Polycyclic aromatic compounds

Abstract

To provide a new compound as a material used for organic EL devices.SOLUTION: A polycyclic aromatic compound has one or more structural units represented by formula (1). In the formula, A ring and B ring each denote an aryl ring or a heteroaryl ring; Y1 is B or the like; RXC is aryl or heteroaryl or the like; RXC may bound to A ring (and / or B ring) via a linking group or a single bond; X1 is >N-R (R is aryl or the like) or the like; adjacent two atoms on an aryl ring or heteroaryl ring in A ring, B ring or RXC are bound with moieties represented by formula (A) at the sites *, and L is >N-R or the like (R is aryl or the like or bound to RA or the like); r is an integer of 1-4; RA is alkyl or the like; the aryl ring or the like may be condensed with cycloalkane.SELECTED DRAWING: None

Description

[Technical Field]

[0001] The present invention relates to a polycyclic aromatic compound. The present invention also relates to a material for an organic device, an organic electroluminescent device, a display device, and a lighting device, each containing 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 (potentially becoming 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] Among them, Patent Document 1 discloses that polycyclic aromatic compounds in which aromatic rings are linked by heteroelements such as boron, phosphorus, oxygen, nitrogen, and sulfur are useful as materials for organic electroluminescent devices, etc. These polycyclic aromatic compounds have a large HOMO-LUMO gap and high triplet excitation energy (E T ) and exhibits thermally activated delayed fluorescence, it has been reported that it is particularly useful as a fluorescent material for organic electroluminescent devices. [Prior art documents] [Patent documents]

[0005] [Patent Document 1] International Publication No. 2015 / 102118 Summary of the Invention [Problem to be solved by the invention]

[0006] As described above, various materials have been developed for use in organic EL devices, but in order to increase the options for materials for organic EL devices, it is desirable to develop materials made of compounds that are different from conventional materials. An object of the present invention is to provide a novel material that is useful as a material for organic devices such as organic EL devices. [Means for solving the problem]

[0007] The present inventors conducted extensive research to solve the above-mentioned problems and succeeded in producing a new polycyclic aromatic compound in which aromatic rings are linked by heteroatoms such as boron, phosphorus, oxygen, nitrogen, and sulfur. They also discovered that an excellent organic EL device can be obtained by disposing a layer containing this polycyclic aromatic compound between a pair of electrodes, thereby completing the present invention. Specifically, the present invention provides the following polycyclic aromatic compounds, as well as materials for organic devices containing the following polycyclic aromatic compounds.

[0008] <1> A polycyclic aromatic compound having a structure consisting of one or more structural units represented by the following formula (1): [ka]

[0009] In formula (1), ring A and ring B are each independently an aryl ring or a heteroaryl ring, and at least one hydrogen atom in these rings may be substituted; Y 1 is B, P, P=O or P=S, R XCis optionally substituted aryl, optionally substituted heteroaryl, optionally substituted alkyl or optionally substituted cycloalkyl; R XC may be bonded to at least one of ring A or ring B via a linking group or single bond shown by a dashed line, X 1 is >C(-R)2, >NR, >O, >Si(-R)2 or >S, R of the >NR is an optionally substituted aryl, an optionally substituted heteroaryl, an optionally substituted alkyl or an optionally substituted cycloalkyl, R of the >C(-R)2 and >Si(-R)2 is hydrogen, an optionally substituted aryl, an optionally substituted alkyl or an optionally substituted cycloalkyl, and may be bonded to each other by a linking group, and at least one of R of the >NR, the >C(-R)2 and the >Si(-R)2 may be bonded to at least one of the A ring or the B ring by a linking group or a single bond, In the above structure, the A ring, the B ring and R XC At least one selected from the group consisting of: contains at least one partial structure represented by formula (A), The partial structure represented by formula (A) is bonded to two adjacent atoms on the aryl or heteroaryl ring at two *'s, respectively. In formula (A), L is >NR, >O, >Si(-R)2 or >S, R of the >NR is an optionally substituted aryl, an optionally substituted heteroaryl, an optionally substituted alkyl or an optionally substituted cycloalkyl, R of the >Si(-R)2 is hydrogen, an optionally substituted aryl, an optionally substituted alkyl or an optionally substituted cycloalkyl, and may be bonded to each other by a linking group, and at least one of R of the >NR and the >Si(-R)2 is connected to the ring A, ring B, or ring R by a linking group or a single bond. XC and R A and optionally linked to at least one selected from the group consisting of: r is an integer from 1 to 4; R A are each independently hydrogen, optionally substituted alkyl, or optionally substituted cycloalkyl, and any R A is any other R A and may be bonded to each other by a linking group or a single bond, At least one selected from the group consisting of an aryl ring and a heteroaryl ring in the above structure 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- or -S-; At least one hydrogen in the structure may be replaced with deuterium, cyano, or halogen.

