JP2017141167A - Compound, material for organic electroluminescent element using the same, organic electroluminescent element using the same, luminaire and display device - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a compound useful as a material for an organic EL element; and to provide an organic EL element using the same, having high luminous efficiency and a long life.SOLUTION: A compound for providing a material useful as an organic electroluminescent element material has, on 9-position of carbazole, a substituent containing 4-fluorenyl group having a specific substituent on 9,9'-positions. A material for an organic electroluminescent element using the same, an organic electroluminescent element using the same, luminaire and a display device are also provided.SELECTED DRAWING: None

Description

  The present invention relates to a compound, a material for an organic electroluminescence element using the compound, an organic electroluminescence element using the same, a lighting device, and a display device.

  In recent years, research on organic thin-film light-emitting devices that emit light when electrons injected from a cathode and holes injected from an anode are recombined in an organic light-emitting body sandwiched between both electrodes has been actively conducted. This light-emitting element is characterized by thin light emission with high luminance under a low driving voltage and multicolor light emission by selecting a light-emitting material.

When a voltage is applied to an organic electroluminescence element (hereinafter referred to as an organic EL element), holes from the anode and electrons from the cathode are injected into the light emitting layer. Then, in the light emitting layer, the injected holes and electrons are recombined to form excitons. At this time, singlet excitons and triplet excitons are generated at a ratio of 25%: 75% according to the statistical rule of electron spin. When classified according to the light emission principle, the fluorescence type uses light emitted from singlet excitons, and therefore the internal quantum efficiency of the organic EL element is said to be limited to 25%. On the other hand, in the phosphorescent type, since light emission by triplet excitons is used, it is known that the internal quantum efficiency can be increased to 100% when intersystem crossing is efficiently performed from singlet excitons.
Conventionally, in an organic EL element, an optimal element design has been made according to a light emission mechanism of a fluorescent type and a phosphorescent type. In particular, it is known that phosphorescent organic EL elements cannot obtain high-performance elements by simple diversion of fluorescent element technology because of their light emission characteristics. The reason is generally considered as follows.
First, since phosphorescence emission is emission using triplet excitons, the energy gap of the compound used in the light emitting layer must be large. This is because the value of the energy gap (hereinafter also referred to as singlet energy) of a compound usually refers to the triplet energy of the compound (in the present invention, the energy difference between the lowest excited triplet state and the ground state). This is because it is larger than the value of).

Therefore, in order to efficiently confine the triplet energy of the phosphorescent dopant material in the device, first, a host material having a triplet energy larger than the triplet energy of the phosphorescent dopant material must be used for the light emitting layer. Don't be. Furthermore, an electron transport layer and a hole transport layer adjacent to the light emitting layer are provided, and a compound having a triplet energy higher than that of the phosphorescent dopant material must be used for the electron transport layer and the hole transport layer. Thus, when based on the element design concept of the conventional organic EL element, a compound having a larger energy gap than the compound used for the fluorescent organic EL element is used for the phosphorescent organic EL element. The drive voltage of the entire element increases.
In addition, hydrocarbon compounds with high oxidation resistance and reduction resistance, which are useful in fluorescent elements, have a large energy gap due to a large spread of π electron clouds. Therefore, in the phosphorescent organic EL element, such a hydrocarbon compound is difficult to select, and an organic compound containing a hetero atom such as oxygen or nitrogen is selected. As a result, the phosphorescent organic EL element is There is a problem that the lifetime is shorter than that of a fluorescent organic EL element.
Furthermore, the fact that the exciton relaxation rate of the triplet exciton of the phosphorescent dopant material is much longer than that of the singlet exciton also greatly affects the device performance. That is, since light emitted from singlet excitons has a high relaxation rate that leads to light emission, the diffusion of excitons to the peripheral layers of the light-emitting layer (for example, a hole transport layer or an electron transport layer) hardly occurs and is efficient. Light emission is expected. On the other hand, light emission from triplet excitons is spin-forbidden and has a slow relaxation rate, so that excitons are likely to diffuse to the peripheral layer, and thermal energy deactivation occurs from other than specific phosphorescent compounds. End up. That is, control of the recombination region of electrons and holes is more important than the fluorescent organic EL element.
For the above reasons, in order to improve the performance of phosphorescent organic EL elements, material selection and element design different from those of fluorescent organic EL elements are required.

  As materials for such organic EL devices, Patent Document 1 discloses a compound having a 2-fluorenyl group at the 9-position of biscarbazole, and Patent Document 2 discloses an alkyl substituent at the 9 and 9 ′ positions. It is disclosed that a compound having a 4-fluorenyl group having 9-position of biscarbazole is used for an organic EL device.

International Publication No. 2012/108388 US Patent Application Publication No. 2015/0318487

However, in the field of organic EL devices, in order to further improve device performance, development of a material system useful for them is required.
The present invention has been made to solve the above-described problems, and provides a compound useful as a material for an organic EL device, and an organic EL device having high emission efficiency and a long lifetime using the compound. Objective.

  As a result of intensive studies by the present inventors to achieve the above object, a compound having a substituent containing a 4-fluorenyl group having a specific substituent at the 9,9′-position at the 9-position of carbazole is organic. It has been found that it is effective for improving device performance as an EL device material.

That is, according to one embodiment of the present invention, the following compounds are provided.
[1] A compound represented by the following formula (1).

In Formula (1), Ar ₁ and Ar ₂ represent a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms or a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms.
X represents an oxygen atom, a sulfur atom, C (R ′) (R ″), or N (—L ₂ —Ar ₃ ).
R ′ and R ″ each independently represents a hydrogen atom or a substituent.
Ar ₃ represents a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms.
L ₁ and L ₂ are each independently a single bond, a substituted or unsubstituted divalent arylene group having 6 to 18 ring carbon atoms, or a substituted or unsubstituted divalent aryl group having 5 to 18 ring atoms. Represents a heteroarylene group.
R _{1 to} R ₆ each independently represent a substituent, and adjacent R _{1 s} , R _{2 s} , R _{3 s} , R _{4 s} , R _{5 s} , and R _{6 s} are independently bonded to each other. To form a ring.
a, c, and f each independently represent an integer of 0 to 4, and b, d, and e each independently represents an integer of 0 to 3.

[2] A material for an organic electroluminescence device containing the compound of [1].
[3] An organic electroluminescence device having a cathode, an anode, and an organic thin film layer composed of one layer or a plurality of layers sandwiched between the cathode and the anode, the organic thin film layer including a light emitting layer, The organic electroluminescent element in which at least 1 layer contains the compound as described in [2].
[4] An illumination device comprising the organic electroluminescence element according to [3].
[5] A display device comprising the organic electroluminescence element according to [3].

  The present invention provides a novel material useful for an organic EL device and an organic EL device having high luminous efficiency and a long lifetime using the same.

It is a figure which shows schematic structure of an example of the organic EL element which concerns on embodiment of this invention.

In the present specification, the “carbon number XX to YY” in the expression “substituted or unsubstituted ZZ group having XX to YY” represents the number of carbon atoms in the case where the ZZ group is unsubstituted. The carbon number of the substituent in the case where it is present is not included.
Further, in this specification, “atom number XX to YY” in the expression “a ZZ group having a substituted or unsubstituted atom number XX to YY” represents the number of atoms when the ZZ group is unsubstituted. In the case of substitution, the number of substituent atoms is not included.

  In this specification, the number of ring-forming carbon atoms constitutes the ring itself of a compound having a structure in which atoms are bonded cyclically (for example, a monocyclic compound, a condensed ring compound, a bridged compound, a carbocyclic compound, or a heterocyclic compound). Represents the number of carbon atoms in the atom. When the ring is substituted with a substituent, the carbon contained in the substituent is not included in the number of ring-forming carbons. The “ring-forming carbon number” described below is the same unless otherwise specified. For example, the benzene ring has 6 ring carbon atoms, the naphthalene ring has 10 ring carbon atoms, the pyridinyl group has 5 ring carbon atoms, and the furanyl group has 4 ring carbon atoms. Further, when an alkyl group is substituted as a substituent on the benzene ring or naphthalene ring, the carbon number of the alkyl group is not included in the number of ring-forming carbons. Further, when a fluorene ring, for example, is bonded to the fluorene ring as a substituent, the number of carbon atoms of the fluorene ring as a substituent is not included in the number of ring-forming carbon atoms.

  In this specification, the number of ring-forming atoms refers to a compound (for example, a monocyclic compound, a condensed ring compound, a bridged compound, or a carbocyclic compound) having a structure in which atoms are bonded in a cyclic manner (for example, a single ring, a condensed ring, or a ring assembly). , A heterocyclic compound) represents the number of atoms constituting the ring itself. An atom that does not constitute a ring (for example, a hydrogen atom that terminates a bond of an atom that constitutes a ring) or an atom contained in a substituent when the ring is substituted by a substituent is not included in the number of ring-forming atoms. The “number of ring-forming atoms” described below is the same unless otherwise specified. For example, the number of ring-forming atoms in the pyridine ring is 6, the number of ring-forming atoms in the quinazoline ring is 10, and the number of ring-forming atoms in the furan ring is 5. A hydrogen atom bonded to a carbon atom of a pyridine ring or a quinazoline ring or an atom constituting a substituent is not included in the number of ring-forming atoms. Further, when, for example, a fluorene ring is bonded to the fluorene ring as a substituent, the number of atoms of the fluorene ring as the substituent is not included in the number of ring-forming atoms.

In the present specification, “hydrogen atom” includes isotopes having different numbers of neutrons, that is, light hydrogen (protium), deuterium (deuterium), and tritium (tritium).
In the present specification, the “heteroaryl group” and the “heteroarylene group” are groups containing at least one heteroatom as a ring-forming atom, and the heteroatom includes a nitrogen atom, an oxygen atom, and a sulfur atom. It is preferable that it is 1 or more types chosen from a silicon atom and a selenium atom.

The substituent in the description of “substituted or unsubstituted” includes an alkyl group having 1 to 50 carbon atoms (preferably 1 to 18, more preferably 1 to 8); 3 to 50 ring carbon atoms (preferably A cycloalkyl group having 3 to 10, more preferably 3 to 8, and even more preferably 5 or 6; an aryl group having 6 to 50 ring carbon atoms (preferably 6 to 25, more preferably 6 to 18); ring formation An aralkyl group having 7 to 51 (preferably 7 to 30, more preferably 7 to 20) carbon atoms having an aryl group having 6 to 50 carbon atoms (preferably 6 to 25, more preferably 6 to 18); ring-forming carbon An aryl group having 6 to 50 (preferably 6 to 25, more preferably 6 to 18) or a heteroaryl group having 3 to 50 ring atoms (preferably 5 to 25, more preferably 5 to 18) amino An alkoxy group having an alkyl group having 1 to 50 carbon atoms (preferably 1 to 18, more preferably 1 to 8); 6 to 50 ring carbon atoms (preferably 6 to 25, more preferably 6 to 18) An aryloxy group having an aryl group; an arylthio group having an aryl group having 6 to 50 ring carbon atoms (preferably 6 to 25, more preferably 6 to 18); 1 to 50 carbon atoms (preferably 1 to 18 or more) Preferably mono-substituted, di-substituted or tri-substituted silyl having a substituent selected from an alkyl group having 1 to 8) and an aryl group having 6 to 50 ring carbon atoms (preferably 6 to 25, more preferably 6 to 18). A heteroaryl group having 5 to 50 ring atoms (preferably 5 to 24, more preferably 5 to 13); a group having 1 to 50 carbon atoms (preferably 1 to 18 and more preferably 1 to 8) Alkyl group; halogen atom (fluorine atom, chlorine atom, bromine atom, iodine atom); cyano group; nitro group; alkyl group having 1 to 50 carbon atoms (preferably 1 to 18, more preferably 1 to 8) and ring formation A sulfonyl group having a substituent selected from an aryl group having 6 to 50 carbon atoms (preferably 6 to 25, more preferably 6 to 18 carbon atoms); 1 to 50 carbon atoms (preferably 1 to 18, more preferably 1 to 8 carbon atoms) ) And a disubstituted phosphoryl group having a substituent selected from an aryl group having 6 to 50 (preferably 6 to 25, more preferably 6 to 18) ring carbon atoms; an alkylsulfonyloxy group; an arylsulfonyloxy group Alkylcarbonyloxy group; arylcarbonyloxy group; boron-containing group; zinc-containing group; tin-containing group; silicon-containing group; A lithium-containing group, a hydroxy group, an alkyl-substituted or aryl-substituted carbonyl group, a carboxyl group, a vinyl group, a (meth) acryloyl group, an epoxy group, and an oxetanyl group.
These substituents may be further substituted with the above-mentioned arbitrary substituents. In addition, these substituents may be bonded to each other to form a ring.
In addition, “unsubstituted” in the description of “substituted or unsubstituted” means that a hydrogen atom is bonded without being substituted by these substituents.

  Among the above substituents, more preferably, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms (preferably 1 to 18, more preferably 1 to 8), substituted or unsubstituted ring forming carbon atoms having 3 to 50 carbon atoms. (Preferably 3 to 10, more preferably 3 to 8, still more preferably 5 or 6) cycloalkyl group, substituted or unsubstituted ring carbon atoms of 6 to 50 (preferably 6 to 25, more preferably 6 to 6) 18) an aryl group, a substituted or unsubstituted heteroaryl group having 5 to 50 ring atoms (preferably 5 to 24, more preferably 5 to 13), a halogen atom, and a cyano group.

  In the present specification, it is possible to arbitrarily select a definition that is preferable, and it can be said that a combination of definitions that is preferable is a more preferable embodiment.

