ORGANIC ELECTROLUMINESCENCE DEVICE AND ELECTRONIC APPARATUS PROVIDED WITH THE SAME

TECHNICAL FIELD

The invention relates to an organic electroluminescence device and an electronic apparatus provided with the organic electroluminescence device.

BACKGROUND ART

When a voltage is applied to an organic electroluminescence device (hereinafter may be referred to as an organic EL device), holes are injected to an emitting layer from an anode and electrons are injected to an emitting layer from a cathode. In the emitting layer, injected holes and electrons are re-combined and excitons are formed.

Although materials for an organic EL device are being improved gradually to increase the performances of the organic EL device (for example, Patent Documents 1 to 6), high performances are further offered. In particular, improvement in lifetime of an organic EL device is an important task relating to a lifetime of commercial products provided with the organic EL device, and thus a material enabling to realize a long-lifetime organic EL device is required.

RELATED ART DOCUMENTS
Patent Documents

Patent Document 1: WO2017/188111

Patent Document 2: Publication of US Patent Application No. 2017/324045

Patent Document 3: WO2010/099534

Patent Document 4: WO2010/135395

Patent Document 5: WO2010/071362

Patent Document 6: WO2018/066830

SUMMARY OF THE INVENTION

An object of the invention is to provide an organic EL device having a long lifetime, and to provide an electronic apparatus provided with the organic EL device.

As a result of extensive studies, the inventors have found that an organic EL device having a long lifetime can be obtained by using compounds having a specific structure in an emitting layer of the organic EL device in combination, and they have achieved the invention.

According to the invention, the following organic EL device and electric apparatus can be provided.

1. An organic electroluminescence device comprising:

a cathode,

an anode, and

an emitting layer disposed between the cathode and the anode, wherein

the emitting layer comprises a compound represented by the following formula (1) and one or more compounds selected from the group consisting of compounds represented by each of formulas (11), (21), (31), (41), (51), (61), (71) and (81):

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wherein in the formula (1),

R₁to R₈are independently

a hydrogen atom,

a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

a substituted a unsubstituted alkynyl group having 2 to 50 carbon atoms,

a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

—Si(R₉₀₁)(R₉₀₂)(R₉₀₃),

—O—(R₉₀₄),
—S—(R₉₀₅),

—N(R₉₀₆)(R₉₀₇),

a halogen atom, a cyano group, a nitro group,

a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms;

R₉₀₁to R₉₀₇are independently

a hydrogen atom,

a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms;

when two or more of R₉₀₁to R₉₀₇exist, two or more of R₉₀₁to R₉₀₇may be the same with or different from each other;

at least one of R₁to R₈is a deuterium atom;

two or more adjacent groups of R₁to R₄and two or more adjacent groups of R₅to R₈do not form a ring;

L₁and L₂are independently

a single bond,

a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or

a substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring atoms;

Ar is

a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms;

one of R₁₁to R₁₈is a single bond bonding to L₂;

R₁₁to R₁₈which are not single bonds bonding to L₂are independently

a hydrogen atom,

a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

—Si(R₉₀₁)(R₉₀₂)(R₉₀₃),

—O—(R₉₀₄),
—S—(R₉₀₅),

R₉₀₁to R₉₀₇are as defined in R₁to R₈; and

two or more adjacent groups of R₁₁to R₁₈do not form a ring;

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wherein, in the formula (11),

one or more pairs of two or more adjacent groups of R₁₀₁to R₁₁₀are bonded with each other to form a substituted or unsubstituted, saturated or unsaturated ring, or do not form a substituted or unsubstituted, saturated or unsaturated ring;

at least one of R₁₀₁to R₁₁₀is a monovalent group represented by the formula (12);

R₁₀₁to R₁₁₀that do not form the substituted or unsubstituted, saturated or unsaturated ring and that are not a monovalent group represented by the following formula (12) are independently

—O—(R₉₀₄),
—S—(R₉₀₅),

R₉₀₁to R₉₀₇are as defined in the formula (1);

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wherein, in the formula (12), Ar₁₀₁and Ar₁₀₂are independently

a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms;

L₁₀₁to L₁₀₃are independently

a single bonded,

a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or

a substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring atoms;

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wherein, in the formula (21),

Zs are independently CR_aor N;

A1 ring and A2 ring are independently a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic ring having 5 to 50 ring atoms;

when a plurality of R_as exist, one or more pairs of two or more adjacent groups of R_aare bonded with each other to form a substituted or unsubstituted, saturated or unsaturated ring, or do not form a substituted or unsubstituted, saturated or unsaturated ring;

when a plurality of R_bs exist, one or more pairs of two or more adjacent groups of R_bare bonded with each other to form a substituted or unsubstituted, saturated or unsaturated ring, or do not form a substituted or unsubstituted, saturated or unsaturated ring;

when a plurality of R_cs exist, one or more pairs of two or more adjacent groups of R_care bonded with each other to form a substituted or unsubstituted, saturated or unsaturated ring, or do not form a substituted or unsubstituted, saturated or unsaturated ring;

n21 and n22 are independently an integer of 0 to 4;

R_ato R_cthat do not form the substituted or unsubstituted, saturated or unsaturated ring are independently

—O—(R₉₀₄),
—S—(R₉₀₅),

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wherein, in the formula (31),

one or more pairs of two or more adjacent groups of R₃₀₁to R₃₀₇and R₃₁₁to R₃₁₇form a substituted or unsubstituted, saturated or unsaturated ring, or do not form a substituted or unsubstituted saturated or unsaturated ring;

R₃₀₁to R₃₀₇and R₃₁₁to R₃₁₇that do not form the substituted or unsubstituted, saturated or unsaturated ring are independently a hydrogen atom,

a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

—Si(R₉₀₁)(R₉₀₂)(R₉₀₃),

—O—(R₉₀₄),
—S—(R₉₀₅),

R₃₂₁and R₃₂₂are independently

—O—(R₉₀₄),
—S—(R₉₀₅),

R₉₀₁to R₉₀₇are as defined in the formula (1);

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wherein, in the formula (41),

a ring, b ring and c ring are independently

a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms, or

a substituted or unsubstituted heterocyclic ring having 5 to 50 ring atoms;

R₄₀₁and R₄₀₂are independently bonded to the a ring, the b ring or the c ring to form a substituted or unsubstituted heterocyclic ring or do not form a substituted or unsubstituted heterocyclic ring;

R₄₀₁and R₄₀₂that do not form the substituted or unsubstituted heterocyclic ring are independently

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wherein, in the formula (51),

r ring is a ring represented by the formula (52) or formula (53) which is fused to an adjacent ring at an arbitrary position;

q ring and s ring are independently a ring represented by the formula (54) which is fused to an adjacent ring at an arbitrary position;

p ring and t ring are independently a ring represented by the formula (55) or the formula (56) which is fused to an adjacent ring at an arbitrary position;

when a plurality of R₅₀₁s exist, adjacent R₅₀₁s are bonded with each other to form a substituted or unsubstituted, saturated or unsaturated ring, or do not form a substituted or unsubstituted, saturated or unsaturated ring;

X₅₀₁is an oxygen atom, a sulfur atom, or NR₅₀₂;

R₅₀₁and R₅₀₂that do not form the substituted or unsubstituted saturated or unsaturated ring are

—O—(R₉₀₄),
—S—(R₉₀₅),

R₉₀₁to R₉₀₇are as defined in the formula (1);

Ar₅₀₁and Ar₅₀₂are independently

L₅₀₁is

a substituted or unsubstituted alkylene group having 1 to 50 carbon atoms,

a substituted or unsubstituted alkenylene group having 2 to 50 carbon atoms,

a substituted or unsubstituted alkynylene group having 2 to 50 carbon atoms,

a substituted or unsubstituted cycloalkylene group having 3 to 50 ring carbon atoms,

a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, or

a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms;

m1 is an integer of 0 to 2, m2 is an integer of 0 to 4, m3s are independently an integer of 0 to 3, and m4s are independently an integer of 0 to 5; when a plurality of R₅₀₁s exist the R₅₀₁s may be the same or different;

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wherein, in the formula (61),

at least one pair of R₆₀₁and R₆₀₂, R₆₀₂and R₆₀₃, and R₆₀₃and R₆₀₄are bonded with each other to form a divalent group represented by the formula (62);

at least one pair of R₆₀₅and R₆₀₆, R₆₀₅and R₆₀₇, and R₆₀₇and R₆₀₈are bonded with each other to form a divalent group represented by formula (63);

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at least one of R₆₀₁to R₆₀₄that does not form the divalent group represented by the formula (62), and R₆₁₁to R₆₁₄is a monovalent group represented by the following formula (64);

at least one of R₆₀₅to R₆₀₆that do not form the divalent group represented by the formula (63), and R₆₂₁to R₆₂₄is a monovalent group represented by the following formula (64);

X₆₀₁is an oxygen atom, a sulfur atom, or NR₆₀₉;

R₆₀₁to R₆₀₆that do not form the divalent group represented by the formulas (62) and (63) and that is not the monovalent group represented by the formula (64), R₆₁₁to R₆₁₄and R₆₁₄to R₆₂₄that are not the monovalent group represented by the formula (64), and R₆₀₉are independently

—O—(R₉₀₄),
—S—(R₉₀₅),

R₉₀₁to R₉₀₇are as defined in the formula (1);

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wherein, in the formula (64), Ar₆₀₁and Ar₆₀₂are independently

a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms;

L₆₀₁to L₆₀₃are independently

a single bonded,

a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms,

a substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring atoms, or

a divalent linking group formed by bonding 2 to 4 above mentioned groups;

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wherein, in the formula (71),

A₇₀₁ring and A₇₀₂ring are independently

a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms, or

a substituted or unsubstituted heterocyclic ring having 5 to 50 ring atoms;

One or more rings selected from the group consisting of A₇₀₁ring and A₇₀₂ring are bonded to the bond * of the structure represented by the following formula (72);

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wherein, in the formula (72),

A₇₀₃rings are independently

a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms, or

a substituted or unsubstituted heterocyclic ring having 5 to 50 ring atoms;

X₇₀₁is NR₇₀₃, C(R₇₀₄)(R₇₀₅), Si(R₇₀₆) (R₇₀₇), Ge(R₇₀₈) (R₇₀₉), O, S or Se;

R₇₀₁and R₇₀₂are bonded with each other to form a substituted or unsubstituted, saturated or unsaturated ring or do not form a substituted or unsubstituted saturated or unsaturated ring;

R₇₀₁and R₇₀₂that do not form the substituted or unsubstituted, saturated or unsaturated ring, and

R₇₀₃to R₇₀₉are independently

a hydrogen atom,

a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

—Si(R₉₀₁)(R₉₀₂)(R₉₀₃),

—O—(R₉₀₄),
—S—(R₉₀₅),

R₉₀₁to R₉₀₇are as defined in the formula (1);

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wherein, in the formula (81),

A₈₀₁ring is a ring represented by the formula (82) which is fused to an adjacent ring at an arbitrary position;

A₈₀₂ring is a ring represented by the formula (83) which is fused to an adjacent ring at an arbitrary position;

two bonds * bond to A₈₀₃ring at an arbitrary position;

X₈₀₁and X₈₀₂are independently C(R₈₀₃)(R₈₀₄), Si(R₈₀₅)(R₈₀₆), an oxygen atom, or a sulfur atom;

A₈₀₃ring is a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic ring having 5 to 50 ring atoms;

Ar₈₀₁is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms;

R₈₀₁to R₈₀₆are independently

—O—(R₉₀₄),
—S—(R₉₀₅),

R₉₀₁to R₉₀₇are as defined in the formula (1);

m801 and m802 are independently an integer of 0 to 2; when these are 2, a plurality of R₈₀₁s or R₈₀₂s may be the same or different;

a801 is an integer of 0 to 2; when a801 is 0 or 1, the structure in the parentheses indicated by “3-a801” may be the same as or different from each other, when a801 is 2, Ar₈₀₁s may be the same or different from each other.

2. An electronic apparatus provided with the organic electroluminescence device according to the above 1.

According to the invention, an organic EL device having a long lifetime, and an electronic apparatus provided with the organic EL device can be provided.

BRIEF DESCRIPTION OF THE DRAWINGS

FIG. 1 is a view showing a schematic configuration of one embodiment of the organic EL device of the invention.

MODE FOR CARRYING OUT THE INVENTION
Definition

In the present specification, a hydrogen atom means an atom including isotopes different in the number of neutrons, namely, a protium, a deuterium and a tritium.

In the present specification, to a bondable position in which a symbol such as “R”, or “D” representing a deuterium atom is not specified in a chemical formula, a hydrogen atom, that is, a light hydrogen atom, a deuterium atom, or a tritium atom is bonded thereto.

In the present specification, a term “ring carbon atoms” represents the number of carbon atoms among atoms forming a subject ring itself of a compound having a structure in which atoms are bonded in a ring form (for example, a monocyclic compound, a fused ring compound, a cross-linked compound, a carbocyclic compound or a heterocyclic compound). When the subject ring is substituted by a substituent, the carbon contained in the substituent is not included in the number of ring carbon atoms. The same shall apply to the “ring carbon atoms” described below, unless otherwise noted. For example, a benzene ring has 6 ring carbon atoms, a naphthalene ring has 10 ring carbon atoms, a pyridine ring has 5 ring carbon atoms, and a furan ring has 4 ring carbon atoms. Further, for example, a 9,9-diphenylfluorenyl group has 13 ring carbon atoms, and a 9,9′-spirobifluorenyl group has 25 ring carbon atoms.

Further, when the benzene ring or the naphthalene ring is substituted by an alkyl group as a substituent, for example, the number of carbon atoms of the alkyl group is not included in the ring carbon atoms.

In the present specification, a term “ring atoms” represents the number of atoms forming a subject ring itself of a compound having a structure in which atoms are bonded in a ring form (for example, a monocycle, a fused ring and a ring assembly) (for example, a monocyclic compound, a fused ring compound, a cross-linked compound, a carbocyclic compound or a heterocyclic compound). The term “ring atoms” does not include atoms which do not form the ring (for example, a hydrogen atom which terminates a bond of the atoms forming the ring) or atoms contained in a substituent when the ring is substituted by the substituent. The same shall apply to the “ring atoms” described below, unless otherwise noted. For example, a pyridine ring has 6 ring atoms, a quinazoline ring has 10 ring atoms, and a furan ring has 5 ring atoms. A hydrogen atom bonded with a carbon atom of the pyridine ring or the quinazoline ring or an atom forming the substituent is not included in the number of the ring atoms.

In the present specification, a term “XX to YY carbon atoms” in an expression of “substituted or unsubstituted ZZ group having XX to YY carbon atoms” represents the number of carbon atoms when the ZZ group is unsubstituted. The number of carbon atoms of a substituent when the ZZ group is substituted is not included. Here, “YY” is larger than “XX”, and “XX” and “YY” each mean an integer of 1 or more.

In the present specification, a term “XX to YY atoms” in an expression of “substituted or unsubstituted ZZ group having XX to YY atoms” represents the number of atoms when the ZZ group is unsubstituted. The number of atoms of a substituent when the group is substituted is not included. Here, “YY” is larger than “XX”, and “XX” and “YY” each mean an integer of 1 or more.

A term “unsubstituted” in the case of “substituted or unsubstituted ZZ group” means that the ZZ group is not substituted by a substituent, and a hydrogen atom is bonded therewith. Alternatively, a term “substituted” in the case of “substituted or unsubstituted ZZ group” means that one or more hydrogen atoms in the ZZ group are substituted by a substituent. Similarly, a term “substituted” in the case of “BB group substituted by an AA group” means that one or more hydrogen atoms in the BB group are substituted by the AA group.

Hereinafter, the substituent described herein will be described.

The number of the ring carbon atoms of the “unsubstituted aryl group” described herein is 6 to 50, preferably 6 to 30, and more preferably 6 to 18, unless otherwise specified.

The number of the ring carbon atoms of the “unsubstituted heterocyclic group” described herein is 5 to 50, preferably 5 to 30, and more preferably 5 to 18, unless otherwise specified.

The number of the carbon atoms of the “unsubstituted alkyl group” described herein is 1 to 50, preferably 1 to 20, and more preferably 1 to 6, unless otherwise specified.

The number of the carbon atoms of the “unsubstituted alkenyl group” described herein is 2 to 50, preferably 2 to 20, and more preferably 2 to 6, unless otherwise specified.

The number of the carbon atoms of the “unsubstituted alkynyl group” described herein is 2 to 50, preferably 2 to 20, and more preferably 2 to 6, unless otherwise specified.

The number of the ring carbon atoms of the “unsubstituted cycloalkyl group” described herein is 3 to 50, preferably 3 to 20, and more preferably 3 to 6, unless otherwise specified.

The number of the ring carbon atoms of the “unsubstituted arylene group” described herein is 6 to 50, preferably 6 to 30, and more preferably 6 to 18, unless otherwise specified.

The number of the ring atoms of the “unsubstituted divalent heterocyclic group” described herein is 5 to 50, preferably 5 to 30, and more preferably 5 to 18, unless otherwise specified.

The number of the carbon atoms of the “unsubstituted alkylene group” described herein is 1 to 50, preferably 1 to 20, and more preferably 1 to 6, unless otherwise specified.

Specific examples (specific example group G1) of the “substituted or unsubstituted aryl group” described herein include an unsubstituted aryl group and a substituted aryl group described below. (Here, a term “unsubstituted aryl group” refers to a case where the “substituted or unsubstituted aryl group” is the “unsubstituted aryl group,” and a term “substituted aryl group” refers to a case where the “substituted or unsubstituted aryl group” is the “substituted aryl group”. Hereinafter, a case of merely “aryl group” includes both the “unsubstituted aryl group” and the “substituted aryl group”.

The “substituted aryl group” refers to a case where the “unsubstituted aryl group” has a substituent, and specific examples thereof include a group in which the “unsubstituted aryl group” has the substituent, and a substituted aryl group described below. It should be noted that examples of the “unsubstituted aryl group” and examples of the “substituted aryl group” listed herein are only one example, and the “substituted aryl group” described herein also includes a group in which a group in which “unsubstituted aryl group” has a substituent further has a substituent, and a group in which “substituted aryl group” further has a substituent, and the like.

An unsubstituted aryl group:

a phenyl group,

a p-biphenyl group,

a m-biphenyl group,

an o-biphenyl group,

a p-terphenyl-4-yl group,

a p-terphenyl-3-yl group,

a p-terphenyl-2-yl group,

a m-terphenyl-4-yl group,

a m-terphenyl-3-yl group,

a m-terphenyl-2-yl group,

an o-terphenyl-4-yl group,

an o-terphenyl-3-yl group,

an o-terphenyl-2-yl group,

a 1-naphthyl group,

a 2-naphthyl group,

an anthryl group,

a benzanthryl group,

a phenanthryl group,

a benzophenanthryl group,

a phenalenyl group,

a pyrenyl group,

a chrysenyl group,

a benzochrysenyl group,

a triphenylenyl group,

a benzotriphenylenyl group,

a tetracenyl group,

a pentacenyl group,

a fluorenyl group,

a 9,9′-spirobifluorenyl group,

a benzofluorenyl group,

a dibenzofluorenyl group,

a fluoranethenyl group,

a benzofluoranethenyl group, and

a perylenyl group.

A substituted aryl group:

an o-tolyl group,

a m-tolyl group,

a p-tolyl group,

a p-xylyl group,

a m-xylyl group,

an o-xylyl group,

a p-isopropyl phenyl group,

a m-isopropyl phenyl group,

an o-isopropyl phenyl group,

a p-t-butylphenyl group,

a m-t-butylphenyl group,

an o-t-butylphenyl group,

a 3,4,5-trimethylphenyl group,

a 9,9-dimethylfluorenyl group,

a 9,9-diphenylfluorenyl group

a 9,9-di(4-methylphenyl)fluorenyl group,

a 9,9-di(4-isopropylphenyl)fluorenyl group,

a 9,9-di(4-t-butylphenyl)fluorenyl group,

a cyanophenyl group,

a triphenylsilylphenyl group,

a trimethylsilylphenyl group,

a phenylnaphthyl group, and

a naphthylphenyl group.

The “heterocyclic group” described herein is a ring group having at least one hetero atom in the ring atom. Specific examples of the hetero atom include a nitrogen atom, an oxygen atom, a sulfur atom, a silicon atom, a phosphorus atom and a boron atom.

The “heterocyclic group” described herein may be a monocyclic group, or a fused ring group.

The “heterocyclic group” described herein may be an aromatic heterocyclic group, or an aliphatic heterocyclic group.

Specific examples (specific example group G2) of the “substituted or unsubstituted heterocyclic group” include an unsubstituted heterocyclic group and a substituted heterocyclic group described below. (Here, the unsubstituted heterocyclic group refers to a case where the “substituted or unsubstituted heterocyclic group” is the “unsubstituted heterocyclic group,” and the substituted heterocyclic group refers to a case where the “substituted or unsubstituted heterocyclic group” is the “substituted heterocyclic group”. Hereinafter, the case of merely “heterocyclic group” includes both the “unsubstituted heterocyclic group” and the “substituted heterocyclic group”.

The “substituted heterocyclic group” refers to a case where the “unsubstituted heterocyclic group” has a substituent, and specific examples thereof include a group in which the “unsubstituted heterocyclic group” has a substituent, and a substituted heterocyclic group described below. It should be noted that examples of the “unsubstituted heterocyclic group” and examples of the “substituted heterocyclic group” listed herein are merely one example, and the “substituted heterocyclic group” described herein also includes a group in which “unsubstituted heterocyclic group” which has a substituent further has a substituent, and a group in which “substituted heterocyclic group” further has a substituent, and the like.

An unsubstituted heterocyclic group having a nitrogen atom:

a pyrrolyl group,

an imidazolyl group,

a pyrazolyl group,

a triazolyl group,

a tetrazolyl group,

an oxazolyl group,

an isoxazolyl group,

an oxadiazolyl group,

a thiazolyl group,

an isothiazolyl group,

a thiadiazolyl group,

a pyridyl group,

a pyridazinyl group,

a pyrimidinyl group,

a pyrazinyl group,

a triazinyl group,

an indolyl group,

an isoindolyl group,

an indolizinyl group,

a quinolizinyl group,

a quinolyl group,

an isoquinolyl group,

a cinnolyl group,

a phthalazinyl group,

a quinazolinyl group,

a quinoxalinyl group,

a benzimidazolyl group,

an indazolyl group,

a phenanthrolinyl group,

a phenanthridinyl group

an acridinyl group,

a phenazinyl group,

a carbazolyl group,

a benzocarbazolyl group,

a morpholino group,

a phenoxazinyl group,

a phenothiazinyl group,

an azacarbazolyl group, and

a diazacarbazolyl group.

An unsubstituted heterocyclic group having an oxygen atom:

a furyl group,

an oxazolyl group,

an isoxazolyl group,

an oxadiazolyl group,

a xanthenyl group,

a benzofuranyl group,

an isobenzofuranyl group,

a dibenzofuranyl group,

a naphthobenzofuranyl group,

a benzooxazolyl group,

a benzisoxazolyl group,

a phenoxazinyl group,

a morpholino group,

a dinaphthofuranyl group,

an azadibenzofuranyl group,

a diazadibenzofuranyl group,

an azanaphthobenzofuranyl group, and

a diazanaphthobenzofuranyl group.

An unsubstituted heterocyclic group having a sulfur atom:

a thienyl group,

a thiazolyl group,

an isothiazolyl group,

a thiadiazolyl group,

a benzothiophenyl group,

an isobenzothiophenyl group,

a dibenzothiophenyl group,

a naphthobenzothiophenyl group,

a benzothiazolyl group,

a benzisothiazolyl group,

a phenothiazinyl group,

a dinaphthothiophenyl group,

an azadibenzothiophenyl group,

a diazadibenzothiophenyl group,

an azanaphthobenzothiophenyl group, and

a diazanaphthobenzothiophenyl group.

A substituted heterocyclic group having a nitrogen atom:

a (9-phenyl)carbazolyl group,

a (9-biphenylyl)carbazolyl group,

a (9-phenyl)phenylcarbazolyl group,

a (9-naphthyl)carbazolyl group,

a diphenylcarbazol-9-yl group,

a phenylcarbazol-9-yl group,

a methylbenzimidazolyl group,

an ethylbenzimidazolyl group,

a phenyltriazinyl group,

a biphenylyltriazinyl group,

a diphenyltriazinyl group,

a phenylquinazolinyl group, and

a biphenylylquinazolinyl group.

A substituted heterocyclic group having an oxygen atom:

a phenyldibenzofuranyl group,

a methyldibenzofuranyl group,

a t-butyidibenzofuranyl group, and

a monovalent residue of spiro[9H-xanthene-9,9′-[9H]fluorene].

A substituted heterocyclic group having a sulfur atom:

a phenyldibenzothiophenyl group,

a methyldibenzothiophenyl group,

a t-butyldibenzothiophenyl group, and

a monovalent residue of spiro[9H-thiaxantene-9,9′-[9H]fluorene].

A monovalent group derived from the following unsubstituted heterocyclic ring containing at least one of a nitrogen atom, an oxygen atom and a sulfur atom by removal of one hydrogen atom bonded to the ring atoms thereof, and a monovalent group in which a monovalent group derived from the following unsubstituted heterocyclic ring has a substituent by removal of one hydrogen atom bonded to the ring atoms thereof:

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In the formulas (XY-1) to (XY-18), X_Aand Y_Aare independently an oxygen atom, a sulfur atom, NH or CH₂. However, at least one of X_Aand Y_Ais aη oxygen atom, a sulfur atom or NH.

The heterocyclic ring represented by the formulas (XY-1) to (XY-18) becomes a monovalent heterocyclic group having a bond at an arbitrary position.