[0010] <2> A ring, B ring and R XC wherein the substituent when at least one hydrogen atom in the aryl ring or heteroaryl ring is replaced is selected from the group consisting of substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted diarylamino, substituted or unsubstituted alkylarylamino, 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; <1> The polycyclic aromatic compound according to claim 1. <3> Y 1 is B, <1> or <2> The polycyclic aromatic compound according to claim 1.

[0011] <4> The structure contains at least one tertiary alkyl group represented by the following formula (tR): <1> ~ <3> The polycyclic aromatic compound according to any one of the preceding claims. [ka] In the formula (tR), Ra , R b and R c are each independently alkyl having 1 to 24 carbon atoms, any —CH2— in the alkyl may be replaced with —O—, and * represents the bonding position.

[0012] <5> The partial structure represented by formula (A) is bonded to an aryl ring or heteroaryl ring in ring B. <1> ~ <4> 1. The polycyclic aromatic compound according to any one of claims 1 to 9. <6> The partial structure represented by formula (A) is bonded to two adjacent carbon atoms on an aryl or heteroaryl ring at two * marks, r is 2, Two Rs bonded to adjacent carbon atoms A are bonded to each other, and other R A are each independently hydrogen or optionally substituted alkyl; <1> ~ <5> 1. The polycyclic aromatic compound according to any one of claims 1 to 9. <7> Two Rs bonded to adjacent carbon atoms A are bonded to each other to form -(CH2)4-, and the remaining R A are all methyl, <6> The polycyclic aromatic compound according to claim 1. <8> L is >NR, and R of said >NR is optionally substituted aryl. <1> ~ <7> 1. The polycyclic aromatic compound according to any one of claims 1 to 9.

[0013] <9> The partial structure represented by (A) is the following structure: <1> ~ <5> the polycyclic aromatic compound according to any one of the preceding claims; [ka]

[0014] In the formula, the two *'s are attached to two adjacent atoms on the aryl or heteroaryl ring, respectively, and Me is methyl. <10> R XC is an optionally substituted aryl or an optionally substituted heteroaryl, and the linking group X 2It is connected to the A ring by X 2 >C(-R) 2、 >NR, >O, >Si(-R)2 or >S, wherein R of the >NR is an optionally substituted aryl, an optionally substituted heteroaryl, an optionally substituted alkyl or an optionally substituted cycloalkyl, R of the >C(-R)2 and >Si(-R)2 is hydrogen, an optionally substituted aryl, an optionally substituted alkyl or an optionally substituted cycloalkyl, and may be bonded to each other by a linking group, and at least one of R of the >NR, the >C(-R)2 and the >Si(-R)2 is connected to the A ring and R by a linking group or a single bond. XC and optionally linked to at least one selected from the group consisting of: <1> ~ <9> 1. The polycyclic aromatic compound according to any one of claims 1 to 9. <11> X 1 is >NR and X 1 R of >NR represented by the formula: is optionally substituted aryl, optionally substituted heteroaryl, optionally substituted alkyl or optionally substituted cycloalkyl, and is optionally bonded to at least one of the A ring or B ring via a linking group or a single bond; X 2 is >NR and X 2 R of >NR is optionally substituted aryl, optionally substituted heteroaryl, optionally substituted alkyl or optionally substituted cycloalkyl, and said A ring and R are connected by a linking group or a single bond. XC and optionally linked to at least one selected from the group consisting of: <10> The polycyclic aromatic compound according to claim 1. <12> R XC is an optionally substituted aryl or an optionally substituted heteroaryl, and is bonded to ring A via a single bond; <1> ~ <9> 1. The polycyclic aromatic compound according to any one of claims 1 to 9.

