JP6830827B2 - Materials for organic electroluminescence devices, electronic devices and organic electroluminescence devices - Google Patents

Description

The present invention relates to organic electroluminescence devices, electronic devices, and materials for organic electroluminescence devices.

When a voltage is applied to an organic electroluminescence device (hereinafter referred to as an organic EL device), holes are injected from the anode and electrons are injected from the cathode into the light emitting layer. Then, in the light emitting layer, the injected holes and electrons are recombined to form excitons.

The organic EL element includes a light emitting layer between the anode and the cathode. In addition, it may have a laminated structure including an organic layer such as a hole injection layer, a hole transport layer, an electron injection layer, and an electron transport layer.

Patent Document 1 discloses an asymmetric pyrene derivative having a specific structure.

Patent Document 2 discloses an organic electroluminescent device in which at least one layer containing at least one novel hydrocarbon compound in which an anthracene ring and a fluorene ring are directly bonded is sandwiched between a pair of electrodes. ..

International Publication No. 2005/1195950 International Publication No. 2002/014244

An object of the present invention is to provide a material for an organic electroluminescence device, an electronic device, and an organic electroluminescence device having a low voltage and a long life.

（式（１）において、Ｒ_１０１〜Ｒ_１１０は、それぞれ独立に、水素原子、ハロゲン原子、シアノ基、置換もしくは無置換の環形成炭素数６〜５０のアリール基、置換もしくは無置換の環形成原子数５〜５０のヘテロアリール基、置換もしくは無置換の炭素数１〜５０のアルキル基、置換もしくは無置換の炭素数２〜５０のアルケニル基、置換もしくは無置換の環形成炭素数３〜５０のシクロアルキル基、置換もしくは無置換の炭素数１〜５０のアルコキシ基、置換もしくは無置換の炭素数７〜５０のアラルキル基、置換もしくは無置換の環形成炭素数６〜５０のアリールオキシ基、置換もしくは無置換のシリル基、又は−Ｌ_１０１−Ａｒ_１０１で表される基である。
ただし、Ｒ_１０１〜Ｒ_１１０の少なくとも１つは、−Ｌ_１０１−Ａｒ_１０１で表される基である。Ｌ_１０１は、単結合、置換もしくは無置換の環形成炭素数６〜１８のアリーレン基、又は置換もしくは無置換の環形成原子数５〜１５のヘテロアリーレン基であり、Ａｒ_１０１は、置換もしくは無置換の環形成炭素数６〜５０のアリール基、又は置換もしくは無置換の環形成原子数５〜５０のヘテロアリール基である。Ｌ_１０１が２以上の場合、２以上のＬ_１０１は同一でもよく、異なっていてもよい。Ａｒ_１０１が２以上の場合、２以上のＡｒ_１０１は同一でもよく、異なっていてもよい。）

（式（２）において、Ｒ_２０１〜Ｒ_２１０は、それぞれ独立に、水素原子、ハロゲン原子、シアノ基、置換もしくは無置換の環形成炭素数６〜５０のアリール基、置換もしくは無置換の環形成原子数５〜５０のヘテロアリール基、置換もしくは無置換の炭素数１〜５０のアルキル基、置換もしくは無置換の炭素数２〜５０のアルケニル基、置換もしくは無置換の環形成炭素数３〜５０のシクロアルキル基、置換もしくは無置換の炭素数１〜５０のアルコキシ基、置換もしくは無置換の炭素数７〜５０のアラルキル基、置換もしくは無置換の環形成炭素数６〜５０のアリールオキシ基、置換もしくは無置換のシリル基、又は−Ｌ_２０１−Ａｒ_２０１で表される基である。
ただし、Ｒ_２０１〜Ｒ_２１０の少なくとも１つは、−Ｌ_２０１−Ａｒ_２０１で表される基である。Ｌ_２０１は、単結合、置換もしくは無置換の環形成炭素数６〜１８のアリーレン基、又は置換もしくは無置換の環形成原子数５〜１５のヘテロアリーレン基であり、Ａｒ_２０１は、置換もしくは無置換の環形成炭素数６〜５０のアリール基、又は置換もしくは無置換の環形成原子数５〜５０のヘテロアリール基である。Ｌ_２０１が２以上の場合、２以上のＬ_２０１は同一でもよく、異なっていてもよい。Ａｒ_２０１が２以上の場合、２以上のＡｒ_２０１は同一でもよく、異なっていてもよい。） According to one aspect of the present invention, the following organic EL elements are provided.
With the cathode
With the anode
A light emitting layer arranged between the cathode and the anode,
Have,
An organic electroluminescence device in which the light emitting layer contains a first material represented by the following formula (1), a second material represented by the following formula (2), and a third material which is an amine compound.

(In the formula (1), R _{101 to} R ₁₁₀ independently form a hydrogen atom, a halogen atom, a cyano group, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, and a substituted or unsubstituted ring formation. Heteroaryl groups with 5 to 50 atoms, substituted or unsubstituted alkyl groups with 1 to 50 carbon atoms, substituted or unsubstituted alkoxy groups with 2 to 50 carbon atoms, substituted or unsubstituted ring-forming carbon atoms 3 to 50 Cycloalkyl group, substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms, substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, substituted or unsubstituted ring-forming aryloxy group having 6 to 50 carbon atoms, It is a substituted or unsubstituted silyl group, or a group represented by −L _101- Ar ₁₀₁ .
However, at least one of R _{101 to} R ₁₁₀ is a group represented by -L _101- Ar ₁₀₁ . L ₁₀₁ is a single-bonded, substituted or unsubstituted ring-forming carbon number 6-18 arylene group, or substituted or unsubstituted ring-forming atomic number 5 to 15 heteroarylene group, and Ar ₁₀₁ is substituted or unsubstituted. A substituted aryl group having 6 to 50 carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 50 ring-forming atoms. When L ₁₀₁ is 2 or more, 2 or more L ₁₀₁ may be the same or different. If Ar ₁₀₁ is 2 or more, two or more _{Ar 101} may be the same or different. )

(In the formula (2), R _{201 to} R ₂₁₀ independently form a hydrogen atom, a halogen atom, a cyano group, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, and a substituted or unsubstituted ring formation. Heteroaryl groups with 5 to 50 atoms, substituted or unsubstituted alkyl groups with 1 to 50 carbon atoms, substituted or unsubstituted alkoxy groups with 2 to 50 carbon atoms, substituted or unsubstituted ring-forming carbon atoms 3 to 50 Cycloalkyl group, substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms, substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, substituted or unsubstituted ring-forming aryloxy group having 6 to 50 carbon atoms, It is a substituted or unsubstituted silyl group, or a group represented by −L _201- Ar ₂₀₁ .
However, at least one of R _{201 to} R ₂₁₀ is a group represented by -L _201- Ar ₂₀₁ . L ₂₀₁ is a single-bonded, substituted or unsubstituted ring-forming carbon number 6 to 18 arylene group, or substituted or unsubstituted ring-forming atomic number 5 to 15 heteroarylene group, and Ar ₂₀₁ is substituted or unsubstituted. A substituted aryl group having 6 to 50 carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 50 ring-forming atoms. When L ₂₀₁ is 2 or more, 2 or more L ₂₀₁ may be the same or different. If Ar ₂₀₁ is 2 or more, two or more _{Ar 201} may be the same or different. )

According to another aspect of the present invention, an electronic device including the organic EL element is provided.

According to another aspect of the present invention, the following materials for organic EL devices are provided.
A material for an organic electroluminescence device containing a first material represented by the above formula (1), a second material represented by the above formula (2), and a third material which is an amine compound.

According to the present invention, it is possible to provide a material for an organic electroluminescence device, an electronic device, and an organic electroluminescence device having a low voltage and a long life.

It is a figure which shows the schematic structure of one Embodiment of the organic EL element of this invention.

In the present specification, the hydrogen atom includes isotopes having different numbers of neutrons, that is, hydrogen (protium), deuterium (deuterium), and tritium (tritium).

In the present specification, the ring-forming carbon number constitutes the ring itself of a compound having a structure in which atoms are cyclically bonded (for example, a monocyclic compound, a fused ring compound, a crosslinked compound, a carbocyclic compound, or a heterocyclic compound). Represents the number of carbon atoms in an atom. When the ring is substituted with a substituent, the carbon contained in the substituent is not included in the ring-forming carbon number. The "ring-forming carbon number" described below shall be the same unless otherwise specified. For example, a benzene ring has 6 ring-forming carbon atoms, a naphthalene ring has 10 ring-forming carbon atoms, a pyridinyl group has 5 ring-forming carbon atoms, and a flanyl group has 4 ring-forming carbon atoms. When, for example, an alkyl group is substituted as a substituent on the benzene ring or naphthalene ring, the number of carbon atoms of the alkyl group is not included in the number of ring-forming carbon atoms. When, for example, a fluorene ring is bonded to the fluorene ring as a substituent (including a spirofluorene ring), the number of carbon atoms of the fluorene ring as a substituent is not included in the number of ring-forming carbon atoms.

In the present specification, the number of ring-forming atoms refers to a compound having a structure in which atoms are cyclically bonded (for example, a monocycle, a fused ring, or a ring assembly) (for example, a monocyclic compound, a fused ring compound, a crosslinked compound, a carbocyclic compound, or a complex). It represents the number of atoms constituting the ring itself of the ring compound). The number of ring-forming atoms does not include atoms that do not form a ring (for example, a hydrogen atom that terminates the bond of an atom that forms a ring) or atoms that are included in the substituent when the ring is substituted by a substituent. The "number of ring-forming atoms" described below shall be the same unless otherwise specified. For example, the pyridine ring has 6 ring-forming atoms, the quinazoline ring has 10 ring-forming atoms, and the furan ring has 5 ring-forming atoms. Hydrogen atoms bonded to carbon atoms of the pyridine ring and quinazoline ring and atoms constituting substituents are not included in the number of ring-forming atoms. When, for example, a fluorene ring is bonded to the fluorene ring as a substituent (including a spirofluorene ring), the number of atoms of the fluorene ring as a substituent is not included in the number of ring-forming atoms.

