Polycyclic aromatic compound

Abstract

To provide a polycyclic aromatic compound or a polymer thereof which can be used in an organic device such as an organic EL device.SOLUTION: There is provided a polycyclic aromatic compound represented by the formula (1). (Wherein, the A, B and C rings are aryl rings or heteroaryl rings which may be substituted, at least one ring selected from the group consisting of the A ring, the B ring and the C ring is a condensed ring comprising two or more rings selected from the group consisting of an aryl ring, a heteroaryl ring and a cyclopentadiene ring, Y1 is B or the like, X1 and X2 are >N-R (R is aryl or the like) or the like, A ring, B ring, C ring or the like may be condensed with a cycloalkane or the like and hydrogen in the formula (1) may be substituted with deuterium, cyano or a halogen atom.)SELECTED DRAWING: None

Description

[Technical Field]

[0001] The present invention relates to a polycyclic aromatic compound. The present invention also relates to an organic electroluminescent element, an organic field-effect transistor, an organic thin-film solar cell, a display device, and a lighting device, each using the polycyclic aromatic compound. [Background technology]

[0002] Display devices using electroluminescent light-emitting elements have been extensively studied because of their potential for power saving and thinning, and organic electroluminescent elements (sometimes referred to as "organic EL elements" or simply "elements" in this specification) made from 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 ability to emit light such as blue, one of the three primary colors of light, and organic materials that have the ability to transport charges such as holes and electrons (which have the potential to become semiconductors or superconductors), regardless of whether they are polymeric or low-molecular-weight compounds.

[0003] An organic EL device has a structure consisting of a pair of electrodes consisting of an anode and a cathode, and one or more layers containing organic compounds 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 (Patent Document 1). As hole-transporting materials, for example, triphenylamine-based compounds have been developed (Patent Document 2). As electron-transporting materials, for example, anthracene-based compounds have been developed (Patent Document 3).

[0005] Recently, improved triphenylamine derivatives have also been reported for use in organic electroluminescent devices and organic thin-film solar cells (Patent Document 4). This material, based on the already commercially available N,N'-diphenyl-N,N'-bis(3-methylphenyl)-1,1'-biphenyl-4,4'-diamine (TPD), is characterized by enhanced planarity by linking the aromatic rings that make up the triphenylamine. While this document evaluates the charge transport properties of, for example, an NO-linked compound (Compound 1 on page 63), it does not describe methods for producing materials other than NO-linked compounds. Furthermore, because different linking elements result in different electronic states for the entire compound, the properties obtainable from materials other than NO-linked compounds are not yet known. Other examples of such compounds can be found (Patent Document 5). For example, compounds with conjugated structures with large triplet exciton energy (T1) are capable of emitting phosphorescence at shorter wavelengths and are therefore useful as materials for blue-emitting layers. Furthermore, compounds with novel conjugated structures with large T1 are also desired as electron-transporting and hole-transporting materials sandwiching the emissive 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 aromatic rings in a conjugated system 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 using phosphorescent materials or thermally activated delayed fluorescent materials require high triplet excitation energy (E T ) is also required, but by connecting donor or acceptor aromatic rings or substituents 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, thereby increasing the triplet excitation energy (E THowever, 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 ) 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] Japanese Patent Application Laid-Open No. 2001-172232 [Patent Document 3] Japanese Patent Application Laid-Open No. 2005-170911 [Patent Document 4] International Publication No. 2012 / 118164 [Patent Document 5] International Publication No. 2011 / 107186 [Patent Document 6] International Publication No. 2015 / 102118 Summary of the Invention [Problem to be solved by the invention]

[0008] As mentioned 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, the development of materials made of unconventional compounds is desired. In particular, the organic EL characteristics obtained from materials other than the NO-linked compounds reported in Patent Documents 1 to 4 and methods for producing such materials are not yet known.

[0009] Furthermore, 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 emitting 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 to solve the above problems, the present inventors have found that the luminous efficiency and device life can be improved by constructing an organic EL device using, as an emitting layer material, a polycyclic aromatic compound having a structure in which a fused ring is further introduced into the polycyclic aromatic compound described in Patent Document 6. The present invention has been completed based on this finding. Specifically, the present invention has the following configuration.

[0011] <1> A polycyclic aromatic compound represented by the following formula (1), or a multimer of a polycyclic aromatic compound having a plurality of structures represented by the following formula (1). [ka] (In 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 is optionally substituted, provided that at least one ring selected from the group consisting of ring A, ring B and ring C is a fused ring composed of two or more rings selected from the group consisting of a monocyclic aryl ring, a monocyclic heteroaryl ring and a cyclopentadiene ring, and at least one hydrogen atom in this fused ring is optionally substituted; Ring B and ring C may be bonded via a single bond or a linking group; Y 1 is B, P, P═O, P═S, Al, Ga, As, Si—R, or Ge—R, wherein R in the Si—R and Ge—R is aryl, alkyl, or cycloalkyl; X 1 and X 2are each independently >O, >NR, >Si(-R)2, >C(-R)2, >S, or >Se, R of the >NR is hydrogen, an optionally substituted aryl (excluding amino as a substituent), an optionally substituted heteroaryl, an optionally substituted alkyl, or an optionally substituted cycloalkyl, R of the >Si(-R)2 is independently hydrogen, an optionally substituted aryl, an optionally substituted heteroaryl, an optionally substituted alkyl, or an optionally substituted cycloalkyl, R of the >C(-R)2 is independently hydrogen, an optionally substituted aryl, an optionally substituted heteroaryl, an optionally substituted alkyl, or an optionally substituted cycloalkyl, the two R of the >Si(-R)2 and >C(-R)2 may be bonded to each other to form a ring, and R of at least one of the >NR, >Si(-R)2, and >C(-R)2 may be bonded to at least one of the rings A, B, and C by a linking group or a single bond, At least one selected from the group consisting of aryl rings and heteroaryl rings in the compound or structure represented by formula (1) may be fused with at least one cycloalkane, at least one hydrogen in the cycloalkane may be substituted, and at least one -CH2- in the cycloalkane may be substituted with -O-; At least one hydrogen atom in the compound or structure represented by formula (1) may be substituted with deuterium, cyano, or halogen.

[0012] <2> at least one ring selected from the group consisting of ring A, ring B, and ring C is a fused ring which is a heteroaryl ring containing a sulfur atom or an oxygen atom, and at least one hydrogen atom in this fused ring is optionally substituted; <1> 2. The polycyclic aromatic compound or a multimer thereof according to claim 1.

[0013] <3> At least one ring selected from the group consisting of ring A, ring B and ring C is a ring represented by formula (BHet). <1> or <2> 2. The polycyclic aromatic compound or a multimer thereof according to claim 1. [ka]

[0014] (In formula (BHet), R a1 ~R a6 is hydrogen or a substituent, with the proviso that R a1 ~R a6 Any two or three of the adjacent ones are Y in formula (1). 1 and X 1 and / or X 2 X is >O, >S, >Se, >NR, >Si(-R)2, or >C(-R)2, and R in >NR, >Si(-R)2, or >C(-R)2 is each independently hydrogen, an optionally substituted aryl, an optionally substituted heteroaryl, an optionally substituted alkyl, or an optionally substituted cycloalkyl, and the two R in >Si(-R)2 and >C(-R)2 may be bonded to each other to form a ring.

[0015] <4> at least one ring selected from the group consisting of ring B and ring C is a ring represented by formula (BHet); In formula (BHet), R a1 ~R a6 Any two of the adjacent ones are Y in formula (1). 1 and X 1 or X 2 It becomes a combination with Other R a1 ~R a6is hydrogen, 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; In ring A and rings B and C that are not the fused rings, the substituent with which hydrogen on the aryl ring or heteroaryl ring may be substituted is one or more selected from the group consisting of 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, and substituted silyl; Rings A, B, and C are all Y 1 , X 1 , and X 2 Formula (1) comprising a 5- or 6-membered ring sharing a bond with the central fused 2-ring structure, The ring B and the ring C may be bonded via a single bond, >O, >NR, >Si(-R)2, >C(-R)2, >S or >Se, and R of the >NR and >Si(-R)2 is each independently hydrogen, aryl which may be substituted with alkyl or cycloalkyl, heteroaryl which may be substituted with alkyl or cycloalkyl, alkyl or cycloalkyl, and R of the >C(-R)2 is hydrogen, aryl which may be substituted with alkyl or cycloalkyl, alkyl or heteroaryl, alkyl or cycloalkyl optionally substituted with cycloalkyl, and R in at least one of said >NR, >Si(-R)2 and >C(-R)2 may be bonded to at least one of said ring B and ring C via -O-, -S-, -C(-R)2- or a single bond, R in said -C(-R)2- is hydrogen, alkyl or cycloalkyl, and two R in said >Si(-R)2 and >C(-R)2 may be bonded to each other to form a ring; X 1 and X 2 are each independently >O, >NR, >Si(-R)2, >C(-R)2, >S, or >Se, and R in the >NR and >Si(-R)2 is each independently hydrogen, aryl optionally substituted with alkyl or cycloalkyl, heteroaryl optionally substituted with alkyl or cycloalkyl, alkyl, or cycloalkyl, and R in the >C(-R)2 is hydrogen, aryl optionally substituted with alkyl or cycloalkyl, alkyl, or cycloalkyl. two Rs of >NR, >Si(-R)2, and >C(-R)2 may be bonded to each other to form a ring, and R in at least one of >NR, >Si(-R)2, and >C(-R)2 may be bonded to at least one of ring A, ring B, and ring C via -O-, -S-, -C(-R)2-, or a single bond, and R in -C(-R)2- is hydrogen, alkyl, or cycloalkyl; In the case of a polymer, it is a dimer or trimer having two or three structures represented by formula (1). <3> 2. The polycyclic aromatic compound or a multimer thereof according to claim 1.

[0016] <5> Contains at least one tertiary alkyl represented by the following formula (tR): <3> or <4> 2. The polycyclic aromatic compound or a multimer thereof according to claim 1. [ka] (In formula (tR), R a , R b and R c are each independently an alkyl having 1 to 24 carbon atoms, any —CH2— in the alkyl may be replaced with —O—, and * indicates the bonding position.

[0017] <6> X 1 and X 2 are all >NR, and X 1 and X 2 wherein at least one R in >NR is optionally substituted 2-biphenylyl or optionally substituted terphenyl-2′-yl; <3> ~ <5> 1. The polycyclic aromatic compound or a multimer thereof according to any one of the preceding claims. <7> At least one selected from the group consisting of an aryl ring and a heteroaryl ring in the compound or structure represented by formula (1) is fused with at least one cycloalkane, at least one hydrogen in the cycloalkane may be substituted, and at least one -CH2- in the cycloalkane may be substituted with -O-; <3> ~ <6> 1. The polycyclic aromatic compound or a multimer thereof according to any one of the preceding claims.

[0018] <8> Represented by the following formula (2), (3), (4), (5), (6), (7), (8), or (9): <1> or <2> 2. The polycyclic aromatic compound or a multimer thereof according to claim 1. [ka]

[0019] [ka]

[0020] (In equations (2), (3), (4), (5), (6), (7), (8), and (9), R 1 ~R 17 , R 21 ~R 24 , R 31 ~R 34 , and R 41 ~R 44 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, or substituted silyl, in which at least one hydrogen may be substituted with an aryl, heteroaryl, alkyl, or cycloalkyl; and R 1 ~R 3 Adjacent groups among these are bonded to each other to form ring a together with R 8 ~R 11 Adjacent groups of the b ring are bonded to each other to form R 4 ~R 7 Adjacent groups among these are bonded to each other to form ring c together with R 12 ~R 14 Adjacent groups among these are bonded to each other to form a12 ring together with R 15 ~R 17 Adjacent groups of the b15 ring are bonded to each other to form R 21 ~R 24 Adjacent groups of the c21 ring are bonded to each other to form R 31 ~R 34 Adjacent groups among these are bonded to each other to form ring b31, and R 41 ~R 44adjacent groups among these may be bonded to each other to form an aryl ring or a heteroaryl ring together with ring b41, and at least one hydrogen atom in the formed ring may be substituted with an 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, or alkyldicycloalkylsilyl, and at least one hydrogen atom in these may be substituted with an aryl, heteroaryl, alkyl, or cycloalkyl; However, in formula (2), R 1 ~R 11 At least one pair of adjacent groups is bonded to form a divalent group represented by the formula (Het), where R 4 and R 5 and R 6 and R 7 and do not simultaneously constitute a divalent group represented by the formula (Het), and R 8 and R 9 and R 10 and R 11 and do not simultaneously constitute a divalent group represented by formula (Het), and in formula (7), R 1 ~R 3 and R 9 ~R 17 at least one pair of adjacent groups is bonded to form a divalent group represented by the formula (Het), In formula (Het), R b1 and R b2 represents hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl (two aryls may be bonded via a single bond or a linking group), alkyl, cycloalkyl, alkoxy, aryloxy, or substituted silyl, in which at least one hydrogen may be substituted with an aryl, heteroaryl, alkyl, or cycloalkyl, * represents the bonding position, X's each independently represent >O, >S, >Se, >NR, >Si(-R)2, or >C(-R)2, and R in said >NR, >Si(-R)2, or >C(-R)2 each independently represents hydrogen, aryl, heteroaryl, alkyl, or cycloalkyl, and two R's in said >Si(-R)2 and >C(-R)2 may be bonded to each other to form a ring; R in Equation (2) 7 and R 8 , R in Equation (3) 8 and R 24 , or R in Eq. (5) 34 and R 24 may be bonded to form a single bond, >O, >NR, >Si(-R)2, >C(-R)2, >S, or >Se, and R in the >NR and >Si(-R)2 are each independently 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 R in the >C(-R)2 is hydrogen, an aryl having 6 to 12 carbon atoms, a heteroaryl having 2 to 15 carbon atoms, or a cycloalkyl having 3 to 14 carbon atoms. two Rs of >NR, >Si(-R)2 and >C(-R)2 may be bonded to each other to form a ring, and R in at least one of >NR, >Si(-R)2 and >C(-R)2 may be bonded to at least one of rings b, ring b31, ring c and ring c21 via -O-, -S-, -C(-R)2- or a single bond; Y 1 are each independently B, P, P═O, P═S, Al, Ga, As, Si—R, or Ge—R, and R in 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 , X 2 , X 3 , and X 4are each independently >O, >NR, >Si(-R)2, >C(-R)2, >S, or >Se, and R in the >NR and >Si(-R)2 is each independently hydrogen, an optionally substituted aryl having 6 to 12 carbon atoms, an optionally substituted heteroaryl having 2 to 15 carbon atoms, an optionally substituted alkyl having 1 to 6 carbon atoms, or an optionally substituted cycloalkyl having 3 to 14 carbon atoms, and R in the >C(-R)2 is hydrogen, an optionally substituted aryl having 6 to 12 carbon atoms, an optionally substituted heteroaryl having 2 to 15 carbon atoms, two Rs of >Si(-R)2 and >C(-R)2 may be bonded to each other to form a ring, and R in at least one of >NR, >Si(-R)2 and >C(-R)2 may be bonded to at least one of rings selected from ring a, ring b, ring c, ring a12, ring b15, a 5-membered ring fused with ring c21, a 5-membered ring fused with ring b31, and ring b41 by -O-, -S-, -C(-R)2-, or a single bond; At least one selected from the group consisting of aryl rings and heteroaryl rings in the compounds represented by formula (2), (3), (4), (5), (6), (7), (8), or (9) may be fused with at least one cycloalkane having 3 to 24 carbon atoms, at least one hydrogen atom 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 -CH2- in the cycloalkane may be substituted with -O-; At least one hydrogen atom in the compound represented by formula (2), (3), (4), (5), (6), (7), (8), or (9) may be substituted with deuterium, cyano, or halogen.

[0021] <9> R 1 ~R 17 , R 21 ~R 24 , R 31 ~R 34 , and R41 ~R 44 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, or a trialkylsilyl (wherein the alkyl is an alkyl having 1 to 6 carbon atoms); and R 1 ~R 3 Adjacent groups among these are bonded to each other to form ring a together with R 8 ~R 11 Adjacent groups of the b ring are bonded to each other to form R 4 ~R 7 Adjacent groups among these are bonded to each other to form ring c together with R 12 ~R 14 Adjacent groups among these are bonded to each other to form a12 ring together with R 15 ~R 17 Adjacent groups of the b15 ring are bonded to each other to form R 21 ~R 24 Adjacent groups of the c21 ring are bonded to each other to form R 31 ~R 34 Adjacent groups among these are bonded to form ring b31, and R 41 ~R 44 adjacent groups among these may be bonded to each other to form, together with ring b41, an aryl ring having 9 to 16 carbon atoms or a heteroaryl ring having 6 to 15 carbon atoms, and at least one hydrogen atom in the formed ring may be substituted by an aryl ring having 6 to 10 carbon atoms, an alkyl ring having 1 to 12 carbon atoms, a cycloalkyl ring having 3 to 16 carbon atoms or a trialkylsilyl ring (wherein the alkyl ring has 1 to 4 carbon atoms); In formula (Het), R b1 and R b2is hydrogen, aryl having 6 to 30 carbon atoms, heteroaryl having 2 to 30 carbon atoms, diarylamino (provided that aryl is aryl having 6 to 12 carbon atoms), diarylboryl (provided that aryl is aryl having 6 to 12 carbon atoms, and two aryls may be bonded via a single bond or a linking group), alkyl having 1 to 24 carbon atoms, cycloalkyl having 3 to 24 carbon atoms, or trialkylsilyl (provided that alkyl is alkyl having 1 to 6 carbon atoms), X's each independently represent >O, >S, >Se, >NR, >Si(-R)2, or >C(-R)2, and R in >NR, >Si(-R)2, or >C(-R)2 represents 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; R 7 and R 8 , or R 15 and R 16 may be bonded to form >O, >NR, >C(-R)2, or >S, wherein R of the >NR is an aryl having 6 to 10 carbon atoms, an alkyl having 1 to 4 carbon atoms, or a cycloalkyl having 5 to 10 carbon atoms, and R of the >C(-R)2 is hydrogen, an aryl having 6 to 10 carbon atoms, an alkyl having 1 to 4 carbon atoms, or a cycloalkyl having 5 to 10 carbon atoms; Y 1 is B, P, P═O, P═S, or Si—R, wherein R in the Si—R is an aryl having 6 to 10 carbon atoms, an alkyl having 1 to 4 carbon atoms, or a cycloalkyl having 5 to 10 carbon atoms; X 1 , X 2 , X 3 and X 4 are each independently >O, >NR, >C(-R)2, or >S, and R of the >NR is an optionally substituted aryl having 6 to 10 carbon atoms, an optionally substituted alkyl having 1 to 4 carbon atoms, or an optionally substituted cycloalkyl having 5 to 10 carbon atoms, and R of the >C(-R)2 is hydrogen, an aryl having 6 to 10 carbon atoms, an alkyl having 1 to 4 carbon atoms, or a cycloalkyl having 5 to 10 carbon atoms, At least one selected from the group consisting of aryl rings and heteroaryl rings in the compounds represented by formulae (2), (3), (4), (5), (6), (7), (8), and (9) may be condensed with at least one cycloalkane having 3 to 20 carbon atoms, and at least one hydrogen atom 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; At least one hydrogen atom in the compound represented by formula (2), (3), (4), (5), (6), (7), (8), or (9) may be substituted with deuterium, cyano, or halogen. <8> 2. The polycyclic aromatic compound or a multimer thereof according to claim 1.

[0022] <10> Contains at least one tertiary alkyl represented by the following formula (tR): <8> or <9> 2. The polycyclic aromatic compound or a multimer thereof according to claim 1. [ka] (In formula (tR), R a , R b and R c are each independently an alkyl having 1 to 24 carbon atoms, any —CH2— in the alkyl may be replaced with —O—, and * indicates the bonding position.

[0023] <11> X in equations (2), (3), (4), (5), and (6) 1 and X 2 and X in formulas (7), (8), and (9) 1 , X 2 , X 3 and X 4 are all >NR, and X 1 , X 2 , X 3 or X 4and containing at least one >NR, wherein R is optionally substituted 2-biphenylyl or optionally substituted terphenyl-2′-yl. <8> ~ <10> 1. The polycyclic aromatic compound or a multimer thereof according to any one of the preceding claims. <12> At least one selected from the group consisting of aryl rings and heteroaryl rings in the compounds represented by formula (2), (3), (4), (5), (6), (7), (8), or (9) is fused with at least one cycloalkane, at least one hydrogen in the cycloalkane is optionally substituted, and at least one -CH2- in the cycloalkane is optionally substituted with -O-; <8> ~ <11> 1. A polycyclic aromatic compound or a multimer thereof according to any one of the above items.

[0024] <13> At least one ring selected from the group consisting of ring A, ring B, and ring C is a ring represented by formula (DBHet). <1> or <2> 2. The polycyclic aromatic compound or a multimer thereof according to claim 1. [ka]

[0025] (In formula (DBHet), R a11 ~R a18 is hydrogen or a substituent, with the proviso that R a11 ~R a18 Any two or three of the adjacent ones are Y in formula (1). 1 and X 1 and / or X 2 X is >O, >S, >Se, >NR, >Si(-R)2, or >C(-R)2, and R in >NR, >Si(-R)2, or >C(-R)2 is hydrogen, an optionally substituted aryl, an optionally substituted heteroaryl, an optionally substituted alkyl, or an optionally substituted cycloalkyl, and the two Rs in >Si(-R)2 and >C(-R)2 may be bonded to each other to form a ring.

[0026] <14> At least one ring selected from the group consisting of ring B and ring C is a ring represented by formula (DBHet), and R a11 ~R a18 Any two of the adjacent ones are Y in formula (1). 1 and X 1 or X 2 It becomes a combination with In the formula (DBHet), other R a11 ~R a18 is hydrogen, 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; the substituent with which hydrogen atoms of the aryl ring or heteroaryl ring in ring A and ring B and ring C that are not the fused rings may be substituted is one or more selected from the group consisting of 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, and substituted silyl; Rings A, B, and C are all Y 1 , X 1 , and X 2 Formula (1) comprising a 5- or 6-membered ring sharing a bond with the central fused 2-ring structure, The ring B and the ring C may be bonded via a single bond, >O, >NR, >Si(-R)2, >C(-R)2, >S, or >Se, and R of the >NR and >Si(-R)2 is each independently hydrogen, aryl which may be substituted with alkyl or cycloalkyl, heteroaryl which may be substituted with alkyl or cycloalkyl, alkyl, or cycloalkyl, and R of the >C(-R)2 is hydrogen, aryl which may be substituted with alkyl or cycloalkyl, alkyl or heteroaryl, alkyl, or cycloalkyl optionally substituted with cycloalkyl, wherein two R of >Si(-R)2 and >C(-R)2 may be bonded to each other to form a ring, and R of at least one of >NR, >Si(-R)2, and >C(-R)2 may be bonded to at least one of ring B and ring C via -O-, -S-, -C(-R)2-, or a single bond, and R of -C(-R)2- is hydrogen, alkyl, or cycloalkyl; X 1 and X 2 are each independently >O, >NR, >Si(-R)2, >C(-R)2, >S, or >Se, and R in the >NR and >Si(-R)2 is each independently hydrogen, aryl optionally substituted with alkyl or cycloalkyl, heteroaryl optionally substituted with alkyl or cycloalkyl, alkyl, or cycloalkyl, and R in the >C(-R)2 is hydrogen, aryl optionally substituted with alkyl or cycloalkyl, alkyl, or cycloalkyl. two Rs of >NR, >Si(-R)2, and >C(-R)2 may be bonded to each other to form a ring, and R in at least one of >NR, >Si(-R)2, and >C(-R)2 may be bonded to at least one of ring A, ring B, and ring C via -O-, -S-, -C(-R)2-, or a single bond, and R in -C(-R)2- is hydrogen, alkyl, or cycloalkyl; In the case of a polymer, it is a dimer or trimer having two or three structures represented by formula (1). <13> 2. The polycyclic aromatic compound or a multimer thereof according to claim 1.

[0027] <15> Contains at least one tertiary alkyl represented by the following formula (tR): <13> or <14> 2. The polycyclic aromatic compound or a multimer thereof according to claim 1. [ka] (In formula (tR), R a , R b and R c are each independently an alkyl having 1 to 24 carbon atoms, any —CH2— in the alkyl may be replaced with —O—, and * indicates the bonding position.

[0028] <16> X 1 and X 2 are all >NR, and X 1 and X 2 wherein at least one R in >NR is optionally substituted 2-biphenylyl or optionally substituted terphenyl-2′-yl; <13> ~ <15> 1. The polycyclic aromatic compound or a multimer thereof according to any one of the preceding claims. <17> At least one selected from the group consisting of an aryl ring and a heteroaryl ring in the compound or structure represented by formula (1) is fused with at least one cycloalkane, at least one hydrogen in the cycloalkane may be substituted, and at least one -CH2- in the cycloalkane may be substituted with -O-; <13> ~ <16> 1. The polycyclic aromatic compound or a multimer thereof according to any one of the preceding claims.

[0029] <18> Represented by the following formula (12), (13), (14), (15), (16), (17), (18), or (19): <1> or <2> 2. The polycyclic aromatic compound or a multimer thereof according to claim 1. [ka]

[0030] [ka]

[0031] (In equations (12), (13), (14), (15), (16), (17), (18), (19), and (20), R 1 ~R 3 and R 8 ~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, alkoxy, aryloxy, tricycloalkylsilyl, dialkylcycloalkylsilyl, or alkyldicycloalkylsilyl, in which at least one hydrogen may be substituted with aryl, heteroaryl, alkyl, or cycloalkyl; R 51 ~R 58 and R 61 ~R 68 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, or substituted silyl, in which at least one hydrogen may be substituted with aryl, heteroaryl, alkyl, or cycloalkyl; R 1 ~R 3 Adjacent groups among these are bonded to each other to form ring a together with R 8 ~R 11 Adjacent groups of the b ring are bonded to each other to form R 51 ~R 54 Adjacent groups of the R 55 ~R 58 Adjacent groups of the R61 ~R 64 Adjacent groups of the b61 ring are bonded to each other to form a ring b61. 65 ~R 68 adjacent groups among these may be bonded to each other to form an aryl ring or a heteroaryl ring together with ring b65, and at least one hydrogen atom in the formed ring may be substituted with an aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl (two aryls may be bonded via a single bond or a linking group), alkyl, cycloalkyl, alkoxy, aryloxy, or substituted silyl; X's each independently represent >O, >S, >Se, >NR, >Si(-R)2, or >C(-R)2, and R in said >NR, >Si(-R)2, or >C(-R)2 each independently represents hydrogen, aryl, heteroaryl, alkyl, or cycloalkyl, and two R in said >Si(-R)2 and >C(-R)2 may be bonded to each other to form a ring; Y 1 are each independently B, P, P═O, P═S, Al, Ga, As, Si—R, or Ge—R, and R in 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 2are each independently >O, >NR, >Si(-R)2, >C(-R)2, >S, or >Se, and R in the >NR and >Si(-R)2 is each independently hydrogen, an optionally substituted aryl having 6 to 12 carbon atoms, an optionally substituted heteroaryl having 2 to 15 carbon atoms, an optionally substituted alkyl having 1 to 6 carbon atoms, or an optionally substituted cycloalkyl having 3 to 14 carbon atoms, and R in the >C(-R)2 is hydrogen, an optionally substituted aryl having 6 to 12 carbon atoms, a substituted the two Rs of >Si(-R)2 and >C(-R)2 may be bonded to each other to form a ring, and R in at least one of >NR, >Si(-R)2 and >C(-R)2 may be bonded to at least one of ring a, ring b, ring c51 and ring b61 via -O-, -S-, -C(-R)2- or a single bond; At least one selected from the group consisting of aryl rings and heteroaryl rings in the compound represented by formula (12), (13), (14), (15), (16), (17), (18), (19), or (20) may be fused 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 -CH2- in the cycloalkane may be substituted with -O-; At least one hydrogen atom in the compounds represented by formulas (12), (13), (14), (15), (16), (17), (18), (19), and (20) may be substituted with deuterium, cyano, or halogen. <19> R 1 ~R 3 and R 8 ~R 11are each independently hydrogen, an aryl having 6 to 30 carbon atoms, a heteroaryl having 2 to 30 carbon atoms, a diarylamino (wherein the aryl is an aryl having 6 to 12 carbon atoms), a diarylboryl (wherein the aryl is an aryl having 6 to 12 carbon atoms, and the two aryls may be bonded via a single bond or a linking group), or an alkyl having 1 to 24 carbon atoms; R 51 ~R 58 and R 61 ~R 68 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, or a trialkylsilyl (wherein the alkyl is an alkyl having 1 to 6 carbon atoms); R 1 ~R 3 Adjacent groups among these are bonded to each other to form ring a together with R 8 ~R 11 Adjacent groups of the b ring are bonded to each other to form R 51 ~R 54 Adjacent groups of the R 55 ~R 58 Adjacent groups of the R 61 ~R 64 Adjacent groups of the b61 ring are bonded to each other to form a ring b61. 65 ~R 68 adjacent groups among these may be bonded to each other to form, together with ring b65, an aryl ring having 9 to 16 carbon atoms or a heteroaryl ring having 6 to 15 carbon atoms, and at least one hydrogen atom in the formed ring may be substituted with an aryl group having 6 to 10 carbon atoms, an alkyl group having 1 to 12 carbon atoms, or a cycloalkyl or trialkylsilyl group having 3 to 16 carbon atoms (wherein the alkyl group is an alkyl group having 1 to 4 carbon atoms); X's each independently represent >O, >S, >Se, >NR, >Si(-R)2, or >C(-R)2, and R in the >NR, >Si(-R)2, or >C(-R)2 represents 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; Y 1 is B, P, P═O, P═S or Si—R, wherein R in the Si—R is an aryl having 6 to 10 carbon atoms, an alkyl having 1 to 4 carbon atoms, or a cycloalkyl having 5 to 10 carbon atoms; X 1 and X 2 are each independently >O, >NR, >C(-R)2, or >S, and R of the >NR is an optionally substituted aryl having 6 to 10 carbon atoms, an optionally substituted alkyl having 1 to 4 carbon atoms, or an optionally substituted cycloalkyl having 5 to 10 carbon atoms, and R of the >C(-R)2 is hydrogen, an aryl having 6 to 10 carbon atoms, an alkyl having 1 to 4 carbon atoms, or a cycloalkyl having 5 to 10 carbon atoms, At least one selected from the group consisting of aryl rings and heteroaryl rings in the compounds represented by formulae (12), (13), (14), (15), (16), (17), (18), (19), and (20) may be condensed with at least one cycloalkane having 3 to 20 carbon atoms, and at least one hydrogen atom 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; At least one hydrogen atom in the compound represented by formula (12), (13), (14), (15), (16), (17), (18), (19), or (20) may be substituted with deuterium, cyano, or halogen. <18> 2. The polycyclic aromatic compound or a multimer thereof according to claim 1.

