Amino-substituted polycyclic aromatic compounds

Abstract

To provide a novel amino-substituted polycyclic aromatic compound and an organic EL device using the same.SOLUTION: Introduction of specific amino groups and specific substituents (Ra group and Rb group) into a polycyclic aromatic compound in which multiple aromatic rings are linked by a boron atom and an oxygen atom, etc. provides more choices of organic device materials such as an organic EL device material. In addition, use of such a novel amino-substituted polycyclic aromatic compound as the organic EL device material provides, for example, an organic EL device having excellent luminous efficiency and device life.SELECTED DRAWING: None

Description

[Technical field]

[0001] The present invention relates to an amino-substituted polycyclic aromatic compound and a multimer thereof (hereinafter, also collectively referred to as "polycyclic aromatic compound"), and an organic electroluminescent device, an organic field effect transistor, an organic thin-film solar cell, a display device, and a lighting device using the same. In this specification, the "organic electroluminescent 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.

[0006] The host material for organic EL devices is generally a molecule in which multiple existing aromatic rings such as benzene or carbazole are linked together with single bonds or phosphorus or silicon atoms. This is because linking a large number of relatively small conjugated aromatic rings ensures the large HOMO-LUMO gap (band gap Eg in a thin film) required for the host material. Furthermore, host materials for organic EL devices that use phosphorescent materials or thermally activated delayed fluorescent materials have high triplet excitation energy (E T ) is also required, but by linking a donor or acceptor aromatic ring or substituent to the molecule, the SOMO1 and SOMO2 in the triplet excited state (T1) are localized, and the exchange interaction between the two orbitals is reduced, allowing the triplet excitation energy (E T) can be improved. However, small aromatic rings in the conjugated system do not have sufficient redox stability, and devices using molecules formed by linking existing aromatic rings as host materials do not have sufficient life spans. On the other hand, polycyclic aromatic compounds with extended π-conjugated systems generally have excellent redox stability, but they have poor HOMO-LUMO gaps (band gaps in thin films, Eg) and triplet excitation energies (E T ) is low, it has been considered unsuitable as a host material. [Prior art documents] [Patent documents]

[0007] [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]

[0008] 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.

[0009] 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 a material for an emission layer, in particular a dopant material, that can improve the luminous efficiency and device life. [Means for solving the problem]

[0010] As a result of intensive research aimed at solving the above problems, the present inventors have found that an excellent organic EL element can be obtained by, for example, constructing an organic EL element by disposing a layer containing a polycyclic aromatic compound having a specific amino group between a pair of electrodes, and have thus completed the present invention. Furthermore, as a result of intensive research aimed at solving the above problems, the present inventors have found that an excellent organic EL element can be obtained by, for example, constructing an organic EL element by disposing, between a pair of electrodes, a layer containing a polycyclic aromatic compound in which an amino group and specific substituents (Ra group and Rb group) are introduced at specific positions, and have thus completed the present invention. That is, the present invention provides the following amino-substituted polycyclic aromatic compounds or multimers thereof, and further provides materials for organic devices, such as materials for organic EL devices, containing the following amino-substituted polycyclic aromatic compounds or multimers thereof.

[0011] 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.

[0012] 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, and at least one hydrogen atom in these rings may be substituted; At least one hydrogen atom in at least one of the rings B and C is substituted with a group represented by the above formula (Am), 1 and Ar 2 are each independently an aryl or heteroaryl, in which at least one hydrogen atom is optionally substituted; Ar 1 and Ar 2 may be bonded via a single bond or a linking group, the group represented by the above formula (Am) is substituted for hydrogen in ring B or ring C at *, Ring B and ring C may be bonded via a linking group; Y 1 is B, P, P=O, P=S, Al, Ga, As, Si-R or Ge-R, wherein R of Si-R and Ge-R is aryl, alkyl or cycloalkyl; X 1 and X 2 are independently >O, >NR, >Si(-R) 2 ,>C(-R) 2 , >S or >Se, and R of the >NR is an optionally substituted aryl (excluding an amino group as a substituent), an optionally substituted heteroaryl, an optionally substituted alkyl or an optionally substituted cycloalkyl, and the >Si(-R) 2 R is optionally substituted aryl, optionally substituted heteroaryl, optionally substituted alkyl or optionally substituted cycloalkyl, and the >C(-R) 2R is hydrogen, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted alkyl or optionally substituted cycloalkyl, and the above-mentioned >NR, >Si(-R) 2 and >C(-R) 2 R in at least one of the above may be bonded to at least one of the rings A, B and C via a linking group or a single bond; 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 -CH 2 - may be replaced by -O-, and At least one hydrogen atom in the compound or structure represented by formula (1) may be replaced with deuterium, cyano, or halogen.

[0013] Section 2. Item 1: A polycyclic aromatic compound according to item 1, represented by the following general formula (1A): or a multimer of the polycyclic aromatic compound according to item 1, having a plurality of structures represented by the following general formula (1A): [ka] (In the above formula (1A), 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; At least one hydrogen atom in at least one of the rings B and C is substituted with a group represented by the above formula (Am), 1 is biphenylyl, and Ar 2 is aryl (excluding biphenylyl) or heteroaryl, at least one hydrogen atom in the biphenylyl, aryl or heteroaryl may be substituted with an alkyl or cycloalkyl, and the group represented by the above formula (Am) is substituted with a hydrogen atom in the B ring or C ring at *, Ring B and ring C may be bonded via a linking group; Y 1 is B, P, P=O, P=S, Al, Ga, As, Si-R or Ge-R, wherein R of Si-R and Ge-R is aryl, alkyl or cycloalkyl; X 1 and X 2 are independently >O, >NR, >Si(-R) 2 ,>C(-R) 2 , >S or >Se, and R of the >NR is an optionally substituted aryl (excluding an amino group as a substituent), an optionally substituted heteroaryl, an optionally substituted alkyl or an optionally substituted cycloalkyl, and the >Si(-R) 2 R is optionally substituted aryl, optionally substituted heteroaryl, optionally substituted alkyl or optionally substituted cycloalkyl, and the >C(-R) 2 R is hydrogen, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted alkyl or optionally substituted cycloalkyl, and the above-mentioned >NR, >Si(-R) 2 and >C(-R) 2 R in at least one of the above may be bonded to at least one of the rings A, B and C via a linking group or a single bond; In the compound or structure represented by formula (1A), 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 -CH 2 - may be replaced by -O-, and At least one hydrogen atom in the compound or structure represented by formula (1A) may be replaced with deuterium, cyano, or halogen.

[0014] Section 3. In the above formula (1A), 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 with 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, and these rings may be substituted with Y 1 , X 1 and X 2 The above formula (1A) has a 5-membered or 6-membered ring sharing a bond with the central fused 2-ring structure, At least one hydrogen atom in at least one of the rings B and C is substituted with a group represented by the above formula (Am); B and C rings are >O, >NR, >Si(-R) 2 ,>C(-R) 2 , >S or >Se, and the >NR and >Si(-R) 2 R is each independently an aryl which may be substituted with an alkyl or cycloalkyl, a heteroaryl which may be substituted with an alkyl or cycloalkyl, an alkyl or a cycloalkyl, and the >C(-R) 2 R is hydrogen, aryl which may be substituted with alkyl or cycloalkyl, heteroaryl which may be substituted with alkyl or cycloalkyl, alkyl or cycloalkyl, and the above-mentioned >NR, >Si(-R) 2 and >C(-R) 2 At least one of R is -O-, -S-, -C(-R) 2 or may be bonded to at least one of the rings B and C via a single bond, and the -C(-R) 2 R in - is hydrogen, alkyl or cycloalkyl; Y1 is B, P, P=O, P=S, Al, Ga, As, Si-R or Ge-R, wherein R of Si-R and Ge-R is aryl, alkyl or cycloalkyl; X 1 and X 2 are independently >O, >NR, >Si(-R) 2 ,>C(-R) 2 , >S or >Se, and the >NR and >Si(-R) 2 R is each independently an aryl which may be substituted with an alkyl or cycloalkyl, a heteroaryl which may be substituted with an alkyl or cycloalkyl, an alkyl or a cycloalkyl, and the >C(-R) 2 R is hydrogen, aryl which may be substituted with alkyl or cycloalkyl, heteroaryl which may be substituted with alkyl or cycloalkyl, alkyl or cycloalkyl, and the above-mentioned >NR, >Si(-R) 2 and >C(-R) 2 At least one of R is -O-, -S-, -C(-R) 2 or may be bonded to at least one of the ring A, ring B and ring C via a single bond, and the -C(-R) 2 R in - is hydrogen, alkyl or cycloalkyl; In the compound or structure represented by formula (1A), 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 -CH 2 - may be replaced by -O-; In the case of a polymer, it is a dimer or trimer having two or three structures represented by general formula (1A), and At least one hydrogen atom in the compound or structure represented by formula (1A) may be replaced by deuterium, cyano or halogen. Item 3. The polycyclic aromatic compound or a multimer thereof according to item 2.

[0015] Section 4. Item 2. The polycyclic aromatic compound according to item 2, which is represented by the following general formula (2A): [ka] (In the above formula (2A), In the ring a, the ring b, and the ring c, any "-C(-R)=" (where R is R in formula (2A) 1 ~R 11 ) may be replaced with "-N=", and any "-C(-R)=C(-R)-" (where R is R in formula (2A) 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 replaced by an aryl, heteroaryl, alkyl, or cycloalkyl; and 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; R 4 ~R 11 is a group represented by the above formula (Am), and / or at least one hydrogen atom in an aryl ring or heteroaryl ring formed together with the b ring or the c ring is substituted with a group represented by the above formula (Am), R 7 and R 8 is bonded to >O, >NR, >Si(-R) 2 ,>C(-R) 2 , >S or >Se, and the above >NR and >Si(-R) 2 R is independently 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, and the >C(-R) 2 R is hydrogen, 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, and the above-mentioned >NR, >Si(-R) 2 and >C(-R) 2 At least one of R is -O-, -S-, -C(-R) 2 or may be bonded to at least one of the rings b and c via a single bond, and the -C(-R) 2 R in - is alkyl having 1 to 6 carbon atoms or cycloalkyl having 3 to 14 carbon atoms, Y1 is B, P, P=O, P=S, Al, Ga, As, Si-R or Ge-R, and R of the Si-R and Ge-R is an aryl having 6 to 12 carbon atoms, an alkyl having 1 to 6 carbon atoms or a cycloalkyl having 3 to 14 carbon atoms; X 1 and X 2 are independently >O, >NR, >Si(-R) 2 ,>C(-R) 2 , >S or >Se, and the >NR and >Si(-R) 2 R is independently 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, and the >C(-R) 2 R is hydrogen, 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, and the above-mentioned >NR, >Si(-R) 2 and >C(-R) 2 At least one of R is -O-, -S-, -C(-R) 2 or may be bonded to at least one of the ring a, ring b and ring c via a single bond, and the -C(-R) 2 R in - is alkyl having 1 to 6 carbon atoms or cycloalkyl having 3 to 14 carbon atoms, In the compound represented by formula (2A), 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, and at least one -CH in the cycloalkane 2 - may be replaced by -O-, and At least one hydrogen atom in the compound represented by formula (2A) may be substituted with deuterium, cyano or halogen.

[0016] Section 5. In the above formula (2A), In the ring a, the ring b, and the ring c, any "-C(-R)=" (where R is R in formula (2A) 1 ~R 11 ) may be replaced with "-N=", and any "-C(-R)=C(-R)-" (where R is R in formula (2A) 1 ~R 11 (which is a radical) may be replaced with "-N(-R)-", "-O-", or "-S-", and R in the "-N(-R)-" is 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; R 1 ~R 11 are 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, 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); and 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 by aryl having 6 to 10 carbon atoms, alkyl having 1 to 12 carbon atoms, cycloalkyl having 3 to 16 carbon atoms, triarylsilyl (wherein aryl is 6 to 12 carbon atoms), or trialkylsilyl (wherein alkyl is 1 to 5 carbon atoms); R 4 ~R 11 is a group represented by the above formula (Am), and / or at least one hydrogen atom in an aryl ring or heteroaryl ring formed together with the b ring or the c ring is substituted with a group represented by the above formula (Am), 1is biphenylyl, and Ar 2 represents an aryl having 6 to 30 carbon atoms (excluding biphenylyl) or a heteroaryl having 2 to 30 carbon atoms, in which at least one hydrogen atom in the biphenylyl, aryl or heteroaryl may be substituted by an alkyl having 1 to 24 carbon atoms or a cycloalkyl having 3 to 24 carbon atoms; R 7 and R 8 combine to form >O, >NR, >C(-R) 2 or >S, in which R in >NR 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, and the >C(-R) 2 R is hydrogen, aryl having 6 to 10 carbon atoms, alkyl having 1 to 5 carbon atoms, or cycloalkyl having 5 to 10 carbon atoms; Y 1 is B, P, P=O, P=S or Si-R, wherein R of the Si-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; X 1 and X 2 are independently >O, >NR, >C(-R) 2 or >S, and R of the >NR 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, and the >C(-R) 2 R is hydrogen, aryl having 6 to 10 carbon atoms, alkyl having 1 to 5 carbon atoms, or cycloalkyl having 5 to 10 carbon atoms; In the compound represented by formula (2A), 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 20 carbon atoms, and at least one hydrogen in the cycloalkane may be substituted with an aryl having 6 to 16 carbon atoms, a heteroaryl having 2 to 22 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 compound represented by formula (2A) may be substituted with deuterium, cyano or halogen. Item 5. The polycyclic aromatic compound according to item 4.

[0017] Section 6. In the above formula (2A), In the ring a, the ring b, and the ring c, any "-C(-R)=" (where R is R in formula (2A) 1 ~R 11 ) may be replaced with "-N=", and any "-C(-R)=C(-R)-" (where R is R in formula (2A) 1 ~R 11 (which is a radical) 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 each independently represents hydrogen, an aryl having 6 to 16 carbon atoms, a heteroaryl having 2 to 20 carbon atoms, a diarylamino (wherein the aryl has 6 to 10 carbon atoms), an alkyl having 1 to 12 carbon atoms, or a cycloalkyl having 3 to 16 carbon atoms; R 5 and R 10 At least one of the above is a group represented by the formula (Am), and in the above formula (Am), 1 is biphenylyl, and Ar 2 represents an aryl having 6 to 16 carbon atoms (excluding biphenylyl) or a heteroaryl having 2 to 20 carbon atoms, in which at least one hydrogen atom in the biphenylyl, aryl or heteroaryl 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 is bonded to >O, >NR or >C(-R) 2 R of the >NR may be 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, and the >C(-R) 2 R is hydrogen, aryl having 6 to 10 carbon atoms, alkyl having 1 to 5 carbon atoms, or cycloalkyl having 5 to 10 carbon atoms; Y1 is B, P, P=O or P=S, X 1 and X 2 are each independently >O, >NR or >C(-R) 2 R of the >NR 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, and the >C(-R) 2 R is hydrogen, aryl having 6 to 10 carbon atoms, alkyl having 1 to 5 carbon atoms, or cycloalkyl having 5 to 10 carbon atoms; In the compound represented by formula (2A), at least one of the ring a, the ring b, the ring c, and the aryl having 6 to 10 carbon atoms as R of >NR 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 At least one hydrogen atom in the compound represented by formula (2A) may be substituted with deuterium, cyano or halogen. Item 5. The polycyclic aromatic compound according to item 4.

[0018] Section 7. In the above formula (2A), R 1 ~R 11 each independently represents a hydrogen atom, an aryl having 6 to 16 carbon atoms, a diarylamino (wherein the aryl has 6 to 10 carbon atoms), an alkyl having 1 to 12 carbon atoms, or a cycloalkyl having 3 to 16 carbon atoms; R 5 and R 10 At least one of the above is a group represented by the formula (Am), and in the above formula (Am), 1 is biphenylyl, and Ar 2 represents an aryl having 6 to 16 carbon atoms (excluding biphenylyl) or a heteroaryl having 2 to 20 carbon atoms, in which at least one hydrogen atom in the biphenylyl, aryl or heteroaryl may be substituted with an alkyl having 1 to 12 carbon atoms or a cycloalkyl having 3 to 16 carbon atoms; Y1 is B, X 1 and X 2 are both >NR or X 1 is >NR and X 2 is >O, and R of the >NR is an aryl having 6 to 10 carbon atoms, an alkyl having 1 to 5 carbon atoms, or a cycloalkyl having 5 to 10 carbon atoms, In the compound represented by formula (2A), at least one of the ring a, the ring b, the ring c, and the aryl having 6 to 10 carbon atoms as R of >NR may be condensed with a cycloalkane having 3 to 14 carbon atoms, and at least one hydrogen atom in the cycloalkane may be substituted with an alkyl having 1 to 5 carbon atoms, and At least one hydrogen atom in the compound represented by formula (2A) may be substituted with deuterium or halogen. Item 5. The polycyclic aromatic compound according to item 4.