[0015] <13> Having a structure represented by the following formula (1-BA1) or formula (1-BA2): <1> the polycyclic aromatic compound according to [ka]

[0016] In formula (1-BA1) and formula (1-BA2), ring c is an optionally substituted benzene ring, an optionally substituted benzofuran ring, or an optionally substituted benzothiophene ring; R is, independently, an optionally substituted phenyl; R 2 ' is hydrogen or alkyl having 1 to 6 carbon atoms, In at least one benzene ring in the structure, hydrogen atoms bonded to adjacent carbon atoms may be substituted with a partial structure represented by formula (B);

[0017] [ka] In formula (B), Me represents methyl, and * represents the bonding position.

[0018] <14> It has a structure represented by one of the following formulas: <13> the polycyclic aromatic compound according to [ka] In the formula, Me represents methyl and tBu represents t-butyl.

[0019] <15> Having a structure represented by the following formula (1-BA3) or formula (1-BA4): <1> the polycyclic aromatic compound according to [ka] In formula (1-BA3) and formula (1-BA4), ring c is an optionally substituted benzene ring, an optionally substituted benzofuran ring, or an optionally substituted benzothiophene ring; R is, independently, an optionally substituted phenyl; R 2' is hydrogen or alkyl having 1 to 6 carbon atoms, In at least one benzene ring in the structure, hydrogen atoms bonded to adjacent carbon atoms may be substituted with a partial structure represented by formula (B);

[0020] [ka] In formula (B), Me represents methyl, and * represents the bonding position.

[0021] <16> It has a structure represented by one of the following formulas: <15> the polycyclic aromatic compound according to [ka] In the formula, Me represents methyl and tBu represents t-butyl.

[0022] <17> Having a structure represented by the following formula (1-BA5), (1-BA6), formula (1-BA7) or formula (1-BA8): <1> the polycyclic aromatic compound according to [ka]

[0023] In formulas (1-BA5), (1-BA6), (1-BA7) and (1-BA8), Ring D is an optionally substituted benzene ring or an optionally substituted cyclohexane ring, R is, independently, an optionally substituted phenyl; R d are each independently hydrogen, optionally substituted alkyl, optionally substituted aryl, optionally substituted heteroaryl, or optionally substituted diarylamino; In at least one benzene ring in the structure, hydrogen atoms bonded to adjacent carbon atoms may be substituted with a partial structure represented by formula (B);

[0024] [ka] In formula (B), Me represents methyl, and * represents the bonding position.

[0025] <18> It has a structure represented by one of the following formulas: <17> the polycyclic aromatic compound according to [ka] In the formula, Me represents methyl and tBu represents t-butyl.

[0026] <19> Having a structure represented by any of the following formulas: <1> the polycyclic aromatic compound according to [ka]

[0027] In formula (1-BA11), formula (1-BA12), formula (1-BA13) and formula (1-BA14), Z is C(-R Z ) or N, and R Z are each independently hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl; R is, independently, an optionally substituted phenyl; R 2 ' is hydrogen or alkyl having 1 to 6 carbon atoms, In at least one benzene ring in the structure, hydrogen atoms bonded to adjacent carbon atoms may be substituted with a partial structure represented by formula (B);

[0028] [ka] In formula (B), Me represents methyl, and * represents the bonding position.

[0029] <20> Having a structure represented by any of the following formulas: <19> the polycyclic aromatic compound according to [ka]

[0030] <21> <1> ~ <20> 1. A reactive compound in which the polycyclic aromatic compound according to any one of the above items is substituted with a reactive substituent. <22> <21> 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. <23> Main chain polymer <21> or a pendant-type crosslinked polymer obtained by further crosslinking the pendant-type polymer compound. <24> <1> ~ <20> 10. A material for an organic device, comprising the polycyclic aromatic compound according to any one of claims 1 to 9. <25> <21> A material for an organic device, comprising the reactive compound according to claim 1. <26> <22> 1. A material for an organic device, comprising the polymer compound or crosslinked polymer described in 1. <27> <23> 10. A material for an organic device, comprising the pendant polymer compound or the pendant polymer crosslinked product according to claim 1. <28> 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; <24> ~ <27> 1. The material for an organic device according to any one of the preceding items. <29> The material for an organic electroluminescent device is a material for a light-emitting layer. <28> The material for an organic device according to claim 1.