[0032] <20> Contains at least one tertiary alkyl represented by the following formula (tR): <18> or <19> 2. The polycyclic aromatic compound or a multimer thereof according to claim 1. [ka] (In formula (tR), R a , R b and R c are each independently an alkyl having 1 to 24 carbon atoms, any —CH2— in the alkyl may be replaced with —O—, and * indicates the bonding position.

[0033] <21> X 1 and X 2 are all >NR, and X 1 and X 2 wherein at least one R in >NR is optionally substituted 2-biphenylyl or optionally substituted terphenyl-2′-yl; <18> ~ <20> 1. The polycyclic aromatic compound or a multimer thereof according to any one of the preceding claims. <22> At least one selected from the group consisting of aryl rings and heteroaryl rings in the compound represented by formula (12), (13), (14), (15), (16), (17), (18), or (19) is fused with at least one cycloalkane, at least one hydrogen in the cycloalkane is optionally substituted, and at least one -CH2- in the cycloalkane is optionally substituted with -O-; <18> ~ <21> 1. The polycyclic aromatic compound or a multimer thereof according to any one of the preceding claims. <23> Ring A is a pyridine ring, a pyrimidine ring, a pyridazine ring, or a 1,2,3-triazine ring. <1> ~ <7> and <13> ~ <17> 1. The polycyclic aromatic compound or a multimer thereof according to any one of the preceding claims. <24> Y 1 is B <1> ~ <23> 1. The polycyclic aromatic compound or a multimer thereof according to any one of the preceding claims.

[0034] <25> X 1 , X 2 , X 3 or X 4 and at least one >NR, where R is one of the following groups: <1> ~ <24> 1. The polycyclic aromatic compound or a multimer thereof according to any one of the preceding claims. [ka] (Me is methyl, tBu is t-butyl, * indicates the bond position.)

[0035] <26> The halogen is fluorine. <1> ~ <25> 1. The polycyclic aromatic compound or a multimer thereof according to any one of the preceding claims.

[0036] <27> Represented by any of the following structural formulas: <1> 2. The polycyclic aromatic compound or a multimer thereof according to claim 1. [ka]

[0037] [ka]

[0038] [ka]

[0039] [ka]

[0040] [ka]

[0041] [ka]

[0042] [ka]

[0043] [ka]

[0044] [ka] (In the above structural formula, "D" represents deuterium, "Me" represents methyl, "tBu" represents t-butyl, and "tAm" represents t-amyl.)

[0045] <28> Represented by any of the following structural formulas: <1> 2. The polycyclic aromatic compound or a multimer thereof according to claim 1. [ka]

[0046] [ka]

[0047] [ka] (In the above structural formula, "Me" represents methyl and "tBu" represents t-butyl.)

[0048] <29> Represented by any of the following structural formulas: <1> 2. The polycyclic aromatic compound or a multimer thereof according to claim 1. [ka]

[0049] <30> <1> ~ <29> 1. A reactive compound in which the polycyclic aromatic compound or a multimer thereof according to any one of the above items is substituted with a reactive substituent. <31> <30> A polymer compound obtained by polymerizing the reactive compound described in the above as a monomer, or a crosslinked polymer obtained by further crosslinking the polymer compound. <32> Main chain polymer <30> or a pendant-type crosslinked polymer obtained by further crosslinking the pendant-type polymer compound. <33> <1> ~ <29> 10. A material for an organic device, comprising the polycyclic aromatic compound or a multimer thereof according to any one of claims 1 to 9. <34> <30> A material for an organic device, comprising the reactive compound according to claim 1. <35> <34> 1. A material for an organic device, comprising the polymer compound or crosslinked polymer described in 1. <36> <32> 10. A material for an organic device, comprising the pendant polymer compound or the pendant polymer crosslinked product according to claim 1. <37> the organic device material 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; <33> ~ <36> 1. The material for an organic device according to any one of the preceding items. <38> The material for an organic electroluminescent device is a material for a light-emitting layer. <37> The material for an organic device according to claim 1. <39> <1> ~ <32> 10. A composition comprising the polycyclic aromatic compound or a multimer thereof according to any one of claims 1 to 9, and an organic solvent. <40> <30> A composition comprising the reactive compound according to claim 1 and an organic solvent. <41> Main chain polymers and <33> A composition comprising the reactive compound according to claim 1 and an organic solvent. <42> <31> 2. A composition comprising the polymer compound or crosslinked polymer described in 1. above and an organic solvent. <43> <32> 2. A composition comprising the pendant polymer compound or pendant polymer crosslinked product according to claim 1 and an organic solvent.

[0050] <44> a pair of electrodes consisting of an anode and a cathode, and a gas supply device disposed between the pair of electrodes; <1> ~ <29> 1. The polycyclic aromatic compound or a multimer thereof according to any one of the preceding claims. <30> a reactive compound according to <31> or the polymer compound or crosslinked polymer described in <32> and an organic layer containing the pendant polymer compound or the pendant polymer crosslinked product according to claim 1. <45> a pair of electrodes consisting of an anode and a cathode, and a gas supply device disposed between the pair of electrodes; <1> ~ <29> 1. The polycyclic aromatic compound or a multimer thereof according to any one of the preceding claims. <30> a reactive compound according to <31> or the polymer compound or crosslinked polymer described in <32> and a light-emitting layer containing the pendant-type polymer compound or the pendant-type crosslinked polymer according to claim 1. <46> the light-emitting layer contains a host and the polycyclic aromatic compound, its polymer, reactive compound, polymer compound, crosslinked polymer, pendant polymer compound, or pendant crosslinked polymer as a dopant; <45> The organic electroluminescent device according to claim 1. <47> the host is an anthracene-based compound, a fluorene-based compound, or a dibenzochrysene-based compound; <46> The organic electroluminescent device according to claim 1.

[0051] <48> an electron transport layer and / or an electron injection layer disposed between the cathode and the light-emitting layer, wherein at least one of the electron transport layer and the electron injection layer contains at least one selected from the group consisting of borane derivatives, pyridine derivatives, fluoranthene derivatives, BO-based derivatives, anthracene derivatives, benzofluorene derivatives, phosphine oxide derivatives, pyrimidine derivatives, arylnitrile derivatives, triazine derivatives, benzimidazole derivatives, phenanthroline derivatives, quinolinol-based metal complexes, thiazole derivatives, benzothiazole derivatives, silole derivatives, and azoline derivatives; <45> ~ <47> 10. The organic electroluminescent device according to claim 9, wherein <49> the electron transport layer and / or 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; <48> The organic electroluminescent device according to claim 1. <50> At least one layer of the hole injection layer, hole transport layer, light emitting layer, electron transport layer and 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 polymer compound obtained by reacting a low molecular weight compound capable of forming each layer with a main chain polymer, or a pendant polymer crosslinked polymer obtained by further crosslinking the pendant polymer compound, <44> ~ <49> 10. The organic electroluminescent device according to claim 9, wherein <51> <44> ~ <50> A display device or a lighting device comprising the organic electroluminescent device according to any one of the preceding claims.

[0052] <52> Using an organic alkali compound, X in the following intermediate-1 is obtained. 1 and X 2 a reaction step of metallating the halogen atom (Hal) between the Y 1 Halides of Y 1 Aminated halides of Y 1 Alkoxylated compounds of Y 1 and Y are reacted with a reagent selected from the group consisting of aryl oxy compounds of the formula 1 and a reaction step of exchanging The Y is then converted to the Y by successive electrophilic aromatic substitution reactions using a Bronsted base. 1 a reaction step of bonding the B ring and the C ring together; Including, <1> 2. A method for producing a polycyclic aromatic compound represented by formula (1) or a multimer of a polycyclic aromatic compound having a plurality of structures represented by formula (1). [ka]

[0053] <53> Further, a Lewis acid is added to promote the reaction. <52> The manufacturing method described in <54> The method includes a reaction step of reacting an acid with the following intermediate-2: <1> 2. A method for producing a polycyclic aromatic compound represented by formula (1) or a multimer of a polycyclic aromatic compound having a plurality of structures represented by formula (1). [ka] (In Intermediate-2, Z is -B(OH)2 which may be esterified.) [Effects of the Invention]

[0054] The present invention provides a novel polycyclic aromatic compound. The polycyclic aromatic compound of the present invention is useful as a material for organic devices, particularly as a material for forming an emitting layer in an organic electroluminescent device. By using the compound of the present invention in the emitting layer, it is possible to provide an organic EL device with high efficiency and long life. [Brief explanation of the drawings]

[0055] [Figure 1] FIG. 1 is a schematic cross-sectional view showing an example of an organic EL element. [Figure 2] FIG. 1 is a diagram illustrating a method for producing an organic EL element on a substrate having a bank by using an inkjet method. DETAILED DESCRIPTION OF THE INVENTION

[0056] The present invention will be described in detail below. The following explanation of the constituent elements may be based on representative embodiments or specific examples, but the present invention is not limited to such embodiments. In this specification, a numerical range expressed using "to" means a range that includes the numerical values ​​before and after "to" as the lower and upper limits. In addition, in this specification, "hydrogen" in the explanation of structural formulas means "hydrogen atom (H)."

[0057] In this specification, chemical structures and substituents are sometimes represented by the number of carbon atoms. However, when a chemical structure is substituted with a substituent or when a substituent is further substituted with a substituent, the number of carbon atoms refers to the number of carbon atoms in each of the chemical structure and the substituent, and does not refer to 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 substituents A and 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 (with no carbon number restriction)," and the carbon number Y is not the total number of carbon atoms in substituents A and B.

[0058] 1. Polycyclic aromatic compounds and their polymers The compound of the present invention is a polycyclic aromatic compound represented by the following formula (1), or a multimer of a polycyclic aromatic compound having a plurality of structures represented by the following formula (1).

[0059] [ka] In formula (1), "A" to "C" are symbols indicating ring structures.

[0060] In formula (1), ring A, ring B, and ring C are each independently an aryl ring or a heteroaryl ring, provided that at least one ring selected from the group consisting of ring A, ring B, and ring C is a fused ring composed of two or more rings selected from the group consisting of monocyclic aryl rings, monocyclic heteroaryl rings, and cyclopentadiene rings. At least one hydrogen atom in these rings may be substituted with a substituent. This 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 having an aryl and a heteroaryl), a substituted or unsubstituted diarylboryl (the 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, the substituent may be an aryl, a heteroaryl, an alkyl, a cycloalkyl, or a diarylamino.

[0061] It is preferable that at least one of the rings A, B, and C has at least one substituent, it is more preferable that all of the rings A, B, and C have at least one substituent, and it is even more preferable that each of the rings A, B, and C has one substituent. The substituent is preferably a substituted or unsubstituted alkyl (especially neopentyl) or a cycloalkyl such as adamantyl, or preferably a tertiary alkyl (tR). Such bulky substituents increase the intermolecular distance, thereby improving the luminescence quantum yield (PLQY). Diarylamino is also a preferred substituent.

[0062] The tertiary alkyl is represented by the following formula (tR): [ka]

[0063] In the formula (tR), R a , R b , and R c are each independently alkyl having 1 to 24 carbon atoms, any -CH2- in the alkyl may be substituted with -O-, and the group represented by formula (tR) substitutes at least one hydrogen in the compound or structure represented by formula (1) at *.

[0064] R a , R b and R c The "alkyl having 1 to 24 carbon atoms" may be either a straight chain or a branched chain, and examples thereof include a straight chain alkyl having 1 to 24 carbon atoms or a branched chain alkyl having 3 to 24 carbon atoms, an alkyl having 1 to 18 carbon atoms (branched chain alkyl having 3 to 18 carbon atoms), an alkyl having 1 to 12 carbon atoms (branched chain alkyl having 3 to 12 carbon atoms), an alkyl having 1 to 6 carbon atoms (branched chain alkyl having 3 to 6 carbon atoms), and an alkyl having 1 to 4 carbon atoms (branched chain alkyl having 3 to 4 carbon atoms).

[0065] R in formula (tR) of formula (1) a , R b , and R c The total number of carbon atoms is preferably 3 to 20, and particularly preferably 3 to 10.

[0066] R a , R b , and R cSpecific examples of alkyl include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, t-butyl, n-pentyl, isopentyl, neopentyl, t-pentyl, n-hexyl, 1-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, n-heptyl, 1-methylhexyl, n-octyl, t-octyl, 1-methylheptyl, 2 1-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.

[0067] Examples of the group represented by formula (tR) include t-butyl, t-amyl, 1-ethyl-1-methylpropyl, 1,1-diethylpropyl, 1,1-dimethylbutyl, 1-ethyl-1-methylbutyl, 1,1,3,3-tetramethylbutyl, 1,1,4-trimethylpentyl, 1,1,2-trimethylpropyl, 1,1-dimethyloctyl, 1,1-dimethylpentyl, 1,1-dimethylheptyl, 1,1,5-trimethylhexyl, 1-ethyl- Examples include 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, 1,1-dimethylhexyl, etc. Among these, t-butyl and t-amyl are preferred.

[0068] Other preferred examples of the substituents in ring A, ring B, and ring C include, for example, diarylamino substituted with a group of formula (tR), carbazolyl (preferably N-carbazolyl) substituted with a group of formula (tR), or benzocarbazolyl (preferably N-benzocarbazolyl) substituted with a group of formula (tR). Examples of "diarylamino" include the groups described below as "first substituents." Examples of the substitution of a group of formula (tR) on diarylamino, carbazolyl, and benzocarbazolyl include examples in which some or all of the hydrogen atoms on the aryl ring or benzene ring in these groups are substituted with a group of formula (tR). The above explanation of the preferred substituents also applies to the polycyclic aromatic compounds and multimers thereof represented by the formulae (2) to (9) and (12) to (19).

[0069] The aryl ring, heteroaryl ring, or fused ring in rings A, B, and C may be Y 1 , X 1 and X 2 The formula (1) may have a 5- or 6-membered ring that shares a bond with the central fused two-ring structure. Here, the "fused two-ring structure" refers to the Y 1 , X 1 and X 2 The term "aryl or heteroaryl ring (which is ring A) having this six-membered ring" means that ring A is formed solely from this six-membered ring, or that ring A is formed by condensing another ring or rings to this six-membered ring so as to include this six-membered ring. In other words, the term "aryl or heteroaryl ring (which is ring A) having a six-membered ring" means that the six-membered ring constituting all or part of ring A is fused to the fused two-ring structure. The same explanation applies to "ring B," "ring C," and "five-membered ring."

[0070] In formula (1), at least one ring selected from the group consisting of ring A, ring B, and ring C is a fused ring (hereinafter, sometimes referred to as "fused ring F") composed of two or more rings selected from the group consisting of monocyclic aryl rings, cyclopentadiene rings, and monocyclic heteroaryl rings. At least one hydrogen atom in this fused ring may be substituted. The present inventors have found that by constructing an organic EL device using a polycyclic aromatic compound having such a fused ring as a material for the light-emitting layer, it is possible to improve the luminous efficiency and device lifetime.

[0071] In formula (1), it is preferable that one or two rings selected from the group consisting of ring A, ring B, and ring C are fused ring F, and it is more preferable that one or two rings selected from the group consisting of ring B and ring C are fused ring F.

[0072] The number of rings constituting the fused ring F is not particularly limited, but is preferably 2 to 5, and more preferably 2 or 3. Examples of the fused ring F include a fused ring of one monocyclic aryl ring and one monocyclic heteroaryl ring, a fused ring of one monocyclic aryl ring and one cyclopentadiene ring, a fused ring of two monocyclic aryl rings and one monocyclic heteroaryl ring, and a fused ring of two monocyclic aryl rings and one cyclopentadiene ring. In this case, the monocyclic aryl ring is preferably a benzene ring. Examples of the monocyclic heteroaryl ring include a furan ring, a thiophene ring, a pyrrole ring, a pyridine ring, a pyrimidine ring, and a pyridazine ring.

[0073] The fused ring F is preferably a combination of a 6-membered ring and a 5-membered ring. In this case, the 6-membered ring may share a bond with the above-mentioned fused bicyclic structure, or the 5-membered ring may share a bond with the above-mentioned fused bicyclic structure. The fused ring F is not composed of only cyclopentadiene rings. The cyclopentadiene ring is preferably a 1,1-dimethyl-2,4-cyclopentadiene ring. In formula (1), among ring A, ring B, and ring C, other than the fused ring F, it is preferable that they are monocyclic aryl rings or monocyclic heteroaryl rings, more preferably benzene rings, pyridine rings, or pyrimidine rings, and further preferably benzene rings.

[0074] In one embodiment, the fused ring F preferably comprises a heteroaryl ring containing a sulfur atom or an oxygen atom. Furthermore, the fused ring F is preferably a ring represented by formula (BHet), a ring represented by formula (DBHet), a ring represented by formula (PBHet), or a ring represented by formula (PPHet), and more preferably a ring represented by formula (BHet) or a ring represented by formula (DBHet). That is, the polycyclic aromatic compound and multimer thereof represented by formula (1) preferably contains at least one fused ring selected from the group consisting of a ring represented by formula (BHet), a ring represented by formula (DBHet), a ring represented by formula (PBHet), and a ring represented by formula (PPHet), and more preferably contains at least one fused ring selected from the group consisting of a ring represented by formula (BHet) and a ring represented by formula (DBHet). The polycyclic aromatic compound represented by formula (1) and a multimer thereof may contain, as the fused ring F, any one type of fused ring selected from the group consisting of a ring represented by formula (BHet), a ring represented by formula (DBHet), a ring represented by formula (PBHet), and a ring represented by formula (PPHet), or may contain any two or more types of fused rings.

[0075] [ka]

[0076] In formula (BHet), R a1 ~R a6 is hydrogen or a substituent, with the proviso that R a1 ~R a6 Any two or three of the adjacent ones are Y in formula (1). 1 and X 1 and / or X2 X is >O, >S, >Se, >NR, >Si(-R) 2、 or >C(-R)2. R in >NR, >Si(-R)2, or >C(-R)2 as X is independently hydrogen, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted alkyl, or optionally substituted cycloalkyl, and two R may be bonded to each other to form a ring.

[0077] R a1 ~R a6 is preferably hydrogen, or 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. a1 ~R a6 It is preferred that 0 to 2 of R are substituents (other than hydrogen) and the rest (excluding the above bond) are hydrogen. a1 ~R a6 It is more preferable that 0 to 1 of the groups be a substituent and the rest be hydrogen. In this case, the substituent is preferably a substituent containing tertiary alkyl (t-butyl, t-amyl, etc.), neopentyl, or adamantyl, as represented by the above formula (tR).

[0078] In formula (BHet), X is preferably >O, >S, >NR, or >C(—R)2, more preferably >O, >S, or >NR, and even more preferably >S. R in >NR is preferably an optionally substituted aryl, more preferably an unsubstituted aryl, and even more preferably an unsubstituted phenyl. Both R in >C(—R)2 are preferably optionally substituted alkyl, more preferably both are unsubstituted alkyl, and even more preferably both are unsubstituted methyl.

[0079] Y 1 and X 1 and / or X 2 The two adjacent R a1 ~R a6 As for R a5 and R a6 , R a2 and R a3 , R a1 and R a2 , and R a3 and R a4 When one or two rings selected from the group consisting of ring B and ring C are rings represented by formula (BHet), R a5 and R a6 , R a2 and R a3 , R a1 and R a2 , or R a3 and R a4 is preferably a bond, and R a5 and R a6 It is more preferable that represents a bond. When ring A in formula (1) is a ring represented by formula (BHet), formula (BHet) is Y 1 , X 1 , and X 2 and R a1 , R a2 , and R a3 , or R a2 , R a3 , and R a4 becomes a bond.

[0080] [ka]

[0081] In the formula (DBHet), R a11 ~R a18 is hydrogen or a substituent, with the proviso that R a11 ~R a18 Any two or three of the adjacent ones are Y in formula (1). 1 and X 1 and / or X 2 and X is >O, >S, >Se, >NR, >Si(-R)2, or >C(-R)2, and R in said >NR, >Si(-R)2, or >C(-R)2 is independently hydrogen, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted alkyl, or optionally substituted cycloalkyl, and two Rs may be bonded to form a ring. R a11 ~R a18 is preferably hydrogen, or 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. a11 ~R a18 It is preferred that 0 to 2 of R are substituents (other than hydrogen) and the rest (excluding the above bond) are hydrogen. a11 ~R a18 It is more preferable that 0 to 1 of the groups be a substituent and the rest be hydrogen. In this case, the substituent is preferably a substituent containing tertiary alkyl (t-butyl, t-amyl, etc.), neopentyl, or adamantyl, as represented by the above formula (tR).

[0082] In formula (DBHet), X is preferably >O, >S, >NR, or >C(-R)2, more preferably >O, >S, or >C(-R)2, and even more preferably >S or >O. R in >NR is preferably an optionally substituted aryl, more preferably an unsubstituted aryl, and even more preferably an unsubstituted phenyl. R in >C(-R)2 is preferably both optionally substituted alkyl, more preferably both unsubstituted alkyl, and even more preferably both unsubstituted methyl.

[0083] Y 1 and X 1 and / or X 2 The two adjacent R a11 ~R a18 As for R a11 and R a12 , R a12 and R a13 , R a13 and R 14 , R a15 and R 16 , R a16 and R 17 , and R a17 and R 18 When one or two rings selected from the group consisting of ring B and ring C are rings represented by formula (DBHet), R a11 and R a12 , R a12 and R a13 , R a13 and R 14 , R a15 and R 16 , R a16 and R 17 , or R a17 and R 18 is preferably a bond. When ring A in formula (1) is a ring represented by formula (BHet), formula (DBHet) is Y 1 , X 1 , and X 2 and Ra11 , R a12 , and R a13 , R a12 , R 13 , and R 14 , R a15 , R 16 , and R a16 , or R 16 , R a17 , and R 18 becomes a bond.

[0084] [ka]

[0085] In formula (PBHet), each Z is independently CR z or N, and at least one Z is N, and R z , R a26 and R a25 is hydrogen or a substituent, with the proviso that R z , R a26 and R a25 Any two or three of the adjacent ones are Y in formula (1). 1 and X 1 and / or X 2 Preferably, R a26 and R a25 is a bond, and X is >O, >S, >Se, >NR, >Si(-R)2, or >C(-R)2, and R in said >NR, >Si(-R)2, or >C(-R)2 is independently hydrogen, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted alkyl, or optionally substituted cycloalkyl.

[0086] Of the four Zs in formula (PBHet), it is preferred that one or two are N, and more preferred that one is N. When two are N, it is preferred that the two Ns are not adjacent to each other.

[0087] R z , R a26 and R a25is preferably hydrogen, or substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted diarylamino, substituted or unsubstituted diheteroarylamino, substituted or unsubstituted arylheteroarylamino, substituted or unsubstituted diarylboryl (the 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. R z , R a26 and R a25 It is preferred that 0 to 2 of R are substituents (other than hydrogen) and the rest (excluding the above bond) are hydrogen. z , R a26 and R a25 It is more preferable that 0 to 1 of the groups be a substituent and the rest be hydrogen. In this case, the substituent is preferably a substituent containing tertiary alkyl (t-butyl, t-amyl, etc.), neopentyl, or adamantyl, as represented by the above formula (tR).

[0088] In formula (PBHet), X is preferably >O, >S, >NR, or >C(-R)2, more preferably >O, >S, or >NR, and even more preferably >S or >O. R in >NR is preferably an optionally substituted aryl, more preferably an unsubstituted aryl, and even more preferably an unsubstituted phenyl. R in >C(-R)2 is preferably both optionally substituted alkyl, more preferably both unsubstituted alkyl, and even more preferably both unsubstituted methyl.

[0089] [ka]

[0090] In formula (PPHet), each Z is independently CR zor N, and at least one Z is N, and R z is hydrogen or a substituent, with the proviso that R z Any two or three of the adjacent ones are Y in formula (1). 1 and X 1 and / or X 2 X is >O, >S, >Se, >NR, >Si(-R)2, or >C(-R)2, and R in >NR, >Si(-R)2, or >C(-R)2 is independently hydrogen, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted alkyl, or optionally substituted cycloalkyl.

[0091] In formula (PBHet), one or two of Z are preferably N, and more preferably one is N. When two are N, it is preferable that the two Ns are not adjacent to each other. R z is preferably hydrogen, or 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. z It is preferred that 0 to 2 of R are substituents (other than hydrogen) and the rest (excluding the above bond) are hydrogen. z , R a26 and R a25 It is more preferable that 0 to 1 of the groups be a substituent and the rest be hydrogen. In this case, the substituent is preferably a substituent containing tertiary alkyl (t-butyl, t-amyl, etc.), neopentyl, or adamantyl, as represented by the above formula (tR).

[0092] In formula (PPHet), X is preferably >O, >S, >NR, or >C(-R)2, more preferably >O, >S, or >NR, and even more preferably >S or >O. R in >NR is preferably an optionally substituted aryl, more preferably an unsubstituted aryl, and even more preferably an unsubstituted phenyl. R in >C(-R)2 is preferably both optionally substituted alkyl, more preferably both unsubstituted alkyl, and even more preferably both unsubstituted methyl.

[0093] Y in Equation (1) 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. In the case of P=O, P=S, Si-R, or Ge-R, the atom bonding 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.

[0094] X in formula (1) 1 and X 2 are each independently >O, >NR, >Si(-R)2, >C(-R)2, >S, or >Se. X in formula (1) 1 and X 2 At least one of the groups is preferably >NR, and all of the groups are preferably >NR or X 1 and X 2 It is more preferred that one of these is >NR and the other is >C(-R)2. X 1 and X 2R of >NR in the above formula (I) is hydrogen, an optionally substituted aryl (excluding amino as a substituent), an optionally substituted heteroaryl, an optionally substituted alkyl, or an optionally substituted cycloalkyl; each R of >Si(-R)2 is independently hydrogen, an optionally substituted aryl, an optionally substituted heteroaryl, an optionally substituted alkyl, or an optionally substituted cycloalkyl; each R of >C(-R)2 is independently hydrogen, an optionally substituted aryl, an optionally substituted heteroaryl, an optionally substituted alkyl, or an optionally substituted cycloalkyl; it is preferred that the two Rs are the same, and the two Rs may be bonded to form a ring.

