TW201945374A - Cycloalkyl-substituted polycyclic aromatic compound - Google Patents

Abstract

The present invention can increase the number of choices of materials for organic devices such as materials for organic EL elements, by introducing a cycloalkyl group into a novel polycyclic aromatic compound which comprises a plurality of aromatic rings connected by, for example, a boron atom and an oxygen atom. The novel cycloalkyl-substituted polycyclic aromatic compound can be used as a material for organic EL elements to provide, for example, an organic EL element excellent in terms of luminescent efficiency and element life.

Description

Cycloalkyl substituted polycyclic aromatic compounds

The invention relates to a cycloalkyl-substituted polycyclic aromatic compound and an organic electroluminescence element using the same, an organic field-effect transistor and an organic thin-film solar cell, and a display device and a lighting device. In addition, in this specification, an "organic electroluminescence device" may be expressed as an "organic EL (electroluminescence) device" or only as an "device."

Previously, various researches have been made on display devices using electroluminescence light-emitting elements because they can be reduced in power and thickness. Furthermore, organic electroluminescence elements including organic materials have been actively researched because they can be easily reduced in weight or increased in size. . In particular, the development of organic materials with light-emitting properties such as blue, which is one of the three primary colors of light, and the development of organic materials with charge-transport capabilities (possibility of becoming semiconductors or superconductors) with holes, electrons, etc. So far, both high-molecular compounds and low-molecular compounds have been actively studied.

The organic EL element has a structure including a pair of electrodes including an anode and a cathode, and one or more layers disposed between the pair of electrodes and containing an organic compound. Among the layers containing an organic compound, there are a light emitting layer, a charge transport / injection layer that transports or injects charges such as holes and electrons, and the like, and various organic materials suitable for these layers have been developed.

As a material for the light-emitting layer, for example, a benzofluorene-based compound has been developed (International Publication No. 2004/061047). In addition, as a hole transport material, for example, a triphenylamine-based compound has been developed (Japanese Patent Laid-Open No. 2001-172232). In addition, as an electron transport material, for example, an anthracene-based compound has been developed (Japanese Patent Laid-Open No. 2005-170911).

In addition, in recent years, as a material used for an organic EL element or an organic thin-film solar cell, a modified material of a triphenylamine derivative has been reported (International Publication No. 2012/118164). This material is a material characterized by referring to N, N'-diphenyl-N, N'-bis (3-methylphenyl) -1,1'-biphenyl-4, which has been put into practical use, 4'-diamine (TPD) improves the planarity by connecting the aromatic rings constituting triphenylamine to each other. In this document, for example, the charge transport characteristics of NO-linked compounds (Compound 1 on page 63) are evaluated. However, the method for producing materials other than NO-linked compounds is not described. In addition, if the elements to be linked are different, The electronic states of the compounds as a whole are different, and therefore, characteristics obtained from materials other than NO-linked compounds are still unknown. Examples of such compounds can also be seen elsewhere (International Publication No. 2011/107186). For example, a compound having a conjugated structure having a large triplet exciton energy (T1) can emit phosphorescence with a shorter wavelength, and therefore, it is useful as a material for a blue light-emitting layer. In addition, as an electron-transporting material or hole-transporting material that sandwiches the light-emitting layer, a compound having a novel conjugate structure having a large T1 is also required.

The host material of an organic EL device is usually a molecule in which a plurality of existing aromatic rings such as benzene or carbazole are connected by a single bond, a phosphorus atom, or a silicon atom. The reason is that by linking a plurality of relatively small conjugated aromatic rings, the highest Occupied Molecular Orbital (HOMO) required by the host material-the lowest unoccupied molecular orbital , LUMO) gap (band gap Eg of the film) is guaranteed. Furthermore, the host material of an organic EL device using a phosphorescent material or a thermally active delayed fluorescent material also requires a high triplet excitation energy (E _T ). However, a donor or acceptor aromatic ring is used. Or the substituents are linked to the molecule, so that the single Occupied Molecular Orbital (SOMO) 1 and SOMO 2 of the triplet excited state (T1) exist locally, and the exchange interaction between the two orbitals is reduced, thereby It can enhance the triplet excitation energy (E _T). However, the redox stability of an aromatic ring with a small conjugated system is insufficient, and the life of an element using a molecule to which a conventional aromatic ring is connected as a host material is insufficient. On the other hand, with the expansion of π polycyclic aromatic compound is generally excellent redox stability of the conjugated system, the HOMO-LUMO gap (band gap film Eg) or triplet excitation energy (E _T) is low, and therefore considered unsuitable for Body material.
[Prior Art Literature]
[Patent Literature]

[Patent Document 1] International Publication No. 2004/061047
[Patent Document 2] Japanese Patent Laid-Open No. 2001-172232
[Patent Document 3] Japanese Patent Laid-Open No. 2005-170911
[Patent Document 4] International Publication No. 2012/118164
[Patent Document 5] International Publication No. 2011/107186
[Patent Document 6] International Publication No. 2015/102118

[Problems to be Solved by the Invention]
As described above, various materials have been developed as materials for organic EL elements. In order to increase the selection of materials for organic EL elements, it is desirable to develop materials containing compounds different from those previously used. In particular, the characteristics of the organic EL obtained from materials other than the NO-linked compounds reported in Patent Documents 1 to 4 or the production method thereof are unknown.

In addition, Patent Document 6 reports a polycyclic aromatic compound containing boron and an organic EL device using the same. However, in order to further improve the characteristics of the device, a material for a light-emitting layer, particularly a dopant, which can improve the luminous efficiency or the life of the device, has been proposed Dopant materials.
[Means for solving problems]

The present inventors made intensive research in order to solve the above problems, and as a result, they found that an organic EL element can be obtained by arranging the following layers between a pair of electrodes, for example, an organic EL element, and completed the present invention The layer contains a polycyclic aromatic compound into which a cycloalkyl group is introduced. That is, the present invention provides the following cycloalkyl-substituted polycyclic aromatic compounds or polymers thereof, and further provides organic devices such as materials for organic EL devices containing the following cycloalkyl-substituted polycyclic aromatic compounds or polymers thereof With materials.

In addition, in this specification, a chemical structure or a substituent may be expressed by a carbon number. However, when a chemical structure is substituted with a substituent, or when a substituent is further substituted with a substituent, the carbon number means The carbon number of each chemical structure or substituent does not mean the total carbon number of the chemical structure and the substituent, or the total carbon number of the substituent and the substituent. For example, "substituent B of carbon number Y substituted with substituent A of carbon number X" means "substituent A of carbon number X" is substituted on "substituent B of carbon number Y", and the carbon number Y is not the total carbon number of the substituent A and the substituent B. In addition, for example, "substituent B of carbon number Y substituted with substituent A" means "substituent A (without carbon number)" is substituted on "substituent B of carbon number Y", and the carbon number Y is not the total carbon number of the substituents A and B.

Item 1.
A polycyclic aromatic compound or a multimer of a polycyclic aromatic compound, wherein the polycyclic aromatic compound is represented by the following general formula (1), and the multimer of the polycyclic aromatic compound has a plurality of A structure represented by the following general formula (1).
[Chemical 5]

(In the formula (1),
A ring, B ring and C ring are each independently an aryl ring or a heteroaryl ring, and at least one hydrogen in these rings may be substituted,
Y ¹ is B, P, P = O, P = S, Al, Ga, As, Si-R or Ge-R, and R of said Si-R and Ge-R is an aryl group or an alkyl group,
X ¹ and X ² are independently>O,>NR,> C (-R) ₂ ,> S, or> Se, and R of> NR is an aryl group that can be substituted and a heteroaryl group that can be substituted An alkyl group which may be substituted or a cycloalkyl group which may be substituted, R of said> C (-R) ₂ is hydrogen, aryl or alkyl group which may be substituted, and R of> NR and / Or the R of the> C (-R) ₂ may be bonded to the A ring, B ring and / or C ring through a linking group or a single bond,
At least one hydrogen in the compound or structure represented by formula (1) may be substituted by deuterium, cyano, or halogen, and,
At least one hydrogen in the compound or structure represented by formula (1) is substituted with a cycloalkyl group)

Item 2.
The polycyclic aromatic compound or a multimer thereof according to item 1, wherein:
A ring, B ring and C ring are each independently an aryl ring or a heteroaryl ring, and at least one hydrogen in these rings may be substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl , Substituted or unsubstituted diarylamino, substituted or unsubstituted diheteroarylamino, substituted or unsubstituted arylheteroarylamine, substituted or unsubstituted Diarylboryl (two aryl groups may be bonded via a single bond or linker), substituted or unsubstituted alkyl, substituted or unsubstituted alkoxy, or substituted or unsubstituted Aryloxy substituted, and these rings have a 5-membered ring or 6-membered ring having a bond with the condensed bicyclic structure at the center of the formula containing Y ¹ , X ¹ and X ² ,
Y ¹ is B, P, P = O, P = S, Al, Ga, As, Si-R or Ge-R, and R of said Si-R and Ge-R is an aryl group or an alkyl group,
X ¹ and X ² are independently>O,>NR,> C (-R) ₂ ,> S, or> Se, and R of> NR is an aryl group which may be substituted by an alkyl group, and a hetero group which may be substituted by an alkyl group. An aryl group, an alkyl group, or a cycloalkyl group, wherein R of the> C (-R) ₂ is hydrogen and an aryl group or an alkyl group which may be substituted by an alkyl group; and R of the> NR and / or the> C R of (-R) ₂ may be bonded to the A ring, B ring, and / or C ring through -O-, -S-, -C (-R) _2- , or a single bond, and -C (-R) ₂ -R is hydrogen or alkyl,
At least one hydrogen in the compound or structure represented by formula (1) may be substituted by deuterium, cyano or halogen,
In the case of a multimer, it is a dimer or trimer having two or three structures represented by the general formula (1), and,
At least one hydrogen in the compound or structure represented by the formula (1) is substituted with a cycloalkyl group.

Item 3.
The polycyclic aromatic compound according to item 1, which is represented by the following general formula (2).
[Chemical 6]

(In the formula (2),
R ¹ to R ¹¹ are each independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, and diarylboryl (two aryl groups may be via a single bond or a linking group be bonded), alkyl, alkoxy or aryloxy group, those in which at least one hydrogen may be aryl, substituted aryl or alkyl heteroaryl, additionally, the R ¹ ~ R ¹¹ is Adjacent groups can be bonded to each other and form an aryl or heteroaryl ring with the a, b, or c ring. At least one hydrogen in the formed ring can be aryl, heteroaryl, or diarylamine. Group, diheteroarylamino group, arylheteroarylamine group, diarylboryl group (two aryl groups may be bonded via a single bond or a linking group), alkyl group, alkoxy group or aryloxy group , At least one of these hydrogens may be substituted by aryl, heteroaryl or alkyl,
Y ¹ is B, P, P = O, P = S, Al, Ga, As, Si-R or Ge-R, and R of the Si-R and Ge-R is an aryl group having 6 to 12 carbon atoms or An alkyl group having 1 to 6 carbon atoms,
X ¹ and X ² are independently>O,>NR,> C (-R) ₂ ,> S, or> Se, and R of> NR is an aryl group having 6 to 12 carbon atoms and 2 to 15 carbon atoms. A heteroaryl group, an alkyl group having 1 to 6 carbon atoms or a cycloalkyl group having 3 to 14 carbon atoms, wherein R of C> -R ₂ is hydrogen, and an aryl group having 6 to 12 carbon atoms or carbon number 1 ~ 6 alkyl groups, and the R of the> NR and / or the R of the> C (-R) ₂ may be -O-, -S-, -C (-R) ₂ -or a single bond And bonded to the a ring, the b ring, and / or the c ring, and R of the -C (-R) ₂ -is an alkyl group having 1 to 6 carbon atoms,
At least one hydrogen in the compound represented by formula (2) may be substituted by deuterium, cyano or halogen, and,
At least one hydrogen in the compound represented by formula (2) is substituted with a cycloalkyl group)

Item 4.
The polycyclic aromatic compound according to item 3, wherein
R ¹ to R ¹¹ are each independently hydrogen, an aryl group having 6 to 30 carbon atoms, a heteroaryl group having 2 to 30 carbon atoms, and a diarylamino group (wherein the aryl group is an aryl group having 6 to 12 carbon atoms) , Diarylboryl (wherein the aryl group is an aryl group having 6 to 12 carbon atoms, and two aryl groups can be bonded via a single bond or a linking group) or an alkyl group having 1 to 24 carbon atoms; Adjacent groups in ¹ to R ¹¹ may be bonded to each other and form an aryl ring having 9 to 16 carbon atoms or a heteroaryl ring having 6 to 15 carbon atoms together with ring a, b or c. At least one hydrogen in the ring may be substituted by an aryl group having 6 to 10 carbon atoms or an alkyl group having 1 to 12 carbon atoms,
Y ¹ is B, P, P = O, P = S or Si-R, and R of the Si-R is an aryl group having 6 to 10 carbon atoms or an alkyl group having 1 to 4 carbon atoms,
X ¹ and X ² are independently>O,>NR,> C (-R) ₂ or> S, and R of> NR is an aryl group having 6 to 10 carbon atoms and an alkyl group having 1 to 4 carbon atoms Or a cycloalkyl group having 5 to 10 carbon atoms, and R of C> -R ₂ is hydrogen, an aryl group having 6 to 10 carbon atoms, or an alkyl group having 1 to 4 carbon atoms,
At least one hydrogen in the compound represented by formula (2) may be substituted by deuterium, cyano or halogen, and,
At least one hydrogen in the compound represented by the formula (2) is substituted with a cycloalkyl group.

Item 5.
The polycyclic aromatic compound according to item 3, wherein
R ¹ to R ¹¹ are each independently hydrogen, an aryl group having 6 to 16 carbon atoms, a heteroaryl group having 2 to 20 carbon atoms, and a diarylamino group (wherein the aryl group is an aryl group having 6 to 10 carbon atoms) Or a C1-C12 alkyl group,
Y ¹ is B, P, P = O or P = S,
X ¹ and X ² are independently>O,> NR, or> C (-R) ₂ , where R of> NR is an aryl group having 6 to 10 carbon atoms, an alkyl group having 1 to 4 carbon atoms, or carbon number A cycloalkyl group of 5 to 10, wherein R of the> C (-R) ₂ is hydrogen, an aryl group having 6 to 10 carbon atoms, or an alkyl group having 1 to 4 carbon atoms;
At least one hydrogen in the compound represented by the formula (2) is substituted with a cycloalkyl group.

Item 6.
The polycyclic aromatic compound according to item 3, wherein
R ¹ to R ¹¹ are each independently hydrogen, an aryl group having 6 to 16 carbon atoms, a diarylamino group (wherein the aryl group is an aryl group having 6 to 10 carbon atoms) or an alkyl group having 1 to 12 carbon atoms,
Y ¹ is B,
X ¹ and X ² are both> NR, or X ¹ is> NR and X ² is> O, and R of the> NR is an aryl group having 6 to 10 carbon atoms, an alkyl group having 1 to 4 carbon atoms, or a carbon number 5 to 10 cycloalkyl groups,
At least one hydrogen in the compound represented by the formula (2) is substituted with a cycloalkyl group.

Item 7.
The polycyclic aromatic compound or a polymer thereof according to any one of items 1 to 6, which is a diarylamino group substituted with a cycloalkyl group, a carbazolyl group substituted with a cycloalkyl group, or a cyclic group Alkyl substituted benzocarbazolyl.

Item 8.
The polycyclic aromatic compound according to any one of items 3 to 6, wherein R ² is a diarylamino group substituted with a cycloalkyl group or a carbazolyl group substituted with a cycloalkyl group.

Item 9.
The polycyclic aromatic compound according to any one of items 1 to 8, wherein the cycloalkyl group is a cycloalkyl group having 3 to 20 carbon atoms.

Item 10.
The polycyclic aromatic compound or a polymer thereof according to any one of items 1 to 9, wherein the halogen is fluorine.

Item 11.
The polycyclic aromatic compound according to item 1, which is represented by any one of the following structural formulas.
[Chemical 7]

[Chemical 8]

("Me" in each structural formula is methyl, and "tBu" represents third butyl)

Item 12.
A reactive compound obtained by substituting a reactive substituent in a polycyclic aromatic compound or a multimer thereof according to any one of items 1 to 11.

Item 13.
A polymer compound or a polymer crosslinked body, wherein the polymer compound is obtained by polymerizing a reactive compound as described in item 12 as a monomer, and the polymer crosslinked body is made by The polymer compound is further cross-linked.

Item 14.
A suspension type polymer compound or a suspension type polymer cross-linked body, wherein the suspension type polymer compound is substituted by the reactive compound according to item 12 in a main chain type polymer, and the suspension type The polymer crosslinked body is obtained by further crosslinking the suspended polymer compound.

Item 15.
An organic device material comprising the polycyclic aromatic compound according to any one of items 1 to 11 or a polymer thereof.

Item 16.
An organic device material comprising the reactive compound according to item 12.

Item 17.
An organic device material containing the polymer compound or polymer crosslinked body according to item 13.

Item 18.
A material for an organic device, comprising the pendant polymer compound or the pendant polymer crosslinked body according to item 14.

Item 19.
The material for an organic device according to any one of items 15 to 18, wherein the material for an organic device is a material for an organic electroluminescence element, a material for an organic field effect transistor, or a material for an organic thin film solar cell.

Item 20.
The material for an organic device according to item 19, wherein the material for an organic electroluminescence element is a material for a light-emitting layer.

Item 21.
An ink composition comprising: the polycyclic aromatic compound or a polymer thereof according to any one of items 1 to 11; and an organic solvent.

Item 22.
An ink composition comprising: the reactive compound according to item 12; and an organic solvent.

Item 23.
An ink composition comprising: a main chain polymer; the reactive compound according to item 12; and an organic solvent.

Item 24.
An ink composition comprising: the polymer compound or polymer crosslinked body according to item 13, and an organic solvent.

Item 25.
An ink composition comprising: the hanging polymer compound or the hanging polymer crosslinked body according to item 14, and an organic solvent.

Item 26.
An organic electroluminescence element comprising: a pair of electrodes including an anode and a cathode; and an organic layer disposed between the pair of electrodes and containing the polycyclic aromatic substance according to any one of items 1 to 11 Group compounds or polymers thereof, the reactive compound according to item 12, the polymer compound or polymer cross-linker according to item 13, or the pendant polymer compound or pendant type according to item 14 Molecular crosslinked body.

Item 27.
An organic electroluminescence element comprising: a pair of electrodes including an anode and a cathode; and a light-emitting layer disposed between the pair of electrodes and containing the polycyclic aromatic substance according to any one of items 1 to 11 Group compounds or polymers thereof, the reactive compound according to item 12, the polymer compound or polymer cross-linker according to item 13, or the pendant polymer compound or pendant type according to item 14 Molecular crosslinked body.

Item 28.
The organic electroluminescence element according to item 27, wherein the light-emitting layer includes: a host; and the polycyclic aromatic compound as a dopant, a polymer thereof, a reactive compound, a polymer compound, a polymer Molecular crosslinked body, suspended polymer compound or suspended polymer crosslinked body.

Item 29.
The organic electroluminescence device according to item 28, wherein the host is an anthracene-based compound, a fluorene-based compound, or a dibenzofluorene-based compound.

Item 30.
The organic electroluminescent element according to any one of items 26 to 29, which has an electron transport layer and / or an electron injection layer disposed between the cathode and the light emitting layer, and the electron transport layer And at least one of the electron injection layer contains a member selected from the group consisting of a borane derivative, a pyridine derivative, a fluoranthene derivative, a BO-based derivative, an anthracene derivative, a benzofluorene derivative, a phosphine oxide derivative, a pyrimidine derivative, At least one of a group consisting of an azole derivative, a triazine derivative, a benzimidazole derivative, a phenanthroline derivative, and a quinolinol-based metal complex.

Item 31.
The organic electroluminescence element according to item 30, wherein the electron transport layer and / or the electron injection layer further contains a member selected from the group consisting of an alkali metal, an alkaline earth metal, a rare earth metal, an oxide of an alkali metal, a halide of an alkali metal, Alkaline earth metal oxides, alkali 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 At least one of the group.

Item 32.
The organic electroluminescence element according to any one of items 26 to 31, wherein at least one of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer comprises: a polymer A compound or a polymer crosslinked body, or a pendant polymer compound or a pendant polymer crosslinked body, the polymer compound is obtained by polymerizing a low-molecular compound capable of forming each layer as a monomer. The molecular cross-linked body is obtained by further cross-linking the polymer compound, and the suspended polymer compound is formed by reacting a low-molecular compound that can form each layer with a main chain polymer. The concatenation is obtained by further cross-linking the suspended polymer compound.

Item 33.
A display device or a lighting device comprising the organic electroluminescence element according to any one of items 26 to 32.
[Effect of the invention]

According to a preferred aspect of the present invention, for example, a novel cycloalkyl-substituted polycyclic aromatic compound that can be used as a material for an organic device such as an organic EL element can be provided, and the polycyclic aromatic can be substituted by using the cycloalkyl. Compounds, and can provide excellent organic devices such as organic EL elements.

Specifically, the present inventors have discovered that a polycyclic aromatic compound (basic skeleton portion) in which aromatic rings are connected by heterogeneous elements such as boron, phosphorus, oxygen, nitrogen, and sulfur has a large HOMO-LUMO gap (thin of a thin film). Band gap Eg) and high triplet excitation energy (E _T ). The reason is considered to be that the 6-membered ring containing a hetero element has a low aromaticity, so the reduction of the HOMO-LUMO gap accompanying the expansion of the conjugate system is suppressed, and the triplet excited state (T1) is caused by the electronic disturbance of the hetero element SOMO1 and SOMO2 exist locally. In addition, the heterocyclic aromatic compound (basic skeleton portion) of the present invention has localized SOMO1 and SOMO2 in the triplet excited state (T1), and the exchange interaction between the two orbitals becomes small, so The energy difference between the triplet excited state (T1) and the singlet excited state (S1) is small, and it exhibits thermally active delayed fluorescence, so it is also useful as a fluorescent material for organic EL devices. In addition, a material having high triplet excitation energy (E _T ) is also useful as an electron transport layer or a hole transport layer of a phosphorescent organic EL element or an organic EL element using a thermally active delayed fluorescence. Furthermore, these polycyclic aromatic compounds (basic skeleton parts) can arbitrarily change the energies of HOMO and LUMO by the introduction of substituents. Therefore, the ionization potential or the electron affinity can be maximized according to the surrounding materials. Optimization.

In addition to the characteristics of such a basic skeleton portion, the compound of the present invention can also be expected to lower the melting point or sublimation temperature by introducing a cycloalkyl group. In this case, since sublimation purification, which is almost indispensable as a method for refining materials for organic devices such as organic EL elements that require high purity, can be refined at a relatively low temperature, thermal decomposition of the material can be avoided, etc. . In addition, this situation is also the same for the vacuum evaporation process. The process can be performed at a relatively low temperature, so that thermal decomposition of the material can be avoided, and as a result, high-performance organic devices can be obtained. The vacuum evaporation process is suitable for It is a powerful method for producing organic devices such as organic EL elements. In addition, as for polymers of polycyclic aromatic compounds, there are many compounds having a high sublimation temperature due to a high molecular weight or a high planarity. Therefore, a reduction in the sublimation temperature by introducing a cycloalkyl group becomes more effective. In addition, since the solubility in an organic solvent is improved by the introduction of a cycloalkyl group, it can also be applied to device production using a coating process. However, the present invention is not particularly limited to these principles.

1. Cycloalkyl-substituted polycyclic aromatic compounds and polymers thereof The invention of this application is a polycyclic aromatic compound represented by the following general formula (1), or has a plurality of polycyclic aromatic compounds represented by the following general formula (1) A polymer of a polycyclic aromatic compound having a structure represented by) is preferably a polycyclic aromatic compound represented by the following general formula (2), or a polymer having a plurality of structures represented by the following general formula (2) A multimer of a polycyclic aromatic compound, at least one of the hydrogens of these compounds or structures is substituted by a cycloalkyl group.
[Chemical 9]

The A ring, B ring, and C ring in the general formula (1) are each independently an aryl ring or a heteroaryl ring, and at least one hydrogen in these rings may be substituted by a substituent. The substituent is preferably a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted diarylamino group, a substituted or unsubstituted diheteroaryl group. Arylamino, substituted or unsubstituted arylheteroarylamine (amine with aryl and heteroaryl), substituted or unsubstituted diarylboryl (both aryl groups Single bond or linker), substituted or unsubstituted alkyl, substituted or unsubstituted alkoxy, or substituted or unsubstituted aryloxy. Examples of the substituent when these groups have a substituent include an aryl group, a heteroaryl group, and an alkyl group. In addition, the aryl ring or heteroaryl ring is preferably a 5-membered ring or a 6-membered ring having a bond in common with the central condensed bicyclic structure of the general formula (1) containing Y ¹ , X ¹ and X ² .

Here, the "condensed bicyclic structure" refers to a structure obtained by condensing two saturated hydrocarbon rings including Y ¹ , X ^1, and X ² shown in the center of the general formula (1). The “6-membered ring shared with the condensed bicyclic structure” means, for example, as shown in the general formula (2), an a ring (benzene ring ( 6 member ring)). In addition, the "(A ring) aryl ring or heteroaryl ring has the 6-membered ring" means that the A-ring is formed only from the 6-membered ring or that the 6-membered ring is included in the 6-membered ring. Further, other rings and the like are condensed to form an A ring. In other words, the "(A ring) aryl ring or heteroaryl ring having a 6-membered ring" herein means that the 6-membered ring constituting all or part of the A ring is condensed in the condensed bicyclic structure. Regarding "B ring (b ring)", "C ring (c ring)", and "5 member ring", the same explanation applies.

The A ring (or B ring, C ring) in the general formula (1) corresponds to the a ring and its substituents R ¹ to R ³ (or the b ring and its substituents R ⁴ to R ⁷ , c) in the general formula (2). The ring and its substituents R ⁸ to R ¹¹ ). That is, the general formula (2) corresponds to a structure in which “A ring to C ring having a 6-membered ring” is selected as the A ring to C ring of the general formula (1). In this meaning, each ring of the general formula (2) is represented by lowercase letters a to c.

In the general formula (2), adjacent groups of the substituents R ¹ to R ¹¹ of the a ring, the b ring, and the c ring may be bonded to each other and form an aryl ring or a hetero ring together with the a ring, the b ring, or the c ring. An aryl ring, at least one of the hydrogens formed in the ring may be aryl, heteroaryl, diarylamino, diheteroarylamine, arylheteroarylamine, diarylboryl (two An aryl group may be bonded via a single bond or a linker), an alkyl group, an alkoxy group, or an aryloxy group, and at least one of these hydrogens may be substituted with an aryl group, a heteroaryl group, or an alkyl group. Therefore, the polycyclic aromatic compound represented by the general formula (2) is as shown in the following formula (2-1) and formula (2-2) according to the mutual bonding form of the substituents in the a ring, the b ring, and the c ring. As shown, the ring structure constituting the compound changes. The A 'ring, B' ring, and C 'ring in each formula correspond to the A ring, the B ring, and the C ring in the general formula (1), respectively.

[Chemical 10]

When the general formula (2) is used for description, the A 'ring, B' ring, and C 'ring in the formulae (2-1) and (2-2) represent adjacent groups in the substituents R ¹ to R ¹¹ The aryl or heteroaryl ring formed by the groups bonded to each other and respectively formed with the a, b, and c rings (also known as other ring structures condensed in the a, b, or c rings) Condensation ring). In addition, although not shown in the formula, there are also compounds in which all of the a ring, the b ring, and the c ring are changed to the A 'ring, the B' ring, and the C 'ring. In addition, as can be seen from the formulas (2-1) and (2-2), for example, R ⁸ of the b ring and R ⁷ of the c ring, R ¹¹ of the b ring and R ¹ and c ring of the a ring R ⁴ and R ^{3 of the} a ring do not conform to "adjacent groups", and these will not be bonded. That is, the "adjacent group" refers to a group adjacent to each other on the same ring.

The compound represented by the formula (2-1) or (2-2) is, for example, a compound having a benzene ring, an indole ring, a pyrrole ring, a benzofuran ring, or a benzothiophene ring. A ring (c ring) is a compound formed by condensing a benzene ring. The condensed ring A '(or condensed ring B' or condensed ring C ') is a naphthalene ring. , Carbazole ring, indole ring, dibenzofuran ring or dibenzothiophene ring.

Y ¹ in the general formula (1) is B, P, P = O, P = S, Al, Ga, As, Si-R or Ge-R, and R of the Si-R and Ge-R is an aryl group Or alkyl. In the case of P = O, P = S, Si-R, or Ge-R, the atom bonded to the A ring, B ring, or C ring is P, Si, or Ge. Y ^{1 is} preferably B, P, P = O, P = S, or Si-R, and particularly preferably B. This description also applies to Y ¹ in the general formula (2).

X ¹ and X ² in the general formula (1) are independently>O,>NR,> C (-R) ₂ ,> S or> Se, and R of> NR is an aryl group which may be substituted, Heteroaryl which may be substituted, alkyl which may be substituted or cycloalkyl which may be substituted, said R of C (-R) ₂ is hydrogen, aryl or alkyl which may be substituted, said> R of NR and / or R of C> -R ₂ may be bonded to the B ring and / or C ring through a linking group or a single bond. As the linking group, -O-, -S- or -C (-R) _2- . In addition, R in the "-C (-R) _2- " is hydrogen or an alkyl group. This description also applies to X ¹ and X ² in the general formula (2).

Here, in the general formula (1), "R of NR and / or said R of C (-R) ₂ is linked to the A ring, B ring, and / or C ring through a linking group or a single bond. The definition of "bonding" corresponds to "R of> NR and / or R of> C (-R) ₂ through -O-, -S-, -C (-R) _2- Or a single bond to the a, b, and / or c ring.

This rule can be expressed by a compound represented by the following formula (2-3-1) and having a ring structure in which X ¹ or X ² is introduced into the condensed ring B ′ and the condensed ring C ′. That is, for example, it is a B 'ring (or C' ring) formed by condensing a benzene ring that is the b ring (or c ring) in the general formula (2) by introducing X ¹ (or X ² ) with other rings. )compound of. The formed condensed ring B '(or condensed ring C') is, for example, an phenoxazine ring, an phenothiazine ring, or an acridine ring.

In addition, the regulation may be expressed by a compound represented by the following formula (2-3-2) or formula (2-3-3) and having X ¹ and / or X ² introduced into the condensation Ring structure in ring A '. That is, it is, for example, a compound having an A ′ ring formed by condensing a benzene ring that is the a ring in the general formula (2) with another ring to introduce X ¹ (and / or X ² ). The condensed ring A ′ formed is, for example, an phenoxazine ring, an phenothiazine ring, or an acridine ring.

[Chemical 11]

Examples of the "aryl ring" of the A ring, the B ring, and the C ring of the general formula (1) include an aryl ring having 6 to 30 carbon atoms, and an aryl ring having 6 to 16 carbon atoms is more preferable, and more preferably The aryl ring having 6 to 12 carbon atoms is particularly preferably an aryl ring having 6 to 10 carbon atoms. Furthermore, the "aryl ring" corresponding to the formula "R ¹ ~ R ¹¹ in adjacent group (2) as defined bonded to each other and form a ring together with a, b or c ring of the aryl ring In addition, since the a ring (or the b ring and the c ring) already contains a benzene ring having 6 carbon atoms, the total number of carbon atoms of a condensed ring formed by condensing a five-membered ring therein is 9 as the lower limit carbon number.

Specific examples of the "aryl ring" include a monocyclic benzene ring, a bicyclic biphenyl ring, a condensed bicyclic naphthalene ring, and a tricyclic bitriphenyl ring (indirect Triphenyl, ortho-triphenyl, para-triphenyl), as condensed tricyclic ring ring, fluorene ring, fluorene ring, phenanthrene ring, as condensed tetracyclic ring triphenylene ring, fluorene ring, fused tetraphenyl The benzene (naphthacene) ring is used as a condensed pentacyclic fluorene ring, a pentacene ring, and the like.

Examples of the "heteroaryl ring" of the A ring, B ring, and C ring of the general formula (1) include a heteroaryl ring having 2 to 30 carbon atoms, and a heteroaryl ring having 2 to 25 carbon atoms is preferred. More preferred is a heteroaryl ring having 2 to 20 carbon atoms, still more preferred is a heteroaryl ring having 2 to 15 carbon atoms, and particularly preferred is a heteroaryl ring having 2 to 10 carbon atoms. The "heteroaryl ring" includes, for example, a heterocyclic ring containing one to five heteroatoms selected from oxygen, sulfur, and nitrogen as ring constituent atoms in addition to carbon. The "heteroaryl ring" corresponds to a heterocycle formed by "adjacent groups in R ¹ to R ¹¹ bonded to each other and formed together with the a ring, b ring, or c ring" specified in the general formula (2). "Aryl ring", and the a ring (or b ring, c ring) already contains a benzene ring with 6 carbon atoms. Therefore, the total number of carbon atoms of a condensed ring formed by condensing a 5-membered ring into 6 is the lower limit carbon number.

