JP2000026324A - Hydrocarbon compound and organic elecroluminescent element - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain a new hydrocarbon compound suitably useful for an organic electroluminescent element having an excellent luminous efficiency and emitting a light with high brightness. SOLUTION: This compound is pref. a bisacenaphtho[1',2':5,6]indeno[1,2,3-cd: 1',2',3'-lm]perylene derivative of formula I (X1 to X24 are each e.g. H, a halogen, an alkyl, an alkoxy, an alkylthio or an alkenyl), e.g. a compound of formula II. The compound of formula I can be obtained by subjecting 3,3'- bisacenaphtho[1,2-k]fluoranthene derivative to cyclization in the presence of an oxidizing agent of e.g. aluminum chloride/copper (II) chloride. An organic electroluminescent element with excellent luminance is provided by sandwiching one layer, pref. a luminescent layer, of at least one kind derivative of formula I between a pair of electrodes.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

The present invention relates to an organic electroluminescent device and a novel compound which can be suitably used for the device.

[0002]

2. Description of the Related Art Conventionally, an inorganic electroluminescent device has been used as a panel-type light source such as a backlight. However, driving the light emitting device requires a high AC voltage. Recently, an organic electroluminescent device (organic electroluminescent device: organic EL device) using an organic material as a light emitting material has been developed [Appl. Phys. Lett., 51 ,
913 (1987)]. The organic electroluminescent element has a structure in which a thin film containing a fluorescent organic compound is sandwiched between an anode and a cathode,
An exciton is generated by injecting electrons and holes into the thin film and recombining them, and emits light using light emitted when the exciton is deactivated. is there. The organic electroluminescent element can emit light at a low DC voltage of about several volts to several tens of volts, and various colors (for example, red, blue, and green) can be obtained by selecting the type of the fluorescent organic compound. ) Is possible. Organic electroluminescent devices having such features include various light emitting devices,
Application to display elements and the like is expected. However,
Generally, the light emission luminance is low and is not practically sufficient.

As a method for improving the light emission luminance, for example, an organic electroluminescent device using tris (8-quinolinolato) aluminum as a host compound, a coumarin derivative, and a pyran derivative as a guest compound (dopant) as a light emitting layer has been proposed. J. Appl. Phys., 65 , 361
0 (1989)]. Further, as a light emitting layer, for example, a screw (2
An organic electroluminescent device using -methyl-8-quinolinolate) (4-phenylphenolate) aluminum as a host compound and an acridone derivative (for example, N-methyl-2-methoxyacridone) as a guest compound has been proposed ( JP-A-8-67873). However, it is difficult to say that these light emitting elements also have sufficient light emission luminance. At present, an organic electroluminescent device that emits light with higher luminance is desired.

The bisacenaphtho [1 ′, 2 ′: 5,6] indeno [1,2,3-cd: 1 ′, 2 ′, 3′-lm] perylene derivative according to the organic electroluminescent device of the present invention includes: 7,12,19,24-tetraphenylbisacenaphtho [1 ', 2': 5,6] indeno [1,2,3-c
d: 1 ', 2', 3'-lm] perylene is known [for example, J. A
mer. Chem. Soc., 120 , 2476 (1998)]. Also, J. Amer. Chem. Soc., 120 , 2476 (1998) describes a method for producing the compound, but does not describe an organic electroluminescent device.

[0005]

SUMMARY OF THE INVENTION An object of the present invention is to provide an organic electroluminescent device which is excellent in luminous efficiency and emits light with high luminance. Another object is to provide a novel hydrocarbon compound that can be suitably used for the device.

[0006]

Means for Solving the Problems The present inventors have made intensive studies on the organic electroluminescent device and the compounds used in the device, and as a result, completed the present invention. That is,
The present invention comprises at least one bisacenaphtho [1 ′, 2 ′: 5,6] indeno [1,2,3-cd: 1 ′, 2 ′, 3′-lm] perylene derivative between a pair of electrodes. Organic electroluminescent device comprising at least one layer to be sandwiched, bisacenaphtho [1 ', 2': 5,6] indeno [1,2,3-cd: 1 ',
The organic electroluminescent device according to the above, wherein the layer containing at least one kind of 2 ′, 3′-lm] perylene derivative is a light emitting layer, and bisacenaphtho [1 ′, 2 ′: 5,6] indeno [1,2,3- cd: 1 ',
A layer containing at least one 2 ′, 3′-lm] perylene derivative containing a luminescent organometallic complex or the organic electroluminescent device described in the above, bisacenaphtho [1 ′, 2 ′: 5,6] indeno [1 , 2,3-cd: 1 ',
The organic electroluminescent device according to or containing a triarylamine derivative in a layer containing at least one kind of 2 ′, 3′-lm] perylene derivative, further comprising a hole injection / transport layer between a pair of electrodes. The organic electroluminescent device according to any one of the above, the organic electroluminescent device according to any one of the above, further comprising an electron injection transport layer between a pair of electrodes, bisacenaphtho [1 ′, 2 ′: 5,6] ] Indeno [1,2,3-cd: 1 ',
[2 ', 3'-lm] perylene derivative has the general formula (1-A)
The present invention relates to the organic electroluminescent device according to any one of the above, which is a compound represented by the formula:

[0007]

Embedded image

[In the formula, X _{1 to} X ₂₄ each independently represent a hydrogen atom, a halogen atom, a linear, branched or cyclic alkyl group which may have a substituent, or a group which may have a substituent. Good straight-chain, branched or cyclic alkoxy group, straight-chain optionally substituted, branched or cyclic alkylthio group, straight-chain branched or cyclic alkenyl group optionally substituted, substituted Straight-chain, branched or cyclic alkenyloxy group which may have a group, straight-chain, branched or cyclic alkenylthio group which may have a substituent, substituted or unsubstituted aralkyl group, substituted or unsubstituted A substituted aralkyloxy group, a substituted or unsubstituted aralkylthio group,
A substituted or unsubstituted aryl group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted arylthio group,
A substituted or unsubstituted amino group, cyano group, hydroxyl group, nitro group, -COOR ₁ group (wherein R ₁ is a hydrogen atom, a linear, branched or cyclic alkyl group which may have a substituent, Represents a linear, branched or cyclic alkenyl group which may have a group, a substituted or unsubstituted aralkyl group, or a substituted or unsubstituted aryl group), -COR
₂ groups (wherein, R ₂ is a hydrogen atom, a linear or branched alkyl group which may have a substituent, a linear or branched or cyclic alkenyl group which may have a substituent, Represents a substituted or unsubstituted aralkyl group, a substituted or unsubstituted aryl group, or an amino group), or —OCO
R ₃ (wherein, R ₃ is a linear, branched or cyclic alkyl group which may have a substituent, a linear, branched or cyclic alkenyl group which may have a substituent, substituted or unsubstituted Represents an substituted aralkyl group or a substituted or unsubstituted aryl group), and further, a mutually adjacent group selected from X _{1 to} X ₂₄ , or X ₃ and X ₄ , X ₁₅ and X ₁₆ ,
X ₇ and X ₂₄ , or X ₁₂ and X ₁₉ may be bonded to each other to form a substituted or unsubstituted carbocyclic aliphatic ring together with the substituted carbon atom. A compound represented by the general formula (1-A)
It is about.

[0009]

Embedded image

[Wherein, X _{1 to} X ₂₄ each independently represent a hydrogen atom, a halogen atom, a linear, branched or cyclic alkyl group which may have a substituent, Good straight-chain, branched or cyclic alkoxy group, straight-chain optionally substituted, branched or cyclic alkylthio group, straight-chain branched or cyclic alkenyl group optionally substituted, substituted Straight-chain, branched or cyclic alkenyloxy group which may have a group, straight-chain, branched or cyclic alkenylthio group which may have a substituent, substituted or unsubstituted aralkyl group, substituted or unsubstituted A substituted aralkyloxy group, a substituted or unsubstituted aralkylthio group,
A substituted or unsubstituted aryl group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted arylthio group,
A substituted or unsubstituted amino group, cyano group, hydroxyl group, nitro group, -COOR ₁ group (wherein R ₁ is a hydrogen atom, a linear, branched or cyclic alkyl group which may have a substituent, Represents a linear, branched or cyclic alkenyl group which may have a group, a substituted or unsubstituted aralkyl group, or a substituted or unsubstituted aryl group), -COR
₂ groups (wherein, R ₂ is a hydrogen atom, a linear or branched alkyl group which may have a substituent, a linear or branched or cyclic alkenyl group which may have a substituent, Represents a substituted or unsubstituted aralkyl group, a substituted or unsubstituted aryl group, or an amino group), or —OCO
R ₃ (wherein, R ₃ is a linear, branched or cyclic alkyl group which may have a substituent, a linear, branched or cyclic alkenyl group which may have a substituent, substituted or unsubstituted Represents an substituted aralkyl group or a substituted or unsubstituted aryl group), and further, a mutually adjacent group selected from X _{1 to} X ₂₄ , or X ₃ and X ₄ , X ₁₅ and X ₁₆ ,
X ₇ and X ₂₄ , or X ₁₂ and X ₁₉ may be bonded to each other to form a substituted or unsubstituted carbocyclic aliphatic ring together with the substituted carbon atom. However, X ₇ , X ₁₂ , X
Except when ₁₉ and X ₂₄ are simultaneously a phenyl group, and all other Xs are hydrogen atoms. ]

[0011]

BEST MODE FOR CARRYING OUT THE INVENTION Hereinafter, the present invention will be described in detail. The organic electroluminescent device of the present invention, between a pair of electrodes,
Bisacenaphtho [1 ', 2': 5,6] indeno [1,2,3-cd: 1 ', 2',
[3'-lm] perylene derivative is sandwiched between at least one layer containing at least one kind thereof. Bisacenaphtho [1 ', 2': 5,6] Indeno [1,2,3-cd: 1 ', 2', 3 '
[-lm] Perylene derivative (hereinafter abbreviated as compound A according to the present invention) represents a compound having a skeleton represented by general formula (1) (formula 5), and represented by general formula (1). The skeleton to be formed may have various substituents, and is preferably a compound represented by the general formula (1-A) (Formula 5).

[0012]

Embedded image [Wherein, X _{1 to} X ₂₄ represent the same meaning as described above. ]

In the compound represented by the general formula (1-A), X _{1 to} X ₂₄ each independently represent a hydrogen atom, a halogen atom, a linear, branched or cyclic alkyl which may have a substituent. Group, straight-chain, branched or cyclic alkoxy group which may have a substituent, straight-chain, branched or cyclic alkylthio group which may have a substituent, straight chain which may have a substituent Chain, branched or cyclic alkenyl group, optionally substituted straight chain, branched or cyclic alkenyloxy group, optionally substituted straight chain, branched or cyclic alkenylthio group, substituted Or an unsubstituted aralkyl group, a substituted or unsubstituted aralkyloxy group, a substituted or unsubstituted aralkylthio group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted Riruchio group, a substituted or unsubstituted amino group, a cyano group, a hydroxyl group, a nitro group, -COOR ₁
A group (in the group, R ₁ represents a hydrogen atom, a linear or branched alkyl group which may have a substituent, a linear or branched or cyclic alkenyl group which may have a substituent, or unsubstituted aralkyl group, or a substituted or unsubstituted aryl group,), - COR ₂ group (wherein, R ₂ is a hydrogen atom, a straight may have a substituent group, alkyl branched or cyclic Group, a linear, branched or cyclic alkenyl group which may have a substituent, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted aryl group, or an amino group), or -OCOR ₃ (group Wherein R ₃ is a linear, branched or cyclic alkyl group which may have a substituent, a linear, branched or cyclic alkenyl group which may have a substituent, a substituted or unsubstituted aralkyl group , Or replaced or not Represents represents the conversion of the aryl group),
Furthermore, mutually adjacent groups selected from X _{1 to} X ₂₄ , or X ₃ and X ₄ , X ₁₅ and X ₁₆ , X ₇ and X ₂₄ , or X
₁₂ and X ₁₉ may be bonded to each other to form a substituted or unsubstituted carbocyclic aliphatic ring together with the substituted carbon atom. Note that the aryl group represents a carbocyclic aromatic group such as a phenyl group and a naphthyl group, for example, a heterocyclic aromatic group such as a furyl group, a thienyl group, and a pyridyl group.

In the general formula (1-A), X ₁ to
Linear X _24, branched or cyclic alkyl group, a linear, branched or cyclic alkoxy group, a straight-chain, branched or cyclic alkylthio group, straight chain, branched or cyclic alkenyl group,
The straight-chain, branched or cyclic alkenyloxy group and the straight-chain, branched or cyclic alkenylthio group may have a substituent, for example, a halogen atom, having 4 to 20 carbon atoms.
Aryl group, C1-20 alkoxy group, C2-20 alkoxyalkoxy group, C2-20 alkenyloxy group, C4-20 aralkyloxy group, C5-20 aralkyl An oxyalkoxy group, an aryloxy group having 3 to 20 carbon atoms, and 4 to 2 carbon atoms
0 aryloxyalkoxy group, C5-20 arylalkenyl group, C6-20 aralkylalkenyl group, C1-20 alkylthio group, C2
To 20 alkoxyalkylthio groups, C2 to C20 alkylthioalkylthio groups, C2 to C20 alkenylthio groups, C4 to C20 aralkylthio groups, C5 to C20 aralkyloxyalkylthio groups, carbon numbers 5 to 20 aralkylthioalkylthio groups, having 3 to 3 carbon atoms
Monosubstituted or polysubstituted with an arylthio group having 20 carbon atoms, an aryloxyalkylthio group having 4 to 20 carbon atoms, an arylthioalkylthio group having 4 to 20 carbon atoms, a cyclic alkyl group having 4 to 20 carbon atoms containing a hetero atom, or a hydroxyl group; It may be. Further, the aryl group contained in these substituents further includes a halogen atom, an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, and a
It may be substituted with an aryl group having 10 or an aralkyl group having 4 to 10 carbon atoms.

In the general formula (1-A), the aralkyl group of X _{1 to} X ₂₄ , the aralkyloxy group, the aralkylthio group, the aryl group, the aryloxy group, and the aryl group in the arylthio group have a substituent. For example, an alkyl group having 1 to 20 carbon atoms, an alkenyl group having 2 to 20 carbon atoms, an aralkyl group having 4 to 20 carbon atoms, and 3 carbon atoms
To 20 aryl groups, C1 to C20 alkoxy groups,
An alkoxyalkyl group having 2 to 20 carbon atoms, 2 to 2 carbon atoms
0 alkoxyalkyloxy group, alkenyloxy group having 2 to 20 carbon atoms, alkenyloxyalkyl group having 3 to 20 carbon atoms, alkenyloxyalkyloxy group having 3 to 20 carbon atoms, aralkyloxy group having 4 to 20 carbon atoms, An aralkyloxyalkyl group having 5 to 20 carbon atoms, 5 carbon atoms
-20 aralkyloxyalkyloxy groups, 3 carbon atoms
An aryloxy group having from 20 to 20, an aryloxyalkyl group having from 4 to 20 carbon atoms, an aryloxyalkyloxy group having from 4 to 20 carbon atoms, an alkylcarbonyl group having from 2 to 20 carbon atoms, an alkenylcarbonyl group having from 3 to 20 carbon atoms, An aralkylcarbonyl group having 5 to 20 carbon atoms, an arylcarbonyl group having 4 to 20 carbon atoms, an alkoxycarbonyl group having 2 to 20 carbon atoms, an alkenyloxycarbonyl group having 3 to 20 carbon atoms, and an aralkyloxycarbonyl having 5 to 20 carbon atoms Group, an aryloxycarbonyl group having 4 to 20 carbon atoms, an alkylcarbonyloxy group having 2 to 20 carbon atoms, 3 carbon atoms
-20 alkenylcarbonyloxy group, 5-2 carbon atoms
0 aralkylcarbonyloxy group, C4-20 arylcarbonyloxy group, C1-20 alkylthio group, C4-20 aralkylthio group, C3-20 arylthio group, nitro group, cyano A substituent such as a group, a formyl group, a halogen atom, a halogenated alkyl group, a hydroxyl group, an amino group, an N-monosubstituted amino group having 1 to 20 carbon atoms, and an N, N-disubstituted amino group having 2 to 40 carbon atoms. It may be monosubstituted or polysubstituted. Further, the aryl group contained in these substituents further includes a halogen atom, an alkyl group having 1 to 10 carbon atoms,
It may be substituted with an alkoxy group having 10 carbon atoms, an aryl group having 6 to 10 carbon atoms, an aralkyl group having 7 to 10 carbon atoms, or the like.

In the general formula (1-A), the amino group of X _{1 to} X ₂₄ may have a substituent, for example, an alkyl group having 1 to 20 carbon atoms, an aralkyl group having 4 to 20 carbon atoms. Or an aryl group having 3 to 20 carbon atoms may be monosubstituted or disubstituted. In the substituents —COOR ₁ , —COR ₂ and —OCOR ₃ of the general formula (1-A), the alkyl group, alkenyl group, aralkyl group and aryl group of R ₁ , R ₂ and R ₃ have a substituent. And may be, for example, mono- or polysubstituted by the substituents mentioned for X _{1 to} X ₂₄ .

R ₁ is more preferably a hydrogen atom, a linear, branched or cyclic alkyl group having a total of 1 to 24 carbon atoms which may have a substituent, or a total group which may have a substituent. A linear, branched or cyclic alkenyl group having 2 to 24 carbon atoms,
An aralkyl group having a total of 7 to 24 carbon atoms which may have a substituent, or a total of 6 to 6 carbon atoms which may have a substituent
24 aryl groups, more preferably a hydrogen atom, a linear, branched or cyclic alkyl group having a total of 1 to 24 carbon atoms, which may have a substituent; It is an aralkyl group having 7 to 24 carbon atoms or an aryl group having 6 to 24 carbon atoms which may have a substituent.

R ₂ is more preferably a hydrogen atom, a linear, branched or cyclic alkyl group having 1 to 24 carbon atoms, which may have a substituent, or a total group which may have a substituent. A linear, branched or cyclic alkenyl group having 2 to 24 carbon atoms,
An aralkyl group having 7 to 24 carbon atoms which may have a substituent, an aryl group having 6 to 24 carbon atoms which may have a substituent, or an amino group, more preferably a hydrogen atom A total carbon number of 1 to 5 which may have a substituent
24 straight-chain, branched or cyclic alkyl groups, aralkyl groups having a total of 7 to 24 carbon atoms which may have a substituent, aryl groups having a total of 6 to 24 carbon atoms which may have a substituent,
Alternatively, it is an amino group.

R ₃ is more preferably a straight-chain, branched or cyclic alkyl group having 1 to 24 carbon atoms which may have a substituent, or 2 carbon atoms which may have a substituent. ~ 2
4 straight-chain, branched or cyclic alkenyl groups, aralkyl groups having 7 to 24 carbon atoms which may have a substituent, or aryl groups having 6 to 24 carbon atoms which may have a substituent And more preferably, a linear, branched or cyclic alkyl group having 1 to 24 carbon atoms which may have a substituent, or an aralkyl having 7 to 24 carbon atoms which may have a substituent. A group or an aryl group having a total of 6 to 24 carbon atoms which may have a substituent.