In the present specification, the "carbon number XX to YY" in the expression "ZZ group of substituted or unsubstituted carbon number XX to YY" represents the carbon number when the ZZ group is unsubstituted, and is substituted. If so, the carbon number of the substituent is not included. Here, "YY" is larger than "XX", and "XX" and "YY" mean integers of 1 or more, respectively.

In the present specification, the "atomic number XX to YY" in the expression "ZZ group of atomic number XX to YY substituted or unsubstituted" represents the number of atoms when the ZZ group is unsubstituted, and is substituted. If so, the number of atoms of the substituent is not included. Here, "YY" is larger than "XX", and "XX" and "YY" mean integers of 1 or more, respectively.

In the case of "substituted or unsubstituted", "unsubstituted" means that the substituent is not substituted and a hydrogen atom is bonded.

（式中、Ｘ_１Ａ〜Ｘ_６Ａ，Ｙ_１Ａ〜Ｙ_６Ａはそれぞれ酸素原子、硫黄原子、窒素原子、−ＮＺ−基、又は−ＮＨ−基である。
Ｚは、置換もしくは無置換の環形成炭素数６〜５０のアリール基、置換もしくは無置換の環形成原子数５〜５０のヘテロアリール基、又は置換もしくは無置換の炭素数１〜５０のアルキル基である。Ｚが２以上の場合、２以上のＺは同一でもよく、異なっていてもよい。） In the present specification, the heteroaryl group also includes the following groups. The heteroarylene group also includes a group based on the following groups as divalent groups.

(In the formula, X _{1A to} X _6A and Y _{1A to} Y _6A are an oxygen atom, a sulfur atom, a nitrogen atom, an -NZ- group, or an -NH- group, respectively.
Z is an aryl group having 6 to 50 substituted or unsubstituted ring-forming carbon atoms, a heteroaryl group having 5 to 50 substituted or unsubstituted ring-forming atoms, or an alkyl group having 1 to 50 substituted or unsubstituted ring-forming atoms. Is. When Z is 2 or more, Z of 2 or more may be the same or different. )

Examples of the aryl group having 6 to 50 ring-forming carbon atoms of Z include those similar to the aryl group having 6 to 50 ring-forming carbon atoms such as R _{101 to} R ₁₁₀ described later.
Examples of the heteroaryl group having 5 to 50 ring-forming atoms in Z include the same heteroaryl groups having 5 to 50 ring-forming atoms as described below, such as R _{101 to} R ₁₁₀ .
Examples of the alkyl group having 1 to 50 carbon atoms of Z include those similar to the alkyl group having 1 to 50 carbon atoms such as R _{101 to} R ₁₁₀ described later.

One aspect of the organic EL device of the present invention includes a cathode, an anode, and a light emitting layer arranged between the cathode and the anode, and the light emitting layer is represented by the following formula (1). It contains a first material, a second material represented by the following formula (2), and a third material which is an amine compound.
As a result, the voltage can be lowered and the life can be extended.

One aspect of the material for an organic EL device of the present invention contains a first material represented by the following formula (1), a second material represented by the following formula (2), and a third material which is an amine compound. ..
As a result, an organic electroluminescence device having a low voltage and a long life can be obtained.

The first material represented by the formula (1) is preferably 4% by mass or more and 92% by mass or less, and 8% by mass or more and 90% by mass or less with respect to 100% by mass of the material for the organic EL device. Is more preferable.
The second material represented by the formula (2) is preferably 4% by mass or more and 92% by mass or less, and 8% by mass or more and 90% by mass or less with respect to 100% by mass of the material for the organic EL device. Is more preferable.
The third material, which is an amine compound, is preferably 1% by mass or more and 20% by mass or less, and more preferably 2% by mass or more and 8% by mass or less with respect to 100% by mass of the material for an organic EL device.

One aspect of the material for an organic EL device of the present invention is essentially from a first material represented by the formula (1), a second material represented by the formula (2), and a third material which is an amine compound. In addition, other unavoidable impurities may be contained as long as the effects of the present invention are not impaired.

In the formula (1), R _{101 to} R ₁₁₀ are independently hydrogen atom, halogen atom, cyano group, substituted or unsubstituted aryl group having 6 to 50 carbon atoms, substituted or unsubstituted ring-forming atom. Heteroaryl groups of 5 to 50, substituted or unsubstituted alkyl groups of 1 to 50 carbon atoms, substituted or unsubstituted alkoxy groups of 2 to 50 carbon atoms, substituted or unsubstituted ring-forming groups of 3 to 50 carbon atoms. Cycloalkyl groups, substituted or unsubstituted alkoxy groups with 1 to 50 carbon atoms, substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms, substituted or unsubstituted ring-forming aryloxy groups with 6 to 50 carbon atoms, substituted Alternatively, it is an unsubstituted silyl group or a group represented by -L _101- Ar ₁₀₁ .
However, at least one (preferably at least two, more preferably two) of R _{101 to} R ₁₁₀ is a group represented by -L _101- Ar ₁₀₁ . L ₁₀₁ is a single-bonded, substituted or unsubstituted ring-forming carbon number 6-18 arylene group, or substituted or unsubstituted ring-forming atomic number 5 to 15 heteroarylene group, and Ar ₁₀₁ is substituted or unsubstituted. A substituted aryl group having 6 to 50 carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 50 ring-forming atoms. When L ₁₀₁ is 2 or more, 2 or more L ₁₀₁ may be the same or different. If Ar ₁₀₁ is 2 or more, two or more _{Ar 101} may be the same or different.

In the formula (2), R _{201 to} R ₂₁₀ are independently hydrogen atom, halogen atom, cyano group, substituted or unsubstituted aryl group having 6 to 50 carbon atoms, substituted or unsubstituted ring-forming atom. Heteroaryl groups of 5 to 50, substituted or unsubstituted alkyl groups of 1 to 50 carbon atoms, substituted or unsubstituted alkoxy groups of 2 to 50 carbon atoms, substituted or unsubstituted ring-forming groups of 3 to 50 carbon atoms. Cycloalkyl groups, substituted or unsubstituted alkoxy groups with 1 to 50 carbon atoms, substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms, substituted or unsubstituted ring-forming aryloxy groups with 6 to 50 carbon atoms, substituted Alternatively, it is an unsubstituted silyl group or a group represented by -L _201- Ar ₂₀₁ .
However, at least one of R _{201 to} R ₂₁₀ is a group represented by -L _201- Ar ₂₀₁ . L ₂₀₁ is a single-bonded, substituted or unsubstituted ring-forming carbon number 6 to 18 arylene group, or substituted or unsubstituted ring-forming atomic number 5 to 15 heteroarylene group, and Ar ₂₀₁ is substituted or unsubstituted. A substituted aryl group having 6 to 50 carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 50 ring-forming atoms. When L ₂₀₁ is 2 or more, 2 or more L ₂₀₁ may be the same or different. If Ar ₂₀₁ is 2 or more, two or more _{Ar 201} may be the same or different.

R _{101 to} R ₁₀₈ of the formula (1) are preferably hydrogen atoms.

R ₁₀₉ and R ₁₁₀ of the formula (1) are groups represented by −L _101- Ar ₁₀₁ , and it is preferable that L ₁₀₁ is a substituted or unsubstituted phenylene group or a substituted or unsubstituted naphthylene group. ..

Further, at least one of R ₁₀₉ and R ₁₁₀ of the formula (1) is a group represented by -L _101- Ar ₁₀₁ , in which Ar ₁₀₁ is a substituted or unsubstituted fluorenyl group, substituted or unsubstituted dibenzofuranyl. It is preferably selected from the group consisting of groups and substituted or unsubstituted dibenzothiophenyl groups.

_R 101 _{to R 110} of Formula (1), _R 201 _{to R 210} in formula (2), _R in the formula below _{(3A), R} 1 to R ₈ of Formula (3) below, described below formula (5) Examples of the halogen atoms of R _{11 to} R _{17 of the above} and R _{21 to} R ₂₇ and R _{31 to} R ₃₇ of the formula (7) described later include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom.

R _{101 to} R ₁₁₀ and Ar _{101 of} the formula (1), R _{201 to} R ₂₁₀ and Ar _{201 of} the formula (2), R and Ar of the formula (3A) described later, R _{1 to} R of the formula (3) described later. _10. Ar ₁ and Ar ₂ of the formula (4) described later, R _{11 to} R ₁₇ of the formula (5) described later, Ar ₃ and Ar ₄ of the formula (6) described later, and R of the formula (7) described later. Examples of the aryl group having 6 to 50 (preferably 6 to 18) ring-forming carbon atoms of _{21 to} R ₂₇ and R _{31 to} R ₃₇ include a phenyl group, a 1-naphthyl group, a 2-naphthyl group, and a 1-anthryl group. , 2-Anthryl group, 9-Anthryl group, 1-Phenyltril group, 2-Phenyltril group, 3-Phenyltril group, 4-Phenyltril group, 9-Phenyltril group, 1-naphthacenyl group, 2-naphthacenyl group, 9-naphthacenyl group , 1-pyrenyl group, 2-pyrenyl group, 4-pyrenyl group, 2-biphenylyl group, 3-biphenylyl group, 4-biphenylyl group, p-terphenyl4-yl group, p-terphenyl3-yl Group, p-terphenyl2-yl group, m-terphenyl4-yl group, m-terphenyl3-yl group, m-terphenyl2-yl group, o-tryl group, m-tryl group, p- Trill group, pt-butylphenyl group, p- (2-phenylpropyl) phenyl group, 3-methyl-2-naphthyl group, 4-methyl-1-naphthyl group, 4-methyl-1-anthryl group, 4 ′ -Methylbiphenylyl group, 4 ″ -t-butyl-p-terphenyl4-yl group, chrysenyl group, fluoranthenyl group, fluorenyl group and the like can be mentioned.
Among these, phenyl group, naphthyl group, biphenyl group, terphenyl group, pyrenyl group, phenanthryl group and fluorenyl group are preferable, and phenyl group, naphthyl group, biphenyl group, terphenyl group, pyrenyl group and It is a fluorenyl group.