[0031] <30> <1> ~ <20> and an organic solvent. <31> <21> and an organic solvent. <32> a main chain polymer; <21> and an organic solvent. <33> <22> 10. An ink composition comprising the polymer compound or crosslinked polymer described in 1 above and an organic solvent. <34> <23> 10. An ink composition comprising the pendant polymer compound or pendant polymer crosslinked product according to claim 1, and an organic solvent.

[0032] <35> a pair of electrodes consisting of an anode and a cathode, and a gas supply device disposed between the pair of electrodes; <1> ~ <20> The polycyclic aromatic compound according to any one of <21> a reactive compound according to <22> or the polymer compound or crosslinked polymer described in <23> and an organic layer containing the pendant polymer compound or the pendant polymer crosslinked product according to claim 1. <36> the organic layer is an emitting layer; <35> The organic electroluminescent device according to claim 1. <37> the light-emitting layer contains a host and the polycyclic aromatic compound, its reactive compound, polymer compound, crosslinked polymer, pendant polymer compound, or pendant crosslinked polymer as a dopant; <36> The organic electroluminescent device according to claim 1. <38> the host is an anthracene-based compound, a fluorene-based compound, or a dibenzochrysene-based compound; <37> The organic electroluminescent device according to claim 1. <39> at least one of an electron transport layer and an electron injection layer is 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, and quinolinol-based metal complexes; <35> ~ <38> 10. The organic electroluminescent device according to claim 9, wherein <40> At least one of the electron transport layer and the electron injection layer further contains at least one selected from the group consisting of alkali metals, alkaline earth metals, rare earth metals, alkali metal oxides, alkali metal halides, alkaline earth metal oxides, alkaline earth metal halides, rare earth metal oxides, rare earth metal halides, alkali metal organic complexes, alkaline earth metal organic complexes, and rare earth metal organic complexes. <39> The organic electroluminescent device according to claim 1. <41> 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, <35> ~ <40> 10. The organic electroluminescent device according to claim 9, wherein <42> <35> ~ <41> A display device or a lighting device comprising the organic electroluminescent device according to any one of the preceding claims. [Effects of the Invention]

[0033] 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 a light-emitting layer in an organic electroluminescent device. [Brief explanation of the drawings]

[0034] [Figure 1] FIG. 1 is a schematic cross-sectional view showing an example of an organic EL element. [Figure 2] 1A to 1C are diagrams 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

[0035] 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)."

[0036] 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.

[0037] 1. Polycyclic aromatic compounds The polycyclic aromatic compound of the present invention is a polycyclic aromatic compound having a structure consisting of one or more structural units represented by the following formula (1): The polycyclic aromatic compound of the present invention has at least one partial structure represented by formula (A).

[0038] [ka]

[0039] 1-1. Partial structure represented by formula (A) In the structure consisting of one or more structural units represented by formula (1), ring A, ring B and R XCAt least one selected from the group consisting of contains at least one partial structure represented by formula (A). In the above structure, it is preferable that one or two partial structures represented by formula (A) are contained. The partial structure represented by formula (A) is preferably a B ring or R XC The partial structure represented by formula (A) is preferably included in the following: XC Each of the partial structures represented by formula (A) is bonded to two adjacent atoms on the ring of one of the aryl or heteroaryl rings. In this case, it is preferable that both adjacent atoms on the ring are carbon atoms. A fused ring structure is formed by bonding the partial structure represented by formula (A) to the aryl or heteroaryl ring. Because the polycyclic aromatic compound of the present invention has this fused ring structure, the compound has a more rigid structure. This rigidity is expected to suppress molecular vibration, improve EQE, increase molecular stability, and extend the device life.

