JP2023134566A - Organic electroluminescent element - Google Patents

Abstract

To provide an organic EL element, having an excellent light emission efficiency, and indicating a good balance performance.SOLUTION: The present invention provides an organic EL element with, for example, a light emission efficiency, by manufacturing an organic EL element by using a light emission layer material in which a pyrene compound expressed by the following formula (2) is a host material, and a polycyclic aromatic compound obtained by coupling a plurality of aromatic rings with a boron atom and a nitrogen atom or an oxygen atom is a dopant material. (Compound 161) In the above formula (2), at least one hydrogen of a pyrene part may be replaced by an aryl or the like of 6 to 10 of carbons, and Ar is an aryl of 14 to 40 of carbons or a hetero aryl of 12 to 40 of carbons, and they may be replaced with the aryl or the like of 6 to 10 of carbons. s and p are an integration number of 1 or 2 independently, and the s and p do not become 2 at the same time. At least one hydrogen in a compound expressed by the formula (2) may be replaced with halogen, cyano, or heavy hydrogen, independently.

Description

The present invention relates to an organic electroluminescent device having a light emitting layer containing a polycyclic aromatic compound as a dopant material and a specific pyrene compound as a host material, and a display device and a lighting device using the same.

Conventionally, display devices using light emitting elements that emit electroluminescence have been studied in various ways because they can save power and be made thinner. Furthermore, organic electroluminescent elements (hereinafter referred to as organic EL elements) made of organic materials have It has been actively studied because it can be easily scaled up and made larger. In particular, efforts have been made to develop organic materials that emit light such as blue, which is one of the three primary colors of light, and to combine multiple materials to achieve optimal light emitting properties, regardless of whether they are high-molecular compounds or low-molecular compounds. has been studied.

An organic EL element has a structure consisting of a pair of electrodes consisting of an anode and a cathode, and one or more layers containing an organic compound and disposed between the pair of electrodes. Layers containing organic compounds include a light-emitting layer and a charge transport/injection layer that transports or injects charges such as holes and electrons, and various organic materials suitable for these layers have been developed.

As materials for the light-emitting layer, benzofluorene compounds, for example, have been developed (International Publication No. 2004/061047). Further, as hole transport materials, for example, triphenylamine compounds have been developed (Japanese Patent Laid-Open No. 2001-172232). Further, as electron transport materials, for example, anthracene compounds have been developed (Japanese Patent Laid-Open No. 2005-170911).

Furthermore, in recent years, compounds in which multiple aromatic rings are condensed with boron or the like as a central atom have been reported (International Publication No. 2015/102118). In this document, a compound in which the plurality of aromatic rings are condensed is selected as the dopant material of the light-emitting layer, and anthracene-based compounds (BH1 on page 442) are selected as the host material among a large number of materials described. Although evaluations of organic EL elements have been carried out in the case of The properties obtained from this are still unknown.

International Publication No. 2004/061047 Japanese Patent Application Publication No. 2001-172232 Japanese Patent Application Publication No. 2005-170911 International Publication No. 2015/102118

As mentioned above, various materials have been developed for use in organic EL devices, but in order to further improve the luminescent properties and increase the selection of materials for the luminescent layer, it is desired to develop material combinations that are different from conventional materials. ing. In particular, it is not known about organic EL properties (particularly optimal light emitting properties) obtained from combinations of hosts and dopants other than the specific host and dopant combinations reported in the example of Patent Document 4.

As a result of intensive studies to solve the above problems, the present inventors found that a light-emitting layer containing a polycyclic aromatic compound in which a plurality of aromatic rings are connected by a boron atom and a nitrogen atom or an oxygen atom and a specific pyrene compound. By arranging between a pair of electrodes to construct an organic EL element, excellent organic E
It was discovered that an L element could be obtained, and the present invention was completed.

According to a preferred embodiment of the present invention, it is possible to provide a compound represented by formula (1) and a compound represented by formula (2), which can be combined with the compound represented by formula (2), and which can be combined with the compound represented by formula (2). By manufacturing an organic EL device using a material for a light emitting layer consisting of the following materials, it is possible to provide an organic EL device that is excellent in one or more of chromaticity, drive voltage, and quantum efficiency.

Item 1.
An organic electroluminescent device comprising a pair of electrodes consisting of an anode and a cathode, and a light emitting layer disposed between the pair of electrodes,
The light-emitting layer includes at least one of a compound represented by the following general formula (1) and a multimer having a plurality of structures represented by the following general formula (1), and a pyrene-based compound represented by the following general formula (2). An organic electroluminescent device comprising at least one compound.
In the above formula (1),
Ring A, Ring B and Ring C are each independently an aryl ring or a heteroaryl ring, and at least one hydrogen in these rings may be substituted,
X ¹ and X ² are each independently >O or >NR, and R in >NR is an optionally substituted aryl, an optionally substituted heteroaryl, an optionally substituted heteroaryl, or an optionally substituted heteroaryl. alkyl or optionally substituted cycloalkyl, and R in >N-R may be bonded to the A ring, B ring and/or C ring through a linking group or a single bond, and ,
At least one hydrogen in the compound or structure represented by formula (1) may be independently substituted with halogen, cyano or deuterium,
In the above formula (2),
s pyrene moieties and p Ar moieties are bonded at any position of * of the pyrene moiety and any position of the Ar moiety,
At least one hydrogen in the pyrene moiety is each independently an aryl having 6 to 10 carbon atoms, a heteroaryl having 2 to 11 carbon atoms, an alkyl having 1 to 30 carbon atoms, a cycloalkyl having 3 to 24 carbon atoms, or a cycloalkyl having 3 to 24 carbon atoms. Alkenyl having 2 to 30 carbon atoms, alkoxy having 1 to 30 carbon atoms or 6 carbon atoms
-30 aryloxy may be substituted, and at least one hydrogen in these may be independently substituted with aryl having 6 to 10 carbon atoms, heteroaryl having 2 to 11 carbon atoms,
Optionally substituted with alkyl having 1 to 30 carbon atoms, cycloalkyl having 3 to 24 carbon atoms, alkenyl having 2 to 30 carbon atoms, alkoxy having 1 to 30 carbon atoms, or aryloxy having 6 to 30 carbon atoms,
Ar is each independently an aryl having 14 to 40 carbon atoms or a heteroaryl having 12 to 40 carbon atoms, and at least one hydrogen therein is each independently an aryl having 6 to 10 carbon atoms, an aryl having 6 to 10 carbon atoms, or a heteroaryl having 12 to 40 carbon atoms. heteroaryl having 2 to 11 carbon atoms, alkyl having 1 to 30 carbon atoms,
Optionally substituted with cycloalkyl having 3 to 24 carbon atoms, alkenyl having 2 to 30 carbon atoms, alkoxy having 1 to 30 carbon atoms, or aryloxy having 6 to 30 carbon atoms,
s and p are each independently an integer of 1 or 2, s and p cannot be 2 at the same time, and when s is 2, the two pyrene moieties are structurally the same including the substituents. or may be different, and when p is 2, the two Ar moieties may be structurally the same or different including the substituents, and,
At least one hydrogen in the compound represented by formula (2) may be independently substituted with halogen, cyano, or deuterium.

Item 2.
Item 1. The organic electroluminescent device according to Item 1, wherein the Ar is each independently a group represented by the following general formula (Ar-1) or general formula (Ar-2).
In each of the above formulas,
Z is >CR ₂ , >NR, >O or >S;
>R in CR ₂ is each independently alkyl having 1 to 6 carbon atoms, or 3 to 14 carbon atoms.
cycloalkyl, aryl having 6 to 12 carbon atoms, or heteroaryl having 2 to 12 carbon atoms, and at least one hydrogen in the aryl and heteroaryl has 1 to 4 carbon atoms.
may be substituted with alkyl or cycloalkyl having 5 to 10 carbon atoms, and R may be bonded to each other to form a ring,
>R in NR is alkyl having 1 to 4 carbon atoms, cycloalkyl having 5 to 10 carbon atoms,
Aryl having 6 to 12 carbon atoms or heteroaryl having 2 to 12 carbon atoms, and at least one hydrogen in the aryl and heteroaryl is substituted with alkyl having 1 to 4 carbon atoms or cycloalkyl having 5 to 10 carbon atoms. It's okay,
R ¹ to R ⁸ and R ¹⁰ to R ¹⁹ each independently represent hydrogen, aryl having 6 to 10 carbon atoms, heteroaryl having 2 to 11 carbon atoms, alkyl having 1 to 30 carbon atoms, and 3 to 2 carbon atoms.
cycloalkyl having 4 to 30 carbon atoms, alkenyl having 2 to 30 carbon atoms, alkoxy having 1 to 30 carbon atoms, or aryloxy having 6 to 30 carbon atoms, in which at least one hydrogen is an alkyl having 1 to 6 carbon atoms or an alkyl having 3 to 6 carbon atoms. may be substituted with ~14 cycloalkyl, R ¹
Adjacent groups among R ⁸ to R 8 or adjacent groups among R ¹⁰ to R ¹⁹ may be bonded to each other to form a condensed ring, and each formed ring independently has a carbon number of 6 ~1
Aryl of 0, heteroaryl of 2 to 11 carbon atoms, alkyl of 1 to 30 carbon atoms, 3 carbon atoms
-24 cycloalkyl, C2-30 alkenyl, C1-30 alkoxy or C6-30 aryloxy, and at least one hydrogen in these is substituted with C1-6 may be substituted with alkyl or cycloalkyl having 3 to 14 carbon atoms, and
At least one hydrogen in the group represented by the above formula (Ar-1) or formula (Ar-2) may be independently substituted with halogen, cyano, or deuterium,
In formula (2), the pyrene moiety is bonded at any position in the group represented by formula (Ar-1) or formula (Ar-2) above.

Item 3.
Item 3. The organic electroluminescent device according to item 1 or 2, wherein the compound represented by the general formula (1) is a compound represented by the following general formula (1').
(In the above formula (1'),
R ¹ to R ¹¹ are each independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, alkyl, cycloalkyl, alkoxy, or aryloxy, in which at least one hydrogen may be each independently substituted with aryl, heteroaryl, alkyl, or cycloalkyl, and adjacent groups among R ¹ to R ¹¹ may be bonded to form ring a, b
The ring or c-ring may form an aryl ring or a heteroaryl ring, and at least one hydrogen in the formed ring is independently aryl, heteroaryl,
Optionally substituted with diarylamino, diheteroarylamino, arylheteroarylamino, alkyl, cycloalkyl, alkoxy or aryloxy, in which at least one hydrogen is independently aryl, heteroaryl, alkyl or Optionally substituted with cycloalkyl,
X ¹ and X ² are each independently >O or >NR, and R in >NR is an aryl having 6 to 12 carbon atoms, a heteroaryl having 2 to 15 carbon atoms, or 1 to 6 carbon atoms. is an alkyl or cycloalkyl having 3 to 14 carbon atoms, and at least one hydrogen in the aryl or heteroaryl may be substituted with an alkyl having 1 to 4 carbon atoms or a cycloalkyl having 5 to 10 carbon atoms, and , R in >N-R is -O-, -S-, -C(-R) ₂
- or may be bonded to the a ring, b ring and/or c ring through a single bond, and the -
R in C(-R) ₂ - is alkyl having 1 to 6 carbon atoms or cycloalkyl having 3 to 14 carbon atoms, and
At least one hydrogen in the compound represented by formula (1') may be independently substituted with halogen, cyano, or deuterium.

Item 4.
The above Ar each independently represents the following general formulas (Ar-1-1) to (Ar-1-12)
and Item 1, which is a group represented by any of the general formulas (Ar-2-1) to (Ar-2-4)
The organic electroluminescent device according to any one of items 1 to 3.
In each of the above formulas,
Z is >CR ₂ , >NR, >O or >S;
>R in CR ₂ is each independently alkyl having 1 to 6 carbon atoms, or 3 to 14 carbon atoms.
is cycloalkyl or aryl having 6 to 12 carbon atoms, and R may be bonded to each other to form a ring,
>R in NR is alkyl having 1 to 4 carbon atoms, cycloalkyl having 5 to 10 carbon atoms, or aryl having 6 to 12 carbon atoms,
At least one hydrogen in the group represented by each of the above formulas each independently has a carbon number of 6
Optionally substituted with an aryl having ~10 carbon atoms, a heteroaryl having 2 to 11 carbon atoms, an alkyl having 1 to 30 carbon atoms, or a cycloalkyl having 3 to 24 carbon atoms, and
At least one hydrogen in the group represented by each of the above formulas may be independently substituted with halogen, cyano, or deuterium,
In formula (2), the pyrene moiety is represented by any of the above formulas (Ar-1-1) to (Ar-1-12) and formulas (Ar-2-1) to (Ar-2-4). bond at any position in the group.

Item 5.
5. The organic electroluminescent device according to any one of Items 1 to 4, wherein the pyrene compound represented by the general formula (2) is a compound represented by any of the following structural formulas.

Item 6.
comprising an electron transport layer and/or an electron injection layer disposed between the cathode and the light emitting layer,
At least one of the electron transport layer and the electron injection layer is a borane derivative, a pyridine derivative, a fluoranthene derivative, a BO derivative, an anthracene derivative, a benzofluorene derivative, a phosphine oxide derivative, a pyrimidine derivative, a carbazole derivative, a triazine derivative, or a benzimidazole derivative. 6. The organic electroluminescent device according to any one of Items 1 to 5, which contains at least one selected from the group consisting of , phenanthroline derivatives, and quinolinol metal complexes.

Section 7.
The electron transport layer and/or the electron injection layer further comprises an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal oxide, an alkali metal halide, an alkaline earth metal oxide, an alkaline earth metal oxide, and an alkaline earth metal oxide. Item 6, containing at least one selected from the group consisting of halides, rare earth metal oxides, rare earth metal halides, alkali metal organic complexes, alkaline earth metal organic complexes, and rare earth metal organic complexes. The organic electroluminescent device described in .

Section 8.
A display device comprising the organic electroluminescent element according to any one of Items 1 to 7.

Item 9.
Item 8. A lighting device comprising the organic electroluminescent element according to any one of Items 1 to 7.

Item 10.
A pyrene compound represented by the following general formula (2).
In the above formula,
s pyrene moieties and p Ar moieties are bonded at any position of * of the pyrene moiety and any position of the Ar moiety,
At least one hydrogen in the pyrene moiety is each independently an aryl having 6 to 10 carbon atoms, a heteroaryl having 2 to 11 carbon atoms, an alkyl having 1 to 30 carbon atoms, a cycloalkyl having 3 to 24 carbon atoms, or a cycloalkyl having 3 to 24 carbon atoms. Alkenyl having 1 to 30 carbon atoms, alkoxy having 1 to 30 carbon atoms, or 1 carbon number
~30 may be substituted with aryloxy, and at least one hydrogen in these may be substituted with alkyl having 1 to 6 carbon atoms or cycloalkyl having 3 to 14 carbon atoms,
Ar is a group represented by the following general formula (Ar-1) or general formula (Ar-3),
In each of the above formulas,
Z is >CR ₂ ,
>R in CR ₂ is each independently alkyl having 1 to 6 carbon atoms, or 3 to 14 carbon atoms.
cycloalkyl, aryl having 6 to 12 carbon atoms, or heteroaryl having 2 to 12 carbon atoms, and at least one hydrogen in the aryl and heteroaryl has 1 to 4 carbon atoms.
may be substituted with alkyl or cycloalkyl having 5 to 10 carbon atoms, and R may be bonded to each other to form a ring,
R ¹ to R ⁸ and R ²⁰ to R ³⁵ each independently represent hydrogen, aryl having 6 to 10 carbon atoms, heteroaryl having 2 to 11 carbon atoms, alkyl having 1 to 30 carbon atoms, and 3 to 2 carbon atoms.
cycloalkyl having 1 to 30 carbon atoms, alkenyl having 1 to 30 carbon atoms, alkoxy having 1 to 30 carbon atoms, or aryloxy having 1 to 30 carbon atoms, in which at least one hydrogen is an alkyl having 1 to 6 carbon atoms or 3 carbon atoms. may be substituted with ~14 cycloalkyl, R ¹
Adjacent groups from R ⁸ are bonded to each other to form a condensed ring, and from R ²⁰ to R ³
Adjacent groups of ⁵ may be bonded to each other to form a condensed ring, and the formed rings are each independently aryl having 6 to 10 carbon atoms, heteroaryl having 2 to 11 carbon atoms, It may be substituted with alkyl having 1 to 30 carbon atoms, cycloalkyl having 3 to 24 carbon atoms, alkenyl having 1 to 30 carbon atoms, alkoxy having 1 to 30 carbon atoms, or aryloxy having 1 to 30 carbon atoms, and these at least one hydrogen in may be substituted with alkyl having 1 to 6 carbon atoms or cycloalkyl having 3 to 14 carbon atoms, and
s and p are each independently an integer of 1 or 2, s and p cannot be 2 at the same time, and when s is 2, the two pyrene moieties are structurally the same including the substituents. or may be different, and when p is 2, the two Ar moieties may be structurally the same or different including the substituents,
At least one hydrogen in the compound represented by formula (2) may be independently substituted with halogen, cyano, or deuterium.

Item 11.
The pyrene compound described in item 10, which is represented by any of the following structural formulas.

According to a preferred embodiment of the present invention, there is provided a polycyclic aromatic compound represented by formula (1) and a pyrene compound represented by formula (2) that can be combined with the polycyclic aromatic compound to obtain optimal luminescent properties. By manufacturing an organic EL device using a material for a light emitting layer formed by combining these, it is possible to provide an organic EL device that exhibits particularly excellent luminous efficiency and well-balanced performance.

Further, by introducing a cycloalkyl group into the compound of the general formula (1) and its multimer, a reduction in melting point and sublimation temperature can be expected. This means that in sublimation purification, which is almost essential as a purification method for materials for organic devices such as organic EL elements that require high purity, thermal decomposition of the material can be avoided because purification can be performed at a relatively low temperature. means. Also, this is
The same is true for the vacuum evaporation process, which is an effective means for producing organic devices such as organic EL elements.Since the process can be carried out at relatively low temperatures, thermal decomposition of the material can be avoided, resulting in high performance. can be obtained for use in organic devices. In addition, since many of the above-mentioned polymers have a high sublimation temperature due to their high molecular weight or high planarity, the introduction of a cycloalkyl group can more effectively lower the sublimation temperature. Furthermore, since the solubility in organic solvents is improved by introducing a cycloalkyl group, it can also be applied to device fabrication using a coating process. Concentration quenching can also be suppressed by introducing a large substituent such as cycloalkyl. However, the present invention is not particularly limited to these principles.

FIG. 1 is a schematic cross-sectional view showing an organic EL element according to the present embodiment.

1. Organic electroluminescent device of the present invention The present invention is an organic electroluminescent device having a pair of electrodes consisting of an anode and a cathode, and a light-emitting layer disposed between the pair of electrodes, the light-emitting layer comprising the following general A polycyclic aromatic compound represented by formula (1) and at least one of its multimers having a plurality of structures represented by the following general formula (1), and a pyrene compound represented by the following general formula (2). An organic electroluminescent device including at least one.
Note that the definitions of the signs in formulas (1) and (2) are the same as the definitions above, and hereinafter, the definitions of signs in other formulas will be the same as the signs in the corresponding formulas above, unless otherwise specified. is the same as the definition of

2. Polycyclic aromatic compound and multimer thereof The polycyclic aromatic compound and multimer thereof used in the present invention are a compound represented by the following general formula (1) or a structure represented by the following general formula (1). Preferably, it is a compound represented by the following general formula (1') or a multimer having a plurality of structures represented by the following general formula (1'). These compounds basically function as dopants.

Ring A, ring B, and ring C in general formula (1) are each independently an aryl ring or a heteroaryl ring, and at least one hydrogen in these rings may be substituted with a substituent. The substituents include substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted diarylamino, substituted or unsubstituted diheteroarylamino, substituted or unsubstituted arylheteroarylamino (aryl and (amino group having heteroaryl), substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkoxy, or substituted or unsubstituted aryloxy are preferred.
When these groups have a substituent, examples of the substituent include aryl, heteroaryl, alkyl, and cycloalkyl. Further, the above aryl ring or heteroaryl ring is a 5-membered ring or a 6-membered ring that shares a bond with the central condensed 2-ring structure of general formula (1) consisting of the central element B (boron), X ¹ and X ² . It is preferable to have.

Here, the "fused two-ring structure" refers to the central element B (boron) shown in the center of general formula (1).
, refers to a structure in which two saturated hydrocarbon rings containing X ¹ and X ² are fused.
In addition, "a 6-membered ring that shares a bond with a fused 2-ring structure" is, for example, a ring a (benzene ring (6-membered ring)) fused to the fused 2-ring structure, as shown in the above general formula (1'). means. Also,"
"The aryl ring or heteroaryl ring (which is Ring A) has this 6-membered ring" means this 6-membered ring.
This means that ring A is formed by only the membered ring, or ring A is formed by further condensing another ring etc. with this 6-membered ring so as to include this 6-membered ring. In other words, the term "aryl ring or heteroaryl ring having a 6-membered ring (which is Ring A)" as used herein means that the 6-membered ring constituting all or part of Ring A is fused to the fused two-ring structure. It means doing. “B ring (b
The same explanation applies to "ring)", "C ring (c ring)", and "5-membered ring".

Ring A (or ring B, ring C) in general formula (1) is ring a and its substituents R ¹ to R ³ in general formula (1') (or ring b and its substituents R ⁸ to R ¹¹ , c ring and its substituents R ⁴ to R
⁷ ). That is, the general formula (1') corresponds to a structure in which "an A to C ring having a 6-membered ring" is selected as the A to C rings of the general formula (1). In this sense, each ring in general formula (1') is represented by lowercase letters a to c.

In the general formula (1'), adjacent groups among the substituents R ¹ to R ¹¹ of rings a, b, and c are bonded together to form an aryl or heteroaryl ring together with rings a, b, or c. and at least one hydrogen in the ring formed is substituted with aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, alkyl, cycloalkyl, alkoxy or aryloxy. At least one hydrogen in these may be substituted with aryl, heteroaryl, alkyl or cycloalkyl. Therefore, the polycyclic aromatic compound represented by the general formula (1') has the following formula (1'-1
) and formula (1'-2), the ring structure constituting the compound changes. A in each formula
'Ring, B' ring and C' ring correspond to A ring, B ring and C ring in general formula (1), respectively.

A' ring, B' ring, and C' ring in the above formulas (1'-1) and (1'-2) are the substituents R ¹ to R ¹¹ when explained using the general formula (1'). Indicates an aryl ring or a heteroaryl ring formed by bonding adjacent groups together with the a-ring, b-ring, and c-ring, respectively. It can also be said to be a fused ring). Although not shown in the formula, there are also compounds in which all of ring a, ring b, and ring c are changed to ring A', ring B', and ring C'. Furthermore, as can be seen from the above formulas (1'-1) and (1'-2), for example, R ⁸ of ring b and R ⁷ of ring c, R ¹¹ of ring b and R ¹ of ring a, c R ⁴ in the ring, R ³ in the a ring, etc. do not fall under "adjacent groups" and do not bond together. That is, "adjacent groups" means groups that are adjacent on the same ring.