R _{101 to} R ₁₁₀ and Ar _{101 of} the formula (1), R _{201 to} R ₂₁₀ and Ar _{201 of} the formula (2), R and Ar of the formula (3A) described later, R _{1 to} R of the formula (3) described later. _10. Ar ₁ and Ar ₂ of the formula (4) described later, R _{11 to} R ₁₇ of the formula (5) described later, Ar ₃ and Ar ₄ of the formula (6) described later, and R of the formula (7) described later. Examples of the heteroaryl group having 5 to 50 ring-forming atoms (preferably 5 to 18) of _{21 to} R ₂₇ and R _{31 to} R ₃₇ include a pyrrolyl group, a pyrazineyl group, a pyridinyl group, an indole group, an isoindryl group and a frill group. Benzofuranyl group, isobenzofuranyl group, dibenzofuranyl group, dibenzothiophenyl group, quinolyl group, isoquinolyl group, quinoxalinyl group, carbazolyl group, phenanthridinyl group, acridinyl group, phenanthrolinyl group, and thienyl group, In addition, pyridine ring, pyrazine ring, pyrimidine ring, pyridazine ring, triazine ring, indole ring, quinoline ring, acrydin ring, pyrrolidine ring, dioxane ring, piperidine ring, morpholine ring, piperazin ring, carbazole ring, furan ring, thiophene ring, Oxazole ring, oxaziazole ring, benzoxazole ring, thiazole ring, thiazazole ring, benzothiazole ring, triazole ring, imidazole ring, benzoimidazole ring, pyran ring, dibenzofuran ring, benzo [a] dibenzofuran ring, benzo [b] dibenzofuran Examples thereof include a monovalent group formed from a ring and a benzo [c] dibenzofuran ring.

_R 101 _{to R 110} of Formula (1), _R 201 _{to R 210} in formula (2), _R in the formula below _{(3A), R} 1 to R ₈ of Formula (3) below, described below formula (5) R _{11 to} R ₁₇ , and R _{21 to} R ₂₇ and R _{31 to} R ₃₇ of the formula (7) described later, examples of the alkyl group having 1 to 50 carbon atoms (preferably 1 to 18) include a methyl group. Ethyl group, propyl group, isopropyl group, n-butyl group, s-butyl group, isobutyl group, t-butyl group, n-pentyl group, n-hexyl group, n-heptyl group, n-octyl group, hydroxymethyl group , 1-Hydroxyethyl group, 2-Hydroxyethyl group, 2-Hydroxyisobutyl group, 1,2-dihydroxyethyl group, 1,3-dihydroxyisopropyl group, 2,3-dihydroxy-t-butyl group, 1,2, 3-Trihydroxypropyl group, chloromethyl group, 1-chloroethyl group, 2-chloroethyl group, 2-chloroisobutyl group, 1,2-dichloroethyl group, 1,3-dichloroisopropyl group, 2,3-dichloro-t -Butyl group, 1,2,3-trichloropropyl group, bromomethyl group, 1-bromoethyl group, 2-bromoethyl group, 2-bromoisobutyl group, 1,2-dibromoethyl group, 1,3-dibromoisopropyl group, 2 , 3-Dibromo-t-butyl group, 1,2,3-tribromopropyl group, iodomethyl group, 1-iodoethyl group, 2-iodoethyl group, 2-iodoisobutyl group, 1,2-diiodoethyl group, 1,3 -Diodeisopropyl group, 2,3-diiodo-t-butyl group, 1,2,3-triiodopropyl group, aminomethyl group, 1-aminoethyl group, 2-aminoethyl group, 2-aminoisobutyl group, 1,2-Diaminoethyl group, 1,3-diaminoisopropyl group, 2,3-diamino-t-butyl group, 1,2,3-triaminopropyl group, cyanomethyl group, 1-cyanoethyl group, 2-cyanoethyl group , 2-Cyanoisobutyl group, 1,2-dicyanoethyl group, 1,3-dicyanoisopropyl group, 2,3-dicyano-t-butyl group, 1,2,3-tricyanopropyl group, nitromethyl group, 1- Nitroethyl group, 2-nitroethyl group, 2-nitroisobutyl group, 1,2-dinitroethyl group, 1,3-dinitroisopropyl group, 2,3-dinitro-t-butyl group, 1,2,3-trinitropropyl Butyl etc. can be mentioned.

_R 101 _{to R 110} of Formula (1), _R 201 _{to R 210} in formula (2), _R in the formula below _{(3A), R} 1 to R ₈ of Formula (3) below, described below formula (5) R _{11 to} R ₁₇ and R _{21 to} R ₂₇ and R _{31 to} R ₃₇ of the formula (7) described later have alkenyl groups having 2 to 50 carbon atoms (preferably 2 to 18) as vinyl groups and allyl groups. , 1-butenyl group, 2-butenyl group, 3-butenyl group, 1,3-butanjienyl group, 1-methylvinyl group, 1-methylallyl group, 1,1-dimethylallyl group, 2-methylallyl group, 1,2 -Examples include a dimethylallyl group.

_R 101 _{to R 110} of Formula (1), _R 201 _{to R 210} in formula (2), _R in the formula below _{(3A), R} 1 to R ₈ of Formula (3) below, described below formula (5) As the cycloalkyl group having 3 to 50 (preferably 3 to 18) ring-forming carbon atoms of R _{11 to} R ₁₇ and R _{21 to} R ₂₇ and R _{31 to} R ₃₇ of the formula (7) described later, cyclopropyl Examples thereof include a group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a 4-methylcyclohexyl group, a 1-adamantyl group, a 2-adamantyl group, a 1-norbornyl group, a 2-norbornyl group and the like.

_R 101 _{to R 110} of Formula (1), _R 201 _{to R 210} in formula (2), _R in the formula below _{(3A), R} 1 to R ₈ of Formula (3) below, described below formula (5) The alkoxy groups (preferably 1 to 18) of R _{11 to} R _{17 of the above} and R _{21 to} R ₂₇ and R _{31 to} R ₃₇ of the formula (7) described later are, for example, the above-mentioned alkyl having 1 to 50 carbon atoms. Examples thereof include a group in which an oxygen atom is bonded to the group.

_R 101 _{to R 110} of Formula (1), _R 201 _{to R 210} in formula (2), _R in the formula below _{(3A), R} 1 to R ₈ of Formula (3) below, described below formula (5) As the aralkyl group having 7 to 50 carbon atoms (preferably 7 to 18) of R _{11 to} R ₁₇ and R _{21 to} R ₂₇ and R _{31 to} R ₃₇ of the formula (7) described later, for example, a benzyl group. 1-phenylethyl group, 2-phenylethyl group, 1-phenylisopropyl group, 2-phenylisopropyl group, phenyl-t-butyl group, α-naphthylmethyl group, 1-α-naphthylethyl group, 2-α-naphthyl Ethyl group, 1-α-naphthyl isopropyl group, 2-α-naphthyl isopropyl group, β-naphthyl methyl group, 1-β-naphthyl ethyl group, 2-β-naphthyl ethyl group, 1-β-naphthyl isopropyl group, 2 -Β-naphthylisopropyl group, 1-pyrrolylmethyl group, 2- (1-pyrrrolyl) ethyl group, p-methylbenzyl group, m-methylbenzyl group, o-methylbenzyl group, p-chlorobenzyl group, m-chlorobenzyl Group, o-chlorobenzyl group, p-bromobenzyl group, m-bromobenzyl group, o-bromobenzyl group, p-iodobenzyl group, m-iodobenzyl group, o-iodobenzyl group, p-hydroxybenzyl group, m-hydroxybenzyl group, o-hydroxybenzyl group, p-aminobenzyl group, m-aminobenzyl group, o-aminobenzyl group, p-nitrobenzyl group, m-nitrobenzyl group, o-nitrobenzyl group, p- Examples thereof include a cyanobenzyl group, an m-cyanobenzyl group, an o-cyanobenzyl group, a 1-hydroxy-2-phenylisopropyl group and a 1-chloro-2-phenylisopropyl group.

_R 101 _{to R 110} of Formula (1), _R 201 _{to R 210} in formula (2), _R in the formula below _{(3A), R} 1 to R ₈ of Formula (3) below, described below formula (5) Examples of the aryloxy group having 6 to 50 (preferably 6 to 18) ring-forming carbon atoms of R _{11 to} R ₁₇ and R _{21 to} R ₂₇ and R _{31 to} R ₃₇ of the formula (7) described later include, for example. Examples thereof include a group in which an oxygen atom is bonded to the above aryl group having 6 to 50 carbon atoms.

_R 101 _{to R 110} of Formula (1), _R 201 _{to R 210} in formula (2), _R in the formula below _{(3A), R} 1 to R ₈ of Formula (3) below, described below formula (5) As the substituted or unsubstituted silyl groups of R _{11 to} R ₁₇ and R _{21 to} R ₂₇ and R _{31 to} R ₃₇ of the formula (7) described later, an unsubstituted silyl group (-SiH ₃ ) and a trialkyl Examples thereof include a silyl group and a triarylsilyl group. The alkyl group and aryl group are as described below for any substituent.