X₁~ X_{twenty four}Is more preferably a hydrogen source
Atom, halogen atom, total carbon number which may have a substituent
1 to 24 linear, branched or cyclic alkyl groups and substituents
May have a linear chain of 1 to 24 carbon atoms, branched or
Is a cyclic alkoxy group, a total coal which may have a substituent
Linear, branched or cyclic alkylthio having a prime number of 1 to 24
Group having a total carbon number of 2 to 24 which may have a substituent.
Having a chain, branched or cyclic alkenyl group or substituent
May be a straight-chain, branched or cyclic alkyl group having 2 to 24 carbon atoms.
Lucenyloxy group, total carbon number which may have a substituent
2-24 linear, branched or cyclic alkenylthio groups,
A substituted or unsubstituted aralkyl group having 7 to 24 carbon atoms in total,
Substituted or unsubstituted aralkyloxy having 7 to 24 carbon atoms in total
Si group, substituted or unsubstituted aralkyl having 7 to 24 carbon atoms
Luthio group, substituted or unsubstituted ant having 6 to 24 carbon atoms in total
Aryl group, substituted or unsubstituted aryl having 6 to 24 carbon atoms
A substituted or unsubstituted alkoxy group having 6 to 24 carbon atoms
Reelthio group, unsubstituted amino group, having 1 to 24 carbon atoms
Substituted amino group, cyano group, hydroxyl group, nitro group, -COO
R ₁, -COR_TwoOr -OCOR_Three(However,
Medium, R₁~ R_ThreeRepresents the same meaning as described above).

More preferably, X _{8 to} X ₁₁ and X ₂₀
X ₂₃ has a hydrogen atom, a halogen atom, a linear, branched or cyclic alkyl group having 1 to 8 carbon atoms, a linear, branched or cyclic alkoxy group having 1 to 8 carbon atoms, or a substituent; X is a hydrogen atom, a halogen atom, a linear, branched or cyclic alkyl group having a total of 1 to 20 carbon atoms which may have a substituent; 1 to total carbon atoms which may have a substituent
20 straight-chain, branched or cyclic alkoxy groups, a total of 1 to 20 carbon atoms which may have a straight-chain, branched or cyclic alkylthio group, a total number of carbon atoms which may have a substituent 2-20 linear, branched or cyclic alkenyl groups,
A straight-chain, branched or cyclic alkenyloxy group having 2 to 20 carbon atoms which may have a substituent, a straight-chain, branched or cyclic alkenyloxy group having 2 to 20 carbon atoms which may have a substituent Alkenylthio group, substituted or unsubstituted total carbon number 7-20
Aralkyl group, substituted or unsubstituted total carbon number 7-20
Aralkyloxy group, substituted or unsubstituted total carbon number 7
To 20 aralkylthio groups, substituted or unsubstituted aryl groups having a total carbon number of 6 to 20, substituted or unsubstituted aryloxy groups having a total carbon number of 6 to 20, substituted or unsubstituted aryl groups having a total carbon number of 6 to 20; Arylthio group, unsubstituted amino group, substituted amino group having 1 to 20 carbon atoms, cyano group, hydroxyl group, nitro group, —COOR ₁ , —COR ₂ , or —OCO
R ₃ (wherein, R _{1 to} R ₃ represent the same meaning as described above).

Particularly preferably, X _{8 to} X ₁₁ and X ₂₀ to
X ₂₃ is a hydrogen atom or a linear alkyl group having 1 to 4 carbon atoms, and other X is a hydrogen atom, a halogen atom,
A straight-chain, branched or cyclic alkyl group having a total of 1 to 16 carbon atoms which may have a substituent, a straight-chain, branched or cyclic alkyl group having a total of 1 to 16 carbon atoms which may have a substituent A straight-chain, branched or cyclic alkylthio group having 1 to 16 carbon atoms which may have a substituent or a substituent; a straight-chain, branched or cyclic alkylthio group having 2 to 16 carbon atoms which may have a substituent Alkenyl group, substituted or unsubstituted aryl group having a total of 6 to 20 carbon atoms, substituted or unsubstituted arylthio group having a total of 6 to 20 carbon atoms, unsubstituted amino group, and substituted amino group having a total carbon number of 1 to 20 , Cyano group, hydroxyl group, nitro group, -COO
R ₁ or —COR ₂ (wherein, R _{1 to} R ₂ represent the same meaning as described above). Furthermore, mutually adjacent groups selected from X _{1 to} X ₂₄ , or X ₃ and X ₄ , X
₁₅ and X ₁₆ , X ₇ and X ₂₄ , or X ₁₂ and X ₁₉ may be bonded to each other to form a substituted or unsubstituted carbocyclic aliphatic ring together with a substituted carbon atom, Preferably, it may form a substituted or unsubstituted carbocyclic aliphatic ring having a total of 4 to 20 carbon atoms.

Specific examples of X _{1 to} X ₂₄ include a hydrogen atom;
For example, a halogen atom such as a fluorine atom, a chlorine atom, and a bromine atom; for example, a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, se
c-butyl group, tert-butyl group, n-pentyl group, isopentyl group, neopentyl group, tert-pentyl group, n-hexyl group, 1-methylpentyl group, 4-methyl-2-pentyl group, 2-ethylbutyl group , N-heptyl group, 1-
Methylhexyl group, n-octyl group, 1-methylheptyl group, 2-ethylhexyl group, 2-propylpentyl group, n-nonyl group, 2,2-dimethylheptyl group, 2,
6-dimethyl-4-heptyl group, 3,5,5-trimethylhexyl group, n-decyl group, 1-ethyloctyl group,
n-undecyl group, 1-methyldecyl group, n-dodecyl group, n-tridecyl group, 1-hexylheptyl group, n-
Tetradecyl group, n-pentadecyl group, 1-heptyloctyl group, n-hexadecyl group, n-heptadecyl group,
1-octylnonyl group, n-octadecyl group, 1-nonyldecyl group, 1-decylundecyl group, n-eicosyl group, n-docosyl group, n-tetracosyl group, cyclohexylmethyl group, (1-isopropylcyclohexyl) methyl group, 2 -Cyclohexylethyl group, bornel group, isobornel group, 1-norbornyl group, 2-norbornanemethyl group, 1-bicyclo [2.2.2] octyl group, 1
-Adamantyl group, 3-noradamantyl group, 1-adamantylmethyl group, cyclobutyl group, cyclopentyl group, 1-methylcyclopentyl group, cyclohexyl group,
4-methylcyclohexyl group, 3-methylcyclohexyl group, 2-methylcyclohexyl group, 2,3-dimethylcyclohexyl group, 2,5-dimethylcyclohexyl group, 2,6-dimethylcyclohexyl group, 3,4-dimethylcyclohexyl group, 3,5-dimethylcyclohexyl group, 2,4,6-trimethylcyclohexyl group, 3,
3,5-trimethylcyclohexyl group, 2,6-diisopropylcyclohexyl group, 4-tert-butylcyclohexyl group, 3-tert-butylcyclohexyl group, 4-phenylcyclohexyl group, 2-phenylcyclohexyl group, cycloheptyl group, cyclooctyl Group, cyclodecyl group, cyclododecyl group, cyclotetradecyl group,

Methoxymethyl group, ethoxymethyl group, n
-Butoxymethyl group, n-hexyloxymethyl group,
(2-ethylbutyloxy) methyl group, n-octyloxymethyl group, n-decyloxymethyl group, 2-methoxyethyl group, 2-ethoxyethyl group, 2-n-propoxyethyl group, 2-isopropoxyethyl group , 2-n-butoxyethyl group, 2-n-pentyloxyethyl group, 2
-N-hexyloxyethyl group, 2- (2'-ethylbutyloxy) ethyl group, 2-n-heptyloxyethyl group, 2-n-octyloxyethyl group, 2- (2'-ethylhexyloxy) ethyl group , 2-n-decyloxyethyl group, 2-n-dodecyloxyethyl group, 2-n-
Tetradecyloxyethyl group, 2-cyclohexyloxyethyl group, 2-methoxypropyl group, 3-methoxypropyl group, 3-ethoxypropyl group, 3-n-propoxypropyl group, 3-isopropoxypropyl group, 3-
(N-butoxy) propyl group, 3- (n-pentyloxy) propyl group, 3- (n-hexyloxy) propyl group, 3- (2'-ethylbutoxy) propyl group, 3-
(N-octyloxy) propyl group, 3- (2'-ethylhexyloxy) propyl group, 3- (n-decyloxy) propyl group, 3- (n-dodecyloxy) propyl group, 3- (n-tetradecyloxy ) Propyl group, 3-
Cyclohexyloxypropyl group, 4-methoxybutyl group, 4-ethoxybutyl group, 4-n-propoxybutyl group, 4-isopropoxybutyl group, 4-n-butoxybutyl group, 4-n-hexyloxybutyl group, 4 -N-octyloxybutyl group, 4-n-decyloxybutyl group, 4-n-dodecyloxybutyl group, 5-methoxypentyl group, 5-ethoxypentyl group, 5-n-propoxypentyl group, 6-ethoxyhexyl Group, 6-isopropoxyhexyl group, 6-n-butoxyhexyl group, 6-
n-hexyloxyhexyl group, 6-n-decyloxyhexyl group, 4-methoxycyclohexyl group, 7-ethoxyheptyl group, 7-isopropoxyheptyl group, 8-
Methoxyoctyl group, 10-methoxydecyl group, 10-
n-butoxydecyl group, 12-ethoxydodecyl group, 1
2-isopropoxide dodecyl group, tetrahydrofurfuryl group, 2- (2′-methoxyethoxy) ethyl group, 2-
(2′-ethoxyethoxy) ethyl group, 2- (2′-n
-Butoxyethoxy) ethyl group, 3- (2'-ethoxyethoxy) propyl group, 2-allyloxyethyl group,
-(4'-pentenyloxy) ethyl group, 3-allyloxypropyl group, 3- (2'-hexenyloxy) propyl group, 3- (2'-heptenyloxy) propyl group,
3- (1′-cyclohexenyloxy) propyl group, 4
An allyloxybutyl group,

Benzyloxymethyl, 2-benzyloxyethyl, 2-phenethyloxyethyl, 2-
(4′-methylbenzyloxy) ethyl group, 2- (2 ′
-Methylbenzyloxy) ethyl group, 2- (4'-fluorobenzyloxy) ethyl group, 2- (4'-chlorobenzyloxy) ethyl group, 3-benzyloxypropyl group, 3- (4'-methoxybenzyloxy) ) Propyl, 4-benzyloxybutyl, 2- (benzyloxymethoxy) ethyl, 2- (4′-methylbenzyloxymethoxy) ethyl, phenyloxymethyl,
-Methylphenyloxymethyl group, 3-methylphenyloxymethyl group, 2-methylphenyloxymethyl group,
4-methoxyphenyloxymethyl group, 4-fluorophenyloxymethyl group, 4-chlorophenyloxymethyl group, 2-chlorophenyloxymethyl group, 2-phenyloxyethyl group, 2- (4′-methylphenyloxy) ethyl group, 2- (4'-ethylphenyloxy) ethyl group, 2- (4'-methoxyphenyloxy) ethyl group, 2- (4'-chlorophenyloxy) ethyl group, 2
-(4'-bromophenyloxy) ethyl group, 2-
(1′-naphthyloxy) ethyl group, 2- (2′-naphthyloxy) ethyl group, 3-phenyloxypropyl group, 3- (2′-naphthyloxy) propyl group, 4-phenyloxybutyl group, 4- (2′-ethylphenyloxy) butyl group, 5- (4′-tert-butylphenyloxy) pentyl group, 6- (2′-chlorophenyloxy) hexyl group, 8-phenyloxyoctyl group, 10
-Phenyloxydecyl group, 10- (3'-chlorophenyloxy) decyl group, 2- (2'-phenyloxyethoxy) ethyl group, 3- (2'-phenyloxyethoxy) propyl group, 4- (2'- Phenyloxyethoxy) butyl, cinnamyl, cinnamylmethyl, 2
A cinnamylethyl group,

N-butylthiomethyl, n-hexylthiomethyl, 2-methylthioethyl, 2-ethylthioethyl, 2-n-butylthioethyl, 2-n-hexylthioethyl, 2- n-octylthioethyl group, 2
-N-decylthioethyl group, 3-methylthiopropyl group, 3-ethylthiopropyl group, 3-n-butylthiopropyl group, 4-ethylthiobutyl group, 4-n-propylthiobutyl group, 4-n- Butylthiobutyl group, 5-ethylthiopentyl group, 6-methylthiohexyl group, 6-ethylthiohexyl group, 6-n-butylthiohexyl group,
8-methylthiooctyl group, 2- (2'-methoxyethylthio) ethyl group, 4- (3'-ethoxypropylthio) butyl group, 2- (2'-ethylthioethylthio) ethyl group, 2-allylthio Ethyl group, 2-benzylthioethyl group, 3- (4'-methylbenzylthio) propyl group, 4-benzylthiobutyl group, 2- (2'-benzyloxyethylthio) ethyl group, 3- (3'- Benzylthiopropylthio) propyl group, 2-phenylthioethyl group, 2- (4′-methoxyphenylthio) ethyl group,
-(2'-phenyloxyethylthio) ethyl group, 3-
(2′-phenylthioethylthio) propyl group, fluoromethyl group, 3-fluoropropyl group, 6-fluorohexyl group, 8-fluorooctyl group, trifluoromethyl group, 1,1-dihydro-perfluoroethyl group, 1,
1-dihydro-perfluoro-n-propyl group, 1,
1,3-trihydro-perfluoro-n-propyl group,
1,1-dihydro-perfluoro-n-butyl group, 1,
1-dihydro-perfluoro-n-pentyl group, 1,1
-Dihydro-perfluoro-n-hexyl group, 6-fluorohexyl group, 4-fluorocyclohexyl group,
1-dihydro-perfluoro-n-octyl group, 1,1
-Dihydro-perfluoro-n-decyl group, 1,1-dihydro-perfluoro-n-dodecyl group, 1,1-dihydro-perfluoro-n-tetradecyl group, 1,1-dihydro-perfluoro-n- Hexadecyl group, perfluoro-n-hexyl group, dichloromethyl group, 2-chloroethyl group, 3-chloropropyl group, 4-chlorocyclohexyl group, 7-chloroheptyl group, 8-chlorooctyl group, 2,2,2- Trichloroethyl group, 2-hydroxyethyl group, 2-hydroxypropyl group, 3-hydroxypropyl group, 3-hydroxybutyl group, 4-hydroxybutyl group, 6-hydroxyhexyl group, 5-hydroxyheptyl group, 8-hydroxyoctyl Group, 10-hydroxydecyl group, 12-hydroxydodecyl group, 2-hydroxycyclohexyl Linear, branched or cyclic alkyl group, such as Le group;

For example, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, sec-butoxy, n-pentyloxy, neopentyloxy, isopentyloxy, cyclopentyl Oxy group, n-hexyloxy group, 2-ethylbutoxy group, 3,3-dimethylbutoxy group, cyclohexyloxy group, n-heptyloxy group, n-octyloxy group, 2-ethylhexyloxy group, n-nonyloxy group, n-decyloxy group, n-dodecyloxy group, n-tetradecyloxy group, n-hexadecyloxy group, n-octadecyloxy group, n-eicosyloxy group, n-docosyloxy group, n-tetracosyloxy group , Fluoromethoxy group, trifluoromethoxy group,
1,1-dihydroperfluoroethoxy group, perfluoroethoxy group, 1,1-dihydroperfluoro-n-propoxy group, 1,1,3-trihydroperfluoro-n
-Propoxy group, 1,1-dihydroperfluoro-n-
Butoxy group, 1,1-dihydroperfluoro-n-pentyloxy group, 1,1-dihydroperfluoro-n-hexyloxy group, 4-chlorocyclohexyloxy group,
1,1-dihydroperfluoro-n-octyloxy group, 1,1-dihydroperfluoro-n-decyloxy group, 1,1-dihydroperfluoro-n-dodecyloxy group, 1,1-dihydroperfluoro-n A hexadecyloxy group,

Ethoxymethoxy, 1-methoxyethoxy, 2-methoxyethoxy, 2-ethoxyethoxy, 2-n-propoxyethoxy, 2-isopropoxyethoxy, 2-n-butoxyethoxy, n-
Hexyloxyethoxy group, 2-n-octyloxyethoxy group, 2- (2'-ethylhexyloxy) ethoxy group, 2-n-decyloxyethoxy group, 2-methoxypropoxy group, 3-methoxypropoxy group, 3-ethoxy Propoxy group, 3-isopropoxypropoxy group, 3
-N-butoxypropoxy group, 3-n-hexyloxypropoxy group, 3-n-octyloxypropoxy group,
2-methoxybutoxy group, 3-methoxybutoxy group, 4
-Methoxybutoxy group, 4-ethoxybutoxy group, 4-
Isopropoxybutoxy group, 4-n-butoxybutoxy group, 4-n-hexyloxybutoxy group, 4-n-decyloxybutoxy group, 4-n-dodecyloxybutoxy group, 5-ethoxypentyloxy group, 6-methoxy Hexyloxy group, 6-ethoxyhexyloxy group, 6-isopropoxyhexyloxy group, 4-methoxycyclohexyloxy group, 7-methoxyheptyloxy group, 8-
Ethoxyoctyloxy group, 10-methoxydecyloxy group, 12-ethoxydodecyloxy group, 2- (2′-
Methoxyethyloxy) ethoxy group, 3- (2′-ethoxyethyloxy) propoxy group, 2-benzyloxyethoxy group, 2- (4-methylbenzyloxy) ethoxy group, 2- (4-methoxybenzyloxy) ethoxy group A 3- (4-ethylbenzyloxy) propoxy group,
4- (3-fluorobenzyloxy) butoxy group, 4-
(4-chlorobenzyloxy) butoxy group, 6- (3-
Methylbenzyloxy) hexyloxy group, phenyloxymethoxy group, 2-phenyloxyethoxy group, 2-
(1′-naphthyloxy) ethoxy group, 2- (2′-naphthyloxy) ethoxy group, 2- (4′-methylphenyloxy) ethoxy group, 2- (4′-methoxyphenyloxy) ethoxy group, 2- (3′-ethoxyphenyloxy) ethoxy group, 2- (4′-chlorophenyloxy) ethoxy group, 3-phenyloxypropoxy group, 3
-(4'-ethylphenyloxy) propoxy group, 3-
(4′-chlorophenyloxy) propoxy group, 3-
Linear, branched or cyclic alkoxy such as (2′-naphthyloxy) propoxy, 4-phenyloxybutoxy, 6-phenyloxyhexyloxy, 8-phenyloxyoctyloxy, and 10-phenyloxydecyloxy Group;