The compound represented by the above formula (1'-1) or formula (1'-2) has a benzene ring, an indole ring, a pyrrole ring, a benzene ring, an indole ring, a pyrrole ring, A' ring (or B' ring or C' ring formed by condensation of benzofuran ring or benzothiophene ring)
The formed fused ring A' (or fused ring B' or fused ring C') is a naphthalene ring, a carbazole ring, an indole ring, a dibenzofuran ring, or a dibenzothiophene ring, respectively.

In general formula (1), X ¹ and X ² are each independently >O or >NR, and R in >NR is optionally substituted aryl or optionally substituted Heteroaryl, optionally substituted alkyl, or optionally substituted cycloalkyl, and R in >N-R may be bonded to the B ring and/or C ring through a linking group or a single bond. Preferably, the linking group is -O-, -S- or -C(-R) ₂ -. Note that R in the above "-C(-R) _2- " is hydrogen, alkyl, or cycloalkyl. This explanation is the same for X ¹ and X ² in general formula (1').

Here, in the general formula (1), "R of NR is a linking group or a single bond to the A ring, B
In general formula (1'), the definition ``bonded with ring and/or ring C'' means ``R of NR is -O-, -S-, -C(-R) ₂ - or a single bond. The a-ring, b-ring and/or c
This corresponds to the stipulation that "is connected to a ring."

This regulation can be expressed by a compound having a ring structure represented by the following formula (1'-3-1) in which X ¹ and X ² are incorporated into fused ring B' and fused ring C'. That is, for example, the general formula (1
') has a B' ring (or C' ring) formed by condensing another ring so as to incorporate X ¹ (or X ² ) to the benzene ring that is the b ring (or c ring). It is a compound. The resulting fused ring B' (or fused ring C') is, for example, a phenoxazine ring, a phenothiazine ring or an acridine ring.

In addition, ^the above provisions apply to ring structures in which X ¹ and/or It can also be expressed by a compound that has That is, for example, a compound having an A' ring formed by condensing another ring so as to incorporate X ¹ (and/or X ² ) to the benzene ring that is the a ring in general formula (1'). be. The resulting fused ring A' is, for example, a phenoxazine ring, a phenothiazine ring or an acridine ring.

Examples of the "aryl ring" which is ring A, ring B, and ring C in general formula (1) include aryl rings having 6 to 30 carbon atoms, preferably aryl rings having 6 to 16 carbon atoms, and 6～
An aryl ring having 12 carbon atoms is more preferred, and an aryl ring having 6 to 10 carbon atoms is particularly preferred. In addition,
This "aryl ring" is an "aryl ring formed with ring a, ring b, or ring c by bonding of adjacent groups among R ¹ to R ¹¹ " defined in general formula (1'). Correspondingly, also a
Since the ring (or b-ring, c-ring) is already composed of a benzene ring with 6 carbon atoms, 5
The total number of carbon atoms in the condensed ring in which the member rings are condensed is 9, which is the lower limit of the number of carbon atoms.

Specific "aryl rings" include a monocyclic benzene ring, a biphenyl ring, a fused bicyclic naphthalene ring, and a tricyclic terphenyl ring (m-terphenyl,
o-terphenyl, p-terphenyl), fused tricyclic ring systems such as acenaphthylene ring, fluorene ring, phenalene ring, phenanthrene ring, fused tetracyclic ring system such as triphenylene ring, pyrene ring, naphthacene ring, and fused pentacyclic ring system. Examples include certain perylene rings and pentacene rings.

Examples of the "heteroaryl ring" which is ring A, ring B, and ring C in general formula (1) include:
Examples include heteroaryl rings having 2 to 30 carbon atoms, preferably heteroaryl rings having 2 to 25 carbon atoms, more preferably heteroaryl rings having 2 to 20 carbon atoms, and even more preferably heteroaryl rings having 2 to 15 carbon atoms. , a heteroaryl ring having 2 to 10 carbon atoms is particularly preferred. Also,
Examples of the "heteroaryl ring" include a heterocycle containing, in addition to carbon, 1 to 5 heteroatoms selected from oxygen, sulfur, and nitrogen as ring constituent atoms. Note that this "heteroaryl ring" is a heteroaryl ring defined in general formula (1') that is formed by bonding adjacent groups of R ¹ to R ¹¹ together with ring a, ring b, or ring c. corresponding to “aryl ring”,
In addition, since the a-ring (or b-ring, c-ring) is already composed of a benzene ring having 6 carbon atoms,
The total number of carbon atoms in the condensed ring, in which a five-membered ring is condensed thereto, is 6, which is the lower limit of the number of carbon atoms.

Specific "heteroaryl rings" include, for example, pyrrole ring, oxazole ring, isoxazole ring, thiazole ring, isothiazole ring, imidazole ring, oxadiazole ring, thiadiazole ring, triazole ring, tetrazole ring, pyrazole ring, pyridine ring,
Pyrimidine ring, pyridazine ring, pyrazine ring, triazine ring, indole ring, isoindole ring, 1H-indazole ring, benzimidazole ring, benzoxazole ring, benzothiazole ring, 1H-benzotriazole ring, quinoline ring, isoquinoline ring, cinnoline ring , quinazoline ring, quinoxaline ring, phthalazine ring, naphthyridine ring, purine ring, pteridine ring, carbazole ring, acridine ring, phenoxathiine ring, phenoxazine ring, phenothiazine ring, phenazine ring, indolizine ring, furan ring, benzofuran ring, Examples include isobenzofuran ring, dibenzofuran ring, thiophene ring, benzothiophene ring, dibenzothiophene ring, furazane ring, and thianthrene ring.

At least one hydrogen in the above "aryl ring" or "heteroaryl ring" is the first substituent, substituted or unsubstituted "aryl", substituted or unsubstituted "heteroaryl", substituted or unsubstituted "aryl", substituted or unsubstituted "heteroaryl", "diarylamino", substituted or unsubstituted "diheteroarylamino", substituted or unsubstituted "arylheteroarylamino", substituted or unsubstituted "alkyl", substituted or unsubstituted "cycloalkyl", substituted or May be substituted with unsubstituted "alkoxy" or substituted or unsubstituted "aryloxy",
As this first substituent, "aryl", "heteroaryl", aryl of "diarylamino", heteroaryl of "diheteroarylamino", aryl and heteroaryl of "arylheteroarylamino", and "aryloxy Examples of the aryl include the monovalent groups of the above-mentioned "aryl ring" or "heteroaryl ring."

Further, the "alkyl" as the first substituent may be either straight chain or branched chain, and includes, for example, straight chain alkyl having 1 to 24 carbon atoms or branched chain alkyl having 3 to 24 carbon atoms. Alkyl having 1 to 18 carbon atoms (branched alkyl having 3 to 18 carbon atoms) is preferable, alkyl having 1 to 12 carbon atoms (branched alkyl having 3 to 12 carbon atoms) is more preferable, and alkyl having 1 to 18 carbon atoms is more preferable.
-6 alkyl (branched alkyl having 3 to 6 carbon atoms) is more preferred, and alkyl having 1 to 4 carbon atoms (branched alkyl having 3 to 4 carbon atoms) is particularly preferred.

Specific alkyls include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, t-butyl, n-pentyl, isopentyl, neopentyl, t-pentyl, n-hexyl, and 1-methyl. pentyl, 4-methyl-2-pentyl, 3,
3-dimethylbutyl, 2-ethylbutyl, n-heptyl, 1-methylhexyl, n-octyl, t-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl , 2,6-dimethyl-4-heptyl, 3,5,
5-trimethylhexyl, n-decyl, n-undecyl, 1-methyldecyl, n-dodecyl, n-tridecyl, 1-hexylheptyl, n-tetradecyl, n-pentadecyl, n
-Hexadecyl, n-heptadecyl, n-octadecyl, n-eicosyl, etc.

In addition, "cycloalkyl" as the first substituent includes cycloalkyl having 3 to 24 carbon atoms, cycloalkyl having 3 to 20 carbon atoms, cycloalkyl having 3 to 16 carbon atoms, and cycloalkyl having 3 to 24 carbon atoms.
Examples include cycloalkyl having 14 carbon atoms, cycloalkyl having 5 to 10 carbon atoms, cycloalkyl having 5 to 8 carbon atoms, cycloalkyl having 5 to 6 carbon atoms, and cycloalkyl having 5 carbon atoms.

Specific cycloalkyls include cyclopropyl, methylcyclopropyl, cyclobutyl, methylcyclobutyl, cyclopentyl, methylcyclopentyl, cyclohexyl,
Methylcyclohexyl, cycloheptyl, methylcycloheptyl, cyclooctyl, methylcyclooctyl, cyclononyl, methylcyclononyl, cyclodecyl, methylcyclodecyl, bicyclo[1.0.1]butyl, bicyclo[1.1.1]pentyl, bicyclo [2
．． 0.1] pentyl, bicyclo[1.2.1]hexyl, bicyclo[3.0.1]hexyl, bicyclo[2.1.2]heptyl, bicyclo[2.2.2]octyl, adamantyl, diamantyl, Examples include decahydronaphthalenyl and decahydroazulenyl.

Examples of "alkoxy" as the first substituent include straight chain alkoxy having 1 to 24 carbon atoms or branched chain alkoxy having 3 to 24 carbon atoms. Alkoxy having 1 to 18 carbon atoms (
Branched chain alkoxy having 3 to 18 carbon atoms) is preferable, alkoxy having 1 to 12 carbon atoms (branched alkoxy having 3 to 12 carbon atoms) is more preferable, and alkoxy having 1 to 6 carbon atoms (branched alkoxy having 3 to 6 carbon atoms) is preferable. Branched alkoxy having 1 to 4 carbon atoms (branched alkoxy having 1 to 4 carbon atoms) is more preferable;
to 4-branched alkoxy) are particularly preferred.

Specific examples of alkoxy include methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, s-butoxy, t-butoxy, pentyloxy, hexyloxy, heptyloxy, octyloxy, and the like.

The first substituent is substituted or unsubstituted "aryl", substituted or unsubstituted "heteroaryl", substituted or unsubstituted "diarylamino", substituted or unsubstituted "diheteroarylamino", substituted or unsubstituted "arylheteroarylamino", substituted or unsubstituted "alkyl", substituted or unsubstituted "cycloalkyl", substituted or unsubstituted "
"alkoxy" or substituted or unsubstituted "aryloxy" may have at least one hydrogen thereof substituted with a second substituent, as described as substituted or unsubstituted. Examples of the second substituent include aryl, heteroaryl, alkyl, or cycloalkyl, and specific examples thereof include the monovalent group of the above-mentioned "aryl ring" or "heteroaryl ring", and Reference may be made to the explanation of "alkyl" or "cycloalkyl" as substituent 1. Aryl and heteroaryl as the second substituent include aryl and heteroaryl in which at least one hydrogen is aryl such as phenyl (specific examples are the groups mentioned above), alkyl such as methyl (specific examples are the groups mentioned above), and cyclohexyl. A group substituted with a cycloalkyl such as (specific examples are the groups mentioned above) is also included in the aryl and heteroaryl as the second substituent. For example, when the second substituent is a carbazolyl group, a carbazolyl group in which at least one hydrogen at the 9-position is substituted with an aryl such as phenyl, an alkyl such as methyl, or a cycloalkyl such as cyclohexyl may also be used as the second substituent. included in heteroaryl as a substituent.

The aryl, heteroaryl, aryl of diarylamino, heteroaryl of diheteroarylamino, aryl and heteroaryl of arylheteroarylamino, or aryl of aryloxy in R ¹ to R ¹¹ of general formula (1') are general Formula (1)
Examples include the monovalent group of the "aryl ring" or "heteroaryl ring" explained in . Also,
As the alkyl, cycloalkyl or alkoxy in R ¹ to R ¹¹ , "alkyl", "cycloalkyl" or "
You can refer to the explanation of "alkoxy". Furthermore, the same applies to aryl, heteroaryl, alkyl or cycloalkyl as a substituent to these groups. Also, R ¹ to R
When adjacent groups of ¹¹ are combined to form an aryl ring or a heteroaryl ring with ring a, ring b, or ring c, heteroaryl, diarylamino, and dihetero which are substituents on these rings The same applies to arylamino, arylheteroarylamino, alkyl, cycloalkyl, alkoxy or aryloxy, and further substituents aryl, heteroaryl, alkyl or cycloalkyl.

R ^of >N-R in X ¹ and At least one hydrogen in alkyl or cycloalkyl may be substituted with, for example, alkyl or cycloalkyl. Examples of the aryl, heteroaryl, alkyl and cycloalkyl include the groups mentioned above. In particular, aryl having 6 to 10 carbon atoms (e.g. phenyl, naphthyl, etc.), heteroaryl having 2 to 15 carbon atoms (e.g. carbazolyl, etc.), alkyl having 1 to 4 carbon atoms (e.g. methyl, ethyl, etc.), 3 carbon atoms
-16 cycloalkyls (eg bicyclooctyl, adamantyl, etc.) are preferred. This explanation is the same for X ¹ and X ² in general formula (1').

R in "-C(-R) ₂ --" which is a linking group in general formula (1) is hydrogen, alkyl or cycloalkyl, and examples of this alkyl or cycloalkyl include the groups mentioned above. In particular, alkyl having 1 to 4 carbon atoms (eg, methyl, ethyl, etc.) is preferred. This explanation also applies to "-C(-R) ₂ --" which is a linking group in general formula (1').

The present invention also provides a multimer of a polycyclic aromatic compound having a plurality of unit structures represented by the general formula (1), preferably a polycyclic aromatic compound having a plurality of unit structures represented by the general formula (1'). It is a multimer of group compounds. The multimer is preferably a dimer to hexamer, more preferably a dimer to trimer, and particularly preferably a dimer. The multimer may have a plurality of the above unit structures in one compound. For example, the above unit structure may be a single bond, a linking group such as an alkylene group having 1 to 3 carbon atoms, a phenylene group, or a naphthylene group. In addition to a form in which multiple units are bonded, a form in which any ring (A ring, B ring, or C ring, a ring, b ring, or c ring) contained in the above unit structure is shared by multiple unit structures. Alternatively, any rings (A ring, B ring or C ring, a ring, b ring or c ring) included in the above unit structure may be bonded in a condensed manner. good.

Examples of such multimers include the following formula (1'-4), formula (1'-4-1), and formula (
Examples include multimeric compounds represented by formulas (1'-4-2), formulas (1'-5-1) to (1'-5-4), or formula (1'-6). The multimer compound represented by the following formula (1'-4) can be explained using the general formula (1').
It is a multimeric compound that has a unit structure represented by ') in one compound. In addition, the following formula (
1'-4-1) If explained in general formula (1'), the multimer compound represented by two general formulas (1') shares a benzene ring which is the a ring. It is a multimeric compound that has a unit structure in one compound. Furthermore, if the multimer compound represented by the following formula (1'-4-2) is explained using the general formula (1'), the three general formulas ( It is a multimeric compound having a unit structure represented by 1') in one compound. In addition, the multimer compounds represented by the following formulas (1'-5-1) to (1'-5-4) are represented by the general formula (
1'), a multimer compound having multiple unit structures represented by the general formula (1') in one compound so that the benzene ring which is the b ring (or c ring) is shared. It is. In addition, if the multimer compound represented by the following formula (1'-6) is explained in general formula (1'), for example, a benzene ring which is the b ring (or a ring, or c ring) of a certain unit structure. A multimeric compound having a plurality of unit structures represented by the general formula (1') in one compound such that the b-ring (or a-ring, c-ring) of a certain unit structure is condensed with the benzene ring. It is.

The multimeric compound has a multimeric form expressed by formula (1'-4), formula (1'-4-1) or formula (1'-4-2), and formula (1'-5-1). ~Equation (1'-5-4) or formula (
It may also be a multimer in which the multimerization form expressed by the formula (1'-6) is combined.
-5-1) to expression (1'-5-4), and expression (1'-6)
It may be a multimer that is a combination of the multimerization form expressed by the formula (1'-4), the formula (1'-4-1), or the formula (1'-4-2). Multimerization form and formula (1'-5-1
) to formula (1'-5-4) and a multimerization form expressed by formula (1'-6) may be combined.

In addition, all or part of hydrogen in the chemical structure of the polycyclic aromatic compound represented by general formula (1) or (1') and its polymer is substituted with halogen, cyano, or deuterium. Good too. For example, in formula (1), ring A, ring B, ring C (rings A to C are aryl rings or heteroaryl rings), substituents to rings A to C, and X ¹ and X ² are >N When R is -R, hydrogen in R (=aryl, heteroaryl, alkyl, cycloalkyl) may be substituted with halogen, cyano, or deuterium, but among these, all or part of hydrogen in aryl or heteroaryl may be substituted with halogen. Examples include embodiments substituted with , cyano or deuterium. Halogen is fluorine, chlorine, bromine or iodine, preferably fluorine,
Chlorine or bromine, more preferably fluorine or chlorine.

Specific examples of the polycyclic aromatic compound of the present invention include compounds represented by the following structural formula. In the structural formula below, "Me" represents a methyl group, "tBu" represents a tertiary butyl group, "iPr" represents an isopropyl group, "Ph" represents a phenyl group, and "D" represents deuterium.

3. Method for producing polycyclic aromatic compounds represented by formula (1) and multimers thereof Polycyclic aromatic compounds represented by general formulas (1) and (1') and multimers thereof are produced according to International Publication No. 2015/ It can be produced according to methods described in many known documents including JP-A No. 102118. For reference, a specific method for producing the polycyclic aromatic compound is explained in the synthesis example described later.

Basically, an intermediate is produced by first bonding ring A (ring a), ring B (ring b), and ring C (ring c) with a bonding group (group containing X ¹ or X ² ). (first reaction), and then the A ring (a ring), the B ring (b ring), and the C ring (c ring) are bonded together with a bonding group (a group containing the central element B (boron)) to form the final product. (second reaction). For the first reaction, for example, a general reaction such as a nucleophilic substitution reaction or an Ullmann reaction can be used for an etherification reaction, and a general reaction such as a Buchwald-Hartwig reaction can be used for an amination reaction. Further, in the second reaction, a tandem hetero Friedel-Crafts reaction (continuous aromatic electrophilic substitution reaction, the same applies hereinafter) can be used. Also, somewhere in these reaction steps, halogenation,
Manufacture compounds that are halogenated, cyanated, or deuterated at desired positions by using cyanated or deuterated raw materials or by adding a halogenation, cyanation, or deuteration step can do.

In the second reaction, as shown in schemes (1) and (2) below, ring A (ring a), ring B (ring b)
This is a reaction that introduces the central element B (boron) that bonds the C ring (c ring), and for example, X
The case where ¹ and X ² are >O is shown below. First, the hydrogen atom between X ¹ and X ² is orthometalized with n-butyllithium, sec-butyllithium, t-butyllithium, or the like.
Next, boron trichloride, boron tribromide, etc. are added to perform a lithium-boron metal exchange, and a Brønsted base such as N,N-diisopropylethylamine is added to cause a tandem Bora-Friedel-Crafts reaction. can get things. In the second reaction, a Lewis acid such as aluminum trichloride may be added to accelerate the reaction. Note that the definitions of the symbols in each structural formula in the following schemes (1) and (2) are the same as the above definitions.

Note that the above schemes (1) and (2) mainly show the method for producing the polycyclic aromatic compound represented by the general formula (1) or (1'), but for the multimer, multiple A ring (a ring), B
It can be produced by using an intermediate having a ring (b ring) and a C ring (c ring). Details will be explained in the following schemes (3) to (5). In this case, the desired product can be obtained by doubling or tripling the amount of the reagent such as butyllithium used.

In addition, even when X ¹ and X ² are >NR, or when either is >NR, it can be produced in the same manner as above by using an amine compound as an intermediate. .

Specific examples of the solvent used in each of the above schemes include t-butylbenzene and xylene.

In addition, as orthometalation reagents, methyllithium, n-butyllithium, sec-
Examples include alkyllithiums such as butyllithium and t-butyllithium, and organic alkali compounds such as lithium diisopropylamide, lithium tetramethylpiperidide, lithium hexamethyldisilazide, and potassium hexamethyldisilazide.

In addition, examples of the Brønsted base include N,N-diisopropylethylamine, triethylamine, 2,2,6,6-tetramethylpiperidine, 1,2,2,6,6-pentamethylpiperidine, N,N-dimethylaniline, N,N-dimethyltoluidine, 2,6-lutidine, sodium tetraphenylborate, potassium tetraphenylborate, triphenylborane, tetraphenylsilane, Ar ₄ BNa, Ar ₄ BK, Ar ₃ B, Ar ₄ Si ( , Ar is aryl such as phenyl).

In addition, examples of Lewis acids include AlCl ₃ , AlBr ₃ , AlF ₃ , BF ₃ .OEt ₂ , B
_Cl3 , _BBr3 , _GaCl3 , _GaBr3 , _InCl3 , _InBr3 , In(OTf)
₃ , _SnCl4 , _SnBr4 , AgOTf, _ScCl3 , Sc(OTf) ₃ , _ZnCl2
, ZnBr ₂ , Zn(OTf) ₂ , MgCl ₂ , MgBr ₂ , Mg(OTf) ₂ , LiO
Tf, NaOTf, KOTf, _Me3SiOTf , Cu(OTf) ₂ , _CuCl2 , YC
l ₃ , Y(OTf) ₃ , TiCl ₄ , TiBr ₄ , ZrCl ₄ , ZrBr ₄ , FeCl ₃
, FeBr ₃ , CoCl ₃ , CoBr ₃ and the like.

4. Pyrene compound represented by general formula (2) The pyrene compound represented by general formula (2) basically functions as a host.

In the above formula (2),
s pyrene moieties and p Ar moieties are bonded at any position of * of the pyrene moiety and any position of the Ar moiety,
At least one hydrogen in the pyrene moiety is each independently an aryl having 6 to 10 carbon atoms, a heteroaryl having 2 to 11 carbon atoms, an alkyl having 1 to 30 carbon atoms, a cycloalkyl having 3 to 24 carbon atoms, or a cycloalkyl having 3 to 24 carbon atoms. Alkenyl having 2 to 30 carbon atoms, alkoxy having 1 to 30 carbon atoms or 6 carbon atoms
-30 aryloxy may be substituted, and at least one hydrogen in these may be independently substituted with aryl having 6 to 10 carbon atoms, heteroaryl having 2 to 11 carbon atoms,
Optionally substituted with alkyl having 1 to 30 carbon atoms, cycloalkyl having 3 to 24 carbon atoms, alkenyl having 2 to 30 carbon atoms, alkoxy having 1 to 30 carbon atoms, or aryloxy having 6 to 30 carbon atoms,
Ar is each independently an aryl having 14 to 40 carbon atoms or a heteroaryl having 12 to 40 carbon atoms, and at least one hydrogen therein is each independently an aryl having 6 to 10 carbon atoms, an aryl having 6 to 10 carbon atoms, or a heteroaryl having 12 to 40 carbon atoms. heteroaryl having 2 to 11 carbon atoms, alkyl having 1 to 30 carbon atoms,
Optionally substituted with cycloalkyl having 3 to 24 carbon atoms, alkenyl having 2 to 30 carbon atoms, alkoxy having 1 to 30 carbon atoms, or aryloxy having 6 to 30 carbon atoms,
s and p are each independently an integer of 1 or 2, s and p cannot be 2 at the same time, and when s is 2, the two pyrene moieties are structurally the same including the substituents. and may be different, and when p is 2, the two Ar moieties may be structurally the same or different including the substituents, and,
At least one hydrogen in the compound represented by formula (2) may be independently substituted with halogen, cyano, or deuterium.