[0019] Section 8. Item 1. A polycyclic aromatic compound according to item 1, represented by the following general formula (2B): or a multimer of the polycyclic aromatic compound according to item 1, having a plurality of structures represented by the following general formula (2B): [ka] (In the above formula (2B), Any "-C(-H)=" in the a, b, and c rings may be replaced with "-N="; R 21 ~R 30 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 21 ~R 30 adjacent groups among the above may be bonded to each other to form an aryl ring or a heteroaryl ring together with the d ring or the e 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 25 and R 26 is bonded to >O, >NR, >Si(-R) 2 ,>C(-R) 2 , >S or >Se, and the above >NR and >Si(-R) 2 R is each independently 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, in which at least one hydrogen may be substituted by 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, and the above >C(-R) 2 R is hydrogen, 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, in which at least one hydrogen may be substituted by 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; Ra is an aryl, heteroaryl, alkyl, cycloalkyl, alkoxy, aryloxy, triarylsilyl, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, or alkyldicycloalkylsilyl, in which at least one hydrogen may be replaced by an aryl, heteroaryl, alkyl, or cycloalkyl; Rb is 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 replaced by aryl, heteroaryl, alkyl, or cycloalkyl; Y 1 is B, P, P=O, P=S, Al, Ga, As, Si-R or Ge-R, and R of the Si-R and Ge-R is an aryl having 6 to 12 carbon atoms, an alkyl having 1 to 6 carbon atoms or a cycloalkyl having 3 to 14 carbon atoms; X 1 and X 2 are independently >O, >NR, >Si(-R) 2 ,>C(-R) 2 , >S or >Se, and the >NR and >Si(-R) 2 R is each independently 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, in which at least one hydrogen may be substituted by 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, and the above >C(-R) 2R is hydrogen, 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, in which at least one hydrogen may be substituted by 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, and the above-mentioned >NR, >Si(-R) 2 and >C(-R) 2 At least one of R is -O-, -S-, -C(-R) 2 or may be bonded to at least one of the ring a, ring b and ring c via a single bond, and the -C(-R) 2 R in - is alkyl having 1 to 6 carbon atoms or cycloalkyl having 3 to 14 carbon atoms, In the compound or structure represented by formula (2B), at least one of the ring a, the ring b, the ring c, the ring d, the ring e, 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, and at least one -CH in the cycloalkane 2 - may be replaced by -O-, and At least one hydrogen atom in the compound or structure represented by formula (2B) may be replaced with deuterium, cyano, or halogen.

[0020] Section 9. In the above formula (2B), Any "-C(-H)=" in the a, b, and c rings may be replaced with "-N="; R 21 ~R 30are 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, 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); R 21 ~R 30 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 d or ring e, and at least one hydrogen in the formed ring may be substituted by 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, 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); R 25 and R 26 combine to form >O, >NR, or >C(-R) 2 R in the >NR may each independently be 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, in which at least one hydrogen may be substituted by 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, and the >C(-R) 2R is hydrogen, 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, in which at least one hydrogen may be substituted by 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; Ra is an aryl having 6 to 30 carbon atoms, an alkyl having 1 to 24 carbon atoms, a cycloalkyl having 3 to 24 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), and at least one hydrogen atom in the aryl may be substituted by an alkyl having 1 to 24 carbon atoms or a cycloalkyl having 3 to 24 carbon atoms; Rb is hydrogen, an aryl having 6 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 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, 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 the aryl may be substituted by an alkyl having 1 to 24 carbon atoms or a cycloalkyl having 3 to 24 carbon atoms; Y 1 is B, P, P=O, P=S or Si-R, wherein R of the Si-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; X 1 and X 2 are independently >O, >NR, >C(-R) 2 or >S, R of the >NR 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, in which at least one hydrogen may be substituted by 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, and the >C(-R) 2R is hydrogen, 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, in which at least one hydrogen may be substituted by 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; In the compound or structure represented by formula (2B), at least one of the ring a, the ring b, the ring c, the ring d, the ring e, the formed ring, the aryl and the heteroaryl may be condensed with at least one cycloalkane having 3 to 20 carbon atoms, and at least one hydrogen in the cycloalkane may be substituted with an aryl having 6 to 16 carbon atoms, a heteroaryl having 2 to 22 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 compound or structure represented by formula (2B) may be replaced by deuterium, cyano or halogen. Item 9. The polycyclic aromatic compound or a multimer thereof according to item 8.

[0021] Section 10. In the above formula (2B), Any "-C(-H)=" in the a, b, and c rings may be replaced with "-N="; R 21 ~R 30 each independently represents a hydrogen atom, an aryl having 6 to 16 carbon atoms, a diarylamino (wherein the aryl has 6 to 10 carbon atoms), a diarylboryl (wherein the aryl has 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, or a cycloalkyl having 3 to 16 carbon atoms; Ra is an aryl having 6 to 30 carbon atoms, an alkyl having 1 to 24 carbon atoms, or a cycloalkyl having 3 to 24 carbon atoms, in which at least one hydrogen atom in the aryl may be substituted by an alkyl having 1 to 24 carbon atoms or a cycloalkyl having 3 to 24 carbon atoms; Rb is hydrogen, an aryl having 6 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 two aryls may be bonded via a single bond or a linking group), an alkyl having 1 to 24 carbon atoms, or a cycloalkyl having 3 to 24 carbon atoms, and at least one hydrogen in the aryl is optionally substituted by an alkyl having 1 to 24 carbon atoms or a cycloalkyl having 3 to 24 carbon atoms; Y 1 is B, P, P=O or P=S, X 1 and X 2 are each independently >O or >NR, and R in the >NR 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, in which at least one hydrogen may be substituted by 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, In the compound or structure represented by formula (2B), at least one of the ring a, the ring b, the ring c, the ring d, the ring e, and the aryl having 6 to 10 carbon atoms as R of >NR 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 At least one hydrogen atom in the compound or structure represented by formula (2B) may be replaced by deuterium, cyano or halogen. Item 9. The polycyclic aromatic compound or a multimer thereof according to item 8.

[0022] Section 11. Item 11. The polycyclic aromatic compound or a multimer thereof according to any one of Items 1 to 10, which is substituted with a diarylamino group fused with a cycloalkane, a carbazolyl group fused with a cycloalkane, or a benzocarbazolyl group fused with a cycloalkane.

[0023] Section 12. R in the above formula (2A) 2 Or the polycyclic aromatic compound according to any one of items 4 to 10, wherein Rb in the above formula (2B) is a diarylamino group condensed with a cycloalkane or a carbazolyl group condensed with a cycloalkane.

[0024] Section 13. Item 13. The polycyclic aromatic compound according to item 11 or 12, wherein the cycloalkane is a cycloalkane having 3 to 20 carbon atoms.

[0025] Section 14. Item 14. The polycyclic aromatic compound or a multimer thereof according to any one of Items 1 to 13, wherein the halogen is fluorine.

[0026] Section 15. Item 3. The polycyclic aromatic compound according to item 1, which is represented by the following structural formula: [ka]

[0027] Section 16. Item 3. The polycyclic aromatic compound according to item 1, which is represented by any one of the following structural formulas: [ka] [ka] [ka] In the above structural formula, "Me" is a methyl group, "tBu" is a t-butyl group, "tAm" is a t-amyl group, and "D" is deuterium.

[0028] Section 17. 17. A reactive compound in which the polycyclic aromatic compound or a multimer thereof according to any one of items 1 to 16 is substituted with a reactive substituent.

[0029] Section 18. Item 18. A polymer compound obtained by polymerizing the reactive compound according to item 17 as a monomer, or a crosslinked polymer obtained by further crosslinking the polymer compound.

[0030] Section 19. Item 17. A pendant polymer compound in which a reactive compound described in item 17 is substituted on a main chain polymer, or a pendant polymer crosslinked product in which the pendant polymer compound is further crosslinked.

[0031] Section 20. Item 17. A material for an organic device, comprising the polycyclic aromatic compound or a multimer thereof according to any one of items 1 to 16.

[0032] Section 21. Item 18. A material for an organic device, comprising the reactive compound according to item 17.

[0033] Section 22. Item 19. A material for an organic device, comprising the polymer compound or crosslinked polymer according to item 18.

[0034] Section 23. Item 19. A material for an organic device comprising the pendant polymer compound or the pendant polymer crosslinked body according to item 19.

[0035] Section 24. 24. The material for an organic device according to any one of items 20 to 23, wherein the material for an organic device 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.

[0036] Section 25. Item 25. The material for an organic device according to item 24, wherein the material for an organic electroluminescent element is a material for a light-emitting layer.

[0037] Section 26. 17. An ink composition comprising the polycyclic aromatic compound or a multimer thereof according to any one of items 1 to 16, and an organic solvent.

[0038] Section 27. Item 18. An ink composition comprising the reactive compound according to item 17 and an organic solvent.

[0039] Section 28. Item 18. An ink composition comprising a main chain polymer, the reactive compound according to item 17, and an organic solvent.

[0040] Section 29. Item 19. An ink composition comprising the polymer compound or crosslinked polymer according to item 18 and an organic solvent.

[0041] Section 30. Item 20. An ink composition comprising the pendant polymer compound or the pendant polymer crosslinked product according to item 19 and an organic solvent.

[0042] Section 31. An organic electroluminescence device comprising a pair of electrodes consisting of an anode and a cathode, and an organic layer disposed between the pair of electrodes and containing the polycyclic aromatic compound or a polymer thereof according to any one of items 1 to 16, the reactive compound according to item 17, the polymer compound or crosslinked polymer according to item 18, or the pendant polymer compound or crosslinked polymer according to item 19.

[0043] Section 32. Item 32. The organic electroluminescent device according to item 31, wherein the organic layer is a light-emitting layer.

[0044] Section 33. Item 33. The organic electroluminescent device according to item 32, wherein the light-emitting layer contains a host and the polycyclic aromatic compound, its multimer, reactive compound, polymer compound, crosslinked polymer, pendant polymer compound, or pendant crosslinked polymer as a dopant.

[0045] Section 34. Item 34. The organic electroluminescent device according to item 33, wherein the host is an anthracene-based compound, a fluorene-based compound, or a dibenzochrysene-based compound.

[0046] Section 35. Item 35. The organic electroluminescence device according to any one of items 32 to 34, comprising at least one of an electron transport layer and an electron injection layer disposed between the cathode and the light emitting layer, and at least one of the electron transport layer and the electron injection layer containing 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, quinolinol metal complexes, thiazole derivatives, benzothiazole derivatives, silole derivatives, and azoline derivatives.

[0047] Section 36. Item 36. The organic electroluminescence device according to item 35, wherein at least one of the electron transport layer and the electron injection layer further contains at least one selected from the group consisting of alkali metals, alkaline earth metals, rare earth metals, alkali metal oxides, alkali metal halides, alkaline earth metal oxides, alkaline earth metal halides, rare earth metal oxides, rare earth metal halides, alkali metal organic complexes, alkaline earth metal organic complexes, and rare earth metal organic complexes.

[0048] Section 37. Item 37. The organic electroluminescence device according to any one of items 31 to 36, wherein at least one layer of the hole injection layer, the hole transport layer, the light-emitting layer, the electron transport layer and the electron injection layer comprises a polymer compound obtained by polymerizing a low molecular weight compound capable of forming each layer as a monomer, or a crosslinked polymer obtained by further crosslinking the polymer compound, or a pendant-type polymer compound obtained by reacting a low molecular weight compound capable of forming each layer with a main-chain polymer, or a pendant-type crosslinked polymer obtained by further crosslinking the pendant-type polymer compound.

[0049] Section 38. Item 38. A display device or lighting device comprising the organic electroluminescent device according to any one of Items 31 to 37. Effect of the Invention

[0050] According to a preferred embodiment of the present invention, it is possible to provide a novel amino-substituted polycyclic aromatic compound that can be used as a material for an organic device, such as a material for an organic electroluminescence (EL) element, and by using this amino-substituted polycyclic aromatic compound, it is possible to provide an excellent organic device, such as an organic electroluminescence (EL) element.

[0051] Specifically, the inventors have demonstrated that polycyclic aromatic compounds (basic skeleton parts) in which aromatic rings are linked by heteroatoms such as boron, phosphorus, oxygen, nitrogen, and sulfur have a large HOMO-LUMO gap (band gap Eg in a thin film) 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, making it useful as a fluorescent material for organic EL devices (including devices using thermally activated delayed fluorescence). In addition, the high triplet excitation energy (E T Materials having the above property are also useful as electron transport layers or hole transport layers in phosphorescent organic EL devices and organic EL devices that use thermally activated delayed fluorescence. 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.

[0052] In addition to these characteristics of the basic skeleton portion, the compounds of the present invention (for example, the compounds of the above-mentioned formula (1A) or formula (2A)) can have improved external quantum efficiency by introducing a specific amino group. Furthermore, in addition to the characteristics of such a basic skeleton portion, the compound of the present invention (for example, the compound of the above-mentioned formula (2B)) can improve the external quantum efficiency and device life by introducing an amino group, an Ra group, and an Rb group into specific positions.

[0053] In addition to the above characteristics, the compound of the present invention is expected to suppress concentration quenching by condensing cycloalkane, and to improve the element life and luminous efficiency. The element life and luminous efficiency are important characteristic values ​​of organic devices, and the use of the compound of the present application is expected to have an effect of improving the characteristics of the device. In addition, a decrease in melting point and sublimation temperature can be expected. This means that in sublimation purification, which is almost essential as a purification method for materials for organic devices such as organic EL elements that require high purity, purification can be performed at a relatively low temperature, so that thermal decomposition of the material can be avoided. This is also true for the vacuum deposition process, which is a powerful means for producing organic devices such as organic EL elements, and since the process can be performed at a relatively low temperature, thermal decomposition of the material can be avoided, and as a result, a high-performance organic device can be obtained. In addition, since many of the multimers of polycyclic aromatic compounds have a high sublimation temperature due to their molecular weight and high planarity, the decrease in sublimation temperature by condensing cycloalkane is more effective. In addition, since the solubility in organic solvents is improved by condensation of cycloalkane, it becomes possible to apply it to the production of elements using a coating process. However, the present invention is not particularly limited to these principles. [Brief description of the drawings]

[0054] [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

[0055] 1. Amino-substituted 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). [ka] (In the above formula (1), ring A, ring B and ring C are each independently an aryl ring or a heteroaryl ring, and at least one hydrogen atom in these rings may be substituted; At least one hydrogen atom in at least one of the rings B and C is substituted with a group represented by the above formula (Am), 1 and Ar 2 are each independently an aryl or heteroaryl, in which at least one hydrogen atom is optionally substituted; Ar 1 and Ar 2 may be bonded via a single bond or a linking group, the group represented by the above formula (Am) is substituted for hydrogen in ring B or ring C at *, Ring B and ring C may be bonded via a linking group; Y 1 is B, P, P=O, P=S, Al, Ga, As, Si-R or Ge-R, wherein R of Si-R and Ge-R is aryl, alkyl or cycloalkyl; X 1 and X 2 are independently >O, >NR, >Si(-R) 2 ,>C(-R) 2 , >S or >Se, and R of the >NR is an optionally substituted aryl (excluding an amino group as a substituent), an optionally substituted heteroaryl, an optionally substituted alkyl or an optionally substituted cycloalkyl, and the >Si(-R) 2 R is optionally substituted aryl, optionally substituted heteroaryl, optionally substituted alkyl or optionally substituted cycloalkyl, and the >C(-R) 2 R is hydrogen, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted alkyl or optionally substituted cycloalkyl, and the above-mentioned >NR, >Si(-R) 2 and >C(-R)2 R in at least one of the above may be bonded to at least one of the rings A, B and C via a linking group or a single bond; 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 -CH 2 - may be replaced by -O-, and At least one hydrogen atom in the compound or structure represented by formula (1) may be replaced with deuterium, cyano, or halogen.

[0056] The explanation of the above formula (1) can be made by referring to the explanation of the formula (1A) given later. In addition, Ar 1 and Ar 2 Regarding the "aryl" and "heteroaryl" as the above, the description of the first substituent in formula (2B) described later can be cited, and examples of the "substituents" on the aryl and heteroaryl include aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl (two aryls may be bonded via a single bond or a linking group), alkyl, cycloalkyl, alkoxy, aryloxy, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, and alkyldicycloalkylsilyl, and the details of these "substituents" can also be cited from the description of the first substituent in formula (2B) described later. In addition, Ar 1 and Ar 2 Regarding the embodiment in which R is bonded via a single bond or a linking group, see R 25 and R 26 The explanation for the case where is combined can be cited.

[0057] 1-1. Type A amino-substituted polycyclic aromatic compounds and their multimers In particular, the present invention relates to a polycyclic aromatic compound represented by the following general formula (1A) or a multimer of a polycyclic aromatic compound having a plurality of structures represented by the following general formula (1A), in which at least one hydrogen atom in at least one of the rings B and C is substituted with a group represented by the following formula (Am). Preferably, the present invention relates to a polycyclic aromatic compound represented by the following general formula (2A) or a multimer of a polycyclic aromatic compound having a plurality of structures represented by the following general formula (2A), in which R 4 ~R 11 At least one of is a group represented by the following formula (Am), and / or at least one hydrogen atom in an aryl ring or heteroaryl ring (details will be described later) formed together with ring b or ring c is substituted with a group represented by the following formula (Am). [ka] In each structural formula, "A" to "C" and "a" to "c" are symbols indicating a ring structure represented by a ring or a benzene ring, and the other symbols are the same as defined above.

[0058] In general formula (1A), 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 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. When 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 selected from the group consisting of Y 1 , X 1 and X2 It is preferable that the ring has a 5- or 6-membered ring which shares a bond with the central fused two-ring structure of general formula (1A) consisting of:

[0059] Here, the "fused bicyclic structure" refers to the Y 1 , X 1 and X 2 means a structure in which two saturated hydrocarbon rings containing the ring are fused together. In addition, the term "six-membered ring sharing a bond with the fused two-ring structure" means, for example, an a-ring (benzene ring (six-membered ring)) fused to the fused two-ring structure as shown in the above general formula (2A). In addition, the term "an aryl ring or heteroaryl ring (A-ring) has this six-membered ring" means that the A-ring is formed only from this six-membered ring, or that the A-ring is formed by further condensing other rings to this six-membered ring so as to include this six-membered ring. In other words, the term "an aryl ring or heteroaryl ring (A-ring) having a six-membered ring" means that the six-membered ring constituting all or part of the A-ring is fused to the fused two-ring structure. The same explanation applies to "B-ring (b-ring)", "C-ring (c-ring)", and "five-membered ring".

