Polycyclic aromatic compound

Abstract

To provide a novel polycyclic aromatic compound and an organic EL element using the same.SOLUTION: A polycyclic aromatic compound is represented by a formula (1). In the formula (1), a ring A, a ring B, and a ring C are mutually independently an aryl ring or a heteroaryl ring, and the ring B and the ring C can be connected with each other via -O-. In a general formula (BiN), a ring D is a heteroaryl ring including at least one N, a ring E is an aromatic ring or a non-aromatic ring including at least one N, between the ring D and the ring E, an aromatic or nonaromatic condensed ring can be formed, and at least one hydrogen in the ring A, the ring B, and the ring C is substituted with a group represented by the formula (BiN) via a linking group.SELECTED DRAWING: None

Description

[Technical field]

[0001] The present invention relates to a polycyclic aromatic compound and a multimer thereof (hereinafter, also collectively referred to as "polycyclic aromatic compound"), and to an electron transport material, an electron injection material, an organic electroluminescence device, an organic field effect transistor, an organic thin-film solar cell, and a display device and a lighting device, each using the same. In this specification, the "organic electroluminescence device" may be referred to as an "organic EL device" or simply as an "device". [Background technology]

[0002] Conventionally, display devices using electroluminescent light-emitting elements have been extensively studied because they can be made thin and energy-efficient, and organic electroluminescent elements made of organic materials have been actively studied because they can be easily made lighter and larger. In particular, there has been active research into the development of organic materials that have the luminescence properties of blue, one of the three primary colors of light, and organic materials that have the ability to transport charges such as holes and electrons (potential to become semiconductors or superconductors), regardless of whether they are polymeric or low molecular weight compounds.

[0003] An organic EL element has a structure consisting of a pair of electrodes consisting of an anode and a cathode, and one or more layers containing organic compounds that are disposed between the pair of electrodes. The layers containing organic compounds include a light-emitting layer and a charge transport / injection layer that transports or injects charges such as holes and electrons, and various organic materials suitable for these layers have been developed.

[0004] As materials for the light-emitting layer, for example, benzofluorene-based compounds have been developed (WO 2004 / 061047), as hole-transporting materials, for example, triphenylamine-based compounds have been developed (JP 2001-172232), and as electron-transporting materials, for example, anthracene-based compounds have been developed (JP 2005-170911).

[0005] In recent years, a material that improves triphenylamine derivatives has also been reported as a material for use in organic electroluminescence devices and organic thin-film solar cells (WO 2012 / 118164). This material is characterized by its improved planarity, which is achieved by linking the aromatic rings that make up the triphenylamine, with reference to N,N'-diphenyl-N,N'-bis(3-methylphenyl)-1,1'-biphenyl-4,4'-diamine (TPD), which has already been put to practical use. For example, this document evaluates the charge transport properties of an NO-linked compound (compound 1 on page 63), but does not describe how to manufacture materials other than NO-linked compounds. In addition, since the electronic state of the entire compound differs depending on the linked element, the properties obtained from materials other than NO-linked compounds are not yet known. There are other examples of such compounds (WO 2011 / 107186). For example, compounds with a conjugated structure that has a large triplet exciton energy (T1) can emit phosphorescence with a shorter wavelength, and are therefore useful as materials for blue light-emitting layers. In addition, compounds having a new conjugated structure with a large T1 are also required as electron transport materials and hole transport materials that sandwich the light-emitting layer. [Prior art documents] [Patent documents]

[0006] [Patent Document 1] International Publication No. 2004 / 061047 [Patent Document 2] JP 2001-172232 A [Patent Document 3] JP 2005-170911 A [Patent Document 4] International Publication No. 2012 / 118164 [Patent Document 5] International Publication No. 2011 / 107186 [Patent Document 6] International Publication No. 2015 / 102118 Summary of the Invention [Problem to be solved by the invention]

[0007] As described above, various materials have been developed for use in organic EL devices, but in order to increase the options for materials for organic EL devices, it is desirable to develop materials made of compounds different from conventional ones. In particular, the organic EL characteristics obtained from materials other than the NO-linked compounds reported in Patent Documents 1 to 4 and the manufacturing methods thereof are not yet known.

[0008] In addition, Patent Document 6 reports a boron-containing polycyclic aromatic compound and an organic EL device using the same. However, in order to further improve the device characteristics, there is a demand for an electron transport material that can improve the luminous efficiency and device life. [Means for solving the problem]

[0009] As a result of intensive research to solve the above problems, the present inventors have found that an excellent organic EL device can be obtained by, for example, constructing an organic EL device by disposing, between a pair of electrodes, an electron transport layer containing a polycyclic aromatic compound into which a nitrogen-containing group having a specific structure has been introduced, and have thus completed the present invention. That is, the present invention provides the following polycyclic aromatic compound.

[0010] In this specification, the chemical structure or the substituent may be expressed by the number of carbon atoms, but the number of carbon atoms in the case where a substituent is substituted on the chemical structure or where a substituent is further substituted on the substituent means the number of carbon atoms in each of the chemical structure and the substituent, and does not mean the total number of carbon atoms in the chemical structure and the substituent, or the total number of carbon atoms in the substituent and the substituent. For example, "substituent B of carbon number Y substituted with substituent A of carbon number X" means that "substituent B of carbon number Y" is substituted with "substituent A of carbon number X", and the carbon number Y is not the total number of carbon atoms in the substituent A and the substituent B. Also, for example, "substituent B of carbon number Y substituted with substituent A" means that "substituent B of carbon number Y" is substituted with "substituent A (without carbon number limit)", and the carbon number Y is not the total number of carbon atoms in the substituent A and the substituent B.

[0011] Section 1. A polycyclic aromatic compound represented by the following general formula (1), or a multimer of a polycyclic aromatic compound having a plurality of structures represented by the following general formula (1). [ka] In the above formula (1), ring A, ring B and ring C are each independently an aryl ring or a heteroaryl ring, at least one hydrogen atom in these rings may be substituted, and ring B and ring C may be linked via -O-; In the above general formula (BiN), ring D is a heteroaryl ring containing at least one N, ring E is an aromatic or non-aromatic ring containing at least one N, an aromatic or non-aromatic fused ring may be formed between ring D and ring E, and at least one hydrogen atom in these rings may be substituted; at least one hydrogen atom in ring A, ring B and ring C is substituted with a group represented by the above formula (BiN) via a linking group, * indicates a bonding position, In the compound or structure represented by formula (1), at least one of the A ring, the B ring, the C ring, the aryl and the heteroaryl may be fused with at least one cycloalkane, at least one hydrogen in the cycloalkane may be substituted, and at least one -CH2- in the cycloalkane may be substituted with -O-, and At least one hydrogen in the compound or a multimer thereof may be substituted with cyano, halogen or deuterium.

[0012] Section 2. at least one hydrogen atom in ring A, ring B, ring C, ring D, ring E and the fused ring may be substituted by a substituted or unsubstituted aryl, a substituted or unsubstituted heteroaryl, a substituted or unsubstituted diarylamino, a substituted or unsubstituted diheteroarylamino, a substituted or unsubstituted arylheteroarylamino, a substituted or unsubstituted diarylboryl (two aryls may be bonded via a single bond or a linking group), a substituted or unsubstituted alkyl, a substituted or unsubstituted cycloalkyl, a substituted or unsubstituted alkoxy, a substituted or unsubstituted aryloxy, or a substituted silyl; The A ring, the B ring and the C ring each have a 5-membered or 6-membered ring that shares a bond with the central fused two-ring structure of formula (1) composed of the central element "B (boron)" and two elements "O (oxygen)"; the linking group is a single bond, an arylene, a heteroarylene, an alkylene, an alkenylene, an alkynylene, -O-, -S-, >NR, or a combination thereof, in which R of >NR is an aryl, a heteroaryl, an alkyl, or a cycloalkyl, and at least one hydrogen atom in the linking group may be replaced by an aryl, a heteroaryl, an alkyl, or a cycloalkyl; In the compound or structure represented by formula (1), at least one of the A ring, the B ring, the C ring, the aryl and the heteroaryl may be fused with at least one cycloalkane, at least one hydrogen in the cycloalkane may be substituted, and at least one -CH2- in the cycloalkane may be substituted with -O-, and In the case of a polymer, it is a dimer or trimer having two or three structures represented by formula (1). Item 1. A polycyclic aromatic compound or a multimer thereof according to item 1.

[0013] Section 3. Item 1. A polycyclic aromatic compound or a multimer thereof according to item 1, which is represented by the following general formula (2): [ka] In the above formula (2), In the ring a, the ring b, and the ring c, any "-C(-R)=" (where R is R in formula (2) 1 ~R 11 ) may be replaced with "-N=", and any "-C(-R)=C(-R)-" (where R is R in formula (2) 1 ~R 11 may be replaced with "-N(-R)-", "-O-", or "-S-", where R in "-N(-R)-" is aryl, alkyl, or cycloalkyl; R 1 ~R 11 are each independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl (two aryls may be bonded via a single bond or a linking group), alkyl, cycloalkyl, alkoxy, aryloxy, triarylsilyl, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl or alkyldicycloalkylsilyl, in which at least one hydrogen may be substituted with an aryl, heteroaryl, alkyl or cycloalkyl; R 1 ~R 11 adjacent groups among the above may be bonded to each other to form an aryl ring or a heteroaryl ring together with the a ring, the b ring or the c ring, and at least one hydrogen atom in the formed ring may be replaced by an aryl, a heteroaryl, a diarylamino, a diheteroarylamino, an arylheteroarylamino, a diarylboryl (two aryls may be bonded via a single bond or a linking group), an alkyl, a cycloalkyl, an alkoxy, an aryloxy, a triarylsilyl, a trialkylsilyl, a tricycloalkylsilyl, a dialkylcycloalkylsilyl or an alkyldicycloalkylsilyl, and at least one hydrogen atom in these may be replaced by an aryl, a heteroaryl, an alkyl or a cycloalkyl; R 7 and R 8 may be bonded to form -O-, In formula (BiN) in Item 1, ring D is a heteroaryl ring containing at least one N and having 2 to 30 carbon atoms, ring E is an aromatic ring containing at least one N and having 2 to 30 carbon atoms or a non-aromatic ring containing 2 to 30 carbon atoms, and an aromatic or non-aromatic fused ring having 2 to 15 carbon atoms may be formed between ring D and ring E; At least one hydrogen atom in the D ring, the E ring and the fused ring may be substituted with an aryl, a heteroaryl, a diarylamino, a diheteroarylamino, an arylheteroarylamino, a diarylboryl (two aryls may be bonded via a single bond or a linking group), an alkyl, a cycloalkyl, an alkoxy, an aryloxy, a triarylsilyl, a trialkylsilyl, a tricycloalkylsilyl, a dialkylcycloalkylsilyl or an alkyldicycloalkylsilyl, and at least one hydrogen atom in these may be substituted with an aryl, a heteroaryl, an alkyl or a cycloalkyl; R 1 ~R 11 is a group represented by formula (BiN) in item 1 via a linking group, or at least one hydrogen atom in the formed aryl ring or heteroaryl ring is replaced with a group represented by formula (BiN) via a linking group, * indicates a bonding position, the linking group is a single bond, an arylene having 6 to 30 carbon atoms, a heteroarylene having 2 to 30 carbon atoms, an alkylene having 1 to 24 carbon atoms, an alkenylene having 1 to 24 carbon atoms, an alkynylene having 1 to 24 carbon atoms, -O-, -S-, >NR, or a combination thereof, in which R in >NR is an aryl having 6 to 16 carbon atoms, a heteroaryl having 2 to 20 carbon atoms, an alkyl having 1 to 12 carbon atoms, or a cycloalkyl having 3 to 16 carbon atoms, and at least one hydrogen atom in the linking group may be substituted by an aryl having 6 to 16 carbon atoms, a heteroaryl having 2 to 20 carbon atoms, an alkyl having 1 to 12 carbon atoms, or a cycloalkyl having 3 to 16 carbon atoms; At least one hydrogen atom in the compound or a multimer thereof may be replaced with a cyano, a halogen, or a deuterium atom; In the compound or structure represented by formula (2), at least one of the ring a, the ring b, the ring c, the formed ring, the aryl and the heteroaryl may be condensed with at least one cycloalkane having 3 to 24 carbon atoms, at least one hydrogen in the cycloalkane may be substituted with an aryl having 6 to 30 carbon atoms, a heteroaryl having 2 to 30 carbon atoms, an alkyl having 1 to 24 carbon atoms or a cycloalkyl having 3 to 24 carbon atoms, at least one -CH2- in the cycloalkane may be substituted with -O-, and In the case of a polymer, it is a dimer or trimer having two or three structures represented by formula (2).

[0014] Section 4. In the above formula (2), In the ring a, the ring b, and the ring c, any "-C(-R)=" (where R is R in formula (2) 1 ~R 11 ) may be replaced with "-N=", and any "-C(-R)=C(-R)-" (where R is R in formula (2) 1 ~R 11 may be replaced with "-N(-R)-", "-O-", or "-S-", and R in the "-N(-R)-" is an aryl having 6 to 10 carbon atoms, an alkyl having 1 to 5 carbon atoms, or a cycloalkyl having 5 to 10 carbon atoms; R 1 ~R 11are each independently hydrogen, an aryl having 6 to 30 carbon atoms, a heteroaryl having 2 to 30 carbon atoms, a diarylamino (wherein the aryl is an aryl having 6 to 12 carbon atoms), a diarylboryl (wherein the aryl is an aryl having 6 to 12 carbon atoms, and the two aryls may be bonded via a single bond or a linking group), an alkyl having 1 to 24 carbon atoms, a cycloalkyl having 3 to 24 carbon atoms, an alkoxy having 1 to 24 carbon atoms, an aryloxy having 6 to 30 carbon atoms, a triarylsilyl (wherein the aryl is an aryl having 6 to 12 carbon atoms), or a trialkylsilyl (wherein the alkyl is an alkyl having 1 to 6 carbon atoms), in which at least one hydrogen may be substituted by an alkyl having 1 to 12 carbon atoms or a cycloalkyl having 3 to 16 carbon atoms; R 1 ~R 11 Adjacent groups among these may be bonded to each other to form an aryl ring having 9 to 16 carbon atoms or a heteroaryl ring having 6 to 15 carbon atoms together with ring a, ring b or ring c, and at least one hydrogen in the formed ring may be substituted with an aryl having 6 to 30 carbon atoms, a heteroaryl having 2 to 30 carbon atoms, diarylamino (wherein the aryl is an aryl having 6 to 12 carbon atoms), diarylboryl (wherein the aryl is an aryl having 6 to 12 carbon atoms, and the two aryls may be bonded via a single bond or a linking group), an alkyl having 1 to 24 carbon atoms, a cycloalkyl having 3 to 24 carbon atoms, an alkoxy having 1 to 24 carbon atoms, an aryloxy having 6 to 30 carbon atoms, triarylsilyl (wherein the aryl is an aryl having 6 to 12 carbon atoms), or trialkylsilyl (wherein the alkyl is an alkyl having 1 to 6 carbon atoms), and at least one hydrogen in these may be substituted with an alkyl having 1 to 12 carbon atoms or a cycloalkyl having 3 to 16 carbon atoms. R 7 and R 8 may be bonded to form -O-, In the above formula (BiN), ring D is a heteroaryl ring containing at least one N and having 2 to 20 carbon atoms, ring E is an aromatic ring containing at least one N and having 2 to 20 carbon atoms or a non-aromatic ring containing 2 to 20 carbon atoms, and an aromatic or non-aromatic fused ring having 2 to 10 carbon atoms may be formed between ring D and ring E; at least one hydrogen in ring D, ring E and the fused ring may be substituted with an aryl having 6 to 30 carbon atoms, a heteroaryl having 2 to 30 carbon atoms, diarylamino (wherein aryl is an aryl having 6 to 12 carbon atoms), diarylboryl (wherein aryl is an aryl having 6 to 12 carbon atoms, and two aryls may be bonded via a single bond or a linking group), an alkyl having 1 to 24 carbon atoms, a cycloalkyl having 3 to 24 carbon atoms, an alkoxy having 1 to 24 carbon atoms, an aryloxy having 6 to 30 carbon atoms, triarylsilyl (wherein aryl is an aryl having 6 to 12 carbon atoms), or trialkylsilyl (wherein alkyl is an alkyl having 1 to 6 carbon atoms), and at least one hydrogen in these may be substituted with an alkyl having 1 to 12 carbon atoms or a cycloalkyl having 3 to 16 carbon atoms; R 1 ~R 11 at least one of the above is a group represented by the above formula (BiN) via a linking group, or at least one hydrogen atom in the formed aryl ring or heteroaryl ring is substituted with a group represented by the formula (BiN) via a linking group, * indicates a bonding position, the linking group is a single bond, an arylene having 6 to 12 carbon atoms, a heteroarylene having 2 to 15 carbon atoms, an alkylene having 1 to 12 carbon atoms, an alkenylene having 1 to 12 carbon atoms, an alkynylene having 1 to 12 carbon atoms, -O-, -S-, >NR, or a combination thereof, in which R in >NR is an aryl having 6 to 10 carbon atoms, a heteroaryl having 2 to 10 carbon atoms, an alkyl having 1 to 4 carbon atoms, or a cycloalkyl having 5 to 10 carbon atoms, and at least one hydrogen atom in the linking group may be substituted by an alkyl having 1 to 4 carbon atoms or a cycloalkyl having 5 to 10 carbon atoms; At least one hydrogen atom in the compound or a multimer thereof may be replaced with a cyano, a halogen, or a deuterium atom; In the compound or structure represented by formula (2), at least one of the ring a, the ring b, the ring c, the formed ring, aryl and heteroaryl may be condensed with at least one cycloalkane having 3 to 16 carbon atoms, and at least one hydrogen in the cycloalkane may be substituted with an alkyl having 1 to 6 carbon atoms or a cycloalkyl having 3 to 14 carbon atoms, and In the case of a polymer, it is a dimer having two structures represented by formula (2). Item 3. A polycyclic aromatic compound or a multimer thereof according to item 3.

[0015] Section 5. In the above formula (2), In the ring a, the ring b, and the ring c, any "-C(-R)=" (where R is R in formula (2) 1 ~R 11 ) may be replaced with "-N=", and any "-C(-R)=C(-R)-" (where R is R in formula (2) 1 ~R 11 may be replaced with "-N(-R)-", "-O-", or "-S-", and R in the "-N(-R)-" is an aryl having 6 to 10 carbon atoms, an alkyl having 1 to 5 carbon atoms, or a cycloalkyl having 5 to 10 carbon atoms; R 1 ~R 11 are each independently hydrogen, an aryl having 6 to 16 carbon atoms, a heteroaryl having 2 to 20 carbon atoms, a diarylamino (wherein the aryl is an aryl having 6 to 10 carbon atoms), a diarylboryl (wherein the aryl is an aryl having 6 to 10 carbon atoms, and the two aryls may be bonded via a single bond or a linking group), an alkyl having 1 to 12 carbon atoms, a cycloalkyl having 3 to 16 carbon atoms, an alkoxy having 1 to 6 carbon atoms, an aryloxy having 6 to 16 carbon atoms, a triarylsilyl (wherein the aryl is an aryl having 6 to 10 carbon atoms), or a trialkylsilyl (wherein the alkyl is an alkyl having 1 to 4 carbon atoms), in which at least one hydrogen may be substituted by an alkyl having 1 to 4 carbon atoms or a cycloalkyl having 5 to 10 carbon atoms; R 1 ~R 11Adjacent groups among these may be bonded to each other to form an aryl ring having 9 to 16 carbon atoms or a heteroaryl ring having 6 to 15 carbon atoms together with ring a, ring b or ring c, and at least one hydrogen in the formed ring may be substituted with an aryl having 6 to 16 carbon atoms, a heteroaryl having 2 to 20 carbon atoms, diarylamino (wherein the aryl is an aryl having 6 to 10 carbon atoms), diarylboryl (wherein the aryl is an aryl having 6 to 10 carbon atoms, and the two aryls may be bonded via a single bond or a linking group), an alkyl having 1 to 12 carbon atoms, a cycloalkyl having 3 to 16 carbon atoms, an alkoxy having 1 to 6 carbon atoms, an aryloxy having 6 to 16 carbon atoms, triarylsilyl (wherein the aryl is an aryl having 6 to 10 carbon atoms), or trialkylsilyl (wherein the alkyl is an alkyl having 1 to 4 carbon atoms), and at least one hydrogen in these may be substituted with an alkyl having 1 to 4 carbon atoms or a cycloalkyl having 5 to 10 carbon atoms. R 7 and R 8 may be bonded to form -O-, In the above formula (BiN), ring D is a heteroaryl ring having 2 to 10 carbon atoms containing at least one N, ring E is an aromatic ring having 2 to 10 carbon atoms or a non-aromatic ring having 2 to 10 carbon atoms containing at least one N, and an aromatic or non-aromatic fused ring having 2 to 10 carbon atoms may be formed between ring D and ring E; at least one hydrogen in ring D, ring E and the fused ring may be substituted with an aryl having 6 to 16 carbon atoms, a heteroaryl having 2 to 20 carbon atoms, diarylamino (wherein aryl is an aryl having 6 to 10 carbon atoms), diarylboryl (wherein aryl is an aryl having 6 to 10 carbon atoms, and two aryls may be bonded via a single bond or a linking group), an alkyl having 1 to 12 carbon atoms, a cycloalkyl having 3 to 16 carbon atoms, an alkoxy having 1 to 6 carbon atoms, an aryloxy having 6 to 16 carbon atoms, triarylsilyl (wherein aryl is an aryl having 6 to 10 carbon atoms), or trialkylsilyl (wherein alkyl is an alkyl having 1 to 4 carbon atoms), and at least one hydrogen in these may be substituted with an alkyl having 1 to 4 carbon atoms or a cycloalkyl having 5 to 10 carbon atoms; R 1 ~R 11 at least one of the above is a group represented by the above formula (BiN) via a linking group, or at least one hydrogen atom in the formed aryl ring or heteroaryl ring is substituted with a group represented by the formula (BiN) via a linking group, * indicates a bonding position, the linking group is a single bond, an arylene having 6 to 10 carbon atoms, an alkylene having 1 to 6 carbon atoms, an alkenylene having 1 to 6 carbon atoms, -O-, or a combination thereof, and at least one hydrogen atom in the linking group may be substituted with an alkyl having 1 to 4 carbon atoms; At least one hydrogen atom in the compound or a multimer thereof may be replaced with a cyano, a halogen, or a deuterium atom; In the compound or structure represented by formula (2), at least one of the ring a, the ring b, the ring c, the formed ring, aryl and heteroaryl may be condensed with at least one cycloalkane having 3 to 16 carbon atoms, and at least one hydrogen in the cycloalkane may be substituted with an alkyl having 1 to 6 carbon atoms or a cycloalkyl having 3 to 14 carbon atoms, and In the case of a polymer, it is a dimer having two structures represented by formula (2). Item 3. A polycyclic aromatic compound or a multimer thereof according to item 3.

[0016] Section 6. In the above formula (2), In the ring a, the ring b, and the ring c, any "-C(-R)=" (where R is R in formula (2) 1 ~R 11 ) may be replaced with "-N=", and any "-C(-R)=C(-R)-" (where R is R in formula (2) 1 ~R 11 may be replaced with "-N(-R)-", "-O-", or "-S-", and R in the "-N(-R)-" is an aryl having 6 to 10 carbon atoms, an alkyl having 1 to 5 carbon atoms, or a cycloalkyl having 5 to 10 carbon atoms; R 1 ~R 11each independently represents hydrogen, aryl having 6 to 12 carbon atoms, heteroaryl having 2 to 15 carbon atoms, diarylamino (wherein aryl is an aryl having 6 to 10 carbon atoms), alkyl having 1 to 6 carbon atoms, cycloalkyl having 3 to 14 carbon atoms, triarylsilyl (wherein aryl is an aryl having 6 to 10 carbon atoms), or trialkylsilyl (wherein alkyl is an alkyl having 1 to 4 carbon atoms), in which at least one hydrogen may be substituted by alkyl having 1 to 4 carbon atoms; R 7 and R 8 may be bonded to form -O-, In the above formula (BiN), D ring is an oxazole ring, an isoxazole ring, a thiazole ring, an isothiazole ring, an imidazole ring, an oxadiazole ring, a thiadiazole ring, a triazole ring, a tetrazole ring, a pyrazole ring, a pyridine ring, a pyrimidine ring, a pyridazine ring, a pyrazine ring, a triazine ring, a 1H-indazole ring, a benzimidazole ring, a benzoxazole ring, a benzothiazole ring, a quinoline ring, an isoquinoline ring, a quinazoline ring, a quinoxaline ring, a phthalazine ring, a naphthyridine ring, a purine ring, a pteridine ring, or a furazan ring; Ring E is an oxazole ring, an isoxazole ring, a thiazole ring, an isothiazole ring, an imidazole ring, an oxadiazole ring, a thiadiazole ring, a triazole ring, a tetrazole ring, a pyrazole ring, a pyridine ring, a pyrimidine ring, a pyridazine ring, a pyrazine ring, a triazine ring, a 1H-indazole ring, a benzimidazole ring, a benzoxazole ring, a benzothiazole ring, a quinoline ring, an isoquinoline ring, a quinazoline ring, a quinoxaline ring, a phthalazine ring, a naphthyridine ring, a purine ring, a pteridine ring, or a furazan ring; the fused ring is a tetrahydrobenzene ring, a dihydrobenzene ring, a cyclopentane ring, or a cyclohexane ring; at least one hydrogen atom in ring D, ring E and the fused ring may be substituted with an aryl having 6 to 12 carbon atoms, a heteroaryl having 2 to 15 carbon atoms, a diarylamino (wherein aryl is an aryl having 6 to 10 carbon atoms), an alkyl having 1 to 6 carbon atoms, a cycloalkyl having 3 to 14 carbon atoms, a triarylsilyl (wherein aryl is an aryl having 6 to 10 carbon atoms), or a trialkylsilyl (wherein alkyl is an alkyl having 1 to 4 carbon atoms), and at least one hydrogen atom in these may be substituted with an alkyl having 1 to 4 carbon atoms; R 1 ~R 11 at least one of the above is a group represented by the above formula (BiN) via a linking group, or at least one hydrogen atom in the formed aryl ring or heteroaryl ring is substituted with a group represented by the formula (BiN) via a linking group, * indicates a bonding position, the linking group is a single bond, phenylene, naphthylene, an alkylene having 1 to 4 carbon atoms, -O-, or a combination thereof, and at least one hydrogen atom in the linking group may be substituted with an alkyl having 1 to 4 carbon atoms; At least one hydrogen atom in the compound or a multimer thereof may be replaced with a cyano, a halogen, or a deuterium atom; In the compound or structure represented by formula (2), at least one of the ring a, the ring b, the ring c, the formed ring, aryl and heteroaryl may be condensed with at least one cycloalkane having 3 to 16 carbon atoms, and at least one hydrogen in the cycloalkane may be substituted with an alkyl having 1 to 6 carbon atoms or a cycloalkyl having 3 to 14 carbon atoms, and In the case of a polymer, it is a dimer having two structures represented by formula (2). Item 3. A polycyclic aromatic compound or a multimer thereof according to item 3.

[0017] Section 7. 6. The polycyclic aromatic compound or a multimer thereof according to any one of items 1 to 5, wherein the group represented by the formula (BiN) is a group represented by any one of the following formulas: [ka] In the above structural formula, Me represents a methyl group, and * represents the bonding position.