Ar is an aryl having 14 to 40 carbon atoms or a heteroaryl having 12 to 40 carbon atoms, and various substituents can be bonded to these, and specific examples of Ar include the following general formula (Ar-1)
Alternatively, a group represented by the general formula (Ar-2) can be mentioned. R ¹ to R ⁸ and R ¹⁰ to R
¹⁹ is a substituent.

Furthermore, in the group represented by formula (Ar-2), an example of a group in which adjacent R ¹⁸ and R ¹⁹ bond to each other to form a condensed ring is a group represented by the following general formula (Ar-3). It will be done. R
²⁰ to ^R35 are substituents.

More specific examples of the group represented by formula (Ar-1) or formula (Ar-2) include groups represented by any of the following general formulas. Among these, formula (Ar-1-1),
A group represented by formula (Ar-1-2), formula (Ar-1-3), formula (Ar-1-4), formula (Ar-2-2) or formula (Ar-2-4) is Preferably, formula (Ar-1-2), formula (Ar-1-
3), a group represented by formula (Ar-1-4) or formula (Ar-2-4) is more preferred. Although substituents are not explicitly shown in each structural formula below, at least one hydrogen in each structure may be substituted. In addition, the group represented by the following formula (Ar-2-4) is the group represented by the above formula (Ar-3)
It corresponds to the group represented by

Aryl having 14 to 40 carbon atoms or heteroaryl having 12 to 40 carbon atoms as Ar;
The first substituent to the pyrene moiety (aryl having 6 to 10 carbon atoms, heteroaryl having 2 to 11 carbon atoms, alkyl having 1 to 30 carbon atoms, cycloalkyl having 3 to 24 carbon atoms, cycloalkyl having 2 to 30 carbon atoms) alkenyl, alkoxy having 1 to 30 carbon atoms or aryloxy having 6 to 30 carbon atoms, preferably aryl having 6 to 10 carbon atoms) and a second substituent to the first substituent (alkoxy having 6 to 30 carbon atoms, preferably aryl having 6 to 10 carbon atoms);
Aryl of 0, heteroaryl of 2 to 11 carbon atoms, alkyl of 1 to 30 carbon atoms, 3 carbon atoms
-24 cycloalkyl, C2-30 alkenyl, C1-30 alkoxy or C6-30 aryloxy, preferably 6-10 aryl), and substituents for Ar ( R ¹ to R ⁸ of formula (Ar-1), R ¹⁰ to R ¹⁹ of formula (Ar-2)
, R ²⁰ to R ³⁵ of formula (Ar-3), and formula (Ar-1-1) to formula (Ar-2-4
) are substituents not specified in C 6-10 aryl, C 2-11 heteroaryl, C 1-30 alkyl, C 3-24 cycloalkyl, C 2-3
0 alkenyl, alkoxy having 1 to 30 carbon atoms, or aryloxy having 6 to 30 carbon atoms,
(preferably alkyl having 1 to 30 carbon atoms) will be summarized below.

Aryl having 14 to 40 carbon atoms or heteroaryl having 12 to 40 carbon atoms as Ar is preferably aryl having 14 to 35 carbon atoms or heteroaryl having 12 to 35 carbon atoms, more preferably 14 to 30 carbon atoms. aryl or heteroaryl having 12 to 30 carbon atoms, more preferably aryl having 14 to 25 carbon atoms or heteroaryl having 12 to 25 carbon atoms, particularly preferably aryl having 14 to 20 carbon atoms or heteroaryl having 12 to 25 carbon atoms. ～20
heteroaryl, most preferably aryl having 14 to 18 carbon atoms or aryl having 12 carbon atoms.
-18 heteroaryl.

Specific aryls include phenyl which is a monocyclic system, biphenylyl which is a bicyclic system, naphthyl which is a fused bicyclic system, terphenylyl (m-terphenylyl, o-terphenylyl, p-terphenylyl) which is a tricyclic system, and fused Examples include tricyclic ring systems such as anthracenyl, acenaphthylenyl, fluorenyl, phenalenyl, and phenanthrenyl, fused tetracyclic ring systems such as triphenylenyl and naphthacenyl, and fused pentacyclic ring systems such as perylenyl and pentacenyl.

Specific heteroaryls include, for example, pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, oxadiazolyl, thiadiazolyl,
Triazolyl, tetrazolyl, pyrazolyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, indolyl, isoindolyl, 1H-indazolyl, benzimidazolyl, benzoxazolyl, benzothiazolyl, 1H-benzotriazolyl, quinolyl, isoquinolyl, cinnolyl, quinazolyl, quinoxalinyl, Phthalazinyl, naphthyridinyl, purinyl, pteridinyl, carbazolyl, acridinyl, phenoxathiinyl, phenoxazinyl, phenothiazinyl, phenazinyl, indolizinyl, furyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, thienyl, benzo[b]thienyl, dibenzothienyl, Examples include furazanil, oxadiazolyl, thianthrenyl, naphthobenzofuranyl and naphthobenzothienyl.

In addition, a first substituent to the pyrene moiety and a second substituent to the first substituent, and A
Regarding the substituent to r, specific examples of aryl having 6 to 10 carbon atoms are phenyl or naphthyl, and specific examples of heteroaryl having 2 to 11 carbon atoms are cited from the above-mentioned heteroaryl groups. I can do it.

Aryloxy having 6 to 30 carbon atoms is a group in which the hydrogen of the hydroxyl group is substituted with aryl having 6 to 30 carbon atoms, and this aryl is preferably aryl having 6 to 25 carbon atoms, and more preferably aryl having 6 to 25 carbon atoms. An aryl having 6 to 20 carbon atoms, more preferably an aryl having 6 to 15 carbon atoms, particularly preferably an aryl having 6 to 10 carbon atoms, and specific examples of the aryl include those cited from the above-mentioned aryl groups. can do.

Alkyl having 1 to 30 carbon atoms may be linear or branched; for example, alkyl having 1 to 30 carbon atoms may be linear or branched.
-24 straight chain alkyl or branched chain alkyl having 3 to 24 carbon atoms is preferable, and preferably 1 to 1 carbon atoms.
8 alkyl (branched alkyl having 3 to 18 carbon atoms) is more preferable, alkyl having 1 to 12 carbon atoms (branched alkyl having 3 to 12 carbon atoms) is even more preferable, and alkyl having 1 to 6 carbon atoms (branched alkyl having 3 to 12 carbon atoms) is more preferable. Branched chain alkyl having 3 to 6 carbon atoms) is particularly preferred, and alkyl having 1 to 4 carbon atoms (branched chain alkyl having 3 to 6 carbon atoms
-4 branched alkyl) are particularly preferred, methyl, ethyl, isopropyl or t-
Butyl is more preferred among them, and methyl or t-butyl is most preferred.

Specific alkyls include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, t-butyl, n-pentyl, isopentyl, neopentyl, t-pentyl, n-hexyl, and 1-methyl. pentyl, 4-methyl-2-pentyl, 3,
3-dimethylbutyl, 2-ethylbutyl, n-heptyl, 1-methylhexyl, n-octyl, t-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl , 2,6-dimethyl-4-heptyl, 3,5,
5-trimethylhexyl, n-decyl, n-undecyl, 1-methyldecyl, n-dodecyl, n-tridecyl, 1-hexylheptyl, n-tetradecyl, n-pentadecyl, n
-hexadecyl, n-heptadecyl, n-octadecyl, n-eicosyl, and the like.

Cycloalkyl having 3 to 24 carbon atoms includes, for example, cycloalkyl having 3 to 20 carbon atoms, cycloalkyl having 3 to 16 carbon atoms, cycloalkyl having 3 to 14 carbon atoms, cycloalkyl having 5 to 10 carbon atoms, and cycloalkyl having 3 to 10 carbon atoms. Cycloalkyl having 5 to 8 carbon atoms, cycloalkyl having 5 to 6 carbon atoms, 5 carbon atoms
Examples include cycloalkyl.

Specific cycloalkyls include cyclopropyl, methylcyclopropyl, cyclobutyl, methylcyclobutyl, cyclopentyl, methylcyclopentyl, cyclohexyl,
Methylcyclohexyl, cycloheptyl, methylcycloheptyl, cyclooctyl, methylcyclooctyl, cyclononyl, methylcyclononyl, cyclodecyl, methylcyclodecyl, bicyclo[1.0.1]butyl, bicyclo[1.1.1]pentyl, bicyclo [2
．． 0.1] pentyl, bicyclo[1.2.1]hexyl, bicyclo[3.0.1]hexyl, bicyclo[2.1.2]heptyl, bicyclo[2.2.2]octyl, adamantyl, diamantyl, Examples include decahydronaphthalenyl and decahydroazulenyl.

The alkenyl having 2 to 30 carbon atoms is, for example, preferably an alkenyl having 2 to 20 carbon atoms, more preferably an alkenyl having 2 to 10 carbon atoms, and even more preferably an alkenyl having 2 to 6 carbon atoms.
Alkenyl having 2 to 4 carbon atoms is particularly preferred.

Specific alkenyls include vinyl, 1-propenyl, 2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl,
Examples include 4-pentenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl and 5-hexenyl.

Alkoxy having 1 to 30 carbon atoms is, for example, preferably alkoxy having 1 to 24 carbon atoms (branched alkoxy having 3 to 24 carbon atoms), and more preferably alkoxy having 1 to 18 carbon atoms (branched alkoxy having 3 to 24 carbon atoms). (branched alkoxy having 18 carbon atoms), more preferably alkoxy having 1 to 12 carbon atoms (branched alkoxy having 3 to 12 carbon atoms), particularly preferably alkoxy having 1 to 12 carbon atoms.
6 alkoxy (branched alkoxy having 3 to 6 carbon atoms), most preferably 1 carbon alkoxy
-4 alkoxy (branched alkoxy having 3 to 4 carbon atoms).

Specific examples of alkoxy include methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, s-butoxy, t-butoxy, pentyloxy, hexyloxy, heptyloxy and octyloxy.

In formulas (Ar-1) and (Ar-2), adjacent groups among R ¹ to R ⁸ and adjacent groups among R ¹⁰ to R ¹⁹ are bonded to each other to form a condensed ring. It's okay. Adjacent groups are combinations other than R ⁴ and R ⁵ or R ¹³ and R ¹⁴ , such as R ¹ and R ² . The structure in which the fused rings are formed in this way is the above formula (Ar-1-2) to formula (
Ar-1-12) and the above formulas (Ar-2-2) to (Ar-2-4) (formula (Ar-3)). On the other hand, the above formula (Ar-1-1) and formula (Ar-2-1) have structures that do not contain a condensed ring. Examples of the formed condensed ring include a benzene ring, a naphthalene ring, a phenanthrene ring, a thiophene ring, a pyrrole ring, or a furan ring, but preferably an aryl ring such as a benzene ring, a naphthalene ring, or a phenanthrene ring. More preferred is a benzene ring.

The condensed ring formed by bonding adjacent groups to each other includes aryl having 6 to 10 carbon atoms, heteroaryl having 2 to 11 carbon atoms, alkyl having 1 to 30 carbon atoms, cycloalkyl having 3 to 24 carbon atoms, carbon It may be substituted with alkenyl having 2 to 30 carbon atoms, alkoxy having 1 to 30 carbon atoms, or aryloxy having 6 to 30 carbon atoms, and these may be substituted with alkyl having 1 to 6 carbon atoms or cycloalkyl having 3 to 14 carbon atoms. The detailed explanation of these groups can be referred to the above explanation.

Moreover, Z is >CR ₂ , >NR, >O or >S, and among these, preferably >CR ₂ or >O, more preferably >CR ₂ , and in >CR ₂ R (aryl having 6 to 12 carbon atoms, which may be substituted with alkyl having 1 to 6 carbon atoms, cycloalkyl having 3 to 14 carbon atoms, alkyl having 1 to 4 carbon atoms, or cycloalkyl having 5 to 10 carbon atoms,
or heteroaryl having 2 to 12 carbon atoms, which may be substituted with alkyl having 1 to 4 carbon atoms or cycloalkyl having 5 to 10 carbon atoms), and R in >NR (having 1 to 4 carbon atoms);
alkyl having 5 to 10 carbon atoms, cycloalkyl having 5 to 10 carbon atoms, alkyl having 1 to 4 carbon atoms or 5 carbon atoms
Aryl having 6 to 12 carbon atoms which may be substituted with cycloalkyl having 1 to 10 carbon atoms, or aryl having 2 to 12 carbon atoms which may be substituted with alkyl having 1 to 4 carbon atoms or cycloalkyl having 5 to 10 carbon atoms. For details of these groups, the above description of alkyl, cycloalkyl, aryl and heteroaryl can be cited.

For Z > CR ₂ , the R's may be bonded to each other to form a ring, in which case a spiro structure is formed.

The above formula (2) means that s pyrene moieties and p Ar moieties are bonded at the * position (1st and/or 2nd position) of the pyrene moiety, and s and p are each independently 1
or an integer of 2, and s and p cannot be 2 at the same time. Since the pyrene moiety has a symmetrical structure, the 1st and 2nd positions of the pyrene moiety can be indicated by two * in the case of s=1, p=1, s=2, p=1, but s=1, When p=2, two Ar moieties can each be bonded to six positions of the pyrene moiety, which is indicated by six asterisks. When s is 2, the two pyrene moieties may be structurally the same or different, including the substituents, and when p is 2, the two Ar moieties, including the substituents, may be structurally the same or different. They may be structurally the same or different. That is, as described above, various substituents may be bonded to the pyrene structure of the pyrene moiety, and when substituents are bonded, the pyrene moiety includes the bonded substituents. Similarly, Ar
The moiety, including the bonded substituents, constitutes the Ar moiety. When the pyrene compound represented by formula (2) contains multiple pyrene moieties or Ar moieties, the pyrene moieties including substituents and the Ar moieties including substituents are structurally the same. may also be different,
Preferably, they are the same.

Regarding the bond between the pyrene moiety and the Ar moiety, in the pyrene moiety, the * position (1
and/or 2-position), but conversely, the pyrene moiety may be bonded at any position in the Ar moiety. For example, in formula (Ar-1) or formula (Ar-2), which is an example of Ar, a pyrene moiety may be bonded at any position from R ¹ to R ⁸ and from R ¹⁰ to R ¹⁹ , and further, When adjacent groups are bonded to each other to form a condensed ring, they may be bonded to the condensed ring. In addition, when a substituent such as aryl is selected as R ¹ to R ⁸ and R ¹⁰ to R ¹⁹ , any position in the aryl, or aryl, etc. as R in >CR ₂ and >NR as Z may be attached at any position on the selected aryl. Among these bonding positions, any one of R ¹ to R ⁸ or R ¹⁰ to R ¹⁹ in formula (Ar-1) or formula (Ar-2) is preferred. These explanations are the same for formulas below formula (Ar-1) and formula (Ar-2).

Furthermore, all or part of hydrogen in the pyrene compound represented by formula (2) may be substituted with halogen, cyano, or deuterium. For example, in formula (2), hydrogen in the pyrene moiety or Ar moiety may be replaced with halogen, cyano, or deuterium. Halogen is fluorine, chlorine, bromine or iodine, preferably fluorine, chlorine or bromine, more preferably fluorine.

Specific examples of the pyrene compound of the present invention include compounds represented by the following structural formula. In the structural formula below, "Me" represents a methyl group, "Et" represents an ethyl group, "tBu" represents a tertiary butyl group, "iPr" represents an isopropyl group, and "D" represents deuterium.

Among the above compounds, formula (2-1), formula (2-2) to formula (2-20), formula (2-41)
) ~ Formula (2-43) Formula (2-46), Formula (2-47) ~ Formula (2-173), Formula (2-17
4), Formula (2-175) to Formula (2-215), Formula (2-351) to Formula (2-354), Formula (2-356), Formula (2-357), Formula (2-358) ), formula (2-359), formula (2-3
60) ~ Formula (2-430), Formula (2-1001), Formula (2-1002) ~ Formula (2-101)
2), Formula (2-1080), Formula (2-1081) to Formula (2-1091) are preferred.

Also, formula (2-1), formula (2-46), formula (2-174), formula (2-350), formula (2
-356), formula (2-359), formula (2-1001), and formula (2-1080) are more preferred.

5. Method for producing a pyrene compound represented by formula (2) The pyrene compound represented by formula (2) has a structure in which various substituents are bonded to the pyrene skeleton or the skeleton of a compound represented by Ar. However, it can be manufactured using a known method. Intermediates are produced by commonly used halogenation reactions, boron oxidation reactions, or boronic acid esterification reactions, and the produced intermediates are used for Suzuki coupling reactions, other metalation reactions, and cross-linking via metal species. By performing a coupling reaction (Negishi coupling reaction, Kumada-Tamao coupling reaction, Kosugi-Migita-Stille coupling reaction, etc.), the formula (2
) can be produced. In addition, after producing an intermediate having a substituent such as an alkoxy group such as a methoxy group and converting it into an -OH form through a demethylation reaction using pyridine hydrochloride, etc., a reagent such as trifluoromethanesulfonic anhydride is used. The pyrene compound represented by formula (2) can also be produced by converting the sulfonic acid ester into a sulfonic acid ester and performing a cross-coupling reaction such as a Suzuki coupling reaction. Moreover, commercially available materials can also be used as intermediates having these halogens, boronic acids, boronic esters, or sulfonic esters. For reference, a specific method for producing the pyrene-based compound is explained in the synthesis example described below.

6. Organic EL device The organic EL device according to this embodiment will be described in detail below based on the drawings. Figure 1
1 is a schematic cross-sectional view showing an organic EL element according to the present embodiment.

<Structure of organic electroluminescent device>
The organic EL element 100 shown in FIG. 1 includes a substrate 101, an anode 102 provided on the substrate 101, a hole injection layer 103 provided on the anode 102, and a A hole transport layer 104 provided, a light emitting layer 105 provided on the hole transport layer 104, an electron transport layer 106 provided on the light emitting layer 105, and a light emitting layer 105 provided on the electron transport layer 106. It has an electron injection layer 107 and a cathode 108 provided on the electron injection layer 107.

Note that the organic EL element 100 can be manufactured in reverse order, for example, by manufacturing the substrate 101 and the substrate 10.
1, an electron injection layer 107 provided on the cathode 108, an electron transport layer 106 provided on the electron injection layer 107, and an electron transport layer 106 provided on the electron transport layer 106. A light emitting layer 105, a hole transport layer 104 provided on the light emitting layer 105, and a hole transport layer 104.
It is also possible to have a configuration including a hole injection layer 103 provided on the hole injection layer 103 and an anode 102 provided on the hole injection layer 103.

All of the above layers are not indispensable, and the minimum structural unit is the anode 102, the light emitting layer 105, and the cathode 108. Layer 107 is an optional layer. Moreover, each of the above layers may be composed of a single layer or a plurality of layers.

In addition to the above-mentioned configuration of "substrate/anode/hole injection layer/hole transport layer/light emitting layer/electron transport layer/electron injection layer/cathode", examples of the layers constituting the organic EL element include ""Substrate/Anode/Hole transport layer/Light emitting layer/Electron transport layer/Electron injection layer/Cathode", "Substrate/Anode/Hole injection layer/Light emitting layer/Electron transport layer/Electron injection layer/Cathode", "Substrate/ Anode / hole injection layer / hole transport layer / light emitting layer / electron injection layer / cathode", "substrate / anode / hole injection layer / hole transport layer / light emitting layer / electron transport layer /
"Cathode", "Substrate/Anode/Emissive layer/Electron transport layer/Electron injection layer/Cathode", "Substrate/Anode/Hole transport layer/Emissive layer/Electron injection layer/Cathode", "Substrate/Anode/Hole transport layer/emissive layer/electron transport layer/cathode", "substrate/anode/hole injection layer/emissive layer/electron injection layer/cathode", "substrate/anode/hole injection layer/emissive layer/electron transport layer/cathode" ”, “Substrate/Anode/Light-emitting layer/Electron transport layer/Cathode”,
The structure may be "substrate/anode/light emitting layer/electron injection layer/cathode".

<Substrate in organic electroluminescent device>
The substrate 101 is a support for the organic EL element 100, and is usually made of quartz, glass, metal, plastic, or the like. The substrate 101 is formed into a plate shape, a film shape, or a sheet shape depending on the purpose. For example, a glass plate, a metal plate, a metal foil, a plastic film, a plastic sheet, etc. are used. Among these, glass plates and plates made of transparent synthetic resins such as polyester, polymethacrylate, polycarbonate, and polysulfone are preferred. If it is a glass substrate, soda lime glass or non-alkali glass may be used, and the thickness may be sufficient to maintain mechanical strength, for example, 0.2 mm or more. The upper limit of the thickness is, for example, 2 mm or less, preferably 1 mm or less. Regarding the material of the glass, alkali-free glass is preferable because fewer ions elute from the glass, but soda lime glass coated with a barrier coating such as SiO ₂ is also commercially available, so it is recommended to use this. can. In addition, the substrate 101 may be provided with a gas barrier film such as a dense silicon oxide film on at least one side of the substrate 101 in order to improve gas barrier properties. In particular, a synthetic resin plate, film, or sheet with low gas barrier properties may be used as the substrate 101. When used, it is preferable to provide a gas barrier film.

<Anode in organic electroluminescent device>
The anode 102 plays the role of injecting holes into the light emitting layer 105. Note that when the hole injection layer 103 and/or the hole transport layer 104 are provided between the anode 102 and the light emitting layer 105, holes are injected into the light emitting layer 105 through these. .

Examples of materials forming the anode 102 include inorganic compounds and organic compounds. Examples of inorganic compounds include metals (aluminum, gold, silver, nickel, palladium, chromium, etc.), metal oxides (indium oxide, tin oxide, indium-tin oxide (I
TO), indium-zinc oxide (IZO), etc.), metal halides (copper iodide, etc.),
Examples include copper sulfide, carbon black, ITO glass, and Nesa glass. Examples of organic compounds include polythiophenes such as poly(3-methylthiophene), polypyrrole,
Examples include conductive polymers such as polyaniline. In addition, materials that are used as anodes for organic EL devices may be selected as appropriate.

The resistance of the transparent electrode is not limited as long as it can supply sufficient current for light emission of the light emitting element, but from the viewpoint of power consumption of the light emitting element, it is desirable that the resistance be low. For example, 300Ω/
□The following ITO substrates can function as element electrodes, but since it is now possible to supply substrates with a resistance of about 10Ω/□, for example, 100 to 5Ω/□, preferably 50 to 5Ω/□.
It is particularly desirable to use a low resistance product with □. The thickness of ITO can be arbitrarily selected according to the resistance value, but it is usually used between 50 and 300 nm.