An expression “the monovalent group derived from the unsubstituted heterocyclic ring represented by the formulas (XY-1) to (XY-18) has a substituent” refers to a case where the hydrogen atom bonded with the carbon atom which constitutes a skeleton of the formulas is substituted by a substituent, or a state in which X_Aor Y_Ais NH or CH₂, and the hydrogen atom in the NH or CH₂is replaced with a substituent

Specific examples (specific example group G3) of the “substituted or unsubstituted alkyl group” include an unsubstituted alkyl group and a substituted alkyl group described below. (Here, the unsubstituted alkyl group refers to a case where the “substituted or unsubstituted alkyl group” is the “unsubstituted alkyl group,” and the substituted alkyl group refers to a case where the “substituted or unsubstituted alkyl group” is the “substituted alkyl group”) Hereinafter, the case of merely “alkyl group” includes both the “unsubstituted alkyl group” and the “substituted alkyl group”.

The “substituted alkyl group” refers to a case where the “unsubstituted alkyl group” has a substituent, and specific examples thereof include a group in which the “unsubstituted alkyl group” has a substituent, and a substituted alkyl group described below. It should be noted that examples of the “unsubstituted alkyl group” and examples of the “substituted alkyl group” listed herein are merely one example, and the “substituted alkyl group” described herein also includes a group in which “unsubstituted alkyl group” has a substituent further has a substituent, a group in which “substituted alkyl group” further has a substituent, and the like.

An unsubstituted alkyl group:

a methyl group,

an ethyl group,

a n-propyl group,

an isopropyl group,

a n-butyl group,

an isobutyl group,

a s-butyl group, and

a t-butyl group.

A substituted alkyl group:

a heptafluoropropyl group (including an isomer),

a pentafluoroethyl group,

a 2,2,2-trifluoroethyl group, and

a trifluoromethyl group.

Specific examples (specific example group G4) of the “substituted or unsubstituted alkenyl group” include an unsubstituted alkenyl group and a substituted alkenyl group described below. (Here, the unsubstituted alkenyl group refers to a case where the “substituted or unsubstituted alkenyl group” is the “unsubstituted alkenyl group,” and the substituted alkenyl group refers to a case where the “substituted or unsubstituted alkenyl group” is the “substituted alkenyl group”). Hereinafter, the case of merely “alkenyl group” includes both the “unsubstituted alkenyl group” and the “substituted alkenyl group”.

The “substituted alkenyl group” refers to a case where the “unsubstituted alkenyl group” has a substituent, and specific examples thereof include a group in which the “unsubstituted alkenyl group” has a substituent, and a substituted alkenyl group described below. It should be noted that examples of the “unsubstituted alkenyl group” and examples of the “substituted alkenyl group” listed herein are merely one example, and the “substituted alkenyl group” described herein also includes a group in which “unsubstituted alkenyl group” has a substituent further has a substituent, a group in which “substituted alkenyl group” further has a substituent, and the like.

An unsubstituted alkenyl group and a substituted alkenyl group:

a vinyl group,

an allyl group,

a 1-butenyl group,

a 2-butenyl group,

a 3-butenyl group,

a 1,3-butanedienyl group,

a 1-methylvinyl group,

a 1-methylallyl group,

a 1,1-dimethylallyl group,

a 2-methylallyl group, and

a 1,2-dimethylallyl group.

Specific examples (specific example group G5) of the “substituted or unsubstituted alkynyl group” include an unsubstituted alkynyl group described below. (Here, the unsubstituted alkynyl group refers to a case where the “substituted or unsubstituted alkynyl group” is the “unsubstituted alkynyl group”). Hereinafter, a case of merely “alkynyl group” includes both the “unsubstituted alkynyl group” and the “substituted alkynyl group”.

The “substituted alkynyl group” refers to a case where the “unsubstituted alkynyl group” has a substituent, and specific examples thereof include a group in which the “unsubstituted alkynyl group” described below has a substituent.

An unsubstituted alkynyl group:

an ethynyl group.

Specific examples (specific example group G6) of the “substituted or unsubstituted cycloalkyl group” described herein include an unsubstituted cycloalkyl group and a substituted cycloalkyl group described below. (Here, the unsubstituted cycloalkyl group refers to a case where the “substituted or unsubstituted cycloalkyl group” is the “unsubstituted cycloalkyl group,” and the substituted cycloalkyl group refers to a case where the “substituted or unsubstituted cycloalkyl group” is the “substituted cycloalkyl group”). Hereinafter, a case of merely “cycloalkyl group” includes both the “unsubstituted cycloalkyl group” and the “substituted cycloalkyl group”.

The “substituted cycloalkyl group” refers to a case where the “unsubstituted cycloalkyl group” a the substituent, and specific examples thereof include a group in which the “unsubstituted cycloalkyl group” has a substituent, and a substituted cycloalkyl group described below. It should be noted that examples of the “unsubstituted cycloalkyl group” and examples of the “substituted cycloalkyl group” listed herein are merely one example, and the “substituted cycloalkyl group” described herein also includes a group in which “unsubstituted cycloalkyl group” has a substituent further has a substituent, a group in which “substituted cycloalkyl group” further has a substituent, and the like.

An unsubstituted aliphatic ring group:

a cyclopropyl group,

a cyclobutyl group,

a cyclopentyl group,

a cyclohexyl group,

a 1-adamantyl group,

a 2-adamantyl group,

a 1-norbornyl group, and

a 2-norbornyl group.

A substituted cycloalkyl group:

a 4-methylcyclohexyl group.

Specific examples (specific example group G7) of the group represented by —Si(R₉₀₁)(R₉₀₂)(R₉₀₃) described herein include

—Si(G1)(G1)(G1),
—Si(G1)(G2)(G2),
—Si(G1)(G1)(G2),
—Si(G2)(G2)(G2),
—Si(G3)(G3)(G3),
—Si(G5)(G5)(G5) and
—Si(G6)(G6)(G6).

In which,

G1 is the “aryl group” described in the specific example group G1.

G2 is the “heterocyclic group” described in the specific example group G2.

G3 is the “alkyl group” described in the specific example group G3.

G5 is the “alkynyl group” described in the specific example group G5.

G6 is the “cycloalkyl group” described in the specific example group G6.

Specific examples (specific example group G8) of the group represented by —O—(R₉₀₄) described herein include

—O(G1),
—O(G2),
—O(G3) and
—O(G6).

In which,

G1 is the “aryl group” described in the specific example group G1.

G2 is the “heterocyclic group” described in the specific example group G2.

G3 is the “alkyl group” described in the specific example group G3.

G6 is the “cycloalkyl group” described in the specific example group G6.

Specific examples (specific example group G9) of the group represented by —S—(R₉₀₅) described herein include

—S(G1),
—S(G2),
—S(G3) and
—S(G6).

In which,

G1 is the “aryl group” described in the specific example group G1.

G2 is the “heterocycle group” described in the specific example group G2.

G3 is the “alkyl group” described in the specific example group G3.

G6 is the “cycloalkyl group” described in the specific example group G6.

Specific examples (specific example group G10) of the group represented by —N(R₉₀₆)(R₉₀₇) described herein include

—N(G1)(G1),
—N(G2)(G2),
—N(G1)(G2),
—N(G3)(G3) and
—N(G6) (G6).

In which,

G1 is the “aryl group” described in the specific example group G1.

G2 is the “heterocycle group” described in the specific example group G2.

G3 is the “alkyl group” described in the specific example group G3.

G6 is the “cycloalkyl group” described in the specific example group G6.

Specific examples (specific example group G11) of the “halogen atom” described herein include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom.

Specific examples of the “alkoxy group” described herein include a group represented by —O(G3), where G3 is the “alkyl group” described in the specific example group G3. The number of carbon atoms of the “unsubstituted alkoxy group” are 1 to 50, preferably 1 to 30, and more preferably 1 to 18, unless otherwise specified.

Specific examples of the “alkylthio group” described herein include a group represented by —S(G3), where G3 is the “alkyl group” described in the specific example group G3. The number of carbon atoms of the “unsubstituted alkylthio group” are 1 to 50, preferably 1 to 30, and more preferably 1 to 18, unless otherwise specified.

Specific examples of the “aryloxy group” described herein include a group represented by —O(G1), where G1 is the “aryl group” described in the specific example group G1. The number of ring carbon atoms of the “unsubstituted aryloxy group” are 6 to 50, preferably 6 to 30, and more preferably 6 to 18, unless otherwise specified.

Specific examples of the “arylthio group” described herein include a group represented by —S(G1), where G1 is the “aryl group” described in the specific example group G1. The number of ring carbon atoms of the “unsubstituted arylthio group” are 6 to 50, preferably 6 to 30, and more preferably 6 to 18, unless otherwise specified.

Specific examples of the “aralkyl group” described herein include a group represented by -(G3)-(G1), where G3 is the “alkyl group” described in the specific example group G3, and G1 is the “aryl group” described in the specific example group G1. Accordingly, the “aralkyl group” is one embodiment of the “substituted alkyl group” substituted by the “aryl group”. The number of carbon atoms of the “unsubstituted aralkyl group,” which is the “unsubstituted alkyl group” substituted by the “unsubstituted aryl group,” are 7 to 50, preferably 7 to 30, and more preferably 7 to 18, unless otherwise specified.

Specific example of the “aralkyl group” include a benzyl group, a 1-phenylethyl group, a 2-phenylethyl group, a 1-phenylisopropyl group, a 2-phenylisopropyl group, a phenyl-t-butyl group, an a-naphthylmethyl group, a 1-α-naphthylethyl group, a 2-α-naphthylethyl group, a 1-a-naphthylisopropyl group, a 2-a-naphthylisopropyl group, a 3-naphthylmethyl group, a 1-β-naphthylethyl group, a 2-β-naphthylethyl group, a 1-β-naphthylisopropyl group, and a 2-β-naphthylisopropyl group.

The substituted or unsubstituted aryl group described herein is, unless otherwise specified, preferably a phenyl group, a p-biphenyl group, a m-biphenyl group, an o-biphenyl group, a p-terphenyl-4-yl group, a p-terphenyl-3-yl group, a p-terphenyl-2-yl group, a m-terphenyl-4-yl group, a m-terphenyl-3-yl group, a m-terphenyl-2-yl group, an o-terphenyl-4-yl group, an o-terphenyl-3-yl group, an o-terphenyl-2-yl group, a 1-naphthyl group, a 2-naphthyl group, an anthryl group, a phenanthryl group, a pyrenyl group, a chrysenyl group, a triphenylenyl group, a fluorenyl group, a 9,9′-spirobifluorenyl group, a 9,9-diphenylfluorenyl group, ex the like.

The substituted or unsubstituted heterocyclic group described herein is, unless otherwise specified, preferably a pyridyl group, a pyrimidinyl group, a triazinyl group, a quinolyl group, an isoquinolyl group, a quinazolinyl group, a benzimidazolyl group, a phenanthrolinyl group, a carbazolyl group (a 1-carbazolyl group, a 2-carbazolyl group, a 3-carbazolyl group, a 4-carbazolyl group, or a 9-carbazolyl group), a benzocarbazolyl group, an azacarbazolyl group, a diazacarbazolyl group, a dibenzofuranyl group, a naphthobenzofuranyl group, an azadibenzofuranyl group, a diazadibenzofuranyl group, a dibenzothiophenyl group, a naphthobenzothiophenyl group, an azadibenzothiophenyl group, a diazadibenzothiophenyl group, a (9-phenyl)carbazolyl group (a (9-phenyl)carbazol-1-yl group, a (9-phenyl)carbazol-2-yl group, a (9-phenyl)carbazol-3-yl group, or a (9-phenyl)carbazol-4-yl group), a (9-biphenylyl)carbazolyl group, a (9-phenyl)phenylcarbazolyl group, a diphenylcarbazole-9-yl group, a phenylcarbazol-9-yl group, a phenyltriazinyl group, a biphenylyltriazinyl group, diphenyltriazinyl group, a phenyldibenzofuranyl group, a phenyldibenzothiophenyl group, an indiocarbazolyl group, a pyrazinyl group, a pyridazinyl group, a quinazolinyl group, a cinnolinyl group, a phthalazinyl group, a quinoxalinyl group, a pyrrolyl group, an indolyl group, a pyrrolo[3,2,1-jk]carbazolyl group, a furanyl group, a benzofuranyl group, a thiophenyl group, a benzothiophenyl group, a pyrazolyl group, an imidazolyl group, a benzimidazolyl group, a triazolyl group, an oxazolyl group, a benzoxazolyl group, a thiazolyl group, a benzothiazolyl group, an isothiazolyl group, a benzisothiazolyl group, a thiadiazolyl group, an isoxazolyl group, a benzisoxazolyl group, a pyrrolidinyl group, a piperidinyl group, a piperazinyl group, an imidazolidinyl group, an indro[3,2,1-jk]carbazolyl group, a dibenzothiophenyl group, or the like.

The dibenzofuranyl group and the dibenzothiophenyl group as described above are specifically any group described below, unless otherwise specified.

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In the formulas (XY-76) to (XY-79), X_Bis an oxygen atom or a sulfur atom.

The substituted or unsubstituted alkyl group described herein is, unless otherwise specified, preferably a methyl group, an ethyl group, a propyl group, an isopropyl group, a n-butyl group, an isobutyl group, a t-butyl group, or the like.

The “substituted or unsubstituted arylene group” descried herein refers to a group in which the above-described “aryl group” is converted into divalence, unless otherwise specified. Specific examples (specific example group G12) of the “substituted or unsubstituted arylene group” include a group in which the “aryl group” described in the specific example group G1 is converted into divalence. Namely, specific examples (specific example group G12) of the “substituted or unsubstituted arylene group” refer to a group derived from the “aryl group” described in specific example group G1 by removal of one hydrogen atom bonded to the ring carbon atoms thereof.

Specific examples (specific example group G13) of the “substituted or unsubstituted divalent heterocyclic group” include a group in which the “heterocyclic group” described in the specific example group G2 is converted into divalence. Namely, specific examples (specific example group G13) of the “substituted or unsubstituted divalent heterocyclic group” refer to a group derived from the “heterocyclic group” described in specific example group G2 by removal of one hydrogen atom bonded to the ring atoms thereof.

Specific examples (specific example group G14) of the “substituted or unsubstituted alkylene group” include a group in which the “alkyl group” described in the specific example group G3 is converted into divalence. Namely, specific examples (specific example group G14) of the “substituted or unsubstituted alkylene group” refer to a group derived from the “alkyl group” described in specific example group G3 by removal of one hydrogen atom bonded to the carbon atoms constituting the alkane structure thereof.

The substituted or unsubstituted arylene group described herein is any group described below, unless otherwise specified.

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In the formulas (XY-20) to (XY-29), (XY-83) and (XY-84), R₉₀₈is a substituent.

Then, m901 is an integer of 0 to 4, and when m901 is 2 or more, a plurality of R₉₀₈may be the same with or different from each other.

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In the formulas (XY-30) to (XY-40), R₉₀₉is independently a hydrogen atom or a substituent. Two of R₉₀₉may be bonded with each other through a single bond to form a ring.

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In the formulas (XY-41) to (XY-46), R₉₁₀is a substituent.

Then, m902 is an integer of 0 to 6. When m902 is 2 or more, a plurality of R₉₁₀may be the same with or different from each other.

The substituted or unsubstituted divalent heterocyclic group described herein is preferably any group described below, unless otherwise specified.

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In the formulas (XY-50) to (XY-60), R₉₁₁is a hydrogen atom or a substituent.

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In the formulas (XY-65) to (XY-75), X_Bis an oxygen atom or a sulfur atom.

Herein, a case where “one or more sets of two or more groups adjacent to each other are bonded with each other to form a substituted or unsubstituted and saturated or unsaturated ring” will be described by taking, as an example, a case of an anthracene compound represented by the following formula (XY-80) in which a mother skeleton is an anthracene ring.

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For example, two adjacent to each other into one set when “one or more sets of two or more groups adjacent to each other are bonded with each other to form the ring” among R₉₂₁to R₉₃₀include R₉₂₁and R₉₂₂, R₉₂₂and R₉₂₃, R₉₂₃and Raw, R₉₂₄and R₉₃₀, R₉₃₀and R₉₂₅, R₉₂₅and R₉₂₆, R₉₂₆and R₉₂₇, R₉₂₇and R₉₂₈, R₉₂₈and R₉₂₉, and R₉₂₉and R₉₂₁.

The above-described “one or more sets” means that two or more sets of two groups adjacent to each other may simultaneously form the ring. For example, a case where R₉₂₁and R₉₂₂are bonded with each other to form a ring A, and simultaneously R₉₂₅and R₉₂₆are bonded with each other to form a ring B is represented by the following formula (XY-81).

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A case where “two or more groups adjacent to each other” form a ring means that, for example, R₉₂₁and R₉₂₂are bonded with each other to form a ring A, and R₉₂₂and R₉₂₃are bonded with each other to form a ring C. A case where the ring A and ring C sharing R₉₂₂are formed, in which the ring A and the ring C are fused to the anthracene mother skeleton by three of R₉₂₁to R₉₂₃adjacent to each other, is represented by the following (XY-82).

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The rings A to C formed in the formulas (XY-81) and (XY-82) are a saturated or unsaturated ring.

A term “unsaturated ring” means an aromatic hydrocarbon ring or an aromatic heterocyclic ring. A term “saturated ring” means an aliphatic hydrocarbon ring or an aliphatic heterocyclic ring.

For example, the ring A formed by R₉₂₁and R₉₂₂being bonded with each other, represented by the formula (XY-81), means a ring formed by a carbon atom of the anthracene skeleton bonded with R₉₂₁, a carbon atom of the anthracene skeleton bonded with R₉₂₂, and one or more arbitrary elements. Specific examples include, when the ring A is formed by R₉₂₁and R₉₂₂, a case where an unsaturated ring is formed of a carbon atom of an anthracene skeleton bonded with R₉₂₁, a carbon atom of the anthracene skeleton bonded with R₉₂₂, and four carbon atoms, in which a ring formed by R₉₂₁and R₉₂₂is formed into a benzene ring. Further, when a saturated ring is formed, the ring is formed into a cyclohexane ring.

Here, “arbitrary elements” are preferably a C element, a N element, an O element and a S element. In the arbitrary elements (for example, a case of the C element or the N element), the bond(s) that is(are) not involved in the formation of the ring may be terminated by a hydrogen atom, or may be substituted by an arbitrary substituent. When the ring contains the arbitrary elements other than the C element, the ring to be formed is a heterocyclic ring.

The number of “one or more arbitrary elements” forming the saturated or unsaturated ring is preferably 2 or more and 15 or less, more preferably 3 or more and 12 or less, and further preferably 3 or more and 5 or less.

As specific examples of the aromatic hydrocarbon ring, a structure in which the aryl group described in specific example group G1 is terminated with a hydrogen atom may be mentioned.

As specific examples of the aromatic heterocyclic ring, a structure in which the aromatic heterocyclic group described in specific example group G2 is terminated with a hydrogen atom may be mentioned.

As specific examples of the aliphatic hydrocarbon ring, a structure in which the cycloalkyl group described in specific example group G6 is terminated with a hydrogen atom may be mentioned.

When the above-described “saturated or unsaturated ring” has a substituent, the substituent is an “arbitrary substituent” as described below, for example. When the above-mentioned “saturated or unsaturated ring” has a substituent, specie examples of the substituent refer to the substituents described in above-mentioned “the substituent described herein”.

In one embodiment of the present specification, the substituent (hereinafter, referred to as an “arbitrary substituent” in several cases) in the case of the “substituted or unsubstituted” is a group selected from the group consisting of

an unsubstituted alkyl group having 1 to 50 carbon atoms,

an unsubstituted alkenyl group having 2 to 50 carbon atoms,

an unsubstituted alkynyl group having 2 to 50 carbon atoms,

an unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

—Si(R₉₀₁)(R₉₀₂)(R₉₀₃),

—O—(R₉₀₄),
—S—(R₉₀₅)

—N(R₉₀₆)(R₉₀₇)

wherein,

R₉₀₁to R₉₀₇are independently

a hydrogen atom,

a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms; and when two or

more of Ran to R₉₀₇exist, two or more of R₉₀₁to R₉₀₇may be the same with or different from each other,

a halogen atom, a cyano group, a nitro group,

an unsubstituted aryl group having 6 to 50 ring carbon atoms, and

an unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

In one embodiment the substituent in the case of “substituted or unsubstituted” is a group selected from the group consisting of

an alkyl group having 1 to 50 carbon atoms,

an aryl group having 6 to 50 ring carbon atoms, and

a monovalent heterocyclic group having 5 to 50 ring atoms.

In one embodiment the substituent in the case of “substituted or unsubstituted” is a group selected from the group consisting of

an alkyl group having 1 to 18 carbon atoms,

an aryl group having 6 to 18 ring carbon atoms, and

a monovalent heterocyclic group having 5 to 18 ring atoms.

Specific examples of each group of the arbitrary substituent described above are as described above.

Herein, unless otherwise specified, the saturated or unsaturated ring (preferably substituted or unsubstituted and saturated or unsaturated five-membered or six-membered ring, more preferably a benzene ring) may be formed by the arbitrary substituents adjacent to each other. Herein, unless otherwise specified, the arbitrary substituent may further have the substituent. Specific examples of the substituent that the arbitrary substituent further has include to the ones same as the arbitrary substituent described above.

[Organic EL Device]

The organic EL device according to one aspect of the invention comprises a cathode, an anode and an emitting layer disposed between the cathode and the anode, and it is characterized in that the emitting layer comprises a compound represented by the following formula (1) and one or more compounds selected from the group consisting of compounds represented by each of formulas (11), (21), (31), (41), (51), (61), (71) and (81).

Each compound is described later.

The organic EL device according to one aspect of the invention exhibits high device performance by possessing the above-mentioned constitution. Specifically, it is possible to provide an organic EL device with longer life.

According to one aspect of the present invention, a method for improving a performance of an organic EL device can also be provided, the method is characterized in that the compound represented by the formula (1) and one or more compounds selected from the group consisting of the formulas (11) to (81) are used in combination in the emitting layer of the organic EL device. Specifically, the method can improve an organic EL device performance as compared with the case where a compound having the same structure as formula (1) except that only protium atoms are contained as hydrogen atoms (hereinafter also referred to as “protium compound”) is used as a host material. The case where the protium compound is used means that a host material in an emitting layer consists essentially of the protium compound (the ratio of the protium compound to the sum of the protium compound and the compound represented by formula (1) is 90 mol % or more, 95 mol % or more, or 99 mol % or more).

That is, it is possible to increase a performance of an organic EL device by, instead of a protium compound or in addition to a protium compound, using a compound obtained by replacing at least one protium atoms on an anthracene skeleton of the protium compound with a deuterium atom (a compound represented by formula (1)) as a host material.

A schematic outline of the organic EL device of one aspect of the invention is explained by reference to the FIGURE.

The organic EL device 1 according to one aspect of the invention comprises substrate 2, anode 3, emitting layer 5, cathode 10, organic layer 4 disposed between the anode 3 and the emitting layer 5, and organic layer 6 disposed between the emitting layer 5 and the cathode 10.

The compound represented by the formula (1) and one or more compounds selected from a group consisting of compounds represented by each of formula (11), (21), (31), (41), (51), (61), (71) and (81) are contained in emitting layer 5 disposed between the anode 3 and the cathode 10. Each compound contained in the emitting layer 5 may be used singly or in combination of two or more.

(Compound Represented by Formula (1))

The compound represented by the formula (1) is explained below.

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In the formula (1),

R₁to R₈are independently

—O—(R₉₀₄),
—S—(R₉₀₅),

R₉₀₁to R₉₀₇are independently

when two or more of R₉₀₁to R₉₀₇exist, two or more of R₉₀₁to R₉₀₇may be the same with or different from each other;

at least one of R₁to R_ais a deuterium atom;

two or more adjacent groups of R₁to R₄and two or more adjacent groups of R₅to R₈do not form a ring;

L₁and L₂are independently

a single bond,

a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or

a substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring atoms;

Ar is

a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms;

one of R₁₁to R₁₈is a single bond bonding to L₂;

R₁₁to R₁₈which are not single bonds bonding to L₂are independently

—O—(R₉₀₄),
—S—(R₉₀₅),

R₉₀₁to R₉₀₇are as defined in R₁to R₈; and

two or more adjacent groups of R₁₁to R₁₈do not form a ring.)

All of R₁to R₈may be deuterium atoms or a part of them (e.g., one or two of R₁to R₈) may be deuterium atoms.

R₁to R₈that are not deuterium atoms are preferably hydrogen atoms (protium atoms).

In one embodiment, at least one hydrogen atom contained in one or more groups selected from a group consisting of L₁and L₂is a deuterium atom. In more detail, in one embodiment, one or more groups selected from the group consisting of L₁and L₂are an unsubstituted arylene group having 6 to 30 ring carbon atoms in which at least one hydrogen atom is a deuterium atom, or an unsubstituted divalent heterocyclic group having 5 to 30 ring atoms in which at least one hydrogen atom is a deuterium atom.

In one embodiment, L₁and L₂are independently a single bond, or a substituted or unsubstituted arylene group having 6 to 14 ring carbon atoms. It is preferable that at least one of L₁and L₂is a single bond.

In one embodiment, among R₁₁to R₁₈, those which are not single bonds bonded to b are hydrogen atoms.

In one embodiment, at least one of R₁₁to R₁₈which is not a single bond bonding to b is a deuterium atom.

In one embodiment at least one hydrogen atom contained in one or more Ar is a deuterium atom. In more detail, in one embodiment, Ar is an unsubstituted aryl group having 6 to 50 ring carbon atoms in which at least one hydrogen atom is a deuterium atom, or an unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms in which at least one hydrogen atom is a deuterium atom.

