic group or substituted amino, more preferably R^1TIs aryl, monovalent heterocyclic group or substituted amino, further preferably R^1TIs aryl or a monovalent heterocyclic radical, particularly preferably R^1TThese groups may have a substituent as the aryl group.

Ring L¹In the case of an isoquinoline ring, R is preferably R in at least 1 group represented by the formula (1-T) because the light-emitting element of the present embodiment has further excellent light-emitting efficiency^1TIs aryl, monovalent heterocyclic group or substituted amino, more preferablyR is selected^1TIs an aryl group or a monovalent heterocyclic group, and further preferably R^1TThese groups may have a substituent as the aryl group.

Ring L¹In the case of an aromatic heterocyclic ring containing a six-membered ring other than an isoquinoline ring (preferably, a pyridine ring, a diazaphenzene ring, a quinoline ring or a diazaphtalene ring, more preferably, a pyridine ring or a quinoline ring, and still more preferably, a pyridine ring), R is preferably selected in at least 1 of the groups represented by the formula (1-T) because the light-emitting element of the present embodiment has further excellent light-emitting efficiency^1TIs alkyl, cycloalkyl, aryl, monovalent heterocyclic group or substituted amino, more preferably R^1TIs an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, and further preferably R^1TIs aryl or a monovalent heterocyclic radical, particularly preferably R^1TThese groups may have a substituent as the aryl group.

R^1TFor the reason that the light-emitting element of this embodiment mode has higher light-emitting efficiency, an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group, or a substituted amino group is preferable, an aryl group, a monovalent heterocyclic group, or a substituted amino group is more preferable, an aryl group or a monovalent heterocyclic group is further preferable, and an aryl group is particularly preferable, and these groups may have a substituent.

Ring L¹When it is an isoquinoline ring, R^1TFor the reason that the light-emitting element of this embodiment mode has further excellent light-emitting efficiency, an aryl group, a monovalent heterocyclic group, or a substituted amino group is preferable, an aryl group or a monovalent heterocyclic group is more preferable, and an aryl group is further preferable, and these groups may have a substituent.

Ring L¹When the heterocyclic ring is an aromatic heterocyclic ring having a six-membered ring other than the isoquinoline ring (preferably a pyridine ring, a diazepine ring, a quinoline ring or a diazepine ring, more preferably a pyridine ring or a quinoline ring, and further preferably a pyridine ring), R^1TFor the reason that the light-emitting element of this embodiment mode has further excellent light-emitting efficiency, an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group, or a substituted amino group is preferable, an alkyl group, a cycloalkyl group, an aryl group, or a monovalent heterocyclic group is more preferable, an aryl group or a monovalent heterocyclic group is further preferable, and an aryl group is particularly preferable, and these groups may have a substituent.

As R^1TThe substituent which may be present is preferably an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, a monovalent heterocyclic group, a substituted amino group, or a fluorine atom, more preferably an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group, or a substituted amino group, and further preferably an alkyl group, a cycloalkyl group, or an aryl group, and these groups may further have a substituent.

R^1TExamples and preferred ranges of aryl, monovalent heterocyclic group and substituted amino group among the substituents which may be possessed are respectively the same as those of R^1TExamples and preferred ranges of the aryl group, the monovalent heterocyclic group and the substituted amino group in (1) are the same.

As R^1TThe substituent which may be present is preferably an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, a monovalent heterocyclic group, a substituted amino group or a fluorine atom, more preferably an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group or a substituted amino group, and further preferably an alkyl group or a cycloalkyl group, and these groups may further have a substituent, but preferably do not further have a substituent.

R^1TExamples and preferable ranges of the aryl group, the monovalent heterocyclic group and the substituted amino group in the substituent which may have the substituent further may be respectively shown as R^1TExamples and preferred ranges of the aryl group, the monovalent heterocyclic group and the substituted amino group in (1) are the same.

[ anionic bidentate ligand ]

As A³－G²－A⁴Examples of the anionic bidentate ligand include those represented by the following formulae. Wherein A is³－G²－A⁴The anionic bidentate ligand shown is conjugated with a suffix n³The ligands defining the number of them are different.

[ chemical formula 14]

Wherein, represents and M²The site of bonding.

Examples of the metal complex represented by the formula (2) include a metal complex represented by the following formula, metal complexes G2 to G4 described later, and metal complexes R3 to R7 described later.

[ chemical formula 15]

[ chemical formula 16]

[ host Material ]

The composition for a light-emitting element of the present embodiment preferably further contains a host material having at least 1 function selected from the group consisting of a hole-injecting property, a hole-transporting property, an electron-injecting property, and an electron-transporting property, because the light-emitting element of the present embodiment has more excellent light-emitting efficiency. The composition for a light-emitting element of the present embodiment may contain only 1 host material, or may contain 2 or more host materials. Wherein the host material is different from the compound (B). The host material is different from the metal complex represented by formula (2).

When the composition for a light-emitting element of the present embodiment further contains a host material, the content of the host material is usually 1 to 99.99 parts by mass, preferably 5 to 99.9 parts by mass, more preferably 10 to 99 parts by mass, further preferably 30 to 97 parts by mass, particularly preferably 50 to 95 parts by mass, and particularly preferably 60 to 90 parts by mass, based on 100 parts by mass of the total of the compound (B), the metal complex represented by formula (2), and the host material.

When the composition for a light-emitting element of the present embodiment further contains a host material, the compound (B), and the metal complex represented by formula (2) preferably interact physically, chemically, or electrically. By this interaction, for example, the light-emitting characteristics, the charge transport characteristics, or the charge injection characteristics of the light-emitting element composition of the present embodiment can be improved or adjusted.