[Compound]
In one embodiment of the present invention, a compound represented by the following formula (1) is provided. The compound represented by formula (1) [hereinafter sometimes referred to as compound (1)] is useful as a material for an organic electroluminescence device.

In Formula (1), Ar ₁ and Ar ₂ represent a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms or a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms.
X represents an oxygen atom, a sulfur atom, C (R ′) (R ″), or N (—L ₂ —Ar ₃ ).
R ′ and R ″ each independently represents a hydrogen atom or a substituent.
Ar ₃ represents a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms.
L ₁ and L ₂ are each independently a single bond, a substituted or unsubstituted divalent arylene group having 6 to 18 ring carbon atoms, or a substituted or unsubstituted divalent aryl group having 5 to 18 ring atoms. Represents a heteroarylene group.
R _{1 to} R ₆ each independently represent a substituent, and adjacent R _{1 s} , R _{2 s} , R _{3 s} , R _{4 s} , R _{5 s} , and R _{6 s} are independently bonded to each other. To form a ring.
a, c, and f each independently represent an integer of 0 to 4, and b, d, and e each independently represents an integer of 0 to 3.

Hereinafter, in the formula (1), a 5-membered ring having N and a 3-ring condensed ring (carbazole ring) composed of two benzene rings adjacent to the 5-membered ring is an N skeleton, a 5-membered ring having X and the 5-membered ring A three-ring condensed ring composed of two benzene rings adjacent to the ring may be referred to as an X skeleton, and a fluorene ring having Ar ₁ and Ar ₂ at the 9,9 ′ positions may be referred to as a C skeleton.
A bonding mode between the N skeleton and the X skeleton in the formula (1) will be described. A partial structure in which the N skeleton and the X skeleton of Formula (1) are extracted and (R ₃ ) _c to (R ₆ ) _f is omitted is shown in Formula (1-1).

  In Formula (1-1), * is bonded to any one carbon atom at positions 5 to 8 of the N skeleton, and ** is bonded to any one carbon atom at positions 5 to 8 in the X skeleton. . The bonding position of * and ** is not particularly limited as long as it is in the above range, but from the viewpoint of improving the function of the organic EL element, it is a bonding position represented by the formula (2-1) or (2-2). Is preferred.

In the formulas (2-1) and (2-2), X represents an oxygen atom, a sulfur atom, C (R ′) (R ″), or N (—L ₂ —Ar ₃ ), and Ar ₁ to Ar ₃ , R ′, R ″, R _{1 to} R ₆ , L ₁ , L ₂ and a to f are the same as those in the formula (1).

In Formula (1), Ar ₁ and Ar ₂ represent a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms or a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms.
Examples of the aryl group having 6 to 30 ring carbon atoms include a non-condensed aryl group and a condensed aryl group. More specifically, a phenyl group, a naphthyl group, a phenanthryl group, a biphenylyl group, a terphenyl group, and a quarterphenyl group. Fluoranthenyl group, triphenylenyl group, phenanthrenyl group, fluorenyl group, benzo [c] phenanthrenyl group, benzo [a] triphenylenyl group, naphtho [1,2-c] phenanthrenyl group, naphtho [1,2-a] triphenylenyl group , Dibenzo [a, c] triphenylenyl group, benzo [b] fluoranthenyl group and the like.

  Examples of the heteroaryl group having 5 to 30 ring atoms include a non-fused aromatic heterocycle and a fused aromatic heterocycle, and more specifically, a pyrrolyl group, a pyrazinyl group, a pyridinyl group, an indolyl group, and an isoindolyl group. , Furyl group, benzofuranyl group, isobenzofuranyl group, dibenzofuranyl group, dibenzothiophenyl group, quinolyl group, isoquinolyl group, quinoxalinyl group, quinazolinyl group, benzoquinazolinyl group, azafluoranthenyl group, carbazolyl group, Azacarbazolyl, phenanthridinyl, azatriphenylenyl, diazatriphenylenyl, acridinyl, phenanthrolinyl, thienyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, indolyl Group, quinolinyl group, acridinyl group, Loridinyl group, dioxanyl group, piperidinyl group, morpholinyl group, piperazinyl group, furanyl group, thiophenyl group, oxazolyl group, oxadiazolyl group, benzoxazolyl group, thiazolyl group, thiadiazolyl group, benzothiazolyl group, triazolyl group, imidazolyl group, benzimidazolyl group , Imidazopyridinyl group, purinyl group, pyranyl group, benzonaphthofuranyl group, benzonaphthothiophenyl group, benzocarbazolyl group, indenocarbazolyl group, indolocarbazolyl group, dibenzocarbazolyl group , Pyrrolocarbazolyl group, thienocarbazolyl group, furocarbazolyl group, imidazocarbazolyl group, benzimidazolobenzimidazolyl group, oxazolocarbazolyl group, thiazolocarbazolyl group, dibenzoazepinyl group, tri Nzoazepiniru group, dibenzo Indian lower benzindolyl group and the like.

Ar ₁ and Ar ₂ are, among the above, as the aryl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted biphenylyl group, a substituted or unsubstituted phenanthryl group, substituted or An unsubstituted triphenylenyl group, a substituted or unsubstituted fluoranthenyl group is preferred, and the heteroaryl group includes a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted carbazolyl Group, substituted or unsubstituted pyrimidinyl group, substituted or unsubstituted triazinyl group, or substituted or unsubstituted quinazolinyl group, particularly when used as a green or yellow phosphorescent host, the triplet energy level is preferably Preferably high substituent, Or an unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted triphenylenyl group, a substituted or unsubstituted dibenzofuranyl group, It is preferably a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted pyrimidinyl group, or a substituted or unsubstituted triazinyl group.

In formula (1), R _{1 to} R ₆ each independently represent a substituent, and a to f represent the number of substituents of R _{1 to} R ₆ , respectively. Specifically, a, c, and f each independently represent an integer of 0 to 4, and b, d, and e each independently represent an integer of 0 to 3.
In formula (1), the C skeleton is represented by formula (1-2), the N skeleton is represented by formula (1-3), and the X skeleton is represented by formula (1-4).

In Formula (1-2), R ₁ can be bonded to the C skeleton in the range of any one or more of the 5 to 8 positions of the C skeleton, and may not be bonded to the C skeleton (a = 0). R ₂ can be bonded to the C skeleton in the range of any one to three of the 1 to 3 positions of the C skeleton, and may not be bonded to the C skeleton (b = 0).

In the formula (1-3), R ₃ can be bonded to the N skeleton in the range of any one to four of the 1 to 4 positions of the N skeleton, and may not be bonded to the N skeleton (c = 0). R ₄ can be bonded to the N skeleton in the range of any one to three of the 5 to 8 positions of the N skeleton (except for the bonding position between the N skeleton and the X skeleton), and bonded to the N skeleton. It is not necessary to do this (d = 0).

In Formula (1-4), R ₅ can be bonded to the X skeleton in the range of any one or more of the 5 to 8 positions of the X skeleton (provided that the bonding position between the N skeleton and the X skeleton). May not be bonded to the X skeleton (e = 0). R ₆ can be bonded to the X skeleton in the range of any one or more of 1 to 4 positions of the X skeleton, and may not be bonded to the X skeleton (f = 0).

R _{1 to} R ₆ are adjacent to each other, R ₁ , R ₂ , R ₃ , R ₄ , R ₅ , and R ₆ are each independently bonded to each other to form a ring (particularly a benzene ring). May be formed. Specifically, for example, in the formula (1-2), or to form a benzene ring bonded 7-position of the _{R 1} of _{R 1} and 8-position, in Formula (1-3), 2-position R ₃ and 3-position R ₃ may combine to form a benzene ring, or in formula (1-4), 3-position R ₆ and 4-position R ₆ may combine to form a benzene ring. it can. The formation position of the ring is not limited to these examples.
a to f are each independently preferably 0 to 2, preferably 0 or 1, and more preferably 0.

Specific examples of the substituent represented by R _{1 to} R ₆ include an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 50 ring carbon atoms, and an aryl group having 6 to 18 ring carbon atoms. , An aralkyl group having 7 to 30 carbon atoms having an aryl group having 6 to 10 ring carbon atoms, an alkoxy group having 1 to 20 carbon atoms, an aryloxy group having 6 to 10 ring carbon atoms; an alkyl having 1 to 20 carbon atoms A mono-substituted, di-substituted or tri-substituted silyl group having a substituent selected from a group and an aryl group having 6 to 10 ring carbon atoms, a heteroaryl group having 5 to 18 ring atoms, and a haloalkyl group having 1 to 20 carbon atoms , A haloalkoxy group having 1 to 20 carbon atoms, a halogen atom, a cyano group, and a nitro group. When there are two or more R _{1 to} R ₆ , a plurality of R ₁ , R ₂ , R ₃ , R ₄ , R ₅ , and R ₆ may be the same or different.

The alkyl group having 1 to 20 carbon atoms may be linear or branched. For example, methyl group, ethyl group, propyl group, isopropyl group, n-butyl group, s-butyl group , Isobutyl group, t-butyl group, n-pentyl group, n-hexyl group, n-heptyl group, n-octyl group, n-nonyl group, n-decyl group, n-undecyl group, n-dodecyl group, n -Tridecyl group, n-tetradecyl group, n-pentadecyl group, n-hexadecyl group, n-heptadecyl group, n-octadecyl group, neopentyl group, 1-methylpentyl group, 2-methylpentyl group, 1-pentylhexyl group, 1-butylpentyl group, 1-heptyloctyl group, 3-methylpentyl group, trifluoromethyl group, 2,2,2-trifluoroethyl group, 1,1,1,3,3,3-hexa Ruoro-2-propyl group and the like.
Carbon number of a C1-C20 alkyl group becomes like this. Preferably it is 1-18, More preferably, it is 1-8.

Examples of the cycloalkyl group having 3 to 50 ring carbon atoms include a cyclopentyl group, a cyclohexyl group, a cyclooctyl group, and a 3,5-tetramethylcyclohexyl group. The ring-forming carbon number of the cycloalkyl group is preferably 6 to 25, more preferably 6 to 18.
Examples of the aryl group having 6 to 18 ring carbon atoms include those having 6 to 18 ring carbon atoms among the aryl groups described as the aryl group having 6 to 30 ring carbon atoms of Ar ₁ and Ar _2. . Specific examples include a phenyl group, a naphthyl group, a phenanthryl group, a biphenylyl group, a terphenyl group, a fluoranthenyl group, a triphenylenyl group, a phenanthrenyl group, and a fluorenyl group.
The ring-forming carbon number of the aryl group is preferably 6-16, more preferably 6-14.

In the aralkyl group having 7 to 30 carbon atoms having an aryl group having 6 to 10 ring carbon atoms, the aryl group having 6 to 10 ring carbon atoms is aryl having 6 to 30 ring carbon atoms of Ar ₁ and Ar _2. Among the aryl groups described as the group, those having 6 to 10 ring carbon atoms can be mentioned. Specific examples include a phenyl group, a naphthyl group, and a biphenylyl group.
The “aralkyl group having 7 to 30 carbon atoms” in the aralkyl group having 7 to 30 carbon atoms having an aryl group having 6 to 10 ring carbon atoms includes 6 to 10 ring carbon atoms of the aryl group. For example, benzyl group (phenylmethyl group) C ₆ H ₅ CH ₂ — is an aralkyl group having 7 carbon atoms having an aryl group having 6 ring carbon atoms.
The divalent alkylene group having 1 to 20 carbon atoms constituting the aralkyl group is represented by a group in which one hydrogen atom is removed from the alkyl group having 1 to 20 carbon atoms represented by R _{1 to} R _6. These are the same as the above-mentioned “C1-20 alkyl group” and may be linear or branched.
Carbon number of the C1-C20 alkylene group which comprises an aralkyl group becomes like this. Preferably it is 1-18, More preferably, it is 1-8.

The alkoxy group having 1 to 20 carbon atoms is a group represented by —OR, and R is the same as the above-mentioned “alkyl group having 1 to 20 carbon atoms”. It may be.
The aryloxy group having 6 to 10 ring carbon atoms is a group represented by —OAr, and Ar is an aryl group described as an aryl group having 6 to 30 ring carbon atoms of Ar ₁ and Ar ₂ . The thing of 6-10 ring forming carbon number is mentioned. Specific examples include a phenyl group, a naphthyl group, and a biphenylyl group.

Examples of the mono-substituted, di-substituted or tri-substituted silyl group having a substituent selected from an alkyl group having 1 to 20 carbon atoms and an aryl group having 6 to 10 ring carbon atoms include, for example, a trimethylsilyl group, a triethylsilyl group, t- Examples thereof include butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, isopropyldimethylsilyl group, triphenylsilyl group, phenyldimethylsilyl group, t-butyldiphenylsilyl group, and tolylsilylsilyl group. These may be further substituted.
The mono-substituted, di-substituted or tri-substituted silyl group is preferably mono-substituted, di-substituted or di-substituted having a substituent selected from the above alkyl group having 1 to 18 carbon atoms and the above aryl group having 6 to 10 ring carbon atoms. A tri-substituted silyl group can be mentioned. These may be further substituted. More preferably, a monosubstituted, disubstituted or trisubstituted silyl group having a substituent selected from the above alkyl group having 1 to 8 carbon atoms and the above aryl group having 6 to 10 ring carbon atoms is exemplified.