[0018] Section 8. In the above formula (2), R 1 and R 3 , R 4 and R 11 , R 5 and R 10 , R 6 and R 9 , R 2 , R 4 and R 11 , R 2 , R 5 and R 10 , or R 2 , R 6 and R 9 is a group represented by the above formula (BiN), or a multimer thereof according to any one of items 3 to 7.

[0019] Section 9. Item 3. The polycyclic aromatic compound according to item 1, which is represented by any one of the following structural formulas: [ka]

[0020] Section 10. 10. A material for an organic device, comprising the polycyclic aromatic compound or a multimer thereof according to any one of items 1 to 9.

[0021] Section 11. Item 11. The material for an organic device according to item 10, which is a material for an organic electroluminescent element, a material for an organic field effect transistor, or a material for an organic thin-film solar cell.

[0022] Section 12. Item 12. The material for an organic device according to item 11, wherein the material for an organic electroluminescent element is a material for an electron transport layer or a material for an electron injection layer.

[0023] Section 13. Item 13. An organic electroluminescence device comprising a pair of electrodes consisting of an anode and a cathode, a light-emitting layer disposed between the pair of electrodes, and at least one of an electron transport layer and an electron injection layer disposed between the cathode and the light-emitting layer, wherein at least one of the electron transport layer and the electron injection layer contains the material for an organic device according to item 12.

[0024] Section 14. Item 14. The organic electroluminescence device according to item 13, wherein at least one of the electron transport layer and the electron injection layer contains at least one selected from the group consisting of borane derivatives, pyridine derivatives, fluoranthene derivatives, BO derivatives, anthracene derivatives, benzofluorene derivatives, phosphine oxide derivatives, pyrimidine derivatives, carbazole derivatives, triazine derivatives, benzimidazole derivatives, phenanthroline derivatives, and quinolinol-based metal complexes.

[0025] Section 15. Item 13. The organic electroluminescence device according to item 13 or 14, wherein at least one of the electron transport layer and the electron injection layer contains at least one selected from the group consisting of alkali metals, alkaline earth metals, rare earth metals, oxides of alkali metals, oxides of alkaline earth metals, oxides of rare earth metals, halides of alkali metals, halides of alkaline 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.

[0026] Section 16. Item 16. The organic electroluminescent device according to any one of items 13 to 15, wherein the light-emitting layer contains at least one selected from the group consisting of a polycyclic aromatic compound represented by the following general formula (6), a polycyclic aromatic compound represented by the following general formula (7), and a polycyclic aromatic compound represented by the following general formula (8): [ka] In the above formula (6), ring A, ring B and ring C are each independently an aryl ring or a heteroaryl ring, and at least one hydrogen atom in these rings may be substituted; X 1 and X 2 are each independently >O, >NR, >C(-R)2, >S or >Se, R of the >NR is an optionally substituted aryl, an optionally substituted heteroaryl, an optionally substituted alkyl or an optionally substituted cycloalkyl, R of the >C(-R)2 is a hydrogen, an optionally substituted aryl, an optionally substituted alkyl or an optionally substituted cycloalkyl, and at least one of R of the >NR and R of the >C(-R)2 may be bonded to at least one of the A ring, the B ring and the C ring via a linking group; In the compound represented by formula (6), at least one of ring A, ring B, ring C, aryl, and heteroaryl may be condensed with at least one cycloalkane, at least one hydrogen in the cycloalkane may be substituted, and at least one -CH2- in the cycloalkane may be substituted with -O-, and At least one hydrogen atom in the compound represented by formula (6) may be substituted with cyano, halogen or deuterium. [ka] In the above formula (7), ring A, ring B and ring C are each independently an aryl ring or a heteroaryl ring, and at least one hydrogen atom in these rings may be substituted; X 1 , X 2 and X 3are each independently >O, >NR, >C(-R)2, >S or >Se, R of the >NR is an optionally substituted aryl, an optionally substituted heteroaryl, an optionally substituted alkyl or an optionally substituted cycloalkyl, R of the >C(-R)2 is a hydrogen, an optionally substituted aryl, an optionally substituted alkyl or an optionally substituted cycloalkyl, and at least one of R of the >NR and R of the >C(-R)2 may be bonded to at least one of the A ring, the B ring and the C ring via a linking group; In the compound or structure represented by formula (7), at least one of the A ring, the B ring, the C ring, the aryl and the heteroaryl may be fused with at least one cycloalkane, at least one hydrogen in the cycloalkane may be substituted, and at least one -CH2- in the cycloalkane may be substituted with -O-, and At least one hydrogen in the compound represented by formula (7) may be substituted with cyano, halogen or deuterium. [ka] In the above formula (8), ring A and ring B are each independently an aryl ring or a heteroaryl ring, and at least one hydrogen atom in these rings may be substituted; X 1 and X 2 are each independently >O, >NR, >C(-R)2, >S or >Se, R of the >NR is an optionally substituted aryl, an optionally substituted heteroaryl, an optionally substituted alkyl or an optionally substituted cycloalkyl, R of the >C(-R)2 is a hydrogen, an optionally substituted aryl, an optionally substituted alkyl or an optionally substituted cycloalkyl, and at least one of R of the >NR and R of the >C(-R)2 may be bonded to at least one of the rings A and B via a linking group, R 4 and R7 each independently represents hydrogen, an aryl having 6 to 12 carbon atoms, a heteroaryl having 2 to 15 carbon atoms, a diarylamino (wherein the aryl has 6 to 12 carbon atoms), an alkyl having 1 to 6 carbon atoms, or a cycloalkyl having 3 to 14 carbon atoms; In the compound or structure represented by formula (8), at least one of the A ring, the B ring, the aryl, and the heteroaryl may be fused with at least one cycloalkane, at least one hydrogen in the cycloalkane may be substituted, and at least one -CH2- in the cycloalkane may be substituted with -O-, and At least one hydrogen in the compound represented by formula (8) may be substituted with cyano, halogen or deuterium.

[0027] Section 17. Item 17. A display device or lighting device comprising the organic electroluminescent device according to any one of items 13 to 16. Effect of the Invention

[0028] According to a preferred embodiment of the present invention, a novel polycyclic aromatic compound can be provided that can be used as a material for an organic device, such as a material for an organic electroluminescence (EL) element. By using this polycyclic aromatic compound, an excellent organic device, such as an organic electroluminescence (EL) element, can be provided.

[0029] Specifically, the inventors have demonstrated that polycyclic aromatic compounds (basic skeletons) in which aromatic rings are linked by heteroatoms of boron and oxygen have a large HOMO-LUMO gap (band gap in thin film Eg) and high triplet excitation energy (E T). This is believed to be due to the fact that the 6-membered ring containing a hetero element has low aromaticity, which suppresses the decrease in the HOMO-LUMO gap accompanying the expansion of the conjugated system, and that the SOMO1 and SOMO2 in the triplet excited state (T1) are localized due to electronic perturbation of the hetero element. In addition, the polycyclic aromatic compound (basic skeleton portion) containing a hetero element according to the present invention has a small energy difference between the triplet excited state (T1) and the singlet excited state (S1), and exhibits thermally activated delayed fluorescence (TADF), making it useful as a fluorescent material for organic electroluminescence devices (including devices using TADF). In addition, the high triplet excitation energy (E T Materials having this property are also useful as electron transport layers and hole transport layers in phosphorescent organic EL devices and organic EL devices that use TADF. Furthermore, the HOMO and LUMO energies of these polycyclic aromatic compounds (basic skeleton parts) can be arbitrarily shifted by introducing substituents, so that the ionization potential and electron affinity can be optimized according to the surrounding materials.

[0030] The nitrogen-containing substituent in the present invention has a chelating structure such as bipyridine or 1,10-phenanthroline in the substituent, and therefore, for example, by chelating with lithium atoms contained in a Li / Al cathode, the electron injection barrier can be reduced. As described above, the BO2-based polycyclic aromatic skeleton, which is the basic skeleton portion, exhibits high electron mobility, and therefore the nitrogen-containing substituent introduced in the present invention enhances the electron injection property, making it a more useful material for an electron transport layer or an electron injection layer. In this way, by using a material for an electron transport layer or an electron injection layer having both high electron injection property and high electron mobility, an organic device with a low driving voltage, such as an organic EL element, can be produced. In addition, since the triplet level of the BO2-based polycyclic aromatic skeleton is increased due to the multiple resonance effect, the compound of the present invention is also useful as a hole blocking material in a phosphorescent organic EL element or a TADF organic EL element. [Brief description of the drawings]

[0031] [Figure 1] FIG. 1 is a schematic cross-sectional view showing an organic EL element according to an embodiment of the present invention. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0032] 1. Polycyclic aromatic compounds and their polymers The present invention relates to a polycyclic aromatic compound represented by the following general formula (1) or a multimer of a polycyclic aromatic compound having a plurality of structures represented by the following general formula (1), in which at least one hydrogen atom in the A ring, the B ring and the C ring is substituted with a group represented by the following general formula (BiN) via a linking group. Also, the present invention relates to a polycyclic aromatic compound represented by the following general formula (2) or a multimer of a polycyclic aromatic compound having a plurality of structures represented by the following general formula (2), in which R 1 ~R 11 is a group represented by the following formula (BiN) via a linking group, or the formed aryl ring or heteroaryl ring (R 1 ~R 11 At least one hydrogen atom in the ring formed together with the a ring, the b ring, or the c ring by bonding adjacent groups among the above is replaced with a group represented by formula (BiN) via a linking group. The definitions of each symbol in the following structural formula are the same as those of each symbol in general formula (1), formula (2), and formula (BiN), and the same applies hereinafter. [ka]

[0033] 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 atom in these rings may be substituted with a substituent. The substituent is preferably a substituted or unsubstituted aryl, a substituted or unsubstituted heteroaryl, a substituted or unsubstituted diarylamino, a substituted or unsubstituted diheteroarylamino, a substituted or unsubstituted arylheteroarylamino (an amino group having an aryl and a heteroaryl), a substituted or unsubstituted diarylboryl (two aryls may be bonded via a single bond or a linking group), a substituted or unsubstituted alkyl, a substituted or unsubstituted cycloalkyl, a substituted or unsubstituted alkoxy, a substituted or unsubstituted aryloxy, or a substituted silyl. Examples of the substituent when these groups have a substituent include an aryl, a heteroaryl, an alkyl or a cycloalkyl. In addition, the aryl ring or the heteroaryl ring preferably has a 5-membered or 6-membered ring that shares a bond with the central fused two-ring structure of the general formula (1) composed of the central element "B (boron)" and two elements "O (oxygen)".

[0034] Here, the term "fused bicyclic structure" refers to a structure in which two saturated hydrocarbon rings, each containing the central element "B (boron)" and two elements "O (oxygen)", are fused together, as shown in the center of general formula (1). The term "six-membered ring sharing a bond with the fused bicyclic structure" refers to an a-ring (benzene ring (six-membered ring)) fused to the fused bicyclic structure, as shown in general formula (2) above. The term "aryl ring or heteroaryl ring (A-ring) has this six-membered ring" refers to the A-ring being formed by this six-membered ring alone, or the A-ring being formed by further condensing other rings to this six-membered ring so as to include this six-membered ring. In other words, the term "aryl ring or heteroaryl ring (A-ring) having a six-membered ring" refers to the six-membered ring constituting all or part of the A-ring being fused to the fused bicyclic structure. The same explanation applies to "B-ring (b-ring)", "C-ring (c-ring)", and "five-membered ring".

[0035] The ring A (or ring B or ring C) in the general formula (1) is the ring a and its substituent R 1 ~R 3 (or ring b and its substituent R 8 ~R 11 , ring c and its substituent R 4 ~R 7 ). In other words, general formula (2) corresponds to a structure in which "rings A to C having 6 members" are selected as rings A to C of general formula (1). In that sense, each ring in general formula (2) is represented by lowercase letters a to c.

[0036] In the general formula (2), the substituents R 1 ~R 11 Adjacent groups among may be bonded together to form an aryl ring or a heteroaryl ring together with the a ring, the b ring or the c ring, and at least one hydrogen atom in the formed ring may be substituted with an aryl, a heteroaryl, a diarylamino, a diheteroarylamino, an arylheteroarylamino, a diarylboryl (two aryls may be bonded via a single bond or a linking group), an alkyl, a cycloalkyl, an alkoxy, an aryloxy, a triarylsilyl, a trialkylsilyl, a tricycloalkylsilyl, a dialkylcycloalkylsilyl or an alkyldicycloalkylsilyl, and at least one hydrogen atom in these may be substituted with an aryl, a heteroaryl, an alkyl or a cycloalkyl. Therefore, the ring structure constituting the polycyclic aromatic compound represented by the general formula (2) changes depending on the mutual bonding form of the substituents in the a ring, the b ring and the c ring, as shown in the following formula (2-1) and formula (2-2). The A' ring, the B' ring and the C' ring in each formula correspond to the A ring, the B ring and the C ring in the general formula (1), respectively.

[0037] [ka]

[0038] The A' ring, B' ring and C' ring in the above formula (2-1) and formula (2-2) are each independently a substituent R1 ~R 11 Adjacent groups among these are bonded to each other to form an aryl or heteroaryl ring together with the ring a, ring b, and ring c, respectively (they may also be considered as condensed rings formed by condensing other ring structures to the ring a, ring b, or ring c). Although not shown in the formula, there are also compounds in which the ring a, ring b, and ring c are all changed to ring A', ring B', and ring C'. As can be seen from the above formulas (2-1) and (2-2), for example, R in ring b 8 and R in c-ring 7 , R in ring b 11 and a-ring R 1 , R in ring c 4 and a-ring R 3 etc. are not considered to be "adjacent groups" and are not bonded to each other unless otherwise specified. In other words, "adjacent groups" refers to groups that are adjacent on the same ring.

[0039] The compounds represented by the above formula (2-1) or formula (2-2) are compounds having ring A' (or ring B' or ring C') formed by condensing a benzene ring, which is ring a (or ring b or ring c), with a benzene ring, an indole ring, a pyrrole ring, a benzofuran ring or a benzothiophene ring, and the condensed ring A' (or condensed ring B' or condensed ring C') thus formed is a naphthalene ring, a carbazole ring, an indole ring, a dibenzofuran ring or a dibenzothiophene ring, respectively.

[0040] In addition, the ring B and the ring C in the general formula (1) may be linked by -O-, and in the general formula (2), for example, R 7 and R 8 may be bonded to form -O-.

[0041] In formula (2), any "-C(-R)=" (where R is R in formula (2)) in the a ring, the b ring, and the c ring 1 ~R 11 ) may be replaced with "-N=". [ka] As shown above, for example, "-C(-R5 In this manner, the c-ring shown as a benzene ring in formula (2) may be changed to a pyridine ring, a pyrimidine ring, a pyridazine ring, a pyrazine ring, or other nitrogen-containing heteroaryl ring. Also, when there is an adjacent group on the c-ring (R 6 and R 7 ) are bonded to form a heteroaryl ring (a quinoline ring in the above formula) together with ring c, and the formed ring may be further substituted (represented by n Rs), as described above. In addition, there are the following variations: [ka] The same applies when other parts are replaced with "-N=" or when the a or b ring changes.

[0042] In formula (2), any of "-C(-R)=C(-R)-" (where R is R in formula (2)) in the ring a, ring b, and ring c 1 ~R 11 The substituents listed here may be replaced with "-N(-R)-", "-O-" or "-S-", and R in the "-N(-R)-" is aryl, alkyl or cycloalkyl. Details of the substituents listed here will be described below. [ka] As shown above, for example, "-C(-R 7 )=C(-R 6 In this manner, the c-ring, which is represented as a benzene ring in formula (2), may be changed to an R-substituted pyrrole ring, furan ring, thiophene ring, or other nitrogen-oxygen-sulfur containing heteroaryl ring. Also, when an adjacent group is present on the c-ring (R in the above formula), 4 and R 5) are bonded to ring c to form a heteroaryl ring (in the above formula, an R-substituted indole ring, benzofuran ring, or benzothiophene ring), and the formed ring may be further substituted (represented by n Rs), as described above. In addition, there are the following variations: [ka] The same applies when other positions are replaced with "-N(-R)-", "-O-", or "-S-", or when the a or b ring changes.

[0043] In the above description of formula (2-1) and formula (2-2), the rings a, b, and c are described as benzene rings. However, the same applies when the rings a to c are changed to a nitrogen-containing heteroaryl ring (6-membered or 5-membered ring) or an oxygen-sulfur-containing heteroaryl ring (5-membered ring).

[0044] The "aryl ring" which is the ring A, ring B and ring C in the general formula (1) is, for example, an aryl ring having 6 to 30 carbon atoms, preferably an aryl ring having 6 to 16 carbon atoms, more preferably an aryl ring having 6 to 12 carbon atoms, and particularly preferably an aryl ring having 6 to 10 carbon atoms. The "aryl ring" is defined as "R 1 ~R 11 In addition, since ring a (or ring b, ring c) is already composed of a benzene ring having six carbon atoms, the lower limit of the carbon number is the total carbon number of the fused rings formed by condensing the five-membered ring to this, which is nine.

[0045] Specific examples of the "aryl ring" include a monocyclic benzene ring, a bicyclic ...

[0046] Examples of the "heteroaryl ring" which is the ring A, ring B and ring C in general formula (1) include heteroaryl rings having 2 to 30 carbon atoms, preferably heteroaryl rings having 2 to 25 carbon atoms, more preferably heteroaryl rings having 2 to 20 carbon atoms, further preferably heteroaryl rings having 2 to 15 carbon atoms, and particularly preferably heteroaryl rings having 2 to 10 carbon atoms. Examples of the "heteroaryl ring" include heterocycles containing, in addition to carbon, 1 to 5 heteroatoms selected from oxygen, sulfur and nitrogen as ring-constituting atoms. The "heteroaryl ring" can be defined as "R 1 ~R 11 In addition, since ring a (or ring b, ring c) is already composed of a benzene ring having 6 carbon atoms, the lower limit of the carbon number is the total carbon number of the fused rings fused to this 5-membered ring, which is 6.

[0047] 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, a tetrazole ring, a pyrazole ring, a pyridine ring, a pyrimidine ring, a pyridazine ring, a pyrazine ring, a triazine ring, an indole ring, an isoindole ring, a 1H-indazole ring, a benzimidazole ring, a benzoxazole ring, a benzothiazole ring, a 1H-benzotriazole ring, a quinoline ring, an isoquinoline ring, a cinnoline ring, a quinazoline ring, a quinoxaline ring, a phenanthroline ring, a phthalazine ring, a naphthyridine ring, a purine ring, a pteridine ring, a carbazole ... Examples of such rings include a benzol ring, an acridine ring, a phenoxathiin ring, a phenoxazine ring, a phenothiazine ring, a phenazine ring, a phenazasiline ring, an indolizine ring, a furan ring, a benzofuran ring, an isobenzofuran ring, a dibenzofuran ring, a naphthobenzofuran ring, a thiophene ring, a benzothiophene ring, an isobenzothiophene ring, a dibenzothiophene ring, a naphthobenzothiophene ring, a benzophosphole ring, a dibenzophosphole ring, a benzophosphole oxide ring, a dibenzophosphole oxide ring, a furazan ring, a thianthrene ring, an indolocarbazole ring, a benzoindolocarbazole ring, a benzobenzoindolocarbazole ring, an imidazoline ring, and an oxazoline ring.

[0048] At least one hydrogen atom in the above-mentioned "aryl ring" or "heteroaryl ring" may be substituted with a first substituent, which is a substituted or unsubstituted "aryl", a substituted or unsubstituted "heteroaryl", a substituted or unsubstituted "diarylamino", a substituted or unsubstituted "diheteroarylamino", a substituted or unsubstituted "arylheteroarylamino", a substituted or unsubstituted "diarylboryl (two aryls may be bonded via a single bond or a linking group)", a substituted or unsubstituted "alkyl", a substituted or unsubstituted "cycloalkyl", a substituted or unsubstituted "alkoxy", a substituted or unsubstituted "aryloxy", or a substituted "silyl". Examples of the first substituent, the "aryl" or "heteroaryl" in the "diarylamino", the heteroaryl in the "diheteroarylamino", the aryl and heteroaryl in the "arylheteroarylamino", the aryl in the "diarylboryl", and the aryl in the "aryloxy" include monovalent groups represented by removing any one hydrogen atom from the above-mentioned "aryl ring" or "heteroaryl ring".

[0049] The "alkyl" as the first substituent may be either linear or branched, and examples thereof include linear alkyl having 1 to 24 carbon atoms or branched alkyl having 3 to 24 carbon atoms. An alkyl having 1 to 18 carbon atoms (branched alkyl having 3 to 18 carbon atoms) is preferred, an alkyl having 1 to 12 carbon atoms (branched alkyl having 3 to 12 carbon atoms) is more preferred, an alkyl having 1 to 6 carbon atoms (branched alkyl having 3 to 6 carbon atoms) is even more preferred, an alkyl having 1 to 5 carbon atoms (branched alkyl having 3 to 5 carbon atoms) is particularly preferred, and an alkyl having 1 to 4 carbon atoms (branched alkyl having 3 to 4 carbon atoms) is most preferred.

[0050] Specific examples of alkyl include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, t-butyl, n-pentyl, isopentyl, neopentyl, t-pentyl (t-amyl), n-hexyl, 1-methylpentyl, 3,3-dimethylbutyl, 2-ethylbutyl, n-heptyl, 1-methylhexyl, n-octyl, t-octyl (1,1,3,3-tetramethylbutyl), 1-methyl Examples include heptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 2,6-dimethyl-4-heptyl, 3,5,5-trimethylhexyl, n-decyl, n-undecyl, 1-methyldecyl, n-dodecyl, n-tridecyl, 1-hexylheptyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, n-heptadecyl, n-octadecyl, and n-eicosyl. Further, for example, 1-ethyl-1-methylpropyl, 1,1-diethylpropyl, 1,1-dimethylbutyl, 1-ethyl-1-methylbutyl, 1,1,4-trimethylpentyl, 1,1,2-trimethylpropyl, 1,1-dimethyloctyl, 1,1-dimethylpentyl, 1,1-dimethylheptyl, 1,1,5-trimethylhexyl, 1-ethyl-1-methylhexyl, 1-ethyl-1,3-dimethylbutyl, 1,1,2,2-tetramethylpropyl, 1-butyl-1-methylpentyl, 1,1-diethylbutyl, 1-ethyl-1-methylpentyl, 1,1,3-trimethylbutyl, 1-propyl-1-methylpentyl, 1,1,2-trimethylpropyl, 1-ethyl-1,2,2-trimethylpropyl, 1-propyl-1-methylbutyl, and 1,1-dimethylhexyl.

[0051] Furthermore, examples of the "cycloalkyl" as the first substituent include cycloalkyl having 3 to 24 carbon atoms, cycloalkyl having 3 to 20 carbon atoms, cycloalkyl having 3 to 16 carbon atoms, cycloalkyl having 3 to 14 carbon atoms, cycloalkyl having 3 to 12 carbon atoms, cycloalkyl having 5 to 10 carbon atoms, cycloalkyl having 5 to 8 carbon atoms, cycloalkyl having 5 to 6 carbon atoms, and cycloalkyl having 5 carbon atoms.

[0052] Specific examples of cycloalkyl include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, and alkyl (particularly methyl) substituted derivatives of these having 1 to 5 or 1 to 4 carbon atoms, as well as norbornenyl, bicyclo[1.0.1]butyl, bicyclo[1.1.1]pentyl, bicyclo[2.0.1]pentyl, bicyclo[1.2.1]hexyl, bicyclo[3.0.1]hexyl, bicyclo[2.1.2]heptyl, bicyclo[2.2.2]octyl, adamantyl, diamantyl, decahydronaphthalenyl, and decahydroazulenyl.

[0053] Furthermore, examples of the "alkoxy" as the first substituent include linear alkoxy having 1 to 24 carbon atoms or branched alkoxy having 3 to 24 carbon atoms. An alkoxy having 1 to 18 carbon atoms (branched alkoxy having 3 to 18 carbon atoms) is preferred, an alkoxy having 1 to 12 carbon atoms (branched alkoxy having 3 to 12 carbon atoms) is more preferred, an alkoxy having 1 to 6 carbon atoms (branched alkoxy having 3 to 6 carbon atoms) is even more preferred, an alkoxy having 1 to 5 carbon atoms (branched alkoxy having 3 to 5 carbon atoms) is particularly preferred, and an alkoxy having 1 to 4 carbon atoms (branched alkoxy having 3 to 4 carbon atoms) is most preferred.

[0054] Specific examples of alkoxy include methoxy, ethoxy, propoxy, isopropoxy, n-butoxy, isobutoxy, s-butoxy, t-butoxy, t-amyloxy, n-pentyloxy, isopentyloxy, neopentyloxy, t-pentyloxy, n-hexyloxy, 1-methylpentyloxy, 3,3-dimethylbutoxy, 2-ethylbutoxy, n-heptyloxy, 1-methylhexyloxy, n-octyloxy, t-octyloxy, 1-methylheptyloxy, and 2-ethylhexyl. Examples of the aryloxy group include oxy, 2-propylpentyloxy, n-nonyloxy, 2,2-dimethylheptyloxy, 2,6-dimethyl-4-heptyloxy, 3,5,5-trimethylhexyloxy, n-decyloxy, n-undecyloxy, 1-methyldecyloxy, n-dodecyloxy, n-tridecyloxy, 1-hexylheptyloxy, n-tetradecyloxy, n-pentadecyloxy, n-hexadecyloxy, n-heptadecyloxy, n-octadecyloxy, and n-eicosyloxy.

[0055] Furthermore, examples of the "substituted silyl" as the first substituent include triarylsilyl, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, and alkyldicycloalkylsilyl, which are silyl substituted with at least one of aryl, alkyl, and cycloalkyl.

[0056] The "triarylsilyl" refers to a silyl group in which three hydrogen atoms are each independently substituted with an aryl, and the aryl can be any of the groups described above as the "aryl" in the first substituent. Specific "triarylsilyl" includes, for example, triphenylsilyl, diphenylmononaphthylsilyl, monophenyldinaphthylsilyl, trinaphthylsilyl, and the like.

[0057] The "trialkylsilyl" includes a group in which three hydrogen atoms in a silyl group are each independently substituted with an alkyl, and the alkyl can be cited from the groups described as the "alkyl" in the first substituent above. The alkyl to be substituted is preferably an alkyl having 1 to 4 carbon atoms, and specific examples thereof include methyl, ethyl, propyl, i-propyl, butyl, sec-butyl, t-butyl, and cyclobutyl.

[0058] Specific examples of trialkylsilyl include trimethylsilyl, triethylsilyl, tripropylsilyl, tri-i-propylsilyl, tributylsilyl, tri-sec-butylsilyl, tri-t-butylsilyl, ethyldimethylsilyl, propyldimethylsilyl, i-propyldimethylsilyl, butyldimethylsilyl, sec-butyldimethylsilyl, t-butyldimethylsilyl, methyldiethylsilyl, propyldiethylsilyl, i-propyldiethylsilyl, butyldiethylsilyl, sec-butyldiethylsilyl, t-butyldiethylsilyl, methyldipropylsilyl, ethyldipropylsilyl, butyldipropylsilyl, sec-butyldipropylsilyl, t-butyldipropylsilyl, methyldi-i-propylsilyl, ethyldi-i-propylsilyl, butyldi-i-propylsilyl, sec-butyldi-i-propylsilyl, and t-butyldi-i-propylsilyl.