For example, a methylthio group, an ethylthio group, n
-Propylthio, isopropylthio, n-butylthio, isobutylthio, sec-butylthio, n-pentylthio, neopentylthio, isopentylthio, cyclopentylthio, n-hexylthio, 2-
Ethylbutylthio group, 3,3-dimethylbutylthio group,
Cyclohexylthio, n-heptylthio, n-octylthio, 2-ethylhexylthio, n-nonylthio, n-decylthio, n-dodecylthio, n-tetradecylthio, n-hexadecylthio, n-octadecyl Thio group, n-eicosylthio group, n-docosylthio group, n-tetracosylthio group, fluoromethylthio group, trifluoromethylthio group, 1,1-dihydroperfluoroethylthio group, perfluoroethylthio group,
1,1-dihydroperfluoro-n-propylthio group,
1,1,3-trihydroperfluoro-n-propylthio group, 1,1-dihydroperfluoro-n-butylthio group, 1,1-dihydroperfluoro-n-pentylthio group, 1,1-dihydroperfluoro- n-hexylthio group, 4-chlorocyclohexylthio group, 1,1-dihydroperfluoro-n-octylthio group, 1,1-dihydroperfluoro-n-decylthio group, 1,1-dihydroperfluoro-n-dodecylthio group A 1,1-dihydroperfluoro-n-hexadecylthio group,

Ethoxymethylthio, 1-methoxyethylthio, 2-methoxyethylthio, 2-ethoxyethylthio, 2-n-propoxyethylthio, 2-isopropoxyethylthio, 2-n-butoxy Ethylthio group, 2-n-hexyloxyethylthio group, 2-n-
Octyloxyethylthio, 2- (2′-ethylhexyloxy) ethylthio, 2-n-decyloxyethylthio, 2-methoxypropylthio, 3-methoxypropylthio, 3-ethoxypropylthio, 3 -Isopropoxypropylthio group, 3-n-butoxypropylthio group, 3-n-hexyloxypropylthio group, 3
-N-octyloxypropylthio group, 2-methoxybutylthio group, 3-methoxybutylthio group, 4-methoxybutylthio group, 4-ethoxybutylthio group, 4-isopropoxybutylthio group, 4-n-butoxy Butylthio group, 4-n-hexyloxybutylthio group, 4-n-decyloxybutylthio group, 4-n-dodecyloxybutylthio group, 5-ethoxypentylthio group, 6-methoxyhexylthio group, 6- Ethoxyhexylthio group, 6-isopropoxyhexylthio group, 4-methoxycyclohexylthio group, 7-methoxyheptylthio group, 8-ethoxyoctylthio group, 10-methoxydecylthio group, 12
-Ethoxydodecylthio, 2- (2'-methoxyethyloxy) ethylthio, 3- (2'-ethoxyethyloxy) propylthio, 2-benzyloxyethylthio, 2- (4-methylbenzyloxy) ethylthio Group, 2- (4-methoxybenzyloxy) ethylthio group, 3- (4-ethylbenzyloxy) propylthio group, 4- (3-fluorobenzyloxy) butylthio group, 4- (4-chlorobenzyloxy) butylthio group,
6- (3-methylbenzyloxy) hexylthio group, phenyloxymethylthio group, 2-phenyloxyethylthio group, 2- (1′-naphthyloxy) ethylthio group,
2- (2′-naphthyloxy) ethylthio group, 2-
(4′-methylphenyloxy) ethylthio group, 2-
(4′-methoxyphenyloxy) ethylthio group, 2-
(3′-ethoxyphenyloxy) ethylthio group, 2-
(4′-chlorophenyloxy) ethylthio group, 3-phenyloxypropylthio group, 3- (4′-ethylphenyloxy) propylthio group, 3- (4′-chlorophenyloxy) propylthio group, 3- (2′-naphthyl) Linear, branched or cyclic alkylthio groups such as oxy) propylthio, 4-phenyloxybutylthio, 6-phenyloxyhexylthio, 8-phenyloxyoctylthio, and 10-phenyloxydecylthio;

For example, vinyl group, allyl group, 2-butenyl group, 3-butenyl group, 1-methyl-4-pentenyl group, 2-pentenyl group, 4-pentenyl group, 1-methyl-2-butenyl group, 2 -Hexenyl group, 3-hexenyl group, 4-hexenyl group, 5-hexenyl group, 2-heptenyl group, 1-vinylhexyl group, 3-nonenyl group, 6-
Nonenyl group, 9-decenyl group, 10-undecenyl group,
13-tetradecenyl group, 15-hexadecenyl group, 1
A 7-octadecenyl group, a 23-n-tetracosenyl group,
1-cyclopentenyl group, 1-cyclohexenyl group, ethoxyvinyl group, n-butoxyvinyl group, benzylvinyl group, cinnamyl group, 2,2-diphenylvinyl group, 2
-(4'-methylphenyl) vinyl group, 2- (3'-methylphenyl) vinyl group, 2- (4'-methoxyphenyl) vinyl group, 2- (4'-chlorophenyl) vinyl group, phenyloxyvinyl group Linear, branched or cyclic alkenyl groups such as vinyloxy, allyloxy, 2-butenyloxy, 3-butenyloxy, 1-methyl-4-pentenyloxy, 2-pentenyloxy, 4-pentenyloxy Group, 1-methyl-
2-butenyloxy group, 2-hexenyloxy group, 3-
Hexenyloxy group, 4-hexenyloxy group, 5-hexenyloxy group, 2-heptenyloxy group, 1-vinylhexyloxy group, 3-nonenyloxy group, 6-nonenyloxy group, 9-decenyloxy group, 10-undecenyloxy group , 13-tetradecenyloxy group, 15-
Hexadecenyloxy group, 17-octadecenyloxy group, 23-tetracosenyloxy group, 1-cyclopentenyloxy group, 1-cyclohexenyloxy group, ethoxyvinyloxy group, n-butoxyvinyloxy group, Linear, branched or cyclic alkenyloxy groups such as benzylvinyloxy, cinnamyloxy, and phenyloxyvinyloxy; for example, vinylthio, allylthio, 2-butenylthio, 3-butenylthio, 4-pentenylthio Group, 5-hexenylthio group, 9-decenylthio group, 13-tetradecenylthio group, 15-hexadecenylthio group, 17-octadecenylthio group, 23-tetracosenylthio group, 1-cyclohexenylthio group Group, n
A straight-chain, branched or cyclic alkenylthio group such as -butoxyvinylthio group,

For example, benzyl group, α-methylbenzyl group, α-ethylbenzyl group, phenethyl group, α-methylphenethyl group, β-methylphenethyl group, α, α-dimethylbenzyl group, α, α-dimethylphenethyl group , 4-
Methylphenethyl group, 4-methylbenzyl group, 3-methylbenzyl group, 2-methylbenzyl group, 4-ethylbenzyl group, 2-ethylbenzyl group, 4-isopropylbenzyl group, 4-tert-butylbenzyl group, 2- tert-butylbenzyl group, 4-tert-pentylbenzyl group, 4-cyclohexylbenzyl group, 4-n-octylbenzyl group, 4-tert-octylbenzyl group, 4-allylbenzyl group, 4-benzylbenzyl group, 4- Phenethylbenzyl group, 4-phenylbenzyl group, 4- (4′-methylphenyl) benzyl group, 4-methoxybenzyl group, 2-methoxybenzyl group, 2-ethoxybenzyl group, 4-n-
Butoxybenzyl group, 4-n-heptyloxybenzyl group, 4-n-decyloxybenzyl group, 4-n-tetradecyloxybenzyl group, 4-n-heptadecyloxybenzyl group, 3,4-dimethoxybenzyl group, 4-methoxymethylbenzyl group, 4-isobutoxymethylbenzyl group, 4-allyloxybenzyl group, 4-vinyloxymethylbenzyl group, 4-benzyloxybenzyl group, 4
-Phenethyloxybenzyl group, 4-phenyloxybenzyl group, 3-phenyloxybenzyl group, 4-hydroxybenzyl group, 3-hydroxybenzyl group, 2-hydroxybenzyl group, 4-hydroxy-3-methoxybenzyl group, 4- Fluorobenzyl group, 2-fluorobenzyl group, 4-chlorobenzyl group, 3-chlorobenzyl group,
2-chlorobenzyl group, 3,4-dichlorobenzyl group,
Substituted or unsubstituted aralkyl groups such as 2-furfuryl group, diphenylmethyl group, 1-naphthylmethyl group, 2-naphthylmethyl group;

For example, benzyloxy, phenethyloxy, β-methylphenethyloxy, 4-methylphenethyloxy, 4-methylbenzyloxy,
Methylbenzyloxy group, 2-methylbenzyloxy group, 4-ethylbenzyloxy group, 4-isopropylbenzyloxy group, 4-tert-butylbenzyloxy group,
4-cyclohexylbenzyloxy group, 4-n-octylbenzyloxy group, 4-allylbenzyloxy group,
-Benzylbenzyloxy group, 4-phenylbenzyloxy group, 4- (4'-methylphenyl) benzyloxy group, 4-methoxybenzyloxy group, 2-methoxybenzyloxy group, 2-ethoxybenzyloxy group, 4-n
-Butoxybenzyloxy group, 4-n-heptyloxybenzyloxy group, 4-n-decyloxybenzyloxy group, 4-n-tetradecyloxybenzyloxy group,
4-n-heptadecyloxybenzyloxy group, 3,4
-Dimethoxybenzyloxy group, 4-methoxymethylbenzyloxy group, 4-isobutoxymethylbenzyloxy group, 4-allyloxybenzyloxy group, 4-vinyloxymethylbenzyloxy group, 4-benzyloxybenzyloxy group, 4- Phenethyloxybenzyloxy group, 4-phenyloxybenzyloxy group, 3-phenyloxybenzyloxy group, 4-hydroxybenzyloxy group, 4-fluorobenzyloxy group, 4-chlorobenzyloxy group, 3-chlorobenzyloxy group, 3,4
A substituted or unsubstituted aralkyloxy group such as -dichlorobenzyloxy group, 1-naphthylmethyloxy group, 2-naphthylmethyloxy group;

For example, benzylthio, phenethylthio, β-methylphenethyloxy, 4-methylphenethylthio, 4-methylbenzylthio, 3-methylbenzylthio, 4-ethylbenzylthio, 4-isopropyl Benzylthio, 4-tert-butylbenzylthio, 4-cyclohexylbenzylthio, 4-n-octylbenzylthio, 4-allylbenzylthio, 4-
Benzylbenzylthio, 4-phenylbenzylthio, 4- (4′-methylphenyl) benzylthio, 4
-Methoxybenzylthio group, 2-methoxybenzylthio group, 2-ethoxybenzylthio group, 4-n-butoxybenzylthio group, 4-n-heptyloxybenzylthio group, 4-n-decyloxybenzylthio group, 4 -N-tetradecyloxybenzylthio group, 4-n-heptadecyloxybenzylthio group, 3,4-dimethoxybenzylthio group, 4-methoxymethylbenzylthio group, 4-allyloxybenzylthio group, 4-benzyloxy Benzylthio, 4-phenethyloxybenzylthio, 4-phenyloxybenzylthio, 3-phenyloxybenzylthio, 4-hydroxybenzylthio, 4-fluorobenzylthio, 4-chlorobenzylthio, 1 −
A substituted or unsubstituted aralkylthio group such as a naphthylmethylthio group or a 2-naphthylmethylthio group;

For example, phenyl, 1-naphthyl, 2
-Naphthyl group, 2-anthracenyl group, 9-anthracenyl group, fluorenyl group, 4-quinolyl group, 4-pyridyl group, 3-pyridyl group, 2-pyridyl group, 3-furyl group, 2-furyl group, 3-thienyl Group, 2-thienyl group,
2-oxazolyl group, 2-thiazolyl group, 2-benzooxazolyl group, 2-benzothiazolyl group, 2-benzimidazolyl group, 4-methylphenyl group, 3-methylphenyl group, 2-methylphenyl group, 4-ethylphenyl Group, 3-ethylphenyl group, 2-ethylphenyl group, 4
-N-propylphenyl group, 4-isopropylphenyl group, 2-isopropylphenyl group, 4-n-butylphenyl group, 4-isobutylphenyl group, 4-sec-butylphenyl group, 2-sec-butylphenyl group, 4 -Tert-
Butylphenyl group, 3-tert-butylphenyl group, 2-
tert-butylphenyl group, 4-n-pentylphenyl group, 4-isopentylphenyl group, 4-tert-pentylphenyl group, 4-n-hexylphenyl group, 4-n-heptylphenyl group, 4-n-octyl Phenyl group, 4-
(2′-ethylhexyl) phenyl group, 4-tert-octylphenyl group, 4-n-nonylphenyl group, 4-n-
Decylphenyl group, 4-n-dodecylphenyl group, 4-
n-tetradecylphenyl group, 4-n-hexadecylphenyl group, 4-n-octadecylphenyl group, 4-cyclopentylphenyl group, 4-cyclohexylphenyl group, 4- (4′-tert-butylcyclohexyl) phenyl group, 4- (4'-methylcyclohexyl) phenyl group, 3-cyclohexylphenyl group, 2-cyclohexylphenyl group, 4-ethyl-1-naphthyl group, 6-n-
Butyl-2-naphthyl group,

2,3-dimethylphenyl group, 2,4-dimethylphenyl group, 2,5-dimethylphenyl group, 3,
4-dimethylphenyl group, 3,5-dimethylphenyl group, 2,6-dimethylphenyl group, 2,3,5-trimethylphenyl group, 3,4,5-trimethylphenyl group,
2,4-diethylphenyl group, 2,3,6-trimethylphenyl group, 2,4,6-trimethylphenyl group, 2,
6-diethylphenyl group, 2,6-diisopropylphenyl group, 2,6-diisobutylphenyl group, 2,4-di-tert-butylphenyl group, 2,5-di-tert-butylphenyl group, 3,5- Di-tert-butylphenyl group,
2,4-dineopentylphenyl group, 2,5-di-tert
-Pentylphenyl group, 4,6-di-tert-butyl-2
-Methylphenyl group, 5-tert-butyl-2-methylphenyl group, 4-tert-butyl-2,6-dimethylphenyl group, 2,3,5,6-tetramethylphenyl group, 5-
Indanyl group, 1,2,3,4-tetrahydro-5-naphthyl group, 1,2,3,4-tetrahydro-6-naphthyl group, 4-methoxyphenyl group, 3-methoxyphenyl group, 2-methoxyphenyl group , 4-ethoxyphenyl group, 2-ethoxyphenyl group, 3-n-propoxyphenyl group, 4-isopropoxyphenyl group, 2-isopropoxyphenyl group, 4-n-butoxyphenyl group, 4-
Isobutoxyphenyl group, 2-isobutoxyphenyl group, 2-sec-butoxyphenyl group, 4-n-pentyloxyphenyl group, 4-isopentyloxyphenyl group, 2-isopentyloxyphenyl group, 2-neopentyloxy A phenyl group, a 4-n-hexyloxyphenyl group, a 2- (2′-ethylbutyl) oxyphenyl group,
4-n-octyloxyphenyl group, 4-n-decyloxyphenyl group, 4-n-dodecyloxyphenyl group,
4-n-tetradecyloxyphenyl group, 4-n-hexadecyloxyphenyl group, 4-n-octadecyloxyphenyl group, 4-cyclohexyloxyphenyl group,
2-cyclohexyloxyphenyl group, 2-methoxy-
1-naphthyl group, 4-methoxy-1-naphthyl group, 4-
n-butoxy-1-naphthyl group, 5-ethoxy-1-naphthyl group, 6-ethoxy-2-naphthyl group, 6-n-butoxy-2-naphthyl group, 6-n-hexyloxy-2
-Naphthyl group, 7-methoxy-2-naphthyl group, 7-n
-Butoxy-2-naphthyl group,

2,3-dimethoxyphenyl group, 2,4-
Dimethoxyphenyl group, 2,5-dimethoxyphenyl group, 2,6-dimethoxyphenyl group, 3,4-dimethoxyphenyl group, 3,5-dimethoxyphenyl group, 3,5
-Diethoxyphenyl group, 3,5-di-n-butoxyphenyl group, 2-methoxy-4-methylphenyl group, 2-
Methoxy-5-methylphenyl group, 2-methyl-4-methoxyphenyl group, 3-methyl-4-methoxyphenyl group, 3-methyl-5-methoxyphenyl group, 3-ethyl-5-methoxyphenyl group, 2- Methoxy-4-ethoxyphenyl group, 2-methoxy-6-ethoxyphenyl group, 3,4,5-trimethoxyphenyl group, 4-fluorophenyl group, 3-fluorophenyl group, 2-fluorophenyl group, 4-chlorophenyl Group, 3-chlorophenyl group, 2-chlorophenyl group, 4-bromophenyl group,
2-bromophenyl group, 4-chloro-1-naphthyl group,
4-chloro-2-naphthyl group, 6-bromo-2-naphthyl group, 2,3-difluorophenyl group, 2,4-difluorophenyl group, 2,5-difluorophenyl group, 2,
6-difluorophenyl group, 3,4-difluorophenyl group, 3,5-difluorophenyl group, 2,3-dichlorophenyl group, 2,4-dichlorophenyl group, 2,5-
Dichlorophenyl group, 2,6-dichlorophenyl group,
3,4-dichlorophenyl group, 3,5-dichlorophenyl group, 2,5-dibromophenyl group, 2,4,6-trichlorophenyl group, 2,3,6-tribromophenyl group, 3,4,5-tri Fluorophenyl group, 2,4-dichloro-1-naphthyl group, 1,6-dichloro-2-naphthyl group,

2-fluoro-4-methylphenyl group, 2
-Fluoro-5-methylphenyl group, 3-fluoro-2
-Methylphenyl group, 3-fluoro-4-methylphenyl group, 4-fluoro-2-methylphenyl group, 5-fluoro-2-methylphenyl group, 2-chloro-4-methylphenyl group, 2-chloro-5 -Methylphenyl group, 2-
Chloro-6-methylphenyl group, 3-chloro-2-methylphenyl group, 4-chloro-2-methylphenyl group, 4
-Chloro-3-methylphenyl group, 2-chloro-4,6
-Dimethylphenyl group, 2-fluoro-4-methoxyphenyl group, 2-fluoro-6-methoxyphenyl group, 3
-Fluoro-4-ethoxyphenyl group, 5-chloro-2
-Methoxyphenyl group, 6-chloro-3-methoxyphenyl group, 5-chloro-2,4-dimethoxyphenyl group,
2-chloro-4-nitrophenyl group, 4-chloro-2-
Nitrophenyl group, 4-trifluoromethylphenyl group, 3-trifluoromethylphenyl group, 2-trifluoromethylphenyl group, 3,5-bis (trifluoromethyl) phenyl group, 4-trifluoromethyloxyphenyl group, 4-allylphenyl group, 2-allylphenyl group, 2-isopropenylphenyl group, 4-benzylphenyl group, 2-benzylphenyl group, 4- (4'-methylbenzyl) phenyl group, 4-cumylphenyl group, 4-
(4'-methoxycumyl) phenyl group, 4-phenylphenyl group, 3-phenylphenyl group, 2-phenylphenyl group, 4- (4'-methylphenyl) phenyl group,
-(4'-ethylphenyl) phenyl group, 4- (4'-
Isopropylphenyl) phenyl group, 4- (4′-tert
-Butylphenyl) phenyl group, 4- (4'-n-hexylphenyl) phenyl group, 4- (4'-n-octylphenyl) phenyl group, 4- (4'-methoxyphenyl) phenyl group, 4- ( 4'-ethoxyphenyl) phenyl group, 4- (4'-n-butoxyphenyl) phenyl group, 2- (2'-methoxyphenyl) phenyl group, 4-
(4′-fluorophenyl) phenyl group, 4- (4′-
Chlorophenyl) phenyl group, 3-methyl-4-phenyl group, 2-methoxy-5-phenylphenyl group, 3-methoxy-4-phenylphenyl group,