<Hole injection layer and hole transport layer in organic electroluminescent device>
The hole injection layer 103 plays a role of efficiently injecting holes moving from the anode 102 into the light emitting layer 105 or the hole transport layer 104. The hole transport layer 104 plays a role of efficiently transporting holes injected from the anode 102 or holes injected from the anode 102 via the hole injection layer 103 to the light emitting layer 105. The hole injection layer 103 and the hole transport layer 104 are each formed by laminating and mixing one or more hole injection/transport materials, or by laminating and mixing one or more hole injection/transport materials, or
Formed by a mixture of transport material and polymeric binder. Alternatively, the layer may be formed by adding an inorganic salt such as iron(III) chloride to the hole injection/transport material.

As a hole injection/transport material, it is necessary to efficiently inject and transport holes from the positive electrode between the electrodes where an electric field is applied, and the material has high hole injection efficiency and efficiently transports the injected holes. It is desirable to do so. For this purpose, it is preferable to use a substance that has a low ionization potential, high hole mobility, excellent stability, and does not easily generate trapping impurities during production and use.

Materials for forming the hole injection layer 103 and the hole transport layer 104 include compounds conventionally used as hole charge transport materials in photoconductive materials, p-type semiconductors, and hole injection layers of organic EL devices. Any compound can be selected and used from among the known compounds used in the hole transport layer. Specific examples thereof include carbazole derivatives (N-phenylcarbazole, polyvinylcarbazole, etc.), biscarbazole derivatives such as bis(N-arylcarbazole) or bis(N-alkylcarbazole), triarylamine derivatives (aromatic tertiary Polymer with amino in main chain or side chain, 1,1-bis(4-di-
p-tolylaminophenyl)cyclohexane, N,N'-diphenyl-N,N'-di(3
-methylphenyl)-4,4'-diaminobiphenyl, N,N'-diphenyl-N,N'
-dinaphthyl-4,4'-diaminobiphenyl, N,N'-diphenyl-N,N'-di(
3-methylphenyl)-4,4'-diphenyl-1,1'-diamine, N,N'-dinaphthyl-N,N'-diphenyl-4,4'-diphenyl-1,1'-diamine, N ⁴ ,N ^4
' -diphenyl-N ⁴ ,N ^4' -bis(9-phenyl-9H-carbazol-3-yl)
-[1,1'-biphenyl]-4,4'-diamine, N ⁴ ,N ⁴ ,N ^4' ,N ^4' -tetra[1,1'-biphenyl]-4-yl)-[1,1 '-biphenyl]-4,4'-diamine, triphenylamine derivatives such as 4,4',4''-tris(3-methylphenyl(phenyl)amino)triphenylamine, starburst amine derivatives, etc.), stilbene derivatives , phthalocyanine derivatives (metal-free, copper phthalocyanine, etc.), pyrazoline derivatives, hydrazone compounds, benzofuran derivatives and thiophene derivatives, oxadiazole derivatives, quinoxaline derivatives (for example, 1,4,5,8,9,12-hexaazatriphenylene) -2,3,6,7,10,11-hexacarbonitrile, etc.), heterocyclic compounds such as porphyrin derivatives, polysilane, etc. In polymer systems, polycarbonates, styrene derivatives, and polyvinyl having the above monomers in their side chains are used. Carbazole, polysilane, and the like are preferred, but there are no particular limitations on the compound as long as it forms a thin film necessary for producing a light emitting device, can inject holes from the anode, and can transport holes.

It is also known that the conductivity of organic semiconductors is strongly influenced by their doping. Such an organic semiconductor matrix material is composed of a compound with good electron donating properties or a compound with good electron accepting properties. Due to the doping of electron donating substances,
Strong electron acceptors such as tetracyanoquinone dimethane (TCNQ) or 2,3,5,6-tetrafluorotetracyano-1,4-benzoquinone dimethane (F4TCNQ) are known (see, for example, the document “M. Pfeiffer, A. Beyer, T. Fritz, K. Leo, Appl. Phys. Lett., 73(22), 32
02-3204(1998)" and the document "J. Blochwitz, M. Pheiffer, T. Fritz, K. Leo, Appl. Phys. Lett.,
73(6), 729-731 (1998)). These generate so-called holes by electron transfer processes in electron-donating base materials (hole-transporting materials). Depending on the number and mobility of holes, the conductivity of the base material varies considerably. As matrix materials having hole transport properties, for example benzidine derivatives (TPD etc.) or starburst amine derivatives (TDATA etc.) or certain metal phthalocyanines (in particular zinc phthalocyanine (ZnPc) etc.) are known ( (Japanese Patent Application Publication No. 2005-167175).

<Light-emitting layer in organic electroluminescent device>
The light-emitting layer 105 is a layer that emits light by recombining holes injected from the anode 102 and electrons injected from the cathode 108 between the electrodes to which an electric field is applied. The material for forming the light-emitting layer 105 may be any compound (luminescent compound) that emits light when excited by recombination of holes and electrons, can form a stable thin film shape, and is in a solid state. It is preferable that the compound is a compound that exhibits strong luminescence (fluorescence) efficiency. In the present invention, as materials for the light emitting layer, for example, a pyrene compound represented by the above general formula (2) as a host material and a polycyclic aromatic compound represented by the above general formula (1) as a dopant material, for example. compounds and multimers thereof.

The light-emitting layer may be a single layer or composed of multiple layers, and each is formed from a material for the light-emitting layer (host material, dopant material). The host material and the dopant material may each be one type or a combination of a plurality of types. The dopant material may be contained entirely or partially in the host material. As a doping method, it can be formed by a co-evaporation method with a host material, but it may also be mixed with the host material in advance and then vapor-deposited at the same time.

The amount of host material used varies depending on the type of host material, and may be determined depending on the characteristics of the host material. The amount of host material to be used is preferably 50 to 50% of the total luminescent layer material.
It is 99.999% by weight, more preferably 80 to 99.95% by weight, even more preferably 90 to 99.9% by weight.

The amount of dopant material to be used varies depending on the type of dopant material, and may be determined according to the characteristics of the dopant material. The amount of the dopant to be used is preferably 0.001 to 50% by weight, more preferably 0.05 to 20% by weight, and even more preferably 0.1 to 10% by weight based on the entire material for the light emitting layer. be. The above range is preferable in that, for example, concentration quenching phenomenon can be prevented.

Host materials that can be used in combination with the pyrene compound represented by formula (2) include fused ring derivatives such as anthracene, which have long been known as luminescent materials, and bisstyryls such as bisstyrylanthracene derivatives and distyrylbenzene derivatives. derivatives, tetraphenylbutadiene derivatives, cyclopentadiene derivatives, fluorene derivatives, benzofluorene derivatives and the like.

The dopant material that can be used in combination with the polycyclic aromatic compound represented by formula (1) and its polymer is not particularly limited, and known compounds can be used, and various dopant materials can be used depending on the desired emission color. You can choose from a variety of materials. Specifically, for example, fused ring derivatives such as phenanthrene, anthracene, tetracene, pentacene, perylene, rubrene and chrysene, benzoxazole derivatives, benzothiazole derivatives, benzimidazole derivatives, benzotriazole derivatives, oxazole derivatives, oxadiazole derivatives, Bis-styryl derivatives such as thiazole derivatives, imidazole derivatives, thiadiazole derivatives, triazole derivatives, pyrazoline derivatives, stilbene derivatives, thiophene derivatives, tetraphenylbutadiene derivatives, cyclopentadiene derivatives, bis-styrylanthracene derivatives and distyrylbenzene derivatives (JP-A-1-245087) ), bisstyrylarylene derivatives (JP-A-2-247278), diazaindacene derivatives, furan derivatives, benzofuran derivatives, phenylisobenzofuran, dimesitylisobenzofuran, di(2-methylphenyl)isobenzofuran, di(2-methylphenyl)isobenzofuran, Isobenzofuran derivatives such as trifluoromethylphenyl)isobenzofuran and phenylisobenzofuran, dibenzofuran derivatives, 7-dialkylaminocoumarin derivatives, 7-piperidinocoumarin derivatives, 7-
Hydroxycoumarin derivative, 7-methoxycoumarin derivative, 7-acetoxycoumarin derivative, 3-benzothiazolylcoumarin derivative, 3-benzimidazolylcoumarin derivative, 3
- Coumarin derivatives such as benzoxazolyl coumarin derivatives, dicyanomethylenepyran derivatives, dicyanomethylenethiopyran derivatives, polymethine derivatives, cyanine derivatives, oxobenzoanthracene derivatives, xanthene derivatives, rhodamine derivatives, fluorescein derivatives, pyrylium derivatives, carbostyryl derivatives , acridine derivatives, oxazine derivatives,
Phenylene oxide derivatives, quinacridone derivatives, quinazoline derivatives, pyrrolopyridine derivatives, furopyridine derivatives, pyrromethene derivatives, perinone derivatives, pyrrolopyrrole derivatives, squarylium derivatives, violanthrone derivatives, phenazine derivatives, acridone derivatives, deazaflavin derivatives, fluorene derivatives and benzofluorene derivatives, etc. can give.

<Electron injection layer and electron transport layer in organic electroluminescent device>
The electron injection layer 107 plays a role of efficiently injecting electrons moving from the cathode 108 into the light emitting layer 105 or the electron transport layer 106. The electron transport layer 106 plays a role of efficiently transporting electrons injected from the cathode 108 or electrons injected from the cathode 108 via the electron injection layer 107 to the light emitting layer 105. The electron transport layer 106 and the electron injection layer 107 are each formed by laminating or mixing one or more types of electron transport/injection materials, or by laminating or mixing one or more types of electron transport/injection materials.
Formed by a mixture of injection material and polymeric binder.

The electron injection/transport layer is a layer that is in charge of injecting electrons from the cathode and further transporting electrons, and it is desirable that the electron injection efficiency is high and that the injected electrons are efficiently transported. For this purpose, it has a high electron affinity, high electron mobility, and excellent stability.
It is preferable to use a substance that is unlikely to generate trapping impurities during manufacture and use.
However, when considering the transport balance of holes and electrons, if the role is to efficiently prevent holes from the anode from flowing to the cathode side without recombining, the electron transport capacity is not so great. Even if it is not high, it has the same effect of improving luminous efficiency as a material with high electron transport ability. Therefore, the electron injection/transport layer in this embodiment may also include the function of a layer that can efficiently block the movement of holes.

As the material (electron transport material) forming the electron transport layer 106 or the electron injection layer 107,
Any compound that has been conventionally used as an electron transfer compound in photoconductive materials and known compounds that are used in the electron injection layer and electron transport layer of organic EL devices can be used.

Materials used for the electron transport layer or electron injection layer include compounds consisting of an aromatic ring or a heteroaromatic ring composed of one or more atoms selected from carbon, hydrogen, oxygen, sulfur, silicon, and phosphorus; It is preferable to contain at least one selected from pyrrole derivatives, fused ring derivatives thereof, and metal complexes having electron-accepting nitrogen. Specifically, fused ring aromatic ring derivatives such as naphthalene and anthracene, styryl aromatic ring derivatives represented by 4,4'-bis(diphenylethenyl)biphenyl, perinone derivatives, coumarin derivatives, and naphthalimide derivatives. , quinone derivatives such as anthraquinone and diphenoquinone,
Examples include phosphorus oxide derivatives, carbazole derivatives, and indole derivatives.
Examples of metal complexes having electron-accepting nitrogen include hydroxyazole complexes such as hydroxyphenyloxazole complexes, azomethine complexes, tropolone metal complexes, flavonol metal complexes, and benzoquinoline metal complexes. These materials can be used alone or in combination with different materials.

Specific examples of other electron transfer compounds include pyridine derivatives, naphthalene derivatives, anthracene derivatives, phenanthroline derivatives, perinone derivatives, coumarin derivatives, naphthalimide derivatives, anthraquinone derivatives, diphenoquinone derivatives, diphenylquinone derivatives, perylene derivatives, and oxadiazoles. derivatives (1,3-bis[(4-t-butylphenyl)1,3,4-oxadiazolyl]phenylene, etc.), thiophene derivatives, triazole derivatives (N-naphthyl-2,5-diphenyl-1,3,4- triazole, etc.), thiadiazole derivatives, metal complexes of oxine derivatives, quinolinol metal complexes, quinoxaline derivatives, polymers of quinoxaline derivatives, benzazole compounds, gallium complexes, pyrazole derivatives, perfluorinated phenylene derivatives, triazine derivatives, pyrazine derivatives, benzoquinolines derivatives (2,2'-bis(benzo[h]quinolin-2-yl)-9,9'-spirobifluorene, etc.), imidazopyridine derivatives, borane derivatives, benzimidazole derivatives (tris(N-phenylbenzimidazole- benzoxazole derivatives, benzothiazole derivatives, quinoline derivatives, oligopyridine derivatives such as terpyridine, bipyridine derivatives, terpyridine derivatives (1,3-bis(4'-(
2,2':6'2''-terpyridinyl))benzene, etc.), naphthyridine derivatives (bis(
(1-naphthyl)-4-(1,8-naphthyridin-2-yl)phenylphosphine oxide, etc.), aldazine derivatives, carbazole derivatives, indole derivatives, phosphorus oxide derivatives, bisstyryl derivatives, etc.

Further, metal complexes having electron-accepting nitrogen can also be used, such as hydroxyazole complexes such as quinolinol metal complexes and hydroxyphenyloxazole complexes, azomethine complexes, tropolone metal complexes, flavonol metal complexes, and benzoquinoline metal complexes. can give.

The above-mentioned materials can be used alone, but they can also be used in combination with different materials.

Among the materials mentioned above, borane derivatives, pyridine derivatives, fluoranthene derivatives, BO
Preferred are anthracene derivatives, benzofluorene derivatives, phosphine oxide derivatives, pyrimidine derivatives, carbazole derivatives, triazine derivatives, benzimidazole derivatives, phenanthroline derivatives, and quinolinol metal complexes.

<Borane derivative>
The borane derivative is, for example, a compound represented by the following general formula (ETM-1), and is disclosed in detail in JP-A No. 2007-27587.
In the above formula (ETM-1), R ¹¹ and R ¹² are each independently hydrogen, alkyl, cycloalkyl, optionally substituted aryl, substituted silyl, optionally substituted nitrogen-containing is at least one of a heterocycle or cyano, and R ¹³ to R ¹⁶ are
Each independently is an optionally substituted alkyl, an optionally substituted cycloalkyl, or an optionally substituted aryl, X is an optionally substituted arylene, and Y is an optionally substituted arylene. an optionally substituted aryl having 16 or less carbon atoms, a substituted boryl, or an optionally substituted carbazolyl, and n is each independently 0 to
It is an integer of 3. Further, examples of the substituent in the case of "optionally substituted" or "substituted" include aryl, heteroaryl, alkyl, and cycloalkyl.

Among the compounds represented by the above general formula (ETM-1), the following general formula (ETM-1-1)
A compound represented by the following formula or a compound represented by the following general formula (ETM-1-2) is preferred.
In formula (ETM-1-1), R ¹¹ and R ¹² are each independently hydrogen, alkyl, cycloalkyl, optionally substituted aryl, substituted silyl, optionally substituted nitrogen is at least one of a containing heterocycle or cyano, and R ¹³ to R ¹⁶ are
Each independently represents optionally substituted alkyl, optionally substituted cycloalkyl, or optionally substituted aryl, and R ²¹ and R ²² each independently represent hydrogen, alkyl, or cycloalkyl. , optionally substituted aryl, substituted silyl, optionally substituted nitrogen-containing heterocycle, or cyano,
X ¹ is an optionally substituted arylene having 20 or less carbon atoms, n is each independently an integer of 0 to 3, and m is each independently an integer of 0 to 4. Further, examples of the substituent in the case of "optionally substituted" or "substituted" include aryl, heteroaryl, alkyl, and cycloalkyl.
In formula (ETM-1-2), R ¹¹ and R ¹² are each independently hydrogen, alkyl, cycloalkyl, optionally substituted aryl, substituted silyl, optionally substituted nitrogen is at least one of a containing heterocycle or cyano, and R ¹³ to R ¹⁶ are
Each independently represents an optionally substituted alkyl, an optionally substituted cycloalkyl, or an optionally substituted aryl, and X ¹ is an optionally substituted carbon number of 2
It is an arylene of 0 or less, and each n is independently an integer of 0 to 3. Also,
Substituents in the case of "may be substituted" or "substituted" include aryl,
Examples include heteroaryl, alkyl, and cycloalkyl.

Specific examples of X ¹ include divalent groups represented by the following formulas (X-1) to (X-9).
(In each formula, R ^a is each independently an alkyl group, a cycloalkyl group, or an optionally substituted phenyl group.)

Specific examples of this borane derivative include the following compounds.

This borane derivative can be produced using known raw materials and known synthesis methods.

<Pyridine derivative>
The pyridine derivative is, for example, a compound represented by the following formula (ETM-2), preferably a compound represented by the formula (ETM-2-1) or formula (ETM-2-2).

φ is an n-valent aryl ring (preferably an n-valent benzene ring, naphthalene ring, anthracene ring, fluorene ring, benzofluorene ring, phenalene ring, phenanthrene ring or triphenylene ring), and n is an integer of 1 to 4; be.

In the above formula (ETM-2-1), R ¹¹ to R ¹⁸ are each independently hydrogen, alkyl (preferably alkyl having 1 to 24 carbon atoms), and cycloalkyl (preferably 3 carbon atoms).
to 12 cycloalkyl) or aryl (preferably aryl having 6 to 30 carbon atoms).

In the above formula (ETM-2-2), R ¹¹ and R ¹² are each independently hydrogen, alkyl (preferably alkyl having 1 to 24 carbon atoms), and cycloalkyl (preferably cycloalkyl having 3 to 12 carbon atoms). alkyl) or aryl (preferably aryl having 6 to 30 carbon atoms)
and R ¹¹ and R ¹² may be combined to form a ring.

In each formula, the "pyridine substituent" is one of the following formulas (Py-1) to (Py-15), and each pyridine substituent is independently an alkyl having 1 to 4 carbon atoms or a carbon It may be substituted with 5 to 10 cycloalkyl groups. Further, the pyridine substituent may be bonded to φ, anthracene ring or fluorene ring in each formula via a phenylene group or naphthylene group.

The pyridine substituent is any of the above formulas (Py-1) to (Py-15), and among these, any of the following formulas (Py-21) to (Py-44) It is preferable.

At least one hydrogen in each pyridine derivative may be substituted with deuterium, and among the two "pyridine substituents" in the above formulas (ETM-2-1) and (ETM-2-2), may be replaced with an aryl.

"Alkyl" in R ¹¹ to R ¹⁸ may be either straight chain or branched,
Examples include straight chain alkyl having 1 to 24 carbon atoms and branched alkyl having 3 to 24 carbon atoms. Preferred "alkyl" is alkyl having 1 to 18 carbon atoms (branched alkyl having 3 to 18 carbon atoms). More preferable “alkyl” is alkyl having 1 to 12 carbon atoms (3 to 12 carbon atoms)
12 branched chain alkyl). More preferred "alkyl" is alkyl having 1 to 6 carbon atoms (branched alkyl having 3 to 6 carbon atoms). Particularly preferable “alkyl” has 1 to 1 carbon atoms.
4 alkyl (branched alkyl having 3 to 4 carbon atoms).

Specific examples of "alkyl" include methyl, ethyl, n-propyl, isopropyl, n-
Butyl, isobutyl, s-butyl, t-butyl, n-pentyl, isopentyl, neopentyl, t-pentyl, n-hexyl, 1-methylpentyl, 4-methyl-2-pentyl,
3,3-dimethylbutyl, 2-ethylbutyl, n-heptyl, 1-methylhexyl, n-
Octyl, t-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 2,6-dimethyl-4-heptyl, 3,
5,5-trimethylhexyl, n-decyl, n-undecyl, 1-methyldecyl, n-dodecyl, n-tridecyl, 1-hexylheptyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, n-heptadecyl, n- Examples include octadecyl and n-eicosyl.

As for the alkyl having 1 to 4 carbon atoms to be substituted with the pyridine substituent, the above description of alkyl can be cited.

Examples of the "cycloalkyl" in R ¹¹ to R ¹⁸ include cycloalkyl having 3 to 12 carbon atoms. Preferred "cycloalkyl" is cycloalkyl having 3 to 10 carbon atoms. More preferred "cycloalkyl" is cycloalkyl having 3 to 8 carbon atoms. More preferred "cycloalkyl" is cycloalkyl having 3 to 6 carbon atoms.
Specific examples of "cycloalkyl" include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, methylcyclopentyl, cycloheptyl, methylcyclohexyl,
Examples include cyclooctyl or dimethylcyclohexyl.

As for the cycloalkyl having 5 to 10 carbon atoms to be substituted with the pyridine substituent, the above description of cycloalkyl can be cited.

As for "aryl" in R ¹¹ to R ¹⁸ , a preferable aryl is an aryl having 6 to 30 carbon atoms, a more preferable aryl is an aryl having 6 to 18 carbon atoms, and even more preferably an aryl having 6 to 14 carbon atoms. Especially preferred is aryl having 6 to 12 carbon atoms.

Specific examples of "aryl having 6 to 30 carbon atoms" include phenyl, which is a monocyclic aryl, (1-,2-)naphthyl, which is a fused bicyclic aryl, and acenaphthylene-(, which is a fused tricyclic aryl). 1-,3-,4-,5-)yl, fluorene-(1-,2-,3-,4-,9
-)yl, phenalen-(1-,2-)yl, (1-,2-,3-,4-,9-)phenanthryl, triphenylene-(1-,2-)yl which is a fused tetracyclic aryl , pyrene (
1-,2-,4-)yl, naphthacen-(1-,2-,5-)yl, fused pentacyclic aryl perylene-(1-,2-,3-)yl, pentacen-(1 -, 2-, 5-, 6-)
Examples include il.

Preferred examples of "aryl having 6 to 30 carbon atoms" include phenyl, naphthyl, phenanthryl, chrysenyl, and triphenylenyl, more preferred are phenyl, 1-naphthyl, 2-naphthyl, and phenanthryl, and particularly preferred are phenyl, 1-naphthyl, and phenanthryl. -Naphthyl or 2-naphthyl.

R ¹¹ and R ¹² in the above formula (ETM-2-2) may be combined to form a ring, and as a result, the five-membered ring of the fluorene skeleton includes cyclobutane, cyclopentane, cyclopentene, cyclopentadiene, Cyclohexane, fluorene or indene may also be spiro-bonded.

Specific examples of this pyridine derivative include the following compounds.

This pyridine derivative can be produced using known raw materials and known synthesis methods.

<Fluoranthene derivative>
The fluoranthene derivative is, for example, a compound represented by the following general formula (ETM-3),
Details are disclosed in International Publication No. 2010/134352.

In the above formula (ETM-3), X ¹² to X ²¹ are hydrogen, halogen, linear, branched or cyclic alkyl, linear, branched or cyclic alkoxy, substituted or unsubstituted aryl, or substituted or unsubstituted Represents a heteroaryl. Here, examples of the substituent when substituted include aryl, heteroaryl, alkyl, and cycloalkyl.

Specific examples of this fluoranthene derivative include the following compounds.

<BO derivative>
The BO derivative is, for example, a polycyclic aromatic compound represented by the following formula (ETM-4) or a multimer of a polycyclic aromatic compound having a plurality of structures represented by the following formula (ETM-4).