In the case where the composition for a light-emitting element of the present embodiment further includes a host material, a light-emitting material is exemplified, and in this case, the host material, the compound (B), and the metal complex represented by formula (2) are electrically interacted with each other, and electric energy is efficiently transmitted from the host material to the compound (B), and further electric energy is efficiently transmitted from the compound (B) to the metal complex represented by formula (2), whereby the metal complex represented by formula (2) can emit light more efficiently, and the light-emitting element of the present embodiment has more excellent light-emitting efficiency.

From the above viewpoint, the host material has the lowest excited triplet state (T) for the reason that the light-emitting element of the present embodiment has more excellent light-emitting efficiency₁) Preferably, the lowest excited triplet state (T) is more preferable than the metal complex represented by the formula (2) and the compound (B)₁) A higher energy level. In addition, the host material has the lowest excited singlet state (S) for the reason that the light-emitting element of this embodiment mode has more excellent light-emitting efficiency₁) Preferably the lowest excited singlet state (S) of the compound (B)₁) A higher energy level.

As the host material, a material exhibiting solubility in a solvent in which the metal complex represented by the formula (2) and the compound (B) can be dissolved is preferable because the light-emitting element of the present embodiment can be produced by a wet method.

The host material is classified into a low molecular compound (low molecular host) and a high molecular compound (high molecular host), and the composition for a light-emitting element of the present embodiment may contain any host material. As a host material that can be contained in the composition for a light-emitting element of the present embodiment, a low-molecular compound is preferable because the light-emitting element of the present embodiment has more excellent light-emitting efficiency.

Examples of the polymer host include a polymer compound as a hole transport material described later and a polymer compound as an electron transport material described later.

The low-molecular host is preferably a compound represented by the formula (H-1) because the light-emitting element of the present embodiment has higher light-emitting efficiency. Here, the compound represented by the formula (H-1) is preferably a compound having no condensed heterocyclic skeleton (b) in the compound.

The molecular weight of the compound represented by the formula (H-1) is preferably 1X 10²～5×10³More preferably 2X 10²～3×10³More preferably 3X 10²～1.5×10³Particularly preferably 4X 10²～1×10³。

Ar^H1And Ar^H2The aryl group in (1) is preferably a group obtained by removing 1 hydrogen atom directly bonded to a ring-constituting atom from a monocyclic or bicyclic to hexacyclic aromatic hydrocarbon, more preferably a group obtained by removing 1 hydrogen atom directly bonded to a ring-constituting atom from a monocyclic or bicyclic to tetracyclic aromatic hydrocarbon, and still more preferably a group obtained by removing 1 hydrogen atom directly bonded to a ring-constituting atom from benzene, naphthalene, fluorene, phenanthrene or triphenylene, and these groups may have a substituent.

L^H1The arylene group in (1) is preferably a group obtained by removing 2 hydrogen atoms directly bonded to ring-constituting atoms from a monocyclic or bicyclic to hexacyclic aromatic hydrocarbon, more preferably a group obtained by removing 2 hydrogen atoms directly bonded to ring-constituting atoms from a monocyclic or bicyclic to tetracyclic aromatic hydrocarbon, and still more preferably a group obtained by removing 2 hydrogen atoms directly bonded to ring-constituting atoms from benzene, naphthalene, fluorene, phenanthrene or triphenylene, and these groups may have a substituent.

Ar^H1And Ar^H2The monovalent heterocyclic group in (b) is preferably a group obtained by removing 1 hydrogen atom directly bonded to a ring-constituting atom from a heterocyclic compound not containing a fused heterocyclic skeleton (b), and the group may have a substituent. Ar (Ar)^H1And Ar^H2Among the monovalent heterocyclic groups in (b), examples of the heterocyclic compound not containing the fused heterocyclic skeleton (b) include heterocyclic compounds not containing a boron atom and a nitrogen atom in the ring, among the heterocyclic compounds described in the above heterocyclic groups. Ar (Ar)^H1And Ar^H2The monovalent heterocyclic group in (b) is preferably a monocyclic or bicyclic to hexacyclic heterocyclic compound (preferably a monocyclic or bicyclic compound not containing a fused heterocyclic skeleton (b))A heterocyclic compound of formula (la) to (lb) from which 1 hydrogen atom directly bonded to an atom constituting a ring is removed, more preferably a group from which 1 hydrogen atom directly bonded to an atom constituting a ring is removed from a monocyclic, bicyclic, tricyclic or pentacyclic heterocyclic compound (preferably a monocyclic, bicyclic, tricyclic or pentacyclic heterocyclic compound not including a fused heterocyclic skeleton (b)), still more preferably a group from which 1 hydrogen atom directly bonded to an atom constituting a ring is removed from pyridine, diazabenzene, triazine, azanaphthalene, naphthyridine, carbazole, dibenzofuran, dibenzothiophene, phenoxazine, phenothiazine, carbazole, dibenzo, indolocarbazole or indenocarbazole, particularly preferably a group from which 1 hydrogen atom directly bonded to an atom constituting a ring is removed from pyridine, diazabenzene, triazine, azanaphthalene, naphthyridine, carbazole, dibenzofuran or dibenzothiophene, these groups may have a substituent.