4-methoxymethylphenyl, 4-ethoxymethylphenyl, 4-n-butoxymethylphenyl, 3-methoxymethylphenyl, 4- (2'-methoxyethyl) phenyl, 4- (2 ' -Ethoxyethyloxy) phenyl group, 4- (2'-n-butoxyethyloxy) phenyl group, 4- (3'-ethoxypropyloxy) phenyl group, 4-vinyloxyphenyl group,
-Allyloxyphenyl group, 3-allyloxyphenyl group, 4- (4′-pentenyloxy) phenyl group, 4-
Allyloxy-1-naphthyl group, 4-allyloxymethylphenyl group, 4- (2′-allyloxyethyloxy) phenyl group, 4-benzyloxyphenyl group, 2-
Benzyloxyphenyl, 4-phenethyloxyphenyl, 4- (4′-chlorobenzyloxy) phenyl, 4- (4′-methylbenzyloxy) phenyl,
4- (4′-methoxybenzyloxy) phenyl group, 4
-(3'-ethoxybenzyloxy) phenyl group, 4-
Benzyloxy-1-naphthyl group, 5- (4′-methylbenzyloxy) -1-naphthyl group, 6-benzyloxy-2-naphthyl group, 6- (4′-methylbenzyloxy) -2-naphthyl group, 7-benzyloxy-2-naphthyl group, 4- (benzyloxymethyl) phenyl group, 4
A-(2'-benzyloxyethyloxy) phenyl group,

4-phenyloxyphenyl, 3-phenyloxyphenyl, 2-phenyloxyphenyl, 4- (4'-methylphenyloxy) phenyl,
4- (4′-methoxyphenyloxy) phenyl group, 4
-(4'-chlorophenyloxy) phenyl group, 4-phenyloxy-1-naphthyl group, 6-phenyloxy-
2-naphthyl group, 7-phenyloxy-2-naphthyl group, 4-phenyloxymethylphenyl group, 4- (2 ′
-Phenyloxyethyloxy) phenyl group, 4-
[2 '-(4'-methylphenyloxy) ethyloxy] phenyl group, 4- [2'-(4'-methoxyphenyloxy) ethyloxy] phenyl group, 4- [2'-
(4'-chlorophenyloxy) ethyloxy] phenyl group, 4-acetylphenyl group, 3-acetylphenyl group, 2-acetylphenyl group, 4-ethylcarbonylphenyl group, 2-ethylcarbonylphenyl group, 4-n-
Butylcarbonylphenyl group, 4-n-hexylcarbonylphenyl group, 4-n-octylcarbonylphenyl group, 4-cyclohexylcarbonylphenyl group, 4-acetyl-1-naphthyl group, 6-acetyl-2-naphthyl group, 6- n-butylcarbonyl-2-naphthyl group, 4-
Allylcarbonylphenyl group, 4-benzylcarbonylphenyl group, 4- (4′-methylbenzyl) carbonylphenyl group, 4-phenylcarbonylphenyl group, 4-
(4′-methylphenyl) carbonylphenyl group, 4-
(4′-chlorophenyl) carbonylphenyl group, 4-
Phenylcarbonyl-1-naphthyl group, 4-methoxycarbonylphenyl group, 2-methoxycarbonylphenyl group, 4-ethoxycarbonylphenyl group, 3-ethoxycarbonylphenyl group, 4-n-propoxycarbonylphenyl group, 4-n-butoxy Carbonylphenyl group,
4-n-hexyloxycarbonylphenyl group, 4-n
-Decyloxycarbonylphenyl group, 4-cyclohexyloxycarbonylphenyl group, 4-ethoxycarbonyl-1-naphthyl group, 6-methoxycarbonyl-2-
Naphthyl group, 6-n-butoxycarbonyl-2-naphthyl group, 4-allyloxycarbonylphenyl group, 4-benzyloxycarbonylphenyl group, 4- (4'-chlorobenzyl) oxycarbonylphenyl group, 4-phenethyloxycarbonyl Phenyl group, 6-benzyloxycarbonyl-2-naphthyl group, 4-phenyloxycarbonylphenyl group, 4- (4′-ethylphenyl) oxycarbonylphenyl group, 4- (4′-chlorophenyl) oxycarbonylphenyl group, -(4'-ethoxyphenyl) oxycarbonylphenyl group, 6-phenyloxycarbonyl-2-naphthyl group,

4-acetyloxyphenyl, 3-acetyloxyphenyl, 2-acetyloxyphenyl, 4-ethylcarbonyloxyphenyl, 2-ethylcarbonyloxyphenyl, 4-n-propylcarbonyloxyphenyl, 4-n-pentylcarbonyloxyphenyl group, 4-n-octylcarbonyloxyphenyl group, 4-cyclohexylcarbonyloxyphenyl group, 3-cyclohexylcarbonyloxyphenyl group, 4-acetyloxy-1-naphthyl group, 4-n- Butylcarbonyloxy-1-naphthyl group, 5-acetyloxy-1-naphthyl group, 6-ethylcarbonyloxy-2-naphthyl group, 7-acetyloxy-2-naphthyl group, 4-allylcarbonyloxyphenyl group, 4- Benzylcarbonyloxy Phenyl group, 4-phenethylcarbonyloxyphenyl group, 6-benzylcarbonyloxy-2-naphthyl group, 4-phenylcarbonyloxyphenyl group, 4- (4′-methylphenyl) carbonyloxyphenyl group, 4- (2′- Methylphenyl) carbonyloxyphenyl group, 4- (4′-chlorophenyl)
Carbonyloxyphenyl group, 4- (2′-chlorophenyl) carbonyloxyphenyl group, 4-phenylcarbonyloxy-1-naphthyl group, 6-phenylcarbonyloxy-2-naphthyl group, 7-phenylcarbonyloxy-2-naphthyl group , 4-methylthiophenyl group, 2
-Methylthiophenyl group, 2-ethylthiophenyl group,
3-ethylthiophenyl group, 4-n-propylthiophenyl group, 2-isopropylthiophenyl group, 4-n-butylthiophenyl group, 2-isobutylthiophenyl group,
2-neopentylphenyl group, 4-n-hexylthiophenyl group, 4-n-octylthiophenyl group, 4-cyclohexylthiophenyl group, 4-benzylthiophenyl group, 3-benzylthiophenyl group, 2-benzylthio Phenyl group, 4- (4'-chlorobenzylthio) phenyl group, 4-phenylthiophenyl group, 3-phenylthiophenyl group, 2-phenylthiophenyl group, 4- (4'-
Methylphenylthio) phenyl group, 4- (3′-methylphenylthio) phenyl group, 4- (4′-methoxyphenylthio) phenyl group, 4- (4′-chlorophenylthio) phenyl group, 2-ethylthio-1 -Naphthyl group, 4
-Methylthio-1-naphthyl group, 6-ethylthio-2-
Naphthyl group, 6-phenylthio-2-naphthyl group,

4-nitrophenyl, 3-nitrophenyl, 2-nitrophenyl, 3,5-dinitrophenyl, 4-nitro-1-naphthyl, 4-formylphenyl, 3-formylphenyl, 2-formylphenyl group, 4-formyl-1-naphthyl group, 1-formyl-
2-naphthyl group, 4-pyrrolidinophenyl group, 4-piperidinophenyl group, 4-morpholinophenyl group, 4-
(N-ethylpiperazino) phenyl group, 4-pyrrolidino-1-naphthyl group, 4-aminophenyl group, 3-aminophenyl group, 2-aminophenyl group, 4- (N-methylamino) phenyl group, 3- (N -Methylamino) phenyl group, 4- (N-ethylamino) phenyl group, 2- (N
-Isopropylamino) phenyl group, 4- (Nn-butylamino) phenyl group, 2- (Nn-butylamino) phenyl group, 4- (Nn-octylamino) phenyl group, 4- (N-butylamino) phenyl group -N-dodecylamino) phenyl group,
4- (N-benzylamino) phenyl group, 4- (N-phenylamino) phenyl group, 2- (N-phenylamino) phenyl group, 4- (N, N-dimethylamino) phenyl group, 3- (N , N-dimethylamino) phenyl group,
4- (N, N-diethylamino) phenyl group, 2-
(N, N-dimethylamino) phenyl group, 2- (N, N
-Diethylamino) phenyl group, 4- (N, N-di-n
-Butylamino) phenyl group, 4- (N, N-di-n-
Hexylamino) phenyl group, 4- (N-cyclohexyl-N-methylamino) phenyl group, 4- (N, N-diethylamino) -1-naphthyl group, 4- (N-benzyl-N-phenylamino) phenyl group , 4- (N, N-diphenylamino) phenyl group, 4- [N-phenyl-N
-(4-methylphenyl) amino] phenyl group, 4-
[N, N-di (3'-methylphenyl) amino] phenyl group, 4- [N, N-di (4'-methylphenyl) amino] phenyl group, 4- [N, N-di (4'- Methoxyphenyl) amino] phenyl group, 2- (N, N-diphenylamino) phenyl group, 4-hydroxyphenyl group, 3
-Hydroxyphenyl group, 2-hydroxyphenyl group,
4-methyl-3-hydroxyphenyl group, 6-methyl-
3-hydroxyphenyl group, 2-hydroxy-1-naphthyl group, 8-hydroxy-1-naphthyl group, 4-hydroxy-1-naphthyl group, 1-hydroxy-2-naphthyl group, 6-hydroxy-2-naphthyl group Substituted or unsubstituted aryl groups such as, 4-cyanophenyl, 2-cyanophenyl, 4-cyano-1-naphthyl, 6-cyano-2-naphthyl;

For example, phenyloxy, 2-methylphenyloxy, 3-methylphenyloxy, 4-methylphenyloxy, 4-ethylphenyloxy,
4-n-propylphenyloxy group, 4-isopropylphenyloxy group, 4-n-butylphenyloxy group,
4-tert-butylphenyloxy group, 4-isopentylphenyloxy group, 4-tert-pentylphenyloxy group, 4-n-hexylphenyloxy group, 4-cyclohexylphenyloxy group, 4-n-octylphenyloxy group , 4-n-decylphenyloxy group, 4-n-octadecylphenyloxy group, 2,3-dimethylphenyloxy group, 2,4-dimethylphenyloxy group, 2,
5-dimethylphenyloxy group, 3,4-dimethylphenyloxy group, 5-indanyloxy group, 1,2,3
4-tetrahydro-5-naphthyloxy group, 1,2,2
3,4-tetrahydro-6-naphthyloxy group, 2-methoxyphenyloxy group, 3-methoxyphenyloxy group, 4-methoxyphenyloxy group, 3-ethoxyphenyloxy group, 4-ethoxyphenyloxy group, 4-n
-Propoxyphenyloxy group, 4-isopropoxyphenyloxy group, 4-n-butoxyphenyloxy group,
4-n-pentyloxyphenyloxy group, 4-n-hexyloxyphenyloxy group, 4-cyclohexyloxyphenyloxy group, 4-n-heptyloxyphenyloxy group, 4-n-octyloxyphenyloxy group, 4- n-decyloxyphenyloxy group, 2,3-
Dimethoxyphenyloxy group, 2,5-dimethoxyphenyloxy group, 3,4-dimethoxyphenyloxy group,
2-methoxy-5-methylphenyloxy group, 3-methyl-4-methoxyphenyloxy group, 2-fluorophenyloxy group, 3-fluorophenyloxy group, 4-fluorophenyloxy group, 2-chlorophenyloxy group, 3 -Chlorophenyloxy group, 4-chlorophenyloxy group, 4-bromophenyloxy group, 4-trifluoromethylphenyloxy group, 3,4-dichlorophenyloxy group, 2-methyl-4-chlorophenyloxy group, 2-chloro-4 -Methylphenyloxy group, 3-chloro-4-methylphenyloxy group, 2-chloro-4-
Methoxyphenyloxy group, 4-phenylphenyloxy group, 3-phenylphenyloxy group, 4- (4′-methylphenyl) phenyloxy group, 4- (4′-methoxyphenyl) phenyloxy group, 1-naphthyloxy group , 2-naphthyloxy group, 4-ethoxy-1-naphthyloxy group, 6-methoxy-2-naphthyloxy group, 7
-Ethoxy-2-naphthyloxy group, 2-furyloxy group, 2-thienyloxy group, 3-thienyloxy group, 2
A substituted or unsubstituted aryloxy group such as -pyridyloxy group, 3-pyridyloxy group, 4-pyridyloxy group;

For example, phenylthio, 3-methylphenylthio, 4-methylphenylthio, 4-ethylphenylthio, 4-n-propylphenylthio, 4-
n-butylphenylthio group, 4-tert-butylphenylthio group, 4-n-hexylphenylthio group, 4-cyclohexylphenylthio group, 4-n-octylphenylthio group, 4-n-dodecylphenylthio group, 4-n-octadecylphenylthio group, 2,3-dimethylphenylthio group, 3,4-dimethylphenylthio group, 3-methoxyphenylthio group, 4-methoxyphenylthio group, 3-ethoxyphenylthio group, 4- An ethoxyphenylthio group,
4-n-propoxyphenylthio group, 4-n-butoxyphenylthio group, 4-n-hexyloxyphenylthio group, 4-n-octyloxyphenylthio group, 4-n-
Decyloxyphenylthio, 3,4-dimethoxyphenylthio, 3-methyl-4-methoxyphenylthio, 3-fluorophenylthio, 4-fluorophenylthio, 4-chlorophenylthio, 2-methyl- 4
-Chlorophenylthio group, 2-chloro-4-methoxyphenylthio group, 4-phenylphenylthio group, 4-
(4′-methylphenyl) phenylthio group, 4- (4 ′
-Methoxyphenyl) substituted or unsubstituted arylthio groups such as phenylthio group, 1-naphthylthio group and 2-naphthylthio group; for example, N-methylamino group, N-ethylamino group, N-isopropylamino group, Nn- Butylamino group, Nn-hexylamino group, Nn-decylamino group, Nn-tetradecylamino group, N, N-
Dimethylamino group, N, N-diethylamino group, N, N
-Di-n-butylamino group, N, N-di-n-hexylamino group, N, N-di-n-octylamino group, N, N
-Di-n-decylamino group, N, N-di-n-dodecylamino group, N-phenylamino group, N- (4-methylphenyl) amino group, N-phenyl-N-methylamino group, N-phenyl -N-ethylamino group, N, N-diphenylamino group, N, N-di (4-methylphenyl) amino group, N, N-di (4-ethylphenyl) amino group,
Substituted amino groups such as N, N-di (4-methoxyphenyl) amino group, N-phenyl-N-naphthylamino group; amino group; cyano group; hydroxyl group;

For example, carboxyl, methoxycarbonyl, ethoxycarbonyl, n-propoxycarbonyl, n-butoxycarbonyl, isobutoxycarbonyl, n-pentyloxycarbonyl, n-hexyloxycarbonyl, n-octyl Oxycarbonyl group, 2-ethylhexyloxycarbonyl group, n-decyloxycarbonyl group, n-dodecyloxycarbonyl group, n-tetradecyloxycarbonyl group, n-hexadecyloxycarbonyl group, n-octadecyloxycarbonyl group, cyclohexyloxy Carbonyl group, benzyloxycarbonyl group, phenethyloxycarbonyl group, (4-methylbenzyloxy) carbonyl group,
(3-methylbenzyloxy) carbonyl group, (4-te
rt-butylbenzyloxy) carbonyl group, (4-methoxybenzyloxy) carbonyl group, (4-chlorobenzyloxy) carbonyl group, phenyloxycarbonyl group, (4-methylphenyloxy) carbonyl group, (3
-Methylphenyloxy) carbonyl group, (4-ethylphenyloxy) carbonyl group, (4-tert-butylphenyloxy) carbonyl group, (4-methoxyphenyloxy) carbonyl group, (2-methoxyphenyloxy) carbonyl group, A -COOR ₁ group such as a (4-ethoxyphenyloxy) carbonyl group or a (4-fluorophenyloxy) carbonyl group, wherein R ₁ has the same meaning as described above;

For example, a formyl group, a methylcarbonyl group, an ethylcarbonyl group, an n-propylcarbonyl group,
n-butylcarbonyl group, n-hexylcarbonyl group,
n-octylcarbonyl group, 2-ethylhexylcarbonyl group, n-decylcarbonyl group, n-dodecylcarbonyl group, n-tetradecylcarbonyl group, n-hexadecylcarbonyl group, n-octadecylcarbonyl group, cyclohexylcarbonyl group, benzylcarbonyl Group, phenethylcarbonyl group, (4-methylbenzyl) carbonyl group, (4-tert-butylbenzyl) carbonyl group,
(4-methoxybenzyl) carbonyl group, (4-chlorobenzyl) carbonyl group, phenylcarbonyl group, (4
-Methylphenyl) carbonyl group, (3-methylphenyl) carbonyl group, (4-ethylphenyl) carbonyl group, (4-tert-butylphenyl) carbonyl group, (4
-COR ₂ groups such as -methoxyphenyl) carbonyl group, (2-methoxyphenyl) carbonyl group, (4-ethoxyphenyl) carbonyl group, (4-fluorophenyl) carbonyl group, and amide (wherein R ₂ is as defined above) Expresses the same meaning);

For example, methylcarbonyloxy, ethylcarbonyloxy, n-propylcarbonyloxy, n-butylcarbonyloxy, n-pentylcarbonyloxy, n-hexylcarbonyloxy, n
-Octylcarbonyloxy group, 2-ethylhexylcarbonyloxy group, n-decylcarbonyloxy group, n
-Dodecylcarbonyloxy group, n-tetradecylcarbonyloxy group, n-hexadecylcarbonyloxy group, n-octadecylcarbonyloxy group, cyclohexylcarbonyloxy group, benzylcarbonyloxy group, phenethylcarbonyloxy group, (4′-methylbenzyl Carbonyl) oxy group, (4′-tert-butylbenzylcarbonyl) oxy group, (4′-methoxybenzylcarbonyl) oxy group, (4′-chlorobenzylcarbonyl) oxy group, phenylcarbonyloxy group,
(4′-methylphenylcarbonyl) oxy group, (3 ′
-Methylphenylcarbonyl) oxy group, (4'-ethylphenylcarbonyl) oxy group, (4'-tert-butylphenylcarbonyl) oxy group, (4'-methoxyphenylcarbonyl) oxy group, (2'-methoxyphenylcarbonyl) ) oxy group, and (4'-ethoxyphenyl) oxy group, (4'-fluorophenyl carbonyl) -OCOR ₃ groups such as oxy group (wherein, R ₃ are as defined above) .

In the organic electroluminescent device of the present invention, bisacenaphtho [1 ', 2': 5,6] indeno [1,2,3-cd: 1 ', 2', 3 '
-lm] perylene derivatives, for example, bisacenaphtho [1 ', 2': 5,6] indeno [1,2,3-cd: 1 ', 2', 3'- When an [lm] perylene derivative is used in a light-emitting layer as a light-emitting component, it is possible to provide an organic electroluminescent element that emits orange to red light with high luminance and excellent durability, which has not existed conventionally. Further, when a light-emitting layer is formed in combination with another light-emitting component, an organic electroluminescent element that emits white light with high luminance and excellent durability can be provided. Specific examples of the compound A according to the present invention include, for example,
The following compounds (Chemical Formulas 6 to 59) can be exemplified, but the present invention is not limited thereto. In the exemplified compounds, Ph represents a phenyl group, and Bz represents a benzyl group.