[0060] The ring A (or ring B or ring C) in the general formula (1A) is the same as the ring a and its substituent R in the general formula (2A). 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 (2A) corresponds to a structure in which "rings A to C having 6 members" are selected as rings A to C of general formula (1A). In that sense, each ring in general formula (2A) is represented by lowercase letters a to c.

[0061] In the general formula (2A), 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. Thus, the ring structure constituting the polycyclic aromatic compound represented by the general formula (2A) changes according to the mutual bonding form of the substituents in the a ring, the b ring, and the c ring, as shown in the following formulas (2A-1) and (2A-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 (1A), respectively.

[0062] [ka]

[0063] The A' ring, B' ring and C' ring in the above formula (2A-1) and formula (2A-2) are each independently a substituent R 1 ~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 fused rings formed by fusing 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 (2A-1) and (2A-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 3etc. 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.

[0064] The compounds represented by the above formula (2A-1) or formula (2A-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.

[0065] Y in general formula (1A) 1 is B, P, P=O, P=S, Al, Ga, As, Si-R or Ge-R, and R of the Si-R and Ge-R is aryl, alkyl or cycloalkyl. In the case of P=O, P=S, Si-R or Ge-R, the atom bonded to the A ring, B ring or C ring is P, Si or Ge. Y 1 is preferably B, P, P=O, P=S or Si-R, and particularly preferably B. This explanation is based on the general formula (2A) 1 But it's the same.

[0066] X in general formula (1A) 1 and X 2 are independently >O, >NR, >Si(-R) 2 ,>C(-R) 2 , >S or >Se, and R of the >NR is an optionally substituted aryl (excluding an amino group as a substituent), an optionally substituted heteroaryl, an optionally substituted alkyl or an optionally substituted cycloalkyl, and the >Si(-R) 2 R is optionally substituted aryl, optionally substituted heteroaryl, optionally substituted alkyl or optionally substituted cycloalkyl, and the >C(-R) 2R is hydrogen, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted alkyl or optionally substituted cycloalkyl, and the above >NR, >Si(-R) 2 and >C(-R) 2 R in at least one of the rings may be bonded to at least one of the rings A, B and C through a linking group or a single bond, and the linking group is -O-, -S- or -C(-R) 2 In addition, the above-mentioned "-C(-R) 2 R in "-" is hydrogen, alkyl or cycloalkyl. This explanation is based on X in general formula (2A). 1 and X 2 But it's the same.

[0067] Here, in the general formula (1A), "the above-mentioned >NR, >Si(-R) 2 and >C(-R) 2 is bonded to at least one of the rings A, B and C through a linking group or a single bond" is defined as "the above >NR, >Si(-R) 2 and >C(-R) 2 At least one of R is -O-, -S-, -C(-R) 2 - or a single bond to at least one of the ring a, ring b and ring c."

[0068] This provision is represented by the following formula (2A-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 compound having X in the benzene ring which is the b ring (or the c ring) in the general formula (2A) 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.

[0069] In addition, the above provision is based on the following formula (2A-3-2) or formula (2A-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 benzene ring that is the a ring in the general formula (2A) 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.

[0070] [ka]

[0071] The ring B and the ring C may be bonded via a linking group. Examples of the linking group include >O, >NR, and >Si(-R). 2 ,>C(-R) 2 , >S or >Se, and the above-mentioned >NR and >Si(-R) 2 R is each independently an optionally substituted aryl, an optionally substituted heteroaryl, an optionally substituted alkyl or an optionally substituted cycloalkyl, and the >C(-R) 2 R is hydrogen, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted alkyl or optionally substituted cycloalkyl. 2 and >C(-R) 2 R in at least one of the above may be bonded to at least one of the B ring and the C ring via a linking group or a single bond, and the linking group is -O-, -S- or -C(-R) 2 In addition, the above-mentioned "-C(-R) 2 R in "-" is hydrogen, alkyl or cycloalkyl. This explanation also applies to the linking group connecting the b ring and the c ring in general formula (2A).

[0072] Here, in the general formula (1A), "the above-mentioned >NR, >Si(-R) 2 and >C(-R) 2 At least one of R is a linking group (-O-, -S- or -C(-R) 2 The provision that "is bonded to at least one of the rings B and C by a single bond such as >NR, >Si(-R) 2 and >C(-R) 2 At least one of R is -O-, -S-, -C(-R) 2 - or a single bond to at least one of the rings b and c."

[0073] The details of the form in which ring B and ring C are bonded via a linking group are as described above for X 1 Or X 2 The explanation using formulas (2A-3-1), (2A-3-2) and (2A-3-3) can be cited.

[0074] In addition, the positions where the ring B and the ring C are bonded are not particularly limited. As explained in the general formula (2A), R 7 and R 8 are bonded, for example, >O, >NR, >Si(-R) 2 ,>C(-R) 2 , >S or >Se. This form is preferred. 1 and (part of) the c-ring and R 7 and R 8 The bond site of Y and a part of the b ring form a six-membered ring. 1 and one side of the benzene ring, which is the c ring, and R 7 and R 8 It can also be said that a six-membered ring is formed by the bonding site of ring b and one side of the benzene ring.

[0075] X 1 and X 2 As a linking group connecting the B ring and the C ring, specific examples include >O, >NR, >Si(-R)2 ,>C(-R) 2 In >S or >Se, >O, >NR, >C(-R) 2 or >S is preferred, >O, >NR or >C(-R) 2 is more preferred, and >O or >NR is particularly preferred.

[0076] In formula (2A), any "-C(-R)=" (where R is R in formula (2A)) in ring a, ring b, and ring c 1 ~R 11 ) may be replaced with "-N=". [ka] As shown above, for example, "-C(-R 5 In this manner, the c-ring shown as a benzene ring in formula (2A) 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.

[0077] In formula (2A), any of "-C(-R)=C(-R)-" (wherein R is R in formula (2A)) in the a ring, the b ring, and the c ring 1 ~R 11The 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 shown as a benzene ring in formula (2A), 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.

[0078] In the above explanation of formulae (2A-1), (2A-2), (2A-3-1), (2A-3-2), and (2A-3-3), ring a, ring b, and ring c are described as benzene rings. However, the same applies when ring a to ring 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).

[0079] The "aryl ring" of ring A, ring B and ring C in general formula (1A) 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.

[0080] Specific examples of the "aryl ring" include a monocyclic benzene ring, a bicyclic ...

[0081] Examples of the "heteroaryl ring" which is the ring A, ring B and ring C in general formula (1A) 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 any of the "R" defined in general formula (2A). 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.

[0082] 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, and the like. Examples of such rings include a phosphorus ring, a quinoxaline ring, a phthalazine ring, a naphthyridine ring, a purine ring, a pteridine ring, a carbazole 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 thiophene ring, a benzothiophene ring, a dibenzothiophene ring, a furazan ring, a thianthrene ring, an indolocarbazole ring, a benzoindolocarbazole ring, a benzobenzoindolocarbazole ring, and a naphthobenzofuran ring.

[0083] 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 the monovalent groups of the above-mentioned "aryl ring" or "heteroaryl ring".

[0084] 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 8 carbon atoms (branched alkyl having 3 to 8 carbon atoms) is even more preferred, an alkyl having 1 to 6 carbon atoms (branched alkyl having 3 to 6 carbon atoms) is particularly preferred, and an alkyl having 1 to 5 carbon atoms (branched alkyl having 3 to 5 carbon atoms) is most preferred.

[0085] 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.

[0086] 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 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.

[0087] 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 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.

[0088] 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, and an alkoxy having 1 to 5 carbon atoms (branched alkoxy having 3 to 5 carbon atoms) is particularly preferred.

[0089] 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, 4-methyl-2-pentyloxy, 3,3-dimethylbutoxy, 2-ethylbutoxy, n-heptyloxy, 1-methylhexyloxy, n-octyloxy, t-octyloxy, 1-methylheptyloxy, 2-ethylbutoxy, n-hexyloxy, 1-methylhexyloxy, n-octyloxy, t-octyloxy, 1-methylheptyloxy, 2-ethylbutoxy, 1-methylhexyl ... n-ethylhexyloxy, 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.

[0090] 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.

[0091] 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.

[0092] The "trialkylsilyl" refers to 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 preferably used for substitution is an alkyl having 1 to 5 carbon atoms, and specific examples thereof include methyl, ethyl, propyl, i-propyl, butyl, sec-butyl, t-butyl, and t-amyl.

[0093] Specific examples of trialkylsilyl include trimethylsilyl, triethylsilyl, tripropylsilyl, tri-i-propylsilyl, tributylsilyl, trisec-butylsilyl, tri-t-butylsilyl, tri-t-amylsilyl, ethyldimethylsilyl, propyldimethylsilyl, i-propyldimethylsilyl, butyldimethylsilyl, sec-butyldimethylsilyl, t-butyldimethylsilyl, t-amyldimethylsilyl, methyldiethylsilyl, propyldiethylsilyl, i-propyldiethylsilyl, and butyldiethylsilyl. Examples of the silyl group include butyldiethylsilyl, sec-butyldiethylsilyl, t-butyldiethylsilyl, t-amyldiethylsilyl, methyldipropylsilyl, ethyldipropylsilyl, butyldipropylsilyl, sec-butyldipropylsilyl, t-butyldipropylsilyl, t-amyldipropylsilyl, methyldi-i-propylsilyl, ethyldi-i-propylsilyl, butyldi-i-propylsilyl, sec-butyldi-i-propylsilyl, t-butyldi-i-propylsilyl, and t-amyldi-i-propylsilyl.

[0094] 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.

[0095] Specific examples of tricycloalkylsilyl include tricyclopentylsilyl and tricyclohexylsilyl.

[0096] 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.

[0097] The "aryl" in the first substituent "diarylboryl" can be quoted from the above description of the aryl. In addition, the two aryls are not bound by a single bond or a linking group (e.g., >C(-R) 2 , >O, >S or >NR), where >C(-R) 2And R in >NR is aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, alkoxy, or aryloxy (the above, first substituent), and the first substituent may be further substituted with aryl, heteroaryl, alkyl, or cycloalkyl (the above, second substituent). As specific examples of these groups, the above-mentioned explanations of aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, alkoxy, or aryloxy as the first substituent can be cited.

[0098] As explained 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 found in the above-mentioned explanation of the monovalent group of the "aryl ring" or "heteroaryl ring", and the explanation of 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.

[0099] R in general formula (2A) 1 ~R 11 The aryl, heteroaryl, aryl of diarylamino, heteroaryl of diheteroarylamino, aryl and heteroaryl of arylheteroarylamino, aryl of diarylboryl, and aryl of aryloxy in the formula (1A) include the monovalent groups of "aryl ring" or "heteroaryl ring" described in the formula (1A). 1 ~R 11 For the alkyl, cycloalkyl, alkoxy or substituted silyl in R, the explanation of "alkyl", "cycloalkyl", "alkoxy" or "substituted silyl" as the first substituent in the explanation of the above general formula (1A) can be referred to. Furthermore, the same applies to aryl, heteroaryl, alkyl or cycloalkyl as the substituent to these groups. In addition, R 1 ~R 11 When adjacent groups among these are bonded to each other to form an aryl ring or heteroaryl ring together with the a ring, the b ring or the c ring, the same applies to the heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl (the two aryls may be bonded via a single bond or a linking group), alkyl, cycloalkyl, alkoxy, aryloxy or substituted silyl that are substituents on these rings, and the aryl, heteroaryl, alkyl or cycloalkyl that are further substituents.

[0100] 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 the first substituent is preferably a group represented by the following structural formula, and more preferably, methyl, t-butyl, t-amyl, t-octyl, 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 more preferably methyl, t-butyl, t-amyl, t-octyl, 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, t-amyl, t-octyl, 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.

[0101] In the structural formulas below, "Me" represents methyl, "tBu" represents t-butyl, "tAm" represents t-amyl, "tOct" represents t-octyl, and * represents the bond position. [ka] [ka] [ka] [ka] [ka]

[0102] In the general formula (2A), any "-C(-R)=C(-R)-" (where R is R in the formula (2A) 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.

[0103] Y in general formula (1A) 1 In the above formula, R in Si-R and Ge-R is aryl, alkyl or cycloalkyl, and examples of the 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 carbon atoms (e.g., methyl, ethyl, etc.) or cycloalkyl having 5 to 10 carbon atoms (preferably cyclohexyl or adamantyl) are preferred. This explanation is based on Y in general formula (2A). 1 But it's the same.

[0104] X in general formula (1A) 1 and X 2 R of >NR in the above formula (I) and R of >NR as a linking group connecting ring B and ring C are aryl, heteroaryl, alkyl or cycloalkyl, each of which may be substituted with the second substituent described above (provided that X 1 and X 2In the above, the aryl as R of >NR is not substituted with an amino group), and at least one hydrogen atom in the aryl, heteroaryl, alkyl or cycloalkyl may be substituted with, for example, an alkyl or cycloalkyl. Examples of the aryl, heteroaryl, alkyl or cycloalkyl include the groups described above. 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, dibenzofuranyl, dibenzothiophenyl, etc.), an alkyl having 1 to 5 carbon atoms (e.g., methyl, ethyl, etc.) or a cycloalkyl having 5 to 10 carbon atoms (preferably cyclohexyl or adamantyl) is preferred, and phenyl, naphthyl, carbazolyl, dibenzofuranyl or dibenzothiophenyl is more preferred, and dibenzofuranyl or dibenzothiophenyl is even more preferred. In addition, it is particularly preferred that dibenzofuranyl or dibenzothiophenyl is substituted with a second substituent, and specifically, examples of the second substituent include t-butyl, phenyl, d5-phenyl, etc., and these substituents are preferably substituted at the para position of an oxygen atom or a sulfur atom. Such a compound includes the compound (1-3838) shown below. This explanation is based on the general formula (2A) X 1 and X 2 The same is true for the linking group connecting the b ring and the c ring. [ka]

[0105] X in general formula (1A) 1 and X 2 >Si(-R) in 2 R and >Si(-R) as a linking group connecting ring B and ring C 2R in the formula (2A) is an aryl, heteroaryl, alkyl or cycloalkyl which may be substituted with the second substituent described above, and at least one hydrogen atom in the aryl, heteroaryl, alkyl or cycloalkyl may be substituted with, for example, an alkyl or cycloalkyl. Examples of the aryl, heteroaryl, alkyl or cycloalkyl include the groups described above. 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 5 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 given for X in the formula (2A). 1 and X 2 The same is true for the linking group connecting the b ring and the c ring.

[0106] X in general formula (1A) 1 and X 2 >C(-R) in 2 R and >C(-R) as a linking group connecting ring B and ring C 2 R is hydrogen, an aryl, heteroaryl, alkyl or cycloalkyl which may be substituted with the second substituent described above, and at least one hydrogen in the aryl or heteroaryl may be substituted with, for example, an alkyl or cycloalkyl. Examples of the aryl, heteroaryl, alkyl or cycloalkyl include the groups described above. 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 5 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 given for X in general formula (2A). 1 and X 2 The same is true for the linking group connecting the b ring and the c ring.

[0107] In general formula (1A), X 1 and X 2and when the linking group connecting the b ring and the c ring is connected to at least one of the A ring, the B ring and the C ring, examples of the linking group include -O-, -S-, -C(-R) 2 - or single bond, etc., among which "-C(-R) 2 R in "-" is hydrogen, alkyl or cycloalkyl, and examples of the alkyl or cycloalkyl include the groups described above. In particular, alkyl having 1 to 5 carbon atoms (e.g., methyl, ethyl, etc.) or cycloalkyl having 5 to 10 carbon atoms (preferably cyclohexyl or adamantyl) is preferred. This explanation applies to the linking group "-C(-R)" in general formula (2A). 2 -" is also the same.

[0108] The present invention also relates to a multimer of a polycyclic aromatic compound having a plurality of unit structures represented by general formula (1A), preferably a multimer of a polycyclic aromatic compound having a plurality of unit structures represented by general formula (2A). 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.

[0109] Examples of such multimers include multimer compounds represented by the following formula (2A-4), formula (2A-4-1), formula (2A-4-2), formula (2A-5-1) to formula (2A-5-4), or formula (2A-6). The multimer compound represented by the following formula (2A-4) is a multimer compound (ring-sharing multimer) having a plurality of unit structures represented by general formula (2A) in one compound, with the benzene ring being a-ring shared, when explained by general formula (2A). The multimer compound represented by the following formula (2A-4-1) is a multimer compound (ring-sharing multimer) having two unit structures represented by general formula (2A) in one compound, with the benzene ring being a-ring shared, when explained by general formula (2A). Moreover, the multimeric compound represented by the following formula (2A-4-2) is a multimeric compound (ring-sharing multimer) having three unit structures represented by the general formula (2A) in one compound, so as to share the benzene ring, which is the a ring, when explained by the general formula (2A). Moreover, the multimeric compound represented by any one of the following formulas (2A-5-1) to (2A-5-4) is a multimeric compound (ring-sharing multimer) having a plurality of unit structures represented by the general formula (2A) in one compound, so as to share the benzene ring, which is the b ring (or c ring), when explained by the general formula (2A). Furthermore, the multimeric compound represented by the following formula (2A-6), when explained using general formula (2A), is a multimeric compound (ring-condensed multimer) having a plurality of unit structures represented by general formula (2A) in one compound, for example, by condensing a benzene ring which is the b ring (or the a ring, the c ring) of a certain unit structure with a benzene ring which is the b ring (or the a ring, the c ring) of another unit structure.