[0095] X 1 and X 2 In the formula (tR), R is preferably an optionally substituted aryl or an optionally substituted heteroaryl. Here, preferred aryls include phenyl, biphenylyl (particularly 2-biphenylyl), and terphenylyl (particularly terphenyl-2'-yl). Preferred heteroaryls include benzothienyl (e.g., 2-benzothienyl, 6-benzothienyl), benzofuranyl (e.g., 2-benzofuranyl, 3-benzofuranyl, 5-benzofuranyl), dibenzofuranyl (e.g., 4-dibenzofuranyl), dimethylxanthenyl (e.g., 2-dimethylxanthenyl), and dibenzodioxinyl. Preferred substituents include tertiary alkyl (e.g., t-butyl) or cycloalkyl (e.g., adamantyl) represented by the formula (tR). The number of substituents in the aryl and heteroaryl is preferably 0 to 2, more preferably 1 or 2, and even more preferably 1. It is also preferred that the aryl ring in the above aryl is condensed with a cycloalkane, as described below.

[0096] X 1 and X 2Particularly preferred examples of R in >NR include optionally substituted 2-biphenylyl, optionally substituted terphenyl-2'-yl, and aryl (optionally substituted) fused with a cycloalkane. As the optionally substituted 2-biphenylyl, 2-biphenylyl substituted with 1 to 3 t-butyl groups is particularly preferred. As the optionally substituted terphenyl-2'-yl, unsubstituted [1,1':3',1"-terphenyl]-2'-yl is particularly preferred. As the aryl fused with a cycloalkane, the following are particularly preferred.

[0097] [ka] (Me is methyl, tBu is t-butyl, * indicates the bond position.)

[0098] The preferred range of R is >NR, and X is 1 or X 2 By using the compound of the present invention having the formula (I) as a light-emitting material, the light-emitting efficiency and the life of the device can be further improved.

[0099] X 1 and X 2 When both are >NR, X 1 and X 2 In the formula, only one of the Rs in >NR is optionally substituted 2-biphenylyl, or X 1 and X 2 In the formula (X), it is more preferable that only one R on the >NR side or both R on the >NR side are optionally substituted terphenyl-2'-yl. Terphenyl-2'-yl is preferably [1,1':3',1''-terphenyl]-2'-yl. 1 and X 2In the above formula, when only one R of >NR is optionally substituted 2-biphenylyl or optionally substituted terphenyl-2'-yl, the other R of >NR is preferably optionally substituted phenyl. Examples of such compounds include the following compounds (1F-25), (1F-90), and (1F-90').

[0100] [ka]

[0101] X 1 and X 2 When both are >NR, X 1 and X 2 It is also preferred that either R of >NR in the above formula is an aryl (which may be substituted) fused with a cycloalkane, and in this case, it is preferred that R of the other >NR is an optionally substituted phenyl. Also, X 1 and X 2 It is also preferred that either R of >NR in the above formula is an optionally substituted 2-biphenylyl, and the other R of >NR is an optionally substituted aryl fused with a cycloalkane.

[0102] X 1 and X 2 In the formula (2-3-1), R in at least one of >NR, >Si(-R)2, and >C(-R)2 may be bonded to at least one of the rings A, B, and C via a linking group or a single bond. As the linking group, -O-, -S-, or -C(-R)2- is preferred. R in the "-C(-R)2-" is hydrogen, alkyl, or cycloalkyl. This definition applies to X represented by the following formula (2-3-1): 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, with respect to the benzene ring which is the b ring (or the c ring) in the formula (2) described later, 1 (or X2 The compound has a ring B' (or ring C') formed by condensing another ring so as to incorporate the ring B'. The condensed ring B' (or condensed ring C') formed is, for example, a carbazole ring, a phenoxazine ring, a phenothiazine ring, or an acridine ring.

[0103] In addition, the above provisions are based on the following formulas (2-3-2) and (2-3-3): 1 and / or X 2 It can also be expressed as a compound having a ring structure in which X is incorporated into the fused ring A'. That is, for example, the a-ring in formula (2) is a benzene ring, and X 1 (and / or 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 carbazole ring, a phenoxazine ring, a phenothiazine ring, or an acridine ring.

[0104] [ka]

[0105] In formula (1), ring B and ring C may be bonded via a single bond or a linking group. Examples of the linking group include >O, >NR, >Si(-R)2, >C(-R)2, >S, and >Se. R in the >NR and >Si(-R)2 is each independently hydrogen, an optionally substituted aryl, an optionally substituted heteroaryl, an optionally substituted alkyl, or an optionally substituted cycloalkyl. R in the >C(-R)2 is hydrogen, an optionally substituted aryl, an optionally substituted heteroaryl, an optionally substituted alkyl, or an optionally substituted cycloalkyl. Furthermore, R in at least one of >NR, >Si(-R)2, and >C(-R)2 may be bonded to at least one of ring B and ring C via a linking group or a single bond. The linking group is preferably -O-, -S-, or -C(-R)2-. R in the "-C(-R)2-" is hydrogen, alkyl, or cycloalkyl. For details of the embodiment in which R in at least one of >NR, >Si(—R) 2 and >C(—R) 2 is bonded to at least one of the B ring and the C ring via a linking group or a single bond, see the above-mentioned X 1 or X 2 The explanation using equations (2-3-1), (2-3-2), and (2-3-3) can be cited.

[0106] When ring B and ring C are bonded via a linking group, the linking group preferably directly bonds the aryl rings and heteroaryl rings in ring B and ring C. It is also preferred that the substituents of the aryl rings and heteroaryl rings in ring B and ring C are bonded via a single bond.

[0107] X 1 , X 2 As the linking group connecting ring B and ring C, and among specific examples of >O, >NR, >Si(-R)2, >C(-R)2, >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.

[0108] The "aryl ring" which is ring A, ring B, and ring C in formula (1) includes, 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.

[0109] Specific examples of the "aryl ring" include a monocyclic benzene ring, a bicyclic bicyclic bicyclic naphthalene ring and an indene ring, a tricyclic terphenyl ring (m-terphenyl, o-terphenyl, p-terphenyl) and a fused tricyclic acenaphthylene ring, a fluorene ring, a phenalene ring, a phenanthrene ring, and an anthracene ring, fused tetracyclic triphenylene ring, a pyrene ring, a naphthacene ring, and a chrysene ring, fused pentacyclic perylene ring and a pentacene ring, etc. Furthermore, the fluorene ring, benzofluorene ring, and indene ring each include a structure in which a fluorene ring, a benzofluorene ring, a cyclopentane ring, etc. are spiro-bonded. The fluorene ring, benzofluorene ring, and indene ring also include rings in which two of the two hydrogen atoms of the methylene are substituted with alkyl such as methyl as the first substituent described below, resulting in a dimethylfluorene ring, a dimethylbenzofluorene ring, a dimethylindene ring, and the like.

[0110] Examples of the "heteroaryl ring" which is the ring A, ring B, and ring C in formula (1) include heteroaryl rings having 2 to 30 carbon atoms, preferably heteroaryl rings having 2 to 25 carbon atoms, more preferably heteroaryl rings having 2 to 20 carbon atoms, even more 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 heterocyclic rings containing, in addition to carbon, 1 to 5 heteroatoms selected from oxygen, sulfur, and nitrogen as ring-constituting atoms. The "heteroaryl ring" can be a heterocyclic ring having "R" defined in formula (2) described below. 1 ~R 11The term "heteroaryl ring" corresponds to "a heteroaryl ring formed together with ring a, ring b, or ring c by bonding adjacent groups among the above, and since ring a (or ring b, ring c) is already composed of a benzene ring with 6 carbon atoms, the lower limit of the carbon number is 6, the total carbon number of the fused rings formed by condensing a 5-membered ring to this.

[0111] Specific examples of the "heteroaryl ring" include a pyrrole ring, an oxazole ring, an isoxazole ring, a thiazole ring, an isothiazole ring, an imidazole ring, an oxadiazole ring, a thiadiazole ring, a triazole ring, a tetrazole ring, a pyrazole ring, a pyridine ring, a pyrimidine ring, a pyridazine ring, a pyrazine ring, a triazine ring, an indole ring, an isoindole ring, a 1H-indazole ring, a benzimidazole ring, a benzoxazole ring, a benzothiazole ring, a 1H-benzotriazole ring, a quinoline ring, an isoquinoline ring, a cinnoline ring, a quinazoline ring, a quinoxaline ring, a phthalazine ring, a naphthyl ring, and the like. Examples of the dihydroacridine ring include an azine 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, a naphthobenzofuran ring, a dioxin ring, a dihydroacridine ring, a xanthene ring, a thioxanthene ring, a dibenzodioxin ring, etc. In addition, the dihydroacridine ring, the xanthene ring, and the thioxanthene ring are also preferably such that two of the two hydrogen atoms of the methylene are each substituted with an alkyl group such as methyl as the first substituent described below, thereby forming a dimethyldihydroacridine ring, a dimethylxanthene ring, a dimethylthioxanthene ring, etc. In addition, bicyclic rings such as bipyridine ring, phenylpyridine ring, and pyridylphenyl ring, and tricyclic rings such as terpyridyl ring, bispyridylphenyl ring, and pyridylbiphenyl ring are also included as "heteroaryl rings." Furthermore, "heteroaryl rings" also include pyran rings.

[0112] At least one hydrogen atom in the "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 (the 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 "aryl" or "heteroaryl" as the first substituent, the aryl of "diarylamino," the heteroaryl of "diheteroarylamino," the aryl and heteroaryl of "arylheteroarylamino," the aryl of "diarylboryl," and the aryl of "aryloxy" include monovalent groups of the "aryl ring" or "heteroaryl ring" described above.

[0113] Specific examples of "aryl" include aryl having 6 to 30 carbon atoms, preferably aryl having 6 to 24 carbon atoms, more preferably aryl having 6 to 20 carbon atoms, still more preferably aryl having 6 to 16 carbon atoms, particularly preferably aryl having 6 to 12 carbon atoms, and most preferably aryl having 6 to 10 carbon atoms.

[0114] Specific examples of the aryl include phenyl, which is a monocyclic aryl; (2-, 3-, 4-)biphenylyl, which is a bicyclic aryl; (1-, 2-)naphthyl and (2-, 3-, 4-, 5-, 6-, 7-)indenyl, which are fused bicyclic aryls; and 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-3-yl, p-terphenyl). fused tricyclic aryls, acenaphthylene-(1-, 3-, 4-, 5-)yl, fluoren-(1-, 2-, 3-, 4-, 9-)yl, phenalen-(1-, 2-)yl, (1-, 2-, 3-, 4-, 9-)phenanthryl; tetracyclic aryls, quaterphenylyl (5'-phenyl-m-terphenyl-2-yl, 5'-phenyl-m-terphenyl-2-yl, 5'-phenyl-m-terphenyl-2-yl); aryls such as 5'-phenyl-m-terphenyl-3-yl, 5'-phenyl-m-terphenyl-4-yl, m-quaterphenylyl; fused tetracyclic aryls such as triphenylen-(1-, 2-)yl, pyren-(1-, 2-, 4-)yl, naphthacene-(1-, 2-, 5-)yl; and fused pentacyclic aryls such as perylene-(1-, 2-, 3-)yl and pentacene-(1-, 2-, 5-, 6-)yl.

[0115] Furthermore, examples of "heteroaryl" include heteroaryls having 2 to 30 carbon atoms, preferably heteroaryls having 2 to 25 carbon atoms, more preferably heteroaryls having 2 to 20 carbon atoms, still more preferably heteroaryls having 2 to 15 carbon atoms, and particularly preferably heteroaryls having 2 to 10 carbon atoms. Furthermore, examples of heteroaryls include heterocycles containing, in addition to carbon, 1 to 5 heteroatoms selected from oxygen, sulfur, and nitrogen as ring-constituting atoms.

[0116] 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, dibenzofuranyl, benzo[b]thienyl, dibenzothienyl, and indyl. hydroxyl, isoindolyl, 1H-indazolyl, benzimidazolyl, benzoxazolyl, benzothiazolyl, 1H-benzotriazolyl, quinolyl, isoquinolyl, cinnolyl, quinazolyl, quinoxalinyl, phthalazinyl, naphthyridinyl, purinyl, pteridinyl, carbazolyl, acridinyl, phenoxazinyl, phenothiazinyl, phenazinyl, phenoxathiinyl, thianthrenyl, indolizinyl, and the like.

[0117] Furthermore, 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. Alkyl having 1 to 18 carbon atoms (branched alkyl having 3 to 18 carbon atoms) is preferred, alkyl having 1 to 12 carbon atoms (branched alkyl having 3 to 12 carbon atoms) is more preferred, alkyl having 1 to 8 carbon atoms (branched alkyl having 3 to 8 carbon atoms) is even more preferred, alkyl having 1 to 6 carbon atoms (branched alkyl having 3 to 6 carbon atoms) is particularly preferred, and alkyl having 1 to 5 carbon atoms (branched alkyl having 3 to 5 carbon atoms) is most preferred.

[0118] Specific alkyls 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, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, n-heptyl, 1-methylhexyl, n-octyl, t-octyl (1,1,3,3-tetramethylbutyl), and the like. ), 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 2,6-dimethyl-4-heptyl, 3,5,5-trimethylhexyl, n-decyl, n-undecyl, 1-methyldecyl, n-dodecyl, n-tridecyl, 1-hexylheptyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, n-heptadecyl, n-octadecyl, and n-eicosyl. Further examples include 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.

[0119] 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.

[0120] 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.

[0121] Furthermore, examples of the "alkoxy" as the first substituent include straight-chain alkoxy having 1 to 24 carbon atoms or branched-chain alkoxy having 3 to 24 carbon atoms. Alkoxy having 1 to 18 carbon atoms (branched-chain alkoxy having 3 to 18 carbon atoms) is preferred, alkoxy having 1 to 12 carbon atoms (branched-chain alkoxy having 3 to 12 carbon atoms) is more preferred, alkoxy having 1 to 6 carbon atoms (branched-chain alkoxy having 3 to 6 carbon atoms) is even more preferred, and alkoxy having 1 to 5 carbon atoms (branched-chain alkoxy having 3 to 5 carbon atoms) is particularly preferred.

[0122] Specific examples of alkoxy include methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, s-butoxy, t-butoxy, t-amyloxy, pentyloxy, hexyloxy, heptyloxy, and octyloxy.

[0123] Furthermore, examples of the "substituted silyl" as the first substituent include silyl substituted with three substituents selected from the group consisting of alkyl, cycloalkyl, and aryl, such as trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, alkyldicycloalkylsilyl, triarylsilyl, dialkylarylsilyl, and alkyldiarylsilyl.

[0124] An example of a "trialkylsilyl" is a group in which three hydrogen atoms in a silyl group are each independently substituted with an alkyl, and the alkyl can be any of the groups described above as the "alkyl" in the first substituent. Preferred alkyl groups for substitution are alkyl groups having 1 to 5 carbon atoms, and specific examples include methyl, ethyl, propyl, i-propyl, butyl, sec-butyl, t-butyl, and t-amyl.

[0125] Specific examples of trialkylsilyl include trimethylsilyl, triethylsilyl, tripropylsilyl, tri-i-propylsilyl, tributylsilyl, tri-sec-butylsilyl, tri-t-butylsilyl, tri-t-amylsilyl, ethyldimethylsilyl, propyldimethylsilyl, i-propyldimethylsilyl, butyldimethylsilyl, sec-butyldimethylsilyl, t-butyldimethylsilyl, t-amyldimethylsilyl, methyldiethylsilyl, propyldiethylsilyl, i-propyldiethylsilyl, and butylsilyl. Examples thereof 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.

[0126] Examples of "tricycloalkylsilyl" include groups in which three hydrogen atoms in a silyl group are each independently substituted with a cycloalkyl, and examples of this cycloalkyl include the groups described as "cycloalkyl" in the first substituent above. Preferred cycloalkyl groups for substitution are cycloalkyl groups having 5 to 10 carbon atoms, and specific examples 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.

[0127] Specific examples of tricycloalkylsilyl include tricyclopentylsilyl and tricyclohexylsilyl.

[0128] 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 above-mentioned specific alkyls and cycloalkyls.

[0129] Specific examples of dialkylarylsilyl substituted with two alkyls and one aryl, alkyldiarylsilyl substituted with one alkyl and two aryls, and triarylsilyl substituted with three aryls include silyl substituted with a group selected from the above-mentioned specific alkyls and aryls. Specific examples of triarylsilyl include triphenylsilyl.

[0130] Furthermore, the "aryl" in the "diarylboryl" of the first substituent can be referenced from the above description of the aryl. Furthermore, the two aryls may be bonded via a single bond or a linking group (for example, >C(-R)2, >O, >S, or >NR). Here, R in >C(-R)2 and >NR is aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, alkoxy, or aryloxy (all of which are first substituents), and the first substituent may be further substituted with aryl, heteroaryl, alkyl, or cycloalkyl (all of which are second substituents). Specific examples of these groups can be referenced from the above description of the aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, alkoxy, or aryloxy as the first substituent.

[0131] As described above for 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 this second substituent include aryl, heteroaryl, alkyl, or cycloalkyl. For specific examples thereof, see the above-mentioned monovalent group of the "aryl ring" or "heteroaryl ring," and the description of "alkyl" or "cycloalkyl" as the first substituent. Furthermore, the aryl and heteroaryl as the second substituent also include structures in which at least one hydrogen atom is substituted with an aryl such as phenyl (specific examples include the groups described above), an alkyl such as methyl or t-butyl (specific examples include the groups described above), or a cycloalkyl such as cyclohexyl (specific examples include the groups described above). For example, when the second substituent is carbazolyl, a carbazolyl 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.

[0132] The emission wavelength can be adjusted by the steric hindrance, electron donating property, and electron withdrawing property of the structure of the first substituent. Preferred are groups represented by the following structural formulas, and more preferred are methyl, t-butyl, t-amyl, t-octyl, neopentyl, adamantyl, 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 are more preferred, and methyl, t-butyl, t-amyl, t-octyl, neopentyl, adamantyl, 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 are more preferred. From the viewpoint of ease of synthesis, a larger steric hindrance is preferred for selective synthesis, and specifically, t-butyl, t-amyl, t-octyl, adamantyl, 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.

[0133] In the structural formula below, "Me" represents methyl, "tBu" represents t-butyl, "tAm" represents t-amyl, "tOct" represents t-octyl, and * represents the bonding position. [ka]

[0134] [ka]

[0135] [ka]

[0136] [ka]

[0137] Y in equation (1) 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. Particularly preferred are aryl having 6 to 10 carbon atoms (e.g., phenyl, naphthyl, etc.), alkyl having 1 to 5 carbon atoms (e.g., methyl, ethyl, etc.), and cycloalkyl having 5 to 10 carbon atoms (preferably cyclohexyl or adamantyl). This explanation is based on the Y in equations (2), (3), (4), (5), (6), (7), (8), (9), (12), (13), (14), (15), (16), (17), (18), (19), (20), (2-1), (3-1), (4-1), (5-1), (6-1), (7-1), (8-1), (9-1), (10-1), (11-1), (12-1), (13-1), (14-1), (15-1), (16-1), (17-1), (18-1), (19-1), and (20-1) described below. 1 The same is true.

[0138] X in equation (1) 1 and X 2 and R of >NR as a linking group connecting ring B and ring C are aryl, heteroaryl, alkyl or cycloalkyl optionally substituted with the second substituent described above (provided that X 1 and X 2In the above formula, the aryl as R of >NR is not substituted with amino. Examples of the aryl, heteroaryl, alkyl, or cycloalkyl include the groups described above. In addition, preferred examples of the second substituent include alkyl such as methyl, tertiary butyl, and amyl, and p-tertiary butylphenyl. The alkyl substitution position is preferably the para position relative to the N substitution position. As R of >NR, particularly preferred are aryl having 6 to 10 carbon atoms (e.g., phenyl, naphthyl, etc.) which may be substituted with a second substituent, heteroaryl having 2 to 15 carbon atoms (e.g., carbazolyl, etc.) which may be substituted with a second substituent, alkyl having 1 to 5 carbon atoms (e.g., methyl, ethyl, etc.), or cycloalkyl having 5 to 10 carbon atoms (preferably cyclohexyl or adamantyl). This explanation is based on the X in equations (2), (3), (4), (5), (6), (7), (8), (9), (12), (13), (14), (15), (16), (17), (18), (19), (20), (2-1), (3-1), (4-1), (5-1), (6-1), (7-1), (8-1), (9-1), (10-1), (11-1), (12-1), (13-1), (14-1), (15-1), (16-1), (17-1), (18-1), (19-1) and (20-1) described below. 1 , X 2 , X 3 , and X 4 The same is true for R in equation (2). 7 and R 8 , R in Eq. (3) 8 and R 24 , or R in Eq. (5) 34 and R 24 The same applies to a linking group formed by bonding.

[0139] X 1 and X 2 In particular, the R in >NR in formula (1) is 1 and X 2 The above-mentioned range is preferable for R in >NR, and the above-mentioned preferable range is also preferable for X in formulas (7), (8), (9), (7-1), (8-1), and (9-1). 3 and X4 But it's the same.

[0140] X in equation (1) 1 and X 2 In the formula (I), R of >Si(-R)2 and R of >Si(-R)2 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. Examples of the aryl, heteroaryl, alkyl, or cycloalkyl include the groups described above. Particularly preferred are aryls having 6 to 10 carbon atoms (e.g., phenyl, naphthyl, etc.), heteroaryls having 2 to 15 carbon atoms (e.g., carbazolyl, etc.), alkyls having 1 to 5 carbon atoms (e.g., methyl, ethyl, etc.), and cycloalkyls having 5 to 10 carbon atoms (preferably cyclohexyl or adamantyl). This explanation is based on the X in equations (2), (3), (4), (5), (6), (7), (8), (9), (12), (13), (14), (15), (16), (17), (18), (19), (20), (2-1), (3-1), (4-1), (5-1), (6-1), (7-1), (8-1), (9-1), (10-1), (11-1), (12-1), (13-1), (14-1), (15-1), (16-1), (17-1), (18-1), (19-1) and (20-1) described below. 1 , X 2 , X 3 , and X 4 The same is true for R in equation (2). 7 and R 8 , R in Eq. (3) 8 and R 24 , or R in Eq. (5) 34 and R 24 The same applies to a linking group formed by bonding.

[0141] X in equation (1) 1 and X 2In the formula (I), R in >C(-R)2 and R in >C(-R)2 as a linking group connecting ring B and ring C are hydrogen, aryl, heteroaryl, alkyl, or cycloalkyl, each of which may be substituted with the second substituent described above. Examples of the aryl, heteroaryl, alkyl, or cycloalkyl include the groups described above. Particularly preferred are aryls having 6 to 10 carbon atoms (e.g., phenyl, naphthyl, etc.), heteroaryls having 2 to 15 carbon atoms (e.g., carbazolyl, etc.), alkyls having 1 to 5 carbon atoms (e.g., methyl, ethyl, etc.), and cycloalkyls having 5 to 10 carbon atoms (preferably cyclohexyl or adamantyl). This explanation is based on the X in equations (2), (3), (4), (5), (6), (7), (8), (9), (12), (13), (14), (15), (16), (17), (18), (19), (20), (2-1), (3-1), (4-1), (5-1), (6-1), (7-1), (8-1), (9-1), (10-1), (11-1), (12-1), (13-1), (14-1), (15-1), (16-1), (17-1), (18-1), (19-1) and (20-1) described below. 1 , X 2 , X 3 , and X 4 However, R in Eq. (2) 7 and R 8 , R in Eq. (3) 8 and R 24 , or R in Eq. (5) 34 and R 24 The same applies to a linking group formed by bonding.

[0142] In formula (1), X 1 , X 2Alternatively, when the linking group connecting ring B and ring C is connected to at least one of rings A, B, and C, examples of the linking group include -O-, -S-, -C(-R)2-, and a single bond. Among these, R in "-C(-R)2-" is hydrogen, alkyl, or cycloalkyl, and examples of this 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) are preferred. This explanation also applies to the linking group "-C(-R)2-" in formulas (2), (3), (4), (5), (6), (7), (8), (9), (12), (13), (14), (15), (16), (17), (18), (19), (20), (2-1), (3-1), (4-1), (5-1), (6-1), (7-1), (8-1), (9-1), (10-1), (11-1), (12-1), (13-1), (14-1), (15-1), (16-1), (17-1), (18-1), (19-1), and (20-1) described below.

[0143] The present invention also relates to a multimer of a polycyclic aromatic compound having a plurality of unit structures represented by formula (1), preferably a multimer of a polycyclic aromatic compound having a plurality of unit structures represented by formulas (2), (3), (4), (5), (6), (12), (13), (14), (15), (16), (17), (18), (19), (20), (2-1), (3-1), (4-1), (5-1), (6-1), (7-1), (8-1), (9-1), (10-1), (11-1), (12-1), (13-1), (14-1), (15-1), (16-1), (17-1), (18-1), (19-1), and (20-1) described below. The polymer is preferably a dimer to a hexamer, more preferably a dimer to a trimer, and particularly preferably a dimer. The polymer may be in a form having a plurality of the above unit structures in one compound, and may be, for example, 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 having 1 to 3 carbon atoms, phenylene, or naphthylene (linked polymer), or a form in which any ring (ring A, ring B, or ring C, or ring a, ring b, or ring c, etc.) contained in the above unit structure is bonded so as to be shared by a plurality of unit structures (ring-shared polymer), or a form in which any ring (ring A, ring B, or ring C, or ring a, ring b, or ring c) contained in the above unit structure is bonded so as to be condensed with each other (ring-fused polymer). However, ring-shared polymers and ring-fused polymers are preferred, and ring-shared polymers are more preferred. An example of the polymer structure is the structure represented by formula (9) described below.

[0144] In addition, all or part of the hydrogen atoms in the chemical structure of the polycyclic aromatic compound represented by formula (1) and its multimer may be deuterium, cyano, or halogen. For example, in formula (1), the rings A, B, and C (rings A to C are aryl rings or heteroaryl rings), the substituents on rings A to C, Y 1 When is Si-R or Ge-R, R (= alkyl, cycloalkyl, aryl), and X 1 and X 2When R is >NR, >C(-R)2, or >Si(-R)2, hydrogen atoms in R (= alkyl, cycloalkyl, aryl) can be substituted with deuterium, cyano, or halogen. Among these, hydrogen atoms in aryl or heteroaryl can be substituted with deuterium, cyano, or halogen. Examples of suitable embodiments include those in which all or some of the hydrogen atoms in aryl or heteroaryl are substituted with deuterium, cyano, or halogen. The halogen atom is fluorine, chlorine, bromine, or iodine, preferably fluorine, chlorine, or bromine, more preferably fluorine or chlorine, and even more preferably fluorine. Furthermore, from the viewpoint of durability, it is also preferable that all or some of the hydrogen atoms in the chemical structure of the polycyclic aromatic compound represented by formula (1) and its multimer are deuterium-substituted.

[0145] Preferred examples of the polycyclic aromatic compound represented by formula (1) and its multimers include polycyclic aromatic compounds represented by the following formulas (2), (3), (4), (5), (6), (7), (8), or (9) and its multimers, as well as polycyclic aromatic compounds represented by the following formulas (12), (13), (14), (15), (16), (17), (18), (19), (20), (2-1), (3-1), (4-1), (5-1), (6-1), (7-1), (8-1), (9-1), (10-1), (11-1), (12-1), (13-1), (14-1), (15-1), (16-1), (17-1), (18-1), (19-1), and (20-1) and its multimers. For the substituents and ring structures contained in formulas (2), (3), (4), (5), (6), (7), (8), (9), (12), (13), (14), (15), (16), (17), (18), (19), (20), (2-1), (3-1), (4-1), (5-1), (6-1), (7-1), (8-1), (9-1), (10-1), (11-1), (12-1), (13-1), (14-1), (15-1), (16-1), (17-1), (18-1), (19-1) and (20-1), reference can be made to the corresponding explanations for formula (1).

[0146] [ka]

[0147] [ka]

[0148] In equations (2), (3), (4), (5), (6), (7), (8), and (9), R 1 ~R 17 , R 21 ~R 24 , R 31 ~R 34 , and R 41 ~R 44 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, or substituted silyl, and at least one hydrogen atom in these may be substituted with an aryl, heteroaryl, alkyl, or cycloalkyl. 1 ~R 3 Adjacent groups among these are bonded to each other to form ring a together with R 8 ~R 11 Adjacent groups of the b ring are bonded to each other to form R 4 ~R 7 Adjacent groups among these are bonded to each other to form ring c together with R 12 ~R 14 Adjacent groups among these are bonded to each other to form a12 ring together with R 15 ~R 17 Adjacent groups of the b15 ring are bonded to each other to form R 21 ~R 24 Adjacent groups of the c21 ring are bonded to each other to form R 31 ~R 34 Adjacent groups among these are bonded to each other to form ring b31, and R 41 ~R 44Adjacent groups among these may be bonded to each other to form an aryl ring or a heteroaryl ring together with ring b41, and at least one hydrogen atom in the formed ring may be substituted with an aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl (the two aryls may be bonded via a single bond or a linking group), alkyl, cycloalkyl, alkoxy, aryloxy, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, or alkyldicycloalkylsilyl, and at least one hydrogen atom in these may be substituted with an aryl, heteroaryl, alkyl, or cycloalkyl.