[0059] Examples of "tricycloalkylsilyl" include groups in which three hydrogen atoms in a silyl group are independently replaced with cycloalkyl, and the cycloalkyl can be cited as the group described as "cycloalkyl" in the first substituent above. Preferred cycloalkyl groups for substitution are cycloalkyl groups having 5 to 10 carbon atoms, specifically cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, bicyclo[1.1.1]pentyl, bicyclo[2.0.1]pentyl, bicyclo[1.2.1]hexyl, bicyclo[3.0.1]hexyl, bicyclo[2.1.2]heptyl, bicyclo[2.2.2]octyl, adamantyl, decahydronaphthalenyl, and decahydroazulenyl.

[0060] Specific examples of tricycloalkylsilyl include tricyclopentylsilyl and tricyclohexylsilyl.

[0061] Specific examples of dialkylcycloalkylsilyl substituted with two alkyls and one cycloalkyl and alkyldicycloalkylsilyl substituted with one alkyl and two cycloalkyls include silyl substituted with a group selected from the specific alkyls and cycloalkyls mentioned above.

[0062] As for the "aryl" in the "diarylboryl" of the first substituent, the above description of the aryl can be cited. In addition, the two aryls may be bonded via a single bond or a linking group (e.g., >C(-R)2, >O, >S, or >NR). Here, R in >C(-R)2 and >NR is aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, alkoxy, or aryloxy (above, the first substituent), and the first substituent may be further substituted with aryl, heteroaryl, alkyl, or cycloalkyl (above, the second substituent), and as specific examples of these groups, the above description of the aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, alkoxy, or aryloxy as the first substituent can be cited.

[0063] In the general formula (2), any "-C(-R)=C(-R)-" (where R is R in formula (2) 1 ~R 11 R in "-N(-R)-" which may be substituted by "-N(-R)-" is aryl, alkyl, or cycloalkyl, and examples of this aryl, alkyl, or cycloalkyl include the groups described above. In particular, aryl having 6 to 10 carbon atoms (e.g., phenyl, naphthyl, etc.), alkyl having 1 to 5 or 1 to 4 carbon atoms (e.g., methyl, ethyl, etc.), or cycloalkyl having 5 to 10 carbon atoms (preferably cyclohexyl or adamantyl) are preferred.

[0064] As described above, the first substituent, substituted or unsubstituted "aryl", substituted or unsubstituted "heteroaryl", substituted or unsubstituted "diarylamino", substituted or unsubstituted "diheteroarylamino", substituted or unsubstituted "arylheteroarylamino", substituted or unsubstituted "diarylboryl (two aryls may be bonded via a single bond or a linking group)", substituted or unsubstituted "alkyl", substituted or unsubstituted "cycloalkyl", substituted or unsubstituted "alkoxy", substituted or unsubstituted "aryloxy", or substituted "silyl" may have at least one hydrogen atom substituted with a second substituent. Examples of the second substituent include aryl, heteroaryl, alkyl, or cycloalkyl, and specific examples thereof can be seen in the description of the monovalent group represented by removing any one hydrogen atom from the above-mentioned "aryl ring" or "heteroaryl ring", and the "alkyl" or "cycloalkyl" as the first substituent. The aryl and heteroaryl as the second substituent also include structures in which at least one hydrogen atom in the aryl and heteroaryl as the second substituent is substituted with an aryl such as phenyl (specific examples are the groups mentioned above), an alkyl such as methyl (specific examples are the groups mentioned above), or a cycloalkyl such as cyclohexyl (specific examples are the groups mentioned above). As an example, when the second substituent is a carbazolyl group, a carbazolyl group in which at least one hydrogen atom at the 9-position is substituted with an aryl such as phenyl, an alkyl such as methyl, or a cycloalkyl such as cyclohexyl is also included in the heteroaryl as the second substituent.

[0065] R in general formula (2) 1 ~R 11The aryl, heteroaryl, aryl of diarylamino, heteroaryl of diheteroarylamino, aryl and heteroaryl of arylheteroarylamino, aryl of diarylboryl, and aryl of aryloxy in the formula (1) include monovalent groups represented by removing any one hydrogen atom from the "aryl ring" or "heteroaryl ring" described in the formula (1). 1 ~R 11 For the alkyl, cycloalkyl, or alkoxy in R , the explanation of "alkyl," "cycloalkyl," or "alkoxy" as the first substituent in the explanation of the above general formula (1) can be referred to. 1 ~R 11 For the triarylsilyl, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, or alkyldicycloalkylsilyl in the above, the explanation of "substituted silyl" as the first substituent in the explanation of the general formula (1) can be referred to. Furthermore, the same applies to aryl, heteroaryl, alkyl, or cycloalkyl as substituents to these groups. In addition, R 1 ~R 11 When adjacent groups among these are bonded to form an aryl ring or a heteroaryl ring together with the a ring, the b ring or the c ring, the same applies to the substituents on these rings, such as aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl (the two aryls may be bonded via a single bond or a linking group), alkyl, cycloalkyl, alkoxy, aryloxy, triarylsilyl, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl or alkyldicycloalkylsilyl, and the further substituents, such as aryl, heteroaryl, alkyl or cycloalkyl.

[0066] Specifically, the emission wavelength can be adjusted by the steric hindrance, electron donating property and electron withdrawing property of the structure of the first substituent, and is preferably a group represented by the following structural formula, more preferably methyl, t-butyl, phenyl, o-tolyl, p-tolyl, 2,4-xylyl, 2,5-xylyl, 2,6-xylyl, 2,4,6-mesityl, diphenylamino, di-p-tolylamino, bis(p-(t-butyl)phenyl)amino, carbazolyl, 3,6-dimethylcarbazolyl, 3,6-di-t-butylcarbazolyl and phenoxy, and even more preferably methyl, t-butyl, phenyl, o-tolyl, 2,6-xylyl, 2,4,6-mesityl, diphenylamino, di-p-tolylamino, bis(p-(t-butyl)phenyl)amino, carbazolyl, 3,6-dimethylcarbazolyl and 3,6-di-t-butylcarbazolyl. From the viewpoint of ease of synthesis, larger steric hindrance is preferred for selective synthesis, and specifically, t-butyl, o-tolyl, p-tolyl, 2,4-xylyl, 2,5-xylyl, 2,6-xylyl, 2,4,6-mesityl, di-p-tolylamino, bis(p-(t-butyl)phenyl)amino, 3,6-dimethylcarbazolyl and 3,6-di-t-butylcarbazolyl are preferred.

[0067] In the structural formulas below, "Me" represents methyl, "tBu" represents t-butyl, "tAm" represents t-amyl, and "tOct" represents t-octyl, and * represents the bond position. [ka] [ka] [ka] [ka] [ka]

[0068] The present invention also relates to a multimer of a polycyclic aromatic compound having a plurality of unit structures represented by general formula (1), preferably a multimer of a polycyclic aromatic compound having a plurality of unit structures represented by general formula (2). The multimer is preferably a dimer to hexamer, more preferably a dimer to trimer, and particularly preferably a dimer. The multimer may have a form having a plurality of the above unit structures in one compound. For example, in addition to a form in which a plurality of the above unit structures are bonded together via a linking group such as a single bond, an alkylene group having 1 to 3 carbon atoms, a phenylene group, or a naphthylene group (linked multimer), the multimer may have a form in which any ring (ring A, ring B or ring C, ring a, ring b or ring c) contained in the above unit structure is bonded together so as to be shared by the plurality of unit structures (ring-shared multimer), or may have a form in which any ring (ring A, ring B or ring C, ring a, ring b or ring c) contained in the above unit structure is bonded together so as to be condensed (ring-condensed multimer). However, ring-shared multimers and ring-condensed multimers are preferred, and ring-shared multimers are more preferred.

[0069] Examples of such multimers include multimer compounds represented by the following formula (2-4), formula (2-4-1), formula (2-4-2), formula (2-5-1) to formula (2-5-4), or formula (2-6). The multimer compound represented by the following formula (2-4) is a multimer compound (ring-sharing multimer) having a plurality of unit structures represented by general formula (2) in one compound, with the benzene ring being the a-ring being shared, as explained in the general formula (2). The multimer compound represented by the following formula (2-4-1) is a multimer compound (ring-sharing multimer) having two unit structures represented by general formula (2) in one compound, with the benzene ring being the a-ring being shared, as explained in the general formula (2). Moreover, the multimeric compound represented by the following formula (2-4-2) is a multimeric compound (ring-sharing type multimer) having three unit structures represented by the general formula (2) in one compound, with the benzene ring being the a ring shared, when described in the general formula (2). Moreover, the multimeric compound represented by any one of the following formulas (2-5-1) to (2-5-4) is a multimeric compound (ring-sharing type multimer) having a plurality of unit structures represented by the general formula (2) in one compound, with the benzene ring being the b ring (or the c ring) shared, when described in the general formula (2). Moreover, the multimeric compound represented by the following formula (2-6) is a multimeric compound (ring-condensed type multimer) having a plurality of unit structures represented by the general formula (2) in one compound, with the benzene ring being the b ring (or the a ring, the c ring) of a certain unit structure condensed with the benzene ring being the b ring (or the a ring, the c ring) of a certain unit structure.

[0070] [ka]

[0071] The multimeric compound may be a multimer in which a multimerization form represented by formula (2-4), formula (2-4-1) or formula (2-4-2) is combined with a multimerization form represented by any one of formulas (2-5-1) to (2-5-4) or formula (2-6), a multimer in which a multimerization form represented by any one of formulas (2-5-1) to (2-5-4) is combined with a multimerization form represented by formula (2-6), or a multimer in which a multimerization form represented by formula (2-4), formula (2-4-1) or formula (2-4-2), a multimerization form represented by any one of formulas (2-5-1) to (2-5-4), and a multimerization form represented by formula (2-6).

[0072] The polycyclic aromatic compound of the present invention has a group represented by the following general formula (BiN) via a linking group. [ka] In the above formula (BiN), ring D is a heteroaryl ring containing at least one N, ring E is an aromatic or non-aromatic ring containing at least one N, an aromatic or non-aromatic condensed ring may be formed between ring D and ring E, and at least one hydrogen in these rings may be substituted. At the position of * in formula (BiN), it is substituted with the structure of general formula (1) or formula (2) via a linking group.

[0073] The "heteroaryl ring containing at least one N" which is ring D is not particularly limited as long as it is a ring having an "-N=C<" group in the ring, and examples thereof include rings having 2 to 30 carbon atoms, preferably rings having 2 to 25 carbon atoms, more preferably rings having 2 to 20 carbon atoms, further preferably rings having 2 to 15 carbon atoms, and particularly preferably rings having 2 to 10 carbon atoms. Examples of the heteroaryl ring include heterocycles containing carbon and nitrogen as ring-constituting atoms and, in addition, 1 to 5 heteroatoms selected from oxygen, sulfur, and nitrogen.

[0074] Specific examples of the "heteroaryl ring containing at least one N" include an oxazole ring, an isoxazole ring, a thiazole ring, an isothiazole ring, an imidazole ring, an oxadiazole ring, a thiadiazole ring, a triazole ring, a tetrazole ring, a pyrazole ring, a pyridine ring, a pyrimidine ring, a pyridazine ring, a pyrazine ring, a triazine ring, a 1H-indazole ring, a benzimidazole ring, a benzoxazole ring, a benzothiazole ring, a quinoline ring, an isoquinoline ring, a quinazoline ring, a quinoxaline ring, a phthalazine ring, a naphthyridine ring, a purine ring, a pteridine ring, or a furazan ring.

[0075] The "aromatic ring or non-aromatic ring containing at least one N" which is ring E is not particularly limited as long as it is a ring having an "-N=C<" group in the ring, and examples thereof include rings having 2 to 30 carbon atoms, preferably rings having 2 to 25 carbon atoms, more preferably rings having 2 to 20 carbon atoms, further preferably rings having 2 to 15 carbon atoms, and particularly preferably rings having 2 to 10 carbon atoms. Examples of aromatic rings or non-aromatic rings include heterocycles containing carbon and nitrogen as ring-constituting atoms and, in addition, 1 to 5 heteroatoms selected from oxygen, sulfur, and nitrogen.

[0076] Specific examples of the "aromatic ring containing at least one N" include an oxazole ring, an isoxazole ring, a thiazole ring, an isothiazole ring, an imidazole ring, an oxadiazole ring, a thiadiazole ring, a triazole ring, a tetrazole ring, a pyrazole ring, a pyridine ring, a pyrimidine ring, a pyridazine ring, a pyrazine ring, a triazine ring, a 1H-indazole ring, a benzimidazole ring, a benzoxazole ring, a benzothiazole ring, a quinoline ring, an isoquinoline ring, a quinazoline ring, a quinoxaline ring, a phthalazine ring, a naphthyridine ring, a purine ring, a pteridine ring, or a furazan ring.

[0077] "Non-aromatic rings containing at least one N" include rings in which the above-mentioned aromatic rings have lost their aromaticity, such as rings in which an unsaturated bond in an aromatic ring has been saturated with a substituent. One example is the ring formed by saturating the unsaturated bond in an oxazole ring as shown below, and the same explanation can be applied to not only oxazole rings but also the other aromatic rings mentioned above. "Me" in the following structural formula is a methyl group. [ka]

[0078] In addition, the aromatic or non-aromatic fused ring formed between the D ring and the E ring may be, for example, a ring having 2 to 15 carbon atoms, preferably a ring having 2 to 10 carbon atoms, specifically, a tetrahydrobenzene ring, a dihydrobenzene ring, a cyclopentane ring, a cyclohexane ring, etc. Specific structures are exemplified below. The definition of each symbol in the following structural formula is the same as the definition of each symbol in the general formula (BiN). [ka]

[0079] At least one hydrogen atom in ring D, ring E and the fused ring may be substituted with an aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl (the two aryls may be bonded via a single bond or a linking group), alkyl, cycloalkyl, alkoxy, aryloxy, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl or alkyldicycloalkylsilyl (all of these are first substituents), and at least one hydrogen atom in these may be substituted with an aryl, heteroaryl, alkyl or cycloalkyl (all of these are second substituents). For details of these groups, the explanations of the first and second substituents in general formula (1) and formula (2) can be cited.

[0080] Specific examples of the group represented by formula (BiN) are shown below. [ka]

[0081] At least one hydrogen atom in the ring A, ring B and ring C in formula (1) is substituted with a group represented by the following general formula (BiN) via a linking group. 1 ~R 11 is a group represented by the following formula (BiN) via a linking group, or the formed aryl ring or heteroaryl ring (R 1 ~R 11 At least one hydrogen atom in the ring formed together with ring a, ring b or ring c by bonding adjacent groups among these is substituted with a group represented by formula (BiN) via a linking group.

[0082] The linking group is, for example, a single bond, arylene, heteroarylene, alkylene, alkenylene, alkynylene, -O-, -S-, >NR, or a combination thereof. The arylene and heteroarylene include divalent groups represented by removing any two hydrogen atoms from the "aryl ring" and "heteroaryl ring" in general formula (1) and formula (2). The alkylene includes a divalent group represented by removing any one hydrogen atom from the "alkyl" as the first substituent in general formula (1) and formula (2). In addition, alkenylene and alkynylene are groups represented by replacing any "-CH2-CH2-" in the alkylene with "-CH=CH-" or "-C≡C-", respectively.

[0083] R in >NR in the linking group is aryl, heteroaryl, alkyl or cycloalkyl. For details of these groups, the explanation of the first and second substituents in general formula (1) and formula (2) can be cited.

[0084] At least one hydrogen atom in the linking group may be substituted with an aryl, heteroaryl, alkyl, or cycloalkyl. For details of these groups, the descriptions of the first and second substituents in general formula (1) and formula (2) can be cited.

[0085] Specific examples of the linking group include a single bond, phenylene, naphthylene, alkylene having 1 to 4 carbon atoms, -O-, combinations thereof, and further groups in which at least one hydrogen is substituted with an alkyl having 1 to 4 carbon atoms. Among these, a single bond, phenylene, naphthylene, methylene, ethylene, -OCH2CH2-, -CH2CH2O-, -OCH2CH2O-, etc. are preferred, and a single bond is more preferred.

[0086] The bonding position of the group represented by formula (BiN) may be any of the positions of the A ring, the B ring, and the C ring in formula (1). 1 ~R 11 or a formed aryl or heteroaryl ring (R 1 ~R 11 The ring may be any position of the ring formed together with the a, b or c ring by bonding adjacent groups among R 1 and R 3 , R 4 and R 11 , R 5 and R 10 , R 6 and R 9 , R 2 , R 4 and R 11 , R 2 , R 5 and R 10 , or R 2 , R 6 and R 9 This is the location.

[0087] In addition, all or a part of hydrogen atoms in the chemical structure of the polycyclic aromatic compound and its multimer represented by general formula (1) or (2) may be substituted with cyano, halogen, or deuterium. For example, in formula (1), hydrogen atoms in rings A, B, and C (rings A to C are aryl or heteroaryl rings), substituents on rings A to C, and the group represented by formula (BiN) may be substituted with cyano, halogen, or deuterium, and among these, embodiments in which all or a part of hydrogen atoms in aryl or heteroaryl are substituted with cyano, halogen, or deuterium can be mentioned. The halogen atom is fluorine, chlorine, bromine, or iodine, preferably fluorine, chlorine, or bromine, and more preferably fluorine or chlorine.

[0088] In addition, at least one of the aromatic rings and heteroaromatic rings in the chemical structure of the polycyclic aromatic compound represented by general formula (1) or (2) and its multimer may be condensed with at least one cycloalkane.

[0089] For example, at least one of the aryl and heteroaryl rings which are ring A, ring B, ring C, ring a, ring b and ring c, the aryl groups (aryl groups in aryl, diarylamino, arylheteroarylamino, diarylboryl, aryloxy or triarylsilyl) and heteroaryl groups (heteroaryl groups in heteroaryl, diheteroarylamino or arylheteroarylamino) as the first and second substituents on ring A to ring C, and the aryl groups (similar to above) and heteroaryl groups (similar to above) as the first and second substituents on ring a to ring c may be condensed with at least one cycloalkane.

[0090] Preferably, at least one of the aryl and heteroaryl rings which are ring A, ring B, ring C, ring a, ring b and ring c, the aryl group (aryl group moiety in aryl, diarylamino, diarylboryl or aryloxy) and the heteroaryl group (heteroaryl moiety in heteroaryl or diheteroarylamino) as the first substituent on ring A to ring C, and the aryl group (similar to above) and the heteroaryl group (similar to above) as the first substituent on ring a to ring c may be condensed with at least one cycloalkane.

[0091] More preferably, at least one of the aryl rings which are ring A, ring B, ring C, ring a, ring b and ring c, the aryl group (aryl group moiety in aryl or diarylamino) and heteroaryl group (heteroaryl moiety in heteroaryl) as the first substituents on ring A to ring C, and the aryl group (similar to above) and heteroaryl group (similar to above) as the first substituents on ring a to ring c may be condensed with at least one cycloalkane.

[0092] More preferably, at least one of the aryl rings which are ring A, ring B, ring C, ring a, ring b and ring c, the aryl group as the first substituent on ring A to ring C (the aryl group portion in aryl or diarylamino), and the aryl group as the first substituent on ring a to ring c (similar to the above) may be condensed with at least one cycloalkane.

[0093] Examples of "cycloalkane" include cycloalkanes having 3 to 24 carbon atoms, cycloalkanes having 3 to 20 carbon atoms, cycloalkanes having 3 to 16 carbon atoms, cycloalkanes having 3 to 14 carbon atoms, cycloalkanes having 5 to 10 carbon atoms, cycloalkanes having 5 to 8 carbon atoms, cycloalkanes having 5 to 6 carbon atoms, and cycloalkanes having 5 carbon atoms.

[0094] Specific examples of cycloalkanes include cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclooctane, cyclononane, cyclodecane, norbornene, bicyclo[1.0.1]butane, bicyclo[1.1.1]pentane, bicyclo[2.0.1]pentane, bicyclo[1.2.1]hexane, bicyclo[3.0.1]hexane, bicyclo[2.1.2]heptane, bicyclo[2.2.2]octane, adamantane, diamantane, decahydronaphthalene, and decahydroazulene, as well as alkyl (particularly methyl) substituted, halogen (particularly fluorine) substituted, and deuterium substituted derivatives of these having 1 to 5 carbon atoms.

[0095] Among these, for example, as shown in the following structural formula, a structure in which at least one hydrogen atom is substituted on the carbon atom at the α-position of a cycloalkane (a carbon atom at a position adjacent to the carbon atom at the condensation site in a cycloalkane condensed to an aromatic ring or a heteroaromatic ring) is preferred, a structure in which two hydrogen atoms are substituted on the carbon atom at the α-position is more preferred, and a structure in which a total of four hydrogen atoms are substituted on the two carbon atoms at the α-position is even more preferred. Examples of this substituent include an alkyl (particularly methyl) substituent having 1 to 5 carbon atoms, a halogen (particularly fluorine) substituent, and a deuterium substituent. [ka]

[0096] The number of cycloalkanes condensed to one aromatic ring or heteroaromatic ring is preferably 1 to 3, more preferably 1 or 2, and even more preferably 1. For example, the following shows an example in which one or more cycloalkanes are condensed to one benzene ring (phenyl group). In each structural formula, * means a benzene ring contained in the skeleton structure of the compound when it is a benzene ring, and means a bond substituted on the skeleton structure of the compound when it is a phenyl group. Cycloalkanes condensed as in formula (Cy-1-4) and formula (Cy-2-4) may be condensed together. The same applies when the condensed ring (group) is an aromatic ring or heteroaromatic ring other than a benzene ring (phenyl group), or when the condensed cycloalkane is a cycloalkane other than cyclopentane or cyclohexane. [ka]

[0097] At least one -CH2- in a cycloalkane may be replaced with -O-. However, when multiple -CH2- are replaced with -O-, adjacent -CH2- are not replaced with -O-. For example, the following shows an example in which one or more -CH2- in a cycloalkane fused to one benzene ring (phenyl group) are replaced with -O-. In each structural formula, * means a benzene ring included in the skeletal structure of the compound when it is a benzene ring, and means a bond that substitutes for the skeletal structure of the compound when it is a phenyl group. The same applies when the fused ring (group) is an aromatic ring or heteroaromatic ring other than a benzene ring (phenyl group), and when the fused cycloalkane is a cycloalkane other than cyclopentane or cyclohexane. [ka]

[0098] At least one hydrogen atom in the cycloalkane may be substituted, and examples of the substituent include aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl (two aryls may be bonded via a single bond or a linking group), alkyl, cycloalkyl, alkoxy, aryloxy, substituted silyl, deuterium, cyano, and halogen. For details of these, the description of the first substituent can be cited. Among these substituents, alkyl (e.g., alkyl having 1 to 6 carbon atoms), cycloalkyl (e.g., cycloalkyl having 3 to 14 carbon atoms), halogen (e.g., fluorine), and deuterium are preferred. In addition, when cycloalkyl is substituted, it may be a substitution form that forms a spiro structure, and for example, an example in which a spiro structure is formed in a cycloalkane condensed to one benzene ring (phenyl group) is shown below. In each structural formula, * means that in the case of a benzene ring, it is a benzene ring included in the skeletal structure of the compound, and in the case of a phenyl group, it means a bond that substitutes in the skeletal structure of the compound. [ka]

[0099] Other forms of cycloalkane condensation include polycyclic aromatic compounds and multimers thereof represented by general formula (1) or (2) substituted with, for example, a diarylamino group condensed with a cycloalkane (condensed to the aryl group portion), a carbazolyl group condensed with a cycloalkane (condensed to the benzene ring portion), or a benzocarbazolyl group condensed with a cycloalkane (condensed to the benzene ring portion). Examples of the "diarylamino group" include the groups described above as the "first substituent."

[0100] Further, specific examples include polycyclic aromatic compounds represented by general formula (2) and R 2 is a diarylamino group fused with a cycloalkane (fused to the aryl group portion) or a carbazolyl group fused with a cycloalkane (fused to the benzene ring portion).

[0101] An example of this is a polycyclic aromatic compound represented by the following general formula (2-Cy), or a multimer of a polycyclic aromatic compound having a plurality of structures represented by the following general formula (2-Cy). In the structural formula below, Cy is a cycloalkane, n is an integer of 1 to 3 (preferably 1), and "=(Cy)n" means that n cycloalkanes are condensed at any position of the structure to be condensed (in the structural formula below, n cycloalkanes are condensed to a benzene ring (phenyl group)), and the definition of each symbol in the structural formula is the same as that of each symbol in general formula (2). [ka]

[0102] Specifically, compounds represented by the following formulas can be mentioned. In the following formulas, "Cy" represents a cycloalkane, and n is each independently 0 to the maximum number that can be condensed (however, all n's are not 0), preferably 0 to 2 (however, all n's are not 0), more preferably 1, and "=(Cy)n" means that n cycloalkanes are condensed at any position of the structure to be condensed (for example, in the following formula "2-Cy-(1)", n cycloalkanes are condensed at any position of each benzene ring). In addition, in the following structural formulas, "OPh" represents a phenoxy group, "Me" represents a methyl group, and each compound may be substituted with the above-mentioned first and second substituents, and at least one of the first substituents is a group represented by the above formula (BiN) via a linking group, or at least one hydrogen atom in the formed aryl ring or heteroaryl ring is substituted with a group represented by the formula (BiN) via a linking group.

[0103] [ka]

[0104] [ka]

[0105] [ka]

[0106] [ka]

[0107] [ka]

[0108] [ka]

[0109] [ka]

[0110] [ka]

[0111] More specific examples of the polycyclic aromatic compound of the present invention include compounds represented by the following structural formulas: Note that the notation of the methyl group (Me) in the structural formulas is omitted.

[0112] [ka]

[0113] [ka]

[0114] [ka]

[0115] [ka]

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[0186] 2. Method for producing polycyclic aromatic compounds and their polymers The polycyclic aromatic compounds represented by general formula (1) or (2) can be produced according to the methods described in many publicly known documents, including WO 2015 / 102118.

[0187] Basically, an intermediate is produced by first bonding the A ring (a-ring) with the B ring (b-ring) and the C ring (c-ring) with a bonding group (a group containing O (oxygen)) (first reaction), and then the A ring (a-ring), B ring (b-ring) and C ring (c-ring) are bonded with a bonding group (a group containing the central element B (boron)) to produce the final product (second reaction). In the first reaction, for example, if it is an etherification reaction, a general reaction such as a nucleophilic substitution reaction or an Ullmann reaction can be used. In the second reaction, a tandem hetero Friedel-Crafts reaction (successive aromatic electrophilic substitution reactions, the same applies below) can be used.

[0188] In addition, by using a raw material that is cyanated, halogenated or deuterated somewhere in these reaction steps, or by adding a step of cyanation, halogenation or deuteration, a compound in which a desired position is cyanated, halogenated or deuterated can be produced. Similarly, by using a raw material that is substituted with a group represented by the general formula (BiN) somewhere in the reaction steps, or by adding a step of substituting this group, the compound of the present invention can be produced.

[0189] The second reaction is a reaction to introduce a central element B (boron) that bonds the A ring (a ring), B ring (b ring) and C ring (c ring) as shown in the following schemes (1) and (2). First, the hydrogen atom between the two elements "O (oxygen)" is orthometalated with n-butyllithium, sec-butyllithium, t-butyllithium or the like. Next, boron trichloride, boron tribromide or the like is added to carry out lithium-boron metal exchange, and then a tandem boron-Friedel-Crafts reaction is carried out by adding a Bronsted base such as N,N-diisopropylethylamine to obtain the target product. In the second reaction, a Lewis acid such as aluminum trichloride may be added to promote the reaction. The symbols in the structural formulas in the following schemes (1) to (5) are defined as above.