As the heteroaryl group having 5 to 18 ring atoms, among the aryl groups described as the heteroaryl group having 5 to 30 ring atoms of Ar ₁ and Ar ₂ , those having 5 to 18 ring carbon atoms are included. Can be mentioned. Specific examples include a phenyl group, a naphthyl group, a phenanthryl group, a biphenylyl group, a terphenyl group, a fluoranthenyl group, a triphenylenyl group, a phenanthrenyl group, and a fluorenyl group.
The number of ring-forming atoms of the heteroaryl group is preferably 5-13.

  As the haloalkyl group having 1 to 20 carbon atoms, all or part of the hydrogen atoms in the alkyl group having 1 to 20 carbon atoms are any one halogen atom (fluorine atom, chlorine atom, bromine atom, iodine atom). And a group substituted with. The number of carbon atoms of the haloalkyl group is preferably 1-18, more preferably 1-8.

As the haloalkoxy group having 1 to 20 carbon atoms, all or part of the hydrogen atoms in the alkoxy group having 1 to 20 carbon atoms are any one halogen atom (fluorine atom, chlorine atom, bromine atom, iodine atom). ). The carbon number of the haloalkoxy group is preferably 1-18, more preferably 1-8.
Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.

In Formula (1), L ₁ represents a single bond, a substituted or unsubstituted divalent arylene group having 6 to 18 ring carbon atoms, or a substituted or unsubstituted divalent hetero atom having 5 to 18 ring atoms. Represents an arylene group.
Examples of the divalent arylene group having 6 to 18 ring carbon atoms include groups in which one hydrogen atom has been removed from the aryl group having 6 to 18 ring carbon atoms described as the substituent represented by R _{1 to} R _6. It is done. The number of ring-forming carbon atoms of the divalent arylene group is preferably 6 to 16, more preferably 6 to 14.
The divalent heteroarylene group having 5 to 18 ring atoms is a group obtained by removing one hydrogen atom from the heteroaryl group having 5 to 18 ring atoms described as the substituent represented by R _{1 to} R _6. Is mentioned. The number of ring-forming carbon atoms of the divalent heteroarylene group is preferably 5 to 13.

Among these, L ₁ is preferably represented by a single bond, the following formula (4-1), the following formula (4-2), or the following formula (4-3), and more preferably a single bond. preferable.
When L ₁ is a single bond, the compound (1) is preferably represented by the following formula (3-1) or (3-2).

In the formulas (3-1) and (3-2), X represents an oxygen atom, a sulfur atom, C (R ′) (R ″), or N (—L ₂ —Ar ₃ ), and Ar ₁ to Ar ₃ , R ′, R ″, R _{1 to} R ₆ , L ₂ and a to f are the same as those in the formula (1).

In formulas (4-1) to (4-3), R _{41 to} R ₄₅ each independently represent a substituent. g, h and i each independently represents an integer of 0 to 3, and j and k each represents an integer of 0 to 2. Z represents an oxygen atom, a sulfur atom, C (R ₄₆ ) (R ₄₇ ), or N (—L ₃ —Ar ₄ ). R ₄₆ and R ₄₇ each independently represents a hydrogen atom or a substituent. L ₃ represents a single bond, a substituted or unsubstituted divalent arylene group having 6 to 18 ring carbon atoms, or a substituted or unsubstituted divalent heteroarylene group having 5 to 18 ring atoms. Ar ₄ represents a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms or a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms.

R _{41 to} R ₄₅ are the same as R _{1 to} R ₆ in the formula (1), and preferred embodiments are also the same.
R ₄₆ and R ₄₇ are the same as R ′ and R ″ in the formula (1), and preferred embodiments are also the same.
L ₃ is the same as L ₂ in the formula (1), and the preferred embodiment is also the same.
Ar ₄ is the same as that in Formula (1) and Ar ₃ , and the preferred embodiment is also the same. A preferred embodiment of Ar ₃ will be described later.
g to k are preferably 0 to 2, more preferably 0 or 1, and may be 0.
Z is preferably an oxygen atom among oxygen atoms, sulfur atoms, C (R ₄₆ ) (R ₄₇ ), and N (—L ₃ —Ar ₄ ).

The arylene group and heteroarylene group represented by the formulas (4-1) to (4-3) are, for example, a C skeleton and an N skeleton in the form represented by the formulas (4-1 ′) to (4-3 ′). To join. N * shown in Formulas (4-1 ′) to (4-3 ′) represents a bonding position with the N skeleton of the bond, and * C represents a bonding position with the C skeleton of the bond.
Hereinafter, in formulas (4-3) and (4-3 ′), a three-ring condensed ring composed of a 5-membered ring having Z and two benzene rings adjacent to the 5-membered ring may be referred to as a Z skeleton. .

In the formula (4-1 ′), a bond bonded to the C skeleton and a bond bonded to the N skeleton are bonded to any one of positions 1 to 6 of the benzene ring. There are no particular restrictions on the position of the bond that binds to the C skeleton and the bond that binds to the N skeleton, but it is preferable that the bonds be in a para-position.
R ₄₁ can be bonded to the benzene ring in any one of the 1 to 6 positions of the benzene ring in the range of 4 to 4 (excluding the bonding position of the bond), but not bonded to the benzene ring. (G = 0).

In Formula (4-2 ′), the bond that bonds to the C skeleton is bonded to any one of positions 1 to 6 of the biphenyl ring (right benzene ring), and the bond that bonds to the N skeleton is biphenyl. It is bonded to any one of 1 ′ to 6 ′ positions of the ring (left benzene ring). Further, in the bond connecting two benzene rings of the biphenyl ring (having # at each of the left end and the right end), one of # is bonded to any one of 1 to 6 positions of the biphenyl ring, and the other is 1 ′ to It binds to any one of the 6 'positions.
R ₄₂ can be bonded to the benzene ring in the range of any 1 to 4 in the 1 ′ to 6 ′ position of the biphenyl ring (except for the position bonded to the N skeleton but bonded to the benzene ring). , It may not be bonded to the benzene ring (h = 0). R ₄₃ can be bonded to the benzene ring in the range of any one of 1 to 6 positions of the biphenyl ring and 4 or less (except for the position bonded to the C skeleton but bonded to the benzene ring). It may not be bonded to the ring (i = 0).

In Formula (4-3 ′), the bond that binds to the C skeleton is bonded to any one of positions 1 to 4 of the Z skeleton, and the bond that bonds to the N skeleton is any of positions 5 to 8 Combine into one.
R ₄₅ can be bonded to the Z skeleton in the range of any one to three of the 1 to 4 positions of the Z skeleton (except for the position where the bond bonding to the C skeleton is bonded to the Z skeleton). , It may not be bonded to the Z skeleton (k = 0). R ₄₄ can be bonded to the Z skeleton in the range of any one to three of the 5 to 8 positions of the Z skeleton (however, it is bonded to the N skeleton but excludes the position bonded to the Z skeleton). It may not be bonded to the skeleton (j = 0).

L ₁ is represented by formulas (4-1) and (4-2) among the arylene groups and heteroarylene groups represented by formulas (4-1), (4-2), and (4-3). The arylene group (more preferably g to i is 0) is preferable, and the arylene group represented by the formula (4-1) (more preferably g is 0) is more preferable.

In the formula (1), X represents an oxygen atom, a sulfur atom, C (R ′) (R ″), or N (—L ₂ —Ar ₃ ), and R ′ and R ″ each independently Represents a hydrogen atom or a substituent. L ₂ represents a single bond, a substituted or unsubstituted divalent arylene group having 6 to 18 ring carbon atoms, or a substituted or unsubstituted divalent heteroarylene group having 5 to 18 ring atoms. , Ar ₃ represents a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms.
L ₂ is the same as L ₁ in the formula (1), and the preferred embodiment is also the same. Thus, _{L 2} is the formula (4-1) can be represented by (4-2), or (4-3). In this case, N * in the formulas (4-1 ′) to (4-3 ′) represents a bonding position with the N skeleton of the bond, and * C represents a bonding position with Ar ₃ of the bond. What is necessary is just to read as a thing.

As already mentioned, a preferred embodiment of the _{L 3} is the same as _{L 2, L 3} has the formula (4-1) can be represented by (4-2), or (4-3). In this case, N * in the formulas (4-1 ′) to (4-3 ′) represents a bonding position with the Z skeleton of the bond, and * C represents a bonding position with Ar ₄ of the bond. What is necessary is just to read as a thing.

When X is C (R ′) (R ″) in the formula (1), the X skeleton is represented as a fluorene ring in which R ′ and R ″ are substituted at the 9,9 ′ positions. When X is _{N (-L 2 -Ar 3),} X skeleton is _-L 2 -Ar ₃ to 9 nitrogen atom at position represented as carbazole ring substituted. The compound (1) is preferably represented by the following formula (5-1) or (5-2).

In the formulas (5-1) and (5-2), Ar _{1 to} Ar ₃ , R _{1 to} R ₆ , L ₁ , L ₂ and a to f are the same as those in the formula (1).

When X in the formula (1) is C (R ′) (R ″), when R ′ and R ″ are substituents, the substituents are R _{1 to} R in the formula (1). It is the same as the substituent explained as the substituent of ₆ and preferred embodiments are also the same.
In the case where X in the formula (1) is N (—L ₂ —Ar ₃ ), L ₂ is the same as L ₂ in the formula (1), and the preferred embodiment is also the same.

In the case where X in the formula (1) is N (—L ₂ —Ar ₃ ), Ar ₃ is the same as Ar ₁ and Ar ₂ in the formula (1).
Ar ₃ is a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted biphenylyl group, a substituted or unsubstituted triphenylenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted dibenzo A furanyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted pyridinyl group, a substituted or unsubstituted pyrimidinyl group, or a substituted or unsubstituted triazolyl group is preferable, a substituted or unsubstituted phenyl group, Substituted or unsubstituted biphenylyl group, substituted or unsubstituted triphenylenyl group, substituted or unsubstituted fluorenyl group, substituted or unsubstituted dibenzofuranyl group, substituted or unsubstituted dibenzothiophenyl group, substituted or unsubstituted pyridinyl Group, substitution or An unsubstituted pyrimidinyl group or a substituted or unsubstituted triazolyl group is more preferred, a substituted or unsubstituted phenyl group is more preferred, and an unsubstituted phenyl group is still more preferred.
However, when X is N (—L ₂ —Ar ₃ ), the substituent substituted at the 9-position of the N skeleton (that is, L ₁ , C skeleton, and all substituents bonded to the C skeleton) is X It is preferably bulkier than the substituent bonded to the 9-position of the skeleton (that is, -L ₂ -Ar ₃ ). From this point of view, (if _{L 2} and Ar ₃ comprises a substituent, including a number of carbon atoms of the substituent) the total number of carbon atoms of the _{L 2} and Ar ₃ are, preferably 6 to 20, more preferably 6 It is -15, More preferably, it is 6-12.

In the formula (1), X represents an oxygen atom, a sulfur atom, C (R ') (R ''), and among _N of _(-L 2 -Ar _3), is _{N (-L} 2 -Ar ₃₎ It is preferable.
Furthermore, the compound (1) is preferably represented by the following formula (6-1) or (6-2).

In the formulas (6-1) and (6-2), Ar _{1 to} Ar ₃ , R _{1 to} R ₆ , and a to f are the same as those in the formula (1).
As described above, it is preferable that R _{1 to} R ₆ are not substituted in the C skeleton, the N skeleton, and the X skeleton in the formula (1). That is, it is preferable that af is 0, and it is preferable that Formula (1) is further represented by the following formula (7-1) or (7-2).

In the formulas (7-1) and (7-2), Ar _{1 to} Ar ₃ are the same as those in the formula (1).
Although the specific example of the compound which belongs to the compound represented by Formula (1) which is 1 aspect of this invention below is shown, the compound represented by Formula (1) is not limited to these.

[Materials for organic EL elements]
The material for an organic EL device of one embodiment of the present invention contains the compound represented by the above formula (1) [compound (1)], and the content of the compound (1) is preferably 50% by mass. Above, more preferably 70% by mass or more, still more preferably 80% by mass or more, particularly preferably 90% by mass or more. The material for an organic EL device of one embodiment of the present invention may be composed of only the compound (1). The preferred embodiment of the formula (1) is as described above. Hereinafter, the description regarding the compound (1) can be read by replacing the compound of the preferred embodiment of the formula (1) described above.
The material for an organic EL element of one embodiment of the present invention is useful as a material for an organic thin film layer composed of one or more layers sandwiched between a cathode and an anode of an organic EL element, and in particular, a material for a hole transport layer. Alternatively, it is more useful as a material for a hole injection layer or a host material (particularly a phosphorescent host material) for a light emitting layer.

[Organic EL device]
Next, the organic EL element of one embodiment of the present invention is described.
The organic EL device of one embodiment of the present invention is an organic electroluminescence device having a cathode, an anode, and an organic thin film layer composed of one layer or a plurality of layers sandwiched between the cathode and the anode, and the organic thin film layer is a light emitting layer And at least one of the organic thin film layers is an organic electroluminescent device containing the compound [compound (1)] represented by the general formula (1).

  In one embodiment of the present invention, the organic EL element may be a fluorescent or phosphorescent monochromatic light emitting element, a fluorescent / phosphorescent hybrid white light emitting element, or a simple type having a single light emitting unit. Alternatively, a tandem type having a plurality of light emitting units may be used, and among them, a phosphorescent type is preferable. Here, the “light emitting unit” refers to a minimum unit that includes one or more organic layers, one of which is a light emitting layer, and can emit light by recombination of injected holes and electrons.