L^H1The divalent heterocyclic group in (b) is preferably a group obtained by removing 2 hydrogen atoms directly bonded to the atoms constituting the ring from a heterocyclic compound not containing the fused heterocyclic skeleton (b). L is^H1Among the divalent heterocyclic groups in (b), examples of the heterocyclic compound not containing the fused heterocyclic skeleton (b) include heterocyclic compounds not containing a boron atom and a nitrogen atom in the ring, among the heterocyclic compounds described in the above heterocyclic groups. L is^H1The divalent heterocyclic group in (3) is preferably a group obtained by removing 2 hydrogen atoms directly bonded to atoms constituting a ring from a monocyclic or bicyclic to hexacyclic heterocyclic compound (preferably a monocyclic or bicyclic to hexacyclic heterocyclic compound not containing a fused heterocyclic skeleton (b)), more preferably a group obtained by removing 2 hydrogen atoms directly bonded to atoms constituting a ring from a monocyclic, bicyclic, tricyclic or pentacyclic heterocyclic compound (preferably a monocyclic, bicyclic, tricyclic or pentacyclic heterocyclic compound not containing a fused heterocyclic skeleton (b)), and still more preferably a group obtained by removing 2 hydrogen atoms directly bonded to atoms constituting a ring from pyridine, diazepine, triazine, azanaphthalene, naphthyridine, carbazole, dibenzofuran, dibenzothiophene, phenoxazine, phenothiazine, dibenzocarbazole, indolocarbazole or indeneThe carbazole is particularly preferably a group obtained by removing 2 hydrogen atoms directly bonded to atoms constituting the ring, and particularly preferably a group obtained by removing 2 hydrogen atoms directly bonded to atoms constituting the ring from pyridine, diazabenzene, triazine, azanaphthalene, naphthyridine, carbazole, dibenzofuran, or dibenzothiophene, and these groups may have a substituent.

Ar^H1And Ar^H2Among the substituted amino groups in (1), the substituent of the amino group is preferably an aryl group or a monovalent heterocyclic group, more preferably an aryl group, and these groups may further have a substituent. Examples and preferred ranges of aryl groups as substituents of amino groups with Ar^H1And Ar^H2Examples and preferred ranges of aryl in (1) are the same. Examples and preferred ranges of the monovalent heterocyclic group as a substituent having an amino group and Ar^H1And Ar^H2Examples and preferred ranges of the monovalent heterocyclic group in (1) are the same.

Ar is because the light-emitting element of this embodiment mode has more excellent light-emitting efficiency^H1And Ar^H2At least 1 of them is preferably an aryl group or a monovalent heterocyclic group, more preferably a monovalent heterocyclic group, further preferably a carbazolyl group, a dibenzothienyl group or a dibenzofuranyl group, particularly preferably a carbazolyl group, and these groups may have a substituent.

Ar is because the light-emitting element of this embodiment mode has more excellent light-emitting efficiency^H1And Ar^H2The aryl group or the monovalent heterocyclic group is preferably an aryl group or a monovalent heterocyclic group, more preferably a group obtained by removing 1 hydrogen atom directly bonded to an atom constituting a ring from benzene, fluorene, pyridine, diazabenzene, triazine, carbazole, dibenzofuran, or dibenzothiophene, further preferably a phenyl group, a fluorenyl group, a dibenzothienyl group, a dibenzofuranyl group, or a carbazolyl group, and particularly preferably a carbazolyl group, and these groups may have a substituent.

L is preferable for the reason that the light-emitting element of this embodiment mode has more excellent light-emitting efficiency^H1At least 1 of them is an arylene group or a divalent heterocyclic group, more preferably a divalent heterocyclic group, and still more preferably a hydrogen atom which is removed from carbazole, dibenzofuran or dibenzothiophene and is directly bonded to an atom (preferably a carbon atom) constituting a ring2, these groups may further have a substituent.

The reason why the light-emitting element of this embodiment mode has more excellent light-emitting efficiency is that L^H1Preferably, the group is an arylene group or a divalent heterocyclic group, more preferably a group obtained by removing 2 hydrogen atoms directly bonded to an atom (preferably a carbon atom) constituting a ring from benzene, naphthalene, fluorene, pyridine, diazabenzene, triazine, azanaphthalene, naphthyridine, carbazole, dibenzofuran, or dibenzothiophene, further preferably a group obtained by removing 2 hydrogen atoms directly bonded to an atom (preferably a carbon atom) constituting a ring from benzene, fluorene, pyridine, diazabenzene, triazine, carbazole, dibenzofuran, or dibenzothiophene, particularly preferably a group obtained by removing 2 hydrogen atoms directly bonded to an atom constituting a ring from dibenzofuran or dibenzothiophene, and these groups may have a substituent.

As Ar^H1、Ar^H2And L^H1The substituent which may be present is preferably an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, a monovalent heterocyclic group, a substituted amino group, or a fluorine atom, more preferably an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group, or a substituted amino group, and further preferably an alkyl group, an aryl group, or a monovalent heterocyclic group, and these groups may further have a substituent.

Ar^H1、Ar^H2And L^H1Examples and preferred ranges of the aryl group, monovalent heterocyclic group and substituted amino group among the substituents which may be contained are each with Ar^H1And Ar^H2Examples and preferred ranges of the aryl group, the monovalent heterocyclic group and the substituted amino group in (1) are the same.

As Ar^H1、Ar^H2And L^H1The substituent which may be present is preferably an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group or a substituted amino group, more preferably an alkyl group or a cycloalkyl group, and these groups may further have a substituent, but preferably do not further have a substituent.