An arylene group having 6 to 18 (preferably 6 to 12) ring-forming carbon atoms of L _{101 of} the formula (1), L ₂₀₁ of the formula (2), and L ₁ , L ₂ and L ₃ of the formula (4) described later. Examples of the phenylene group (for example, m-phenylene group), naphthylene group, biphenylene group, anthranylene group, pyrenylene group and the like can be mentioned.

Heteroarylene of formula (1) L ₁₀₁ , formula (2) L ₂₀₁ , and ring-forming atoms 5 to 15 (preferably 5 to 12) of formula (4) L ₁ , L ₂ and L ₃ described later. Examples of the group include a non-condensed heteroarylene group and a condensed heteroarylene group, and more specifically, a pyrrolyl group, a pyrazinyl group, a pyridinyl group, an indole group, an isoindryl group, a frill group, a benzofuranyl group and an isobenzofuranyl group. , Dibenzofuranyl group, dibenzothiophenyl group, quinolyl group, isoquinolyl group, quinoxalinyl group, carbazolyl group, phenanthridinyl group, acridinyl group, phenanthrolinyl group, and thienyl group-based group, In addition, pyridine ring, pyrazine ring, pyrimidine ring, pyridazine ring, triazine ring, indole ring, quinoline ring, aclysin ring, pyrrolidine ring, dioxane ring, piperidine ring, morpholine ring, piperazine ring, carbazole ring, furan ring, thiophene ring, Oxazole ring, oxaziazole ring, benzoxazole ring, thiazole ring, thiazazole ring, benzothiazole ring, triazole ring, imidazole ring, benzoimidazole ring, pyrane ring, dibenzofuran ring, benzo [a] dibenzofuran ring, benzo [b] dibenzofuran Examples thereof include a divalent group formed from a ring and a benzo [c] dibenzofuran ring.

Specific examples of the first material represented by the formula (1) include the compounds shown below.

Further, as the first material represented by the formula (1), the following compounds and the like may be used.

R _{202 to} R ₂₁₀ of the formula (2) are preferably hydrogen atoms.

R ₂₀₁ of the formula (2) is a group represented by −L _201- Ar ₂₀₁ , and it is preferable that Ar ₂₀₁ is a substituted or unsubstituted phenyl group or a substituted or unsubstituted naphthyl group.

Further, R ₂₀₁ of the formula (2) is a group represented by -L _201- Ar ₂₀₁ , in which Ar ₂₀₁ is a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted dibenzofuranyl group, and a substituted or absent. It is preferably selected from the group consisting of substituted dibenzothiophenyl groups.

Specific examples of the second material represented by the formula (2) include the compounds shown below.

Further, as the second material represented by the formula (2), the following compounds and the like may be used.

In the following structural formula, Me represents a methyl group.

（式（３Ａ）において、Ａｒは、置換もしくは無置換の環形成炭素数６〜５０のアリール基、又は置換もしくは無置換の環形成原子数５〜５０のヘテロアリール基である。
Ｒは、それぞれ独立に、ハロゲン原子、シアノ基、置換もしくは無置換の環形成炭素数６〜５０のアリール基、置換もしくは無置換の環形成原子数５〜５０のヘテロアリール基、置換もしくは無置換の炭素数１〜５０のアルキル基、置換もしくは無置換の炭素数２〜５０のアルケニル基、置換もしくは無置換の環形成炭素数３〜５０のシクロアルキル基、置換もしくは無置換の炭素数１〜５０のアルコキシ基、置換もしくは無置換の炭素数７〜５０のアラルキル基、置換もしくは無置換の環形成炭素数６〜５０のアリールオキシ基、置換もしくは無置換のシリル基、又は下記式（４）で表される基を示す。Ｒの少なくとも１つは下記式（４）で表される基である。
ｍは１以上の整数である。

（式（４）において、Ａｒ_１及びＡｒ_２は、それぞれ独立に、置換もしくは無置換の環形成炭素数６〜５０のアリール基、又は置換もしくは無置換の環形成原子数５〜５０のヘテロアリール基である。Ｌ_１、Ｌ_２及びＬ_３は、それぞれ独立に、単結合、置換もしくは無置換の環形成炭素数６〜１８のアリーレン基、又は置換もしくは無置換の環形成原子数５〜１５のヘテロアリーレン基である。）
Ｒ，Ａｒ_１、Ａｒ_２、Ｌ_１、Ｌ_２及びＬ_３が２以上の場合、２以上のＲ，Ａｒ_１、Ａｒ_２、Ｌ_１、Ｌ_２及びＬ_３は同一でもよく、異なっていてもよい。） The third material, which is an amine compound, is preferably represented by the following formula (3A).

(In formula (3A), Ar is a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 50 ring-forming atoms.
R is independently a halogen atom, a cyano group, a substituted or unsubstituted aryl group having 6 to 50 ring-forming atoms, a substituted or unsubstituted heteroaryl group having 5 to 50 ring-forming atoms, substituted or unsubstituted. Alkyl groups having 1 to 50 carbon atoms, substituted or unsubstituted alkenyl groups having 2 to 50 carbon atoms, substituted or unsubstituted ring-forming groups having 3 to 50 carbon atoms, substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms. 50 alkoxy groups, substituted or unsubstituted aralkyl groups having 7 to 50 carbon atoms, substituted or unsubstituted ring-forming aryloxy groups having 6 to 50 carbon atoms, substituted or unsubstituted silyl groups, or the following formula (4). Indicates a group represented by. At least one of R is a group represented by the following formula (4).
m is an integer of 1 or more.

(In the formula (4), Ar ₁ and Ar ₂ are independently substituted or unsubstituted aryl groups having 6 to 50 ring-forming atoms, or substituted or unsubstituted heteroaryls having 5 to 50 ring-forming atoms. The groups L ₁ , L ₂ and L ₃ are independently single-bonded, substituted or unsubstituted arylene groups having 6 to 18 ring-forming carbon atoms, or substituted or unsubstituted ring-forming atoms having 5 to 15 atoms, respectively. It is a heteroarylene group of.)
When R, Ar ₁ , Ar ₂ , L ₁ , L ₂ and L ₃ are 2 or more, 2 or more R, Ar ₁ , Ar ₂ , L ₁ , L ₂ and L ₃ may be the same or different. Good. )

The aryl group having 6 to 50 carbon atoms and the heteroaryl group having 5 to 50 ring-forming atoms of Ar in the formula (3A) are m hydrogen atoms substituted with R.

（式（３）において、Ｒ_１〜Ｒ_１０は、それぞれ独立に、水素原子、ハロゲン原子、シアノ基、置換もしくは無置換の環形成炭素数６〜５０のアリール基、置換もしくは無置換の環形成原子数５〜５０のヘテロアリール基、置換もしくは無置換の炭素数１〜５０のアルキル基、置換もしくは無置換の炭素数２〜５０のアルケニル基、置換もしくは無置換の環形成炭素数３〜５０のシクロアルキル基、置換もしくは無置換の炭素数１〜５０のアルコキシ基、置換もしくは無置換の炭素数７〜５０のアラルキル基、置換もしくは無置換の環形成炭素数６〜５０のアリールオキシ基、置換もしくは無置換のシリル基、又は前記式（４）で表される基を示す。Ｒ_１〜Ｒ_１０の少なくとも１つ（好ましくは２つ以上、より好ましくは２つ）は前記式（４）で表される基である。Ｒ_１〜Ｒ_１０は隣接する置換基同士で飽和又は不飽和の環（好ましくは、飽和もしくは不飽和の、置換もしくは無置換の５員環又は６員環、より好ましくは、ベンゼン環）を形成してもよい。 The third material, which is an amine compound, is preferably represented by the following formula (3).

(In the formula (3), R _{1 to} R ₁₀ independently form a hydrogen atom, a halogen atom, a cyano group, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, and a substituted or unsubstituted ring formation. Heteroaryl groups with 5 to 50 atoms, substituted or unsubstituted alkyl groups with 1 to 50 carbon atoms, substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms, substituted or unsubstituted ring-forming carbon groups with 3 to 50 carbon atoms. Cycloalkyl group, substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms, substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, substituted or unsubstituted ring-forming aryloxy group having 6 to 50 carbon atoms, A substituted or unsubstituted silyl group or a group represented by the above formula (4) is shown. At least one (preferably two or more, more preferably two) of R _{1 to} R ₁₀ is the above formula (4). R _{1 to} R ₁₀ are groups represented by (preferably a saturated or unsaturated, substituted or unsubstituted 5-membered ring or 6-membered ring) of adjacent substituents. Preferably, a benzene ring) may be formed.

At least one of Ar ₁ and Ar ₂ of the formula (4) is preferably a heteroaryl group represented by the following formula (5).