[0110] [ka]

[0111] The multimeric compound may be a multimer in which a multimerization form represented by formula (2A-4), formula (2A-4-1) or formula (2A-4-2) is combined with a multimerization form represented by any one of formulas (2A-5-1) to (2A-5-4) or formula (2A-6), a multimer in which a multimerization form represented by any one of formulas (2A-5-1) to (2A-5-4) is combined with a multimerization form represented by formula (2A-6), or a multimer in which a multimerization form represented by formula (2A-4), formula (2A-4-1) or formula (2A-4-2), a multimerization form represented by any one of formulas (2A-5-1) to (2A-5-4), and a multimerization form represented by formula (2A-6) are combined.

[0112] 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 (1A) or (2A) may be deuterium, cyano, or halogen. For example, in formula (1A), ring A, ring B, and ring C (rings A to C are aryl rings or heteroaryl rings), substituents on rings A to C, Y 1 is Si-R or Ge-R, R (=alkyl, cycloalkyl, aryl), and X 1 and X 2 >NR, >C(-R) 2 or >Si(-R) 2 In the above formula, hydrogen atoms in R (=alkyl, cycloalkyl, aryl) may be replaced by deuterium, cyano, or halogen atoms, and among these, examples include embodiments in which all or a part of hydrogen atoms in aryl or heteroaryl are replaced by deuterium, cyano, or halogen atoms. Halogen atoms are fluorine, chlorine, bromine, or iodine, preferably fluorine, chlorine, or bromine, and more preferably fluorine or chlorine.

[0113] The polycyclic aromatic compound and its multimer according to the present invention can be used as a material for an organic device. Examples of the organic device include an organic electroluminescence device, an organic field effect transistor, and an organic thin-film solar cell. In particular, in an organic electroluminescence device, Y is preferably used as a dopant material for the light-emitting layer. 1 B, X1 and X 2 Compounds where Y is >NR 1 B, X 1 >O,X 2 Compounds where Y is >NR 1 B, X 1 and X 2 As a host material of the light-emitting layer, a compound in which Y 1 B, X 1 >O,X 2 Compounds where Y is >NR 1 B, X 1 and X 2 As the electron transport material, a compound in which Y 1 B, X 1 and X 2 Compounds in which Y is >O 1 P=O, X 1 and X 2 Compounds in which is >O are preferably used.

[0114] 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 (1A) or (2A) and its multimer may be condensed with at least one cycloalkane.

[0115] For example, aryl and heteroaryl rings which are ring A, ring B, ring C, ring a, ring b and ring c, aryl groups (aryl moieties in aryl, diarylamino, arylheteroarylamino, diarylboryl or aryloxy) and heteroaryl groups (heteroaryl moieties in heteroaryl, diheteroarylamino or arylheteroarylamino) as the first and second substituents on ring A to ring C, aryl groups (similar to above) and heteroaryl groups (similar to above) as the first and second substituents on ring a to ring c, Y 1 Aryl groups as R in Si—R and Ge—R (as above), and X 1 and X 2 >NR, >Si(-R) 2 and >C(-R) 2At least one of the aryl group (similar to above) and the heteroaryl group (similar to above) as R in the formula (I) may be condensed with at least one cycloalkane.

[0116] Preferably, the aryl and heteroaryl rings 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 substituents on ring A to ring C, the aryl group (similar to above) and the heteroaryl group (similar to above) as the first substituents on ring a to ring c, and X 1 and X 2 >NR, >Si(-R) 2 and >C(-R) 2 At least one of the aryl group (similar to above) and the heteroaryl group (similar to above) as R in the formula (I) may be condensed with at least one cycloalkane.

[0117] More preferably, the rings A, B, C, a, b and c are aryl rings, the rings A to C are aryl groups (aryl group moieties in aryl or diarylamino) and heteroaryl groups (heteroaryl moieties in heteroaryl) are the first substituents, the rings A to C are aryl groups (similar to above) and heteroaryl groups (similar to above) are the first substituents, and X 1 and X 2 >NR, >Si(-R) 2 and >C(-R) 2 At least one of the aryl groups (similar to those described above) as R may be condensed with at least one cycloalkane.

[0118] More preferably, the aryl rings 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 (aryl group moiety in aryl or diarylamino), the aryl group as the first substituent on ring a to ring c (similar to the above), and X1 and X 2 >NR, >Si(-R) 2 and >C(-R) 2 At least one of the aryl groups (similar to those described above) as R may be condensed with at least one cycloalkane.

[0119] 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.

[0120] 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.

[0121] 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]

[0122] 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]

[0123] At least one -CH in the cycloalkane 2 - may be replaced by -O-, provided that multiple -CH 2 When - is replaced by -O-, the adjacent -CH 2 - cannot be replaced by -O-. For example, one or more -CH 2 Examples in which - is replaced by -O- are shown below. 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 substituting the skeletal structure of the compound when it is a phenyl group. The same applies when the condensed ring (group) is an aromatic ring or heteroaromatic ring other than a benzene ring (phenyl group), and when the condensed cycloalkane is a cycloalkane other than cyclopentane or cyclohexane. [ka]

[0124] At least one hydrogen atom in the cycloalkane may be substituted. 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, see the description of the first substituent. 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. For example, an example of a spiro structure formed in a cycloalkane condensed to one benzene ring (phenyl group) is shown below. 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 in the skeletal structure of the compound when it is a phenyl group. [ka]

[0125] Other forms of cycloalkane condensation include polycyclic aromatic compounds and multimers thereof represented by general formula (1A) or (2A) 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."

[0126] Further, specific examples include polycyclic aromatic compounds represented by general formula (2A) and R 2is 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).

[0127] An example of this is a polycyclic aromatic compound represented by the following general formula (2A-Cy), or a multimer of a polycyclic aromatic compound having a plurality of structures represented by the following general formula (2A-Cy). In the following structural formula, 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 (n cycloalkanes are condensed to a benzene ring (phenyl group) in the following structural formula), and the definition of each symbol in the structural formula is the same as that of each symbol in the general formula (2A). In addition, at least one ring of the aryl ring or heteroaryl ring formed together with the b ring, c ring, b ring or c ring is substituted with the formula (Am) described later. [ka]

[0128] 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 "2A-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 first and second substituents described above, and at least one of the rings corresponding to the b and c rings is substituted with the formula (Am) described later.

[0129] [ka]

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[0142] [ka]

[0143] In the polycyclic aromatic compound or multimer represented by the general formula (1A), at least one hydrogen atom in at least one of the rings B and C is substituted with a group represented by the following formula (Am). In addition, in the polycyclic aromatic compound or multimer represented by the general formula (2A), R 4 ~R 11 At least one of is a group represented by the following formula (Am), and / or at least one hydrogen atom in an aryl ring or heteroaryl ring formed together with ring b or ring c is substituted with a group represented by the following formula (Am). [ka]

[0144] In formula (Am), Ar 1 is biphenylyl, and Ar 2 is aryl (excluding biphenylyl) or heteroaryl, at least one hydrogen atom in the biphenylyl, aryl or heteroaryl may be substituted by alkyl or cycloalkyl, and the group represented by the above formula (Am) at * substitutes for a hydrogen atom in ring B or ring C in general formula (1A), or a hydrogen atom in an aryl ring or heteroaryl ring formed together with ring b or ring c in general formula (2A).

[0145] As for these aryl, heteroaryl, alkyl and cycloalkyl, the description of the aryl, heteroaryl, alkyl and cycloalkyl as the first substituent in the general formula (1A) can be cited.

[0146] Ar 2 Specific examples of such groups include phenyl, naphthyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl (wherein N may be substituted with an alkyl group having 1 to 5 carbon atoms, phenyl, etc.), and fluorenyl. These groups may be substituted with an alkyl group having 1 to 5 carbon atoms (e.g., methyl, ethyl, etc.) or a cycloalkyl group having 5 to 10 carbon atoms (preferably cyclohexyl or adamantyl).

[0147] The bonding position of the group represented by formula (Am) is preferably the same as R 5 and R 10 At least one position of.

[0148] More specific examples of the amino-substituted polycyclic aromatic compounds of the present invention include compounds represented by the following structural formulas: In the structural formulas, "D" represents deuterium, "Me" represents a methyl group, "tBu" represents a t-butyl group, "tAm" represents a t-amyl group, and "Hex" represents a hexyl group.

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[0335] 1-2. Type B amino-substituted polycyclic aromatic compounds and their multimers In particular, the present invention relates to a polycyclic aromatic compound represented by the following general formula (2B) or a multimer of a polycyclic aromatic compound having a plurality of structures represented by the following general formula (2B), in which an amino group is substituted at a specific position of the b ring, and an Ra group and an Rb group are substituted at specific positions of the c ring and the a ring, respectively. [ka] In the above structural formula and the following structural formulas, "a" to "e" are symbols indicating ring structures represented by benzene rings, and the other symbols are the same as defined above.

[0336] In the above formula (2B), R 21 ~R 30 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 (all of these are referred to as first substituents), and at least one hydrogen in these may be substituted with aryl, heteroaryl, alkyl, or cycloalkyl (all of these are referred to as second substituents). Details of each of these groups will be described later.

[0337] In the above formula (2B), the substituents R 21 ~R 30Adjacent groups among may be bonded to each other to form an aryl ring or a heteroaryl ring together with the d ring or the e 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 (these are the first substituents), and at least one hydrogen atom in these may be substituted with an aryl, a heteroaryl, an alkyl, or a cycloalkyl (these are the second substituents). Details of these groups and the aryl and heteroaryl rings will be described later.

[0338] In the above formula (2B), the substituent R 21 ~R 30 The aryl or heteroaryl ring formed by bonding adjacent groups among the above together with the d and e rings can also be said to be a condensed ring formed by fusing another ring structure to the d or e ring, which is a benzene ring. Examples of such a condensed ring include a naphthalene ring, a carbazole ring, an indole ring, a dibenzofuran ring, or a dibenzothiophene ring, which are formed by fusing another ring structure, a benzene ring, an indole ring, a pyrrole ring, a benzofuran ring, or a benzothiophene ring, to the d ring (or e ring). Note that the R of the d ring 25 and e-ring R 26 does not fall under the category of "adjacent groups." In other words, "adjacent groups" refers to groups that are adjacent on the same ring.

[0339] In the above formula (2B), R 25 and R 26 is bonded to >O, >NR, >Si(-R) 2 ,>C(-R) 2, >S or >Se. As a result, an amino group having a d ring and an e ring is formed as a whole by bonding the d ring and the e ring to form a heteroaryl having at least N (N derived from the amino group). 2 R are each independently 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 (these are the first substituents), in which at least one hydrogen may be substituted with 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 (these are the second substituents), and the above-mentioned >C(-R) 2 R is hydrogen, aryl having 6 to 12 carbon atoms, heteroaryl having 2 to 15 carbon atoms, alkyl having 1 to 6 carbon atoms, or cycloalkyl having 3 to 14 carbon atoms (these are referred to as the first substituent), and at least one hydrogen in these may be substituted with aryl having 6 to 12 carbon atoms, heteroaryl having 2 to 15 carbon atoms, alkyl having 1 to 6 carbon atoms, or cycloalkyl having 3 to 14 carbon atoms (these are referred to as the second substituent). Details of each of these groups will be described later.

[0340] In the above formula (2B), Ra is aryl, heteroaryl, alkyl, cycloalkyl, alkoxy, aryloxy, triarylsilyl, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, or alkyldicycloalkylsilyl (these are the first substituents), and at least one hydrogen in these may be substituted with aryl, heteroaryl, alkyl, or cycloalkyl (these are the second substituents). As the first substituent, alkyl, triarylsilyl, trialkylsilyl, and cycloalkyl are preferred, and alkyl and cycloalkyl are more preferred. As specific groups of the first substituent, adamantyl, t-butyl, and t-amyl are preferred. Details of each of these groups will be described later.

[0341] In the above formula (2B), Rb is 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 (the above are the first substituents), and at least one hydrogen in these may be substituted with aryl, heteroaryl, alkyl, or cycloalkyl (the above are the second substituents). As the first substituent, alkyl and cycloalkyl are preferred. As specific groups of the first substituent, hydrogen, methyl, adamantyl, t-butyl, and t-amyl are preferred. Details of each of these groups will be described later.

[0342] In the above formula (2B), Y 1 is B, P, P=O, P=S, Al, Ga, As, Si-R or Ge-R, and R in the Si-R and Ge-R is aryl, alkyl or cycloalkyl (these are the first substituents). Details of each of these groups will be described later. In the case of P=O, P=S, Si-R or Ge-R, the atom bonded to the a ring, the b ring or the c ring is P, Si or Ge. Y 1 is preferably B, P, P=O, P=S or Si-R, more preferably B, P, P=O or P=S, and particularly preferably B.

[0343] In the above formula (2B), X 1 and X 2 are independently >O, >NR, >Si(-R) 2 ,>C(-R) 2 , >S or >Se, and the >NR and >Si(-R) 2R are each independently 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 (these are the first substituents), in which at least one hydrogen may be substituted with 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 (these are the second substituents), and the above-mentioned >C(-R) 2 R in the formula (1) is hydrogen, 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 (these are referred to as the first substituent), and at least one hydrogen in these may be substituted with 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 (these are referred to as the second substituent). Details of each of these groups will be described later. In addition, the above-mentioned >NR and >Si(-R) 2 and >C(-R) 2 At least one of R is -O-, -S-, -C(-R) 2 or may be bonded to at least one of the ring a, ring b and ring c via a single bond, and the -C(-R) 2 R in - is alkyl having 1 to 6 carbon atoms or cycloalkyl having 3 to 14 carbon atoms (these are the first substituents). The details of each of these groups will be described later.

[0344] Here, "the above-mentioned >NR, >Si(-R) 2 and >C(-R) 2 At least one of R is -O-, -S-, -C(-R) 2 The provision that "is bonded to at least one of the ring a, ring b and ring c through a single bond" refers to X represented by the following formula (2B-3-1): 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 (2B) 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'. 1 (or X 2) to another ring. The fused ring b' (or fused ring c') formed is, for example, a phenoxazine ring, a phenothiazine ring, or an acridine ring. In addition, although the amino group and Ra group shown in formula (2B) are omitted in formula (2B-3-1), the substitution position of the amino group in the b' ring is the same as the substitution position shown in the b ring of formula (2B) present in the b' ring, and the substitution position of the Ra group in the c' ring is the same as the substitution position shown in the c ring of formula (2B) present in the c' ring.

[0345] [ka]

[0346] In addition, "the above-mentioned >NR, >Si(-R) 2 and >C(-R) 2 At least one of R is -O-, -S-, -C(-R) 2 The provision that "is bonded to at least one of the ring a, ring b and ring c through a single bond" refers to X represented by the above formula (2B-3-2) or formula (2B-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 (2B) is a benzene ring. 1 (or X 2 , or X 1 Oyo X 2 ) to another ring is condensed to form the a' ring. The condensed ring a' formed is, for example, a phenoxazine ring, a phenothiazine ring, or an acridine ring. In addition, "Am" in formula (2B-3-2) and formula (2B-3-3) means the amino group shown in formula (2B). In addition, in formula (2B-3-2) and formula (2B-3-3), the Rb group shown in formula (2B) is omitted, but the substitution position of the Rb group in the a' ring is the same as the substitution position shown in the a ring of formula (2B) present in the a' ring.

[0347] In formula (2B), any "-C(-H)=" in ring a, ring b, and ring c may be replaced with "-N=". The partial structures of each ring are shown below. "Am" in the structural formula is the amino group shown in formula (2B). [ka] [ka] [ka]

[0348] In the above formula (2B), R 21 ~R 30 Examples of the "aryl ring" formed together with ring d or ring e by bonding adjacent groups among the above include aryl rings having 9 to 30 carbon atoms, preferably aryl rings having 9 to 20 carbon atoms, more preferably aryl rings having 9 to 16 carbon atoms, further preferably aryl rings having 9 to 12 carbon atoms, and particularly preferably aryl rings having 9 to 10 carbon atoms. Since ring d or ring e 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 with a 5-membered ring, which is 9.

[0349] Specific examples of the "aryl ring" include a bicyclic ring, a bicyclic ring, a naphthalene ring, a fused bicyclic ring, a terphenyl ring (m-terphenyl, o-terphenyl, p-terphenyl), a tricyclic ring, an acenaphthylene ring, a fluorene ring, a phenalene ring, a phenanthrene ring, a fused tricyclic ring, a triphenylene ring, a pyrene ring, a naphthacene ring, a fused tetracyclic ring, a perylene ring, a pentacene ring, and the like.

[0350] In the above formula (2B), R 21 ~R 30Examples of the "heteroaryl ring" formed with the d-ring or e-ring by bonding adjacent groups among the above include heteroaryl rings having 6 to 30 carbon atoms, preferably heteroaryl rings having 6 to 25 carbon atoms, more preferably heteroaryl rings having 6 to 20 carbon atoms, even more preferably heteroaryl rings having 6 to 15 carbon atoms, and particularly preferably heteroaryl rings having 6 to 10 carbon atoms. Examples of the "heteroaryl ring" include heterocycles containing 1 to 5 heteroatoms selected from oxygen, sulfur, and nitrogen other than carbon as ring-constituting atoms. Since the d-ring or e-ring 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 ring fused with the 5-membered ring, which is 6.