[0190] [ka] [ka]

[0191] The above schemes (1) and (2) mainly show the method for producing the polycyclic aromatic compounds represented by the general formulas (1) and (2), but the multimers can be produced by using intermediates having multiple A rings (a rings), B rings (b rings) and C rings (c rings). Details are explained in the following schemes (3) to (5). In this case, the target product can be obtained by doubling or tripling the amount of the reagent such as butyl lithium used.

[0192] [ka] [ka] [ka]

[0193] Specific examples of solvents that can be used in the above reactions include t-butylbenzene and xylene.

[0194] Examples of orthometalation reagents include alkyllithium such as methyllithium, n-butyllithium, sec-butyllithium, and t-butyllithium, and organic alkali compounds such as lithium diisopropylamide, lithium tetramethylpiperidide, lithium hexamethyldisilazide, and potassium hexamethyldisilazide.

[0195] In addition, examples of metal exchange reagents for the metal-central element "B (boron)" include boron halides such as boron trifluoride, boron trichloride, boron tribromide, and boron triiodide, boron amino halides such as CIPN(NEt2)2, boron alkoxylates, and boron aryloxylates.

[0196] Examples of Bronsted bases include N,N-diisopropylethylamine, triethylamine, 2,2,6,6-tetramethylpiperidine, 1,2,2,6,6-pentamethylpiperidine, N,N-dimethylaniline, N,N-dimethyltoluidine, 2,6-lutidine, sodium tetraphenylborate, potassium tetraphenylborate, triphenylborane, tetraphenylsilane, Ar4BNa, Ar4BK, Ar3B, and Ar4Si (wherein Ar is an aryl such as phenyl).

[0197] Furthermore, examples of Lewis acids include AlCl3, AlBr3, AlF3, BF3·OEt2, BCl3, BBr3, GaCl3, GaBr3, InCl3, InBr3, In(OTf)3, SnCl4, SnBr4, AgOTf, ScCl3, Sc(OTf)3, ZnCl2, ZnBr2, Zn(OTf)2, MgCl2, MgBr2, Mg(OTf)2, LiOTf, NaOTf, KOTf, Me3SiOTf, Cu(OTf)2, CuCl2, YCl3, Y(OTf)3, TiCl4, TiBr4, ZrCl4, ZrBr4, FeCl3, FeBr3, CoCl3, and CoBr3.

[0198] In each of the above schemes, a Bronsted base or Lewis acid may be used to promote the tandem hetero Friedel-Crafts reaction. However, when a boron halide such as boron trifluoride, boron trichloride, boron tribromide, or boron triiodide is used, acids such as hydrogen fluoride, hydrogen chloride, hydrogen bromide, and hydrogen iodide are generated as the aromatic electrophilic substitution reaction proceeds, so it is effective to use a Bronsted base to capture the acid. On the other hand, when a boron amino halide or a boron alkoxylate is used, amines and alcohols are generated as the aromatic electrophilic substitution reaction proceeds, so it is not necessary to use a Bronsted base in many cases, but since the ability of amino groups and alkoxy groups to be removed is low, it is effective to use a Lewis acid to promote their removal.

[0199] 3. Organic Devices The polycyclic aromatic compound according to the present invention can be used as a material for an organic device, such as an organic electroluminescent element, an organic field effect transistor, or an organic thin-film solar cell.

[0200] 3-1. Organic electroluminescent device The organic EL element according to the present embodiment will be described in detail below with reference to the drawings. Fig. 1 is a schematic cross-sectional view showing the organic EL element according to the present embodiment.

[0201] <Structure of organic electroluminescent device> The organic EL element 100 shown in FIG. 1 has a substrate 101, an anode 102 provided on the substrate 101, a hole injection layer 103 provided on the anode 102, a hole transport layer 104 provided on the hole injection layer 103, an emitting layer 105 provided on the hole transport layer 104, an electron transport layer 106 provided on the emitting layer 105, an electron injection layer 107 provided on the electron transport layer 106, and a cathode 108 provided on the electron injection layer 107.

[0202] The organic EL element 100 may be fabricated in the reverse order, for example, to have a substrate 101, a cathode 108 provided on the substrate 101, an electron injection layer 107 provided on the cathode 108, an electron transport layer 106 provided on the electron injection layer 107, an emitting layer 105 provided on the electron transport layer 106, a hole transport layer 104 provided on the emitting layer 105, a hole injection layer 103 provided on the hole transport layer 104, and an anode 102 provided on the hole injection layer 103.

[0203] Not all of the above layers are essential, and the minimum structural unit is a structure consisting of an anode 102, an emitting layer 105, and a cathode 108. The hole injection layer 103, the hole transport layer 104, the electron transport layer 106, and the electron injection layer 107 are layers that may be provided optionally. Each of the above layers may consist of a single layer or multiple layers.

[0204] In addition to the above-mentioned "substrate / anode / hole injection layer / hole transport layer / light-emitting layer / electron transport layer / electron injection layer / cathode" configuration, the layers constituting the organic EL element may be configured as "substrate / anode / hole transport layer / light-emitting layer / electron transport layer / electron injection layer / cathode", "substrate / anode / hole injection ...hole transport layer / light-emitting layer / electron injection layer / cathode", "substrate / anode / hole injection layer / hole transport layer / light-emitting layer / electron injection layer / cathode", or "substrate / anode / hole injection layer / hole transport layer / light-emitting layer / electron transport The configuration may be, for example, "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 transport layer / light-emitting layer / electron injection 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 / hole injection layer / light-emitting layer / electron transport layer / cathode", "substrate / anode / light-emitting layer / electron transport layer / cathode", or "substrate / anode / light-emitting layer / electron injection layer / cathode".

[0205] <Substrate for organic electroluminescence device> The substrate 101 is a support for the organic EL element 100, and is usually made of quartz, glass, metal, plastic, or the like. The substrate 101 is formed into a plate, film, or sheet shape depending on the purpose, and for example, a glass plate, a metal plate, a metal foil, a plastic film, a plastic sheet, or the like is used. Among them, a glass plate and a plate made of a transparent synthetic resin such as polyester, polymethacrylate, polycarbonate, or polysulfone are preferable. For a glass substrate, soda-lime glass or alkali-free glass is used, and the thickness is sufficient to maintain mechanical strength, so that it may be, for example, 0.2 mm or more. The upper limit of the thickness is, for example, 2 mm or less, preferably 1 mm or less. As for the material of the glass, it is preferable that the amount of ions eluted from the glass is small, so alkali-free glass is preferable, but soda-lime glass with a barrier coat such as SiO2 is also commercially available, and this can be used. In addition, in order to improve the gas barrier properties of the substrate 101, a gas barrier film such as a dense silicon oxide film may be provided on at least one side thereof. It is particularly preferable to provide a gas barrier film when a synthetic resin plate, film or sheet having poor gas barrier properties is used as the substrate 101.

[0206] <Anode in organic electroluminescent device> The anode 102 serves to inject holes into the light-emitting layer 105. When at least one of the hole injection layer 103 and the hole transport layer 104 is provided between the anode 102 and the light-emitting layer 105, holes are injected into the light-emitting layer 105 via these layers.

[0207] Materials for forming the anode 102 include inorganic compounds and organic compounds. Examples of inorganic compounds include metals (aluminum, gold, silver, nickel, palladium, chromium, etc.), metal oxides (indium oxide, tin oxide, indium-tin oxide (ITO), indium-zinc oxide (IZO), etc.), metal halides (copper iodide, etc.), copper sulfide, carbon black, ITO glass, and Nesa glass. Examples of organic compounds include polythiophenes such as poly(3-methylthiophene), polypyrrole, polyaniline, and other conductive polymers. In addition, materials that are used as anodes in organic EL elements can be appropriately selected and used.

[0208] The resistance of the transparent electrode is not limited as long as it can supply a sufficient current for the light emission of the light emitting element, but it is desirable that the resistance is low from the viewpoint of the power consumption of the light emitting element. For example, an ITO substrate of 300Ω / □ or less functions as an element electrode, but since it is now possible to supply substrates of about 10Ω / □, it is particularly desirable to use a low resistance product of, for example, 100 to 5Ω / □, preferably 50 to 5Ω / □. The thickness of the ITO can be selected arbitrarily according to the resistance value, but it is usually used in the range of 50 to 300 nm.

[0209] <Hole injection layer and hole transport layer in organic electroluminescence device> The hole injection layer 103 plays a role of efficiently injecting holes moving from the anode 102 into the light emitting layer 105 or the hole transport layer 104. The hole transport layer 104 plays a role of efficiently transporting holes injected from the anode 102 or holes injected from the anode 102 via the hole injection layer 103 to the light emitting layer 105. The hole injection layer 103 and the hole transport layer 104 are each formed by laminating and mixing one or more types of hole injection / transport materials, or by a mixture of a hole injection / transport material and a polymer binder. Alternatively, a layer may be formed by adding an inorganic salt such as iron (III) chloride to the hole injection / transport material.

[0210] A hole injection / transport material is required to efficiently inject / transport holes from the positive electrode between electrodes to which an electric field is applied, and it is desirable for the material to have high hole injection efficiency and efficiently transport the injected holes. For this purpose, it is preferable for the material to have a small ionization potential, a large hole mobility, excellent stability, and a low probability of generating impurities that act as traps during manufacture and use.

[0211] As the material for forming the hole injection layer 103 and the hole transport layer 104, any compound can be selected from compounds conventionally used as charge transport materials for holes in photoconductive materials, p-type semiconductors, and known compounds used in hole injection layers and hole transport layers of organic EL elements. Specific examples of such compounds include carbazole derivatives (N-phenylcarbazole, polyvinylcarbazole, etc.), biscarbazole derivatives such as bis(N-arylcarbazole) or bis(N-alkylcarbazole), triarylamine derivatives (polymers having an aromatic tertiary amino in the main chain or side chain, 1,1-bis(4-di-p-tolylaminophenyl)cyclohexane, N,N'-diphenyl-N,N'-di(3-methylphenyl)-4,4'-diaminobiphenyl, N,N'-diphenyl-N,N'-dinaphthyl-4,4'-diaminobiphenyl, N,N'-diphenyl-N,N'-di(3-methylphenyl)-4,4'-diphenyl-1,1'-diamine, N,N'-dinaphthyl-N,N'-diphenyl-4,4'-diphenyl-1,1'-diamine, N4 ,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"-tris(3-methylphenyl(phenyl)amino)triphenylamine and other triphenylamine derivatives, starburst amine derivatives, etc.), stilbene derivatives, phthalocyanine derivatives (metal-free, copper phthalocyanine, etc.), pyrazoline derivatives, hydrazone compounds, benzofuran derivatives, thiophene derivatives, oxadiazole derivatives, quinoxaline derivatives Conductors (e.g., 1,4,5,8,9,12-hexaazatriphenylene-2,3,6,7,10,11-hexacarbonitrile, etc.), heterocyclic compounds such as porphyrin derivatives, polysilanes, etc. As polymers, polycarbonates and styrene derivatives having the above-mentioned monomers in their side chains, polyvinylcarbazole, polysilanes, etc. are preferred, but there are no particular limitations on the compounds as long as they can form a thin film required for fabricating a light-emitting device, can inject holes from the anode, and can transport holes.

[0212] It is also known that the electrical conductivity of organic semiconductors is strongly influenced by their doping. Such organic semiconductor matrix substances consist of compounds with good electron donating or accepting properties. For doping with electron donating substances, strong electron acceptors such as tetracyanoquinone dimethane (TCNQ) or 2,3,5,6-tetrafluorotetracyano-1,4-benzoquinone dimethane (F4TCNQ) are known (see, for example, the literature "M. Pfeiffer, A. Beyer, T. Fritz, K. Leo, Appl. Phys. Lett., 73(22), 3202-3204 (1998)" and the literature "J. Blochwitz, M. Pheiffer, T. Fritz, K. Leo, Appl. Phys. Lett., 73(6), 729-731 (1998)"). These generate so-called holes by an electron transfer process in the electron donating base substance (hole transport substance). The conductivity of the base material varies considerably depending on the number and mobility of holes. Matrix materials having hole transport properties are known, for example, benzidine derivatives (TPD, etc.) or starburst amine derivatives (TDATA, etc.), or certain metal phthalocyanines (especially zinc phthalocyanine (ZnPc) and the like) (JP 2005-167175 A).

[0213] <Light-emitting layer in organic electroluminescent device> The light-emitting layer 105 is a layer that emits light by recombining holes injected from the anode 102 and electrons injected from the cathode 108 between electrodes to which an electric field is applied. The material for the light-emitting layer 105 may be a compound (light-emitting compound) that is excited and emits light by the recombination of holes and electrons, and is preferably a compound that can be formed into a stable thin film shape and exhibits strong luminescence (fluorescence) efficiency in a solid state.

[0214] The light-emitting layer may be a single layer or multiple layers, each of which is formed from materials for the light-emitting layer (host material, dopant material). The host material and the dopant material may each be one type or a combination of multiple types. The dopant material may be contained in the entire host material or may be contained partially in the host material. As a doping method, the dopant material may be formed by co-evaporation with the host material, but it may also be mixed with the host material in advance and then vapor-deposited at the same time.

[0215] The amount of the host material used varies depending on the type of the host material and may be determined according to the properties of the host material. The amount of the host material used is preferably 50 to 99.999% by weight, more preferably 80 to 99.95% by weight, and even more preferably 90 to 99.9% by weight, of the total material for the light-emitting layer.

[0216] The amount of the dopant material used varies depending on the type of dopant material, and may be determined according to the properties of the dopant material. The amount of the dopant used is preferably 0.001 to 50% by weight, more preferably 0.05 to 20% by weight, and even more preferably 0.1 to 10% by weight, based on the total material for the light-emitting layer. The above range is preferable in that, for example, concentration quenching can be prevented. In addition, from the viewpoint of durability, it is also preferable that some or all of the hydrogen atoms of the dopant material are deuterated.

[0217] Examples of the host material include condensed ring derivatives such as anthracene, pyrene, dibenzochrysene, or fluorene, which have been known as light emitters for a long time, bisstyryl derivatives such as bisstyryl anthracene derivatives and distyrylbenzene derivatives, tetraphenylbutadiene derivatives, and cyclopentadiene derivatives. In particular, anthracene-based compounds, fluorene-based compounds, or dibenzochrysene-based compounds are preferred. In addition, from the viewpoint of durability, it is also preferred that some or all of the hydrogen atoms of the host material are deuterated. Furthermore, it is also preferred to form the light emitting layer by combining a host compound in which some or all of the hydrogen atoms are deuterated with a dopant compound in which some or all of the hydrogen atoms are deuterated.

[0218] <Anthracene compounds> The anthracene compound as the host is, for example, a compound represented by the following general formula (3). [ka]

[0219] In formula (3), X and Ar 4 are each independently hydrogen, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted diarylamino, optionally substituted diheteroarylamino, optionally substituted arylheteroarylamino, optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted alkenyl, optionally substituted alkoxy, optionally substituted aryloxy, optionally substituted arylthio or optionally substituted silyl; and all X and Ar 4 cannot simultaneously become hydrogen, At least one hydrogen in the compound represented by formula (3) may be substituted with halogen, cyano, deuterium or an optionally substituted heteroaryl.

[0220] In addition, a polymer (preferably a dimer) may be formed using the structure represented by formula (3) as a unit structure. In this case, for example, the unit structures represented by formula (3) may be bonded to each other via X, and examples of X include a single bond, arylene (phenylene, biphenylene, naphthylene, etc.), and heteroarylene (a group having a divalent bond such as a pyridine ring, a dibenzofuran ring, a dibenzothiophene ring, a carbazole ring, a benzocarbazole ring, and a phenyl-substituted carbazole ring).

[0221] The details of the above aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, alkyl, cycloalkyl, alkenyl, alkoxy, aryloxy, arylthio, or silyl will be described in the following preferred embodiment section. The substituents on these include aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, alkyl, cycloalkyl, alkenyl, alkoxy, aryloxy, arylthio, or silyl, and the details of these are also described in the following preferred embodiment section.

[0222] Preferred embodiments of the above anthracene-based compounds are described below. The symbols in the structures below are defined as above. [ka]

[0223] In the general formula (3), X is each independently a group represented by the above formula (3-X1), formula (3-X2) or formula (3-X3), and the group represented by formula (3-X1), formula (3-X2) or formula (3-X3) is bonded to the anthracene ring of formula (3) at *. Preferably, two Xs are not simultaneously a group represented by formula (3-X3). More preferably, two Xs are not simultaneously a group represented by formula (3-X2).

[0224] In addition, a polymer (preferably a dimer) may be formed using the structure represented by formula (3) as a unit structure. In this case, for example, the unit structures represented by formula (3) may be bonded to each other via X, and examples of X include a single bond, arylene (phenylene, biphenylene, naphthylene, etc.), and heteroarylene (a group having a divalent bond such as a pyridine ring, a dibenzofuran ring, a dibenzothiophene ring, a carbazole ring, a benzocarbazole ring, and a phenyl-substituted carbazole ring).

[0225] The naphthylene moieties in formula (3-X1) and formula (3-X2) may be condensed with one benzene ring. The condensed structures are as follows: [ka]

[0226] Ar 1 and Ar 2 are each independently hydrogen, phenyl, biphenylyl, terphenylyl, quaterphenylyl, naphthyl, phenanthryl, fluorenyl, benzofluorenyl, chrysenyl, triphenylenyl, pyrenylyl, or a group represented by the above formula (A) (including a carbazolyl group, a benzocarbazolyl group, and a phenyl-substituted carbazolyl group). 1 or Ar 2 is a group represented by formula (A), the group represented by formula (A) is bonded to the naphthalene ring in formula (3-X1) or formula (3-X2) at the *.

[0227] Ar 3 is phenyl, biphenylyl, terphenylyl, quaterphenylyl, naphthyl, phenanthryl, fluorenyl, benzofluorenyl, chrysenyl, triphenylenyl, pyrenylyl, or a group represented by the above formula (A) (including a carbazolyl group, a benzocarbazolyl group, and a phenyl-substituted carbazolyl group). 3is a group represented by formula (A), the group represented by formula (A) is bonded to the single bond represented by a straight line in formula (3-X3) at the *. That is, the anthracene ring in formula (3) and the group represented by formula (A) are directly bonded.

[0228] Also, Ar 3 may have a substituent, and Ar 3 At least one hydrogen atom in may be further substituted with an alkyl group having 1 to 4 carbon atoms, a cycloalkyl group having 5 to 10 carbon atoms, phenyl, biphenylyl, terphenylyl, naphthyl, phenanthryl, fluorenyl, chrysenyl, triphenylenyl, pyrenylyl, or a group represented by the above formula (A) (including a carbazolyl group and a phenyl-substituted carbazolyl group). 3 is a group represented by formula (A), the group represented by formula (A) is Ar 3 and combine.

[0229] Ar 4 are each independently hydrogen, phenyl, biphenylyl, terphenylyl, naphthyl, or silyl substituted with alkyl having 1 to 4 carbon atoms (eg, methyl, ethyl, t-butyl) and / or cycloalkyl having 5 to 10 carbon atoms.

[0230] Examples of the alkyl group having 1 to 4 carbon atoms that substitutes for the silyl include methyl, ethyl, propyl, i-propyl, butyl, sec-butyl, t-butyl, and cyclobutyl, and three hydrogen atoms in the silyl are each independently substituted with these alkyl groups.

[0231] Specific examples of "silyl substituted with alkyl having 1 to 4 carbon atoms" include trimethylsilyl, triethylsilyl, tripropylsilyl, tri-i-propylsilyl, tributylsilyl, tri-sec-butylsilyl, tri-t-butylsilyl, ethyldimethylsilyl, propyldimethylsilyl, i-propyldimethylsilyl, butyldimethylsilyl, sec-butyldimethylsilyl, t-butyldimethylsilyl, methyldiethylsilyl, propyldiethylsilyl, i-propyldiethylsilyl, butyldiethylsilyl, sec-butyldiethylsilyl, t-butyldiethylsilyl, methyldipropylsilyl, ethyldipropylsilyl, butyldipropylsilyl, sec-butyldipropylsilyl, t-butyldipropylsilyl, methyldi-i-propylsilyl, ethyldi-i-propylsilyl, butyldi-i-propylsilyl, sec-butyldi-i-propylsilyl, and t-butyldi-i-propylsilyl.

[0232] Examples of the cycloalkyl having 5 to 10 carbon atoms substituting the silyl include cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, norbornenyl, bicyclo[1.1.1]pentyl, bicyclo[2.0.1]pentyl, bicyclo[1.2.1]hexyl, bicyclo[3.0.1]hexyl, bicyclo[2.1.2]heptyl, bicyclo[2.2.2]octyl, adamantyl, decahydronaphthalenyl, and decahydroazulenyl, and three hydrogen atoms in the silyl are each independently substituted with these cycloalkyls.

[0233] Specific examples of the "silyl substituted with cycloalkyl having 5 to 10 carbon atoms" include tricyclopentylsilyl and tricyclohexylsilyl.

[0234] Substituted silyls include dialkylcycloalkylsilyls, which are substituted with two alkyl groups and one cycloalkyl group, and alkyldicycloalkylsilyls, which are substituted with one alkyl group and two cycloalkyl groups. Specific examples of the alkyl and cycloalkyl groups are as described above.

[0235] In addition, hydrogen in the chemical structure of the anthracene compound represented by general formula (3) may be substituted with a group represented by the above formula (A). When substituted with a group represented by formula (A), the group represented by formula (A) replaces at least one hydrogen in the compound represented by formula (3) at the *.

[0236] The group represented by formula (A) is one of the substituents that the anthracene compound represented by formula (3) can have. [ka]

[0237] In the above formula (A), Y is -O-, -S- or >NR 29 and R 21 ~R 28 are each independently hydrogen, optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted alkoxy, optionally substituted aryloxy, optionally substituted arylthio, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, alkyldicycloalkylsilyl, optionally substituted amino, halogen, hydroxy or cyano; R 21 ~R 28 adjacent groups among R may be bonded to each other to form a hydrocarbon ring, an aryl ring, or a heteroaryl ring; 29 is hydrogen or optionally substituted aryl.

[0238] R 21 ~R 28The "alkyl" in the "optionally substituted alkyl" may be either linear or branched, and examples thereof include linear alkyl having 1 to 24 carbon atoms or branched alkyl having 3 to 24 carbon atoms. An alkyl having 1 to 18 carbon atoms (branched alkyl having 3 to 18 carbon atoms) is preferred, an alkyl having 1 to 12 carbon atoms (branched alkyl having 3 to 12 carbon atoms) is more preferred, an alkyl having 1 to 6 carbon atoms (branched alkyl having 3 to 6 carbon atoms) is even more preferred, and an alkyl having 1 to 4 carbon atoms (branched alkyl having 3 to 4 carbon atoms) is particularly preferred.

[0239] Specific examples of "alkyl" include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, t-butyl, n-pentyl, isopentyl, neopentyl, t-pentyl (t-amyl), n-hexyl, 1-methylpentyl, 3,3-dimethylbutyl, 2-ethylbutyl, n-heptyl, 1-methylhexyl, n-octyl, t-octyl (1,1,3,3-tetramethylbutyl), 1-methyl, Examples of the aryl group include n-hexyl, n-butyl, n-hexyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 2,6-dimethyl-4-heptyl, 3,5,5-trimethylhexyl, n-decyl, n-undecyl, 1-methyldecyl, n-dodecyl, n-tridecyl, 1-hexylheptyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, n-heptadecyl, n-octadecyl, and n-eicosyl.

[0240] R 21 ~R 28 Examples of the "cycloalkyl" in the "optionally substituted cycloalkyl" include cycloalkyl having 3 to 24 carbon atoms, cycloalkyl having 3 to 20 carbon atoms, cycloalkyl having 3 to 16 carbon atoms, cycloalkyl having 3 to 14 carbon atoms, cycloalkyl having 5 to 10 carbon atoms, cycloalkyl having 5 to 8 carbon atoms, cycloalkyl having 5 to 6 carbon atoms, and cycloalkyl having 5 carbon atoms.

[0241] Specific examples of "cycloalkyl" include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, and alkyl (especially methyl) substituted derivatives of these having 1 to 4 carbon atoms, as well as norbornenyl, bicyclo[1.0.1]butyl, bicyclo[1.1.1]pentyl, bicyclo[2.0.1]pentyl, bicyclo[1.2.1]hexyl, bicyclo[3.0.1]hexyl, bicyclo[2.1.2]heptyl, bicyclo[2.2.2]octyl, adamantyl, diamantyl, decahydronaphthalenyl, and decahydroazulenyl.

[0242] R 21 ~R 28 In the above, the "aryl" in the "optionally substituted aryl" includes, for example, aryl having 6 to 30 carbon atoms, preferably aryl having 6 to 16 carbon atoms, more preferably aryl having 6 to 12 carbon atoms, and particularly preferably aryl having 6 to 10 carbon atoms.

[0243] Specific examples of "aryl" include a monocyclic ring system such as phenyl, a bicyclic ring system such as biphenylyl, a fused bicyclic ring system such as naphthyl, a tricyclic ring system such as terphenylyl (m-terphenylyl, o-terphenylyl, p-terphenylyl), a fused tricyclic ring system such as acenaphthylenyl, fluorenyl, phenalenyl, and phenanthrenyl, a fused tetracyclic ring system such as triphenylenyl, pyrenyl, and naphthacenyl, and a fused pentacyclic ring system such as perylenyl and pentacenyl.

[0244] R 21 ~R 28 Examples of the "heteroaryl" in the "optionally substituted heteroaryl" include heteroaryl having 2 to 30 carbon atoms, preferably heteroaryl having 2 to 25 carbon atoms, more preferably heteroaryl having 2 to 20 carbon atoms, further preferably heteroaryl having 2 to 15 carbon atoms, and particularly preferably heteroaryl having 2 to 10 carbon atoms. Examples of the heteroaryl include heterocycles containing, as ring-constituting atoms other than carbon, 1 to 5 heteroatoms selected from oxygen, sulfur, and nitrogen.

[0245] Specific examples of "heteroaryl" include pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, oxadiazolyl, thiadiazolyl, triazolyl, tetrazolyl, pyrazolyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, indolyl, isoindolyl, 1H-indazolyl, benzimidazolyl, benzoxazolyl, benzothiazolyl, 1H-benzotriazolyl, quinolyl, isoquinolyl, cyclohex ... Examples of such aryl groups include aryl, aryloxy, aryloxy, aryloxy, and aryloxy groups. Examples of such aryl groups include aryloxy, aryloxy, aryloxy, and aryloxy groups include aryloxy, aryloxy, and aryloxy groups. Examples of such aryl groups include aryloxy, aryloxy, and aryloxy groups include aryloxy, aryloxy, and aryloxy groups. Examples of such aryl groups include aryloxy, aryloxy, and aryloxy groups include aryloxy, aryloxy, and aryloxy groups.