R ¹ to R ¹¹ are each independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, alkyl, cycloalkyl, alkoxy, or aryloxy, in which at least one hydrogen may be substituted with aryl, heteroaryl, alkyl or cycloalkyl.

Further, adjacent groups among R ¹ to R ¹¹ may be bonded to each other to form an aryl ring or a heteroaryl ring together with ring a, ring b, or ring c, and at least one hydrogen in the formed ring may be substituted with aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, alkyl, cycloalkyl, alkoxy or aryloxy, in which at least one hydrogen is substituted with aryl, heteroaryl, alkyl or Optionally substituted with cycloalkyl.

Furthermore, at least one hydrogen in the compound or structure represented by formula (ETM-4) may be substituted with halogen or deuterium.

Regarding the explanation of the substituents and the form of ring formation in formula (ETM-4), please refer to the above general formula (1).
The explanation of the polycyclic aromatic compound represented by can be cited.

Specific examples of this BO derivative include the following compounds.

This BO derivative can be produced using known raw materials and known synthesis methods.

<Anthracene derivative>
One of the anthracene derivatives is, for example, a compound represented by the following formula (ETM-5-1).

Ar is each independently divalent benzene or naphthalene, and R ¹ to R ⁴ are
Each independently represents hydrogen, alkyl having 1 to 6 carbon atoms, cycloalkyl having 3 to 6 carbon atoms, or aryl having 6 to 20 carbon atoms.

Ar can be appropriately selected independently from divalent benzene or naphthalene, and the two Ars may be different or the same, but from the viewpoint of ease of synthesis of the anthracene derivative, they are the same. It is preferable that Ar combines with pyridine to form a "site consisting of Ar and pyridine", and this site is formed by, for example, the following formulas (Py-1) to (
Py-12) is bonded to anthracene.

Among these groups, groups represented by any of the above formulas (Py-1) to (Py-9) are preferred, and groups represented by any of the above formulas (Py-1) to (Py-6) are preferred. More preferred are groups such as The two "sites consisting of Ar and pyridine" that bind to anthracene may have the same or different structures, but preferably have the same structure from the viewpoint of ease of synthesizing the anthracene derivative. However, from the viewpoint of device characteristics, it is preferable that the structures of the two "sites consisting of Ar and pyridine" be the same or different.

The alkyl having 1 to 6 carbon atoms in R ¹ to R ⁴ may be either straight chain or branched chain. That is, it is a straight chain alkyl having 1 to 6 carbon atoms or a branched alkyl having 3 to 6 carbon atoms. More preferred is alkyl having 1 to 4 carbon atoms (branched alkyl having 3 to 4 carbon atoms). Specific examples include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, t-butyl, n-pentyl, isopentyl, neopentyl, t-pentyl, n-hexyl, 1-methylpentyl, Examples include 4-methyl-2-pentyl, 3,3-dimethylbutyl, or 2-ethylbutyl, with methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, or t-butyl being preferred. , methyl, ethyl or t-butyl are more preferred.

Specific examples of cycloalkyl having 3 to 6 carbon atoms in R ¹ to R ⁴ include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, methylcyclopentyl, cycloheptyl, methylcyclohexyl, cyclooctyl, and dimethylcyclohexyl.

The aryl having 6 to 20 carbon atoms in R ¹ to R ⁴ is preferably an aryl having 6 to 16 carbon atoms, more preferably an aryl having 6 to 12 carbon atoms, and particularly preferably an aryl having 6 to 10 carbon atoms.

Specific examples of "aryl having 6 to 20 carbon atoms" include phenyl, which is a monocyclic aryl, (
o-,m-,p-)tolyl, (2,3-,2,4-,2,5-,2,6-,3,4-,3
,5-)xylyl, mesityl (2,4,6-trimethylphenyl), (o-,m-,p-
) cumenyl, (2-,3-,4-)biphenylyl which is a bicyclic aryl, (1-,2-)naphthyl which is a fused bicyclic aryl, and terphenylyl (m-terphenyl-) which is a tricyclic aryl. 2'-yl, m-terphenyl-4'-yl, m-terphenyl-5'-yl,
o-terphenyl-3'-yl, o-terphenyl-4'-yl, p-terphenyl-2
'-yl, m-terphenyl-2-yl, m-terphenyl-3-yl, m-terphenyl-4-yl, o-terphenyl-2-yl, o-terphenyl-3-yl, o -terphenyl-4-yl, p-terphenyl-2-yl, p-terphenyl-3-yl, p-terphenyl-4-yl), fused tricyclic aryl, anthracene-(1-, 2-,9
-)yl, acenaphthylene-(1-,3-,4-,5-)yl, fluorene-(1-,2
-,3-,4-,9-)yl, phenalen-(1-,2-)yl, (1-,2-,3-,
4-,9-)phenanthryl, fused tetracyclic aryl triphenylene-(1-,2-
)yl, pyrene-(1-,2-,4-)yl, tetracen-(1-,2-,5-)yl,
Examples include perylene-(1-,2-,3-)yl, which is a fused pentacyclic aryl.

Preferred "aryl having 6 to 20 carbon atoms" is phenyl, biphenylyl, terphenylyl or naphthyl, more preferably phenyl, biphenylyl, 1-naphthyl, 2-
Naphthyl or m-terphenyl-5'-yl, more preferably phenyl, biphenylyl, 1-naphthyl or 2-naphthyl, most preferably phenyl.

One of the anthracene derivatives is, for example, a compound represented by the following formula (ETM-5-2).

Ar ¹ each independently represents a single bond, divalent benzene, naphthalene, anthracene,
Fluorene or phenalene.

Ar ² is each independently an aryl having 6 to 20 carbon atoms, and is represented by the above formula (ETM-5
The same explanation as "aryl having 6 to 20 carbon atoms" in -1) can be cited. Aryl having 6 to 16 carbon atoms is preferable, aryl having 6 to 12 carbon atoms is more preferable, and aryl having 6 to 12 carbon atoms is preferable.
Aryls of ˜10 are particularly preferred. Specific examples include phenyl, biphenylyl, naphthyl, terphenylyl, anthracenyl, acenaphthylenyl, fluorenyl, phenalenyl,
Examples include phenanthryl, triphenylenyl, pyrenyl, tetracenyl, perylenyl, and the like.

R ¹ to R ⁴ are each independently hydrogen, alkyl having 1 to 6 carbon atoms, cycloalkyl having 3 to 6 carbon atoms, or aryl having 6 to 20 carbon atoms, and the above formula (ETM-5-1) You can cite the explanation in .

Specific examples of these anthracene derivatives include the following compounds.

These anthracene derivatives can be produced using known raw materials and known synthesis methods.

<Benzofluorene derivative>
The benzofluorene derivative is, for example, a compound represented by the following formula (ETM-6).

Ar ¹ is each independently an aryl having 6 to 20 carbon atoms, and is represented by the above formula (ETM-5
The same explanation as "aryl having 6 to 20 carbon atoms" in -1) can be cited. Aryl having 6 to 16 carbon atoms is preferable, aryl having 6 to 12 carbon atoms is more preferable, and aryl having 6 to 12 carbon atoms is preferable.
Aryls of ˜10 are particularly preferred. Specific examples include phenyl, biphenylyl, naphthyl, terphenylyl, anthracenyl, acenaphthylenyl, fluorenyl, phenalenyl,
Examples include phenanthryl, triphenylenyl, pyrenyl, tetracenyl, perylenyl, and the like.

Ar ² is each independently hydrogen, alkyl (preferably alkyl having 1 to 24 carbon atoms), cycloalkyl (preferably cycloalkyl having 3 to 12 carbon atoms), or aryl (preferably aryl having 6 to 30 carbon atoms). ), and two Ar ² may be bonded to form a ring.

The "alkyl" in Ar ² may be either straight chain or branched chain, for example,
Examples include straight chain alkyl having 1 to 24 carbon atoms and branched alkyl having 3 to 24 carbon atoms. Preferred "alkyl" is alkyl having 1 to 18 carbon atoms (branched alkyl having 3 to 18 carbon atoms)
It is. More preferred "alkyl" is alkyl having 1 to 12 carbon atoms (branched alkyl having 3 to 12 carbon atoms). More preferred "alkyl" is alkyl having 1 to 6 carbon atoms (branched alkyl having 3 to 6 carbon atoms). Particularly preferred "alkyl" is alkyl having 1 to 4 carbon atoms (branched alkyl having 3 to 4 carbon atoms). Specific examples of "alkyl" include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, t-butyl, n-pentyl, isopentyl, neopentyl, t-pentyl, n-hexyl, 1 -
Examples include methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, n-heptyl, and 1-methylhexyl.

Examples of the "cycloalkyl" in Ar ² include cycloalkyl having 3 to 12 carbon atoms. Preferred "cycloalkyl" is cycloalkyl having 3 to 10 carbon atoms. More preferred "cycloalkyl" is cycloalkyl having 3 to 8 carbon atoms. More preferred "cycloalkyl" is cycloalkyl having 3 to 6 carbon atoms. Specific examples of "cycloalkyl" include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, methylcyclopentyl, cycloheptyl, methylcyclohexyl, cyclooctyl, and dimethylcyclohexyl.

As for "aryl" in Ar ² , preferable aryl is aryl having 6 to 30 carbon atoms, more preferable aryl is aryl having 6 to 18 carbon atoms, still more preferably aryl having 6 to 14 carbon atoms, and especially Aryl having 6 to 12 carbon atoms is preferred.

Specific examples of "aryl having 6 to 30 carbon atoms" include phenyl, naphthyl, acenaphthylenyl, fluorenyl, phenalenyl, phenanthryl, triphenylenyl, pyrenyl, naphthacenyl, perylenyl, and pentacenyl.

Two Ar ² may be combined to form a ring, and as a result, cyclobutane, cyclopentane, cyclopentene, cyclopentadiene, cyclohexane, fluorene, indene, etc. are spiro-bonded to the 5-membered ring of the fluorene skeleton. It's okay.

Specific examples of this benzofluorene derivative include the following compounds.

This benzofluorene derivative can be produced using known raw materials and known synthesis methods.

<Phosphine oxide derivative>
The phosphine oxide derivative is, for example, a compound represented by the following formula (ETM-7-1). Details are also described in International Publication No. 2013/079217.
R ⁵ is substituted or unsubstituted alkyl having 1 to 20 carbon atoms, cycloalkyl having 3 to 20 carbon atoms, aryl having 6 to 20 carbon atoms, or heteroaryl having 5 to 20 carbon atoms;
R ⁶ is CN, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, cycloalkyl having 3 to 20 carbon atoms, heteroalkyl having 1 to 20 carbon atoms, aryl having 6 to 20 carbon atoms, or 5 carbon atoms;
~20 heteroaryl, alkoxy having 1 to 20 carbon atoms, or aryloxy having 6 to 20 carbon atoms,
R ⁷ and R ⁸ are each independently substituted or unsubstituted aryl having 6 to 20 carbon atoms or heteroaryl having 5 to 20 carbon atoms,
^R9 is oxygen or sulfur;
j is 0 or 1, k is 0 or 1, r is an integer from 0 to 4, and q is 1 to 3
is an integer.
Here, examples of the substituent when substituted include aryl, heteroaryl, alkyl, and cycloalkyl.

The phosphine oxide derivative may be, for example, a compound represented by the following formula (ETM-7-2).

R ¹ to R ³ may be the same or different, and represent hydrogen, an alkyl group, a cycloalkyl group,
Aralkyl group, alkenyl group, cycloalkenyl group, alkynyl group, alkoxy group, alkylthio group, cycloalkylthio group, aryl ether group, arylthioether group, aryl group, heterocyclic group, halogen, cyano group, aldehyde group, carbonyl group, carboxyl group, an amino group, a nitro group, a silyl group, and a fused ring formed between adjacent substituents.

Ar ¹ may be the same or different and is an arylene group or a heteroarylene group. Ar ² may be the same or different and are an aryl group or a heteroaryl group. However, at least one of Ar ¹ and Ar ² has a substituent, or forms a condensed ring with an adjacent substituent. n is an integer from 0 to 3; when n is 0, no unsaturated structural moiety exists; when n is 3, R ¹ does not exist.

Among these substituents, the alkyl group refers to a saturated aliphatic hydrocarbon group such as a methyl group, an ethyl group, a propyl group, a butyl group, and may be unsubstituted or substituted. When substituted, there are no particular limitations on the substituent, and examples thereof include an alkyl group, an aryl group, a heterocyclic group, and the like, and this point is also common to the following description. Further, the number of carbon atoms in the alkyl group is not particularly limited, but is usually in the range of 1 to 20 from the viewpoint of availability and cost.

Further, the cycloalkyl group refers to, for example, a saturated alicyclic hydrocarbon group such as cyclopropyl, cyclohexyl, norbornyl, and adamantyl, which may be unsubstituted or substituted. The number of carbon atoms in the alkyl group moiety is not particularly limited, but is usually in the range of 3 to 20.

Furthermore, an aralkyl group refers to an aromatic hydrocarbon group via an aliphatic hydrocarbon such as a benzyl group or a phenylethyl group, and both aliphatic hydrocarbons and aromatic hydrocarbons may be unsubstituted or substituted. It doesn't matter. The number of carbon atoms in the aliphatic moiety is not particularly limited, but is usually 1.
~20.

Further, the alkenyl group refers to an unsaturated aliphatic hydrocarbon group containing a double bond, such as a vinyl group, an allyl group, a butadienyl group, etc., and it may be unsubstituted or substituted. The number of carbon atoms in the alkenyl group is not particularly limited, but is usually in the range of 2 to 20.

Furthermore, a cycloalkenyl group refers to an unsaturated alicyclic hydrocarbon group containing a double bond, such as a cyclopentenyl group, a cyclopentadienyl group, or a cyclohexene group, and may be unsubstituted or substituted. I don't mind.

Further, the alkynyl group refers to, for example, an unsaturated aliphatic hydrocarbon group containing a triple bond such as an acetylenyl group, which may be unsubstituted or substituted. The number of carbon atoms in the alkynyl group is not particularly limited, but is usually in the range of 2 to 20.

Further, the alkoxy group refers to, for example, an aliphatic hydrocarbon group such as a methoxy group via an ether bond, and the aliphatic hydrocarbon group may be unsubstituted or substituted. The number of carbon atoms in the alkoxy group is not particularly limited, but is usually in the range of 1 to 20.

Moreover, an alkylthio group is a group in which the oxygen atom of the ether bond of an alkoxy group is substituted with a sulfur atom.

Moreover, a cycloalkylthio group is a group in which the oxygen atom of the ether bond of a cycloalkoxy group is substituted with a sulfur atom.

Further, the aryl ether group refers to an aromatic hydrocarbon group such as a phenoxy group via an ether bond, and the aromatic hydrocarbon group may be unsubstituted or substituted. The number of carbon atoms in the aryl ether group is not particularly limited, but is usually in the range of 6 to 40.

Further, the arylthioether group is a group in which the oxygen atom of the ether bond of the aryl ether group is substituted with a sulfur atom.

Further, the aryl group refers to an aromatic hydrocarbon group such as a phenyl group, a naphthyl group, a biphenyl group, a phenanthryl group, a terphenyl group, and a pyrenyl group. The aryl group may be unsubstituted or substituted. The number of carbon atoms in the aryl group is not particularly limited, but is usually in the range of 6 to 40.

In addition, the heterocyclic group refers to a cyclic structural group having an atom other than carbon, such as a furanyl group, a thiophenyl group, an oxazolyl group, a pyridyl group, a quinolinyl group, and a carbazolyl group,
This may be unsubstituted or substituted. The number of carbon atoms in the heterocyclic group is not particularly limited, but is usually in the range of 2 to 30.

Halogen refers to fluorine, chlorine, bromine, and iodine.

The aldehyde group, carbonyl group, and amino group can also include groups substituted with aliphatic hydrocarbons, alicyclic hydrocarbons, aromatic hydrocarbons, heterocycles, and the like.

Furthermore, aliphatic hydrocarbons, alicyclic hydrocarbons, aromatic hydrocarbons, and heterocycles may be unsubstituted or substituted.

The silyl group refers to a silicon compound group such as a trimethylsilyl group, which may be unsubstituted or substituted. The number of carbon atoms in the silyl group is not particularly limited, but is usually 3
~20. Further, the silicon number is usually 1 to 6.

The condensed ring formed between adjacent substituents is, for example, Ar ¹ and R ² , Ar ¹ and R ³ , A
It is a conjugated or non-conjugated condensed ring formed between r ² and R ² , Ar ² and R ³ , R ² and R ³ , Ar ¹ and Ar ² , etc. Here, when n is 1, two R ¹ may form a conjugated or non-conjugated condensed ring. These fused rings may contain nitrogen, oxygen, or sulfur atoms in the ring structure, or may be fused with another ring.

Specific examples of this phosphine oxide derivative include the following compounds.

This phosphine oxide derivative can be produced using known raw materials and known synthesis methods.

<Pyrimidine derivative>
The pyrimidine derivative is, for example, a compound represented by the following formula (ETM-8), preferably a compound represented by the following formula (ETM-8-1). For details, see International Publication No. 2011/02
It is also described in Publication No. 1689.

Each Ar is independently an optionally substituted aryl or an optionally substituted heteroaryl. n is an integer of 1 to 4, preferably an integer of 1 to 3,
More preferably 2 or 3.

For example, "aryl" in "optionally substituted aryl" has 6 to 30 carbon atoms.
Preferably aryl having 6 to 24 carbon atoms, more preferably 6 to 24 carbon atoms.
-20 aryl, more preferably 6 to 12 carbon atoms.

Specific examples of "aryl" include phenyl, which is a monocyclic aryl, (2-,3-,4-)biphenylyl, which is a bicyclic aryl, and (1-,2-)naphthyl, which is a fused bicyclic aryl. , tricyclic aryl terphenylyl (m-terphenyl-2'-yl, m-terphenyl-4'-yl, m-terphenyl-5'-yl, o-terphenyl-3'-yl,
o-terphenyl-4'-yl, p-terphenyl-2'-yl, m-terphenyl-2
-yl, m-terphenyl-3-yl, m-terphenyl-4-yl, o-terphenyl-2-yl, o-terphenyl-3-yl, o-terphenyl-4-yl, p- terphenyl-2-yl, p-terphenyl-3-yl, p-terphenyl-4-yl), acenaphthylene-(1-,3-,4-,5-)yl, which is a fused tricyclic aryl , fluorene-
(1-,2-,3-,4-,9-)yl, phenalen-(1-,2-)yl, (1-,2-yl)
-,3-,4-,9-)phenanthryl, tetracyclic aryl quaterphenylyl (5
'-phenyl-m-terphenyl-2-yl, 5'-phenyl-m-terphenyl-3-
yl, 5'-phenyl-m-terphenyl-4-yl, m-quaterphenylyl), fused tetracyclic aryl triphenylen-(1-,2-)yl, pyrene-(1-,2- ,4
-)yl, naphthacen-(1-,2-,5-)yl, fused pentacyclic aryl perylene-(1-,2-,3-)yl, pentacen-(1-,2-,5- , 6-) il etc.

Examples of "heteroaryl" in "optionally substituted heteroaryl" include heteroaryl having 2 to 30 carbon atoms, preferably heteroaryl having 2 to 25 carbon atoms, and heteroaryl having 2 to 20 carbon atoms. Aryl is more preferred, heteroaryl having 2 to 15 carbon atoms is even more preferred, and heteroaryl having 2 to 10 carbon atoms is particularly preferred. Examples of the heteroaryl include, for example, a heterocycle containing 1 to 5 heteroatoms selected from oxygen, sulfur, and nitrogen in addition to carbon as ring constituent atoms.

Specific examples of heteroaryl include furyl, thienyl, pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, pyrazolyl, oxadiazolyl, furazanyl, thiadiazolyl, triazolyl, tetrazolyl, pyridyl,
Pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, benzofuranyl, isobenzofuranyl, benzo[b]thienyl, indolyl, isoindolyl, 1H-indazolyl,
Benzimidazolyl, benzoxazolyl, benzothiazolyl, 1H-benzotriazolyl, quinolyl, isoquinolyl, cinnolyl, quinazolyl, quinoxalinyl, phthalazinyl, naphthyridinyl, purinyl, pteridinyl, carbazolyl, acridinyl, phenoxazinyl, phenothiazinyl, phenazinyl, phenoxathiinyl, Examples include thianthrenyl and indolizinyl.

Further, the above aryl and heteroaryl may be substituted, for example, each may be substituted with the above aryl or heteroaryl.

Specific examples of this pyrimidine derivative include the following compounds.

This pyrimidine derivative can be produced using known raw materials and known synthesis methods.

<Carbazole derivative>
The carbazole derivative is, for example, a compound represented by the following formula (ETM-9), or a multimer of a plurality of compounds bonded together through a single bond or the like. For details, see US Publication No. 2014/0197386
It is stated in the No.

Each Ar is independently an optionally substituted aryl or an optionally substituted heteroaryl. n is each independently an integer of 0 to 4, preferably 0 to 4;
It is an integer of 3, more preferably 0 or 1.

For example, "aryl" in "optionally substituted aryl" has 6 to 30 carbon atoms.
Preferably aryl having 6 to 24 carbon atoms, more preferably 6 to 24 carbon atoms.
-20 aryl, more preferably 6 to 12 carbon atoms.

Specific examples of "aryl" include phenyl, which is a monocyclic aryl, (2-,3-,4-)biphenylyl, which is a bicyclic aryl, and (1-,2-)naphthyl, which is a fused bicyclic aryl. , tricyclic aryl terphenylyl (m-terphenyl-2'-yl, m-terphenyl-4'-yl, m-terphenyl-5'-yl, o-terphenyl-3'-yl,
o-terphenyl-4'-yl, p-terphenyl-2'-yl, m-terphenyl-2
-yl, m-terphenyl-3-yl, m-terphenyl-4-yl, o-terphenyl-2-yl, o-terphenyl-3-yl, o-terphenyl-4-yl, p- terphenyl-2-yl, p-terphenyl-3-yl, p-terphenyl-4-yl), acenaphthylene-(1-,3-,4-,5-)yl, which is a fused tricyclic aryl , fluorene-
(1-,2-,3-,4-,9-)yl, phenalen-(1-,2-)yl, (1-,2-yl)
-,3-,4-,9-)phenanthryl, tetracyclic aryl quaterphenylyl (5
'-phenyl-m-terphenyl-2-yl, 5'-phenyl-m-terphenyl-3-
yl, 5'-phenyl-m-terphenyl-4-yl, m-quaterphenylyl), fused tetracyclic aryl triphenylen-(1-,2-)yl, pyrene-(1-,2- ,4
-)yl, naphthacen-(1-,2-,5-)yl, fused pentacyclic aryl perylene-(1-,2-,3-)yl, pentacen-(1-,2-,5- , 6-) il etc.

Examples of "heteroaryl" in "optionally substituted heteroaryl" include heteroaryl having 2 to 30 carbon atoms, preferably heteroaryl having 2 to 25 carbon atoms, and heteroaryl having 2 to 20 carbon atoms. Aryl is more preferred, heteroaryl having 2 to 15 carbon atoms is even more preferred, and heteroaryl having 2 to 10 carbon atoms is particularly preferred. Examples of the heteroaryl include, for example, a heterocycle containing 1 to 5 heteroatoms selected from oxygen, sulfur, and nitrogen in addition to carbon as ring constituent atoms.