As typical element configurations of the simple organic EL element, the following (1) to (13) may be mentioned, but the invention is not particularly limited thereto. The element configuration (8) is preferably used.
(1) Anode / light emitting layer / cathode (2) Anode / hole injection layer / light emitting layer / cathode (3) Anode / light emitting layer / electron injection layer / cathode (4) Anode / hole injection layer / light emitting layer / electron Injection layer / cathode (5) anode / organic semiconductor layer / light emitting layer / cathode (6) anode / organic semiconductor layer / electron barrier layer / light emitting layer / cathode (7) anode / organic semiconductor layer / light emitting layer / adhesion improving layer / Cathode (8) Anode (/ hole injection layer) / Hole transport layer / Light emitting layer / Electron transport layer (/ electron injection layer) / Cathode (9) Anode / insulating layer / light emitting layer / insulating layer / cathode (10) Anode / inorganic semiconductor layer / insulating layer / light emitting layer / insulating layer / cathode (11) anode / organic semiconductor layer / insulating layer / light emitting layer / insulating layer / cathode (12) anode / insulating layer (/ hole injection layer) / Hole transport layer / light emitting layer / insulating layer / cathode (13) anode / insulating layer (/ hole injection layer) / hole transport layer / light emitting layer / electron transport layer (/ electron injection layer) / cathode

FIG. 1 shows a schematic configuration of an example of the organic EL element of one embodiment of the present invention.
The organic EL element 1 includes a substrate 2, an anode 3, a cathode 4, and a light emitting unit 10 disposed between the anode 3 and the cathode 4. The light emitting unit 10 includes a light emitting layer 5 containing a host material and a dopant (light emitting material). In the light emitting unit 10, a hole injection / transport layer 6 (anode-side organic thin film layer 6) between the light emitting layer 5 and the anode 3, and an electron injection / transport layer 7 (cathode) between the light emitting layer 5 and the cathode 4. A side organic thin film layer 7) or the like may be included. Further, an electron barrier layer may be provided on the anode 3 side of the light emitting layer 5, and a hole barrier layer may be provided on the cathode 4 side of the light emitting layer 5. Thereby, electrons and holes can be confined in the light emitting layer 5, and the exciton generation probability in the light emitting layer 5 can be increased.

The organic thin film layer containing the compound (1) includes an anode-side organic thin film layer (hole transport layer, hole injection layer, etc.) provided between the anode and the light emitting layer, a light emitting layer, a cathode and a light emitting layer. Examples include, but are not limited to, a cathode-side organic thin film layer (electron transport layer, electron injection layer, etc.), a space layer, a barrier layer, and the like provided between the layers.
The compound (1) may be used for any organic thin film layer of the organic EL element, but from the viewpoint of light emission efficiency, a hole injection layer or a hole transport layer, an electron injection layer or an electron transport layer, or a light emitting layer. It is preferable to use for.
That is, as the organic EL element of one embodiment of the present invention, the light emitting layer is more preferably an organic EL element containing the compound (1). When the light emitting layer is an organic EL device containing the compound (1), it is preferable that the light emitting layer further contains a phosphorescent material described later. Moreover, as an organic EL element of 1 aspect of this invention, it is also preferable that a positive hole transport layer or an electron carrying layer contains the said compound (1).

When a light emitting layer contains the said compound (1), content of the said compound (1) in a light emitting layer becomes like this. Preferably it is 30-100 mass% with respect to the whole quantity of the component of a light emitting layer, More preferably, it is 50-100. It is 80 mass%, More preferably, it is 80-100 mass%, More preferably, it is 90-99 mass%.
Moreover, when organic thin film layers other than a light emitting layer contain the said compound (1), content of the said compound (1) in the organic thin film layer (preferably a positive hole transport layer or an electron carrying layer) is the organic thin film. Preferably it is 30-100 mass% with respect to the whole quantity of the component of a layer, More preferably, it is 50-100 mass%, More preferably, it is 80-100 mass%, More preferably, it is 95-100 mass%.
Furthermore, as an organic EL element of 1 aspect of this invention, the organic EL element which emits red light is mentioned preferably.

(substrate)
The substrate is used as a support for the light emitting element. For example, glass, quartz, plastic, or the like can be used as the substrate. Further, a flexible substrate may be used. The flexible substrate is a substrate that can be bent (flexible), and examples thereof include plastic substrates made of polycarbonate, polyarylate, polyethersulfone, polypropylene, polyester, polyvinyl fluoride, and polyvinyl chloride. . Moreover, an inorganic vapor deposition film can also be used.

(anode)
For the anode formed on the substrate, it is preferable to use a metal, an alloy, an electrically conductive compound, a mixture thereof, or the like having a high work function (specifically, 4.0 eV or more). Specifically, for example, indium oxide-tin oxide (ITO: Indium Tin Oxide), indium oxide-tin oxide containing silicon or silicon oxide, indium oxide-zinc oxide, tungsten oxide, and indium oxide containing zinc oxide. And graphene. In addition, gold (Au), platinum (Pt), nickel (Ni), tungsten (W), chromium (Cr), molybdenum (Mo), iron (Fe), cobalt (Co), copper (Cu), palladium ( Pd), titanium (Ti), or a metal material nitride (for example, titanium nitride).

  These materials are usually formed by sputtering. For example, indium oxide-zinc oxide is a target in which 1 to 10% by mass of zinc oxide is added to indium oxide, tungsten oxide, and indium oxide containing zinc oxide is 0.5 wt. By using a target containing ˜5% by mass and 0.1 to 1% by mass of zinc oxide, it can be formed by a sputtering method. In addition, you may produce by the vacuum evaporation method, the apply | coating method, the inkjet method, a spin coat method, etc.

Of the EL layers formed on the anode, the hole injection layer formed in contact with the anode is formed using a composite material that facilitates hole injection regardless of the work function of the anode. A material that can be used as an electrode material (for example, a metal, an alloy, an electrically conductive compound, a mixture thereof, and other elements belonging to Group 1 or Group 2 of the periodic table) can be used.
Elements belonging to Group 1 or Group 2 of the periodic table of elements, which are materials having a low work function, that is, alkali metals such as lithium (Li) and cesium (Cs), and magnesium (Mg), calcium (Ca), and strontium Alkaline earth metals such as (Sr), and alloys containing these (eg, MgAg, AlLi), rare earth metals such as europium (Eu), ytterbium (Yb), and alloys containing these can also be used. Note that when an anode is formed using an alkali metal, an alkaline earth metal, and an alloy containing these, a vacuum evaporation method or a sputtering method can be used. Furthermore, when using a silver paste etc., the apply | coating method, the inkjet method, etc. can be used.

(Hole injection layer)
The hole injection layer is a layer containing a substance having a high hole injection property.
Substances with high hole injection properties include molybdenum oxide, titanium oxide, vanadium oxide, rhenium oxide, ruthenium oxide, chromium oxide, zirconium oxide, hafnium oxide, tantalum oxide, silver oxide, Tungsten oxide, manganese oxide, or the like can be used.

  4,4 ′, 4 ″ -tris (N, N-diphenylamino) triphenylamine (abbreviation: TDATA), 4,4 ′, 4 ″ -tris [N- (3- Methylphenyl) -N-phenylamino] triphenylamine (abbreviation: MTDATA), 4,4′-bis [N- (4-diphenylaminophenyl) -N-phenylamino] biphenyl (abbreviation: DPAB), 4,4 '-Bis (N- {4- [N'-(3-methylphenyl) -N'-phenylamino] phenyl} -N-phenylamino) biphenyl (abbreviation: DNTPD), 1,3,5-tris [N -(4-Diphenylaminophenyl) -N-phenylamino] benzene (abbreviation: DPA3B), 3- [N- (9-phenylcarbazol-3-yl) -N-phenylamino] -9-fur Nylcarbazole (abbreviation: PCzPCA1), 3,6-bis [N- (9-phenylcarbazol-3-yl) -N-phenylamino] -9-phenylcarbazole (abbreviation: PCzPCA2), 3- [N- (1 An aromatic amine compound such as -naphthyl) -N- (9-phenylcarbazol-3-yl) amino] -9-phenylcarbazole (abbreviation: PCzPCN1) is also used.

  Polymer compounds (oligomers, dendrimers, polymers, etc.) can also be used. For example, poly (N-vinylcarbazole) (abbreviation: PVK), poly (4-vinyltriphenylamine) (abbreviation: PVTPA), poly [N- (4- {N ′-[4- (4-diphenylamino)] Phenyl] phenyl-N′-phenylamino} phenyl) methacrylamide] (abbreviation: PTPDMA), poly [N, N′-bis (4-butylphenyl) -N, N′-bis (phenyl) benzidine] (abbreviation: Polymer compounds such as Poly-TPD). In addition, a polymer compound to which an acid such as poly (3,4-ethylenedioxythiophene) / poly (styrenesulfonic acid) (PEDOT / PSS), polyaniline / poly (styrenesulfonic acid) (PAni / PSS) is added is used. You can also

(Hole transport layer)
The hole transport layer is a layer containing a substance having a high hole transport property.
The organic EL device of one embodiment of the present invention may include the compound (1) of one embodiment of the present invention alone or in combination with the following compound in the hole transport layer.

An aromatic amine compound, a carbazole derivative, an anthracene derivative, or the like can be used for the hole transport layer. Specifically, 4,4′-bis [N- (1-naphthyl) -N-phenylamino] biphenyl (abbreviation: NPB) or N, N′-bis (3-methylphenyl) -N, N′— Diphenyl- [1,1′-biphenyl] -4,4′-diamine (abbreviation: TPD), 4-phenyl-4 ′-(9-phenylfluoren-9-yl) triphenylamine (abbreviation: BAFLP), 4 , 4′-bis [N- (9,9-dimethylfluoren-2-yl) -N-phenylamino] biphenyl (abbreviation: DFLDPBi), 4,4 ′, 4 ″ -tris (N, N-diphenylamino) ) Triphenylamine (abbreviation: TDATA), 4,4 ′, 4 ″ -tris [N- (3-methylphenyl) -N-phenylamino] triphenylamine (abbreviation: MTDATA), 4,4′-bis [N- (Spiro-9,9'-Biff Oren-2-yl) -N- phenylamino] biphenyl (abbreviation: BSPB) can be used aromatic amine compounds such as. The substances described here are mainly substances having a hole mobility of 10 ⁻⁶ cm ² / Vs or higher.

A carbazole derivative such as CBP, CzPA, or PCzPA, or an anthracene derivative such as t-BuDNA, DNA, or DPAnth may be used for the hole transport layer. A high molecular compound such as poly (N-vinylcarbazole) (abbreviation: PVK) or poly (4-vinyltriphenylamine) (abbreviation: PVTPA) can also be used.
Note that other than these substances, any substance that has a property of transporting more holes than electrons may be used.
The hole transport material is preferably an arylamine derivative or a carbazole derivative. When the material of the present invention is used as a host material of a phosphorescent device, the hole transport layer adjacent to the light emitting layer is a triplet in the light emitting layer. From the viewpoint of confining excitons, it is preferable to select a hole transport material having a high triplet energy level. Hole transport materials with high triplet energy levels include tetraaryl or partially heterocyclic substituted benzidine derivatives, triaryl substituted monoamines, heterocyclic substituted triarylamines, heterocyclic substituted amines, bicarbazole derivatives, condensed Bicarbazole derivatives having a ring structure and the like, and aryl substituents include phenyl group, biphenyl group, terphenyl group, quarterphenyl group, kinkphenyl group, naphthyl group, phenanthryl group, fluorenyl group, spirofluorenyl group The heterocyclic substituent is preferably a substituent containing dibenzofuran, dibenzothiophene, or carbazole. In particular, when the material of the present invention is used in a green phosphor element, the hole transport material preferably has a higher triplet energy level, and the aryl substituent is preferably a substituent with a higher triplet energy level. Specifically, a phenyl group, a biphenyl group, a metaterphenyl group, a quarterphenyl group having no paraterphenylene structure, a kinkphenyl group, a fluorenyl group, and a spirofluorenyl group are preferable.
Note that the layer containing a substance having a high hole-transport property is not limited to a single layer, and two or more layers containing the above substances may be stacked.

In the organic EL device of one embodiment of the present invention, a layer (acceptor layer) containing an electron-accepting compound (also referred to as an acceptor material) is bonded to the positive electrode side of the hole transport layer or the first hole transport layer. Also good. This is expected to reduce drive voltage and manufacturing costs.
As the electron-accepting compound, a compound represented by the following formula (A) or (B) is preferable.

In the above formula (A), R ^{311 to} R ³¹⁶ may be the same as or different from each other, and each independently represents a cyano group, —CONH ₂ , a carboxyl group, or —COOR ³¹⁷ (R ³¹⁷ has 1 to 20 carbon atoms). Represents an alkyl group or a cycloalkyl group having 3 to 20 carbon atoms). However, one or two or more pairs of R ³¹¹ and R ³¹² , R ³¹³ and R ³¹⁴ , and R ³¹⁵ and R ³¹⁶ may be combined to form a group represented by —CO—O—CO—.
^Examples of R ³¹⁷ include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a t-butyl group, a cyclopentyl group, and a cyclohexyl group.

In the general formula (B), R ⁴¹ ~R ⁴⁴ may each be the same or different from each other, hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted carbon atoms 6 -50 aryl groups, substituted or unsubstituted heterocyclic groups having 5 to 50 ring atoms, halogen atoms, substituted or unsubstituted fluoroalkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted 1 to 5 carbon atoms 20 alkoxy groups, substituted or unsubstituted aryloxy groups having 6 to 50 carbon atoms, or cyano groups. R ^{41 to} R ⁴⁴ that are adjacent to each other may be bonded to each other to form a ring.
Y ^{1 to} Y ⁴ may be the same as or different from each other, and are N, CH, or C (R ⁴⁵ ), and R ⁴⁵ is a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, substituted or unsubstituted. An aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, a halogen atom, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted carbon It is an aryloxy group of formula 6-50, or a cyano group.
Ar ¹⁰ is a condensed ring having 6 to 24 ring carbon atoms or a heterocyclic ring having 6 to 24 ring atoms. ar ¹ and ar ² each independently represent a ring of the following general formula (i) or (ii).