[0149] In equation (2), R 1 ~R 11 At least one pair of adjacent groups is bonded to form a divalent group represented by the formula (Het). 4 and R 5 and R 6 and R 7 and R 8 and R 9 and R 10 and R 11 and (Het) simultaneously constitute a divalent group represented by the formula (Het). In other words, neither the b ring nor the c ring is formed by bonding two or more divalent groups represented by the formula (Het) to form a fused tricyclic ring. In equation (7), R 1 ~R 3 and R 9 ~R 17 At least one pair of adjacent groups in the formula (Het) are bonded to form a divalent group represented by the formula (Het).

[0150] In equations (2), (3), (4), (5), (6), (7), (8), and (9), R 1 ~R 17 , R 21 ~R 24 , R 31 ~R 34, and R 41 ~R 44 are each independently preferably 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, or a trialkylsilyl (wherein the alkyl is an alkyl having 1 to 6 carbon atoms). 1 ~R 3 Adjacent groups among these are bonded to each other to form ring a together with R 8 ~R 11 Adjacent groups of the b ring are bonded to each other to form R 4 ~R 7 Adjacent groups among these are bonded to each other to form ring c together with R 12 ~R 14 Adjacent groups among these are bonded to each other to form a12 ring together with R 15 ~R 17 Adjacent groups of the b15 ring are bonded to each other to form R 21 ~R 24 Adjacent groups of the c21 ring are bonded to each other to form R 31 ~R 34 Adjacent groups among these are bonded to form ring b31, and R 41 ~R 44 Adjacent groups among these may be bonded to each other to form, together with ring b41, an aryl ring having 9 to 16 carbon atoms or a heteroaryl ring having 6 to 15 carbon atoms, and at least one hydrogen atom in the formed ring may be substituted with an aryl ring having 6 to 10 carbon atoms, an alkyl ring having 1 to 12 carbon atoms, a cycloalkyl ring having 3 to 16 carbon atoms, or a trialkylsilyl ring (wherein the alkyl ring is an alkyl ring having 1 to 4 carbon atoms).

[0151] R in equations (2), (3), (4), (5), and (6) 2 is preferably alkyl (methyl, t-butyl, etc.), substituted phenyl (2,6, dimethylphenyl, etc.), diarylamino (diphenylamino, etc.) or carbazolyl (N-carbazolyl, etc.).2 R is a group other than 1 , R 3 is preferably each hydrogen.

[0152] In formula (2) (formula (Het)), formula (3), formula (4), formula (5), formula (6), formula (7) (formula (Het)), formula (8), and formula (9), X is >O, >S, >Se, >NR, >Si(-R)2, or >C(-R)2. R in >NR, >Si(-R)2, or >C(-R)2 as X is independently hydrogen, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted alkyl, or optionally substituted cycloalkyl, and is preferably optionally substituted aryl having 6 to 30 carbon atoms, optionally substituted heteroaryl having 2 to 30 carbon atoms, optionally substituted alkyl having 1 to 24 carbon atoms, or optionally substituted cycloalkyl having 3 to 24 carbon atoms. R in >NR is preferably optionally substituted aryl, more preferably unsubstituted aryl, and even more preferably unsubstituted phenyl. In >C(-R)2, each R is preferably an alkyl which may be substituted, more preferably an unsubstituted alkyl, and even more preferably an unsubstituted methyl. X is preferably >O, >S, >NR, or >C(-R)2, more preferably >O, >S, or >NR, and even more preferably >S or >O.

[0153] In formula (Het), R b1 and R b2is hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl (two aryls may be bonded via a single bond or a linking group), alkyl, cycloalkyl, alkoxy, aryloxy, or substituted silyl, in which at least one hydrogen may be substituted with an aryl, heteroaryl, alkyl, or cycloalkyl, * represents the bonding position (bond as a substituent), X is >O, >S, >Se, >NR, >Si(-R)2, or >C(-R)2, and R in the >NR, >Si(-R)2, or >C(-R)2 is aryl, heteroaryl, alkyl, or cycloalkyl. In formula (Het), R b1 and R b2 is preferably hydrogen, aryl having 6 to 30 carbon atoms, heteroaryl having 2 to 30 carbon atoms, diarylamino (provided that aryl is aryl having 6 to 12 carbon atoms), diarylboryl (provided that aryl is aryl having 6 to 12 carbon atoms, and two aryls may be bonded via a single bond or a linking group), alkyl having 1 to 24 carbon atoms, cycloalkyl having 3 to 24 carbon atoms, or trialkylsilyl (provided that alkyl is alkyl having 1 to 6 carbon atoms).

[0154] R in Equation (2) 7 and R 8 , R in Eq. (3) 8 and R 24 , or R in Eq. (5) 34 and R 24 may be bonded to form a single bond, >O, >NR, >Si(-R)2, >C(-R)2, >S, or >Se (preferably >O, >NR, >C(-R)2, or >S). This is an example of when ring B and ring C are bonded in formula (1). For example, R 7 and R 8 The bonding form is Y 1 and (part of) the c-ring and R 7 and R 8 The binding site of Y and a part of the b ring form a six-membered ring. 1and one side of the benzene ring, which is the c-ring, and R 7 and R 8 and one side of the benzene ring, which is ring b, to form a 5- or 6-membered ring. R in the >NR and >Si(-R)2 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; R in the >C(-R)2 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 R in at least one of the >NR, >Si(-R)2, and >C(-R)2 may be bonded to at least one of the rings b and c via -O-, -S-, -C(-R)2-, or a single bond. R in the >NR is preferably an aryl having 6 to 10 carbon atoms, an alkyl having 1 to 4 carbon atoms, or a cycloalkyl having 5 to 10 carbon atoms. R in the above >C(-R)2 is preferably hydrogen, aryl having 6 to 10 carbon atoms, alkyl having 1 to 4 carbon atoms, or cycloalkyl having 5 to 10 carbon atoms.

[0155] Y in equations (2), (3), (4), (5), (6), (7), (8) and (9) 1 are each independently B, P, P=O, P=S, Al, Ga, As, Si-R, or Ge-R, and R in 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. Y 1 is preferably B, P, P═O, P═S, or Si—R, and particularly preferably B.

[0156] X in equations (2), (3), (4), (5), and (6) 1 , X 2 , and X in (7), (8) and (9) 1 , X 2 , X 3 and X 4are each independently >O, >NR, >Si(-R)2, >C(-R)2, >S, or >Se, and R in the >NR and >Si(-R)2 is each independently hydrogen, an optionally substituted aryl having 6 to 12 carbon atoms, an optionally substituted heteroaryl having 2 to 15 carbon atoms, an optionally substituted alkyl having 1 to 6 carbon atoms, or a cycloalkyl having 3 to 14 carbon atoms, and R in the >C(-R)2 is hydrogen, an optionally substituted aryl having 6 to 12 carbon atoms, an optionally substituted heteroaryl having 2 to 15 carbon atoms, an optionally substituted alkyl having 1 to 6 carbon atoms, or an optionally substituted cycloalkyl having 3 to 14 carbon atoms. Furthermore, R in at least one of >NR, >Si(-R)2, and >C(-R)2 may be bonded via -O-, -S-, -C(-R)2-, or a single bond to at least one ring selected from the group consisting of a 5-membered ring fused with ring a, ring b, ring c, ring a12, ring b15, ring c21, and a 5-membered ring fused with ring b31.

[0157] Here, the provision in formula (1) that "R in at least one of said >NR, >Si(-R)2, and >C(-R)2 is bonded to at least one of said ring A, ring B, and ring C by a linking group or a single bond" corresponds to the provision in formulas (2), (3), (4), (5), (6), (7), (8), and (9) that "R in at least one of said >NR, >Si(-R)2, and >C(-R)2 is bonded to at least one ring selected from the group consisting of ring a, ring b, ring c, ring a12, ring b15, a 5-membered ring fused with ring c21, a 5-membered ring fused with ring b31, and ring b41 by -O-, -S-, -C(-R)2-, or a single bond."

[0158] X 1 , X 2 , X 3 , and X 4are each independently >O, >NR, >C(-R)2, or >S, and R in the >NR is preferably an optionally substituted aryl having 6 to 10 carbon atoms, an optionally substituted alkyl having 1 to 4 carbon atoms, or an optionally substituted cycloalkyl having 5 to 10 carbon atoms, and R in the >C(-R)2 is preferably hydrogen, an optionally substituted aryl having 6 to 10 carbon atoms, an optionally substituted alkyl having 1 to 4 carbon atoms, or an optionally substituted cycloalkyl having 5 to 10 carbon atoms.

[0159] In the compounds represented by formulae (2), (3), (4), (5), (6), (7), (8), and (9), at least one selected from the group consisting of aryl rings and heteroaryl rings (ring a, ring b, ring c, ring a12, ring b15, ring c21, ring b31, and ring b41, the formed ring, at least one of the aryl and the heteroaryl) may be fused with at least one cycloalkane having 3 to 24 carbon atoms, at least one hydrogen atom 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 -CH2- in the cycloalkane may be substituted with -O-.

[0160] In the compound represented by formula (2), (3), (4), (5), (6), (7), (8), or (9), when at least one selected from the group consisting of aryl rings and heteroaryl rings is condensed with at least one cycloalkane, it is preferable that the at least one cycloalkane is a cycloalkane having 3 to 20 carbon atoms, in which at least one hydrogen atom 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.

[0161] At least one hydrogen atom in the compound represented by formula (2), (3), (4), (5), (6), (7), (8), or (9) may be substituted with deuterium, cyano, or halogen.

[0162] Each of the compounds represented by formulas (2), (3), (4), (5), (6), (7), (8), and (9) preferably has a structure containing at least one tertiary alkyl group represented by the above formula (tR). In particular, R in each of formulas (2) and (7) b1 , R b2 and one or more of the substituents of the ring to which the formula Het is bonded, R in each of formulas (3) and (4). 21 ~R 24 One or more of the following, R in each of formulas (5) and (6) 21 ~R 24 , R 31 ~R 34 One or more of the following, R in formula (8) 41 ~R 44 and R in formula (9) 31 ~R 34 and R 41 ~R 44 is preferably a substituent containing tertiary alkyl (such as t-butyl or t-amyl), neopentyl or adamantyl represented by the above formula (tR).

[0163] Among the polycyclic aromatic compounds represented by formula (2), (3), (4), (5), (6), (7), (8), or (9) or multimers thereof, polycyclic aromatic compounds represented by formula (3), (4), (5), (6), (7), (8), or (9) or multimers thereof are more preferred, and polycyclic aromatic compounds represented by formula (3) or (4) or multimers thereof are even more preferred.

[0164] [ka]

[0165] [ka]

[0166] In equations (12), (13), (14), (15), (16), (17), (18), (19) and (20), R 1 ~R 3 and R 8 ~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, alkoxy, aryloxy, tricycloalkylsilyl, dialkylcycloalkylsilyl, or alkyldicycloalkylsilyl, and at least one hydrogen in these may be substituted with an aryl, heteroaryl, alkyl, or cycloalkyl. 1 ~R 3 and R 8 ~R 11 are preferably 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), or an alkyl having 1 to 24 carbon atoms.

[0167] In equations (12), (13), (14), (15), (16), (17), (18), (19) and (20), R 51 ~R 58 and R 61 ~R 68 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, or substituted silyl, and at least one hydrogen in these may be substituted with an aryl, heteroaryl, alkyl, or cycloalkyl. 51 ~R58 and R 61 ~R 68 are preferably each independently hydrogen, aryl having 6 to 30 carbon atoms, heteroaryl having 2 to 30 carbon atoms, diarylamino (provided that the aryl is an aryl having 6 to 12 carbon atoms), diarylboryl (provided that 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), alkyl having 1 to 24 carbon atoms, cycloalkyl having 3 to 24 carbon atoms, or trialkylsilyl (provided that the alkyl is an alkyl having 1 to 6 carbon atoms).

[0168] In equations (12), (13), (14), (15), (16), (17), (18), (19) and (20), R 1 ~R 3 Adjacent groups among these are bonded to each other to form ring a together with R 8 ~R 11 Adjacent groups of the b ring are bonded to each other to form R 51 ~R 54 Adjacent groups of the R 55 ~R 58 Adjacent groups of the R 61 ~R 64 Adjacent groups of the b61 ring are bonded to each other to form a ring b61. 65 ~R 68Adjacent groups among these may be bonded to each other to form an aryl ring or a heteroaryl ring together with ring b65, and at least one hydrogen atom in the formed ring may be substituted with an aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl (the two aryls may be bonded via a single bond or a linking group), alkyl, cycloalkyl, alkoxy, aryloxy, or substituted silyl. The aryl or heteroaryl ring formed is preferably an aryl ring having 9 to 16 carbon atoms or a heteroaryl ring having 6 to 15 carbon atoms, and at least one hydrogen atom in the formed ring may be substituted with an aryl ring having 6 to 10 carbon atoms, an alkyl ring having 1 to 12 carbon atoms, or a cycloalkyl or trialkylsilyl ring having 3 to 16 carbon atoms (wherein the alkyl is an alkyl having 1 to 4 carbon atoms).

[0169] R in equations (12), (13), (14), (15), (16), (17), (18), (19) and (20) 2 is preferably alkyl (methyl, t-butyl, etc.), substituted phenyl (2,6, dimethylphenyl, etc.), diarylamino (diphenylamino, etc.) or carbazolyl (N-carbazolyl, etc.). 2 R is a group other than 1 , R 3 is preferably each hydrogen.

[0170] In formulas (12), (13), (14), (15), (16), (17), (18), (19), and (20), X is each independently >O, >S, >Se, >NR, >Si(-R)2, or >C(-R)2. R in >NR, >Si(-R)2, or >C(-R)2 is hydrogen, aryl, heteroaryl, alkyl, or cycloalkyl, and is preferably 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. R in >NR is preferably an optionally substituted aryl, more preferably an unsubstituted aryl, and even more preferably an unsubstituted phenyl. R in >C(-R)2 is preferably both optionally substituted alkyl, more preferably both unsubstituted alkyl, and even more preferably both unsubstituted methyl. Furthermore, X is preferably >O, >S, >NR, or >C(—R) 2 , more preferably >O, >S, or >NR, and even more preferably >O or >S.

[0171] In equations (12), (13), (14), (15), (16), (17), (18), (19) and (20), Y 1 are each independently B, P, P=O, P=S, Al, Ga, As, Si-R, or Ge-R, and R in 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. Y 1 is preferably B, P, P═O, P═S, or Si—R, and particularly preferably B.

[0172] In equations (12), (13), (14), (15), (16), (17), (18), (19) and (20), X 1 and X 2are each independently >O, >NR, >Si(-R)2, >C(-R)2, >S, or >Se, and R in the >NR and >Si(-R)2 is each independently hydrogen, an optionally substituted aryl having 6 to 12 carbon atoms, an optionally substituted heteroaryl having 2 to 15 carbon atoms, an optionally substituted alkyl having 1 to 6 carbon atoms, or an optionally substituted cycloalkyl having 3 to 14 carbon atoms, and R in the >C(-R)2 is hydrogen, an optionally substituted and R in at least one of >NR, >Si(-R)2, and >C(-R)2 may be bonded to at least one ring selected from the group consisting of ring a, ring b, ring c51, and ring b61 via -O-, -S-, -C(-R)2-, or a single bond.

[0173] In the compound represented by formula (12), (13), (14), (15), (16), (17), (18), (19), or (20), at least one selected from the group consisting of aryl rings and heteroaryl rings (at least one of ring a, ring b, ring c51, ring c55, ring b61, ring b65, the formed ring, the aryl, and the heteroaryl) may be fused with at least one cycloalkane having 3 to 24 carbon atoms, at least one hydrogen atom 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 -CH2- in the cycloalkane may be substituted with -O-. In the compound represented by formula (12), (13), (14), (15), (16), (17), (18), (19), or (20), when at least one selected from the group consisting of aryl rings and heteroaryl rings is condensed with at least one cycloalkane, the at least one cycloalkane is preferably a cycloalkane having 3 to 20 carbon atoms, in which at least one hydrogen atom 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.

[0174] At least one hydrogen atom in the compound represented by formula (12), (13), (14), (15), (16), (17), (18), (19) or (20) may be substituted with deuterium, cyano or halogen.

[0175] The compounds represented by formula (12), (13), (14), (15), (16), (17), (18), (19), or (20) preferably have a structure containing at least one tertiary alkyl group represented by the above formula (tR). In particular, in each of formulas (12), (13), (14), (15), (16), (17), (18), (19), and (20), R 51 ~R 58 and R 61 ~R 68 is preferably a substituent containing tertiary alkyl (t-butyl, t-amyl, etc.), neopentyl, or adamantyl, represented by the above formula (tR).

[0176] [ka]

[0177] [ka]

[0178] [ka]

[0179] [ka]

[0180] In formulas (2-1), (3-1), (4-1), (5-1), (6-1), (7-1), (8-1), (9-1), (10-1), (11-1), (12-1), (13-1), (14-1), (15-1), (16-1), (17-1), (18-1), (19-1) and (20-1), Z is independently CR z Alternatively, N, at least one Z is N, and R z 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, or substituted silyl, and at least one hydrogen in these may be substituted with an aryl, heteroaryl, alkyl, or cycloalkyl. z are preferably 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), or an alkyl having 1 to 24 carbon atoms.

[0181] In formulae (2-1), (3-1), (4-1), (5-1), (6-1), (7-1), (8-1), (9-1), (10-1), (11-1), (12-1), (13-1), (14-1), (15-1), (16-1), (17-1), (18-1), (19-1) and (20-1), R in the a' ring z Adjacent groups in the a' ring are bonded to each other to form R in the b' ring. zAdjacent groups in the b' ring are bonded to each other to form R z Adjacent groups among these are bonded to each other to form R in ring c21' together with ring c'. z Adjacent groups in the b31' ring are bonded to each other to form the R z Adjacent groups among these are bonded to each other to form R in ring b15' together with ring b31'. z Adjacent groups among these are bonded to each other to form R in the a12' ring together with the b15' ring. z Adjacent groups among these are bonded to each other to form R in ring b41' together with ring a12'. z Adjacent groups in the b41' ring are bonded to each other to form R z Adjacent groups in the c51' ring are bonded to each other to form R z Adjacent groups in the b61' ring are bonded to each other to form the c55' ring and the R z Adjacent groups among these are bonded to each other to form R in ring b65' together with ring b61'. z Adjacent groups in the b65' ring are bonded to each other, and together with the b65' ring, R z Adjacent groups in the b70' ring are bonded to each other to form the R z Adjacent groups among may be bonded to each other to form an aryl ring or a heteroaryl ring together with the b70' ring, and at least one hydrogen atom in the formed ring may be substituted with an aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl (the two aryls may be bonded via a single bond or a linking group), alkyl, cycloalkyl, alkoxy, aryloxy, or substituted silyl. The aryl or heteroaryl ring formed is preferably an aryl ring having 9 to 16 carbon atoms or a heteroaryl ring having 6 to 15 carbon atoms, and at least one hydrogen atom in the formed ring may be substituted with an aryl ring having 6 to 10 carbon atoms, an alkyl ring having 1 to 12 carbon atoms, or a cycloalkyl or trialkylsilyl ring having 3 to 16 carbon atoms (wherein the alkyl is an alkyl having 1 to 4 carbon atoms).

[0182] In each of the formulae (2-1), (3-1), (4-1), (5-1), (6-1), (7-1), (8-1), (9-1), (10-1), (11-1), (12-1), (13-1), (14-1), (15-1), (16-1), (17-1), (18-1), (19-1), and (20-1), the number of rings (monocycles) containing Z as N is preferably 1 to 4, more preferably 1 to 3, still more preferably 1 or 2, and particularly preferably 1. In each of formulas (2-1), (3-1), (4-1), (5-1), (6-1), (10-1), (11-1), (12-1), (13-1), (14-1), (15-1), (16-1), (17-1), (18-1), (19-1), and (20-1), it is preferable that at least the a' ring is a ring containing Z that is N, and it is more preferable that only the a' ring is a ring containing Z that is N. Furthermore, in each of formulas (7-1), (8-1), and (9-1), it is preferable that at least the a' ring and the a12' ring are rings containing Z that is N, and it is more preferable that only the a' ring and the a12' ring are rings containing Z that is N. In formulas (2-1), (3-1), (4-1), (5-1), (6-1), (7-1), (8-1), (9-1), (10-1), (11-1), (12-1), (13-1), (14-1), (15-1), (16-1), (17-1), (18-1), (19-1), and (20-1), in a ring (monocyclic ring) containing Z as N, it is preferable that one or two of the multiple Zs are N, and when two are N, it is preferable that the two Ns are not adjacent to each other. The ring (monocyclic ring) containing Z as N is preferably a pyridine ring or a pyrimidine ring. When ring a' is a ring containing Z as N, it is preferably a pyridine ring, a pyrimidine ring, a pyridazine ring, or a 1,2,3-triazine ring, and more preferably a pyridine ring or a pyrimidine ring.

[0183] In formulas (2-1), (3-1), (4-1), (5-1), (6-1), (7-1), (8-1), (9-1), (10-1), (11-1), (12-1), (13-1), (14-1), (15-1), (16-1), (17-1), (18-1), (19-1), and (20-1), each X is independently >O, >S, >Se, >NR, >Si(—R)2, or >C(—R)2. R in the above >NR, >Si(-R)2, or >C(-R)2 is each independently hydrogen, aryl, heteroaryl, alkyl, or cycloalkyl, and two R may be bonded to form a ring, preferably 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. R in >NR is preferably an optionally substituted aryl, more preferably an unsubstituted aryl, and even more preferably an unsubstituted phenyl. R in >C(-R)2 is preferably both optionally substituted alkyl, more preferably both unsubstituted alkyl, and even more preferably both unsubstituted methyl. Furthermore, X is preferably >O, >S, >NR, or >C(-R)2, more preferably >O, >S, or >NR, and even more preferably >O or >S.

[0184] In equations (2-1), (3-1), (4-1), (5-1), (6-1), (7-1), (8-1), (9-1), (10-1), (11-1), (12-1), (13-1), (14-1), (15-1), (16-1), (17-1), (18-1), (19-1), and (20-1), Y 1 are each independently B, P, P=O, P=S, Al, Ga, As, Si-R, or Ge-R, and R in 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. Y 1 is preferably B, P, P═O, P═S, or Si—R, and particularly preferably B.

[0185] X in formulas (2-1), (3-1), (4-1), (5-1), (6-1), (10-1), (11-1), (12-1), (13-1), (14-1), (15-1), (16-1), (17-1), (18-1), (19-1), and (20-1) 1 and X 2 , and X in formulas (7-1), (8-1), and (9-1) 1 , X 2 , X 3 , and X 4 are each independently >O, >NR, >Si(-R)2, >C(-R)2, >S, or >Se, and R in the >NR and >Si(-R)2 is each independently an optionally substituted aryl having 6 to 12 carbon atoms, an optionally substituted heteroaryl having 2 to 15 carbon atoms, an optionally substituted alkyl having 1 to 6 carbon atoms, or an optionally substituted cycloalkyl having 3 to 14 carbon atoms, and R in the >C(-R)2 is hydrogen, an optionally substituted aryl having 6 to 12 carbon atoms, an optionally substituted heteroaryl having 2 to 15 carbon atoms, an optionally substituted alkyl having 1 to 6 carbon atoms, or an optionally substituted cycloalkyl having 3 to 14 carbon atoms. and R in at least one of >NR, >Si(-R)2, and >C(-R)2 is optionally bonded via -O-, -S-, -C(-R)2-, or a single bond to at least one ring selected from the group consisting of ring a', ring b', ring c', ring a12', ring b15', a 5-membered ring fused with ring c21', a 5-membered ring fused with ring b31', ring c51', and ring b61'.

[0186] At least one (among ring a', ring b', ring c', ring c21', ring b31', ring b15', ring a12', ring b41', ring c51', ring c55') selected from the group consisting of aryl rings and heteroaryl rings in the compounds represented by formula (2-1), (3-1), (4-1), (5-1), (6-1), (7-1), (8-1), (9-1), (10-1), (11-1), (12-1), (13-1), (14-1), (15-1), (16-1), (17-1), (18-1), (19-1) or (20-1) In the ring, at least one of ring b61', ring b65', the formed ring, the aryl, and the heteroaryl may be fused with at least one cycloalkane having 3 to 24 carbon atoms, at least one hydrogen atom 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 -CH2- in the cycloalkane may be substituted with -O-.

[0187] In the compounds represented by formula (2-1), (3-1), (4-1), (5-1), (6-1), (7-1), (8-1), (9-1), (10-1), (11-1), (12-1), (13-1), (14-1), (15-1), (16-1), (17-1), (18-1), (19-1) or (20-1), when at least one selected from the group consisting of aryl rings and heteroaryl rings is condensed with at least one cycloalkane, it is preferable that the at least one cycloalkane is a cycloalkane having 3 to 20 carbon atoms, in which at least one hydrogen atom 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.

[0188] At least one hydrogen atom in the compounds represented by formulas (2-1), (3-1), (4-1), (5-1), (6-1), (7-1), (8-1), (9-1), (10-1), (11-1), (12-1), (13-1), (14-1), (15-1), (16-1), (17-1), (18-1), (19-1) and (20-1) may be substituted with deuterium, cyano or halogen.

[0189] The compounds represented by formula (2-1), (3-1), (4-1), (5-1), (6-1), (7-1), (8-1), (9-1), (10-1), (11-1), (12-1), (13-1), (14-1), (15-1), (16-1), (17-1), (18-1), (19-1) or (20-1) preferably have a structure containing at least one tert-alkyl (t-butyl, t-amyl, etc.), neopentyl or adamantyl group represented by the above formula (tR).

[0190] Compound (1F-86) and compound (1F-87) of the examples correspond to compounds of formula (4-1) and formula (13-1), respectively, in which only the a' ring is a ring (pyridine ring) containing Z, where N. As shown in the examples (Table 2), it can be seen that organic EL devices using these compounds in the light-emitting layer can maintain high brightness for a long time, and the device life can be improved.

[0191] As described above, at least one of the aryl rings and heteroaryl rings in the chemical structure of the polycyclic aromatic compound represented by formula (1), or formula (2), (3), (4), (5), (6), (7), (8), (9), (12), (13), (14), (15), (16), (17), (18), (19), (20), (2-1), (3-1), (4-1), (5-1), (6-1), (7-1), (8-1), (9-1), (10-1), (11-1), (12-1), (13-1), (14-1), (15-1), (16-1), (17-1), (18-1), (19-1) or (20-1), and the multimer thereof, may be fused with at least one cycloalkane. By using the compound of the present invention having such a structure as a light-emitting material, the light-emitting efficiency and the life of the device can be further improved.

[0192] For example, aryl and heteroaryl rings which are rings A, B, C, a, b, c, a12, b15, c21, b31, b41, c51, c55, b61, b65, ring a', b', c', c21', b31', b15', a12', b41', c51', c55', b61', and b65'; aryl and heteroaryl rings in fused rings; aryls (aryl, diaryl) as the first and second substituents in rings A to C; aryl (an aryl moiety in heteroaryl, diheteroarylamino, diarylboryl, or aryloxy) and heteroaryl (a heteroaryl moiety in heteroaryl, diheteroarylamino, or arylheteroarylamino); aryl (similar to above) and heteroaryl (similar to above) as the first and second substituents on ring a, ring b, ring c, ring a12, ring b15, ring c21, ring b31, ring b41, ring c51, ring c55, ring b61, and ring b65; Y 1 Aryl as R in Si—R and Ge—R (as above), and X 1 , X 2 , X 3 , X 4At least one of the aryl (as above) and heteroaryl (as above) as R in >NR, >Si(—R) and >C(—R) may be fused with at least one cycloalkane.

[0193] Preferably, the aryl and heteroaryl rings are rings b61′ and b65′ in ring A, ring B, ring C, ring a, ring b, ring c, ring a12, ring b15, ring c21, ring b31, ring b41, ring c51, ring c55, ring b61, ring b65, ring a′, ring b′, ring c′, ring c21′, ring b31′, ring b15′, ring a12′, ring b41′, ring c51′, ring c55′, and ring b61′ and b65′; aryl (aryl moiety in aryl, diarylamino, diarylboryl, or aryloxy) and heteroaryl (heteroaryl moiety in heteroaryl or diheteroarylamino) as first substituents in rings A to C; aryl (similar to above) and heteroaryl (similar to above) as first substituents on rings a to c; and X 1 , X 2 , X 3 , X 4 At least one of the aryl (as above) and heteroaryl (as above) as R in >NR, >Si(—R) and >C(—R) may be fused with at least one cycloalkane.