Existence of a deuterium atom in the compound is confirmed by Mass Spectrometry or ¹H-NMR Spectrometry. The bonding position of a deuterium atom in the compound is identified by ¹H-NMR Spectrometry. In concrete terms, it is confirmed as follows.

If it is identified that, by Mass Spectrometry, a molecular weight of a target compound is greater by “one” than a molecular weight of a corresponding compound in which all hydrogen atoms are protium atoms, it is confirmed that one deuterium atom exists in the target compound. Further, the number of deuterium atoms in a molecule can be confirmed by an integration value obtained by ¹H-NMR analysis on the target compound, since no signal is observed by performing ¹H-NMR analysis on a deuterium atom. The bonding position of a deuterium can be identified by performing ¹H-NMR analysis on the target compound and assigning signals.

In the organic EL device according to one aspect of the invention, the content ratio of the protium compound to the total of the compound represented by formula (1) and the protium compound in the emitting layer is preferably 99 mol % or less. The content ratio of the protium compound is confirmed by Mass Spectrometry.

In one embodiment, the emitting layer of the organic EL device according to one aspect of the invention includes the compound represented by the formula (1) and a protium compound, and the content ratio of the former to the total thereof is 30 mol % or more, 50 mol % or more, 70 mol % or more, 90 mol % or more, 95 mol % or more, 99 mol % or more, or 100 mol %.

Ar is preferably a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, more preferably selected from groups represented by the following formulas (a1) to (a4).

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wherein in the formulas (a1) to (a4),

* is a angle bond bonding to L₁;

R₂₁is

—O—(R₉₀₄),
—S—(R₉₀₅),

R₉₀₁to R₉₀₇are as defined in the formula (1);

m1 is an integer of 0 to 4;

m2 is an integer of 0 to 5;

m3 is an integer of 0 to 7;

when each of m1 to m3 is 2 or more, a plurality of R₂₁s may be the same or different; and

when each of m1 to m3 is 2 or more, adjacent R₂₁s are bonded with each other to form a substituted or unsubstituted, saturated or unsaturated ring, or do not form a substituted or unsubstituted, saturated or unsaturated ring.

Preferably, L₁and L₂are independently a single bond, or a substituted or unsubstituted arylene group having 6 to 14 ring carbon atoms. It is preferable that at least one of L₁and L₂is a single bond.

In one embodiment, the compound represented by the formula (1) is a compound represented by following formula (2).

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wherein in the formula (2), R₁to R₈, Ar, L₁and L₂are as defined in the formula (1).

In one embodiment, the compound represented by the formula (1) is a compound represented by following formula (3).

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wherein in the formula (3), Ar, L₁and L₂are as defined in the formula (1).

In one embodiment, the compound represented by the formula (1) is a compound represented by following formula (1A) or (1B).

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wherein in the formula (1A) and (1B),

R_1Ato R_8Aare independently a hydrogen atom, and at least one of R_1Ato R_8Ais a deuterium atom;

L_1Aand L_2Aare independently a single bond, an unsubstituted phenylene group, or an unsubstituted naphthylene group;

Ar_1Ais a substituted or unsubstituted phenyl group or a substituted or unsubstituted naphthyl group, and the substituent for Ar_1Ais a phenyl group;

R_11Ato R_14Aare independently a hydrogen atom, or an unsubstituted aryl group including 6 to 50 ring carbon atoms; and

two or more adjacent groups of R_11Ato R_14Ado not form a ring.

In one embodiment, in the formula (1A) or (1B), at least two of R_1Ato R_1Aare deuterium atoms.

In one embodiment, in the formula (1A) or (1B), R_1Ato R_8Aare all deuterium atoms.

In one embodiment, in the formula (1A) or (1B), at least one hydrogen atom contained in Ar_1Ais a deuterium atom.

In one embodiment, in the formula (1A) or (1B), R_11Ato R_14Aare hydrogen atoms.

In one embodiment, in the formula (1A) or (1B), R_11Ato R_14Aare deuterium atoms.

The compound represented by the formula (1) can be synthesized in accordance with the synthesis process described in Examples by using publicly known alternative reactions or materials corresponding to a target compound.

Examples of the compound represented by formula (1) include the following compounds.

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(Compound Represented by Formula (11))

The compound represented by the formula (11) is explained below.

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In the formula (11),

at least one of R₁₀₁to R₁₁₀is a monovalent group represented by the formula (12);

R₁₀₁to R₁₁₀that do not form the substituted or unsubstituted, saturated or unsaturated ring and that are not a monovalent group represented by the following formula (12) are independently

—O—(R₉₀₄),
—S—(R₉₀₅),

R₉₀₁to R₉₀₇are as defined in the formula (1);

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wherein, in the formula (12), Ar₁₀₁and Ar₁₀₂are independently

a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms;

L₁₀₁to L₁₀₃are independently

a single bonded,

a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or

a substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring atoms;

In the formula (11), it is preferable that two of R₁₀₁to R₁₁₀are the group represented by the formula (12).

In one embodiment, the compound represented by the formula (11) is represented by the following formula (13):

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wherein in the formula (13), R₁₁₁to R₁₁₈are the same as R₁₀₁to R₁₁₀that is not a monovalent group represented by the formula (12) in the formula (11). Ar₁₀₁, Ar₁₀₂, L₁₀₁, L₁₀₂and L₁₀₃are as defined in the formula (12).

In the formula (11), L₁₀₁is preferably a single bond and L₁₀₂and L₁₀₃are preferably a single bond.

In one embodiment, the compound represented by the formula (11) is represented by the formula (14) or (15).

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wherein in the formula (14), R₁₁₁to R₁₁₈are as defined in the formula (13). Ar₁₀₁, Ar₁₀₂, L₁₀₂and L₁₀₃are as defined in the formula (12).

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wherein in the formula (15), R₁₁₁to R₁₁₈are as defined in the formula (13). Ar₁₀₁and Ar₁₀₂are as defined in the formula (12).

In the formula (11) and formula (12), it is preferable that at least one of Ar₁₀₁and Ar₁₀₂is the group represented by the following formula (16).

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wherein to the formula (16),

X₁₀₁is an oxygen atom or a sulfur atom;

One or more pairs of two or more adjacent groups of R₁₂₁to R₁₂₇are bonded with each other to form a substituted or unsubstituted, saturated or unsaturated ring, or do not form a substituted or unsubstituted, saturated or unsaturated ring:

R₁₂₁to R₁₂₇that do not form the substituted or unsubstituted, saturated or unsaturated ring are independently

—O—(R₉₀₄),
—S—(R₉₀₆),

R₉₀₁to R₉₀₇are as defined in the formula (1).

It is preferable that X₁₀₁is an oxygen atom.

It is preferable that at least one of R₁₂₁to R₁₂₇is

a substituted or unsubstituted alky) group having 1 to 50 carbon atoms,

a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

It is preferable that in the formula (11) and formula (12), Ar₁₀₁is a group represented by the formula (16) and Ar₁₀₂is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.

In one embodiment, the compound represented by the formula (11) is represented by the following formula (17).

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wherein to the formula (17), R₁₁₁to R₁₁₈are as defined in the formula (13), and R₁₂₁to R₁₂₇are as defined in the formula (16);

R₁₃₁to R₁₃₅are independently

—O—(R₉₀₄),
—S—(R₉₀₅),

As the compound represented by the formula (11), the following compounds can be given as specific examples, for example. In the following example compounds, Me represents a methyl group.

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(Compound Represented by Formula (21))

The compound represented by the formula (21) is explained below.

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wherein, in the formula (21),

Zs are independently CR_aor N;

n21 and n22 are independently an integer of 0 to 4;

R_ato R_cthat do not form the substituted or unsubstituted, saturated or unsaturated ring are independently

—O—(R₉₀₄),
—S—(R₉₀₅),

The “aromatic hydrocarbon ring” of A1 ring and A2 ring has the same structure as the compound obtained by introducing a hydrogen atom into the “aryl group” described above.

The “aromatic hydrocarbon ring” of the A1 ring and the A2 ring contains two carbon atoms in the fused bicyclic structure at the center of the formula (21) as ring atoms. Examples of “substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms” include compounds in which a hydrogen atom is introduced into the “aryl group” described in the example group G1.

The “heterocyclic ring” of A1 ring and A2 ring has the same structure as the compound obtained by introducing a hydrogen atom into toe “heterocyclic group” described above. The “heterocyclic ring” of the A1 ring and toe A2 ring contains two carbon atoms in the (used bicyclic structure at the center of the formula (21) as ring atoms. Examples of “substituted or unsubstituted heterocyclic ring having 5 to 50 ring atoms” include compounds in which a hydrogen atom is introduced into toe “heterocyclic group” described in the example group G2.

R_bis bonded to one of carbon atoms which form toe aromatic hydrocarbon ring of A1 ring, or one of atoms which form toe heterocycle of A1 ring.

R_cis bonded to one of carbon atoms which form the aromatic hydrocarbon ring of A2 ring, or one of atoms which form the heterocycle of A2 ring.

R_cis preferable that at least one (preferably two) of R_ato R_cis a group represented by the following formula (21a).

-L₂₀₁-Ar₂₀₁ (21a)

wherein to the formula (21a),

L₂₀₁is

a single bond,

a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or

a substituted or unsubstituted bivalent heterocyclic group having 5 to 30 ring atoms;

Ar₂₀₁is

a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms,

a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms, or

a group represented by toe following formula (21b):

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wherein in the formula (21 b),

L₂₁₁and L₂₁₂are independently

a single bond,

a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or

a substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring atoms;

Ar₂₁₁and Ar₂₁₂are bonded with each other to form a substituted or unsubstituted, saturated or unsaturated ring, or do not form a substituted or unsubstituted, saturated or unsaturated ring; and

Ar₂₁₁and Ar₂₁₂that do not form a substituted or unsubstituted, saturated or unsaturated ring are independently

a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms or

a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms,

In one embodiment, the compound represented by the formula (21) is represented by foe following formula (22).

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wherein in the formula (22),

one or more pairs of two or more adjacent groups of R₂₀₁to R₂₁₁are bonded with each other to form a substituted or unsubstituted, saturated or unsaturated ring, or do not form a substituted or unsubstituted saturated or unsaturated ring;

R₂₀₁to R₂₁₁that do not form the substituted or unsubstituted, saturated or unsaturated ring are independently

—O—(R₉₀₁),
—S—(R₉₀₅),

R₉₀₁to R₉₀₇are as defined in the formula (1))

It is preferable that at least one (preferably two) of R₂₀₁to R₂₁₁is the group represented by the formula (21a). It is preferable that R₂₀₄and R₂₁₁are the group represented by the formula (21a).

In one embodiment, the compound represented by the formula (21) is a compound obtained by bonding the structure represented by the following formula (21-1) or (21-2) to A1 ring. In one embodiment, the compound represented by the formula (22) is a compound obtained by bonding the structure represented by the following formula (21-1) or (21-2) to the ring to which R₂₀₄to R₂₀₇bonds to.

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wherein in the formula (21-1), two bonds shown by * independently bond to a ring carbon atom in the aromatic hydrocarbon ring or a ring atom in the heterocyclic group in A1 ring in the formula (21), or bond to one of R₂₀₄to R₂₀₇in the formula (22);

wherein in the formula (21-2), three bonds shown by * independently bond to a ring carbon atom in the aromatic hydrocarbon ring or a ring atom in the heterocyclic group in A1 ring in the formula (21), or bond to one of R₂₀₄to R₂₀₇in the formula (22);

One or more pairs of two or more adjacent groups of R₂₂₁to R₂₂₇and R₂₂₁to R₂₃₉are bonded with each other to form a substituted or unsubstituted, saturated or unsaturated ring, or do not form a substituted or unsubstituted, saturated or unsaturated ring;

R₂₂₁to R₂₂₇and R₂₃₁to R₂₃₉that do not form the substituted or unsubstituted, saturated or unsaturated ring are independently

—O—(R₉₀₄),
—S—(R₉₀₅),

R₉₀₁to R₉₀₇are as defined in the formula (1)

In one embodiment, the compound represented by the formula (21) is a compound represented by the following formula (21-3), (21-4), or (21-5).

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wherein in the formulas (21-3), (21-4) and (21-5),

A1 ring is as defined in the formula (21);

R₂₄₀₁to R₂₄₀₇are the same as R₂₂₁to R₂₂₇in the formulas (21-1) and (21-2);

R₂₄₁₀to R₂₄₁₇are the same as R₂₀₁to R₂₁₁in the formula (22); and the two R₂₄₁₇s may be the same or different.

In one embodiment, the substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms of A1 ring in the formula (21-5) is a substituted or unsubstituted napthalene ring, or a substituted or unsubstituted fluorene ring.

In one embodiment, the substituted or unsubstituted heterocycle having 5 to 50 ring atoms of A1 ring in the formula (21-5) is a substituted or unsubstituted dibenzofuran ring, a substituted or unsubstituted carbazole ring, or a substituted or unsubstituted dibenzothiophene ring.

In one embodiment, the compound represented by the formula (21) or (22) is selected from foe group consisting of the compounds represented by the following formulas (21-6-1) to (21-6-7).

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wherein in the formulas (21-6-1) to (21-6-7),

R₂₄₂₁to R₂₄₂₇are the same as R₂₂₁to R₂₂₇in the formulas (21-1) and (21-2);

R₂₄₃₀to R₂₄₃₇and R₂₄₄₁to R₂₄₄₄are the same as R₂₀₁to R₂₁₁in the formula (22);

X is O, NR₉₀₁, or C(R₉₀₂) (R₉₀₃); and

R₉₀₁to R₉₀₃are as defined in the formula (1).

In one embodiment, in the compound represented by the formula (22), one or more pairs of two or more adjacent groups of R₂₀₁to R₂₁₁are bonded with each other to form a substituted or unsubstituted, saturated or unsaturated ring. This embodiment is described in the following formula (25).

(Compound Represented by Formula (25))

The compound represented by the formula (25) is explained below.

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wherein in the formula (25),

two or more pairs selected from a group consisting of R₂₅₁and R₂₅₂, R₂₅₂and R₂₅₃, R₂₅₃and R₂₅₅, R₂₅₅and R₂₅₆, R₂₅₆and R₂₅₇, R₂₅₈and R₂₅₉, R₂₅₉and R₂₆₀, and R₂₆₀and R₂₆₁bond with each other to form a substituted or unsubstituted, saturated or unsaturated ring;

Provided that the pair of R₂₅₁and R₂₅₂and the pair of R₂₅₂and R₂₅₃do not form a ring simultaneously; the pair of R₂₅₄and R₂₅₆and the pair of R₂₅₅and R₂₅₆do not form a ring simultaneously; the pair of R₂₅₆and R₂₅₆and the pair of R₂₅₆and R₂₅₇do not form a ring simultaneously; the pair of R₂₅₈and R₂₅₉and the pair of R₂₅₉and R₂₆₀do not form a ring simultaneously; and the pair of R₂₅₉and R₂₆₀and the pair of R₂₆₀and R₂₆₁do not form a ring simultaneously;

When two or more rings are formed by R₂₅₁to R₂₆₁, the rings may be the same or different;

R₂₅₁to R₂₆₁that do not form the substituted or unsubstituted, saturated or unsaturated ring are independently

—O—(R₉₀₄),
—S—(R₉₀₅),

R₉₀₁to R₉₀₇are as defined in the formula (1).

In the formula (25), R_nand R_n+1(n is an integer selected from 251, 252, 254 to 256 and 258 to 260) bond with each other to form a substituted or unsubstituted, saturated or unsaturated ring together with two ring carbon atoms to which R_nand R_n+1bond with. The ring is preferably configured with atoms selected from C atom, O atom, S atom and N atom, and the number of atoms is preferably 3 to 7, more preferably 5 or 6.

The number of the above-described ring structures in the compound represented by the formula (25) is, for example, 2, 3 or 4. Two or more ring structures may exist in the same benzene ring of the main skeleton in the formula (25), or may exist in different benzene rings. For example, the compound has three ring structures, one ring structure may exist in each of the three benzene rings in the formula (25).

As the above-mentioned ring structure in the compound represented by the formula (25), structures represented by the following formulas (251) to (260) can be given, for example.

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wherein in the formulas (251) to (257),

each of *1 and *2, *3 and *4, *5 and *6, *7 and *8, *9 and *10, *11 and *12, and * 13 and * 14 represents two ring carbon atoms to which R_nand R_n+1bond, and R_nmay bond to either one of the two ring carbon atoms of *1 and *2, *3 and *4, *5 and *6, *7 and *8, *9 and *10, *11 and *12, and *13 and *14;

X₂₅₀₁is C(R₂₅₁₂) (R₂₅₁₃), NR₂₅₁₄, O or S;

one or more pairs of two or more adjacent groups of R₂₅₀₁to R₂₅₀₆and R₂₅₁₂to R₂₅₁₃are bonded with each other to form a substituted or unsubstituted, saturated or unsaturated ring, or do not form a substituted or unsubstituted saturated or unsaturated ring; and

R₂₅₀₁to R₂₅₁₄that do not form a substituted or unsubstituted saturated or unsaturated ring are the same as R₂₅₁to R₂₆₁.

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wherein in the formulas (258) to (260),

each of * 1 and * 2, and * 3 and * 4 represents two ring carbon atoms to which R_nand R_n+1bond, and R_nmay bond to either one of the two ring carbon atoms of * 1 and *2, or *3 and *4;

X₂₅₀₁is C(R₂₅₁₂) (R₂₅₁₃), NR₂₅₁₄, O or S;

one or more pairs of two or more adjacent groups of R₂₅₁₅to R₂₅₂₅bond to each other to form a substituted or unsubstituted, saturated or unsaturated ring, or do not form a substituted or unsubstituted saturated or unsaturated ring; and

R₂₅₁₅to R₂₅₂₁and R₂₅₂₂to R₂₅₂₅that do not form a substituted or unsubstituted saturated or unsaturated ring are the same as R₂₅₁to R₂₆₁.

In the formula (25), it is preferable that at least one of R₂₅₂, R₂₅₄, R₂₅₅, R₂₆₀and R₂₆₁(preferably at least one of R₂₅₂, R₂₅₅, and R₂₆₀, more preferably R₂₅₂) is a group which does not form a ring.

(i) Substituent in the case where the ring structure formed by R_nand R_n+1has a substituent in the formula (25),
(ii) R₂₅₁to R₂₆₁that do not form a ring structure in the formula (25), and
(iii) R₂₅₀₁to R₂₅₁₄and R₂₅₁₅to R₂₅₂₅in the formulas (251) to (260) are preferably independently

a hydrogen atom,

a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

—N(R₉₀₆) (R₉₀₇),

a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms,

a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms, or

a group selected from the following groups.

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wherein in the formulas (261) to (264),

R_ds are independently

—O—(R₉₀₄),
—S—(R₉₀₅),

X is C(R₉₀₁)(R₉₀₂), NR₉₀₃, O, or S;

R₉₀₁to R₉₀₇are as defined to the formula (1); and

p1 is independently an integer of 0 to 5, p2 is independently an integer of 0 to 4, p3 is an integer of 0 to 3, and p4 is an integer of 0 to 7.

In one embodiment, the compound represented by the formula (25) is represented by the following formulas (25-1) to (25-6).

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wherein in the formulas (25-1) to (25-6), ring d to ring i are independently a substituted or unsubstituted, saturated or unsaturated ring; and R₂₅₁to R₂₆₁are the same as defined in the formula (25).

In one embodiment, the compound represented by the formula (25) is represented by the following formulas (25-7) to (25-12).

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wherein in the formulas (25-7) to (25-12), ring d to ring f, ring k, and ring j are independently a substituted or unsubstituted, saturated or unsaturated ring; and R₂₅₁to R₂₆₁are the same as defined in the formula (25).

In one embodiment, toe compound represented by toe formula (25) is represented by the following formulas (25-13) to (25-21).

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wherein in toe formulas (25-13) to (25-21), ring d to ring k are independently a substituted or unsubstituted, saturated or unsaturated ring; and R₂₅₁to R₂₆₁are the same as defined in the formula (25).

As a substituent in the case where toe ring g or ring h further has a substituent,

a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

a group represented by the formula (261), (263) or (264) can be given for example.

In one embodiment, the compound represented by toe formula (25) is represented by one of toe following formulas (25-22) to (25-25).

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wherein in the formulas (25-22) to (25-25), X₂₅₀is independently C(R₉₀₁)(R₉₀₂), NR₉₀₃, O or S;

R₂₅₁to R₂₆₁, and R₂₇₁to R₂₇₈are the same as R₂₅₁to R₂₆₁in the formula (25); and R₉₀₁to R₉₀₃are as defined in the formula (1).

In one embodiment, the compound represented by the formula (25) is represented by the following formula (25-26).

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wherein in the formula (25-26), X₂₅₀is C(R₉₀₁)(R₉₀₂), NR₉₀₃, O or S; R₂₅₃, R₂₅₄, R₂₅₇, R₂₅₈, R₂₆₁, and R₂₇₁to R₂₆₂are the same as R₂₅₁to R₂₆₁in the formula (25); and R₉₀₁to R₉₀₃are as defined in the formula (1).

As the compound represented by the formula (21), the following compounds can be shown for example. In the following example compounds, Me represents methyl group.

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(Compound Represented by Formula (31))

The compound represented by the formula (31) is explained below.

The compound represented by formula (31) is a compound corresponding to the compound represented by the formula (21-3).

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wherein in the formula (31),

R₃₀₁to R₃₀₇and R₃₁₁to R₃₁₇that do not form the substituted or unsubstituted, saturated or unsaturated ring are independently

—O—(R₉₀₄),
—S—(R₉₀₅),

R₃₂₁and R₃₂₂are independently

—O—(R₆₀₄),
—S—(R₉₀₅),

R₉₀₁to R₉₀₇are as defined in the formula (1).

Example of “One pair of two or more adjacent groups of R₃₀₁to R₃₀₇and R₃₁₁to R₃₁₇” is pairs of R₃₀₁and R₃₀₂, R₃₀₂and R₃₀₃R₃₀₃and R₃₀₄, R₃₀₅and R₃₀₆, R₃₀₆and R₃₀₇, and R₃₀₁, R₃₀₂and R₃₀₃, and the like.

In one embodiment, at least one of R₃₀₁to R₃₀₇and R₃₁₁to R₃₁₇, preferably two of R₃₀₁to R₃₀₇and R₃₁₁to R₃₁₇is a group represented by —N(R₉₀₆)(R₉₀₇).

In one embodiment, R₃₀₁to R₃₀₇and R₃₁₁to R₃₁₇are independently a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

In one embodiment, the compound represented by the formula (31) is a compound represented by the following formula (32).

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wherein in the formula (32),

one or more pairs of two or more adjacent groups of R₃₃₁to R₃₃₄and R₃₄₁to R₃₄₄form a substituted or unsubstituted, saturated or unsaturated ring, or do not form a substituted or unsubstituted saturated or unsaturated ring;

R₃₃₁to R₃₃₄and R₃₄₁to R₃₄₄that do not form the substituted or unsubstituted, saturated or unsaturated ring and R₃₅₁and R₃₅₂are independently

a hydrogen atom,

a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms; and

R₃₆₁to Raw are independently

a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

In one embodiment, the compound represented by the formula (31) is a compound represented by the formula (33).

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wherein in the formula (33), R₃₅₁, R₃₅₂, and R₃₆₁to R₃₀₄are as defined in the formula (32).

In one embodiment, the compound represented by the formula (31) is a compound represented by the formula (34) or (35).

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wherein in the formulas (34) and (35),

R₃₆₁to R₃₆₄are as defined in the formula (32);

one or more pairs of two or more adjacent groups of R₃₇₁to R₃₇₇and R₃₈₀to R₃₈₆form a substituted or unsubstituted, saturated or unsaturated ring, or do not form a substituted or unsubstituted saturated or unsaturated ring; and

R₃₇₁to R₃₇₇and R₃₈₀to R₃₈₆that do not form the substituted or unsubstituted, saturated or unsaturated ring and R₃₀₇are independently

a hydrogen atom,

a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms, and two R₃₆₇s may be the same with or different from each other.

In one embodiment, fee compound represented by the formula (31) is a compound represented by the formula (34-2) or (35-2).

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wherein in the formulas (34-2) and (35-2), R₃₆₁to R₃₆₄, R₃₇₅to R₃₇₇and R₃₆₄to R₃₆₇are as defined in the formulas (34) and (35).

In one embodiment, R₃₆₁to R₃₆₄in the formulas (32), (33), (34), (35), (34-2) and (35-2) are independently a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms (preferably a substituted or unsubstituted phenyl group).

In one embodiment, R₃₂₁and R₃₂₂in the formula (31) and R₃₅₁, R352 and R₃₈₇in fee formulas (32), (33), (34), (35), (34-2) and (35-2) are independently a hydrogen atom or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms (preferably a substituted or unsubstituted phenyl group).

In one embodiment, fee compound represented by fee formula (31) is one or more compounds selected from fee group consisting of fee following formulas (32-11), (34-11) and (35-11).

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wherein in the formulas (32-11), (34-11) and (35-11),

one or more pairs of two or more adjacent groups of R₃₃₀₁to R₃₃₀₇and R₃₃₁₁to R₃₃₁₇form a substituted or unsubstituted, saturated or unsaturated ring, or do not form a substituted or unsubstituted, saturated or unsaturated ring;

R₃₃₀₁to R₃₃₀₇and R₃₃₁₁to R₃₃₁₇that do not form the substituted or unsubstituted, saturated or unsaturated ring, and R₃₃₃₁are independently

a hydrogen atom,

a substituted or unsubstituted aryl group having 6 to 20 ring carbon atoms, or

a substituted or unsubstituted monovalent heterocyclic group having 5 to 20 ring atoms;

two R₃₃₃₁s may be the same with or different from each other; and

R₃₃₂₁to R₃₃₂₄are independently

a substituted or unsubstituted aryl group having 6 to 20 ring carbon atoms, or

a substituted or unsubstituted monovalent heterocyclic group having 5 to 20 ring atoms.