Specific examples of the "heteroaryl ring" include a pyrrole ring, an oxazole ring, an isoxazole ring, a thiazole ring, an isothiazole ring, an imidazole ring, an oxadiazole ring, a thiadiazole ring, a 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, pyrimidine ring, carbazole ring, acridine ring, phenoxathia ring, phenoxazine ring, phenothiazine ring, phenazine ring, indazine ring, furan ring, benzofuran ring, isobenzofuran ring , Dibenzofuran ring, thiophene ring, benzothiophene ring, dibenzothiophene ring, furazan ring, oxadiazole ring, thiathracene ring, and the like.

At least one hydrogen in the "aryl ring" or "heteroaryl ring" may be substituted or unsubstituted "aryl" as a first substituent, and a substituted or unsubstituted "heteroaryl" , Substituted or unsubstituted "diarylamino", substituted or unsubstituted "diheteroarylamino", substituted or unsubstituted "arylheteroarylamino", Substituted or unsubstituted "diarylboryl (two aryl groups may be bonded via a single bond or a linker)", substituted or unsubstituted "alkyl", substituted or unsubstituted " "Alkoxy", or substituted or unsubstituted "aryloxy", "aryl" or "heteroaryl" as the first substituent, aryl of "diarylamino", " The "heteroarylamino" heteroaryl, "arylheteroarylamino" aryl and heteroaryl, "diarylboryl" aryl, and "aryloxy" aryl may be The monovalent radicals of the "aryl ring" or "heteroaryl ring" are listed.

The "alkyl group" as the first substituent may be either a straight chain or a branched chain, and examples thereof include a linear alkyl group having 1 to 24 carbon atoms or a branched chain alkyl group having 3 to 24 carbon atoms. An alkyl group having 1 to 18 carbons (a branched alkyl group having 3 to 18 carbon atoms) is preferred, an alkyl group having 1 to 12 carbon atoms (a branched alkyl group having 3 to 12 carbon atoms) is more preferred, and still more preferred An alkyl group having 1 to 6 carbons (a branched alkyl group having 3 to 6 carbon atoms), and an alkyl group having 1 to 4 carbon atoms (a branched alkyl group having 3 to 4 carbon atoms) is particularly preferred.

Specific examples of the alkyl group include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, second butyl, third butyl, n-pentyl, isopentyl, and neo Pentyl, third pentyl, n-hexyl, 1-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, n-heptyl, 1 -Methylhexyl, n-octyl, third 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- Hexyl heptyl, normal fourteen base, normal fifteen base, normal sixteen base, normal seventeen base, normal eighteen base, normal twenty base, etc.

Examples of the "alkoxy group" as the first substituent include a linear alkoxy group having 1 to 24 carbon atoms or a branched alkoxy group having 3 to 24 carbon atoms. An alkoxy group having 1 to 18 carbons (branched alkoxy group having 3 to 18 carbons) is preferred, and an alkoxy group having 1 to 12 carbons (branched chain alkoxy group having 3 to 12 carbons) is more preferred Alkoxy), further preferably alkoxy having 1 to 6 carbons (branched alkoxy having 3 to 6 carbons), and particularly preferably alkoxy having 1 to 4 carbons (3 to 4 carbons) Branched alkoxy).

Specific alkoxy groups include methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, second butoxy, third butoxy, and pentyloxy. Group, hexyloxy, heptyloxy, octyloxy and the like.

In addition, as the "boryl group" in the "diarylboryl group" as the first substituent, the description of the aryl group can be cited. In addition, the two aryl groups may be bonded via a single bond or a linking group (for example,> C (-R) ₂ ,>O,> S, or> NR). Here, R of> C (-R) ₂ and> NR is an aryl group, a heteroaryl group, a diarylamino group, an alkyl group, a cycloalkyl group, an alkoxy group, or an aryloxy group (the above is the first substituent) ), An aryl group, a heteroaryl group, an alkyl group or a cycloalkyl group may be further substituted on the first substituent (the above is the second substituent). As specific examples of these groups, reference may be made as described Explanation of the aryl group, heteroaryl group, diarylamino group, alkyl group, cycloalkyl group, alkoxy group, or aryloxy group of the first substituent.

Substituted or unsubstituted "aryl" as the first substituent, substituted or unsubstituted "heteroaryl", substituted or unsubstituted "diarylamino", substituted or unsubstituted Substituted "diheteroarylamino", substituted or unsubstituted "arylheteroarylamino", substituted or unsubstituted "diarylboryl (two aryl groups can be Bond or linking group) ", substituted or unsubstituted" alkyl ", substituted or unsubstituted" alkoxy ", or substituted or unsubstituted" aryloxy "as described As substituted or unsubstituted, at least one of these hydrogens may be substituted by a second substituent. Examples of the second substituent include an aryl group, a heteroaryl group, and an alkyl group. For specific examples, refer to the monovalent group of the "aryl ring" or "heteroaryl ring" and the first substitution. Explanation of the "alkyl" of the radical. In the aryl or heteroaryl group as the second substituent, at least one of these hydrogens is an aryl group such as a phenyl group (a specific example is the group described above) or an alkyl group such as a methyl group (a specific example) A structure substituted by the group described above is also included in the aryl or heteroaryl group as the second substituent. As an 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 group such as a phenyl group or an alkyl group such as a methyl group is also included in the second substituent group. Heteroaryl.

As the aryl group, heteroaryl group, diarylamino group aryl group, diheteroarylamine group heteroaryl group, arylheteroarylamine group aryl group in R ¹ to R ¹¹ in the general formula (2) And heteroaryl, diarylboryl aryl, or aryloxy aryl include monovalent groups such as "aryl ring" or "heteroaryl ring" described in general formula (1) . As the alkyl or alkoxy group in R ¹ to R ¹¹ , reference may be made to the description of the “alkyl” or “alkoxy” group as the first substituent in the description of the general formula (1). Furthermore, the same applies to an aryl group, a heteroaryl group, or an alkyl group as a substituent to these groups. In addition, when adjacent groups in R ¹ to R ¹¹ are bonded to each other and form an aryl ring or a heteroaryl ring together with the a ring, the b ring, or the c ring, the heteroaryl group is a substituent for these rings. , Diarylamino, diheteroarylamino, arylheteroarylamine, diarylboryl (two aryl groups can be bonded via a single bond or a linking group), alkyl, alkoxy Or aryloxy, as well as aryl, heteroaryl or alkyl as further substituents.

Specifically, the light emission wavelength can be adjusted by the steric hindrance, electron donating property, and electron withdrawing property of the structure of the first substituent. The group represented by the following structural formula is preferable, and the methyl group and the third group are more preferable. Butyl, phenyl, o-tolyl, p-tolyl, 2,4-xylyl, 2,5-xylyl, 2,6-xylyl, 2,4,6-mesityl, dimethyl Phenylamino, di-p-tolylamino, bis (p- (third-butyl) phenyl) amino, carbazolyl, 3,6-dimethylcarbazolyl, 3,6-di- Tributylcarbazolyl and phenoxy, further preferably methyl, third butyl, phenyl, o-tolyl, 2,6-xylyl, 2,4,6-mesityl, diphenyl Amino, di-p-tolylamino, bis (p- (third-butyl) phenyl) amino, carbazolyl, 3,6-dimethylcarbazolyl, and 3,6-di-third Butylcarbazolyl. From the standpoint of ease of synthesis, those with large steric hindrance are preferred for selective synthesis, and specifically, third butyl, o-tolyl, p-tolyl, 2,4-xylyl, 2,5-xylyl, 2,6-xylyl, 2,4,6-mesylylyl, di-p-tolylamino, bis (p- (thirdbutyl) phenyl) amino, 3,6-dimethylcarbazolyl and 3,6-di-third-butylcarbazolyl.

In the following structural formula, "Me" represents a methyl group, and "tBu" represents a third butyl group.
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Si-R and Ge-R in Y ¹ in the general formula (1) are an aryl group or an alkyl group, and examples of the aryl group or the alkyl group include the groups described above. Particularly preferred are aryl groups (e.g., phenyl, naphthyl, etc.) having 6 to 10 carbon atoms, and alkyl groups (e.g., methyl, ethyl, etc.) having 1 to 4 carbon atoms. This description also applies to Y ¹ in the general formula (2).

X Formula (1) and in ¹ X ^2> NR R is substituted by the second group substituted aryl, heteroaryl, or cycloalkyl, the aryl, heteroaryl, alkoxy At least one hydrogen in the radical or cycloalkyl may be substituted by, for example, an alkyl group. Examples of the aryl group, heteroaryl group, or alkyl group include the groups described above. In addition, as a cycloalkyl group, description is mentioned later. Particularly preferred are aryl groups having 6 to 10 carbon atoms (such as phenyl, naphthyl, etc.), heteroaryl groups having 2 to 15 carbon atoms (such as carbazolyl), and alkyl groups having 1 to 4 carbon atoms (such as methyl , Ethyl, etc.). This description also applies to X ¹ and X ² in the general formula (2).

In X ¹ and X ² of the general formula (1), R of> C (-R) ₂ is hydrogen, an aryl group or an alkyl group which may be substituted with the second substituent, and at least one hydrogen in the aryl group may be, for example, an alkane Radical substitution. Examples of the aryl group or the alkyl group include the groups described above. Particularly preferred are aryl groups (e.g., phenyl, naphthyl, etc.) having 6 to 10 carbon atoms, and alkyl groups (e.g., methyl, ethyl, etc.) having 1 to 4 carbon atoms. This description also applies to X ¹ and X ² in the general formula (2).

R of "-C (-R) _2- " which is a linking group in the general formula (1) is hydrogen or an alkyl group, and examples of the alkyl group include the groups described above. Particularly preferred is an alkyl group having 1 to 4 carbon atoms (for example, methyl, ethyl, etc.). This description also applies to "-C (-R) _2- " which is a linking group in the general formula (2).

The invention of the present application is a polymer of a polycyclic aromatic compound having a plurality of unit structures represented by the general formula (1), and preferably a polymer having a plurality of unit structures represented by the general formula (2). Multimers of polycyclic aromatic compounds. The multimer is preferably a dimer to a hexamer, more preferably a dimer to a trimer, and particularly preferably a dimer. The multimer may be in the form of having a plurality of such unit structures in one compound. For example, in addition to using a single bond, a linking group such as an alkylene group having 1 to 3 carbon atoms, a phenylene group, and a naphthyl group, In addition to the form in which the unit structure is bonded, an arbitrary ring (A ring, B ring, or C ring, a ring, b ring, or c ring) contained in the unit structure may be shared by a plurality of unit structures. Ring), and may be condensed with any of the rings (A ring, B ring or C ring, a ring, b ring or c ring) contained in the unit structure. Way to carry out the bonding form.

Examples of such a multimer include the following formula (2-4), formula (2-4-1), formula (2-4-2), formula (2-5-1) to formula (2) -5-4) or a multimeric compound represented by formula (2-6). If the general formula (2) is used for description, the multimer compound represented by the following formula (2-4) has a plurality of general formulas (2) in one compound so as to share a benzene ring as the a ring. Multimer compound of the unit structure shown. In addition, if the general formula (2) is used for explanation, the multimeric compound represented by the following formula (2-4-1) has a benzene ring as the a ring, and has two general groups in one compound. Multimer compound having a unit structure represented by formula (2). In addition, if the general formula (2) is used for explanation, the multimeric compound represented by the following formula (2-4-2) has a benzene ring as the a ring and shares three compounds in one compound. Multimer compound having a unit structure represented by formula (2). In addition, if the general formula (2) is used for description, the multimer compounds represented by the following formulae (2-5-1) to (2-5-4) are those which share the b ring (or c ring) in common. In the form of a benzene ring, a polymer compound having a plurality of unit structures represented by the general formula (2) in one compound. In addition, if the general formula (2) is used for description, the multimer compound represented by the following formula (2-6) is a benzene ring having, for example, a b ring (or a ring, c ring) as a certain unit structure. A polymer compound having a plurality of unit structures represented by the general formula (2) in one compound by a method of condensing with a benzene ring of a b-ring (or a-ring or c-ring) as a certain unit structure.

[Chemical 17]

The multimer compound may be a multimerized form represented by Formula (2-4), Formula (2-4-1), or Formula (2-4-2) and Formula (2-5-1) to Formula ( 2-5-4) or a multimer formed by combining the multimerization forms represented by formula (2-6) may be a combination of formulae (2-5-1) to (2-5) A polymer formed by combining the multimerization form expressed by any of -4) and the multimerization form expressed by formula (2-6) may also be a combination of formulae (2-4) and (2) -4-1) or the multimerization form represented by formula (2-4-2) and the multimerization form represented by any of formulas (2-5-1) to (2-5-4) , And a multimer formed by combining the multimerization forms represented by formula (2-6).

In addition, all or part of hydrogen in the chemical structure of the polycyclic aromatic compound represented by the general formula (1) or the general polymer (2) may be deuterium, cyano, or halogen. For example, in Formula (1), A ring, B ring, C ring (A ring to C ring are aryl ring or heteroaryl ring), a substituent for ring A to C ring, and Y ¹ is Si-R When R (= alkyl, aryl) or Ge-R, and hydrogen at R (= alkyl, aryl) when X ¹ and X ² are> NR or> C (-R) ₂ may be deuterium, A cyano group or a halogen group is substituted. Among these, the form in which all or a part of hydrogen in an aryl group or a heteroaryl group is substituted with deuterium, a cyano group, or a halogen is mentioned. Halogen is fluorine, chlorine, bromine or iodine, preferably fluorine, chlorine or bromine, and more preferably fluorine or chlorine.

In addition, the polycyclic aromatic compound and its multimers of the present invention can be used as materials for organic devices. Examples of the organic device include an organic electroluminescence element, an organic field-effect transistor, and an organic thin-film solar cell. In particular, in the organic electroluminescent device, as a dopant material of the light emitting layer, a compound in which Y ¹ is B, X ¹ and X ² are> NR, and Y ¹ is B, X ¹ is> O, X ² is a> NR, compounds, Y ¹ is B, X ¹ and X ² are> O compound, as a host material for the emitting layer, Y ¹ is preferably B, X ¹ is> O, X ² is> NR, A compound in which Y ¹ is a compound in which B, X ¹ and X ² are> O, and as an electron transporting material, a compound in which Y ¹ is B, X ¹ and X ² are> O, and Y ¹ is P = O , X ¹ and X ² are compounds of> O.

In addition, at least one hydrogen in the chemical structure of the polycyclic aromatic compound represented by the general formula (1) or the general polymer (2) has been substituted with a cycloalkyl group, and all or part of the hydrogen may be a ring. alkyl.

Examples of other forms of cycloalkyl substitution include polycyclic aromatic compounds represented by the general formula (1) or the general formula (2) and polymers thereof such as a diarylamino group substituted with a cycloalkyl group, Examples of carbazolyl substituted with cycloalkyl or benzocarbazolyl substituted with cycloalkyl. Examples of the "diarylamino group" include the groups described as the "first substituent". Examples of the substituted form of the cycloalkyl group with respect to the diarylamino group, carbazolyl group, and benzocarbazolyl group include a part or all of hydrogens of the aryl ring or benzene ring of these groups are substituted with cycloalkyl groups. example of.

In addition, as a more specific example, a polycyclic aromatic compound represented by the general formula (2) and its multimer R ² is a diarylamino group substituted with a cycloalkyl group or substituted with a cycloalkyl group. Examples of carbazolyl.

Examples thereof include polycyclic aromatic compounds represented by the following general formula (2-A) or polycyclic aromatic compounds having a plurality of structures represented by the following general formula (2-A). Polymer. Cy is a cycloalkyl group, n is an integer of 1 to 5 (preferably 1), and the definition of each symbol in the structural formula is the same as the definition of each symbol in the general formula (2).
[Chemical 18]

In addition, as specific examples of the cycloalkyl-substituted polycyclic aromatic compound and its polymer of the present invention, at least one hydrogen of one or more aromatic rings in the compound may be composed of one or more rings. Examples of the alkyl-substituted compound include compounds substituted with one to two cycloalkyl groups.

Specific examples include compounds represented by the following formulae (1-1-Cy) to (1-4401-Cy). N in the following formula is independently 0 to 2 (wherein, not all n becomes 0), and 1 is preferable. In the following structural formula, "Cy" represents a cycloalkyl group, "OPh" represents a phenoxy group, and "Me" represents a methyl group.

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Examples of the cycloalkyl group include a cycloalkyl group having 3 to 24 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, a cycloalkyl group having 3 to 16 carbon atoms, a cycloalkyl group having 3 to 14 carbon atoms, and carbon number. A cycloalkyl group having 5 to 10 carbon atoms, a cycloalkyl group having 5 to 8 carbon atoms, a cycloalkyl group having 5 to 6 carbon atoms, a cycloalkyl group having 5 carbon atoms, and the like.

Specific examples of cycloalkyl include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, and the number of carbons of these groups. 1 to 4 alkyl (especially methyl) substituents, or norbornenyl, bicyclo [1.0.1] butyl, bicyclo [1.1.1] pentyl, bicyclo [2.0.1] pentyl, bicyclic [ 1.2.1] hexyl, bicyclo [3.0.1] hexyl, bicyclo [2.1.2] heptyl, bicyclo [2.2.2] octyl, adamantyl, diadamantyl, decahydronaphthalenyl, ten Decahydroazulenyl, etc.

As a more specific example of the cycloalkyl substituted polycyclic aromatic compound of this invention, the compound represented by the following structural formula is mentioned. In the following structural formula, "D" represents deuterium, "Me" represents methyl, "tBu" represents third butyl, and "Ph" represents phenyl.

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The polycyclic aromatic compound represented by the general formula (1) of the present invention and a polymer thereof can also be used as a polymer compound (the monomer used to obtain the polymer compound has a polymerizable substituent) or A molecular crosslinked body (the polymer compound used to obtain the polymer crosslinked body has a crosslinkable substituent), or a pendant polymer compound (the reaction used to obtain the pendant polymer compound) The reactive compound has a reactive substituent) or a pendant polymer crosslinked body (the pendant polymer compound used to obtain the pendant polymer crosslinked body has a crosslinkable substituent) and is used as a material for an organic device For example, a material for an organic electroluminescent device, a material for an organic field effect transistor, or a material for an organic thin film solar cell, wherein the polymer compound is a polycyclic aromatic compound represented by the general formula (1) A reactive compound in which a reactive substituent is substituted in a polymer thereof is polymerized as a monomer, and the polymer crosslinked body further crosslinks the polymer compound. To the suspension-type polymer compound is a polymer main chain with the reactive compound obtained by reacting the pendant polymer is crosslinked so that the suspension is further crosslinked type polymer compound.

As the reactive substituent (including the polymerizable substituent, the crosslinkable substituent, and a reactive substituent for obtaining a pendant polymer, hereinafter, also simply referred to as a "reactive substituent") If it is a substituent capable of polymerizing the polycyclic aromatic compound or a polymer thereof, a substituent capable of further crosslinking the polymer compound obtained in this way, and a main chain type The substituent that undergoes a hanging reaction in the polymer is not particularly limited, but is preferably a substituent having the following structure. * In each structural formula represents a bonding position.
[Chemical 48]

L is independently a single bond, -O-, -S-,> C = O, -OC (= O)-, an alkylene group having 1 to 12 carbon atoms, an oxyalkylene group having 1 to 12 carbon atoms, and Polyoxyalkylene having 1 to 12 carbon atoms. Among the substituents, formula (XLS-1), formula (XLS-2), formula (XLS-3), formula (XLS-9), formula (XLS-10) or formula (XLS-17) are preferred The group represented by) is more preferably a group represented by formula (XLS-1), formula (XLS-3), or formula (XLS-17).

For details of the applications of such polymer compounds, polymer crosslinked bodies, pendant polymer compounds, and pendant polymer crosslinked bodies (hereinafter, also simply referred to as "polymer compounds and polymer crosslinked bodies"), It will be described later.

2. Production method of polycyclic aromatic compound substituted by cycloalkyl group and multimer thereof About the polycyclic aromatic compound represented by general formula (1) or general formula (2) and multimer thereof, basically First, an A ring (a ring), a B ring (b ring), and a C ring (c ring) are bonded by a bonding group (a group containing X ¹ or X ² ) to produce an intermediate (first reaction) Then, the A ring (a ring), the B ring (b ring), and the C ring (c ring) are bonded by a bonding group (a group containing Y ¹ ), whereby the final product can be produced (second reaction ). In the first reaction, for example, if it is an etherification reaction, a normal reaction such as a nucleophilic substitution reaction or a Ullmann reaction can be used, and if it is an amination reaction, Buchwald-Hart can be used The usual reactions such as the Buchwald-Hartwig Reaction. In the second reaction, a Tandem Hetero-Friedel-Crafts Reaction (a continuous aromatic electrophilic substitution reaction, which is the same below) can be used. In addition, by using a cycloalkyl substituted raw material or adding a step of introducing a cycloalkyl at one of these reaction steps, the present invention can be produced in which a cycloalkyl is substituted at a desired position. compound of.

As shown in the following scheme (1) or (2), the second reaction is a reaction in which Y ¹ which is bonded to A ring (a ring), B ring (b ring), and C ring (c ring) is introduced as an example. The following shows the case where Y ¹ is a boron atom and X ¹ and X ² are oxygen atoms. First, hydrogen atoms between X ¹ and X ² are ortho-metalized using n-butyllithium, second butyllithium, or third butyllithium, or the like. Next, boron trichloride or boron tribromide is added to perform lithium-boron metal exchange, and then a Bronsted base such as N, N-diisopropylethylamine is added to perform tandem boron. Tandem Bora-Friedel-Crafts Reaction, so that the target can be obtained. In the second reaction, in order to promote the reaction, a Lewis acid such as aluminum trichloride may be added. It should be noted that the definitions of the symbols of the structural formulas in the following flow (1) and flow (2), and in the subsequent flow (3) to flow (28) are the same as the above definitions.

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In addition, the said process (1) or (2) mainly shows the manufacturing method of the polycyclic aromatic compound represented by General formula (1) or general formula (2), However, regarding the multimer, it can be used by It is manufactured by having multiple intermediates of A ring (a ring), B ring (b ring) and C ring (c ring). Specifically, the following processes (3) to (5) will be described. In this case, the target substance can be obtained by setting the amount of the reagent such as butyllithium to be used to be 2 times or 3 times.

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In the process described above, lithium is introduced to a desired position by ortho metallization, but a bromine atom or the like may be introduced at a position where lithium is to be introduced as in the following process (6) and process (7), and also Lithium is introduced to a desired position by halogen-metal exchange.

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In addition, as for the method for producing the multimer described in the process (3), halogens such as a bromine atom or a chlorine atom may be introduced at a position where lithium is to be introduced as in the above-mentioned processes (6) and (7), and also Lithium is introduced to a desired position by halogen-metal exchange (the following flow (8), flow (9), and flow (10)).

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[Chem 58]

According to this method, it is useful to synthesize a target object even when ortho metallization cannot be performed due to the influence of a substituent.

By appropriately selecting the synthesis method and also appropriately selecting the raw materials used, it is possible to synthesize a cycloalkyl group at a desired position, have a substituent at a desired position, and Y ¹ is a boron atom, X ¹ and X ² is an oxygen atom, a polycyclic aromatic compound, and a polymer thereof.

Next, a case where Y ¹ is a boron atom and X ¹ and X ² are nitrogen atoms is shown as an example in the following scheme (11) and scheme (12). As in the case where X ¹ and X ² are oxygen atoms, first, hydrogen atoms between X ¹ and X ² are ortho-metalized using n-butyllithium or the like. Next, boron tribromide and the like are added to perform lithium-boron metal exchange, and then, a Bronst base such as N, N-diisopropylethylamine is added to perform a tandem boronfriedel-quarfte The reaction can obtain the target. Here, in order to promote the reaction, a Lewis acid such as aluminum trichloride may be added. In addition, by using a cycloalkyl substituted raw material or adding a step of introducing a cycloalkyl at one of these reaction steps, the present invention can be produced in which a cycloalkyl is substituted at a desired position. compound of.

[Chemical 59]

[Chemical 60]

In addition, as for the polymer when Y ¹ is a boron atom and X ¹ and X ² are nitrogen atoms, a bromine atom or chlorine may be introduced at a position where lithium is to be introduced, as in the above-mentioned schemes (6) and (7). A halogen such as an atom is also introduced into a desired position by halogen-metal exchange (the following flow (13), flow (14), and flow (15)).

[Chem 61]

[Chem 62]

[Chem 63]

Next, a case where Y ¹ is a phosphorus sulfide, a phosphorus oxide, or a phosphorus atom, and X ¹ and X ² are an oxygen atom is shown as an example in the following schemes (16) to (19). As in the prior art, first, hydrogen atoms between X ¹ and X ² are ortho-metalized using n-butyllithium or the like. Then, phosphorus trichloride and sulfur are sequentially added, and finally Lewis acids such as aluminum trichloride and Brnister bases such as N, N-diisopropylethylamine are added in order to perform tandem phosphofreder-quar The Fudan reaction (Tandem Phospha-Friedel-Crafts Reaction), so as to obtain Y ¹ is a phosphorus sulfide compound. In addition, by treating the obtained phosphorus sulfide compound with m-chloroperbenzoic acid (m-CPBA), a compound in which Y ¹ is a phosphorus oxide can be obtained, and by treating with triethylphosphine, A compound in which Y ¹ is a phosphorus atom can be obtained. In addition, by using a cycloalkyl substituted raw material or adding a step of introducing a cycloalkyl at one of these reaction steps, the present invention can be produced in which a cycloalkyl is substituted at a desired position. compound of.

[Chemical 64]

[Chem 65]

[Chemical 66]

[Chemical 67]

In addition, as for the polymer when Y ¹ is phosphorus sulfide and X ¹ and X ² are oxygen atoms, a bromine atom or chlorine may be introduced at a position where lithium is to be introduced, as in the above-mentioned processes (6) and (7). A halogen such as an atom is also introduced into a desired position by halogen-metal exchange (the following flow (20), flow (21), and flow (22)). In addition, the multimer formed when Y ¹ is phosphorus sulfide and X ¹ and X ² are oxygen atoms formed in the manner described above is also the same as in the above scheme (18) and (19), by using m-chloroperbenzoic acid. A compound in which Y ¹ is a phosphorus oxide can be obtained by treatment with (m-CPBA), and a compound in which Y ¹ is a phosphorus atom can be obtained by treatment with triethylphosphine.

[Chemical 68]

[Chemical 69]

[Chem 70]

Here, an example in which Y ¹ is B, P, P = O, or P = S and X ¹ and X ² are O or NR is described. However, Y ¹ can be synthesized into Al, Ga, and As by changing the raw materials appropriately. , Si-R or Ge-R, or a compound in which X ¹ and X ² are S.

Specific examples of the solvent used in the above reaction are third butylbenzene, xylene, and the like.

In the general formula (2), adjacent groups in the substituents R ¹ to R ¹¹ of the a ring, the b ring, and the c ring may be bonded to each other and form an aryl ring together with the a ring, the b ring, or the c ring. Or heteroaryl ring, at least one hydrogen in the formed ring may be substituted by an aryl or heteroaryl group. Therefore, the polycyclic aromatic compound represented by the general formula (2) is represented by formula (2) of the following scheme (23) and scheme (24) according to the mutual bonding form of the substituents in the a ring, b ring, and c ring -1) and the formula (2-2) change the ring structure of the compound. These compounds can be synthesized by applying the synthesis methods shown in the above schemes (1) to (19) to the intermediates shown in the following schemes (23) and (24). In addition, by using a cycloalkyl substituted raw material or adding a step of introducing a cycloalkyl at one of these reaction steps, the present invention can be produced in which a cycloalkyl is substituted at a desired position. compound of.

[Chemical 71]

[Chemical 72]

The A 'ring, B' ring, and C 'ring in the formula (2-1) and the formula (2-2) represent that adjacent groups in the substituents R ¹ to R ¹¹ are bonded to each other and are respectively connected to the a ring. , Aryl ring or heteroaryl ring formed by ring b, ring c and ring c (also known as condensed ring formed by condensing other ring structures in ring a, ring b or ring c). In addition, although not shown in the formula, there are also compounds in which all of the a ring, the b ring, and the c ring are changed to the A 'ring, the B' ring, and the C 'ring.

In the general formula (2), "R of> NR and / or said> -C (-R) ₂ -R is -O-, -S-, -C (-R) ₂ -or mono The bond is bonded to the a ring, b ring and / or c ring. The rule "can be expressed by a compound represented by the formula (2-3-1) of the following scheme (25) and having X ¹ or X ² is introduced into the ring structure of condensed ring B ′ and condensed ring C ′, or is represented by formula (2-3-2) or formula (2-3-3), and has X ¹ or X ² by A ring structure introduced into the condensed ring A '. These compounds can be synthesized by applying the synthesis methods shown in the above schemes (1) to (19) to the intermediates shown in the following scheme (25). In addition, by using a cycloalkyl substituted raw material or adding a step of introducing a cycloalkyl at one of these reaction steps, the present invention can be produced in which a cycloalkyl is substituted at a desired position. compound of.

[Chemical 73]

In addition, in the synthesis methods of the above schemes (1) to (17) and (20) to (25), it is shown that before adding boron trichloride or boron tribromide, etc., An example of a tandem heterofrieder-quarfte reaction in which a hydrogen atom (or a halogen atom) between X ¹ and X ² is ortho metallized, but an ortho using a butyl lithium or the like is not required. Metallized in situ, and the reaction is performed by adding boron trichloride, boron tribromide, or the like.

When Y ¹ is a phosphorus-based compound, as shown in the following scheme (26) or scheme (27), X ¹ and X ^{2 are} paired with n-butyllithium, second butyl lithium, or third butyl lithium. Hydrogen atoms between (O in the following formula) are ortho-metalized, then bis (diethylamino) chlorophosphine is added, and after lithium-phosphorous metal exchange, a Lewis acid such as aluminum trichloride is added. This performs a tandem phosphofreder-quarft reaction, thereby obtaining a target. This reaction method is also described in International Publication No. 2010/104047 (for example, page 27). In addition, by using a cycloalkyl substituted raw material or adding a step of introducing a cycloalkyl at one of these reaction steps, the present invention can be produced in which a cycloalkyl is substituted at a desired position. compound of.

[Chemical 74]

[Chemical 75]

Furthermore, in the process (26) or process (27), two-times or three-times the molar amount of butyl lithium such as butyl lithium is used relative to the molar amount of the intermediate 1 to thereby Multimeric compounds can also be synthesized. In addition, by introducing a halogen such as a bromine atom or a chlorine atom in advance at a position where a metal such as lithium is to be introduced, and performing a halogen-metal exchange, a metal can be introduced at a desired position.

In addition, as for the polycyclic aromatic compound represented by the general formula (2-A), a cycloalkyl-substituted intermediate is synthesized and cyclized as in the following scheme (28), whereby a naphthene can be synthesized and utilized. A polycyclic aromatic compound in which a group is substituted at a desired position. In the scheme (28), X represents halogen or hydrogen, and the definitions of other symbols are the same as the definitions of the symbols in the general formula (20).

[Chemical 76]

The intermediate before cyclization in the scheme (28) can also be synthesized by the method shown in the scheme (1) and the like. That is, an intermediate having a desired substituent can be synthesized by an appropriate combination of a Buchwald-Hartwig reaction or a Suzuki coupling reaction, or an etherification reaction using a nucleophilic substitution reaction or a Ullman reaction. Thing. In these reactions, a commercially available product can also be used as a raw material to be a cycloalkyl-substituted precursor.

A compound of the general formula (2-A) having a diphenylamino group substituted with a cycloalkyl group can also be synthesized, for example, by the following method. That is, the p-cycloalkyl-substituted bromobenzene and the trihalogenated aniline are introduced into a diphenylamino group substituted with a cycloalkyl group by an amination reaction such as a Buchwald-Hartwig reaction, and are then introduced at X ¹ , When X ² is NR, it is derivatized into an intermediate (M-3) by an amination reaction such as the Buchwald-Hartwig reaction. When X ¹ and X ² are O, borrow Derived into an intermediate (M-3) by etherification using phenol, and then, for example, by trans-metallizing a metallizing agent such as butyllithium and then halogenating a boron tribromide A tandem Borzafried-Quarft reaction in which boron functions and then acts as a diethylisopropylamine-based Brnister base can synthesize a compound of the general formula (2-A). These reactions can also be applied to other cycloalkyl substituted compounds.

In addition, examples of the ortho-metallation reagents used in the above schemes (1) to (28) include methyllithium, n-butyllithium, second butyllithium, and third butyllithium. Organic basic compounds such as lithium lithium, lithium diisopropylphosphonium amine, lithium tetramethylpiperidine, lithium hexamethyldisilazide, and potassium hexamethyldisilazide.

Further, as the processes (1) to the metal flow (28) used in a metal exchange reagent -Y ¹ include: trifluoride of Y ^1, Y ¹ trichloride, tribromo of Y ¹ Y halide compounds, Y ¹ triiodide like ^1, CIPN (NEt _{2) 2} group Y of the halide and the like ^1, Y ¹ alkoxylates, Y aryloxides like ^1.