[0194] More preferably, the aryl ring is ring b61' or b65' among ring A, ring B, ring C, ring a, ring b, ring c, ring a12, ring b15, ring c21, ring b31, ring b41, ring c51, ring c55, ring b61, ring b65', ring a', ring b', ring c', ring c21', ring b31', ring b15', ring a12', ring b41', ring c51' or ring c55', an aryl (aryl moiety in aryl or diarylamino) as the first substituent in rings A to C, and Heteroaryl (heteroaryl moiety in heteroaryl), a ring, b ring, c ring, a12 ring, b15 ring, c21 ring, b31 ring, b41 ring, c51 ring, c55 ring, b61 ring, b65 ring, a' ring, b' ring, c' ring, c21' ring, b31' ring, b15' ring, a12' ring, b41' ring, c51' ring, c55' ring, aryl (similar to above) and heteroaryl (similar to above) as the first substituent on the b61' ring and b65' ring, and X 1 , X 2 , X 3 , X 4 At least one of the aryl (as above) as R in >NR, >Si(—R) 2 and >C(—R) 2 may be fused with at least one cycloalkane.

[0195] More preferred are aryl rings that are ring b61' and ring b65' among ring A, ring B, ring C, ring a, ring b, ring c, ring a12, ring b15, ring c21, ring b31, ring b41, ring c51, ring c55, ring b61, ring b65, ring a', ring b', ring c', ring c21', ring b31', ring b15', ring a12', ring b41', ring c51' and ring c55', and aryl (aryl) as the first substituent in rings A to C. or the aryl moiety in diarylamino), an aryl (similar to above) as a first substituent on ring a, ring b, ring c, ring a12, ring b15, ring c21, ring b31, ring b41, ring c51, ring c55, ring b61, ring b65, ring a', ring b', ring c', ring c21', ring b31', ring b15', ring a12', ring b41', ring c51', ring c55', ring b61', ring b65', and X 1 , X 2 , X 3 , X 4At least one of the aryl (as above) as R in >NR, >Si(—R) 2 and >C(—R) 2 may be fused with at least one cycloalkane.

[0196] Examples of the "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.

[0197] Specific examples of the cycloalkane 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 compounds having 1 to 5 carbon atoms.

[0198] Among these, for example, as shown in the following structural formula, a structure in which at least one hydrogen atom is substituted on the α-carbon atom of a cycloalkane (in a cycloalkyl fused to an aryl ring or heteroaryl ring, the carbon atom adjacent to the fused carbon atom) is preferred, a structure in which two hydrogen atoms are substituted on the α-carbon atom is more preferred, and a structure in which a total of four hydrogen atoms are substituted on the two α-carbon atoms is even more preferred. Examples of this substituent include a C1-C5 alkyl (particularly methyl) substituent, a halogen (particularly fluorine) substituent, and a deuterium substituent.

[0199] [ka]

[0200] The number of cycloalkanes fused to one aryl ring or heteroaryl ring is preferably 1 to 3, more preferably 1 or 2, and even more preferably 1. For example, an example in which one or more cycloalkanes are fused to one benzene ring (phenyl) is shown below. * indicates the bonding position and may be any carbon that constitutes the benzene ring but not the cycloalkane. Fused cycloalkanes such as those in formula (Cy-1-4) and formula (Cy-2-4) may also be fused together. The same applies when the fused ring (group) is an aryl ring or heteroaryl ring other than a benzene ring (phenyl), or when the fused cycloalkane is a cycloalkane other than cyclopentane or cyclohexane. [ka]

[0201] At least one -CH2- in a cycloalkane may be replaced with -O-. For example, an example in which one or more -CH2- in a cycloalkane fused to a benzene ring (phenyl) are replaced with -O- is shown below. The same applies even when the fused ring (group) is an aromatic ring or heteroaromatic ring other than a benzene ring (phenyl), or when the fused cycloalkane is a cycloalkane other than cyclopentane or cyclohexane.

[0202] [ka]

[0203] At least one hydrogen atom in the cycloalkane may be substituted. Examples of the substituent include aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl (the 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 above. 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. Furthermore, when cycloalkyl is substituted, it may be substituted to form a spiro structure, examples of which are shown below.

[0204] [ka]

[0205] As for the form of cycloalkane condensation, first, the A ring, B ring, and C ring in formula (1) (formulas (2), (3), (4), (5), (6), (7), (8), (9), (12), (13), (14), (15), (16), (17), (18), (19), (20), (2-1), (3-1), (4-1), (5-1), (6-1), (7-1), (8-1), (9-1), (10-1), (11-1), (12-1), (13-1), (14-1), (15-1), (16-1), (17) In particular, the ring b of formula (3) (particularly R 9 and R 10are bonded to form a ring), the c21 ring of formula (3), the b ring of formula (4) (especially R 9 and R 10 are bonded to form a ring), the c21 ring of formula (4) (especially R 22 and R 23 is preferably condensed with a cycloalkane such that the bond forms a ring.

[0206] Other forms of cycloalkane condensation include those represented by formula (1) or formulas (2), (3), (4), (5), (6), (7), (8), (9), (12), (13), (14), (15), (16), (17), (18), (19), (20), (2-1), (3-1), (4-1), (5-1), (6-1), (7-1), (8-1), (9-1), (10-1), (11-1), (12-1), (13-1), (14-1), (15-1), (16-1), ( Examples of polycyclic aromatic compounds and multimers thereof represented by 17-1), (18-1), (19-1), or (20-1) include those having >NR, where R is an aryl fused with a cycloalkane, a diarylamino fused with a cycloalkane (fused to the aryl moiety), a carbazolyl fused with a cycloalkane (fused to the benzene ring moiety), or a benzocarbazolyl fused with a cycloalkane (fused to the benzene ring moiety). Examples of "diarylamino" include the groups described above as the "first substituent."

[0207] Further, more specific examples include polycyclic aromatic compounds represented by formula (2), (3), (4), (5), (6), (7), (8), (9), (12), (13), (14), (15), (16), (17), (18), (19), (20), (2-1), (3-1), (4-1), (5-1), (6-1), (7-1), (8-1), (9-1), (10-1), (11-1), (12-1), (13-1), (14-1), (15-1), (16-1), (17-1), (18-1), (19-1), or (20-1), and R in the multimers thereof. 2is a diarylamino fused to a cycloalkane (fused to the aryl moiety) or a carbazolyl fused to a cycloalkane (fused to the benzene ring moiety).

[0208] An example of this is a polycyclic aromatic compound represented by the following formula (2-A), or a multimer of a polycyclic aromatic compound having a plurality of structures represented by the following formula (2-A): Cy is a cycloalkane, n is each independently an integer of 1 to 3 (preferably 1), and "=(Cy)n" means that n cycloalkanes are fused at any position of the structure to be condensed (in the following formula (2-A), n cycloalkanes are fused to a benzene ring (phenyl)), and the definition of each symbol in the structural formula is the same as the definition of each symbol in formula (2). In the following formulae, at least one of ring a, ring b, and ring c is a fused ring according to the formula (2), (3), (4), (5), (6), (7), (8), (9), (12), (13), (14), (15), (16), (17), (18), (19), (20), (2-1), (3-1), (4-1), (5-1), (6-1), (7-1), (8-1), (9-1), (10-1), (11-1), (12-1), (13-1), (14-1), (15-1), (16-1), (17-1), (18-1), (19-1), or (20-1).

[0209] [ka]

[0210] Specifically, compounds represented by the following formulas are exemplified. In the following formulas, "Cy" represents a cycloalkane, and each n is independently 0 to the maximum number that can be condensed (however, not all n's are 0), preferably 0 to 2 (however, not all n's are 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 "1-Cy-(1)", n cycloalkanes are condensed at any position of each benzene ring). In the following structural formulas, "OPh" represents phenoxy, "Me" represents methyl, and each compound may be substituted with the first and second substituents described above. In the following formulas, Y in formula (1) 1 At least one of the rings bonded to an element corresponding to formula (2), (3), (4), (5), (6), (7), (8), (9), (12), (13), (14), (15), (16), (17), (18), (19), (20), (2-1), (3-1), (4-1), (5-1), (6-1), (7-1), (8-1), (9-1), (10-1 ), (11-1), (12-1), (13-1), (14-1), (15-1), (16-1), (17-1), (18-1), (19-1), or (20-1), and is a fused ring composed of two or more rings selected from the group consisting of a monocyclic aryl ring, a monocyclic heteroaryl ring, and a cyclopentadiene ring.

[0211] [ka]

[0212] [ka]

[0213] [ka]

[0214] [ka]

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[0225] 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 electroluminescent device, an organic field effect transistor, and an organic thin-film solar cell. In particular, in an organic electroluminescent device, a compound represented by Y in any of the above formulas can be used as a dopant material for the light-emitting layer. 1 is B, X 1 and X 2 (and X 3 and X 4 ) is >NR, Y 1 is B, X 1 (and X 4 or X 3 ) is > O, X 2 (and X 3 or X 4 ) is >NR, Y 1 is B, X 1 and X 2 (and X 3 and X 4 ) is >O, Y 1 is B, X 1 and X 2 (and X 3 and X 4 ) is >C(-R)2, and Y 1 is B, X 1 and X 2 (and X 3 and X 4 ) is >NR, Y 1 is B, X 1 and X 2 (and X 3 and X 4 ) is more preferably >C(-R)2, and Y 1 is B, X 1 and X 2 (and X 3 and X 4 The most preferred compound is a compound in which Y is a fluorine-containing compound. 1 is B, X 1 (and X 4 or X 3 ) is > O, X 2 (and X 3or X 4 ) is >NR, Y 1 is B, X 1 and X 2 (and X 3 and X 4 ) is >O, and as an electron transporting material, Y 1 is B, X 1 and X 2 (and X 3 and X 4 ) is >O, Y 1 P=O,X 1 and X 2 (and X 3 and X 4 ) is preferably used.

[0226] Further specific examples of the polycyclic aromatic compound of the present invention include compounds represented by the following structural formulas: In the structural formulas, "D" represents deuterium, "Me" represents methyl, "tBu" represents t-butyl, and "tAm" represents t-amyl.

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[0709] [ka]

[0710] The polycyclic aromatic compound represented by formula (1) according to the present invention and its multimer can also be used as a material for organic devices, such as 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 crosslinked polymer obtained by further crosslinking the pendant polymer compound (the pendant polymer compound for obtaining this crosslinked pendant polymer has a crosslinkable substituent).

[0711] The reactive substituents mentioned above (including the polymerizable substituents, crosslinkable substituents, and reactive substituents for obtaining a pendant polymer, hereinafter simply referred to 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 pendantly reacting with a main-chain polymer, but examples include unsaturated alkenyl, alkynyl, and cycloalkyl (e.g., cyclobutenyl), groups in which at least one -CH2- in a cycloalkyl is replaced with -O- (e.g., epoxy), and unsaturated condensed cycloalkanes (e.g., condensed cyclobutene), and substituents with the following structures are preferred: * in each structural formula indicates a bond position.

[0712] [ka]

[0713] L's are each independently a single bond, -O-, -S-, >C=O, -OC(=O)-, alkylene having 1 to 12 carbon atoms, oxyalkylene having 1 to 12 carbon atoms, and polyoxyalkylene having 1 to 12 carbon atoms. Among the above substituents, groups represented by formula (XLS-1), formula (XLS-2), formula (XLS-3), formula (XLS-9), formula (XLS-10) or formula (XLS-17) are preferred, and groups represented by formula (XLS-1), formula (XLS-3) or formula (XLS-17) are more preferred.

[0714] The uses of such polymer compounds, crosslinked polymers, pendant polymer compounds, and pendant crosslinked polymers (hereinafter simply referred to as "polymer compounds and crosslinked polymers") will be described in detail below.

[0715] 2. Method for producing polycyclic aromatic compounds and their polymers The polycyclic aromatic compounds and their multimers represented by formula (1) or formula (2), (3), (4), (5), (6), (7), (8), (9), (12), (13), (14), (15), (16), (17), (18), or (19) are basically prepared by first connecting the A ring (a ring) with the B ring (b ring) and the C ring (c ring) through bonding groups (X 1 or X 2 A ring A (ring a), a ring B (ring b) and a ring C (ring c) are bonded together with a bonding group (Y 1The final product can be produced by bonding the two rings together with a group containing a nucleophilic substitution group (the second reaction). For example, in the first reaction, etherification reactions can be performed using common reactions such as nucleophilic substitution or the Ullmann reaction, while amination reactions can be performed using common reactions such as the Buchwald-Hartwig reaction. Furthermore, in the second reaction, a tandem hetero-Friedel-Crafts reaction (sequential aromatic electrophilic substitution reaction, hereinafter the same) can be used. By using a raw material with the desired fused ring somewhere in the reaction process or by adding a ring fusion step, it is possible to produce a compound with a fused ring structure in which at least one ring selected from the group consisting of ring A, ring B, and ring C is composed of two or more rings selected from the group consisting of a monocyclic aryl ring, a monocyclic heteroaryl ring, and a cyclopentadiene ring.

[0716] Manufacturing method via intermediate-1 The polycyclic aromatic compound of the present invention can be produced by a production method including the following steps. For each of the steps, reference can be made to the description in WO 2015 / 102118. Using an organic alkali compound, X in the following intermediate-1 is obtained. 1 and X 2 a reaction step of metallating the halogen atom (Hal) between Y 1 Halides of Y 1 Aminated halides of Y 1 Alkoxylated compounds of Y 1 and Y are reacted with a reagent selected from the group consisting of aryl oxy compounds of the formula 1 and a reaction step of exchanging Y with a Bronsted base by successive electrophilic aromatic substitution reactions. 1 and a reaction step of bonding the B ring and the C ring together.

[0717] [ka]

[0718] Manufacturing method via intermediate-2 The polycyclic aromatic compound of the present invention is also preferably produced by a production method including a reaction step of reacting the following intermediate-2 with an acid. [ka] (In Intermediate-2, Z is -B(OH)2 which may be esterified.)

[0719] Z in Intermediate-2 is -B(OH)2 which may be esterified. 1 is the group to which -B(OH)2 has been esterified.

[0720] The group (-B(OR)2) obtained by esterifying -B(OH)2 is not particularly limited, and examples thereof include groups obtained by reacting alcohols including diols or carboxylic acids with boronic acids. R in -B(OR)2 includes optionally substituted alkyls having 1 to 4 carbon atoms (branched alkyls having 3 to 4 carbon atoms), and R groups may be bonded to each other to form a ring, or the formed ring may contain an aromatic ring such as benzene. Specific examples include groups with the following structures. In the following structures, "Me" represents methyl, "Et" represents ethyl, "iPr" represents isopropyl, and * represents the bonding position.

[0721] [ka]

[0722] Method for producing boronic acids or boronic esters such as intermediate-2 The compound represented by Intermediate-2 (boronic acid or boronic acid ester) basically has a bonding group (X 1 and X 2 ) to produce an intermediate (first reaction), followed by Y 1By introducing a group, a boronic acid ester can be produced, and then hydrolysis of this ester produces the corresponding boronic acid. For the first reaction, for example, etherification reactions can be performed using common reactions such as nucleophilic substitution or the Ullmann reaction, while amination reactions can be performed using common reactions such as the Buchwald-Hartwig reaction. The symbols in the structural formulas shown below are defined as above.

[0723] The second reaction is carried out by reacting the intermediate obtained in the first reaction with Y as shown in the following scheme (1) or (2). 1 This reaction introduces a boronic ester such as Bpin (pinacolatoboryl).

[0724] [ka]

[0725] In the above schemes (1) and (2), the hydrogen atom is first orthometalated with n-butyllithium, sec-butyllithium, or t-butyllithium, etc., to form a lithiated product. While n-butyllithium, sec-butyllithium, or t-butyllithium is used alone, N,N,N',N'-tetramethylethylenediamine or other suitable amines may be added to improve reactivity. The resulting lithiated product can then be treated with a boronate esterification reagent, such as 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane, to produce a pinacol ester of boronic acid. While 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane is used here, other suitable reagents, such as trimethoxyborane and triisopropoxyborane, can also be used. Furthermore, 4,4,5,5-tetramethyl-1,3,2-dioxaborolane can also be used, as described in International Publication WO 2013 / 016185.

[0726] Furthermore, as shown in the following scheme (3) or (4), a boronic acid can be produced by hydrolyzing the boronic acid ester produced by the method of the above scheme (1) or (2).

[0727] [ka]

[0728] Furthermore, by reacting a suitable alcohol with the boronic acid ester or boronic acid obtained in the above schemes (1) to (4), a different boronic acid ester can be produced through transesterification or re-esterification.

[0729] While the above schemes (1) and (2) show methods for producing boronic acid esters represented by formula (1) or (2), multimeric compounds having multiple structures represented by formula (1) or (2) 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 (5) to (7). In this case, target products such as dimeric compounds and trimeric compounds can be obtained by doubling or tripling the amount of the reagent, such as butyllithium, used.

[0730] [ka]

[0731] [ka]

[0732] [ka]

[0733] The above schemes (5) to (7) show methods for producing polymeric compounds of boronate esters. However, the boronic acid derivatives can be produced by hydrolysis according to the above scheme (4), and different ester derivatives can also be produced by transesterification or re-esterification using alcohols.

[0734] By appropriately selecting the above synthesis method and the raw materials to be used, a boronic acid or a boronic acid ester having a substituent at a desired position can be synthesized.

[0735] In the above schemes (1) to (7), lithium was introduced into the desired position by orthometalation, but lithium can also be introduced into the desired position by introducing a halogen such as a bromine atom into the desired position and then performing halogen-metal exchange, as in the following schemes (8) or (9).A boronate ester can then be produced from the resulting lithiated product.

[0736] [ka]

[0737] In the above schemes (8) and (9), the halogen atom is first lithiated by halogen-lithium exchange with n-butyllithium, sec-butyllithium, or t-butyllithium. While n-butyllithium, sec-butyllithium, or t-butyllithium alone is used here, N,N,N',N'-tetramethylethylenediamine or other suitable amines may be added to improve reactivity. The resulting lithiated product can then be treated with a boronate esterification reagent such as 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane to produce pinacol esters of boronic acid. While 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane is used here, other suitable reagents, such as trimethoxyborane and triisopropoxyborane, can also be used. Furthermore, 4,4,5,5-tetramethyl-1,3,2-dioxaborolane can be used in a similar manner, as described in International Publication WO 2013 / 016185.

[0738] The above schemes (8) and (9) show methods for producing boronic acid esters represented by formula (1) or (2). However, boronic acids can be produced by hydrolyzing the boronic acid esters thus obtained (see schemes (3) or (4) above). Furthermore, by reacting these boronic acid esters or boronic acids with an appropriate alcohol, different boronic acid esters can be produced through transesterification or re-esterification. Furthermore, multimeric compounds having multiple structures represented by formula (1) or (2) can also be produced by using intermediates having multiple A rings (a-rings), B rings (b-rings), and C rings (c-rings) (see schemes (5) to (7) above).

[0739] Alternatively, as shown in the following schemes (10) or (11), a boronate ester can be similarly synthesized by coupling the brominated product with bis(pinacolato)diboron or 4,4,5,5-tetramethyl-1,3,2-dioxaborolane, etc., using a palladium catalyst and a base.

[0740] [ka]

[0741] The above schemes (10) and (11) show methods for producing boronic acid esters represented by formula (1) or (2). However, boronic acids can be produced by hydrolyzing the boronic acid esters thus obtained (see schemes (3) or (4) above). Furthermore, by reacting these boronic acid esters or boronic acids with an appropriate alcohol, different boronic acid esters can be produced through transesterification or re-esterification. Furthermore, multimeric compounds having multiple structures represented by formula (1) or (2) can also be produced by using intermediates having multiple A rings (a-rings), B rings (b-rings), and C rings (c-rings) (see schemes (5) to (7) above).

[0742] Metalating reagents used in the halogen-metal exchange reaction in the schemes explained so far include alkyllithiums such as methyllithium, n-butyllithium, sec-butyllithium, and t-butyllithium, isopropylmagnesium chloride, isopropylmagnesium bromide, phenylmagnesium chloride, phenylmagnesium bromide, and lithium chloride complexes of isopropylmagnesium chloride, known as turboGrignard reagents.

[0743] In addition to the reagents mentioned above, the metalation reagents used in the ortho-metalation reactions in the schemes described so far include organic alkali compounds such as lithium diisopropylamide, lithium tetramethylpiperidide, lithium hexamethyldisilazide, potassium hexamethyldisilazide, lithium chloride tetramethylpiperidinylmagnesium-lithium chloride complex, and lithium tri-n-butylmagnesium oxide.

[0744] Furthermore, when alkyllithium is used as the metalation reagent, additives that promote the reaction include N,N,N',N'-tetramethylethylenediamine, 1,4-diazabicyclo[2.2.2]octane, and N,N-dimethylpropyleneurea.

[0745] The boronic acids or boronic acid esters of the present invention also include those in which at least a portion of the hydrogen atoms is substituted with deuterium or with a halogen such as fluorine or chlorine. Such compounds can be synthesized in the same manner as described above by using starting materials in which the desired positions are deuterated, fluorinated, or chlorinated.

[0746] Intermediate-2: A method for producing polycyclic aromatic compounds from boronic acids, etc. Next, methods for producing polycyclic aromatic compounds and polycyclic aromatic multimeric compounds using boronic acids or boronic acid esters represented by intermediate-2 compounds, etc. will be described. Note that the symbols in the structural formulae in each of the schemes shown below are the same as defined above.

[0747] In the following scheme (12) or (13), a polycyclic aromatic compound can be produced by reacting a boronic acid or a boronic acid ester represented by an intermediate-2 compound or the like with a Lewis acid such as aluminum chloride.

[0748] [ka]

[0749] Alternatively, a Bronsted acid such as p-toluenesulfonic acid can be used. In particular, when the reaction is carried out using a Lewis acid, a base such as diisopropylethylamine can be added to improve selectivity and yield.

[0750] Furthermore, polycyclic aromatic polymeric compounds can also be produced using polymeric compounds having multiple structures represented by Intermediate-2 by the methods shown in the following schemes (14) to (16). In this case, the target products such as dimeric compounds and trimeric compounds can be obtained by doubling or tripling the amount of a reagent such as aluminum chloride used depending on the structure of the polymeric compound.

[0751] [ka]

[0752] [ka]

[0753] [ka]

[0754] Examples of Lewis acids used in the above schemes (12) to (16) include AlCl3, AlBr3, AlF3, BF3·OEt2, BCl3, BBr3, GaCl3, GaBr3, InCl3, InBr3, In(OTf)3, SnCl4, SnBr4, AgOTf, ScCl3, Sc(OTf)3, ZnCl2, ZnBr2, Zn(OTf)2, MgCl2, MgBr2, Mg(OTf)2, LiOTf, NaOTf, KOTf, Me3SiOTf, Cu(OTf)2, CuCl2, YCl3, Y(OTf)3, TiCl4, TiBr4, ZrCl4, ZrBr4, FeCl3, FeBr3, CoCl3, and CoBr3. Solid-supported versions of these Lewis acids can also be used.

[0755] Examples of Bronsted acids used in the above schemes (12) to (16) include p-toluenesulfonic acid, methanesulfonic acid, trifluoromethanesulfonic acid, fluorosulfonic acid, carborane acid, trifluoroacetic acid, (trifluoromethanesulfonyl)imide, tris(trifluoromethanesulfonyl)methane, hydrogen chloride, hydrogen bromide, and hydrogen fluoride. Examples of solid Bronsted acids include Amberlyst (Dow Chemical), Nafion (DuPont), zeolite, and Teikacure (Teika Corporation).

[0756] Examples of amines that may be added in the above schemes (12) to (16) include diisopropylethylamine, triethylamine, tributylamine, 1,4-diazabicyclo[2.2.2]octane, N,N-dimethyl-p-toluidine, N,N-dimethylaniline, pyridine, 2,6-lutidine, and 2,6-di-t-butylamine.

[0757] Examples of solvents used in the above schemes (12) to (16) include o-dichlorobenzene, chlorobenzene, toluene, benzene, methylene chloride, chloroform, dichloroethylene, benzotrifluoride, decalin, cyclohexane, hexane, heptane, 1,2,4-trimethylbenzene, xylene, diphenyl ether, anisole, cyclopentyl methyl ether, tetrahydrofuran, dioxane, and methyl t-butyl ether.

[0758] Next, as an example, Y 1 is a phosphorus sulfide, a phosphorus oxide, or a phosphorus atom, and X 1 and X 2 The cases where X is an oxygen atom are shown in the following schemes (17-1), (17-2), (18) to (19). 1 and X 2The hydrogen atom between the two is orthometalated with n-butyllithium or the like. Then, 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 a tandem phospha-Friedel-Crafts reaction, resulting in the formation of 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 is a phosphorus atom.

[0759] [ka]

[0760] Also, Y 1 is phosphorus sulfide, X 1 and X 2 For polymers in which Y is an oxygen atom, lithium can also be introduced to the desired position by introducing a halogen atom such as a bromine atom or a chlorine atom into the desired position as in the above schemes (6) and (7), and then by halogen-metal exchange (see schemes (20), (21), and (22) below). 1 is phosphorus sulfide, X 1 and X 2 The polymers in which Y is an oxygen atom can also be obtained by treating with m-chloroperbenzoic acid (m-CPBA) as in the above schemes (18) and (19). 1 is a phosphorus oxide, and by treating with triethylphosphine, Y 1 is a phosphorus atom.

[0761] [ka]

[0762] Here, Y 1is B, P, P=O or P=S, and X 1 and X 2 Although the examples where is O or NR have been described, by changing the raw materials appropriately, Y 1 is Al, Ga, As, Si-R or Ge-R, or 1 and X 2 Compounds where is S can also be synthesized.

[0763] Specific examples of solvents used in the above reactions include t-butylbenzene and xylene.

[0764] In addition, in formula (2), the substituents R 1 ~R 11 Adjacent groups among these may be bonded to form an aryl or heteroaryl ring together with ring a, ring b, or ring c, and at least one hydrogen atom in the formed ring may be substituted with an aryl or heteroaryl. Therefore, the ring structure constituting the polycyclic aromatic compound represented by formula (2) changes depending on the mutual bonding form of the substituents in ring a, ring b, and ring c, as shown in formulas (2-1) and (2-2) in schemes (23) and (24) below. These compounds can be synthesized by applying the synthetic methods shown in schemes (1) to (19) above to the intermediates shown in schemes (23) and (24) below.

[0765] [ka]

[0766] The A' ring, the B' ring and the C' ring in the formula (2-1) and the formula (2-2) are each independently a substituent R 1 ~R 11 Adjacent groups in the above are bonded to form an aryl or heteroaryl ring together with ring a, ring b, and ring c, respectively (this can also be considered a fused ring formed by fusing ring a, ring b, or ring c with another ring structure). Although not shown in the formula, there are also compounds in which ring a, ring b, and ring c are all replaced by ring A', ring B', and ring C'.

[0767] In addition, the provision in formula (2) that "R in at least one of the >NR, >Si(-R)2, and >C(-R)2 is bonded to at least one of the ring a, ring b, and ring c via -O-, -S-, -C(-R)2-, or a single bond" is also applicable to X represented by formula (2-3-1) 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 (2-3-2) or formula (2-3-3), 1 or X 2 These compounds can be synthesized by applying the synthetic methods shown in the above schemes (1) to (19) to the intermediates shown in the following scheme (25).

[0768] [ka]

[0769] In the synthesis methods of the above schemes (17-1), (17-2) and (20) to (25), before adding boron trichloride, boron tribromide, etc., X 1 and X 2 In the example shown, the hydrogen atom (or halogen atom) between the two is orthometalated with butyllithium or the like to perform a tandem hetero-Friedel-Crafts reaction. However, the reaction can also proceed by adding boron trichloride or boron tribromide without orthometalation using butyllithium or the like.

[0770] Also, Y 1 When the compound is phosphorus-based, X 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 bis(diethylaminochlorophosphine) is added to perform lithium-phosphorus metal exchange. A Lewis acid such as aluminum trichloride is then added to carry out a tandem phosphat-Friedel-Crafts reaction, thereby obtaining the target compound. This reaction method is also described in WO 2010 / 104047 (e.g., page 27).

[0771] [ka]

[0772] In the above schemes (26) and (27), a polymeric compound can also be synthesized by using an orthometalation reagent such as butyllithium in a molar amount that is two or three times the molar amount of intermediate 1. Furthermore, a halogen atom such as a bromine atom or a chlorine atom can be introduced in advance to the position where a metal such as lithium is to be introduced, and then the metal can be introduced to the desired position by halogen-metal exchange.

[0773] Furthermore, for compounds condensed with a cycloalkane, 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.