Specific examples of heteroaryl include furyl, thienyl, pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, pyrazolyl, oxadiazolyl, furazanyl, thiadiazolyl, triazolyl, tetrazolyl, pyridyl,
Pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, benzofuranyl, isobenzofuranyl, benzo[b]thienyl, indolyl, isoindolyl, 1H-indazolyl,
Benzimidazolyl, benzoxazolyl, benzothiazolyl, 1H-benzotriazolyl, quinolyl, isoquinolyl, cinnolyl, quinazolyl, quinoxalinyl, phthalazinyl, naphthyridinyl, purinyl, pteridinyl, carbazolyl, acridinyl, phenoxazinyl, phenothiazinyl, phenazinyl, phenoxathiinyl, Examples include thianthrenyl and indolizinyl.

Further, the above aryl and heteroaryl may be substituted, for example, each may be substituted with the above aryl or heteroaryl.

The carbazole derivative may be a multimer in which a plurality of compounds represented by the above formula (ETM-9) are bonded through a single bond or the like. In this case, in addition to a single bond, they may be bonded through an aryl ring (preferably a polyvalent benzene ring, naphthalene ring, anthracene ring, fluorene ring, benzofluorene ring, phenalene ring, phenanthrene ring, or triphenylene ring).

Specific examples of this carbazole derivative include the following compounds.

This carbazole derivative can be produced using known raw materials and known synthesis methods.

<Triazine derivative>
The triazine derivative is, for example, a compound represented by the following formula (ETM-10), preferably a compound represented by the following formula (ETM-10-1). For details, see US Publication No. 2011
It is described in the /0156013 publication.

Each Ar is independently an optionally substituted aryl or an optionally substituted heteroaryl. n is an integer from 1 to 3, preferably 2 or 3.

For example, "aryl" in "optionally substituted aryl" has 6 to 30 carbon atoms.
Preferably aryl having 6 to 24 carbon atoms, more preferably 6 to 24 carbon atoms.
-20 aryl, more preferably 6 to 12 carbon atoms.

Specific examples of "aryl" include phenyl, which is a monocyclic aryl, (2-,3-,4-)biphenylyl, which is a bicyclic aryl, and (1-,2-)naphthyl, which is a fused bicyclic aryl. , tricyclic aryl terphenylyl (m-terphenyl-2'-yl, m-terphenyl-4'-yl, m-terphenyl-5'-yl, o-terphenyl-3'-yl,
o-terphenyl-4'-yl, p-terphenyl-2'-yl, m-terphenyl-2
-yl, m-terphenyl-3-yl, m-terphenyl-4-yl, o-terphenyl-2-yl, o-terphenyl-3-yl, o-terphenyl-4-yl, p- terphenyl-2-yl, p-terphenyl-3-yl, p-terphenyl-4-yl), acenaphthylene-(1-,3-,4-,5-)yl, which is a fused tricyclic aryl , fluorene-
(1-,2-,3-,4-,9-)yl, phenalen-(1-,2-)yl, (1-,2-yl)
-,3-,4-,9-)phenanthryl, tetracyclic aryl quaterphenylyl (5
'-phenyl-m-terphenyl-2-yl, 5'-phenyl-m-terphenyl-3-
yl, 5'-phenyl-m-terphenyl-4-yl, m-quaterphenylyl), fused tetracyclic aryl triphenylen-(1-,2-)yl, pyrene-(1-,2- ,4
-)yl, naphthacen-(1-,2-,5-)yl, fused pentacyclic aryl perylene-(1-,2-,3-)yl, pentacen-(1-,2-,5- , 6-) il etc.

Examples of "heteroaryl" in "optionally substituted heteroaryl" include heteroaryl having 2 to 30 carbon atoms, preferably heteroaryl having 2 to 25 carbon atoms, and heteroaryl having 2 to 20 carbon atoms. Aryl is more preferred, heteroaryl having 2 to 15 carbon atoms is even more preferred, and heteroaryl having 2 to 10 carbon atoms is particularly preferred. Examples of the heteroaryl include, for example, a heterocycle containing 1 to 5 heteroatoms selected from oxygen, sulfur, and nitrogen in addition to carbon as ring constituent atoms.

Specific examples of heteroaryl include furyl, thienyl, pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, pyrazolyl, oxadiazolyl, furazanyl, thiadiazolyl, triazolyl, tetrazolyl, pyridyl,
Pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, benzofuranyl, isobenzofuranyl, benzo[b]thienyl, indolyl, isoindolyl, 1H-indazolyl,
Benzimidazolyl, benzoxazolyl, benzothiazolyl, 1H-benzotriazolyl, quinolyl, isoquinolyl, cinnolyl, quinazolyl, quinoxalinyl, phthalazinyl, naphthyridinyl, purinyl, pteridinyl, carbazolyl, acridinyl, phenoxazinyl, phenothiazinyl, phenazinyl, phenoxathiinyl, Examples include thianthrenyl and indolizinyl.

Further, the above aryl and heteroaryl may be substituted, for example, each may be substituted with the above aryl or heteroaryl.

Specific examples of this triazine derivative include the following compounds.

This triazine derivative can be produced using known raw materials and known synthesis methods.

<Benzimidazole derivative>
The benzimidazole derivative is, for example, a compound represented by the following formula (ETM-11).

φ is an n-valent aryl ring (preferably an n-valent benzene ring, naphthalene ring, anthracene ring, fluorene ring, benzofluorene ring, phenalene ring, phenanthrene ring or triphenylene ring), and n is an integer of 1 to 4; "benzimidazole substituent" means that the pyridyl group in the "pyridine substituent" in the above formula (ETM-2), formula (ETM-2-1) and formula (ETM-2-2) is A substituent substituted for an imidazole group,
At least one hydrogen in the benzimidazole derivative may be substituted with deuterium.

R ¹¹ in the above benzimidazole group is hydrogen, alkyl having 1 to 24 carbon atoms, cycloalkyl having 3 to 12 carbon atoms, or aryl having 6 to 30 carbon atoms, and is represented by the above formula (ETM-
2-1) and the explanation of R ¹¹ in formula (ETM-2-2) can be cited.

Further, φ is preferably an anthracene ring or a fluorene ring, and the structure in this case can be cited from the explanation for the above formula (ETM-2-1) or formula (ETM-2-2), and each R ¹¹ to R ¹⁸ in the formula are the above formula (ETM-2-1) or formula (ETM-2-2)
You can cite the explanation in . In addition, the above formula (ETM-2-1) or the formula (ETM-
2-2) describes a form in which two pyridine-based substituents are bonded, but when replacing these with benzimidazole-based substituents, both pyridine-based substituents may be replaced with benzimidazole-based substituents. (i.e. n=2), one of the pyridine-based substituents is replaced with a benzimidazole-based substituent, and the other pyridine-based substituent is replaced with R ¹¹ to R ^1
8 (ie, n=1). Furthermore, for example, at least one of R ¹¹ to R ¹⁸ in the above formula (ETM-2-1) may be replaced with a benzimidazole substituent, and the "pyridine substituent" may be replaced with R ¹¹ to R ¹⁸ .

Specific examples of this benzimidazole derivative include 1-phenyl-2-(4-(
10-phenylanthracen-9-yl)phenyl)-1H-benzo[d]imidazole, 2-(4-(10-(naphthalen-2-yl)anthracen-9-yl)phenyl)-
1-phenyl-1H-benzo[d]imidazole, 2-(3-(10-(naphthalene-2
-yl)anthracen-9-yl)phenyl)-1-phenyl-1H-benzo[d]imidazole, 5-(10-(naphthalen-2-yl)anthracen-9-yl)-1,2-
diphenyl-1H-benzo[d]imidazole, 1-(4-(10-(naphthalene-2-
yl)anthracen-9-yl)phenyl)-2-phenyl-1H-benzo[d]imidazole, 2-(4-(9,10-di(naphthalen-2-yl)anthracen-2-yl)
phenyl)-1-phenyl-1H-benzo[d]imidazole, 1-(4-(9,10-
Di(naphthalen-2-yl)anthracen-2-yl)phenyl)-2-phenyl-1H
-benzo[d]imidazole, 5-(9,10-di(naphthalen-2-yl)anthracen-2-yl)-1,2-diphenyl-1H-benzo[d]imidazole, and the like.

This benzimidazole derivative can be produced using known raw materials and known synthesis methods.

<Phenanthroline derivative>
The phenanthroline derivative has, for example, the following formula (ETM-12) or the formula (ETM-12-
This is a compound represented by 1). Details are described in International Publication No. 2006/021982.

φ is an n-valent aryl ring (preferably an n-valent benzene ring, naphthalene ring, anthracene ring, fluorene ring, benzofluorene ring, phenalene ring, phenanthrene ring or triphenylene ring), and n is an integer of 1 to 4; be.

R ¹¹ to R ¹⁸ in each formula are each independently hydrogen, alkyl (preferably carbon number 1 to
24 alkyl), cycloalkyl (preferably cycloalkyl having 3 to 12 carbon atoms), or aryl (preferably aryl having 6 to 30 carbon atoms). In addition, the above formula (ETM-1
In 2-1), any one of R ¹¹ to R ¹⁸ is bonded to φ, which is an aryl ring.

At least one hydrogen in each phenanthroline derivative may be replaced with deuterium.

The alkyl, cycloalkyl and aryl in R ¹¹ to R ¹⁸ are represented by the above formula (
The explanation of R ¹¹ to R ¹⁸ in ETM-2) can be cited. Further, in addition to the above-mentioned examples, φ may have the following structural formula, for example. Note that R in the following structural formula is each independently hydrogen, methyl, ethyl, isopropyl, cyclohexyl, phenyl, 1-naphthyl, 2-naphthyl, biphenylyl, or terphenylyl.

Specific examples of this phenanthroline derivative include 4,7-diphenyl-1,10
-phenanthroline, 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline, 9,10-di(1,10-phenanthrolin-2-yl)anthracene, 2,6-
Di(1,10-phenanthrolin-5-yl)pyridine, 1,3,5-tri(1,10-
phenanthrolin-5-yl)benzene, 9,9'-difluoro-bis(1,10-phenanthrolin-5-yl), bathocuproine, 1,3-bis(2-phenyl-1,10-
Examples include phenanthrolin-9-yl)benzene and compounds represented by the following structural formula.

This phenanthroline derivative can be produced using known raw materials and known synthesis methods.

<Quinolinol metal complex>
The quinolinol metal complex is, for example, a compound represented by the following general formula (ETM-13).
In the formula, R ¹ to R ⁶ are each independently hydrogen, fluorine, alkyl, cycloalkyl,
aralkyl, alkenyl, cyano, alkoxy or aryl, M is Li, Al,
Ga, Be or Zn, and n is an integer from 1 to 3.

Specific examples of quinolinol metal complexes include 8-quinolinol lithium, tris(8-
quinolinolate) aluminum, tris(4-methyl-8-quinolinolate) aluminum, tris(5-methyl-8-quinolinolate) aluminum, tris(3,4-dimethyl-8-quinolinolate) aluminum, tris(4,5-dimethyl- 8-quinolinolate)aluminum, tris(4,6-dimethyl-8-quinolinolate)aluminum, bis(2-methyl-8-quinolinolate)(phenolate)aluminum, bis(2-methyl-8-quinolinolate)(2-methylphenolate) Aluminum, bis(2-methyl-8-quinolinolate)(3-methylphenolate)aluminum, bis(2-methyl-
8-quinolinolate)(4-methylphenolate)aluminum, bis(2-methyl-8
-quinolinolate)(2-phenylphenolate)aluminum, bis(2-methyl-8
-quinolinolate)(3-phenylphenolate)aluminum, bis(2-methyl-8
-quinolinolate)(4-phenylphenolate)aluminum, bis(2-methyl-8
-quinolinolate)(2,3-dimethylphenolate)aluminum, bis(2-methyl-8-quinolinolate)(2,6-dimethylphenolate)aluminum, bis(2-methyl-8-quinolinolate)(3,4- dimethylphenolate) aluminum, bis(2
-Methyl-8-quinolinolate)(3,5-dimethylphenolate)aluminum, bis(2-methyl-8-quinolinolate)(3,5-di-t-butylphenolate)aluminum, bis(2-methyl-8-quinolinolate)(3,5-di-t-butylphenolate)aluminum -quinolinolate)(2,6-diphenylphenolate)aluminum, bis(2-methyl-8-quinolinolate)(2,4,6-triphenylphenolate)aluminum, bis(2-methyl-8-quinolinolate)(2 ,4,6-trimethylphenolate)aluminum,bis(2-methyl-8-quinolinolate)(2,4
, 5,6-tetramethylphenolate)aluminum, bis(2-methyl-8-quinolinolate)(1-naphthlate)aluminum, bis(2-methyl-8-quinolinolate)
(2-naphtholate)aluminum, bis(2,4-dimethyl-8-quinolinolate)(
2-phenylphenolate) aluminum, bis(2,4-dimethyl-8-quinolinolate)(3-phenylphenolate) aluminum, bis(2,4-dimethyl-8-quinolinolate)(4-phenylphenolate) aluminum, Bis(2,4-dimethyl-8-
quinolinolate)(3,5-dimethylphenolate)aluminum, bis(2,4-dimethyl-8-quinolinolate)(3,5-di-t-butylphenolate)aluminum, bis(2-methyl-8-quinolinolate) Aluminum-μ-oxo-bis(2-methyl-
8-quinolinolate)aluminum, bis(2,4-dimethyl-8-quinolinolate)aluminum-μ-oxo-bis(2,4-dimethyl-8-quinolinolate)aluminum, bis(2-methyl-4-ethyl-8- quinolinolate) aluminum-μ-oxo-bis(2-methyl-4-ethyl-8-quinolinolate)aluminum, bis(2-methyl-
4-methoxy-8-quinolinolate)aluminum-μ-oxo-bis(2-methyl-4
-methoxy-8-quinolinolate) aluminum, bis(2-methyl-5-cyano-8-
quinolinolate)aluminum-μ-oxo-bis(2-methyl-5-cyano-8-quinolinolate)aluminum, bis(2-methyl-5-trifluoromethyl-8-quinolinolate)aluminum-μ-oxo-bis(2- Methyl-5-trifluoromethyl-8-
quinolinolate) aluminum, bis(10-hydroxybenzo[h]quinoline) beryllium, and the like.

This quinolinol metal complex can be produced using known raw materials and known synthesis methods.

<Thiazole derivatives and benzothiazole derivatives>
The thiazole derivative is, for example, a compound represented by the following formula (ETM-14-1).
The benzothiazole derivative is, for example, a compound represented by the following formula (ETM-14-2).

In each formula, φ is an n-valent aryl ring (preferably an n-valent benzene ring, naphthalene ring, anthracene ring, fluorene ring, benzofluorene ring, phenalene ring, phenanthrene ring, or triphenylene ring), and n is 1 to 4. is an integer of the above formula (ETM-2), formula (ETM-2-1) and formula (E
The pyridyl group in the "pyridine substituent" in TM-2-2) is a substituent substituted with the following thiazole group or benzothiazole group, and at least one hydrogen in the thiazole derivative and benzothiazole derivative is deuterium. May be replaced.

Further, φ is preferably an anthracene ring or a fluorene ring, and the structure in this case can be cited from the explanation for the above formula (ETM-2-1) or formula (ETM-2-2), and each R ¹¹ to R ¹⁸ in the formula are the above formula (ETM-2-1) or formula (ETM-2-2)
You can cite the explanation in . In addition, the above formula (ETM-2-1) or the formula (ETM-
2-2) describes the form in which two pyridine substituents are bonded, but when replacing these with a thiazole substituent (or benzothiazole substituent), both pyridine substituents are replaced with a thiazole substituent. (or a benzothiazole-based substituent) (i.e., n = 2), or by replacing one of the pyridine-based substituents with a thiazole-based substituent (or benzothiazole-based substituent) to replace the other pyridine-based substituent. Substituents R ¹¹ to R ¹⁸
(i.e., n=1). Further, for example, by replacing at least one of R ¹¹ to R ¹⁸ in the above formula (ETM-2-1) with a thiazole substituent (or benzothiazole substituent), the "pyridine substituent" can be replaced with R ¹¹ to R ¹⁸ You can also replace it with

These thiazole derivatives or benzothiazole derivatives can be produced using known raw materials and known synthesis methods.

The electron transport layer or the electron injection layer may further contain a substance that can reduce the material forming the electron transport layer or the electron injection layer. A variety of substances can be used as this reducing substance as long as it has a certain reducing property, such as alkali metals, alkaline earth metals, rare earth metals, alkali metal oxides, alkali metal halides, and alkali metals. earth metal oxides,
At least one selected from the group consisting of alkaline earth metal halides, rare earth metal oxides, rare earth metal halides, alkali metal organic complexes, alkaline earth metal organic complexes, and rare earth metal organic complexes. It can be suitably used.

Preferred reducing substances include Na (work function: 2.36 eV) and K (work function: 2.28 eV).
, Rb (2.16 eV) or Cs (1.95 eV), Ca (
Examples include alkaline earth metals such as Sr (2.0 to 2.5 eV), Ba (2.52 eV), and substances with a work function of 2.9 eV or less are particularly preferred. Among these, more preferable reducing substances are alkali metals such as K, Rb, or Cs, still more preferably Rb or Cs, and most preferable is Cs. These alkali metals have particularly high reducing ability, and by adding a relatively small amount to the material forming the electron transport layer or the electron injection layer, the luminance of the organic EL element can be improved and the life of the organic EL element can be extended. Further, as a reducing substance with a work function of 2.9 eV or less, combinations of two or more of these alkali metals are also preferable, and in particular, combinations containing Cs, such as Cs and Na, Cs and K, Cs and Rb,
Alternatively, a combination of Cs, Na, and K is preferred. By including Cs, the reducing ability can be efficiently exhibited, and by adding it to the material forming the electron transport layer or the electron injection layer, the luminance of light emission and the longevity of the organic EL element can be improved.

<Cathode in organic electroluminescent device>
The cathode 108 serves to inject electrons into the light emitting layer 105 via the electron injection layer 107 and the electron transport layer 106.

The material forming the cathode 108 is not particularly limited as long as it can efficiently inject electrons into the organic layer, but the same material as the material forming the anode 102 can be used. Among them, metals such as tin, indium, calcium, aluminum, silver, copper, nickel, chromium, gold, platinum, iron, zinc, lithium, sodium, potassium, cesium, and magnesium, or their alloys (magnesium-silver alloy, magnesium - indium alloys, aluminum-lithium alloys such as lithium fluoride/aluminum), etc.) are preferred.
In order to increase electron injection efficiency and improve device characteristics, lithium, sodium, potassium, cesium, calcium, magnesium, or alloys containing these low work function metals are effective. However, these low work function metals are generally unstable in the atmosphere. In order to improve this point, a method is known in which, for example, the organic layer is doped with a trace amount of lithium, cesium, or magnesium to use a highly stable electrode. Other dopants that can also be used are inorganic salts such as lithium fluoride, cesium fluoride, lithium oxide, and cesium oxide. However, it is not limited to these.

Additionally, metals such as platinum, gold, silver, copper, iron, tin, aluminum and indium, or alloys of these metals, as well as inorganic materials such as silica, titania and silicon nitride, polyvinyl alcohol, and vinyl chloride, are used to protect the electrodes. A preferred example is to laminate a hydrocarbon polymer compound or the like. The method for producing these electrodes is not particularly limited as long as conduction can be achieved, such as resistance heating, electron beam evaporation, sputtering, ion plating, and coating.

<Binders that may be used in each layer>
The above materials used for the hole injection layer, hole transport layer, light emitting layer, electron transport layer and electron injection layer can be used alone to form each layer, but polyvinyl chloride, polycarbonate, Polystyrene, poly(N-vinylcarbazole), polymethyl methacrylate, polybutyl methacrylate, polyester, polysulfone, polyphenylene oxide, polybutadiene, hydrocarbon resin, ketone resin, phenoxy resin, polyamide, ethyl cellulose, vinyl acetate resin, ABS resin, polyurethane resin Solvent-soluble resins such as
It is also possible to use it by dispersing it in curable resins such as phenol resins, xylene resins, petroleum resins, urea resins, melamine resins, unsaturated polyester resins, alkyd resins, epoxy resins, and silicone resins.

<Method for manufacturing organic electroluminescent device>
Each layer constituting an organic EL element is prepared by using a vapor deposition method, resistance heating vapor deposition, electron beam vapor deposition, sputtering, molecular lamination method, printing method, spin coating method, or casting method.
It can be formed by forming a thin film using a method such as a coating method. The thickness of each layer formed in this way is not particularly limited and can be set appropriately depending on the properties of the material, but is usually in the range of 2 nm to 5000 nm. The film thickness can usually be measured using a crystal oscillation type film thickness measuring device. When forming a thin film using an evaporation method, the evaporation conditions vary depending on the type of material, the intended crystal structure and association structure of the film, and so on. Generally, the deposition conditions are: boat heating temperature +50 to +400°C, degree of vacuum 10 ^-6 to 10 ^-3 Pa, and deposition rate 0.01 to +400°C.
It is preferable to appropriately set the speed at 50 nm/sec, the substrate temperature from -150 to +300° C., and the film thickness from 2 nm to 5 μm.

Next, as an example of a method for producing an organic EL device, an organic EL device consisting of an anode/hole injection layer/hole transport layer/light emitting layer made of a host material and dopant material/electron transport layer/electron injection layer/cathode will be described. The manufacturing method will be explained. After a thin film of an anode material is formed on a suitable substrate by vapor deposition or the like to produce an anode, thin films of a hole injection layer and a hole transport layer are formed on this anode. On top of this, a host material and a dopant material are co-deposited to form a thin film to form a light emitting layer.
The desired organic EL device can be obtained by forming an electron transport layer and an electron injection layer on this light emitting layer, and further forming a thin film of a cathode material by vapor deposition or the like to serve as a cathode. In addition, in the production of the above-mentioned organic EL element, it is also possible to reverse the production order and produce the cathode, electron injection layer, electron transport layer, light emitting layer, hole transport layer, hole injection layer, and anode in this order. It is.

When applying a direct current voltage to the organic EL element obtained in this way, it is sufficient to apply it with the anode as + polarity and the cathode as - polarity. Luminescence can be observed from the sides (anode or cathode, or both). This organic EL element also emits light when pulsed current or alternating current is applied. Note that the waveform of the applied alternating current may be arbitrary.

<Application examples of organic electroluminescent devices>
Further, the present invention can be applied to a display device equipped with an organic EL element or a lighting device equipped with an organic EL element.
A display device or a lighting device equipped with an organic EL element can be manufactured by a known method such as connecting the organic EL element according to this embodiment with a known drive device, and can be manufactured by a known method such as direct current drive, pulse drive, alternating current drive, etc. It can be driven using a known driving method as appropriate.

Examples of display devices include panel displays such as color flat panel displays, flexible displays such as flexible color organic electroluminescent (EL) displays, etc. (Refer to the official gazette, Japanese Patent Application Laid-open No. 2004-281086, etc.). In addition, examples of display methods include matrix and/or segment methods. Note that matrix display and segment display may coexist in the same panel.