（式（５）において、Ｒ_１１〜Ｒ_１７は、それぞれ独立に、水素原子、ハロゲン原子、シアノ基、置換もしくは無置換の環形成炭素数６〜５０のアリール基、置換もしくは無置換の環形成原子数５〜５０のヘテロアリール基、置換もしくは無置換の炭素数１〜５０のアルキル基、置換もしくは無置換の炭素数２〜５０のアルケニル基、置換もしくは無置換の環形成炭素数３〜５０のシクロアルキル基、置換もしくは無置換の炭素数１〜５０のアルコキシ基、置換もしくは無置換の炭素数７〜５０のアラルキル基、置換もしくは無置換の環形成炭素数６〜５０のアリールオキシ基、又は置換もしくは無置換のシリル基を示す。Ｒ_１１〜Ｒ_１７は隣接する置換基同士で飽和又は不飽和の環（好ましくは、飽和もしくは不飽和の、置換もしくは無置換の５員環又は６員環、より好ましくは、ベンゼン環）を形成してもよい。
Ｘ_１は酸素原子又は硫黄原子を示す。）

(In the formula (5), R _{11 to} R ₁₇ independently form a hydrogen atom, a halogen atom, a cyano group, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, and a substituted or unsubstituted ring formation. Heteroaryl groups with 5 to 50 atoms, substituted or unsubstituted alkyl groups with 1 to 50 carbon atoms, substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms, substituted or unsubstituted ring-forming carbon groups with 3 to 50 carbon atoms. Cycloalkyl group, substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms, substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, substituted or unsubstituted ring-forming aryloxy group having 6 to 50 carbon atoms, Alternatively, it indicates a substituted or unsubstituted silyl group. R _{11 to} R ₁₇ are saturated or unsaturated rings (preferably saturated or unsaturated, substituted or unsubstituted 5-membered ring or 6-membered) between adjacent substituents. A ring, more preferably a benzene ring) may be formed.
X ₁ represents an oxygen atom or a sulfur atom. )

It is preferable that X ₁ of the formula (5) is an oxygen atom.

It is preferable that two of R _{1 to} R ₁₀ of the formula (3) are groups represented by the formula (4).

The third material, which is an amine compound, is preferably represented by the following formula (6).

（式（６）において、Ｒ_１〜Ｒ_８は、前記式（３）で定義した通りである。Ａｒ_１及びＡｒ_２は、前記式（４）で定義した通りである。
Ａｒ_３及びＡｒ_４は、それぞれ独立に、置換もしくは無置換の環形成炭素数６〜５０のアリール基、又は置換もしくは無置換の環形成原子数５〜５０のヘテロアリール基を示す。
ただし、Ａｒ_３及びＡｒ_４のうち少なくとも１つが前記式（５）で表されるヘテロアリール基である。）

(In the formula (6), R _{1 to} R ₈ are as defined by the above formula (3). Ar ₁ and Ar ₂ are as defined by the above formula (4).
Ar ₃ and Ar ₄ independently represent a substituted or unsubstituted aryl group having 6 to 50 ring-forming atoms, or a substituted or unsubstituted heteroaryl group having 5 to 50 ring-forming atoms.
However, at least one of Ar ₃ and Ar ₄ is a heteroaryl group represented by the above formula (5). )

（式（７）において、Ｒ_１〜Ｒ_８、Ａｒ_２及びＡｒ_４は、前記式（６）で定義した通りである。
Ｒ_２１〜Ｒ_２７及びＲ_３１〜Ｒ_３７は、それぞれ独立に、水素原子、ハロゲン原子、シアノ基、置換もしくは無置換の環形成炭素数６〜５０のアリール基、置換もしくは無置換の環形成原子数５〜５０のヘテロアリール基、置換もしくは無置換の炭素数１〜５０のアルキル基、置換もしくは無置換の炭素数２〜５０のアルケニル基、置換もしくは無置換の環形成炭素数３〜５０のシクロアルキル基、置換もしくは無置換の炭素数１〜５０のアルコキシ基、置換もしくは無置換の炭素数７〜５０のアラルキル基、置換もしくは無置換の環形成炭素数６〜５０のアリールオキシ基、又は置換もしくは無置換のシリル基を示す。Ｒ_２１〜Ｒ_２７及びＲ_３１〜Ｒ_３７は隣接する置換基同士で飽和又は不飽和の環（好ましくは、飽和もしくは不飽和の、置換もしくは無置換の５員環又は６員環、より好ましくは、ベンゼン環）を形成してもよい。
Ｘ_２及びＸ_３は、それぞれ独立に酸素原子又は硫黄原子を示す。） The third material, which is an amine compound, is preferably represented by the following formula (7).

(In the formula (7), R _{1 to} R ₈ , Ar ₂ and Ar ₄ are as defined in the above formula (6).
R _{21 to} R ₂₇ and R _{31 to} R ₃₇ are independently hydrogen atom, halogen atom, cyano group, substituted or unsubstituted aryl group having 6 to 50 carbon atoms, substituted or unsubstituted ring forming atom, respectively. Heteroaryl groups of 5 to 50, substituted or unsubstituted alkyl groups of 1 to 50 carbon atoms, substituted or unsubstituted alkoxy groups of 2 to 50 carbon atoms, substituted or unsubstituted ring-forming carbon atoms of 3 to 50 Cycloalkyl groups, substituted or unsubstituted alkoxy groups with 1 to 50 carbon atoms, substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms, substituted or unsubstituted ring-forming aryloxy groups with 6 to 50 carbon atoms, or Indicates a substituted or unsubstituted silyl group. R _{21 to} R ₂₇ and R _{31 to} R ₃₇ are saturated or unsaturated rings of adjacent substituents (preferably saturated or unsaturated, substituted or unsubstituted 5- or 6-membered rings, more preferably. , Benzene ring) may be formed.
X ₂ and X ₃ independently represent an oxygen atom or a sulfur atom, respectively. )

It is preferable that X ₂ and X ₃ of the formula (7) are oxygen atoms.

It is preferable that R _{1 to} R ₈ of the formulas (3), (6) and (7) are hydrogen atoms.

Specific examples of the third material, which is an amine compound, include the compounds shown below.

In the present specification, as the substituent (hereinafter, also referred to as an arbitrary substituent) in the case of "substituent or unsubstituted", for example, the halogen atom, cyano group, and unsubstituted group described above for R _{101 to} R _{110 and the} like are used. Ring-forming aryl group having 6 to 50 carbon atoms, unsubstituted heteroaryl group having 5 to 50 ring-forming atoms, unsubstituted alkyl group having 1 to 50 carbon atoms, and unsubstituted alkenyl group having 2 to 50 carbon atoms. , An unsubstituted cycloalkyl group having 3 to 50 carbon atoms, an unsubstituted alkoxy group having 1 to 50 carbon atoms, an unsubstituted aralkyl group having 7 to 50 carbon atoms, and an unsubstituted ring forming carbon number of 6 to 50 carbon atoms. The aryloxy group of the above, an unsubstituted silyl group (-SiH ₃ ) and the like can be mentioned.
Specific examples of each of these substituents are the same as those described above as substituents such as R _{101 to} R ₁₁₀ , respectively.

In the present specification, optional substituents include an arylthio group having an unsubstituted ring-forming carbon number of 6 to 50 (preferably 6 to 18), a silyl group substituted with an alkyl group having 1 to 10 carbon atoms, and a carbon number of carbon atoms. Alkyl halide groups 1 to 10 and the like may be used.
Examples of the arylthio group having 6 to 50 carbon atoms for ring formation include a sulfur atom in the alkyl group having 1 to 50 carbon atoms of R _{101 to} R _{110 of the} above formula (1) and R _{201 to} R ₂₁₀ of the formula (2). A group to which is bonded can be mentioned.
Examples of the silyl group substituted with an alkyl group having 1 to 10 carbon atoms include a trimethylsilyl group.
Examples of the alkyl halide group having 1 to 10 carbon atoms include a trifluoromethyl group.

In the present specification, a saturated or unsaturated ring (preferably a saturated or unsaturated, substituted or unsubstituted 5-membered ring or 6-membered ring) may be formed between any adjacent substituents.
As used herein, any substituent may further have a substituent. Examples of the substituent further possessed by the arbitrary substituent include those similar to those of the above-mentioned arbitrary substituent.

One aspect of the organic EL device of the present invention preferably has a hole transport layer between the anode and the light emitting layer.
One aspect of the organic EL device of the present invention preferably has an electron transport layer between the cathode and the light emitting layer.

As a light emitting layer of one aspect of the organic EL device of the present invention, for example, the light emitting layer shown in Table 1 below can be mentioned as a specific example.

Compounds X1 to X4, compounds Y1 to Y3, and compounds Z1 to Z2 in Table 1 are shown below.

As a typical element configuration of the organic EL element of the present invention,
(1) Anophode / light emitting layer / cathode (2) Anodium / hole injection layer / light emitting layer / cathode (3) Anodium / light emitting layer / electron injection / transport layer / cathode (4) Anodium / hole injection layer / light emitting layer / Electron injection / transport layer / Cathode (5) Anodic / Organic semiconductor layer / Light emitting layer / Cathode (6) Anodic / Organic semiconductor layer / Electronic barrier layer / Light emitting layer / Cathode (7) Anodic / Organic semiconductor layer / Light emitting layer / Adhesion improvement layer / cathode (8) anode / hole injection / transport layer / light emitting layer / electron injection / transport layer / cathode (9) anode / insulating layer / light emitting layer / insulating layer / cathode (10) anode / inorganic semiconductor layer / Insulating layer / light emitting layer / insulating layer / cathode (11) anode / organic semiconductor layer / insulating layer / light emitting layer / insulating layer / cathode (12) anode / insulating layer / hole injection / transport layer / light emitting layer / insulating layer / Cathode (13) Structures such as an anode / insulating layer / hole injection / transport layer / light emitting layer / electron injection / transport layer / cathode can be mentioned.
Of the above, the configuration (8) is preferably used, but is not limited thereto.

Further, the light emitting layer may be a phosphorescent light emitting layer or a fluorescent light emitting layer, or may have a plurality of light emitting layers. When there are a plurality of light emitting layers, a space layer may be provided between the light emitting layers in order to prevent excitons generated in the phosphorescent light emitting layer from diffusing into the fluorescent light emitting layer.