[0774] In addition, for the polycyclic aromatic compound represented by formula (2-A), a cycloalkane-fused intermediate can be synthesized and then cyclized to synthesize a polycyclic aromatic compound fused with a cycloalkane at a desired position, 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 in formula (2).

[0775] [ka]

[0776] The intermediate before cyclization in Scheme (28) can also be used to synthesize intermediates with desired substituents by appropriately combining Buchwald-Hartwig reaction, Suzuki coupling reaction, or etherification reaction such as nucleophilic substitution reaction or Ullmann reaction. In these reactions, commercially available raw materials can be used as the cycloalkane-condensed precursor.

[0777] The compound of formula (2-A) having a cycloalkane-fused diphenylamino can also be synthesized by the following method: That is, after introducing a cycloalkane-fused diphenylamino by an amination reaction such as the Buchwald-Hartwig reaction of a cycloalkane-fused bromobenzene with a trihalogenated aniline, X 1 , X 2 When is NR, X 1 , X 2 When is O, etherification with phenol can lead to intermediate (M-3), which can then be transmetallated with a metalating agent such as butyllithium, followed by a tandem B-Friedel-Crafts reaction with a boron halide such as boron tribromide and a Brønsted base such as diethylisopropylamine to give compounds of formula (2-A). These reactions can also be applied to other cycloalkane-fused compounds.

[0778] Examples of orthometalation reagents used in the above scheme 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 sodium.

[0779] The metal-Y used in the above scheme 1 As a metal exchange reagent for1 trifluoride, Y 1 trichloride, Y 1 tribromide, Y 1 Y triiodide etc. 1 Halides of Y such as CIPN(NEt2)2 1 Aminated halides of Y 1 Alkoxylated compounds of Y 1 Examples include aryloxy compounds of the above.

[0780] Examples of Bronsted bases used in the above scheme 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, ArBNa, ArBK, ArB, and ArSi (wherein Ar is an aryl such as phenyl).

[0781] Lewis acids used in the above scheme include AlCl3, AlBr3, AlF3, BF3·OEt2, BCl3, BBr3, GaCl3, GaBr3, InCl3, InBr3, In(OTf)3, SnCl4, SnBr4, AgOTf, ScCl3, Sc(OTf)3, ZnCl2, ZnBr2, Zn(OTf)2, MgCl2, MgBr2, Mg(OTf)2, LiOTf, NaOTf, KOTf, Me3SiOTf, Cu(OTf)2, CuCl2, YCl3, Y(OTf)3, TiCl4, TiBr4, ZrCl4, ZrBr4, FeCl3, FeBr3, CoCl3, and CoBr3.

[0782] In the above scheme, a Bronsted base or Lewis acid may be used to promote the tandem hetero-Friedel-Crafts reaction. 1 trifluoride, Y 1 trichloride, Y 1 tribromide, Y 1 Y triiodide etc. 1When 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 is used, an amine or alcohol is produced as the aromatic electrophilic substitution reaction proceeds, so in many cases it is not necessary to use a Brønsted base. However, because the amino and alkoxy groups have low elimination ability, it is effective to use a Lewis acid to promote their elimination.

[0783] The polycyclic aromatic compound and its multimer of the present invention also include compounds in which at least some of the hydrogen atoms are substituted with deuterium or cyano, or compounds in which at least some of the hydrogen atoms are substituted with halogen such as fluorine or chlorine. Such compounds can be synthesized in the same manner as described above by using raw materials in which the desired positions are deuterated, cyanated, fluorinated, or chlorinated.

[0784] 3. Organic Devices The amino-substituted polycyclic aromatic compound according to the present invention can be used as a material for organic devices, such as organic electroluminescent devices, organic field-effect transistors, and organic thin-film solar cells.

[0785] 3-1. Organic electroluminescent device The organic EL element according to this embodiment will be described in detail below with reference to the drawings: Figure 1 is a schematic cross-sectional view showing the organic EL element according to this embodiment.

[0786] <Structure of organic electroluminescent device> The organic EL device 100 shown in FIG. 1 includes a substrate 101, an anode 102 provided on the substrate 101, a hole injection layer 103 provided on the anode 102, a hole 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.

[0787] 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.

[0788] Not all of the above layers are essential, and the minimum structural unit is a configuration 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 optionally provided. Furthermore, each of the above layers may consist of a single layer or multiple layers.

[0789] The layers constituting the organic EL element may be configured as follows: "substrate / anode / hole injection layer / hole transport layer / light-emitting layer / electron transport layer / electron injection layer / cathode" as described above, as well as "substrate / anode / hole transport layer / light-emitting layer / electron transport layer / electron injection layer / cathode", "substrate / anode / hole injection layer / light-emitting layer / electron transport layer / electron injection layer / cathode", "substrate / anode / hole injection layer / hole transport layer / light-emitting ... 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 injection layer / cathode," "substrate / anode / hole transport layer / light-emitting layer / electron transport layer / cathode," "substrate / anode / hole injection layer / light-emitting layer / electron injection layer / cathode," "substrate / anode / hole injection layer / light-emitting layer / electron transport layer / cathode," "substrate / anode / light-emitting layer / electron transport layer / cathode," or "substrate / anode / light-emitting layer / electron injection layer / cathode."

[0790] <Substrate in organic electroluminescent device> The substrate 101 is a support for the organic EL device 100 and is typically made of quartz, glass, metal, plastic, or the like. The substrate 101 may be formed into a plate, film, or sheet shape depending on the purpose, and may be, for example, a glass plate, a metal plate, a metal foil, a plastic film, or a plastic sheet. Glass plates and plates made of transparent synthetic resins such as polyester, polymethacrylate, polycarbonate, and polysulfone are preferred. For glass substrates, soda-lime glass or alkali-free glass may be used. The thickness should be sufficient to maintain mechanical strength, e.g., 0.2 mm or more. The upper limit of the thickness is, for example, 2 mm or less, preferably 1 mm or less. Regarding the glass material, alkali-free glass is preferred because it minimizes ion elution from the glass. However, commercially available soda-lime glass coated with a barrier coating such as SiO2 can also be used. In addition, in order to improve the gas barrier properties of the substrate 101, a gas barrier film such as a dense silicon oxide film may be provided on at least one side thereof, and it is particularly preferable to provide a gas barrier film when a synthetic resin plate, film, or sheet with poor gas barrier properties is used as the substrate 101.

[0791] <Anode in organic electroluminescent device> The anode 102 serves to inject holes into the light-emitting layer 105. When the hole injection layer 103 and / or the hole transport layer 104 are provided between the anode 102 and the light-emitting layer 105, holes are injected into the light-emitting layer 105 via these layers.

[0792] Materials for forming the anode 102 include inorganic 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), and conductive polymers such as polypyrrole and polyaniline. In addition, materials can be appropriately selected from those used as anodes in organic EL devices.

[0793] The resistance of the transparent electrode is not limited as long as it can supply sufficient current to light the light-emitting element, but low resistance is desirable from the perspective of the power consumption of the light-emitting element. For example, an ITO substrate with a resistance of 300 Ω / □ or less can function as an element electrode, but since substrates with a resistance of about 10 Ω / □ are now available, it is particularly desirable to use a low resistance product with a resistance of, for example, 100 to 5 Ω / □, preferably 50 to 5 Ω / □. The thickness of the ITO can be selected arbitrarily depending on the resistance value, but it is usually between 50 and 300 nm.

[0794] <Hole injection layer and hole transport layer in organic electroluminescent device> The hole injection layer 103 serves to efficiently inject holes migrating from the anode 102 into the light-emitting layer 105 or the hole transport layer 104. The hole transport layer 104 serves to efficiently transport 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 or 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.

[0795] A hole injection / transport material must be able to efficiently inject and transport holes from the positive electrode between electrodes to which an electric field is applied, and it is desirable for it to have high hole injection efficiency and efficiently transport the injected holes. To achieve this, it is desirable for the material to have a low ionization potential, high hole mobility, excellent stability, and a low tendency for impurities that act as traps to be generated during production and use.

[0796] As materials 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 devices. Specific examples thereof 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 group in the main chain or side chain, 1,1-bis(4-di-p-tolylaminophenyl)cyclohexane, N,N'-diphenyl-N,N'-di(3-methylphenyl)-4,4'-diaminobiphenyl, N,N'-diphenyl-N,N'-dinaphthyl-4,4'-diaminobiphenyl, N,N'-diphenyl-N,N'-di(3-methylphenyl)-4,4'-diphenyl-1,1'-diamine, N,N'-dinaphthyl-N,N'-diphenyl-4,4'-diphenyl-1,1'-diamine, N4 ,N 4’ -diphenyl-N 4 ,N 4’ -bis(9-phenyl-9H-carbazol-3-yl)-[1,1'-biphenyl]-4,4'-diamine, N 4 ,N 4 ,N 4’ ,N 4’ -tetra[1,1'-biphenyl]-4-yl)-[1,1'-biphenyl]-4,4'-diamine, 4,4',4"-tris(3-methylphenyl(phenyl)amino)triphenylamine, N-([1,1'-biphenyl]-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluoren-2-amine, N,N-bis(4-(dibenzo[b,d]furan-4-yl)phenyl)-[1,1':4',1"-terphenyl]- Examples of suitable polymers include triphenylamine derivatives such as 4-amine, starburst amine derivatives, stilbene derivatives, phthalocyanine derivatives (metal-free, copper phthalocyanine, etc.), pyrazoline derivatives, hydrazone compounds, benzofuran derivatives, thiophene derivatives, oxadiazole derivatives, quinoxaline derivatives (e.g., 1,4,5,8,9,12-hexaazatriphenylene-2,3,6,7,10,11-hexacarbonitrile), heterocyclic compounds such as porphyrin derivatives, and polysilanes. Among polymers, polycarbonates and styrene derivatives having the above-mentioned monomers in their side chains, polyvinylcarbazole, and polysilanes are preferred, but any suitable polymer may be used as long as it can form a thin film necessary for fabricating a light-emitting device, can inject holes from the anode, and can transport holes.

[0797] It is also known that the conductivity of organic semiconductors is strongly influenced by doping. Organic semiconductor matrix materials consist of compounds with good electron-donating or electron-accepting properties. Strong electron acceptors such as tetracyanoquinone dimethane (TCNQ) or 2,3,5,6-tetrafluorotetracyano-1,4-benzoquinone dimethane (F4TCNQ) are known for doping with electron-donating substances (see, for example, M. Pfeiffer, A. Beyer, T. Fritz, K. Leo, Appl. Phys. Lett., 73(22), 3202-3204 (1998) and J. Blochwitz, M. Pfeiffer, T. Fritz, K. Leo, Appl. Phys. Lett., 73(6), 729-731 (1998)). These generate so-called holes via an electron transfer process in the electron-donating base material (hole-transporting material). The conductivity of the base material varies considerably depending on the number and mobility of holes. Known matrix materials with hole transport properties include benzidine derivatives (such as TPD) or starburst amine derivatives (such as TDATA), as well as certain metal phthalocyanines (e.g., zinc phthalocyanine (ZnPc)) (see JP 2005-167175 A).

[0798] The hole injection layer material and the hole transport layer material described above can also be used as hole layer materials in the form of polymer compounds 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. Regarding the reactive substituent in this case, the same explanation as for the polycyclic aromatic compound represented by formula (1) can be cited. The uses of such polymer compounds and crosslinked polymers will be described in detail below.

[0799] <Light-emitting layer in organic electroluminescent device> The light-emitting layer 105 is a layer that emits light by recombining holes injected from the anode 102 and electrons injected from the cathode 108 between electrodes to which an electric field is applied. The material for the light-emitting layer 105 may be a compound (light-emitting compound) that is excited and emits light by the recombination of holes and electrons, and is preferably a compound that can be formed into a stable thin film and exhibits strong luminescence (fluorescence) efficiency in a solid state. In the present invention, the material for the light-emitting layer can be a host material and, for example, a polycyclic aromatic compound represented by formula (1) as a dopant material.

[0800] The light-emitting layer may be a single layer or multiple layers, each 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 entirely or partially in the host material. As a doping method, the dopant material can be formed by co-evaporation with the host material, or it may be mixed with the host material in advance and then vapor-deposited simultaneously.

[0801] The amount of the host material used varies depending on the type of 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 mass, more preferably 80 to 99.95% by mass, and even more preferably 90 to 99.9% by mass of the total materials for the light-emitting layer.

[0802] The amount of 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 dopant used is preferably 0.001 to 50% by mass, more preferably 0.05 to 20% by mass, and even more preferably 0.1 to 10% by mass, of the total material for the light-emitting layer. The above ranges are preferable in that, for example, concentration quenching can be prevented. Furthermore, from the viewpoint of durability, it is also preferable that some or all of the hydrogen atoms of the dopant material are deuterated.

[0803] Examples of host materials include fused ring derivatives of anthracene, pyrene, dibenzochrysene, or fluorene, which have long been known as light emitters; bisstyryl derivatives such as bisstyryl anthracene derivatives and distyrylbenzene derivatives; tetraphenylbutadiene derivatives; cyclopentadiene derivatives; and compounds represented by any of the following formulae (H1), (H2), and (H3). Anthracene-based compounds, fluorene-based compounds, or dibenzochrysene-based compounds, and compounds represented by any of the following formulae (H1), (H2), and (H3), are preferred, with anthracene-based compounds or compounds represented by any of the following formulae (H1), (H2), and (H3) being more preferred. From the perspective of durability, it is also preferred that some or all of the hydrogen atoms in the host material be deuterated. Furthermore, it is also preferred to form an emitting layer by combining a host compound in which some or all of the hydrogen atoms have been deuterated with a dopant compound in which some or all of the hydrogen atoms have been deuterated.

[0804] <Compounds represented by any of formulas (H1), (H2) and (H3)> [ka]

[0805] In the above formulas (H1), (H2) and (H3), L 1represents an arylene having 6 to 24 carbon atoms, a heteroarylene having 2 to 24 carbon atoms, a heteroarylenearylene having 6 to 24 carbon atoms, or an aryleneheteroarylenearylene having 6 to 24 carbon atoms, preferably an arylene having 6 to 16 carbon atoms, more preferably an arylene having 6 to 12 carbon atoms, and particularly preferably an arylene having 6 to 10 carbon atoms, and specific examples thereof include divalent groups such as a benzene ring, a biphenyl ring, a terphenyl ring, and a fluorene ring. The heteroarylene is preferably a heteroarylene having 2 to 24 carbon atoms, more preferably a heteroarylene having 2 to 20 carbon atoms, still more preferably a heteroarylene having 2 to 15 carbon atoms, and particularly preferably a heteroarylene having 2 to 10 carbon atoms. Specific examples thereof 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 benzophenone ... and divalent groups such as a benzoimidazole 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 purine ring, a pteridine ring, a carbazole ring, an acridine ring, a phenoxathiin ring, a phenoxazine ring, a phenothiazine ring, a phenazine 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, an oxadiazole ring, and a thianthrene ring. At least one hydrogen atom in the compounds represented by the above formulas may be substituted with alkyl having 1 to 6 carbon atoms, cyano, halogen, or deuterium.

[0806] Preferred specific examples include compounds represented by any of the structural formulas listed below. In the structural formulas listed below, Me is methyl. In the structural formulas listed below, at least one hydrogen may be substituted with halogen, cyano, alkyl having 1 to 4 carbon atoms (e.g., methyl or t-butyl), phenyl, naphthyl, or the like.

[0807] [ka]

[0808] [ka]

[0809] [ka]

[0810] [ka]

[0811] <Anthracene compounds> The anthracene-based compound as the host is, for example, a compound represented by the following formula (3-H) or (3-2-H). [ka]

[0812] In formula (3-H), 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 atom in the compound represented by formula (3-H) may be substituted with halogen, cyano, deuterium, or an optionally substituted heteroaryl.

[0813] Furthermore, a multimer (preferably a dimer) may be formed using the structure represented by formula (3-H) as a unit structure. In this case, for example, the unit structures represented by formula (3-H) may be bonded to each other via X, where X may be a single bond, an arylene (such as phenylene, biphenylene, or naphthylene), or a heteroarylene (a divalent group such as a pyridine ring, a dibenzofuran ring, a dibenzothiophene ring, a carbazole ring, a benzocarbazole ring, or a phenyl-substituted carbazole ring).

[0814] The details of the aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, alkyl, cycloalkyl, alkenyl, alkoxy, aryloxy, arylthio, and silyl will be described in the section on preferred embodiments below. Substituents therefor include aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, alkyl, cycloalkyl, alkenyl, alkoxy, aryloxy, arylthio, and silyl, and the details of these will also be described in the section on preferred embodiments below.

[0815] Preferred embodiments of the above anthracene-based compounds are described below. The symbols in the following structures are defined as above. [ka]

[0816] In formula (3-H), X's are each independently a group represented by 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-H) at *. Preferably, no two X's are simultaneously a group represented by formula (3-X3). More preferably, no two X's are simultaneously a group represented by formula (3-X2).

[0817] Furthermore, a multimer (preferably a dimer) may be formed using the structure represented by formula (3-H) as a unit structure. In this case, for example, the unit structures represented by formula (3-H) may be bonded to each other via X, where X may be a single bond, an arylene (such as phenylene, biphenylene, or naphthylene), or a heteroarylene (a divalent group such as a pyridine ring, a dibenzofuran ring, a dibenzothiophene ring, a carbazole ring, a benzocarbazole ring, or a phenyl-substituted carbazole ring).

[0818] The naphthylene moieties in formula (3-X1) and formula (3-X2) may be fused with one benzene ring. The fused structures are as follows: [ka]

[0819] 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 formula (A) (including carbazolyl, benzocarbazolyl, and phenyl-substituted carbazolyl). 1 or Ar 2 is a group represented by formula (A) described below, the group represented by formula (A) is bonded to the naphthalene ring in formula (3-X1) or formula (3-X2) at the *.

[0820] Ar 3 is phenyl, biphenylyl, terphenylyl, quaterphenylyl, naphthyl, phenanthryl, fluorenyl, benzofluorenyl, chrysenyl, triphenylenyl, pyrenylyl, or a group represented by formula (A) (including carbazolyl, benzocarbazolyl, and phenyl-substituted carbazolyl). 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 of formula (3-H) and the group represented by formula (A) are directly bonded.

[0821] Also, Ar 3 may have a substituent, and Ar 3 At least one hydrogen atom in the formula (A) 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 formula (A) (including carbazolyl and phenyl-substituted carbazolyl). 3 When the substituent of is a group represented by formula (A), the group represented by formula (A) is Ar in formula (3-X3) at *. 3 and combine.

[0822] Ar 4 are each independently hydrogen, phenyl, biphenylyl, terphenylyl, naphthyl, or silyl substituted with alkyl having 1 to 4 carbon atoms (such as methyl, ethyl, and t-butyl) and / or cycloalkyl having 5 to 10 carbon atoms.

[0823] Examples of the alkyl having 1 to 4 carbon atoms that substitutes on 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 alkyls.

[0824] 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.

[0825] 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 one of these cycloalkyls.

[0826] Specific examples of "silyl substituted with cycloalkyl having 5 to 10 carbon atoms" include tricyclopentylsilyl and tricyclohexylsilyl.

[0827] Substituted silyls include dialkylcycloalkylsilyls, which are substituted with two alkyls and one cycloalkyl, and alkyldicycloalkylsilyls, which are substituted with one alkyl and two cycloalkyls. Specific examples of the alkyl and cycloalkyl substituents are the groups described above.

[0828] Furthermore, hydrogen atoms in the chemical structure of the anthracene-based compound represented by formula (3-H) may be substituted with a group represented by formula (A). When substituted with a group represented by formula (A), the group represented by formula (A) replaces at least one hydrogen atom in the compound represented by formula (3-H) at the *.

[0829] The group represented by formula (A) is one of the substituents that the anthracene compound represented by formula (3-H) can have. [ka]

[0830] In 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.

[0831] R 21 ~R 28The "alkyl" in the "optionally substituted alkyl" may be either a straight chain or a branched chain, and examples thereof include a straight chain alkyl having 1 to 24 carbon atoms or a branched chain alkyl having 3 to 24 carbon atoms. An alkyl having 1 to 18 carbon atoms (branched chain alkyl having 3 to 18 carbon atoms) is preferred, an alkyl having 1 to 12 carbon atoms (branched chain alkyl having 3 to 12 carbon atoms) is more preferred, an alkyl having 1 to 6 carbon atoms (branched chain alkyl having 3 to 6 carbon atoms) is even more preferred, and an alkyl having 1 to 4 carbon atoms (branched chain alkyl having 3 to 4 carbon atoms) is particularly preferred.

[0832] Specific examples of "alkyl" include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, t-butyl, n-pentyl, isopentyl, neopentyl, t-pentyl, n-hexyl, 1-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, n-heptyl, 1-methylhexyl, n-octyl, t-octyl, 1-methylheptyl, Examples include 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.

[0833] 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.

[0834] 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.

[0835] R 21 ~R 28 Examples of the "aryl" in the "optionally substituted aryl" include 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.

[0836] 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, naphthacenyl, which are fused tetracyclic ring systems; perylenyl, pentacenyl, etc.

[0837] 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, still more preferably heteroaryl having 2 to 15 carbon atoms, and particularly preferably heteroaryl having 2 to 10 carbon atoms. Examples of heteroaryl include heterocycles containing, as ring-constituting atoms other than carbon, 1 to 5 heteroatoms selected from oxygen, sulfur, and nitrogen.

[0838] 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 thereof include benzoyl, quinazolyl, quinoxalinyl, phthalazinyl, naphthyridinyl, purinyl, pteridinyl, carbazolyl, acridinyl, phenoxathiinyl, phenoxazinyl, phenothiazinyl, phenazinyl, indolizinyl, furyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, thienyl, benzo[b]thienyl, dibenzothienyl, furazanyl, oxadiazolyl, thianthrenyl, naphthobenzofuranyl, and naphthobenzothienyl.

[0839] R 21 ~R 28 Examples of the "alkoxy" in "optionally substituted alkoxy" include straight-chain alkoxy having 1 to 24 carbon atoms or branched-chain alkoxy having 3 to 24 carbon atoms. Alkoxy having 1 to 18 carbon atoms (branched-chain alkoxy having 3 to 18 carbon atoms) is preferred, alkoxy having 1 to 12 carbon atoms (branched-chain alkoxy having 3 to 12 carbon atoms) is more preferred, alkoxy having 1 to 6 carbon atoms (branched-chain alkoxy having 3 to 6 carbon atoms) is even more preferred, and alkoxy having 1 to 4 carbon atoms (branched-chain alkoxy having 3 to 4 carbon atoms) is particularly preferred.

[0840] Specific examples of "alkoxy" include methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, s-butoxy, t-butoxy, pentyloxy, hexyloxy, heptyloxy, octyloxy, and the like.

[0841] R 21 ~R 28The "aryloxy" in the "optionally substituted aryloxy" is a group in which the hydrogen of the -OH group is substituted with 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.

[0842] R 21 ~R 28 The "arylthio" in the "optionally substituted arylthio" is a group in which the hydrogen of the -SH group is substituted with 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.

[0843] R 21 ~R 28 The "trialkylsilyl" in the above formula is a group in which three hydrogen atoms in the silyl group are each independently substituted with an alkyl, and this alkyl is the same as the above-mentioned R 21 ~R 28 Examples of the alkyl group include those described as "alkyl" in the above. 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.

[0844] 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.

[0845] R 21 ~R 28 The "tricycloalkylsilyl" in the above formula is a group in which three hydrogen atoms in the silyl group are each independently substituted with a cycloalkyl, and this cycloalkyl is one of the above-mentioned R 21 ~R 28 Examples of the cycloalkyl groups described above as "cycloalkyl" include those described above. Preferred cycloalkyl groups for substitution are cycloalkyl groups having 5 to 10 carbon atoms, and specific examples 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.

[0846] Specific examples of "tricycloalkylsilyl" include tricyclopentylsilyl, tricyclohexylsilyl, and the like.

[0847] 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 above-mentioned specific alkyls and cycloalkyls.

[0848] R 21 ~R 28 The "substituted amino" in the "optionally substituted amino" includes, for example, amino in which two hydrogen atoms are substituted with aryl or heteroaryl. An amino in which two hydrogen atoms are substituted with aryl atoms is a diaryl-substituted amino, an amino in which two hydrogen atoms are substituted with heteroaryl atoms is a diheteroaryl-substituted amino, and an amino in which two hydrogen atoms are substituted with an aryl and a heteroaryl atom is an arylheteroaryl-substituted amino. The aryl and heteroaryl atoms are substituted with the R 21 ~R 28 The groups described as "aryl" and "heteroaryl" in the above can be cited.

[0849] Specific examples of the "substituted amino" include diphenylamino, dinaphthylamino, phenylnaphthylamino, dipyridylamino, phenylpyridylamino, naphthylpyridylamino, and the like.

[0850] R 21 ~R 28 The "halogen" in the above formula includes fluorine, chlorine, bromine, and iodine.

[0851] R 21 ~R 28 Some of the groups described as may be substituted as described above, and in this 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 Reference can be made to groups described as "alkyl", "cycloalkyl", "aryl" or "heteroaryl" in the above.

[0852] Y as 'NR' 29 "R" 29 is hydrogen or an optionally substituted aryl, and the aryl is the same as R 21 ~R 28 The groups described as "aryl" in the above formula can be cited, and the substituents thereof include R 21 ~R 28 The groups described as substituents for the following can be cited.

[0853] 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 formula (A-1) below does not form a ring, and examples of the group represented by formulas (A-2) to (A-14) below include groups represented by formulas (A-1) to (A-14). At least one hydrogen atom in the group represented by any of formulas (A-1) to (A-14) may be substituted with alkyl, cycloalkyl, aryl, heteroaryl, alkoxy, aryloxy, arylthio, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, alkyldicycloalkylsilyl, diaryl-substituted amino, diheteroaryl-substituted amino, arylheteroaryl-substituted amino, halogen, hydroxy, or cyano. [ka]

[0854] Examples of rings formed by bonding adjacent groups to each other include hydrocarbon rings such as cyclohexane rings, and examples of aryl and heteroaryl rings include the above-mentioned R 21 ~R 28 These rings are formed so as to be fused with one or two benzene rings in formula (A-1).

[0855] Examples of the group represented by formula (A) include groups represented by any of formulas (A-1) to (A-14), preferably groups represented by any of formulas (A-1) to (A-5) and formulas (A-12) to (A-14), more preferably groups represented by any of formulas (A-1) to (A-4), still more preferably groups represented by any of formulas (A-1), (A-3) and (A-4), and particularly preferably groups represented by formula (A-1).

[0856] The group represented by formula (A) may be a naphthalene ring in formula (3-X1) or formula (3-X2), a single bond in formula (3-X3), Ar in formula (3-X3), or a hydroxyl group in formula (3-X4). 3 As described above, the naphthalene ring in formula (3-X1) or formula (3-X2), the single bond in formula (3-X3), and / or Ar in formula (3-X3) are bonded to the naphthalene ring in formula (3-X1) or formula (3-X2), and are substituted with at least one hydrogen atom in the compound represented by formula (3-H). 3 The form in which it is bound to is preferred.

[0857] 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 where R is bonded, and the position where at least one hydrogen atom in the compound represented by formula (3-H) is substituted in the structure of the group represented by formula (A), may be any position in the structure of formula (A), for example, either of the two benzene rings in the structure of formula (A), or R 21 ~R 28 Any ring formed by bonding adjacent groups to each other, or ">NR 29 "R" 29 The bond can be at any position within the

[0858] Examples of the group represented by formula (A) include the following groups: In the formula, Y and * are defined as above. [ka]

[0859] [ka]

[0860] In addition, all or part of the hydrogen atoms in the chemical structure of the anthracene-based compound represented by formula (3-H) may be deuterium atoms.

[0861] Further, examples of the anthracene-based compound include an anthracene-based compound represented by the following formula (3-2-H). [ka]

[0862] In formula (3-2-H), Ar c ', Ar 14 ', and Ar 15 Each of the ' is independently phenyl, biphenylyl, terphenylyl, naphthyl, phenanthryl, fluorenyl, benzofluorenyl, chrysenyl, triphenylenyl, pyrenyl, or a group represented by any one of the above formulae (A-1) to (A-14), and at least one hydrogen atom in these groups may be substituted with phenyl, biphenylyl, terphenylyl, naphthyl, phenanthryl, fluorenyl, benzofluorenyl, chrysenyl, triphenylenyl, pyrenyl, or a group represented by any one of the formulae (A-1) to (A-14). When both hydrogen atoms of the methylenes in the fluorenyl and benzofluorenyl are substituted with phenyl, these phenyls may be bonded to each other via a single bond. In addition, Ar c ', Ar 14 ', and Ar 15 The carbon atom on the anthracene ring to which "'" is not bonded may be substituted with methyl or t-butyl instead of hydrogen. At least one hydrogen in the compound represented by formula (3-2-H) may be substituted with halogen or cyano, and at least one hydrogen in the compound represented by formula (3-2-H) is substituted with deuterium.