In a matrix, display pixels are arranged two-dimensionally in a grid or mosaic pattern, and characters or images are displayed as a collection of pixels. The shape and size of pixels are determined by the application. For example, rectangular pixels with sides of 300 μm or less are usually used to display images and characters on computers, monitors, and televisions, and in the case of large displays such as display panels, pixels with sides of mm order are used. become. In the case of monochrome display, pixels of the same color may be arranged, but in the case of color display, red, green, and blue pixels are displayed side by side. In this case, there are typically delta types and striped types. As a driving method for this matrix, either a line sequential driving method or an active matrix driving method may be used. Line sequential driving has the advantage of a simpler structure, but when considering operating characteristics, active matrix driving may be superior in some cases, so it is necessary to use it properly depending on the application.

In the segment method (type), a pattern is formed to display predetermined information, and a predetermined area is caused to emit light. Examples include time and temperature displays on digital clocks and thermometers, operating status displays on audio equipment and electromagnetic cookers, and panel displays on automobiles.

Examples of lighting devices include lighting devices for indoor lighting, backlights for liquid crystal display devices, etc.
(See Publication No. 19211, etc.) Backlights are mainly used for the purpose of improving the visibility of display devices that do not emit light by themselves, and are used in liquid crystal display devices, watches, audio devices, automobile panels, display boards, signs, and the like. In particular, considering that it is difficult to reduce the thickness of liquid crystal display devices, especially backlights for personal computers where thinning is an issue, since conventional systems consist of fluorescent lamps and light guide plates, this embodiment A backlight using a light emitting element according to the above is characterized by being thin and lightweight.

EXAMPLES Hereinafter, the present invention will be explained in more detail with reference to Examples, but the present invention is not limited thereto. First, examples of synthesis of polycyclic aromatic compounds and pyrene compounds will be described below.

Synthesis example (1): Synthesis of compound (1-290)

Under a nitrogen atmosphere, methyl 4-methoxysalicylate (50.0 g), pyridine (dehydrated) (3
The flask containing 50 ml) was cooled in an ice bath. Trifluoromethanesulfonic anhydride (154.9 g) was then added dropwise to this solution. After dropping, remove the ice bath and incubate at room temperature for 2 hours.
The mixture was stirred for an hour and water was added to stop the reaction. After adding toluene and separating the organic layer, methyl 4-methoxy-2-(((trifluoromethyl)sulfonyl)oxy)benzoate was obtained by purifying with a silica gel short pass column (eluent: toluene). (86.0
g).

Under nitrogen atmosphere, methyl 4-methoxy-2-(((trifluoromethyl)sulfonyl)
oxy)benzoate (23.0 g), (4-(diphenylamino)phenyl)boronic acid (25.4 g), tripotassium phosphate (31.1 g), toluene (184 ml), ethanol (27.6 ml) and water. (27.6 ml) of Pd(PPh ₃ ) ₄ (2.
5 g) was added thereto, and the mixture was stirred at reflux temperature for 3 hours. The reaction solution was cooled to room temperature, water and toluene were added to separate the organic layer, and the solvent in the organic layer was distilled off under reduced pressure. The obtained solid was purified with a silica gel column (eluent: heptane/toluene mixed solvent) to obtain methyl 4'-(diphenylamino)-5-methoxy-[1,1'-biphenyl]-2-carboxylate. (29
．． 7g). At this time, gradually increase the ratio of toluene in the eluent by referring to the method described in "Guidelines for Organic Chemistry Experiments (1) - Substance Handling Methods and Separation and Purification Methods" published by Kagaku Doujin Publishing Co., Ltd., page 94. The target product was eluted by increasing the amount.

Under a nitrogen atmosphere, methyl 4'-(diphenylamino)-5-methoxy-[1,1'-biphenyl]-2-carboxylate (11.4 g) was dissolved in THF (111.4 ml).
The solution was cooled in a water bath and a solution of methylmagnesium bromide in THF (1.0M,
295 ml) was added dropwise. After the dropwise addition was completed, the water bath was removed, the temperature was raised to reflux temperature, and the mixture was stirred for 4 hours. Thereafter, the mixture was cooled in an ice bath, an aqueous ammonium chloride solution was added to stop the reaction, ethyl acetate was added to separate the organic layer, and the solvent was distilled off under reduced pressure. The obtained solid was transferred to a silica gel column (
Eluent: toluene) to give 2-(4'-(diphenylamino)-5-methoxy-[1
, 1'-biphenyl]-2-yl)propan-2-ol was obtained (8.3 g).

Under nitrogen atmosphere, 2-(4'-(diphenylamino)-5-methoxy-[1,1'-biphenyl]-2-yl)propan-2-ol (27.0 g), TAYCACURE-15
(13.5 g) and toluene (162 ml) was stirred at reflux temperature for 2 hours. The reaction solution was cooled to room temperature, passed through a silica gel short pass column (eluent: toluene) to remove TAYCACURE-15, and the solvent was distilled off under reduced pressure to obtain 6-methoxy-9,9'- Dimethyl-N,N-diphenyl-9H-fluoren-2-amine was obtained (25.8 g).

Under nitrogen atmosphere, 6-methoxy-9,9'-dimethyl-N,N-diphenyl-9H-fluoren-2-amine (25.0 g), pyridine hydrochloride (36.9 g) and N-methyl-
A flask containing 2-pyrrolidone (NMP) (22.5 ml) was stirred at reflux temperature for 6 hours. The reaction solution was cooled to room temperature, water and ethyl acetate were added, and the organic layer was separated. After distilling off the solvent under reduced pressure, the product was purified using a silica gel column (eluent: toluene) to obtain 7-(diphenylamino)-9,9'-dimethyl-9H-fluoren-3-ol (22.0 g
).

7-(diphenylamino)-9,9'-dimethyl-9H-fluorene- under nitrogen atmosphere
A flask containing 3-ol (14.1 g), 2-bromo-1,3-difluorobenzene (3.6 g), potassium carbonate (12.9 g) and NMP (30 ml) was heated at reflux temperature for 5 minutes.
The mixture was heated and stirred for hours. After the reaction was stopped, the reaction solution was cooled to room temperature, water was added, and the precipitate was collected by suction filtration. The obtained precipitate was washed with water and then with methanol, and then purified with a silica gel column (eluent: heptane/toluene mixed solvent) to obtain 6,6'-((2-bromo-1,3-phenylene). Bis(oxy))bis(9,9-dimethyl-N,N-diphenyl-9H-fluoren-2-amine) was obtained (12.6 g). At this time, the target product was eluted by gradually increasing the ratio of toluene in the eluent.

Under nitrogen atmosphere, 6,6'-((2-bromo-1,3-phenylene)bis(oxy))bis(9,9-dimethyl-N,N-diphenyl-9H-fluoren-2-amine) (11 ．．
A flask containing 0g) and xylene (60.5ml) was cooled to -40°C, and 2.6
A hexane solution (5.1 ml) of n-butyllithium M was added dropwise. After the dropwise addition was completed, the mixture was stirred at this temperature for 0.5 hours, and then heated to 60°C and stirred for 3 hours. Thereafter, the reaction solution was depressurized to distill off low-boiling components, and then cooled to -40° C. and boron tribromide (4.3 g) was added. The mixture was heated to room temperature and stirred for 0.5 hours, then cooled to 0°C, N-ethyl-N-isopropylpropan-2-amine (3.8g) was added, and the mixture was heated and stirred at 125°C for 8 hours. The reaction solution was cooled to room temperature, an aqueous sodium acetate solution was added to stop the reaction, and toluene was added to separate the organic layer. The organic layer was purified using a silica gel short pass column, then a silica gel column (eluent: heptane/toluene = 4 (volume ratio)), and then an activated carbon column (eluent: toluene) to obtain compound (1-290) ( 1.2g).

The structure of the obtained compound (1-290) was confirmed by NMR measurement.
¹ H-NMR (400 MHz, CDCl ₃ ): δ = 8.64 (s, 2H), 7.75 (m
, 3H), 7.69 (d, 2H), 7.30 (t, 8H), 7.25 (s, 2H), 7.
20 (m, 10H), 7.08 (m, 6H), 1.58 (s, 12H).

Synthesis example (2): Synthesis of compound (1-139)

Compound (1-139) was synthesized using the same method as in the synthesis example described above.

The structure of the obtained compound (1-139) was confirmed by NMR measurement.
¹ H-NMR (500 MHz, CDCl ₃ ): δ = 1.47 (s, 36 H), 2.17 (
s, 3H), 5.97 (s, 2H), 6.68 (d, 2H), 7.28 (d, 4H), 7
．． 49 (dd, 2H), 7.67 (d, 4H), 8.97 (d, 2H).

Synthesis example (3): Synthesis of compound (1-151)

Compound (1-151) was synthesized using the same method as in the synthesis example described above.

The structure of the obtained compound (1-151) was confirmed by NMR measurement.
¹ H-NMR (500 MHz, CDCl ₃ ): δ = 1.46 (s, 18H), 1.47 (
s, 18H), 6.14 (d, 2H), 6.75 (d, 2H), 7.24 (t, 1H),
7.29 (d, 4H), 7.52 (dd, 2H), 7.67 (d, 4H), 8.99 (d
, 2H).

Synthesis example (4): Synthesis of compound (2-1) “11,11-diphenyl-6-(pyren-1-yl)-11H-benzo[a]fluorene”

Under a nitrogen atmosphere, 1-bromo-2-methoxynaphthalene (9.5 g) and bis(
pinacolato) diboron (12.2 g), potassium acetate (11.8 g), (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride/dichloromethane complex (0.98 g) and cyclopentylmethyl as a palladium catalyst. Ether (CP
ME, 143 mL) was placed in a flask and stirred at reflux temperature for 4 hours under nitrogen atmosphere. The reaction solution was cooled to room temperature, water was added, and ethyl acetate was further added for liquid separation and extraction. After separating the organic layer, it was dried, concentrated, and purified using an activated carbon short-pass column (eluent: toluene) to obtain intermediate A.
(11.3 g) was obtained.

Under a nitrogen atmosphere, Intermediate A (11.3 g), methyl 2-bromobenzoate (8.6 g), potassium phosphate (16.9 g), tetrakis(triphenylphosphine)palladium (1.4 g) as a palladium catalyst, Toluene (85 mL), ethanol (17 mL) and water (9 mL) were placed in a flask and stirred at reflux temperature for 7 hours under a nitrogen atmosphere. The reaction solution was cooled to room temperature, water was added, and toluene was further added for liquid separation and extraction. After separating the organic layer, it was dried and concentrated, and the crude product was purified using a silica gel column (eluent: toluene) to obtain intermediate B (9.1
g).

Intermediate B (9.1 g) and tetrahydrofuran (THF, 21 mL) under nitrogen atmosphere
was placed in a flask and cooled in an ice bath, then 1M phenylmagnesium bromide/THF solution (94 mL) was added dropwise under a nitrogen atmosphere, and the mixture was stirred at reflux temperature for 3 hours. After cooling, saturated ammonium chloride aqueous solution was added to stop the reaction, and ethyl acetate was added to perform solvent extraction. After separating the organic layer, it was dried and concentrated, and the crude product was purified using a silica gel column (eluent: toluene) to obtain Intermediate C (12.3 g).

Intermediate C (12.3 g) and acetic acid (117 mL) were placed in a flask under a nitrogen atmosphere, and one drop of concentrated sulfuric acid was added thereto, followed by stirring at 90° C. for 3 hours under a nitrogen atmosphere. After cooling, water was added, the precipitate was filtered, and the precipitate was washed with water and dried to obtain Intermediate D (10.6 g).

Under a nitrogen atmosphere, Intermediate D (10.6 g), pyridine hydrochloride (15.4 g) and N-methylpyrrolidone (NMP, 10 mL) were placed in a flask and stirred at 185° C. for 4 hours under a nitrogen atmosphere. After cooling and adding water, the precipitate was filtered, washed with water, and dried to obtain Intermediate E (10.1 g).

Under a nitrogen atmosphere, intermediate E (10 g) and pyridine (100 mL) were placed in a flask,
After cooling in an ice bath, trifluoromethanesulfonic anhydride (18.3 g) was added under nitrogen atmosphere.
was dripped. After stirring as it was for 3 hours, water was added to stop the reaction. Intermediate F (13.4 g) was obtained by filtering the precipitate and purifying it with a silica gel short pass column (eluent: toluene).

Under a nitrogen atmosphere, intermediate F (3 g), 1-pyreneboronic acid (2.1 g), potassium phosphate (2.5 g), tetrakis(triphenylphosphine)palladium (0.2 g) as a palladium catalyst, 1,2, 4-trimethylbenzene (24 mL), t-butyl alcohol (
3 mL) and water (1.5 mL) were placed in a flask and stirred at reflux temperature for 4 hours under a nitrogen atmosphere. The reaction solution was cooled to room temperature, water was added, and toluene was further added for liquid separation and extraction. After separating the organic layer, it was dried and concentrated, and the crude product was passed through a silica gel column (eluent: toluene/heptane =
Compound (2-1) was obtained by purification at a ratio of 3/1 (volume ratio) and then sublimation purification (1
．． 2g).

The structure of compound (2-1) obtained was confirmed by NMR measurement.
¹ H-NMR (CDCl ₃ ): 6.0 (d, 1H), 6.6 (dt, 1H), 7.0 (d
t, 1H), 7.2 to 7.5 (m, 13H), 7.9 to 8.0 (m, 5H), 8.0 (t
, 1H), 8.2-8.3 (m, 5H), 8.4 (d, 1H).

Synthesis example (5): Compound (2-46) “6-(6-(naphthalen-2-yl)pyrene-1
Synthesis of "-yl)-11,11-diphenyl-11H-benzo[a]fluorene"

Under nitrogen atmosphere, 1,6-dibromopyrene (3.5g), 2-naphthylboronic acid (1.7g)
g), potassium carbonate (2.7 g), tetrakis(triphenylphosphine)palladium (0.3 g) as a palladium catalyst, toluene (35 mL), and water (9 mL) were placed in a flask and heated under a nitrogen atmosphere at reflux temperature for 3 hours. Stir for hours. The reaction solution was cooled to room temperature, water was added, and toluene was further added for liquid separation and extraction. After separating the organic layer, it was dried and concentrated, and the crude product was purified with a silica gel column (eluent: toluene/heptane = 6/1 (volume ratio)) to obtain Intermediate G (2.1 g).

Under a nitrogen atmosphere, Intermediate F (7 g), bis(pinacolato)diboron (4.1 g), potassium acetate (4.0 g), and (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) as a palladium catalyst. ) Dichloride dichloromethane complex (0.3 g) and cyclopentyl methyl ether (CPME, 67 mL) were placed in a flask and stirred at reflux temperature for 4 hours under a nitrogen atmosphere. The reaction solution was cooled to room temperature, water was added, and ethyl acetate was further added for liquid separation and extraction. After separating the organic layer, it was dried, concentrated, and purified using an activated carbon short-pass column (eluent: toluene) to obtain Intermediate H (4.6 g).

Under a nitrogen atmosphere, Intermediate G (0.8 g), Intermediate H (0.9 g), potassium phosphate (0.
9g), tetrakis(triphenylphosphine)palladium (0.9g) as a palladium catalyst.
1g), 1,2,4-trimethylbenzene (12mL), t-butyl alcohol (2mL
) and water (1 mL) were placed in a flask and stirred at reflux temperature for 14 hours under a nitrogen atmosphere.
The reaction solution was cooled to room temperature, water was added, and toluene was further added to perform liquid separation extraction. After separating the organic layer, it was dried and concentrated, and the crude product was passed through a silica gel column (eluent: toluene/heptane = 1/
3 (volume ratio)) and then sublimation purification to obtain compound (2-46) (1.0
g).

The structure of the obtained compound (2-46) was confirmed by NMR measurement.
¹ H-NMR (CDCl ₃ ): 6.0 (d, 1H), 6.6 (dt, 1H), 7.0 (d
t, 1H), 7.2-7.6 (m, 15H), 7.8-8.2 (m, 14H), 8.2-
8.3 (m, 2H).

Synthesis example (6): Synthesis of compound (2-1001) "3,9-di(pyren-1-yl)spiro[benzo[a]fluorene-11,9'-fluorene]"

Under a nitrogen atmosphere, a flask containing pyrene-1-boronic acid (5 g), ethylene glycol (3.8 g) and toluene (30 mL) was stirred at reflux temperature for 3 hours. After the reaction, the mixture was cooled, water was added and stirred, and the organic layer was separated, and the organic layer was concentrated under reduced pressure to obtain a crude product. After passing the crude product through a silica gel short pass column (eluent: toluene), the eluate was concentrated to obtain 2-(pyren-1-yl)-1,3,2-dioxaborolane (4.2 g). .

Intermediate I synthesized by the method described in Patent Publication No. 2009-184993 under a nitrogen atmosphere
(3.8g), 2-(pyren-1-yl)-1,3,2-dioxaborolane (3.3g)
, chlorophenylallyl[1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene]palladium(II) (19 mg), potassium carbonate (3.2 g), tetrabutylammonium bromide (TBAB, 0.6 g), cyclopentyl methyl ether (CPME, 20 mL), and water (2 mL) were placed in a flask, and the mixture was heated and stirred at reflux temperature for 9 hours. After the reaction, the mixture was cooled, water was added to the reaction mixture, and the mixture was stirred, and then the precipitate was filtered. After drying the precipitate, heat and dissolve in chlorobenzene, filter through a silica gel short pass column (eluent: toluene), concentrate the eluate, filter the solid obtained, dry, and purify by sublimation. Compound (2-1001) was obtained (2.2 g).

The structure of the obtained compound (2-1001) was confirmed by NMR measurement.
¹ H-NMR (CDCl ₃ ): 6.9-7.0 (m, 4H), 7.2 (t, 2H), 7.
4 (dd, 1H), 7.4 (dt, 2H), 7.7 (dd, 1H), 7.8-7.9 (m
, 2H), 7.9-8.1 (m, 9H), 8.1-8.2 (m, 13H).

Synthesis example (7): Synthesis of compound (2-350) “2-(pyren-1-yl)triphenylene”

4,4,5,5-tetramethyl-2-(triphenylene-2) was added to the flask under a nitrogen atmosphere.
-yl)-1,3,2-dioxaborolane (3.0g), 1-bromopyrene (2.2g)
, chlorophenylallyl[1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene]palladium(II) (25 mg), potassium carbonate (2.2 g), tetrabutylammonium bromide (TBAB, 0.8 g), cyclopentyl methyl ether (CPME, 20 mL), and water (2 mL) were placed in a flask, and the mixture was heated and stirred at reflux temperature for 2 hours. After the reaction, the mixture was cooled, water was added to the reaction mixture, and the mixture was stirred, and then the precipitate was filtered. After drying the precipitate, it is heated and dissolved in chlorobenzene, filtered with a silica gel short pass column (eluent: toluene), and the solid obtained by concentrating the eluate is filtered and purified by sublimation after drying. Compound (2-350) was obtained (3.3 g).

The structure of the obtained compound (2-350) was confirmed by NMR measurement.
¹ H-NMR (CDCl ₃ ): 7.6-7.7 (m, 4H), 7.9 (dd, 1H), 8
．． 0 (m, 2H), 8.1-8.2 (m, 4H), 8.2 (m, 1H), 8.3 (m, 2H)
H), 8.7-8.8 (m, 4H), 8.8 (d, 1H), 8.9 (d, 1H).

Synthesis example (8): Compound (2-1080) “3,9-bis(7-(t-butyl)pyrene-
Synthesis of ``2-yl)spiro[benzo[a]fluorene-11,9'-fluorene]''

Intermediate J (1.7 g) synthesized by the method described in International Publication No. 2015/141608 under a nitrogen atmosphere, 2-bromo-7-(t-butyl)pyrene (2 g), and chlorophenylallyl [as a palladium catalyst] 1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene]palladium(II) (9 mg), potassium carbonate (1.6 g), tetrabutylammonium bromide (TBAB, 0.3 g), cyclopentylmethyl ether (C
PME (20 mL) and water (2 mL) were placed in a flask, and the mixture was heated and stirred at reflux temperature for 4 hours. After the reaction, the mixture was cooled, water was added to the reaction mixture, and the mixture was stirred, and then the precipitate was filtered. After drying the precipitate, heat and dissolve it in chlorobenzene, filter it with a silica gel short pass column (eluent: toluene), concentrate the eluate, filter the solid obtained, dry it, and purify it by sublimation. Compound (2-1080) was obtained (1.6 g).

The structure of the obtained compound (2-1080) was confirmed by NMR measurement.
¹ H-NMR (CDCl ₃ ): 1.6 (s, 9H), 1.6 (s, 9H), 6.9 (d,
2H), 6.9 (d, 1H), 7.1 (dt, 2H), 7.2 (d, 1H), 7.5 (d
t, 2H), 7.6 (dd, 1H), 7.9 (dd, 1H), 8.0 to 8.2 (m, 19
H), 8.3(s, 3H).

Synthesis example (9): Compound (2-174) “2-(pyren-1-yl)naphtho[2,3-b
] Synthesis of “Benzofuran”

Under nitrogen atmosphere, 1-pyreneboronic acid (1.0g), International Publication No. 2014/141725
2-bromobenzo[b]naphtho[2,3-d]furan (
1.1 g), tetrakis(triphenylphosphine)palladium (
0.09 g), potassium phosphate (1.7 g), xylene (15 mL), t-butyl alcohol (5 mL) and water (3 mL) were placed in a flask, and the mixture was heated and stirred at reflux temperature for 2 hours.
After the reaction, the mixture was cooled, water and ethyl acetate were added to the reaction mixture, and the mixture was stirred. The precipitate was filtered, and the crude product was washed with water and methanol. After drying the precipitate, it was heated and dissolved in chlorobenzene, filtered through a silica gel short pass column (eluent: toluene), and the solid obtained by concentrating the eluate was further purified by chlorobenzene/re-precipitation. The obtained solid was dried and purified by sublimation to obtain compound (2-174) (1.0 g).

The structure of the obtained compound (2-174) was confirmed by NMR measurement.
¹ H-NMR (CDCl ₃ ): 7.5 (m, 1H), 7.5-7.6 (m, 1H), 7.
7-7.8 (m, 2H), 8.0-8.3 (m, 13H), 8.5 (s, 1H).

Synthesis Example (10): Compound (2-356) “2-(pyren-1-yl)dibenzo[g,p
] Synthesis of “Chrysene”

Under a nitrogen atmosphere, 3-bromodibenzo[g,p]chrysene (14 g) synthesized by the method described in Patent Publication No. 2011-006397 and tetrahydrofuran (THF, 200 g)
mL) was put into a flask to make a homogeneous solution, which was then cooled to -78 degrees in a dry ice-acetone bath, and a 1.6M n-butyllithium/hexane solution (28 mL) was added dropwise. After stirring at the same temperature for 0.5 hours, 2-isopropoxy-4,4,5,5-tetramethyl-1,
3,2-dioxaborolane (12.8g) was added. After stirring at the same temperature for 3 hours, the temperature was raised and diluted hydrochloric acid was added to stop the reaction. After adding toluene and extracting, the organic layer was concentrated, and the resulting crude product was purified with a silica gel column (eluent: toluene/heptane = 7/3 (volume ratio)) to obtain intermediate K ( 11.5g).