[0351] Specific examples of the "heteroaryl ring" include 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 phthalazine ring, a naphthyridine ring, a carbazole ring, an acridine ring, a phenoxathiin ring, a phenoxazine ring, a phenothiazine ring, a phenazine ring, a phenazasiline ring, a benzofuran ring, an isobenzofuran ring, a dibenzofuran ring, a benzothiophene ring, a dibenzothiophene ring, a thianthrene ring, an indolocarbazole ring, a benzoindolocarbazole ring, a benzobenzoindolocarbazole ring, and a naphthobenzofuran ring.

[0352] The "aryl" (first substituent) is, for example, an aryl having 6 to 30 carbon atoms, preferably an aryl having 6 to 20 carbon atoms, more preferably an aryl having 6 to 16 carbon atoms, still more preferably an aryl having 6 to 12 carbon atoms, and particularly preferably an aryl having 6 to 10 carbon atoms.

[0353] Specific examples of aryl include phenyl, which is a monocyclic ring system, biphenylyl, which is a bicyclic ring system, naphthyl, which is a fused bicyclic ring system, terphenylyl (m-terphenylyl, o-terphenylyl, p-terphenylyl), which is a tricyclic ring system, acenaphthylenyl, fluorenyl, phenalenyl, phenanthrenyl, which are fused tricyclic ring systems, triphenylenyl, pyrenyl, and naphthacenyl, which are fused tetracyclic ring systems, and perylenyl and pentacenyl, which are fused pentacyclic ring systems.

[0354] The "heteroaryl" (first substituent) is, for example, a heteroaryl having 2 to 30 carbon atoms, preferably a heteroaryl having 2 to 25 carbon atoms, more preferably a heteroaryl having 2 to 20 carbon atoms, still more preferably a heteroaryl having 2 to 15 carbon atoms, and particularly preferably a heteroaryl having 2 to 10 carbon atoms. In addition, the heteroaryl is, for example, a heterocycle containing, as a ring-constituting atom other than carbon, 1 to 5 heteroatoms selected from oxygen, sulfur, and nitrogen.

[0355] Specific examples of heteroaryl include pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, oxadiazolyl, thiadiazolyl, triazolyl, tetrazolyl, pyrazolyl, pyridinyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, indolyl, isoindolyl, 1H-indazolyl, benzimidazolyl, benzoxazolyl, benzothiazolyl, 1H-benzotriazolyl, quinolinyl, isoquinolinyl, cinnolinyl, quinazolinyl, quinoxalinyl, phthalazinyl, naphthyridinyl, purinyl, pteridinyl, carbazolyl, Examples include acridinyl, phenoxathiinyl, phenoxazinyl, phenothiazinyl, phenazinyl, phenazasilinyl, indolizinyl, furanyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, naphthobenzofuranyl, thiophenyl, benzothiophenyl, dibenzothiophenyl, naphthobenzothiophenyl, benzophosphoryl, dibenzophosphoryl, a monovalent group of a benzophosphole oxide ring, a monovalent group of a dibenzophosphole oxide ring, furazanyl, thianthrenyl, indolocarbazolyl, benzoindolocarbazolyl, and benzobenzoindolocarbazolyl.

[0356] The aryl and heteroaryl in “diarylamino”, “diheteroarylamino”, “arylheteroarylamino” and “diarylboryl” (all of which are first substituents) can be cited from the above-mentioned explanation of “aryl” or “heteroaryl”.

[0357] In addition, the two aryls in "diarylboryl" are single bonds or linking groups (e.g., >C(-R) 2 , >O, >S or >NR), where >C(-R) 2And R in >NR is aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, alkoxy or aryloxy (the above, first substituent), and the first substituent may be further substituted with aryl, heteroaryl, alkyl or cycloalkyl (the above, second substituent). As specific examples of these groups, the above-mentioned explanation of aryl, heteroaryl, diarylamino or aryloxy as the first substituent, and the below-mentioned explanation of alkyl, cycloalkyl or alkoxy as the first substituent can be cited.

[0358] The "alkyl" (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 8 carbon atoms (branched alkyl having 3 to 8 carbon atoms) is even more preferred, an alkyl having 1 to 6 carbon atoms (branched alkyl having 3 to 6 carbon atoms) is particularly preferred, and an alkyl having 1 to 5 carbon atoms (branched alkyl having 3 to 5 carbon atoms) is most preferred.

[0359] 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.

[0360] Examples of the "cycloalkyl" (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 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.

[0361] 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 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.

[0362] Examples of the "alkoxy" (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, and an alkoxy having 1 to 5 carbon atoms (branched alkoxy having 3 to 5 carbon atoms) is particularly preferred.

[0363] 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, 4-methyl-2-pentyloxy, 3,3-dimethylbutoxy, 2-ethylbutoxy, n-heptyloxy, 1-methylhexyloxy, n-octyloxy, t-octyloxy, 1-methylheptyloxy, 2-ethylbutoxy, n-hexyloxy, 1-methylhexyloxy, n-octyloxy, t-octyloxy, 1-methylheptyloxy, 2-ethylbutoxy, 1-methylhexyl ... n-ethylhexyloxy, 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.

[0364] The aryl in "aryloxy" (first substituent) can be cited from the above explanation of "aryl".

[0365] The "triarylsilyl" (first substituent) is a group in which three hydrogen atoms in a silyl group are each independently substituted with an aryl, and the aryl can be cited from the group explained as the "aryl" in the first substituent above. The aryl preferably used for substitution is an aryl having 6 to 10 carbon atoms, specifically phenyl and naphthyl. Specific examples of triarylsilyl include triphenylsilyl, diphenylmononaphthylsilyl, monophenyldinaphthylsilyl, and trinaphthylsilyl.

[0366] The "trialkylsilyl" (first substituent) is 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. Preferred alkyl groups for substitution are alkyl groups having 1 to 5 carbon atoms, and specific examples thereof include methyl, ethyl, propyl, i-propyl, butyl, sec-butyl, t-butyl, and t-amyl.

[0367] Specific examples of trialkylsilyl include trimethylsilyl, triethylsilyl, tripropylsilyl, tri-i-propylsilyl, tributylsilyl, trisec-butylsilyl, tri-t-butylsilyl, tri-t-amylsilyl, ethyldimethylsilyl, propyldimethylsilyl, i-propyldimethylsilyl, butyldimethylsilyl, sec-butyldimethylsilyl, t-butyldimethylsilyl, t-amyldimethylsilyl, methyldiethylsilyl, propyldiethylsilyl, i-propyldiethylsilyl, and butyldiethylsilyl. Examples of the silyl group include butyldiethylsilyl, sec-butyldiethylsilyl, t-butyldiethylsilyl, t-amyldiethylsilyl, methyldipropylsilyl, ethyldipropylsilyl, butyldipropylsilyl, sec-butyldipropylsilyl, t-butyldipropylsilyl, t-amyldipropylsilyl, methyldi-i-propylsilyl, ethyldi-i-propylsilyl, butyldi-i-propylsilyl, sec-butyldi-i-propylsilyl, t-butyldi-i-propylsilyl, and t-amyldi-i-propylsilyl.

[0368] Examples of the "tricycloalkylsilyl" (first substituent) include a group in which three hydrogen atoms in a silyl group are each independently substituted with a cycloalkyl, and the cycloalkyl can be cited from the groups described as the "cycloalkyl" in the first substituent above. Preferred cycloalkyl groups for substitution are cycloalkyl groups 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.

[0369] Specific examples of tricycloalkylsilyl include tricyclopentylsilyl and tricyclohexylsilyl.

[0370] Specific examples of the "dialkylcycloalkylsilyl" (first substituent) substituted with two alkyls and one cycloalkyl, and the "alkyldicycloalkylsilyl" (first substituent) substituted with one alkyl and two cycloalkyls include silyl substituted with a group selected from the specific alkyls and cycloalkyls mentioned above.

[0371] For details of the second substituent, the explanation of the first substituent can be cited.

[0372] Specifically, the emission wavelength can be adjusted by the steric hindrance, electron donating property and electron withdrawing property of the structures of the first and second substituents, and the groups represented by the following structural formulas are preferred, and more preferred are methyl, t-butyl, t-amyl, t-octyl, 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) Preferred are amino, carbazolyl, 3,6-dimethylcarbazolyl, 3,6-di-t-butylcarbazolyl and phenoxy, and more preferred are methyl, t-butyl, t-amyl, t-octyl, 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, t-amyl, t-octyl, 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.

[0373] In the structural formulas below, "Me" represents methyl, "tBu" represents t-butyl, "tAm" represents t-amyl, "tOct" represents t-octyl, and * represents the bond position. [ka] [ka] [ka] [ka] [ka]

[0374] Y in formula (2B) 1 In the above formula, R in Si-R and Ge-R is aryl, alkyl or cycloalkyl, and is particularly preferably aryl having 6 to 10 carbon atoms (e.g., phenyl, naphthyl, etc.), alkyl having 1 to 5 carbon atoms (e.g., methyl, ethyl, etc.), or cycloalkyl having 5 to 10 carbon atoms (preferably cyclohexyl or adamantyl).

[0375] X in formula (2B) 1 and X 2 As >NR's R, as well as R 25 and R 26 R in >NR as a linking group formed by bonding is aryl, heteroaryl, alkyl, or cycloalkyl (the above, first substituents), which may be substituted with aryl, heteroaryl, alkyl, or cycloalkyl (the above, second substituents). As these (the first substituent and the second substituent), particularly, aryl having 6 to 10 carbon atoms (e.g., phenyl, naphthyl, etc.), heteroaryl having 2 to 15 carbon atoms (e.g., carbazolyl, dibenzofuranyl, dibenzothiophenyl, etc.), alkyl having 1 to 5 carbon atoms (e.g., methyl, ethyl, etc.), or cycloalkyl having 5 to 10 carbon atoms (preferably cyclohexyl or adamantyl) is preferable, phenyl, naphthyl, carbazolyl, dibenzofuranyl, or dibenzothiophenyl is more preferable, and dibenzofuranyl or dibenzothiophenyl is even more preferable. In addition, it is particularly preferable that dibenzofuranyl or dibenzothiophenyl is substituted with a second substituent. Specific examples of the second substituent include t-butyl, phenyl, d5-phenyl, etc., and these substituents are preferably substituted at the para position of the oxygen atom or sulfur atom.

[0376] X in formula (2B) 1 and X 2 >Si(-R) as 2 R, and R 25 and R 26 >Si(-R) as a linking group formed by bonding 2R is aryl, heteroaryl, alkyl or cycloalkyl (the above are first substituents), which may be substituted with aryl, heteroaryl, alkyl or cycloalkyl (the above are second substituents), and these (first and second substituents) are particularly preferably aryl having 6 to 10 carbon atoms (e.g., phenyl, naphthyl, etc.), heteroaryl having 2 to 15 carbon atoms (e.g., carbazolyl, etc.), alkyl having 1 to 5 carbon atoms (e.g., methyl, ethyl, etc.), or cycloalkyl having 5 to 10 carbon atoms (preferably cyclohexyl or adamantyl).

[0377] X in formula (2B) 1 and X 2 >C(-R) as 2 R, and R 25 and R 26 >C(-R) as a linking group formed by bonding 2 R is aryl, heteroaryl, alkyl or cycloalkyl (the above are first substituents), which may be substituted with aryl, heteroaryl, alkyl or cycloalkyl (the above are second substituents), and these (first and second substituents) are particularly preferably aryl having 6 to 10 carbon atoms (e.g., phenyl, naphthyl, etc.), heteroaryl having 2 to 15 carbon atoms (e.g., carbazolyl, etc.), alkyl having 1 to 5 carbon atoms (e.g., methyl, ethyl, etc.), or cycloalkyl having 5 to 10 carbon atoms (preferably cyclohexyl or adamantyl).

[0378] In formula (2B), X 1 and X 2 When the ring is bonded to at least one of the rings a, b and c, examples of the linking group include -O-, -S-, -C(-R) 2 - or single bond, etc., among which "-C(-R) 2 R in "-" is hydrogen, alkyl or cycloalkyl, and is particularly preferably alkyl having 1 to 5 carbon atoms (such as methyl, ethyl, etc.) or cycloalkyl having 5 to 10 carbon atoms (preferably cyclohexyl or adamantyl).

[0379] The present invention is also a multimer of a polycyclic aromatic compound having a plurality of unit structures represented by general formula (2B). 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 in which a plurality of the unit structures are contained in one compound, and may be, for example, a form in which the unit structures are bonded together by 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), or may be a form in which any ring (a ring, b ring, or c ring) contained in the unit structure is bonded together so as to be shared by a plurality of unit structures (ring-shared multimer), or may be a form in which any ring (a ring, b ring, or c ring) contained in the unit structure is bonded together so as to be condensed (ring-condensed multimer), but ring-shared multimers and ring-condensed multimers are preferred, and ring-shared multimers are more preferred.

[0380] Examples of such multimers include multimer compounds represented by the following formula (2B-4), formula (2B-4-1), or formula (2B-6). The multimer compounds represented by the following formula (2B-4) or formula (2B-4-1) are multimer compounds (ring-sharing multimers) having unit structures represented by two general formulas (2B) in one compound, with the benzene ring being the a-ring being shared when explained using general formula (2B). The multimer compounds represented by the following formula (2B-6) are multimer compounds (ring-condensed multimers) having unit structures represented by two general formulas (2B) in one compound, with the benzene ring being the a-ring of one unit structure being condensed with the benzene ring being the a-ring of another unit structure.

[0381] [ka] In addition, "Am" in the above structural formula is the amino group shown in formula (2B).

[0382] The multimeric compound may be a multimer in which the multimeric form represented by formula (2B-4) or formula (2B-4-1) is combined with the multimeric form represented by formula (2B-6).

[0383] In addition, all or a part of the hydrogen atoms in the chemical structure of the polycyclic aromatic compound represented by the general formula (2B) and its multimer may be deuterium, cyano, or halogen. For example, in the formula (2B), the rings a to e, the substituents on these rings, Y 1 R (=aryl, alkyl, cycloalkyl) when is Si-R or Ge-R, and X 1 and X 2 >NR, >C(-R) 2 or >Si(-R) 2 In the above, hydrogen in R (=aryl, heteroaryl, alkyl, cycloalkyl) may be replaced by deuterium, cyano, or halogen, and among these, an embodiment in which all or a part of hydrogen in the aryl or heteroaryl is replaced by deuterium, cyano, or halogen is exemplified. The halogen is fluorine, chlorine, bromine, or iodine, preferably fluorine, chlorine, or bromine, and more preferably fluorine or chlorine.

[0384] The polycyclic aromatic compound and its multimer according to the present invention can be used as a material for an organic device. Examples of the organic device include an organic electroluminescence device, an organic field effect transistor, and an organic thin-film solar cell. In particular, in an organic electroluminescence device, Y is preferably used as a dopant material for the light-emitting layer. 1 B, X 1 and X 2 Compounds where Y is >NR 1 B, X 1 >O,X 2 Compounds where Y is >NR 1 B, X 1 and X 2 As a host material of the light-emitting layer, a compound in which Y 1 B, X 1 >O,X 2 Compounds where Y is >NR 1 B, X 1 and X 2 As the electron transport material, a compound in which Y 1 B, X 1 and X 2Compounds in which Y is >O 1 P=O, X 1 and X 2 Compounds in which is >O are preferably used.

[0385] 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 (2B) and its multimer may be condensed with at least one cycloalkane.

[0386] For example, aryl and heteroaryl rings which are rings a to e, aryl groups (aryl moieties in aryl, diarylamino, arylheteroarylamino, diarylboryl, or aryloxy) and heteroaryl groups (heteroaryl moieties in heteroaryl, diheteroarylamino, or arylheteroarylamino) as the first and second substituents on these rings, Y 1 an aryl group as R in Si—R and Ge—R, and X 1 and X 2 >NR, >Si(-R) 2 and >C(-R) 2 At least one of the aryl and heteroaryl groups as the first and second substituents for R may be fused with at least one cycloalkane.

[0387] Preferably, the aryl and heteroaryl rings are rings a to e, and the first substituents on these rings are aryl groups (aryl, diarylamino, diarylboryl, or the aryl group moiety in aryloxy) and heteroaryl groups (heteroaryl or the heteroaryl moiety in diheteroarylamino), and X 1 and X 2 >NR, >Si(-R) 2 and >C(-R) 2 At least one of the aryl and heteroaryl groups as the first substituent for R may be fused with at least one cycloalkane.

[0388] More preferably, the aryl rings are rings a to e, and the first substituents on these rings are aryl groups (aryl groups in aryl or diarylamino) and heteroaryl groups (heteroaryl groups in heteroaryl), and X 1 and X 2 >NR, >Si(-R) 2 and >C(-R) 2 At least one of the aryl groups as the first substituent for R may be fused with at least one cycloalkane.

[0389] More preferably, the aryl rings a to e, the aryl group as the first substituent on these rings (the aryl group portion in an aryl or diarylamino), and X 1 and X 2 >NR, >Si(-R) 2 and >C(-R) 2 At least one of the aryl groups as the first substituent for R may be fused with at least one cycloalkane.

[0390] 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.

[0391] 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.

[0392] 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] In the above structural formula, "Am" is the amino group shown in formula (2B), and "Me" is a methyl group.

[0393] 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]

[0394] At least one -CH in the cycloalkane 2 - may be replaced by -O-, provided that multiple -CH 2 When - is replaced by -O-, the adjacent -CH 2 - cannot be replaced by -O-. For example, one or more -CH 2 Examples in which - is replaced by -O- are shown below. 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 substituting the skeletal structure of the compound when it is a phenyl group. The same applies when the condensed ring (group) is an aromatic ring or heteroaromatic ring other than a benzene ring (phenyl group), and when the condensed cycloalkane is a cycloalkane other than cyclopentane or cyclohexane. [ka]

[0395] 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]

[0396] Other forms of cycloalkane condensation include polycyclic aromatic compounds represented by general formula (2B) and their multimers 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."