[0040] In formula (A), L is >NR, >O, >Si(-R)2, or >S. By selecting the type of L in the partial structure represented by formula (A), it is possible to control the HOMO and LUMO of the compound of the present invention. When L is >NR, >O, or >S, the HOMO and LUMO become shallower, and when L is >Si(-R)2, the HOMO and LUMO become deeper. If the HOMO and LUMO become shallower, TTF devices using these are expected to have longer lifetimes, higher efficiency, and lower driving voltages. On the other hand, if the HOMO and LUMO become deeper, the hole-trapping properties of the dopant will disappear, and the driving voltage is expected to be significantly lower.

[0041] R of >NR as L in formula (A) is optionally substituted aryl, optionally substituted heteroaryl, optionally substituted alkyl, or optionally substituted cycloalkyl. R of >Si(-R)2 as L in formula (A) is hydrogen, optionally substituted aryl, optionally substituted alkyl, or optionally substituted cycloalkyl, and may be bonded to each other via a linking group. In addition, at least one of R of >NR as L and R of >Si(-R)2 as L is connected to the A ring, B ring, or R via a linking group or a single bond.XC (C ring) and R A L is preferably >NR, >O or >S, more preferably >NR or >O, and even more preferably >NR.

[0042] When L is >NR, R is preferably aryl optionally substituted with alkyl or cycloalkyl, heteroaryl optionally substituted with alkyl or cycloalkyl, alkyl or cycloalkyl, more preferably aryl optionally substituted with alkyl or cycloalkyl, or heteroaryl optionally substituted with alkyl or cycloalkyl, still more preferably aryl optionally substituted with alkyl or cycloalkyl, and particularly preferably phenyl optionally substituted with alkyl or cycloalkyl.

[0043] In formula (A), r is an integer of 1 to 4, preferably 2 or 3, and more preferably 2 (the structure below). [ka]

[0044] In formula (A), R A are each independently hydrogen, optionally substituted alkyl, or optionally substituted cycloalkyl, and any R A is any other R A and may be linked to each other via a linking group or a single bond.

[0045] R A Among these, it is preferable that at least one pair of two R are bonded to each other by a linking group or a single bond, and two R A are more preferably bonded to each other via a linking group or a single bond. Examples of the linking group include >O and >S. The divalent group formed by bonding together includes alkylene. At least one hydrogen atom in the alkylene may be substituted with an alkyl or cycloalkyl, and at least one (preferably one) -CH2- group in the alkylene may be substituted with -O- and -S-. The divalent group formed by bonding together is preferably a linear alkylene group having 2 to 5 carbon atoms, more preferably a linear alkylene group having 3 or 4 carbon atoms, and even more preferably a linear alkylene group having 4 carbon atoms (-(CH2)4-). It is particularly preferred that the linear alkylene group having 4 carbon atoms (-(CH2)4-) is unsubstituted.

[0046] Two Rs bonded to adjacent carbon atoms A are bonded to each other by a linking group or a single bond, the remaining R A are preferably each independently hydrogen or optionally substituted alkyl, or are bonded to R of >NR which is L.

[0047] Two Rs bonded to adjacent carbon atoms A are bonded to each other by a linking group or a single bond, the remaining R A The optionally substituted alkyl as represented by is more preferably an optionally substituted alkyl having 1 to 6 carbon atoms, further preferably an unsubstituted alkyl having 1 to 6 carbon atoms, and most preferably methyl in both cases. That is, a preferred example of the partial structure represented by formula (A) is a structure represented by formula (Aa-1).

[0048] [ka] In the formula, Me is methyl.

[0049] At least one of R in >NR and >Si(-R)2 in L is connected to the ring A, ring B, or R by a linking group or a single bond. XC (C ring) and R AWhen L is >NR, examples of such a structure include a structure represented by any of the following formulae, and a structure represented by formula (Ab-1) is preferred.

[0050] [ka]

[0051] In each formula, Me is methyl. In each formula, * indicates ring A, ring B and R XC and each bond to two or three consecutive (adjacent) atoms on the ring of any aryl or heteroaryl ring in the ring.