[0863] In formula (3-2-H), Ar c ', Ar 14 ', and Ar 15 Each of the ' is preferably independently phenyl, biphenylyl, terphenylyl, naphthyl, phenanthryl, fluorenyl, or a group represented by any one of the above formulas (A-1) to (A-4), and at least one hydrogen atom in these groups may be substituted with phenyl, naphthyl, phenanthryl, fluorenyl, or a group represented by any one of the above formulas (A-1) to (A-4).

[0864] In the compound represented by formula (3-2-H), at least the carbon atom at the 10-position of the anthracene ring (Ar c It is preferable that the hydrogen bonded to the carbon atom (the carbon atom to which Ar′ is bonded is the 9th position) is substituted with deuterium. That is, the compound represented by formula (3-2-H) is preferably a compound represented by the following formula (3-2-Hb). In formula (1Ab), D is deuterium, and Ar c ', Ar 14 ', and Ar 15 "'" is the same as defined in formula (3-2-H). D in formula (3-2-Hb) indicates that at least this position is deuterium, and any one or more other hydrogen atoms in formula (3-2-Hb) may also be deuterium. It is also preferred that all hydrogen atoms in formula (3-2-Hb) are deuterium.

[0865] [ka]

[0866] Specific examples of anthracene compounds include compounds represented by the following formulas (3-1) to (3-72): In the following structural formulas, "Me" represents methyl, "D" represents deuterium, and "tBu" represents t-butyl.

[0867] [ka]

[0868]

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[0869]

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[0870]

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[0871]

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[0872]

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[0873]

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[0874]

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[0875] Other specific examples of the anthracene compounds include compounds represented by the following formulae (3-131-Y) to (3-179-Y), compounds represented by the following formulae (3-180-Y) to (3-182-Y), compounds represented by the following formulae (3-183-N), compounds represented by the following formulae (3-184-Y) to (3-254-Y), compounds represented by the following formulae (3-254-Y) to (3-269-Y), and compounds represented by the following formulae (3-500) to (3-557). In the compounds represented by the following formulae (3-131-Y) to (3-179-Y), the compounds represented by the following formulae (3-180-Y) to (3-182-Y), the following formula (3-183-N), the following formulae (3-184-Y) to (3-254-Y), the formulae (3-254-Y) to (3-269-Y), and the following formulae (3-500) to (3-557), hydrogen atoms may be partially or completely substituted with deuterium. In the formulae, Y represents -O-, -S-, >NR 29 (R 29 is defined as above) or >C(-R 30 )2(R 30 may be either an optionally linked aryl or alkyl, and R 29 is, for example, phenyl, R 30 For example, when Y is O, the formula (3-131-Y) becomes the formula (3-131-O), and when Y is -S- or >NR 29 In the case of (3-131-S) or (3-131-N), respectively.

[0876] [ka]

[0877] [ka]

[0878] [ka]

[0879] [ka]

[0880]

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[0881]

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[0882]

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[0883]

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[0884]

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[0885]

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[0886]

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[0887]

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[0888]

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[0889]

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[0890] [ka]

[0891] [ka]

[0892] [ka]

[0893] [ka]

[0894] [ka]

[0895] Among these compounds, the compounds of formula (3-131-Y) to formula (3-134-Y), formula (3-138-Y), formula (3-140-Y) to formula (3-143-Y), formula (3-150-Y), formula (3-153-Y) to formula (3-156-Y), formula (3-166-Y), formula (3-168-Y), formula (3-173-Y), formula (3-177-Y), formula (3-180-Y) to formula (3-183-N), formula (3-185-Y), formula (3-1 Compounds represented by formula (3-90-Y), formula (3-223-Y), formula (3-241-Y), formula (3-250-Y), formula (3-252-Y) to formula (3-254-Y), formula (3-501), formula (3-507), formula (3-508), formula (3-509), formula (3-513), formula (3-514), formula (3-519), formula (3-521), formula (3-538) to formula (3-547), or formula (3-600) to (3-620) are preferred. Y is preferably -O-.

[0896] The anthracene compound represented by formula (3-H) is a compound having a reactive group at a desired position of the anthracene skeleton, and X, Ar 4The compound can be produced by applying Suzuki coupling, Negishi coupling, or other known coupling reactions using a compound having a reactive group in a partial structure such as the structure of formula (A) as a starting material. Examples of reactive groups in these reactive compounds include halogens and boronic acids. For specific production methods, reference can be made to the synthesis methods described in paragraphs

[0089] to

[0175] of International Publication No. 2014 / 141725. The anthracene compound represented by formula (3-2-H) can be produced by a method similar to the production methods described in International Publication No. 2006 / 003842, Korean Patent Publication No. 2017-116885, International Publication No. 2009 / 142230, etc.

[0897] <Fluorene-based compounds> The compound represented by formula (4-H) basically functions as a host. [ka]

[0898] In formula (4-H), R 1 From R 10 are each independently a hydrogen atom, an aryl atom, a heteroaryl atom (the heteroaryl atom may be bonded to the fluorene skeleton in Formula (4-H) 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, wherein at least one hydrogen atom in each of these groups 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, and 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, and at least one hydrogen atom in these may be substituted with an aryl, a heteroaryl, an alkyl, or a cycloalkyl; At least one hydrogen atom in the compound represented by formula (4-H) may be substituted with halogen, cyano, or deuterium.

[0899] For details of each group in the definition of formula (4-H), the explanation for the polycyclic aromatic compound of formula (1) can be cited.

[0900] R 1 From R 10 Examples of the alkenyl in the 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, still more preferably alkenyl having 2 to 6 carbon atoms, and particularly preferably alkenyl having 2 to 4 carbon atoms. Preferred alkenyls include 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, and 5-hexenyl.

[0901] 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).

[0902] [ka]

[0903] In formulas (4-Ar1) to (4-Ar5), Y 1 are each independently O, S, or NR, and R is phenyl, biphenylyl, naphthyl, anthracenyl, or hydrogen; At least one hydrogen atom in the structures of formulae (4-Ar1) to (4-Ar5) may be substituted with phenyl, biphenylyl, naphthyl, anthracenyl, phenanthrenyl, methyl, ethyl, propyl, or butyl.

[0904] These heteroaryls may be bonded to the fluorene skeleton in formula (4-H) via a linking group. That is, the fluorene skeleton and the heteroaryl in formula (4-H) may not only be bonded directly, but also may be bonded therebetween via a linking group. Examples of such linking groups include phenylene, biphenylene, naphthylene, anthracenylene, methylene, ethylene, -OCH2CH2-, -CH2CHO-, or -OCH2CHO-.

[0905] Furthermore, R in formula (4-H) 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-H), and is an aliphatic ring or an aromatic ring. An aromatic ring is preferable, and examples of the structure containing the benzene ring in formula (4-H) include a naphthalene ring and a phenanthrene ring. 9 and R 10The spiro ring formed by the formula (4-H) is a ring spiro-bonded to the five-membered ring in formula (4-H), and is an aliphatic ring or an aromatic ring. An aromatic ring, such as a fluorene ring, is preferred.

[0906] The compound represented by formula (4-H) is preferably a compound represented by the following formula (4-H-1), formula (4-H-2), or formula (4-H-3), and in formula (4-H), R 1 and R 2 In formula (4-H), R 3 and R 4 In formula (4-H), R 1 From R 8 is a compound in which none of the above is bound.

[0907] [ka]

[0908] R in formula (4-H-1), formula (4-H-2) and formula (4-H-3) 1 From R 10 The definition of R in formula (4-H) corresponds to 1 From R 10 and R in formula (4-H-1) and formula (4-H-2) 11 From R 14 The definition of R in formula (4-H) 1 From R 10 is the same as

[0909] The compound represented by formula (4-H) is more preferably a compound represented by the following formula (4-H-1A), formula (4-H-2A), or formula (4-H-3A), and in formula (4-H-1), formula (4-H-1), or formula (4-H-3), R 9 and R 10 is a compound in which a spiro-fluorene ring is formed by bonding.

[0910] [ka]

[0911] 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

[0912] In addition, all or part of the hydrogen atoms in the compound represented by formula (4-H) may be substituted with halogen, cyano, or deuterium.

[0913] More specific examples of fluorene-based compounds as hosts in the present invention include compounds represented by the following structural formulas: wherein "Me" represents methyl. [ka]

[0914] <Dibenzochrysene compounds> The dibenzochrysene compound as the host is, for example, a compound represented by the following formula (5-H). [ka]

[0915] In formula (5-H), R 1 From R 16are each independently a hydrogen atom, an aryl group, a heteroaryl group (the heteroaryl group may be bonded to the dibenzochrysene skeleton in Formula (5-H) via a linking group), a diarylamino group, a diheteroarylamino group, an arylheteroarylamino group, an alkyl group, a cycloalkyl group, an alkenyl group, an alkoxy group, or an aryloxy group, wherein at least one hydrogen atom in each of these groups may be substituted with an aryl group, a heteroaryl group, an alkyl group, or a cycloalkyl group; Also, R 1 From R 16 adjacent groups among these may be bonded to each other to form a fused ring, and 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, and at least one hydrogen atom in these may be substituted with an aryl, a heteroaryl, an alkyl, or a cycloalkyl; At least one hydrogen atom in the compound represented by formula (5-H) may be substituted with halogen, cyano, or deuterium.

[0916] For details of each group in the definition of formula (5-H), the explanation for the polycyclic aromatic compound of formula (1) can be cited.

[0917] Examples of alkenyl in the definition of formula (5-H) 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, still more preferably alkenyl having 2 to 6 carbon atoms, and particularly preferably alkenyl having 2 to 4 carbon atoms. Preferred alkenyls include 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, and 5-hexenyl.

[0918] 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).

[0919] [ka]

[0920] In formula (5-Ar1) to formula (5-Ar5), Y 1 are each independently O, S, or NR, and R is phenyl, biphenylyl, naphthyl, anthracenyl, or hydrogen; At least one hydrogen atom in the structures of formulae (5-Ar1) to (5-Ar5) may be substituted with phenyl, biphenylyl, naphthyl, anthracenyl, phenanthrenyl, methyl, ethyl, propyl, or butyl.

[0921] These heteroaryls may be bonded to the dibenzochrysene skeleton in formula (5-H) via a linking group. That is, the dibenzochrysene skeleton and the heteroaryl in formula (5-H) may be bonded not only directly but also via a linking group. Examples of the linking group include phenylene, biphenylene, naphthylene, anthracenylene, methylene, ethylene, -OCH2CH2-, -CH2CHO-, and -OCH2CHO-.

[0922] The compound represented by formula (5-H) 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-H) 2 , R 3 , R 6 , R 7 , R 10 , R 11 , R 14and R 15 are preferably each independently hydrogen, phenyl, biphenylyl, naphthyl, anthracenyl, phenanthrenyl, a monovalent group having a structure of formula (5-Ar1), formula (5-Ar2), formula (5-Ar3), formula (5-Ar4), or formula (5-Ar5) (the monovalent group having such a structure may be bonded to the dibenzochrysene skeleton in formula (5-H) via phenylene, biphenylene, naphthylene, anthracenylene, methylene, ethylene, -OCHCH-, -CHCHO-, or -OCHCHO-), methyl, ethyl, propyl, or butyl.

[0923] The compound represented by formula (5-H) 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-H) 3 , R 6 , R 11 and R 14 at least one (preferably one or two, more preferably one) of the formulas (5-Ar1), (5-Ar2), (5-Ar3), (5-Ar4) or (5-Ar5) is a monovalent group having a structure represented by formula (5-Ar1), (5-Ar2), (5-Ar3), (5-Ar4) or (5-Ar5) via a single bond, phenylene, biphenylene, naphthylene, anthracenylene, methylene, ethylene, -OCHCH-, -CHCHO- or -OCHCHO-; The positions other than the at least one (i.e., positions other than the position substituted by the monovalent group having the structure) are 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.

[0924] Furthermore, R in formula (5-H) 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 formula (5-Ar1) to formula (5-Ar5) is selected as the group, at least one hydrogen atom in the structure is selected from the group represented by R 1 From R 16 may be bonded to any one of the following to form a single bond.

[0925] More specific examples of dibenzochrysene compounds as hosts in the present invention include compounds represented by the following structural formula: wherein "tBu" represents t-butyl.

[0926] [ka] [ka]

[0927] The above-mentioned light-emitting layer materials (host materials and dopant materials) can also be used as light-emitting layer materials in the form of polymer compounds obtained by polymerizing a reactive compound substituted with a reactive substituent as a monomer, or a crosslinked polymer thereof, or a pendant-type polymer compound obtained by reacting a main-chain polymer with the reactive compound, or a crosslinked pendant-type polymer thereof. Regarding the reactive substituent in this case, the same explanation as for the polycyclic aromatic compound represented by formula (1) can be cited. The uses of such polymer compounds and crosslinked polymers will be described in detail below.

[0928] <Example of polymer host material> [ka]

[0929] In formula (SPH-1), Each MU is independently a divalent aromatic group, each EC is independently a monovalent aromatic group, two hydrogen atoms in MU are replaced by EC or MU, and k is an integer of 2 to 50,000.

[0930] More specifically, Each MU is independently arylene, heteroarylene, diarylylenearylamino, diarylylenearylboryl, oxaborine-diyl, or azaborine-diyl; each EC is independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, or aryloxy; At least one hydrogen atom 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 of 20 to 50,000, and more preferably an integer of 100 to 50,000.

[0931] At least one hydrogen atom in MU and EC in formula (SPH-1) may be substituted with alkyl having 1 to 24 carbon atoms, cycloalkyl having 3 to 24 carbon atoms, halogen, or deuterium; further, any -CH2- in the alkyl may be substituted with -O- or -Si(CH3)2-; any -CH2- in the alkyl except for the -CH2- directly bonded to EC in formula (SPH-1) may be substituted with arylene having 6 to 24 carbon atoms; and any hydrogen atom in the alkyl may be substituted with fluorine.

[0932] Examples of MU include a divalent group represented by removing any two hydrogen atoms from any of the following compounds: [ka]

[0933] More specifically, the divalent group may be any of the following structures: In these, MU is bonded to another MU or EC at *.

[0934] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka]

[0935] Examples of EC include monovalent groups represented by any of the following structures: In these, EC is bonded to MU at *.

[0936] [ka] [ka]

[0937] From the viewpoints of solubility and film-forming properties, the compound represented by formula (SPH-1) preferably has 10 to 100% of the total number of MUs (k) in the molecule having alkyls of 1 to 24 carbon atoms, more preferably 30 to 100% of the total number of MUs (k) in the molecule having alkyls of 1 to 18 carbon atoms (branched-chain alkyls of 3 to 18 carbon atoms), and even more preferably 50 to 100% of the total number of MUs (k) in the molecule having alkyls of 1 to 12 carbon atoms (branched-chain alkyls of 3 to 12 carbon atoms). On the other hand, from the viewpoints of in-plane alignment and charge transport, preferably has 10 to 100% of the total number of MUs (k) in the molecule having alkyls of 7 to 24 carbon atoms, and more preferably 30 to 100% of the total number of MUs (k) in the molecule having alkyls of 7 to 24 carbon atoms (branched-chain alkyls of 7 to 24 carbon atoms).

[0938] The uses of such polymer compounds and crosslinked polymers will be described in detail below.

[0939] <Electron injection layer and electron transport layer in organic electroluminescent device> The electron injection layer 107 plays a role of efficiently injecting electrons moving from the cathode 108 into the light-emitting layer 105 or the electron transport layer 106. The electron transport layer 106 plays a role of efficiently transporting electrons injected from the cathode 108 or electrons injected from the cathode 108 via the electron injection layer 107 to the light-emitting layer 105. The electron transport layer 106 and the electron injection layer 107 are each formed by laminating or mixing one or more electron transport / injection materials, or by a mixture of an electron transport / injection material and a polymer binder.

[0940] The electron injection / transport layer is a layer responsible for injecting electrons from the cathode and transporting them. It is desirable for the layer to have high electron injection efficiency and efficiently transport the injected electrons. To achieve this, it is preferable for the material to have high electron affinity, high electron mobility, excellent stability, and be less likely to generate trapping impurities during manufacture and use. However, considering the balance between hole and electron transport, if a material primarily serves to efficiently block holes from the anode from flowing to the cathode without recombining, it can have the same effect of improving luminous efficiency as a material with high electron transport ability, even if it does not have a particularly high electron transport ability. Therefore, the electron injection / transport layer in this embodiment may also function as a layer that can efficiently block the movement of holes.

[0941] 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 electron injection layers and electron transport layers of organic EL devices.

[0942] Materials used in the electron transport layer or electron injection layer preferably contain at least one selected from the group consisting of aromatic or heteroaromatic ring compounds composed of one or more atoms selected from carbon, hydrogen, oxygen, sulfur, silicon, and phosphorus; pyrrole derivatives and their fused ring derivatives; and metal complexes containing electron-accepting nitrogen. Specific examples include fused ring aromatic derivatives such as naphthalene and anthracene; styryl aromatic derivatives such as 4,4'-bis(diphenylethenyl)biphenyl; perinone derivatives; coumarin derivatives; naphthalimide derivatives; quinone derivatives such as anthraquinone and diphenoquinone; phosphorus oxide derivatives; arylnitrile derivatives; and indole derivatives. Examples of metal complexes containing 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 other materials.

[0943] Specific examples of other electron transport compounds include pyridine derivatives, naphthalene derivatives, anthracene derivatives, benzofluorene 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, and triazine derivatives. Examples of the compound include pyrazine 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, arylnitrile derivatives, indole derivatives, phosphine oxide derivatives, and bisstyryl derivatives.

[0944] 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.

[0945] The above-mentioned materials may be used alone or in combination with other materials.

[0946] Among the above-mentioned materials, borane derivatives, pyridine derivatives, fluoranthene derivatives, BO-based derivatives, anthracene derivatives, benzofluorene derivatives, phosphine oxide derivatives, pyrimidine derivatives, arylnitrile derivatives, triazine derivatives, benzimidazole derivatives, phenanthroline derivatives, and quinolinol-based metal complexes are preferred.

[0947] <Borane derivatives> The borane derivative is, for example, a compound represented by the following formula (ETM-1), and is disclosed in detail in JP-A-2007-27587. [ka] In 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 fewer 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.

[0948] Among the compounds represented by formula (ETM-1), compounds represented by the following formula (ETM-1-1) and compounds represented by the following 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 an optionally substituted alkyl, an optionally substituted cycloalkyl, or an optionally substituted aryl, and 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 represents 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 of "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 arylene having 20 or less carbon atoms which may be substituted, 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.

[0949] X 1 Specific examples of include divalent groups represented by any of the following formulae (X-1) to (X-9). [ka] (In each formula, R a are each independently alkyl, cycloalkyl or optionally substituted phenyl, and * represents the bonding position.

[0950] Specific examples of the borane derivative include the following compounds: [ka]

[0951] This borane derivative can be produced using known raw materials and known synthesis methods.

[0952] <Pyridine derivatives> The pyridine derivative is, for example, a compound represented by the following formula (ETM-2), and is preferably a compound represented by formula (ETM-2-1) or formula (ETM-2-2). [ka]

[0953] 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.

[0954] In 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).

[0955] In formula (ETM-2-2), R 11 and R 12are 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 R 11 and R 12 may be bonded to form a ring.

[0956] In each formula, the "pyridine-based substituent" is any of the following formulae (Py-1) to (Py-15) (in the formula, * represents a bonding position), and each pyridine-based substituent may be independently substituted with alkyl having 1 to 4 carbon atoms or cycloalkyl having 5 to 10 carbon atoms. Specific examples include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, and t-butyl, with methyl being preferred. In addition, 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.

[0957] [ka]

[0958] The pyridine-based substituent is any one of formulas (Py-1) to (Py-15) (in the formula, * represents a bonding position), and among these, any one of formulas (Py-21) to (Py-44) below is preferred. [ka]

[0959] At least one hydrogen atom in each pyridine derivative may be replaced with deuterium, and one of the two "pyridine-based substituents" in formula (ETM-2-1) and formula (ETM-2-2) may be replaced with aryl.

[0960] 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).

[0961] Specific examples of "alkyl" include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, t-butyl, n-pentyl, isopentyl, neopentyl, t-pentyl, n-hexyl, 1-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, n-heptyl, 1-methylhexyl, n-octyl, t-octyl, 1-methylheptyl, Examples include 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.

[0962] The above description of alkyl can be cited for the alkyl having 1 to 4 carbon atoms that substitutes the pyridine-based substituent.

[0963] R 11 ~R 18 Examples of the "cycloalkyl" in the above include cycloalkyl having 3 to 12 carbon atoms. A preferred "cycloalkyl" is cycloalkyl having 3 to 10 carbon atoms. A more preferred "cycloalkyl" is cycloalkyl having 3 to 8 carbon atoms. An even more preferred "cycloalkyl" is cycloalkyl having 3 to 6 carbon atoms. Specific examples of "cycloalkyl" include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, methylcyclopentyl, cycloheptyl, methylcyclohexyl, cyclooctyl, and dimethylcyclohexyl.

[0964] R 11 ~R 18 As for the "aryl" in the above, preferred aryl is aryl having 6 to 30 carbon atoms, more preferred aryl is aryl having 6 to 18 carbon atoms, still more preferred aryl is aryl having 6 to 14 carbon atoms, and particularly preferred is aryl having 6 to 12 carbon atoms.

[0965] Specific examples of the "aryl having 6 to 30 carbon atoms" include phenyl, which is a monocyclic aryl; (1-, 2-)naphthyl, which is a fused bicyclic aryl; acenaphthylene-(1-, 3-, 4-, 5-)yl, fluoren-(1-, 2-, 3-, 4-, 9-)yl, phenalene-(1-, 2-)yl, and (1-, 2-, 3-, 4-, 9-)phenanthryl, which are fused tricyclic aryl; triphenylene-(1-, 2-)yl, pyren-(1-, 2-, 4-)yl, and naphthacene-(1-, 2-, 5-)yl, which are fused tetracyclic aryl; and perylene-(1-, 2-, 3-)yl and pentacene-(1-, 2-, 5-, 6-)yl, which are fused pentacyclic aryl.

[0966] 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.

[0967] R in Equation (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.

[0968] Specific examples of this pyridine derivative include, for example, the following compounds.

Chemical formula

[0969] This pyridine derivative can be produced using known raw materials and known synthesis methods.

[0970] <Fluoranthene derivative> The fluoranthene derivative is, for example, a compound represented by the following formula (ETM-3), and specifically, it is disclosed in International Publication No. 2010 / 134352.

Chemical formula

[0971] In formula (ETM-3), X 12 ~X 21 represents hydrogen, halogen, linear, branched or cyclic alkyl, linear, branched or cyclic alkoxy, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl. Here, examples of the substituent when it is substituted include aryl, heteroaryl, alkyl or cycloalkyl.

[0972] Specific examples of this fluoranthene derivative include, for example, the following compounds.

Chemical formula

[0973] <BO-based derivative> The BO-based derivative is, for example, a polycyclic aromatic compound represented by the following formula (ETM-4), or a multimer of a polycyclic aromatic compound having a plurality of structures represented by the following formula (ETM-4).

Chemical formula

[0974] R 1 ~R 11 are each independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, alkyl, cycloalkyl, alkoxy, or aryloxy, and at least one hydrogen atom in these may be substituted with aryl, heteroaryl, alkyl, or cycloalkyl.

[0975] Also, R 1 ~R 11 Adjacent groups among these may be bonded to each other to form an aryl ring or a heteroaryl ring together with ring a, ring b, or ring c, and at least one hydrogen atom in the formed ring may be substituted with aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, alkyl, cycloalkyl, alkoxy, or aryloxy, and at least one hydrogen atom in these rings may be substituted with aryl, heteroaryl, alkyl, or cycloalkyl.

[0976] In addition, at least one hydrogen atom in the compound or structure represented by formula (ETM-4) may be substituted with a halogen or deuterium atom.

[0977] For an explanation of the substituents and ring formation form in formula (ETM-4), the explanation of the polycyclic aromatic compound represented by formula (1) etc. can be cited.

[0978] Specific examples of the BO derivative include the following compounds: [ka]

[0979] This BO derivative can be produced using known raw materials and known synthesis methods.

[0980] <Anthracene derivatives> One of the anthracene derivatives is, for example, a compound represented by the following formula (ETM-5). [ka]

[0981] Ar 1 are each independently a single bond, a divalent benzene, a divalent naphthalene, a divalent anthracene, a divalent fluorene, or a divalent phenalene.

[0982] Ar 2are each independently an aryl having 6 to 20 carbon atoms, preferably an aryl having 6 to 16 carbon atoms, more preferably an aryl having 6 to 12 carbon atoms, and particularly preferably an aryl having 6 to 10 carbon atoms. Specific examples of "aryl having 6 to 20 carbon atoms" include 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; fused bicyclic aryls such as (1-, 2-)naphthyl; 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-ter phenyl-4-yl, o-terphenyl-2-yl, o-terphenyl-3-yl, o-terphenyl-4-yl, p-terphenyl-2-yl, p-terphenyl-3-yl, p-terphenyl-4-yl), fused tricyclic aryls such as anthracene-(1-, 2-, 9-)yl, 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 aryls such as triphenylene-(1-, 2-)yl, pyren-(1-, 2-, 4-)yl, tetracene-(1-, 2-, 5-)yl, and fused pentacyclic aryls such as perylene-(1-, 2-, 3-)yl. Specific examples of the "aryl having 6 to 10 carbon atoms" include phenyl, biphenylyl, naphthyl, terphenylyl, anthracenyl, acenaphthylenyl, fluorenyl, phenalenyl, phenanthryl, triphenylenyl, pyrenyl, tetracenyl, and perylenyl.

[0983] 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. R 1 ~R4 The alkyl having 1 to 6 carbon atoms in the formula (I) may be either linear or branched. That is, it is a linear alkyl having 1 to 6 carbon atoms or a branched alkyl having 3 to 6 carbon atoms. It is more preferably 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, n-hexyl, 1-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, and 2-ethylbutyl. Methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, or t-butyl is preferred, and methyl, ethyl, or t-butyl is more preferred.

[0984] 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.

[0985] R 1 ~R 4 In the above, the aryl having 6 to 20 carbon atoms is preferably an aryl having 6 to 16 carbon atoms, more preferably an aryl having 6 to 12 carbon atoms, and particularly preferably an aryl having 6 to 10 carbon atoms. Specific examples of "aryl having 6 to 20 carbon atoms" include Ar 2 Specific examples of "aryl having 6 to 20 carbon atoms" in the above can be cited. Preferred "aryl having 6 to 20 carbon atoms" are phenyl, biphenylyl, terphenylyl, and naphthyl, more preferably phenyl, biphenylyl, 1-naphthyl, 2-naphthyl, and m-terphenyl-5'-yl, even more preferably phenyl, biphenylyl, 1-naphthyl, and 2-naphthyl, and most preferably phenyl.

[0986] Specific examples of these anthracene derivatives include the following compounds: [ka]

[0987] These anthracene derivatives can be produced using known raw materials and known synthesis methods.

[0988] <Benzofluorene derivatives> The benzofluorene derivative is, for example, a compound represented by the following formula (ETM-6). [ka]

[0989] Ar 1 are each independently an aryl having 6 to 20 carbon atoms, and Ar in formula (ETM-5) 2 The same explanation as for "aryl having 6 to 20 carbon atoms" in the above can be cited. An aryl having 6 to 16 carbon atoms is preferred, an aryl having 6 to 12 carbon atoms is more preferred, and an aryl having 6 to 10 carbon atoms is particularly preferred. Specific examples include phenyl, biphenylyl, naphthyl, terphenylyl, anthracenyl, acenaphthylenyl, fluorenyl, phenalenyl, phenanthryl, triphenylenyl, pyrenyl, tetracenyl, perylenyl, etc.

[0990] 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.

[0991] Ar 2The "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, n-hexyl, 1-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, n-heptyl, and 1-methylhexyl.

[0992] Ar 2 In the above, "cycloalkyl" includes, for example, cycloalkyl having 3 to 12 carbon atoms. Preferred "cycloalkyl" is cycloalkyl having 3 to 10 carbon atoms. More preferred "cycloalkyl" is cycloalkyl having 3 to 8 carbon atoms. Even more preferred "cycloalkyl" is cycloalkyl having 3 to 6 carbon atoms. Specific examples of "cycloalkyl" include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, methylcyclopentyl, cycloheptyl, methylcyclohexyl, cyclooctyl, and dimethylcyclohexyl.