In the formula, X ¹ and X ² may be the same as or different from each other, and are any of the divalent groups shown in the following (a) to (g).

In the formula, each of R ^{51 to} R ⁵⁴ may be the same as or different from each other, and is a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 50 carbon atoms. Alternatively, it is a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, and R ⁵² and R ⁵³ may be bonded to each other to form a ring.

Examples of groups of R ^{41 to} R ⁴⁴ and R ^{51 to} R ⁵⁴ are as follows.
Examples of the alkyl group include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a tert-butyl group, a cyclopentyl group, and a cyclohexyl group.
Examples of the aryl group include a phenyl group, a biphenyl group, and a naphthyl group.
Examples of the heterocyclic group include residues such as pyridine, pyrazine, furan, imidazole, benzimidazole, and thiophene.
Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.
Examples of the alkoxy group include a methoxy group and an ethoxy group.
Examples of the aryloxy group include a phenyloxy group.

(Guest material for light emitting layer)
The light-emitting layer is a layer including a substance having high light-emitting properties, and various materials can be used. For example, as the substance having high light-emitting property, a fluorescent compound that emits fluorescence or a phosphorescent compound that emits phosphorescence can be used. A fluorescent compound is a compound that can emit light from a singlet excited state, and a phosphorescent compound is a compound that can emit light from a triplet excited state.
As a blue fluorescent material that can be used for the light emitting layer, pyrene derivatives, styrylamine derivatives, chrysene derivatives, fluoranthene derivatives, fluorene derivatives, diamine derivatives, triarylamine derivatives, and the like can be used. Specifically, N, N′-bis [4- (9H-carbazol-9-yl) phenyl] -N, N′-diphenylstilbene-4,4′-diamine (abbreviation: YGA2S), 4- (9H -Carbazol-9-yl) -4 '-(10-phenyl-9-anthryl) triphenylamine (abbreviation: YGAPA), 4- (10-phenyl-9-anthryl) -4'-(9-phenyl-9H -Carbazol-3-yl) triphenylamine (abbreviation: PCBAPA) and the like.

  An aromatic amine derivative or the like can be used as a green fluorescent material that can be used for the light emitting layer. Specifically, N- (9,10-diphenyl-2-anthryl) -N, 9-diphenyl-9H-carbazol-3-amine (abbreviation: 2PCAPA), N- [9,10-bis (1,1 '-Biphenyl-2-yl) -2-anthryl] -N, 9-diphenyl-9H-carbazol-3-amine (abbreviation: 2PCABPhA), N- (9,10-diphenyl-2-anthryl) -N, N ', N'-triphenyl-1,4-phenylenediamine (abbreviation: 2DPAPA), N- [9,10-bis (1,1'-biphenyl-2-yl) -2-anthryl] -N, N' , N′-triphenyl-1,4-phenylenediamine (abbreviation: 2DPABPhA), N- [9,10-bis (1,1′-biphenyl-2-yl)]-N- [4- (9H-carbazole) -9-Ile Phenyl] -N- phenyl-anthracene-2-amine (abbreviation: 2YGABPhA), N, N, 9- triphenylamine anthracene-9-amine (abbreviation: DPhAPhA), and the like.

  Tetracene derivatives, diamine derivatives, and the like can be used as red fluorescent materials that can be used for the light emitting layer. Specifically, N, N, N ′, N′-tetrakis (4-methylphenyl) tetracene-5,11-diamine (abbreviation: p-mPhTD), 7,14-diphenyl-N, N, N ′, And N′-tetrakis (4-methylphenyl) acenaphtho [1,2-a] fluoranthene-3,10-diamine (abbreviation: p-mPhAFD).

  In one embodiment of the present invention, the fluorescent material preferably contains at least one selected from anthracene derivatives, fluoranthene derivatives, styrylamine derivatives, and arylamine derivatives.

As a blue phosphorescent material that can be used for the light emitting layer, a metal complex such as an iridium complex, an osmium complex, or a platinum complex is used. Specifically, bis [2- (4 ′, 6′-difluorophenyl) pyridinato-N, C2 ′] iridium (III) tetrakis (1-pyrazolyl) borate (abbreviation: FIr ₆ ), bis [2- (4 ', 6'-difluorophenyl) pyridinato-N, C2'] iridium (III) picolinate (abbreviation: FIrpic), bis [2- (3 ', 5'bistrifluoromethylphenyl) pyridinato-N, C2'] iridium ( III) Picolinate (abbreviation: Ir (CF ₃ ppy) ₂ (pic)), bis [2- (4 ′, 6′-difluorophenyl) pyridinato-N, C2 ′] iridium (III) acetylacetonate (abbreviation: FIracac) ) And the like.

An iridium complex or the like is used as a green phosphorescent material that can be used for the light emitting layer. Tris (2-phenylpyridinato-N, C2 ′) iridium (III) (abbreviation: Ir (ppy) ₃ ), bis (2-phenylpyridinato-N, C2 ′) iridium (III) acetylacetonate ( Abbreviations: Ir (ppy) ₂ (acac)), bis (1,2-diphenyl-1H-benzimidazolato) iridium (III) acetylacetonate (abbreviation: Ir (pbi) ₂ (acac)), bis (benzo [ h] quinolinato) iridium (III) acetylacetonate (abbreviation: Ir (bzq) ₂ (acac)) and the like.

As a red phosphorescent material that can be used for the light emitting layer, a metal complex such as an iridium complex, a platinum complex, a terbium complex, or a europium complex is used. Specifically, bis [2- (2′-benzo [4,5-α] thienyl) pyridinato-N, C3 ′] iridium (III) acetylacetonate (abbreviation: Ir (btp) ₂ (acac)), Bis (1-phenylisoquinolinato-N, C2 ′) iridium (III) acetylacetonate (abbreviation: Ir (piq) ₂ (acac)), (acetylacetonato) bis [2,3-bis (4-fluoro Phenyl) quinoxalinato] iridium (III) (abbreviation: Ir (Fdpq) ₂ (acac)), 2,3,7,8,12,13,17,18-octaethyl-21H, 23H-porphyrin platinum (II) (abbreviation) : PtOEP) and the like.

In addition, tris (acetylacetonato) (monophenanthroline) terbium (III) (abbreviation: Tb (acac) ₃ (Phen)), tris (1,3-diphenyl-1,3-propanedionato) (monophenanthroline) europium (III) (abbreviation: Eu (DBM) ₃ (Phen)), tris [1- (2-thenoyl) -3,3,3-trifluoroacetonato] (monophenanthroline) europium (III) (abbreviation: Eu ( Since rare earth metal complexes such as TTA) ₃ (Phen)) emit light from rare earth metal ions (electron transition between different multiplicity), they can be used as phosphorescent compounds.

As one embodiment of the present invention, the phosphorescent material is preferably an orthometalated complex of a metal atom selected from iridium (Ir), osmium (Os), and platinum (pt).
The phosphorescent material that is an orthometalated complex of a metal atom selected from iridium (Ir), osmium (Os), and platinum (Pt) is preferably a complex represented by the following formula (α).

In the formula (α), M represents at least one metal selected from osmium, iridium and platinum, and n represents the valence of the metal.
Ring A ₁ represents a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms or a heteroaryl group having 5 to 30 ring atoms, and ring A ₂ is a substituent containing nitrogen as a hetero ring forming atom. Alternatively, it represents an unsubstituted heteroaryl group having 5 to 30 ring atoms.

Examples of the aryl group having 6 to 30 ring carbon atoms in the ring A ₁ of the formula (α) include the groups exemplified as the aryl group having 6 to 30 ring carbon atoms represented by R _{1 to} R ₆ in the formula (1). From which one hydrogen atom is removed.
The heteroaryl group having 5 to 30 ring atoms in the ring A ₁ and the ring A ₂ of the formula (α) is a heteroaryl group having 5 to 30 ring atoms represented by R _{1 to} R ₆ in the formula (1). A group obtained by removing one hydrogen atom from an aryl group is exemplified.
The substituent that the ring A ₁ and the ring A _{2 of the} formula (α) may have is the same as the substituent represented by R _{1 to} R ₆ of the formula (1).
Furthermore, the complex represented by the formula (α) is preferably a complex represented by the following formula (T) or (U).

In formula (T), M represents a metal, and ring B and ring C each independently represent an aryl group or heteroaryl group having 5 or 6 ring atoms.
Ring A-ring B represents a bond pair of an aryl group or a heteroaryl group, and is coordinated to the metal M through the nitrogen atom of ring A and the sp ² hybrid atom of ring B.
Ring A-ring C represents an aryl group or heteroaryl group bond pair.
R _a , R _b and R _c are each independently selected from the group consisting of a hydrogen atom, an alkyl group, an alkoxy group, an amino group, an alkenyl group, an alkynyl group, an aralkyl group, an aryl group and a heteroaryl group. And each is independently 1 to 4.
X _{1 to} X ₉ each independently represent a carbon atom or a nitrogen atom.
R _d and R _e each independently represents any one selected from the group consisting of a hydrogen atom, an alkyl group, an alkoxy group, an amino group, an alkenyl group, an alkynyl group, an aralkyl group, an aryl group, and a heteroaryl group; At least one of R _c , R _d and R _e bonded to the ring C is not a hydrogen atom.
m represents an oxidation state of the metal M, and n is 1 or more. L ′ represents a monoanionic bidentate ligand.

In the formula (T), examples of M include osmium, iridium, platinum, etc. Among them, iridium is preferable.
As the aryl group having 5 or 6 ring atoms represented by ring B and ring C, among the aryl groups having 6 to 30 ring carbon atoms represented by R _{1 to} R ₆ in formula (1), a ring A group obtained by removing one hydrogen atom from an aryl group having 6 carbon atoms is exemplified.
The heteroaryl group having 5 or 6 ring atoms represented by ring B and ring C is a heteroaryl group having 5 to 30 ring carbon atoms represented by R _{1 to} R ₆ in formula (1). And a group obtained by removing one hydrogen atom from a heteroaryl group having 5 or 6 ring carbon atoms.
The alkyl group, alkoxy group, aralkyl group, aryl group and heteroaryl group represented by R ₁ , R ₂ , R _a , R _b and R _c are each represented by R _{1 to} R ₆ in the formula (1). A C1-C20 alkyl group, a C1-C20 haloalkoxy group, a C7-C30 aralkyl group having a ring-forming C6-C10 aryl group, a ring-forming C6-C18 Examples thereof include the same groups as the aryl group and the heteroaryl group having 5 to 18 ring atoms.
As the alkenyl group represented by R ₁ , R ₂ , R _a , R _b and R _c and the alkynyl group, respectively, an alkyl having 2 to 20 carbon atoms represented by R _{1 to} R ₆ in the formula (1) Examples include groups obtained by removing two hydrogen atoms from a group, and groups obtained by removing three hydrogen atoms from an alkyl group having 2 to 20 carbon atoms represented by R _{1 to} R ₆ in formula (1).
Examples of the monoanionic bidentate ligand represented by L ′ include a ligand represented by the following formula (L ′).

In the formula _{(L '), X 4 ~X} 9, R a, and _{R b} are the same as _X 4 _~X 9, _{R a,} and _{R b} in Formula (T), preferable embodiments thereof are also the same.
The ligand represented by the formula (L ′) is represented by the formula (T) through a solid line extending from the ring X ₉ to the outside of the ring B and a broken line extending from the nitrogen atom of the ring A to the outside of the ring A. Coordinates to metal M.

In the formula (U), X represents any one selected from the group consisting of NR, oxygen atom, sulfur atom, BR, and selenium atom, and R is a hydrogen atom or an alkyl group.
R ₁ , R ₂ , R ₃ and R ₄ each independently represent any one selected from the group consisting of a hydrogen atom, an alkyl group and an aryl group, and each is independently 1 to 4.

In the formula (U), examples of the alkyl group represented by R, R ₁ , R ₂ , R ₃ and R ₄ include groups exemplified as the alkyl groups represented by R _{1 to} R ₆ in the formula (1). The preferred embodiments are also the same.
In addition, examples of the aryl group represented by R ₁ , R ₂ , R ₃ and R ₄ include the groups exemplified as the aryl groups represented by R _{1 to} R ₆ in the formula (1), and the preferred embodiments are also the same. It is.

  As the complex represented by the formula (T) or (U), the following compounds are suitable, but not particularly limited thereto.

  As the complex represented by the formula (α), in addition to the complex represented by the formula (T) or (U), the complex represented by the following formula (V), (X), (Y) or (Z) It can also be used.

In the formula (V), (X), (Y) or (Z), R ^{50 to} R ⁵⁴ are hydrogen atoms or substituents, k is an integer of 1 to 4, and l is an integer of 1 to 4. , M is an integer of 1-2. M is Ir, Os, or Pt.
Examples of the substituent represented by R ^{50 to} R ⁵⁴ include the same substituents as those described as the substituent for R _{1 to} R ₆ in the formula (1).
The formula (V) is preferably represented by the following formula (V-1), and the formula (X) is preferably represented by the following formula (X-1) or the formula (X-2). In the following formulas (X-1), (X-1), and (X-1), R ⁵⁰ , k, and M are the same as R ⁵⁰ , k, and M described above.