In addition, examples of the Brewster base used in the above schemes (1) to (28) include N, N-diisopropylethylamine, triethylamine, 2,2,6,6- Tetramethylpiperidine, 1,2,2,6,6-pentamethylpiperidine, N, N-dimethylaniline, N, N-dimethyltoluidine, 2,6-dimethylpyridine, tetramethyl Sodium phenylborate, potassium tetraphenylborate, triphenylborane, tetraphenylsilane, Ar ₄ BNa, Ar ₄ BK, Ar ₃ B, Ar ₄ Si (in addition, Ar is an aryl group such as phenyl), etc. .

Examples of the Lewis acid used in the above schemes (1) to (28) include AlCl ₃ , AlBr ₃ , AlF ₃ , BF ₃ · OEt ₂ , BCl ₃ , BBr ₃ , GaCl ₃ , GaBr ₃ , and InCl. ₃ , InBr ₃ , In (OTf) ₃ , SnCl ₄ , SnBr ₄ , AgOTf, ScCl ₃ , Sc (OTf) ₃ , ZnCl ₂ , ZnBr ₂ , Zn (OTf) ₂ , MgCl ₂ , MgBr ₂ , Mg (OTf) ₂ , LiOTf, NaOTf, KOTf, Me ₃ SiOTf, Cu (OTf) ₂ , CuCl ₂ , YCl ₃ , Y (OTf) ₃ , TiCl ₄ , TiBr ₄ , ZrCl ₄ , ZrBr ₄ , FeCl ₃ , FeBr ₃ , CoCl ₃ , CoBr ₃ and so on.

In the above schemes (1) to (28), in order to promote the tandem heterofrieder-quarft reaction, a Brnister base or a Lewis acid may be used. In the case where a halide, using trifluoride of Y ^1, Y ¹ trichloride, Y ¹ tribromide, Y ¹ triiodide other of Y ^1, with the aromatic electrophilic substitution reaction It progresses to generate acids such as hydrogen fluoride, hydrogen chloride, hydrogen bromide, and hydrogen iodide. Therefore, it is effective to use a Brnister base that captures the acid. On the other hand, the use of amine Y ¹ is a halide, in the case of the alkoxide of Y ^1, as for the aromatic electrophilic substitution reaction, to generate an amine, an alcohol, and therefore in most cases, without Bronister base is used, but it is effective to use a Lewis acid which promotes the detachment of the amine group or the alkoxy group.

In addition, the polycyclic aromatic compound of the present invention or a multimer thereof also includes a compound in which at least a part of hydrogen atoms is substituted by deuterium or cyano or a compound substituted by halogen such as fluorine or chlorine. Such compounds and the like can be used by Desired, cyanated, fluorinated, or chlorinated raw materials at desired positions are synthesized in the same manner as described above.

3. Organic device The cycloalkyl-substituted polycyclic aromatic compound of the present invention can be used as a material for an organic device. Examples of the organic device include an organic electroluminescence element, an organic field-effect transistor, and an organic thin-film solar cell.

3-1. Organic Electroluminescence Element Hereinafter, the organic EL element of this embodiment will be described in detail based on the drawings. FIG. 1 is a schematic cross-sectional view showing the organic EL element of this embodiment.

<Structure of Organic Electroluminescence Element>
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, a hole transmission layer 104 provided on the hole injection layer 103, The light-emitting layer 105 provided on the hole-transport layer 104, the electron-transport layer 106 provided on the light-emitting layer 105, the electron-injection layer 107 provided on the electron-transport layer 106, and the cathode 108 provided on the electron-injection layer 107.

In addition, the organic EL element 100 may be formed in a reversed order to form, for example, a structure including a substrate 101, a cathode 108 provided on the substrate 101, an electron injection layer 107 provided on the cathode 108, and an electron The electron transport layer 106 on the injection layer 107, the light emitting layer 105 provided on the electron transport layer 106, the hole transport layer 104 provided on the light emitting layer 105, the hole injection layer 103 provided on the hole transport layer 104, And an anode 102 disposed on the hole injection layer 103.

Not all of the layers are required, and the minimum constituent unit is configured to include the anode 102, the light-emitting layer 105, and the cathode 108. The hole injection layer 103, the hole transport layer 104, the electron transport layer 106, and the electron injection layer 107 are arbitrary. Set the layers. In addition, each of the layers may include a single layer or a plurality of layers.

As the form of the layer constituting the organic EL element, in addition to the constitution form of the "substrate / anode / hole injection layer / hole transport layer / light-emitting layer / electron transport layer / electron injection layer / cathode", it may be " 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 / Light-emitting layer / Electron transport layer / Electron injection layer / Cathode "," Substrate / Anode / hole transport layer / Light-emitting layer / Electron injection layer / Cathode "," Substrate / Anode / Hole transport layer / Light-emitting layer / Electron "Transport layer / cathode", "Substrate / Anode / hole injection layer / Light-emitting layer / Electron injection layer / Cathode", "Substrate / Anode / hole injection layer / Light-emitting layer / Electron transport layer / Cathode", "Substrate / Anode / Light-emitting layer / electron transport layer / cathode "," substrate / anode / light-emitting layer / electron injection layer / cathode " Into shape.

<Substrate in organic electroluminescence element>
The substrate 101 is a support for the organic EL element 100, and generally quartz, glass, metal, plastic, or the like is used. The substrate 101 is formed into a plate shape, a film shape, or a sheet shape according to the purpose. For example, a glass plate, a metal plate, a metal foil, a plastic film, a plastic sheet, or the like can be used. Among them, glass plates and transparent synthetic resin plates such as polyester, polymethacrylate, polycarbonate, and polyfluorene are preferred. If it is a glass substrate, soda-lime glass, alkali-free glass, etc. can be used, and what is necessary is just to have a thickness sufficient to maintain mechanical strength, for example, it is sufficient to have 0.2 mm or more. The upper limit of the thickness is, for example, 2 mm or less, and preferably 1 mm or less. Regarding the material of the glass, the less dissolved ions from the glass, the better, so alkali-free glass is preferred. Since soda-lime glass with a barrier coating such as SiO _{2 is} also commercially available, this soda-lime glass can be used. . In addition, in order to improve the gas barrier property, a gas barrier film such as a fine silicon oxide film may be provided on at least one side of the substrate 101, and particularly a board, film, or sheet made of a synthetic resin having low gas barrier property is used as the substrate 101 In this case, it is preferable to provide a gas barrier film.

<Anode in organic electroluminescence element>
The anode 102 plays a role of injecting a hole into the light emitting layer 105. When a hole injection layer 103 and / or a 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 layers.

Examples of the material forming the anode 102 include inorganic compounds and organic compounds. Examples of the inorganic compound include metals (aluminum, gold, silver, nickel, palladium, chromium, etc.), metal oxides (indium oxide, tin oxide, and indium tin oxide (ITO)) , Indium Zinc Oxide (IZO), etc.), metal halide (copper iodide, etc.), copper sulfide, carbon black, ITO glass or NESA glass. Examples of the organic compound include polythiophene such as poly (3-methylthiophene), and conductive polymers such as polypyrrole and polyaniline. Moreover, it can select suitably from the substance used as the anode of an organic EL element, and can use it.

The resistance of the transparent electrode is not limited as long as it can supply a sufficient current for light emission of the light emitting element, but from the viewpoint of power consumption of the light emitting element, low resistance is desirable. For example, if the ITO substrate is 300 Ω / □ or less, it functions as an element electrode. However, substrates of about 10 Ω / □ can be supplied now. Therefore, it is particularly desirable to use, for example, 100 Ω / □ to 5 Ω / □. A low-resistance product of 50 Ω / □ to 5 Ω / □ is preferred. The thickness of ITO can be arbitrarily selected according to the resistance value, but it is often used between 50 nm and 300 nm.

<A hole injection layer and a hole transport layer in an organic electroluminescence element>
The hole injection layer 103 plays a role of efficiently injecting holes migrated 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 transmitting holes injected from the anode 102 or holes injected from the anode 102 through the hole injection layer 103 to the light emitting layer 105. The hole injection layer 103 and the hole transmission layer 104 are formed by laminating and mixing one or two or more hole injection / transport materials, or are formed by a mixture of a hole injection / transport material and a polymer binder. Alternatively, an inorganic salt such as iron (III) chloride may be added to the hole injection / transport material to form a layer.

As a hole injection / transporting substance, it is necessary to efficiently inject / transmit a hole from a positive electrode between electrodes to which an electric field is applied, and it is desirable that the hole injection is highly efficient and efficiently transmits the injected hole. Therefore, a substance having a small free potential, a large hole mobility, and excellent stability is also preferred, and impurities that do not easily generate traps during manufacture and use are preferred.

As a material for forming the hole injection layer 103 and the hole transport layer 104, a compound that has been conventionally used as a hole charge transport material in photoconductive materials can be used for hole injection in p-type semiconductors and organic EL devices. Any of the well-known compounds of the layer and the hole transport layer is selected and used. Specific examples of these materials are carbazole derivatives such as carbazole derivatives (N-phenylcarbazole, polyvinylcarbazole, etc.), bis (N-arylcarbazole), or bis (N-alkylcarbazole). Compounds, triarylamine derivatives (polymers with aromatic tertiary amine groups on the main or side chain, 1,1-bis (4-di-p-tolylaminophenyl) cyclohexane, N, N '-Diphenyl-N, N'-bis (3-methylphenyl) -4,4'-diaminobiphenyl, N, N'-diphenyl-N, N'-dinaphthyl- 4,4'-diaminobiphenyl, N, N'-diphenyl-N, N'-bis (3-methylphenyl) -4,4'-diphenyl-1,1'-di Amine, 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, 4,4', 4 ''-tri (3-methylphenyl (phenyl) amino) triphenylamine derivatives such as triphenylamine, starburst amine derivatives, etc.), stilbene derivatives, phthalocyanine derivatives (metal-free, copper Phthalocyanine, etc.), pyrazoline derivatives, perylene compounds, benzofuran derivatives or thiophene derivatives, oxadiazole derivatives, quinoxaline derivatives (Such as 1,4,5,8,9,12-hexaazatriphenylene-2,3,6,7,10,11-hexacarbonitrile, etc.), heterocyclic compounds such as porphyrin derivatives, polymer Silane, etc. Among the polymer systems, polycarbonates or styrene derivatives, polyvinyl carbazoles, and polysilanes having the above-mentioned monomers on the side chains are preferred. However, as long as it is a film required for the production of a light-emitting device, The compound in which an anode is injected into a hole, and thereby a hole can be transmitted, is not particularly limited.

It is also known that the conductivity of an organic semiconductor is strongly affected by its doping. Such an organic semiconductor matrix material includes a compound having a good electron donating property or a compound having a good electron accepting property. In order to dope the electron-donating substance, Tetracyanoquinodimethane (TCNQ) or 2,3,5,6-tetrafluorotetracyano-1,4-benzoquinone dimethane (2,3,5 , 6-tetrafluorotetracyano- 1,4-benzoquinodimethane (F4TCNQ) and other strong electron acceptors (for example, refer to the literature "M. Pfeiffer, A. Bayer, T. Fritz, K. Leo (M. Pfeiffer, A. Beyer, T. Fritz, K. Leo), Applied Physics Letters (Appl. Phys. Lett.), 73 (22), 3202-3204 (1998) "and the document" J. Blochewitz, M Feife, T. Fritz, K. Leo (J. Blochwitz, M. Pheiffer, T. Fritz, K. Leo), Applied Physics Letters (Appl. Phys. Lett.), 73 (6) 729-731 (1998) "). These are called so-called holes through the electron migration process of the electron-donating basic substance (hole-transporting substance). The conductivity of basic substances varies considerably depending on the number of holes and mobility. As a matrix material having hole-transport properties, for example, a benzidine derivative (TPD, etc.) or a starburst amine derivative (4,4 ', 4' '-tri (N, N-diphenylamine group) is known. ) Triphenylamine (4,4 ', 4' '-tris (N, N-diphenylamino) triphenylamine, TDATA), etc.), or specific metal phthalocyanine (especially zinc phthalocyanine (ZnPc), etc.) (Japanese Patent Laid-Open) 2005-167175).

The materials for the hole injection layer and the hole transport layer can also be used as the following polymer compounds or polymer crosslinked bodies thereof, or the following suspended polymer compounds or suspended polymer crosslinked bodies thereof In the material for the hole layer, the polymer compound is made of a reactive compound substituted with a reactive substituent in the material for the hole injection layer and the material for the hole transport layer as a monomer to polymerize it. The suspension type polymer compound is obtained by reacting a main chain type polymer with the reactive compound. As a reactive substituent in this case, the description in the polycyclic aromatic compound represented by Formula (1) can be cited.
Details of applications of such a polymer compound and a polymer crosslinked body will be described later.

<Light-emitting layer in organic electroluminescence element>
The light emitting layer 105 is a layer that emits light by recombining the hole injected from the anode 102 and the electron 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 a compound (light-emitting compound) that emits light by being excited by recombination of holes and electrons, and is preferably one that can form a stable thin film shape and exhibit strong solid state. Luminescent (fluorescent) efficiency compound. In the present invention, as the material for the light-emitting layer, a host material and a polycyclic aromatic compound represented by the general formula (1) as a dopant material can be used, for example.

The light emitting layer may be a single layer or may include a plurality of layers, and any of them may be used. The light emitting layer is formed of a material (host material, dopant material) for the light emitting layer, respectively. The host material and the dopant material may be one kind or a combination of plural kinds, and any of them may be used. The dopant material may be contained in the entire host material, or may be contained in a part of the host material, either. The doping method may be formed by a co-evaporation method with the host material, or may be simultaneously vapor-deposited after being mixed with the host material in advance.

The amount of the host material to be used varies depending on the type of the host material, as long as it is determined in accordance with the characteristics of the host material. The basis of the amount of the host material used is preferably 50% to 99.999% by weight, more preferably 80% to 99.95% by weight, and still more preferably 90% to 99.9% by weight.

The amount of the dopant material used varies depending on the type of the dopant material, as long as it is determined in accordance with the characteristics of the dopant material. The use amount of the dopant is preferably 0.001% to 50% by weight, more preferably 0.05% to 20% by weight, and still more preferably 0.1% to 10% by weight. If it is the said range, it is preferable at the point which can prevent a concentration quenching phenomenon, for example.

Examples of the host material include condensed ring derivatives such as anthracene, fluorene, dibenzofluorene, and fluorene, bisstyryl anthracene derivatives, and distyryl benzene derivatives such as stilbene derivatives. , Tetraphenylbutadiene derivatives, cyclopentadiene derivatives, and the like. Particularly preferred are anthracene-based compounds, fluorene-based compounds or dibenzofluorene-based compounds.

<Anthracene-based compound>
The main anthracene-based compound is, for example, a compound represented by the following general formula (3).
[Chemical 77]

In equation (3),
X and Ar ⁴ are independently hydrogen, aryl which may be substituted, heteroaryl which may be substituted, diarylamino which may be substituted, diheteroarylamine which may be substituted, and Arylheteroarylamino, substituted alkyl, substituted cycloalkyl, substituted alkenyl, substituted alkoxy, substituted aryloxy, substituted Arylthio or substituted silyl groups, all X and Ar ⁴ will not be hydrogen at the same time.
At least one hydrogen in the compound represented by the formula (3) may be substituted with a halogen, a cyano group, a deuterium or a substituted heteroaryl group.

In addition, a multimer (preferably a dimer) may be formed using the structure represented by the formula (3) as a unit structure. In this case, for example, the form in which unit structures represented by formula (3) are bonded to each other through X, and X may be a single bond, an arylene group (such as a phenylene group, a phenylene group, or a naphthyl group). ) And extended heteroaryl groups (pyridine ring, dibenzofuran ring, dibenzothiophene ring, carbazole ring, benzocarbazole ring, and phenyl-substituted carbazole ring having divalent atomic valence groups), etc. .

The aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, alkyl, cycloalkyl, alkenyl, alkoxy, aryloxy, arylthio The details of the radical or silane group are described in the column of the preferred embodiment below. Examples of the substituents for these groups include aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, alkyl, cycloalkyl, Alkenyl, alkoxy, aryloxy, arylthio, or silane groups, etc. The details of these groups are also described in the column of the preferred form below.

Hereinafter, preferred embodiments of the anthracene-based compound will be described. The definitions of the symbols in the following structures are the same as those described above.
[Chem. 78]

In the general formula (3), X is independently a group represented by the formula (3-X1), formula (3-X2), or formula (3-X3), and the formula (3-X1), formula (3 -X2) or a group represented by formula (3-X3) is bonded to an anthracene ring of formula (3) at *. It is preferred that two Xs do not simultaneously form a group represented by formula (3-X3). More preferably, two Xs do not simultaneously form a group represented by formula (3-X2).

In addition, a multimer (preferably a dimer) may be formed using the structure represented by the formula (3) as a unit structure. In this case, for example, the form in which unit structures represented by formula (3) are bonded to each other through X, and X may be a single bond, an arylene group (such as a phenylene group, a phenylene group, or a naphthyl group). ) And extended heteroaryl groups (pyridine ring, dibenzofuran ring, dibenzothiophene ring, carbazole ring, benzocarbazole ring, and phenyl-substituted carbazole ring having divalent atomic valence groups), etc. .

The naphthyl sites in formulas (3-X1) and (3-X2) may be condensed by a benzene ring. The structure condensed in this way is shown below.
[Chem. 79]

Ar ¹ and Ar ² are independently hydrogen, phenyl, biphenyl, bitriphenyl, bitetraphenyl, naphthyl, phenanthryl, fluorenyl, benzofluorenyl, fluorenyl, triphenyl, A fluorenyl group or a group represented by the formula (A) (including carbazolyl, benzocarbazolyl, and phenyl-substituted carbazolyl). When Ar ¹ or Ar ² is a group represented by the formula (A), the group represented by the formula (A) is at the same position as the formula (3-X1) or the formula (3-X2). The naphthalene ring is bonded.

Ar ³ is phenyl, biphenyl, bitriphenyl, bitetraphenyl, naphthyl, phenanthryl, fluorenyl, benzofluorenyl, fluorenyl, triphenylene, fluorenyl, or the formula ( The group represented by A) (including carbazolyl, benzocarbazolyl, and phenyl substituted carbazolyl). When Ar ³ is a group represented by the formula (A), the group represented by the formula (A) is bonded to a single bond represented by a straight line in the formula (3-X3) at its * position. . That is, the anthracene ring of the formula (3) is directly bonded to the group represented by the formula (A).

Further, Ar ³ may have a substituent group, Ar ³ is at least one hydrogen may be further alkyl having 1 to 4 carbon atoms, cycloalkyl having 5 to 10, phenyl, biphenyl, terphenyl, Naphthyl, phenanthryl, fluorenyl, fluorenyl, triphenylene, fluorenyl, or a group represented by the formula (A) (which also includes carbazolyl and phenyl substituted carbazolyl) is substituted. In addition, when the substituent which Ar ³ has is a group represented by formula (A), the group represented by formula (A) is bonded to Ar ³ in formula (3-X3) at * Knot.

Ar ^{4 is} independently hydrogen, phenyl, biphenyl, bitriphenyl, naphthyl, or alkyl group (methyl, ethyl, third butyl, etc.) having 1 to 4 carbon atoms and / or carbon Cycloalkyl substituted silyl groups of 5 to 10.

Examples of the alkyl group having 1 to 4 carbon atoms substituted in the silane group include methyl, ethyl, propyl, isopropyl, butyl, second butyl, third butyl, and cyclobutyl. The three hydrogens in each are independently substituted by these alkyl groups.

Specific examples of the "silyl group substituted with an alkyl group having 1 to 4 carbon atoms" include trimethylsilyl group, triethylsilyl group, tripropylsilyl group, triisopropylsilyl group, and tributyl group. Silyl, tri-second butylsilyl, tri-third butylsilyl, ethyldimethylsilyl, propyldimethylsilyl, isopropyldimethylsilyl, butyldimethyl Silyl, second butyldimethylsilyl, third butyldimethylsilyl, methyldiethylsilyl, propyldiethylsilyl, isopropyldiethylsilyl, butyl Diethylsilyl, second butyldiethylsilyl, third butyldiethylsilyl, methyldipropylsilyl, ethyldipropylsilyl, butyldipropylsilyl , Second butyl dipropyl silyl group, third butyl dipropyl silyl group, methyl diisopropyl silyl group, ethyl diisopropyl silyl group, butyl diisopropyl silyl group, second Butyldiisopropylsilyl, tertiary butyldiisopropylsilyl, and the like.

Examples of the cycloalkyl group having 5 to 10 carbon atoms substituted in the silane group include cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, norbornenyl, and bicyclic [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, diamond Alkyl, decahydronaphthyl, decahydrofluorenyl and the like, the three hydrogens in the silane group are independently substituted by these cycloalkyl groups.

Specific examples of the "silyl group substituted by a cycloalkyl group having 5 to 10 carbon atoms" include a tricyclopentylsilyl group, a tricyclohexylsilyl group, and the like.

As the substituted silyl group, there are also a dialkylcycloalkylsilyl group substituted with 2 alkyl groups and 1 cycloalkyl group, and an alkyldialkyl group substituted with 1 alkyl group and 2 cycloalkyl groups. As a specific example of a substituted alkyl group and a cycloalkyl group, the cycloalkyl silyl group mentioned above is mentioned.

The hydrogen in the chemical structure of the anthracene-based compound represented by the general formula (3) may be substituted by a group represented by the formula (A). When substituted with a group represented by the formula (A), the group represented by the formula (A) is substituted with at least one hydrogen in the compound represented by the formula (3) at *.

The group represented by formula (A) is one of the substituents which the anthracene-based compound represented by formula (3) may have.
[Chemical 80]

In the formula (A), Y is -O-, -S-, or> NR ²⁹ , and R ²¹ to R ²⁸ are each independently hydrogen, an alkyl group that may be substituted, a cycloalkyl group that may be substituted, and Substituted aryl, heteroaryl which may be substituted, alkoxy which may be substituted, aryloxy which may be substituted, arylthio which may be substituted, trialkylsilyl, tricycloalkylsilyl, Dialkylcycloalkylsilyl, alkyldicycloalkylsilyl, amine, halogen, hydroxy, or cyano which may be substituted. Adjacent groups in R ²¹ to R ²⁸ may be bonded to each other to form a hydrocarbon. Ring, aryl ring or heteroaryl ring, and R ²⁹ is hydrogen or an aryl group which may be substituted.

The "alkyl group" as the "substitutable alkyl group" in R ²¹ to R ²⁸ may be any of a linear chain and a branched chain, and examples thereof include a linear alkyl group having 1 to 24 carbon atoms or a carbon number of 3 ~ 24 branched chain alkyl. An alkyl group having 1 to 18 carbons (a branched alkyl group having 3 to 18 carbon atoms) is preferred, an alkyl group having 1 to 12 carbon atoms (a branched alkyl group having 3 to 12 carbon atoms) is more preferred, and still more preferred An alkyl group having 1 to 6 carbons (a branched alkyl group having 3 to 6 carbon atoms), and an alkyl group having 1 to 4 carbon atoms (a branched alkyl group having 3 to 4 carbon atoms) is particularly preferred.

Specific "alkyl" includes methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, second butyl, third butyl, n-pentyl, and isopentyl , Neopentyl, third pentyl, n-hexyl, 1-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, n-heptyl , 1-methylhexyl, n-octyl, third 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, normal fourteen, normal fifteen, normal sixteen, normal seventeen, normal eighteen, normal twenty, etc.

Examples of the "cycloalkyl group" of the "substitutable cycloalkyl group" in R ²¹ to R ²⁸ include a cycloalkyl group having 3 to 24 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, and 3 carbon atoms. Cycloalkyl of 16 to 16, cycloalkyl of 3 to 14 carbon, cycloalkyl of 5 to 10 carbon, cycloalkyl of 5 to 8 carbon, cycloalkyl of 5 to 6 carbon, 5 of carbon Cycloalkyl and so on.

Specific "cycloalkyl" includes cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, and carbons of these groups. 1 to 4 alkyl (especially methyl) substituents, or norbornenyl, bicyclo [1.0.1] butyl, bicyclo [1.1.1] pentyl, bicyclo [2.0.1] pentyl, bicyclic [1.2.1] Hexyl, bicyclic [3.0.1] hexyl, bicyclic [2.1.2] heptyl, bicyclic [2.2.2] octyl, adamantyl, diadamantyl, decahydronaphthyl, decahydrofluorene Base etc.

Examples of the "aryl group" of the "substitutable aryl group" in R ²¹ to R ²⁸ include an aryl group having 6 to 30 carbon atoms, preferably an aryl group having 6 to 16 carbon atoms, and more preferably carbon The aryl group having 6 to 12 is particularly preferably an aryl group having 6 to 10 carbon atoms.

Specific examples of the "aryl group" include: a phenyl group which is a monocyclic system; a biphenyl group which is a bicyclic system; a naphthyl group which is a condensed bicyclic system; Phenyl, ortho-triphenyl, para-triphenyl); fluorenyl, fluorenyl, fluorenyl, and phenanthryl as condensed tricyclic systems; triphenyl, fluorenyl, and condensed tetraphenyl as condensed tricyclic systems Pentyl; fluorenyl as a condensed pentacyclic system, fused pentaphenyl, and the like.

Examples of the "heteroaryl group" as the "optionally substituted heteroaryl group" in R ²¹ to R ²⁸ include a heteroaryl group having 2 to 30 carbon atoms, and a heteroaryl group having 2 to 25 carbon atoms is preferred. Heteroaryl groups having 2 to 20 carbon atoms are more preferred, heteroaryl groups having 2 to 15 carbon atoms are even more preferred, and heteroaryl groups having 2 to 10 carbon atoms are particularly preferred. Examples of the heteroaryl group include a heterocyclic ring containing one to five heteroatoms selected from oxygen, sulfur, and nitrogen as ring constituent atoms in addition to carbon.

Specific "heteroaryl" includes, for example, pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, oxadiazolyl, thiadiazolyl, triazolyl, Oxazolyl, pyrazolyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, indolyl, isoindolyl, 1H-indazolyl, benzimidazolyl, benzoxazolyl , Benzothiazolyl, 1H-benzotriazolyl, quinolinyl, isoquinolyl, perylene, quinazolinyl, quinoxaline, phthalazinyl, naphthyridinyl, purinyl, pyridinyl Base, carbazolyl, acridinyl, phenoxathiazyl, phenoxazinyl, phenothiazinyl, morphazinyl, indazinyl, furanyl, benzofuranyl, isobenzofuranyl, dibenzo Furyl, thienyl, benzo [b] thienyl, dibenzothienyl, furfuryl, oxadiazolyl, thiathranyl, naphthobenzofuranyl, naphthobenzothienyl, and the like.

Examples of the "alkoxy group" of the "substitutable alkoxy group" in R ²¹ to R ²⁸ include a linear alkoxy group having 1 to 24 carbon atoms or a branched alkane group having 3 to 24 carbon atoms. Oxygen. An alkoxy group having 1 to 18 carbons (branched alkoxy group having 3 to 18 carbons) is preferred, and an alkoxy group having 1 to 12 carbons (branched chain alkoxy group having 3 to 12 carbons) is more preferred Alkoxy), more preferably alkoxy having 1 to 6 carbons (branched alkoxy having 3 to 6 carbons), particularly preferably alkoxy having 1 to 4 carbons (3 to 4 carbon Branched alkoxy).

Specific “alkoxy” includes methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, second butoxy, third butoxy, Pentyloxy, hexyloxy, heptyloxy, octyloxy and the like.

The "aryloxy group" as the "substitutable aryloxy group" in R ²¹ to R ²⁸ is a group in which the hydrogen of the -OH group is substituted with an aryl group, and the aryl group can be cited as the R ²¹ to R "Aryl" in ²⁸ .

The "arylthio group" as the "substitutable arylthio group" in R ²¹ to R ²⁸ is a group in which the hydrogen of the -SH group is substituted with an aryl group, and the aryl group can be cited as the R ²¹ to R "Aryl" in ²⁸ .

Examples of the "trialkylsilyl group" in R ²¹ to R ²⁸ include a group in which three hydrogens in the silyl group are each independently substituted with an alkyl group, and the alkyl group can be cited as the R ²¹ to R ^{28 group} . "Alkyl" group. A preferable alkyl group for substitution is an alkyl group having 1 to 4 carbon atoms. Specific examples include methyl, ethyl, propyl, isopropyl, butyl, second butyl, and third butyl. Base, cyclobutyl and the like.

Specific examples of the "trialkylsilyl group" include trimethylsilyl group, triethylsilyl group, tripropylsilyl group, triisopropylsilyl group, tributylsilyl group, and tri-second butyryl group. Silyl, tri-third butylsilyl, ethyldimethylsilyl, propyldimethylsilyl, isopropyldimethylsilyl, butyldimethylsilyl, second butyl Dimethylsilyl, third butyldimethylsilyl, methyldiethylsilyl, propyldiethylsilyl, isopropyldiethylsilyl, butyldiethylsilyl, Dibutyldiethylsilyl, third butyldiethylsilyl, methyldipropylsilyl, ethyldipropylsilyl, butyldipropylsilyl, second butyldipropyl Silyl, third butyldipropylsilyl, methyldiisopropylsilyl, ethyldiisopropylsilyl, butyldiisopropylsilyl, second butyldiisopropylsilyl , Third butyl diisopropylsilyl, and the like.

Examples of the "tricycloalkylsilyl group" in R ²¹ to R ²⁸ include a group in which three hydrogens in the silyl group are each independently substituted with a cycloalkyl group. This cycloalkyl group can be cited as the R ²¹ to R ²⁸ is a "cycloalkyl" group. The preferred cycloalkyl group for substitution is a cycloalkyl group having 5 to 10 carbon atoms. Specific examples include cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, and cyclodecyl. , Bicyclic [1.1.1] pentyl, bicyclic [2.0.1] pentyl, bicyclic [1.2.1] hexyl, bicyclic [3.0.1] hexyl, bicyclic [2.1.2] heptyl, bicyclic [2.2.2] Octyl, adamantyl, decahydronaphthyl, decahydrofluorenyl and the like.

Specific examples of the "tricycloalkylsilyl group" include tricyclopentylsilyl group and tricyclohexylsilyl group.

Specific examples of a dialkylcycloalkylsilyl group substituted with two alkyl groups and one cycloalkyl group, and an alkyldicycloalkylsilyl group substituted with one alkyl group and two cycloalkyl groups Examples include a silyl group in which a group selected from the specific alkyl group and the cycloalkyl group is substituted.

Examples of the "substituted amino group" of the "substitutable amino group" in R ²¹ to R ²⁸ include an amino group in which two hydrogens are substituted with an aryl group or a heteroaryl group. Two amines substituted with aryl are diaryl substituted amines, two hydrogens substituted with heteroaryl are diheteroaryl substituted amines, and two hydrogens are substituted with aryl and heteroaryl Amine is an arylheteroaryl substituted amine. The aryl or heteroaryl group may be a group described as "aryl" or "heteroaryl" in R ²¹ to R ²⁸ .

Specific "substituted amino groups" include diphenylamino, dinaphthylamino, phenylnaphthylamino, dipyridylamino, phenylpyridylamine, and naphthylpyridyl. Amine groups, etc.

Examples of the "halogen" in R ²¹ to R ²⁸ include fluorine, chlorine, bromine, and iodine.

Some of the groups described as R ²¹ to R ²⁸ may be substituted as described above. Examples of the substituent in this case include an alkyl group, a cycloalkyl group, an aryl group, and a heteroaryl group. The alkyl group, cycloalkyl group, aryl group, or heteroaryl group can be described as "alkyl group", "cycloalkyl group", "aryl group", or "heteroaryl group" in R ²¹ to R ²⁸ . Group.

R ²⁹ in "＞ NR ²⁹ " as Y is hydrogen or an aryl group which may be substituted, and as the aryl group, a group described as the "aryl group" in R ²¹ to R ²⁸ may be cited, and As the substituent, a group described as a substituent for R ²¹ to R ²⁸ can be cited.

Adjacent groups in R ²¹ to R ²⁸ may be bonded to each other to form a hydrocarbon ring, an aryl ring, or a heteroaryl ring. When a ring is not formed, it is a group represented by the following formula (A-1), and when a ring is formed, a group represented by the following formula (A-2) to formula (A-14) can be mentioned, for example. In addition, at least one hydrogen in the group represented by any of formulas (A-1) to (A-14) may be an alkyl group, a cycloalkyl group, an aryl group, a heteroaryl group, an alkoxy group, or an aromatic group. Oxy, arylthio, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, alkylbicycloalkylsilyl, diaryl substituted amino, diheteroaryl substituted Amine, arylheteroaryl is substituted with amine, halogen, hydroxyl or cyano.
[Chemical 81]

As a ring in which adjacent groups are bonded to each other, if it is a hydrocarbon ring, for example, a cyclohexane ring may be mentioned, and as an aryl ring or heteroaryl ring, the "aryl" in R ²¹ to R ²⁸ may be mentioned. Or "heteroaryl", and these rings are formed by condensing with one or two benzene rings in the formula (A-1).