Ar^H1、Ar^H2And L^H1Aryl group, monovalent heterocyclic group and substituted amino group among the substituents which may be presentWith Ar and each of the examples and preferred ranges of^H1And Ar^H2Examples and preferred ranges of the aryl group, the monovalent heterocyclic group and the substituted amino group in (1) are the same.

n^H1It is usually an integer of 0 to 10 inclusive, preferably an integer of 0 to 5 inclusive, more preferably an integer of 1 to 3 inclusive, and particularly preferably 1.

Examples of the compound represented by the formula (H-1) include compounds represented by the following formulae. In the formula, Z¹Represents an oxygen atom or a sulfur atom. In the formula, Z²Represents a group represented by-CH ═ or a group represented by-N ═ or a salt thereof.

[ chemical formula 17]

[ chemical formula 18]

[ other ingredients ]

The composition for a light-emitting element of the present embodiment may be a composition containing the metal complex represented by formula (2), the compound (B), and at least 1 selected from the group consisting of the host material, the hole-transporting material, the hole-injecting material, the electron-transporting material, the electron-injecting material, the light-emitting material, the antioxidant, and the solvent. Wherein the hole transporting material, the hole injecting material, the electron transporting material, the electron injecting material, and the light emitting material are different from the metal complex and the compound (B) represented by formula (2).

[ ink ]

The composition containing the metal complex represented by formula (2), the compound (B) and the solvent (hereinafter referred to as "ink") is suitable for the production of a light-emitting element by using a wet method such as a spin coating method, a flow coating method, a microgravure coating method, a gravure coating method, a bar coating method, a roll coating method, a wire bar coating method, a dip coating method, a spray coating method, a screen printing method, a flexographic printing method, an offset printing method, an ink jet printing method, a capillary coating method, a nozzle coating method, or the like. The viscosity of the ink may be adjusted depending on the type of printing method, and is preferably 1 to 20mPa · s at 25 ℃.

The solvent contained in the ink is preferably a solvent capable of dissolving or uniformly dispersing the solid components in the ink. Examples of the solvent include a chlorine-based solvent, an ether-based solvent, an aromatic hydrocarbon-based solvent, an aliphatic hydrocarbon-based solvent, a ketone-based solvent, an ester-based solvent, a polyol-based solvent, an alcohol-based solvent, a sulfoxide-based solvent, and an amide-based solvent.

The amount of the solvent to be added to the ink is usually 1000 to 10000000 parts by mass, based on 100 parts by mass of the total of the metal complex represented by the formula (2) and the compound (B).

One solvent may be used alone, or two or more solvents may be used in combination.

Hole transport Material

The hole transport material is classified into a low molecular compound and a high molecular compound, and is preferably a high molecular compound having a crosslinking group.

Examples of the polymer compound include polyvinylcarbazole and derivatives thereof; polyarylene having an aromatic amine structure in a side chain or a main chain, and a derivative thereof. The polymer compound may be a compound to which an electron accepting site such as fullerene, tetrafluorotetracyanoquinodimethane, tetracyanoethylene, trinitrofluorenone, or the like is bonded.

In the composition for a light-emitting element of the present embodiment, when the hole-transporting material is contained, the amount of the hole-transporting material to be blended is usually 1 part by mass to 10000 parts by mass when the total amount of the metal complex represented by formula (2) and the compound (B) is 100 parts by mass.

One kind of the hole transport material may be used alone, or two or more kinds may be used in combination.

Electron transport Material

The electron transport materials are classified into low molecular compounds and high molecular compounds. The electron transport material may have a crosslinking group.

Examples of the low-molecular compound include metal complexes having 8-hydroxyquinoline as a ligand, oxadiazoles, anthraquinone dimethanes, benzoquinones, naphthoquinones, anthraquinones, tetracyanoanthraquinone dimethanes, fluorenones, dicyanstilbene and diphenoquinones, and derivatives thereof.

Examples of the polymer compound include polyphenylene, polyfluorene, and derivatives thereof. The polymer compound may be doped with a metal.

In the composition for a light-emitting element of the present embodiment, when the composition contains an electron-transporting material, the amount of the electron-transporting material is usually 1 part by mass to 10000 parts by mass, assuming that the total amount of the metal complex represented by formula (2) and the compound (B) is 100 parts by mass.

The electron-transporting material may be used singly or in combination of two or more.

Hole injection material and electron injection material

The hole injection material and the electron injection material are each classified into a low molecular compound and a high molecular compound. The hole injection material and the electron injection material may have a crosslinking group.

Examples of the low-molecular-weight compound include metal phthalocyanines such as copper phthalocyanine; carbon; metal oxides of molybdenum, tungsten, and the like; metal fluorides such as lithium fluoride, sodium fluoride, cesium fluoride and potassium fluoride.

Examples of the polymer compound include polyaniline, polythiophene, polypyrrole, polyphenylene vinylene, polythiophene vinylene, polyquinoline, polyquinoxaline, and derivatives thereof; and a conductive polymer such as a polymer having an aromatic amine structure in a main chain or a side chain.

In the composition for a light-emitting element of the present embodiment, when the hole injecting material and/or the electron injecting material are contained, the amount of the hole injecting material and the electron injecting material to be mixed is usually 1 part by mass to 10000 parts by mass when the total of the metal complex represented by the formula (2) and the compound (B) is 100 parts by mass.

The hole injection material and the electron injection material may be used singly or in combination of two or more.