  Specific examples of preferred metal complexes are shown below, but are not particularly limited thereto.

(Host material for light emitting layer)
The light-emitting layer may have a structure in which the above-described highly light-emitting substance (guest material) is dispersed in another substance (host material). Various materials can be used as a material for dispersing a highly luminescent substance. The lowest vacant orbital level (LUMO level) is higher than that of a highly luminescent substance, and the highest occupied molecular orbital level ( It is preferable to use a substance having a low HOMO level.
As one aspect of the organic EL device of the present invention, the compound (1) of the present invention can also be used as a host material of the light emitting layer.

As a substance (host material) for dispersing a highly luminescent substance,
(1) Metal complexes such as aluminum complexes, lithium complexes, beryllium complexes, zinc complexes,
(2) heterocyclic compounds such as oxadiazole derivatives, benzimidazole derivatives, phenanthroline derivatives,
(3) condensed aromatic compounds such as carbazole derivatives, anthracene derivatives, phenanthrene derivatives, pyrene derivatives, chrysene derivatives,
(4) Aromatic amine compounds such as triarylamine derivatives and condensed polycyclic aromatic amine derivatives are used.
Specifically, tris (8-quinolinolato) aluminum (III) (abbreviation: Alq), tris (4-methyl-8-quinolinolato) aluminum (III) (abbreviation: Almq ₃ ), 8-quinolinolatolithium (Liq) ), Bis (10-hydroxybenzo [h] quinolinato) beryllium (II) (abbreviation: BeBq ₂ ), bis (2-methyl-8-quinolinolato) (4-phenylphenolato) aluminum (III) (abbreviation: BAlq) , Bis (8-quinolinolato) zinc (II) (abbreviation: Znq), bis [2- (2-benzoxazolyl) phenolato] zinc (II) (abbreviation: ZnPBO), bis [2- (2-benzothiazolyl) Phenolate] zinc (II) (abbreviation: ZnBTZ) and other metal complexes, 2- (4-biphenylyl) -5- (4-tert-butylphenyl) -1, 3,4-oxadiazole (abbreviation: PBD), 1,3-bis [5- (p-tert-butylphenyl) -1,3,4-oxadiazol-2-yl] benzene (abbreviation: OXD- 7), 3- (4-biphenylyl) -4-phenyl-5- (4-tert-butylphenyl) -1,2,4-triazole (abbreviation: TAZ), 2,2 ′, 2 ″-(1 , 3,5-benzenetriyl) tris (1-phenyl-1H-benzimidazole) (abbreviation: TPBI), bathophenanthroline (abbreviation: BPhen), bathocuproin (abbreviation: BCP), and 9- [ 4- (10-phenyl-9-anthryl) phenyl] -9H-carbazole (abbreviation: CzPA), 3,6-diphenyl-9- [4- (10-phenyl-9-anthryl) phenyl] -9 -Carbazole (abbreviation: DPCzPA), 9,10-bis (3,5-diphenylphenyl) anthracene (abbreviation: DPPA), 9,10-di (2-naphthyl) anthracene (abbreviation: DNA), 2-tert-butyl -9,10-di (2-naphthyl) anthracene (abbreviation: t-BuDNA), 9,9'-bianthryl (abbreviation: BANT), 9,9 '-(stilbene-3,3'-diyl) diphenanthrene ( Abbreviation: DPNS), 9,9 ′-(stilbene-4,4′-diyl) diphenanthrene (abbreviation: DPNS2), 3,3 ′, 3 ″-(benzene-1,3,5-triyl) tripyrene ( _{abbreviation:} TPB 3), 9,10- diphenyl anthracene (abbreviation: DPAnth), 6,12-condensed aromatic compounds such as dimethoxy-5,11-diphenyl chrysene, N N-diphenyl-9- [4- (10-phenyl-9-anthryl) phenyl] -9H-carbazol-3-amine (abbreviation: CzA1PA), 4- (10-phenyl-9-anthryl) triphenylamine (abbreviation) : DPhPA), N, 9-diphenyl-N- [4- (10-phenyl-9-anthryl) phenyl] -9H-carbazol-3-amine (abbreviation: PCAPA), N, 9-diphenyl-N- {4 -[4- (10-phenyl-9-anthryl) phenyl] phenyl} -9H-carbazol-3-amine (abbreviation: PCAPBA), N- (9,10-diphenyl-2-anthryl) -N, 9-diphenyl Fragrance such as -9H-carbazol-3-amine (abbreviation: 2PCAPA), NPB (or α-NPD), TPD, DFLDPBi, BSPB Group amine compounds can be used. In addition, a plurality of substances (host materials) for dispersing a substance having high luminescence (guest material) can be used.

In particular, the compound [compound (1)] represented by the formula (1) of the present invention is preferably used as the phosphorescent host, and more preferably, the compound (1) is converted into the second host material (“second host”). And may be used as a mixture. That is, it is preferable that a light emitting layer contains the compound (1) (1st host) and the compound (2nd host) represented by following formula (8) as a host material.
A preferred second host material is a compound represented by the following formula (8).

In formula (8),
X ^{1 to} X ³ each independently represent CR ¹¹ or N.
R ⁵ to R ⁷ and ^{R 11} are each _{^{independently, - (B 5) s -}} (B 6) t - shows the _{^{(B 8) v -R 8 -}} (B 7) u.
s, t, u and v each independently represent 0 or 1.
B ^{5 to} B ⁸ each independently represents a substituted or unsubstituted arylene group having 6 to 24 ring carbon atoms or a substituted or unsubstituted heteroarylene group having 5 to 30 ring atoms.
R ⁸ represents a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 25 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 25 carbon atoms, or a substituted or unsubstituted alkynyl group having 2 to 25 carbon atoms. Group, substituted or unsubstituted cycloalkyl group having 3 to 25 ring carbon atoms, substituted or unsubstituted alkoxy group having 1 to 25 carbon atoms, substituted or unsubstituted aryl group having 6 to 24 ring carbon atoms, substituted Or an unsubstituted heteroaryl group having 5 to 30 ring atoms, a substituted or unsubstituted aryloxy group having 6 to 24 ring carbon atoms, a substituted or unsubstituted alkylthio group having 1 to 25 carbon atoms, substituted or unsubstituted 1 or more selected from the group consisting of a substituted arylthio group having 6 to 24 ring carbon atoms, an alkyl group having 1 to 25 carbon atoms, and an aryl group having 6 to 24 ring carbon atoms A silyl group, a cyano group, or —P (═O) R ¹⁴ R ¹⁵ substituted with a group of Adjacent substituents on R ⁸ may combine with each other to form a ring.
R ¹⁴ and R ¹⁵ each independently represent a substituted or unsubstituted alkyl group having 1 to 25 carbon atoms, a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms, or a substituted or unsubstituted ring formation. A heteroaryl group having 5 to 18 atoms is shown.

<Preferred Embodiment of Compound Represented by Formula (8)>
In one embodiment of the present invention, the compound represented by the formula (8) is preferably a compound represented by the following formula (81).

In formula (81),
X ^{1 to} X ³ , R ⁵ and R ⁶ are as defined in the above formula (8).
L ¹ is a substituted or unsubstituted arylene group having 6 to 24 ring carbon atoms or a substituted or unsubstituted heteroarylene group having 5 to 30 ring atoms.
f is an integer of 0 or 1.
Y ¹ is a carbon atom or a nitrogen atom.
Ar ¹ is a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 24 ring carbon atoms that shares the carbon atom of adjacent nitrogen-containing five-membered ring and Y ¹ and is fused to the nitrogen-containing five-membered ring. Or a substituted or unsubstituted heteroaromatic ring having 5 to 30 ring atoms that shares the nitrogen atom of adjacent nitrogen-containing five-membered ring and Y ¹ and is fused to the nitrogen-containing five-membered ring. .
R ⁵⁰ and R ⁵¹ are each independently a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 25 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 25 carbon atoms, substituted or unsubstituted. An alkynyl group having 2 to 25 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 25 ring carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 25 carbon atoms, and a substituted or unsubstituted ring carbon number. 6-24 aryl group, substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms, substituted or unsubstituted aryloxy group having 6 to 24 ring carbon atoms, substituted or unsubstituted 1 to 2 carbon atoms 25 alkylthio groups, substituted or unsubstituted arylthio groups having 6 to 24 ring carbon atoms, alkyl groups having 1 to 25 carbon atoms, and aryls having 6 to 24 ring carbon atoms Substituted with one or more groups selected from the group consisting of silyl group, a cyano group, or a ^{-P (= O) R 14 R} 15. Adjacent substituents on R ⁵⁰ and R ⁵¹ may combine with each other to form a ring.
R ¹⁴ and R ¹⁵ are as defined in the above formula (8).

  The compound represented by the formula (81) is preferably a compound represented by the following formula (82).

In formula (82),
X ^{1 to} X ³ , R ⁵ , R ⁶ , L ¹ , f, Y ¹ and Ar ¹ are as defined in the formula (81).
R ⁵² represents a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 25 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 25 carbon atoms, or a substituted or unsubstituted alkynyl group having 2 to 25 carbon atoms. Group, substituted or unsubstituted cycloalkyl group having 3 to 25 ring carbon atoms, substituted or unsubstituted alkoxy group having 1 to 25 carbon atoms, substituted or unsubstituted aryl group having 6 to 24 ring carbon atoms, substituted Or an unsubstituted heteroaryl group having 5 to 30 ring atoms, a substituted or unsubstituted aryloxy group having 6 to 24 ring carbon atoms, a substituted or unsubstituted alkylthio group having 1 to 25 carbon atoms, substituted or unsubstituted 1 or more selected from the group consisting of a substituted arylthio group having 6 to 24 ring carbon atoms, an alkyl group having 1 to 25 carbon atoms, and an aryl group having 6 to 24 ring carbon atoms A silyl group, a cyano group, or —P (═O) R ¹⁴ R ¹⁵ substituted with the above group is shown. Adjacent substituents on R ⁵² may combine with each other to form a ring.
R ¹⁴ and R ¹⁵ are as defined in the above formula (8).
c is an integer of 0 to 4, and when c is 2 to 4, a plurality of R ⁵² may be the same or different from each other, and adjacent R ⁵² may be bonded to form a ring. .

  The compound represented by the formula (82) is preferably a compound represented by the following formula (83).

In formula (83),
X ^{1 to} X ³ , R ⁵ , R ⁶ , L ¹ , f, R ⁵² and c are as defined in the formula (82).

  The compound represented by the formula (83) is preferably a compound represented by the following formula (84).

In formula (84),
X ^{1 to} X ³ , R ⁵ , R ⁶ , L ¹ , f, R ⁵² and c are as defined in the above formula (83).
d is an integer of 0 to 3. When d is 2 or 3, a plurality of R ⁵² may be the same as or different from each other.
R ⁵³ represents a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 25 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 25 carbon atoms, or a substituted or unsubstituted alkynyl group having 2 to 25 carbon atoms. Group, substituted or unsubstituted cycloalkyl group having 3 to 25 ring carbon atoms, substituted or unsubstituted alkoxy group having 1 to 25 carbon atoms, substituted or unsubstituted aryl group having 6 to 24 ring carbon atoms, substituted Or an unsubstituted heteroaryl group having 5 to 30 ring atoms, a substituted or unsubstituted aryloxy group having 6 to 24 ring carbon atoms, a substituted or unsubstituted alkylthio group having 1 to 25 carbon atoms, substituted or unsubstituted 1 or more selected from the group consisting of a substituted arylthio group having 6 to 24 ring carbon atoms, an alkyl group having 1 to 25 carbon atoms, and an aryl group having 6 to 24 ring carbon atoms A silyl group, a cyano group, or —P (═O) R ¹⁴ R ¹⁵ substituted with the above group is shown. Adjacent substituents on R ⁵³ may combine with each other to form a ring.
R ¹⁴ and R ¹⁵ are as defined in the above formula (8).

  In another embodiment, the compound represented by Formula (82) is preferably a compound represented by Formula (85) below.

In formula (85),
X ^{1 to} X ³ , R ⁵ , R ⁶ , L ¹ , f, R ⁵² and c are as defined in the formula (82).
Y ² is CR ⁵⁴ R ⁵⁵ , NR ⁵⁶ , an oxygen atom or a sulfur atom.
R ⁵⁴ to R ⁵⁶ are each independently a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 25 carbon atoms, a substituted or unsubstituted alkenyl group having a carbon number of 2 to 25, a substituted or unsubstituted An alkynyl group having 2 to 25 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 25 ring carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 25 carbon atoms, and a substituted or unsubstituted ring carbon number. 6-24 aryl group, substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms, substituted or unsubstituted aryloxy group having 6 to 24 ring carbon atoms, substituted or unsubstituted 1 to 2 carbon atoms 25 alkylthio groups, substituted or unsubstituted arylthio groups having 6 to 24 ring carbon atoms, alkyl groups having 1 to 25 carbon atoms, and aryl groups having 6 to 24 ring carbon atoms One or more silyl group substituted with a group selected from Ranaru group, a cyano group, or a ^{-P (= O) R 14 R} 15. Adjacent substituents on R ^{54 to} R ⁵⁶ may be bonded to each other to form a ring.
R ¹⁴ and R ¹⁵ are as defined in the above formula (8).
Ar ² is a substituted or unsubstituted aromatic carbon atom having 6 to 24 ring carbon atoms that shares two carbon atoms constituting two adjacent five-membered rings and is fused to the two five-membered rings. A substituted or unsubstituted heteroaromatic group having 5 to 30 ring atoms that shares a hydrogen ring or two adjacent carbon atoms constituting two adjacent five-membered rings and is fused to the two five-membered rings It is a family ring.