In one embodiment, the one or more compounds selected from the group consisting of the formulas (32-11), (34-11) and (35-11) is one or more compounds selected from a group consisting of the following formulas (32-12), (34-12) and (35-12).

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wherein in the formulas (32-12), (34-12) and (35-12), R₃₃₂₁to R₃₃₂₄and R₃₃₃₁are as defined in the formulas (32-11), (34-11) and (35-11).

In one embodiment, in the formulas (32-11), (34-11), (35-11), (32-12), (34-12) and (35-12), R₃₃₂₁to R₃₃₂₄are independently a substituted or unsubstituted phenyl group.

In one embodiment, in the formulas (32-11), (34-11), (35-11), (32-12), (34-12) and (35-12), two R₃₃₃₁s are independently a hydrogen atom.

In one embodiment, in the formulas (32-11), (34-11), (35-11), (32-12), (34-12) and (35-12), the substituent in the case of “substituted or unsubstituted” is selected from the group consisting of an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 20 ring carbon atoms, and a monovalent heterocyclic group having 5 to 20 ring atoms.

In one embodiment, in the formulas (32-11), (34-11), (35-11), (32-12), (34-12) and (35-12), the substituent in the case of “substituted or unsubstituted” is an alkyl group having 1 to 5 carbon atoms.

In one embodiment, in the formulas (32-11), (34-11), (35-11), (32-12), (34-12) and (35-12), R₃₃₂₁to R₃₃₂₄are independently a substituted or unsubstituted phenyl group, and two R₃₃₃₁s are independently a hydrogen atom.

In one embodiment, in the formulas (32-11), (34-11), (35-11), (32-12), (34-12) and (35-12), R₃₃₂₁to R₃₃₂₄are independently a substituted or unsubstituted phenyl group, two R₃₃₃₁s are independently a hydrogen atom, and the substituent in the case of “substituted or unsubstituted” is selected from the group consisting of an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 20 ring carbon atoms, and a monovalent heterocyclic group having 5 to 20 ring atoms.

In one embodiment, in the compound represented by the formula (31), one or more pairs of two or more adjacent groups of Ran to R₃₀₇and R₃₁₁to R₃₁₇form a substituted or unsubstituted, saturated or unsaturated ring.

In one embodiment, the compound represented by the formula (31) is one or more compounds selected from the group consisting of the following formulas (36-1) to (36-6).

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wherein in the formulas (36-1) to (36-6),

one or more pairs of two or more adjacent groups of R₃₆₀₅to R₃₆₀₇, R₃₆₁₅to R₃₆₁₇and R₃₆₃₁bond with each other to form a substituted or unsubstituted, saturated or unsaturated ring or do not form the ring;

one or more pairs of two or more adjacent groups of R₃₆₀₁to R₃₆₀₄, R₃₆₁₁to R₃₆₁₄and R₃₆₂₁to R₃₆₂₈bond with each other to form a substituted or unsubstituted, saturated or unsaturated ring or do not form the ring;

R₃₆₀₁to R₃₆₀₇, R₃₆₁₁to R₃₆₁₇, R₃₆₂₈to R₃₆₂₈and R₃₆₃₁that do not form the ring are independently

a hydrogen atom, a halogen atom, a cyano group, a nitro group,

a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

—Si(R₉₀₁)(R₉₀₂)(R₉₀₃),

—O—(R₉₀₄),
—S—(R₉₀₅),

—N(R₉₀₆)(R₉₀₇),

a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms;

R₉₀₁to R₉₀₇are independently

when two or more of R₉₀₁to R₉₀₇exist, two or more of R₉₀₁to R₉₀₇may be the same with or different from each other,

X₁is selected from O, S and N(R₃₆₄₁), and two X₁s may be the same with or different from each other;

R₃₆₄₁and one or more groups selected from R₃₆₀₁to R₃₆₀₄, R₃₆₁₁to R₃₆₁₄, R₃₆₂₄and R₃₆₂₈bond with each other to form a substituted or unsubstituted, saturated or unsaturated ring or do not form the ring; and

R₃₆₄₁that do not form the ring is a hydrogen atom,

a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

In one embodiment, the compound represented by the formula (31) is a compound represented by the formula (36-1) or (36-2), In one embodiment, the compound represented by the formula (31) is a compound represented by the formula (36-1).

In one embodiment, in the compound represented by the formulas (36-1) to (36-6), two R₃₆₃₁s are phenyl groups.

In one embodiment, in the compound represented by the formulas (36-1) to (36-6), X₁is N(R₃₆₄₁).

In one embodiment, in the compound represented by the formulas (36-1) to (36-6), R₃₆₄₁is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.

In one embodiment, the compound represented by the formula (31) is a compound represented by the following formula (36-1-1).

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wherein in the formula (36-1-1),

one or more pairs of two or more adjacent groups of R₃₀₀₁, R₃₀₀₂, R₃₀₀₅to R₃₀₀₇, R₃₀₁₀, R₃₀₁₁, R₃₀₁₄to R₃₀₁₆and R₃₀₃₁to R₃₀₃₄bond with each other to form a substituted or unsubstituted, saturated or unsaturated ring or do not torn toe ring;

X_as are independently selected from O, S and N(R₃₀₃₅);

R₃₀₃₅and R₃₀₃₁bond with each other to form a substituted or unsubstituted, saturated or unsaturated ring or do not form the ring; and

R₃₀₀₁, R₃₀₀₂, R₃₀₀₆to R₃₀₀₇, R₃₀₁₀, R₃₀₁₁, R₃₀₁₄to R₃₀₁₆and R₃₀₃₁to R₃₀₃₅that do not form toe ring and R₃₀₂₁and R₃₀₂₂are independently

a hydrogen atom,

a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

In one embodiment, a substituent in toe case of “substituted or unsubstituted” in toe formulas (31) to (35), (34-2), (35-2), (32-11), (34-11), (35-11), (32-12), (34-12), (35-12), (36-1) to (36-6) and (36-1-1) is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

As the compound represented by the formula (31), the fallowing compounds can be given for example. In the following example compounds, Me represents methyl group.

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(Compound Represented by Formula (41))

The compound represented by the formula (41) is explained below.

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wherein, in the formula (41),

a ring, b ring and c ring are independently

a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms, or

a substituted or unsubstituted heterocyclic ring having 5 to 50 ring atoms;

R₄₀₁and R₄₀₂that do not form the substituted or unsubstituted heterocyclic ring are independently

The a ring, b ring and c ring are rings (a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms or a substituted or unsubstituted heterocyclic ring having 5 to 50 ring atoms) fuse to the fused bicyclic structure composed of B atom and two N atoms in the center of the formula (41).

The “aromatic hydrocarbon ring” of the a ring, the b ring and the c ring has the same structure as the compound obtained by introducing a hydrogen atom into the “aryl group” described above. The “aromatic hydrocarbon ring” of the a ring contains three carbon atoms in the fused bicyclic structure in the center of the formula (41) as ring atoms. The “aromatic hydrocarbon ring” of the b ring and the c ring contain two carbon atoms in the fused bicyclic structure in the center of the formula (41) as ring atoms. As examples of “substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms”, compounds in which a hydrogen atom is introduced into the “aryl group” described in the group G1 and the like can be given.

The “heterocyclic ring” of the a ring, the b ring and the c ring has the same structure as the compound obtained by introducing a hydrogen atom into the “heterocyclic group” described above. The “heterocyclic ring” of the a ring contains three carbon atoms in the fused bicyclic structure in the center of the formula (41) as ring atoms. The “heterocyclic ring” of the b ring and the c ring contain two carbon atoms in the fused bicyclic structure in the center of the formula (41) as ring atoms. As examples of “substituted or unsubstituted heterocyclic ring having 5 to 50 ring atoms”, compounds in which a hydrogen atom is introduced into the “heterocyclic group” described in the group G2.

R₄₀₁and R₄₀₂may be independently bonded to the a ring, the b ring or the c ring to form a substituted or unsubstituted heterocyclic ring. This heterocyclic ring contains the nitrogen atom in the fused bicyclic structure in the center of the formula (41). This heterocyclic ring may contain a heteroatom other than the nitrogen atom. “R₄₀₁and R₄₀₂are bonded to the a ring, the bring or the c ring” means, specifically, an atom forming the a ring, the bring or the c ring is bonded to an atom forming R₄₀₁and R₄₀₂. For example, it is possible that R₄₀₁is bonded to the a ring to form a nitrogen-containing heterocyclic ring having a two-ring fused structure (or three or more rings fused structure) in which a ring containing R₄₀₁and the a ring are fused.

The same applies to the case where R₄₀₁is bonded to the b ring, R₄₀₂is bonded to the a ring, and R₄₀₂is bonded to the c ring.

In one embodiment, the a ring, the b ring and the c ring in the formula (41) are independently a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms.

In one embodiment the a ring, the b ring and the c ring in the formula (41) are independently a substituted or unsubstituted benzene ring or a substituted or unsubstituted naphthalene ring.

In one embodiment R₄₀₁and R₄₀₂in the formula (41) are independently a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms, and preferably a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.

In one embodiment, the compound represented by the formula (41) is a compound represented by the following formula (42).

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wherein in the formula (42),

R_401Ais bonded with one or more groups selected from R₄₁₁or R₄₂₁to form a substituted or unsubstituted heterocyclic ring, or does not form a substituted or unsubstituted heterocyclic ring; R_402Ais bonded with one or more group selected from R₄₁₃or R₄₁₄to form a substituted or unsubstituted heterocyclic ring, or does not form a substituted or unsubstituted heterocyclic ring;

R_401Aand R_402Athat do not form a substituted or unsubstituted heterocyclic ring are independently

One or more pairs of two or more adjacent groups of R₄₁₁to R₄₂₁are bonded with each other to form a substituted or unsubstituted, saturated or unsaturated ring, or do not form a substituted or unsubstituted, saturated or unsaturated ring;

R₄₁₁to R₄₂₁that do not form the substituted or unsubstituted heterocyclic ring or the substituted or unsubstituted, saturated or unsaturated ring are independently

—O—(R₉₀₄),
—S—(R₉₀₅),

R₉₀₁to R₉₀₇are as defined in the formula (1).

R_401Aand R_402Ain the formula (42) correspond to R₄₀₁and R₄₀₂in the formula (41).

R_401Aand R₄₁₁may be bonded with each other to form a nitrogen-containing heterocyclic ring having two-ring fused structure (or three or more rings fused structure) which is a fused ring of a ring containing R_401Aand R₄₁₁and the benzene ring of the a ring, for example. As examples of the nitrogen-containing heterocyclic ring, compounds correspond to nitrogen-containing heterocyclic group having two or more ring fused structure in the group G2 can be given. The same applies to the cases where R_401Aand R₄₁₂are bonded, R_402Aand R₄₁₃are bonded, and R_402Aand R₄₁₄are bonded.

One or more pairs of two or more adjacent groups of R₄₁₁to R₄₂₁are bonded with each other to form a substituted or unsubstituted, saturated or unsaturated ring. For example, R₄₁₁and R₄₁₂are bonded to form a benzene ring, an indole ring, a pyrrole ring, a benzofuran ring, a benzothiophene ring or the like which fuses to the six-membered ring to which R₄₁₁and R₄₁₂bond, and the formed fused ring is a naphthalene ring, a carbazole ring, an indole ring, a dibenzofuran ring or a dibenzothiophene ring.

In one embodiment, R₄₁₁to R₄₂₁that do not contribute to form a ring are independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

In one embodiment, R₄₁₁to R₄₂₁that do not contribute to form a ring are independently a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

In one embodiment, R₄₁₁to R₄₂₁that do not contribute to form a ring are independently a hydrogen atom or a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms.

In one embodiment, R₄₁₁to R₄₂₁that do not contribute to form a ring are independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, and at least one of R₄₁₁to R₄₂₁is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms.

In one embodiment, toe compound represented by the formula (42) is a compound represented by toe following formula (43).

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wherein in toe formula (43),

R₄₃₁is bonded with R₄₄₆to form a substituted or unsubstituted heterocyclic ring, or does not form a substituted or unsubstituted heterocyclic ring; R₄₃₃is bonded with R₄₄₇to form a substituted or unsubstituted heterocyclic ring, or does not form a substituted or unsubstituted heterocyclic ring; R₄₃₄is bonded with R₄₅₁to form a substituted or unsubstituted heterocyclic ring, or does not form a substituted or unsubstituted heterocyclic ring; R₄₄₁is bonded with R₄₄₂to form a substituted or unsubstituted heterocyclic ring, or does not form a substituted or unsubstituted heterocyclic ring;

One or more pairs of two or more adjacent groups of R₄₃₁to R₄₅₁are bonded with each other to form a substituted or unsubstituted, saturated or unsaturated ring, or do not form a substituted or unsubstituted, saturated or unsaturated ring;

R₄₃₁to R₄₅₁that do not form a substituted or unsubstituted heterocyclic ring are independently a hydrogen atom,

—O—(R₉₀₄),
—S—(R₉₀₅),

R₉₀₁to R₉₀₇are as defined in the formula (1).

R₄₃₁may bond to R₄₄₆to form a substituted or unsubstituted heterocyclic ring. For example, R₄₃₁may bonds with R₄₄₆form a nitrogen-containing heterocyclic ring with three or more fused rings of the benzene ring to which R₄₆bond, a nitrogen-containing ring and the benzene ring of the a ring. As examples of the nitrogen-containing heterocyclic ring, compounds correspond to nitrogen-containing heterocyclic group having three or more ring fused structure in the group G2 can be given. The same applies to the cases where R₄₃₃and R₄₄₇are bonded, R₄₃₄and R₄₅₁are bonded, and R₄₄₁and R₄₄₂are bonded.

In one embodiment, R₄₃₁to R451 that do not contribute to form a ring are independently, a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

In one embodiment, R₄₃₁to R451 that do not contribute to form a ring are independently, a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

In one embodiment, R₄₃₁to R451 that do not contribute to form a ring are independently a hydrogen atom or a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms.

In one embodiment, R₄₃₁to R451 that do not contribute to form a ring are independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, and at least one of R₄₃₁to R451 is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms.

In one embodiment, the compound represented by the formula (43) is a compound represented by the following formula (43A).

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wherein in the formula (43A),

R₄₆₁is

R₄₆₂to R465 are independently

In one embodiment, R₄₆₁to R465 are independently a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.

In one embodiment, R₄₆₁and R465 are independently a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms.

In one embodiment, the compound represented by the formula (43) is a compound represented by the following formula (43B).

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wherein in the formula (43B),

R₄₇₁and R₄₇₂are independently,

R₄₇₃to R₄₇₅are independently,

R₉₀₆and R₉₀₇are as defined in the formula (1).

In one embodiment, the compound represented by the formula (43) is the compound represented by the following formula (43B′).

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wherein in the formula (43B′), R₄₇₂to R₄₇₅are as defined in the formula (43B).

In one embodiment, at least one of R₄₇₁to R₄₇₅is

In one embodiment,

R₄₇₂is

a hydrogen atom,

a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

—N(R₉₀₆) (R₉₀₇), or

a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms; and

R₄₇₁and R₄₇₃to R₄₇₅are independently

a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

—N(R₉₀₆) (R₉₀₇), or

a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.

In one embodiment, the compound represented by the formula (43) is a compound represented by the formula (43C).

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wherein in the formula (43C),

R₄₈₁and R₄₈₂are independently

R₄₈₃to R₄₈₆are independently

In one embodiment, the compound represented by the formula (43) is the compound represented by the following formula (43C′).

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wherein in the formula (43C′), R₄₈₃to R₄₈₆are as defined in the formula (43C).

In one embodiment, R₄₈₁to R₄₈₆are independently a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.

In one embodiment, R₄₈₁to R₄₈₆are independently a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.

In one embodiment, the compound represented by the formula (43) is the compound represented by the following formula (43D).

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wherein in the formula (43D),

R₄₆₁₁is a hydrogen atom, an unsubstituted alkyl group including 1 to 6 carbon atoms, an unsubstituted cycloalkyl group including 3 to 10 ring carbon atoms, —Si(R₉₁₁)(R₉₁₂)(R₉₁₃), or —N(R₉₁₄)(R₉₁₅);

R₄₆₁₂to R₄₆₁₅are independently an unsubstituted alkyl group including 1 to 6 carbon atoms, an unsubstituted cycloalkyl group including 3 to 10 ring carbon atoms, or —Si(R₉₁₁)(R₉₁₂)(R₉₁₃);

R₉₁₁to R₉₁₃are independently an unsubstituted alkyl group including 1 to 6 carbon atoms or an unsubstituted aryl group including 6 to 18 ring carbon atoms;

R₉₁₄to R₉₁₅are independently an unsubstituted aryl group including 6 to 18 ring carbon atoms.

In one embodiment, in the formula (43D), Roan is a hydrogen atom, an unsubstituted alkyl group including 1 to 6 carbon atoms, or —N(R₉₁₄)(R₉₁₅).

In one embodiment, in the formula (43D), R₄₆₁₂to R₄₆₁₅are independently an unsubstituted alkyl group including 1 to 6 carbon atoms, or an unsubstituted cycloalkyl group including 3 to 10 ring carbon atoms.

In one embodiment, in the formula (43D), R₄₆₁₁is —N(R₉₁₄)(R₉₁₅), and R₄₆₁₂to R₄₆₁₅are independently an unsubstituted alkyl group including 1 to 6 carbon atoms.

In one embodiment in the formula (43D), R₄₆₁₁is an unsubstituted alkyl group including 1 to 6 carbon atoms, and R₄₆₁₂to R₄₆₁₅are independently an unsubstituted alkyl group including 1 to 6 carbon atoms.

In one embodiment in the formula (43D), R₄₆₁₁is a hydrogen atom, and R₄₆₁₂to R₄₆₁₅are independently an unsubstituted alkyl group including 1 to 6 carbon atoms, or an unsubstituted cycloalkyl group inducing 3 to 10 ring carbon atoms.

In one embodiment, in the formula (43D), at least one of the hydrogen atoms included in one or more selected from the group consisting of R₉₁₄and R₉₁₅is a deuterium atom.

The compound represented by the formula (41) can be synthesized by the following method: An intermediate is obtained by bonding the a ring, the b ring and the c ring with linking groups (a group containing N—R₁and a group containing N—R₂) (first reaction), and a final compound is obtained by bonding the a ring, the b ring and the c ring with a linking group (a group containing B) (second reaction). In the first reaction, an amination reaction such as Buchwald-Hartwig reaction can be applied. In the second reaction, tandem hetero-Friedel-Crafts reaction or the like can be applied.

Examples of the compound represented by the formula (41) are described below. They are just exemplified compounds and the compound represented by the formula (41) is not limited to the following examples. In the following example compounds, Me represents methyl group, and tBu represents tert-butyl group.

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(Compound Represented by Formula (51))

The compound represented by the formula (51) is explained below.

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wherein, in the formula (51),

r ring is a ring represented by the formula (52) or formula (53) which is fused to an adjacent ring at an arbitrary position;

q ring and s ring are independently a ring represented by the formula (54) which is fused to an adjacent ring at an arbitrary position;

p ring and t ring are independently a ring represented by the formula (55) or the formula (56) which is fused to an adjacent ring at an arbitrary position;

when a plurality of R₅₀₁s exist, adjacent Rans are bonded with each other to form a substituted or unsubstituted, saturated or unsaturated ring, or do not form a substituted or unsubstituted, saturated or unsaturated ring;

X₅₀₁is an oxygen atom, a sulfur atom, or NR₅₀₂;

R₅₀₁and R₅₀₂that do not form the substituted or unsubstituted saturated or unsaturated ring are a hydrogen atom,

—O—(R₉₀₄),
—S—(R₉₀₅),

R₉₀₁to R₉₀₇are as defined in the formula (1);

Ar₅₀₁and Ar₅₀₂are independently

L₅₀₁is

m1 is independently an integer of 0 to 2, m2 is independently an integer of 0 to 4, m3s are independently an integer of 0 to 3, and m4s are independently an integer of 0 to 5; when a plurality of R₃₀₁s exist, R₅₀₁s may be the same or different;

In the formula (51), each of the p ring to the t ring is fused to an adjacent ring by sharing two carbon atoms. The position and direction of fusing are not limited, and condensation is possible at any position and direction.

In one embodiment, in the formula (52) or (53) of the r ring, R₅₀₁is a hydrogen atom.

In one embodiment, the compound represented by the formula (51) is represented by any one of the following formulas (51-1) to (51-6).

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wherein in the formulas (51-1) to (51-6), R₅₀₁, X₅₀₁, Ar₅₀₁, Ar₅₀₂, L₅₀₁, m1 and m3 are as defined in the formula (51).

In one embodiment, the compound represented by the formula (51) is represented by any one of the following formulas (51-11) to (51-13).

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wherein in the formulas (51-11) to (51-13), R₅₀₁, X₅₀₁, Ar₅₀₁, Ar₅₀₂, L₅₀₁, m1, m3 and m4 are as defined in the formula (51).

In one embodiment, the compound represented by the formula (51) is represented by any one of the following formulas (51-21) to (51-25).

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wherein in the formulas (51-21) to (51-25), R₅₀₁, X₅₀₁, Ar₅₀₁, Ar₅₀₂, L₅₀₁, m1 and m4 are as defined in the formula (51).

In one embodiment, the compound represented by the formula (51) is represented by any one of the following formulas (51-31) to (51-33).

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wherein in the formulas (51-31) to (51-33), R₅₀₁, X₅₀₁, Ar₅₀₁, Ar₅₀₂, L₅₀₁, m2 to m4 are as defined in the formula (51).

In one embodiment, Ar₅₀₁and Ar₅₀₂are independently a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.

In one embodiment, one of Ar₅₀₁and Ar₅₀₂is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms and toe other is a substituted or unsubstituted monovalent heterocyclic ring having 5 to 50 ring atoms.

As examples of toe compound represented by the formula (51), toe following compounds can be given, for example. In the following example compounds, Me represents methyl group.

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(Compound Represented by Formula (61))

The compound represented by the formula (61) is explained below.

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wherein, in the formula (61),

at least one pair of R₆₀₁and R₆₀₂, R₆₀₂and R₆₀₃, and R₆₀₃and R₆₀₄are bonded with each other to form a divalent group represented by the formula (62);

at least one pair of R₆₀₅and R₆₀₆, R₆₀₆and R₆₀₇, and R₆₀₇and R₆₀₈are bonded with each other to form a divalent group represented by formula (63);

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at least one of R₈₀₅to R₈₀₈that do not form the divalent group represented by the formula (63), and R₆₂₁to R₆₂₄is a monovalent group represented by the following formula (64);

X₈₀₁is an oxygen atom, a sulfur atom, or NR₈₀₉;

R₆₀₁to R₆₀₈that do not form the divalent group represented by the formulas (62) and (63) and that is not the monovalent group represented by the formula (64), R₆₁₁to R₆₁₄and R₆₂₁to R₆₂₄that are not the monovalent group represented by the formula (64), and R₆₀₉are independently

—O—(R₉₀₄),
—S—(R₉₀₅),

R₉₀₁to R₉₀₇are as defined in the formula (1);

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wherein, in the formula (64), Ar₆₀₁and Ar₆₀₂are independently

a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms;

L₆₀₁to L₆₀₃are independently

In the formula (61), positions at which the divalent group represented by the formula (62) and the divalent group represented by the formula (63) are formed are not limited, and said groups can be formed at possible positions in R₆₀₁to R₆₀₈.

In one embodiment, the compound represented by the formula (61) is represented by any one of the following formulas (61-1) to (61-6).

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wherein in the formulas (61-1) to (61-6), Xan is as defined in the formula (61);

at least two of Rem to R₆₂₄are monovalent groups represented by the formula (64);

R₆₀₁to R₆₂₄that are not monovalent groups represented by the formula (64) are independently

a hydrogen atom,

a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

a substituted a unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

—Si(R₉₀₁)(R₉₀₂)(R₉₀₃),

—O—(R₉₀₄),
—S—(R₉₀₅),

R₉₀₁to R₉₀₇are as defined in the formula (1).

In one embodiment, the compound represented by the formula (61) is represented by any one of the following formulas (61-7) to (61-18).

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wherein in the formulas (61-7) to (61-18), X₆₀₁is as defined in the formula (61); * is a single bond bonding to the monovalent group represented by the formula (64); and R₆₀₁to R₆₂₄are the sane as Rem to R₆₂₄that are not monovalent groups represented by the formula (64).

R₆₀₁to R₆₀₈which do not form the divalent group represented by the formula (62) and (63) and are not monovalent groups represented by the formula (64), and R₆₁₁to R₆₁₄and R₆₂₁to R₆₂₄which are not monovalent groups represented by the formula (64) are preferably independently

The monovalent group represented by the formula (64) is preferably represented by the following formulas (65) or (66).

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wherein in the formula (65), R₆₃₁to R₆₄₀are independently

—O—(R₉₀₄),
—S—(R₉₀₅),

R₉₀₁to R₉₀₇are as defined in the formula (1).

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wherein in the formula (66), Ar₆₀₁, L₆₀₁and L₆₀₃are as defined in the formula (64); and HAr₆₀₁is a structure represented by the following formula (67);

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wherein in the formula (67) X₆₀₂is an oxygen atom or a sulfur atom;

any one of R₆₄₁to R₆₄₈is a single bond bonding to L₈₀₃;

R₆₄₁to R₆₄₈which are not single bonds are independently

—O—(R₉₀₄),
—S—(R₉₀₅),

R₉₀₁to R₉₀₇are as defined in the formula (1).)