[0052] 1-2. Structural unit (skeletal structure) represented by formula (1) In formula (1), "A" and "B" are symbols indicating ring structures. In formula (1), ring A and ring B are each independently an aryl ring or a heteroaryl ring, and at least one hydrogen atom in these rings may be substituted. R XC is optionally substituted aryl, optionally substituted heteroaryl, optionally substituted alkyl or optionally substituted cycloalkyl. R XC may be bonded to at least one of the rings A and B via a linking group or a single bond shown by a broken line. 2 Examples of the linking group include the following: R XC is preferably an optionally substituted aryl or an optionally substituted heteroaryl. XC is an optionally substituted aryl or an optionally substituted heteroaryl, and a single bond or a linking group X 2 It is more preferable that the ring A is bonded to the ring B via the following formula (1):

[0053] [ka]

[0054] In formula (2), the same symbols as those in formula (1) have the same meanings as those in formula (1). "C" is a symbol indicating a ring structure, and R in formula (1) XC (X 2 ) n represents one embodiment of the dashed line in formula (1), and n is 0 or 1. When n is 0, it indicates that ring A and ring C are bonded by a single bond, and when n is 1, it indicates that ring A and ring C are bonded by a linking group X 2 indicates that the bond is established. (X 2 ) n is Y in the A ring 1 is preferably bonded to an atom adjacent to the atom to which it is bonded.

[0055] The rings A and B in formula (1) and the rings A, B and C in formula (2) are each independently an aryl ring or a heteroaryl ring. The aryl or heteroaryl rings in the rings A, B and C in formula (2) are each independently selected from the group consisting of Y 1 , X 1 and (X 2 ) n It is preferable that the fused two-ring structure of formula (2) has a five- or six-membered ring that shares a bond with the central fused two-ring structure.

[0056] Here, the "fused two-ring structure" refers to the center of formula (2), Y 1 , X 1 and (X 2 ) nIt is preferable that both rings in this fused bicyclic structure are six-membered rings. The "six-membered ring sharing a bond with the fused bicyclic structure" refers to a six-membered ring (e.g., a benzene ring) fused to the fused bicyclic structure. Furthermore, the phrase "an aryl ring or heteroaryl ring (which is ring A) has this six-membered ring" means that ring A is formed solely from this six-membered ring, or that ring A is formed by further condensing another ring to this six-membered ring so as to include this six-membered ring. In other words, the "aryl ring 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 bicyclic structure. The same explanation applies to "ring B," "ring C," and "five-membered ring." When n is 0, that is, when ring A and ring C are bonded by a single bond, ring C is an aryl ring or heteroaryl ring having a fused ring structure, and it is preferred that any two directly fused monocyclic rings in this fused ring structure are each fused to the fused bicyclic structure.

[0057] Examples of polycyclic aromatic compounds having a structure consisting of one of the structural units represented by formula (2) include polycyclic aromatic compounds represented by any of the following formulas (2-1) to (2-9). [ka]

[0058] In formulas (2-1) to (2-9), Z is C(-R Z ) or N. R Zare each independently hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted diarylamino, substituted or unsubstituted alkylarylamino, 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, and R bonded to an adjacent C (carbon atom) Z They 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 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.

[0059] In formulas (2-1) to (2-9), Y 1 , X 1 and X 2 is Y in equation (2) 1 , X 1 and X 2 are synonymous with each other. In formulas (2-2) to (2-6), (2-8), and (2-9), X 3 and X 4 are independently >C(-R) 2、>NR, >O, >Si(-R)2 or >S, wherein R of the >NR is an aryl having 6 to 12 carbon atoms, a heteroaryl having 2 to 15 carbon atoms, an alkyl having 1 to 6 carbon atoms or a cycloalkyl having 3 to 14 carbon atoms, and R of the >C(-R)2 and >Si(-R)2 is hydrogen, an aryl having 6 to 12 carbon atoms, an alkyl having 1 to 6 carbon atoms or a cycloalkyl having 3 to 14 carbon atoms.

[0060] In each of the formulas (2-1) to (2-9), the partial structure represented by formula (A) is a ring, b ring, c ring, and R Z The partial structure represented by formula (A) is preferably bonded to two adjacent carbon atoms on ring b and / or ring c at two * positions, and more preferably bonded to two adjacent carbon atoms on ring b at two * positions, in each of formulas (2-1) to (2-9).

[0061] In formulas (2-2) to (2-6), (2-8), and (2-9), X 3 and X 4 are independently >C(-R) 2、 It is preferably >NR, >O or >S, and more preferably >O or >S.