Under a nitrogen atmosphere, Intermediate K (1.0 g), 1-bromopyrene (0.59 g), bis(di-t-butyl(4-dimethylaminophenyl)phosphine) dichloropalladium (16 mg) as a palladium catalyst, potassium phosphate ( 0.9 g), xylene (10 mL), t-butyl alcohol (3 mL) and water (2 mL) were placed in a flask and stirred at reflux temperature for 2 hours. After the reaction, the reaction solution was cooled, water and ethyl acetate were added thereto, and the mixture was stirred, and then the deposited precipitate was filtered. The obtained crude product was purified using a silica gel short pass column (eluent: toluene), and then reprecipitated with toluene/heptane for purification. The obtained solid was dried and purified by sublimation to obtain compound (2-356) (0.7 g).

The structure of the obtained compound (2-356) was confirmed by NMR measurement.
¹ H-NMR (CDCl ₃ ): 7.7 (m, 6H), 7.9 (dd, 1H) 8.0-8.
1 (m, 2H), 8.1-8.3 (m, 5H), 8.3 (d, 1H), 8.4 (d, 1H
), 8.7-8.8 (m, 5H), 8.9 (m, 1H), 8.9 (d, 1H), 9.0 (
d, 1H).

Synthesis Example (11): Synthesis of compound (2-359) “1,6-bis(naphtho[2,3-b]benzofuran-2-yl)-3a ¹ ,5a ¹ -dihydropyrene”

2, synthesized by the method described in International Publication No. 2014/141725 under a nitrogen atmosphere
-Bromobenzo[b]naphtho[2,3-d]furan (10.8 g) and tetrahydrofuran (THF, 200 mL) were placed in a flask and cooled to -78°C in a dry ice-acetone bath. A 1.6M n-butyllithium/heptane solution (25 mL) was added dropwise thereto. After stirring at the same temperature for 1 hour, 2-isopropoxy-4,4,5,5-tetramethyl-1,
3,2-dioxaborolane (10 g) was added. After stirring at the same temperature for 2 hours, the temperature was raised and diluted hydrochloric acid was added to stop the reaction. After adding toluene and extracting, the organic layer was concentrated, and the resulting crude product was purified with a silica gel column (eluent: toluene/heptane = 7/3 (volume ratio)) to obtain intermediate L ( 9.2g).

Under a nitrogen atmosphere, 1,6-dibromopyrene (1.0 g), Intermediate L (2.0 g), bis(di-t-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium (20 mg) as a palladium catalyst, phosphorus potassium acid (2.4 g), xylene (15 mL), t-
Butyl alcohol (3 mL) and water (2 mL) were placed in a flask and stirred at reflux temperature for 2 hours. After the reaction, the reaction solution was cooled, water and ethyl acetate were added thereto, and the mixture was stirred, and then the deposited precipitate was filtered. The obtained crude product was purified using a silica gel short pass column (eluent: toluene), and then washed and purified with hot chlorobenzene. The obtained solid was dried and purified by sublimation to obtain compound (2-359) (1.6 g).

The obtained compound (2-359) was confirmed by LC-MS measurement.
MS (ACPI) m/z=635 (M+H)

By appropriately changing the raw material compounds, other compounds used in the present invention can be synthesized by a method similar to the above-mentioned synthesis example.

EXAMPLES Hereinafter, in order to explain the present invention in more detail, examples of organic EL devices using the compounds of the present invention will be shown, but the present invention is not limited thereto.

Organic EL devices according to Examples 1 to 12 and Comparative Example 1 were produced, and each had a 1000 cd/
Voltage (V), emission wavelength (nm), and external quantum efficiency (%), which are characteristics during ^m2 emission, were measured.

The quantum efficiency of a light-emitting element includes internal quantum efficiency and external quantum efficiency.
It shows the rate at which external energy injected as electrons (or holes) into the light-emitting layer of a light-emitting element is converted into pure photons. On the other hand, external quantum efficiency is calculated based on the amount of photons emitted to the outside of the light-emitting element, and some of the photons generated in the light-emitting layer are absorbed or continue to be reflected inside the light-emitting element. Since the light is not emitted to the outside of the light emitting device, the external quantum efficiency is lower than the internal quantum efficiency.

The method for measuring external quantum efficiency is as follows. Advantest voltage/current generator R6
144, a voltage was applied so that the luminance of the device was 1000 cd/m ² to cause the device to emit light. Spectral radiance in the visible light region was measured in the direction perpendicular to the light emitting surface using a spectral radiance meter SR-3AR manufactured by TOPCON. Assuming that the light-emitting surface is a completely diffusing surface, the number of photons at each wavelength is obtained by dividing the measured spectral radiance value of each wavelength component by the wavelength energy and multiplying it by π. Next, the number of photons was integrated over the entire observed wavelength range to obtain the total number of photons emitted from the element. The value obtained by dividing the applied current value by the elementary charge is the number of carriers injected into the device, and the value obtained by dividing the total number of photons emitted from the device by the number of carriers injected into the device is the external quantum efficiency.

Material composition of each layer in the organic EL devices according to Examples 1 to 12 and Comparative Example 1 produced,
and EL characteristic data are shown in Table 1 below.

In Table 1, "HI" is N ⁴ ,N ^4' -diphenyl-N ⁴ ,N ^4' -bis(9-phenyl-9H-carbazol-3-yl)-[1,1'-biphenyl]-4, 4'-diamine, "HAT-CN" is 1,4,5,8,9,12-hexaazatriphenylenehexacarbonitrile, and "HT-1" is N-([1,1'-biphenyl ]-4-yl-9,9-dimethyl-N-[4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluoren-2-amine[1,1'-biphenyl]-4 - is an amine;
"HT-2" is N,N-bis(4-(dibenzo[b,d]furan-4-yl)phenyl)
-[1,1':4',1"-terphenyl]-4-amine, and "HT-3" is N-(
[1,1'-biphenyl]-2-yl)-N-(9,9-dimethyl-9H-fluorene-
2-yl)-9,9'-spirobi[fluorene]-4-amine, and "ET-1" is 4
,6,8,10-tetraphenyl[1,4]benzoxaborinino[2,3,4-kl]phenoxaborinine, and "ET-2" is 3,3'-((2-phenylanthracene -9
,10-diyl)bis(4,1-phenylene))bis(4-methylpyridine), and “
ET-3" is 9-(7-(dimesitylboryl)-9,9-dimethyl-9H-fluorene-
2-yl)-3,6-dimethyl-9H-carbazole, "ET-4" is 4-(3-(
4-(10-phenylanthracen-9-yl)naphthalen-1-yl)phenyl)pyridine, and comparative compound A is 9-([1,2'-binaphthalen]-7-yl)-10-phenylanthracene. It is. The chemical structure is shown below along with "Liq".

<Example 1>
<Element in which the host is a compound (2-1) and the dopant is a compound (1-139)>
An ITO film formed to a thickness of 180 nm by sputtering was polished to a thickness of 150 nm.
A 26 mm x 28 mm x 0.7 mm glass substrate (manufactured by Optoscience Co., Ltd.) was used as a transparent support substrate. This transparent support substrate was fixed to a substrate holder of a commercially available vapor deposition apparatus (manufactured by Showa Shinku Co., Ltd.), and HI, HAT-CN, HT-1, HT-2, compound (2-1), compound (1-1)
39), molybdenum deposition boat containing ET-1 and ET-2, Liq,
An aluminum nitride deposition boat containing magnesium and silver was installed.

The following layers were sequentially formed on the ITO film of the transparent support substrate. Vacuum chamber at 5×10 ^-4 Pa
First, HI was heated and deposited to a thickness of 40 nm, and then HAT-C
N is heated to deposit it to a thickness of 5 nm, then HT-1 is heated to deposit it to a thickness of 15 nm, and then HT-2 is heated to a thickness of 10 nm. A hole injection/transport layer consisting of four layers was formed by vapor deposition. Next, compound (2-1) and compound (1-139) were simultaneously heated and deposited to a thickness of 25 nm to form a light-emitting layer. Compound (2-1)
The vapor deposition rate was adjusted so that the weight ratio of compound (1-139) and compound (1-139) was approximately 98:2. Next, ET-1 was heated and deposited to a thickness of 5 nm to form an electron transport layer 1. Next, ET-2 and Liq were simultaneously heated and deposited to a thickness of 25 nm to form an electron transport layer 2. The deposition rate was adjusted so that the weight ratio of ET-2 to Liq was approximately 50:50. The deposition rate of each layer was 0.01-1 nm/sec. After that, Liq is heated to a film thickness of 1
0.01 to 0.1 nm/sec, then simultaneously heat magnesium and silver to form a cathode with a thickness of 100 nm, and form an organic EL element. Obtained. At this time, the atomic ratio of magnesium and silver is 10:1.
The deposition rate was adjusted between 0 nm/sec.

A DC voltage was applied using the ITO electrode as the anode and the magnesium/silver electrode as the cathode, and the voltage was 1000c.
When the characteristics at the time of d/m ² emission were measured, blue light emission with a wavelength of 462 nm was obtained. Also,
The driving voltage was 4.1 V, and the external quantum efficiency was 6.7%.

<Examples 2 to 12 and Comparative Example 1>
The materials listed in Table 1 were selected as the materials for each layer, and an organic EL element was obtained in the same manner as in Example 1. In Example 11, one electron transport layer was formed by co-evaporating ET-1 and LIq to a thickness of 30 nm. Further, the organic EL characteristics were also evaluated in the same manner as in Example 1 (Table 1). Note that blue light emission was obtained in all elements.

As mentioned above, some of the compounds according to the present invention have been evaluated as materials for the light-emitting layer of organic EL devices, and their usefulness has been shown, but other compounds that have not been evaluated also have the same basic skeleton,
These compounds have a similar structure as a whole, and those skilled in the art will understand that they are similarly excellent materials for light emitting layers.

According to a preferred embodiment of the present invention, there is provided a polycyclic aromatic compound represented by formula (1) and a pyrene compound represented by formula (2) that can be combined with the polycyclic aromatic compound to obtain optimal luminescent properties. By manufacturing an organic EL device using a material for a light emitting layer formed by combining these, it is possible to provide an organic EL device that exhibits particularly excellent luminous efficiency and well-balanced performance.

100 Organic electroluminescent device 101 Substrate 102 Anode 103 Hole injection layer 104 Hole transport layer 105 Light emitting layer 106 Electron transport layer 107 Electron injection layer 108 Cathode

Claims (11)

An organic electroluminescent device comprising a pair of electrodes consisting of an anode and a cathode, and a light emitting layer disposed between the pair of electrodes,
The light-emitting layer includes at least one of a compound represented by the following general formula (1) and a multimer having a plurality of structures represented by the following general formula (1), and a pyrene-based compound represented by the following general formula (2). An organic electroluminescent device comprising at least one compound.
In the above formula (1),
Ring A, Ring B and Ring C are each independently an aryl ring or a heteroaryl ring, and at least one hydrogen in these rings may be substituted,
X ¹ and X ² are each independently >O or >NR, and R in >NR is an optionally substituted aryl, an optionally substituted heteroaryl, an optionally substituted heteroaryl, or an optionally substituted heteroaryl. alkyl or optionally substituted cycloalkyl, and R in >N-R may be bonded to the A ring, B ring and/or C ring through a linking group or a single bond, and ,
At least one hydrogen in the compound or structure represented by formula (1) may be independently substituted with halogen, cyano or deuterium,
In the above formula (2),
s pyrene moieties and p Ar moieties are bonded at any position of * of the pyrene moiety and any position of the Ar moiety,
At least one hydrogen in the pyrene moiety is each independently an aryl having 6 to 10 carbon atoms, a heteroaryl having 2 to 11 carbon atoms, an alkyl having 1 to 30 carbon atoms, a cycloalkyl having 3 to 24 carbon atoms, or a cycloalkyl having 3 to 24 carbon atoms. Alkenyl having 2 to 30 carbon atoms, alkoxy having 1 to 30 carbon atoms or 6 carbon atoms
-30 aryloxy may be substituted, and at least one hydrogen in these may be independently substituted with aryl having 6 to 10 carbon atoms, heteroaryl having 2 to 11 carbon atoms,
Optionally substituted with alkyl having 1 to 30 carbon atoms, cycloalkyl having 3 to 24 carbon atoms, alkenyl having 2 to 30 carbon atoms, alkoxy having 1 to 30 carbon atoms, or aryloxy having 6 to 30 carbon atoms,
Ar is each independently an aryl having 14 to 40 carbon atoms or a heteroaryl having 12 to 40 carbon atoms, and at least one hydrogen therein is each independently an aryl having 6 to 10 carbon atoms, an aryl having 6 to 10 carbon atoms, or a heteroaryl having 12 to 40 carbon atoms. heteroaryl having 2 to 11 carbon atoms, alkyl having 1 to 30 carbon atoms,
Optionally substituted with cycloalkyl having 3 to 24 carbon atoms, alkenyl having 2 to 30 carbon atoms, alkoxy having 1 to 30 carbon atoms, or aryloxy having 6 to 30 carbon atoms,
s and p are each independently an integer of 1 or 2, s and p cannot be 2 at the same time, and when s is 2, the two pyrene moieties are structurally the same including the substituents. or may be different, and when p is 2, the two Ar moieties may be structurally the same or different including the substituents, and,
At least one hydrogen in the compound represented by formula (2) may be independently substituted with halogen, cyano, or deuterium. The organic electroluminescent device according to claim 1, wherein the Ar is each independently a group represented by the following general formula (Ar-1) or general formula (Ar-2).
In each of the above formulas,
Z is >CR ₂ , >NR, >O or >S;
>R in CR ₂ is each independently alkyl having 1 to 6 carbon atoms, or 3 to 14 carbon atoms.
cycloalkyl, aryl having 6 to 12 carbon atoms, or heteroaryl having 2 to 12 carbon atoms, and at least one hydrogen in the aryl and heteroaryl has 1 to 4 carbon atoms.
may be substituted with alkyl or cycloalkyl having 5 to 10 carbon atoms, and R may be bonded to each other to form a ring,
>R in NR is alkyl having 1 to 4 carbon atoms, cycloalkyl having 5 to 10 carbon atoms,
Aryl having 6 to 12 carbon atoms or heteroaryl having 2 to 12 carbon atoms, and at least one hydrogen in the aryl and heteroaryl is substituted with alkyl having 1 to 4 carbon atoms or cycloalkyl having 5 to 10 carbon atoms. It's okay,
R ¹ to R ⁸ and R ¹⁰ to R ¹⁹ each independently represent hydrogen, aryl having 6 to 10 carbon atoms, heteroaryl having 2 to 11 carbon atoms, alkyl having 1 to 30 carbon atoms, and 3 to 2 carbon atoms.
cycloalkyl having 4 to 30 carbon atoms, alkenyl having 2 to 30 carbon atoms, alkoxy having 1 to 30 carbon atoms, or aryloxy having 6 to 30 carbon atoms, in which at least one hydrogen is an alkyl having 1 to 6 carbon atoms or an alkyl having 3 to 6 carbon atoms. may be substituted with ~14 cycloalkyl, R ¹
Adjacent groups among R ⁸ to R 8 or adjacent groups among R ¹⁰ to R ¹⁹ may be bonded to each other to form a condensed ring, and each formed ring independently has a carbon number of 6 ~1
Aryl of 0, heteroaryl of 2 to 11 carbon atoms, alkyl of 1 to 30 carbon atoms, 3 carbon atoms
-24 cycloalkyl, C2-30 alkenyl, C1-30 alkoxy or C6-30 aryloxy, and at least one hydrogen in these is substituted with C1-6 may be substituted with alkyl or cycloalkyl having 3 to 14 carbon atoms, and
At least one hydrogen in the group represented by the above formula (Ar-1) or formula (Ar-2) may be independently substituted with halogen, cyano, or deuterium,
In formula (2), the pyrene moiety is bonded at any position in the group represented by formula (Ar-1) or formula (Ar-2) above. The organic electroluminescent device according to claim 1 or 2, wherein the compound represented by the general formula (1) is a compound represented by the following general formula (1').
(In the above formula (1'),
R ¹ to R ¹¹ are each independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, alkyl, cycloalkyl, alkoxy, or aryloxy, in which at least one hydrogen may be each independently substituted with aryl, heteroaryl, alkyl, or cycloalkyl, and adjacent groups among R ¹ to R ¹¹ may be bonded to form ring a, b
The ring or c-ring may form an aryl ring or a heteroaryl ring, and at least one hydrogen in the formed ring is independently aryl, heteroaryl,
Optionally substituted with diarylamino, diheteroarylamino, arylheteroarylamino, alkyl, cycloalkyl, alkoxy or aryloxy, in which at least one hydrogen is independently aryl, heteroaryl, alkyl or Optionally substituted with cycloalkyl,
X ¹ and X ² are each independently >O or >NR, and R in >NR is an aryl having 6 to 12 carbon atoms, a heteroaryl having 2 to 15 carbon atoms, or 1 to 6 carbon atoms. is an alkyl or cycloalkyl having 3 to 14 carbon atoms, and at least one hydrogen in the aryl or heteroaryl may be substituted with an alkyl having 1 to 4 carbon atoms or a cycloalkyl having 5 to 10 carbon atoms, and , R in >N-R is -O-, -S-, -C(-R) ₂
- or may be bonded to the a ring, b ring and/or c ring through a single bond, and the -
R in C(-R) ₂ - is alkyl having 1 to 6 carbon atoms or cycloalkyl having 3 to 14 carbon atoms, and
At least one hydrogen in the compound represented by formula (1') may be independently substituted with halogen, cyano, or deuterium. The above Ar each independently represents the following general formulas (Ar-1-1) to (Ar-1-12)
and the organic electroluminescent device according to claim 1, which is a group represented by any one of formulas (Ar-2-1) to (Ar-2-4).
In each of the above formulas,
Z is >CR ₂ , >NR, >O or >S;
>R in CR ₂ is each independently alkyl having 1 to 6 carbon atoms, or 3 to 14 carbon atoms.
is cycloalkyl or aryl having 6 to 12 carbon atoms, and R may be bonded to each other to form a ring,
>R in NR is alkyl having 1 to 4 carbon atoms, cycloalkyl having 5 to 10 carbon atoms, or aryl having 6 to 12 carbon atoms,
At least one hydrogen in the group represented by each of the above formulas each independently has a carbon number of 6
Optionally substituted with an aryl having ~10 carbon atoms, a heteroaryl having 2 to 11 carbon atoms, an alkyl having 1 to 30 carbon atoms, or a cycloalkyl having 3 to 24 carbon atoms, and
At least one hydrogen in the group represented by each of the above formulas may be independently substituted with halogen, cyano, or deuterium,
In formula (2), the pyrene moiety is represented by any of the above formulas (Ar-1-1) to (Ar-1-12) and formulas (Ar-2-1) to (Ar-2-4). bond at any position in the group. 5. The organic electroluminescent device according to claim 1, wherein the pyrene compound represented by the general formula (2) is a compound represented by one of the following structural formulas.
comprising an electron transport layer and/or an electron injection layer disposed between the cathode and the light emitting layer,
At least one of the electron transport layer and the electron injection layer is a borane derivative, a pyridine derivative, a fluoranthene derivative, a BO derivative, an anthracene derivative, a benzofluorene derivative, a phosphine oxide derivative, a pyrimidine derivative, a carbazole derivative, a triazine derivative, or a benzimidazole derivative. 6. The organic electroluminescent device according to claim 1, comprising at least one selected from the group consisting of , phenanthroline derivatives, and quinolinol metal complexes. The electron transport layer and/or the electron injection layer further comprises an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal oxide, an alkali metal halide, an alkaline earth metal oxide, an alkaline earth metal oxide, and an alkaline earth metal oxide. A claim containing at least one selected from the group consisting of halides, rare earth metal oxides, rare earth metal halides, alkali metal organic complexes, alkaline earth metal organic complexes, and rare earth metal organic complexes. 6. The organic electroluminescent device according to 6. A display device comprising the organic electroluminescent element according to any one of claims 1 to 7. A lighting device comprising the organic electroluminescent element according to any one of claims 1 to 7. A pyrene compound represented by the following general formula (2).
In the above formula,
s pyrene moieties and p Ar moieties are bonded at any position of * of the pyrene moiety and any position of the Ar moiety,
At least one hydrogen in the pyrene moiety is each independently an aryl having 6 to 10 carbon atoms, a heteroaryl having 2 to 11 carbon atoms, an alkyl having 1 to 30 carbon atoms, a cycloalkyl having 3 to 24 carbon atoms, or a cycloalkyl having 3 to 24 carbon atoms. Alkenyl having 1 to 30 carbon atoms, alkoxy having 1 to 30 carbon atoms, or 1 carbon number
~30 may be substituted with aryloxy, and at least one hydrogen in these may be substituted with alkyl having 1 to 6 carbon atoms or cycloalkyl having 3 to 14 carbon atoms,
Ar is a group represented by the following general formula (Ar-1) or general formula (Ar-3),
In each of the above formulas,
Z is >CR ₂ ;
>R in CR ₂ is each independently alkyl having 1 to 6 carbon atoms, or 3 to 14 carbon atoms.
cycloalkyl, aryl having 6 to 12 carbon atoms, or heteroaryl having 2 to 12 carbon atoms, and at least one hydrogen in the aryl and heteroaryl has 1 to 4 carbon atoms.
may be substituted with alkyl or cycloalkyl having 5 to 10 carbon atoms, and R may be bonded to each other to form a ring,
R ¹ to R ⁸ and R ²⁰ to R ³⁵ each independently represent hydrogen, aryl having 6 to 10 carbon atoms, heteroaryl having 2 to 11 carbon atoms, alkyl having 1 to 30 carbon atoms, and 3 to 2 carbon atoms.
cycloalkyl having 1 to 30 carbon atoms, alkenyl having 1 to 30 carbon atoms, alkoxy having 1 to 30 carbon atoms, or aryloxy having 1 to 30 carbon atoms, in which at least one hydrogen is an alkyl having 1 to 6 carbon atoms or 3 carbon atoms. may be substituted with ~14 cycloalkyl, R ¹
Adjacent groups from R ⁸ are bonded to each other to form a condensed ring, and from R ²⁰ to R ³
Adjacent groups of ⁵ may be bonded to each other to form a condensed ring, and the formed rings are each independently aryl having 6 to 10 carbon atoms, heteroaryl having 2 to 11 carbon atoms, It may be substituted with alkyl having 1 to 30 carbon atoms, cycloalkyl having 3 to 24 carbon atoms, alkenyl having 1 to 30 carbon atoms, alkoxy having 1 to 30 carbon atoms, or aryloxy having 1 to 30 carbon atoms, and these at least one hydrogen in may be substituted with alkyl having 1 to 6 carbon atoms or cycloalkyl having 3 to 14 carbon atoms, and
s and p are each independently an integer of 1 or 2, s and p cannot be 2 at the same time, and when s is 2, the two pyrene moieties are structurally the same including the substituents. or may be different, and when p is 2, the two Ar moieties may be structurally the same or different including the substituents,
At least one hydrogen in the compound represented by formula (2) may be independently substituted with halogen, cyano, or deuterium. The pyrene compound according to claim 10, which is represented by one of the following structural formulas.