[0246] R 21 ~R 28 Examples of the "alkoxy" in the "optionally substituted alkoxy" include linear alkoxy having 1 to 24 carbon atoms or branched alkoxy having 3 to 24 carbon atoms. An alkoxy having 1 to 18 carbon atoms (branched alkoxy having 3 to 18 carbon atoms) is preferred, an alkoxy having 1 to 12 carbon atoms (branched alkoxy having 3 to 12 carbon atoms) is more preferred, an alkoxy having 1 to 6 carbon atoms (branched alkoxy having 3 to 6 carbon atoms) is even more preferred, and an alkoxy having 1 to 4 carbon atoms (branched alkoxy having 3 to 4 carbon atoms) is particularly preferred.

[0247] Specific examples of "alkoxy" include methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, s-butoxy, t-butoxy, pentyloxy, hexyloxy, heptyloxy, octyloxy, and the like.

[0248] R 21 ~R 28The "aryloxy" in the "optionally substituted aryloxy" is a group in which the hydrogen of the -OH group is replaced by an aryl, and this aryl is one of the above-mentioned R 21 ~R 28 The groups described as "aryl" in the above formula can be cited.

[0249] R 21 ~R 28 The "arylthio" in the "optionally substituted arylthio" is a group in which the hydrogen of the -SH group is replaced by an aryl, and this aryl is the same as R 21 ~R 28 The groups described as "aryl" in the above formula can be cited.

[0250] R 21 ~R 28 The "trialkylsilyl" in the above formula is a silyl group in which each of the three hydrogen atoms is independently replaced by an alkyl group, and the alkyl group is the same as R 21 ~R 28 The groups described as "alkyl" in the above can be cited. Preferred alkyl groups for substitution are alkyl groups having 1 to 4 carbon atoms, and specific examples thereof include methyl, ethyl, propyl, i-propyl, butyl, sec-butyl, t-butyl, and cyclobutyl.

[0251] Specific examples of the "trialkylsilyl" include trimethylsilyl, triethylsilyl, tripropylsilyl, tri-i-propylsilyl, tributylsilyl, tri-sec-butylsilyl, tri-t-butylsilyl, ethyldimethylsilyl, propyldimethylsilyl, i-propyldimethylsilyl, butyldimethylsilyl, sec-butyldimethylsilyl, t-butyldimethylsilyl, methyldiethylsilyl, propyldiethylsilyl, i-propyldiethylsilyl, butyldiethylsilyl, sec-butyldiethylsilyl, t-butyldiethylsilyl, methyldipropylsilyl, ethyldipropylsilyl, butyldipropylsilyl, sec-butyldipropylsilyl, t-butyldipropylsilyl, methyldi-i-propylsilyl, ethyldi-i-propylsilyl, butyldi-i-propylsilyl, sec-butyldi-i-propylsilyl, and t-butyldi-i-propylsilyl.

[0252] R 21 ~R 28 The "tricycloalkylsilyl" in the above formula is a silyl group in which each of the three hydrogen atoms is independently replaced by a cycloalkyl, and the cycloalkyl is the same as R 21 ~R 28 The groups described as "cycloalkyl" in the above can be cited. Preferred cycloalkyl for substitution is cycloalkyl having 5 to 10 carbon atoms, and specific examples thereof include cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, bicyclo[1.1.1]pentyl, bicyclo[2.0.1]pentyl, bicyclo[1.2.1]hexyl, bicyclo[3.0.1]hexyl, bicyclo[2.1.2]heptyl, bicyclo[2.2.2]octyl, adamantyl, decahydronaphthalenyl, and decahydroazulenyl.

[0253] Specific examples of the "tricycloalkylsilyl" include tricyclopentylsilyl, tricyclohexylsilyl, and the like.

[0254] Specific examples of dialkylcycloalkylsilyl substituted with two alkyls and one cycloalkyl and alkyldicycloalkylsilyl substituted with one alkyl and two cycloalkyls include silyl substituted with a group selected from the specific alkyls and cycloalkyls mentioned above.

[0255] R 21 ~R 28 The "substituted amino" in the "optionally substituted amino" in the above is, for example, an amino group in which two hydrogen atoms are substituted with aryl or heteroaryl. An amino group in which two hydrogen atoms are substituted with aryl is a diaryl-substituted amino, an amino group in which two hydrogen atoms are substituted with heteroaryl is a diheteroaryl-substituted amino, and an amino group in which two hydrogen atoms are substituted with an aryl and a heteroaryl is an arylheteroaryl-substituted amino. The aryl and heteroaryl are as defined above in R 21 ~R 28 The groups described above as "aryl" and "heteroaryl" can be cited.

[0256] Specific examples of the "substituted amino" include diphenylamino, dinaphthylamino, phenylnaphthylamino, dipyridylamino, phenylpyridylamino, naphthylpyridylamino, and the like.

[0257] R 21 ~R 28 "Halogen" in the above formula includes fluorine, chlorine, bromine, and iodine.

[0258] R 21 ~R 28 Some of the groups described as may be substituted as described above, in which case the substituents include alkyl, cycloalkyl, aryl, or heteroaryl. The alkyl, cycloalkyl, aryl, or heteroaryl may be any of the groups described above as R 21 ~R 28 In the above, reference can be made to a group described as "alkyl", "cycloalkyl", "aryl" or "heteroaryl".

[0259] Y as 'NR' 29 " R in 29 is hydrogen or an optionally substituted aryl, and the aryl is as defined above in R 21 ~R 28 The group described as "aryl" in the above formula can be cited, and the substituents thereof include R 21 ~R 28 The groups described above as substituents for the above can be cited.

[0260] R 21 ~R 28 Among these, adjacent groups may be bonded to each other to form a hydrocarbon ring, an aryl ring, or a heteroaryl ring. The group represented by the following formula (A-1) does not form a ring, and the group represented by any of the following formulas (A-2) to (A-14) may be used as examples of the group represented by any of the following formulas (A-1) to (A-14). At least one hydrogen atom in the group represented by any of the formulas (A-1) to (A-14) may be substituted with an alkyl, cycloalkyl, aryl, heteroaryl, alkoxy, aryloxy, arylthio, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, alkyldicycloalkylsilyl, diaryl-substituted amino, diheteroaryl-substituted amino, arylheteroaryl-substituted amino, halogen, hydroxy, or cyano. Y and * in the formulas are defined as above. [ka]

[0261] Examples of rings formed by bonding adjacent groups to each other include a hydrocarbon ring such as a cyclohexane ring, and examples of aryl and heteroaryl rings include the above-mentioned R 21 ~R 28 Examples of the ring structures include those described for "aryl" and "heteroaryl" in the above formula (A-1), and these rings are formed so as to be condensed with one or two benzene rings in the above formula (A-1).

[0262] Examples of the group represented by formula (A) include groups represented by any of the above formulas (A-1) to (A-14). Groups represented by any of the above formulas (A-1) to (A-5) and (A-12) to (A-14) are preferred. Groups represented by any of the above formulas (A-1) to (A-4) are more preferred. Groups represented by any of the above formulas (A-1), (A-3) and (A-4) are even more preferred. Groups represented by the above formula (A-1) are particularly preferred.

[0263] The group represented by formula (A) is a naphthalene ring in formula (3-X1) or formula (3-X2), a single bond in formula (3-X3), Ar in formula (3-X3), 3 As described above, the naphthalene ring in formula (3-X1) or formula (3-X2), the single bond in formula (3-X3), and Ar in formula (3-X3) are substituted with at least one hydrogen atom in the compound represented by formula (3). 3 A form in which the compound is bound to at least one of the above is preferred.

[0264] In addition, in the structure of the group represented by formula (A), a naphthalene ring in formula (3-X1) or formula (3-X2), a single bond in formula (3-X3), Ar in formula (3-X3), 3 The position at which R is bonded, and the position at which at least one hydrogen atom in the compound represented by formula (3) is substituted in the structure of the group represented by formula (A), may be any position in the structure of formula (A), for example, any of the two benzene rings in the structure of formula (A) or R 21 ~R 28 Any of the rings formed by bonding adjacent groups to each other, or ">NR 29 " R in 29 The bond can be at any position within the

[0265] Examples of the group represented by formula (A) include the following groups: In the formula, Y and * are defined as above. [ka] [ka]

[0266] All or a part of the hydrogen atoms in the chemical structure of the anthracene compound represented by the general formula (3) may be deuterium atoms.

[0267] Specific examples of the anthracene-based compound include compounds represented by any of the following formulae (3-1) to (3-142): In the following structural formulae, "Me" represents a methyl group, "D" represents deuterium, and "tBu" represents a t-butyl group.

[0268] [ka]

[0269] [ka]

[0270] [ka]

[0271] [ka]

[0272] [ka]

[0273] [ka]

[0274] [ka]

[0275] The anthracene compound represented by formula (3) is a compound having a reactive group at a desired position of an anthracene skeleton, and X, Ar 4 The compound having a reactive group in a partial structure such as the structure of formula (A) can be used as a starting material to produce the compound by applying Suzuki coupling, Negishi coupling, or other known coupling reactions. Examples of reactive groups in these reactive compounds include halogens and boronic acids. As a specific production method, for example, the synthesis methods in paragraphs

[0089] to

[0175] of International Publication No. 2014 / 141725 can be referred to.

[0276] <Fluorene-based compounds> The compound represented by the general formula (4) basically functions as a host. [ka]

[0277] In the above formula (4), R 1 From R 10 are each independently a hydrogen atom, an aryl atom, a heteroaryl atom (wherein the heteroaryl atom may be bonded to the fluorene skeleton in the above formula (4) via a linking group), a diarylamino atom, a diheteroarylamino atom, an arylheteroarylamino atom, an alkyl atom, a cycloalkyl atom, an alkenyl atom, an alkoxy atom, or an aryloxy atom, in which at least one hydrogen atom may be substituted with an aryl atom, a heteroaryl atom, an alkyl atom, or a cycloalkyl atom; Also, 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 10may each independently bond to form a fused ring or a spiro ring, at least one hydrogen in the formed ring may be replaced with an aryl, a heteroaryl (the heteroaryl may be bonded to the formed ring via a linking group), a diarylamino, a diheteroarylamino, an arylheteroarylamino, an alkyl, a cycloalkyl, an alkenyl, an alkoxy, or an aryloxy, at least one hydrogen in these may be replaced with an aryl, a heteroaryl, an alkyl, or a cycloalkyl, and At least one hydrogen in the compound represented by formula (4) may be substituted with halogen, cyano or deuterium.

[0278] For details of each group in the definition of the above formula (4), the explanation for the polycyclic aromatic compound of the above formula (1) or formula (2) can be cited.

[0279] R 1 From R 10 Examples of the alkenyl in the above formula include alkenyl having 2 to 30 carbon atoms, preferably alkenyl having 2 to 20 carbon atoms, more preferably alkenyl having 2 to 10 carbon atoms, further preferably alkenyl having 2 to 6 carbon atoms, and particularly preferably alkenyl having 2 to 4 carbon atoms. Preferred alkenyls 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.

[0280] Specific examples of heteroaryl include monovalent groups represented by removing any one hydrogen atom from a compound of the following formula (4-Ar1), formula (4-Ar2), formula (4-Ar3), formula (4-Ar4), or formula (4-Ar5). [ka] In formulas (4-Ar1) to (4-Ar5), Y 1are each independently O, S or NR, R is phenyl, biphenylyl, naphthyl, anthracenyl or hydrogen; At least one hydrogen atom in the structures of the above formulae (4-Ar1) to (4-Ar5) may be substituted with phenyl, biphenylyl, naphthyl, anthracenyl, phenanthrenyl, methyl, ethyl, propyl, or butyl.

[0281] These heteroaryls may be bonded to the fluorene skeleton in the above formula (4) via a linking group. That is, the fluorene skeleton in the formula (4) and the above heteroaryls may be bonded directly, or may be bonded to each other via a linking group. Examples of the linking group include phenylene, biphenylene, naphthylene, anthracenylene, methylene, ethylene, -OCH2CH2-, -CH2CH2O-, or -OCH2CH2O-.

[0282] In addition, R in formula (4) 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 are each independently bonded to form a fused ring, R 9 and R 10 may be bonded to form a spiro ring. 1 From R 8 The condensed ring formed by is a ring condensed to the benzene ring in formula (4), and is an aliphatic ring or an aromatic ring. An aromatic ring is preferable, and examples of the structure including the benzene ring in formula (4) include a naphthalene ring and a phenanthrene ring. 9 and R 10 The spiro ring formed by the formula (4) is a ring that is spiro-bonded to the five-membered ring in the formula (4), and is an aliphatic ring or an aromatic ring. An aromatic ring, such as a fluorene ring, is preferred.

[0283] The compound represented by the general formula (4) is preferably a compound represented by the following formula (4-1), formula (4-2) or formula (4-3), 1 and R 2 A compound having a condensed benzene ring formed by bonding with R 3 and R 4 A compound having a condensed benzene ring formed by bonding with R 1 From R 8 is a compound in which none of the above is bound. [ka]

[0284] R in formula (4-1), formula (4-2) and formula (4-3) 1 From R 10 The definition of R in Eq. (4) corresponds to 1 From R 10 is the same as R in formula (4-1) and formula (4-2). 11 From R 14 The definition of R in Eq. (4) 1 From R 10 is the same as:

[0285] The compound represented by general formula (4) is more preferably a compound represented by the following formula (4-1A), formula (4-2A) or formula (4-3A), in which R 9 and R 10 is a compound in which a spiro-fluorene ring is formed by bonding. [ka]

[0286] R in formula (4-1A), formula (4-2A) and formula (4-3A) 2 From R 7 The definition of is the corresponding R in formula (4-1), formula (4-2) and formula (4-3). 2 From R 7and R in formula (4-1A) and formula (4-2A) 11 From R 14 The definition of R in formula (4-1) and formula (4-2) 11 From R 14 is the same as:

[0287] In addition, all or a part of the hydrogen atoms in the compound represented by formula (4) may be substituted with halogen, cyano or deuterium.

[0288] Specific examples of the fluorene-based compound include compounds represented by any of the following formulas (4-4) to (4-22): In addition, "Me" in the following structural formulas represents a methyl group. [ka]

[0289] <Dibenzochrysene compounds> The dibenzochrysene compound as the host is, for example, a compound represented by the following general formula (5). [ka]

[0290] In the above formula (5), R 1 From R 16 are each independently a hydrogen atom, an aryl, a heteroaryl (wherein the heteroaryl may be bonded to the dibenzochrysene skeleton in the above formula (5) via a linking group), a diarylamino, a diheteroarylamino, an arylheteroarylamino, an alkyl, a cycloalkyl, an alkenyl, an alkoxy, or an aryloxy, in which at least one hydrogen atom may be substituted with an aryl, a heteroaryl, an alkyl, or a cycloalkyl; Also, R 1 From R 16adjacent groups among these may be bonded to each other to form a condensed ring, at least one hydrogen atom in the formed ring may be substituted with an aryl, a heteroaryl (the heteroaryl may be bonded to the formed ring via a linking group), a diarylamino, a diheteroarylamino, an arylheteroarylamino, an alkyl, a cycloalkyl, an alkenyl, an alkoxy, or an aryloxy, at least one hydrogen atom in these may be substituted with an aryl, a heteroaryl, an alkyl, or a cycloalkyl, and At least one hydrogen in the compound represented by formula (5) may be substituted with halogen, cyano or deuterium.

[0291] For details of each group in the definition of the above formula (5), the explanation for the polycyclic aromatic compound of the above formula (1) or formula (2) can be cited.

[0292] The alkenyl in the definition of the above formula (5) is, for example, an alkenyl having 2 to 30 carbon atoms, preferably an alkenyl having 2 to 20 carbon atoms, more preferably an alkenyl having 2 to 10 carbon atoms, further preferably an alkenyl having 2 to 6 carbon atoms, and particularly preferably an alkenyl having 2 to 4 carbon atoms. Preferred alkenyls 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.

[0293] Specific examples of heteroaryl include monovalent groups represented by removing any one hydrogen atom from a compound of the following formula (5-Ar1), formula (5-Ar2), formula (5-Ar3), formula (5-Ar4), or formula (5-Ar5). [ka] In formula (5-Ar1) to formula (5-Ar5), Y 1are each independently O, S or NR, R is phenyl, biphenylyl, naphthyl, anthracenyl or hydrogen; At least one hydrogen atom in the structures of the above formulae (5-Ar1) to (5-Ar5) may be substituted with phenyl, biphenylyl, naphthyl, anthracenyl, phenanthrenyl, methyl, ethyl, propyl, or butyl.

[0294] These heteroaryls may be bonded to the dibenzochrysene skeleton in the above formula (5) via a linking group. That is, the dibenzochrysene skeleton and the above heteroaryl in the formula (5) may be bonded directly, or may be bonded to each other via a linking group. Examples of the linking group include phenylene, biphenylene, naphthylene, anthracenylene, methylene, ethylene, -OCH2CH2-, -CH2CH2O-, or -OCH2CH2O-.

[0295] The compound represented by the general formula (5) is preferably R 1 , R 4 , R 5 , R 8 , R 9 , R 12 , R 13 and R 16 is hydrogen. In this case, R in formula (5) 2 , R 3 , R 6 , R 7 , R 10 , R 11 , R 14 and R 15are preferably each independently hydrogen, phenyl, biphenylyl, naphthyl, anthracenyl, phenanthrenyl, a monovalent group having the structure of the above formula (5-Ar1), (5-Ar2), (5-Ar3), (5-Ar4) or (5-Ar5) (the monovalent group having the structure may be bonded to the dibenzochrysene skeleton in the above formula (5) via phenylene, biphenylene, naphthylene, anthracenylene, methylene, ethylene, -OCHCH-, -CHCHO- or -OCHCHO-), methyl, ethyl, propyl or butyl.

[0296] 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 is hydrogen. In this case, R in formula (5) 3 , R 6 , R 11 and R 14 at least one (preferably one or two, more preferably one) of the formulae (5-Ar1), (5-Ar2), (5-Ar3), (5-Ar4) or (5-Ar5) is a monovalent group having a structure represented by the formula (5-Ar1), (5-Ar2), (5-Ar3), (5-Ar4) or (5-Ar5) via a single bond, phenylene, biphenylene, naphthylene, anthracenylene, methylene, ethylene, -OCHCH-, -CHCHO-, or -OCHCHO-; The other than the at least one (i.e., other than the position substituted by the monovalent group having the structure) is hydrogen, phenyl, biphenylyl, naphthyl, anthracenyl, methyl, ethyl, propyl, or butyl, and at least one hydrogen in these may be substituted with phenyl, biphenylyl, naphthyl, anthracenyl, methyl, ethyl, propyl, or butyl.

[0297] In addition, R in formula (5)2 , R 3 , R 6 , R 7 , R 10 , R 11 , R 14 and R 15 When a monovalent group having a structure represented by the above formula (5-Ar1) to formula (5-Ar5) is selected as the aryl group, at least one hydrogen atom in the structure is R 1 From R 16 may be bonded to any one of the following to form a single bond.

[0298] Specific examples of the dibenzochrysene compound include compounds represented by any of the following formulas (5-1) to (5-39): In addition, "tBu" in the following structural formulas represents a t-butyl group. [ka]

[0299] [ka]

[0300] <Polycyclic aromatic compounds> The polycyclic aromatic compound as the host is, for example, a polycyclic aromatic compound represented by the following general formula (6), a polycyclic aromatic compound represented by the following general formula (7), or a polycyclic aromatic compound represented by the following general formula (8). The preferred form of each compound is a polycyclic aromatic compound represented by the following general formula (6'), a polycyclic aromatic compound represented by the following general formula (7'), or a polycyclic aromatic compound represented by the following general formula (8'). The definition of each symbol in the following structural formula is the same as the definition of each symbol in general formula (6), formula (7), and formula (8), and general formula (6'), formula (7'), and formula (8'), and the same applies hereinafter. For details of the structural form and substituents of the compound in each formula, the explanation in the above general formula (1) and formula (2) can be cited. [ka] [ka] [ka]

[0301] In the above formulas (6), (7) and (8), ring A, ring B and ring C are each independently an aryl ring or a heteroaryl ring, and at least one hydrogen atom in these rings may be substituted; X 1 , X 2 and X 3 are each independently >O, >NR, >C(-R)2, >S or >Se, R of the >NR is an optionally substituted aryl, an optionally substituted heteroaryl, an optionally substituted alkyl or an optionally substituted cycloalkyl, R of the >C(-R)2 is a hydrogen, an optionally substituted aryl, an optionally substituted alkyl or an optionally substituted cycloalkyl, and at least one of R of the >NR and R of the >C(-R)2 may be bonded to at least one of the A ring, the B ring and the C ring via a linking group; R 4 and R 7 each independently represents hydrogen, an aryl having 6 to 12 carbon atoms, a heteroaryl having 2 to 15 carbon atoms, a diarylamino (wherein the aryl has 6 to 12 carbon atoms), an alkyl having 1 to 6 carbon atoms, or a cycloalkyl having 3 to 14 carbon atoms; In the compound represented by formula (6), formula (7), or formula (8), at least one of ring A, ring B, ring C, aryl, and heteroaryl may be condensed with at least one cycloalkane, at least one hydrogen in the cycloalkane may be substituted, and at least one -CH2- in the cycloalkane may be substituted with -O-, and At least one hydrogen atom in the compound represented by formula (6), formula (7) or formula (8) may be substituted with cyano, halogen or deuterium. For details of the structural form and substituents of the compounds in each formula, the explanations for the above general formulas (1) and (2) can be cited.

[0302] In the above formula (6'), formula (7') and formula (8'), In the ring a, ring b, and ring c, any "-C(-R)=" (where R is R in each formula) 1 ~R 11 ) may be replaced with "-N=", and any "-C(-R)=C(-R)-" (where R is R in each formula) may be replaced with "-N=", 1 ~R 11 In the formula (8'), any "-C(-R)=" in the ring c (where R is R in the formula (8')) may be replaced with "-N(-R)-", "-O-", or "-S-", and R in the "-N(-R)-" is aryl, alkyl, or cycloalkyl. 4 or R 7 ) may be replaced with "-N=", R 1 ~R 11 are each independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl (two aryls may be bonded via a single bond or a linking group), alkyl, cycloalkyl, alkoxy, aryloxy, triarylsilyl, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl or alkyldicycloalkylsilyl, in which at least one hydrogen may be substituted with an aryl, heteroaryl, alkyl or cycloalkyl; Also, R 1 ~R 11adjacent groups among the above may be bonded to each other to form an aryl ring or a heteroaryl ring together with the a ring, the b ring or the c ring, and at least one hydrogen atom in the formed ring may be replaced by an aryl, a heteroaryl, a diarylamino, a diheteroarylamino, an arylheteroarylamino, a diarylboryl (two aryls may be bonded via a single bond or a linking group), an alkyl, a cycloalkyl, an alkoxy, an aryloxy, a triarylsilyl, a trialkylsilyl, a tricycloalkylsilyl, a dialkylcycloalkylsilyl or an alkyldicycloalkylsilyl, and at least one hydrogen atom in these may be replaced by an aryl, a heteroaryl, an alkyl or a cycloalkyl; However, R in formula (8') 4 and R 7 each independently represents hydrogen, an aryl having 6 to 12 carbon atoms, a heteroaryl having 2 to 15 carbon atoms, a diarylamino (wherein the aryl has 6 to 12 carbon atoms), an alkyl having 1 to 6 carbon atoms, or a cycloalkyl having 3 to 14 carbon atoms; X 1 , X 2 and X 3 are each independently >O, >NR, >C(-R)2, >S or >Se, R of the >NR is an aryl having 6 to 12 carbon atoms, a heteroaryl having 2 to 15 carbon atoms, an alkyl having 1 to 6 carbon atoms or a cycloalkyl having 3 to 14 carbon atoms, R of the >C(-R)2 is hydrogen, an aryl having 6 to 12 carbon atoms, an alkyl having 1 to 6 carbon atoms or a cycloalkyl having 3 to 14 carbon atoms, at least one of R of the >NR and R of the >C(-R)2 may be bonded to at least one of the ring a, ring b and ring c via a single bond, -O-, -S- or -C(-R)2-, R of the -C(-R)2- is an alkyl having 1 to 6 carbon atoms or a cycloalkyl having 3 to 14 carbon atoms, In the compound represented by formula (6'), formula (7') or formula (8'), at least one of the ring a, the ring b, the ring c, the formed ring, the aryl and the heteroaryl may be condensed with at least one cycloalkane having 3 to 24 carbon atoms, at least one hydrogen in the cycloalkane may be substituted with an aryl having 6 to 30 carbon atoms, a heteroaryl having 2 to 30 carbon atoms, an alkyl having 1 to 24 carbon atoms or a cycloalkyl having 3 to 24 carbon atoms, at least one -CH2- in the cycloalkane may be substituted with -O-, and At least one hydrogen atom in the compound represented by formula (6'), formula (7') or formula (8') may be substituted with cyano, halogen or deuterium. For details of the structural form and substituents of the compounds in each formula, the explanations for the above general formulas (1) and (2) can be cited.

[0303] In the compound of formula (6) or formula (6'), ring B and ring C (ring b and ring c) are X 1 and X 2 Equivalent to X 3 The compound linked by is a compound of formula (7) or formula (7'), and the dimer formed by sharing the C ring (c ring) in the compound of formula (6) or formula (6') is a compound of formula (8) or formula (8'). Since the compounds have similar structures, the compound of formula (6) or formula (6') will be described below as a representative, but the description also applies to the compound of formula (7) or formula (7') and the compound of formula (8) or formula (8').

[0304] The A ring, B ring and C ring in the general formula (6) are each independently an aryl ring or a heteroaryl ring, and at least one hydrogen atom in these rings may be substituted with a substituent. The substituent is preferably a substituted or unsubstituted aryl, a substituted or unsubstituted heteroaryl, a substituted or unsubstituted diarylamino, a substituted or unsubstituted diheteroarylamino, a substituted or unsubstituted arylheteroarylamino (an amino group having an aryl and a heteroaryl), a substituted or unsubstituted diarylboryl (two aryls may be bonded via a single bond or a linking group), a substituted or unsubstituted alkyl, a substituted or unsubstituted cycloalkyl, a substituted or unsubstituted alkoxy, a substituted or unsubstituted aryloxy, or a substituted silyl. In the case where these groups have a substituent, examples of the substituent include an aryl, a heteroaryl, an alkyl or a cycloalkyl. In addition, the aryl ring or the heteroaryl ring may be a ring having a central element "B (boron)", "X 1 " and "X 2 " and preferably has a 5- or 6-membered ring sharing a bond with the central fused two-ring structure of general formula (6).

[0305] The ring A (or ring B or ring C) in the general formula (6) is the ring a and its substituent R 1 ~R 3 (or ring b and its substituent R 8 ~R 11 , ring c and its substituent R 4 ~R 7 ). In other words, general formula (6') corresponds to a structure in which "rings A to C having 6 members" are selected as rings A to C of general formula (6). In that sense, each ring in general formula (6') is represented by lowercase letters a to c.

[0306] In the general formula (6'), the substituents R 1 ~R 11Adjacent groups among may be bonded to each other to form an aryl ring or a heteroaryl ring together with the a ring, the b ring, or the c ring, and at least one hydrogen atom in the formed ring may be substituted with an aryl, a heteroaryl, a diarylamino, a diheteroarylamino, an arylheteroarylamino, a diarylboryl (two aryls may be bonded via a single bond or a linking group), an alkyl, a cycloalkyl, an alkoxy, an aryloxy, a triarylsilyl, a trialkylsilyl, a tricycloalkylsilyl, a dialkylcycloalkylsilyl, or an alkyldicycloalkylsilyl, and at least one hydrogen atom in these may be substituted with an aryl, a heteroaryl, an alkyl, or a cycloalkyl. Therefore, the polycyclic aromatic compound represented by the general formula (6') has a ring structure that constitutes the compound that changes depending on the mutual bonding form of the substituents in the a ring, the b ring, and the c ring. This is as explained using the formula (2-1) and the formula (2-2) in the explanation of the general formula (1).