FIG. 1 shows a schematic configuration of an example of an organic EL device according to an embodiment of the present invention.
The organic EL element 1 has a transparent substrate 2, an anode 3, a cathode 4, and an organic thin film layer 10 arranged between the anode 3 and the cathode 4.
The organic thin film layer 10 has the above-mentioned light emitting layer 5, but has a hole injection / transport layer 6 or the like between the light emitting layer 5 and the anode 3, and an electron injection / transport layer 7 between the light emitting layer 5 and the cathode 4. Etc. may be provided.
Further, an electron barrier layer may be provided on the anode 3 side of the light emitting layer 5, and a hole barrier layer may be provided on the cathode 4 side of the light emitting layer 5, respectively.
As a result, electrons and holes can be confined in the light emitting layer 5 to increase the probability of exciton generation in the light emitting layer 5.

Further, in the present specification, "hole injection / transport layer" means "at least one of a hole injection layer and a hole transport layer", and "electron injection / transport layer" means "electron injection layer". And at least one of the electron transport layers. "

The substrate is used as a support for the light emitting element. As the substrate, for example, glass, quartz, plastic or the like can be used. Moreover, you may use a flexible substrate. The flexible substrate is a foldable (flexible) substrate, and examples thereof include a plastic substrate made of polycarbonate and polyvinyl chloride.

For the anode formed on the substrate, it is preferable to use a metal having a large work function (specifically, 4.0 eV or more), an alloy, an electrically conductive compound, a mixture thereof, or the like. Specifically, for example, indium-tin oxide (ITO: Indium Tin Oxide), indium tin oxide containing silicon or silicon oxide, indium oxide-zinc oxide, tungsten oxide, and indium oxide containing zinc oxide. , Graphene and the like. In addition, gold (Au), platinum (Pt), a nitride of a metallic material (for example, titanium nitride) and the like can be mentioned.

The hole injection layer is a layer containing a substance having a high hole injection property. Substances with high hole injection properties include molybdenum oxide, titanium oxide, vanadium oxide, renium oxide, ruthenium oxide, chromium oxide, zirconium oxide, hafnium oxide, tantalum oxide, silver oxide, etc. Ladder compounds such as tungsten oxides, manganese oxides, aromatic amine compounds, fluorene derivatives, or polymer compounds (oligoforms, dendrimers, polymers, etc.) can also be used.

The hole transport layer is a layer containing a substance having a high hole transport property. An aromatic amine compound, a carbazole derivative, an anthracene derivative, or the like can be used for the hole transport layer. 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 hole transport property than electrons. The layer containing the substance having a high hole transport property is not limited to a single layer, but may be a layer in which two or more layers made of the above substances are laminated.

The electron transport layer is a layer containing a substance having a high electron transport property. The electron transport layer includes 1) metal complexes such as lithium complex, aluminum complex, beryllium complex and zinc complex, 2) complex aromatic compounds such as imidazole derivative, benzimidazole derivative, azine derivative, carbazole derivative and phenanthroline derivative, and 3). High molecular weight compounds can be used.

The electron injection layer is a layer containing a substance having a high electron injection property. The electron injection layer contains alkali metals such as lithium (Li), lithium complex, lithium fluoride (LiF), cesium fluoride (CsF), calcium fluoride (CaF2), lithium oxide (LiOx), and alkaline soil. Alkaline metals or compounds thereof can be used.

As the cathode, it is preferable to use a metal having a small work function (specifically, 3.8 eV or less), an alloy, an electrically conductive compound, a mixture thereof, or the like. Specific examples of such a cathode material include elements belonging to Group 1 or Group 2 of the Periodic Table of the Elements, that is, alkali metals such as lithium (Li) and cesium (Cs), and alkaline soil such as magnesium (Mg). Examples thereof include similar metals and alloys containing them (for example, MgAg, AlLi) and the like.

In one aspect of the organic EL device of the present invention, the method for forming each layer is not particularly limited. A conventionally known forming method such as a vacuum vapor deposition method or a spin coating method can be used. Each layer such as a light emitting layer is known by a vacuum vapor deposition method, a molecular beam epitaxy method (MBE method), a dipping method of a solution dissolved in a solvent, a spin coating method, a casting method, a bar coating method, a roll coating method, or the like. It can be formed by a method.

In forming the light emitting layer, the first material represented by the formula (1), the second material represented by the formula (2), and the third material which is an amine compound may be co-deposited.
Further, the first material represented by the formula (1), the second material represented by the formula (2), and the third material which is an amine compound are premixed to obtain a material for an organic EL device, which is used for an organic EL device. The material may be deposited.
The premix is preferably a mixture of powders of the first material represented by the formula (1), the second material represented by the formula (2), and the third material which is an amine compound.

In one aspect of the organic EL device of the present invention, the film thickness of each layer is not particularly limited, but generally, in order to suppress defects such as pinholes, keep the applied voltage low, and improve efficiency, it is usually several nm to 1 μm. The range is preferred.

The organic EL element of the present invention can be used for display components such as organic EL panel modules, display devices such as televisions, mobile phones, and personal computers, and electronic devices such as lighting or light emitting devices such as vehicle lamps. ..

Example 1
A glass substrate (manufactured by Geomatic Co., Ltd.) with an ITO transparent electrode (anodide) having a thickness of 25 mm × 75 mm × 1.1 mm was ultrasonically cleaned in isopropyl alcohol for 5 minutes, and then UV ozone cleaning was performed for 30 minutes. The film thickness of ITO was 130 nm.
The glass substrate with the transparent electrode line after cleaning is mounted on the substrate holder of the vacuum vapor deposition apparatus, and the compound HI is first vapor-deposited on the surface on the side where the transparent electrode line is formed so as to cover the transparent electrode, and the film thickness is 5 nm. The compound HI film of the above was formed. This HI membrane functions as a hole injection layer.
Following the film formation of this HI film, the compound HT-1 is deposited, an HT-1 film having a film thickness of 80 nm is formed on the HI film, and the compound HT-2 is further deposited on the HT-1 film. An HT-2 film having a film thickness of 10 nm was formed. These HT-1 membrane and HT-2 membrane function as a hole transport layer.
Further, compound BH1-1 as a first material, compound BH2-1 as a second material, and compound BD as a third material were co-deposited on the HT-2 film to form a light emitting layer having a film thickness of 25 nm. In this light emitting layer, the mass ratio of compound BH1-1 as the first material, compound BH2-1 as the second material, and compound BD as the third material was set to 86: 10: 4.
Compound HBL was deposited on this light emitting layer to form an HBL film having a film thickness of 10 nm. This HBL film functions as a barrier layer.
A compound ET, which is an electron-transporting compound, was deposited on the HBL film to form an ET film having a film thickness of 15 nm. This ET film functions as an electron transport layer.
LiF was deposited on this ET film to form a LiF film having a film thickness of 1 nm.
A metal Al was vapor-deposited on the LiF film to form a metal Al cathode having a film thickness of 80 nm, and an organic EL device was produced.

The initial characteristics of the obtained organic EL element were measured at room temperature with a DC (direct current) constant current of 10 mA / cm ² drive. The voltage measurement results are shown in Table 2. Table 2 shows the results of the lifetime LT95 obtained by applying a voltage to the organic EL element so that the current density becomes 50 mA / cm ² and measuring the time until the brightness becomes 95% with respect to the initial brightness.

The compounds used are shown below.

Example 2 and Comparative Examples 1-2
An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the compounds and mass ratios shown in Table 2 were used. The results are shown in Table 2.

Compound BH1-2 is shown below.

Examples 1 and 2 had a lower voltage than Comparative Example 1 and a longer life than Comparative Example 2.

Further, the value of LT95 in Example 1 was equivalent to the value of LT95 in Comparative Example 1, and the value of LT95 in Example 1 was larger than the value of LT95 in Comparative Example 2. Further, the voltage value of Example 1 was smaller than the voltage value of Comparative Example 1.
The reason for exhibiting the above effects is presumed to be as follows. In the element of the first embodiment, the value of the voltage becomes low as the hole transport is promoted by BH2-1. Further, in the element of the first embodiment, the value of LT95 becomes large as the electrons flow through the LUMO (minimum empty orbit) of the BH1-1 and the deterioration of the BD due to the electrons can be suppressed.

Claims (34)

With the cathode
With the anode
A light emitting layer arranged between the cathode and the anode,
Have,
The light emitting layer contains an organic electroluminescence containing a first material represented by the following formula (1), a second material represented by the following formula (2), and a third material represented by the following formula (3). element.

(In the formula _{(1), R 101 ~ R} 108 are each independently a hydrogen atom, a halogen atom, a cyano group, substitution or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted C 2 50 alkenyl group, a substituted or unsubstituted ring formed cycloalkyl group having 3 to 50 carbon atoms, or a substituted or unsubstituted silyl group.
R ₁₀₉ and R ₁₁₀ are independent groups represented by -L _101- Ar ₁₀₁ .
L ₁₀₁ is a single-bonded, substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted anthranylene group, or a substituted or unsubstituted fluorenylene group.
Ar ₁₀₁ is a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted spiro. A fluorenyl group, a substituted or unsubstituted benzofluorenyl group , or a substituted or unsubstituted heteroaryl group having 5 to 50 ring-forming atoms.
When L ₁₀₁ is 2 or more, 2 or more L ₁₀₁ may be the same or different. If Ar ₁₀₁ is 2 or more, two or more _{Ar 101} may be the same or different.
In the above formula (1), the substituent in the case of "substituted or unsubstituted" is a halogen atom, a cyano group, a phenyl group, a 1-naphthyl group, a 2-naphthyl group, a biphenyl group, a terphenyl group, a phenanthryl group, and the like. Fluolenyl group, unsubstituted heteroaryl group having 5 to 18 carbon atoms, unsubstituted alkyl group having 1 to 18 carbon atoms, unsubstituted alkenyl group having 2 to 18 carbon atoms, and unsubstituted ring forming carbon number 3 Cycloalkyl groups of ~ 18, unsubstituted alkoxy groups of 1-18 carbon atoms, unsubstituted aralkyl groups of 7-18 carbon atoms, unsubstituted ring-forming aryloxy groups of 6-18 carbon atoms, or substituted or absent It is a substituted silyl group. )