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[0050]

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[0053]

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[0054]

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[0055]

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[0056]

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[0057]

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[0058]

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[0059]

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[0060]

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[0061]

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[0062]

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[0063]

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[0064]

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[0065]

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[0066]

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[0067]

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[0068]

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[0069]

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[0070]

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[0071]

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[0072]

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[0073]

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[0074]

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[0075]

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[0076]

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[0077]

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[0078]

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[0079]

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[0080]

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[0081]

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[0082]

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[0083]

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[0084]

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[0085]

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[0086]

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[0087]

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[0088]

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[0089]

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[0090]

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[0091]

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[0092]

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[0093]

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[0094]

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[0095]

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[0102]

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The compound A according to the present invention, for example, the compound represented by the general formula (1-A) is, for example, a compound represented by the general formula (2)
3,3′-Biasenaphtho [1,2-k] represented by (Formula 60)
Reacting the fluoranthene derivative in the presence of an oxidizing agent (eg, aluminum chloride / cupric chloride, aluminum chloride / sodium chloride, cobalt trifluoride, thallium trifluoroacetate, lead tetraacetate, or ferric chloride) Ring closure (for example, J. Amer. Chem. Soc., 102, 6504 (198
0), and the method described in Chem. Rev., 87 , 357 (1987) can be referred to].

[0104]

Embedded image [Wherein, X _{1 to} X ₂₄ represent the same meaning as in the case of the general formula (1-A)]

The compound represented by the general formula (2) may be, for example, acenaphtho represented by the general formula (3) (Chemical Formula 61).
[1,2-k] fluoranthene derivative and general formula (4)
The acenaphtho [1,2-k] fluoranthene derivative represented by 1) is reacted in the presence of, for example, nickel chloride, triphenylphosphine and zinc, and, if desired, sodium bromide [for example, J. Org. Chem., 51 ,
2627 (1986).)
It can be manufactured by the following. Further, for example, an acenaphtho [1,2-k] fluoranthene derivative represented by the general formula (3) and an acenaphtho [1,2-k] fluoranthene derivative represented by the general formula (4) are combined with, for example, palladium acetate With tetra-n-butylammonium bromide [see, for example, Tetrahedron Lett., 39 , 2559 (19
98) can be referred to]].

[0106]

Embedded image[Where X₁~ X_{twenty four}Has the same meaning as in formula (1-A)
Represents the taste, Z₁And Z _TwoRepresents a halogen atom.] In the general formulas (3) and (4), Z₁and
Z_TwoRepresents a halogen atom, preferably a chlorine atom,
Represents an element atom or an iodine atom.

The compounds represented by the general formulas (3) and (4) are described, for example, in J. Amer. Chem. Soc., 115 , 1
1542 (1993). That is, for example, a cyclopenta [a] acenaphthylene-8-one derivative [for example, Chem. Rev., 65 , 261 (1
965)] and a 1,5-dihalogenoacenaphthylene derivative. Furthermore, for example, cyclopenta [a]
After reacting the acenaphthylene-8-one derivative with the 5-halogenoacenaphthylene derivative, dehydrogenation [for example, chloranyl, 2,3-dichloro-5,6-
Using dicyano-1,4-benzoquinone (DDQ)] [for example,
J. Chem. Soc., 1462 (1958), Indian J. Chem. Sect.
B, 22B , 225 (1983)].

Further, the general formulas (3) and (4)
Is obtained by reacting a 3-halogenocyclopenta [a] acenaphthylene-8-one derivative with a 1-halogenoacenaphthylene derivative, or for example, by reacting a 3-halogenocyclopenta [a] acenaphthylene After reacting the -8-one derivative with the acenaphthylene derivative, dehydrogenation [for example, chloranyl, 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) is used as a dehydrogenating agent] [For example, Angew. Chem. Int. Ed.
Engl., 30 , 172 (1991) can be referred to]. Further, after forming the skeleton of the general formula (1-A), a compound having a desired substituent can also be produced by conversion of the substituent according to a usual method.

In addition, bisacenaft [1 ', 2': 5,6] indeno
[1,2,3-cd: 1 ′, 2 ′, 3′-lm] perylene derivatives include 7,
12,19,24-tetraphenylbisacenaphtho [1 ',
2 ': 5,6] Indeno [1,2,3-cd: 1', 2 ', 3'-lm] perylene
That is, in the general formula (1-A), X ₇ , X ₁₂ , X
Compounds in which ₁₉ and X ₂₄ are simultaneously a phenyl group and all other X's are hydrogen atoms are already known [J. Amer. Chem. Soc., 120 , 2476 (1998)], Is not known. The compound A according to the present invention may be produced in a form in which a solvate is formed with a solvent (for example, an aromatic hydrocarbon solvent such as toluene) used in some cases. , And such solvates. Needless to say, a non-solvate containing no solvent is also included. In the organic electroluminescent device of the present invention, not only a non-solvate of the compound A of the present invention but also such a solvate can be used. When the compound A according to the present invention is used for an organic electroluminescent device, a recrystallization method, a column chromatography method,
It is preferable to use a purification method such as a sublimation purification method, or a compound having an increased purity by using these methods in combination.

The organic electroluminescent device usually has at least one light-emitting layer containing at least one light-emitting component sandwiched between a pair of electrodes. In consideration of the functional levels of hole injection and hole transport, electron injection and electron transport of the compound used in the light emitting layer, a hole injection transport layer containing a hole injection transport component and / or an electron may be provided as desired. An electron injection / transport layer containing an injection / transport component can also be provided. For example, when the hole injection function, hole transport function and / or electron injection function, and electron transport function of the compound used for the light emitting layer are good, the light emitting layer is formed of the hole injection transport layer and / or the electron injection transport layer. The element can also be configured to serve as Needless to say, depending on the case, a structure of a device (single-layer device) in which both the hole injection transport layer and the electron injection transport layer are not provided may be employed. Further, each of the hole injection transport layer, the electron injection transport layer and the light emitting layer may have a single-layer structure or a multilayer structure,
The hole injecting and transporting layer and the electron injecting and transporting layer can be formed by separately providing a layer having an injection function and a layer having a transport function in each layer.

In the organic electroluminescent device of the present invention, the compound A according to the present invention is preferably used for a hole injecting and transporting component, a light emitting component or an electron injecting and transporting component. Is more preferable,
It is particularly preferable to use it for a light emitting component. In the organic electroluminescent device of the present invention, the compound A according to the present invention may be used alone or in combination.

The structure of the organic electroluminescent device of the present invention is not particularly limited.
(B) anode / hole injection / transport layer / light emitting layer / cathode device (FIG. 2), (C) anode / light emission Layer / electron injection / transport layer / cathode device (FIG. 3), (D) anode / light-emitting layer / cathode device (FIG. 4), and the like. Further, the device is of a type in which a light emitting layer is sandwiched between electron injection and transport layers (E).
Anode / hole injection / transport layer / electron injection / transport layer / emission layer / electron injection / transport layer / cathode device (FIG. 5).
The element configuration of the (D) type is, of course, an element of a type in which a light emitting component is sandwiched between a pair of electrodes in a single layer form, and further, for example, (F) a hole injection / transport component, a light emitting component, An element of the type sandwiched between a pair of electrodes in the form of a single layer in which an electron injecting and transporting component is mixed (FIG. 6). (G) Between the pair of electrodes in a single layer in which a hole injecting and transporting component and a light emitting component are mixed. There is an element of the sandwiched type (FIG. 7) and an element of the type (H) sandwiched between a pair of electrodes in the form of a single layer in which a light emitting component and an electron injection / transport component are mixed (FIG. 8).

The organic electroluminescent device of the present invention is not limited to these device configurations, but may be provided with a plurality of hole injection / transport layers, light emitting layers, and electron injection / transport layers in each type of device. Can be. Further, in each type of device, between the hole injection transport layer and the light emitting layer,
A mixed layer of a light emitting component and an electron injecting and transporting component may be provided between the light emitting layer and the electron injecting and transporting layer. More preferred configurations of the organic electroluminescent element include (A) type element, (B) type element, (C) type element, (E) type element, (F) type element,
(G) type element or (H) type element, more preferably (A) type element, (B) type element, (C) type element,
(F) type element or (H) type element.

As the organic electroluminescent device of the present invention, for example, (A) anode / hole injection / transport layer / light emitting layer / electron injection / transport layer / cathode type device shown in FIG. 1 will be described.
In FIG. 1, 1 is a substrate, 2 is an anode, 3 is a hole injection / transport layer, 4 is a light emitting layer, 5 is an electron injection / transport layer, 6 is a cathode,
Reference numeral 7 denotes a power supply.

The organic electroluminescent device of the present invention is preferably supported on a substrate 1. The substrate is not particularly limited, but is preferably transparent or translucent. For example, a glass plate, Transparent plastic sheet (for example, polyester, polycarbonate, polysulfone, polymethyl methacrylate, polypropylene,
A sheet made of polyethylene or the like), a translucent plastic sheet, quartz, a transparent ceramic, or a composite sheet combining these. Further, the luminescent color can be controlled by combining, for example, a color filter film, a color conversion film, and a dielectric reflection film on the substrate.

As the anode 2, it is preferable to use a metal, an alloy or an electrically conductive compound having a relatively large work function as an electrode material. As the electrode material used for the anode, for example, gold, platinum, silver, copper, cobalt, nickel,
Palladium, vanadium, tungsten, tin oxide, zinc oxide, ITO (indium tin oxide), polythiophene, polypyrrole, and the like can be given. These electrode substances may be used alone or in combination of two or more. The anode can be formed on the substrate by using such an electrode material by, for example, a vapor deposition method, a sputtering method, or the like. Further, the anode may have a single-layer structure or a multilayer structure. The sheet electric resistance of the anode is preferably several hundred Ω / □.
Hereinafter, more preferably, it is set to about 5 to 50 Ω / □. The thickness of the anode depends on the material of the electrode substance used, but is generally about 5 to 1000 nm, more preferably,
It is set to about 10 to 500 nm.

The hole injecting / transporting layer 3 is a layer containing a compound having a function of facilitating the injection of holes (holes) from the anode and a function of transporting the injected holes. The hole injecting and transporting layer is formed of the compound A according to the present invention and / or another compound having a hole injecting and transporting function (for example, a phthalocyanine derivative, a triarylmethane derivative, a triarylamine derivative, an oxazole derivative, a hydrazone derivative, a stilbene derivative). , Pyrazoline derivatives, polysilane derivatives, polyphenylenevinylene and its derivatives,
Polythiophene and a derivative thereof, a poly-N-vinyl carbazole derivative, and the like). The compounds having a hole injection / transport function may be used alone or in combination of two or more.

Other compounds having a hole injection / transport function used in the present invention include triarylamine derivatives (for example, 4,4′-bis [N-phenyl-N- (4 ″)).
-Methylphenyl) amino] biphenyl, 4,4'-bis [N-phenyl-N- (3 "-methylphenyl) amino] biphenyl, 4,4'-bis [N-phenyl-N-
(3 "-methoxyphenyl) amino] biphenyl, 4,
4'-bis [N-phenyl-N- (1 "-naphthyl) amino] biphenyl, 3,3'-dimethyl-4,4'-bis [N-phenyl-N- (3" -methylphenyl) amino] Biphenyl, 1,1-bis [4 '-[N, N-di (4 "-methylphenyl) amino] phenyl] cyclohexane, 9,10-bis [N- (4'-methylphenyl) -N- (4 "-N-butylphenyl) amino] phenanthrene, 3,8-bis (N, N-diphenylamino) -6-phenylphenanthridine, 4-methyl-
N, N-bis [4 ", 4"'-bis[N',N'-di (4
-Methylphenyl) amino] biphenyl-4-yl] aniline, N, N'-bis [4- (diphenylamino) phenyl] -N, N'-diphenyl-1,3-diaminobenzene, N, N'-bis [4- (diphenylamino) phenyl] -N, N'-diphenyl-1,4-diaminobenzene, 5,5 "-bis [4- (bis [4-methylphenyl] amino) phenyl] -2,2 ' : 5 ', 2 "-terthiophene, 1,3,5-tris (diphenylamino) benzene, 4,4', 4" -tris (N-carbazoyl) triphenylamine, 4,4 ', 4 "-tris [N- (3 "'-methylphenyl) -N-phenylamino) triphenylamine, 4,4', 4" -tris [N, N-bis (4 ""-tert-butylbiphenyl-
4 ""-yl) amino] triphenylamine, 1,3
5-tris [N- (4'-diphenylaminophenyl)
-N-phenylaminobenzene, etc.), polythiophene and derivatives thereof, and poly-N-vinylcarbazole derivatives are more preferred. When the compound A according to the present invention is used in combination with another compound having a hole injecting and transporting function, the proportion of the compound A according to the present invention in the hole injecting and transporting layer is preferably 0.1 to 40% by weight. Prepare to about.

The light emitting layer 4 has a hole and electron injection function,
This is a layer containing a compound having a transport function thereof and a function of generating excitons by recombination of holes and electrons. The light-emitting layer is formed of the compound A according to the present invention and / or a compound having a light-emitting function (eg, an acridone derivative, a quinacridone derivative, a diketopyrrolopyrrole derivative, a polycyclic aromatic compound [eg, rubrene, anthracene, tetracene, pyrene). , Perylene, chrysene, decacyclene, coronene, tetraphenylcyclopentadiene, pentaphenylcyclopentadiene, 9,10-diphenylanthracene, 9,10-bis (phenylethynyl) anthracene, 1,4-bis (9'-ethynylanthracenyl) ) Benzene, 4,4′-bis (9 ″ -ethynylanthracenyl) biphenyl], a triarylamine derivative (for example, the compounds described above as compounds having a hole injecting and transporting function), and organometallic complexes [For example, Tris (8- Rinorato) aluminum, bis (10-benzo [h] quinolinolato) beryllium, 2
Zinc salt of-(2'-hydroxyphenyl) benzoxazole, zinc salt of 2- (2'-hydroxyphenyl) benzothiazole, zinc salt of 4-hydroxyacridine,
Zinc salt of 3-hydroxyflavone, beryllium salt of 5-hydroxyflavone, aluminum salt of 5-hydroxyflavone], stilbene derivative [for example, 1,1,4,
4-tetraphenyl-1,3-butadiene, 4,4′-
Bis (2,2-diphenylvinyl) biphenyl, 4,
4'-bis [(1,1,2-triphenyl) ethenyl]
Biphenyl], coumarin derivatives [for example, coumarin 1,
Coumarin 6, Coumarin 7, Coumarin 30, Coumarin 10
6, Coumarin 138, Coumarin 151, Coumarin 15
2, Coumarin 153, Coumarin 307, Coumarin 31
1. Coumarin 314, Coumarin 334, Coumarin 33
8, coumarin 343, coumarin 500], pyran derivatives [eg, DCM1, DCM2], oxazone derivatives [eg, Nile Red], benzothiazole derivatives,
Benzoxazole derivatives, benzimidazole derivatives, pyrazine derivatives, cinnamate derivatives, poly-
N-vinyl carbazole and its derivatives, polythiophene and its derivatives, polyphenylene and its derivatives, polyfluorene and its derivatives, polyphenylene vinylene and its derivatives, polybiphenylene vinylene and its derivatives, polyterphenylene vinylene and its derivatives, polynaphthylene vinylene and Derivatives, polythienylenevinylene and derivatives thereof) can be used.

In the organic electroluminescent device of the present invention, the light emitting layer preferably contains the compound A of the present invention. When the compound A according to the present invention and a compound having another light-emitting function are used in combination, the ratio of the compound A according to the present invention in the light-emitting layer is preferably 0.001 to 99.99.
About 9% by weight, more preferably 0.01 to 99.99
% By weight, more preferably about 0.1 to 99.9% by weight. As the other compound having a light-emitting function used in the present invention, a light-emitting organometallic complex is more preferable. For example, J. Appl. Phys., 65 , 3610 (1989),
As described in JP-A-5-214332, the light emitting layer can be composed of a host compound and a guest compound (dopant).

The compound A according to the present invention can be used as a host compound to form a light-emitting layer, and further, can be used as a guest compound to form a light-emitting layer. When the compound A according to the present invention is used as a guest compound to form a light-emitting layer, examples of the host compound include the compounds having the other light-emitting functions, such as a light-emitting organometallic complex or Triarylamine derivatives are more preferred. In this case, the compound A according to the present invention is preferably used in an amount of about 0.001 to 40% by weight, more preferably about 0.01 to 30% by weight, based on the luminescent organometallic complex or the triarylamine derivative. Particularly preferably, about 0.1 to 20% by weight is used.

The light-emitting organometallic complex used in combination with the compound A according to the present invention is not particularly limited, but a light-emitting organic aluminum complex is preferable, and a light-emitting organic compound having a substituted or unsubstituted 8-quinolinolate ligand. Organic aluminum complexes are more preferred. Preferred luminescent organic metal complexes include, for example, luminescent organic aluminum complexes represented by general formulas (a) to (c). (Q) ₃ -Al (a) (wherein Q represents a substituted or unsubstituted 8-quinolinolate ligand) (Q) ₂ -Al-OL (b) (wherein Q represents substituted 8 Represents a quinolinolate ligand, OL represents a phenolate ligand, and L represents a hydrocarbon group having 6 to 24 carbon atoms including a phenyl moiety.) (Q) ₂ -Al-O-Al- (Q ) ₂ (c) (wherein Q represents a substituted 8-quinolinolate ligand)

Specific examples of the luminescent organometallic complex include, for example, tris (8-quinolinolate) aluminum, tris (4-methyl-8-quinolinolate) aluminum, tris (5-methyl-8-quinolinolate) aluminum, tris ( 3,4-dimethyl-8-quinolinolate) aluminum, tris (4,5-dimethyl-8-quinolinolate) aluminum, tris (4,6-dimethyl-8-quinolinolate) aluminum, bis (2-methyl-8-quinolinolate) (Phenolate) aluminum, bis (2-methyl-8-quinolinolate) (2-
Methylphenolate) aluminum, bis (2-methyl-8-quinolinolate) (3-methylphenolate) aluminum, bis (2-methyl-8-quinolinolate)
(4-methylphenolate) aluminum, bis (2-
Methyl-8-quinolinolate) (2-phenylphenolate) aluminum, bis (2-methyl-8-quinolinolate) (3-phenylphenolate) aluminum,
Bis (2-methyl-8-quinolinolate) (4-phenylphenolate) aluminum, bis (2-methyl-8
-Quinolinolate) (2,3-dimethylphenolate)
Aluminum, bis (2-methyl-8-quinolinolate) (2,6-dimethylphenolate) aluminum,
Bis (2-methyl-8-quinolinolate) (3,4-dimethylphenolate) aluminum, bis (2-methyl-8-quinolinolate) (3,5-dimethylphenolate) aluminum, bis (2-methyl-8- Quinolinolate) (3,5-di-tert-butylphenolate) aluminum, bis (2-methyl-8-quinolinolate)
(2,6-diphenylphenolate) aluminum, bis (2-methyl-8-quinolinolate) (2,4,6-
Triphenylphenolate) aluminum, bis (2-
Methyl-8-quinolinolate) (2,4,6-trimethylphenolate) aluminum, bis (2-methyl-8
-Quinolinolate) (2,4,5,6-tetramethylphenolate) aluminum, bis (2-methyl-8-quinolinolate) (1-naphtholate) aluminum, bis (2-methyl-8-quinolinolate) (2-naphtholate) ) Aluminum, bis (2,4-dimethyl-8-quinolinolate) (2-phenylphenolate) aluminum, bis (2,4-dimethyl-8-quinolinolate)
(3-phenylphenolato) aluminum, bis (2,4-dimethyl-8-quinolinolate) (4-phenylphenolate) aluminum, bis (2,4-dimethyl-8-quinolinolate) (3,5-dimethylphenolate) ) Aluminum, bis (2,4-dimethyl-8-)
Quinolinolate) (3,5-di-tert-butylphenolato) aluminum, bis (2-methyl-8-quinolinolate) aluminum-μ-oxo-bis (2-methyl-8-quinolinolate) aluminum, bis (2,4 −
Dimethyl-8-quinolinolate) aluminum-μ-oxo-bis (2,4-dimethyl-8-quinolinolate)
Aluminum, bis (2-methyl-4-ethyl-8-quinolinolate) aluminum-μ-oxo-bis (2-
Methyl-4-ethyl-8-quinolinolate) aluminum, bis (2-methyl-4-methoxy-8-quinolinolate) aluminum-μ-oxo-bis (2-methyl-
4-methoxy-8-quinolinolate) aluminum, bis (2-methyl-5-cyano-8-quinolinolate) aluminum-μ-oxo-bis (2-methyl-5-cyano-8-quinolinolate) aluminum, bis (2- Methyl-5-trifluoromethyl-8-quinolinolate)
Aluminum-μ-oxo-bis (2-methyl-5-trifluoromethyl-8-quinolinolate) aluminum and the like can be mentioned. Of course, the luminescent organometallic complex may be used alone or in combination.