[0307] The explanation of general formula (1) can be cited for the "aryl ring" and "heteroaryl ring" which are rings A, B, and C in general formula (6). In addition, the explanation of general formula (1) and formula (2) can be cited for the first and second substituents substituted on the "aryl ring" and "heteroaryl ring".

[0308] X in general formula (6) 1 and X 2are each independently >O, >NR, >C(-R)2, >S or >Se, R of the >NR is an optionally substituted aryl, an optionally substituted heteroaryl, an optionally substituted alkyl or an optionally substituted cycloalkyl, R of the >C(-R)2 is hydrogen, an optionally substituted aryl, an optionally substituted alkyl or an optionally substituted cycloalkyl, and at least one of the R of the >NR and the R of the >C(-R)2 may be bonded to at least one of the A ring, the B ring and the C ring by a linking group, and the linking group is preferably -O-, -S- or -C(-R)2-. Note that R of the "-C(-R)2-" is hydrogen, an alkyl or a cycloalkyl. This explanation is based on X in the general formula (6'). 1 and X 2 But it's the same.

[0309] Here, the provision in general formula (6) that "at least one of R of >NR and R of >C(-R)2 is bonded to at least one of the rings A, B and C via a linking group" corresponds to the provision in general formula (6') that "at least one of R of >NR and R of >C(-R)2 is bonded to at least one of the rings a, b and c via a single bond, -O-, -S-, or -C(-R)2-".

[0310] This provision is represented by the following formula (6'-3-1), X 1 Or X 2 can be expressed as a compound having a ring structure in which X is incorporated into the fused ring B' and the fused ring C'. That is, for example, the benzene ring which is the b ring (or the c ring) in the general formula (6') is 1 (or X 2 The compound has a ring B' (or ring C') formed by condensing another ring so as to incorporate the ring A. The condensed ring B' (or condensed ring C') formed is, for example, a phenoxazine ring, a phenothiazine ring, or an acridine ring.

[0311] In addition, the above provisions are applicable to X represented by the following formula (6'-3-2) or formula (6'-3-3). 1 and X 2 In other words, for example, the compound having a ring structure in which X is incorporated into the fused ring A' in the general formula (6') is a benzene ring, 1 (or X 2 , or X 1 and X 2 The compound has a ring A' formed by condensing another ring so as to incorporate the ring A'. The condensed ring A' formed is, for example, a phenoxazine ring, a phenothiazine ring, or an acridine ring.

[0312] [ka]

[0313] X in general formula (6) 1 and X 2 In the formula (6'), R in >NR is an aryl, heteroaryl, alkyl or cycloalkyl which may be substituted with the second substituent described above, and at least one hydrogen in the aryl, heteroaryl, alkyl or cycloalkyl may be substituted with, for example, an alkyl or cycloalkyl. The explanations for the aryl, heteroaryl, alkyl or cycloalkyl can also be cited for the aryl, heteroaryl, alkyl or cycloalkyl. In particular, an aryl having 6 to 10 carbon atoms (e.g., phenyl, naphthyl, etc.), a heteroaryl having 2 to 15 carbon atoms (e.g., carbazolyl, etc.), an alkyl having 1 to 4 carbon atoms (e.g., methyl, ethyl, etc.) or a cycloalkyl having 5 to 10 carbon atoms (preferably cyclohexyl or adamantyl) is preferred. This explanation is also applicable to X in the formula (6'). 1 and X 2 But it's the same.

[0314] X in general formula (6) 1 and X 2In the formula, R in >C(-R)2 is hydrogen, an aryl, an alkyl or a cycloalkyl which may be substituted with the second substituent described above, and at least one hydrogen in the aryl may be substituted with, for example, an alkyl. The explanations for the aryl, alkyl or cycloalkyl can also be cited for the general formula (1) and formula (2). In particular, an aryl having 6 to 10 carbon atoms (e.g., phenyl, naphthyl, etc.), an alkyl having 1 to 4 carbon atoms (e.g., methyl, ethyl, etc.) or a cycloalkyl having 5 to 10 carbon atoms (preferably cyclohexyl or adamantyl) is preferred. This explanation is also applicable to X in the general formula (6'). 1 and X 2 But it's the same.

[0315] R in the linking group "-C(-R)2-" in general formula (6') is hydrogen, alkyl, or cycloalkyl, and the explanation of general formula (1) and formula (2) can also be cited for this alkyl or cycloalkyl. In particular, alkyl having 1 to 4 carbon atoms (e.g., methyl, ethyl, etc.) or cycloalkyl having 5 to 10 carbon atoms (preferably cyclohexyl or adamantyl) is preferred.

[0316] In addition, all or a part of the hydrogen atoms in the chemical structure of the polycyclic aromatic compound represented by general formula (6) or (6') may be replaced with cyano, halogen, or deuterium. For example, in formula (6), the A ring, B ring, and C ring (A to C rings are aryl rings or heteroaryl rings), the substituents on the A to C rings, and X 1 and X 2 When is >NR or >C(-R)2, hydrogen in R (=aryl, heteroaryl, alkyl, cycloalkyl) can be replaced by cyano, halogen or deuterium, among which, all or a part of hydrogen in aryl or heteroaryl is replaced by cyano, halogen or deuterium. Halogen is fluorine, chlorine, bromine or iodine, preferably fluorine, chlorine or bromine, more preferably fluorine or chlorine.

[0317] The explanation of general formula (1) and formula (2) can also be cited for the form in which at least one of ring A, ring B, ring C, ring a, ring b, ring c, "formed ring", aryl and heteroaryl in the compound represented by formula (6) or (6') is condensed with at least one cycloalkane.

[0318] In the compound represented by formula (6'), any "-C(-R)=" (where R is R in the formula 1 ~R 11 ) is replaced with "-N=", any "-C(-R)=C(-R)-" (where R is R in the formula 1 ~R 11 The explanation of general formula (2) can also be cited for the form in which "-N(-R)-", "-O-", or "-S-" is replaced with "-N(-R)-", "-O-", or "-S-".

[0319] The compounds represented by general formula (6), (7), (8), (6'), (7'), and (8') can be produced in the same manner as the compounds represented by general formula (1) and (2).

[0320] <Electron injection layer and electron transport layer in organic electroluminescence device> The electron injection layer 107 plays a role of efficiently injecting electrons moving from the cathode 108 into the light-emitting layer 105 or the electron transport layer 106. The electron transport layer 106 plays a role of efficiently transporting electrons injected from the cathode 108 or electrons injected from the cathode 108 via the electron injection layer 107 to the light-emitting layer 105. The electron transport layer 106 and the electron injection layer 107 are each formed by laminating or mixing one or more types of electron transport / injection materials, or by a mixture of an electron transport / injection material and a polymer binder.

[0321] The electron injection / transport layer is a layer that is responsible for injecting electrons from the cathode and transporting the electrons. It is desirable that the electron injection efficiency is high and that the injected electrons are efficiently transported. For this purpose, it is preferable that the material has a large electron affinity, a large electron mobility, and excellent stability, and impurities that become traps are unlikely to occur during manufacture and use. However, when considering the balance of transport of holes and electrons, if the material mainly plays a role of efficiently preventing holes from flowing from the anode to the cathode without recombining, even if the electron transport ability is not so high, it has the effect of improving the luminous efficiency equivalent to a material with a high electron transport ability. Therefore, the electron injection / transport layer in this embodiment may also include the function of a layer that can efficiently block the movement of holes.

[0322] The material (electron transport material) forming the electron transport layer 106 or the electron injection layer 107 can be arbitrarily selected from compounds conventionally used as electron transport compounds in photoconductive materials and known compounds used in the electron injection layer and electron transport layer of organic EL devices. In the present invention, the electron transport material can be a polycyclic aromatic compound represented by general formula (1) or formula (2).

[0323] Materials used in the electron transport layer or electron injection layer preferably contain at least one selected from compounds consisting of aromatic rings or heteroaromatic rings composed of one or more atoms selected from carbon, hydrogen, oxygen, sulfur, silicon, and phosphorus, pyrrole derivatives and their condensed ring derivatives, and metal complexes having electron-accepting nitrogen. Specific examples include condensed ring aromatic ring derivatives such as naphthalene and anthracene, styryl aromatic ring derivatives such as 4,4'-bis(diphenylethenyl)biphenyl, perinone derivatives, coumarin derivatives, naphthalimide derivatives, quinone derivatives such as anthraquinone and diphenoquinone, phosphorus oxide derivatives, carbazole derivatives, and indole derivatives. Examples of metal complexes having electron-accepting nitrogen include hydroxyazole complexes such as hydroxyphenyloxazole complexes, azomethine complexes, tropolone metal complexes, flavonol metal complexes, and benzoquinoline metal complexes. These materials can be used alone or in combination with different materials.

[0324] Specific examples of other electron transport compounds include pyridine derivatives, naphthalene derivatives, anthracene derivatives, phenanthroline derivatives, perinone derivatives, coumarin derivatives, naphthalimide derivatives, anthraquinone derivatives, diphenoquinone derivatives, diphenylquinone derivatives, perylene derivatives, oxadiazole derivatives (e.g., 1,3-bis[(4-t-butylphenyl)1,3,4-oxadiazolyl]phenylene), thiophene derivatives, triazole derivatives (e.g., N-naphthyl-2,5-diphenyl-1,3,4-triazole), thiadiazole derivatives, metal complexes of oxine derivatives, quinolinol-based metal complexes, quinoxaline derivatives, polymers of quinoxaline derivatives, benzazole compounds, gallium complexes, pyrazole derivatives, perfluorinated phenylene derivatives, triazine derivatives, pyridine derivatives, etc. Examples of the compound include arylazine derivatives, benzoquinoline derivatives (such as 2,2'-bis(benzo[h]quinolin-2-yl)-9,9'-spirobifluorene), imidazopyridine derivatives, borane derivatives, benzimidazole derivatives (such as tris(N-phenylbenzimidazol-2-yl)benzene), benzoxazole derivatives, benzothiazole derivatives, quinoline derivatives, oligopyridine derivatives such as terpyridine, bipyridine derivatives, terpyridine derivatives (such as 1,3-bis(4'-(2,2':6'2"-terpyridinyl))benzene), naphthyridine derivatives (such as bis(1-naphthyl)-4-(1,8-naphthyridin-2-yl)phenylphosphine oxide), aldazine derivatives, carbazole derivatives, indole derivatives, phosphorus oxide derivatives, and bisstyryl derivatives.

[0325] Furthermore, metal complexes having an electron-accepting nitrogen atom can also be used, and examples thereof include hydroxyazole complexes such as quinolinol metal complexes and hydroxyphenyloxazole complexes, azomethine complexes, tropolone metal complexes, flavonol metal complexes, and benzoquinoline metal complexes.

[0326] The above-mentioned materials may be used alone or in combination with different materials.

[0327] Among the above-mentioned materials, borane derivatives, pyridine derivatives, fluoranthene derivatives, BO-based derivatives, anthracene derivatives, benzofluorene derivatives, phosphine oxide derivatives, pyrimidine derivatives, carbazole derivatives, triazine derivatives, benzimidazole derivatives, phenanthroline derivatives, and quinolinol-based metal complexes are preferable.

[0328] <Borane derivatives> The borane derivative is, for example, a compound represented by the following general formula (ETM-1), and is disclosed in detail in JP-A-2007-27587. [ka] In the above formula (ETM-1), R 11 and R 12 are each independently at least one of hydrogen, alkyl, cycloalkyl, optionally substituted aryl, substituted silyl, optionally substituted nitrogen-containing heterocycle, or cyano; R 13 ~R 16 are each independently an optionally substituted alkyl, an optionally substituted cycloalkyl, or an optionally substituted aryl, X is an optionally substituted arylene, Y is an optionally substituted aryl having 16 or less carbon atoms, a substituted boryl, or an optionally substituted carbazolyl, and each n is independently an integer of 0 to 3. In addition, examples of the substituent in the case of "optionally substituted" or "substituted" include aryl, heteroaryl, alkyl, and cycloalkyl.

[0329] Among the compounds represented by the above general formula (ETM-1), compounds represented by the following general formula (ETM-1-1) and compounds represented by the following general formula (ETM-1-2) are preferred. [ka] In formula (ETM-1-1), R 11 and R 12are each independently at least one of hydrogen, alkyl, cycloalkyl, optionally substituted aryl, substituted silyl, optionally substituted nitrogen-containing heterocycle, or cyano; R 13 ~R 16 are each independently optionally substituted alkyl, optionally substituted cycloalkyl, or optionally substituted aryl; R 21 and R 22 are each independently at least one of hydrogen, alkyl, cycloalkyl, optionally substituted aryl, substituted silyl, optionally substituted nitrogen-containing heterocycle, or cyano; X 1 is an optionally substituted arylene having 20 or less carbon atoms, each n is independently an integer of 0 to 3, and each m is independently an integer of 0 to 4. In addition, examples of the substituent in the case where "optionally substituted" or "substituted" include aryl, heteroaryl, alkyl, and cycloalkyl. [ka] In formula (ETM-1-2), R 11 and R 12 are each independently at least one of hydrogen, alkyl, cycloalkyl, optionally substituted aryl, substituted silyl, optionally substituted nitrogen-containing heterocycle, or cyano; R 13 ~R 16 are each independently an optionally substituted alkyl, an optionally substituted cycloalkyl, or an optionally substituted aryl; X 1 is an optionally substituted arylene having 20 or less carbon atoms, and each n is independently an integer of 0 to 3. Examples of the substituent in the case where it is "optionally substituted" or "substituted" include aryl, heteroaryl, alkyl, and cycloalkyl.

[0330] X 1Specific examples of include divalent groups represented by any of the following formulae (X-1) to (X-9): In each structural formula, * represents the bonding position. [ka] (In each formula, R a are each independently an alkyl group, a cycloalkyl group, or an optionally substituted phenyl group.

[0331] Specific examples of the borane derivative include the following compounds: [ka]

[0332] The borane derivative can be produced using known raw materials and known synthesis methods.

[0333] <Pyridine derivatives> The pyridine derivative is, for example, a compound represented by the following formula (ETM-2), preferably a compound represented by formula (ETM-2-1) or formula (ETM-2-2). [ka]

[0334] φ is an n-valent aryl ring (preferably an n-valent benzene ring, naphthalene ring, anthracene ring, fluorene ring, benzofluorene ring, phenalene ring, phenanthrene ring or triphenylene ring), and n is an integer of 1 to 4.

[0335] In the above formula (ETM-2-1), R 11 ~R 18 are each independently hydrogen, alkyl (preferably alkyl having 1 to 24 carbon atoms), cycloalkyl (preferably cycloalkyl having 3 to 12 carbon atoms) or aryl (preferably aryl having 6 to 30 carbon atoms).

[0336] In the above formula (ETM-2-2), R11 and R 12 are each independently hydrogen, alkyl (preferably alkyl having 1 to 24 carbon atoms), cycloalkyl (preferably cycloalkyl having 3 to 12 carbon atoms) or aryl (preferably aryl having 6 to 30 carbon atoms); R 11 and R 12 may be bonded to form a ring.

[0337] In each formula, the "pyridine-based substituent" is any one of the following formulae (Py-1) to (Py-15), and each pyridine-based substituent may be independently substituted with an alkyl having 1 to 4 carbon atoms or a cycloalkyl having 5 to 10 carbon atoms. The pyridine-based substituent may be bonded to the φ, anthracene ring, or fluorene ring in each formula via a phenylene group or naphthylene group. * in each structural formula indicates a bonding position.

[0338] [ka]

[0339] The pyridine-based substituent is any one of the above formulae (Py-1) to (Py-15), and among these, any one of the following formulae (Py-21) to (Py-44) is preferable. In each structural formula, * indicates a bonding position. [ka]

[0340] At least one hydrogen atom in each pyridine derivative may be replaced by deuterium, and one of the two "pyridine-based substituents" in the above formulas (ETM-2-1) and (ETM-2-2) may be replaced by aryl.

[0341] R 11 ~R 18The "alkyl" in the above may be either linear or branched, and examples thereof include linear alkyl having 1 to 24 carbon atoms or branched alkyl having 3 to 24 carbon atoms. A preferred "alkyl" is an alkyl having 1 to 18 carbon atoms (branched alkyl having 3 to 18 carbon atoms). A more preferred "alkyl" is an alkyl having 1 to 12 carbon atoms (branched alkyl having 3 to 12 carbon atoms). An even more preferred "alkyl" is an alkyl having 1 to 6 carbon atoms (branched alkyl having 3 to 6 carbon atoms). An especially preferred "alkyl" is an alkyl having 1 to 4 carbon atoms (branched alkyl having 3 to 4 carbon atoms).

[0342] Specific examples of "alkyl" include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, t-butyl, n-pentyl, isopentyl, neopentyl, t-pentyl (t-amyl), n-hexyl, 1-methylpentyl, 3,3-dimethylbutyl, 2-ethylbutyl, n-heptyl, 1-methylhexyl, n-octyl, t-octyl (1,1,3,3-tetramethylbutyl), 1-methyl, Examples of the aryl group include n-hexyl, n-butyl, n-hexyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 2,6-dimethyl-4-heptyl, 3,5,5-trimethylhexyl, n-decyl, n-undecyl, 1-methyldecyl, n-dodecyl, n-tridecyl, 1-hexylheptyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, n-heptadecyl, n-octadecyl, and n-eicosyl. Further, for example, 1-ethyl-1-methylpropyl, 1,1-diethylpropyl, 1,1-dimethylbutyl, 1-ethyl-1-methylbutyl, 1,1,4-trimethylpentyl, 1,1,2-trimethylpropyl, 1,1-dimethyloctyl, 1,1-dimethylpentyl, 1,1-dimethylheptyl, 1,1,5-trimethylhexyl, 1-ethyl-1-methylhexyl, 1-ethyl-1,3-dimethylbutyl, 1,1,2,2-tetramethylpropyl, 1-butyl-1-methylpentyl, 1,1-diethylbutyl, 1-ethyl-1-methylpentyl, 1,1,3-trimethylbutyl, 1-propyl-1-methylpentyl, 1,1,2-trimethylpropyl, 1-ethyl-1,2,2-trimethylpropyl, 1-propyl-1-methylbutyl, and 1,1-dimethylhexyl.

[0343] As for the alkyl having 1 to 4 carbon atoms with which the pyridine-based substituent is substituted, the above description of the alkyl can be cited.

[0344] R 11 ~R 18 In the above, the "cycloalkyl" is, for example, a cycloalkyl having 3 to 12 carbon atoms. A preferred "cycloalkyl" is a cycloalkyl having 3 to 10 carbon atoms. A more preferred "cycloalkyl" is a cycloalkyl having 3 to 8 carbon atoms. An even more preferred "cycloalkyl" is a cycloalkyl having 3 to 6 carbon atoms. Specific examples of "cycloalkyl" include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, methylcyclopentyl, cycloheptyl, methylcyclohexyl, cyclooctyl, and dimethylcyclohexyl.

[0345] R 11 ~R 18 As for the "aryl" in the above, a preferable aryl is an aryl having 6 to 30 carbon atoms, a more preferable aryl is an aryl having 6 to 18 carbon atoms, an even more preferable aryl is an aryl having 6 to 14 carbon atoms, and an especially preferable aryl is an aryl having 6 to 12 carbon atoms.

[0346] Specific examples of the "aryl having 6 to 30 carbon atoms" include monocyclic aryl phenyl, fused bicyclic aryl (1-, 2-)naphthyl, fused tricyclic aryl acenaphthylene-(1-, 3-, 4-, 5-)yl, fluoren-(1-, 2-, 3-, 4-, 9-)yl, phenalene-(1-, 2-)yl, (1-, 2-, 3-, 4-, 9-)phenanthryl, fused tetracyclic aryl triphenylene-(1-, 2-)yl, pyrene-(1-, 2-, 4-)yl, naphthacene-(1-, 2-, 5-)yl, fused pentacyclic aryl perylene-(1-, 2-, 3-)yl, pentacene-(1-, 2-, 5-, 6-)yl, and the like.

[0347] Preferred examples of the "aryl having 6 to 30 carbon atoms" include phenyl, naphthyl, phenanthryl, chrysenyl, and triphenylenyl, more preferably phenyl, 1-naphthyl, 2-naphthyl, and phenanthryl, and particularly preferably phenyl, 1-naphthyl, and 2-naphthyl.

[0348] R in the above formula (ETM-2-2) 11 and R 12 may be bonded to form a ring, and as a result, cyclobutane, cyclopentane, cyclopentene, cyclopentadiene, cyclohexane, fluorene, indene, or the like may be spiro-bonded to the five-membered ring of the fluorene skeleton.

[0349] Specific examples of the pyridine derivative include the following compounds: [ka]

[0350] This pyridine derivative can be produced using known raw materials and known synthesis methods.

[0351] <Fluoranthene derivatives> The fluoranthene derivative is, for example, a compound represented by the following general formula (ETM-3), and specifically, it is disclosed in International Publication No. 2010 / 134352. [Chemical formula]

[0352] In the above formula (ETM-3), X 12 ~X 21 represents hydrogen, halogen, linear, branched or cyclic alkyl, linear, branched or cyclic alkoxy, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl. Here, examples of the substituent when it is substituted include aryl, heteroaryl, alkyl or cycloalkyl.

[0353] Specific examples of this fluoranthene derivative include, for example, the following compounds. [Chemical formula]

[0354] <BO-based derivative> 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). [Chemical formula]

[0355] R 1 ~R 11 are each independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, alkyl, cycloalkyl, alkoxy or aryloxy, and at least one hydrogen in these may be substituted with aryl, heteroaryl, alkyl or cycloalkyl.

[0356] Also, R 1 ~R 11Adjacent groups among these may be bonded to each other to form an aryl ring or a heteroaryl ring together with the a ring, the b ring, or the c ring, and at least one hydrogen atom in the formed ring may be substituted with an aryl, a heteroaryl, a diarylamino, a diheteroarylamino, an arylheteroarylamino, an alkyl, a cycloalkyl, an alkoxy, or an aryloxy, and at least one hydrogen atom in these rings may be substituted with an aryl, a heteroaryl, an alkyl, or a cycloalkyl.

[0357] In addition, at least one hydrogen in the compound or structure represented by formula (ETM-4) may be substituted with a halogen or deuterium.

[0358] For an explanation of the substituents and the form of ring formation in formula (ETM-4), the explanation of the polycyclic aromatic compound represented by the above general formula (1) or formula (2) can be cited.

[0359] Specific examples of the BO derivative include the following compounds: [ka]

[0360] The BO derivative can be produced using known raw materials and known synthesis methods.

[0361] <Anthracene derivatives> One of the anthracene derivatives is, for example, a compound represented by the following formula (ETM-5-1). [ka]

[0362] Ar is independently a divalent benzene or naphthalene; R 1 ~R 4 are each independently hydrogen, alkyl having 1 to 6 carbon atoms, cycloalkyl having 3 to 6 carbon atoms, or aryl having 6 to 20 carbon atoms.

[0363] Each Ar can be independently selected from divalent benzene or naphthalene, and the two Ar may be different or the same, but it is preferable that they are the same from the viewpoint of ease of synthesis of the anthracene derivative. Ar is bonded to pyridine to form a "moiety consisting of Ar and pyridine", and this moiety is bonded to anthracene as a group represented by any one of the following formulas (Py-1) to (Py-12). * in each structural formula indicates a bonding position.

[0364] [ka]

[0365] Among these groups, a group represented by any one of the above formulas (Py-1) to (Py-9) is preferred, and a group represented by any one of the above formulas (Py-1) to (Py-6) is more preferred. The two "Ar and pyridine moieties" bonded to anthracene may have the same or different structures, but from the viewpoint of ease of synthesis of anthracene derivatives, it is preferable that they have the same structure. However, from the viewpoint of element characteristics, it is preferable that the two "Ar and pyridine moieties" have the same or different structures.

[0366] R 1 ~R 4 The alkyl having 1 to 6 carbon atoms in the formula (I) may be either linear or branched. That is, it is a linear alkyl having 1 to 6 carbon atoms or a branched alkyl having 3 to 6 carbon atoms. More preferably, it is an alkyl having 1 to 4 carbon atoms (branched alkyl having 3 to 4 carbon atoms). Specific examples include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, t-butyl, n-pentyl, isopentyl, neopentyl, t-pentyl (t-amyl), n-hexyl, 1-methylpentyl, 3,3-dimethylbutyl, and 2-ethylbutyl. Methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, and t-butyl are preferred, and methyl, ethyl, and t-butyl are more preferred.

[0367] R 1 ~R 4 Specific examples of the cycloalkyl having 3 to 6 carbon atoms include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, methylcyclopentyl, cycloheptyl, methylcyclohexyl, cyclooctyl, and dimethylcyclohexyl.

[0368] R 1 ~R 4 With regard to the aryl having 6 to 20 carbon atoms in the above formula, aryl having 6 to 16 carbon atoms is preferable, aryl having 6 to 12 carbon atoms is more preferable, and aryl having 6 to 10 carbon atoms is particularly preferable.

[0369] Specific examples of "aryl having 6 to 20 carbon atoms" include monocyclic aryls such as phenyl, (o-, m-, p-)tolyl, (2,3-, 2,4-, 2,5-, 2,6-, 3,4-, 3,5-)xylyl, mesityl (2,4,6-trimethylphenyl), and (o-, m-, p-)cumenyl, bicyclic aryls such as (2-, 3-, 4-)biphenylyl, condensed bicyclic aryls such as (1-, 2-)naphthyl, and tricyclic aryls such as terphenylyl (m-terphenyl-2'-yl, m-terphenyl-4'-yl, m-terphenyl-5'-yl, o-terphenyl-3'-yl, o-terphenyl-4'-yl, p-terphenyl-2'-yl, m-terphenyl-2-yl, m-terphenyl-3-yl, m-terphenyl-4'-yl, p-terphenyl-2 ...4'-yl, p-terphenyl-2-yl, m-terphenyl-2-yl, m-terphenyl-3-yl, m-terphenyl-4'-yl, p-terphenyl-2-yl, m-terphenyl-4'-yl, p-terphenyl-2-yl, m-terphenyl-2-yl, m-terphenyl-3-yl, m aryl, o-terphenyl-4-yl, o-terphenyl-2-yl, o-terphenyl-3-yl, o-terphenyl-4-yl, p-terphenyl-2-yl, p-terphenyl-3-yl, p-terphenyl-4-yl; condensed tricyclic aryls, anthracene-(1-,2-,9-)yl, acenaphthylene-(1-,3-,4-,5-)yl, fluorene-(1-,2-,3-,4-,9-)yl, phenalene-(1-,2-)yl, (1-,2-,3-,4-,9-)phenanthryl; condensed tetracyclic aryls, triphenylene-(1-,2-)yl, pyrene-(1-,2-,4-)yl, tetracene-(1-,2-,5-)yl; condensed pentacyclic aryls, perylene-(1-,2-,3-)yl, and the like.

[0370] The "aryl having 6 to 20 carbon atoms" is preferably phenyl, biphenylyl, terphenylyl or naphthyl, more preferably phenyl, biphenylyl, 1-naphthyl, 2-naphthyl or m-terphenyl-5'-yl, even more preferably phenyl, biphenylyl, 1-naphthyl or 2-naphthyl, and most preferably phenyl.