As specific example of toe compound represented by the formula (61), in addition to toe compounds described in WO2014/104144, the following compounds can be given, for example. In the following example compounds. Me represents methyl group.

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(Compound Represented by Formula (71))

The compound represented by the formula (71) is explained below.

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wherein, in the formula (71),

A₇₀₁ring and A₇₀₂ring are independently

a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms, or

a substituted or unsubstituted heterocyclic ring having 5 to 50 ring atoms;

One or more rings selected from the group consisting of A₇₀₁ring and A₇₀₂ring are bonded to the bond * of the structure represented by the following formula (72);

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wherein, in the formula (72),

A₇₀₃rings are independently

a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms, a

a substituted or unsubstituted heterocyclic ring having 5 to 50 ring atoms;

X₇₀₁is NR₇₀₃, C(R₇₀₄)(R₇₀₅), Si(R₇₀₆) (R₇₀₇), Ge(R₇₀₈)(R₇₀₉), O, S or Se;

R₇₀₁and R₇₀₂are bonded with each other to form a substituted or unsubstituted, saturated or unsaturated ring or do not form a substituted or unsubstituted saturated or unsaturated ring;

R₇₀₁and R₇₀₂that do not form the substituted or unsubstituted, saturated or unsaturated ring, and R₇₀₃to R₇₀₉are independently

—O—(R₉₀₄),
—S—(R₉₀₅),

R₉₀₁to R₉₀₇are as defined in the formula (1);

One or more selected from the group consisting of A701 ring and A702 ring is bonded to * in the structure represented by the formula (72). That is, in one embodiment, the ring carbon atom of the aromatic hydrocarbon ring or the ring atom of the heterocyclic ring of A701 ring is bonded to * in the structure represented by the formula (72). In one embodiment, the ring carbon atom of the aromatic hydrocarbon ring or the ring atom of the heterocyclic ring of A702 ring is bonded to * in the structure represented by the formula (72).

In one embodiment the group represented by the formula (73) is bonded to one or both of A701 ring and A702 ring.

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wherein in the formula (73), Ar₇₀₁and Ar₇₀₂are independently

a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms; and

L₇₀₁to L₇₀₃are independently

In one embodiment, in addition to A₇₀₁ring, the ring carbon atom of the aromatic hydrocarbon ring or the ring atom of the heterocyclic ring of Ar₇₀₂ring is bonded to * in the structure represented by the formula (72). In this case, the structures represented by formula (72) may be the same or different.

In one embodiment, R₇₀₁and R₇₀₂are independently a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.

In one embodiment, R₇₀₁and R₇₀₂are bonded with each other to form a fluorene structure.

In one embodiment, Ar₇₀₁ring and Ar₇₀₂ring are substituted or unsubstituted aromatic hydrocarbon rings having 6 to 50 ring carbon atoms, and they are substituted or unsubstituted benzene rings, for example.

In one embodiment, Ar₇₀₃ring is a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms, and it is a substituted or unsubstituted benzene ring, for example.

In one embodiment, X₇₀₁is O or S.

As specific example of the compound represented by the formula (71), the following compounds can be given, for example. In the following example compounds, Me represents methyl group.

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(Compound Represented by Formula (81))

The compound represented by the formula (81) is explained below.

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wherein, in the formula (81),

A₈₀₁ring is a ring represented by the formula (82) which is fused to an adjacent ring at an arbitrary position;

A₈₀₂ring is a ring represented by the formula (83) which is fused to an adjacent ring at an arbitrary position;

two bonds * bond to A₈₀₃ring at an arbitrary position;

X₈₀₁and X₈₀₂are independently C(R₈₀₃)(R₈₀₄), Si(R₈₀₅)(R₈₀₆), an oxygen atom, or a sulfur atom;

A₈₀₃ring is a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic ring having 5 to 50 ring atoms;

Ar₈₀₁is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms;

R₈₀₁to R₈₀₆are independently

—O—(R₉₀₄),
—S—(R₉₀₅),

R₉₀₁to R₉₀₇are as defined in the formula (1);

m801 and m802 are independently an integer of 0 to 2; when these are 2, Rams or ROBS may be the same or different;

a801 is an integer of 0 to 2; when a801 is 0 or 1, the structure in the parentheses indicated by “3-a801” may be the same or different from each other; when a801 is 2, Ar₈₀₁s may be the same or different from each other.

In one embodiment, Ar₈₀₁is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.

In one embodiment, Ar₈₀₃ring is a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms, and it is a substituted or unsubstituted benzene ring, a substituted or unsubstituted naphthalene ring, or a substituted or unsubstituted anthracene ring, for example.

In one embodiment, R₈₀₃and R₈₀₄are independently a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms.

In one embodiment, a801 is 1.

As specific example of the compound represented by the formula (81), the following compounds can be given, for example.

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Specific examples of the above groups are as described in [Definition] of this specification.

In the organic EL device according to one aspect of the invention, known materials and device configurations may be applied as long as the device includes a cathode, an anode, and an emitting layer disposed between the cathode and the anode, and the emitting layer includes a compound represented by the following formula (1) and one or more compounds selected from the group consisting of compounds represented by each of formulas (11), (21), (31), (41), (51), (61), (71) and (81) as described above, and as long as the effect of the invention is not impaired.

In one embodiment, the emitting layer contains one or more selected from the group consisting of a compound represented by the formula (1A) and a compound represented by the formula (1B), and a compound represented by the formula (43D).

In one embodiment, the compound represented by the formula (1A) or (1B) is one or more selected from the group consisting of the compound represented by the formula BH-1, BH-2, BH-3, and BH-5 to BH-17, and the compound represented by the formula (43D) is one or more selected from the group consisting of the compound represented by the formula BD-9, BD-10, BD-1 land BD-12.

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A content of the compound represented by the formula (1) in the emitting layer is preferably 80 mass % or more and 99 mass % or less based on the total mass of the emitting layer.

A content of the one or more compounds selected from the group consisting of compounds represented by each of formulas (11), (21), (31), (41), (51), (61), (71) and (81) is preferably 1 mass % or more and 20 mass % or less based on a total mass of the emitting layer.

One embodiment of the organic EL device preferably has the hole-transporting layer between the anode and the emitting layer.

One embodiment of the organic EL device preferably has the electron-transporting layer between the cathode and the emitting layer.

Specific examples of a typified device configuration of the organic EL device of the invention include structures such as

(1) an anode/an emitting layer/a cathode,

(2) an anode/a hole-injecting layer/an emitting layer/a cathode,

(3) an anode/an emitting layer/an electron-injecting-transporting layer/a cathode,

(4) an anode/a hole-injecting layer/an emitting layer/an electron-injecting-transporting layer/a cathode,

(5) an anode/an organic semiconductor layer/an emitting layer/a cathode,

(6) an anode/an organic semiconductor layer/an electron barrier layer/an emitting layer/a cathode,

(7) an anode/an organic semiconductor layer/an emitting layer/an adhesion improving layer/a cathode,

(8) an anode/a hole-injecting-transporting layer/an emitting layer/an electron-injecting-transporting layer /a cathode,

(9) an anode/an insulating layer/an emitting layer/an insulating layer/a cathode,

(10) an anode/an inorganic semiconductor layer/an insulating layer/an emitting layer/an insulating layer /a cathode,

(11) an anode/an organic semiconductor layer/an insulating layer/an emitting layer/an insulating layer /a cathode,

(12) an anode/an insulating layer/a hole-injecting-transporting layer/an emitting layer/an insulating layer /a cathode, and

(13) an anode/an insulating layer/a hole-injecting-transporting layer/an emitting layer/an electron-injecting-transporting layer/a cathode.

Among the above-described structures, a configuration of (8) is preferably used, but the configuration is not limited thereto.

In this specification, the term “hole-injecting-transporting layer” herein means “at least one of the hole-injecting layer and the hole-transporting layer”, and the term “electron-injecting-transporting layer” herein means “at least one of the electron-injecting layer and the electron-transporting layer”.

Hereinbelow, an explanation will be made on elements and materials other than the above-mentioned compound constituting each layer that can be used in the organic EL device according to one aspect of the invention.

(Substrate)

The substrate is used as a supporting body of the emitting device. As the substrate, glass, quarts, plastic or the like can be used. Further, a flexible substrate may be used. The flexible substrate means a substrate that can be bent. For example, a plastic substrate made of polycarbonate or vinyl polychloride or the like can be given.

(Anode)

In an anode formed on a substrate, it is preferable to use a metal having a large work function (specifically, 4.0 eV or more), an alloy, an electric conductive compound, a mixture of these or the like. Specifically, indium oxide-tin oxide (ITO: Indium Tin Oxide), indium oxide-tin oxide containing silicon or silicon oxide, indium oxide-zinc oxide, tungsten oxide, indium oxide containing zinc oxide, graphene, or the like can be given. In addition, gold (Au), platinum (Pt) or a nitride of a metal material (e.g. titanium nitride) or the like can be given.

(Hole-Injecting Layer)

The hole-injecting layer is a layer containing a substance having a high hole-injecting property. As a substance having a high hole-injecting property, a substance selected from molybdenum oxide, titanium oxide, vanadium oxide, rhenium oxide, ruthenium oxide, chromium oxide, zirconium oxide, hafnium oxide, tantalum oxide, silver oxide, tungsten oxide, manganese oxide, an aromatic amine compound, a polymer compound (oligomer, dendrimer, polymer, etc.) or the like can also be used

(Hole-Transporting Layer)

The hole-transporting layer is a layer containing a substance having a high hole-transporting property. For the hole-transporting layer, aromatic amine compounds, carbazole derivatives, anthracene derivatives and the like can be used. Polymer compounds such as poly (N-vinylcarbazole) (abbreviation: PVK) and poly(4-vinyltriphenylamine) (abbreviation: PVTPA) can also be used. However, any substance other than these may be used as long as it is a substance having a higher transporting property for holes than electrons. Note that the layer containing a substance having a high hole-transporting property is not limited to a single layer, but may be a stacked body of two or more layers made of the above substances.

(Guest Material of the Emitting Layer)

The emitting layer is a layer that comprises a substance having high luminous property, and various materials can be used. For example, as the substance having high luminous property, a fluorescent compound that emits fluorescent light or a phosphorescent compound that emits phosphorescent light can be used. The fluorescent compound is a compound capable of emitting light from a singlet excited state and the phosphorescent compound is a compound capable of emitting light from a triplet excited state.

As a blue fluorescent material that can be used for the emitting layer, pyrene derivatives, styrylamine derivatives, chrysene derivatives, fluoranthene derivatives, fluorene derivatives, diamine derivatives, triarylamine derivatives and the like can be used. An aromatic amine derivative or the like can be used as a green fluorescent light-emitting material that can be used in the emitting layer. As a red fluorescent material which can be used in emitting layer, a tetracene derivative, a diamine derivative or the like can be used.

Metal complexes such as iridium complexes, osmium complexes, platinum complexes and the like are used as the blue phosphorescent material that can be used in the emitting layer. An iridium complex or the like is used as a green phosphorescent material that can be used in the emitting layer. Metal complexes such as iridium complexes, platinum complexes, terbium complexes, europium complexes and the like are used as red phosphorescent materials that can be used in the emitting layer.

(Host Material of Emitting Layer)

The emitting layer may have a structure in which the substance having high luminescent property (guest material) described above is dispersed in another substance (host material). Various materials other than the compound represented by the formula (1) (for example, the compound represented by the formula (1A) or (1B)) can be used as substances for dispersing substances with high luminescent properties, and it is preferable to use a material having a high lowest unoccupied molecular orbital level (LUMO level) and a low highest occupied molecular orbital level (HOMO level), rather than a material having a high luminous property.

As a substance (host material) for dispersing a substance having a high luminous property, 1) a metal complex such as an aluminum complex, a beryllium complex or a zinc complex, 2) a heterocyclic compound such as an oxadiazole derivative, a benzimidazole derivative, a phenanthroline derivative or the like, 3) a fused aromatic compound such as a carbazole derivative, an anthracene derivative, a phenanthrene derivative, a pyrene derivative or a chrysene derivative, and 4) an aromatic amine compound such as a triarylamine derivative or a fused polycyclic aromatic amine derivative are used.

(Electron-Transporting Layer)

The electron-transporting layer is a layer containing a substance having a high election-transporting property. For the electron-transporting layer, 1) a metal complex such as an aluminum complex, a beryllium complex, or a zinc complex 2) a heteroaromatic compound such as an imidazole derivative, a benzimidazole derivative, an azine derivative, a carbazole derivative or a phenanthroline derivative, and 3) a polymer compound can be used.

(Electron-Injecting Layer)

The electron-injection layer is a layer containing a substance having a high electron-injection property. For the electron-injection layer, alkali metals, alkaline earth metals or a compound thereof such as lithium (Li), ytterbium (Yb), lithium fluoride (LiF), cesium fluoride (CsF), calcium fluoride (CaF₂), metal complex compound such as 8-quinolinolato lithium (Liq), lithium oxide (LiOx) or the like can be used.

(Cathode)

It is preferable to use a metal, an alloy, an electrically conductive compound, a mixture thereof, or the like having a small work function (specifically, 3.8 eV or less) for the cathode. Specific examples of such cathode material include elements belonging to Group 1 or Group 2 of the periodic table of elements, that is, alkali metals such as lithium (Li) and cesium (Cs), alkaline earth metals such as magnesium (Mg), calcium (Ca), and strontium (Sr),

an alloy containing these metals (for example, MgAg and AlLi), a rare earth metal such as europium (Eu) and ytterbium (Yb), and an alloy containing a rare earth metal.

In the organic EL device according to one aspect of the invention, the method for forming each layer is not particularly restricted. A conventionally known forming method such as a vacuum deposition method, a spin coating method or tee like can be used. Each layer such as the emitting layer or the like can be formed by a vacuum deposition method, a molecular beam evaporation method (MBE method), or a known coating method such as a dipping method, a solution spin coating method, a casting method, a bar coating method, or the like, that uses a solution of a material forming each layer dissolved in a solvent

In the organic EL device according to one aspect of the invention, the thickness of each layer is not particularly restricted. In general, in order to suppress occurrence of defects such as pinholes and to suppress the applied voltage and to improve luminous efficiency, tee thickness is normally preferably in a range of several nm to 1 μm.

[Electronic Device]

The electronic device according to one aspect of tee invention is characterized in that it is provided with the organic EL device according to one aspect of tee invention.

Specific examples of tee electronic device includes a display element such as an organic EL panel module; a display such as a TV, a mobile phone or a PC; and emitting devices such as lightings and lights for automobiles or the like.

EXAMPLES

The invention will specifically be explained with the examples and tee comparative examples below, and shall not be limited to tee contents of the examples in any way.

Synthesis Example 1 [Synthesis of Compound BH-1]
Synthesis of Intermediate 1

To 13.3 g (50.0 mmol) of 9-bromoanthracene-d9, 6.4 g (52.5 mmol) of phenylboronic add and 1.2 g (1.00 mmol) of Pd[PPh₃]₄, 75 ml of toluene, 75 ml of dimethoxyethane and 75 ml (150.0 mmol) of 2M Na₂CO₃aqueous solution were added under an atmosphere of argon, followed by being heated to reflux while stirring for 10 hours.

After completion of the reaction, having been cooled to room temperature, the sample was transferred to a separating funnel and extracted with dichloromethane. The resulting organic phase was dried with MgSO₄, followed by being filtered and concentrated. The concentrated residue was purified with silica gel column chromatography to obtain 10.9 g of white solid. By conducting FD-MS analysis, the resulting compound was identified as Intermediate 1 as follows (yield: 83%).

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Synthesis of Intermediate 2

5.3 g (20.0 mmol) of Intermediate 1 was solubilized in 120 ml of dichloromethane, and the resulting solution was dropped into the solution of 3.2 g (20.0 mmol) of bromine in 12 ml of dichloromethane at room temperature, followed by being stirred for one hour.

After completion of the reaction, the sample was transferred to a separating funnel and washed with 2M Na₂S₂O₃aqueous solution. The organic phase was further washed with 10% Na₂CO₃, and thereafter with water, and the separated organic phase was dried with MgSO₄, followed by being filtered and concentrated.

The concentrated residue was dispersed in methanol (100 mL), and the precipitated crystal was dried to obtain 6.5 g of white solid. By conducting FD-MS analysis, the resulting compound was identified as Intermediate 2 as follows (yield: 95%).

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Synthesis of Compound BH-1

To 1.7 g (5.0 mmol) of Intermediate 2, 1.1 g (5.3 mmol) of dibenzofuran-2-boronic add and 0.1 g (0.1 mmol) of Pd[PPh₃]₄, 7.5 ml of toluene, 7.5 ml of dimethoxyethane and 7.5 ml (15.0 mmol) of 2M Na₂CO₃aqueous solution were added under an atmosphere of argon, followed by being heated to reflux while stirring for 10 hours.

After completion of the reaction, having been cooled to room temperature, the sample was transferred to a separating funnel and extracted with dichloromethane. The resulting organic phase was dried with MgSO₄, followed by being filtered and concentrated. The concentrated residue was purified with silica gel column chromatography to obtain 1.6 g of white solid. By conducting FD-MS analysis, the resulting compound was identified as Compound BH-1 as follows (yield: 75%).

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Synthesis Example 2 [Synthesis of Compound BH-2]
Synthesis of Intermediate 3

To 13.3 g (50.0 mmol) of 9-bromoanthracene-d9, 9.0 g (52.5 mmol) of 1-naphthalene boronic add and 1.2 g (1.00 mmol) of Pd[PPh₃]₄, 75 ml of toluene, 75 ml of dimethoxyethane and 75 ml (150.0 mmol) of 2M Na₂CO₃aqueous solution were added under an atmosphere of argon, followed by being heated to reflux while stirring for 10 hours.

After completion of the reaction, having been cooled to room temperature, the sample was transferred to a separating funnel and extracted with dichloromethane. The resulting organic phase was dried with MgSO₄, followed by being filtered and concentrated. The concentrated residue was purified with silica gel column chromatography to obtain 13.3 g of white solid. By conducting FD-MS analysis, the resulting compound was identified as Intermediate 3 as follows (yield: 85%).

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Synthesis of Intermediate 4

6.3 g (20.0 mmol) of Intermediate 3 was solubilized in 120 ml of dichloromethane, and the resulting solution was dropped into the solution of 3.2 g (20.0 mmol) of bromine in 12 ml of dichloromethane at room temperature, followed by being stirred for one hour.

After completion of the reaction, the sample was transferred to a separating funnel and washed with 2M Na₂S₂O₃aqueous solution. The organic phase was further washed with 10% Na₂CO₃, and thereafter with water three times. The organic phase was dried with MgSO₄, followed by being filtered and concentrated.

The concentrated residue was dispersed in methanol (100 mL), and the precipitated crystal was dried to obtain 7.5 g of white solid. By conducting FD-MS analysis, the resulting compound was identified as Intermediate 4 as follows (yield: 96%).

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Synthesis of Compound BH-2

To 2.0 g (5.0 mmol) of Intermediate 4, 1.1 g (5.3 mmol) of dibenzofuran-2-boronic add and 0.1 g (0.1 mmol) of Pd[PPh₃]₄, 7.5 ml of toluene, 7.5 ml of dimethoxyethane and 7.5 ml (15.0 mmol) of 2M Na₂CO₃aqueous solution were added under an atmosphere of argon, followed by being heated to reflux while stirring for 10 hours.

After completion of the reaction, having been cooled to room temperature, the sample was transferred to a separating funnel and extracted with dichloromethane. The resulting organic phase was dried with MgSO₄, followed by being filtered and concentrated. The concentrated residue was purified with silica gel column chromatography to obtain 1.7 g of white solid. By conducting FD-MS analysis, the resulting compound was identified as Compound BH-2 as follows (yield: 70%).

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Synthesis Example 3 [Synthesis of Compound BH-3]

Except that 1.1 g (5.3 mmol) of dibenzofuran-1-boronic add was used instead of dibenzofuran-2-boronic acid, the reaction was carried out in the same way as in the synthesis example 1, thereby obtaining 1.3 g of white crystal. By conducting FD-MS analysis, the resulting compound was identified as Compound BH-3 as follows (yield: 62%).

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Synthesis Example 4 [Synthesis of Compound BH-4]

Except feat 1.1 g (5.3 mmd) of dibenzofuran-4-boronic add was used instead of dibenzofuran-2-boronic acid, the reaction was carried out in the same way as in the synthesis example 1, thereby obtaining 1.2 g of white crystal. By conducting FD-MS analysis, the resulting compound was identified as Compound BH-4 as follows (yield: 55%).

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Synthesis Example 5 [Synthesis of Compound BH-5]

Except that 1.5 g (5.3 mmol) of 4-(2-dibenzofuranyl)phenyl boronic add was used instead of dibenzofuran-2-boronic add, the reaction was carried out in the same way as in the synthesis example 1, thereby obtaining 1.8 g of white crystal. By conducting FD-MS analysis, the resulting compound was identified as Compound BH-5 as follows (yield: 71%).

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Synthesis Example 6 [Synthesis of Compound BH-6]

Except that 1.5 g (5.3 mmd) of 4-(2-dibenzofuranyl)phenyl boronic add was used instead of dibenzofuran-2-boronic add, the reaction was carried out in the same way as in the synthesis example 2, thereby obtaining 2.0 g of white crystal By conducting FD-MS analysis, the resulting compound was identified as Compound BH-6 as follows (yield: 73%).

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Synthesis Example 7 [Synthesis of Compound BH-7]
Synthesis of Intermediate 5

To 13.3 g (50.0 mmol) of 9-bromoanthracene-d9, 10.4 g (52.5 mmol) of 4-biphenylboronic add and 1.2 g (1.00 mmol) of Pd[PPh₃]₄, 75 ml of toluene, 75 ml of dimethoxyethane and 75 ml (150.0 mmol) of 2M Na₂CO₃aqueous solution were added under an atmosphere of argon, followed by being heated to reflux while stirring for 10 hours.

After completion of the reaction, having been cooled to room temperature, the sample was transferred to a separating funnel and extracted with dichloromethane. The resulting organic phase was dried with MgSO₄, followed by being filtered and concentrated. The concentrated residue was purified with silica gel column chromatography to obtain 14.1 g of white solid. By conducting FD-MS analysis, the resulting compound was identified as Intermediate 5 as follows (yield: 83%).

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Synthesis of Intermediate 6

6.8 g (20.0 mmol) of Intermediate 5 was solubilized in 120 ml of dichloromethane, and the resulting solution was dropped into the solution of 3.2 g (20.0 mmol) of bromine in 12 ml of dichloromethane at room temperature, followed by being stirred for one hour.

After completion of the reaction, the sample was transferred to a separating funnel and washed with 2M Na₂S₂O₃aqueous solution. The organic phase was further washed with 10% Na₂CO₃, and thereafter with water three times. The organic phase was dried with MgSO₄, followed by being filtered and concentrated.

The concentrated residue was dispersed in methanol (100 mL), and the precipitated crystal was dried to obtain 8.0 g of white solid. By conducting FD-MS analysis, the resulting compound was identified as Intermediate 6 as follows (yield: 96%).

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Synthesis of Compound BH-7

To 2.1 g (5.0 mmol) of Intermediate 6, 1.1 g (5.3 mmol) of dibenzofuran-2-boronic acid and 0.1 g (0.1 mmol) of Pd[PPh₃]₄, 7.5 ml of toluene, 7.5 ml of dimethoxyethane and 7.5 ml (15.0 mmol) of 2M Na₂CO₃aqueous solution were added under an atmosphere of argon, followed by being heated to reflux while stirring for 10 hours.

After completion of the reaction, having been cooled to room temperature, the sample was transferred to a separating funnel and extracted with dichloromethane. The resulting organic phase was dried with MgSO₄, followed by being filtered and concentrated. The concentrated residue was purified with silica gel column chromatography to obtain 1.6 g of white solid. By conducting FD-MS analysis, the resulting compound was identified as Compound BH-7 as follows (yield: 64%).

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Synthesis Example 8 [Synthesis of Compound BH-8]
Synthesis of Intermediate 7

To 13.3 g (50.0 mmol) of 9-bromoanthracene-d9, 10.4 g (52.5 mmol) of 3-biphenylboronic add and 1.2 g (1.00 mmol) of Pd[PPh₃]₄, 75 ml of toluene, 75 ml of dimethoxyethane and 75 ml (150.0 mmol) of 2M Na₂CO₃aqueous solution were added under an atmosphere of argon, followed by being heated to reflux while storing for 10 hours.

After completion of the reaction, having been cooled to room temperature, the sample was transferred to a separating funnel and extracted with dichloromethane. The resulting organic phase was dried with MgSO₄, followed by being filtered and concentrated. The concentrated residue was purified with silica gel column chromatography to obtain 13.6 g of white solid. By conducting FD-MS analysis, the resulting compound was identified as Intermediate 7 as follows (yield: 80%).

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Synthesis of Intermediate 8

6.8 g (20.0 mmol) of Intermediate 7 was solubilized in 120 ml of dichloromethane, and the resulting solution was dropped into the solution of 3.2 g (20.0 mmol) of bromine in 12 ml of dichloromethane at room temperature, followed by being stirred for one hour.

After completion of the reaction, the sample was transferred to a separating funnel and washed with 2M Na₂S₂O₃aqueous solution. The organic phase was further washed with 10% Na₂CO₃, and thereafter with water three times. The organic phase was dried with MgSO₄, followed by being filtered and concentrated.