[0993] Ar 2 As for the "aryl" in the above, preferred aryl is aryl having 6 to 30 carbon atoms, more preferred aryl is aryl having 6 to 18 carbon atoms, still more preferred aryl is aryl having 6 to 14 carbon atoms, and particularly preferred is aryl having 6 to 12 carbon atoms.

[0994] Specific examples of the "aryl having 6 to 30 carbon atoms" include phenyl, naphthyl, acenaphthylenyl, fluorenyl, phenalenyl, phenanthryl, triphenylenyl, pyrenyl, naphthacenyl, perylenyl, and pentacenyl.

[0995] 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.

[0996] Specific examples of the benzofluorene derivative include the following compounds: [ka]

[0997] This benzofluorene derivative can be produced using known raw materials and known synthesis methods.

[0998] <Phosphine oxide derivatives> The phosphine oxide derivative is, for example, a compound represented by the following formula (ETM-7-1): Details are also described in WO 2013 / 079217 and WO 2013 / 079678. [ka]

[0999] 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, cycloalkyl having 3 to 16 carbon atoms, heteroalkyl having 1 to 20 carbon atoms, aryl having 6 to 20 carbon atoms, heteroaryl having 5 to 20 carbon atoms, alkoxy having 1 to 20 carbon atoms, or aryloxy having 6 to 20 carbon atoms, R 7 and R 8 are each independently 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.

[1000] The phosphine oxide derivative may be, for example, a compound represented by the following formula (ETM-7-2). [ka]

[1001] R 1 ~R 3 may be the same or different and are selected from hydrogen, alkyl, cycloalkyl, aralkyl, alkenyl, cycloalkenyl, alkynyl, alkoxy, alkylthio, cycloalkylthio, aryl ether (aryl ether group), aryl thioether (aryl thioether group), aryl, heterocyclic group, halogen, cyano, aldehyde, carbonyl, carboxyl, amino, nitro, silyl, and a fused ring formed between adjacent substituents.

[1002] Ar 1 may be the same or different and are arylene or heteroarylene. 2 may be the same or different and are aryl or heteroaryl, 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, and when n is 3, R 1 does not exist.

[1003] Among these substituents, alkyl refers to saturated aliphatic hydrocarbon groups such as methyl, ethyl, propyl, and butyl, which may be unsubstituted or substituted. When substituted, the substituent is not particularly limited, and examples thereof include alkyl, aryl, and heterocyclic groups, which also apply to the following description. The number of carbon atoms in the alkyl is not particularly limited, but is usually in the range of 1 to 20 from the viewpoints of availability and cost.

[1004] The term "cycloalkyl" refers to a saturated alicyclic hydrocarbon group, such as cyclopropyl, cyclohexyl, norbornyl, adamantyl, etc., which may be substituted or unsubstituted. The number of carbon atoms in the alkyl moiety is not particularly limited, but is usually in the range of 3 to 20.

[1005] The term "aralkyl" refers to an aromatic hydrocarbon group mediated by an aliphatic hydrocarbon such as benzyl or phenylethyl, and both the aliphatic hydrocarbon and the aromatic hydrocarbon may be substituted or unsubstituted. The number of carbon atoms in the aliphatic moiety is not particularly limited, but is usually in the range of 1 to 20.

[1006] The term "alkenyl" refers to an unsaturated aliphatic hydrocarbon group containing a double bond, such as vinyl, allyl, or butadienyl, which may be substituted or unsubstituted. The number of carbon atoms in the alkenyl is not particularly limited, but is usually in the range of 2 to 20.

[1007] Furthermore, cycloalkenyl refers to an unsaturated alicyclic hydrocarbon group containing a double bond, such as cyclopentenyl, cyclopentadienyl, cyclohexenyl, etc., which may be unsubstituted or substituted.

[1008] The term "alkynyl" refers to an unsaturated aliphatic hydrocarbon group containing a triple bond, such as acetylenyl, which may be substituted or unsubstituted. The number of carbon atoms in the alkynyl is not particularly limited, but is usually in the range of 2 to 20.

[1009] The term "alkoxy" refers to an aliphatic hydrocarbon group such as methoxy, which may be unsubstituted or substituted via an ether bond. The number of carbon atoms in the alkoxy is not particularly limited, but is usually in the range of 1 to 20.

[1010] Moreover, alkylthio is a group in which the oxygen atom of the ether bond of alkoxy is substituted with a sulfur atom.

[1011] Moreover, cycloalkylthio is a group in which the oxygen atom of the ether bond of cycloalkoxy is substituted with a sulfur atom.

[1012] The aryl ether refers to an aromatic hydrocarbon group such as phenoxy, which may be unsubstituted or substituted via an ether bond. The number of carbon atoms in the aryl ether is not particularly limited, but is usually in the range of 6 to 40.

[1013] An aryl thioether is a group in which the oxygen atom of the ether bond of an aryl ether is substituted with a sulfur atom.

[1014] The aryl group refers to an aromatic hydrocarbon group such as phenyl, naphthyl, biphenylyl, phenanthryl, terphenylyl, or pyrenyl. 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.

[1015] The heterocyclic group refers to a cyclic structural group having atoms other than carbon, such as furanyl, thienyl, oxazolyl, pyridyl, quinolinyl, carbazolyl, 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.

[1016] Halogen refers to fluorine, chlorine, bromine, and iodine.

[1017] The aldehyde, carbonyl and amino groups may also include groups substituted with aliphatic hydrocarbons, alicyclic hydrocarbons, aromatic hydrocarbons, heterocycles and the like.

[1018] The aliphatic hydrocarbons, alicyclic hydrocarbons, aromatic hydrocarbons and heterocyclic rings may be either unsubstituted or substituted.

[1019] Silyl refers to a silicon compound group such as trimethylsilyl, which may be unsubstituted or substituted. The number of carbon atoms in the silyl is not particularly limited, but is usually in the range of 3 to 20. The number of silicon atoms is usually 1 to 6.

[1020] The fused 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 with each other. These fused rings may contain nitrogen, oxygen, or sulfur atoms in the ring structure, and may be fused with another ring.

[1021] Specific examples of the phosphine oxide derivative include the following compounds: [ka]

[1022] This phosphine oxide derivative can be produced using known raw materials and known synthesis methods.

[1023] <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]

[1024] 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.

[1025] The "aryl" in "optionally substituted aryl" includes, for example, aryl having 6 to 30 carbon atoms, preferably aryl having 6 to 24 carbon atoms, more preferably aryl having 6 to 20 carbon atoms, and even more preferably aryl having 6 to 12 carbon atoms.

[1026] Specific examples of "aryl" include phenyl, which is a monocyclic aryl; (2-, 3-, 4-)biphenylyl, which is a bicyclic aryl; (1-, 2-)naphthyl, which is a fused bicyclic aryl; terphenylyl, which is a tricyclic aryl (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), and fused tricyclic aryl. Examples of the aryl include acenaphthylene-(1-, 3-, 4-, 5-)yl, fluoren-(1-, 2-, 3-, 4-, 9-)yl, phenalene-(1-, 2-)yl, (1-, 2-, 3-, 4-, 9-)phenanthryl, tetracyclic aryl quaterphenylyl (5'-phenyl-m-terphenyl-2-yl, 5'-phenyl-m-terphenyl-3-yl, 5'-phenyl-m-terphenyl-4-yl, m-quaterphenylyl), fused tetracyclic aryl triphenylene-(1-, 2-)yl, pyren-(1-, 2-, 4-)yl, naphthacene-(1-, 2-, 5-)yl, and fused pentacyclic aryl perylene-(1-, 2-, 3-)yl and pentacene-(1-, 2-, 5-, 6-)yl.

[1027] 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, still more preferably heteroaryl having 2 to 15 carbon atoms, and particularly preferably heteroaryl having 2 to 10 carbon atoms. Examples of heteroaryl include heterocycles containing, in addition to carbon, 1 to 5 heteroatoms selected from oxygen, sulfur, and nitrogen as ring-constituting atoms.

[1028] 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.

[1029] The aryl and heteroaryl may be substituted, for example, by the above-mentioned aryl or heteroaryl, respectively.

[1030] Specific examples of the pyrimidine derivative include the following compounds: [ka]

[1031] This pyrimidine derivative can be produced using known raw materials and known synthesis methods.

[1032] <Arylnitrile derivatives> The arylnitrile 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 via single bonds, etc. Details are described in the specification of U.S. Application Publication No. 2014 / 0197386. [ka]

[1033] Ar niFrom the viewpoint of fast electron transporting property, it is preferable that the number of carbon atoms is large, and from the viewpoint of high T1, it is preferable that the number of carbon atoms is small. ni Specifically, when used in a layer adjacent to the light-emitting layer, it is preferable that the aryl group has a high T1, and is an aryl having 6 to 20 carbon atoms, preferably an aryl having 6 to 14 carbon atoms, and more preferably an aryl having 6 to 10 carbon atoms. Furthermore, the number of nitrile group substitutions, n, is preferably large from the viewpoint of a high T1, and is preferably small from the viewpoint of a high S1. Specifically, the number of nitrile group substitutions, n, is an integer of 1 to 4, preferably an integer of 1 to 3, more preferably an integer of 1 or 2, and even more preferably 1.

[1034] Each Ar is independently an optionally substituted aryl or an optionally substituted heteroaryl. From the viewpoint of high S1 and high T1, donor heteroaryl is preferred, and since it is used as an electron transport layer, it is preferred that there are fewer donor heteroaryls. From the viewpoint of charge transportability, aryl or heteroaryl with a large number of carbon atoms is preferred, and it is preferred that there are many substituents. The number of substitutions m of Ar is specifically an integer of 1 to 4, preferably an integer of 1 to 3, and more preferably 1 to 2.

[1035] The "aryl" in "optionally substituted aryl" includes, for example, aryl having 6 to 30 carbon atoms, preferably aryl having 6 to 24 carbon atoms, more preferably aryl having 6 to 20 carbon atoms, and even more preferably aryl having 6 to 12 carbon atoms.

[1036] Specific examples of "aryl" include phenyl, which is a monocyclic aryl; (2-, 3-, 4-)biphenylyl, which is a bicyclic aryl; (1-, 2-)naphthyl, which is a fused bicyclic aryl; terphenylyl, which is a tricyclic aryl (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), and fused tricyclic aryl. Examples of the aryl include acenaphthylene-(1-, 3-, 4-, 5-)yl, fluoren-(1-, 2-, 3-, 4-, 9-)yl, phenalene-(1-, 2-)yl, (1-, 2-, 3-, 4-, 9-)phenanthryl, tetracyclic aryl quaterphenylyl (5'-phenyl-m-terphenyl-2-yl, 5'-phenyl-m-terphenyl-3-yl, 5'-phenyl-m-terphenyl-4-yl, m-quaterphenylyl), fused tetracyclic aryl triphenylene-(1-, 2-)yl, pyren-(1-, 2-, 4-)yl, naphthacene-(1-, 2-, 5-)yl, and fused pentacyclic aryl perylene-(1-, 2-, 3-)yl and pentacene-(1-, 2-, 5-, 6-)yl.

[1037] 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, still more preferably heteroaryl having 2 to 15 carbon atoms, and particularly preferably heteroaryl having 2 to 10 carbon atoms. Examples of heteroaryl include heterocycles containing, in addition to carbon, 1 to 5 heteroatoms selected from oxygen, sulfur, and nitrogen as ring-constituting atoms.

[1038] 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.

[1039] The aryl and heteroaryl may be substituted, for example, by the above-mentioned aryl or heteroaryl, respectively.

[1040] The aryl nitrile derivative may be a polymer in which a plurality of compounds represented by formula (ETM-9) are bonded together via single bonds, etc. In this case, they may be bonded together via an aryl ring (preferably a polyvalent benzene ring, naphthalene ring, anthracene ring, fluorene ring, benzofluorene ring, phenalene ring, phenanthrene ring, or triphenylene ring) in addition to a single bond.

[1041] Specific examples of the arylnitrile derivative include the following compounds: [ka]

[1042] The arylnitrile derivative can be produced using known raw materials and known synthesis methods.

[1043] This carbazole derivative can be produced using known raw materials and known synthesis methods.

[1044] <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 U.S. Patent Application Publication No. 2011 / 0156013. [ka]

[1045] 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.

[1046] The "aryl" in "optionally substituted aryl" includes, for example, aryl having 6 to 30 carbon atoms, preferably aryl having 6 to 24 carbon atoms, more preferably aryl having 6 to 20 carbon atoms, and even more preferably aryl having 6 to 12 carbon atoms.

[1047] Specific examples of "aryl" include phenyl, which is a monocyclic aryl; (2-, 3-, 4-)biphenylyl, which is a bicyclic aryl; (1-, 2-)naphthyl, which is a fused bicyclic aryl; terphenylyl, which is a tricyclic aryl (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), and fused tricyclic aryl. Examples of the aryl include acenaphthylene-(1-, 3-, 4-, 5-)yl, fluoren-(1-, 2-, 3-, 4-, 9-)yl, phenalene-(1-, 2-)yl, (1-, 2-, 3-, 4-, 9-)phenanthryl, tetracyclic aryl quaterphenylyl (5'-phenyl-m-terphenyl-2-yl, 5'-phenyl-m-terphenyl-3-yl, 5'-phenyl-m-terphenyl-4-yl, m-quaterphenylyl), fused tetracyclic aryl triphenylene-(1-, 2-)yl, pyren-(1-, 2-, 4-)yl, naphthacene-(1-, 2-, 5-)yl, and fused pentacyclic aryl perylene-(1-, 2-, 3-)yl and pentacene-(1-, 2-, 5-, 6-)yl.

[1048] 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, still more preferably heteroaryl having 2 to 15 carbon atoms, and particularly preferably heteroaryl having 2 to 10 carbon atoms. Examples of heteroaryl include heterocycles containing, in addition to carbon, 1 to 5 heteroatoms selected from oxygen, sulfur, and nitrogen as ring-constituting atoms.

[1049] 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.

[1050] The aryl and heteroaryl may be substituted, for example, by the above-mentioned aryl or heteroaryl, respectively.

[1051] Specific examples of the triazine derivative include the following compounds: [ka]

[1052] This triazine derivative can be produced using known raw materials and known synthesis methods.

[1053] <Benzimidazole derivatives> The benzimidazole derivative is, for example, a compound represented by the following formula (ETM-11). [ka]

[1054] 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 "benzimidazole-based substituent" is a substituent in which the pyridyl group in the "pyridine-based substituent" in formulae (ETM-2), (ETM-2-1), and (ETM-2-2) is replaced with benzimidazolyl, and at least one hydrogen in the benzimidazole derivative may be replaced with deuterium.

[1055] [ka] * indicates the bond position.

[1056] R in the benzimidazolyl 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 in formula (ETM-2-1) and formula (ETM-2-2) 11 The explanation can be cited.

[1057] φ is preferably an anthracene ring or a fluorene ring, and in this case, the structure can be as described in formula (ETM-2-1) or formula (ETM-2-2), and R 11 ~R 18 The explanation for formula (ETM-2-1) or formula (ETM-2-2) can be cited. In addition, formula (ETM-2-1) or formula (ETM-2-2) is explained in a form in which two pyridine-based substituents are 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 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 replaced with .

[1058] 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-(naphthalen-2-yl)anthracen-9-yl)phenyl)-2-phenyl-1H-benzo[d]imidazole, 2-(4-(9,10-di(naphthalen-2-yl)anthracen-2-yl)phenyl)-1-phenyl-1H-benzo[d]imidazole, 1-(4-(9,10-di(naphthalen-2-yl)anthracen-2-yl)phenyl)-2-phenyl-1H-benzo[d]imidazole, 5-(9,10-di(naphthalen-2-yl)anthracen-2-yl)-1,2-diphenyl-1H-benzo[d]imidazole, and the like.

[1059] [ka]

[1060] The benzimidazole derivative can be produced using known raw materials and known synthesis methods.

[1061] <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]

[1062] 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.

[1063] R in 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 of these bonds to φ, an aryl ring.

[1064] At least one hydrogen atom in each phenanthroline derivative may be substituted with deuterium.

[1065] R 11 ~R 18 The alkyl, cycloalkyl and aryl in formula (ETM-2) include R 11 ~R 18 can be cited. In addition to the examples given above, φ can have the following structural formula: In the structural formula, each R is independently hydrogen, methyl, ethyl, isopropyl, cyclohexyl, phenyl, 1-naphthyl, 2-naphthyl, biphenylyl, or terphenylyl, and * indicates the bonding position.

[1066] [ka]

[1067] 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-phenanthrolin-2-yl)anthracene, 2,6-di(1,10-phenanthrolin-5-yl)pyridine, 1,3,5-tri(1,10-phenanthrolin-5-yl)benzene, 9,9'-difluoro-bi(1,10-phenanthrolin-5-yl), bathocuproine, 1,3-bis(2-phenyl-1,10-phenanthrolin-9-yl)benzene, and compounds represented by the following structural formula: [ka]

[1068] This phenanthroline derivative can be produced using known raw materials and known synthesis methods.

[1069] <Quinolinol-based metal complexes> The quinolinol metal complex is, for example, a compound represented by the following formula (ETM-13). [ka] In the formula, R 1 ~R 6 are each independently hydrogen, fluorine, alkyl, cycloalkyl, aralkyl, al...

Claims

1. A polycyclic aromatic compound represented by the following formula (1) or a dimer having two unit structures represented by the following formula (1): 【Chemistry 1】 (In formula (1), ring A, ring B and ring C are each independently an aryl ring having 6 to 30 carbon atoms or a heteroaryl ring having 2 to 30 carbon atoms, at least one hydrogen atom in these rings may be substituted with a substituent selected from the group consisting of substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted diarylamino, substituted or unsubstituted diheteroarylamino, substituted or unsubstituted arylheteroarylamino, substituted or unsubstituted diarylboryl, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryloxy, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, alkyldicycloalkylsilyl, triarylsilyl, dialkylarylsilyl, and alkyldiarylsilyl, and when these groups have a substituent, the substituent is an aryl, heteroaryl, alkyl or cycloalkyl, or diarylamino, provided that at least one ring selected from the group consisting of ring A, ring B, and ring C is a ring represented by formula (BHet); 【Chemistry 2】 In formula (BHet), R a1 to R a6 are hydrogen or a substituent selected from the group consisting of substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted diarylamino, substituted or unsubstituted diheteroarylamino, substituted or unsubstituted arylheteroarylamino, substituted or unsubstituted diarylboryl, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryloxy, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, alkyldicycloalkylsilyl, triarylsilyl, dialkylarylsilyl, and alkyldiarylsilyl. When these groups have a substituent, the substituent is aryl, heteroaryl, alkyl, or cycloalkyl, with the proviso that any two or three adjacent of R a1 to R a6 are bonds to Y 1 and X 1 and / or X 2 in formula (1), and X is >O, >S, >N—R, or >C(—R) 2 . wherein R in said >N-R or >C(-R) 2 is independently hydrogen, aryl which may be substituted with alkyl or cycloalkyl, heteroaryl which may be substituted with alkyl or cycloalkyl, alkyl, or cycloalkyl, and the two R in said >C(-R) 2 may be bonded to each other to form a ring; Y １ is B, P=O, or P=S; X １ and X ２ are each independently >O, >N-R, or >C(-R) 2 , R of the >N-R is hydrogen, aryl which may be substituted with alkyl or cycloalkyl, heteroaryl which may be substituted with alkyl or cycloalkyl, alkyl, or cycloalkyl, R of the >C(-R) 2 is hydrogen, aryl which may be substituted with alkyl or cycloalkyl, heteroaryl which may be substituted with alkyl or cycloalkyl, alkyl, or cycloalkyl, two R of the >C(-R) 2 may be bonded to each other to form a ring, and R of at least one of the >N-R and >C(-R) 2 may be bonded to at least one of the rings A, B, and C by -O-, -S-, -C(-R) 2 -, or a single bond, and R of the -C(-R) 2 - is hydrogen, alkyl, or cycloalkyl, At least one selected from the group consisting of aryl rings and heteroaryl rings in the polycyclic aromatic compound 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, heteroaryl, alkyl, or cycloalkyl, and at least one —CH ２ - may be replaced by -O-; the polycyclic aromatic compound has at least one substituent selected from the group consisting of trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, alkyldicycloalkylsilyl, triarylsilyl, dialkylarylsilyl, and alkyldiarylsilyl; At least one hydrogen atom in the polycyclic aromatic compound may be replaced with deuterium, cyano, or halogen; In formula (1), each of the aryls is an aryl having 6 to 30 carbon atoms, each of the heteroaryls is a heteroaryl having 2 to 30 carbon atoms, each of the alkyls is an alkyl having 1 to 24 carbon atoms, and each of the cycloalkyls is a cycloalkyl having 3 to 24 carbon atoms. The dimer is in a form in which the A ring, the B ring, or the C ring is bonded to two of the unit structures so as to be shared by each other.

2. A polycyclic aromatic compound represented by the following formula (3), (4), (5), (6), (8), or (9): 【Chemistry 3】 【Chemistry 4】 (In formulas (3), (4), (5), (6), (8), and (9), R １ ~R １７ , R ２１ ~R ２４ , R ３１ ~R ３４ , and R ４１ ~R ４４ are each independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl, alkyl, cycloalkyl, alkoxy, aryloxy, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, alkyldicycloalkylsilyl, triarylsilyl, dialkylarylsilyl, or alkyldiarylsilyl, in which at least one hydrogen may be replaced by aryl, heteroaryl, alkyl, or cycloalkyl; and R １ ~R ３ Adjacent groups among these are bonded to each other to form, together with ring a, R ８ ~R １１ Adjacent groups among these are bonded to each other to form, together with ring b, R ４ ~R ７ Adjacent groups among these are bonded to each other to form, together with ring c, R １２ ~R １４ Adjacent groups among these are bonded to each other to form, together with the a12 ring, R １５ ~R １７ Adjacent groups among these are bonded to each other to form, together with the b15 ring, R ２１ ~R ２４ Adjacent groups among these are bonded to each other to form, together with the c21 ring, R ３１ ~R ３４ adjacent groups are bonded to each other together with the b31 ring, and R ４１ ~R ４４ adjacent groups among the above may be bonded to each other to form, together with ring b41, an aryl ring having 6 to 30 carbon atoms or a heteroaryl ring having 2 to 30 carbon atoms, and at least one hydrogen atom in the formed ring may be substituted with an aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl, alkyl, cycloalkyl, alkoxy, aryloxy, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, or alkyldicycloalkylsilyl, and at least one hydrogen atom in these rings may be substituted with an aryl, heteroaryl, alkyl, or cycloalkyl, Each X is independently >O, >S, >N-R, or >C(-R). ２ wherein R in the >N-R or >C(-R) 2 is independently hydrogen, aryl, heteroaryl, alkyl or cycloalkyl, and the two R in the >C(-R) 2 may be bonded to each other to form a ring; Y １ are each independently B, P=O, or P=S; X １ , X ２ , X ３ , and X ４ are each independently >O, >N-R, or >C(-R)2, and each R in the >N-R is independently hydrogen, an optionally substituted aryl having 6 to 12 carbon atoms, an optionally substituted heteroaryl having 2 to 15 carbon atoms, an optionally substituted alkyl having 1 to 6 carbon atoms, or an optionally substituted cycloalkyl having 3 to 14 carbon atoms, and the >C(-R) ２ R is hydrogen, an optionally substituted aryl having 6 to 12 carbon atoms, an optionally substituted heteroaryl having 2 to 15 carbon atoms, an optionally substituted alkyl having 1 to 6 carbon atoms, or an optionally substituted cycloalkyl having 3 to 14 carbon atoms, and two R in the >C(-R)2 may be bonded to each other to form a ring, and R in at least one of the >N-R and >C(-R)2 is -O-, -S-, -C(-R) ２ may be bonded to at least one of ring a, ring b, ring c, ring a12, ring b15, a 5-membered ring fused to ring c21, a 5-membered ring fused to ring b31, and ring b41 via a single bond, ２ R in - is hydrogen, alkyl, or cycloalkyl; At least one selected from the group consisting of aryl rings and heteroaryl rings in the compound represented by formula (3), (4), (5), (6), (8), or (9) 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, heteroaryl, alkyl, or cycloalkyl, and at least one -CH in the cycloalkane may be condensed with at least one -CH ２ - may be replaced by -O-; the polycyclic aromatic compound has at least one substituent selected from the group consisting of trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, alkyldicycloalkylsilyl, triarylsilyl, dialkylarylsilyl, and alkyldiarylsilyl; At least one hydrogen atom in the compound represented by formula (3), (4), (5), (6), (8), or (9) may be substituted with deuterium, cyano, or halogen; In formula (3), (4), (5), (6), (8), or (9), each of the aryls is an aryl having 6 to 30 carbon atoms, each of the heteroaryls is a heteroaryl having 2 to 30 carbon atoms, each of the alkyls is an alkyl having 1 to 24 carbon atoms, and each of the cycloalkyls is a cycloalkyl having 3 to 24 carbon atoms.

3. The polycyclic aromatic compound according to claim 2, represented by formula (3), (4), (5), or (6).

4. The polycyclic aromatic compound according to claim 1, wherein X is >O or >S.

5. The polycyclic aromatic compound according to any one of claims 1 to 4, which contains at least one tertiary alkyl group represented by the following formula (tR): 【Chemistry 5】 (In formula (tR), R ａ , R ｂ and R ｃ are each independently an alkyl group having 1 to 24 carbon atoms, and any —CH ２ - may be replaced with -O-, and * indicates the bonding position.

6. X 1 , X 2 , X 3 and X 4 are all >N-R, and X １ , X ２ , X ３ or X ４ The polycyclic aromatic compound according to any one of claims 1 to 5, comprising at least one >N-R, in which R is optionally substituted 2-biphenylyl or optionally substituted terphenyl-2'-yl.

7. At least one selected from the group consisting of an aryl ring and a heteroaryl ring is condensed with at least one cycloalkane having 3 to 24 carbon atoms, at least one hydrogen in the cycloalkane is optionally substituted, and at least one -CH in the cycloalkane is ２ The polycyclic aromatic compound according to any one of claims 1 to 6, wherein - may be substituted with -O-.

8. Y １ The polycyclic aromatic compound according to any one of claims 1 to 7, wherein B is

9. X １ , X ２ , X ３ or X ４ The polycyclic aromatic compound according to any one of claims 1 to 8, comprising at least one >N-R, in which R is any of the following groups: 【Chemistry 6】 (Me is methyl, tBu is t-butyl, * indicates the bond position.)

10. The polycyclic aromatic compound according to any one of claims 1 to 9, wherein the halogen is fluorine.

11. The polycyclic aromatic compound according to claim 1 , which is represented by any one of the following structural formulas: 【Chemistry 7】 【Chemistry 8】

12. A material for an organic device, comprising the polycyclic aromatic compound according to any one of claims 1 to 11.

13. The material for an organic device according to claim 12 , which is a material for an organic electroluminescent element, a material for an organic field effect transistor, or a material for an organic thin-film solar cell.

14. The material for an organic device according to claim 13 , wherein the material for an organic electroluminescent element is a material for a light-emitting layer.

15. A composition comprising the polycyclic aromatic compound according to claim 1 and an organic solvent.

16. 12. 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 according to claim 1.

17. 12. An organic electroluminescence device comprising a pair of electrodes consisting of an anode and a cathode, and a light-emitting layer disposed between the pair of electrodes and containing the polycyclic aromatic compound according to claim 1.

18. The organic electroluminescent device according to claim 17 , wherein the light-emitting layer comprises a host and the polycyclic aromatic compound as a dopant.

19. The organic electroluminescent device according to claim 18, wherein the host is an anthracene-based compound, a fluorene-based compound, or a dibenzochrysene-based compound.

20. The organic electroluminescence device according to any one of claims 17 to 19, further comprising an electron transport layer and / or an electron injection layer disposed between the cathode and the light emitting layer, and at least one of the electron transport layer and the electron injection layer contains at least one selected from the group consisting of borane derivatives, pyridine derivatives, fluoranthene derivatives, BO-based derivatives, anthracene derivatives, benzofluorene derivatives, phosphine oxide derivatives, pyrimidine derivatives, arylnitrile derivatives, triazine derivatives, benzimidazole derivatives, phenanthroline derivatives, quinolinol-based metal complexes, thiazole derivatives, benzothiazole derivatives, silole derivatives and azoline derivatives.

21. 21. The organic electroluminescent device according to claim 20, wherein the electron transport layer and / or the electron injection layer further contains at least one selected from the group consisting of alkali metals, alkaline earth metals, rare earth metals, oxides of alkali metals, halides of alkali metals, oxides of alkaline earth metals, halides of alkaline earth metals, oxides of rare earth metals, halides of rare earth metals, organic complexes of alkali metals, organic complexes of alkaline earth metals, and organic complexes of rare earth metals.

22. A display device or lighting device comprising an organic electroluminescent element according to any one of claims 16 to 21.

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