[0397] Further, as a more specific example, there can be mentioned an example in which Rb in the polycyclic aromatic compound represented by general formula (2B) and its multimer is a diarylamino group condensed with a cycloalkane (condensed to the aryl group portion) or a carbazolyl group condensed with a cycloalkane (condensed to the benzene ring portion).

[0398] An example of this is a polycyclic aromatic compound or a multimer thereof represented by the following general formula (2B-Cy): In the structural formula below, "Am" is the amino group shown in formula (2B), "Cy" is a cycloalkane, and each n is independently 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 (2B). [ka]

[0399] Specifically, examples include compounds represented by the following formulas: In the following formulas, "Cy" represents a cycloalkane, and each n is independently 0 to the maximum number that can be condensed (however, all n's cannot be 0), preferably 0 to 2 (however, all n's cannot be 0), and 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 "2B-Cy-(11)", n cycloalkanes are condensed at any position of each benzene ring).

[0400] [ka] [ka] [ka]

[0401] The compounds represented by each structural formula may be substituted with the first and second substituents described above. It should be understood that the structural formulas shown above are also exemplified by structural formulas in which "B" in the structural formula is changed to P, P=O, P=S, Al, Ga, As, Si-R, or Ge-R. It should be understood that the structural formulas shown above are also exemplified by structural formulas in which "O" in the structural formula is changed to ">N-Ph=(Cy)n" (the "Ph=(Cy)n" is a phenyl group to which a cycloalkane may be condensed). It should be understood that the structural formulas shown above are also exemplified by structural formulas in which "B" in the structural formula is changed to P, P=O, P=S, Al, Ga, As, Si-R, or Ge-R, and "O" in the structural formula is changed to ">N-Ph=(Cy)n" (the "Ph=(Cy)n" is a phenyl group to which a cycloalkane may be condensed).

[0402] More specific examples of the amino-substituted polycyclic aromatic compounds of the present invention include compounds represented by the following structural formulas: In the structural formulas, "Me" represents a methyl group, "tBu" represents a t-butyl group, "tAm" represents a t-amyl group, and "Hex" represents a hexyl group.

[0403] [ka]

[0404] [ka]

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[0460] 1-3. Explanation common to compounds of general formula (1), type A and type B The polycyclic aromatic compound and its multimer represented by the general formula (1), formula (1A), formula (2A) or formula (2B) according to the present invention can be used as a material for organic devices, for example, a material for organic electroluminescent elements, a material for organic field effect transistors or a material for organic thin film solar cells, in the form of a polymer compound obtained by polymerizing a reactive compound substituted with a reactive substituent as a monomer (the monomer for obtaining this polymer compound has a polymerizable substituent), a crosslinked polymer obtained by further crosslinking the polymer compound (the polymer compound for obtaining this crosslinked polymer has a crosslinkable substituent), a pendant polymer compound obtained by reacting a main chain polymer with the reactive compound (the reactive compound for obtaining this pendant polymer compound has a reactive substituent), or a pendant polymer crosslinked polymer obtained by further crosslinking the pendant polymer compound (the pendant polymer compound for obtaining this pendant polymer crosslinked polymer has a crosslinkable substituent).

[0461] The reactive substituents described above (including the polymerizable substituents, the crosslinkable substituents, and the reactive substituents for obtaining a pendant polymer, hereinafter also referred to simply as "reactive substituents") are not particularly limited as long as they are substituents capable of increasing the molecular weight of the polycyclic aromatic compound or its multimer, substituents capable of further crosslinking the polymer compound thus obtained, and substituents capable of reacting as pendants with the main chain polymer, but are not particularly limited thereto, and include alkenyl groups, alkynyl groups, unsaturated cycloalkyl groups (e.g., cyclobutenyl groups), at least one -CH in the cycloalkyl group, and the like. 2 Examples include a group in which - is replaced with -O- (e.g., an epoxy group), and an unsaturated product of a condensed cycloalkane (e.g., a condensed cyclobutene), and the following structures are preferred: * in each structural formula indicates the bond position. [ka]

[0462] Each L is independently a single bond, -O-, -S-, >C=O, -OC(=O)-, an alkylene having 1 to 12 carbon atoms, an oxyalkylene having 1 to 12 carbon atoms, or a polyoxyalkylene having 1 to 12 carbon atoms. Among the above substituents, a group represented by formula (XLS-1), formula (XLS-2), formula (XLS-3), formula (XLS-9), formula (XLS-10) or formula (XLS-17) is preferred, and a group represented by formula (XLS-1), formula (XLS-3) or formula (XLS-17) is more preferred.

[0463] The uses of such polymer compounds, crosslinked polymers, pendant type polymer compounds and pendant type crosslinked polymers (hereinafter sometimes simply referred to as "polymer compounds and crosslinked polymers") will be described later in detail.

[0464] 2. Method for producing amino-substituted polycyclic aromatic compounds and their multimers The polycyclic aromatic compound and its multimer represented by the general formula (1), formula (1A), formula (2A) or formula (2B) are basically produced by first bonding the A ring (a ring) to the B ring (b ring) and the C ring (c ring) through bonding groups (X 1 Or X 2 (a) to produce an intermediate (first reaction), and then, the A ring (a ring), the B ring (b ring) and the C ring (c ring) are bonded with a bonding group (Y 1 The final product can be produced by bonding with a group containing (second reaction). In the first reaction, for example, in the case of an etherification reaction, a general reaction such as a nucleophilic substitution reaction or an Ullmann reaction can be used, and in the case of an amination reaction, a general reaction such as a Buchwald-Hartwig reaction can be used. In addition, in the second reaction, a tandem hetero Friedel-Crafts reaction (sequential aromatic electrophilic substitution reaction, the same applies below) can be used. In addition, by using a raw material substituted with a specific amino group somewhere in these reaction steps or adding a step of substitution with a specific amino group, the compound of the present invention in which a desired position is substituted with a specific amino group can be produced.

[0465] The second reaction is, as shown in the following schemes (1) and (2), a Y bond that bonds the A ring (ring a), the B ring (ring b), and the C ring (ring c). 1This is a reaction that introduces Y 1 is a boron atom, X 1 and X 2 The case where X is an oxygen atom is shown below. First, 1 and X 2 The hydrogen atom between is orthometalated with n-butyllithium, sec-butyllithium, t-butyllithium, or the like. Then, boron trichloride, boron tribromide, or the like is added to carry out lithium-boron metal exchange, and then a tandem boron-Friedel-Crafts reaction can be carried out by adding a Bronsted base such as N,N-diisopropylethylamine to obtain the target compound. In the second reaction, a Lewis acid such as aluminum trichloride may be added to promote the reaction. The symbols in the structural formulae in the following schemes (1) and (2), and the subsequent schemes (3) to (28), are defined as above.

[0466] [ka] [ka]

[0467] The above schemes (1) and (2) mainly show the method for producing the polycyclic aromatic compounds represented by the general formulas (1A) and (2A), but the multimers thereof 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.

[0468] [ka] [ka] [ka]

[0469] In the above scheme, lithium was introduced into the desired position by orthometalation. However, as in the following schemes (6) and (7), lithium can also be introduced into the desired position by introducing a bromine atom or the like into the desired position and then by halogen-metal exchange.

[0470] [ka] [ka]

[0471] In addition, in the method for producing a polymer explained in scheme (3), lithium can also be introduced into the desired position by introducing a halogen such as a bromine atom or a chlorine atom into the position where lithium is to be introduced as in the above schemes (6) and (7), and then by halogen-metal exchange (the following schemes (8), (9), and (10)).

[0472] [ka] [ka] [ka]

[0473] This method is useful because it allows the synthesis of the target compound even in cases where ortho-metallation is not possible due to the influence of substituents.

[0474] By appropriately selecting the above synthesis method and the raw materials to be used, a specific amino group can be substituted at a desired position, and a substituent can be provided at the desired position, and Y 1 is a boron atom, X 1 and X 2 It is possible to synthesize polycyclic aromatic compounds and polymers thereof in which the ring is an oxygen atom.

[0475] Next, as an example, Y1 is a boron atom, X 1 and X 2 The case where X is a nitrogen atom is shown in the following schemes (11) and (12). 1 and X 2 As in the case where X is an oxygen atom, first 1 and X 2 The hydrogen atom between is orthometalated with n-butyllithium or the like. Then, boron tribromide or the like is added to perform 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 compound. Here, a Lewis acid such as aluminum trichloride may be added to promote the reaction. In addition, by using a raw material substituted with a specific amino group somewhere in these reaction steps or by adding a step of substitution with a specific amino group, the compound of the present invention in which the desired position is substituted with a specific amino group can be produced.

[0476] [ka] [ka]

[0477] Also, Y 1 is a boron atom, X 1 and X 2 For the polymers in which is a nitrogen atom, lithium can also be introduced to the desired position by introducing a halogen such as a bromine atom or a chlorine atom into the position where lithium is to be introduced as in the above schemes (6) and (7), and then by halogen-metal exchange (the following schemes (13), (14), and (15)).

[0478] [ka] [ka] [ka]

[0479] Next, as an example, Y 1 is phosphorus sulfide, phosphorus oxide or phosphorus atom, and X 1 and X 2 The cases where X is an oxygen atom are shown in the following schemes (16) to (19). 1 and X 2 The hydrogen atom between the two is orthometalated with n-butyllithium or the like. Next, phosphorus trichloride and sulfur are added in that order, and finally a Lewis acid such as aluminum trichloride and a Bronsted base such as N,N-diisopropylethylamine are added to carry out the tandem phospha-Friedel-Crafts reaction to give Y. 1 A compound in which Y is a phosphorus sulfide can be obtained. In addition, by treating the obtained phosphorus sulfide compound with m-chloroperbenzoic acid (m-CPBA), Y can be obtained. 1 is a phosphorus oxide, and by treating with triethylphosphine, Y 1 In addition, by using a raw material substituted with a specific amino group somewhere in these reaction steps or by adding a step of substituting with a specific amino group, it is possible to produce the compound of the present invention in which a desired position is substituted with a specific amino group.

[0480] [ka] [ka] [ka] [ka]

[0481] Also, Y 1 is phosphorus sulfide, X 1 and X 2For the polymers in which Y is an oxygen atom, lithium can be introduced to the desired position by introducing halogens such as bromine and chlorine atoms to the desired position as in the above schemes (6) and (7), and then by halogen-metal exchange (see the following schemes (20), (21), and (22)). 1 is phosphorus sulfide, X 1 and X 2 The polymers in which Y is an oxygen atom can also be obtained by treating Y with m-chloroperbenzoic acid (m-CPBA) as shown in schemes (18) and (19). 1 is a phosphorus oxide, and by treating with triethylphosphine, Y 1 It is possible to obtain a compound in which is a phosphorus atom.

[0482] [ka] [ka] [ka]

[0483] Here, Y 1 is B, P, P=O or P=S, and X 1 and X 2 Although the examples where is O or NR are described, by changing the raw material appropriately, Y 1 is Al, Ga, As, Si-R or Ge-R, or X 1 and X 2 Compounds in which is S can also be synthesized.

[0484] Specific examples of solvents that can be used in the above reactions include t-butylbenzene and xylene.

[0485] In addition, in the general formula (2A), the substituents R 1 ~R 11Adjacent groups among the above may be bonded together to form an aryl or heteroaryl ring together with the a, b or c ring, and at least one hydrogen in the formed ring may be substituted with an aryl or heteroaryl. Thus, the polycyclic aromatic compound represented by the general formula (2A) has a ring structure that constitutes the compound, as shown in the formulas (2A-1) and (2A-2) in the following schemes (23) and (24), depending on the mutual bonding form of the substituents in the a, b and c rings. These compounds can be synthesized by applying the synthesis methods shown in the above schemes (1) to (19) to the intermediates shown in the following schemes (23) and (24). In addition, by using a raw material substituted with a specific amino group somewhere in these reaction steps or adding a step of substituting with a specific amino group, the compound of the present invention in which a desired position is substituted with a specific amino group can be produced.

[0486] [ka] [ka]

[0487] The A' ring, the B' ring and the C' ring in the above formula (2A-1) and formula (2A-2) each independently represent a substituent R 1 ~R 11 Adjacent groups in the above are bonded to form an aryl or heteroaryl ring together with the a, b, and c rings (they can also be considered condensed rings formed by condensing the a, b, or c ring with other ring structures). Although not shown in the formula, there are also compounds in which the a, b, and c rings are all changed to A', B', and C' rings.

[0488] In addition, in the general formula (2A), "the above-mentioned >NR, >Si(-R) 2 and >C(-R) 2 At least one of R is -O-, -S-, -C(-R) 2The provision that "is bonded to at least one of the ring a, ring b and ring c through a single bond" refers to X represented by formula (2A-3-1) in the following scheme (25). 1 Or X 2 Compounds having a ring structure in which X is incorporated into the fused ring B' and the fused ring C', and compounds represented by formula (2A-3-2) or formula (2A-3-3), 1 Or X 2 can be expressed as a compound having a ring structure in which is incorporated into the fused ring A'. These compounds can be synthesized by applying the synthesis methods shown in the above schemes (1) to (19) to the intermediates shown in the following scheme (25). In addition, by using a raw material substituted with a specific amino group somewhere in these reaction steps or adding a step of substituting with a specific amino group, the compound of the present invention in which a desired position is substituted with a specific amino group can be produced.

[0489] [ka]

[0490] In the above synthesis schemes (1) to (17) and (20) to (25), before adding boron trichloride, boron tribromide, etc., X 1 and X 2 In the example shown here, the hydrogen atom (or halogen atom) between the rings was ortho-metallated with butyllithium or the like to perform the tandem hetero Friedel-Crafts reaction. However, the reaction can also be carried out by adding boron trichloride, boron tribromide, or the like without ortho-metallation using butyllithium or the like.

[0491] Also, Y 1 In the case of phosphorus-based, X is as shown in the following schemes (26) and (27). 1 and X 2The hydrogen atom between (O in the following formula) is orthometalated with n-butyllithium, sec-butyllithium, t-butyllithium, or the like, and then bisdiethylaminochlorophosphine is added to carry out lithium-phosphorus metal exchange, followed by adding a Lewis acid such as aluminum trichloride to carry out a tandem phosphine Friedel-Crafts reaction to obtain the target product. This reaction method is also described in International Publication No. 2010 / 104047 (e.g., page 27). In addition, by using a raw material substituted with a specific amino group somewhere in these reaction steps or adding a step of substituting with a specific amino group, the compound of the present invention in which the desired position is substituted with a specific amino group can be produced.

[0492] [ka] [ka]

[0493] In the above schemes (26) and (27), a polymeric compound can be synthesized by using an orthometalation reagent such as butyllithium in a molar amount two or three times that of intermediate 1. In addition, a halogen such as a bromine atom or a chlorine atom is first introduced into the position where a metal such as lithium is to be introduced, and then a metal can be introduced into the desired position by halogen-metal exchange.

[0494] In addition, for compounds condensed with a cycloalkane, similarly to the introduction of an amino group described above, a compound condensed with a cycloalkane at a desired position can be produced by using a cycloalkane-condensed raw material somewhere in the reaction steps in each scheme or by adding a step of condensing a cycloalkane.

[0495] In addition, for the polycyclic aromatic compound represented by the general formula (2A-Cy), a polycyclic aromatic compound fused with a cycloalkane at a desired position can be synthesized by synthesizing a cycloalkane-condensed intermediate and cyclizing it as shown in the following scheme (28). In scheme (28), X represents a halogen or hydrogen, and the definitions of the other symbols are the same as those of the symbols in the general formula (2A).

[0496] [ka]

[0497] The intermediate before cyclization in scheme (28) can also be synthesized by the method shown in scheme (1) etc. In other words, by appropriately combining the Buchwald-Hartwig reaction, Suzuki coupling reaction, or etherification reaction by nucleophilic substitution reaction, Ullmann reaction etc., an intermediate having a desired substituent can be synthesized. In these reactions, the raw material that becomes the cycloalkane condensed precursor can also be a commercially available product.

[0498] The compound of general formula (2A-Cy) having a cycloalkane-condensed diphenylamino group can also be synthesized by the following method. That is, after introducing a cycloalkane-condensed diphenylamino group by an amination reaction such as the Buchwald-Hartwig reaction between a cycloalkane-condensed bromobenzene and a trihalogenated aniline, X 1 , X 2 When is NR, X can be used in an amination reaction such as the Buchwald-Hartwig reaction. 1 , X 2When is O, it is possible to synthesize the compound of general formula (2A-Cy) by tandem boron-Friedel-Crafts reaction using a metallation reagent such as butyllithium to convert the intermediate (M-3), a boron halide such as boron tribromide, and a Brønsted base such as diethylisopropylamine. These reactions can also be applied to other cycloalkane-fused compounds.

[0499] Examples of the ortho-metallation reagent used in the above schemes (1) to (28) include alkyllithiums such as methyllithium, n-butyllithium, sec-butyllithium, and t-butyllithium; organic alkali compounds such as lithium diisopropylamide, lithium tetramethylpiperidide, lithium hexamethyldisilazide, and potassium hexamethyldisilazide; and dispersed alkali metals such as organic solvent-dispersed Na.

[0500] In addition, the metal-Y used in the above schemes (1) to (28) 1 The metal exchange reagent for Y 1 trifluoride, Y 1 trichloride, Y 1 Tribromide of Y 1 of triiodide, etc. 1 Halide of CIPN(NEt 2 ) 2 Y etc. 1 Aminated halides of Y 1 Alkoxylated compounds of Y 1 and aryloxy compounds of the above.