Doping of ions

When the hole injection material or the electron injection material contains a conductive polymer, the conductivity of the conductive polymer is preferably 1 × 10^-5S/cm～1×10³S/cm. In order to set the conductivity of the conductive polymer within this range, an appropriate amount of ions may be doped into the conductive polymer. The species of the doped ions is an anion in the case of a hole injection material, and a cation in the case of an electron injection material. Examples of the anion include a polystyrene sulfonate ion, an alkylbenzene sulfonate ion, and a camphor sulfonate ion. Examples of the cation include lithium ion, sodium ion, potassium ion, and tetrabutylammonium ion.

One kind of the doping ions may be used alone, or two or more kinds may be used in combination.

Luminescent materials

Light emitting materials are classified into low molecular compounds and high molecular compounds. The light-emitting material may have a crosslinking group.

Examples of the low-molecular compound include naphthalene and its derivatives, anthracene and its derivatives, perylene and its derivatives, and a triplet light-emitting complex having iridium, platinum, or europium as a central metal.

Examples of the triplet light-emitting complex include metal complexes shown below.

[ chemical formula 19]

Examples of the polymer compound include arylene groups including phenylene, naphthalenediyl, fluorenediyl, phenanthrenediyl, dihydrophenanthrenediyl, anthracenediyl, and pyrenediyl; aromatic amine residues such as groups obtained by removing 2 hydrogen atoms from aromatic amines; and divalent heterocyclic groups such as carbazole diyl, phenoxazinediyl, and phenothiazindiyl.

In the composition for a light-emitting element of the present embodiment, when the composition contains a light-emitting material, the content of the light-emitting material is usually 1 part by mass to 10000 parts by mass when the total of the metal complex represented by the formula (2) and the compound (B) is 100 parts by mass.

One kind of the luminescent material may be used alone, or two or more kinds may be used in combination.

An antioxidant

The antioxidant may be a compound that is soluble in the same solvent as the metal complex represented by formula (2) and the compound (B) and does not impair light emission and charge transport, and examples thereof include a phenol-based antioxidant and a phosphorus-based antioxidant.

In the composition for a light-emitting element of the present embodiment, when an antioxidant is contained, the amount of the antioxidant to be blended is usually 0.00001 to 10 parts by mass, assuming that the total amount of the metal complex represented by formula (2) and the compound (B) is 100 parts by mass.

The antioxidant may be used alone or in combination of two or more.

< membrane >

The film of the present embodiment contains the composition for a light-emitting element. The film of the present embodiment is suitable as a light-emitting layer in a light-emitting element. The film of the present embodiment can be produced by a wet method using ink, for example. The film of the present embodiment can be produced by a dry method such as a vacuum deposition method. Examples of the method for producing the film of the present embodiment by a dry method include a method of depositing the above-described composition for a light-emitting element; and a method of co-evaporating the metal complex represented by the formula (2) and the compound (B).

The thickness of the film is usually 1nm to 10 μm.

< light emitting element >

The light-emitting element of the present embodiment contains the composition for a light-emitting element.

The light-emitting element of the present embodiment may include, for example, an anode, a cathode, and an organic layer containing the light-emitting element composition provided between the anode and the cathode.

[ layer constitution ]

The layer containing the composition for a light-emitting element of the present embodiment is usually 1 or more layers selected from a light-emitting layer, a hole-transporting layer, a hole-injecting layer, an electron-transporting layer, and an electron-injecting layer, and is preferably a light-emitting layer. Each of these layers contains a light emitting material, a hole transporting material, a hole injecting material, an electron transporting material, and an electron injecting material. Each of these layers can be formed by the same method as in the above-described film formation using a light-emitting material, a hole-transporting material, a hole-injecting material, an electron-transporting material, and an electron-injecting material.

The light-emitting element has a light-emitting layer between an anode and a cathode. The light-emitting element of this embodiment preferably has at least 1 of the hole injection layer and the hole transport layer between the anode and the light-emitting layer from the viewpoint of hole injection property and hole transport property, and preferably has at least 1 of the electron injection layer and the electron transport layer between the cathode and the light-emitting layer from the viewpoint of electron injection property and electron transport property.

The materials of the hole transport layer, the electron transport layer, the light-emitting layer, the hole injection layer, and the electron injection layer include the composition for a light-emitting element of the present embodiment, and the hole transport material, the electron transport material, the light-emitting material, the hole injection material, the electron injection material, and the like described above.

In the case where the material for the hole transport layer, the material for the electron transport layer, and the material for the light-emitting layer are soluble in the solvents used for forming the layers adjacent to the hole transport layer, the electron transport layer, and the light-emitting layer, respectively, in the production of the light-emitting element, it is preferable that the materials have a crosslinking group in order to avoid the dissolution of the materials in the solvents. After each layer is formed using a material having a crosslinking group, the crosslinking group is crosslinked, whereby the layer can be insolubilized.

In the light-emitting element of the present embodiment, when a low molecular weight compound is used, examples of a method for forming each layer such as the light-emitting layer, the hole transport layer, the electron transport layer, the hole injection layer, and the electron injection layer include a dry method such as a vacuum deposition method using powder, a wet method such as a method of forming a film using a solution or a molten state, and when a high molecular weight compound is used, examples of a wet method such as a method of forming a film using a solution or a molten state. The order, number, and thickness of the stacked layers are adjusted in consideration of, for example, light emission efficiency, driving voltage, and luminance lifetime.

[ substrate/electrode ]

The substrate in the light-emitting element may be any substrate that can be provided with an electrode and that does not chemically change when the organic layer is formed, and examples of the substrate include substrates made of materials such as glass, plastic, and silicon. In the case of an opaque substrate, the electrode furthest from the substrate is preferably transparent or translucent.