The electron injecting / transporting layer 5 is a layer containing a compound having a function of facilitating the injection of electrons from the cathode and a function of transporting the injected electrons. The electron injecting and transporting layer is formed of the compound A according to the present invention and / or another compound having an electron injecting and transporting function (for example, an organometallic complex [for example, tris (8-quinolinolate) aluminum, bis (10-benzo [h] quinolinolate) ) Beryllium, 5
-Beryllium salt of hydroxyflavone, aluminum salt of 5-hydroxyflavone], oxadiazole derivative, triazole derivative, triazine derivative, perylene derivative, quinoline derivative, quinoxaline derivative, diphenylquinone derivative, nitro-substituted fluorenone derivative, thiopyrandioxide derivative And the like can be formed using at least one of them. When the compound A according to the present invention and a compound having another electron injecting and transporting function are used in combination, the proportion of the compound A according to the present invention in the electron injecting and transporting layer is preferably about 0.1 to 40% by weight. Prepare.
In the present invention, the compound A according to the present invention and an organometallic complex [for example, the compounds represented by the general formulas (a) to (c)] are used together to form an electron injecting and transporting layer. preferable.

As the cathode 6, a metal, an alloy or an electrically conductive compound having a relatively small work function is preferably used as an electrode material. Examples of the electrode material used for the cathode include lithium, lithium-indium alloy, sodium, sodium-potassium alloy, calcium, magnesium, magnesium-silver alloy, magnesium-indium alloy, indium, ruthenium, titanium,
Manganese, yttrium, aluminum, an aluminum-lithium alloy, an aluminum-calcium alloy, an aluminum-magnesium alloy, a graphite thin film and the like can be given. These electrode substances may be used alone or in combination of two or more. The cathode, these electrode substances, for example, a vapor deposition method, a sputtering method,
It can be formed on the electron injection transport layer by a method such as an ionization vapor deposition method, an ion plating method, and a cluster ion beam method. Further, the cathode may have a single-layer structure or a multilayer structure. The sheet electric resistance of the cathode is preferably set to several hundreds Ω / □ or less. The thickness of the cathode depends on the material of the electrode substance used, but is generally about 5 to 1000 nm, more preferably,
It is set to about 10 to 500 nm. In order to efficiently extract light emitted from the organic electroluminescent device, it is preferable that at least one of the anode and the cathode is transparent or translucent, and the transmittance of emitted light is generally 70% or more. It is more preferable to set the material and thickness of the anode.

Further, in the organic electroluminescent device of the present invention, at least one of the layers may contain a singlet oxygen quencher. The singlet oxygen quencher is not particularly limited and includes, for example, rubrene,
Nickel complexes, diphenylisobenzofuran and the like can be mentioned, and rubrene is particularly preferable. The layer containing the singlet oxygen quencher is not particularly limited, but is preferably a light emitting layer or a hole injection transport layer, and more preferably a hole injection transport layer.
For example, when a singlet oxygen quencher is contained in the hole injecting and transporting layer, the singlet oxygen quencher may be contained uniformly in the hole injecting and transporting layer. (Electron injection / transport layer having a light emitting function). The content of the singlet oxygen quencher is 0.01 to 50% by weight, preferably 0.0
5 to 30% by weight, more preferably 0.1 to 20% by weight
It is.

The method for forming the hole injecting and transporting layer, the light emitting layer, and the electron injecting and transporting layer is not particularly limited, and may be, for example, a vacuum deposition method, an ionization deposition method, a solution coating method (eg, a spin coating method, a casting method, Method, dip coating method,
It can be manufactured by forming a thin film by a bar coating method, a roll coating method, a Langmuir-Brosette method, or the like. When forming each layer by a vacuum deposition method, the conditions of the vacuum deposition are not particularly limited,
It is carried out under a vacuum of about 10 ^-5 Torr or less, a boat temperature of about 50 to 400 ° C. (evaporation source temperature), a substrate temperature of about −50 to 300 ° C., and a deposition rate of about 0.005 to 50 nm / sec. Is preferred. In this case, by forming each layer such as a hole injection transport layer, a light emitting layer, and an electron injection transport layer continuously under a vacuum, an organic electroluminescent element having more excellent characteristics can be manufactured. When each layer such as a hole injection transport layer, a light emitting layer, and an electron injection transport layer is formed using a plurality of compounds by a vacuum deposition method, each boat containing the compounds is individually temperature-controlled and co-deposited. Is preferred.

When each layer is formed by a solution coating method,
The components forming each layer or the components and a binder resin or the like are dissolved or dispersed in a solvent to form a coating liquid. Examples of the binder resin that can be used for each of the hole injection transport layer, the light emitting layer, and the electron injection transport layer include poly-N-vinylcarbazole, polyarylate, polystyrene, polyester, polysiloxane, polymethyl acrylate, and the like.
Polymethyl methacrylate, polyether, polycarbonate, polyamide, polyimide, polyamide imide,
High molecular compounds such as polyparaxylene, polyethylene, polyphenylene oxide, polyethersulfone, polyaniline and its derivatives, polythiophene and its derivatives, polyphenylenevinylene and its derivatives, polyfluorene and its derivatives, and polythienylenevinylene and its derivatives. . The binder resin may be used alone or in combination.

When each layer is formed by a solution coating method,
The components forming each layer or the components and a binder resin are combined with a suitable organic solvent (for example, hexane, octane,
Decane, toluene, xylene, ethylbenzene, hydrocarbon solvents such as 1-methylnaphthalene, for example, acetone, methyl ethyl ketone, methyl isobutyl ketone, ketone solvents such as cyclohexanone, for example, dichloromethane, chloroform, tetrachloromethane, dichloroethane, trichloroethane, Halogenated hydrocarbon solvents such as tetrachloroethane, chlorobenzene, dichlorobenzene, and chlorotoluene, for example, ester solvents such as ethyl acetate, butyl acetate, and amyl acetate, for example, methanol, propanol, butanol, pentanol, hexanol, and cyclohexanol , Methyl cellosolve, ethyl cellosolve, alcohol solvents such as ethylene glycol, for example, dibutyl ether, tetrahydrofuran,
Dioxane, ether solvents such as anisole, for example,
Polar solvents such as N, N-dimethylformamide, N, N-dimethylacetamide, 1-methyl-2-pyrrolidone, 1,3-dimethyl-2-imidazolidinone, dimethylsulfoxide) and / or dissolved in water Alternatively, a thin film can be formed by various coating methods by dispersing the mixture into a coating liquid.

The method of dispersion is not particularly limited. For example, the particles can be dispersed into fine particles using a ball mill, sand mill, paint shaker, attritor, homogenizer or the like. The concentration of the coating solution is not particularly limited, and can be set to a concentration range suitable for producing a desired thickness depending on a coating method to be performed, and is generally about 0.1 to 50% by weight. Preferably, the solution concentration is about 1 to 30% by weight. When a binder resin is used, the amount of the binder resin is not particularly limited. However, in general, the amount of the binder resin is limited to the components forming each layer (when forming a single-layer element, the total 5) to 99.9% by weight
Level, preferably about 10 to 99% by weight, more preferably about 15 to 90% by weight.

The thicknesses of the hole injecting and transporting layer, the light emitting layer and the electron injecting and transporting layer are not particularly limited, but are generally preferably set to about 5 nm to 5 μm.
A protective layer (sealing layer) may be provided on the fabricated device for the purpose of preventing contact with oxygen, moisture, or the like, or the device may be formed of, for example, paraffin, liquid paraffin, silicon oil, fluorocarbon oil, zeolite, or the like. It can be protected by being enclosed in an inert substance such as a contained fluorocarbon oil. Examples of the material used for the protective layer include organic polymer materials (for example, fluorinated resin, epoxy resin, silicone resin, epoxy silicone resin, polystyrene, polyester, polycarbonate, polyamide, polyimide, polyamideimide, polyparaxylene, polyethylene) , Polyphenylene oxide), inorganic materials (for example, diamond thin film, amorphous silica, electrically insulating glass, metal oxide, metal nitride, metal carbide,
Metal sulfide), and a photocurable resin. The material used for the protective layer may be used alone or in combination of two or more. The protective layer may have a single-layer structure or a multilayer structure.

Further, a metal oxide film (for example, an aluminum oxide film) or a metal fluoride film can be provided as a protective film on the electrode. Also, for example, on the surface of the anode,
For example, an interface layer (intermediate layer) composed of an organic phosphorus compound, polysilane, an aromatic amine derivative, and a phthalocyanine derivative
Can also be provided. Further, electrodes, eg, anodes, can be used by treating the surface with, eg, acid, ammonia / hydrogen peroxide, or plasma. The organic electroluminescent device of the present invention is generally used as a DC-driven device, but can also be used as a pulse-driven or AC-driven device. Incidentally, the applied voltage is generally about 2 to 30 V. The organic electroluminescent device of the present invention can be used for, for example, a panel light source, various light emitting devices, various display devices, various labels, various sensors, and the like.

[0133]

EXAMPLES Hereinafter, the present invention will be described in more detail with reference to Production Examples and Examples, but of course, the present invention is not limited thereto. Production Example 1: Production of Compound of Exemplified Compound No. F-7 7,7 ′, 14,14′-Tetra (4 ″ -methylphenyl) -3,3′-biasenaphtho [1,2-k] fluoranthene 3 g and anhydrous 4 g of aluminum chloride and 2 g of anhydrous cupric chloride were dissolved in 1,2-dichloroethane (150 ml) in 10 ml.
Heated and refluxed for hours. After cooling, 1N hydrochloric acid (50 ml) was added to the reaction mixture, followed by extraction with 1,2-dichloroethane. After washing the 1,2-dichloroethane solution with water,
After the 1,2-dichloroethane was distilled off under reduced pressure, the residue was subjected to silica gel column chromatography (eluent: toluene). After the toluene was distilled off under reduced pressure, the residue was recrystallized from a mixed solvent of toluene and acetone to give 2.2 g of the compound of Exemplified Compound No. F-7 as blue-violet crystals.
Obtained. Melting point: 250 ° C. or higher This compound could be sublimated under the conditions of 450 ° C. and 10 ⁻⁵ torr. Absorption maximum (in toluene) 618n
m

The 7,7 ', 14,14'-tetra (4 "-methylphenyl) -3,3'-biasenaphtho [1,2-k] fluoranthene used was produced by the following method. Nickel chloride 150 mg, triphenylphosphine 2.1 g, zinc dust 3 g, sodium bromide 3.5 g
In N, N-dimethylacetamide (20 ml)
Stirred at 0 ° C. until the solution turned red. In this solution,
A mixed solvent of N, N-dimethylformamide and N, N-dimethylacetamide in which 5 g of bromo-7,14-di (4-methylphenyl) acenaphtho [1,2-k] fluoranthene is dissolved [1: 1 (by volume)] 50 ml] solution and add 80
Stirred at C for 18 hours. After cooling, 2N hydrochloric acid was added to the reaction mixture, followed by extraction with dichloromethane. After washing the dichloromethane solution with water, the dichloromethane was distilled off under reduced pressure, and the residue was treated by silica gel column chromatography (eluent: toluene). After the toluene was distilled off under reduced pressure, the residue was recrystallized from a mixed solvent of toluene and acetone to give 7,7 ′, 14,14′-tetra (4 ″ -methylphenyl) -3,3′-biasenaphtho [1 3.3 g of fluoranthene were obtained as yellow crystals, mp 25.
0 ° C or higher

Production Examples 2 to 63 In Production Example 1, 7,7 ', 14,14'-tetra (4 "-methylphenyl) -3,3'-biasenaphtho
According to the method described in Production Example 1, except for using various 3,3′-biasenaphtho [1,2-k] fluoranthene derivatives instead of using [1,2-k] fluoranthene, various bisacenaphtho [ 1 ', 2': 5,6] Indeno [1,2,3-cd:
[1 ', 2', 3'-lm] perylene derivatives were prepared. Table 1 (Table 1
~ Table 16) shows the used 3,3'-biasenaftide [1,2-
k] The fluoranthene derivative and the produced bisacenaphtho [1 ′, 2 ′: 5,6] indeno [1,2,3-cd: 1 ′, 2 ′, 3′-lm] perylene derivative are shown by example compound numbers. . The maximum absorption (nm) in toluene is also shown. In addition, the produced compound was blue-violet to blue crystals, and the melting point of the compound was 250 ° C. or higher. In addition, 3,3'-
When the biacenaphtho [1,2-k] fluoranthene derivative is a mixture of isomers, the compound to be produced is also produced as a mixture.

[0136]

[Table 1]

[0137]

[Table 2]

[0138]

[Table 3]

[0139]

[Table 4]

[0140]

[Table 5]

[0141]

[Table 6]

[0142]

[Table 7]

[0143]

[Table 8]

[0144]

[Table 9]

[0145]

[Table 10]

[0146]

[Table 11]

[0147]

[Table 12]

[0148]

[Table 13]

[0149]

[Table 14]

[0150]

[Table 15]

[0151]

[Table 16]

Production Example 64: Production of Compound of Exemplified Compound No. A-1 2 g of Exemplified Compound No. G-9, soda lime 2
After mixing 0 g with 10 g of potassium hydroxide and water (5 ml), the mixture was heated at 350 to 400 ° C. for 30 minutes under a nitrogen atmosphere. The cooled reaction mixture was placed in a sublimation apparatus, sublimated at 400 ° C. and 10 ⁻⁵ torr, and a blue-violet solid was collected to obtain 900 mg of the compound of Exemplified Compound No. A-1. Melting point 250 ° C or higher, absorption maximum (in toluene) 616
nm

Production Example 65: Exemplified Compound Nos. C-11 and C
Production of Compound (Mixture) of Compound No.-12 Compounds of Exemplified Compound Nos. A-8 and A-9 (Equivalent mixture)
2 g and sodium salt of isopropyl mercaptan 1 g
(Prepared from isopropyl mercaptan and sodium metal) was converted to hexamethylphosphoric triamide (H
(MPA) (50 ml) at room temperature for 4 days. After adding water (50 ml), the precipitated solid was filtered and washed with water. The filtered solid was subjected to an alumina column chromatography (eluent: toluene). After the toluene was distilled off under reduced pressure, the residue was recrystallized from a mixed solvent of toluene and isopropanol, and 2 g of the compound of Exemplified Compound Nos. C-11 and C-12 (a mixture of the same amount) was obtained as blue crystals.
Obtained. Melting point 250 ° C or higher, absorption maximum (in toluene) 62
0 nm

Production Example 66: Exemplified Compound Nos. E-10 and E
Production of Compound (Mixture) of Compound No.-11 Compounds of Exemplified Compound Nos. A-8 and A-9 (Equivalent mixture)
2 g and 1.6 g of sodium salt of 4-methylphenylmercaptan (prepared from 4-methylphenylmercaptan and sodium metal) were stirred in hexamethylphosphoric triamide (50 ml) at room temperature for 4 days. After adding water (50 ml), the precipitated solid was filtered and washed with water. The filtered solid was subjected to an alumina column chromatography (eluent: toluene). After the toluene was distilled off under reduced pressure, the residue was recrystallized from a mixed solvent of toluene and isopropanol to give the compound of Exemplified Compound Nos. E-10 and E-11 (a mixture of the same amount) as blue crystals.
1 g was obtained. Melting point 250 ° C or higher, absorption maximum (in toluene)
620 nm

Production Example 67: Production of Compound of Exemplified Compound No. G-11 To a solution of 1 g of compound of Exemplified Compound No. C-6 in methylene chloride was added 15 ml (1 mol solution) of a solution of boron tribromide in methylene chloride. The mixture was heated under reflux for 4 hours under an argon atmosphere. After adding hydrochloric acid, methylene chloride was distilled off under reduced pressure. The solid was filtered and separated, and then subjected to alumina column chromatography [eluent: toluene-ethyl acetate (1
0: 1 volume ratio)]. After distilling off toluene and ethyl acetate under reduced pressure, the residue was washed with a mixed solvent of toluene and acetone to obtain 800 mg of a compound of Exemplified Compound No. G-11 as blue-violet crystals. 250 ° C
Above, absorption maximum (in toluene) 620 nm

Preparation Example 68 Preparation of Compound of Exemplified Compound No. H-5 2 g of Exemplified Compound No. H-7, potassium hydroxide 2
5 g was heated to reflux in ethyl cellosolve (300 ml) for 40 hours. The mixture was poured into ice water (400 ml), acidified with hydrochloric acid, and the precipitated red-violet solid was collected, washed with water and dried, and 1.7 g of the compound of Exemplified Compound No. H-5 was obtained as a blue-violet solid. Obtained. Melting point 250 ° C or higher, absorption maximum (in dimethyl sulfoxide) 618 nm

Production Example 69: Production of Compound of Exemplified Compound No. F-2 2 g of Exemplified Compound No. H-4, soda lime 2
After mixing 0 g with 10 g of potassium hydroxide and water (5 ml), the mixture was heated at 350 to 400 ° C. for 30 minutes under a nitrogen atmosphere. The cooled reaction mixture was placed in a sublimation apparatus and sublimated at 450 ° C. at 10 ⁻⁵ torr, and a blue-violet solid was collected to obtain 1.1 g of a compound of Exemplified Compound No. F-2. Melting point 250 ° C or higher, absorption maximum (in toluene) 617 nm