[0062] In formulas (2-1) to (2-9), Z is C(-R Z ) or N. In each of formulas (2-1) to (2-9), the number of rings (monocycles) containing Z, which is N, is preferably 0 to 4, more preferably 0 to 3, further preferably 0 to 2, and particularly preferably 0 to 1. In each of formulas (2-1) to (2-9), all of Z are C(-R Z ) is also preferred.

[0063] In formulas (2-1) to (2-9), in a ring (monocycle) 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. When the 6-membered ring is a ring containing Z as N, it is preferably a pyridine ring, pyrimidine ring, pyridazine ring, pyrazine ring, or 1,2,3-triazine ring, and more preferably a pyridine ring or pyrimidine ring. When the 5-membered ring is a ring containing Z as N, it is preferably an imidazole ring, thiazole ring, or oxazole ring.

[0064] In formulas (2-1) to (2-9), Y 1 , X 1 , X 2 , and Z is C(-R Z ) in R Z The preferred ranges for each of these will be described later.

[0065] In each of the formulas (2-1) to (2-9), R bonded to adjacent C (carbon atom) Z They may be bonded together to form an aryl ring or a heteroaryl ring together with ring a, ring b or ring c. For example, in the case of a compound represented by formula (2-1), the ring structure constituting the compound changes depending on the mutual bonding form of the substituents in ring a, ring b, and ring c, as shown in the following formulas (2-1-1) and (2-1-2). Ring A', ring B', and ring C' in each formula correspond to ring A, ring B, and ring C in formula (2-1), respectively. In addition, Z, a, b, c, and Y in each formula 1 , X 1 and X 2 The definition of is the same as that in formula (2-1).

[0066] [ka]

[0067] The A' ring, B' ring and C' ring in formula (2-1-1) and formula (2-1-2) are, as explained in formula (2-1), R bonded to the adjacent C (carbon atom). ZThese rings are bonded to each other to form an aryl or heteroaryl ring together with the a, b, and c rings (these rings can also be considered fused rings formed by fusing other ring structures to the a, b, or c rings). Although not shown in the formula, there are also compounds in which all of the a, b, and c rings are replaced by A', B', and C' rings.

[0068] For example, the fused ring A' (or fused ring B' or fused ring C') which is the ring A' (or ring B' or ring C') formed by fusing a benzene ring, an indole ring, a pyrrole ring, a furan ring, a thiophene ring, a benzofuran ring, a benzothiophene ring, a cyclopentadiene ring, or an indene ring to a benzene ring which is the ring a (or ring b or ring c) is a naphthalene ring, a carbazole ring, an indole ring, a benzofuran ring, a benzothiophene ring, a dibenzofuran ring, a dibenzothiophene ring, an indene ring, or a fluorene ring, respectively.

[0069] Similarly, in each of formulas (2-2) to (2-9), a fused ring may be formed by fusing another ring structure to ring a, ring b, or ring c. For example, the benzene ring of ring a or ring b may be fusing with another ring structure to form a fused ring, similar to the benzene ring in formula (2-1). In the formulas (2-2) to (2-6), (2-8), and (2-9), in the 5-membered ring that is the b ring or the c ring, R bonded to the adjacent carbon atom Z It is particularly preferred that R bonded to adjacent Cs to form a ring, i.e., a fused ring. For example, in the c rings of formulas (2-2) and (2-3), and the b rings and c rings of formulas (2-4), (2-5), and (2-6), R bonded to adjacent Cs Z When these rings are bonded to each other to form a ring, a fused ring B' or C' can be formed. When the ring formed is a benzene ring, examples of the fused ring include an indene ring, an indole ring, a benzofuran ring, and a benzothiophene ring.

[0070] In formulas (2-1) to (2-6), Z is C(-R Z) are shown in the following formulas (3-1) to (3-11). The following formulas (3-7) to (3-11) show the R bonded to the adjacent C in the 5-membered ring that is the b ring or the c ring in formulas (2-2) to (2-6). Z These are examples of structures in which fused rings are formed by bonding together to form a benzene ring.

[0071] [ka]

[0072] In formulas (3-1) to (3-11), Y 1 , X 1 ~X 4 is Y in formulas (2-1) to (2-6). 1 , X 1 ~X 4 are synonymous with each other. In formulas (3-1) to (3-11), R 1 ~R 11 is hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted diarylamino, substituted or unsubstituted alkylarylamino, 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.