Examples of the material of the anode include conductive metal oxides and translucent metals, and indium oxide, zinc oxide, and tin oxide are preferable; conductive compounds such as Indium Tin Oxide (ITO) and indium zinc oxide; silver and palladium and copper complexes (APC); NESA, gold, platinum, silver, copper.

Examples of the material of the cathode include metals such as lithium, sodium, potassium, rubidium, cesium, beryllium, magnesium, calcium, strontium, barium, aluminum, zinc, and indium; alloys of 2 or more of them; alloys of 1 or more of them with 1 or more of silver, copper, manganese, titanium, cobalt, nickel, tungsten, and tin; and graphite intercalation compounds. Examples of the alloy include a magnesium-silver alloy, a magnesium-indium alloy, a magnesium-aluminum alloy, an indium-silver alloy, a lithium-aluminum alloy, a lithium-magnesium alloy, a lithium-indium alloy, and a calcium-aluminum alloy.

The anode and the cathode may have a laminated structure of 2 or more layers.

[ use ]

The light-emitting element of the present embodiment can be suitably used as a light source for a backlight of a liquid crystal display device, a light source for illumination, an organic EL illumination, a display device (for example, an organic EL display or an organic EL television) such as a computer, a television, or a mobile terminal.

Although the preferred embodiments of the present invention have been described above, the present invention is not limited to these embodiments.

Examples

The present invention will be described in further detail with reference to examples below, but the present invention is not limited to these examples.

In the examples, the number average molecular weight (Mn) of the polymer compound in terms of polystyrene and the weight average molecular weight (Mw) of the polymer compound in terms of polystyrene were determined by Size Exclusion Chromatography (SEC) described below using tetrahydrofuran as a mobile phase.

The high molecular compound to be measured was dissolved in tetrahydrofuran at a concentration of about 0.05 mass%, and 10. mu.L was injected into SEC. The mobile phase was circulated at a flow rate of 1.0 mL/min. As the column, PLGel MIXED-B (manufactured by Polymer Laboratories) was used. As the detector, a UV-VIS detector (trade name: UV-8320GPC, manufactured by Tosoh corporation) was used.

In the examples, Δ E for compounds_STFor the calculation of the value (c), the ground state of the compound is structurally optimized by the density functional method at the B3LYP level, in which case 6-31G is used as the basis function. Then, using Gaussian09 as a quantum chemical computation program, Δ E of the compound was calculated by a time-dependent density functional method of B3LYP level_ST。

In the examples, the maximum peak wavelength of the emission spectrum of the metal complex was measured at room temperature by a spectrophotometer (FP-6500, manufactured by Nippon spectral Co., Ltd.). The metal complex is dissolved in xylene at about 0.8X 10^-4A xylene solution dissolved at a concentration of mass% was used as a sample. As the excitation light, UV light having a wavelength of 325nm was used.

Synthesis example M Synthesis of Compounds M1 to M7

Compound M1 was synthesized according to the method described in International publication No. 2015/145871.

Compound M2 was synthesized according to the method described in International publication No. 2013/146806.

Compound M3 was synthesized according to the method described in International publication No. 2005/049546.

Compound M4 was synthesized according to the method described in Japanese patent application laid-open No. 2010-189630.

Compound M5 and compound M7 were synthesized according to the method described in International publication No. 2002/045184.

Compound M6 was synthesized according to the method described in International publication No. 2011/049241.

[ chemical formula 20]

< Synthesis example HTL-1 > Synthesis of high molecular Compound HTL-1

The high molecular compound HTL-1 was synthesized using compound M1, compound M2, and compound M3 according to the method described in international publication No. 2015/145871. Mn of Polymer HTL-1 was 2.3X 10⁴Mw of 1.2X 10⁵。

The molar ratio of the high molecular compound HTL-1 was calculated from the theoretical value obtained from the amount of the raw materials charged, and the molar ratio was 45: 5: a copolymer having a structural unit derived from the compound M1, a structural unit derived from the compound M2, and a structural unit derived from the compound M3 at a molar ratio of 50.

< Synthesis example HTL-C1 > Synthesis of high molecular Compound HTL-C1

The polymer compound HTL-C1 was synthesized using compound M4 and compound M3 according to the method described in international publication No. 2015/194448. Mn of the high molecular weight Compound HTL-C1 was 4.5X 10⁴Mw of 1.5X 10⁵。

The molecular weight compound HTL-C1 was a molecular weight ratio of 50: a molar ratio of 50 with a copolymer of a structural unit derived from compound M4 and a structural unit derived from compound M3.

< Synthesis example HTL-2 > Synthesis of high molecular Compound HTL-2

The polymer compound HTL-2 was synthesized using compound M7, compound M5, and compound M6 according to the method described in international publication No. 2011/049241. Mn of the Polymer HTL-2 was 8.9X 10⁴Mw of 4.2X 10⁵。

The molecular compound HTL-2 was a copolymer of 50: 42.5: a copolymer having a structural unit derived from the compound M7, a structural unit derived from the compound M5, and a structural unit derived from the compound M6 at a molar ratio of 7.5.

< Synthesis and obtention of Metal complexes G1-G4, Firpic and Metal complexes R1-R7 >

As the metal complex G1, the metal complex R2, the metal complex R3 and the metal complex R4, those manufactured by Luminescence Technology, inc.

The metal complex G2 is synthesized according to the method described in Japanese patent laid-open publication No. 2013-237789.

The metal complex G3 was synthesized according to the method described in international publication No. 2009/131255.