Examples of the group represented by the formula (A) include groups represented by any one of the formulae (A-1) to (A-14), and the formula (A-1) is preferred. The group represented by any one of formula (A-5) and formula (A-12) to formula (A-14) is more preferably a group represented by formula (A-1) to formula (A-4) The group represented by any one is more preferably a group represented by any one of the formula (A-1), (A-3), and (A-4), and particularly preferably the formula The group represented by (A-1).

The group represented by formula (A) is at the position * in formula (A) with a naphthalene ring in formula (3-X1) or (3-X2), a single bond in formula (3-X3), and The case where Ar ³ in 3-X3) is bonded and substituted with at least one hydrogen in the compound represented by formula (3) is as described above, but among these bonding forms, it is preferred to be bonded to formula (3) -X1) or a naphthalene ring in the formula (3-X2), a single bond in the formula (3-X3), and / or an Ar ³ bond in the formula (3-X3).

Moreover, regarding the structure of the group represented by Formula (A), the naphthalene ring in Formula (3-X1) or Formula (3-X2), the single bond in Formula (3-X3), and Formula (3-X3) The position where Ar ³ in) is bonded, and the position substituted with at least one hydrogen in the compound represented by formula (3) in the structure of the group represented by formula (A) may be formula (A) At any position in the structure, for example, adjacent groups in R ²¹ to R ²⁸ in the structure of the formula (A) or R ²¹ to R ²⁸ in the structure of the formula (A) may be bonded to each other. Any ring formed or any position of R ²⁹ of "> NR ²⁹ " as Y in the structure of the formula (A) is bonded.

Examples of the group represented by the formula (A) include the following groups. Y and * in the formula have the same definitions as described above.
[Chem 82]

In addition, all or a part of hydrogen in the chemical structure of the anthracene-based compound represented by the general formula (3) may be deuterium.

Specific examples of the anthracene-based compound include compounds represented by the following formulae (3-1) to (3-72). In the following structural formula, "Me" represents a methyl group, "D" represents deuterium, and "tBu" represents a third butyl group.

[Chemical 83]

[Chemical 84]

[Chemical 85]

[Chem. 86]

The anthracene-based compound represented by the formula (3) may be a compound having a reactive group at a desired position of the anthracene skeleton, or a compound having a reactive group at a partial structure such as X, Ar ⁴ and the structure of the formula (A). The compound is used as a starting material, and is produced by Suzuki coupling, Negishi coupling, and other known coupling reactions. Examples of the reactive group of these reactive compounds include halogen and boric acid. As a specific manufacturing method, for example, reference may be made to the synthesis methods in paragraphs [0089] to [0175] of International Publication No. 2014/141725.

＜ Actinide compounds ＞
The compound represented by the general formula (4) basically functions as a host.
[Chemical 87]

In the formula (4),
R ¹ to R ¹⁰ are each independently hydrogen, aryl, heteroaryl (the heteroaryl may be bonded to the fluorene skeleton in the formula (4) via a linking group), diarylamino, and dihetero Arylamino, arylheteroarylamino, alkyl, cycloalkyl, alkenyl, alkoxy, or aryloxy, at least one of these hydrogens may be aryl, heteroaryl, alkyl, or ring Alkyl substitution,
In addition, R ¹ and R ² , R ² and R ³ , R ³ and R ⁴ , R ⁵ and R ⁶ , R ⁶ and R ⁷ , R ⁷ and R ⁸ or R ⁹ and R ¹⁰ may be independently bonded to each other, and Forming a condensed ring or a spiro ring, at least one hydrogen in the formed ring may be aryl, heteroaryl (the heteroaryl may be bonded to the formed ring via a linking group), diarylamine, di Heteroarylamino, arylheteroarylamino, alkyl, cycloalkyl, alkenyl, alkoxy or aryloxy, at least one of these hydrogens may be substituted by aryl, heteroaryl, alkyl Or cycloalkyl substitution, and,
At least one hydrogen in the compound represented by formula (4) may be substituted with halogen, cyano, or deuterium.

For details of each group defined by the formula (4), reference may be made to the description of the polycyclic aromatic compound of the formula (1) described above.

Examples of the alkenyl group in R ¹ to R ¹⁰ include an alkenyl group having 2 to 30 carbon atoms, preferably an alkenyl group having 2 to 20 carbon atoms, more preferably an alkenyl group having 2 to 10 carbon atoms, and even more preferably The alkenyl group having 2 to 6 carbon atoms is particularly preferably an alkenyl group having 2 to 4 carbon atoms. Preferred alkenyl groups are vinyl, 1-propenyl, 2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3 -Pentenyl, 4-pentenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl or 5-hexenyl.

In addition, as specific examples of the heteroaryl group, the following formula (4-Ar1), (4-Ar2), (4-Ar3), (4-Ar4), or (4-Ar5) ) Is a monovalent group expressed by removing any hydrogen atom from a compound.
[Chem 88]

In formulae (4-Ar1) to (4-Ar5), Y ^{1 is} independently O, S or NR, and R is phenyl, biphenyl, naphthyl, anthracenyl or hydrogen,
At least one hydrogen in the structure of the formula (4-Ar1) to the formula (4-Ar5) may be phenyl, biphenyl, naphthyl, anthracenyl, phenanthryl, methyl, ethyl, propyl, or butyl To replace.

These heteroaryl groups may be bonded to the fluorene skeleton in the formula (4) through a linking group. That is, the fluorene skeleton in the formula (4) and the heteroaryl group may not only be directly bonded, but may also be bonded through these through a linking group. Examples of the linking group include phenylene, phenylene, naphthyl, anthracene, methylene, ethylidene, -OCH ₂ CH _2- , -CH ₂ CH ₂ O-, or -OCH ₂ CH ₂ O- and so on.

In addition, R ¹ and R ² , R ² and R ³ , R ³ and R ⁴ , R ⁵ and R ⁶ , R ⁶ and R ^7, or R ⁷ and R ⁸ in the formula (4) may be independently bonded to each other, and A condensed ring is formed, and R ⁹ and R ¹⁰ may be bonded to form a spiro ring. The condensed ring formed by R ¹ to R ⁸ is a ring condensed with a benzene ring in formula (4) and is an aliphatic ring or an aromatic ring. An aromatic ring is preferred, and examples of the structure including a benzene ring in formula (4) include a naphthalene ring and a phenanthrene ring. The spiro ring formed by R ⁹ and R ¹⁰ is a ring that is spirally bonded to the 5-membered ring in formula (4) and is an aliphatic ring or an aromatic ring. An aromatic ring is preferable, and a fluorene ring etc. are mentioned.

The compound represented by the general formula (4) is preferably a compound represented by the following formula (4-1), (4-2), or (4-3), and each is R in the general formula (4) ¹ A compound obtained by condensing a benzene ring formed by bonding R ² , a compound obtained by condensing a benzene ring formed by bonding R ³ and R ⁴ in general formula (4), and R in general formula (4) A compound which is not bonded to any of ¹ to R ⁸ .
[Chem 89]

The definitions of R ¹ to R ¹⁰ in formula (4-1), formula (4-2), and formula (4-3) are the same as the corresponding R ¹ to R ¹⁰ in formula (4), and formula (4 The definitions of R ¹¹ to R ¹⁴ in -1) and formula (4-2) are also the same as R ¹ to R ¹⁰ in formula (4).

The compound represented by the general formula (4) is further preferably a compound represented by the following formula (4-1A), formula (4-2A) or formula (4-3A), and is a compound represented by the formula (4-1), A compound in which R ⁹ and R ^{10 are} bonded to form a spiro-fluorene ring in formula (4-1) or formula (4-3).
[Chemical 90]

The definitions of R ² to R ⁷ in formula (4-1A), formula (4-2A), and formula (4-3A) are the same as those in formula (4-1), formula (4-2), and formula (4-3) The corresponding R ² to R ^{7 in) are the} same, and the definitions of R ¹¹ to R ¹⁴ in formula (4-1A) and formula (2-2A) are also the same as those in formulas (4-1) and (4-2). R ¹¹ to R ^{14 are the} same.

Moreover, all or a part of hydrogen in the compound represented by Formula (4) may be substituted by halogen, cyano, or deuterium.

<Dibenzopyrene compounds>
The main dibenzofluorene-based compound is, for example, a compound represented by the following general formula (5).
[Chemical 91]

In the formula (5),
R ¹ to R ¹⁶ are each independently hydrogen, aryl, heteroaryl (the heteroaryl may be bonded to the dibenzofluorene skeleton in the formula (5) via a linking group), and diarylamino , Diheteroarylamino, arylheteroarylamino, alkyl, cycloalkyl, alkenyl, alkoxy, or aryloxy, at least one of these hydrogens may be aryl, heteroaryl, or alkoxy Radical or cycloalkyl substitution,
In addition, adjacent groups in R ¹ to R ¹⁶ may be bonded to each other to form a condensed ring, and at least one hydrogen in the formed ring may be an aryl group or a heteroaryl group (the heteroaryl group may be connected to the ring via a linking group) The resulting ring bond), diarylamino, diheteroarylamino, arylheteroarylamino, alkyl, cycloalkyl, alkenyl, alkoxy, or aryloxy substituted, these At least one of the hydrogens may be substituted by aryl, heteroaryl, alkyl, or cycloalkyl, and,
At least one hydrogen in the compound represented by formula (5) may be substituted with halogen, cyano, or deuterium.

For details of each group defined by the formula (5), reference may be made to the description of the polycyclic aromatic compound of the formula (1) described above.

Examples of the alkenyl group defined by the formula (5) include an alkenyl group having 2 to 30 carbon atoms, preferably an alkenyl group having 2 to 20 carbon atoms, more preferably an alkenyl group having 2 to 10 carbon atoms, and furthermore An alkenyl group having 2 to 6 carbon atoms is preferred, and an alkenyl group having 2 to 4 carbon atoms is particularly preferred. Preferred alkenyl groups are vinyl, 1-propenyl, 2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3 -Pentenyl, 4-pentenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl or 5-hexenyl.

Furthermore, as specific examples of the heteroaryl group, the following formula (5-Ar1), (5-Ar2), (5-Ar3), (5-Ar4), or (5-Ar5) ) A monovalent group formed by removing any hydrogen atom from a compound.
[Chemical 92]

In formulae (5-Ar1) to (5-Ar5), Y ^{1 is} independently O, S or NR, and R is phenyl, biphenyl, naphthyl, anthracenyl or hydrogen,
At least one hydrogen in the structure of the formula (5-Ar1) to the formula (5-Ar5) may be phenyl, biphenyl, naphthyl, anthryl, phenanthryl, methyl, ethyl, propyl, or butyl To replace.

These heteroaryl groups may be bonded to the dibenzofluorene skeleton in the formula (5) via a linking group. That is, the dibenzofluorene skeleton in the formula (5) and the heteroaryl group may not only be directly bonded, but may also be bonded through these through a linking group. Examples of the linking group include phenylene, phenylene, naphthyl, anthracene, methylene, ethylidene, -OCH ₂ CH _2- , -CH ₂ CH ₂ O-, or -OCH ₂ CH ₂ O- and so on.

The compound represented by the general formula (5) is preferably such that R ¹ , R ⁴ , R ⁵ , R ⁸ , R ⁹ , R ¹² , R ¹³ and R ¹⁶ are hydrogen. In this case, R ² , R ³ , R ⁶ , R ⁷ , R ¹⁰ , R ¹¹ , R ¹⁴ and R ¹⁵ in the formula (5) are preferably each independently hydrogen, phenyl, biphenyl, and naphthalene. Monovalent, anthracenyl, phenanthryl, monovalent having a structure of the formula (5-Ar1), formula (5-Ar2), formula (5-Ar3), formula (5-Ar4) or formula (5-Ar5) (A monovalent group having this structure can be passed through phenylene, phenylene, naphthyl, anthracene, methylene, ethylene, -OCH ₂ CH _2- , -CH ₂ CH ₂ O- Or -OCH ₂ CH ₂ O- and bonded to the dibenzofluorene skeleton in the formula (5)), methyl, ethyl, propyl, or butyl.

The compound represented by the general formula (5) is more preferably R ¹ , R ² , R ⁴ , R ⁵ , R ⁷ , R ⁸ , R ⁹ , R ¹⁰ , R ¹² , R ¹³ , R ¹⁵ and R ¹⁶ are hydrogen. In this case, at least one (preferably one or two, more preferably one) of R ³ , R ⁶ , R ^11, and R ¹⁴ in Formula (5) is a compound having a single bond, a phenylene group, and a crosslinker. Formula (5-Ar1) of phenyl, naphthyl, anthracenyl, methylene, ethylene, -OCH ₂ CH _2- , -CH ₂ CH ₂ O-, or -OCH ₂ CH ₂ O- , A monovalent group of a structure of formula (5-Ar2), formula (5-Ar3), formula (5-Ar4), or formula (5-Ar5),
The at least one other (that is, other than the position substituted by the monovalent group having the structure) is hydrogen, phenyl, biphenyl, naphthyl, anthracenyl, methyl, ethyl, propyl, or butyl, At least one of these hydrogens may be substituted by phenyl, biphenyl, naphthyl, anthracenyl, methyl, ethyl, propyl or butyl.

In addition, a monovalent group having a structure represented by the formulae (5-Ar1) to (5-Ar5) is selected as R ² , R ³ , R ⁶ , R ⁷ , R ¹⁰ , In the case of R ¹¹ , R ¹⁴ and R ¹⁵ , at least one hydrogen in the structure may be bonded to any one of R ¹ to R ¹⁶ in formula (5) to form a single bond.

The light-emitting layer materials (host material and dopant material) can also be used as the following polymer compounds or polymer crosslinked bodies thereof, or the following suspended polymer compounds or suspended polymer crosslinked bodies thereof A material for a light-emitting layer, wherein the polymer compound is a monomer obtained by polymerizing a reactive compound having a reactive substituent in the material for a light-emitting layer (host material and dopant material) as a monomer. The suspension type polymer compound is obtained by reacting a main chain type polymer with the reactive compound. As a reactive substituent in this case, the description in the polycyclic aromatic compound represented by Formula (1) can be cited.
Details of applications of such a polymer compound and a polymer crosslinked body will be described later.

<An example of a polymer host material>
[Chemical 93]

In the formula (SPH-1),
MU is independently a divalent aromatic compound, EC is independently a monovalent aromatic compound, two hydrogens in MU are substituted with EC or MU, and k is an integer of 2 to 50000.

More specifically,
MU is independently an aryl group, a hetero aryl group, a bis aryl arylamino group, a bis aryl aryl boryl group, an oxaborane-diyl group, an azaborane-diyl group,
EC is independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino or aryloxy,
At least one hydrogen in MU and EC may be further substituted by aryl, heteroaryl, diarylamino, alkyl and cycloalkyl,
k is an integer from 2 to 50000.
k is preferably an integer of 20 to 50,000, and more preferably an integer of 100 to 50,000.

At least one hydrogen in MU and EC in the formula (SPH-1) may be substituted by an alkyl group having 1 to 24 carbon atoms, a cycloalkyl group having 3 to 24 carbon atoms, halogen, or deuterium. -CH ₂ -may be substituted by -O- or -Si (CH ₃ ) _2- , and any of the alkyl groups except -CH ₂ -which is directly bonded to EC in formula (SPH-1)- CH ₂ -may be substituted by an arylene group having 6 to 24 carbon atoms, and any hydrogen in the alkyl group may be substituted by fluorine.

Examples of the MU include a divalent group represented by removing any two hydrogen atoms from any of the following compounds.
[Chemical 94]

More specifically, a divalent group represented by any one of the following structures may be mentioned. Among these, the MU is bonded to other MU or EC at *.

[Chem 95]

[Chem 96]


[Chem 97]

[Chemical 98]

[Chemical 99]

[Chemical 100]

[Chemical 101]


[Chemical 102]

[Chemical 103]

Examples of the EC include a monovalent group represented by any of the following structures. Among these, EC is bonded to MU at *.

[Chemical 104]

[Chem. 105]

From the viewpoint of solubility and film-forming properties, the compound represented by the formula (SPH-1) is preferably 10% to 100% of the total number of MUs (k) in the molecule. MU has a carbon number of 1 to 24. Alkyl is more preferably 30% to 100% of the total number of MUs (k) in the molecule. The MU has an alkyl group having 1 to 18 carbon atoms (a branched alkyl group having 3 to 18 carbon atoms), and further preferably an intramolecular group. 50% to 100% of the total MUs (k) have an alkyl group having 1 to 12 carbons (a branched alkyl group having 3 to 12 carbons). On the other hand, from the viewpoint of in-plane alignment and charge transport, it is preferred that 10% to 100% of the total number of MUs (k) in the molecule have MUs having 7 to 24 carbon groups, and more preferably a molecule. 30% to 100% of the total MUs (k) in the MU have an alkyl group having 7 to 24 carbon atoms (a branched alkyl group having 7 to 24 carbon atoms).

Details of applications of such a polymer compound and a polymer crosslinked body will be described later.

<Electron injection layer and electron transport layer in organic electroluminescence element>
The electron injection layer 107 plays a role of efficiently injecting electrons migrated from the cathode 108 into the light emitting layer 105 or the electron transport layer 106. The electron transport layer 106 functions to efficiently transfer electrons injected from the cathode 108 or electrons injected from the cathode 108 through 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 and mixing one or two or more kinds of electron transport / injection materials, or are formed of a mixture of an electron transport / injection material and a polymer binder.

The electron injection / transport layer is a layer that injects electrons from the cathode and then transports the electrons. It is desirable that the electron injection efficiency is high and that the injected electrons are efficiently transmitted. Therefore, a substance having a large electron affinity, a large electron mobility, and further excellent stability, and is less likely to generate impurities that become traps during manufacture and use. However, in consideration of the hole and electron transport balance, when the main function is to effectively prevent holes from the anode from flowing to the cathode side without recombination, even if the electron transport capability is not so high, It also has the effect of improving the luminous efficiency as well as a material with a high electron transport capacity. Therefore, the electron injection / transport layer in this embodiment may include a function of a layer capable of efficiently preventing hole migration.

As a material (electron transport material) for forming the electron transport layer 106 or the electron injection layer 107, it can be a conventional compound used as an electron transport compound in a photoconductive material, an electron injection layer and an electron transport layer for an organic EL device. Any of the well-known compounds can be arbitrarily selected and used.

As a material used in the electron transport layer or the electron injection layer, it is preferable to contain at least one selected from the group consisting of an aromatic substance containing one or more kinds of atoms selected from carbon, hydrogen, oxygen, sulfur, silicon, and phosphorus. A compound of a family ring or a heteroaromatic ring, a pyrrole derivative and a condensed ring derivative thereof, and a metal complex having an electron-accepting nitrogen. Specific examples include condensed-ring aromatic ring derivatives such as naphthalene and anthracene; styryl-based aromatic ring derivatives represented by 4,4'-bis (diphenylvinyl) biphenyl; purple Cyclic ketone derivatives, coumarin derivatives, naphthalene dimethyl imine derivatives, quinone derivatives such as anthraquinone or biphenylquinone, phosphorus oxide derivatives, carbazole derivatives and indole derivatives, etc. Examples of the metal complex having an electron-accepting nitrogen include hydroxyazole complexes such as hydroxyphenyloxazole complexes, methylimine complexes, cycloheptatrienone metal complexes, and flavones. Alcohol metal complexes and benzoquinoline metal complexes. These materials can be used alone or mixed with different materials.

Specific examples of the other electron-transporting compound include a pyridine derivative, a naphthalene derivative, an anthracene derivative, a phenanthrene derivative, a ringtone derivative, a coumarin derivative, and a naphthalene dimethylimine derivative. Compounds, anthraquinone derivatives, biphenylquinone derivatives, diphenylquinone derivatives, fluorene derivatives, oxadiazole derivatives (1,3-bis [(4-thirdbutylphenyl) 1,3, 4-oxadiazolyl] phenylene, etc.), thiophene derivatives, triazole derivatives (N-naphthyl-2,5-diphenyl-1,3,4-triazole, etc.), thiadiazole derivatives Compounds, metal complexes of 8-hydroxyquinoline (oxine) derivatives, hydroxyquinoline metal complexes, quinoxaline derivatives, polymers of quinoxaline derivatives, benzazole compounds, Gallium complex, pyrazole derivative, perfluorinated phenylene derivative, triazine derivative, pyrazine derivative, benzoquinoline derivative (2,2'-bis (benzo [h] quinoline -2-yl) -9,9'-spirobifluorene, etc.), imidazopyridine derivatives, borane derivatives, benzimidazole derivatives (tris (N-phenylbenzimidazol-2-yl) benzene, etc. ), Benzoxazole derivatives, benzothiazole derivatives, quinoline derivatives Compounds, oligopyridine derivatives such as terpyridine, bipyridine derivatives, terpyridine derivatives (1,3-bis (4 '-(2,2': 6'2 ''-terpyridyl)) 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.

In addition, metal complexes having electron-accepting nitrogen can also be used, and examples thereof include hydroxyazole complexes such as hydroxyquinoline-based metal complexes and hydroxyphenyloxazole complexes, and methylimine complexes. , Cycloheptatrienol ketone metal complex, flavonol metal complex, and benzoquinoline metal complex.

The materials can be used alone or mixed with different materials.

Among the materials, a borane derivative, a pyridine derivative, a fluoranthene derivative, a BO-based derivative, an anthracene derivative, a benzofluorene derivative, a phosphine oxide derivative, a pyrimidine derivative, and a carbazole derivative are preferable. , Triazine derivatives, benzimidazole derivatives, phenanthroline derivatives, and hydroxyquinoline-based 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 Japanese Patent Laid-Open No. 2007-27587.
[Chem. 106]

In the formula (ETM-1), R ¹¹ and R ¹² are each independently hydrogen, alkyl, cycloalkyl, substituted aryl, substituted silane, substituted nitrogen-containing heterocyclic ring, or At least one of cyano groups, R ¹³ to R ¹⁶ are each independently a substituted alkyl group, a substituted cycloalkyl group, or a substituted aryl group, X is a substituted arylene group, and Y is An aryl group having 16 or less carbon atoms that may be substituted, a substituted boron group, or a carbazolyl group that may be substituted, and n are each independently an integer of 0 to 3. Moreover, examples of the substituent in the case of "substitutable" or "substituted" include an aryl group, a heteroaryl group, an alkyl group, and a cycloalkyl group.

Among the compounds represented by the general formula (ETM-1), a compound represented by the following general formula (ETM-1-1) or a compound represented by the following general formula (ETM-1-2) is preferred.
[Chemical 107]

In the formula (ETM-1-1), R ¹¹ and R ¹² are each independently hydrogen, alkyl, cycloalkyl, substituted aryl, substituted silyl, substituted nitrogen-containing heterocyclic ring, or At least one of the cyano groups, R ¹³ to R ¹⁶ are each independently a substituted alkyl group, a substituted cycloalkyl group, or a substituted aryl group, and R ²¹ and R ²² are each independently hydrogen, At least one of an alkyl group, a cycloalkyl group, a substituted aryl group, a substituted silane group, a substituted nitrogen-containing heterocyclic ring, or a cyano group, X ¹ is an extension of 20 or less carbon atoms For aryl, n is an integer of 0 to 3, and m is an integer of 0 to 4, respectively. Moreover, examples of the substituent in the case of "substitutable" or "substituted" include an aryl group, a heteroaryl group, an alkyl group, and a cycloalkyl group.
[Chemical 108]

In the formula (ETM-1-2), R ¹¹ and R ¹² are each independently hydrogen, alkyl, cycloalkyl, substituted aryl, substituted silyl, substituted nitrogen-containing heterocyclic ring, or At least one of the cyano groups, R ¹³ to R ¹⁶ are each independently a substituted alkyl group, a substituted cycloalkyl group or a substituted aryl group, and X ¹ is a substituted carbon number of 20 or less. An arylene group and n are each independently an integer of 0 to 3. Moreover, examples of the substituent in the case of "substitutable" or "substituted" include an aryl group, a heteroaryl group, an alkyl group, and a cycloalkyl group.

Specific examples of X ¹ include a divalent group represented by any one of the following formulae (X-1) to (X-9).
[Chem. 109]

(In each formula, R ^{a is} independently an alkyl group, a cycloalkyl group, or a phenyl group which may be substituted)

Specific examples of the borane derivative include the following compounds.
[Chemical 110]

This borane derivative can be produced using a known raw material and a known synthesis method.

<Pyridine derivatives>
The pyridine derivative is, for example, a compound represented by the following formula (ETM-2), and is preferably a compound represented by the formula (ETM-2-1) or the formula (ETM-2-2).
[Chemical 111]

ϕ is n-valent aryl ring (preferably n-valent benzene ring, naphthalene ring, anthracene ring, fluorene ring, benzofluorene ring, fluorene ring, phenanthrene ring or triphenylene ring), and n is 1 to 4 Integer.

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

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

In each formula, the "pyridine-based substituent" is any one of the following formulae (Py-1) to (Py-15), and the pyridine-based substituents may be each independently an alkyl group having 1 to 4 carbon atoms or A cycloalkyl group having 5 to 10 carbon atoms is substituted. The pyridine-based substituent may be bonded to the fluorene, anthracene ring, or fluorene ring in each formula via a phenylene group or a naphthyl group.

[Chemical 112]

The pyridine-based substituent is any one of the formulae (Py-1) to (Py-15), and any of these is preferably any one of the following formulae (Py-21) to (Py-44) .
[Chem 113]

At least one hydrogen in each pyridine derivative may be substituted by deuterium, and one of the two "pyridine-based substituents" in the formula (ETM-2-1) and (ETM-2-2) may be substituted by aromatic Radical substitution.

The "alkyl group" in R ¹¹ to R ¹⁸ may be any of a linear chain and a branched chain, and examples thereof include a linear alkyl group having 1 to 24 carbon atoms or a branched alkyl group having 3 to 24 carbon atoms. A preferred "alkyl group" is an alkyl group having 1 to 18 carbons (a branched alkyl group having 3 to 18 carbons). A more preferable "alkyl group" is an alkyl group having 1 to 12 carbons (a branched alkyl group having 3 to 12 carbons). Further preferred "alkyl" is an alkyl group having 1 to 6 carbons (a branched alkyl group having 3 to 6 carbons). Particularly preferred "alkyl" is an alkyl group having 1 to 4 carbons (a branched alkyl group having 3 to 4 carbons).

Specific "alkyl" includes methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, second butyl, third butyl, n-pentyl, and isopentyl , Neopentyl, third pentyl, n-hexyl, 1-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, n-heptyl , 1-methylhexyl, n-octyl, third 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, normal fourteen, normal fifteen, normal sixteen, normal seventeen, normal eighteen, normal twenty, etc.

As the alkyl group having 1 to 4 carbon atoms substituted in the pyridine-based substituent, the description of the alkyl group can be cited.

Examples of the "cycloalkyl group" in R ¹¹ to R ¹⁸ include a cycloalkyl group having 3 to 12 carbon atoms. A preferred "cycloalkyl group" is a cycloalkyl group having 3 to 10 carbon atoms. A more preferable "cycloalkyl group" is a cycloalkyl group having 3 to 8 carbon atoms. A further preferred "cycloalkyl group" is a cycloalkyl group having 3 to 6 carbon atoms.
Specific "cycloalkyl" includes cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, methylcyclopentyl, cycloheptyl, methylcyclohexyl, cyclooctyl, or dimethyl ring. Jiji et al.

As the "aryl group" in R ¹¹ to R ¹⁸ , a preferable aryl group is an aryl group having 6 to 30 carbon atoms, a more preferable aryl group is an aryl group having 6 to 18 carbon atoms, and further preferably 6 to 18 carbon atoms. The aryl group of 14 is particularly preferably an aryl group having 6 to 12 carbon atoms.

Specific examples of the "aryl group having 6 to 30 carbon atoms" include a phenyl group which is a monocyclic aryl group, a (1-, 2-) naphthyl group which is a condensed bicyclic system aryl group, and a condensed tricyclic system. Aryl- (1-, 3-, 4-, 5-) group, fluorene- (1-, 2-, 3-, 4-, 9-) group, fluorene- (1-, 2-) group , (1-, 2-, 3-, 4-, 9-) phenanthrene, triphenylene- (1-, 2-) group as condensed tetracyclic aryl group, fluorene- (1-, 2-, 4-) group, fused tetraphenyl- (1-, 2-, 5-) group, fluorene- (1-, 2-, 3-) group as condensed pentacyclic aryl group, fused pentaphenyl- (1- , 2-, 5-, 6-) groups and the like.

Preferable "aryl groups having 6 to 30 carbon atoms" include phenyl, naphthyl, phenanthryl, fluorenyl, and triphenylene, and more preferably phenyl, 1-naphthyl, and 2-naphthyl Or phenanthryl, particularly preferably phenyl, 1-naphthyl or 2-naphthyl.

R ¹¹ and R ^{12 in} the formula (ETM-2-2) may be bonded to form a ring. As a result, cyclobutane, cyclopentane, and cyclopentane may be bonded to the 5-membered ring of the fluorene skeleton. Ene, cyclopentadiene, cyclohexane, osmium or indene and the like.

Specific examples of the pyridine derivative include the following compounds.
[Chemical 114]

This pyridine derivative can be manufactured using a well-known raw material and a well-known synthetic method.

<Fluoranthene derivative>
The fluoranthene derivative is, for example, a compound represented by the following general formula (ETM-3), and is disclosed in detail in International Publication No. 2010/134352.
[Chem 115]

In the formula (ETM-3), X ¹² to X ²¹ represent hydrogen, halogen, straight chain, branched or cyclic alkyl group, straight chain, branched or cyclic alkoxy group, substituted or unsubstituted Aryl, or substituted or unsubstituted heteroaryl. Here, examples of the substituent in the case of substitution include an aryl group, a heteroaryl group, an alkyl group, and a cycloalkyl group.

Specific examples of the fluoranthene derivative include the following compounds.
[Chem 116]

<BO-based derivatives>
The BO-based 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).
[Chem. 117]

R ¹ to R ¹¹ are each independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, alkyl, cycloalkyl, alkoxy, or Aryloxy, at least one of these hydrogens may be substituted by aryl, heteroaryl, alkyl, or cycloalkyl.

In addition, adjacent groups in R ¹ to R ¹¹ may be bonded to each other and form an aryl ring or a heteroaryl ring with the a ring, the b ring, or the c ring, and at least one hydrogen in the formed ring may be an aryl group , Heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, alkyl, cycloalkyl, alkoxy or aryloxy, at least one of these hydrogens may be substituted by Aryl, heteroaryl, alkyl or cycloalkyl substitution.

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

The description of the form of a substituent or a ring in Formula (ETM-4) can refer to the description of the polycyclic aromatic compound represented by the said General formula (1).

Specific examples of the BO-based derivative include the following compounds.
[Chemical 118]

This BO-based derivative can be produced using a known raw material and a known synthesis method.

<Anthracene derivative>
One of the anthracene derivatives is, for example, a compound represented by the following formula (ETM-5-1).
[Chemical 119]

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

Ar can be appropriately selected independently from divalent benzene or naphthalene, and two Ars can be different or the same. From the viewpoint of ease of synthesis of anthracene derivatives, Ar is preferably the same. Ar is bonded to pyridine to form a "site containing Ar and pyridine", and this site is bonded to anthracene as a group represented by any one of the following formulae (Py-1) to (Py-12), for example.

[Chem 120]

Among these groups, a group represented by any of the formulae (Py-1) to (Py-9) is preferable, and the groups (Py-1) to (Py-) 6) The group represented by any one. The structures of two "sites containing Ar and pyridine" bonded to anthracene may be the same or different, and from the viewpoint of ease of synthesis of anthracene derivatives, the same structure is preferred. Among them, from the viewpoint of element characteristics, it is preferable that the structures of the two "parts including Ar and pyridine" are the same or different.

The alkyl group having 1 to 6 carbons in R ¹ to R ⁴ may be either a straight chain or a branched chain. That is, it is a linear alkyl group having 1 to 6 carbon atoms or a branched alkyl group having 3 to 6 carbon atoms. More preferred is an alkyl group having 1 to 4 carbons (a branched alkyl group having 3 to 4 carbons). Specific examples include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, second butyl, third butyl, n-pentyl, isopentyl, neopentyl, Third pentyl, n-hexyl, 1-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl or 2-ethylbutyl, etc., preferably methyl, ethyl Methyl, n-propyl, isopropyl, n-butyl, isobutyl, second butyl or third butyl, more preferably methyl, ethyl or third butyl.

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

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

Specific examples of the "aryl group having 6 to 20 carbon atoms" include a phenyl group which is a monocyclic aryl group, (o-, m-, p-) tolyl group, (2,3-, 2,4-, 2) , 5-, 2,6-, 3,4-, 3,5-) Xylyl, mesityl (2,4,6-trimethylphenyl), (o-, m-, p-) cumene Group, (2-, 3-, 4-) biphenyl group as a bicyclic aryl group, (1-, 2-) naphthyl group as a condensed bicyclic aryl group, and bitriphenyl group as a tricyclic aryl group Phenyl (m-terphenyltriphenyl-2'-yl, m-phenyltriphenyl-4'-yl, m-phenyltriphenyl-5'-yl, o-phenyltriphenyl-3'-yl, o-phenyltriphenyl-4'-yl -Yl, p-terphenyl-2'-yl, m-phenyltriphenyl-2-yl, m-phenyltriphenyl-3-yl, m-phenyltriphenyl-4-yl, o-phenyltriphenyl-2-yl, o-phenyl Triphenyl-3-yl, o-triphenyl-4-yl, p-triphenyl-2-yl, p-triphenyl-3-yl, p-triphenyl-4-yl), anthracene as condensed tricyclic aryl group -(1-, 2-, 9-) group, fluorene- (1-, 3-, 4-, 5-) group, fluorene- (1-, 2-, 3-, 4-, 9-) group, Fluorene- (1-, 2-) group, (1-, 2-, 3-, 4-, 9-) phenanthrene group, triphenylene- (1-, 2-) group as condensed tetracyclic aryl group , Fluorene- (1-, 2-, 4-) group, fused tetraphenyl- (1-, 2-, 5-) group, as condensation Aryl perylene ring system - (1-, 2-, 3-) group.