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Synthesis of Compound BH-8

To 2.1 g (5.0 mmol) of Intermediate 8, 1.1 g (5.3 mmol) of dibenzofuran-2-boronic acid and 0.1 g (0.1 mmol) of Pd[PPh₃]₄, 7.5 ml of toluene, 7.5 ml of dimethoxyethane and 7.5 ml (15.0 mmol) of 2M Na₂CO₃aqueous solution were added under an atmosphere of argon, followed by being heated to reflux while stirring for 10 hours.

After completion of the reaction, having been cooled to room temperature, the sample was transferred to a separating funnel and extracted with dichloromethane. The resulting organic phase was dried with MgSO₄, followed by being filtered and concentrated. The concentrated residue was purified with silica gel column chromatography to obtain 1.5 g of white solid. By conducting FD-MS analysis, the resulting compound was identified as Compound BH-8 as follows (yield: 59%).

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Synthesis Example 9 [Synthesis of Compound BH-9]
Synthesis of Intermediate 9

To 13.3 g (50.0 mmol) of 9-bromoanthracene-d9, 10.4 g (52.5 mmol) of 2-biphenylboronic acid and 12 g (1.00 mmol) of Pd[PPh₃]₄, 75 ml of toluene, 75 ml of dimethoxyethane and 75 ml (150.0 mmol) of 2M Na₂CO₃aqueous solution were added under an atmosphere of argon, followed by being heated to reflux while stirring for 10 hours.

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Synthesis of Intermediate 10

6.8 g (20.0 mmol) of Intermediate 9 was solubilized in 120 ml of dichloromethane, and the resulting solution was dropped into the solution of 3.2 g (20.0 mmol) of bromine in 12 ml of dichloromethane at room temperature, followed by being stirred for one hour.

After completion of the reaction, the sample was transferred to a separating funnel and washed with 2M Na₂S₂O₃aqueous solution. The organic phase was further washed with 10% Na₂CO₃, and thereafter with water three times. The organic phase was dried with MgSO₄, followed by being filtered and concentrated.

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Synthesis of Compound BH-9

To 2.1 g (5.0 mmol) of Intermediate 10, 1.1 g (5.3 mmol) of dibenzofuran-2-boronic add and 0.1 g (0.1 mmol) of Pd[PPh₃]₄, 7.5 ml of toluene, 7.5 ml of dimethoxyethane and 7.5 ml (15.0 mmol) of 2M Na₂CO₃aqueous solution were added under an atmosphere of argon, followed by being heated to reflux while stirring for 10 hours.

After completion of the reaction, having been cooled to room temperature, the sample was transferred to a separating fennel and extracted with dichloromethane. The resulting organic phase was dried with MgSO₄, followed by being filtered and concentrated. The concentrated residue was purified with silica gel column chromatography to obtain 1.6 g of white solid. By conducting FD-MS analysis, the resulting compound was identified as Compound BH-9 as follows (yield: 63%).

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Synthesis Example 10 [Synthesis of Compound BH-10]
Synthesis of Intermediate 11

To 13.3 g (50.0 mmol) of 9-bromoanthracene-d9, 13.0 g (52.5 mmol) of 4-(1-naphthyl)phenylboronic add and 12 g (1.00 mmol) of Pd[PPh₃]₄, 75 ml of toluene, 75 ml of dimethoxyethane and 75 ml (150.0 mmol) of 2M Na₂CO₃aqueous solution were added under an atmosphere of argon, followed by being heated to reflux while stirring for 10 hours.

After completion of toe reaction, having been cooled to room temperature, toe sample was transferred to a separating funnel and extracted with dichloromethane. The resulting organic phase was dried with MgSO₄, followed by being filtered and concentrated. The concentrated residue was purified with silica gel column chromatography to obtain 15.6 g of white solid. By conducting FD-MS analysis, the resulting compound was identified as Intermediate 11 as follows (yield: 80%).

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Synthesis of Intermediate 12

7.8 g (20.0 mmol) of Intermediate 11 was solubilized in 120 ml of dichloromethane, and the resulting solution was dropped into the solution of 3.2 g (20.0 mmol) of bromine in 12 ml of dichloromethane at room temperature, followed by being stirred for one hour.

After completion of toe reaction, the sample was transferred to a separating funnel and washed with 2M Na₂S₂O₃aqueous solution. The organic phase was further washed with 10% Na₂CO₃, and thereafter with water three times. The organic phase was dried with MgSO₄, followed by being filtered and concentrated.

The concentrated residue was dispersed in methanol (100 mL), and the precipitated crystal was dried to obtain 8.6 g of white solid. By conducting FD-MS analysis, the resulting compound was identified as Intermediate 12 as follows (yield: 92%).

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Synthesis of Compound BH-10

To 2.3 g (5.0 mmol) of Intermediate 12, 1.1 g (5.3 mmol) of dibenzofuran-2-boronic add and 0.1 g (0.1 mmol) of Pd[PPh₃]₄, 7.5 ml of toluene, 7.5 ml of dimethoxyethane and 7.5 ml (15.0 mmol) of 2M Na₂CO₃aqueous solution were added under an atmosphere of argon, followed by being heated to reflux while stirring for 10 hours.

After completion of the reaction, having been cooled to room temperature, the sample was transferred to a separating funnel and extracted with dichloromethane. The resulting organic phase was dried with MgSO₄, followed by being filtered and concentrated. The concentrated residue was purified with silica gel column chromatography to obtain 1.9 g of white solid. By conducting FD-MS analysis, the resulting compound was identified as Compound BH-10 as follows (yield: 68%).

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Synthesis Example 11 [Synthesis of Compound BH-11]

Except that 1.8 g (5.3 mmol) of 4-(2-dibenzofuranyl)-1-naphtalenyl boronic add was used instead of dibenzofuran-2-boronic acid, the reaction was carried out in the same way as in the synthesis example 1, thereby obtaining 1.7 g of white crystal. By conducting FD-MS analyse, the resulting compound was identified as Compound BH-11 as follows (yield: 60%)

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Synthesis Example 12 [Synthesis of Compound BH-12]

Except that 1.8 g (5.3 mmol) of 6-(2-dibenzofuranyl)-2-naphtalenyl boron acid was used instead of dibenzofuran-2-boronic add, the reaction was carried out in the same way as in the synthesis example 1, thereby obtaining 1.5 g of white crystal. By conducting FD-MS analysis, the resulting compound was identified as Compound BH-12 as follows (yield: 55%).

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Synthesis Example 13 [Synthesis of Compound BH-13]

Except that 1.8 g (5.3 mmd) of 6-(2-dibenzofuranyl)-2-naphtalenyl boronic add was used instead of dibenzofuran-2-boronic acid, the reaction was carried out in the same way as in the synthesis example 2, thereby obtaining 2.0 g of white crystal. By conducting FD-MS analysis, the resulting compound was identified as Compound BH-13 as follows (yield: 65%).

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Synthesis Example 14 [Synthesis of Compound BH-14]

Except that 1.5 g (5.3 mmol) of 3-(2-dibenzofuranyl)phenyl boronic add was used instead of dibenzofuran-2-boronic add, the reaction was carried out in the same way as in the synthesis example 1, thereby obtaining 1.3 g of white crystal. By conducting FD-MS analyse, the resulting compound was identified as Compound BH-14 as follows (yield: 52%).

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Synthesis Example 15 [Synthesis of Compound BH-15]

Except that 1.5 g (5.3 mmol) of 3-(2-dibenzofuranyl)phenyl boronic add was used instead of dibenzofuran-2-boronic add, the reaction was carried out in the same way as in the synthesis example 2, thereby obtaining 1.4 g of white crystal. By conducting FD-MS analysis, the resulting compound was identified as Compound BH-15 as follows (yield: 50%).

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Synthesis Example 16 [Synthesis of Compound BH-16]

Except that 1.5 g (5.3 mmol) of 4-(1-dibenzofuranyl)phenyl boronic add was used instead of dibenzofuran-2-boronic add, the reaction was carried out in the same way as in the synthesis example 1, thereby obtaining 1.6 g of white crystal. By conducting FD-MS analysis, the resulting compound was identified as Compound BH-16 as follows (yield: 62%).

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Synthesis Example 17 [Synthesis of Compound BH-17]
Synthesis of Intermediate 13

To 1.33 g (5.00 mmol) of 9-bromoanthracene-d9, 0.67 g (5.25 mmol) of phenyl-d5-boronic acid and 0.12 g (0.10 mmol) of Pd[PPh₃]₄, 7.5 ml of toluene, 7.5 ml of dimethoxyethane and 7.5 ml (15.0 mmol) of 2M Na₂CO₃aqueous solution were added under an atmosphere of argon, followed by being heated to reflux while stirring for 10 hours.

After completion of the reaction, having been cooled to room temperature, the sample was transferred to a separating funnel and extracted with dichloromethane. The resulting organic phase was dried with MgSO₄, followed by being filtered and concentrated. The concentrated residue was purified with silica gel column chromatography to obtain 1.07 got white solid. By conducting FD-MS analysis, the resulting compound was identified as Intermediate 13 as follows (yield: 80%).

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Synthesis of Intermediate 14

1.07 g (4.0 mmol) of Intermediate 13 was solubilized in 25 ml of dichloromethane, and the resulting solution was dropped into the solution of 0.64 g (4.0 mmol) of bromine in 3 ml of dichloromethane at room temperature, followed by being stirred for one hour.

After completion of the reaction, the sample was transferred to a separating funnel and washed with 2M Na₂S₂O₃aqueous solution. The organic phase was further washed with 10% Na₂CO₃, and thereafter with water. The organic phase was dried with MgSO₄, followed by being filtered and concentrated.

The concentrated residue was dispersed in methanol (100 mL), and the precipitated crystal was dried to obtain 1.3 g of white solid. By conducting FD-MS analysis, the resulting compound was identified as Intermediate 14 as follows (yield: 95%).

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Synthesis of Compound BH-17

To 0.87 g (2.5 mmol) of Intermediate 14, 0.58 g (2.65 mmol) of dibenzofuran-d7-2-boronic add and 0.06 g (0.05 mmol) of Pd[PPh₃]₄, 5 ml of toluene, 5 ml of dimethoxyethane and 5 ml (10.0 mmol) of 2M Na₂CO₃aqueous solution were added under an atmosphere of argon, followed by being heated to reflux while stirring for 10 hours.

After completion of the reaction, having been cooled to room temperature, the sample was transferred to a separating funnel and extracted with dichloromethane. The resulting organic phase was dried with MgSO₄, followed by being filtered and concentrated. The concentrated residue was purified with silica gel column chromatography to obtain 0.77 g of white solid. By conducting FD-MS analysis, the resulting compound was identified as Compound BH-17 as follows (yield: 70%).

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Example 1
(Fabrication of Organic EL Device)

A glass substrate of 25 mm by 75 mm by 1.1 mm thick with an ITO transparent electrode (anode) (manufactured by GEOMATEC Co., Ltd.) was subjected to ultrasonic cleaning in isopropyl alcohol for 5 minutes, and then subjected to UV-ozone cleaning for 30 minutes. The thickness of ITO was 130 nm.

The cleaned glass substrate with a transparent electrode was mounted in a substrate holder of a vacuum vapor deposition apparatus. First, compound HI was deposited on the surface where the transparent electrode was formed so as to cover the transparent electrode, thereby forming an HI film having a thickness of 5 nm. This HI film functioned as a hole-injecting layer.

Subsequent to the formation of the HI film, compound HT-1 was deposited to form an HT-1 film in a thickness of 80 nm on the HI film. This HT-1 film functioned as a hole-transporting layer (a first hole-transporting layer).

Subsequent to the formation of the HT-1 film, compound HT-2 was deposited to form an HT-2 film in a thickness of 10 nm on the HT-1 film. This HT-2 film functioned as an electron-blocking layer (a second hole-transporting layer).

Compound BH-1 (host material) and compound BD-1 (dopant material) were co-deposited on the HT-2 film so that the ratio of compound BD-1 was 4 mass % to form a BH-1:BD-1 film in a thickness of 25 nm. This BH-1:BD-1 film functioned as an emitting layer.

Compound ET-1 was deposited on the emitting layer to form an ET-1 film in a thickness of 10 nm. This ET-1 film functioned as a hole-barrier layer.

Compound ET-2 was deposited on the ET-1 layer to form an ET-2 layer in a thickness of 15 nm. This ET-2 layer functioned as an electron-transporting layer. LiF was deposited on the ET-2 layer to form a LiF film in a thickness of 1 nm. A1 metal was deposited on the LiF film to form a metal cathode in a thickness of 80 nm. An organic EL device was thus fabricated.

The layer construction of the fabricated organic EL device was as follows. ITO (130)/HI (5)/HT-1 (80)/HT-2 (10)/BH-1:BD-1 (25:4 mass %)/ET-1 (10)/ET-2 (15)/LiF (1)/Al (80)

The numbers in the parenthesis denote the thickness of each layer (unit: nm).

The compounds used in Example 1 as well as the subsequent examples and comparative examples are shown below.

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(Evaluation of Organic EL Device)

A voltage was applied to the obtained organic EL device so that the current density was 50 mA/cm², and the time until the luminance reached 95% with respect to the initial luminance (LT95) was measured. The results are shown in Table 1.

Further, a voltage was applied to the obtained organic EL device so that the current density was 10 mA/cm², and spectral radiance spectrum was measured using a spectroradimeter “CS-1000” (manufactured by Konica Minolta, Inc.) to determine CIE1931 chromaticity coordinate (CIEx, CIEy). The results are shown in Table 1.

Comparative Example 1

Except that the compound shown in the blowing table was used as the host material of the emitting layer, the organic EL device was fabricated and evaluated in the same manner as in Example 1. The results are shown in Table 1.

TABLE 1

Emitting layer

Host
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 1
BH-1
BD-1
155
0.139
0.090

Comparative
BH-1-a
BD-1
94
0.139
0.090

Example 1

Example 2, Comparative Example 2

Except that the compounds shown in Table 2 were used as the materials of the emitting layer, the organic EL devices were fabricated and evaluated in the same manner as in Example 1. The results are shown in Table 2.

TABLE 2

Emitting layer

Host
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 2
BH-1
BD-2
43
0.137
0.068

Comparative
BH-1-a
BD-2
28
0.137
0.067

Example 2

Example 3, Comparative Example 3

Except that the compounds shown in Table 3 were used as the materials of the emitting layer, the organic EL devices were fabricated and evaluated in the same manner as in Example 1. The results are shown in Table 3.

TABLE 3

Emitting layer

Host
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 3
BH-2
BD-1
80
0.139
0.090

Comparative
BH-2-a
BD-1
49
0.139
0.090

Example 3

Example 4, Comparative Example 4

Except that the compounds shown in Table 4 were used as the materials of the emitting layer, the organic EL devices were fabricated and evaluated in the same manner as in Example 1. The results are shown in Table 4.

TABLE 4

Emitting layer

Host
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 4
BH-2
BD-2
25
0.137
0.067

Comparative
BH-2-a
BD-2
15
0.137
0.067

Example 4

Example 5, Comparative Example 5

Except that the compounds shown in Table 5 were used as the materials of the emitting layer, the organic EL devices were fabricated and evaluated in the same manner as in Example 1. The results are shown in Table 5.

TABLE 5

Emitting layer

Host
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 5
BH-3
BD-1
70
0.139
0.090

Comparative
BH-3-a
BD-1
40
0.139
0.090

Example 5

Example 6, Comparative Example 6

Except that the compounds shown in Table 6 were used as the materials of the emitting layer, the organic EL devices were fabricated and evaluated in the same manner as in Example 1. The results are shown in Table 6.

TABLE 6

Emitting layer

Host
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 6
BH-3
BD-2
20
0.137
0.067

Comparative
BH-3-a
BD-2
12
0.137
0.067

Example 6

Example 7, Comparative Example 7

Except that the compounds shown in Table 7 were used as the materials of the emitting layer, the organic EL devices were fabricated and evaluated in the same manner as in Example 1. The results are shewn in Table 7.

TABLE 7

Emitting layer

Host
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 7
BH-4
BD-1
65
0.139
0.090

Comparative
BH-4-a
BD-1
38
0.139
0.090

Example 7

Example 8, Comparative Example 8

Except that the compounds shown in Table 8 were used as the materials of the emitting layer, the organic EL devices were fabricated and evaluated in the same manner as in Example 1. The results are shown in Table 8.

TABLE 8

Emitting layer

Host
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 8
BH-4
BD-2
20
0.137
0.065

Comparative
BH-4-a
BD-2
13
0.137
0.065

Example 8

Example 11, Comparative Example 11

Except that the compounds shown in the following table were used as the materials of the emitting layer (host material and dopant material), the organic EL devices were fabricated and evaluated in the same manner as in Example 1. The results are shown in Table 9.

TABLE 9

Emitting layer

Host
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 11
BH-1
BD-3
130
0.140
0.080

Comparative
BH-1-a
BD-3
83
0.140
0.080

Example 11

Example 12, Comparative Example 12

TABLE 10

Emitting layer

Host
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 12
BH-2
BD-3
71
0.140
0.081

Comparative
BH-2-a
BD-3
45
0.140
0.080

Example 12

Example 13, Comparative Example 13

TABLE 11

Emitting layer

Host
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 13
BH-3
BD-3
56
0.140
0.080

Comparative
BH-3-a
BD-3
36
0.140
0.080

Example 13

Example 14, Comparative Example 14

TABLE 12

Emitting layer

Host
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 14
BH-4
BD-3
57
0.140
0.080

Comparative
BH-4-a
BD-3
30
0.140
0.080

Example 14

Example 15, Comparative Example 15

Except that the compounds shown in the following table were used as the materials of the emitting layer (host material and dopant material), the organic EL devices were fabricated and evaluated in foe same manner as in Example 1. The results are shown in Table 13.

TABLE 13

Emitting layer

Host
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 15
BH-5
BD-3
146
0.140
0.080

Comparative
BH-5-a
BD-3
82
0.140
0.080

Example 15

Example 16, Comparative Example 16

Except that the compounds shown in the following table were used as the materials of foe emitting layer (host material and dopant material), the organic EL devices were fabricated and evaluated in the same manner as in Example 1. The results are shown in Table 14.

TABLE 14

Emitting layer

Host
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 16
BH-6
BD-3
126
0.140
0.080

Comparative
BH-6-a
BD-3
78
0.140
0.080

Example 16

Example 17, Comparative Example 17

TABLE 15

Emitting layer

Host
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 17
BH-7
BD-3
127
0.140
0.080

Comparative
BH-7-a
BD-3
80
0.140
0.080

Example 17

Example 21, Comparative Example 21

TABLE 16

Emitting layer

Host
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 21
BH-1
BD-4
155
0.135
0.098

Comparative
BH-1-a
BD-4
96
0.135
0.098

Example 21

Example 22, Comparative Example 22

TABLE 17

Emitting layer

Host
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 22
BH-2
BD-4
77
0.135
0.098

Comparative
BH-2-a
BD-4
50
0.135
0.099

Example 22

Example 23, Comparative Example 23

TABLE 18

Emitting layer

Host
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 23
BH-3
BD-4
73
0.135
0.098

Comparative
BH-3-a
BD-4
43
0.135
0.098

Example 23

Example 24, Comparative Example 24

TABLE 19

Emitting layer

Host
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 24
BH-4
BD-4
60
0.135
0.098

Comparative
BH-4-a
BD-4
41
0.135
0.098

Example 24

Example 25, Comparative Example 25

TABLE 20

Emitting layer

Host
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 25
BH-5
BD-4
167
0.135
0.098

Comparative
BH-5-a
BD-4
105
0.135
0.098

Example 25

Example 26, Comparative Example 26

TABLE 21

Emitting layer

Host
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 26
BH-6
BD-4
147
0.135
0.098

Comparative
BH-6-a
BD-4
92
0.135
0.098

Example 26

Example 27, Comparative Example 27

Except that the compounds shown In the following table were used as the materials of the emitting layer (host material and dopant material), the organic EL devices were fabricated and evaluated in the same manner as in Example 1. The results are shown in Table 22.

TABLE 22

Emitting layer

Host
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 27
BH-7
BD-4
150
0.135
0.098

Comparative
BH-7-a
BD-4
96
0.135
0.098

Example 27

Example 31, Comparative Example 31

TABLE 23

Emitting layer

Host
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 31
BH-1
BD-5
163
0.135
0.086

Comparative
BH-1-a
BD-5
98
0.135
0.086

Example 31

Example 32, Comparative Example 32

TABLE 24

Emitting layer

Host
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 32
BH-2
BD-5
78
0.135
0.086

Comparative
BH-2-a
BD-5
51
0.135
0.086

Example 32

Example 33, Comparative Example 33

Except that the compounds shown in the following (able were used as the materials of the emitting layer (host material and dopant material), the organic EL devices were fabricated and evaluated in the same manner as in Example 1. The results are shown in Table 25.

TABLE 25

Emitting layer

Host
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 33
BH-3
BD-5
73
0.135
0.086

Comparative
BH-3-a
BD-5
39
0.135
0.086

Example 33

Example 34, Comparative Example 34

TABLE 26

Emitting layer

Host
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 34
BH-4
BD-5
62
0.135
0.085

Comparative
BH-4-a
BD-5
43
0.135
0.086

Example 34

Example 35, Comparative Example 35

TABLE 27

Emitting layer

Host
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 35
BH-5
BD-5
170
0.135
0.086

Comparative
BH-5-a
BD-5
105
0.135
0.086

Example 35

Example 36, Comparative Example 36

TABLE 28

Emitting layer

Host
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 36
BH-6
BD-5
152
0.135
0.086

Comparative
BH-6-a
BD-5
89
0.135
0.086

Example 36

Example 37, Comparative Example 37

TABLE 29

Emitting layer

Host
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 37
BH-7
BD-5
161
0.135
0.086

Comparative
BH-7-a
BD-5
102
0.135
0.086

Example 37

Example 41, Comparative Example 41

TABLE 30

Emitting layer

Host
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 41
BH-1
BD-6
195
0.135
0.080

Comparative
BH-1-a
BD-6
123
0.135
0.080

Example 41

Example 42, Comparative Example 42

TABLE 31

Emitting layer

Host
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 42
BH-2
BD-6
106
0.135
0.080

Comparative
BH-2-a
BD-6
66
0.135
0.080

Example 42

Example 43, Comparative Example 43

TABLE 32

Emitting layer

Host
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 43
BH-3
BD-6
90
0.135
0.080

Comparative
BH-3-a
BD-6
53
0.135
0.080

Example 43

Example 44, Comparative Example 44

TABLE 33

Emitting layer

Host
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 44
BH-4
BD-6
84
0.135
0.080

Comparative
BH-4-a
BD-6
52
0.135
0.080

Example 44

Example 45, Comparative Example 45

TABLE 34

Emitting layer

Host
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 45
BH-5
BD-6
211
0.135
0.080

Comparative
BH-5-a
BD-6
133
0.135
0.081

Example 45

Example 46, Comparative Example 46

TABLE 35

Emitting layer

Host
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 46
BH-6
BD-6
179
0.135
0.080

Comparative
BH-6-a
BD-6
112
0.135
0.080

Example 46

Example 47, Comparative Example 47

TABLE 36

Emitting layer

Host
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 47
BH-7
BD-6
202
0.135
0.080

Comparative
BH-7-a
BD-6
125
0.135
0.080

Example 47

Example 51, Comparative Example 51

TABLE 37

Emitting layer

Host
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 51
BH-1
BD-7
253
0.136
0.090

Comparative
BH-1-a
BD-7
146
0.136
0.090

Example 51

Example 52, Comparative Example 52

TABLE 38

Emitting layer

Host
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 52
BH-2
BD-7
125
0.136
0.090

Comparative
BH-2-a
BD-7
73
0.136
0.090

Example 52

Example 53, Comparative Example 53

TABLE 39

Emitting layer

Host
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 53
BH-3
BD-7
102
0.136
0.090

Comparative
BH-3-a
BD-7
64
0.136
0.090

Example 53

Example 54, Comparative Example 54

TABLE 40

Emitting layer

Host
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 54
BH-4
BD-7
99
0.136
0.090

Comparative
BH-4-a
BD-7
64
0.136
0.090

Example 54

Example 55, Comparative Example 55

TABLE 41

Emitting layer

Host
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 55
BH-5
BD-7
257
0.136
0.090

Comparative
BH-5-a
BD-7
161
0.136
0.091

Example 55

Example 56, Comparative Example 56

Except that the compounds shown in the following table were used as the materials of the emitting layer (host material and dopant material), the organic EL devices were fabricated and evaluated In the same manner as in Example 1. The results are shown in Table 42.

TABLE 42

Emitting layer

Host
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 56
BH-6
BD-7
215
0.136
0.090

Comparative
BH-6-a
BD-7
137
0.136
0.090

Example 56

Example 57, Comparative Example 57

TABLE 43

Emitting layer

Host
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 57
BH-7
BD-7
241
0.136
0.090

Comparative
BH-7-a
BD-7
141
0.136
0.090

Example 57

Example 61, Comparative Example 61

TABLE 44

Emitting layer

Host
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 61
BH-1
BD-8
104
0.144
0.061

Comparative
BH-1-a
BD-8
65
0.144
0.061

Example 61

Example 62, Comparative Example 62

Except that the compounds shown In the following fable were used as the materials of the emitting layer (host material and dopant material), the organic EL devices were fabricated and evaluated in the same manner as in Example 1. The results are shown in Table 45.

TABLE 45

Emitting layer

Host
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 62
BH-2
BD-8
53
0.144
0.061

Comparative
BH-2-a
BD-8
37
0.144
0.061

Example 62

Example 63, Comparative Example 63

TABLE 46

Emitting layer

Host
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 63
BH-3
BD-8
51
0.144
0.060

Comparative
BH-3-a
BD-8
32
0.144
0.061

Example 63

Example 64, Comparative Example 64

Except that the compounds shown in the following fable were used as the materials of the emitting layer (host material and dopant material), the organic EL devices were fabricated and evaluated in the same manner as in Example 1. The results are shown in Table 47.