(In equation (2)
R ₂₀₁ is a group represented by −L ₂₀₁ −Ar ₂₀₁ .
R _{202 to} R ₂₁₀ are each independently a hydrogen atom, a halogen atom, a cyano group, an aryl group having 6 to 50 substituted or unsubstituted ring-forming atoms, and a hetero having 5 to 50 substituted or unsubstituted ring-forming atoms. Aryl groups, substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms, substituted or unsubstituted alkenyl groups having 2 to 50 carbon atoms, substituted or unsubstituted ring-forming cycloalkyl groups having 3 to 50 carbon atoms, substituted or unsubstituted. Unsubstituted alkoxy group with 1 to 50 carbon atoms, substituted or unsubstituted aralkyl group with 7 to 50 carbon atoms, substituted or unsubstituted ring-forming aryloxy group with 6 to 50 carbon atoms, substituted or unsubstituted silyl group , Or -L _201- Ar ₂₀₁ .
L ₂₀₁ is a single-bonded, substituted or unsubstituted ring-forming carbon number 6 to 50 arylene group, or a substituted or unsubstituted ring-forming atom number 5 to 50 heteroarylene group.
Ar ₂₀₁ is a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 50 ring-forming atoms. When L ₂₀₁ is 2 or more, 2 or more L ₂₀₁ may be the same or different. If Ar ₂₀₁ is 2 or more, two or more _{Ar 201} may be the same or different.
In the above formula (2), the substituent in the case of "substituted or unsubstituted" is a halogen atom, a cyano group, an aryl group having an unsubstituted ring-forming carbon number of 6 to 50, and an unsubstituted ring-forming atom number 5 to 5. 50 heteroaryl groups, unsubstituted alkyl groups with 1 to 50 carbon atoms, unsubstituted alkenyl groups with 2 to 50 carbon atoms, unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, unsubstituted carbon atoms 1 to 50 alkoxy groups, unsubstituted 7 to 50 carbon number aralkyl groups, unsubstituted ring-forming carbon number 6 to 50 aryloxy groups, unsubstituted ring forming carbon number 6 to 50 arylthio groups, or substituted Alternatively, it is an unsubstituted silyl group. )

(In the formula (3), R _{1 to} R ₁₀ are independently hydrogen atom, halogen atom, cyano group, substituted or unsubstituted aryl group having 6 to 50 carbon atoms, and substituted or unsubstituted carbon number. Alkyl groups from 1 to 50, substituted or unsubstituted alkenyl groups having 2 to 50 carbon atoms, substituted or unsubstituted ring-forming cycloalkyl groups having 3 to 50 carbon atoms, substituted or unsubstituted silyl groups, or the following formula ( at least one of _.R 1 _{to R 10,} which represents a group represented by 4) is a group represented by the following formula (4) _.R 1 _{to R 10} is a saturated or unsaturated adjacent substituents Does not form a ring.)

(In the formula (4), Ar ₁ and Ar ₂ are independently substituted or unsubstituted aryl groups having 6 to 50 ring-forming atoms, or substituted or unsubstituted heteroaryls having 5 to 50 ring-forming atoms. The groups L ₁ , L ₂ and L ₃ are independently single-bonded, substituted or unsubstituted arylene groups having 6 to 18 ring-forming carbon atoms.)
When Ar ₁ , Ar ₂ , L ₁ , L ₂ and L ₃ are 2 or more, 2 or more Ar ₁ , Ar ₂ , L ₁ , L ₂ and L ₃ may be the same or different. ) R in the above formula (1) ₁₀₁ ~ R ₁₀₈ The organic electroluminescence element according to claim 1, wherein each is independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 18 carbon atoms, or a substituted or unsubstituted silyl group. The organic electroluminescence device according to claim 1 or 2 , wherein R _{101 to} R ₁₀₈ in the formula (1) are hydrogen atoms. L in the above formula (1) ₁₀₁ The organic electroluminescence element according to any one of claims 1 to 3, wherein is a single-bonded or substituted or unsubstituted phenylene group, a substituted or unsubstituted fluorenylene group, or a substituted or unsubstituted naphthylene group. The organic electroluminescence element according to any one of claims 1 to 4 , wherein L ₁₀₁ in the above formula (1) is a substituted or unsubstituted phenylene group or a substituted or unsubstituted naphthylene group. L in the above formula (1) ₁₀₁ The organic electroluminescence device according to any one of claims 1 to 5, wherein is a single-bonded or unsubstituted phenylene group. Ar in the above formula (1) ₁₀₁ However, the number of substituted or unsubstituted phenyl groups, substituted or unsubstituted naphthyl groups, substituted or unsubstituted biphenyl groups, substituted or unsubstituted phenanthryl groups, substituted or unsubstituted fluorenyl groups, or unsubstituted ring-forming atoms. The organic electroluminescence element according to any one of claims 1 to 6, which is a heteroaryl group of 5 to 18. In Formula (1), A r ₁₀₁ is a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted dibenzofuranyl group, substitution or unsubstituted The organic electroluminescence element according to any one of claims 1 to 7 , which is selected from the group consisting of a substituted dibenzothiophenyl group and a substituted or unsubstituted naphthobenzofuranyl group. Ar in the above formula (1) ₁₀₁ Is an unsubstituted phenyl group, an unsubstituted 1-naphthyl group, an unsubstituted 2-naphthyl group, a 9,9-dimethylfluorene-2-yl group, or an unsubstituted naphthobenzofuran-2-yl group. Item 8. The organic electroluminescence element according to any one of Items 1 to 8. R in the above formula (2) ₂₀₂ ~ R ₂₁₀ However, each independently has a hydrogen atom, an alkyl group having 1 to 18 substituted or unsubstituted carbon atoms, an aryl group having 6 to 18 substituted or unsubstituted ring-forming carbon atoms, or 5 substituted or unsubstituted ring-forming atomic numbers. The organic electroluminescence element according to any one of claims 1 to 9, which is a heteroaryl group of ~ 18. R in the above formula (2) ₂₀₂ ~ R ₂₁₀ However, each independently has a hydrogen atom, a methyl group, an ethyl group, a propyl group, an isopropyl group, an n-butyl group, an s-butyl group, an isobutyl group, a t-butyl group, an unsubstituted phenyl group, or an unsubstituted biphenyl. The organic electroluminescence element according to any one of claims 1 to 10, which is an yl group. The organic electroluminescence device according to any one of claims 1 to 11 , wherein R _{202 to} R ₂₁₀ in the formula (2) are hydrogen atoms. L in the above formula (2) ₂₀₁ However, a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted fluorenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted terphenylene group, a substituted or unsubstituted phenylene group. Phenylene group,

The organic electroluminescence device according to any one of claims 1 to 12. L in the above formula (2) ₂₀₁ The organic electroluminescence device according to any one of claims 1 to 13, wherein the organic electroluminescence device is a single-bonded, unsubstituted phenylene group, or a 9,9-dimethyl-fluorenylene group. Ar in the above formula (2) ₂₀₁ The organic electro-organic according to any one of claims 1 to 14, wherein is an aryl group having 6 to 18 substituted or unsubstituted ring-forming carbon atoms or a heteroaryl group having 5 to 18 substituted or unsubstituted ring-forming atoms. Luminescence element. Ar in the above formula (2) ₂₀₁ The organic electroluminescence according to any one of claims 1 to 15, wherein is a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted fluorenyl group, or a substituted or unsubstituted pyrenyl group. element. In the above formula (3), R _{1 to} R ₁₀ are independently hydrogen atoms, substituted or unsubstituted ring-forming aryl groups having 6 to 50 carbon atoms, and substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms. , Or the organic electroluminescence element according to any one of claims 1 to 16, which is a group represented by the above formula (4). The organic electroluminescence device according to any one of claims 1 to 17, wherein at least one of Ar ₁ and Ar ₂ in the formula (4) is a heteroaryl group represented by the following formula (5).

(In the formula (5), R _{11 to} R ₁₇ independently form a hydrogen atom, a halogen atom, a cyano group, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, and a substituted or unsubstituted ring formation. Heteroaryl groups with 5 to 50 atoms, substituted or unsubstituted alkyl groups with 1 to 50 carbon atoms, substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms, substituted or unsubstituted ring-forming carbon groups with 3 to 50 carbon atoms. Cycloalkyl group, substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms, substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, substituted or unsubstituted ring-forming aryloxy group having 6 to 50 carbon atoms, Alternatively, it indicates a substituted or unsubstituted silyl group. R _{11 to} R ₁₇ may form a saturated or unsaturated ring between adjacent substituents.
X ₁ represents an oxygen atom or a sulfur atom. ) The organic electroluminescence device according to claim 18 , wherein X ₁ is an oxygen atom in the above formula (5) . Two Organic electroluminescent device according to any one of claims 1 to 19 is a group represented by the formula (4) of said at formula _{(3), R 1 ~R 10} . The organic electroluminescence device according to any one of claims 1 to 20 , wherein the third material is represented by the following formula (6).

(In the formula (6), R _{1 to} R ₈ are as defined by the above formula (3). Ar ₁ and Ar ₂ are as defined by the above formula (4).
Ar ₃ and Ar ₄ independently represent a substituted or unsubstituted aryl group having 6 to 50 ring-forming atoms, or a substituted or unsubstituted heteroaryl group having 5 to 50 ring-forming atoms.
However, at least one of Ar ₃ and Ar ₄ is a heteroaryl group represented by the above formula (5). ) The organic electroluminescence device according to any one of claims 1 to 21 , wherein the third material is represented by the following formula (7).