Preparation Example 70: Preparation of Compound of Exemplified Compound No. I-5 1 g of Compound of Exemplified Compound No. G-9 and potassium hydroxide 5
0 g was heated under reflux in ethyl cellosolve (300 ml) for 80 hours. After the mixture was poured into ice water (400 ml), the precipitated solid was filtered and washed. After drying, the solid is placed in a sublimation apparatus at 450 ° C. and 10 ^-5 torr.
And a blue-violet solid is collected. Exemplified Compound No. I
700 mg of compound (-5) was obtained. Melting point 250 ° C or higher, absorption maximum (in toluene) 618 nm

Preparation Example 71: Preparation of Compound of Exemplified Compound No. F-55 2 g of Compound of Exemplified Compound No. F-57 was treated with dioxane (1
00 ml) and N, N-dimethylformamide (100 m
1) in the presence of 5% by weight of Pd / carbon in a mixed solvent of
Hydrogenated at ° C. After filtering off Pd / carbon from the reaction mixture, dioxane and N, N-dimethylformamide were distilled off under reduced pressure. The residue was washed with acetone and then filtered to obtain 1.4 g of the compound of Exemplified Compound No. F-55 as blue-violet crystals. Melting point 250 ° C or higher, absorption maximum (in toluene) 618 nm

Preparation Example 72: Preparation of Compound of Exemplified Compound No. F-63 2 g of Compound of Exemplified Compound No. F-62 was treated with dioxane (1
00 ml) and N, N-dimethylformamide (100 m
1) in the presence of 5% by weight of Pd / carbon in a mixed solvent of
Hydrogenated at ° C. After filtering off Pd / carbon from the reaction mixture, dioxane and N, N-dimethylformamide were distilled off under reduced pressure. The residue was washed with acetone and filtered to give the compound of Exemplified Compound No. F-63 as blue crystals, 1.7.
g was obtained. Melting point 250 ° C or higher, absorption maximum (in toluene) 6
22nm

Production Example 73: Preparation of Compound of Exemplified Compound No. F-32 1 g of Exemplified Compound No. F-63, 4 g of iodobenzene, 5 g of copper powder, 20 g of potassium carbonate, and 18-crown-6 (0.5 g) were obtained. o-Dichlorobenzene (50 ml)
The mixture was heated under reflux for 20 hours. After o-dichlorobenzene was distilled off by steam distillation, the residue was filtered and washed with water.
The filtered solid was subjected to an alumina column chromatography (eluent: toluene). After the toluene was distilled off under reduced pressure, the residue was recrystallized from a mixed solvent of toluene and isopropanol to give Exemplified Compound No. F as blue crystals.
1 g of the compound of -32 was obtained. Melting point 250 ° C or higher, absorption maximum (in toluene) 620 nm

Production Example 74: Exemplified compound numbers G-3 and G-
Production of Compound 4 (Mixture) Compounds of Exemplified Compound Nos. G-1 and G-2 (Equivalent mixture)
2 g of 5% by weight Pd in a mixed solvent of dioxane (100 ml) and N, N-dimethylformamide (100 ml)
/ Hydrogenated at 40 ° C. in the presence of carbon. After filtering off Pd / carbon from the reaction mixture, dioxane and N, N-dimethylformamide were distilled off under reduced pressure. The residue was washed with acetone and filtered to give Exemplified Compound No. G- as blue crystals.
1.7 g of a compound of 3 and G-4 (a mixture of the same amount) was obtained. Melting point 250 ° C or higher, absorption maximum (in toluene) 624 nm

Production Example 75: Exemplified Compound Nos. G-6 and G-
Production of Compound 7 (Mixture) Compounds of Exemplified Compound Nos. G-3 and G-4 (Equivalent mixture)
1 g, 5 g of 4-iodotoluene, 5 g of copper powder, 20 g of potassium carbonate, and 18-crown-6 (0.5 g) were heated and refluxed in o-dichlorobenzene (50 ml) for 20 hours.
After o-dichlorobenzene was distilled off by steam distillation, the residue was filtered and washed with water. The filtered solid was subjected to an alumina column chromatography (eluent: toluene). After the toluene was distilled off under reduced pressure, the residue was recrystallized from a mixed solvent of toluene and isopropanol to obtain 1.1 g of the compound of Exemplified Compound Nos. G-6 and G-7 (a mixture of the same amount) as blue crystals. . Melting point 250 ° C or higher, absorption maximum (in toluene) 622 nm

Example 1 A glass substrate having a 200-nm-thick ITO transparent electrode (anode) was subjected to ultrasonic cleaning using a neutral detergent, acetone, and ethanol. The substrate was dried using nitrogen gas, further washed with UV / ozone, fixed to a substrate holder of a vapor deposition device, and then the pressure in the vapor deposition tank was reduced to 3 × 10 ⁻⁶ Torr. First, 4,4′-bis [N-phenyl-N- (3 ″ -methylphenyl) amino] biphenyl was vapor-deposited on the ITO transparent electrode to a thickness of 75 nm at a vapor deposition rate of 0.2 nm / sec. Next, bis (2-methyl-8-quinolinolate) (4-phenylphenolate) aluminum and 7,12,19,24-tetraphenylbisacenaphtho [1 ′, 2] were formed thereon. ': 5,6] Indeno [1,
2,3, -cd: 1 ′, 2 ′, 3′-lm] perylene (Exemplified Compound No. F-
6) from different evaporation sources at an evaporation rate of 0.2 n
m / sec at a thickness of 50 nm (weight ratio 100:
0.5) to form a light emitting layer. Next, tris (8-quinolinolate) aluminum was deposited at a deposition rate of 0.2 nm / sec.
Was deposited to a thickness of 50 nm to form an electron injection transport layer. Further, magnesium and silver were further deposited thereon at a deposition rate of 0.2 n.
Co-deposition at 200 m / sec to a thickness of 200 nm (weight ratio 10:
1) The resultant was used as a cathode to produce an organic electroluminescent device. still,
The vapor deposition was performed while maintaining the reduced pressure state of the vapor deposition tank. When a DC voltage of 12 V was applied to the manufactured organic electroluminescent device in a dry atmosphere, a current of 55 mA / cm ² flowed. Red light emission with a luminance of 2350 cd / m ² was confirmed.

Examples 2 to 45 In Example 1, instead of using the compound of Exemplified Compound No. F-6 in forming the light emitting layer, the compound of Exemplified Compound No. A-1 (Example 2) A-8
(Example 3), compound of Exemplified Compound No. B-8 (Example 4), compound of Exemplified Compound No. B-9 (Example 5), Exemplified Compound No. B- 10
(Example 6), the compound of Exemplified Compound No. B-11 (Example 7), the compound of Exemplified Compound No. B-12 (Example 8), the compound of Exemplified Compound No. B-15 (Example 9), Exemplified Compound No. B-25 (Example 10), Exemplified Compound No. B-32 (Example 11), Exemplified Compound No. B-33 (Example 12), Exemplified Compound No. C-6 (Ex. Example 13), Exemplified Compound No. D-1
(Example 14), the compound of Exemplified Compound No. F-2 (Example 15), the compound of Exemplified Compound Nos. F-3 and F-4 (mixture of the same amount) (Example 16), Exemplified Compound No. F
-7 (Example 17), Exemplified Compound No. F-8 (Example 18), Exemplified Compound No. F-10 (Example 19), Exemplified Compound No. F-11 (Example 20) ), The compound of Exemplified Compound No. F-14 (Example 21), the compound of Exemplified Compound No. F-24 (Example 22), and the compound of Exemplified Compound Nos. F-27 and F-28 (equivalent mixture) (Example) 23), Exemplified Compound No. F-3
Compound No. 0 (Example 24), Compound Compound No. F-31 (Example 25), Compound Compound No. F-32 (Example 26), Compound Compound No. F-33 (Example 27) Compound of Exemplified Compound No. F-34 (Example 28), Compound of Exemplified Compound No. F-36 (Example 29), Compound of Exemplified Compound No. F-44 (Example 3)
0), Compound of Exemplified Compound No. F-45 (Example 3)
1), Compound of Exemplified Compound No. F-48 (Example 3)
2), Compound of Exemplified Compound No. F-49 (Example 3)
3), Compound of Exemplified Compound No. F-51 (Example 3)
4), Compound of Exemplified Compound No. F-53 (Example 3)
5), Compound of Exemplified Compound No. F-54 (Example 3)
6), Compound of Exemplified Compound No. F-55 (Example 3)
7), Compound of Exemplified Compound No. F-64 (Example 3)
8), Compound of Exemplified Compound No. F-66 (Example 3)
9), Compounds of Exemplified Compound Nos. G-6 and G-7 (Equivalent mixture) (Example 40), Compound of Exemplified Compound No. G-11 (Example 41), Compound of Exemplified Compound No. H-4 (Example Example 42), Compound of Exemplified Compound No. H-7 (Example 4)
3), a compound of Exemplified Compound No. I-2 (Example 44),
An organic electroluminescent device was produced by the method described in Example 1 except that the compound of Exemplified Compound No. I-6 (Example 45) was used. Each element was dried under an atmosphere of 12
When a DC voltage of V was applied, orange-red to red light emission was confirmed. The characteristics were further examined, and the results are shown in Table 2 (Tables 17 to 19).

Comparative Example 1 In Example 1, when forming the light emitting layer, the compound of Exemplified Compound No. F-6 was not used, and bis (2-methyl-
An organic electroluminescent device was prepared by the method described in Example 1, except that only 8-quinolinolate) (4-phenylphenolate) aluminum was used to form a light emitting layer by vapor deposition to a thickness of 50 nm. 1
When a DC voltage of 2 V was applied, blue light emission was confirmed. The characteristics were further examined, and the results are shown in Table 2.

Comparative Example 2 In Example 1, when forming the light emitting layer, instead of using the compound of Exemplified Compound No. F-6, N-methyl-
An organic electroluminescent device was produced by the method described in Example 1 except that 2-methoxyacridone was used. When a DC voltage of 12 V was applied to this device under a dry atmosphere, blue light emission was confirmed. Further investigate its properties,
The results are shown in Table 2.

[0168]

[Table 17]

[0169]

[Table 18]

[0170]

[Table 19]

Example 46 A glass substrate having a 200 nm-thick ITO transparent electrode (anode) was ultrasonically cleaned using a neutral detergent, acetone and ethanol. The substrate was dried using nitrogen gas, further washed with UV / ozone, fixed to a substrate holder of a vapor deposition device, and then the pressure in the vapor deposition tank was reduced to 3 × 10 ⁻⁶ Torr. First, 4,4′-bis [N-phenyl-N- (3 ″ -methylphenyl) amino] biphenyl was vapor-deposited on the ITO transparent electrode to a thickness of 75 nm at a vapor deposition rate of 0.2 nm / sec. Next, bis (2-methyl-8-quinolinolate) (2-phenylphenolate) aluminum and the compound of Exemplified Compound No. F-7 were deposited thereon from different evaporation sources at a deposition rate of 0. .2 nm / sec
Co-deposition to a thickness of 50 nm (weight ratio 100: 1.0)
Thus, a light emitting layer was obtained. Next, tris (8-quinolinolato) aluminum is deposited at a deposition rate of 0.2 nm / sec.
It was deposited to a thickness of nm to form an electron injection transport layer. Further thereon, magnesium and silver were deposited at a deposition rate of 0.2 nm / se.
A co-evaporation (weight ratio 10: 1) was carried out to a thickness of 200 nm at c to obtain a cathode, thereby producing an organic electroluminescent device. In addition, evaporation is
The test was performed while maintaining the reduced pressure of the vapor deposition tank. When a DC voltage of 12 V was applied to the produced organic electroluminescent device in a dry atmosphere, a current of 58 mA / cm ² flowed. Brightness 2
Red light emission of 370 cd / m ² was confirmed.

Example 47 A glass substrate having a 200-nm-thick ITO transparent electrode (anode) was ultrasonically cleaned with a neutral detergent, acetone, and ethanol. The substrate was dried using nitrogen gas, further washed with UV / ozone, fixed to a substrate holder of a vapor deposition device, and then the pressure in the vapor deposition tank was reduced to 3 × 10 ⁻⁶ Torr. First, 4,4′-bis [N-phenyl-N- (3 ″ -methylphenyl) amino] biphenyl was vapor-deposited on the ITO transparent electrode to a thickness of 75 nm at a vapor deposition rate of 0.2 nm / sec. A hole injecting and transporting layer was formed thereon, and then bis (2-methyl-8-quinolinolate) aluminum-μ was formed thereon.
-Oxo-bis (2-methyl-8-quinolinolato) aluminum and the compound of Exemplified Compound No. F-10 were co-deposited from different evaporation sources at a deposition rate of 0.2 nm / sec to a thickness of 50 nm (weight ratio: 100: 2.0) to form a light emitting layer. Next, tris (8-quinolinolato) aluminum was deposited at a deposition rate of 0.2 nm / sec to a thickness of 50 nm to form an electron injection transport layer. Further thereon, magnesium and silver were co-deposited (weight ratio 10: 1) at a deposition rate of 0.2 nm / sec to a thickness of 200 nm to form an organic electroluminescent device. In addition, vapor deposition was performed while maintaining the reduced pressure state of the vapor deposition tank. In the manufactured organic electroluminescent element,
When a DC voltage of 12 V was applied in a dry atmosphere,
A current of 7 mA / cm ² flowed. Brightness 2320 cd / m ²
Red light emission was confirmed.

Example 48 A glass substrate having a 200 nm-thick ITO transparent electrode (anode) was ultrasonically cleaned using a neutral detergent, acetone and ethanol. The substrate was dried using nitrogen gas, further washed with UV / ozone, fixed to a substrate holder of a vapor deposition device, and then the pressure in the vapor deposition tank was reduced to 3 × 10 ⁻⁶ Torr. First, 4,4′-bis [N-phenyl-N- (3 ″ -methylphenyl) amino] biphenyl was vapor-deposited on the ITO transparent electrode to a thickness of 75 nm at a vapor deposition rate of 0.2 nm / sec. Next, bis (2,4-dimethyl-8-quinolinolate) aluminum-μ-oxo-bis (2,4-dimethyl-8-quinolinolate) aluminum and Exemplified Compound No. F- were formed thereon. Forty-four compounds were obtained from different evaporation sources at a deposition rate of 0.2 nm / sec.
To co-deposit to a thickness of 50 nm (weight ratio 100: 4.0)
Thus, a light emitting layer was obtained. Next, tris (8-quinolinolato) aluminum is deposited at a deposition rate of 0.2 nm / sec.
It was deposited to a thickness of nm to form an electron injection transport layer. Further thereon, magnesium and silver were deposited at a deposition rate of 0.2 nm / se.
A co-evaporation (weight ratio 10: 1) was carried out to a thickness of 200 nm at c to obtain a cathode, thereby producing an organic electroluminescent device. In addition, evaporation is
The test was performed while maintaining the reduced pressure of the vapor deposition tank. When a DC voltage of 12 V was applied to the manufactured organic electroluminescent device in a dry atmosphere, a current of 60 mA / cm ² flowed. Brightness 2
Red light emission of 130 cd / m ² was confirmed.

Example 49 A glass substrate having a 200 nm-thick ITO transparent electrode (anode) was ultrasonically cleaned using a neutral detergent, acetone and ethanol. The substrate was dried using nitrogen gas, further washed with UV / ozone, fixed to a substrate holder of a vapor deposition device, and then the pressure in the vapor deposition tank was reduced to 3 × 10 ⁻⁶ Torr. First, 4,4′-bis [N-phenyl-N- (3 ″ -methylphenyl) amino] biphenyl was vapor-deposited on the ITO transparent electrode to a thickness of 75 nm at a vapor deposition rate of 0.2 nm / sec. Next, tris (8-quinolinolato) aluminum and the compound of Exemplified Compound No. F-8 were deposited thereon from different evaporation sources at a deposition rate of 0.2.
Co-deposition to a thickness of 50 nm at nm / sec (weight ratio 100:
6.0) to form a light emitting layer. Next, tris (8-quinolinolate) aluminum was deposited at a deposition rate of 0.2 nm / sec.
Was deposited to a thickness of 50 nm to form an electron injection transport layer. Further, magnesium and silver were further deposited thereon at a deposition rate of 0.2 n.
Co-deposition at 200 m / sec to a thickness of 200 nm (weight ratio 10:
1) The resultant was used as a cathode to produce an organic electroluminescent device. still,
The vapor deposition was performed while maintaining the reduced pressure state of the vapor deposition tank. When a DC voltage of 12 V was applied to the manufactured organic electroluminescent device in a dry atmosphere, a current of 60 mA / cm ² flowed. Red light emission with a luminance of 2150 cd / m ² was confirmed.

Example 50 A glass substrate having a 200 nm-thick ITO transparent electrode (anode) was ultrasonically cleaned using a neutral detergent, acetone and ethanol. The substrate was dried using nitrogen gas, further washed with UV / ozone, fixed to a substrate holder of a vapor deposition device, and then the pressure in the vapor deposition tank was reduced to 3 × 10 ⁻⁶ Torr. First, 4,4′-bis [N-phenyl-N- (3 ″ -methylphenyl) amino] biphenyl was vapor-deposited on the ITO transparent electrode to a thickness of 75 nm at a vapor deposition rate of 0.2 nm / sec. Next, tris (8-quinolinolato) aluminum and the compound of Exemplified Compound No. F-66 were deposited thereon from different evaporation sources at a deposition rate of 0.
Co-deposition to a thickness of 50 nm at 2 nm / sec (weight ratio 10
0:10) to form a light emitting layer. Next, tris (8-quinolinolate) aluminum was deposited at a deposition rate of 0.2 nm / se.
The film was vapor-deposited to a thickness of 50 nm at c to form an electron injection transport layer.
Further, magnesium and silver were further deposited thereon at a deposition rate of 0.2.
at 200 nm / sec to a thickness of 200 nm (weight ratio: 10:
1) The resultant was used as a cathode to produce an organic electroluminescent device. still,
The vapor deposition was performed while maintaining the reduced pressure state of the vapor deposition tank. When a DC voltage of 12 V was applied to the manufactured organic electroluminescent device in a dry atmosphere, a current of 60 mA / cm ² flowed. Red light emission with a luminance of 2250 cd / m ² was confirmed.

Example 51 A glass substrate having a 200 nm-thick ITO transparent electrode (anode) was ultrasonically cleaned using a neutral detergent, acetone and ethanol. The substrate was dried using nitrogen gas, further washed with UV / ozone, fixed to a substrate holder of a vapor deposition device, and then the pressure in the vapor deposition tank was reduced to 3 × 10 ⁻⁶ Torr. First, 4,4′-bis [N-phenyl-N- (3 ″ -methylphenyl) amino] biphenyl was vapor-deposited on the ITO transparent electrode to a thickness of 75 nm at a vapor deposition rate of 0.2 nm / sec. Next, tris (8-quinolinolato) aluminum and the compound of Exemplified Compound No. A-1 were deposited thereon from different evaporation sources at an evaporation rate of 0.2.
Co-deposition to a thickness of 50 nm at nm / sec (weight ratio 100:
1.0) to form a light-emitting layer also serving as an electron injection / transport layer. Further, magnesium and silver were further deposited thereon at a deposition rate of 0.2 n.
Co-deposition at 200 m / sec to a thickness of 200 nm (weight ratio 10:
1) The resultant was used as a cathode to produce an organic electroluminescent device. still,
The vapor deposition was performed while maintaining the reduced pressure state of the vapor deposition tank. When a DC voltage of 12 V was applied to the produced organic electroluminescent device in a dry atmosphere, a current of 58 mA / cm ² flowed. Red light emission with a luminance of 1970 cd / m ² was confirmed.