The preferred "aryl group having 6 to 20 carbon atoms" is phenyl, biphenyl, bitriphenyl or naphthyl, more preferably phenyl, biphenyl, 1-naphthyl, 2-naphthyl or m-naphthyl. Bitriphenyl-5'-yl, further preferably phenyl, biphenyl, 1-naphthyl or 2-naphthyl, and most preferably phenyl.

One of the anthracene derivatives is, for example, a compound represented by the following formula (ETM-5-2).
[Chemical 121]

Ar ^{1 is} each independently a single bond, divalent benzene, naphthalene, anthracene, fluorene, or fluorene.

Ar ^{2 is} each independently an aryl group having 6 to 20 carbon atoms, and the same explanation as the “aryl group having 6 to 20 carbon atoms” in the formula (ETM-5-1) can be cited. An aryl group having 6 to 16 carbon atoms is preferred, an aryl group having 6 to 12 carbon atoms is more preferred, and an aryl group having 6 to 10 carbon atoms is particularly preferred. Specific examples include phenyl, biphenyl, naphthyl, bitriphenyl, anthracenyl, fluorenyl, fluorenyl, fluorenyl, phenanthryl, triphenylene, fluorenyl, and condensed tetraphenyl ( tetracenyl), fluorenyl and the like.

R ¹ to R ⁴ are each independently hydrogen, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms or an aryl group having 6 to 20 carbon atoms, and the formula (ETM-5-1 ).

Specific examples of the anthracene derivatives include the following compounds.
[Chem 122]

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

<Benzofluorene Derivatives>
The benzofluorene derivative is, for example, a compound represented by the following formula (ETM-6).
[化 123]

Ar ^{1 is} each independently an aryl group having 6 to 20 carbon atoms, and the same explanation as the "aryl group having 6 to 20 carbon atoms" in the formula (ETM-5-1) can be cited. An aryl group having 6 to 16 carbon atoms is preferred, an aryl group having 6 to 12 carbon atoms is more preferred, and an aryl group having 6 to 10 carbon atoms is particularly preferred. Specific examples include phenyl, biphenyl, naphthyl, bitriphenyl, anthracenyl, fluorenyl, fluorenyl, fluorenyl, phenanthryl, triphenylene, fluorenyl, and condensed tetraphenyl ( tetracenyl), fluorenyl and the like.

Ar ^{2 is} independently hydrogen, alkyl (preferably alkyl having 1 to 24 carbon atoms), cycloalkyl (preferably cycloalkyl having 3 to 12 carbon atoms), or aryl (preferably carbon number) 6-30 aryl groups), two Ar ² may be bonded to form a ring.

The "alkyl group" in Ar ² may be any of a linear chain and a branched chain, and examples thereof include a linear alkyl group having 1 to 24 carbon atoms or a branched chain alkyl group having 3 to 24 carbon atoms. A preferred "alkyl group" is an alkyl group having 1 to 18 carbons (a branched alkyl group having 3 to 18 carbons). A more preferable "alkyl group" is an alkyl group having 1 to 12 carbons (a branched alkyl group having 3 to 12 carbons). Further preferred "alkyl" is an alkyl group having 1 to 6 carbons (a branched alkyl group having 3 to 6 carbons). Particularly preferred "alkyl" is an alkyl group having 1 to 4 carbons (a branched alkyl group having 3 to 4 carbons). Specific "alkyl" includes methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, second butyl, third butyl, n-pentyl, and isopentyl , Neopentyl, third pentyl, n-hexyl, 1-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, n-heptyl , 1-methylhexyl and the like.

Examples of the "cycloalkyl group" in Ar ² include a cycloalkyl group having 3 to 12 carbon atoms. A preferred "cycloalkyl group" is a cycloalkyl group having 3 to 10 carbon atoms. A more preferable "cycloalkyl group" is a cycloalkyl group having 3 to 8 carbon atoms. A further preferred "cycloalkyl group" is a cycloalkyl group having 3 to 6 carbon atoms. Specific "cycloalkyl" includes cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, methylcyclopentyl, cycloheptyl, methylcyclohexyl, cyclooctyl, or dimethyl ring. Jiji et al.

As the "aryl group" in Ar ² , a preferable aryl group is an aryl group having 6 to 30 carbon atoms, a more preferable aryl group is an aryl group having 6 to 18 carbon atoms, and further preferably an aryl group having 6 to 14 carbon atoms. A particularly preferred group is an aryl group having 6 to 12 carbon atoms.

Specific "aryl groups having 6 to 30 carbon atoms" include phenyl, naphthyl, fluorenyl, fluorenyl, fluorenyl, phenanthryl, triphenylene, fluorenyl, fused tetraphenyl, and fluorenyl , Thick pentaphenyl and so on.

Two Ar ² may be bonded to form a ring. As a result, cyclobutane, cyclopentane, cyclopentene, cyclopentadiene, cyclohexane, fluorene, or Indene et al.

Specific examples of the benzofluorene derivative include the following compounds.
[Chem 124]

This benzofluorene derivative can be manufactured using a well-known raw material and a well-known synthetic method.

<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.
[Chemical 125]

R ⁵ is substituted or unsubstituted alkyl having 1 to 20 carbons, cycloalkyl having 3 to 16 carbons, aryl having 6 to 20 carbons or heteroaryl having 5 to 20 carbons,
R ⁶ is CN, substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, cycloalkyl group having 3 to 16 carbon atoms, heteroalkyl group having 1 to 20 carbon atoms, and aryl group having 6 to 20 carbon atoms , Heteroaryl having 5 to 20 carbons, alkoxy having 1 to 20 carbons or aryloxy having 6 to 20 carbons,
R ⁷ and R ⁸ are each independently a substituted or unsubstituted aryl group having 6 to 20 carbon atoms or a heteroaryl group having 5 to 20 carbon atoms,
R ⁹ is oxygen or sulfur,
j is 0 or 1, k is 0 or 1, r is an integer of 0 to 4, and q is an integer of 1 to 3.
Here, examples of the substituent in the case of substitution include an aryl group, a heteroaryl group, an alkyl group, and a cycloalkyl group.

The phosphine oxide derivative may be, for example, a compound represented by the following formula (ETM-7-2).
[Chem. 126]

R ¹ to R ³ may be the same or different and are selected from hydrogen, alkyl, cycloalkyl, aralkyl, alkenyl, cycloalkenyl, alkynyl, alkoxy, alkylthio, and cycloalkylthio , Aryl ether, aryl thio ether, aryl, heterocyclic, halogen, cyano, aldehyde, carbonyl, carboxyl, amine, nitro, silyl and adjacent substituents in.

Ar ¹ may be the same or different, and is an arylene or a heteroaryl. Ar ² may be the same or different, and is aryl or heteroaryl. Among them, 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 of 0 to 3; when n is 0, there is no unsaturated structure; when n is 3, R ¹ does not exist.

Among these substituents, the alkyl group means, for example, a saturated aliphatic hydrocarbon group such as methyl, ethyl, propyl, or butyl, which may be unsubstituted or substituted. The substituent in the case of substitution is not particularly limited, and examples thereof include an alkyl group, an aryl group, and a heterocyclic group. This aspect is also common to the following description. The number of carbon atoms of the alkyl group is not particularly limited, and is usually in the range of 1 to 20 in terms of availability and cost.

The "cycloalkyl group" means, 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 portion is not particularly limited, but is usually in the range of 3 to 20.

The aralkyl group means, for example, an aromatic hydrocarbon group such as a benzyl group or a phenylethyl group via an aliphatic hydrocarbon. Both the aliphatic hydrocarbon and the aromatic hydrocarbon may be unsubstituted or substituted. The number of carbons in the aliphatic portion is not particularly limited, but is usually in the range of 1 to 20.

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

The term "cycloalkenyl" refers to, for example, an unsaturated alicyclic hydrocarbon group containing a double bond, such as a cyclopentenyl group, a cyclopentadienyl group, or a cyclohexenyl group, which may be unsubstituted or substituted.

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

The alkoxy group means, 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 of the alkoxy group is not particularly limited, but is usually in the range of 1 to 20.

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

The cycloalkylthio group is a group in which an oxygen atom of an ether bond of a cycloalkoxy group is substituted with a sulfur atom.

The aryl ether group means, for example, 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 of the aryl ether group is not particularly limited, but is usually in the range of 6 to 40.

The arylthioether group is a group in which an oxygen atom of an ether bond of an arylether group is substituted with a sulfur atom.

The aryl group means, for example, an aromatic hydrocarbon group such as a phenyl group, a naphthyl group, a biphenyl group, a phenanthryl group, a bitriphenyl group, or a fluorenyl group. Aryl may be unsubstituted or substituted. The number of carbon atoms of the aryl group is not particularly limited, but is usually in the range of 6 to 40.

The heterocyclic group means, for example, a cyclic structure group having an atom other than carbon, such as a furyl group, a thienyl group, an oxazolyl group, a pyridyl group, a quinolyl group, and a carbazolyl group. . The number of carbon atoms of the heterocyclic group is not particularly limited, but is usually in the range of 2 to 30.

The halogen means fluorine, chlorine, bromine and iodine.

The aldehyde group, carbonyl group, and amine group may include a group substituted with an aliphatic hydrocarbon, an alicyclic hydrocarbon, an aromatic hydrocarbon, a heterocyclic ring, or the like.

In addition, aliphatic hydrocarbons, alicyclic hydrocarbons, aromatic hydrocarbons, and heterocyclic rings may be unsubstituted or substituted.

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

The condensed ring formed between the adjacent substituents is, for example, Ar ¹ and R ² , Ar ¹ and R ³ , Ar ² and R ² , Ar ² and R ³ , R ² and R ³ , and Ar ¹ and A conjugated or non-conjugated condensed ring formed between Ar ² and the like. Here, when n is 1, two R ¹ may form a conjugated or non-conjugated condensed ring with each other. These condensed rings may include nitrogen, oxygen, and sulfur atoms in the ring structure, and may also be condensed with other rings.

Specific examples of the phosphine oxide derivative include the following compounds.
[Chemical 127]

This phosphine oxide derivative can be manufactured using a well-known raw material and a well-known synthetic method.

<Pyrimidine derivatives>
The pyrimidine derivative is, for example, a compound represented by the following formula (ETM-8), and is preferably a compound represented by the following formula (ETM-8-1). Details are also described in International Publication No. 2011/021689.
[Chem 128]

Ar is each independently a substituted aryl group or a substituted heteroaryl group. n is an integer of 1 to 4, preferably an integer of 1 to 3, and more preferably 2 or 3.

Examples of the "aryl group" as the "substitutable aryl group" include an aryl group having 6 to 30 carbon atoms, preferably an aryl group having 6 to 24 carbon atoms, and more preferably an aryl group having 6 to 20 carbon atoms. And further preferably an aryl group having 6 to 12 carbon atoms.

Specific examples of the "aryl group" include a phenyl group which is a monocyclic aryl group, a (2-, 3-, 4-) biphenyl group which is a bicyclic aryl group, and a condensed bicyclic aryl group. (1-, 2-) naphthyl, bitriphenyl (tris (triphenyl-2'-yl), tris (triphenyl-4'-yl), tris (triphenyl-5'-)) Phenyl, o-terphenyltriphenyl-3'-yl, o-terphenyltriphenyl-4'-yl, p-terphenyltriphenyl-2'-yl, m-phenyltriphenyl-2-yl, m-phenyltriphenyl-3-yl, m-phenylene Triphenyl-4-yl, o-triphenyl-2-yl, o-triphenyl-3-yl, o-triphenyl-4-yl, p-triphenyl-2-yl, p-triphenyl-3-yl , P-triphenyl-4-yl), fluorene- (1-, 3-, 4-, 5-) group as condensed tricyclic aryl group, fluorene- (1-, 2-, 3-, 4-, 9-) group, fluorene- (1-, 2-) group, (1-, 2-, 3-, 4-, 9-) phenanthryl group, bi-tetraphenyl group (5'- Phenyl-m-terphenyl-2-yl, 5'-phenyl-m-terphenyl-3-yl, 5'-phenyl-m-terphenyl-4-yl, m-tetraphenyl), as Condensed triphenylene- (1-, 2-) group, fluorene- (1-, 2-, 4-) group, condensed tetraphenyl- (1-, 2-, 5-) group, Fluorene- (1-, 2-, 3-) group as condensed pentacyclic aryl group, thick Pentaphenyl- (1-, 2-, 5-, 6-) and the like.

Examples of the "heteroaryl group" as the "substitutable heteroaryl group" include a heteroaryl group having 2 to 30 carbon atoms, a heteroaryl group having 2 to 25 carbon atoms is preferable, and a 2 to carbon number is more preferable. The heteroaryl group of 20 is more preferably a heteroaryl group having 2 to 15 carbon atoms, and particularly preferably a heteroaryl group having 2 to 10 carbon atoms. Examples of the heteroaryl group include a heterocyclic ring containing one to five heteroatoms selected from oxygen, sulfur, and nitrogen as ring constituent atoms in addition to carbon.

Specific examples of the heteroaryl group include furyl, thienyl, pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, pyrazolyl, oxadiazolyl, furfuryl , Thiadiazolyl, triazolyl, tetrazolyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, benzofuranyl, isobenzofuranyl, benzo [b] thiophene , Indolyl, isoindolyl, 1H-indazolyl, benzimidazolyl, benzoxazolyl, benzothiazolyl, 1H-benzotriazolyl, quinolinyl, isoquinolinyl, Fluorinyl, quinazolinyl, quinoxaline, phthalazinyl, naphthyridine, purinyl, pyridinyl, carbazolyl, acridinyl, phenoxazinyl, phenothiazinyl, morphazinyl , Phenoxathial, thiathranyl, indazinyl and the like.

The aryl group and the heteroaryl group may be substituted, and may be substituted, for example, by the aryl group or the heteroaryl group.

Specific examples of the pyrimidine derivative include the following compounds.
[Chem. 129]

This pyrimidine derivative can be manufactured using a well-known raw material and a well-known synthetic method.

<Carbazole derivative>
The carbazole derivative is, for example, a compound represented by the following formula (ETM-9) or a multimer in which a plurality of them are bonded by a single bond or the like. Details are described in US Publication No. 2014/0197386.
[Chem 130]

Ar is each independently a substituted aryl group or a substituted heteroaryl group. n is an integer of 0 to 4, preferably an integer of 0 to 3, and more preferably 0 or 1.

Examples of the "aryl group" as the "substitutable aryl group" include an aryl group having 6 to 30 carbon atoms, preferably an aryl group having 6 to 24 carbon atoms, and more preferably an aryl group having 6 to 20 carbon atoms. And further preferably an aryl group having 6 to 12 carbon atoms.

Specific examples of the "aryl group" include a phenyl group which is a monocyclic aryl group, a (2-, 3-, 4-) biphenyl group which is a bicyclic aryl group, and a condensed bicyclic aryl group. (1-, 2-) naphthyl, bitriphenyl (tris (triphenyl-2'-yl), tris (triphenyl-4'-yl), tris (triphenyl-5'-)) Phenyl, o-terphenyltriphenyl-3'-yl, o-terphenyltriphenyl-4'-yl, p-terphenyltriphenyl-2'-yl, m-phenyltriphenyl-2-yl, m-phenyltriphenyl-3-yl, m-phenylene Triphenyl-4-yl, o-triphenyl-2-yl, o-triphenyl-3-yl, o-triphenyl-4-yl, p-triphenyl-2-yl, p-triphenyl-3-yl , P-triphenyl-4-yl), fluorene- (1-, 3-, 4-, 5-) group as condensed tricyclic aryl group, fluorene- (1-, 2-, 3-, 4-, 9-) group, fluorene- (1-, 2-) group, (1-, 2-, 3-, 4-, 9-) phenanthryl group, bi-tetraphenyl group (5'- Phenyl-m-terphenyl-2-yl, 5'-phenyl-m-terphenyl-3-yl, 5'-phenyl-m-terphenyl-4-yl, m-tetraphenyl), as Condensed triphenylene- (1-, 2-) group, fluorene- (1-, 2-, 4-) group, condensed tetraphenyl- (1-, 2-, 5-) group, Fluorene- (1-, 2-, 3-) group as condensed pentacyclic aryl group, thick Pentaphenyl- (1-, 2-, 5-, 6-) and the like.

Examples of the "heteroaryl group" as the "substitutable heteroaryl group" include a heteroaryl group having 2 to 30 carbon atoms, a heteroaryl group having 2 to 25 carbon atoms is preferable, and a 2 to carbon number is more preferable. The heteroaryl group of 20 is more preferably a heteroaryl group having 2 to 15 carbon atoms, and particularly preferably a heteroaryl group having 2 to 10 carbon atoms. Examples of the heteroaryl group include a heterocyclic ring containing one to five heteroatoms selected from oxygen, sulfur, and nitrogen as ring constituent atoms in addition to carbon.

Specific examples of the heteroaryl group include furyl, thienyl, pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, pyrazolyl, oxadiazolyl, furfuryl , Thiadiazolyl, triazolyl, tetrazolyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, benzofuranyl, isobenzofuranyl, benzo [b] thiophene , Indolyl, isoindolyl, 1H-indazolyl, benzimidazolyl, benzoxazolyl, benzothiazolyl, 1H-benzotriazolyl, quinolinyl, isoquinolinyl, Fluorinyl, quinazolinyl, quinoxaline, phthalazinyl, naphthyridine, purinyl, pyridinyl, carbazolyl, acridinyl, phenoxazinyl, phenothiazinyl, morphazinyl , Phenoxathial, thiathranyl, indazinyl and the like.

The aryl group and the heteroaryl group may be substituted, and may be substituted, for example, by the aryl group or the heteroaryl group.

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

Specific examples of the carbazole derivative include the following compounds.
[Chemical 131]

This carbazole derivative can be manufactured using a well-known raw material and a well-known synthetic method.

＜ Triazine derivatives ＞
The triazine derivative is, for example, a compound represented by the following formula (ETM-10), and preferably a compound represented by the following formula (ETM-10-1). Details are described in US Publication No. 2011/0156013.
[Chem 132]

Ar is each independently a substituted aryl group or a substituted heteroaryl group. n is an integer of 1 to 3, and preferably 2 or 3.

Examples of the "aryl group" as the "substitutable aryl group" include an aryl group having 6 to 30 carbon atoms, preferably an aryl group having 6 to 24 carbon atoms, and more preferably an aryl group having 6 to 20 carbon atoms. And further preferably an aryl group having 6 to 12 carbon atoms.

Specific examples of the "aryl group" include a phenyl group which is a monocyclic aryl group, a (2-, 3-, 4-) biphenyl group which is a bicyclic aryl group, and a condensed bicyclic aryl group. (1-, 2-) naphthyl, bitriphenyl (tris (triphenyl-2'-yl), tris (triphenyl-4'-yl), tris (triphenyl-5'-)) Phenyl, o-terphenyltriphenyl-3'-yl, o-terphenyltriphenyl-4'-yl, p-terphenyltriphenyl-2'-yl, m-phenyltriphenyl-2-yl, m-phenyltriphenyl-3-yl, m-phenylene Triphenyl-4-yl, o-triphenyl-2-yl, o-triphenyl-3-yl, o-triphenyl-4-yl, p-triphenyl-2-yl, p-triphenyl-3-yl , P-triphenyl-4-yl), fluorene- (1-, 3-, 4-, 5-) group as condensed tricyclic aryl group, fluorene- (1-, 2-, 3-, 4-, 9-) group, fluorene- (1-, 2-) group, (1-, 2-, 3-, 4-, 9-) phenanthryl group, bi-tetraphenyl group (5'- Phenyl-m-terphenyl-2-yl, 5'-phenyl-m-terphenyl-3-yl, 5'-phenyl-m-terphenyl-4-yl, m-tetraphenyl), as Condensed triphenylene- (1-, 2-) group, fluorene- (1-, 2-, 4-) group, condensed tetraphenyl- (1-, 2-, 5-) group, Fluorene- (1-, 2-, 3-) group as condensed pentacyclic aryl group, thick Pentaphenyl- (1-, 2-, 5-, 6-) and the like.

Examples of the "heteroaryl group" as the "substitutable heteroaryl group" include a heteroaryl group having 2 to 30 carbon atoms, a heteroaryl group having 2 to 25 carbon atoms is preferable, and a 2 to carbon number is more preferable. The heteroaryl group of 20 is more preferably a heteroaryl group having 2 to 15 carbon atoms, and particularly preferably a heteroaryl group having 2 to 10 carbon atoms. Examples of the heteroaryl group include a heterocyclic ring containing one to five heteroatoms selected from oxygen, sulfur, and nitrogen as ring constituent atoms in addition to carbon.

Specific examples of the heteroaryl group include furyl, thienyl, pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, pyrazolyl, oxadiazolyl, furfuryl , Thiadiazolyl, triazolyl, tetrazolyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, benzofuranyl, isobenzofuranyl, benzo [b] thiophene , Indolyl, isoindolyl, 1H-indazolyl, benzimidazolyl, benzoxazolyl, benzothiazolyl, 1H-benzotriazolyl, quinolinyl, isoquinolinyl, Fluorinyl, quinazolinyl, quinoxaline, phthalazinyl, naphthyridine, purinyl, pyridinyl, carbazolyl, acridinyl, phenoxazinyl, phenothiazinyl, morphazinyl , Phenoxathial, thiathranyl, indazinyl and the like.

The aryl group and the heteroaryl group may be substituted, and may be substituted, for example, by the aryl group or the heteroaryl group.

Specific examples of the triazine derivative include the following compounds.
[Chemical 133]

This triazine derivative can be manufactured using a well-known raw material and a well-known synthetic method.

<Benzimidazole derivatives>
The benzimidazole derivative is, for example, a compound represented by the following formula (ETM-11).
[Chemical 134]

ϕ is n-valent aryl ring (preferably n-valent benzene ring, naphthalene ring, anthracene ring, fluorene ring, benzofluorene ring, fluorene ring, phenanthrene ring or triphenylene ring), and n is 1 to 4 Integer, the "benzimidazole-based substituent" is a pyridyl group substituted for the "pyridine-based substituent" of the formula (ETM-2), (ETM-2-1), and (ETM-2-2) Is a substituent of a benzimidazolyl group, and at least one hydrogen in the benzimidazole derivative may be substituted by deuterium.
[Chem. 135]

R ¹¹ in the benzimidazolyl group is hydrogen, an alkyl group having 1 to 24 carbon atoms, a cycloalkyl group having 3 to 12 carbon atoms or an aryl group having 6 to 30 carbon atoms, and the formula (ETM-2 -1) and R ¹¹ in Formula (ETM-2-2).

ϕ is further preferably an anthracene ring or a fluorene ring, and the structure in this case can be referred to the description in the formula (ETM-2-1) or formula (ETM-2-2), and R ¹¹ to R ^{18 in each} formula may be The description in the formula (ETM-2-1) or the formula (ETM-2-2) is cited. In the formula (ETM-2-1) or the formula (ETM-2-2), two pyridine-based substituents have been described. However, these are substituted with benzimidazole-based substituents. In this case, two pyridine-based substituents (ie, n = 2) may be replaced by benzimidazole-based substituents, or any pyridine-based substituent may be replaced by benzimidazole-based substituents and another pyridine-based substituent may be replaced by R ¹¹ to R ¹⁸ . Substituents (ie n = 1). Furthermore, for example, a benzimidazole-based substituent may be substituted for at least one of R ¹¹ to R ¹⁸ in the formula (ETM-2-1), and a "pyridine-based substituent" may be substituted with R ¹¹ to R ¹⁸ .

Specific examples of the benzimidazole derivative include 1-phenyl-2- (4- (10-phenylanthracene-9-yl) phenyl) -1H-benzo [d] imidazole, 2 -(4- (10- (naphthalen-2-yl) anthracene-9-yl) phenyl) -1-phenyl-1H-benzo [d] imidazole, 2- (3- (10- (naphthalene-2 -Yl) anthracene-9-yl) phenyl) -1-phenyl-1H-benzo [d] imidazole, 5- (10- (naphth-2-yl) anthracene-9-yl) -1,2- Diphenyl-1H-benzo [d] imidazole, 1- (4- (10- (naphthalen-2-yl) anthracene-9-yl) phenyl) -2-phenyl-1H-benzo [d] Imidazole, 2- (4- (9,10-bis (naphthalene-2-yl) anthracen-2-yl) phenyl) -1-phenyl-1H-benzo [d] imidazole, 1- (4- ( 9,10-bis (naphthalene-2-yl) anth-2-yl) phenyl) -2-phenyl-1H-benzo [d] imidazole, 5- (9,10-bis (naphthalene-2-yl) ) Anthracen-2-yl) -1,2-diphenyl-1H-benzo [d] imidazole and the like.
[Chemical 136]

This benzimidazole derivative can be manufactured using a well-known raw material and a well-known synthetic method.

＜ Phenoline derivatives ＞
The morpholine derivative is, for example, a compound represented by the following formula (ETM-12) or (ETM-12-1). Details are described in International Publication No. 2006/021982.
[Chemical 137]

ϕ is n-valent aryl ring (preferably n-valent benzene ring, naphthalene ring, anthracene ring, fluorene ring, benzofluorene ring, fluorene ring, phenanthrene ring or triphenylene ring), and n is 1 to 4 Integer.

Each of R ¹¹ to R ^{18 is} independently hydrogen, an alkyl group (preferably an alkyl group having 1 to 24 carbon atoms), a cycloalkyl group (preferably a cycloalkyl group having 3 to 12 carbon atoms), or an aryl group. (Preferably an aryl group having 6 to 30 carbon atoms). In the formula (ETM-12-1), any one of R ¹¹ to R ¹⁸ is bonded to fluorene, which is an aryl ring.

At least one hydrogen in each morpholine derivative may be substituted by deuterium.

As R ¹¹ ~ R ¹⁸ is alkyl, cycloalkyl, and aryl groups, may be explained by reference (ETM-2) of the formula R ¹¹ ~ R ¹⁸ is. In addition to fluorene, in addition to the above examples, for example, the following structural formulas may be mentioned. In addition, R in the following structural formulas are each independently hydrogen, methyl, ethyl, isopropyl, cyclohexyl, phenyl, 1-naphthyl, 2-naphthyl, biphenyl, or triphenyl. .
[Chemical 138]

Specific examples of the morpholine derivative include, for example, 4,7-diphenyl-1,10-morpholine, 2,9-dimethyl-4,7-diphenyl-1,10-morphine Phthaloline, 9,10-bis (1,10-morpholin-2-yl) anthracene, 2,6-bis (1,10-morpholin-5-yl) pyridine, 1,3,5-tris (1, 10-morpholin-5-yl) benzene, 9,9'-difluoro-bis (1,10-morpholin-5-yl), 2,9-dimethyl-4,7-biphenyl-1, 10-morpholine (bathocuproine), 1,3-bis (2-phenyl-1,10-morpholine-9-yl) benzene or a compound represented by the following structural formula, and the like.
[Chemical 139]

The morpholine derivative can be produced using a known raw material and a known synthesis method.

<Hydroxyquinoline metal complex>
The hydroxyquinoline-based metal complex is, for example, a compound represented by the following general formula (ETM-13).
[Chem 140]

In the formula, R ¹ to R ⁶ are each independently hydrogen, fluorine, alkyl, cycloalkyl, aralkyl, alkenyl, cyano, alkoxy or aryl, and M is Li, Al, Ga, Be or Zn, n is an integer of 1 to 3.

Specific examples of the hydroxyquinoline-based metal complex include lithium 8-hydroxyquinoline, tris (8-hydroxyquinoline) aluminum, tris (4-methyl-8-hydroxyquinoline) aluminum, and tris ( 5-methyl-8-hydroxyquinoline) aluminum, tris (3,4-dimethyl-8-hydroxyquinoline) aluminum, tris (4,5-dimethyl-8-hydroxyquinoline) aluminum, tris (4,6-dimethyl-8-hydroxyquinoline) aluminum, bis (2-methyl-8-hydroxyquinoline) (phenol) aluminum, bis (2-methyl-8-hydroxyquinoline) (2 -Methylphenol) aluminum, bis (2-methyl-8-hydroxyquinoline) (3-methylphenol) aluminum, bis (2-methyl-8-hydroxyquinoline) (4-methylphenol) aluminum , Bis (2-methyl-8-hydroxyquinoline) (2-phenylphenol) aluminum, bis (2-methyl-8-hydroxyquinoline) (3-phenylphenol) aluminum, bis (2-methyl Yl-8-hydroxyquinoline) (4-phenylphenol) aluminum, bis (2-methyl-8-hydroxyquinoline) (2,3-dimethylphenol) aluminum, bis (2-methyl-8 -Hydroxyquinoline) (2,6-dimethylphenol) aluminum, bis (2-methyl-8-hydroxyquinoline) (3,4-dimethylphenol) aluminum, bis (2-methyl-8 -Hydroxyquinoline) (3,5-dimethylphenol) aluminum, bis (2-methyl-8-hydroxyquinoline) (3,5-di-third-butylphenol) aluminum, bis (2-methyl Yl-8-hydroxyquinoline) (2,6-diphenylphenol) aluminum, bis (2-methyl-8-hydroxyquinoline) (2,4,6-triphenylphenol) aluminum, bis (2-methyl-8-hydroxyquinoline) (2,4,6-trimethylphenol) aluminum, bis (2-methyl-8- Hydroxyquinoline) (2,4,5,6-tetramethylphenol) aluminum, bis (2-methyl-8-hydroxyquinoline) (1-naphthol) aluminum, bis (2-methyl-8- Hydroxyquinoline) (2-naphthol) aluminum, bis (2,4-dimethyl-8-hydroxyquinoline) (2-phenylphenol) aluminum, bis (2,4-dimethyl-8-hydroxyl Quinoline) (3-phenylphenol) aluminum, bis (2,4-dimethyl-8-hydroxyquinoline) (4-phenylphenol) aluminum, bis (2,4-dimethyl-8-hydroxyl (Quinoline) (3,5-dimethylphenol) aluminum, bis (2,4-dimethyl-8-hydroxyquinoline) (3,5-di-third-butylphenol) aluminum, bis (2- Methyl-8-hydroxyquinoline) aluminum-μ-oxo-bis (2-methyl-8-hydroxyquinoline) aluminum, bis (2,4-dimethyl-8-hydroxyquinoline) aluminum-μ -Oxo-bis (2,4-dimethyl-8-hydroxyquinoline) aluminum, bis (2-methyl-4-ethyl-8-hydroxyquinoline) aluminum-μ-oxo-bis (2 -Methyl-4-ethyl-8-hydroxyquinoline) aluminum, bis (2-methyl-4-methoxy-8-hydroxyquinoline) aluminum-μ-oxo-bis (2-methyl- 4-methoxy-8-hydroxyquinoline) aluminum, bis (2-methyl-5-cyano-8-hydroxyquinoline) aluminum-μ-oxo-bis (2-methyl-5-cyano) -8-hydroxyquinoline) aluminum, bis (2-methyl-5-trifluoromethyl) -8-hydroxyquinoline) aluminum-μ-oxo-bis (2-methyl-5-trifluoromethyl-8-hydroxyquinoline) aluminum, bis (10-hydroxybenzo [h] quinoline) beryllium Wait.

The hydroxyquinoline-based metal complex can be produced using a known raw material and a known synthesis method.

<Thiazole derivatives and benzothiazole derivatives>
The thiazole derivative is, for example, a compound represented by the following formula (ETM-14-1).
[Chem. 141]

The benzothiazole derivative is, for example, a compound represented by the following formula (ETM-14-2).
[Chem. 142]

Each fluorene is n-valent aryl ring (preferably n-valent benzene ring, naphthalene ring, anthracene ring, fluorene ring, benzofluorene ring, fluorene ring, phenanthrene ring or triphenylene ring), n is 1 An integer of from 4 to "thiazole-based substituent" or "benzothiazole-based substituent" is a combination of "ETM-2", "ETM-2-1" and "ETM-2-2" The pyridyl group in the "pyridine-based substituent" is substituted with the following thiazolyl or benzothiazolyl substituent, and at least one hydrogen in the thiazolyl derivative and the benzothiazole derivative may be substituted with deuterium.
[Chemical 143]

ϕ is further preferably an anthracene ring or a fluorene ring, and the structure in this case can be referred to the description in the formula (ETM-2-1) or formula (ETM-2-2), and R ¹¹ to R ^{18 in each} formula may be The description in the formula (ETM-2-1) or the formula (ETM-2-2) is cited. The formula (ETM-2-1) or the formula (ETM-2-2) has been described in a form in which two pyridine-based substituents are bonded, but these are substituted with thiazole-based substituents (or In the case of benzothiazole-based substituents, two pyridine-based substituents (that is, n = 2) may be substituted by thiazole-based substituents (or benzothiazole-based substituents), or substituted by thiazole-based substituents (or benzothiazole-based substituents) Group) in which any pyridine-based substituent is substituted and another pyridine-based substituent is substituted with R ¹¹ to R ¹⁸ (that is, n = 1). Further, for example, by a substituted thiazole group (benzothiazole-based or substituents) in the formula ^{(ETM-2-1) R 11 ~} R ¹⁸ being substituted at least one of "a pyridine-based substituent R ¹¹ ~ R ¹⁸ base".