(In the formula (7), R _{1 to} R ₈ , Ar ₂ and Ar ₄ are as defined in the above formula (6).
R _{21 to} R ₂₇ and R _{31 to} R ₃₇ are independently hydrogen atom, halogen atom, cyano group, substituted or unsubstituted aryl group having 6 to 50 carbon atoms, substituted or unsubstituted ring forming atom, respectively. Heteroaryl groups of 5 to 50, substituted or unsubstituted alkyl groups of 1 to 50 carbon atoms, substituted or unsubstituted alkoxy groups of 2 to 50 carbon atoms, substituted or unsubstituted ring-forming carbon atoms of 3 to 50 Cycloalkyl groups, substituted or unsubstituted alkoxy groups with 1 to 50 carbon atoms, substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms, substituted or unsubstituted ring-forming aryloxy groups with 6 to 50 carbon atoms, or Indicates a substituted or unsubstituted silyl group. R _{21 to} R ₂₇ and R _{31 to} R ₃₇ do not form saturated or unsaturated rings between adjacent substituents.
X ₂ and X ₃ independently represent an oxygen atom or a sulfur atom, respectively. ) R in the above formula (7) ₁ ~ R ₈ Each independently has a hydrogen atom, an aryl group having 6 to 18 substituted or unsubstituted ring-forming carbon atoms, an alkyl group having 1 to 18 substituted or unsubstituted carbon atoms, or a substituted or unsubstituted ring-forming carbon number of 3 carbon atoms. The organic electroluminescence element according to claim 22, which is a cycloalkyl group of ~ 18. The organic electroluminescence device according to claim 22 or 23 , wherein R _{1 to} R ₈ in the formula (7) are hydrogen atoms. Ar in the above formula (7) ₂ And Ar ₄ 22 to 24, respectively, which are independently substituted or unsubstituted aryl groups having 6 to 18 ring-forming carbon atoms or substituted or unsubstituted heteroaryl groups having 5 to 18 ring-forming atoms. The organic electroluminescence element described. Ar in the above formula (7) ₂ And Ar ₄ The organic electroluminescence device according to any one of claims 22 to 25, wherein the organic electroluminescence device is an unsubstituted phenyl group. R in the above formula (7) ₂₁ ~ R ₂₇ And R ₃₁ ~ R ₃₇ Are each independently a hydrogen atom, a substituted or unsubstituted ring-forming aryl group having 6 to 18 carbon atoms, a substituted or unsubstituted alkyl group having 1 to 18 carbon atoms, or a substituted or unsubstituted silyl group. Item 2. The organic electroluminescence element according to any one of Items 22 to 26. R in the above formula (7) ₂₁ ~ R ₂₇ And R ₃₁ ~ R ₃₇ The organic electroluminescence device according to any one of claims 22 to 27, wherein is a hydrogen atom. The organic electroluminescence device according to any one of claims 22 to 28, wherein X ₂ and X ₃ are oxygen atoms in the above formula (7) . The organic electro of claim 1, wherein the first material contains one or more compounds selected from the following A1 group, the second material from the following B1 group, and the third material from the following C1 group. Luminescence element.
Group A1:

Group B1:

Group C1:

The organic electro of claim 1, wherein the first material contains one or more compounds selected from the following A2 group, the second material from the following B2 group, and the third material from the following C2 group. Luminescence element.
Group A2:

Group B2:

Group C2:

An electronic device comprising the organic electroluminescence device according to any one of claims 1 to 31 . A material for an organic electroluminescence device containing a first material represented by the following formula (1), a second material represented by the following formula (2), and a third material represented by the following formula (3) .

(In the formula _{(1), R 101 ~ R} 108 are each independently a hydrogen atom, a halogen atom, a cyano group, substitution or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted C 2 50 alkenyl group, a substituted or unsubstituted ring formed cycloalkyl group having 3 to 50 carbon atoms, or a substituted or unsubstituted silyl group.
R ₁₀₉ and R ₁₁₀ are independent groups represented by -L _101- Ar ₁₀₁ .
L ₁₀₁ is a single-bonded, substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted anthranylene group, or a substituted or unsubstituted fluorenylene group.
Ar ₁₀₁ is a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted spiro. A fluorenyl group, a substituted or unsubstituted benzofluorenyl group , or a substituted or unsubstituted heteroaryl group having 5 to 50 ring-forming atoms.
When L ₁₀₁ is 2 or more, 2 or more L ₁₀₁ may be the same or different. If Ar ₁₀₁ is 2 or more, two or more _{Ar 101} may be the same or different.
In the above formula (1), the substituent in the case of "substituted or unsubstituted" is a halogen atom, a cyano group, a phenyl group, a 1-naphthyl group, a 2-naphthyl group, a biphenyl group, a terphenyl group, a phenanthryl group, and the like. Fluolenyl group, unsubstituted heteroaryl group having 5 to 18 carbon atoms, unsubstituted alkyl group having 1 to 18 carbon atoms, unsubstituted alkenyl group having 2 to 18 carbon atoms, and unsubstituted ring forming carbon number 3 Cycloalkyl groups of ~ 18, unsubstituted alkoxy groups of 1-18 carbon atoms, unsubstituted aralkyl groups of 7-18 carbon atoms, unsubstituted ring-forming aryloxy groups of 6-18 carbon atoms, or substituted or absent It is a substituted silyl group. )

(In equation (2)
R ₂₀₁ is a group represented by −L ₂₀₁ −Ar ₂₀₁ .
R _{202 to} R ₂₁₀ are each independently a hydrogen atom, a halogen atom, a cyano group, an aryl group having 6 to 50 substituted or unsubstituted ring-forming atoms, and a hetero having 5 to 50 substituted or unsubstituted ring-forming atoms. Aryl groups, substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms, substituted or unsubstituted alkenyl groups having 2 to 50 carbon atoms, substituted or unsubstituted ring-forming cycloalkyl groups having 3 to 50 carbon atoms, substituted or unsubstituted. Unsubstituted alkoxy group with 1 to 50 carbon atoms, substituted or unsubstituted aralkyl group with 7 to 50 carbon atoms, substituted or unsubstituted ring-forming aryloxy group with 6 to 50 carbon atoms, substituted or unsubstituted silyl group , Or -L _201- Ar ₂₀₁ .
L ₂₀₁ is a single-bonded, substituted or unsubstituted ring-forming carbon number 6 to 50 arylene group, or a substituted or unsubstituted ring-forming atom number 5 to 50 heteroarylene group.
Ar ₂₀₁ is a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 50 ring-forming atoms. When L ₂₀₁ is 2 or more, 2 or more L ₂₀₁ may be the same or different. If Ar ₂₀₁ is 2 or more, two or more _{Ar 201} may be the same or different.
In the above formula (2), the substituent in the case of "substituted or unsubstituted" is a halogen atom, a cyano group, an aryl group having an unsubstituted ring-forming carbon number of 6 to 50, and an unsubstituted ring-forming atom number 5 to 5. 50 heteroaryl groups, unsubstituted alkyl groups with 1 to 50 carbon atoms, unsubstituted alkenyl groups with 2 to 50 carbon atoms, unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, unsubstituted carbon atoms 1 to 50 alkoxy groups, unsubstituted 7 to 50 carbon number aralkyl groups, unsubstituted ring-forming carbon number 6 to 50 aryloxy groups, unsubstituted ring forming carbon number 6 to 50 arylthio groups, or substituted Alternatively, it is an unsubstituted silyl group. )

(In the formula (3), R _{1 to} R ₁₀ are independently hydrogen atom, halogen atom, cyano group, substituted or unsubstituted aryl group having 6 to 50 carbon atoms, and substituted or unsubstituted carbon number. Alkyl groups from 1 to 50, substituted or unsubstituted alkenyl groups having 2 to 50 carbon atoms, substituted or unsubstituted ring-forming cycloalkyl groups having 3 to 50 carbon atoms, substituted or unsubstituted silyl groups, or the following formula ( at least one of _.R 1 _{to R 10,} which represents a group represented by 4) is a group represented by the following formula (4) _.R 1 _{to R 10} is a saturated or unsaturated adjacent substituents Does not form a ring.)

(In the formula (4), Ar ₁ and Ar ₂ are independently substituted or unsubstituted aryl groups having 6 to 50 ring-forming atoms, or substituted or unsubstituted heteroaryls having 5 to 50 ring-forming atoms. The groups L ₁ , L ₂ and L ₃ are independently single-bonded, substituted or unsubstituted arylene groups having 6 to 18 ring-forming carbon atoms.)
When Ar ₁ , Ar ₂ , L ₁ , L ₂ and L ₃ are 2 or more, 2 or more Ar ₁ , Ar ₂ , L ₁ , L ₂ and L ₃ may be the same or different. ) The material for an organic electroluminescence device according to claim 33 , wherein at least one of Ar ₁ and Ar ₂ in the formula (4) is a heteroaryl group represented by the following formula (5).

(In the formula (5), R _{11 to} R ₁₇ independently form a hydrogen atom, a halogen atom, a cyano group, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, and a substituted or unsubstituted ring formation. Heteroaryl groups with 5 to 50 atoms, substituted or unsubstituted alkyl groups with 1 to 50 carbon atoms, substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms, substituted or unsubstituted ring-forming carbon groups with 3 to 50 carbon atoms. Cycloalkyl group, substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms, substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, substituted or unsubstituted ring-forming aryloxy group having 6 to 50 carbon atoms, Alternatively, it indicates a substituted or unsubstituted silyl group. R _{11 to} R ₁₇ may form a saturated or unsaturated ring between adjacent substituents.
X ₁ represents an oxygen atom or a sulfur atom. )

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