  The compound represented by the formula (85) is preferably a compound represented by any of the following formulas (86A) to (86C).

In formulas (86A) to (86C),
X ^{1 to} X ³ , R ⁵ , R ⁶ , L ¹ , f, R ⁵² , R ⁵³ and c are as defined in the formula (85).
e is an integer of 0 to 2, and when e is 2, a plurality of R ⁵² may be the same as or different from each other.

  The compound represented by the formula (85) is preferably a compound represented by any of the following formulas (87A) to (87C).

In formulas (87A) to (87C),
X ^{1 to} X ³ , R ⁵ , R ⁶ , L ¹ , f, R ⁵² , R ⁵³ and c are as defined in the formula (85).
e is an integer of 0 to 2, and when e is 2, a plurality of R ⁵² may be the same as or different from each other.

In the formula (8), X ^{1 to} X ³ are preferably N. That is, the compound represented by the formula (8) is preferably represented by the following formula (82a).

In formula (82a), R ⁵ , R ⁶ , R ⁵² , c, L ¹ , f, Y ¹ and Ar ¹ are the same as those in formula (82).
Specific examples of the compound represented by the formula (8) are described below, but are not limited thereto.

(Electron transport layer)
The electron transport layer is a layer containing a substance having a high electron transport property. In the electron transport layer,
(1) Metal complexes such as aluminum complexes, beryllium complexes, zinc complexes,
(2) heteroaromatic compounds such as imidazole derivatives, benzimidazole derivatives, azine derivatives, carbazole derivatives, phenanthroline derivatives,
(3) A polymer compound can be used.
Specifically, as a low-molecular organic compound, Alq, tris (4-methyl-8-quinolinolato) aluminum (abbreviation: Almq ₃ ), bis (10-hydroxybenzo [h] quinolinato) beryllium (abbreviation: BeBq ₂ ), A metal complex such as BAlq, Znq, ZnPBO, ZnBTZ, or the like can be used. In addition to metal complexes, 2- (4-biphenylyl) -5- (4-tert-butylphenyl) -1,3,4-oxadiazole (abbreviation: PBD), 1,3-bis [5- (Pert-butylphenyl) -1,3,4-oxadiazol-2-yl] benzene (abbreviation: OXD-7), 3- (4-tert-butylphenyl) -4-phenyl-5- (4- Biphenylyl) -1,2,4-triazole (abbreviation: TAZ), 3- (4-tert-butylphenyl) -4- (4-ethylphenyl) -5- (4-biphenylyl) -1,2,4- Triazole (abbreviation: p-EtTAZ), bathophenanthroline (abbreviation: BPhen), bathocuproin (abbreviation: BCP), 4,4′-bis (5-methylbenzoxazol-2-yl) stilbene (abbreviation: B) Heteroaromatic compounds such as zOs) can also be used. The substances mentioned here are mainly substances having an electron mobility of 10 ⁻⁶ cm ² / Vs or higher. Note that any substance other than the above substances may be used for the electron-transport layer as long as the substance has a higher electron-transport property than the hole-transport property. Further, the electron-transport layer is not limited to a single layer, and two or more layers including the above substances may be stacked.
Moreover, a high molecular compound can also be used for an electron carrying layer. For example, poly [(9,9-dihexylfluorene-2,7-diyl) -co- (pyridine-3,5-diyl)] (abbreviation: PF-Py), poly [(9,9-dioctylfluorene-2) , 7-diyl) -co- (2,2′-bipyridine-6,6′-diyl)] (abbreviation: PF-BPy) and the like can be used.
In one embodiment of the present invention, the electron transport layer preferably contains the heteroaromatic compound. Examples of the heteroaromatic compound include pyridine, pyrimidine, pyrazine, triazine, quinoline, isoquinoline, quinazoline, quinoxaline, naphthyridine, and benzoquinoline. , Benzoisoquinoline, phenanthroline, benzoquinazoline, azatriphenylene, dibenzoquinazoline, dibenzoquinoxaline, dinaphthopyridine and other electron-deficient nitrogen-containing 6-membered heteroaromatic compounds, imidazole, benzimidazole, oxazole, benzoxazole , Imidazopyridine and other electron-deficient nitrogen-containing rings, furan, benzofuran, dibenzofuran, naphthobenzofuran, thiophene, benzothiophene, dibenzothiophene, naphthoben 5-membered ring heteroaromatic compounds such as furan, pyrrole, indole, carbazole, and benzocarbazole are preferred, and compounds having a further condensed ring structure in the heteroaromatic compound, and further heteroheteroaromatic compounds are more complex. Aromatic substituents and compounds substituted with aromatic substituents are preferred. As the heteroaromatic compound responsible for electron injection and transport, it is particularly preferable to contain an electron-deficient heterocycle in the molecular structure. Condensed aromatic hydrocarbons, which are compounds having high electron mobility, are also preferred as the electron transport layer, such as naphthalene, anthracene, phenanthrene, benzanthracene, pyrene, triphenylene, chrysene, benzochrysene, dibenzanthracene, fluorene, fluoranthene, benzofluorene. Aromatic hydrocarbons such as benzofluoranthene are preferred, compounds having a further condensed ring structure in the aromatic condensed ring, and those aromatic condensed rings further substituted with a heteroaromatic substituent or aromatic substituent Compounds are preferred.

(Electron injection layer)
The electron injection layer is a layer containing a substance having a high electron injection property. For the electron injection layer, lithium (Li), cesium (Cs), calcium (Ca), lithium fluoride (LiF), cesium fluoride (CsF), calcium fluoride (CaF ₂ ), lithium oxide (LiOx), etc. An alkali metal, an alkaline earth metal, or a compound thereof can be used. In addition, a substance containing an electron transporting property containing an alkali metal, an alkaline earth metal, or a compound thereof, specifically, a substance containing magnesium (Mg) in Alq may be used. In this case, electron injection from the cathode can be performed more efficiently.
Alternatively, a composite material obtained by mixing an organic compound and an electron donor (donor) may be used for the electron injection layer. Such a composite material is excellent in electron injecting property and electron transporting property because electrons are generated in the organic compound by the electron donor. In this case, the organic compound is preferably a material excellent in transporting the generated electrons. Specifically, for example, a substance (metal complex, heteroaromatic compound, or the like) constituting the electron transport layer described above is used. be able to. The electron donor may be any substance that exhibits an electron donating property to the organic compound. Specifically, alkali metals, alkaline earth metals, and rare earth metals are preferable, and lithium, cesium, magnesium, calcium, erbium, ytterbium, and the like can be given. Alkali metal oxides and alkaline earth metal oxides are preferable, and lithium oxide, calcium oxide, barium oxide, and the like can be given. A Lewis base such as magnesium oxide can also be used. Alternatively, an organic compound such as tetrathiafulvalene (abbreviation: TTF) can be used.

(cathode)
It is preferable to use a metal, an alloy, an electrically conductive compound, a mixture thereof, or the like having a low work function (specifically, 3.8 eV or less) for the cathode. Specific examples of such a cathode material include elements belonging to Group 1 or Group 2 of the periodic table of elements, that is, alkali metals such as lithium (Li) and cesium (Cs), and magnesium (Mg) and calcium (Ca ), Alkaline earth metals such as strontium (Sr), and alloys containing these (for example, rare earth metals such as MgAg, AlLi), europium (Eu), ytterbium (Yb), and alloys containing these.
Note that in the case where the cathode is formed using an alkali metal, an alkaline earth metal, or an alloy containing these, a vacuum evaporation method or a sputtering method can be used. Moreover, when using a silver paste etc., the apply | coating method, the inkjet method, etc. can be used.
By providing an electron injection layer, a cathode is formed using various conductive materials such as indium oxide-tin oxide containing Al, Ag, ITO, graphene, silicon, or silicon oxide regardless of the work function. can do. These conductive materials can be formed by a sputtering method, an inkjet method, a spin coating method, or the like.

  For the formation of each layer of the organic EL element, any of dry film forming methods such as vacuum deposition, sputtering, plasma, and ion plating, and wet film forming methods such as spin coating, dipping, and flow coating can be used.

  In the case of a wet film forming method, a thin film is formed using a solution or dispersion in which the material for forming each layer is dissolved or dispersed in an appropriate solvent such as ethanol, chloroform, tetrahydrofuran, or dioxane. The solution or dispersion may contain a resin or an additive for improving film formability, preventing pinholes in the film, and the like. Examples of the resin include insulating resins such as polystyrene, polycarbonate, polyarylate, polyester, polyamide, polyurethane, polysulfone, polymethyl methacrylate, polymethyl acrylate, and cellulose, and copolymers thereof, poly-N-vinylcarbazole, polysilane. And photoconductive resins such as polythiophene and polypyrrole. Examples of the additive include an antioxidant, an ultraviolet absorber, and a plasticizer.

  The film thickness of each layer is not particularly limited, and may be selected so as to obtain good element performance. If the film thickness is too thick, a large applied voltage is required to obtain a constant light output, resulting in poor efficiency. If the film thickness is too thin, pinholes and the like are generated, and sufficient light emission luminance cannot be obtained even when an electric field is applied. The film thickness is usually 5 nm to 10 μm, and more preferably 10 nm to 0.2 μm. In particular, the thickness of the light emitting layer is not particularly limited, but is preferably 5 nm to 100 nm, more preferably 7 nm to 70 nm, and still more preferably 10 nm to 50 nm. Moreover, it is preferable that the film thickness of a positive hole transport layer is 10 nm-300 nm.

[Electronics]
An electronic device of one embodiment of the present invention includes the above-described organic EL element of one embodiment of the present invention.
Examples of such electronic devices include display components such as organic EL panel modules, display devices such as televisions, mobile phones, and personal computers, and illumination devices (light-emitting devices) for vehicle lamps.

EXAMPLES Next, although an Example and a comparative example are given and this invention is demonstrated in more detail, this invention is not restrict | limited to the description content of these Examples at all.
In addition, it is possible to synthesize | combine a compound prescribed | regulated by the claim of this application by using the known alternative reaction and raw material match | combined with the target object with reference to the following synthetic reactions.

<Synthesis Example>
(1) Synthesis of Compound 1 As shown in the following reaction formula, under an argon atmosphere, 4.08 g of Intermediate A, 3.96 g of 4-bromo-9,9-diphenylfluorene, tris (dibenzylideneacetone) dipalladium The flask was charged with 91 mg of (0), 114 mg of tri-t-butylphosphonium tetrafluoroborate, 1.34 g of sodium-t-butoxide, and 100 mL of toluene, and heated to reflux for 5 hours. After heating to reflux, the reaction solution was cooled to room temperature, and the reaction solution was extracted with toluene. The obtained organic layer was dried and concentrated. The obtained residue was purified by column chromatography to obtain 3.26 g of Compound 1. The yield of compound 1 was 45%.
As a result of mass spectrum analysis, the molecular weight of Compound 1 was 724, and m / e = 724.

(2) Synthesis of Compound 2 As shown in the following reaction formula, synthesis was performed in the same manner using Compound B instead of Intermediate A in the synthesis of Compound 1. As a result of mass spectrum analysis, m / e = 800 with respect to a molecular weight of 800 of Compound 2.

(3) Synthesis of Compound 3 As shown in the following reaction formula, the intermediate C was used instead of the intermediate A in the synthesis of the compound 1, and the same method was used. As a result of mass spectrum analysis, it was m / e = 724 with respect to the molecular weight 724 of compound 3.

(4) Synthesis of Compound 4 As shown in the following reaction formula, 4- (4-bromophenyl) -9,9-diphenylfluorene was used instead of 4-bromo-9,9-diphenylfluorene in the synthesis of Compound 1. And synthesized in the same manner. As a result of mass spectrum analysis, m / e = 800 with respect to a molecular weight of 800 of Compound 4.

(5) Synthesis of Compound 5 As shown in the following reaction formula, 4- (3-bromophenyl) -9,9-diphenylfluorene was used instead of 4-bromo-9,9-diphenylfluorene in the synthesis of Compound 1. And synthesized in the same manner. As a result of mass spectrum analysis, m / e = 800 with respect to a molecular weight of 800 of compound 5.

(6) Synthesis of Compound 6 As shown in the following reaction formula, synthesis was performed in the same manner using Intermediate D instead of Intermediate A in the synthesis of Compound 1. As a result of mass spectrum analysis, it was m / e = 649 with respect to the molecular weight 649 of compound 6.

<Element Example (Manufacture of Organic EL Element)>
[Example 1]
A glass substrate (manufactured by Geomatic) with an ITO transparent electrode (anode) having a thickness of 25 mm × 75 mm × 1.1 mm was subjected to ultrasonic cleaning in isopropyl alcohol for 5 minutes and then UV ozone cleaning for 30 minutes. The film thickness of ITO was 130 nm.
The glass substrate with the transparent electrode line after the cleaning is mounted on the substrate holder of the vacuum deposition apparatus, and first, the following compound HA-1 is deposited so as to cover the transparent electrode on the surface where the transparent electrode line is formed. Then, an HA-1 film having a thickness of 5 nm was formed to form a hole injection layer.
Next, the following compound HT-1 was vapor-deposited on this hole injection layer to form an HT-1 film having a thickness of 130 nm, thereby forming a first hole transport layer.
Next, the following compound HT-2 was vapor-deposited on the first hole transport layer to form an HT-2 film having a thickness of 20 nm to form a second hole transport layer.