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

The electron transport layer or the electron injection layer may further include a substance capable of reducing a material forming the electron transport layer or the electron injection layer. As long as the reducing substance is a substance having a certain reducing property, various substances can be used. For example, a material selected from the group consisting of an alkali metal, an alkaline earth metal, a rare earth metal, an oxide of an alkali metal, an alkali metal halide, and an alkaline earth metal can be appropriately used. Of oxides, halides of alkaline earth metals, oxides of rare earth metals, halides of rare earth metals, organic complexes of alkali metals, organic complexes of alkaline earth metals, and organic complexes of rare earth metals At least one of.

Examples of preferred reducing substances include alkali metals such as Na (work function: 2.36 eV), K (work function: 2.28 eV), Rb (work function: 2.16 eV), or Cs (work function: 1.95 eV). Or alkaline earth metals such as Ca (work function is 2.9 eV), Sr (work function is 2.0 eV to 2.5 eV), or Ba (work function is 2.52 eV), particularly those having a work function of 2.9 eV or less. Among these reducing materials, the more preferable reducing material is an alkali metal of K, Rb, or Cs, more preferably Rb or Cs, and most preferably Cs. The reducing ability of these alkali metals is particularly high. By adding a relatively small amount of these alkali metals to the material forming the electron transporting layer or the electron injection layer, it is possible to improve the luminous brightness or extend the life of the organic EL device. In addition, as a reducing substance having a work function of 2.9 eV or less, a combination of two or more of the above-mentioned alkali metals is also preferable, and a combination including Cs is particularly preferable, such as Cs and Na, Cs and K, Cs and Rb, or Combination of Cs with Na and K. By including Cs, the reducing ability can be efficiently exhibited, and by adding to the material forming the electron transporting layer or the electron injecting layer, it is possible to improve the luminous brightness or extend the life of the organic EL element.

The materials for the electron injecting layer and the material for the electron transporting layer can also be used as the following polymer compounds or polymer crosslinked bodies thereof, or the following suspended polymer compounds or suspended polymer crosslinked bodies thereof A material for an electron layer, wherein the polymer compound is obtained by polymerizing a reactive compound substituted with a reactive substituent in the material for the electron transport layer and the material for the electron transport layer as a monomer, The suspension type polymer compound is obtained by reacting a main chain type polymer with the reactive compound. As a reactive substituent in this case, the description in the polycyclic aromatic compound represented by Formula (1) can be cited.
Details of applications of such a polymer compound and a polymer crosslinked body will be described later.

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

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

Furthermore, the following preferable examples can be cited: in order to protect the electrode, metals such as platinum, gold, silver, copper, iron, tin, aluminum, and indium, or alloys using these metals, and silicon dioxide, titanium dioxide, and nitride Inorganic substances such as silicon, polyvinyl alcohol, vinyl chloride, and hydrocarbon polymer compounds are laminated. The methods for producing these electrodes are not particularly limited as long as they can be conducted by resistance heating, electron beam evaporation, sputtering, ion plating, and coating.

＜ Adhesive for each layer ＞
The materials used for the above hole injection layer, hole transport layer, light emitting layer, electron transport layer, and electron injection layer can be formed separately, and can also be dispersed in polyvinyl chloride, polycarbonate, Polystyrene, poly (N-vinylcarbazole), polymethyl methacrylate, polybutyl methacrylate, polyester, polyfluorene, polyphenylene oxide, polybutadiene, hydrocarbon resin, ketone Resins, phenoxy resins, polyamides, ethyl cellulose, vinyl acetate resins, acrylonitrile-butadiene styrene (ABS) resins, solvent-soluble resins such as polyurethane resins Or used in hardening resins such as phenol resin, xylene resin, petroleum resin, urea resin, melamine resin, unsaturated polyester resin, alkyd resin, epoxy resin, and silicone resin.

<Manufacturing method of organic electroluminescence element>
Each layer constituting the organic EL element can be formed by a method such as vapor deposition method, resistance heating vapor deposition, electron beam vapor deposition, sputtering, molecular lamination method, printing method, spin coating method, casting method, or coating method. The material is made into a thin film. The film thickness of each layer formed as described above is not particularly limited and can be appropriately set according to the properties of the material, but it is usually in the range of 2 nm to 5000 nm. The film thickness can be usually measured by a crystal oscillation type film thickness measuring device or the like. When a thin film is formed by a vapor deposition method, the vapor deposition conditions differ depending on the type of the material, the target crystal structure and the association structure of the film, and the like. The vapor deposition conditions are usually preferably at a boat heating temperature of + 50 ° C to + 400 ° C, a degree of vacuum of 10 ^-6 Pa to 10 ^-3 Pa, a vapor deposition rate of 0.01 nm / sec to 50 nm / sec, and a substrate temperature of -150 ° C. It is appropriately set within a range of ˜ + 300 ° C and a film thickness of 2 nm to 5 μm.

In the case where a DC voltage is applied to the organic EL element obtained as described above, it is only necessary to apply the anode as a polarity and the cathode as a polarity. If a voltage of about 2 V to 40 V is applied, it may be applied. Luminescence was observed from the transparent or translucent electrode side (anode or cathode, and both). The organic EL element emits light even when a pulse current or an alternating current is applied. In addition, the waveform of the applied alternating current may be arbitrary.

Next, as an example of a method of manufacturing an organic EL device, an organic EL device including an anode / hole injection layer / hole transport layer / light emitting layer including a host material and a dopant material / electron transport layer / electron injection layer / cathode A method for manufacturing the device will be described.

＜ Evaporation method ＞
After an anode is formed on a suitable substrate by forming a thin film of an anode material by a vapor deposition method or the like, a thin film of a hole injection layer and a hole transport layer is formed on the anode. A host material and a dopant material are co-evaporated thereon to form a thin film as a light emitting layer, an electron transport layer and an electron injection layer are formed on the light emitting layer, and a thin film containing a substance for a cathode is formed by a vapor deposition method or the like As a cathode, a target organic EL element was obtained. Furthermore, in the production of the organic EL device, the production order can be reversed, and the cathode, the electron injection layer, the electron transport layer, the light emitting layer, the hole transport layer, the hole injection layer, and the anode can be produced in this order.

＜ Wet film formation method ＞
A low-molecular compound capable of forming each organic layer of an organic EL element is prepared as a liquid organic layer-forming composition, and a wet film formation method is performed using the composition. In the absence of a suitable organic solvent for dissolving the low-molecular compound, a composition for forming an organic layer can also be prepared from a high-molecular compound that is substituted for the low-molecular compound. Other monomers having a reactive substituent and having a dissolving function or a main chain polymer are polymerized together.

The wet film formation method generally forms a coating film by going through the steps of applying a composition for forming an organic layer on a substrate and removing a solvent from the coated composition for forming an organic layer. Drying step. When the polymer compound has a crosslinkable substituent (also referred to as a crosslinkable polymer compound), the polymer is further crosslinked by this drying step to form a polymer crosslinked body. According to different coating steps, the method using a spin coater is called a spin coating method, the method using a slit coater is called a slit coating method, and the method using a plate is called a gravure, lithography, reverse flat For the plate and flexographic printing method, a method using an inkjet printer is referred to as an inkjet method, and a method of blowing into a mist is referred to as a spray method. The drying step includes methods such as air drying, heating, and drying under reduced pressure. The drying step may be performed only once, or multiple times using different methods or conditions. In addition, for example, different methods may be used in combination with calcination under reduced pressure.

The wet film formation method is a film formation method using a solution, and is, for example, a partial printing method (inkjet method), a spin coating method, a casting method, a coating method, or the like. The wet film formation method is different from the vacuum evaporation method, and does not require the use of an expensive vacuum evaporation device, and can be formed at atmospheric pressure. In addition, the wet film formation method can be produced in a large area or continuously, thereby reducing manufacturing costs.

On the other hand, when compared with the vacuum evaporation method, the wet film formation method may be difficult to be laminated. When a laminated film is produced by a wet film formation method, it is necessary to prevent dissolution of the bottom layer caused by the composition of the upper layer, and use a composition that controls solubility, cross-linking of the bottom layer, and an orthogonal solvent (Orthogonal solvent, each other). Insoluble solvent) and so on. However, even when these techniques are used, there are cases where it is difficult to apply the wet film formation method to the coating of all films.

Therefore, generally, a method is used in which only a few layers are made using a wet film formation method, and the remaining layers are made using a vacuum evaporation method to produce an organic EL element.

For example, the following shows a part of a procedure for producing an organic EL element by applying a wet film formation method.
(Procedure 1) Film formation of anode by vacuum evaporation method (Procedure 2) Formation of composition of hole injection layer including material for hole injection layer by wet film formation method (Procedure 3) Film formation by a wet film formation method including a hole transport layer-forming composition containing a material for a hole transport layer (procedure 4) Use of a composition for forming a light-emitting layer including a host material and a dopant material by a wet method Film formation by the film formation method (Procedure 5) Film formation by vacuum evaporation method (Procedure 6) Electron injection layer film formation by vacuum evaporation method (Program 7) Cathode vacuum evaporation Through the process of film formation by the plating method, an organic material including an anode / hole injection layer / hole transport layer / light emitting layer including a host material and a dopant material / electron transport layer / electron injection layer / cathode can be obtained. EL element.
Of course, there are means for preventing dissolution of the underlying light-emitting layer, and means for forming a film from the cathode side as opposed to the procedure described above, as a composition for forming a layer including a material for an electron transport layer or a material for an electron injection layer These materials can be prepared by a wet film forming method.

＜ Other film forming methods ＞
For the formation of the organic layer-forming composition, a laser heating drawing method (LITI) can be used. The LITI is a method for thermally vapor-depositing a compound attached to a substrate by laser, and a composition for forming an organic layer can be used for a material coated on the substrate.

＜ Arbitrary steps ＞
Appropriate processing steps, washing steps, and drying steps may also be added before and after each step of film formation. Examples of the treatment steps include exposure treatment, plasma surface treatment, ultrasonic treatment, ozone treatment, cleaning treatment using a suitable solvent, and heat treatment. Furthermore, a series of steps for producing a bank can be listed.

Photolithography can be used in the production of the embankment. As a bank material that can use photolithography, a positive resist material and a negative resist material can be used. In addition, a pattern printing method such as an inkjet method, gravure lithography, reverse lithography, or screen printing can also be used. In this case, a permanent resist material may be used.

Examples of the material used for the bank include polysaccharides and derivatives thereof, homopolymers and copolymers of ethylenic monomers having a hydroxyl group, biopolymers, polypropylene compounds, polyesters, polystyrene, Polyimide, polyimide, imine, polyether, imine, polysulfide, polyfluorene, polyphenylene, polyphenyl ether, polyurethane, (methyl ) Epoxy acrylate, melamine (meth) acrylate, polyolefin, cyclic polyolefin, acrylonitrile-butadiene-styrene copolymer (ABS), silicone resin, polyvinyl chloride, chlorinated polyethylene , Chlorinated polypropylene, polyacetate, polynorbornene, synthetic rubber, polyvinylidene fluoride, polytetrafluoroethylene, polyhexafluoropropylene and other fluorinated polymers, fluoroolefin-hydrocarbon olefin copolymers And fluorocarbon polymer, but it is not limited to this.

<Composition for forming organic layer used in wet film formation method>
The composition for forming an organic layer is obtained by dissolving a low-molecular compound that can form each organic layer of an organic EL element or a high-molecular compound obtained by polymerizing the low-molecular compound in an organic solvent. For example, the composition for forming a light-emitting layer contains at least one polycyclic aromatic compound (or a polymer compound thereof) as a dopant material as a first component, at least one host material as a second component, and at least one organic solvent as a third component. ingredient. The first component functions as a dopant component of the light-emitting layer obtained from the composition, and the second component functions as a host component of the light-emitting layer. The third component functions as a solvent that dissolves the first component and the second component in the composition, and at the time of coating, a smooth and uniform surface shape is obtained by the controlled evaporation rate of the third component itself.

＜ Organic solvent ＞
The composition for forming an organic layer contains at least one organic solvent. The evaporation rate of the organic solvent is controlled during film formation, thereby controlling and improving the film-forming property and the presence or absence of defects, surface roughness, and smoothness of the coating film. In addition, when using the inkjet method to form a film, the meniscus stability at the pinhole of the inkjet head can be controlled, and the ejection performance can be controlled and improved. In addition, by controlling the drying speed of the film and the orientation of the derivative molecules, it is possible to improve the electrical characteristics, light emission characteristics, efficiency, and lifetime of an organic EL device having an organic layer obtained from the composition for forming an organic layer.

(1) Physical properties of organic solvent The boiling point of at least one organic solvent is 130 ° C to 300 ° C, more preferably 140 ° C to 270 ° C, and even more preferably 150 ° C to 250 ° C. From the viewpoint of the ejectability of inkjet, a case where the boiling point is higher than 130 ° C is preferred. From the viewpoint of defects, surface roughness, residual solvent, and smoothness of the coating film, a case where the boiling point is lower than 300 ° C is preferred. From the viewpoint of good inkjet ejectability, film-forming property, smoothness, and low residual solvent, the organic solvent is more preferably a structure including two or more organic solvents. On the other hand, it may be a composition which is made into a solid state by removing a solvent from the composition for forming an organic layer, considering transportability and the like, as appropriate.

Furthermore, the organic solvent includes a good solvent (GS) and a poor solvent (PS) for at least one of the solutes. It is particularly preferred that the boiling point (BP _GS ) of the good solvent (GS) is lower than the poor solvent ( PS) composition of boiling point (BP _PS ).
By adding a poor solvent with a high boiling point, a good solvent with a low boiling point is volatilized at the time of film formation, and the concentration of the content in the composition and the concentration of the poor solvent are increased to promote rapid film formation. Thereby, a coating film with few defects, small surface roughness, and high smoothness can be obtained.

The difference in solubility (S _GS -S _PS ) is preferably 1% or more, more preferably 3% or more, and even more preferably 5% or more. The difference in boiling points (BP _PS -BP _GS ) is preferably 10 ° C or higher, more preferably 30 ° C or higher, and even more preferably 50 ° C or higher.

The organic solvent is removed from the coating film by drying steps such as vacuum, reduced pressure, and heating after film formation. In the case of heating, from the viewpoint of improving the coating film formability, the glass transition temperature (Tg) of at least one of the solutes is preferably 30 ° C or lower. In addition, from the viewpoint of reducing the residual solvent, the glass transition temperature (Tg) of at least one of the solutes is preferably -30 ° C or higher. Even if the heating temperature is lower than the boiling point of the organic solvent, the organic solvent is sufficiently removed because the film is thin. In addition, drying can be performed multiple times at different temperatures, or multiple drying methods can be used in combination.

(2) Specific examples of organic solvents As the organic solvent used in the composition for forming an organic layer, an alkylbenzene-based solvent, a phenyl ether-based solvent, an alkyl ether-based solvent, a cyclic ketone-based solvent, and an aliphatic A ketone solvent, a monocyclic ketone solvent, a solvent having a diester skeleton, and a fluorine-containing solvent. Specific examples include pentanol, hexanol, heptanol, octanol, nonanol, decanol, and eleven Alcohol, dodecanol, tetradecanol, hexane-2-ol, heptane-2-ol, octane-2-ol, decane-2-ol, dodecane-2-ol, cyclohexanol, α-terpineol, β-terpineol, γ-terpineol, δ-terpineol, pinoresinol (mixture), ethylene glycol monomethyl ether acetate, propylene glycol monomethyl ether acetate, two Ethylene glycol dimethyl ether, dipropylene glycol dimethyl ether, diethylene glycol ethyl methyl ether, diethylene glycol isopropyl methyl ether, dipropylene glycol monomethyl ether, diethylene glycol diethyl ether, diethylene glycol Alcohol monomethyl ether, diethylene glycol butyl methyl ether, tripropylene glycol dimethyl ether, triethylene glycol dimethyl ether, diethylene glycol monobutyl ether, ethylene glycol monophenyl ether, triethylene glycol monomethyl ether, Diethylene glycol di Butyl ether, triethylene glycol butyl methyl ether, polyethylene glycol dimethyl ether, tetraethylene glycol dimethyl ether, para-xylene, m-xylene, o-xylene, 2,6-dimethylpyridine, 2-fluoro -M-xylene, 3-fluoro-o-xylene, 2-chlorobenzotrifluoride, cumene, toluene, 2-chloro-6-fluorotoluene, 2-fluoroanisole, anisole, 2,3 -Dimethylpyrazine, bromobenzene, 4-fluoroanisole, 3-fluoroanisole, 3-trifluoromethylanisole, mesitylene, 1,2,4-trimethylbenzene, Tributylbenzene, 2-methylanisole, phenyl ether, benzodioxole, 4-methylanisole, second butylbenzene, 3-methylanisole, 4-fluoro 3-methylanisole, cymene, 1,2,3-trimethylbenzene, 1,2-dichlorobenzene, 2-fluorobenzonitrile, 4-fluoro-o-dimethoxy Benzene (4-fluoroveratrole), 2,6-dimethylanisole, n-butylbenzene, 3-fluorobenzonitrile, decahydronaphthalene, neopentylbenzene, 2,5-dimethylbenzene Methyl ether, 2,4-dimethylanisole, benzonitrile, 3,5-dimethylanisole, diphenylether, 1-fluoro-3,5-dimethoxybenzene, methyl benzoate Esters, isoamylbenzene, 3,4-dimethylbenzene Ether, o-tolunitrile, n-pentylbenzene, veratrole, 1,2,3,4-tetrahydronaphthalene, ethyl benzoate, n-hexylbenzene, propyl benzoate Ester, cyclohexylbenzene, 1-methylnaphthalene, butyl benzoate, 2-methylbiphenyl, 3-phenoxytoluene, 2,2'-dimethylbiphenyl (2,2'-bitolyl), Dodecylbenzene, dipentylbenzene, tetramethylbenzene, trimethoxybenzene, trimethoxytoluene, 2,3-dihydrobenzofuran, 1-methyl-4- (propoxymethyl) benzene , 1-methyl-4- (butoxymethyl) benzene, 1-methyl-4- (pentoxymethyl) benzene, 1-methyl-4- (hexyloxymethyl) benzene, 1 -Methyl-4- (heptyloxymethyl) benzyl butyl ether, benzyl pentyl ether, benzyl hexyl ether, benzyl heptyl ether, benzyl octyl ether, etc., but it is not limited to this . The solvent may be used singly or in combination.

＜ Arbitrary ingredients ＞
The composition for forming an organic layer may contain an arbitrary component so long as it does not impair its properties. Examples of the optional component include a binder and a surfactant.

(1) Binder The composition for forming an organic layer may contain a binder. Regarding the adhesive, at the time of film formation, the obtained film is bonded to the substrate while forming the film. In addition, in the composition for forming an organic layer, functions of dissolving, dispersing, and binding other components are exerted.

Examples of the binder used in the composition for forming an organic layer include acrylic resin, polyethylene terephthalate, ethylene-vinyl acetate copolymer, ethylene-vinyl alcohol copolymer, and acrylonitrile-ethylene- Acrylonitrile- ethylene-styrene (AES) resin, ionomer, chlorinated polyether, diallyl phthalate resin, unsaturated polyester resin, polyethylene, polypropylene, poly Vinyl chloride, polyvinylidene chloride, polystyrene, polyvinyl acetate, Teflon, acrylonitrile-butadiene-styrene copolymer (ABS) resin, acrylonitrile-styrene Copolymer (Acrylonitrile-Styrene, AS) resin, phenol resin, epoxy resin, melamine resin, urea resin, alkyd resin, polyurethane, and copolymer of the resin and polymer, but it is not limited herein.

The binder used in the composition for forming an organic layer may be only one type, or a plurality of types may be used in combination.

(2) Surfactant For example, in order to control the uniformity of the film surface of the composition for forming an organic layer, the compatibility of the film surface, and the liquid repellency, the composition for forming an organic layer may contain a surfactant. Surfactants are classified into ionic and nonionic based on the structure of a hydrophilic group, and further classified into alkyl-based, silicon-based, and fluorine-based based on the structure of a hydrophobic group. In addition, according to the molecular structure, they are classified into a single molecular system having a relatively small molecular weight and a simple structure, and a high molecular weight having a side chain or a branched polymer system. In addition, they are classified into a single system by a composition, and a mixed system in which two or more kinds of surfactants and a substrate are mixed. As the surfactant that can be used in the composition for forming an organic layer, all kinds of surfactants can be used.

Examples of the surfactant include: Polyflow No. 45, Polyflow KL-245, Polyflow No. 75, and Polyflow No. .90, Polyflow No.95 (trade name, manufactured by Kyoeisha Chemical Industry Co., Ltd.), Disperbyk 161, Disperbyk 162, Dis Disperbyk 163, Disperbyk 164, Disperbyk 166, Disperbyk 170, Disperbyk 180, Dis Disperbyk 181, Disperbyk 182, BYK 300, BYK 306, BYK 310, BYK 320, BYK ) 330, BYK 342, BYK 344, BYK 346 (trade name, manufactured by BYK-Chemie Japan), KP-341, KP-358 , KP-368, KF-96-50CS, KF-50-100CS (trade names, manufactured by Shin-Etsu Chemical Industry Co., Ltd.), Surflon SC-101, Surflon KH-40 ( Product name, manufactured by Seimi Chemical (stock), Ftergent 222F, Ftergent 251, FTX-218 (trade name, manufactured by NEOS), Ai Eftop (EFTOP) EF-351, Eftop (EFTOP) EF-352, Eftop (EFTOP) EF-601, Eftop (EFTOP) EF-801, Eftop (EFTOP) EF-802 (Commodities Name, manufactured by Mitsubishi Material (stock), Megafac F-470, Megafac F-471, Megafac F-475, Megafac R-08, Megafac F-477, Megafac F-479, Megafac F-553, Megafac F-554 (trade name, manufactured by DIC) Fluoroalkylbenzene sulfonate, fluoroalkyl carboxylate, fluoroalkyl polyoxyethylene ether, fluoroalkyl ammonium iodide, fluoroalkyl betaine, fluoroalkyl sulfonate, diglycerol tetra (fluoroalkyl (Polyoxyethylene ether), fluoroalkyltrimethylammonium salt, fluoroalkylaminosulfonate, polyoxyethylene nonylphenyl ether, polyoxyethylene octylphenyl ether, polyoxyethylene alkyl ether , Polyoxyethylene laurate, polyoxyethylene oleate, polyoxyethylene stearate, polyoxyethylene laurylamine, sorbitan laurate, sorbitan palmitate, sorbitan Stearate, sorbitan oleate, sorbitan fatty acid ester, polyoxyethylene sorbitan laurate, polyoxyethylene sorbitan palmitate, polyoxyethylene sorbitan Stearate, polyoxyethylene sorbitan oleate, polyoxyethylene naphthyl ether, alkylbenzene sulfonate and alkyl diphenyl ether disulfonate.

The surfactant may be used singly or in combination of two or more kinds.

<Composition and physical properties of the composition for forming an organic layer>
Considering the good solubility, storage stability, and film-forming properties of each component in the composition for forming an organic layer, and the good film quality of the coating film obtained from the composition for forming an organic layer, and good ejection when an inkjet method is used The content of each component in the organic layer-forming composition is determined from the viewpoints of good electrical properties, good electrical characteristics, light-emitting characteristics, efficiency, and lifetime of an organic EL element having an organic layer produced using the composition. For example, in the case of the composition for forming a light-emitting layer, it is preferable that the first component is 0.0001 to 2.0% by weight based on the total weight of the composition for forming a light-emitting layer, and the second component is used for forming the light-emitting layer. The total weight of the composition is 0.0999% to 8.0% by weight, and the third component is 90.0% to 99.9% by weight based on the total weight of the light-emitting layer-forming composition.

More preferably, the first component is 0.005% to 1.0% by weight based on the total weight of the composition for forming a light-emitting layer, and the second component is 0.095% to 4.0% by weight relative to the total weight of the composition for forming a light-emitting layer. %, And the 3rd component is 95.0 weight%-99.9 weight% with respect to the total weight of the composition for light emitting layer formation. Still more preferably, the first component is 0.05 to 0.5% by weight based on the total weight of the composition for forming a light emitting layer, and the second component is 0.25% to 2.5% by weight based on the total weight of the composition for forming a light emitting layer. % By weight, and the third component is 97.0% by weight to 99.7% by weight based on the total weight of the composition for forming a light emitting layer.

The composition for forming an organic layer can be produced by appropriately selecting the components by a known method, and stirring, mixing, heating, cooling, dissolving, dispersing, and the like. In addition, filtration, degassing (also referred to as degas), ion exchange treatment, and inert gas replacement / encapsulation treatment can be appropriately selected after preparation.

Regarding the viscosity of the composition for forming an organic layer, a person with a high viscosity can obtain a good film-forming property and a good ejection property when an inkjet method is used. On the other hand, people with low viscosity can easily make films. Therefore, the viscosity of the composition for forming an organic layer is preferably 0.3 mPa · s to 3 mPa · s at 25 ° C, and more preferably 1 mPa · s to 3 mPa · s. In the present invention, the viscosity is a value measured using a cone-plate type rotary viscometer (cone-plate type).

Regarding the surface tension of the composition for forming an organic layer, the lower one can obtain a good film-forming property and a defect-free coating film. On the other hand, the higher one can obtain good ink jetting properties. Therefore, the viscosity of the composition for forming an organic layer is preferably 20 mN / m to 40 mN / m, and more preferably 20 mN / m to 30 mN / m at 25 ° C. In the present invention, the surface tension is a value measured using the hanging drop method.

<Crosslinkable polymer compound: Compound represented by general formula (XLP-1)>
Next, a case where the polymer compound has a crosslinkable substituent will be described. Such a crosslinkable polymer compound is, for example, a compound represented by the following general formula (XLP-1).
[Chemical 144]

In the formula (XLP-1),
MUx, ECx, and k have the same definitions as MU, EC, and k in the formula (SPH-1), wherein the compound represented by formula (XLP-1) has at least one crosslinkable substituent (XLS), and The content of the monovalent or divalent aromatic compound having a crosslinkable substituent is preferably 0.1% to 80% by weight in the molecule.

The content of the monovalent or divalent aromatic compound having a crosslinkable substituent is preferably 0.5 to 50% by weight, and more preferably 1 to 20% by weight.

The crosslinkable substituent (XLS) is not particularly limited as long as it is a group capable of further crosslinking the polymer compound, and is preferably a substituent having the following structure. * In each structural formula represents a bonding position.
[Chem. 145]

L is independently a single bond, -O-, -S-,> C = O, -OC (= O)-, an alkylene group having 1 to 12 carbon atoms, an oxyalkylene group having 1 to 12 carbon atoms, and Polyoxyalkylene having 1 to 12 carbon atoms. Among the substituents, formula (XLS-1), formula (XLS-2), formula (XLS-3), formula (XLS-9), formula (XLS-10) or formula (XLS-17) are preferred The group represented by) is more preferably a group represented by formula (XLS-1), formula (XLS-3), or formula (XLS-17).

Examples of the divalent aromatic compound having a crosslinkable substituent include compounds having the following partial structure.
[Chemical 146]

[Chemical 147]


[Chemical 148]

[Chem. 149]

<Production method of polymer compound and crosslinkable polymer compound>
The manufacturing method of a polymer compound and a crosslinkable polymer compound is demonstrated using the compound represented by said formula (SPH-1) and the compound represented by formula (XLP-1) as an example. These compounds can be synthesized by appropriately combining known production methods.

Examples of the solvent used in the reaction include an aromatic solvent, a saturated / unsaturated hydrocarbon solvent, an alcohol solvent, and an ether solvent. Examples of the solvent include dimethoxyethane and 2- (2-methoxyethoxy). Group), ethane), 2- (2-ethoxyethoxy) ethane, and the like.

Alternatively, the reaction can be performed in a two-phase system. In the case where the reaction is performed in a two-phase system, an interphase transfer catalyst such as a quaternary ammonium salt may be added if necessary.

When the compound of the formula (SPH-1) and the compound of the formula (XLP-1) are produced, they can be produced in one stage or in multiple stages. In addition, it can be carried out by a collective polymerization method in which all the raw materials are put into a reaction vessel and the reaction can be started. Alternatively, it can be carried out by a dropwise polymerization method in which raw materials are dropped into a reaction vessel. It is carried out by a precipitation polymerization method in which precipitation is carried out, and these may be appropriately combined for synthesis. For example, when a compound represented by the formula (SPH-1) is synthesized in one stage, a target substance is obtained by performing a reaction in a state where a monomer unit (MU) and a capping unit (EC) are added to a reaction container. . In addition, when the compound represented by the general formula (SPH-1) is synthesized in multiple stages, a target substance is obtained by polymerizing a monomer unit (MU) to a target molecular weight and adding an end-capping unit (EC) and reacting it. . If different types of monomer units (MU) are added for reaction in multiple stages, a polymer having a concentration gradient in the structure of the monomer units can be produced. In addition, after the precursor polymer is prepared, the target polymer can be obtained by a subsequent reaction.

In addition, if a polymerizable group of a monomer unit (MU) is selected, the primary structure of the polymer can be controlled. For example, as shown in 1 to 3 of the synthesis scheme, a polymer having a random primary structure (1 of the synthesis scheme), a polymer having a regular primary structure (2 and 3 of the synthesis scheme), and the like can be synthesized. Use the appropriate combination according to the target. Furthermore, when a monomer unit having three or more polymerizable groups is used, a hyperbranched polymer or a dendrimer can be synthesized.

[Chemical 150]

As the monomer unit usable in the present invention, it can be based on Japanese Patent Laid-Open No. 2010-189630, International Publication No. 2012/086671, International Publication No. 2013/191088, International Publication No. 2002/045184, International Publication No. 2011/049241, International Publication No. 2013/146806, International Publication No. 2005/049546, International Publication No. 2015/145871, Japanese Patent Laid-Open No. 2010-215886, Japanese Patent Laid-Open No. 2008-106241, Japanese Patent Japanese Patent Application Publication No. 2010-215886, International Publication No. 2016/031639, Japanese Patent Application Publication No. 2011-174062, International Publication No. 2016/031639, International Publication No. 2016/031639, International Publication No. 2002/045184 Documented method to synthesize.

In addition, specific polymer synthesis procedures can be based on Japanese Patent Laid-Open No. 2012-036388, International Publication No. 2015/008851, Japanese Patent Laid-Open No. 2012-36381, Japanese Patent Laid-Open No. 2012-144722, International Publication No. 2015/194448, International Publication No. 2013/146806, International Publication No. 2015/145871, International Publication No. 2016/031639, International Publication No. 2016/125560, International Publication No. 2016/031639, International Publication No. 2016/031639, International Publication No. 2016/125560, International Publication No. 2015/145871, International Publication No. 2011/049241, and Japanese Patent Laid-Open No. 2012-144722.

<Application example of organic electroluminescence element>
The present invention is also applicable to a display device including an organic EL element, a lighting device including an organic EL element, and the like.
A display device or an illumination device including an organic EL element can be manufactured by a known method such as connecting the organic EL element of this embodiment to a known driving device, and known driving such as DC driving, pulse driving, and AC driving can be appropriately used. Method to drive.

Examples of the display device include a panel display such as a color flat panel display, a flexible display such as a flexible color organic electroluminescence (EL) display, and the like (for example, refer to Japanese Patent Laid-Open No. 10-335066 and Japanese Patent Laid-Open No. 2003). -321546, Japanese Patent Laid-Open No. 2004-281086, etc.). Examples of the display method of the display include a matrix and / or a segment method. Furthermore, the matrix display and the segment display can coexist in the same panel.

A matrix is a two-dimensional arrangement of pixels for display in a grid or mosaic shape, etc., and displays characters or images by a set of pixels. The shape or size of the pixels is determined according to the application. For example, in personal computers, monitors, and televisions, it is common to use quad pixels with a side of 300 μm or less in the image and text display. In the case of large displays such as display panels, the side is mm. Pixels. In the case of monochrome display, it is only necessary to arrange pixels of the same color. In the case of color display, red, green, and blue pixels are displayed in parallel. In this case, a triangle type and a stripe type are typical. Moreover, as the driving method of the matrix, either a line-sequential driving method or an active matrix can be used. The line-sequential drive has the advantage of a simple structure. However, when the operating characteristics are considered, the active matrix is sometimes better. Therefore, the driving method needs to be used according to the application.