[0371] One example of the anthracene derivative is a compound represented by the following formula (ETM-5-2). [ka]

[0372] Ar 1 are each independently a single bond, or a divalent benzene, naphthalene, anthracene, fluorene, or phenalene.

[0373] Ar 2 are each independently an aryl having 6 to 20 carbon atoms, and the same explanation as for "aryl having 6 to 20 carbon atoms" in the above formula (ETM-5-1) can be cited. An aryl having 6 to 16 carbon atoms is preferable, an aryl having 6 to 12 carbon atoms is more preferable, and an aryl having 6 to 10 carbon atoms is particularly preferable. Specific examples include phenyl, biphenylyl, naphthyl, terphenylyl, anthracenyl, acenaphthylenyl, fluorenyl, phenalenyl, phenanthryl, triphenylenyl, pyrenyl, tetracenyl, perylenyl, etc.

[0374] R 1 ~R 4 are each independently hydrogen, alkyl having 1 to 6 carbon atoms, cycloalkyl having 3 to 6 carbon atoms, or aryl having 6 to 20 carbon atoms, and the explanation in the above formula (ETM-5-1) can be cited.

[0375] Specific examples of these anthracene derivatives include the following compounds. [ka]

[0376] These anthracene derivatives can be produced using known raw materials and known synthesis methods.

[0377] <Benzofluorene derivatives> The benzofluorene derivative is, for example, a compound represented by the following formula (ETM-6). [ka]

[0378] Ar 1are each independently an aryl having 6 to 20 carbon atoms, and the same explanation as for "aryl having 6 to 20 carbon atoms" in the above formula (ETM-5-1) can be cited. An aryl having 6 to 16 carbon atoms is preferable, an aryl having 6 to 12 carbon atoms is more preferable, and an aryl having 6 to 10 carbon atoms is particularly preferable. Specific examples include phenyl, biphenylyl, naphthyl, terphenylyl, anthracenyl, acenaphthylenyl, fluorenyl, phenalenyl, phenanthryl, triphenylenyl, pyrenyl, tetracenyl, perylenyl, etc.

[0379] Ar 2 are each independently hydrogen, alkyl (preferably alkyl having 1 to 24 carbon atoms), cycloalkyl (preferably cycloalkyl having 3 to 12 carbon atoms) or aryl (preferably aryl having 6 to 30 carbon atoms), and two Ar 2 may be bonded to form a ring.

[0380] Ar 2 The "alkyl" in the above may be either linear or branched, and examples thereof include linear alkyl having 1 to 24 carbon atoms or branched alkyl having 3 to 24 carbon atoms. A preferred "alkyl" is an alkyl having 1 to 18 carbon atoms (branched alkyl having 3 to 18 carbon atoms). A more preferred "alkyl" is an alkyl having 1 to 12 carbon atoms (branched alkyl having 3 to 12 carbon atoms). An even more preferred "alkyl" is an alkyl having 1 to 6 carbon atoms (branched alkyl having 3 to 6 carbon atoms). An especially preferred "alkyl" is an alkyl having 1 to 4 carbon atoms (branched alkyl having 3 to 4 carbon atoms). Specific examples of "alkyl" include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, t-butyl, n-pentyl, isopentyl, neopentyl, t-pentyl (t-amyl), n-hexyl, 1-methylpentyl, 3,3-dimethylbutyl, 2-ethylbutyl, n-heptyl, 1-methylhexyl, and the like.

[0381] Ar 2In the above, the "cycloalkyl" is, for example, a cycloalkyl having 3 to 12 carbon atoms. A preferred "cycloalkyl" is a cycloalkyl having 3 to 10 carbon atoms. A more preferred "cycloalkyl" is a cycloalkyl having 3 to 8 carbon atoms. An even more preferred "cycloalkyl" is a cycloalkyl having 3 to 6 carbon atoms. Specific examples of the "cycloalkyl" include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, methylcyclopentyl, cycloheptyl, methylcyclohexyl, cyclooctyl, and dimethylcyclohexyl.

[0382] Ar 2 As for the "aryl" in the above, a preferable aryl is an aryl having 6 to 30 carbon atoms, a more preferable aryl is an aryl having 6 to 18 carbon atoms, an even more preferable aryl is an aryl having 6 to 14 carbon atoms, and an especially preferable aryl is an aryl having 6 to 12 carbon atoms.

[0383] Specific examples of the "aryl having 6 to 30 carbon atoms" include phenyl, naphthyl, acenaphthylenyl, fluorenyl, phenalenyl, phenanthryl, triphenylenyl, pyrenyl, naphthacenyl, perylenyl, and pentacenyl.

[0384] Two Ar 2 may be bonded to form a ring, and as a result, cyclobutane, cyclopentane, cyclopentene, cyclopentadiene, cyclohexane, fluorene, indene, or the like may be spiro-bonded to the five-membered ring of the fluorene skeleton.

[0385] Specific examples of the benzofluorene derivative include the following compounds: [ka]

[0386] The benzofluorene derivative can be produced using known raw materials and known synthesis methods.

[0387] <Phosphine oxide derivatives> The phosphine oxide derivative is, for example, a compound represented by the following formula (ETM-7-1), the details of which are also described in WO 2013 / 079217. [ka] R 5 is a substituted or unsubstituted alkyl having 1 to 20 carbon atoms, cycloalkyl having 3 to 16 carbon atoms, aryl having 6 to 20 carbon atoms, or heteroaryl having 5 to 20 carbon atoms, R 6 is CN, a substituted or unsubstituted alkyl having 1 to 20 carbon atoms, a cycloalkyl having 3 to 16 carbon atoms, a heteroalkyl having 1 to 20 carbon atoms, an aryl having 6 to 20 carbon atoms, a heteroaryl having 5 to 20 carbon atoms, an alkoxy having 1 to 20 carbon atoms, or an aryloxy having 6 to 20 carbon atoms, R 7 and R 8 each independently represents a substituted or unsubstituted aryl having 6 to 20 carbon atoms or a heteroaryl 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. When substituted, the substituent may be an aryl, heteroaryl, alkyl or cycloalkyl.

[0388] The phosphine oxide derivative may be, for example, a compound represented by the following formula (ETM-7-2). [ka]

[0389] R 1 ~R 3may be the same or different and are selected from hydrogen, an alkyl group, a cycloalkyl group, an aralkyl group, an alkenyl group, a cycloalkenyl group, an alkynyl group, an alkoxy group, an alkylthio group, a cycloalkylthio group, an aryl ether group, an aryl thioether group, an aryl group, a heterocyclic group, a halogen, a cyano group, an aldehyde group, a carbonyl group, a carboxyl group, an amino group, a nitro group, a silyl group, and a fused ring formed between an adjacent substituent.

[0390] Ar 1 may be the same or different and are an arylene group or a heteroarylene group. Ar 2 may be the same or different and are aryl or heteroaryl groups, provided that Ar 1 and Ar 2 At least one of R has a substituent or forms a condensed ring with the adjacent substituent. n is an integer of 0 to 3. When n is 0, there is no unsaturated structural portion. When n is 3, R 1 does not exist.

[0391] Among these substituents, the alkyl group refers to a saturated aliphatic hydrocarbon group such as a methyl group, an ethyl group, a propyl group, or a butyl group, which may be unsubstituted or substituted. If substituted, the substituent is not particularly limited, and may be, for example, an alkyl group, an aryl group, or a heterocyclic group, which is also the case in the following description. The number of carbon atoms in the alkyl group is not particularly limited, but is usually in the range of 1 to 20 in terms of availability and cost.

[0392] The cycloalkyl group refers to a saturated alicyclic hydrocarbon group, such as cyclopropyl, cyclohexyl, norbornyl, adamantyl, etc., which may be unsubstituted or substituted. The number of carbon atoms in the alkyl group is not particularly limited, but is usually in the range of 3 to 20.

[0393] The aralkyl group refers to an aromatic hydrocarbon group mediated by an aliphatic hydrocarbon, such as a benzyl group or a phenylethyl group, and both the aliphatic hydrocarbon and the aromatic hydrocarbon may be unsubstituted or substituted. The number of carbon atoms in the aliphatic portion is not particularly limited, but is usually in the range of 1 to 20.

[0394] The alkenyl group refers to an unsaturated aliphatic hydrocarbon group containing a double bond, such as a vinyl group, an allyl group, or a butadienyl group, which may be unsubstituted or substituted. The number of carbon atoms in the alkenyl group is not particularly limited, but is usually in the range of 2 to 20.

[0395] Moreover, the cycloalkenyl group refers to an unsaturated alicyclic hydrocarbon group containing a double bond, such as a cyclopentenyl group, a cyclopentadienyl group, or a cyclohexene group, which may be either unsubstituted or substituted.

[0396] The alkynyl group refers to an unsaturated aliphatic hydrocarbon group containing a triple bond, such as an acetylenyl group, which may be unsubstituted or substituted. The number of carbon atoms in the alkynyl group is not particularly limited, but is usually in the range of 2 to 20.

[0397] The alkoxy group refers to an aliphatic hydrocarbon group having an ether bond, such as a methoxy group, and the aliphatic hydrocarbon group may be unsubstituted or substituted. The number of carbon atoms in the alkoxy group is not particularly limited, but is usually in the range of 1 to 20.

[0398] An alkylthio group is a group in which the oxygen atom of the ether bond of an alkoxy group is substituted with a sulfur atom.

[0399] In addition, the cycloalkylthio group is a group in which the oxygen atom of the ether bond of a cycloalkoxy group is replaced with a sulfur atom.

[0400] The aryl ether group refers to an aromatic hydrocarbon group, such as a phenoxy group, which is bonded via an ether bond, and the aromatic hydrocarbon group may be unsubstituted or substituted. The number of carbon atoms in the aryl ether group is not particularly limited, but is usually in the range of 6 to 40.

[0401] An aryl thioether group is a group in which the oxygen atom of the ether bond of an aryl ether group is substituted with a sulfur atom.

[0402] The aryl group refers to an aromatic hydrocarbon group such as a phenyl group, a naphthyl group, a biphenyl group, a phenanthryl group, a terphenyl group, or a pyrenyl group. The aryl group may be unsubstituted or substituted. The number of carbon atoms in the aryl group is not particularly limited, but is usually in the range of 6 to 40.

[0403] The heterocyclic group refers to a cyclic structure group having atoms other than carbon, such as a furanyl group, a thiophenyl group, an oxazolyl group, a pyridyl group, a quinolinyl group, a carbazolyl group, etc., which may be unsubstituted or substituted. The number of carbon atoms in the heterocyclic group is not particularly limited, but is usually in the range of 2 to 30.

[0404] Halogen refers to fluorine, chlorine, bromine and iodine.

[0405] The aldehyde group, carbonyl group and amino group may also include groups substituted with an aliphatic hydrocarbon, an alicyclic hydrocarbon, an aromatic hydrocarbon, a heterocycle or the like.

[0406] Furthermore, the aliphatic hydrocarbons, alicyclic hydrocarbons, aromatic hydrocarbons and heterocycles may be either unsubstituted or substituted.

[0407] The silyl group refers to a silicon compound group such as a trimethylsilyl group, which may be unsubstituted or substituted. The number of carbon atoms in the silyl group is not particularly limited, but is usually in the range of 3 to 20. The number of silicon atoms is usually 1 to 6.

[0408] The condensed ring formed between 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 , Ar 1 and Ar 2 etc., where n is 1, two R 1 They may form conjugated or non-conjugated fused rings together. These fused rings may contain nitrogen, oxygen, or sulfur atoms in the ring structure, and may be fused to further rings.

[0409] Specific examples of the phosphine oxide derivative include the following compounds: [ka]

[0410] The phosphine oxide derivative can be produced using known raw materials and known synthesis methods.

[0411] <Pyrimidine derivatives> The pyrimidine derivative is, for example, a compound represented by the following formula (ETM-8), preferably a compound represented by the following formula (ETM-8-1). Details are also described in WO 2011 / 021689. [ka]

[0412] Each Ar is independently an optionally substituted aryl or an optionally substituted heteroaryl, and n is an integer of 1 to 4, preferably an integer of 1 to 3, and more preferably 2 or 3.

[0413] The "aryl" in the "optionally substituted aryl" includes, for example, an aryl having 6 to 30 carbon atoms, preferably an aryl having 6 to 24 carbon atoms, more preferably an aryl having 6 to 20 carbon atoms, and further preferably an aryl having 6 to 12 carbon atoms.

[0414] Specific examples of "aryl" include monocyclic aryl phenyl, bicyclic aryl (2-, 3-, 4-) biphenylyl, condensed bicyclic aryl (1-, 2-) naphthyl, tricyclic aryl terphenylyl (m-terphenyl-2'-yl, m-terphenyl-4'-yl, m-terphenyl-5'-yl, o-terphenyl-3'-yl, o-terphenyl-4'-yl, p-terphenyl-2'-yl, m-terphenyl-2-yl, m-terphenyl-3-yl, m-terphenyl-4-yl, o-terphenyl-2-yl, o-terphenyl-3-yl, o-terphenyl-4-yl, p-terphenyl-2-yl, p-terphenyl-3-yl, p-terphenyl-4-yl), condensed tricyclic aryl Examples of the aryl include acenaphthylene-(1-,3-,4-,5-)yl, fluorene-(1-,2-,3-,4-,9-)yl, phenalene-(1-,2-)yl, (1-,2-,3-,4-,9-)phenanthryl, the tetracyclic aryl group is quaterphenylyl (5'-phenyl-m-terphenyl-2-yl, 5'-phenyl-m-terphenyl-3-yl, 5'-phenyl-m-terphenyl-4-yl, m-quaterphenylyl), the condensed tetracyclic aryl group is triphenylene-(1-,2-)yl, pyrene-(1-,2-,4-)yl, naphthacene-(1-,2-,5-)yl, the condensed pentacyclic aryl group is perylene-(1-,2-,3-)yl, pentacene-(1-,2-,5-,6-)yl, and the like.

[0415] Examples of the "heteroaryl" in "optionally substituted heteroaryl" include heteroaryl having 2 to 30 carbon atoms, preferably heteroaryl having 2 to 25 carbon atoms, more preferably heteroaryl having 2 to 20 carbon atoms, further preferably heteroaryl having 2 to 15 carbon atoms, and particularly preferably heteroaryl having 2 to 10 carbon atoms. Examples of the heteroaryl include heterocycles containing, as ring-constituting atoms other than carbon, 1 to 5 heteroatoms selected from oxygen, sulfur, and nitrogen.

[0416] Specific examples of heteroaryl include furyl, thienyl, pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, pyrazolyl, oxadiazolyl, furazanyl, thiadiazolyl, triazolyl, tetrazolyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, benzofuranyl, isobenzofuranyl, benzo[b]thienyl, indolyl, isoindolyl, 1H-indazolyl, benzimidazolyl, benzoxazolyl, benzothiazolyl, 1H-benzotriazolyl, quinolyl, isoquinolyl, cinnolyl, quinazolyl, quinoxalinyl, phthalazinyl, naphthyridinyl, purinyl, pteridinyl, carbazolyl, acridinyl, phenoxazinyl, phenothiazinyl, phenazinyl, phenoxathiinyl, thianthrenyl, and indolizinyl.

[0417] The above aryl and heteroaryl may be substituted, for example, by the above aryl or heteroaryl, respectively.

[0418] Specific examples of the pyrimidine derivative include the following compounds: [ka]

[0419] The pyrimidine derivative can be produced using known raw materials and known synthesis methods.

[0420] <Carbazole derivatives> The carbazole derivative is, for example, a compound represented by the following formula (ETM-9), or a multimer in which a plurality of such compounds are bonded together via single bonds, etc. Details are described in U.S. Patent Publication No. 2014 / 0197386. [ka]

[0421] Each Ar is independently an optionally substituted aryl or an optionally substituted heteroaryl, and each n is independently an integer of 0 to 4, preferably an integer of 0 to 3, and more preferably 0 or 1.

[0422] The "aryl" in the "optionally substituted aryl" includes, for example, an aryl having 6 to 30 carbon atoms, preferably an aryl having 6 to 24 carbon atoms, more preferably an aryl having 6 to 20 carbon atoms, and further preferably an aryl having 6 to 12 carbon atoms.

[0423] Specific examples of "aryl" include monocyclic aryl phenyl, bicyclic aryl (2-, 3-, 4-) biphenylyl, condensed bicyclic aryl (1-, 2-) naphthyl, tricyclic aryl terphenylyl (m-terphenyl-2'-yl, m-terphenyl-4'-yl, m-terphenyl-5'-yl, o-terphenyl-3'-yl, o-terphenyl-4'-yl, p-terphenyl-2'-yl, m-terphenyl-2-yl, m-terphenyl-3-yl, m-terphenyl-4-yl, o-terphenyl-2-yl, o-terphenyl-3-yl, o-terphenyl-4-yl, p-terphenyl-2-yl, p-terphenyl-3-yl, p-terphenyl-4-yl), condensed tricyclic aryl Examples of the aryl include acenaphthylene-(1-,3-,4-,5-)yl, fluorene-(1-,2-,3-,4-,9-)yl, phenalene-(1-,2-)yl, (1-,2-,3-,4-,9-)phenanthryl, the tetracyclic aryl group is quaterphenylyl (5'-phenyl-m-terphenyl-2-yl, 5'-phenyl-m-terphenyl-3-yl, 5'-phenyl-m-terphenyl-4-yl, m-quaterphenylyl), the condensed tetracyclic aryl group is triphenylene-(1-,2-)yl, pyrene-(1-,2-,4-)yl, naphthacene-(1-,2-,5-)yl, the condensed pentacyclic aryl group is perylene-(1-,2-,3-)yl, pentacene-(1-,2-,5-,6-)yl, and the like.

[0424] Examples of the "heteroaryl" in "optionally substituted heteroaryl" include heteroaryl having 2 to 30 carbon atoms, preferably heteroaryl having 2 to 25 carbon atoms, more preferably heteroaryl having 2 to 20 carbon atoms, further preferably heteroaryl having 2 to 15 carbon atoms, and particularly preferably heteroaryl having 2 to 10 carbon atoms. Examples of the heteroaryl include heterocycles containing, as ring-constituting atoms other than carbon, 1 to 5 heteroatoms selected from oxygen, sulfur, and nitrogen.

[0425] Specific examples of heteroaryl include furyl, thienyl, pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, pyrazolyl, oxadiazolyl, furazanyl, thiadiazolyl, triazolyl, tetrazolyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, benzofuranyl, isobenzofuranyl, benzo[b]thienyl, indolyl, isoindolyl, 1H-indazolyl, benzimidazolyl, benzoxazolyl, benzothiazolyl, 1H-benzotriazolyl, quinolyl, isoquinolyl, cinnolyl, quinazolyl, quinoxalinyl, phthalazinyl, naphthyridinyl, purinyl, pteridinyl, carbazolyl, acridinyl, phenoxazinyl, phenothiazinyl, phenazinyl, phenoxathiinyl, thianthrenyl, and indolizinyl.

[0426] The above aryl and heteroaryl may be substituted, for example, by the above aryl or heteroaryl, respectively.

[0427] The carbazole derivative may be a polymer in which a plurality of compounds represented by the above formula (ETM-9) are bonded together by single bonds, etc. In this case, they may be bonded together by an aryl ring (preferably a polyvalent benzene ring, naphthalene ring, anthracene ring, fluorene ring, benzofluorene ring, phenalene ring, phenanthrene ring, or triphenylene ring) other than a single bond.

[0428] Specific examples of the carbazole derivative include the following compounds. [ka]

[0429] The carbazole derivative can be produced using known raw materials and known synthesis methods.

[0430] <Triazine derivatives> The triazine derivative is, for example, a compound represented by the following formula (ETM-10), preferably a compound represented by the following formula (ETM-10-1), the details of which are described in US Patent Publication No. 2011 / 0156013. [ka]

[0431] Each Ar is independently an optionally substituted aryl or an optionally substituted heteroaryl, and n is an integer of 1 to 3, preferably 2 or 3.

[0432] The "aryl" in the "optionally substituted aryl" includes, for example, an aryl having 6 to 30 carbon atoms, preferably an aryl having 6 to 24 carbon atoms, more preferably an aryl having 6 to 20 carbon atoms, and further preferably an aryl having 6 to 12 carbon atoms.

[0433] Specific examples of "aryl" include monocyclic aryl phenyl, bicyclic aryl (2-, 3-, 4-) biphenylyl, condensed bicyclic aryl (1-, 2-) naphthyl, tricyclic aryl terphenylyl (m-terphenyl-2'-yl, m-terphenyl-4'-yl, m-terphenyl-5'-yl, o-terphenyl-3'-yl, o-terphenyl-4'-yl, p-terphenyl-2'-yl, m-terphenyl-2-yl, m-terphenyl-3-yl, m-terphenyl-4-yl, o-terphenyl-2-yl, o-terphenyl-3-yl, o-terphenyl-4-yl, p-terphenyl-2-yl, p-terphenyl-3-yl, p-terphenyl-4-yl), condensed tricyclic aryl Examples of the aryl include acenaphthylene-(1-,3-,4-,5-)yl, fluorene-(1-,2-,3-,4-,9-)yl, phenalene-(1-,2-)yl, (1-,2-,3-,4-,9-)phenanthryl, the tetracyclic aryl group is quaterphenylyl (5'-phenyl-m-terphenyl-2-yl, 5'-phenyl-m-terphenyl-3-yl, 5'-phenyl-m-terphenyl-4-yl, m-quaterphenylyl), the condensed tetracyclic aryl group is triphenylene-(1-,2-)yl, pyrene-(1-,2-,4-)yl, naphthacene-(1-,2-,5-)yl, the condensed pentacyclic aryl group is perylene-(1-,2-,3-)yl, pentacene-(1-,2-,5-,6-)yl, and the like.

[0434] Examples of the "heteroaryl" in "optionally substituted heteroaryl" include heteroaryl having 2 to 30 carbon atoms, preferably heteroaryl having 2 to 25 carbon atoms, more preferably heteroaryl having 2 to 20 carbon atoms, further preferably heteroaryl having 2 to 15 carbon atoms, and particularly preferably heteroaryl having 2 to 10 carbon atoms. Examples of the heteroaryl include heterocycles containing, as ring-constituting atoms other than carbon, 1 to 5 heteroatoms selected from oxygen, sulfur, and nitrogen.

[0435] Specific examples of heteroaryl include furyl, thienyl, pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, pyrazolyl, oxadiazolyl, furazanyl, thiadiazolyl, triazolyl, tetrazolyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, benzofuranyl, isobenzofuranyl, benzo[b]thienyl, indolyl, isoindolyl, 1H-indazolyl, benzimidazolyl, benzoxazolyl, benzothiazolyl, 1H-benzotriazolyl, quinolyl, isoquinolyl, cinnolyl, quinazolyl, quinoxalinyl, phthalazinyl, naphthyridinyl, purinyl, pteridinyl, carbazolyl, acridinyl, phenoxazinyl, phenothiazinyl, phenazinyl, phenoxathiinyl, thianthrenyl, and indolizinyl.

[0436] The above aryl and heteroaryl may be substituted, for example, by the above aryl or heteroaryl, respectively.

[0437] Specific examples of the triazine derivative include the following compounds: [ka]

[0438] The triazine derivative can be produced using known raw materials and known synthesis methods.

[0439] <Benzimidazole derivatives> The benzimidazole derivative is, for example, a compound represented by the following formula (ETM-11). [ka]

[0440] φ is an n-valent aryl ring (preferably an n-valent benzene ring, naphthalene ring, anthracene ring, fluorene ring, benzofluorene ring, phenalene ring, phenanthrene ring or triphenylene ring), n is an integer of 1 to 4, and the "benzoimidazole-based substituent" is a substituent in which the pyridyl group in the "pyridine-based substituent" in the above formula (ETM-2), formula (ETM-2-1) and formula (ETM-2-2) is replaced with a benzimidazole group, and at least one hydrogen in the benzimidazole derivative may be replaced with a deuterium. * in the following structural formula indicates a bond position. [ka]

[0441] R in the benzimidazole group 11 is hydrogen, alkyl having 1 to 24 carbon atoms, cycloalkyl having 3 to 12 carbon atoms, or aryl having 6 to 30 carbon atoms, and R 11 The explanation can be cited.

[0442] It is further preferable that φ is an anthracene ring or a fluorene ring. In this case, the structure can be as described in the above formula (ETM-2-1) or formula (ETM-2-2). 11 ~R 18 The explanation for formula (ETM-2-1) or formula (ETM-2-2) above can be cited. In addition, in formula (ETM-2-1) or formula (ETM-2-2) above, the two pyridine-based substituents are explained as being bonded, but when these are replaced with benzimidazole-based substituents, both pyridine-based substituents may be replaced with benzimidazole-based substituents (i.e., n=2), or one of the pyridine-based substituents may be replaced with a benzimidazole-based substituent and the other pyridine-based substituent may be replaced with R 11 ~R 18 (i.e., n=1). Furthermore, for example, R in the above formula (ETM-2-1) 11 ~R 18At least one of the above is replaced with a benzimidazole-based substituent to form a "pyridine-based substituent" R 11 ~R 18 may be substituted.

[0443] Specific examples of the benzimidazole derivative include 1-phenyl-2-(4-(10-phenylanthracen-9-yl)phenyl)-1H-benzo[d]imidazole, 2-(4-(10-(naphthalen-2-yl)anthracen-9-yl)phenyl)-1-phenyl-1H-benzo[d]imidazole, 2-(3-(10-(naphthalen-2-yl)anthracen-9-yl)phenyl)-1-phenyl-1H-benzo[d]imidazole, and 5-(10-(naphthalen-2-yl)anthracen-9-yl)-1,2-diphenyl-1H-benzo[d]imidazole. , 1-(4-(10-(naphthalene-2-yl)anthracen-9-yl)phenyl)-2-phenyl-1H-benzo[d]imidazole, 2-(4-(9,10-di(naphthalene-2-yl)anthracen-2-yl)phenyl)-1-phenyl-1H-benzo[d]imidazole, 1-(4-(9,10-di(naphthalene-2-yl)anthracen-2-yl)phenyl)-2-phenyl-1H-benzo[d]imidazole, 5-(9,10-di(naphthalene-2-yl)anthracen-2-yl)-1,2-diphenyl-1H-benzo[d]imidazole, and the like. [ka]

[0444] The benzimidazole derivative can be produced using known raw materials and known synthesis methods.

[0445] <Phenanthroline derivatives> The phenanthroline derivative is, for example, a compound represented by the following formula (ETM-12) or formula (ETM-12-1), the details of which are described in WO 2006 / 021982. [ka]

[0446] φ is an n-valent aryl ring (preferably an n-valent benzene ring, naphthalene ring, anthracene ring, fluorene ring, benzofluorene ring, phenalene ring, phenanthrene ring or triphenylene ring), and n is an integer of 1 to 4.

[0447] R of each formula 11 ~R 18 are each independently hydrogen, alkyl (preferably alkyl having 1 to 24 carbon atoms), cycloalkyl (preferably cycloalkyl having 3 to 12 carbon atoms), or aryl (preferably aryl having 6 to 30 carbon atoms). 11 ~R 18 Either one of the rings is bonded to φ, which is an aryl ring.

[0448] At least one hydrogen atom in each of the phenanthroline derivatives may be replaced with deuterium atom.