[0501] The Bronsted bases used in the above schemes (1) to (28) include N,N-diisopropylethylamine, triethylamine, 2,2,6,6-tetramethylpiperidine, 1,2,2,6,6-pentamethylpiperidine, N,N-dimethylaniline, N,N-dimethyltoluidine, 2,6-lutidine, sodium tetraphenylborate, potassium tetraphenylborate, triphenylborane, tetraphenylsilane, Ar 4 BNa, Ar 4 B.K., Ar 3 B, Ar 4 Si (wherein Ar is aryl such as phenyl).

[0502] The Lewis acid used in the above schemes (1) to (28) is AlCl 3 , AlBr 3 , AlF 3 , B.F. 3 ·OEt 2 , BCl 3 , BBr 3 , GaCl 3 , GaBr 3 , InCl 3 , InBr 3 , In(OTf) 3 , SnCl 4 , SnBr 4 , AgOTf, ScCl 3 , Sc(OTf) 3 , ZnCl 2 , ZnBr 2 , Zn(OTf) 2 , MgCl 2 , MgBr 2 , Mg(OTf) 2 , LiOTf, NaOTf, KOTf, Me 3 SiOTf, Cu(OTf) 2 , CuCl 2 , Y.C.L. 3 , Y(OTf) 3 , TiCl 4 , TiBr 4 , ZrCl 4 , ZrBr 4 , FeCl 3 , FeBr 3 , CoCl3 , CoBr 3 etc.

[0503] In the above schemes (1) to (28), a Brønsted base or Lewis acid may be used to promote the tandem hetero Friedel-Crafts reaction. 1 trifluoride, Y 1 trichloride, Y 1 Tribromide of Y 1 of triiodide, etc. 1 When using halides of Y, acids such as hydrogen fluoride, hydrogen chloride, hydrogen bromide, and hydrogen iodide are generated as the aromatic electrophilic substitution reaction proceeds, so the use of a Brønsted base to capture the acid is effective. 1 Aminated halides of Y 1 When an alkoxylated compound of the above is used, since amines and alcohols are produced as the aromatic electrophilic substitution reaction proceeds, it is often not necessary to use a Brønsted base. However, since the amino and alkoxy groups have low ability to be eliminated, it is effective to use a Lewis acid that promotes their elimination.

[0504] The polycyclic aromatic compound and its multimer of the present invention also include compounds in which at least a portion of hydrogen atoms is substituted with deuterium or cyano, or compounds in which hydrogen atoms are substituted with halogens such as fluorine or chlorine. Such compounds can be synthesized in the same manner as described above by using raw materials in which desired positions are deuterated, cyanated, fluorinated or chlorinated.

[0505] The polycyclic aromatic compound represented by the general formula (2B) and its multimer can be synthesized by applying the method disclosed in, for example, International Publication No. 2015 / 102118. That is, as shown in the following scheme (29), an intermediate having an Am group (an amino group represented by the formula (2B)), an Ra group, and an Rb group is synthesized, and the intermediate is cyclized by a tandem hetero Friedel-Crafts reaction (successive aromatic electrophilic substitution reaction), thereby synthesizing the desired polycyclic aromatic compound and its multimer. In the following scheme, X represents a halogen or hydrogen, and the definitions of the other symbols are the same as those described above. [ka]

[0506] The intermediate before cyclization in the above scheme (29) can also be synthesized by the method shown in WO 2015 / 102118, etc. That is, an intermediate having a desired substituent can be synthesized by appropriately combining the Buchwald-Hartwig reaction, Suzuki coupling reaction, or etherification reaction by nucleophilic substitution reaction, Ullmann reaction, etc.

[0507] The cyclization by the tandem hetero Friedel-Crafts reaction shown in the above scheme (29) can be carried out by reacting Y 1 (boron) is introduced. First, X 1 and X 2 The hydrogen atom between Y is orthometalated with n-butyllithium, sec-butyllithium, t-butyllithium, or the like. 1 After performing lithium-boron metal exchange, a tandem boron-Friedel-Crafts reaction can be carried out by adding a Brønsted base such as N,N-diisopropylethylamine to obtain the desired product. In this case, a Lewis acid such as aluminum trichloride may be added to promote the reaction.

[0508] In addition to the method of introducing lithium into the desired position by orthometalation, lithium can also be introduced into the desired position by introducing a halogen such as a bromine atom into the position where lithium is to be introduced and then carrying out halogen-metal exchange.

[0509] The polycyclic aromatic compound and its multimer of the present invention also include compounds in which at least a portion of hydrogen atoms is substituted with deuterium or cyano, or compounds in which hydrogen atoms are substituted with halogens such as fluorine or chlorine. Such compounds can be synthesized in the same manner as described above by using raw materials in which desired positions are deuterated, cyanated, fluorinated or chlorinated.

[0510] In addition, in the synthesis of the polycyclic aromatic compound of formula (2B) and its multimer, the explanation of the synthesis method of the compound of formula (1A) or formula (2A) described above can be referred to as appropriate.

[0511] 3. Organic Devices The amino-substituted polycyclic aromatic compound according to the present invention can be used as a material for an organic device, such as an organic electroluminescent device, an organic field effect transistor, or an organic thin-film solar cell.

[0512] 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.

[0513] <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.

[0514] 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.

[0515] 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.

[0516] 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".

[0517] <Substrate for organic electroluminescent device> The substrate 101 is a support for the organic EL element 100, and is usually made of quartz, glass, metal, plastic, or the like. The substrate 101 is formed into a plate, 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 non-alkali glass is used, and the thickness is sufficient to maintain mechanical strength, and may be, for example, 0.2 mm or more. The upper limit of the thickness is, for example, 2 mm or less, and preferably 1 mm or less. As for the material of the glass, it is preferable to use non-alkali glass because less ions are eluted from the glass, but SiO 2 Soda lime glass coated with a barrier coat such as a silicon oxide film is commercially available and can be used. In order to improve the gas barrier properties, a gas barrier film such as a dense silicon oxide film may be provided on at least one side of the substrate 101. In particular, when a synthetic resin plate, film, or sheet with low gas barrier properties is used as the substrate 101, it is preferable to provide a gas barrier film.

[0518] <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.

[0519] 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.

[0520] 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.

[0521] <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.

[0522] 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.

[0523] 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, N 4 ,N 4’ -Diphenyl-N 4 ,N 4’ -Bis(9-phenyl-9H-carbazol-3-yl)-[1,1'-biphenyl]-4,4'-diamine, N 4 ,N 4 ,N 4’ ,N 4’-Tetra[1,1'-biphenyl]-4-yl)-[1,1'-biphenyl]-4,4'-diamine, 4,4',4"-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.

[0524] 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).

[0525] The above-mentioned hole injection layer material and hole transport layer material can be used as a hole layer material in the form of a polymer compound obtained by polymerizing a reactive compound substituted with a reactive substituent as a monomer, or a crosslinked polymer thereof, or a pendant polymer compound obtained by reacting a main chain polymer with the reactive compound, or a crosslinked pendant polymer thereof. In this case, the reactive substituent can be quoted from the explanation of the polycyclic aromatic compound represented by the above formula (1), formula (1A), formula (2A) or formula (2B). The applications of such polymer compounds and crosslinked polymers will be described in detail below.

[0526] <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 forming 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 form a stable thin film shape and exhibits strong light-emitting (fluorescence) efficiency in a solid state. In the present invention, the material for the light-emitting layer may be a host material and, for example, a polycyclic aromatic compound represented by the above formula (1), formula (1A), formula (2A) or formula (2B) as a dopant material.

[0527] 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.

[0528] 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.

[0529] 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.

[0530] 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.

[0531] <Anthracene compounds> The anthracene compound as the host is, for example, a compound represented by the following general formula (3). [ka]

[0532] 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.

[0533] 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).

[0534] 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.

[0535] Preferred embodiments of the above anthracene-based compounds are described below. The symbols in the structures below are defined as above. [ka]

[0536] 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).

[0537] 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).

[0538] 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]

[0539] 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 *.

[0540] 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.

[0541] 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.

[0542] 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.

[0543] 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.

[0544] 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.

[0545] 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.

[0546] Specific examples of the "silyl substituted with cycloalkyl having 5 to 10 carbon atoms" include tricyclopentylsilyl and tricyclohexylsilyl.

[0547] 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.

[0548] 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 *.

[0549] The group represented by formula (A) is one of the substituents that the anthracene compound represented by formula (3) can have. [ka]

[0550] 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.

[0551] 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.

[0552] 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.

[0553] 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.

[0554] 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.

[0555] 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.

[0556] 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.

[0557] 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.

[0558] 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.

[0559] 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.

[0560] Specific examples of "alkoxy" include methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, s-butoxy, t-butoxy, pentyloxy, hexyloxy, heptyloxy, octyloxy, and the like.

[0561] 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 group described as "aryl" in the above formula can be used.

[0562] 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 group described as "aryl" in the above formula can be used.

[0563] 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.

[0564] 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.

[0565] 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.

[0566] Specific examples of the "tricycloalkylsilyl" include tricyclopentylsilyl, tricyclohexylsilyl, and the like.

[0567] 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.

[0568] 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.

[0569] Specific examples of the "substituted amino" include diphenylamino, dinaphthylamino, phenylnaphthylamino, dipyridylamino, phenylpyridylamino, naphthylpyridylamino, and the like.

[0570] R 21 ~R 28 "Halogen" in the above formula includes fluorine, chlorine, bromine, and iodine.

[0571] 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".

[0572] 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.

[0573] 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]

[0574] 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).

[0575] 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.

[0576] 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.

[0577] In addition, in the structure of the group represented by formula (A), the naphthalene ring in formula (3-X1) or formula (3-X2), the single bond in formula (3-X3), 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

[0578] Examples of the group represented by formula (A) include the following groups: In the formula, Y and * are defined as above. [ka] [ka]

[0579] 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.

[0580] 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.

[0581] [ka]

[0582] [ka]

[0583] [ka]

[0584] [ka]

[0585] [ka]

[0586] [ka]

[0587] [ka]

[0588] 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.

[0589] <Fluorene-based compounds> The compound represented by the general formula (4) basically functions as a host. [ka]

[0590] 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.

[0591] 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), formula (1A), formula (2A) or formula (2B) can be cited.

[0592] 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.

[0593] 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.

[0594] These heteroaryls may be bonded to the fluorene skeleton in the above formula (4) via a linking group. That is, the fluorene skeleton and the above heteroaryls in the formula (4) 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, -OCH 2 CH 2 -, -CH 2 CH 2 O- or -OCH 2 CH 2 Examples include O-.

[0595] 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 fused ring formed by is a ring fused 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 10The 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.

[0596] 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]

[0597] 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:

[0598] 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]

[0599] 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 7 and 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:

[0600] 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.

[0601] 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]

[0602] <Dibenzochrysene compounds> The dibenzochrysene compound as the host is, for example, a compound represented by the following general formula (5). [ka]

[0603] In the above formula (5), R 1 From R 16are 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 16 adjacent 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.

[0604] 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), formula (1A), formula (2A) or formula (2B) can be cited.

[0605] 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.

[0606] 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 1 are 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.

[0607] 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 via a linking group. Examples of the linking group include phenylene, biphenylene, naphthylene, anthracenylene, methylene, ethylene, -OCH 2 CH 2 -, -CH 2 CH 2 O- or -OCH 2 CH 2 Examples include O-.

[0608] 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 15 each independently represents hydrogen, phenyl, biphenylyl, naphthyl, anthracenyl, phenanthrenyl, or a monovalent group having the structure of the above formula (5-Ar1), formula (5-Ar2), formula (5-Ar3), formula (5-Ar4), or formula (5-Ar5) (the monovalent group having the structure is phenylene, biphenylene, naphthylene, anthracenylene, methylene, ethylene, -OCH 2 CH 2 -, -CH 2 CH 2 O- or -OCH 2 CH 2 (which may be bonded to the dibenzochrysene skeleton in the above formula (5) via O-), methyl, ethyl, propyl, or butyl is preferred.

[0609] 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 above is a single bond, phenylene, biphenylene, naphthylene, anthracenylene, methylene, ethylene, -OCH 2 CH 2 -, -CH 2 CH 2 O- or -OCH 2 CH 2 a monovalent group having the structure of the above formula (5-Ar1), formula (5-Ar2), formula (5-Ar3), formula (5-Ar4) or formula (5-Ar5) via O-; 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.

[0610] 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.

[0611] 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]

[0612] [ka]

[0613] The above-mentioned light-emitting layer materials (host materials and dopant materials) can be used as light-emitting layer materials as polymer compounds obtained by polymerizing a reactive compound substituted with a reactive substituent as a monomer, or as crosslinked polymers thereof, or as pendant polymer compounds obtained by reacting a main-chain polymer with the reactive compound, or as crosslinked pendant polymers thereof. In this case, the reactive substituents can be cited from the explanation of the polycyclic aromatic compounds represented by the above formula (1), formula (1A), formula (2A) or formula (2B). The applications of such polymer compounds and crosslinked polymers will be described in detail below.

[0614] <Example of polymer host material> [ka]

[0615] In formula (SPH-1), Each MU is independently a divalent group represented by removing any two hydrogen atoms from an aromatic compound, each EC is independently a monovalent group represented by removing any one hydrogen atom from an aromatic compound, in which two hydrogen atoms in MU are replaced by EC or MU, and k is an integer from 2 to 50,000.

[0616] More specifically, Each MU is independently arylene, heteroarylene, diarylenarylamino, diarylenarylboryl, oxaborine-diyl, or azaborine-diyl; each E C is independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, or aryloxy; At least one hydrogen in MU and EC may be further substituted with aryl, heteroaryl, diarylamino, alkyl, and cycloalkyl; k is an integer from 2 to 50,000. k is preferably an integer from 20 to 50,000, and more preferably an integer from 100 to 50,000.

[0617] At least one hydrogen atom in MU and EC in formula (SPH-1) may be substituted with an alkyl group having 1 to 24 carbon atoms, a cycloalkyl group having 3 to 24 carbon atoms, a halogen atom, or a deuterium atom. 2 - is -O- or -Si(CH 3 ) 2 -, and -CH directly bonded to EC in formula (SPH-1) in the alkyl 2 Any -CH except 2 - may be substituted with an arylene having 6 to 24 carbon atoms, and any hydrogen in the alkyl may be substituted with a fluorine.

[0618] Examples of MU include a divalent group represented by removing any two hydrogen atoms from any of the following compounds: [ka]

[0619] More specifically, the divalent group may be any of the following structures: In these, MU bonds to another MU or EC at *.

[0620] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka]

[0621] Examples of EC include monovalent groups represented by any of the following structures: In these, EC is bonded to MU at *.

[0622] [ka] [ka]

[0623] From the viewpoint of solubility and coating film-forming property, the compound represented by formula (SPH-1) is preferably such that 10 to 100% of the total number of MUs (k) in the molecule have an alkyl having 1 to 24 carbon atoms, more preferably 30 to 100% of the total number of MUs (k) in the molecule have an alkyl having 1 to 18 carbon atoms (branched chain alkyl having 3 to 18 carbon atoms), and even more preferably 50 to 100% of the total number of MUs (k) in the molecule have an alkyl having 1 to 12 carbon atoms (branched chain alkyl having 3 to 12 carbon atoms). On the other hand, from the viewpoint of in-plane alignment and charge transport, it is preferable that 10 to 100% of the total number of MUs (k) in the molecule have an alkyl having 7 to 24 carbon atoms, and more preferably 30 to 100% of the total number of MUs (k) in the molecule have an alkyl having 7 to 24 carbon atoms (branched chain alkyl having 7 to 24 carbon atoms).

[0624] The applications of such polymer compounds and crosslinked polymers will be described in detail below.

[0625] <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.

[0626] 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.

[0627] The material (electron transport material) for 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 elements.

[0628] 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.

[0629] 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, pyrazole derivatives, pyridine ... Examples of the compound include quinazine derivatives, benzoquinoline derivatives (e.g., 2,2'-bis(benzo[h]quinolin-2-yl)-9,9'-spirobifluorene), imidazopyridine derivatives, borane derivatives, benzimidazole derivatives (e.g., tris(N-phenylbenzimidazol-2-yl)benzene), benzoxazole derivatives, benzothiazole derivatives, quinoline derivatives, oligopyridine derivatives such as terpyridine, bipyridine derivatives, terpyridine derivatives (e.g., 1,3-bis(4'-(2,2':6',2"-terpyridinyl))benzene), naphthyridine derivatives (e.g., bis(1-naphthyl)-4-(1,8-naphthyridin-2-yl)phenylphosphine oxide), aldazine derivatives, carbazole derivatives, indole derivatives, phosphorus oxide derivatives, and bisstyryl derivatives.

[0630] 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.

[0631] The above-mentioned materials may be used alone or in combination with different materials.

[0632] 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.

[0633] <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.

[0634] 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.

[0635] 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.

[0636] Specific examples of the borane derivative include the following compounds: [ka]

[0637] The borane derivative can be produced using known raw materials and known synthesis methods.

[0638] <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]

[0639] 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.

[0640] 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).

[0641] 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.

[0642] 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.

[0643] [ka]

[0644] 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]

[0645] 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.

[0646] 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).

[0647] 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.

[0648] 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.

[0649] 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.

[0650] 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.

[0651] 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.

[0652] 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.

[0653] 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.

[0654] Specific examples of the pyridine derivative include the following compounds: [ka]

[0655] This pyridine derivative can be produced using known raw materials and known synthesis methods.