In the segmentation method (type), a pattern is formed to display information determined in advance, and the determined area is made to emit light. For example, the time or temperature display in a digital clock or thermometer, the operation status display of an audio equipment or an induction cooker, and the panel display of an automobile are mentioned.

Examples of the lighting device include lighting devices such as indoor lighting and backlights of liquid crystal display devices (for example, refer to Japanese Patent Laid-Open No. 2003-257621, Japanese Patent Laid-Open No. 2003-277741, and Japanese Patent Laid-Open No. 2003-277741). 2004-119211, etc.). The backlight is mainly used to improve the visibility of a display device that does not emit light by itself, and is used for a liquid crystal display device, a clock, an audio device, a car panel, a display panel, and a logo. In particular, as a backlight for personal computer applications where thinning is a problem in a liquid crystal display device, considering that the thinning was difficult due to the conventional method including a fluorescent lamp or a light guide plate, the backlight using the light-emitting element of this embodiment is used. Features thin and light weight.

3-2. Other organic devices In addition to the organic electroluminescence element, the polycyclic aromatic compound of the present invention can be used in the production of organic field effect crystals or organic thin-film solar cells.

The organic field effect transistor is a transistor that uses an electric field generated by a voltage input to control the current. In addition to the source electrode and the drain electrode, a gate electrode is provided. In order to generate an electric field if a voltage is applied to the gate electrode, a transistor that controls the current by arbitrarily blocking the flow of electrons (or holes) flowing between the source electrode and the drain electrode. Compared with a single transistor (bipolar transistor), a field effect transistor is easy to be miniaturized, and is often used as an element constituting an integrated circuit or the like.

The structure of an organic field-effect transistor is usually provided by contacting a source electrode and a drain electrode with an organic semiconductor active layer formed using the polycyclic aromatic compound of the present invention, and further via an insulating layer (dielectric layer) that contacts the organic semiconductor active layer. ) To set the gate electrode. Examples of the element structure include the following structures.
(1) substrate / gate electrode / insulator layer / source electrode / drain electrode / organic semiconductor active layer (2) substrate / gate electrode / insulator layer / organic semiconductor active layer / source electrode / drain electrode (3) substrate / organic semiconductor activity Layer / source electrode · drain electrode / insulator layer / gate electrode (4) substrate / source electrode · drain electrode / organic semiconductor active layer / insulator layer / gate electrode A pixel-driven switching element of a liquid crystal display or an organic electroluminescence display.

Organic thin-film solar cells have a structure in which an anode such as ITO, a hole transport layer, a photoelectric conversion layer, an electron transport layer, and a cathode are laminated on a transparent substrate such as glass. The photoelectric conversion layer has a p-type semiconductor layer on the anode side and an n-type semiconductor layer on the cathode side. The polycyclic aromatic compound of the present invention can be used as a material for a hole transport layer, a p-type semiconductor layer, an n-type semiconductor layer, and an electron transport layer according to its physical properties. In organic thin-film solar cells, the polycyclic aromatic compound of the present invention can function as a hole transporting material or an electron transporting material. In addition to the organic thin-film solar cell, a hole blocking layer, an electron blocking layer, an electron injection layer, a hole injection layer, a smoothing layer, and the like may be appropriately provided. In the organic thin-film solar cell, known materials used for the organic thin-film solar cell can be appropriately selected and used in combination.
[Example]

Hereinafter, the present invention will be further specifically described by examples, but the present invention is not limited to these examples. First, a synthesis example of the polycyclic aromatic compound will be described below.

Synthesis Example (1): Synthesis of Compound (1-25)
[Chemical 151]

Under a nitrogen environment, 4- (1-adamantyl) aniline (15.0 g) was dissolved in acetonitrile (300 ml), bromine (21.1 g) was added dropwise thereto under ice-cooling, and the mixture was stirred for 0.5 hours. After the reaction, water and ethyl acetate were added to the reaction solution and the mixture was stirred. Toluene was further added, and the organic layer was separated and washed with water. Thereafter, the organic layer was concentrated to obtain a crude product. The crude product was purified using a silica gel short column (eluent: toluene), and then washed with heptane to obtain an intermediate (IA) (21.0 g).
[Chemical 152]

Under a nitrogen environment, the intermediate (IA) (21.0 g) was dissolved in acetonitrile (200 ml), and a third butyl nitrite (50 ml) dissolved in acetonitrile (50 ml) was added dropwise thereto at 60 ° C. 8.4 g), and stirred at 60 ° C for 30 minutes. After the reaction, dilute hydrochloric acid and ethyl acetate were added to the reaction solution, and the organic layer was separated and washed with water. Thereafter, the organic layer was concentrated to obtain a crude product. The crude product was purified using a silica gel short column (eluent: toluene / heptane = 1/3 (volume ratio)) to obtain an intermediate (IB) (16.0 g).
[Chemical 153]

Under a nitrogen atmosphere, an intermediate (IB) (12.0 g), N- (3-tert-butylphenyl) -3,5-di-tert-butylaniline (21.0 g), Dichlorobis [(di-third-butyl (4-dimethylaminophenyl) phosphino) palladium (Pd-132, 0.21 g), sodium tert-butoxide (NaOtBu, 7.1 g), and xylene ( 120 ml) into a flask and heated at 100 ° C for 1.5 hours. After the reaction, water and ethyl acetate were added to the reaction solution and the mixture was stirred, and then the organic layer was separated and washed with water. Thereafter, the organic layer was concentrated to obtain a crude product. The crude product was purified using a silica gel short column (eluent: toluene / heptane = 2/8 (volume ratio)) to obtain an intermediate (IC) (26.0 g).
[Chemical 154]

In a nitrogen atmosphere, and at 0 ° C, a flask containing an intermediate (IC) (24.0 g) and a third butylbenzene (120 ml) was charged with 1.56 M of a solution of the third butyl lithium in pentane ( 33.5 ml). After completion of the dropwise addition, the temperature was raised to 60 ° C. and the mixture was stirred for 1 hour, and then the components having a boiling point lower than that of the third butylbenzene were distilled off under reduced pressure. Cool to -50 ° C and add boron tribromide (13.1 g), warm to room temperature and stir for 0.5 hours. Thereafter, it was cooled to 0 ° C again, and N, N-diisopropylethylamine (6.8 g) was added. After stirring at room temperature until the end of heating, the temperature was raised to 100 ° C and the mixture was heated and stirred for 1 hour. The reaction solution was cooled to room temperature, and an aqueous sodium acetate solution cooled with an ice bath and ethyl acetate were sequentially added to carry out liquid separation. After the organic layer was concentrated, it was purified using a short silica gel column (eluent: toluene / heptane = 2/8 (volume ratio)). The obtained crude product was dissolved in toluene and reprecipitated with methanol, whereby Compound (1-25) (6.0 g) was obtained.
[Chem. 155]

The structure of the obtained compound was confirmed by nuclear magnetic resonance (NMR) measurement.
¹ H-NMR (CDCl ₃ ): δ = 1.21 (s, 18H), 1.36 (s, 36H), 1.48-1.66 (m, 12H), 1.89 (s, 3H), 6.18 (s, 2H), 6.78 ( s, 2H), 7.22 (d, 4H), 7.25-7.28 (m, 2H), 7.59 (t, 2H), 8.86 (d, 2H).

Synthesis Example (2): Synthesis of Compound (1-16)
[Chemical 156]

Under a nitrogen atmosphere, intermediate (IB) (10.0 g), N- (4-tert-butylphenyl) -4-tert-butylaniline (14.0 g), and Pd-132 as a palladium catalyst ( 0.18 g), sodium tert-butoxide (NaOtBu, 5.9 g) and xylene (80 ml) were placed in a flask and heated at 100 ° C for 1.5 hours. After the reaction, water and ethyl acetate were added to the reaction solution and the mixture was stirred, and then the organic layer was separated and washed with water. Thereafter, the organic layer was concentrated to obtain a crude product. The crude product was purified using a silica gel short column (eluent: toluene) to obtain an intermediate (ID) (13.1 g).
[Chemical 157]

In a nitrogen atmosphere, and at 0 ° C, a flask containing the intermediate (ID) (13.0 g) and third butylbenzene (100 ml) was charged with 1.56 M of a solution of third butyl lithium in pentane ( 18.3 ml). After the completion of the dropwise addition, the temperature was raised to 70 ° C. and the mixture was stirred for 1 hour, and then a component having a boiling point lower than that of the third butylbenzene was distilled off under reduced pressure. Cool to -50 ° C and add boron tribromide (7.0 g), warm to room temperature and stir for 0.5 hours. Thereafter, it was cooled to 0 ° C again, and N, N-diisopropylethylamine (3.6 g) was added. After stirring at room temperature until the end of heating, the temperature was raised to 80 ° C and the mixture was heated and stirred for 1 hour. The reaction solution was cooled to room temperature, and an aqueous sodium acetate solution cooled with an ice bath and ethyl acetate were sequentially added to carry out liquid separation. After the organic layer was concentrated, a small amount of ethyl acetate was added, and the mixture was heated and dissolved, and then heptane was added. After cooling, the precipitated crystals were separated by filtration, and the crystals were washed with cooled heptane. This crystal was purified using a silica gel short column (eluent: toluene). To the obtained crude product, heptane was added, and after heating and stirring, cooling was performed, and the obtained crystal was separated by filtration. After that, it was dissolved in toluene and concentrated, heptane was added, crystals were precipitated, and then filtered, and this step was repeated to obtain compound (1-16) (5.3 g).
[化 158]

The structure of the obtained compound was confirmed by NMR measurement.
¹ H-NMR (CDCl ₃ ): δ = 1.46 (s, 18H), 1.47 (s, 18H), 1.51-1.54 (m, 9H), 1.62-1.65 (m, 3H), 1.87-1.89 (m, 3H ), 6.05 (s, 2H), 6.79 (d, 2H), 7.30 (d, 4H), 7.50 (dd, 2H), 7.69 (d, 4H), 8.98 (d, 2H).

Synthesis Example (3): Synthesis of Compound (1-321)
[Chemical 159]

Under a nitrogen atmosphere, the intermediate (IE) (40.0 g) was dissolved in chloroform (100 ml), iron (powder) (0.53 g) was added thereto, and bromine (45 g) was added dropwise at room temperature. Stir at room temperature for 4 hours. After adding water, sodium carbonate was slowly added until foaming was completed, and thereafter, an appropriate amount of sodium bisulfite was added. After the organic layer was washed with water, the organic layer was concentrated to obtain a crude product. The crude product was purified using a silica gel short column (eluent: heptane), and then the organic layer was concentrated to obtain a crude product. Heptane was added to the crude product, and after cooling, it was filtered to obtain an intermediate (IF) (44.0 g).
[Chemical 160]

Under a nitrogen atmosphere, intermediate (IG) (10.0 g), intermediate (IF) (11.8 g), Pd-132 (0.26 g) as a palladium catalyst, and sodium tert-butoxide (NaOtBu, 5.3 g) And xylene (70 ml) was put into a flask and heated at 100 ° C for 1 hour. After the reaction, water and ethyl acetate were added to the reaction solution and the mixture was stirred, and then the organic layer was separated and washed with water. Thereafter, heptane was added to the crude product obtained by concentrating the organic layer and the mixture was cooled, and then the obtained crystal was filtered. The crude product was purified using a silica gel short column (eluent: toluene / heptane = 1/1 (volume ratio)), heptane was added to the crude product obtained by concentrating the organic layer, and the mixture was cooled. The obtained crystal was filtered to obtain an intermediate (IH) (10.0 g).
[Chemical 161]

Under nitrogen atmosphere, intermediate (IH) (10.0 g), N- (4-third butylphenyl) -4-third butylaniline (12.8 g), bis (dibenzylideneacetone) palladium (0) (Pd (dba) ₂ , 0.24 g), dicyclohexyl (2 ', 6'-dimethoxy- [1,1'-biphenyl] -2-yl) phosphine (SPhos), third Sodium butoxide (NaOtBu, 5.0 g) and xylene (80 ml) were placed in a flask and heated at 100 ° C for 1 hour. After the reaction, water and ethyl acetate were added to the reaction solution and the mixture was stirred, and then the organic layer was separated and washed with water. To the crude product obtained by concentrating the organic layer, heptane was added and cooled, and then the obtained crystal was filtered. The crude product was purified using a silica gel short column (eluent: toluene), heptane was added to the crude product obtained by concentrating the organic layer and cooled, and then the obtained crystal was filtered to obtain an intermediate ( II) (10.2 g).
[Chemical 162]

In a nitrogen atmosphere, and at 0 ° C, a flask containing the intermediate (II) (10.0 g) and third butylbenzene (70 ml) was charged with 1.56 M of a solution of third butyl lithium in pentane ( 13.5 ml). After the completion of the dropwise addition, the temperature was raised to 70 ° C. and the mixture was stirred for 1 hour, and then a component having a boiling point lower than that of the third butylbenzene was distilled off under reduced pressure. Cool to -50 ° C and add boron tribromide (5.2 g), warm to room temperature and stir for 0.5 hours. Thereafter, it was cooled to 0 ° C again, and N, N-diisopropylethylamine (2.7 g) was added. After stirring at room temperature until the end of heating, the temperature was raised to 80 ° C and the mixture was heated and stirred for 1 hour. The reaction solution was cooled to room temperature, and the sodium acetate aqueous solution cooled with an ice bath and ethyl acetate were sequentially added and stirred for 1 hour. The precipitated yellow precipitate was filtered, and the reaction mixture was sequentially washed with methanol, distilled water, and methanol. The filter was washed. After the yellow precipitate was washed about 2 times with hot heptane, it was further purified using a silica gel short column (eluent: toluene / heptane = 3/7 (volume ratio)). After that, it was dissolved in toluene and concentrated, heptane was added, crystals were precipitated, and then filtered, and this step was repeated to obtain compound (1-321) (5.5 g).
[Chemical 163]

¹ H-NMR (CDCl ₃ ): δ = 1.33 (s, 18H), 1.46 (s, 18H), 1.72-1.80 (m, 6H), 1.84-1.85 (m, 6H), 2.07-2.09 (m, 3H ), 5.69 (s, 2H), 6.67 (d, 2H), 6.86-6.92 (m, 5H), 7.03-7.07 (m, 4H), 7.14 (dt, 4H), 7.43-7.46 (m, 6H), 8.94 (d, 2H).

Synthesis Example (4): Synthesis of Compound (1-328)
[Chemical 164]

Under a nitrogen atmosphere, 4- (1-adamantyl) aniline (25.0 g), intermediate (IF) (32.0 g), Pd-132 (0.78 g) as a palladium catalyst, and sodium tert-butoxide ( NaOtBu, 15.9 g) and xylene (100 ml) were placed in a flask and heated at 130 ° C for 2 hours. After the reaction, water and ethyl acetate were added to the reaction solution and the mixture was stirred, and then the organic layer was separated and washed with water. Thereafter, methanol was added to the crude product obtained by concentrating the organic layer and the mixture was cooled, and then the obtained crystal was filtered. The crude product was purified using a silica gel short column (eluent: toluene), heptane was added to the crude product obtained by concentrating the organic layer and cooled, and then the obtained crystal was filtered to obtain an intermediate (IJ) (41.0 g).
[Chemical 165]

Under a nitrogen environment, intermediate (IJ) (7.6 g), intermediate (IK) (8.0 g), Pd-132 (0.12 g) as a palladium catalyst, and sodium tert-butoxide (NaOtBu, 2.5 g) And xylene (40 ml) was placed in a flask and heated at 120 ° C for 1 hour. After the reaction, water and toluene were added to the reaction solution and stirred, and then the organic layer was separated and washed with water. To the crude product obtained by concentrating the organic layer, heptane was added and cooled, and then the obtained crystal was filtered. The crystals were purified using a silica gel short column (eluent: toluene), heptane was added to the crude product obtained by concentrating the organic layer and cooled, and then the obtained crystals were filtered to obtain an intermediate. (IL) (13.6 g).
[Chemical 166]

In a nitrogen atmosphere, and at 0 ° C, a flask containing the intermediate (IL) (13.5 g) and third butylbenzene (100 ml) was charged with 1.56 M of a solution of third butyl lithium in pentane ( 18.9 ml). After the completion of the dropwise addition, the temperature was raised to 70 ° C. and the mixture was stirred for 1 hour, and then a component having a boiling point lower than that of the third butylbenzene was distilled off under reduced pressure. Cool to -50 ° C and add boron tribromide (7.2 g), warm to room temperature and stir for 0.5 hours. Thereafter, it was cooled to 0 ° C again, and N, N-diisopropylethylamine (3.7 g) was added. After stirring at room temperature until the end of heating, the temperature was raised to 90 ° C and the mixture was heated and stirred for 1 hour. The reaction solution was cooled to room temperature, and an aqueous sodium acetate solution cooled with an ice bath and ethyl acetate were sequentially added and stirred for 1 hour. Then, heptane was added, and then the precipitated yellow precipitate was filtered, and methanol, The filtered matter was washed with distilled water and methanol. The yellow precipitate was washed with hot toluene, and then purified using a silica gel short column (eluent: toluene). After that, it was dissolved in toluene and concentrated, heptane was added, crystals were precipitated, and then filtered, and this step was repeated to obtain compound (1-328) (5.7 g).
[Chemical 167]

¹ H-NMR (CDCl ₃ ): δ = 1.47 (s, 9H), 1.48 (s, 9H), 1.78-1.87 (m, 12H), 2.07-2.09 (m, 12H), 2.14-2.18 (m, 6H ), 2.17 (s, 3H), 5.95 (d, 1H), 6.68 (d, 2H), 7.27 (t, 2H), 7.28 (d, 2H), 7.45 (dd, 1H), 7.49 (dd, 1H) , 7.64 (dd, 2H), 7.67 (dd, 2H), 8.98 (d, 1H), 9.01 (d, 1H).

Synthesis Example (5): Synthesis of Compound (1-327)
[Chemical 168]

Under a nitrogen environment, intermediate (IJ) (5.9 g), intermediate (IM) (6.0 g), Pd-132 (0.10 g) as a palladium catalyst, and sodium tert-butoxide (NaOtBu, 1.9 g) And xylene (30 ml) was put into a flask and heated at 120 ° C for 1 hour. After the reaction, water and toluene were added to the reaction solution and stirred, and then the organic layer was separated and washed with water. To the crude product obtained by concentrating the organic layer, heptane was added and cooled, and then the obtained crystal was filtered. The crystals were purified using a silica gel short column (eluent: toluene), heptane was added to the crude product obtained by concentrating the eluent and cooled, and then the obtained crystals were filtered to obtain an intermediate. (IN) (7.0 g).
[Chemical 169]

In a nitrogen atmosphere, and at 0 ° C, a flask containing the intermediate (IM) (7.0 g) and the third butylbenzene (60 ml) was charged with 1.56 M of a solution of the third butyl lithium in pentane ( 11.1 ml). After the completion of the dropwise addition, the temperature was raised to 70 ° C. and the mixture was stirred for 1 hour, and then a component having a boiling point lower than that of the third butylbenzene was distilled off under reduced pressure. Cool to -50 ° C and add boron tribromide (4.2 g), warm to room temperature and stir for 0.5 hours. Thereafter, it was cooled to 0 ° C again, and N, N-diisopropylethylamine (2.2 g) was added. After stirring at room temperature until the end of heating, the temperature was raised to 80 ° C and the mixture was heated and stirred for 1 hour. The reaction solution was cooled to room temperature, and an aqueous sodium acetate solution cooled with an ice bath and ethyl acetate were sequentially added and stirred for 1 hour. Then, heptane was added, and then the precipitated yellow precipitate was filtered, and methanol, The filtered matter was washed with distilled water and methanol. Furthermore, it was purified using a short silica gel column (eluent: toluene). After that, it was dissolved in toluene and concentrated, heptane was added, and crystals were precipitated and then filtered. This step was repeated to obtain compound (1-327) (3.0 g).
[Chem 170]

¹ H-NMR (CDCl ₃ ): δ = 1.45 (s, 9H), 1.49 (s, 9H), 1.79-1.86 (m, 12H), 2.05-2.10 (m, 12H), 2.15-2.17 (m, 6H ), 6.11 (d, 1H), 6.13 (d, 1H), 6.74 (d, 2H), 7.24 (t, 2H), 7.28 (d, 2H), 7.30 (d, 2H), 7.47 (dd, 1H) , 7.52 (dd, 1H), 7.64 (dd, 2H), 7.67 (dd, 2H), 9.00 (d, 1H), 9.02 (d, 1H).

Synthesis Example (6): Synthesis of Compound (1-332)
[Chemical 171]

Under a nitrogen environment, intermediate (IJ) (6.6 g), intermediate (IO) (5.0 g), Pd-132 (0.11 g) as a palladium catalyst, and sodium tert-butoxide (NaOtBu, 2.2 g) And xylene (35 ml) was placed in a flask and heated at 120 ° C for 1 hour. After the reaction, water and ethyl acetate were added to the reaction solution and the mixture was stirred, and then the organic layer was separated and washed with water. To the crude product obtained by concentrating the organic layer, ethyl acetate was added and cooled, and then the obtained crystals were filtered. The crystals were purified using a silica gel short column (eluent: toluene), heptane was added to the crude product obtained by concentrating the eluent and cooled, and then the obtained crystals were filtered to obtain an intermediate. (IP) (9.6 g).
[Chemical 172]

In a nitrogen atmosphere, and at 0 ° C, a flask containing an intermediate (IP) (9.5 g) and a third butylbenzene (100 ml) was charged with 1.56 M of a solution of the third butyl lithium in pentane ( 18.9 ml). After the completion of the dropwise addition, the temperature was raised to 70 ° C. and the mixture was stirred for 1 hour, and then a component having a boiling point lower than that of the third butylbenzene was distilled off under reduced pressure. Cool to -50 ° C and add boron tribromide (7.2 g), warm to room temperature and stir for 0.5 hours. Thereafter, it was cooled to 0 ° C again, and N, N-diisopropylethylamine (3.7 g) was added. After stirring at room temperature until the end of heating, the temperature was raised to 80 ° C and the mixture was heated and stirred for 1 hour. The reaction solution was cooled to room temperature, and an aqueous sodium acetate solution and ethyl acetate, which were cooled in an ice bath, were sequentially added, and after stirring for 1 hour, the organic layer was separated. After the organic solvent was distilled off, it was purified using a short silica gel column (eluent: toluene / heptane = 2/8 (volume ratio)). After that, it was dissolved in toluene and concentrated, heptane was added, and crystals were precipitated and then filtered. This step was repeated to obtain the compound (1-332) (3.8 g).
[Chemical 173]

The structure of the obtained compound was confirmed by NMR measurement.
¹ H-NMR (CDCl ₃ ): δ = 1.81-1.87 (m, 12H), 2.05-2.07 (m, 12H), 2.16-2.17 (m, 6H), 6.09 (d, 1H), 6.16 (d, 1H ), 6.75 (dd, 2H), 7.23-7.31 (m, 6H), 7.39 (d, 2H), 7.43 (dt, 1H), 7.50 (dd, 1H), 7.59 (dt, 1H), 7.65 (dd, 2H), 7.69 (t, 2H), 8.88 (d, 1H), 8.93 (d, 1H).

Synthesis Example (7): Synthesis of Compound (1-334)
[Chemical 174]

Under nitrogen, 4- (1-adamantyl) aniline (12.7 g), 3,5-di-tert-butyl bromobenzene (15.0 g), and Pd-132 (0.39 g) as a palladium catalyst , Sodium tert-butoxide (NaOtBu, 8.0 g) and xylene (100 ml) were placed in a flask and heated at 130 ° C for 2 hours. After the reaction, water and ethyl acetate were added to the reaction solution and the mixture was stirred, and then the organic layer was separated and washed with water. Thereafter, Solmix (A-11) was added to the crude product obtained by concentrating the organic layer, followed by cooling, and then the obtained crystal was filtered. The crude product was purified using a silica gel short column (eluent: toluene), heptane was added to the crude product obtained by concentrating the organic layer and cooled, and then the obtained crystal was filtered to obtain an intermediate (IQ) (16.0 g).
[Chemical 175]

Under a nitrogen atmosphere, intermediate (IQ) (8.0 g), intermediate (IK) (8.9 g), Pd-132 (0.14 g) as a palladium catalyst, and sodium tert-butoxide (NaOtBu, 2.8 g) And xylene (40 ml) was placed in a flask and heated at 120 ° C for 1 hour. After the reaction, water and toluene were added to the reaction solution and stirred, and then the organic layer was separated and washed with water. To the crude product obtained by concentrating the organic layer, heptane was added and cooled, and then the obtained crystal was filtered. The crystals were purified using a silica gel short column (eluent: toluene), heptane was added to the crude product obtained by concentrating the organic layer and cooled, and then the obtained crystals were filtered to obtain an intermediate. (IR) (13.0 g).
[Chemical 176]

In a nitrogen atmosphere, and at 0 ° C, a flask containing the intermediate (IR) (13.0 g) and the third butylbenzene (100 ml) was charged with 1.56 M of a solution of the third butyl lithium in pentane ( 20.9 ml). After the completion of the dropwise addition, the temperature was raised to 70 ° C. and the mixture was stirred for 1 hour, and then a component having a boiling point lower than that of the third butylbenzene was distilled off under reduced pressure. Cool to -50 ° C and add boron tribromide (7.9 g), warm to room temperature and stir for 0.5 hours. Thereafter, it was cooled to 0 ° C again, and N, N-diisopropylethylamine (4.1 g) was added. After stirring at room temperature until the end of heating, the temperature was raised to 90 ° C and the mixture was heated and stirred for 1 hour. The reaction solution was cooled to room temperature, and an aqueous sodium acetate solution and ethyl acetate cooled in an ice bath were sequentially added, and after stirring for 1 hour, the organic layer was separated by liquid separation. After the organic solvent was distilled off, it was purified using a short silica gel column (eluent: toluene). Thereafter, it was dissolved in toluene and concentrated, ethyl acetate was added, and crystals were precipitated and then filtered. This step was repeated to obtain a compound (1-334) (7.2 g).
[Chemical 177]

The structure of the obtained compound was confirmed by NMR measurement.
¹ H-NMR (CDCl ₃ ): δ = 1.37 (s, 18H), 1.47 (s, 9H), 1.49 (s, 9H), 1.79-1.85 (m, 6H), 2.10-2.11 (m, 6H), 2.15-2.16 (m, 6H), 5.96 (s, 1H), 5.97 (s, 1H), 6.68 (d, 1H), 6.70 (d, 1H), 7.20 (d, 2H), 7.26-7.28 (m, 2H), 7.47 (dd, 1H), 7.50 (dd, 2H), 7.60 (t, 2H), 7.67 (tt, 2H), 9.00 (d, 1H), 9.01 (d, 1H).

Synthesis Example (8): Synthesis of Compound (1-339)
[Chemical 178]

Under a nitrogen atmosphere, 2,3-dichloroaniline (10.0 g), 4-cyclohexyl bromobenzene (36.9 g), Pd-132 (0.44 g) as a palladium catalyst, and sodium tert-butoxide (NaOtBu, 14.8 g) and xylene (120 ml) were placed in a flask and heated at 120 ° C for 1 hour. After the reaction, water and ethyl acetate were added to the reaction solution and the mixture was stirred, and then the organic layer was separated and washed with water. The crude product obtained by concentrating the organic layer was purified using a silica gel short column (eluent: toluene / heptane = 2/8 (volume ratio)), and Sormi was added to the crude product obtained by concentrating the eluent. Solmix (A-11) and cooled, and then the obtained crystals were filtered to obtain an intermediate (IS) (25.5 g).
[Chemical 179]

Under a nitrogen atmosphere, N- (4-tert-butylphenyl) -4-tert-butylaniline (4.5 g), intermediate (IS) (36.9 g), Pd-132 ( 0.11 g), sodium tert-butoxide (NaOtBu, 2.3 g) and xylene (35 ml) were placed in a flask, and heated at 120 ° C. for 1 hour. After the reaction, water and ethyl acetate were added to the reaction solution and the mixture was stirred, and then the organic layer was separated and washed with water. The crude product obtained by concentrating the organic layer was purified using a silica gel short column (eluent: toluene). To the crude product obtained by concentrating the eluent, heptane was added and cooled, and the obtained crystals were filtered. Thereby, an intermediate (IT) (10.5 g) was obtained.
[Chemical 180]

In a nitrogen atmosphere, and at 0 ° C, a flask containing the intermediate (IT) (10.5 g) and third butylbenzene (100 ml) was charged with 1.56 M of a solution of third butyl lithium in pentane ( 19.1 ml). After the completion of the dropwise addition, the temperature was raised to 70 ° C. and the mixture was stirred for 1 hour, and then a component having a boiling point lower than that of the third butylbenzene was distilled off under reduced pressure. Cool to -50 ° C and add boron tribromide (7.2 g), warm to room temperature and stir for 0.5 hours. Thereafter, it was cooled to 0 ° C again, and N, N-diisopropylethylamine (3.7 g) was added. After stirring at room temperature until the end of heating, the temperature was raised to 80 ° C and the mixture was heated and stirred for 1 hour. The reaction solution was cooled to room temperature, and an aqueous sodium acetate solution cooled with an ice bath and ethyl acetate were sequentially added and stirred for 1 hour. Then, heptane was added, and the precipitated yellow precipitate was filtered. Refining was performed using a silica gel short column (eluent: toluene). After that, it was dissolved in toluene and concentrated, ethyl acetate was added, and then heptane was added. After crystallization, the mixture was filtered, and this step was repeated to obtain compound (1-339) (5.3 g).
[Chemical 181]

The structure of the obtained compound was confirmed by NMR measurement.
¹ H-NMR (CDCl ₃ ): δ = 1.25-1.64 (m, 28H), 1.79-1.81 (m, 2H), 1.89-1.93 (m, 4H), 2.03-2.07 (m, 4H), 2.61-2.70 (m, 2H), 6.12 (t, 2H), 6.71 (d, 1H), 6.74 (d, 1H), 7.22-7.30 (m, 6H), 7.48-7.53 (m, 3H), 7.67 (d, 2H ), 8.83 (d, 1H), 8.99 (d, 1H).

By appropriately changing the compounds of the raw materials, other polycyclic aromatic compounds of the present invention can be synthesized by the method according to the synthesis example described above.

Next, examples of the organic EL element using the compound of the present invention will be described in order to explain the present invention in more detail, but the present invention is not limited to these examples.

<Evaluation of vapor-deposited organic EL elements>
The organic EL elements of Example 1, Example 2 to Example 3, and Example 4 to Example 28 were fabricated, and the voltage (V), emission wavelength (nm), and external quantum of the characteristics when emitting light at 1000 cd / m ^{2 were} measured. The efficiency (%) was measured in the following time: the time during which the brightness was maintained at 90% or more of the initial brightness when the constant current drive was performed at a current density of 10 mA / cm ² .

The quantum efficiency of a light-emitting element includes an internal quantum efficiency and an external quantum efficiency. The internal quantum efficiency indicates a ratio in which external energy injected as an electron (or hole) into a light-emitting layer of a light-emitting element is purely converted into a photon. On the other hand, the external quantum efficiency is calculated based on the amount of the photon released to the outside of the light emitting element. A part of the photons generated in the light emitting layer is absorbed or continuously reflected by the inside of the light emitting element without being released to the outside of the light emitting element. External quantum efficiency is lower than internal quantum efficiency.

The external quantum efficiency is measured as follows. A voltage / current generator R6144 manufactured by Advantest was used, and a voltage of 1000 cd / m ^{2 was} applied to the element to cause the element to emit light. A spectroradiometer SR-3AR manufactured by TOPCON was used to measure the spectroradiation brightness in the visible region from a direction perpendicular to the light emitting surface. Assuming that the light-emitting surface is a fully diffused surface, the value obtained by dividing the measured spectral emission brightness of each wavelength component by the wavelength energy and multiplying by π is the number of photons at each wavelength. Then, the number of photons is accumulated in the observed full wavelength region, and it is set as the total number of photons released from the element. The value obtained by dividing the value of the applied current by the elementary charge is the number of carriers injected into the element, and the total number of photons released from the element divided by the number of carriers injected into the element The value is the external quantum efficiency.

<Example 1>
The material configuration and EL characteristic data of each layer of the organic EL element of Example 1 are shown in Tables 1A and 1B below.

[Table 1A]
[Table 1B]

In Table 1A, "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-hexaazatriphenylene hexacarbonitrile, and "HT-1" is N- ( [1,1'-Biphenyl] -4-yl-9,9-dimethyl-N- [4- (9-phenyl-9H-carbazol-3-yl) phenyl) -9H-fluorene- 2-amine [1,1'-biphenyl] -4-amine, "HT-2" is N, N-bis (4- (dibenzo [b, d] furan-4-yl) phenyl) -[1,1 ': 4', 1 ''-bitriphenyl] -4-amine, "BH-1" is 2- (10-phenylanthracene-9-yl) naphtho [2,3- b] benzofuran, "ET-1" is 4,6,8,10-tetraphenyl [1,4] benzoxaborocyclohexene [2,3,4-k1] phenoxyboron Heterocyclohexene, "ET-2" is 3,3 '-((2-phenylanthracene-9,10-diyl) bis (4,1-phenylene)) bis (4-methylpyridine) . The chemical structure is shown below along with "Liq".