[0449] R 11 ~R 18 The alkyl, cycloalkyl and aryl in the above formula (ETM-2) are 11 ~R 18 can be cited. In addition to the above examples, φ can have the following structural formulas. In the structural formulas below, R is independently hydrogen, methyl, ethyl, isopropyl, cyclohexyl, phenyl, 1-naphthyl, 2-naphthyl, biphenylyl, or terphenylyl. In each structural formula, * indicates a bond position. [ka]

[0450] Specific examples of the phenanthroline derivative include 4,7-diphenyl-1,10-phenanthroline, 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline, 9,10-di(1,10-phenanthroline-2-yl)anthracene, 2,6-di(1,10-phenanthroline-5-yl)pyridine, 1,3,5-tri(1,10-phenanthroline-5-yl)benzene, 9,9'-difluoro-bi(1,10-phenanthroline-5-yl), bathocuproine, 1,3-bis(2-phenyl-1,10-phenanthroline-9-yl)benzene, and compounds represented by the following structural formula. [ka]

[0451] The phenanthroline derivative can be produced using known raw materials and known synthesis methods.

[0452] <Quinolinol metal complexes> The quinolinol metal complex is, for example, a compound represented by the following general formula (ETM-13). [ka] In the formula, R 1 ~R 6 are each independently hydrogen, fluorine, alkyl, cycloalkyl, aralkyl, alkenyl, cyano, alkoxy or aryl; M is Li, Al, Ga, Be or Zn; and n is an integer of 1 to 3.

[0453] Specific examples of quinolinol-based metal complexes include 8-quinolinol lithium, tris(8-quinolinolato)aluminum, tris(4-methyl-8-quinolinolato)aluminum, tris(5-methyl-8-quinolinolato)aluminum, tris(3,4-dimethyl-8-quinolinolato)aluminum, tris(4,5-dimethyl-8-quinolinolato)aluminum, tris(4,6-dimethyl-8-quinolinolato)aluminum, bis(2-methyl-8-quinolinolato)(phenolate)aluminum, bis(2-methyl-8-quinolinolato)(phenolate), and bis(2-methyl-8-quinolinolato). Bis(2-methylphenolate)aluminum, bis(2-methyl-8-quinolinate)(3-methylphenolate)aluminum, bis(2-methyl-8-quinolinate)(4-methylphenolate)aluminum, bis(2-methyl-8-quinolinate)(2-phenylphenolate)aluminum, bis(2-methyl-8-quinolinate)(3-phenylphenolate)aluminum, bis(2-methyl-8-quinolinate)(4-phenylphenolate)aluminum, bis(2-methyl-8-quinolinate)(2,3 -dimethylphenolate)aluminum, bis(2-methyl-8-quinolinate)(2,6-dimethylphenolate)aluminum, bis(2-methyl-8-quinolinate)(3,4-dimethylphenolate)aluminum, bis(2-methyl-8-quinolinate)(3,5-dimethylphenolate)aluminum, bis(2-methyl-8-quinolinate)(3,5-di-t-butylphenolate)aluminum, bis(2-methyl-8-quinolinate)(2,6-diphenylphenolate)aluminum, bis(2-methyl-8-quinolinate)(3,5-di-t-butylphenolate)aluminum linolate)(2,4,6-triphenylphenolate)aluminum, bis(2-methyl-8-quinolinolate)(2,4,6-trimethylphenolate)aluminum, bis(2-methyl-8-quinolinolate)(2,4,5,6-tetramethylphenolate)aluminum, bis(2-methyl-8-quinolinolate)(1-naphtholate)aluminum, bis(2-methyl-8-quinolinolate)(2-naphtholate)aluminum, bis(2,4-dimethyl-8-quinolinolate)(2-phenylphenolate)aluminum, bis(2,4-Dimethyl-8-quinolinolate)(3-phenylphenolate)aluminum, bis(2,4-dimethyl-8-quinolinolate)(4-phenylphenolate)aluminum, bis(2,4-dimethyl-8-quinolinolate)(3,5-dimethylphenolate)aluminum, bis(2,4-dimethyl-8-quinolinolate)(3,5-di-t-butylphenolate)aluminum, bis(2-methyl-8-quinolinolate)aluminum-μ-oxo-bis(2-methyl-8-quinolinolate)aluminum, bis(2,4-dimethyl-8-quinolinolate)aluminum-μ-oxo-bis(2,4-dimethyl-8-quinolinolate)aluminum, bis(2-methyl-4-ethyl-8- quinolinolate)aluminum-μ-oxo-bis(2-methyl-4-ethyl-8-quinolinolate)aluminum, bis(2-methyl-4-methoxy-8-quinolinolate)aluminum-μ-oxo-bis(2-methyl-4-methoxy-8-quinolinolate)aluminum, bis(2-methyl-5-cyano-8-quinolinolate)aluminum-μ-oxo-bis(2-methyl-5-cyano-8-quinolinolate)aluminum, bis(2-methyl-5-trifluoromethyl-8-quinolinolate)aluminum-μ-oxo-bis(2-methyl-5-trifluoromethyl-8-quinolinolate)aluminum, bis(10-hydroxybenzo[h]quinoline)beryllium, etc.

[0454] The quinolinol metal complex can be produced using known raw materials and known synthesis methods.

[0455] <Thiazole derivatives and benzothiazole derivatives> The thiazole derivative is, for example, a compound represented by the following formula (ETM-14-1). [ka] The benzothiazole derivative is, for example, a compound represented by the following formula (ETM-14-2). [ka]

[0456] In each formula, φ is an n-valent aryl ring (preferably an n-valent benzene ring, naphthalene ring, anthracene ring, fluorene ring, benzofluorene ring, phenalene ring, phenanthrene ring or triphenylene ring), n is an integer from 1 to 4, and the "thiazole-based substituent" or "benzothiazole-based substituent" is a substituent in which the pyridyl group in the "pyridine-based substituent" in the above formula (ETM-2), formula (ETM-2-1) and formula (ETM-2-2) is replaced with the below-mentioned thiazole group or benzothiazole group, and at least one hydrogen in the thiazole derivative and benzothiazole derivative may be replaced with deuterium. * in the following structural formula indicates a bond position. [ka]

[0457] It is further preferable that φ is an anthracene ring or a fluorene ring. In this case, the structure can be as described in the above formula (ETM-2-1) or formula (ETM-2-2). 11 ~R 18 The explanation for formula (ETM-2-1) or formula (ETM-2-2) above can be cited. In addition, in formula (ETM-2-1) or formula (ETM-2-2) above, the two pyridine-based substituents are explained as being bonded together, but when these are replaced with a thiazole-based substituent (or a benzothiazole-based substituent), both pyridine-based substituents may be replaced with a thiazole-based substituent (or a benzothiazole-based substituent) (i.e., n=2), or one of the pyridine-based substituents may be replaced with a thiazole-based substituent (or a benzothiazole-based substituent) and the other pyridine-based substituent may be replaced with R 11 ~R 18 (i.e., n=1). Furthermore, for example, R in the above formula (ETM-2-1) 11 ~R 18 At least one of the substituents is replaced with a thiazole-based substituent (or a benzothiazole-based substituent) to form a "pyridine-based substituent" R 11 ~R 18 may be substituted.

[0458] These thiazole or benzothiazole derivatives can be produced using known raw materials and known synthesis methods.

[0459] The electron transport layer or the electron injection layer may further contain a substance capable of reducing the material forming the electron transport layer or the electron injection layer. As the reducing substance, various substances can be used as long as they have a certain degree of reducing ability, and for example, at least one selected from the group consisting of alkali metals, alkaline earth metals, rare earth metals, oxides of alkali metals, halides of alkali metals, oxides of alkaline earth metals, 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 can be suitably used.

[0460] Preferred reducing substances include alkali metals such as Na (work function 2.36 eV), K (2.28 eV), Rb (2.16 eV) or Cs (1.95 eV) and alkaline earth metals such as Ca (2.9 eV), Sr (2.0 to 2.5 eV) or Ba (2.52 eV), and substances with a work function of 2.9 eV or less are particularly preferred. Among these, more preferred reducing substances are alkali metals such as K, Rb or Cs, more preferably Rb or Cs, and most preferably Cs. These alkali metals have particularly high reducing ability, and by adding a relatively small amount to the material forming the electron transport layer or electron injection layer, the luminance of the organic EL element can be improved and the life can be extended. Furthermore, as a reducing substance having a work function of 2.9 eV or less, a combination of two or more of these alkali metals is also preferred, and in particular, a combination containing Cs is preferred, for example, a combination of Cs and Na, Cs and K, Cs and Rb, or a combination of Cs, Na and K. By containing Cs, the reducing ability can be efficiently exhibited, and by adding it to a material forming an electron transport layer or an electron injection layer, the luminance of the organic EL element can be improved and the life span can be extended.

[0461] <Cathode in organic electroluminescent device> The cathode 108 serves to inject electrons into the light-emitting layer 105 through the electron injection layer 107 and the electron transport layer 106 .

[0462] The material for forming the cathode 108 is not particularly limited as long as it is a substance that can efficiently inject electrons into the organic layer, but the same material as the material for forming the anode 102 can be used. Among them, metals such as tin, indium, calcium, aluminum, silver, copper, nickel, chromium, gold, platinum, iron, zinc, lithium, sodium, potassium, cesium, and magnesium, or alloys thereof (magnesium-silver alloy, magnesium-indium alloy, aluminum-lithium alloy such as lithium fluoride / aluminum, etc.), etc. are preferable. In order to increase the electron injection efficiency and improve the device characteristics, lithium, sodium, potassium, cesium, calcium, magnesium, or alloys containing these low work function metals are effective. However, these low work function metals are generally unstable in the air. To improve this point, for example, a method is known in which a trace amount of lithium, cesium, or magnesium is doped into the organic layer to use a highly stable electrode. As other dopants, inorganic salts such as lithium fluoride, cesium fluoride, lithium oxide, and cesium oxide can also be used. However, they are not limited to these.

[0463] Further, for electrode protection, preferred examples include lamination of metals such as platinum, gold, silver, copper, iron, tin, aluminum, and indium, or alloys using these metals, inorganic substances such as silica, titania, and silicon nitride, polyvinyl alcohol, vinyl chloride, hydrocarbon polymer compounds, etc. The method of producing these electrodes is also not particularly limited as long as it can provide electrical continuity, and may be resistance heating, electron beam deposition, sputtering, ion plating, coating, or the like.

[0464] <Binding agents that may be used in each layer> The materials used for the hole injection layer, hole transport layer, light emitting layer, electron transport layer and electron injection layer can form each layer alone, but they can also be used as a polymer binder by being dispersed in a solvent-soluble resin such as polyvinyl chloride, polycarbonate, polystyrene, poly(N-vinylcarbazole), polymethyl methacrylate, polybutyl methacrylate, polyester, polysulfone, polyphenylene oxide, polybutadiene, hydrocarbon resin, ketone resin, phenoxy resin, polyamide, ethyl cellulose, vinyl acetate resin, ABS resin, polyurethane resin, or a curable resin such as phenol resin, xylene resin, petroleum resin, urea resin, melamine resin, unsaturated polyester resin, alkyd resin, epoxy resin, silicone resin, or the like.

[0465] <Method for producing organic electroluminescent device> Each layer constituting an organic EL element can be formed by forming the material to be formed into a thin film by a method such as vapor deposition, resistance heating vapor deposition, electron beam vapor deposition, sputtering, molecular lamination, printing, spin coating or casting, coating, etc. The thickness of each layer thus formed is not particularly limited and can be set appropriately according to the properties of the material, but is usually in the range of 2 nm to 5000 nm. The thickness of the film can usually be measured with a quartz crystal oscillation type film thickness measuring device, etc. When forming a thin film by vapor deposition, the vapor deposition conditions vary depending on the type of material, the desired crystal structure and association structure of the film, etc. The vapor deposition conditions are generally a boat heating temperature of +50 to +400°C, a vacuum degree of 10, and a vacuum of 10. -6 ~10 -3 It is preferable to appropriately set the pressure, pressure Pa, deposition rate 0.01 to 50 nm / sec, substrate temperature -150 to +300°C, and film thickness in the range of 2 nm to 5 µm.

[0466] Next, as an example of a method for producing an organic EL element, a method for producing an organic EL element consisting of an anode / hole injection layer / hole transport layer / light-emitting layer consisting of a host material and a dopant material / electron transport layer / electron injection layer / cathode will be described. After forming a thin film of an anode material on a suitable substrate by a deposition method or the like to produce an anode, thin films of a hole injection layer and a hole transport layer are formed on the anode. A host material and a dopant material are co-deposited on the anode to form a thin film to produce a light-emitting layer, an electron transport layer and an electron injection layer are formed on the light-emitting layer, and a thin film consisting of a cathode material is further formed by a deposition method or the like to produce a cathode, thereby obtaining a desired organic EL element. In the production of the above-mentioned organic EL element, the production order can also be reversed, and the elements can be produced in the order of a cathode, an electron injection layer, an electron transport layer, a light-emitting layer, a hole transport layer, a hole injection layer, and an anode.

[0467] When applying a DC voltage to the organic EL element obtained in this way, the anode should be set to + and the cathode to -. When a voltage of about 2 to 40 V is applied, light emission can be observed from the transparent or semi-transparent electrode side (anode or cathode, or both). This organic EL element also emits light when a pulse current or an AC current is applied. The waveform of the AC current applied may be any waveform.

[0468] <Applications of organic electroluminescent devices> The present invention can also be applied to a display device having an organic EL element or a lighting device having an organic EL element. A display device or lighting device including an organic EL element can be manufactured by a known method, for example by connecting the organic EL element according to this embodiment to a known driving device, and can be driven appropriately using a known driving method such as DC driving, pulse driving, or AC driving.

[0469] Examples of the display device include panel displays such as color flat panel displays, and flexible displays such as flexible color organic electroluminescent (EL) displays (see, for example, JP-A-10-335066, JP-A-2003-321546, JP-A-2004-281086, etc.). Examples of the display method include matrix and segment methods. Note that matrix display and segment display may coexist in the same panel.

[0470] In a matrix, pixels for display are arranged two-dimensionally, such as in a grid or mosaic pattern, and a collection of pixels displays characters and images. The shape and size of the pixels are determined by the application. For example, square pixels with sides of 300 μm or less are usually used to display images and characters on computers, monitors, and televisions, and pixels with sides of mm order are used for large displays such as display panels. For monochrome display, pixels of the same color are arranged, but for color display, red, green, and blue pixels are displayed side by side. In this case, there are typically delta type and stripe type. The driving method for this matrix can be either line sequential driving method or active matrix. Line sequential driving has the advantage of being simpler in structure, but when considering the operating characteristics, active matrix may be superior, so it is necessary to use it according to the application.

[0471] In the segment type, a pattern is formed to display predetermined information, and a predetermined area is illuminated. Examples include time and temperature displays in digital clocks and thermometers, operating status displays in audio equipment and induction cookers, and panel displays in automobiles.

[0472] Examples of the lighting device include lighting devices for indoor lighting, backlights for liquid crystal display devices, etc. (see, for example, JP 2003-257621 A, JP 2003-277741 A, JP 2004-119211 A, etc.). Backlights are mainly used for the purpose of improving the visibility of non-self-luminous display devices, and are used in liquid crystal display devices, clocks, audio devices, automobile panels, display boards, signs, etc. In particular, for liquid crystal display devices, particularly backlights for personal computers, where thinning is an issue, it is difficult to make them thin because conventional methods are made of fluorescent lamps and light guide plates, so the backlight using the light-emitting element according to this embodiment is characterized by its thinness and light weight.

[0473] 3-2. Other organic devices The polycyclic aromatic compound according to the present invention can be used for producing the organic electroluminescent device described above, as well as an organic field effect transistor or an organic thin-film solar cell.

[0474] An organic field-effect transistor is a transistor that controls current by an electric field generated by voltage input, and has a gate electrode in addition to a source electrode and a drain electrode. When a voltage is applied to the gate electrode, an electric field is generated, and the flow of electrons (or holes) flowing between the source electrode and the drain electrode can be arbitrarily blocked to control the current. Field-effect transistors are easier to miniaturize than simple transistors (bipolar transistors), and are often used as elements that make up integrated circuits.

[0475] The structure of an organic field effect transistor is usually such that a source electrode and a drain electrode are provided in contact with an organic semiconductor active layer formed using the polycyclic aromatic compound according to the present invention, and a gate electrode is provided sandwiching an insulating layer (dielectric layer) in contact with the organic semiconductor active layer. Examples of the element structure include the following structure. (1) Substrate / gate electrode / insulating layer / source and drain electrodes / organic semiconductor active layer (2) Substrate / gate electrode / insulating layer / organic semiconductor active layer / source electrode and drain electrode (3) Substrate / organic semiconductor active layer / source electrode / drain electrode / insulator layer / gate electrode (4) Substrate / source electrode / drain electrode / organic semiconductor active layer / insulator layer / gate electrode The organic field effect transistor thus configured can be used as a pixel driving switching element for an active matrix driving type liquid crystal display or an organic electroluminescence display.

[0476] The organic thin-film solar cell has 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 according to 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 depending on its physical properties. The polycyclic aromatic compound according to the present invention can function as a hole transport material or an electron transport material in an organic thin-film solar cell. In addition to the above, the organic thin-film solar cell may appropriately include a hole blocking layer, an electron blocking layer, an electron injection layer, a hole injection layer, a smoothing layer, and the like. The organic thin-film solar cell can be used by appropriately selecting and combining known materials used in organic thin-film solar cells. EXAMPLES

[0477] The present invention will be described in more detail below with reference to examples, but the present invention is not limited thereto. First, synthesis examples of polycyclic aromatic compounds will be described below.

[0478] Synthesis Example (1): Synthesis of Compound (1-901) [ka]

[0479] In a nitrogen atmosphere, compound (I-1) (3.05 g, 10 mmol), compound (I-2) (3.35 g, 12 mmol), potassium carbonate (4.10 g, 30 mmol), bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II) (Pd-132: 0.0783 g, 0.1 mmol) and tetrabutylammonium bromide (TBAB: 0.97 g, 3 mmol) were placed in a flask, toluene (30 ml) and distilled water (15 ml) were added, and the mixture was heated under reflux for 2 hours. The precipitated solid was filtered by suction and washed with water and heptane, and the obtained crude product was purified with a silica gel short column (eluent: chlorobenzene) to obtain compound (1-901) as a white solid (yield: 0.56 g). [ka]

[0480] Synthesis Example (2): Synthesis of Compound (1-902) [ka]

[0481] In a nitrogen atmosphere, compound (I-3) (3.08 g, 10 mmol), compound (I-2) (3.35 g, 12 mmol), potassium carbonate (4.08 g, 30 mmol), bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II) (Pd-132: 0.0775 g, 0.1 mmol) and tetrabutylammonium bromide (TBAB: 1.00 g, 3 mmol) were placed in a flask, toluene (30 ml) and distilled water (15 ml) were added, and the mixture was heated under reflux for 14 hours. The precipitated solid was filtered by suction and washed with water and heptane, and the obtained crude product was purified with a silica gel short column (eluent: chlorobenzene) to obtain compound (1-902) as a white solid (yield: 1.27 g). [ka]

[0482] By appropriately changing the raw material compounds, other polycyclic aromatic compounds of the present invention can be synthesized according to the methods of the above-mentioned synthesis examples.

[0483] Next, in order to explain the present invention in more detail, examples of organic EL devices using the compounds of the present invention will be shown, but the present invention is not limited to these.

[0484] <Evaluation of deposition-type organic EL elements> Organic EL devices according to Example 1, Example 2 and Comparative Example 1 were fabricated, and each had a luminance of 1000 cd / m 2 The light-emitting characteristics, such as the driving voltage (V) and external quantum efficiency (%), were measured.

[0485] The quantum efficiency of a light-emitting element includes internal quantum efficiency and external quantum efficiency, and the internal quantum efficiency indicates the ratio at which the external energy injected as electrons (or holes) into the light-emitting layer of the light-emitting element is converted purely into photons. On the other hand, the external quantum efficiency is calculated based on the amount of these photons that are emitted to the outside of the light-emitting element, and since some of the photons generated in the light-emitting layer are absorbed or continue to be reflected inside the light-emitting element and are not emitted to the outside of the light-emitting element, the external quantum efficiency is lower than the internal quantum efficiency.

[0486] The external quantum efficiency was measured as follows: The luminance of the element was 1000 cd / m using an Advantest voltage / current generator R6144. 2 The element was made to emit light by applying a voltage that would result in a value of 10 ...

[0487] The material configurations of the layers in the organic EL devices according to Example 1, Example 2 and Comparative Example 1 are shown in Table 1 below. [Table 1]

[0488] In Table 1, "HI" stands for 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, "HT-1" is N-([1,1'-biphenyl]-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluoren-2-amine, "Host1" is 9-phenyl-10-(4-phenylnaphthalen-1-yl)anthracene, and "ET-1" is 9-(4'-(dimesitylboranyl)-[1,1'-binaphthalen]-4-yl)-9H-carbazole. The chemical structures of these, along with "Dopant1", are shown below.

[0489] [ka]

[0490] <Example 1> A 26 mm × 28 mm × 0.7 mm glass substrate (manufactured by Optoscience Co., Ltd.) on which an ITO film having a thickness of 180 nm was formed by sputtering and polished to 120 nm was used as a transparent support substrate. This transparent support substrate was fixed to the substrate holder of a commercially available deposition device (manufactured by Nagasu Sangyo Co., Ltd.), and a tungsten deposition boat containing HI, HAT-CN, HT-1, Host1, Dopant1, ET-1, compound (1-901), LiF, and aluminum was attached.

[0491] The following layers were formed in order on the ITO film of the transparent support substrate. -4The pressure was reduced to Pa. First, HI was heated and vapor-deposited to a film thickness of 65 nm to form a hole injection layer 1. Next, HAT-CN was heated and vapor-deposited to a film thickness of 5 nm to form a hole injection layer 2. Next, HT-1 was heated and vapor-deposited to a film thickness of 90 nm to form a hole transport layer. Next, Host1 and Dopant1 were simultaneously heated and vapor-deposited to a film thickness of 25 nm to form a light-emitting layer. The deposition rate was adjusted so that the mass ratio of Host1 to Dopant1 was approximately 95 to 5. Next, ET-1 was heated and vapor-deposited to a film thickness of 20 nm to form an electron transport layer 1. Next, the compound (1-901) was heated and vapor-deposited to a film thickness of 10 nm to form an electron transport layer 2. The deposition rate of each layer was 0.01 to 1 nm / second. Thereafter, LiF was heated and vapor-deposited at a deposition rate of 0.01 to 0.1 nm / second to a film thickness of 1 nm, and then aluminum was heated and vapor-deposited to a film thickness of 100 nm to form a cathode, obtaining an organic EL element. At this time, the deposition rate was adjusted between 0.1 nm and 10 nm / second.

[0492] <Example 2> An organic EL element was fabricated in the same manner as in Example 1 except that the electron transport layer 2 was replaced with the compound (1-902).

[0493] <Comparative Example 1> An organic EL element was fabricated in the same manner as in Example 1 except that the electron transport layer 2 was replaced with ET-1 (that is, an electron transport layer of 30 nm was formed only with ET-1).

[0494] A DC voltage was applied with the ITO electrode as the anode and the aluminum electrode as the cathode, and the characteristics during light emission were measured, resulting in the results shown in Table 2 below. From these results, by using the compound of the present invention as the electron transport layer, the driving voltage can be lowered. 2 <Estimation of electron transport characteristics using TOF measurement>

Table 2

[0495] <Estimation of electron transport characteristics using TOF measurement> By measuring the time of flight (TOF), the electron mobility of the material can be measured separately from the electron injection property. The electron mobility of a comparative compound (BPy-TP2), which is a representative electron injection material having a bipyridyl group, was measured as a comparative example, and the electron mobility of a reference compound (BO2), which has the same basic structure as the polycyclic aromatic compound of the present invention, was measured as a reference example. [ka]

[0496] The electron mobility at an applied electric field of 0.4 MV / cm is 9.7 × 10 for the comparative compound (BPy-TP2). -7 cm 2 / V·s, and for the reference compound (BO2) it is 1.6×10 -6 cm 2 / V·s. This result shows that the basic skeleton of the polycyclic aromatic compound of the present invention has superior electron transport properties compared to the comparative compounds. Therefore, a polycyclic aromatic compound in which a nitrogen-containing substituent (a group of the above formula (BiN)) that enhances the electron injection property, such as bipyridyl, has been introduced into this basic skeleton can be expected to be an excellent material for electron transport layers or electron injection layers.

[0497] As described above, some of the compounds according to the present invention have been evaluated as materials for organic EL devices and shown to be excellent materials, but other compounds that have not been evaluated also have the same basic skeleton and have similar structures overall, and it will be understood by those skilled in the art that they are similarly excellent materials for organic EL devices. [Industrial Applicability]

[0498] In the present invention, by introducing a nitrogen-containing substituent of formula (BiN) into a polycyclic aromatic compound of formula (1) in which a plurality of aromatic rings are linked by boron atoms, oxygen atoms, or the like, it is possible to provide a material for an electron transport layer or a material for an electron injection layer having both high electron injection properties and high electron mobility, and thus it is possible to fabricate an organic device with a low driving voltage, such as an organic EL element. [Explanation of symbols]

[0499] 100 Organic electroluminescent device 101 Substrate 102 Anode 103 Hole injection layer 104 Hole transport layer 105 Light-emitting layer 106 Electron transport layer 107 Electron injection layer 108 Cathode

Claims

1. A polycyclic aromatic compound represented by the following general formula (2): 【Chemistry 2】 In the above formula (2), R １ ~R １１ are each independently a hydrogen atom, a group represented by formula (BiN-1), or a group represented by formula (BiN-2), １ ~R １１ at least one of the formulas is a group represented by formula (BiN-1) or (BiN-2), in which * indicates a bonding position; At least one hydrogen in the compound may be replaced with cyano, halogen, or deuterium.

2. A polycyclic aromatic compound described in claim 1, represented by any of the following structural formulas. 【Chemistry 4】

3. A material for organic devices containing the polycyclic aromatic compound described in claim 1 or 2.

4. The material for an organic device according to claim 3 , which is a material for an organic electroluminescent element, a material for an organic field effect transistor, or a material for an organic thin-film solar cell.

5. The material for an organic device according to claim 4 , wherein the material for an organic electroluminescent device is a material for an electron transport layer or a material for an electron injection layer.

6. 6. An organic electroluminescent device comprising a pair of electrodes consisting of an anode and a cathode, a light-emitting layer disposed between the pair of electrodes, and at least one of an electron transport layer and an electron injection layer disposed between the cathode and the light-emitting layer, wherein at least one of the electron transport layer and the electron injection layer contains the material for an organic device according to claim 5.

7. 7. The organic electroluminescence device according to claim 6, wherein at least one of the electron transport layer and the electron injection layer contains at least one selected from the group consisting of borane derivatives, pyridine derivatives, fluoranthene derivatives, BO-based derivatives, anthracene derivatives, benzofluorene derivatives, phosphine oxide derivatives, pyrimidine derivatives, carbazole derivatives, triazine derivatives, benzimidazole derivatives, phenanthroline derivatives, and quinolinol-based metal complexes.

8. 8. The organic electroluminescent device according to claim 6, wherein at least one of the electron transport layer and the electron injection layer contains at least one selected from the group consisting of alkali metals, alkaline earth metals, rare earth metals, oxides of alkali metals, oxides of alkaline earth metals, oxides of rare earth metals, halides of alkali metals, halides of alkaline 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.

9. A display device or lighting device comprising the organic electroluminescent element according to claim 6.

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