Next, on the second hole transport layer, the following compound PGH-N1, compound 1 synthesized in Synthesis Example (1), and Irppy3 were formed by co-evaporation to form a light-emitting layer having a thickness of 40 nm. . Compound PGH-N1 and Compound 1 contained in the light emitting layer were 1: 1 by mass (both 95% by mass in total), and the concentration of Irppy3 was 5% by mass.
Following the formation of the light emitting layer, the following compound ET and 8-quinolinolatolithium (Liq) were formed by co-evaporation at a mass ratio of 50:50 to form an electron transport layer having a thickness of 25 nm.
Liq was vapor-deposited on this electron transport layer to form an electron injection layer having a thickness of 1 nm.
Metal Al was vapor-deposited on the electron injection layer to form a metal cathode having a thickness of 80 nm.
Thus, the organic EL element of Example 1 was produced.

[Example 2]
The organic EL device of Example 2 was prepared in the same manner as in the manufacture of the organic EL device of Example 1, except that the following compound PGH-N2 was used instead of the compound PGH-N1.

[Comparative Examples 1 and 2]
In the production of the organic EL device of Example 1, the organic EL devices of Comparative Examples 1 and 2 were produced in the same manner except that the following Comparative Compound 1 or 2 was used instead of Compound 1.

[Evaluation of organic EL elements]
Table 1 shows the results of measuring the external quantum efficiency (luminescence efficiency) at a current density of 10 mA / cm ² by causing the obtained organic EL device to emit light by direct current drive. Further, Table 1 shows the results of measuring the half life of light emission at an initial luminance of 5000 cd / m ² , room temperature, and DC constant current driving.

  From the above results, it is clear that the compound of the present invention is superior in that it has high luminous efficiency and has a longer lifetime than the compound used in the comparative example. That is, it was found that a compound having a substituent containing a 4-fluorenyl group having a specific substituent at the 9,9′-position at the 9-position of carbazole is important for improving the performance of the host material.

  INDUSTRIAL APPLICABILITY The present invention can be used as an organic EL element that has a long life, has high luminous efficiency, can be driven at a low voltage necessary for power saving, and a material for an organic EL element that realizes the organic EL element.

DESCRIPTION OF SYMBOLS 1 Organic EL element 2 Board | substrate 3 Anode 4 Cathode 5 Light emitting layer 6 Anode side organic thin film layer 7 Cathode side organic thin film layer 10 Light emitting unit

Claims (26)

A compound represented by the following formula (1).

[In formula (1), Ar ₁ and Ar ₂ represent a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms or a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms.
X represents an oxygen atom, a sulfur atom, C (R ′) (R ″), or N (—L ₂ —Ar ₃ ).
R ′ and R ″ each independently represents a hydrogen atom or a substituent.
Ar ₃ represents a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms.
L ₁ and L ₂ are each independently a single bond, a substituted or unsubstituted divalent arylene group having 6 to 18 ring carbon atoms, or a substituted or unsubstituted divalent aryl group having 5 to 18 ring atoms. Represents a heteroarylene group.
R _{1 to} R ₆ each independently represent a substituent, and adjacent R _{1 s} , R _{2 s} , R _{3 s} , R _{4 s} , R _{5 s} , and R _{6 s} are independently bonded to each other. To form a ring.
a, c, and f each independently represent an integer of 0 to 4, and b, d, and e each independently represents an integer of 0 to 3. ] The compound of Claim 1 represented by a following formula (2-1) or (2-2).

[In Formulas (2-1) and (2-2), X represents an oxygen atom, a sulfur atom, C (R ′) (R ″), or N (—L ₂ —Ar ₃ ), and Ar ₁ ˜Ar ₃ , R ′, R ″, R _{1 to} R ₆ , L ₁ , L ₂ and a to f are the same as those in the formula (1). ] The compound of Claim 1 or 2 represented by a following formula (3-1) or (3-2).

[In Formulas (3-1) and (3-2), X represents an oxygen atom, a sulfur atom, C (R ′) (R ″), or N (—L ₂ —Ar ₃ ), and Ar ₁ ˜Ar ₃ , R ′, R ″, R _{1 to} R ₆ , L ₂ and a to f are the same as those in the formula (1). ] The compound according to claim 1 or 2, wherein L ₁ is represented by the following formula (4-1), (4-2), or (4-3).

In [Equation _{(4-1) ~ (4-3),} R 41 ~R 45 each independently represent a substituent. g, h and i each independently represents an integer of 0 to 3, and j and k each represents an integer of 0 to 2. Z represents an oxygen atom, a sulfur atom, C (R ₄₆ ) (R ₄₇ ), or N (—L ₃ —Ar ₄ ). R ₄₆ and R ₄₇ are the same as R ′ and R ″ in the formula (1), L ₃ is the same as L ₂ in the formula (1), and Ar ₄ is Ar ₃ in the formula (1). Is the same. ]   Said X is an oxygen atom or a sulfur atom, The compound of any one of Claims 1-4. The compound of any one of Claims 1-4 represented by following formula (5-1) or (5-2).

[In the formulas (5-1) and (5-2), Ar _{1 to} Ar ₃ , R _{1 to} R ₆ , L ₁ , L ₂ and a to f are the same as those in the formula (1). . ] The compound of Claim 1 or 2 represented by a following formula (6-1) or (6-2).

[In Formulas (6-1) and (6-2), Ar _{1 to} Ar ₃ , R _{1 to} R ₆ , and a to f are the same as those in Formula (1). ] The substituents represented by R _{1 to} R ₆ and the substituents represented by R ′ and R ″ are each independently an alkyl group having 1 to 20 carbon atoms or a cyclohexane having 3 to 50 ring carbon atoms. An alkyl group, an aryl group having 6 to 18 ring carbon atoms, an aralkyl group having 7 to 30 carbon atoms having an aryl group having 6 to 10 ring carbon atoms, an alkoxy group having 1 to 20 carbon atoms, and 6 to 6 ring carbon atoms A monosubstituted, disubstituted or trisubstituted silyl group having a substituent selected from an alkyl group having 1 to 20 carbon atoms and an aryl group having 6 to 10 ring carbon atoms, 5 to 18 ring atoms The compound according to any one of claims 1 to 7, which is a heteroaryl group, a haloalkyl group having 1 to 20 carbon atoms, a haloalkoxy group having 1 to 20 carbon atoms, a halogen atom, a cyano group, or a nitro group. The compound of Claim 1 or 2 represented by a following formula (7-1) or (7-2).

[In Formulas (7-1) and (7-2), Ar _{1 to} Ar ₃ are the same as those in Formula (1), respectively. ] Wherein X is, _{N (-L} 2 -Ar _{3) [L 2} and Ar _3, X in the formula (1) is the same as that representing a _{N (-L} 2 -Ar _3). A], when the total number of carbon atoms of the L ₂ and the Ar ₃ which is 6 to 15 [wherein L ₂ and the Ar ₃ comprises a substituent claim 1 which is containing] a number of carbon atoms of the substituent 5. The compound according to any one of 4. Ar ₁ and Ar ₂ are each independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted biphenylyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted triphenylenyl. Group, substituted or unsubstituted fluoranthenyl group, substituted or unsubstituted dibenzofuranyl group, substituted or unsubstituted dibenzothiophenyl group, substituted or unsubstituted carbazolyl group, substituted or unsubstituted pyrimidinyl group, substituted or The compound according to any one of claims 1 to 10, which is an unsubstituted triazinyl group or a substituted or unsubstituted quinazolinyl group. Ar ₃ is a substituted or unsubstituted phenyl group, substituted or unsubstituted naphthyl group, substituted or unsubstituted biphenylyl group, substituted or unsubstituted triphenylenyl group, substituted or unsubstituted fluorenyl group, substituted or unsubstituted The dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted pyridinyl group, a substituted or unsubstituted pyrimidinyl group, or a substituted or unsubstituted triazolyl group. The compound according to item 1. The compound according to any one of claims 1 to 12, wherein Ar ₁ and Ar ₂ are each independently a substituted or unsubstituted phenyl group.   The organic electroluminescent element material containing the compound of any one of Claims 1-13.   An organic electroluminescence device having a cathode, an anode, and an organic thin film layer composed of one or more layers sandwiched between the cathode and the anode, the organic thin film layer including a light emitting layer, and at least one of the organic thin film layers Organic electroluminescent element containing the compound of any one of Claims 1-13.   The organic electroluminescent element according to claim 15, wherein the light emitting layer contains the compound as a host material. The organic electroluminescence device according to claim 16, wherein the light emitting layer further contains a compound represented by the following formula (8) as a host material.

[In Formula (8),
X ^{1 to} X ³ each independently represent CR ¹¹ or N.
R ⁵ to R ⁷ and ^{R 11} are each ^{_{independently, - (B 5) s -}} (B 6) t - shows the ^{_{(B 8) v -R 8 -}} (B 7) u.
s, t, u and v each independently represent 0 or 1.
B ^{5 to} B ⁸ each independently represents a substituted or unsubstituted arylene group having 6 to 24 ring carbon atoms or a substituted or unsubstituted heteroarylene group having 5 to 30 ring atoms.
R ⁸ represents a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 25 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 25 carbon atoms, or a substituted or unsubstituted alkynyl group having 2 to 25 carbon atoms. Group, substituted or unsubstituted cycloalkyl group having 3 to 25 ring carbon atoms, substituted or unsubstituted alkoxy group having 1 to 25 carbon atoms, substituted or unsubstituted aryl group having 6 to 24 ring carbon atoms, substituted Or an unsubstituted heteroaryl group having 5 to 30 ring atoms, a substituted or unsubstituted aryloxy group having 6 to 24 ring carbon atoms, a substituted or unsubstituted alkylthio group having 1 to 25 carbon atoms, substituted or unsubstituted 1 or more selected from the group consisting of a substituted arylthio group having 6 to 24 ring carbon atoms, an alkyl group having 1 to 25 carbon atoms, and an aryl group having 6 to 24 ring carbon atoms A silyl group, a cyano group, or —P (═O) R ¹⁴ R ¹⁵ substituted with a group of Adjacent substituents on R ⁸ may combine with each other to form a ring.
R ¹⁴ and R ¹⁵ each independently represent a substituted or unsubstituted alkyl group having 1 to 25 carbon atoms, a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms, or a substituted or unsubstituted ring formation. A heteroaryl group having 5 to 18 atoms is shown. ] The organic electroluminescence device according to claim 17, wherein the compound represented by the formula (8) is represented by the following formula (82).

[In the formula (82), X ^{1 to} X ³ , R ⁵ and R ⁶ are the same as those in the formula (8).
L ¹ is a substituted or unsubstituted arylene group having 6 to 24 ring carbon atoms or a substituted or unsubstituted heteroarylene group having 5 to 30 ring atoms.
f is an integer of 0 or 1.
Y ¹ is a carbon atom or a nitrogen atom.
Ar ¹ is a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 24 ring carbon atoms that shares the carbon atom of adjacent nitrogen-containing five-membered ring and Y ¹ and is fused to the nitrogen-containing five-membered ring. Or a substituted or unsubstituted heteroaromatic ring having 5 to 30 ring atoms that shares the nitrogen atom of adjacent nitrogen-containing five-membered ring and Y ¹ and is fused to the nitrogen-containing five-membered ring. .
R ⁵² represents a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 25 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 25 carbon atoms, or a substituted or unsubstituted alkynyl group having 2 to 25 carbon atoms. Group, substituted or unsubstituted cycloalkyl group having 3 to 25 ring carbon atoms, substituted or unsubstituted alkoxy group having 1 to 25 carbon atoms, substituted or unsubstituted aryl group having 6 to 24 ring carbon atoms, substituted Or an unsubstituted heteroaryl group having 5 to 30 ring atoms, a substituted or unsubstituted aryloxy group having 6 to 24 ring carbon atoms, a substituted or unsubstituted alkylthio group having 1 to 25 carbon atoms, substituted or unsubstituted 1 or more selected from the group consisting of a substituted arylthio group having 6 to 24 ring carbon atoms, an alkyl group having 1 to 25 carbon atoms, and an aryl group having 6 to 24 ring carbon atoms A silyl group, a cyano group, or —P (═O) R ¹⁴ R ¹⁵ substituted with the above group is shown. Adjacent substituents on R ⁵² may combine with each other to form a ring.
R ¹⁴ and R ¹⁵ are as defined in the above formula (8).
c is an integer of 0 to 4, and when c is 2 to 4, a plurality of R ⁵² may be the same or different from each other, and adjacent R ⁵² may be bonded to form a ring. . ] The organic electroluminescence device according to claim 17 or 18, wherein the compound represented by the formula (8) is represented by the following formula (82a).

[In the formula (82a), R ⁵ , R ⁶ , R ⁵² , c, L ¹ , f, Y ¹ and Ar ¹ are the same as those in the formula (82). ]   The organic electroluminescent element according to claim 15, wherein the light emitting layer contains a phosphorescent material.   21. The organic electroluminescence device according to claim 20, wherein the phosphorescent material is an orthometalated complex of a metal atom selected from iridium (Ir), osmium (Os), and platinum (Pt).   The organic electroluminescent element according to claim 15, wherein the light emitting layer contains a fluorescent light emitting material.   The organic electroluminescence device according to any one of claims 15 to 22, further comprising an electron transport layer between the cathode and the light emitting layer, wherein the electron transport layer contains the compound.   The organic electroluminescence device according to any one of claims 15 to 23, further comprising a hole transport layer between the anode and the light emitting layer, wherein the hole transport layer contains the compound.   An illuminating device provided with the organic electroluminescent element of any one of Claims 15-24.   A display apparatus provided with the organic electroluminescent element of any one of Claims 15-24.