[0656] <Fluoranthene derivatives> The fluoranthene derivative is a compound represented by, for example, the following general formula (ETM-3), and is specifically disclosed in International Publication No. 2010 / 134352. [Chemical formula]

[0657] 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 in the case of being substituted include aryl, heteroaryl, alkyl or cycloalkyl.

[0658] Specific examples of this fluoranthene derivative include, for example, the following compounds. [Chemical formula]

[0659] <BO-based derivative> The BO-based derivative is a polycyclic aromatic compound represented by, for example, 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]

[0660] 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.

[0661] 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.

[0662] In addition, at least one hydrogen in the compound or structure represented by formula (ETM-4) may be substituted with a halogen or deuterium.

[0663] 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 formula (1), formula (1A), formula (2A) or formula (2B) above can be cited.

[0664] Specific examples of the BO derivative include the following compounds: [ka]

[0665] The BO derivative can be produced using known raw materials and known synthesis methods.

[0666] <Anthracene derivatives> One of the anthracene derivatives is, for example, a compound represented by the following formula (ETM-5-1). [ka]

[0667] 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.

[0668] 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.

[0669] [ka]

[0670] 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.

[0671] R 1 ~R 4The 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.

[0672] 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.

[0673] 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.

[0674] 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.

[0675] 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.

[0676] One example of the anthracene derivative is a compound represented by the following formula (ETM-5-2). [ka]

[0677] Ar 1 are each independently a single bond, or a divalent benzene, naphthalene, anthracene, fluorene, or phenalene.

[0678] 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.

[0679] 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.

[0680] Specific examples of these anthracene derivatives include the following compounds. [ka]

[0681] These anthracene derivatives can be produced using known raw materials and known synthesis methods.

[0682] <Benzofluorene derivatives> The benzofluorene derivative is, for example, a compound represented by the following formula (ETM-6). [ka]

[0683] 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.

[0684] 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.

[0685] 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.

[0686] 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.

[0687] 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.

[0688] Specific examples of the "aryl having 6 to 30 carbon atoms" include phenyl, naphthyl, acenaphthylenyl, fluorenyl, phenalenyl, phenanthryl, triphenylenyl, pyrenyl, naphthacenyl, perylenyl, and pentacenyl.

[0689] 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.

[0690] Specific examples of the benzofluorene derivative include the following compounds: [ka]

[0691] The benzofluorene derivative can be produced using known raw materials and known synthesis methods.

[0692] <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.

[0693] The phosphine oxide derivative may be, for example, a compound represented by the following formula (ETM-7-2). [ka]

[0694] 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.

[0695] 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.

[0696] 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.

[0697] 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.

[0698] 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.

[0699] 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.

[0700] 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.

[0701] 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.

[0702] 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.

[0703] 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.

[0704] 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.

[0705] 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.

[0706] 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.

[0707] 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.

[0708] 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.

[0709] Halogen refers to fluorine, chlorine, bromine and iodine.

[0710] 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.

[0711] Furthermore, the aliphatic hydrocarbons, alicyclic hydrocarbons, aromatic hydrocarbons and heterocycles may be either unsubstituted or substituted.

[0712] 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.

[0713] 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.

[0714] Specific examples of the phosphine oxide derivative include the following compounds: [ka]

[0715] The phosphine oxide derivative can be produced using known raw materials and known synthesis methods.

[0716] <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]

[0717] 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.

[0718] 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.

[0719] 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.

[0720] 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.

[0721] 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.

[0722] The above aryl and heteroaryl may be substituted, for example, by the above aryl or heteroaryl, respectively.

[0723] Specific examples of the pyrimidine derivative include the following compounds: [ka]

[0724] The pyrimidine derivative can be produced using known raw materials and known synthesis methods.

[0725] <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]

[0726] 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.

[0727] 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.

[0728] 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.

[0729] 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.

[0730] 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.

[0731] The above aryl and heteroaryl may be substituted, for example, by the above aryl or heteroaryl, respectively.

[0732] 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.

[0733] Specific examples of the carbazole derivative include the following compounds. [ka]

[0734] The carbazole derivative can be produced using known raw materials and known synthesis methods.

[0735] <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]

[0736] 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.

[0737] 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.

[0738] 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.

[0739] 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.

[0740] 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.

[0741] The above aryl and heteroaryl may be substituted, for example, by the above aryl or heteroaryl, respectively.

[0742] Specific examples of the triazine derivative include the following compounds: [ka]

[0743] The triazine derivative can be produced using known raw materials and known synthesis methods.

[0744] <Benzimidazole derivatives> The benzimidazole derivative is, for example, a compound represented by the following formula (ETM-11). [ka]

[0745] 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]

[0746] 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.

[0747] 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.

[0748] 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]

[0749] The benzimidazole derivative can be produced using known raw materials and known synthesis methods.

[0750] <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]

[0751] 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.

[0752] 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.

[0753] At least one hydrogen atom in each of the phenanthroline derivatives may be replaced with deuterium.

[0754] R 11 ~R 18 The alkyl, cycloalkyl and aryl in the above formula (ETM-2) are R 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]

[0755] 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]

[0756] The phenanthroline derivative can be produced using known raw materials and known synthesis methods.

[0757] <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.

[0758] 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.

[0759] The quinolinol metal complex can be produced using known raw materials and known synthesis methods.

[0760] <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]

[0761] 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]

[0762] 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.

[0763] These thiazole or benzothiazole derivatives can be produced using known raw materials and known synthesis methods.

[0764] <Silole derivatives> The silole derivative is, for example, a compound represented by the following formula (ETM-15), the details of which are described in JP-A-9-194487. [ka]

[0765] X and Y are each independently alkyl, cycloalkyl, alkenyl, alkynyl, alkoxy, alkenyloxy, alkynyloxy, aryl, or heteroaryl, which may be substituted. For details of these groups, the explanations in the above formula (1), formula (1A), formula (2A), and formula (2B), and further the explanation in the above formula (ETM-7-2) can be cited. In addition, alkenyloxy and alkynyloxy are groups in which the alkyl portion of alkoxy is replaced with alkenyl or alkynyl, respectively, and for details of these alkenyls and alkynyls, the explanation in the above formula (ETM-7-2) can be cited. In addition, X and Y may be bonded to form a cycloalkyl ring (or a ring in which a part of the ring is unsaturated), and details of this cycloalkyl ring can be found in the description of cycloalkyl in the above formula (1), formula (1A), formula (2A), and formula (2B).

[0766] R 1 ~R 4are each independently hydrogen, halogen, alkyl, cycloalkyl, alkoxy, aryloxy, amino, alkylcarbonyl, arylcarbonyl, alkoxycarbonyl, aryloxycarbonyl, azo group, alkylcarbonyloxy, arylcarbonyloxy, alkoxycarbonyloxy, aryloxycarbonyloxy, sulfinyl, sulfonyl, sulfanyl, silyl, carbamoyl, aryl, heteroaryl, alkenyl, alkynyl, nitro, formyl, nitroso, formyloxy, isocyano, cyanate group, isocyanate group, thiocyanate group, isothiocyanate group, or cyano, which may be substituted with alkyl, cycloalkyl, aryl or halogen, and may form a condensed ring with an adjacent substituent.

[0767] R 1 ~R 4 For details of halogen, alkyl, cycloalkyl, alkoxy, aryloxy, amino, aryl, heteroaryl, alkenyl and alkynyl in, the explanations in the above formula (1), formula (1A), formula (2A) and formula (2B) can be cited.

[0768] R 1 ~R 4 For details of the alkyl, aryl and alkoxy in the alkylcarbonyl, arylcarbonyl, alkoxycarbonyl, aryloxycarbonyl, alkylcarbonyloxy, arylcarbonyloxy, alkoxycarbonyloxy and aryloxycarbonyloxy in the above, the explanations in the above formulas (1), (1A), (2A) and (2B) can be cited.

[0769] Examples of silyl include a silyl group and a group in which at least one of the three hydrogen atoms of the silyl group is independently substituted with an aryl, an alkyl, or a cycloalkyl, and tri-substituted silyl is preferable, such as triarylsilyl, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, and alkyldicycloalkylsilyl. For details of the aryl, alkyl, and cycloalkyl in these, the explanations in the above formula (1), formula (1A), formula (2A), and formula (2B) can be cited.

[0770] The condensed ring formed between adjacent substituents is, for example, R 1 and R 2 , R 2 and R 3 , R 3 and R 4 etc. These fused rings may contain nitrogen, oxygen, or sulfur atoms in the ring structure, and may be fused with another ring.

[0771] However, preferably, R 1 and R 4 is a phenyl group, X and Y are not alkyl or phenyl. 1 and R 4 When R is a thienyl group, X and Y are alkyl groups, R 2 and R 3 is alkyl, aryl, alkenyl or R 2 and R 3 In addition, it is preferable that R 1 and R 4 When is a silyl group, R 2 , R 3 , X and Y are not each independently hydrogen or alkyl having 1 to 6 carbon atoms. 1 and R 2 In the case of a structure in which a benzene ring is condensed, X and Y are not alkyl and phenyl.

[0772] These silole derivatives can be produced using known raw materials and known synthesis methods.

[0773] <Azoline derivatives> The azoline derivative is, for example, a compound represented by the following formula (ETM-16), the details of which are described in WO 2017 / 014226. [ka]

[0774] In formula (ETM-16), φ is an m-valent group derived from an aromatic hydrocarbon having 6 to 40 carbon atoms or an m-valent group derived from an aromatic heterocycle having 2 to 40 carbon atoms, and at least one hydrogen of φ is optionally substituted by alkyl having 1 to 6 carbon atoms, cycloalkyl having 3 to 14 carbon atoms, aryl having 6 to 18 carbon atoms, or heteroaryl having 2 to 18 carbon atoms; Y's are each independently -O-, -S- or >N-Ar, Ar is an aryl having 6 to 12 carbon atoms or a heteroaryl having 2 to 12 carbon atoms, at least one hydrogen of Ar may be substituted by an alkyl having 1 to 4 carbon atoms, a cycloalkyl having 5 to 10 carbon atoms, an aryl having 6 to 12 carbon atoms or a heteroaryl having 2 to 12 carbon atoms, R 1 ~R 5 are each independently hydrogen, alkyl having 1 to 4 carbon atoms, or cycloalkyl having 5 to 10 carbon atoms, provided that Ar in the >N-Ar and R 1 ~R 5 one of which is a site for binding to L; L is independently selected from the group consisting of a divalent group represented by the following formula (L-1) and a divalent group represented by the following formula (L-2): [ka] In formula (L-1), X 1 ~X 6 are each independently =CR 6 - or =N- and X 1 ~X 6At least two of the =CR 6 - and X 1 ~X 6 Two of =CR 6 -R in 6 is the site of binding to φ or the azoline ring, and the other =CR 6 -R in 6 is hydrogen, In formula (L-2), X 7 ~X 14 are each independently =CR 6 - or =N- and X 7 ~X 14 At least two of the =CR 6 - and X 7 ~X 14 Two of =CR 6 -R in 6 is the site of binding to φ or the azoline ring, and the other =CR 6 -R in 6 is hydrogen, at least one hydrogen atom of L may be substituted with alkyl having 1 to 4 carbon atoms, cycloalkyl having 5 to 10 carbon atoms, aryl having 6 to 10 carbon atoms, or heteroaryl having 2 to 10 carbon atoms; m is an integer of 1 to 4, and when m is an integer of 2 to 4, the groups formed by the azoline ring and L may be the same or different, and At least one hydrogen atom in the compound represented by formula (ETM-16) may be substituted with deuterium.

[0775] Specific azoline derivatives are compounds represented by the following general formula (ETM-16-1) or general formula (ETM-16-2). [ka] In formula (ETM-16-1) and formula (ETM-16-2), φ is an m-valent group derived from an aromatic hydrocarbon having 6 to 40 carbon atoms or an m-valent group derived from an aromatic heterocycle having 2 to 40 carbon atoms, and at least one hydrogen of φ is optionally substituted by alkyl having 1 to 6 carbon atoms, cycloalkyl having 3 to 14 carbon atoms, aryl having 6 to 18 carbon atoms, or heteroaryl having 2 to 18 carbon atoms; In formula (ETM-16-1), each Y is independently -O-, -S- or >N-Ar, Ar is an aryl having 6 to 12 carbon atoms or a heteroaryl having 2 to 12 carbon atoms, and at least one hydrogen of Ar is optionally substituted by an alkyl having 1 to 4 carbon atoms, a cycloalkyl having 5 to 10 carbon atoms, an aryl having 6 to 12 carbon atoms, or a heteroaryl having 2 to 12 carbon atoms; In formula (ETM-16-1), R 1 ~R 4 are each independently hydrogen, alkyl having 1 to 4 carbon atoms, or cycloalkyl having 5 to 10 carbon atoms, with the proviso that R 1 and R 2 are identical, and R 3 and R 4 are identical, In formula (ETM-16-2), R 1 ~R 5 are each independently hydrogen, alkyl having 1 to 4 carbon atoms, or cycloalkyl having 5 to 10 carbon atoms, with the proviso that R 1 and R 2 are identical, and R 3 and R 4 are identical, In formula (ETM-16-1) and formula (ETM-16-2), L is independently selected from the group consisting of a divalent group represented by the following formula (L-1) and a divalent group represented by the following formula (L-2): [ka] In formula (L-1), X 1 ~X 6 are each independently =CR 6 - or =N- and X 1 ~X 6 At least two of the =CR 6 - and X1 ~X 6 Two of =CR 6 -R in 6 is the site of binding to φ or the azoline ring, and the other =CR 6 -R in 6 is hydrogen, In formula (L-2), X 7 ~X 14 are each independently =CR 6 - or =N- and X 7 ~X 14 At least two of the =CR 6 - and X 7 ~X 14 Two of =CR 6 -R in 6 is the site of binding to φ or the azoline ring, and the other =CR 6 -R in 6 is hydrogen, at least one hydrogen atom of L may be substituted with alkyl having 1 to 4 carbon atoms, cycloalkyl having 5 to 10 carbon atoms, aryl having 6 to 10 carbon atoms, or heteroaryl having 2 to 10 carbon atoms; m is an integer of 1 to 4, and when m is an integer of 2 to 4, the groups formed by the azoline ring and L may be the same or different, and At least one hydrogen atom in the compound represented by formula (ETM-16-1) or formula (ETM-16-2) may be replaced with deuterium.

[0776] Preferably, φ is selected from the group consisting of monovalent groups represented by the following formulae (φ1-1) to (φ1-18), divalent groups represented by the following formulae (φ2-1) to (φ2-34), trivalent groups represented by the following formulae (φ3-1) to (φ3-3), and tetravalent groups represented by the following formulae (φ4-1) to (φ4-2), and at least one hydrogen of φ may be substituted with an alkyl having 1 to 6 carbon atoms, a cycloalkyl having 3 to 14 carbon atoms, an aryl having 6 to 18 carbon atoms, or a heteroaryl having 2 to 18 carbon atoms. * in the following structural formulae represents a bonding position. [ka] [ka] [ka] In the above formula, Z is >CR 2 , >N-Ar, >NL, -O- or -S-, >CR 2 R in the above formula (1) is independently an alkyl group having 1 to 4 carbon atoms, a cycloalkyl group having 5 to 10 carbon atoms, an aryl group having 6 to 12 carbon atoms, or a heteroaryl group having 2 to 12 carbon atoms, and R may be bonded to each other to form a ring; Ar in >N-Ar is an aryl group having 6 to 12 carbon atoms or a heteroaryl group having 2 to 12 carbon atoms; and L in >NL is L in the above formula (ETM-16), formula (ETM-16-1), or formula (ETM-16-2).

[0777] Preferably, L is a divalent ring group selected from the group consisting of benzene, naphthalene, pyridine, pyrazine, pyrimidine, pyridazine, triazine, quinoline, isoquinoline, naphthyridine, phthalazine, quinoxaline, quinazoline, cinnoline, and pteridine, and at least one hydrogen of L may be substituted with an alkyl group having 1 to 4 carbon atoms, a cycloalkyl group having 5 to 10 carbon atoms, an aryl group having 6 to 10 carbon atoms, or a heteroaryl group having 2 to 10 carbon atoms.

[0778] Preferably, Ar in >N-Ar as Y or Z is selected from the group consisting of phenyl, naphthyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, naphthyridinyl, phthalazinyl, quinoxalinyl, quinazolinyl, cinnolinyl, and pteridinyl, and at least one hydrogen of Ar in >N-Ar as Y may be substituted with alkyl having 1 to 4 carbon atoms, cycloalkyl having 5 to 10 carbon atoms, or aryl having 6 to 10 carbon atoms.

[0779] Preferably, R 1 ~R 4are each independently hydrogen, alkyl having 1 to 4 carbon atoms, or cycloalkyl having 5 to 10 carbon atoms, with the proviso that R 1 and R 2 are identical, and R 3 and R 4 are identical, and R 1 ~R 4 are not all hydrogen at the same time, and m is 1 or 2. When m is 2, the groups formed by the azoline ring and L are the same.

[0780] Specific examples of azoline derivatives include the following compounds: In the structural formula, "Me" represents a methyl group. [ka] [ka]

[0781] More preferably, φ is selected from the group consisting of divalent groups represented by the following ...

Claims

[Claim 1] A polycyclic aromatic compound represented by any of the following structural formulas. [Formula 1] [chemical 2] [C3] [C4] In the above structural formula, "Me" is a methyl group, "tBu" is a t-butyl group, "tAm" is a t-amyl group, "D" is a deuterium group, and "Hex" is a hexyl group.

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