Example 52 A glass substrate having a 200 nm-thick ITO transparent electrode (anode) was ultrasonically cleaned using a neutral detergent, acetone and ethanol. The substrate was dried using nitrogen gas, further washed with UV / ozone, fixed to a substrate holder of a vapor deposition device, and then the pressure in the vapor deposition tank was reduced to 3 × 10 ⁻⁶ Torr. First, 4,4′-bis [N-phenyl-N- (3 ″ -methylphenyl) amino] biphenyl was vapor-deposited on the ITO transparent electrode to a thickness of 75 nm at a vapor deposition rate of 0.2 nm / sec. Next, the compound of Exemplified Compound No. F-6 was further deposited thereon with a vapor deposition rate of 0.2 nm / sec.
Was deposited to a thickness of 50 nm to form a light emitting layer. Then, thereover, 1,3-bis [5 ′-(p-tert-butylphenyl) -1,3,4-oxadiazol-2′-yl]
Benzene was deposited at a deposition rate of 0.2 nm / sec to a thickness of 50 nm to form an electron injection transport layer. Further on that,
Magnesium and silver are deposited at a deposition rate of 0.2 nm / sec.
A cathode was formed by co-evaporation (weight ratio: 10: 1) to a thickness of 0 nm to produce an organic electroluminescent device. In addition, vapor deposition was performed while maintaining the reduced pressure state of the vapor deposition tank. When a DC voltage of 14 V was applied to the manufactured organic electroluminescent device in a dry atmosphere, a current of 48 mA / cm ² flowed. Brightness 1840
Red emission of cd / m ² was confirmed.

Example 53 A glass substrate having a 200 nm-thick ITO transparent electrode (anode) was ultrasonically cleaned using a neutral detergent, acetone and ethanol. The substrate was dried using nitrogen gas, further washed with UV / ozone, fixed to a substrate holder of a vapor deposition device, and then the pressure in the vapor deposition tank was reduced to 3 × 10 ⁻⁶ Torr. First, a compound of Exemplified Compound No. F-6 was deposited on an ITO transparent electrode at a deposition rate of 0.2 nm / sec to a thickness of 55 nm to form a light emitting layer. Then, on top of that, 1,3-bis [5 ′-(p-tert-butylphenyl) -1,3,4-
[Oxadiazol-2'-yl] benzene was deposited at a deposition rate of 0.2 nm / sec to a thickness of 75 nm to form an electron injecting and transporting layer. On top of that, magnesium and silver,
A co-deposition (weight ratio: 10: 1) was performed at a deposition rate of 0.2 nm / sec to a thickness of 200 nm to form a cathode, thereby producing an organic electroluminescent device. In addition, vapor deposition was performed while maintaining the reduced pressure state of the vapor deposition tank. When a DC voltage of 15 V was applied to the produced organic electroluminescent device under a dry atmosphere, the voltage was 68 mA / cm.
^Two currents flowed. Red light emission with a luminance of 1250 cd / m ² was confirmed.

Example 54 A glass substrate having a 200 nm-thick ITO transparent electrode (anode) was ultrasonically cleaned using a neutral detergent, acetone and ethanol. The substrate was dried using nitrogen gas, further washed with UV / ozone, fixed to a substrate holder of a vapor deposition device, and then the pressure in the vapor deposition tank was reduced to 3 × 10 ⁻⁶ Torr. First, 4,4 ′, 4 ″ -tris [N
-(3 "'-methylphenyl) -N-phenylamino] triphenylamine at a deposition rate of 0.1 nm / sec.
The first hole injection transport layer was deposited to a thickness of nm. Next, 4,4′-bis [N-phenyl-N- (1 ″ -naphthyl) amino] biphenyl and the exemplary compound F-6 were prepared from different evaporation sources at an evaporation rate of 0.2 nm / sec.
Co-evaporation (weight ratio: 100: 5) was performed to a thickness of 20 nm to form a light emitting layer also serving as a second hole injection / transport layer. Next, tris (8-quinolinolato) aluminum was deposited thereon to a thickness of 50 nm at a deposition rate of 0.2 nm / sec to form an electron injection transport layer. Further thereon, magnesium and silver were co-deposited (weight ratio 10: 1) at a deposition rate of 0.2 nm / sec to a thickness of 200 nm to form an organic electroluminescent device. In addition, vapor deposition was performed while maintaining the reduced pressure state of the vapor deposition tank. When a DC voltage of 15 V was applied to the manufactured organic electroluminescent device under a dry atmosphere, the voltage was 68 mA /
cm ² of current flowed. Red light emission with a luminance of 2650 cd / m ² was confirmed.

Examples 55 to 64 In Example 54, instead of using the compound of Exemplified Compound No. F-6, the compound of Exemplified Compound No. A-1 (Example 55) and the compound of Exemplified Compound No. B-8 (Example Example 5
6), Compound of Exemplified Compound No. B-11 (Example 5)
7), Compound of Exemplified Compound No. C-6 (Example 58),
Compound of Exemplified Compound No. D-2 (Example 59), Compound of Exemplified Compound No. F-13 (Example 60), Compound of Exemplified Compound No. F-31 (Example 61), Compound of Exemplified Compound No. F-33 (Example 62), Exemplified Compound No. F-
51 compound (Example 63), Exemplified Compound No. F-66
Example 54 except that the compound of Example 64 was used.
An organic electroluminescent device was produced by the method described in (1). When a DC voltage of 12 V was applied to each device under a dry atmosphere, orange-red to red light emission was confirmed. The characteristics were further examined, and the results are shown in Table 3 (Table 20).

[0181]

[Table 20]

Example 65 A glass substrate having a 200-nm-thick ITO transparent electrode (anode) was subjected to ultrasonic cleaning using a neutral detergent, acetone, and ethanol. The substrate was dried using nitrogen gas and further washed with UV / ozone. Next, on the ITO transparent electrode, poly-N-vinylcarbazole (weight average molecular weight 1
50,000), 1,1,4,4-tetraphenyl-1,
3-butadiene (blue light-emitting component), coumarin 6 ["3
-(2'-benzothiazolyl) -7-diethylaminocoumarin "(green light-emitting component)] and the compound of Exemplified Compound No. F-14 at a weight ratio of 100: 5: 3:
A 400 nm light emitting layer was formed by dip coating using a 3% by weight dichloroethane solution containing 2 parts by weight. Next, after fixing the glass substrate having the light emitting layer to the substrate holder of the vapor deposition device, the vapor deposition tank was set to 3 × 10 ^−6.
The pressure was reduced to Torr. Furthermore, 3- (4′-
tert-butylphenyl) -4-phenyl-5- (4 "
-Biphenyl) -1,2,4-triazole was deposited at a deposition rate of 0.2 nm / sec to a thickness of 20 nm, and then tris (8-quinolinolate) aluminum was further deposited thereon at a deposition rate of 0.2 nm / An electron injection / transport layer was formed by vapor deposition to a thickness of 30 nm in sec. Further, magnesium and silver are further deposited thereon at a deposition rate of 0.2 nm / sec at 200 nm.
And a cathode was formed by co-evaporation (weight ratio: 10: 1) to obtain an organic electroluminescent device. When a DC voltage of 12 V was applied to the manufactured organic electroluminescent device in a dry atmosphere, a current of 74 mA / cm ² flowed. Brightness 1120cd
/ M ² was confirmed.

Examples 66 to 79 In Example 65, instead of using the compound of Exemplified Compound No. F-14, the compound of Exemplified Compound No. B-17 (Example 66), the compound of Exemplified Compound No. B-19 ( Example 67), compound of Exemplified Compound No. B-22 (Example 68), compound of Exemplified Compound No. B-35 (Example 6)
9), Compounds of Exemplified Compound Numbers C-11 and C-12 (Equivalent Mixture) (Example 70), Compounds of Exemplified Compound Numbers E-10 and E-11 (Equivalent Mixture) (Example 71), Exemplified Compound No. F-16 (Example 72), Compound No. F-19 (Example 73), Compound No. F-41 (Example 74), Compound No. F
-58 (Example 75), Exemplified Compound No. F-6
Compound No. 0 (Example 76), Compound No. H-11 (Example 77), Compound No. H-13 (Example 78), Compound No. H-17 (Example 79) An organic electroluminescent device was prepared by the method described in Example 65 except that was used. When a DC voltage of 12 V was applied to each element under a dry atmosphere, white light emission was confirmed. Further investigate its properties,
The results are shown in Table 4 (Table 21).

[0184]

[Table 21]

Example 80 A glass substrate having a 200 nm-thick ITO transparent electrode (anode) was ultrasonically cleaned using a neutral detergent, acetone and ethanol. The substrate was dried using nitrogen gas and further washed with UV / ozone. Next, on the ITO transparent electrode, poly-N-vinylcarbazole (weight average molecular weight 1
50000), 1,3-bis [5 '-(p-tert-butylphenyl) -1,3,4-oxadiazole-2'-
[Il] benzene and a compound of Exemplified Compound No. F-18 were formed at a weight ratio of 100: 30: 3 using a 3 wt% dichloroethane solution to form a 300 nm light emitting layer by dip coating. Next, after fixing the glass substrate having the light emitting layer to a substrate holder of a vapor deposition device, the pressure in the vapor deposition tank was reduced to 3 × 10 ⁻⁶ Torr. Further, on the light emitting layer, magnesium and silver were deposited at a deposition rate of 0.1.
Co-deposition to a thickness of 200 nm at 2 nm / sec (weight ratio 1
0: 1) to form a cathode to produce an organic electroluminescent device.
When a DC voltage of 15 V was applied to the manufactured organic electroluminescent device in a dry atmosphere, a current of 76 mA / cm ² flowed. Red light emission with a luminance of 1420 cd / m ² was confirmed.

Comparative Example 3 In Example 80, when forming the light emitting layer, 1,1,4,4-
An organic electroluminescent device was produced by the method described in Example 80 except that tetraphenyl-1,3-butadiene was used. In the dry atmosphere, 1
When a DC voltage of 5 V was applied, a current of 86 mA / cm ² flowed. Blue light emission with a luminance of 680 cd / m ² was confirmed.

Example 81 A glass substrate having a 200 nm-thick ITO transparent electrode (anode) was subjected to ultrasonic cleaning using a neutral detergent, acetone and ethanol. The substrate was dried using nitrogen gas and further washed with UV / ozone. Next, on the ITO transparent electrode, polycarbonate (weight average molecular weight: 50,000),
4,4'-bis [N-phenyl-N- (3 "-methylphenyl) amino] biphenyl, bis (2-methyl-8-
Quinolinolate) aluminum-μ-oxo-bis (2
-Methyl-8-quinolinolato) aluminum and the compound of Exemplified Compound No. F-14 were each added at a weight ratio of 10
Using a 3% by weight dichloroethane solution containing 0: 40: 60: 1 at a ratio of 300 by dip coating.
A light emitting layer of nm was formed. Next, after fixing the glass substrate having the light emitting layer to a substrate holder of a vapor deposition device, the pressure in the vapor deposition tank was reduced to 3 × 10 ⁻⁶ Torr. Further, on the light emitting layer, magnesium and silver were co-deposited (weight ratio: 10: 1) to a thickness of 200 nm at a deposition rate of 0.2 nm / sec to form an organic electroluminescent device. When a DC voltage of 15 V was applied to the manufactured organic electroluminescent device in a dry atmosphere, a current of 66 mA / cm ² flowed. Brightness 770
Red emission of cd / m ² was confirmed.

[0188]

According to the present invention, it has become possible to provide an organic electroluminescent device having excellent light emission luminance. Further, it has become possible to provide a hydrocarbon suitable for the light-emitting element.

[Brief description of the drawings]

FIG. 1 is a schematic structural diagram of an example of an organic electroluminescent device.

FIG. 2 is a schematic structural diagram of an example of an organic electroluminescent device.

FIG. 3 is a schematic structural diagram of an example of an organic electroluminescent device.

FIG. 4 is a schematic structural diagram of an example of an organic electroluminescent device.

FIG. 5 is a schematic structural diagram of an example of an organic electroluminescent device.

FIG. 6 is a schematic structural diagram of an example of an organic electroluminescent device.

FIG. 7 is a schematic structural diagram of an example of an organic electroluminescent device.

FIG. 8 is a schematic structural diagram of an example of an organic electroluminescent device.

[Explanation of symbols]

 1: substrate 2: anode 3: hole injection / transport layer 3a: hole injection / transport component 4: light emitting layer 4a: light emitting component 5: electron injection / transport layer 5 ″: electron injection / transport layer 5a: electron injection / transport component 6: cathode 7: Power supply

──────────────────────────────────────────────────続 き Continued on the front page (51) Int.Cl. ⁷ Identification code FI Theme coat ゛ (Reference) C07C 43/215 C07C 43/215 43/225 43/225 C 43/275 43/275 47/546 47/546 63/49 63/49 69/78 69/78 205/06 205/06 211/50 211/50 211/54 211/54 255/52 255/52 321/28 321/28 C09K 11/06 610 C09K 11 / 06 610

Claims (8)

[Claims] A bisacenaphtho [1 ′,
2 ′: 5,6] An organic electroluminescent device comprising at least one layer containing at least one layer containing at least one indeno [1,2,3-cd: 1 ′, 2 ′, 3′-lm] perylene derivative. 2. Bisacenaphtho [1 ', 2': 5,6] indeno
[1,2,3-cd: 1 ', 2', 3'-lm] Perylene derivative with at least one
The organic electroluminescent device according to claim 1, wherein the seed-containing layer is a light emitting layer. [3] Bisacenaphtho [1 ', 2': 5,6] indeno
[1,2,3-cd: 1 ', 2', 3'-lm] Perylene derivative with at least one
3. The organic electroluminescent device according to claim 1, wherein the seed-containing layer contains a luminescent organometallic complex. 4. Bisacenaphtho [1 ', 2': 5,6] indeno
[1,2,3-cd: 1 ', 2', 3'-lm] Perylene derivative with at least one
3. The organic electroluminescent device according to claim 1, wherein the seed-containing layer contains a triarylamine derivative. 5. The organic electroluminescent device according to claim 1, further comprising a hole injection transport layer between the pair of electrodes. 6. The organic electroluminescent device according to claim 1, further comprising an electron injection / transport layer between the pair of electrodes. 7. Bisacenaphtho [1 ', 2': 5,6] indeno
[1,2,3-cd: 1 ′, 2 ′, 3′-lm] perylene derivative has the general formula (1-
The organic electroluminescent device according to any one of claims 1 to 6, wherein A) is a compound represented by formula (1). Embedded image [In the formula, X _{1 to} X ₂₄ each independently represent a hydrogen atom, a halogen atom, a straight chain optionally having a substituent, a branched or cyclic alkyl group, a straight chain optionally having a substituent. , A branched or cyclic alkoxy group, a linear group which may have a substituent, a branched or cyclic alkylthio group, a linear group which may have a substituent, a branched or cyclic alkenyl group,
Straight-chain, branched or cyclic alkenyloxy group which may have a substituent, straight-chain, branched or cyclic alkenylthio group which may have a substituent, a substituted or unsubstituted aralkyl group, Unsubstituted aralkyloxy group,
A substituted or unsubstituted aralkylthio group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted arylthio group, a substituted or unsubstituted amino group, a cyano group, a hydroxyl group, a nitro group, -CO
OR ₁ group (wherein, R ₁ is a hydrogen atom, a linear or branched or cyclic alkyl group which may have a substituent, a linear or branched or cyclic alkenyl group which may have a substituent ,
Represents a substituted or unsubstituted aralkyl group or a substituted or unsubstituted aryl group), a —COR ₂ group (in the group, R
₂ is a hydrogen atom, an optionally substituted straight-chain, branched or cyclic alkyl group, an optionally substituted straight-chain, branched or cyclic alkenyl group, a substituted or unsubstituted aralkyl group during a substituted or unsubstituted aryl group or an amino group), or -OCOR _3, (group,
R ₃ is a linear or branched or cyclic alkyl group which may have a substituent, a linear or branched or cyclic alkenyl group which may have a substituent, a substituted or unsubstituted aralkyl group, or Represents a substituted or unsubstituted aryl group)
And further, mutually adjacent groups selected from X _{1 to} X ₂₄ , or X ₃ and X ₄ , X ₁₅ and X ₁₆ , X ₆ and X ₂₄ ,
Alternatively, X ₁₂ and X ₁₉ may be bonded to each other to form a substituted or unsubstituted carbocyclic aliphatic ring together with the substituted carbon atom. ] 8. A compound represented by the general formula (1-A): Embedded image [In the formula, X _{1 to} X ₂₄ each independently represent a hydrogen atom, a halogen atom, a straight chain optionally having a substituent, a branched or cyclic alkyl group, a straight chain optionally having a substituent. , A branched or cyclic alkoxy group, a linear group which may have a substituent, a branched or cyclic alkylthio group, a linear group which may have a substituent, a branched or cyclic alkenyl group,
Straight-chain, branched or cyclic alkenyloxy group which may have a substituent, straight-chain, branched or cyclic alkenylthio group which may have a substituent, a substituted or unsubstituted aralkyl group, Unsubstituted aralkyloxy group,
A substituted or unsubstituted aralkylthio group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted arylthio group, a substituted or unsubstituted amino group, a cyano group, a hydroxyl group, a nitro group, -CO
OR ₁ group (wherein, R ₁ is a hydrogen atom, a linear or branched or cyclic alkyl group which may have a substituent, a linear or branched or cyclic alkenyl group which may have a substituent ,
Represents a substituted or unsubstituted aralkyl group or a substituted or unsubstituted aryl group), a —COR ₂ group (in the group, R
₂ is a hydrogen atom, an optionally substituted straight-chain, branched or cyclic alkyl group, an optionally substituted straight-chain, branched or cyclic alkenyl group, a substituted or unsubstituted aralkyl group during a substituted or unsubstituted aryl group or an amino group), or -OCOR _3, (group,
R ₃ is a linear or branched or cyclic alkyl group which may have a substituent, a linear or branched or cyclic alkenyl group which may have a substituent, a substituted or unsubstituted aralkyl group, or Represents a substituted or unsubstituted aryl group)
And further, mutually adjacent groups selected from X _{1 to} X ₂₄ , or X ₃ and X ₄ , X ₁₅ and X ₁₆ , X ₇ and X ₂₄ ,
Alternatively, X ₁₂ and X ₁₉ may be bonded to each other to form a substituted or unsubstituted carbocyclic aliphatic ring together with the substituted carbon atom. However, X ₇ , X ₁₂ , X ₁₉ and X ₂₄
Are simultaneously a phenyl group, and all other X's are hydrogen atoms. ]