[Chemical 182]

A 26 mm × 28 mm × 0.7 mm glass substrate (manufactured by Opto Science Co., Ltd.), which was ground to a thickness of 150 nm by sputtering to a thickness of 180 nm, 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 Vacuum Co., Ltd.), and HI, HAT-CN, HT-1, HT-2, BH-1, and The compound (1-25), ET-1, and ET-2 are boats for vapor deposition made of molybdenum, and boats for vapor deposition made of aluminum nitride to which Liq, LiF, and aluminum are added, respectively.

The following layers are sequentially formed on the ITO film of the transparent support substrate. The vacuum chamber was decompressed to 5 × 10 ^-4 Pa. First, HI was heated so that the film thickness was 40 nm, and then HAT-CN was heated so that the film thickness was 5 nm. HT-1 was vapor-deposited, and then HT-1 was heated so that the film thickness was 45 nm, and then HT-2 was heated so that the film thickness was 10 nm. Thereby, a hole layer including four layers is formed. Then, BH-1 and the compound (1-25) were simultaneously heated and vapor-deposited so that the film thickness became 25 nm to form a light-emitting layer. The vapor deposition rate was adjusted so that the weight ratio of BH-1 to the compound (1-25) was approximately 98 to 2. Next, ET-1 was heated and vapor-deposited so that the film thickness became 5 nm, and ET-2 and Liq were simultaneously heated and vapor-deposited so that the film thickness became 25 nm, thereby forming Two electronic layers. The vapor deposition rate was adjusted so that the weight ratio of ET-2 to Liq was approximately 50 to 50. The vapor deposition rate of each layer is 0.01 nm / sec to 1 nm / sec. After that, LiF was heated and vapor-deposited at a deposition rate of 0.01 nm / sec to 0.1 nm / sec so that the film thickness became 1 nm, and then aluminum was heated to a film thickness of 100 nm The cathode was formed by vapor deposition in this manner to obtain an organic EL element.

Using an ITO electrode as an anode and a LiF / aluminum electrode as a cathode to apply a DC voltage and measuring the characteristics at 1000 cd / m ² when emitting light, the result was a blue light emission with a wavelength of 458 nm, a driving voltage of 3.68 V, and an external quantum efficiency of 7.96%. . In addition, the time for which the brightness of 90% or more of the initial brightness was maintained was 329 hours.

<Example 2 and Example 3>
The material configuration of each layer of the organic EL element of Example 2 and Example 3 and the EL characteristic data are shown in Tables 2A and 2B below.

[Table 2A]
[Table 2B]

<Example 2>
A 26 mm × 28 mm × 0.7 mm glass substrate (manufactured by Opto Science Co., Ltd.), which was ground to a thickness of 150 nm by sputtering to a thickness of 180 nm, 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 Vacuum Co., Ltd.), and HI, HAT-CN, HT-1, HT-2, BH-1, and The compound (1-16), ET-1, and ET-2 are boats for vapor deposition made of molybdenum, and boats for vapor deposition made of aluminum nitride to which Liq, LiF, and aluminum are added, respectively.

The following layers are sequentially formed on the ITO film of the transparent support substrate. The vacuum chamber was decompressed to 5 × 10 ^-4 Pa. First, HI was heated so that the film thickness was 40 nm, and then HAT-CN was heated so that the film thickness was 5 nm. HT-1 was vapor-deposited, and then HT-1 was heated so that the film thickness was 45 nm, and then HT-2 was heated so that the film thickness was 10 nm. Thereby, a hole layer including four layers is formed. Then, BH-1 and the compound (1-16) were simultaneously heated and vapor-deposited so that the film thickness became 25 nm to form a light-emitting layer. The vapor deposition rate was adjusted so that the weight ratio of BH-1 to the compound (1-16) was approximately 98 to 2. Next, ET-1 was heated and vapor-deposited so that the film thickness became 5 nm, and ET-2 and Liq were simultaneously heated and vapor-deposited so that the film thickness became 25 nm, thereby forming Two electronic layers. The vapor deposition rate was adjusted so that the weight ratio of ET-2 to Liq was approximately 50 to 50. The vapor deposition rate of each layer is 0.01 nm / sec to 1 nm / sec. After that, LiF was heated and vapor-deposited at a deposition rate of 0.01 nm / sec to 0.1 nm / sec so that the film thickness became 1 nm, and then aluminum was heated to a film thickness of 100 nm The cathode was formed by vapor deposition in this manner to obtain an organic EL element.

Using an ITO electrode as an anode and a LiF / aluminum electrode as a cathode to apply a DC voltage, and measuring the characteristics at 1000 cd / m ² when emitting light, the result was a blue light emission with a wavelength of 464 nm, a driving voltage of 3.49 V, and an external quantum efficiency of 8.57%. . In addition, the time for which the brightness of 90% or more of the initial brightness was maintained was 111 hours.

<Example 3>
An organic EL element was prepared by the method according to Example 2 (Table 2A), and EL characteristics were measured (Table 2B).

<Example 4 to Example 28>
The material configuration of each layer of the organic EL elements of Examples 4 to 28 and EL characteristic data are shown in Tables 3A and 3B below.
[Table 3A]

[Table 3B]

<Example 4>
A 26 mm × 28 mm × 0.7 mm glass substrate (manufactured by Opto Science Co., Ltd.), which was ground to a thickness of 150 nm by sputtering to a thickness of 180 nm, 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 Vacuum Co., Ltd.), and HI, HAT-CN, HT-1, HT-2, BH-1, and The compound (1-16), ET-1, and ET-2 are boats for vapor deposition made of molybdenum, and boats for vapor deposition made of aluminum nitride to which Liq, LiF, and aluminum are added, respectively.

The following layers are sequentially formed on the ITO film of the transparent support substrate. The vacuum chamber was decompressed to 5 × 10 ^-4 Pa. First, HI was heated so that the film thickness was 40 nm, and then HAT-CN was heated so that the film thickness was 5 nm. HT-1 was vapor-deposited, and then HT-1 was heated so that the film thickness was 45 nm, and then HT-2 was heated so that the film thickness was 10 nm. Thereby, a hole layer including four layers is formed. Then, BH-1 and the compound (1-16) were simultaneously heated and vapor-deposited so that the film thickness became 25 nm to form a light-emitting layer. The vapor deposition rate was adjusted so that the weight ratio of BH-1 to the compound (1-16) was approximately 98 to 2. Next, ET-1 was heated and vapor-deposited so that the film thickness became 5 nm, and ET-2 and Liq were simultaneously heated and vapor-deposited so that the film thickness became 25 nm, thereby forming Two electronic layers. The vapor deposition rate was adjusted so that the weight ratio of ET-2 to Liq was approximately 50 to 50. The vapor deposition rate of each layer is 0.01 nm / sec to 1 nm / sec. After that, LiF was heated and vapor-deposited at a deposition rate of 0.01 nm / sec to 0.1 nm / sec so that the film thickness became 1 nm, and then aluminum was heated to a film thickness of 100 nm The cathode was formed by vapor deposition in this manner to obtain an organic EL element.

Using an ITO electrode as an anode and a LiF / aluminum electrode as a cathode to apply a DC voltage, and measuring the characteristics at 1000 cd / m ² when emitting light, the result was a blue light emission with a wavelength of 464 nm, a driving voltage of 3.49 V, and an external quantum efficiency of 8.57%. . In addition, the time for which the brightness of 90% or more of the initial brightness was maintained was 111 hours.

<Example 5 to Example 28>
An organic EL element was prepared by the method according to Example 4 (Table 3A), and EL characteristics were measured (Table 3B).

<Evaluation of coating organic EL element>
Next, an organic EL element obtained by coating and forming an organic layer will be described.

<Polymer Host Compound: Synthesis of SPH-101>
SPH-101 was synthesized according to the method described in International Publication No. 2015/008851. A copolymer obtained by binding M2 or M3 to the ortho position of M1 is estimated from the loading ratio: each unit is 50:26:24 (Molar ratio).
[化 183]

<Polymer Hole Transporting Compound: Synthesis of XLP-101>
XLP-101 was synthesized according to the method described in Japanese Patent Laid-Open No. 2018-61028. A copolymer obtained by bonding M2 or M3 to the ortho position of M7 was estimated from the loading ratio: each unit was 40:10:50 (Molar ratio).
[Chemical 184]

<Example 29 to Example 37>
A coating solution for a material forming each layer is prepared, and a coating-type organic EL element is produced.

<Fabrication of Organic EL Elements of Examples 29 to 31>
The material composition of each layer in the organic EL element is shown in Table 4.

[Table 4]

The structure of "ET1" in Table 4 is shown below.
[Chemical 185]

<Preparation of the composition (1) for forming a light emitting layer>
The composition (1) for forming a light-emitting layer was prepared by stirring the following components until a uniform solution was obtained. The prepared composition for forming a light-emitting layer was spin-coated on a glass substrate and dried under reduced pressure to obtain a coating film having no film defects and excellent smoothness.
Compound (A) 0.04% by weight
SPH-101 1.96% by weight
Xylene 69.00% by weight
Decahydronaphthalene 29.00% by weight

Furthermore, the compound (A) is a polycyclic aromatic compound represented by the general formula (1), a multimer thereof, the polycyclic aromatic compound, or a multimer thereof as a monomer (that is, the monomer has Reactive substituent) a polymer compound obtained by polymerizing, or a polymer crosslinked body obtained by further crosslinking the polymer compound. The polymer compound used to obtain the polymer crosslinked body has a crosslinkable substituent.

<PEDOT: PSS solution>
A commercially available PEDOT: PSS solution (Clevios (TM) P VP AI4083, PEDOT: an aqueous dispersion of PSS, manufactured by Heraeus Holdings) was used.
[Chemical 186]

＜ Preparation of OTPD solution ＞
OTPD (LT-N159, manufactured by Luminescence Technology Corp.) and IK-2 (photocationic polymerization initiator, manufactured by Sanapro) were dissolved in toluene to prepare an OTPD concentration of 0.7 An OTPD solution with a wt% and IK-2 concentration of 0.007 wt%.
[Chemical 187]

<Preparation of XLP-101 solution>
XLP-101 was dissolved in xylene at a concentration of 0.6% by weight to prepare a 0.7% by weight XLP-101 solution.

＜ Preparation of PCz solution ＞
PCz (polyvinylcarbazole) was dissolved in dichlorobenzene to prepare a 0.7% by weight PCz solution.
[Chemical 188]

<Example 29>
PEDOT: PSS solution was spin-coated on a glass substrate on which ITO was deposited to a thickness of 150 nm, and then fired on a hot plate at 200 ° C for 1 hour. Floor). Next, the OTPD solution was spin-coated, dried on a hot plate at 80 ° C for 10 minutes, and then exposed with an exposure machine at an exposure intensity of 100 mJ / cm ² , and calcined on a hot plate at 100 ° C for 1 hour to make it insoluble OTPD film (hole transport layer) with a film thickness of 30 nm. Then, the light-emitting layer-forming composition (1) was spin-coated and fired on a hot plate at 120 ° C. for 1 hour, thereby producing a light-emitting layer having a film thickness of 20 nm.

The produced multilayer film was fixed to a substrate holder of a commercially available vapor deposition device (manufactured by Showa Vacuum Co., Ltd.), and a molybdenum vapor deposition boat to which ET1 was added, and a molybdenum vapor deposition to which LiF was added Boats, boats made of tungsten with aluminum added to it. The vacuum chamber was decompressed to 5 × 10 ^-4 Pa, and then ET1 was heated and vapor-deposited so that the film thickness became 30 nm to form an electron transport layer. The deposition rate when the electron transport layer was formed was set to 1 nm / sec. Thereafter, LiF was heated and vapor-deposited at a vapor deposition rate of 0.01 nm / sec to 0.1 nm / sec so that the film thickness became 1 nm. Next, aluminum was heated and vapor-deposited so that a film thickness might become 100 nm, and the cathode was formed. An organic EL element was obtained in this manner.

<Example 30>
An organic EL element was obtained by the same method as in Example 29. In addition, as for the hole transport layer, the XLP-101 solution was spin-coated and calcined on a hot plate at 200 ° C for 1 hour, thereby forming a film with a thickness of 30 nm.

<Example 31>
An organic EL element was obtained by the same method as in Example 29. Furthermore, the hole transporting layer was spin-coated with a PCz solution and calcined on a hot plate at 120 ° C. for 1 hour, thereby forming a film having a thickness of 30 nm.

<Fabrication of Organic EL Device of Example 32 to Example 34>
The material configuration of each layer in the organic EL element is shown in Table 5.
[table 5]

<Preparation of the composition (2) for forming a light-emitting layer to the composition (4) for forming a light-emitting layer>
The composition (2) for forming a light-emitting layer was prepared by stirring the following components until a uniform solution was obtained.
Compound (A) 0.02% by weight
mCBP 1.98% by weight
98.00% by weight of toluene

The composition (3) for forming a light-emitting layer was prepared by stirring the following components until a uniform solution was obtained.
Compound (A) 0.02% by weight
SPH-101 1.98% by weight
Xylene 98.00% by weight

The composition (4) for forming a light-emitting layer was prepared by stirring the following components until a uniform solution was obtained.
Compound (A) 0.02% by weight
DOBNA 1.98% by weight
98.00% by weight of toluene

In Table 5, "DOBNA" is 3,11-di-o-tolyl-5,9-dioxa-13b-boronaphtho [3,2,1-de] anthracene. The chemical structure is shown below.
[Chemical 189]

<Example 32>
A solution of ND-3202 (manufactured by Nissan Chemical Industries) was spin-coated on a glass substrate having a thickness of 45 nm formed on the glass substrate, and then heated at 50 ° C for 3 minutes in an atmospheric environment, and further heated at 230 ° C for 15 minutes, thereby preparing a solution. ND-3202 (hole injection layer) was formed with a thickness of 50 nm. Then, the XLP-101 solution was spin-coated and heated on a hot plate at 200 ° C for 30 minutes under a nitrogen atmosphere, thereby forming an XLP-101 film (hole transport layer) with a thickness of 20 nm. Next, the light-emitting layer-forming composition (2) was spin-coated, and heated at 130 ° C. for 10 minutes under a nitrogen atmosphere to prepare a 20 nm light-emitting layer.

The produced multilayer film was fixed to a substrate holder of a commercially available vapor deposition device (manufactured by Showa Vacuum Co., Ltd.), and a molybdenum vapor deposition boat to which TSPO1 was added, and a molybdenum vapor deposition to which LiF was added were mounted. Boats, boats made of tungsten with aluminum added to it. The vacuum chamber was decompressed to 5 × 10 ^-4 Pa, and then TSPO1 was heated and vapor-deposited so that the film thickness became 30 nm to form an electron transport layer. The deposition rate when the electron transport layer was formed was set to 1 nm / sec. Thereafter, LiF was heated and vapor-deposited at a vapor deposition rate of 0.01 nm / sec to 0.1 nm / sec so that the film thickness became 1 nm. Next, aluminum was heated and vapor-deposited so that a film thickness might become 100 nm, and the cathode was formed. An organic EL element was obtained in this manner.

<Example 33 and Example 34>
An organic EL element was obtained by using the composition (3) for forming a light-emitting layer or the composition (4) for forming a light-emitting layer by the same method as in Example 32.

<Fabrication of Organic EL Device of Example 35 to Example 37>
The material composition of each layer in the organic EL element is shown in Table 6.
[TABLE 6]

<Preparation of the composition (5) for forming a light-emitting layer to the composition (7) for forming a light-emitting layer>
The composition for forming a light emitting layer was prepared by stirring the following components until a uniform solution was obtained.
Compound (A) 0.02% by weight
2PXZ-TAZ 0.18% by weight
mCBP 1.80% by weight
98.00% by weight of toluene

The composition for forming a light emitting layer was prepared by stirring the following components until a uniform solution was obtained.
Compound (A) 0.02% by weight
2PXZ-TAZ 0.18% by weight
SPH-101 1.80% by weight
Xylene 98.00% by weight

The composition for forming a light emitting layer was prepared by stirring the following components until a uniform solution was obtained.
Compound (A) 0.02% by weight
2PXZ-TAZ 0.18% by weight
DOBNA 1.80% by weight
98.00% by weight of toluene

In Table 6, "2PXZ-TAZ" is 10,10 '-((4-phenyl-4H-1,2,4-triazole-3,5-diyl) bis (4,1-phenyl) ) Bis (10H-morphoxazine). The chemical structure is shown below.
[Chemical 190]

<Example 35>
A solution of ND-3202 (manufactured by Nissan Chemical Industries) was spin-coated on a glass substrate having a thickness of 45 nm formed on the glass substrate, and then heated at 50 ° C for 3 minutes in an atmospheric environment, and further heated at 230 ° C for 15 minutes, thereby preparing a solution. ND-3202 (hole injection layer) was formed with a thickness of 50 nm. Then, the XLP-101 solution was spin-coated and heated on a hot plate at 200 ° C for 30 minutes under a nitrogen atmosphere, thereby forming an XLP-101 film (hole transport layer) with a thickness of 20 nm. Next, the light-emitting layer-forming composition (5) was spin-coated, and heated at 130 ° C. for 10 minutes in a nitrogen atmosphere to prepare a 20 nm light-emitting layer.

The produced multilayer film was fixed to a substrate holder of a commercially available vapor deposition device (manufactured by Showa Vacuum Co., Ltd.), and a molybdenum vapor deposition boat to which TSPO1 was added and a molybdenum vapor deposition to which LiF was added Boats, boats made of tungsten with aluminum added to it. The vacuum chamber was decompressed to 5 × 10 ^-4 Pa, and then TSPO1 was heated and vapor-deposited so that the film thickness became 30 nm to form an electron transport layer. The deposition rate when the electron transport layer was formed was set to 1 nm / sec. Thereafter, LiF was heated and vapor-deposited at a vapor deposition rate of 0.01 nm / sec to 0.1 nm / sec so that the film thickness became 1 nm. Next, aluminum was heated and vapor-deposited so that a film thickness might become 100 nm, and the cathode was formed. An organic EL element was obtained in this manner.

<Example 36 and Example 37>
An organic EL device was obtained by using the composition (6) for forming a light-emitting layer or the composition (7) for forming a light-emitting layer by the same method as in Example 35.
[Industrial availability]

In the present invention, by providing a novel cycloalkyl-substituted polycyclic aromatic compound, options for materials for organic devices such as materials for organic EL elements can be increased. In addition, by using a novel cycloalkyl-substituted polycyclic aromatic compound as a material for an organic EL element, it is possible to provide, for example, an organic EL element excellent in light emission efficiency and element life, a display device including the same, and a lighting device including the same. Wait.

100‧‧‧Organic electroluminescence element (organic EL element)

101‧‧‧ substrate

102‧‧‧Anode

103‧‧‧ Hole injection layer

104‧‧‧ Hole Transmission Layer

105‧‧‧Light-emitting layer

106‧‧‧ electron transmission layer

107‧‧‧ electron injection layer

108‧‧‧ cathode

FIG. 1 is a schematic cross-sectional view showing the organic EL element of this embodiment.

Claims (33)

A polycyclic aromatic compound or a multimer of a polycyclic aromatic compound, wherein the polycyclic aromatic compound is represented by the following general formula (1), and the multimer of the polycyclic aromatic compound has a plurality of A structure represented by the following general formula (1), In the formula (1), the A ring, the B ring and the C ring are independently an aryl ring or a heteroaryl ring, and at least one hydrogen in these rings may be substituted, and Y ¹ is B, P, and P = O, P = S, Al, Ga, As, Si-R or Ge-R, wherein R of the Si-R and Ge-R is an aryl group or an alkyl group, and X ¹ and X ² are each independently> O, >NR,> C (-R) ₂ ,> S, or> Se, where R of> NR is a aryl group that may be substituted, a heteroaryl group that may be substituted, an alkyl group that may be substituted, or a substituted Cycloalkyl, the R of the> C (-R) ₂ is hydrogen, an aryl or an alkyl group which may be substituted, and the R of the> NR and / or the R of the> C (-R) ₂ The A ring, B ring and / or C ring may be bonded through a linking group or a single bond, and at least one hydrogen in the compound or structure represented by formula (1) may be substituted by deuterium, cyano or halogen, At least one hydrogen in the compound or structure represented by the formula (1) is substituted with a cycloalkyl group. The polycyclic aromatic compound or the polymer thereof according to item 1 of the scope of the patent application, wherein the A ring, the B ring, and the C ring are each independently an aryl ring or a heteroaryl ring. One hydrogen can be substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted diarylamino, substituted or unsubstituted diheteroarylamine , Substituted or unsubstituted arylheteroarylamine, substituted or unsubstituted diarylboryl (two aryl groups may be bonded via a single bond or a linker), substituted or unsubstituted A substituted alkyl group, a substituted or unsubstituted alkoxy group, or a substituted or unsubstituted aryloxy group. In addition, these rings have a central group of the formula containing Y ¹ , X ^1, and X ² . The condensed bicyclic structure has a 5-membered ring or a 6-membered ring, Y ¹ is B, P, P = O, P = S, Al, Ga, As, Si-R, or Ge-R. The Si-R And R of Ge-R is an aryl group or an alkyl group, X ¹ and X ² are independently>O,>NR,> C (-R) ₂ ,> S or> Se, and R of Alkyl-substituted aryl, alkyl-substituted heteroaryl, An alkyl group or a cycloalkyl group, R of the> C (-R) ₂ is hydrogen, and an aryl group or an alkyl group which may be substituted by an alkyl group; and R of the> NR and / or the> C (-R R of ₂ ) may be bonded to the A ring, the B ring, and / or the C ring through -O-, -S-, -C (-R) _2- , or a single bond, and the -C (-R ) ₂ -R is hydrogen or alkyl, and at least one hydrogen in the compound or structure represented by formula (1) may be substituted by deuterium, cyano, or halogen, and in the case of a polymer, it has 2 or 3 A dimer or trimer having a structure represented by the general formula (1), and at least one hydrogen in the compound or structure represented by the formula (1) is substituted with a cycloalkyl group. The polycyclic aromatic compound according to item 1 of the scope of patent application, which is represented by the following general formula (2), In the formula (2), R ¹ to R ¹¹ are each independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, and diaryl. Boron (two aryl groups may be bonded via a single bond or a linking group), an alkyl group, an alkoxy group, or an aryloxy group, at least one of which may be substituted by an aryl group, a heteroaryl group, or an alkyl group, and Adjacent groups in R ¹ to R ¹¹ may be bonded to each other and form an aryl ring or a heteroaryl ring together with the a ring, the b ring, or the c ring. At least one hydrogen in the formed ring may be an aryl group, Heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamine, diarylboryl (two aryl groups may be bonded via a single bond or a linking group), an alkyl group, Alkoxy or aryloxy substituted, at least one of these hydrogens may be substituted by aryl, heteroaryl or alkyl, Y ¹ is B, P, P = O, P = S, Al, Ga, As, Si -R or Ge-R, wherein R of the Si-R and Ge-R is an aryl group having 6 to 12 carbon atoms or an alkyl group having 1 to 6 carbon atoms, and X ¹ and X ² are independently>O,>NR,> C (-R) ₂ ,> S or> Se, where R of> NR is an aryl group having 6 to 12 carbon atoms and a hetero group having 2 to 15 carbon atoms An aryl group, an alkyl group having 1 to 6 carbon atoms, or a cycloalkyl group having 3 to 14 carbon atoms, and R of C> -R ₂ is hydrogen, and an aryl group having 6 to 12 carbon atoms or 1 to 6 carbon atoms In addition, the R of the> NR and / or the R of the> C (-R) ₂ may be bonded to -O-, -S-, -C (-R) _2- , or a single bond. The a ring, b ring, and / or c ring are bonded, R of the -C (-R) ₂ -is an alkyl group having 1 to 6 carbon atoms, and at least one hydrogen in the compound represented by formula (2) It may be substituted with deuterium, cyano or halogen, and at least one hydrogen in the compound represented by formula (2) is substituted with a cycloalkyl group. The polycyclic aromatic compound according to item 3 of the scope of patent application, wherein R ¹ to R ¹¹ are each independently hydrogen, an aryl group having 6 to 30 carbon atoms, a heteroaryl group having 2 to 30 carbon atoms, and a diaryl group. Amino group (wherein, the aryl group is an aryl group having 6 to 12 carbon atoms), diaryl boron group (wherein the aryl group is an aryl group having 6 to 12 carbon atoms), and the two aryl groups may be connected through a single bond or a linkage And bond)) or an alkyl group having 1 to 24 carbon atoms. In addition, adjacent groups in R ¹ to R ¹¹ may be bonded to each other and form an a, b, or c ring with a carbon number of 9 to 16. An aryl ring or a heteroaryl ring having 6 to 15 carbons. At least one hydrogen in the formed ring may be substituted by an aryl group having 6 to 10 carbons or an alkyl group having 1 to 12 carbons. Y ¹ is B, P , P = O, P = S or Si-R, wherein R of said Si-R is an aryl group having 6 to 10 carbon atoms or an alkyl group having 1 to 4 carbon atoms, and X ¹ and X ² are each independently> O ,>NR,> C (-R) ₂ or> S, where R of> NR is an aryl group having 6 to 10 carbon atoms, an alkyl group having 1 to 4 carbon atoms or a cycloalkyl group having 5 to 10 carbon atoms, The R of the> C (-R) ₂ is hydrogen, an aryl group having 6 to 10 carbon atoms or an alkyl group having 1 to 4 carbon atoms. At least one hydrogen in the compound represented by formula (2) may be deuterium. , Cyano or halogen, and at least one hydrogen in the compound represented by the formula (2) is substituted with a cycloalkyl group. The polycyclic aromatic compound according to item 3 of the scope of patent application, wherein R ¹ to R ¹¹ are each independently hydrogen, an aryl group having 6 to 16 carbon atoms, a heteroaryl group having 2 to 20 carbon atoms, and a diaryl group. Amino group (wherein the aryl group is an aryl group having 6 to 10 carbon atoms) or an alkyl group having 1 to 12 carbon atoms, Y ¹ is B, P, P = O, or P = S, and X ¹ and X ² are independent of each other Is>O,> NR or> C (-R) ₂ , where R of> NR is an aryl group having 6 to 10 carbon atoms, an alkyl group having 1 to 4 carbon atoms or a cycloalkyl group having 5 to 10 carbon atoms Wherein R of the> C (-R) ₂ is hydrogen, an aryl group having 6 to 10 carbon atoms or an alkyl group having 1 to 4 carbon atoms, and at least one hydrogen in the compound represented by formula (2) is Cycloalkyl substitution. The polycyclic aromatic compound according to item 3 of the scope of patent application, wherein R ¹ to R ¹¹ are each independently hydrogen, an aryl group having 6 to 16 carbon atoms, and a diarylamino group (wherein the aryl group is carbon Aryl group having 6 to 10) or alkyl group having 1 to 12 carbons, Y ¹ is B, X ¹ and X ² are both> NR, or X ¹ is> NR and X ² is> O, which is> NR R is an aryl group having 6 to 10 carbon atoms, an alkyl group having 1 to 4 carbon atoms or a cycloalkyl group having 5 to 10 carbon atoms, and at least one hydrogen in the compound represented by formula (2) is a cycloalkane Radical substitution. The polycyclic aromatic compound or the polymer thereof according to any one of claims 1 to 6 in the scope of the patent application, which is composed of a diarylamino group substituted with a cycloalkyl group, An oxazolyl or benzocarbazolyl substituted with cycloalkyl. The polycyclic aromatic compound according to any one of items 3 to 6 of the scope of the patent application, wherein R ² is a diarylamino group substituted with a cycloalkyl group or a carbazolyl group substituted with a cycloalkyl group . The polycyclic aromatic compound according to any one of claims 1 to 8 in the scope of patent application, wherein the cycloalkyl group is a cycloalkyl group having 3 to 20 carbon atoms. The polycyclic aromatic compound or the polymer thereof according to any one of claims 1 to 9 in the scope of the patent application, wherein the halogen is fluorine. The polycyclic aromatic compound according to item 1 of the scope of patent application, which is represented by any one of the following structural formulas, "Me" in each structural formula is a methyl group, and "tBu" represents a third butyl group. A reactive compound obtained by substituting a reactive substituent in a polycyclic aromatic compound or a multimer thereof according to any one of claims 1 to 11 of the scope of patent application. A polymer compound or a polymer crosslinked body, wherein the polymer compound is obtained by polymerizing a reactive compound as described in item 12 of a patent application as a monomer, and the polymer crosslinked body It is formed by further cross-linking the polymer compound. A suspension type polymer compound or a suspension type polymer cross-linked body, wherein the suspension type polymer compound is substituted in the main chain type polymer by the reactive compound described in item 12 of the patent application scope, The suspended polymer crosslinked body is obtained by further crosslinking the suspended polymer compound. A material for an organic device, comprising the polycyclic aromatic compound or a multimer thereof according to any one of claims 1 to 11 of the scope of patent application. A material for an organic device, comprising the reactive compound described in item 12 of the scope of patent application. A material for an organic device, which contains a polymer compound or a polymer crosslinked body as described in item 13 of the scope of patent application. A material for an organic device, which comprises a pendant polymer compound or a pendant polymer crosslinked body as described in item 14 of the scope of patent application. The material for an organic device according to any one of claims 15 to 18, wherein the material for an organic device is a material for an organic electroluminescence element, a material for an organic field effect transistor, or an organic thin film Materials for solar cells. The material for an organic device according to item 19 of the scope of application for a patent, wherein the material for an organic electroluminescent element is a material for a light emitting layer. An ink composition comprising: the polycyclic aromatic compound or a polymer thereof according to any one of claims 1 to 11 of the scope of patent application; and an organic solvent. An ink composition comprising: the reactive compound according to item 12 of the scope of patent application; and an organic solvent. An ink composition includes: a main chain polymer; a reactive compound according to item 12 of the scope of patent application; and an organic solvent. An ink composition, comprising: the polymer compound or polymer crosslinked body as described in item 13 of the scope of patent application; and an organic solvent. An ink composition includes: a hanging polymer compound or a hanging polymer crosslinked body according to item 14 of the scope of application for a patent; and an organic solvent. An organic electroluminescence element includes: a pair of electrodes including an anode and a cathode; and an organic layer disposed between the pair of electrodes, and including any one of items 1 to 11 of a patent application range. The polycyclic aromatic compound or its multimer, the reactive compound described in item 12 of the patent application scope, the polymer compound or polymer crosslinked body described in item 13 of the patent application scope, or The pendant polymer compound or the pendant polymer cross-linked body according to item 14 of the patent scope. An organic electroluminescence element includes: a pair of electrodes including an anode and a cathode; and a light-emitting layer disposed between the pair of electrodes, and containing any one of items 1 to 11 of the scope of patent application The polycyclic aromatic compound or its multimer, the reactive compound described in item 12 of the patent application scope, the polymer compound or polymer crosslinked body described in item 13 of the patent application scope, or The pendant polymer compound or the pendant polymer cross-linked body according to item 14 of the patent scope. The organic electroluminescence element according to item 27 of the scope of patent application, wherein the light emitting layer includes: a host; and the polycyclic aromatic compound as a dopant, a polymer thereof, a reactive compound, Molecular compounds, polymer crosslinked bodies, suspended polymer compounds or suspended polymer crosslinked bodies. The organic electroluminescence device according to item 28 of the scope of application for a patent, wherein the host is an anthracene-based compound, a fluorene-based compound, or a dibenzofluorene-based compound. The organic electroluminescence element according to any one of claims 26 to 29, which has an electron transport layer and / or an electron injection layer disposed between the cathode and the light emitting layer, and At least one of the electron transport layer and the electron injection layer contains a material selected from the group consisting of a borane derivative, a pyridine derivative, a fluoranthene derivative, a BO-based derivative, an anthracene derivative, a benzofluorene derivative, a phosphine oxide derivative, At least one of a group consisting of a pyrimidine derivative, a carbazole derivative, a triazine derivative, a benzimidazole derivative, a phenanthroline derivative, and a hydroxyquinoline metal complex. The organic electroluminescence device according to item 30 of the scope of patent application, wherein the electron transport layer and / or the electron injection layer further contains a member selected from the group consisting of an alkali metal, an alkaline earth metal, a rare earth metal, an oxide of an alkali metal, and an alkali metal. Halide, oxide of alkaline earth metal, halide of alkaline earth metal, oxide of rare earth metal, halide of rare earth metal, organic complex of alkali metal, organic complex of alkaline earth metal, and organic complex of rare earth metal At least one of a group of objects. The organic electroluminescence device according to any one of claims 26 to 31, wherein at least one of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer The layer includes a polymer compound or a polymer crosslinked body, or a pendant polymer compound or a pendant polymer crosslinked body. The polymer compound is obtained by polymerizing a low molecular compound capable of forming each layer as a monomer. The polymer cross-linked body is obtained by further cross-linking the polymer compound, and the pendant polymer compound is formed by reacting a low-molecular compound capable of forming each layer with a main chain polymer. The suspended polymer crosslinked body is obtained by further crosslinking the suspended polymer compound. A display device or lighting device includes the organic electroluminescence element according to any one of the 26th to the 32nd patent application scope.