TABLE 47

Emitting layer

Host
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 64
BH-4
BD-8
47
0.144
0.061

Comparative
BH-4-a
BD-8
29
0.144
0.061

Example 64

Example 65, Comparative Example 65

TABLE 48

Emitting layer

Host
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 65
BH-5
BD-8
117
0.144
0.061

Comparative
BH-5-a
BD-8
75
0.144
0.061

Example 65

Example 66, Comparative Example 66

TABLE 49

Emitting layer

Host
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 66
BH-6
BD-8
105
0.144
0.061

Comparative
BH-6-a
BD-8
65
0.144
0.061

Example 66

Example 67, Comparative Example 67

TABLE 50

Emitting layer

Host
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 67
BH-7
BD-8
110
0.144
0.061

Comparative
BH-7-a
BD-8
66
0.144
0.061

Example 67

Example 68, Comparative Example 68

Except that the compounds shown in following table were used as the materials of the emitting layer (host material and dopant material), the organic EL devices were fabricated and evaluated in the same manner as in Example 1. The results are shown in Table 51.

TABLE 51

Emitting layer

Host
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 68
BH-1
BD-9
111
0.141
0.056

Comparative
BH-1-a
BD-9
88
0.141
0.056

Example 68

Example 69, Comparative Example 69

TABLE 52

Emitting layer

Host
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 69
BH-2
BD-9
65
0.141
0.056

Comparative
BH-2-a
BD-9
46
0.141
0.056

Example 69

Example 70, Comparative Example 70

TABLE 53

Emitting layer

Host
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 70
BH-3
BD-9
60
0.141
0.056

Comparative
BH-3-a
BD-9
42
0.141
0.056

Example 70

Example 71, Comparative Example 71

TABLE 54

Emitting layer

Host
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 71
BH-5
BD-9
137
0.141
0.057

Comparative
BH-5-a
BD-9
94
0.141
0.057

Example 71

Example 72, Comparative Example 72

TABLE 55

Emitting layer

Host
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 72
BH-6
BD-9
118
0.141
0.056

Comparative
BH-6-a
BD-9
84
0.141
0.056

Example 72

Example 73, Comparative Example 73

TABLE 56

Emitting layer

Host
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 73
BH-7
BD-9
136
0.141
0.056

Comparative
BH-7-a
BD-9
88
0.141
0.056

Example 73

Example 74, Comparative Example 74

TABLE 57

Emitting layer

Host
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 74
BH-8
BD-9
89
0.141
0.056

Comparative
BH-8-a
BD-9
63
0.141
0.056

Example 74

Example 75, Comparative Example 75

TABLE 58

Emitting layer

Host
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 75
BH-9
BD-9
100
0.141
0.056

Comparative
BH-9-a
BD-9
66
0.141
0.056

Example 75

Example 76, Comparative Example 76

TABLE 59

Emitting layer

Host
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 76
BH-10
BD-9
90
0.141
0.056

Comparative
BH-10-a
BD-9
61
0.141
0.056

Example 76

Example 77, Comparative Example 77

TABLE 60

Emitting layer

Host
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 77
BH-11
BD-9
77
0.141
0.056

Comparative
BH-11-a
BD-9
55
0.141
0.056

Example 77

Example 78, Comparative Example 78

TABLE 61

Emitting layer

Host
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 78
BH-12
BD-9
73
0.141
0.057

Comparative
BH-12-a
BD-9
47
0.141
0.057

Example 78

Example 79, Comparative Example 79

TABLE 62

Emitting layer

Host
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 79
BH-13
BD-9
66
0.141
0.056

Comparative
BH-13-a
BD-9
44
0.141
0.056

Example 79

Example 80, Comparative Example 80

TABLE 63

Emitting layer

Hosting
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 80
BH-14
BD-9
115
0.141
0.056

Comparative
BH-14-a
BD-9
83
0.141
0.056

Example 80

Example 81, Comparative Example 81

TABLE 64

Emitting layer

Hosting
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 81
BH-15
BD-9
80
0.141
0.056

Comparative
BH-15-a
BD-9
55
0.141
0.056

Example 81

Example 82, Comparative Example 82

TABLE 65

Emitting layer

Hosting
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 82
BH-16
BD-9
72
0.141
0.056

Comparative
BH-16-a
BD-9
55
0.141
0.056

Example 82

Example 83

TABLE 66

Emitting layer

Hosting
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 83
BH-17
BD-9
110
0.141
0.056

Example 84, Comparative Example 84

TABLE 67

Emitting layer

Hosting
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 84
BH-1
BD-10
203
0.133
0.078

Comparative
BH-1-a
BD-10
143
0.133
0.078

Example 84

Example 85, Comparative Example 85

TABLE 68

Emitting layer

Hosting
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 85
BH-2
BD-10
111
0.133
0.078

Comparative
BH-2-a
BD-10
77
0.133
0.078

Example 85

Example 86, Comparative Example 86

TABLE 69

Emitting layer

Hosting
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 86
BH-3
BD-10
93
0.133
0.078

Comparative
BH-3-a
BD-10
64
0.133
0.078

Example 86

Example 87, Comparative Example 87

TABLE 70

Emitting layer

Hosting
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 87
BH-5
BD-10
217
0.133
0.079

Comparative
BH-5-a
BD-10
154
0.133
0.079

Example 87

Example 88, Comparative Example 88

TABLE 71

Emitting layer

Hosting
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 88
BH-6
BD-10
208
0.133
0.078

Comparative
BH-6-a
BD-10
138
0.133
0.078

Example 88

Example 89, Comparative Example 89

TABLE 72

Emitting layer

Hosting
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 89
BH-7
BD-10
218
0.133
0.078

Comparative
BH-7-a
BD-10
143
0.133
0.078

Examole 89

Example 90, Comparative Example 90

TABLE 73

Emitting layer

Hosting
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 90
BH-8
BD-10
155
0.133
0.078

Comparative
BH-8-a
BD-10
110
0.133
0.078

Example 90

Example 91, Comparative Example 91

TABLE 74

Emitting layer

Hosting
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 91
BH-9
BD-10
151
0.133
0.078

Comparative
BH-9-a
BD-10
110
0.133
0.078

Example 91

Example 92, Comparative Example 92

Except that the compounds shown in the following table were used as the materials of the emitting layer (host material and dopant material), the organic EL devices were fabricated and evaluated in foe same manner as in Example 1. The results are shown in Table 75.

TABLE 75

Emitting layer

Hosting
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 92
BH-10
BD-10
161
0.133
0.078

Comparative
BH-10-a
BD-10
105
0.133
0.078

Example 92

Example 93, Comparative Example 93

TABLE 76

Emitting layer

Hosting
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 93
BH-11
BD-10
137
0.133
0.078

Comparative
BH-11-a
BD-10
92
0.133
0.078

Example 93

Example 94, Comparative Example 94

TABLE 77

Emitting layer

Hosting
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 94
BH-12
BD-10
117
0.133
0.079

Comparative
BH-12-a
BD-10
77
0.133
0.079

Example 94

Example 95, Comparative Example 95

TABLE 78

Emitting layer

Hosting
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 95
BH-13
BD-10
113
0.133
0.078

Comparative
BH-13-a
BD-10
75
0.133
0.078

Example 95

Example 96, Comparative Example 96

TABLE 79

Emitting layer

Hosting
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 96
BH-14
BD-10
191
0.133
0.078

Comparative
BH-14-a
BD-10
138
0.133
0.078

Example 96

Example 97, Comparative Example 97

TABLE 80

Emitting layer

Hosting
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 97
BH-15
BD-10
138
0.133
0.078

Comparative
BH-15-a
BD-10
94
0.133
0.078

Example 97

Example 98, Comparative Example 98

TABLE 81

Emitting layer

Hosting
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 98
BH-16
BD-10
141
0.133
0.078

Comparative
BH-16-a
BD-10
90
0.133
0.078

Example 98

Example 99

TABLE 82

Emitting layer

Hosting
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 99
BH-17
BD-11
209
0.133
0.078

Example 100, Comparative Example 100

TABLE 83

Emitting layer

Hosting
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 100
BH-1
BD-11
191
0.133
0.076

Comparative
BH-1-a
BD-11
138
0.133
0.076

Example 100

Example 101, Comparative Example 101

TABLE 84

Emitting layer

Hosting
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 101
BH-2
BD-11
97
0.133
0.076

Comparative
BH-2-a
BD-11
72
0.133
0.076

Example 101

Example 102, Comparative Example 102

TABLE 85

Emitting layer

Hosting
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 102
BH-3
BD-11
91
0.133
0.076

Comparative
BH-3-a
BD-11
61
0.133
0.076

Example 102

Example 103, Comparative Example 103

TABLE 86

Emitting layer

Hosting
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 103
BH-5
BD-11
207
0.133
0.077

Comparative
BH-5-a
BD-11
147
0.133
0.077

Example 103

Example 104, Comparative Example 104

TABLE 87

Emitting layer

Hosting
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 104
BH-6
BD-11
181
0.133
0.076

Comparative
BH-6-a
BD-11
132
0.133
0.076

Example 104

Example 105, Comparative Example 105

TABLE 88

Emitting layer

Hosting
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 105
BH-7
BD-11
199
0.133
0.076

Comparative
BH-7-a
BD-11
138
0.133
0.076

Example 105

Example 106, Comparative Example 106

TABLE 89

Emitting layer

Hosting
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 106
BH-8
BD-11
153
0.133
0.076

Comparative
BH-8-a
BD-11
105
0.133
0.076

Example 106

Example 107, Comparative Example 107

TABLE 90

Emitting layer

Hosting
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 107
BH-9
BD-11
145
0.133
0.076

Comparative
BH-9-a
BD-11
102
0.133
0.076

Example 107

Example 108, Comparative Example 108

TABLE 91

Emitting layer

Hosting
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 108
BH-10
BD-11
124
0.133
0.076

Comparative
BH-10-a
BD-11
97
0.133
0.076

Example 108

Example 109, Comparative Example 109

TABLE 92

Emitting layer

Hosting
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 109
BH-11
BD-11
108
0.133
0.076

Comparative
BH-11-a
BD-11
83
0.133
0.076

Example 109

TABLE 93

Emitting layer

Hosting
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 110
BH-12
BD-11
101
0.133
0.077

Comparative
BH-12-a
BD-11
74
0.133
0.077

Example 110

Example 111, Comparative Example 111

TABLE 94

Emitting layer

Hosting
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 111
BH-13
BD-11
102
0.133
0.076

Comparative
BH-13-a
BD-11
66
0.133
0.076

Example 111

Example 112, Comparative Example 112

TABLE 95

Emitting layer

Hosting
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 112
BH-14
BD-11
186
0.133
0.076

Comparative
BH-14-a
BD-11
130
0.133
0.076

Example 112

Example 113, Comparative Example 113

TABLE 96

Emitting layer

Hosting
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 113
BH-15
BD-11
128
0.133
0.076

Comparative
BH-15-a
BD-11
88
0.133
0.076

Example 113

Example 114, Comparative Example 114

TABLE 97

Emitting layer

Hosting
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 114
BH-16
BD-11
128
0.133
0.076

Comparative
BH-16-a
BD-11
87
0.133
0.076

Example 114

Example 115

TABLE 98

Emitting layer

Hosting
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 115
BH-17
BD-11
190
0.133
0.076

Example 116, Comparative Example 116

TABLE 99

Emitting layer

Hosting
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 116
BH-1
BD-12
123
0.141
0.058

Comparative
BH-1-a
BD-12
94
0.141
0.058

Example 116

Example 117, Comparative Example 117

TABLE 100

Emitting layer

Hosting
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 117
BH-2
BD-12
70
0.141
0.058

Comparative
BH-2-a
BD-12
52
0.141
0.058

Example 117

Example 118, Comparative Example 118

TABLE 101

Emitting layer

Hosting
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 118
BH-3
BD-12
66
0.141
0.058

Comparative
BH-3-a
BD-12
44
0.141
0.058

Example 118

Example 119, Comparative Example 119

Except that the compounds shown in following fable were used as the materials of the emitting layer (host material and dopant material), the organic EL devices were fabricated and evaluated in the same manner as in Example 1. The results are shown in Table 102.

TABLE 102

Emitting layer

Hosting
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 119
BH-5
BD-12
149
0.141
0.059

Comparative
BH-5-a
BD-12
101
0.141
0.059

Example 119

Example 120, Comparative Example 120

TABLE 103

Emitting layer

Hosting
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 120
BH-6
BD-12
123
0.141
0.058

Comparative
BH-6-a
BD-12
92
0.141
0.058

Example 120

Example 121, Comparative Example 121

TABLE 104

Emitting layer

Hosting
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 121
BH-7
BD-12
145
0.141
0.058

Comparative
BH-7-a
BD-12
96
0.141
0.058

Example 121

Example 122, Comparative Example 122

TABLE 105

Emitting layer

Hosting
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 122
BH-8
BD-12
115
0.141
0.058

Comparative
BH-8-a
BD-12
79
0.141
0.058

Example 122

Example 123, Comparative Example 123

TABLE 106

Emitting layer

Hosting
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 123
BH-9
BD-12
106
0.141
0.058

Comparative
BH-9-a
BD-12
72
0.141
0.058

Example 123

Example 124, Comparative Example 124

TABLE 107

Emitting layer

Hosting
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 124
BH-10
BD-12
98
0.141
0.058

Comparative
BH-10-a
BD-12
65
0.141
0.058

Example 124

Example 125, Comparative Example 125

TABLE 108

Emitting layer

Hosting
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 125
BH-11
BD-12
82
0.141
0.058

Comparative
BH-11-a
BD-12
57
0.141
0.058

Example 125

Example 126, Comparative Example 126

TABLE 109

Emitting layer

Hosting
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 126
BH-12
BD-12
79
0.141
0.059

Comparative
BH-12-a
BD-12
52
0.141
0.059

Example 126

Example 127, Comparative Example 127

TABLE 110

Emitting layer

Hosting
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 127
BH-13
BD-12
79
0.141
0.058

Comparative
BH-13-a
BD-12
55
0.141
0.058

Example 127

Example 128, Comparative Example 128

TABLE 111

Emitting layer

Hosting
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 128
BH-14
BD-12
123
0.141
0.058

Comparative
BH-14-a
BD-12
88
0.141
0.058

Example 128

Example 129, Comparative Example 129

TABLE 112

Emitting layer

Hosting
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 129
BH-15
BD-12
93
0.141
0.058

Comparative
BH-15-a
BD-12
63
0.141
0.058

Example 129

Example 130, Comparative Example 130

TABLE 113

Emitting layer

Hosting
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 130
BH-16
BD-12
81
0.141
0.058

Comparative
BH-16-a
BD-12
61
0.141
0.058

Example 130

Example 131

TABLE 114

Emitting layer

Hosting
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 131
BH-17
BD-12
120
0.141
0.058

Example 132 and Comparative Example 132

TABLE 115

Emitting layer

Hosting
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 132
BH-8
BD-3
98
0.140
0.080

Comparative
BH-8-a
BD-3
64
0.140
0.080

Example 132

Example 133 and Comparative Example 133

TABLE 116

Emitting layer

Hosting
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 133
BH-9
BD-3
100
0.140
0.080

Comparative
BH-9-a
BD-3
64
0.140
0.080

Example 133

Example 134 and Comparative Example 134

TABLE 117

Emitting layer

Hosting
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 134
BH-10
BD-3
94
0.140
0.080

Comparative
BH-10-a
BD-3
58
0.140
0.080

Example 134

Example 135 and Comparative Example 135

TABLE 118

Emitting layer

Hosting
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 135
BH-11
BD-3
83
0.140
0.081

Comparative
BH-11-a
BD-3
50
0.140
0.080

Example 135

Example 136 and Comparative Example 136

TABLE 119

Emitting layer

Hosting
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 136
BH-12
BD-3
73
0.140
0.080

Comparative
BH-12-a
BD-3
45
0.140
0.080

Example 136

Example 137 and Comparative Example 137

TABLE 120

Emitting layer

Hosting
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 137
BH-13
BD-3
65
0.140
0.080

Comparative
BH-13-a
BD-3
40
0.140
0.080

Example 137

Example 138 and Comparative Example 138

TABLE 121

Emitting layer

Hosting
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 138
BH-14
BD-3
127
0.140
0.080

Comparative
BH-14-a
BD-3
75
0.140
0.080

Example 138

Example 139 and Comparative Example 139

TABLE 122

Emitting layer

Hosting
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 139
BH-15
BD-3
88
0.140
0.080

Comparative
BH-15-a
BD-3
54
0.140
0.080

Example 139

Example 140 and Comparative Example 140

TABLE 123

Emitting layer

Host
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 140
BH-16
BD-3
84
0.140
0.080

Comparative
BH-16-a
BD-3
52
0.140
0.080

Example 140

Example 141

Except that the compounds shown in following table were used as the materials of the emitting layer (host material and dopant material), the organic EL device was fabricated and evaluated in the same manner as in Example 1. The results are shown in the following Table.

TABLE 124

Emitting layer

Host
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 141
BH-17
BD-3
131
0.140
0.080

Example 142 and Comparative Example 142

TABLE 125

Emitting layer

Host
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 142
BH-8
BD-4
118
0.135
0.098

Comparative
BH-8-a
BD-4
75
0.135
0.098

Example 142

Example 143 and Comparative Example 143

TABLE 126

Emitting layer

Host
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 143
BH-9
BD-4
112
0.135
0.098

Comparative
BH-9-a
BD-4
72
0.135
0.098

Example 143

Example 144 and Comparative Example 144

TABLE 127

Emitting layer

Host
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 144
BH-10
BD-4
105
0.135
0.098

Comparative
BH-10-a
BD-4
66
0.135
0.098

Example 144

Example 145 and Comparative Example 145

TABLE 128

Emitting layer

Host
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 145
BH-11
BD-4
90
0.135
0.098

Comparative
BH-11-a
BD-4
60
0.135
0.098

Example 145

Example 146 and Comparative Example 146

TABLE 129

Emitting layer

Host
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 146
BH-12
BD-4
80
0.135
0.098

Comparative
BH-12-a
BD-4
53
0.135
0.098

Example 146

Example 147 and Comparative Example 147

TABLE 130

Emitting layer

Host
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 147
BH-13
BD-4
70
0.135
0.098

Comparative
BH-13-a
BD-4
46
0.135
0.098

Example 147

Example 148 and Comparative Example 148

TABLE 131

Emitting layer

Host
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 148
BH-14
BD-4
150
0.135
0.098

Comparative
BH-14-a
BD-4
92
0.135
0.098

Example 148

Example 149 and Comparative Example 149

TABLE 132

Emitting layer

Host
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 149
BH-15
BD-4
102
0.135
0.098

Comparative
BH-15-a
BD-4
64
0.135
0.098

Example 149

Example 150 and Comparative Example 150

TABLE 133

Emitting layer

Host
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 150
BH-16
BD-4
96
0.135
0.098

Comparative
BH-16-a
BD-4
60
0.135
0.099

Example 150

Example 151

Except that the compounds shown in following table were used as the materials erf the emitting layer (host material and dopant material), the organic EL device was fabricated and evaluated in the same manner as in Example 1. The results are shown in the following Table.

TABLE 134

Emitting layer

Host
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 151
BH-17
BD-4
157
0.135
0.098

Example 152 and Comparative Example 152

TABLE 135

Emitting layer

Host
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 152
BH-8
BD-5
126
0.135
0.086

Comparative
BH-8-a
BD-5
80
0.135
0.086

Example 152

Example 153 and Comparative Example 153

TABLE 136

Emitting layer

Host
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 153
BH-9
BD-5
126
0.135
0.086

Comparative
BH-9-a
BD-5
76
0.135
0.086

Example 153

Example 154 and Comparative Example 154

TABLE 137

Emitting layer

Host
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 154
BH-10
BD-5
110
0.135
0.085

Comparative
BH-10-a
BD-5
70
0.135
0.086

Example 154

Example 155 and Comparative Example 155

TABLE 138

Emitting layer

Host
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 155
BH-11
BD-5
103
0.135
0.086

Comparative
BH-11-a
BD-5
60
0.135
0.086

Example 155

Example 156 and Comparative Example 156

TABLE 139

Emitting layer

Host
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 156
BH-12
BD-5
90
0.135
0.086

Comparative
BH-12-a
BD-5
56
0.135
0.086

Example 156

Example 157 and Comparative Example 157

TABLE 140

Emitting layer

Host
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 157
BH-13
BD-5
80
0.135
0.086

Comparative
BH-13-a
BD-5
50
0.135
0.086

Example 157

Example 158 and Comparative Example 158

TABLE 141

Emitting layer

Host
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 158
BH-14
BD-5
157
0.135
0.086

Comparative
BH-14-a
BD-5
92
0.135
0.085

Example 158

Example 159 and Comparative Example 159

TABLE 142

Emitting layer

Host
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 159
BH-15
BD-5
110
0.135
0.086

Comparative
BH-15-a
BD-5
65
0.135
0.086

Example 159

Example 160 and Comparative Example 160

TABLE 143

Emitting layer

Host
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 160
BH-16
BD-5
100
0.135
0.086

Comparative
BH-16-a
BD-5
60
0.135
0.086

Example 160

Example 161

TABLE 144

Emitting layer

Host
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 161
BH-17
BD-5
165
0.135
0.086

Example 162 and Comparative Example 162

TABLE 145

Emitting layer

Host
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 162
BH-8
BD-6
150
0.135
0.080

Comparative
BH-8-a
BD-6
90
0.135
0.080

Example 162

Example 163 and Comparative Example 163

TABLE 146

Emitting layer

Host
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 163
BH-9
BD-6
155
0.135
0.080

Comparative
BH-9-a
BD-6
90
0.135
0.080

Example 163

Example 164 and Comparative Example 164

TABLE 147

Emitting layer

Host
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 164
BH-10
BD-6
143
0.135
0.080

Comparative
BH-10-a
BD-6
88
0.135
0.080

Example 164

Example 165 and Comparative Example 165

Except that the compounds shown in following table were used as the materials of the emitting layer (host material and dopant material), the organic EL devices were fabricated and evaluated fa the same manner as in Example 1. The results are shown in the following Table.

TABLE 148

Emitting layer

Host
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 165
BH-11
BD-6
124
0.135
0.080

Comparative
BH-11-a
BD-6
75
0.135
0.080

Example 165

Example 166 and Comparative Example 166

TABLE 149

Emitting layer

Host
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 166
BH-12
BD-6
106
0.135
0.080

Comparative
BH-12-a
BD-6
68
0.135
0.080

Example 166

Example 167 and Comparative Example 167

TABLE 150

Emitting layer

Host
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 167
BH-13
BD-6
90
0.135
0.081

Comparative
BH-13-a
BD-6
62
0.135
0.080

Example 167

Example 168 and Comparative Example 168

TABLE 151

Emitting layer

Host
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 168
BH-14
BD-6
195
0.135
0.080

Comparative
BH-14-a
BD-6
117
0.135
0.080

Example 168

Example 169 and Comparative Example 169

Except that the compounds shown in following table were used as the materials of the emitting layer (host material and dopant material), the organic EL devices were fabricated and evaluated fa the same manner as in Example 1. The results are shown in the following Table.