The metal complex G4 is synthesized by the method described in Japanese patent laid-open publication No. 2014-224101 and International publication No. 2009/131255.

As Firpic, a product manufactured by Aldrich was used.

As the metal complex R1, a metal complex manufactured by American Dye Source was used.

The metal complex R5 is synthesized according to the method described in Japanese patent laid-open No. 2006-188673.

The metal complex R6 is synthesized according to the method described in Japanese patent application laid-open No. 2011-105701.

The metal complex R7 is synthesized according to the method described in Japanese patent application laid-open No. 2008-179617.

[ chemical formula 21]

[ chemical formula 22]

[ chemical formula 23]

The maximum peak wavelength of the light emission spectrum of the metal complex G1 was 510 nm.

Metal complex G²The maximum peak wavelength of the emission spectrum of (2) is 508 nm.

The maximum peak wavelength of the light emission spectrum of the metal complex G3 was 514 nm.

The maximum peak wavelength of the light emission spectrum of the metal complex G4 was 544 nm.

The maximum peak wavelength of the luminescence spectrum of Firpic is 470 nm.

The maximum peak wavelength of the light emission spectrum of the metal complex R1 was 618 nm.

The maximum peak wavelength of the light emission spectrum of the metal complex R2 was 579 nm.

The maximum peak wavelength of the light emission spectrum of the metal complex R3 was 620 nm.

The maximum peak wavelength of the light emission spectrum of the metal complex R4 was 580 nm.

The maximum peak wavelength of the emission spectrum of the metal complex R5 was 619 nm.

The maximum peak wavelength of the light emission spectrum of the metal complex R6 was 611 nm.

The maximum peak wavelength of the light emission spectrum of the metal complex R7 was 594 nm.

< acquisition and Synthesis of Compounds H1, T1 and B1-B3 >

As compound H1 and compound B1, compounds manufactured by luminence Technology, inc.

Compound T1 was synthesized according to the method described in International publication No. 2018/062278.

Compound B2 and compound B3 were synthesized according to the method described in international publication No. 2015/102118.

[ chemical formula 24]

[ chemical formula 25]

Delta E of Compound T1_STIs 0.109 eV.

Delta E of Compound B1_STIs 0.494eV。

Delta E of Compound B2_STIs 0.471 eV.

Delta E of Compound B3_STIs 0.479 eV.

< example D1 > production and evaluation of light-emitting element D1

(formation of Anode and hole-injecting layer)

An ITO film was provided on a glass substrate by a sputtering method at a thickness of 45nm, thereby forming an anode. On the anode, ND-3202 (manufactured by Nissan chemical industry) as a hole injection material was formed in a thickness of 35nm by spin coating. The substrate on which the hole injection layer was laminated was heated on a hot plate at 50 ℃ for 3 minutes and further at 230 ℃ for 15 minutes in an atmospheric atmosphere, thereby forming a hole injection layer.

(formation of hole transport layer)

The high molecular compound HTL-1 was dissolved in xylene at a concentration of 0.7 mass%. Using the obtained xylene solution, a film was formed on the hole injection layer by spin coating at a thickness of 20nm, and heated on a hot plate at 180 ℃ for 60 minutes under a nitrogen atmosphere, thereby forming a hole transport layer.

(formation of luminescent layer)

Compound H1, compound B1, and metal complex G3 (compound H1/compound B1/metal complex G3 ═ 66 mass%/4 mass%/30 mass%) were dissolved in toluene at a concentration of 2 mass%. The obtained toluene solution was used to form a film on the hole transport layer by spin coating at a thickness of 60nm, and the film was heated at 130 ℃ for 10 minutes in a nitrogen atmosphere, thereby forming a light-emitting layer.

(formation of cathode)

The substrate with the light emitting layer was reduced in pressure to 1.0X 10 in a deposition machine^-4After Pa or less, sodium fluoride was deposited on the light-emitting layer by about 4nm as a cathode, and then aluminum was deposited on the sodium fluoride layer by about 80 nm. After the vapor deposition, the substrate on which the cathode was formed was sealed with a glass substrate, thereby producing a light-emitting element D1.

(evaluation of light-emitting element)

EL emission was observed by applying a voltage to the light-emitting element D1. MeasuringFixed 100cd/m²Luminous efficiency [ lm/W ] of]And CIE chromaticity coordinates.

< examples D2 to D3 and comparative examples CD1 to CD2 > production and evaluation of light-emitting elements D2, D3, CD1 and CD2

Light-emitting elements D2, D3, CD1, and CD2 were produced in the same manner as in example D1, except that the materials described in table 1 were used instead of "compound H1, compound B1, and metal complex G3 (compound H1/compound B1/metal complex G3 ═ 66 mass%/4 mass%/30 mass%)" in example D1 (formation of a light-emitting layer).

EL emission was observed by applying voltages to the light-emitting elements D2, D3, CD1, and CD 2. Measurement of 100cd/m²Luminous efficiency [ lm/W ] of]And CIE chromaticity coordinates.

The results of examples D1 to D3 and comparative examples CD1 to CD2 are shown in Table 1. Relative values of the light-emitting efficiencies of the light-emitting elements D1 to D3 and CD2 are shown when the light-emitting efficiency of the light-emitting element CD1 is 1.0.

[ Table 1]

< examples D4 to D6 and comparative example CD3 > production and evaluation of light-emitting elements D4 to D6 and CD3

Light-emitting elements D4 to D6 and CD3 were produced in the same manner as in example D1, except that the materials described in table 2 were used instead of "compound H1, compound B1 and metal complex G3 (compound H1/compound B1/metal complex G3 ═ 66 mass%/4 mass%/30 mass%)" in example D1 (formation of a light-emitting layer) ".

EL emission was observed by applying a voltage to the light-emitting elements D4 to D6 and CD 3. Determination of 2000cd/m²Luminous efficiency [ lm/W ] of]And CIE chromaticity coordinates.

The results of examples D4-D6 and comparative example CD3 are shown in Table 2. The relative values of the light-emitting efficiencies of the light-emitting elements D4 to D6 are shown when the light-emitting efficiency of the light-emitting element CD3 is 1.0.

[ Table 2]

< examples D7 to D8 and comparative example CD4 > production and evaluation of light-emitting elements D7, D8 and CD4

Light-emitting elements D7, D8, and CD4 were fabricated in the same manner as in example D1, except that the materials shown in table 3 were used instead of "compound H1, compound B1, and metal complex G3" (compound H1/compound B1/metal complex G3 ═ 66 mass%/4 mass%/30 mass%), and "polymer compound HTL-C1" was used instead of "polymer compound HTL-1" in example D1 (formation of a hole-transporting layer) in example D1.

By applying a voltage to the light emitting elements D7, D8, and CD4, EL emission was observed. Measurement 10000cd/m²Luminous efficiency [ lm/W ] of]And CIE chromaticity coordinates.

The results of examples D7-D8 and comparative example CD4 are shown in Table 3. A relative value of the light emitting efficiencies of the light emitting elements D7 and D8 when the light emitting efficiency of the light emitting element CD4 was set to 1.0 is shown.

[ Table 3]

< example D9 > production and evaluation of light-emitting element D9

(formation of Anode and hole-injecting layer)

An ITO film was provided on a glass substrate by a sputtering method at a thickness of 45nm, thereby forming an anode. On the anode, ND-3202 (manufactured by Nissan chemical industry) as a hole injection material was formed in a thickness of 50nm by spin coating. The substrate on which the hole injection layer was laminated was heated on a hot plate at 50 ℃ for 3 minutes and further at 230 ℃ for 15 minutes in an atmospheric atmosphere, thereby forming a hole injection layer.

(formation of hole transport layer)

The polymer compound HTL-2 was dissolved in xylene at a concentration of 0.7 mass%. Using the obtained xylene solution, a film was formed on the hole injection layer by spin coating at a thickness of 20nm, and heated on a hot plate at 180 ℃ for 60 minutes under a nitrogen atmosphere, thereby forming a hole transport layer.

(formation of luminescent layer)

The compound H1, the compound B1, and the metal complex R7 (the compound H1/the compound B1/the metal complex R7 ═ 81 mass%/4 mass%/15 mass%) were dissolved in toluene at a concentration of 2 mass%. The obtained toluene solution was used to form a film on the hole transport layer by spin coating at a thickness of 60nm, and the film was heated at 130 ℃ for 10 minutes in a nitrogen atmosphere, thereby forming a light-emitting layer.

(formation of cathode)

The substrate with the light-emitting layer formed thereon is reduced in pressure to 1.0 × 10-⁴After Pa or less, sodium fluoride was deposited on the light-emitting layer by about 4nm as a cathode, and then aluminum was deposited on the sodium fluoride layer by about 80 nm. After the vapor deposition, the substrate on which the cathode was formed was sealed with a glass substrate, thereby producing a light-emitting element D9.

(evaluation of light-emitting element)

EL emission was observed by applying a voltage to the light-emitting element D9. Measurement 1000cd/m²Luminous efficiency [ lm/W ] of]And CIE chromaticity coordinates.

< examples D10 to D11 and comparative example CD5 > production and evaluation of light-emitting elements D10, D11 and CD5

Light-emitting elements D10, D11, and CD5 were produced in the same manner as in example D9, except that the materials described in table 4 were used instead of "compound H1, compound B1, and metal complex R7 (compound H1/compound B1/metal complex R7 ═ 81 mass%/4 mass%/15 mass%)" in example D9 (formation of a light-emitting layer) ".

By applying a voltage to the light emitting elements D10, D11, and CD5, EL emission was observed. Measurement 1000cd/m²Luminous efficiency [ lm/W ] of]And CIE chromaticity coordinates.

The results of examples D9 to D11 and comparative example CD5 are shown in Table 4. The relative values of the light-emitting efficiencies of the light-emitting elements D9 to D11 are shown when the light-emitting efficiency of the light-emitting element CD5 is 1.0.

[ Table 4]

< examples D12 to D13 and comparative example CD6 > production and evaluation of light-emitting elements D12, D13 and CD6

Light-emitting elements D12, D13, and CD6 were produced in the same manner as in example D9, except that the materials described in table 5 were used instead of "compound H1, compound B1, and metal complex R7 (compound H1/compound B1/metal complex R7 ═ 81 mass%/4 mass%/15 mass%)" in example D9 (formation of a light-emitting layer) ".

By applying a voltage to the light emitting elements D12, D13, and CD6, EL emission was observed. Measurement 2500cd/m²Luminous efficiency [ lm/W ] of]And CIE chromaticity coordinates.

The results of examples D12 to D13 and comparative example CD6 are shown in Table 5. A relative value of the light emitting efficiencies of the light emitting elements D12 and D13 when the light emitting efficiency of the light emitting element CD6 was set to 1.0 is shown.

[ Table 5]

Industrial applicability

The composition of the present invention is useful for producing a light-emitting element having excellent luminous efficiency.