TABLE 152

Emitting layer

Host
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 169
BH-15
BD-6
138
0.135
0.080

Comparative
BH-15-a
BD-6
80
0.135
0.080

Example 169

Example 170 and Comparative Example 170

TABLE 153

Emitting layer

Host
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 170
BH-16
BD-6
130
0.135
0.080

Comparative
BH-16-a
BD-6
77
0.135
0.080

Example 170

Example 171

TABLE 154

Emitting layer

Host
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 171
BH-17
BD-6
200
0.135
0.080

Example 172 and Comparative Example 172

TABLE 155

Emitting layer

Host
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 172
BH-8
BD-7
190
0.136
0.090

Comparative
BH-8-a
BD-7
114
0.136
0.090

Example 172

Example 173 and Comparative Example 173

TABLE 156

Emitting layer

Host
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 173
BH-9
BD-7
179
0.136
0.090

Comparative
BH-9-a
BD-7
110
0.136
0.090

Example 173

Example 174 and Comparative Example 174

TABLE 157

Emitting layer

Host
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 174
BH-10
BD-7
164
0.136
0.090

Comparative
BH-10-a
BD-7
98
0.136
0.090

Example 174

Example 175 and Comparative Example 175

TABLE 158

Emitting layer

Host
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 175
BH-11
BD-7
147
0.136
0.090

Comparative
BH-11-a
BD-7
88
0.136
0.090

Example 175

Example 176 and Comparative Example 176

TABLE 159

Emitting layer

Host
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 176
BH-12
BD-7
122
0.136
0.090

Comparative
BH-12-a
BD-7
80
0.136
0.090

Example 176

Example 177 and Comparative Example 177

TABLE 160

Emitting layer

Host
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 177
BH-13
BD-7
118
0.136
0.090

Comparative
BH-13-a
BD-7
72
0.136
0.090

Example 177

Example 178 and Comparative Example 178

TABLE 161

Emitting layer

Host
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 178
BH-14
BD-7
242
0.136
0.090

Comparative
BH-14-a
BD-7
140
0.136
0.090

Example 178

Example 179 and Comparative Example 179

TABLE 162

Emitting layer

Host
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 179
BH-15
BD-7
155
0.136
0.090

Comparative
BH-15-a
BD-7
92
0.136
0.090

Example 179

Example 180 and Comparative Example 180

TABLE 163

Emitting layer

Host
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 180
BH-16
BD-7
146
0.144
0.061

Comparative
BH-16-a
BD-7
90
0.144
0.061

Example 180

Example 181

TABLE 164

Emitting layer

Host
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 181
BH-17
BD-7
245
0.136
0.090

Example 182 and Comparative Example 182

TABLE 165

Emitting layer

Host
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 182
BH-8
BD-8
82
0.144
0.061

Comparative
BH-8-a
BD-8
50
0.144
0.061

Example 182

Example 183 and Comparative Example 183

TABLE 166

Emitting layer

Host
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 183
BH-9
BD-8
82
0.144
0.061

Comparative
BH-9-a
BD-8
50
0.144
0.061

Example 183

Example 184 and Comparative Example 184

TABLE 167

Emitting layer

Host
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 184
BH-10
BD-8
74
0.144
0.060

Comparative
BH-10-a
BD-8
48
0.144
0.060

Example 184

Example 185 and Comparative Example 185

TABLE 168

Emitting layer

Host
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 185
BH-11
BD-8
63
0.144
0.061

Comparative
BH-11-a
BD-8
42
0.144
0.061

Example 185

Example 186 and Comparative Example 186

TABLE 169

Emitting layer

Host
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 186
BH-12
BD-8
61
0.144
0.061

Comparative
BH-12-a
BD-8
37
0.144
0.061

Example 186

Example 187 and Comparative Example 187

TABLE 170

Emitting layer

Host
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 187
BH-13
BD-8
55
0.144
0.061

Comparative
BH-13-a
BD-8
33
0.144
0.061

Example 187

Example 188 and Comparative Example 188

TABLE 171

Emitting layer

Host
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 188
BH-14
BD-8
105
0.144
0.061

Comparative
BH-14-a
BD-8
65
0.144
0.061

Example 188

Example 189 and Comparative Example 189

TABLE 172

Emitting layer

Host
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 189
BH-15
BD-8
75
0.144
0.061

Comparative
BH-15-a
BD-8
50
0.144
0.061

Example 189

Example 190 and Comparative Example 190

TABLE 173

Emitting layer

Host
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 190
BH-16
BD-8
70
0.144
0.061

Comparative
BH-16-a
BD-8
43
0.144
0.061

Example 190

Example 191

TABLE 174

Emitting layer

Host
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 191
BH-17
BD-8
107
0.144
0.061

Example 192 and Comparative Example 192

TABLE 175

Emitting layer

Host
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 192
BH-1
BD-13
129
0.138
0.117

Comparative
BH-1-a
BD-13
87
0.138
0.117

Example 192

Example 193 and Comparative Example 193

TABLE 176

Emitting layer

Host
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 193
BH-2
BD-13
67
0.138
0.117

Comparative
BH-2-a
BD-13
44
0.138
0.117

Example 193

Example 194 and Comparative Example 194

TABLE 177

Emitting layer

Host
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 194
BH-3
BD-13
57
0.138
0.117

Comparative
BH-3-a
BD-13
40
0.138
0.117

Example 194

Example 195 and Comparative Example 195

TABLE 178

Emitting layer

Host
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 195
BH-4
BD-13
54
0.138
0.117

Comparative
BH-4-a
BD-13
40
0.138
0.117

Example 195

Example 196 and Comparative Example 196

TABLE 179

Emitting layer

Host
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 196
BH-5
BD-13
140
0.138
0.117

Comparative
BH-5-a
BD-13
92
0.138
0.117

Example 196

Example 197 and Comparative Example 197

TABLE 180

Emitting layer

Host
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 197
BH-6
BD-13
123
0.138
0.118

Comparative
BH-6-a
BD-13
80
0.138
0.118

Example 197

Example 198 and Comparative Example 198

TABLE 181

Emitting layer

Host
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 198
BH-7
BD-13
129
0.138
0.117

Comparative
BH-7-a
BD-13
90
0.138
0.117

Example 198

Example 199 and Comparative Example 199

TABLE 182

Emitting layer

Host
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 199
BH-8
BD-13
95
0.138
0.117

Comparative
BH-8-a
BD-13
67
0.138
0.117

Example 199

Example 200 and Comparative Example 200

TABLE 183

Emitting layer

Host
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 200
BH-9
BD-13
94
0.138
0.117

Comparative
BH-9-a
BD-13
63
0.138
0.117

Example 200

Example 201 and Comparative Example 201

TABLE 184

Emitting layer

Host
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 201
BH-10
BD-13
88
0.138
0.117

Comparative
BH-10-a
BD-13
63
0.138
0.117

Example 201

Example 202 and Comparative Example 202

TABLE 185

Emitting layer

Host
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 202
BH-11
BD-13
72
0.138
0.117

Comparative
BH-11-a
BD-13
52
0.138
0.117

Example 202

Example 203 and Comparative Example 203

TABLE 186

Emitting layer

Host
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 203
BH-12
BD-13
70
0.138
0.118

Comparative
BH-12-a
BD-13
48
0.138
0.118

Example 203

Example 204 and Comparative Example 204

TABLE 187

Emitting layer

Host
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 204
BH-13
BD-13
63
0.138
0.117

Comparative
BH-13-a
BD-13
48
0.138
0.117

Example 204

Example 205 and Comparative Example 205

TABLE 188

Emitting layer

Host
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 205
BH-14
BD-13
128
0.138
0.117

Comparative
BH-14-a
BD-13
84
0.138
0.117

Example 205

Example 206 and Comparative Example 206

TABLE 189

Emitting layer

Host
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 206
BH-15
BD-13
81
0.138
0.117

Comparative
BH-15-a
BD-13
59
0.138
0.117

Example 206

Example 207 and Comparative Example 207

TABLE 190

Emitting layer

Host
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 207
BH-16
BD-13
82
0.138
0.117

Comparative
BH-16-a
BD-13
56
0.138
0.117

Example 207

Example 208

TABLE 191

Emitting layer

Host
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 208
BH-17
BD-13
117
0.138
0.117

Example 209 and Comparative Example 209

TABLE 192

Emitting layer

Host
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 209
BH-1
BD-14
108
0.139
0.121

Comparative
BH-1-a
BD-14
72
0.139
0.121

Example 209

Example 210 and Comparative Example 210

TABLE 193

Emitting layer

Host
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 210
BH-2
BD-14
50
0.139
0.121

Comparative
BH-2-a
BD-14
35
0.139
0.121

Example 210

Example 211 and Comparative Example 211

Except that the compounds shown in following table were used as the materials of the emitting layer (host material and dopant material), the organic EL devices were fabricated and evaluated fa the same manner as in Example 1. The results are shown in the following Table.

TABLE 194

Emitting layer

Host
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 211
BH-3
BD-14
49
0.139
0.121

Comparative
BH-3-a
BD-14
35
0.139
0.121

Example 211

Example 212 and Comparative Example 212

TABLE 195

Emitting layer

Host
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 212
BH-4
BD-14
47
0.139
0.121

Comparative
BH-4-a
BD-14
32
0.139
0.121

Example 212

Example 213 and Comparative Example 213

TABLE 196

Emitting layer

Host
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 213
BH-5
BD-14
118
0.139
0.121

Comparative
BH-5-a
BD-14
78
0.139
0.121

Example 213

Example 214 and Comparative Example 214

TABLE 197

Emitting layer

Host
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 214
BH-6
BD-14
106
0.139
0.121

Comparative
BH-6-a
BD-14
70
0.139
0.121

Example 214

Example 215 and Comparative Example 215

TABLE 198

Emitting layer

Host
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 215
BH-7
BD-14
102
0.139
0.121

Comparative
BH-7-a
BD-14
70
0.139
0.121

Example 215

Example 216 and Comparative Example 216

TABLE 199

Emitting layer

Host
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 216
BH-8
BD-14
81
0.139
0.121

Comparative
BH-8-a
BD-14
54
0.139
0.121

Example 216

Example 217 and Comparative Example 217

TABLE 200

Emitting layer

Host
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 217
BH-9
BD-14
72
0.139
0.121

Comparative
BH-9-a
BD-14
54
0.139
0.121

Example 217

Example 218 and Comparative Example 218

TABLE 201

Emitting layer

Host
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 218
BH-10
BD-14
72
0.139
0.121

Comparative
BH-10-a
BD-14
53
0.139
0.121

Example 218

Example 219 and Comparative Example 219

TABLE 202

Emitting layer

Host
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 219
BH-11
BD-14
68
0.139
0.121

Comparative
BH-11-a
BD-14
50
0.139
0.121

Example 219

Example 220 and Comparative Example 220

TABLE 203

Emitting layer

Host
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 220
BH-12
BD-14
63
0.139
0.122

Comparative
BH-12-a
BD-14
43
0.139
0.122

Example 220

Example 221 and Comparative Example 221

TABLE 204

Emitting layer

Host
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 221
BH-13
BD-14
49
0.139
0.121

Comparative
BH-13-a
BD-14
40
0.139
0.121

Example 221

Example 222 and Comparative Example 222

TABLE 205

Emitting layer

Host
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 222
BH-14
BD-14
101
0.139
0.121

Comparative
BH-14-a
BD-14
67
0.139
0.121

Example 222

Example 223 and Comparative Example 223

TABLE 206

Emitting layer

Host
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 223
BH-15
BD-14
73
0.139
0.121

Comparative
BH-15-a
BD-14
48
0.139
0.121

Example 223

Example 224 and Comparative Example 224

TABLE 207

Emitting layer

Host
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 224
BH-16
BD-14
68
0.139
0.121

Comparative
BH-16-a
BD-14
48
0.139
0.121

Example 224

Example 225

TABLE 208

Emitting layer

Host
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 225
BH-17
BD-14
104
0.139
0.121

Example 226 and Comparative Example 226

TABLE 209

Emitting layer

Host
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 226
BH-1
BD-15
63
0.140
0.094

Comparative
BH-1-a
BD-15
44
0.140
0.094

Example 226

Example 227 and Comparative Example 227

TABLE 210

Emitting layer

Host
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 227
BH-2
BD-15
33
0.140
0.094

Comparative
BH-2-a
BD-15
25
0.140
0.094

Example 227

Example 228 and Comparative Example 228

TABLE 211

Emitting layer

Host
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 228
BH-3
BD-15
29
0.140
0.094

Comparative
BH-3-a
BD-15
21
0.140
0.094

Example 228

Example 229 and Comparative Example 229

TABLE 212

Emitting layer

Host
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 229
BH-4
BD-15
32
0.140
0.094

Comparative
BH-4-a
BD-15
25
0.140
0.094

Example 229

Example 230 and Comparative Example 230

TABLE 213

Emitting layer

Host
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 230
BH-5
BD-15
66
0.140
0.094

Comparative
BH-5-a
BD-15
44
0.140
0.094

Example 230

Example 231 and Comparative Example 231

TABLE 214

Emitting layer

Host
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 231
BH-6
BD-15
63
0.140
0.094

Comparative
BH-6-a
BD-15
41
0.140
0.094

Example 231

Example 232 and Comparative Example 232

TABLE 215

Emitting layer

Host
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 232
BH-7
BD-15
63
0.140
0.094

Comparative
BH-7-a
BD-15
41
0.140
0.094

Example 232

Example 233 and Comparative Example 233

TABLE 216

Emitting layer

Host
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 233
BH-8
BD-15
45
0.140
0.094

Comparative
BH-8-a
BD-15
34
0.140
0.094

Example 233

Example 234 and Comparative Example 234

TABLE 217

Emitting layer

Host
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 234
BH-9
BD-15
47
0.140
0.094

Comparative
BH-9-a
BD-15
32
0.140
0.094

Example 234

Example 235 and Comparative Example 235

TABLE 218

Emitting layer

Host
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 235
BH-10
BD-15
42
0.140
0.094

Comparative
BH-10-a
BD-15
30
0.140
0.094

Example 235

Example 236 and Comparative Example 236

TABLE 219

Emitting layer

Host
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 236
BH-11
BD-15
37
0.140
0.094

Comparative
BH-11-a
BD-15
28
0.140
0.094

Example 236

Example 237 and Comparative Example 237

Except that the compounds shown in fallowing table were used as the materials of the emitting layer (host material and dopant material), the organic EL devices were fabricated and evaluated in the same manner as in Example 1. The results are shown in the following Table.

TABLE 220

Emitting layer

Host
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 237
BH-12
BD-15
35
0.140
0.095

Comparative
BH-12-a
BD-15
27
0.140
0.095

Example 237

Example 238 and Comparative Example 238

TABLE 221

Emitting layer

Host
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 238
BH-13
BD-15
33
0.140
0.094

Comparative
BH-13-a
BD-15
27
0.140
0.094

Example 238

Example 239 and Comparative Example 239

TABLE 222

Emitting layer

Host
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 239
BH-14
BD-15
63
0.140
0.094

Comparative
BH-14-a
BD-15
43
0.140
0.094

Example 239

Example 240 and Comparative Example 240

TABLE 223

Emitting layer

Host
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 240
BH-15
BD-15
41
0.140
0.094

Comparative
BH-15-a
BD-15
30
0.140
0.094

Example 240

Example 241 and Comparative Example 241

TABLE 224

Emitting layer

Host
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 241
BH-16
BD-15
38
0.140
0.094

Comparative
BH-16-a
BD-15
26
0.140
0.094

Example 241

Example 242

TABLE 225

Emitting layer

Host
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 242
BH-17
BD-11
67
0.140
0.094

Example 243 and Comparative Example 243

TABLE 226

Emitting layer

Host
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 243
BH-1
BD-16
95
0.141
0.098

Comparative
BH-1-a
BD-16
62
0.141
0.098

Example 243

Example 244 and Comparative Example 244

TABLE 227

Emitting layer

Host
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 244
BH-2
BD-16
54
0.141
0.098

Comparative
BH-2-a
BD-16
35
0.141
0.098

Example 244

Example 245 and Comparative Example 245

TABLE 228

Emitting layer

Host
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 245
BH-3
BD-16
45
0.141
0.098

Comparative
BH-3-a
BD-16
35
0.141
0.098

Example 245

Example 246 and Comparative Example 246

TABLE 229

Emitting layer

Host
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 246
BH-4
BD-16
45
0.141
0.098

Comparative
BH-4-a
BD-16
30
0.141
0.098

Example 246

Example 247 and Comparative Example 247

TABLE 230

Emitting layer

Host
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 247
BH-5
BD-16
104
0.141
0.098

Comparative
BH-5-a
BD-16
70
0.141
0.098

Example 247

Example 248 and Comparative Example 248

TABLE 231

Emitting layer

Host
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 248
BH-6
BD-16
92
0.141
0.098

Comparative
BH-6-a
BD-16
60
0.141
0.098

Example 248

Example 249 and Comparative Example 249

TABLE 232

Emitting layer

Host
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 249
BH-7
BD-16
95
0.141
0.098

Comparative
BH-7-a
BD-16
70
0.141
0.098

Example 249

Example 250 and Comparative Example 250

TABLE 233

Emitting layer

Host
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 250
BH-8
BD-16
72
0.141
0.098

Comparative
BH-8-a
BD-16
50
0.141
0.098

Example 250

Example 251 and Comparative Example 251

TABLE 234

Emitting layer

Host
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 251
BH-9
BD-16
68
0.141
0.098

Comparative
BH-9-a
BD-16
51
0.141
0.098

Example 251

Example 252 and Comparative Example 252

Except that the compounds shown in following (able were used as the materials of the emitting layer (host material and dopant material), the organic EL devices were fabricated and evaluated in the same manner as in Example 1. The results are shown in the following Table.

TABLE 235

Emitting layer

Host
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 252
BH-10
BD-16
63
0.141
0.098

Comparative
BH-10-a
BD-16
48
0.141
0.098

Example 252

Example 253 and Comparative Example 253

TABLE 236

Emitting layer

Host
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 253
BH-11
BD-16
54
0.141
0.098

Comparative
BH-11-a
BD-16
42
0.141
0.098

Example 253

Example 254 and Comparative Example 254

TABLE 237

Emitting layer

Host
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 254
BH-12
BD-16
55
0.141
0.098

Comparative
BH-12-a
BD-16
37
0.141
0.098

Example 254

Example 255 and Comparative Example 255

TABLE 238

Emitting layer

Host
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 255
BH-13
BD-16
50
0.141
0.098

Comparative
BH-13-a
BD-16
33
0.141
0.098

Example 255

Example 256 and Comparative Example 256

TABLE 239

Emitting layer

Host
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 256
BH-14
BD-16
90
0.141
0.098

Comparative
BH-14-a
BD-16
61
0.141
0.098

Example 256

Example 257 and Comparative Example 257

TABLE 240

Emitting layer

Host
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 257
BH-15
BD-16
70
0.141
0.098

Comparative
BH-15-a
BD-16
47
0.141
0.098

Example 257

Example 258 and Comparative Example 258

TABLE 241

Emitting layer

Host
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 258
BH-16
BD-16
63
0.141
0.098

Comparative
BH-16-a
BD-16
42
0.141
0.098

Example 258

Example 259

TABLE 242

Emitting layer

Host
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 259
BH-17
BD-16
99
0.141
0.098

Example 260 and Comparative Example 260

TABLE 243

Emitting layer

Host
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 260
BH-1
BD-17
95
0.140
0.096

Comparative
BH-1-a
BD-17
63
0.140
0.096

Example 260

Example 261 and Comparative Example 261

TABLE 244

Emitting layer

Host
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 261
BH-2
BD-17
44
0.140
0.096

Comparative
BH-2-a
BD-17
30
0.140
0.096

Example 261

Example 262 and Comparative Example 262

TABLE 245

Emitting layer

Host
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 262
BH-3
BD-17
45
0.140
0.096

Comparative
BH-3-a
BD-17
30
0.140
0.096

Example 262

Example 263 and Comparative Example 263

TABLE 246

Emitting layer

Host
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 263
BH-4
BD-17
45
0.140
0.096

Comparative
BH-4-a
BD-17
30
0.140
0.096

Example 263

Example 264 and Comparative Example 264

TABLE 247

Emitting layer

Host
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 264
BH-5
BD-17
105
0.140
0.096

Comparative
BH-5-a
BD-17
71
0.140
0.096

Example 264

Example 265 and Comparative Example 265

TABLE 248

Emitting layer

Host
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 265
BH-6
BD-17
90
0.140
0.096

Comparative
BH-6-a
BD-17
60
0.140
0.096

Example 265

Example 266 and Comparative Example 266

TABLE 249

Emitting layer

Host
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 266
BH-7
BD-17
90
0.140
0.096

Comparative
BH-7-a
BD-17
63
0.140
0.096

Example 266

Example 267 and Comparative Example 267

TABLE 250

Emitting layer

Host
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 267
BH-8
BD-17
72
0.140
0.096

Comparative
BH-8-a
BD-17
50
0.140
0.096

Example 267

Example 268 and Comparative Example 268

TABLE 251

Emitting layer

Host
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 268
BH-9
BD-17
72
0.140
0.096

Comparative
BH-9-a
BD-17
50
0.140
0.096

Example 268

Example 269 and Comparative Example 269

TABLE 252

Emitting layer

Host
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 269
BH-10
BD-17
59
0.140
0.096

Comparative
BH-10-a
BD-17
48
0.140
0.096

Example 269

Example 270 and Comparative Example 270

Except that the compounds shown in following table were used as the materials of the emitting layer (host material and dcpant material), the organic EL devices were fabricated and evaluated in the same manner as in Example 1. The results are shown in the following Table.

TABLE 253

Emitting layer

Host
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 270
BH-11
BD-17
59
0.140
0.096

Comparative
BH-11-a
BD-17
40
0.140
0.096

Example 270

Example 271 and Comparative Example 271

TABLE 254

Emitting layer

Host
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 271
BH-12
BD-17
56
0.140
0.096

Comparative
BH-12-a
BD-17
38
0.140
0.096

Example 271

Example 272 and Comparative Example 272

TABLE 255

Emitting layer

Host
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 272
BH-13
BD-17
50
0.140
0.096

Comparative
BH-13-a
BD-17
34
0.140
0.096

Example 272

Example 273 and Comparative Example 273

TABLE 256

Emitting layer

Host
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 273
BH-14
BD-17
97
0.140
0.096

Comparative
BH-14-a
BD-17
63
0.140
0.096

Example 273

Example 274 and Comparative Example 274

TABLE 257

Emitting layer

Host
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 274
BH-15
BD-17
61
0.140
0.096

Comparative
BH-15-a
BD-17
42
0.140
0.096

Example 274

Example 275 and Comparative Example 275

TABLE 258

Emitting layer

Host
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 275
BH-16
BD-17
67
0.140
0.096

Comparative
BH-16-a
BD-17
45
0.140
0.096

Example 275

Example 276

TABLE 259

Emitting layer

Host
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 276
BH-17
BD-17
95
0.140
0.096

Example 277 and Comparative Example 277

TABLE 260

Emitting layer

Host
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 277
BH-1
BD-18
77
0.143
0.109

Comparative
BH-1-a
BD-18
52
0.143
0.109

Example 277

Example 278 and Comparative Example 278

TABLE 261

Emitting layer

Host
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 278
BH-2
BD-18
36
0.143
0.109

Comparative
BH-2-a
BD-18
29
0.143
0.109

Example 278

Example 279 and Comparative Example 279

TABLE 262

Emitting layer

Host
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 279
BH-3
BD-18
36
0.143
0.109

Comparative
BH-3-a
BD-18
25
0.143
0.109

Example 279

Example 280 and Comparative Example 280

TABLE 263

Emitting layer

Host
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 280
BH-4
BD-18
33
0.143
0.109

Comparative
BH-4-a
BD-18
24
0.143
0.109

Example 280

Example 281 and Comparative Example 281

TABLE 264

Emitting layer

Host
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 281
BH-5
BD-18
81
0.143
0.109

Comparative
BH-5-a
BD-18
53
0.143
0.109

Example 281

Example 282 and Comparative Example 282

TABLE 265

Emitting layer

Host
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 282
BH-6
BD-18
72
0.143
0.109

Comparative
BH-6-a
BD-18
50
0.143
0.109

Example 282

Example 283 and Comparative Example 283

TABLE 266

Emitting layer

Host
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 283
BH-7
BD-18
72
0.143
0.109

Comparative
BH-7-a
BD-18
52
0.143
0.109

Example 283

Example 284 and Comparative Example 284

TABLE 267

Emitting layer

Host
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 284
BH-8
BD-18
54
0.143
0.109

Comparative
BH-8-a
BD-18
40
0.143
0.109

Example 284

Example 285 and Comparative Example 285

TABLE 268

Emitting layer

Host
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 285
BH-9
BD-18
54
0.143
0.109

Comparative
BH-9-a
BD-18
37
0.143
0.109

Example 285

Example 286 and Comparative Example 286

TABLE 269

Emitting layer

Host
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 286
BH-10
BD-18
51
0.143
0.109

Comparative
BH-10-a
BD-18
35
0.143
0.109

Example 286

Example 287 and Comparative Example 287

TABLE 270

Emitting layer

Host
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 287
BH-11
BD-18
48
0.143
0.109

Comparative
BH-11-a
BD-18
31
0.143
0.109

Example 287

Example 288 and Comparative Example 288

TABLE 271

Emitting layer

Host
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 288
BH-12
BD-18
43
0.143
0.110

Comparative
BH-12-a
BD-18
31
0.143
0.110

Example 288

Example 289 and Comparative Example 289

TABLE 272

Emitting layer

Host
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 289
BH-13
BD-18
36
0.143
0.109

Comparative
BH-13-a
BD-18
25
0.143
0.109

Example 289

Example 290 and Comparative Example 290

TABLE 273

Emitting layer

Host
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 290
BH-14
BD-18
71
0.143
0.109

Comparative
BH-14-a
BD-18
48
0.143
0.109

Example 290

Example 291 and Comparative Example 291

TABLE 274

Emitting layer

Host
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 291
BH-15
BD-18
56
0.143
0.109

Comparative
BH-15-a
BD-18
38
0.143
0.109

Example 291

Example 292 and Comparative Example 292

TABLE 275

Emitting layer

Host
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 292
BH-16
BD-18
46
0.143
0.109

Comparative
BH-16-a
BD-18
32
0.143
0.109

Example 292

Example 293 and Comparative Example 293

TABLE 276

Emitting layer

Host
Dopant
Chromaticity

material
material
LT95(h)
CIEx
CIEy

Example 293
BH-17
BD-18
75
0.143
0.109

From the results of Tables 1 to 276, it can be recognized that, if the compound represented by the formula (1) (host material) having a deuterium atom at the particular position is used in combination with the particular dopant material in the emitting layer of the organic EL device, the lifetime of the organic EL device is prolonged compared with the case where the compound (host material) having no deuterium atom at the particular position is used in combination with the corresponding dopant material.

Several embodiments and/or examples of the present invention have been described in detail above. However, without substantially departing from novel teachings and effects of the present invention, the person skilled in the art can readily make a number of modifications to the embodiments and/or examples which are exemplifications of these teachings and effects. Thus, these modifications are inducted in the scope of the present invention.

The documents described in this specification and the contents of the application that serves as the basis of priority claim under Paris convention are incorporated herein by reference in its entirety.

Number	Date	Country	Kind
2018-190838	Oct 2018	JP	national
2018-191224	Oct 2018	JP	national
2019-101578	May 2019	JP	national
2019-101675	May 2019	JP	national

	Number	Date	Country
Parent	16557675	Aug 2019	US
Child	17282971		US
Parent	16593743	Oct 2019	US
Child	16557675		US

ORGANIC ELECTROLUMINESCENCE DEVICE AND ELECTRONIC APPARATUS PROVIDED WITH THE SAME

Information

Publication Number

Date Filed

Date Published

Inventors

Original Assignees

CPC

International Classifications

Abstract

Description

Claims

Priority Claims (4)

PCT Information

Continuation in Parts (2)