[0073] In each of formulas (3-1) to (3-11), the partial structure represented by formula (A) is bonded to two adjacent carbon atoms on one or more rings selected from the group consisting of ring a, ring b, and ring c at the positions marked with two *. In each of formulas (3-1) to (3-11), the partial structure represented by formula (A) is preferably bonded to two adjacent carbon atoms on ring b and / or ring c at the positions marked with two *.

[0074] In formulas (3-1) to (3-11), X 3 and X 4 are independently >C(-R) 2、 It is preferably >NR, >O or >S, and more preferably >O or >S. In formulas (3-1) to (3-11), Y 1 , X 1 , X 2 , and R 1 ~R 11 The preferred ranges for each of these will be described later.

[0075] Among the formulas (3-1) to (3-11), the formula (3-1), the formula (3-2), the formula (3-3), the formula (3-7), or the formula (3-8) is preferred, and the formula (3-1) or the formula (3-7) is more preferred.

[0076] Among formulas (2-7) to (2-9), formula (2-7) is preferred. Preferred examples of the compound represented by formula (2-7) include compounds represented by the following formula (3-21) or formula (3-22).

[0077] [ka]

[0078] In formulas (3-21) to (3-22), Y 1 , X 1 is Y in formulas (2-1) to (2-9). 1 , X 1 are synonymous with R. 1 ~R 12 is R in formulas (3-1) to (3-11). 1 ~R 11 is synonymous with.

[0079] 1-2. Structure consisting of two or more structural units represented by formula (1) The polycyclic aromatic compound of the present invention is a polycyclic aromatic compound having a structure consisting of one or more structural units represented by formula (1). Examples of polycyclic aromatic compounds having a structure consisting of one of the structural units include polycyclic aromatic compounds represented by the formulas described above for the structural unit represented by formula (1). Examples of polycyclic aromatic compounds having a structure consisting of two or more structural units represented by formula (1) include compounds corresponding to multimers of polycyclic aromatic compounds represented by the formulas described above for the structural unit represented by formula (1). The multimer is preferably a dimer to a hexamer, more preferably a dimer to a trimer, and particularly preferably a dimer. The multimer may be in a form in which a plurality of the above unit structures are bonded together so that any ring (ring A, ring B or ring C, ring a, ring b or ring c) contained in the above unit structure is shared by multiple unit structures, or may be in a form in which any ring (ring A, ring B or ring C, ring a, ring b or ring c) contained in the above unit structure is bonded together so that they are fused together. Furthermore, the above unit structures may be in a form in which a plurality of them are bonded together via a linking group such as a single bond, alkylene having 1 to 3 carbon atoms, phenylene, or naphthylene.

[0080] Examples of structures consisting of two or more structural units represented by formula (1) include structures represented by the following formulas, in which the structural unit represented by formula (1) is a structural unit represented by formula (3-1). In each of the following formulas, the ring a, ring b, ring c, and Y 1 , X 1 , X 2 , R 1 ~R 11 represents the a ring, b ring, c ring, and Y in formula (3-1). 1 , X 1 , X 2 , R 1 ~R 11 and (iii) are the same as those in the formula (I). In each of the formulas below, at least one ring selected from the group consisting of ring a, ring b, and ring c contains at least one partial structure represented by formula (A). The partial structure represented by formula (A) may or may not be contained in each structural unit represented by formula (1), as long as at least one partial structure is contained in the overall structure of the polycyclic aromatic compound.

[0081] [ka]

[0082] [ka]

[0083] In the formulas (3-1-4), (3-1-4-1), (3-1-4-2), (3-1-5-1) to (3-1-5-5), (3-1-6), and (3-1-7), X 1 , X 2 , R 1 ~R 11The a-ring, b-ring, and c-ring have the same meanings as those in formula (3-1). The multimeric compound represented by formula (3-1-4), when explained in terms of formula (3-1), is a multimeric compound (dimer) having multiple unit structures represented by formula (3-1) in one compound, with the benzene ring (a-ring) being shared between them. The multimeric compound represented by formula (3-1-4-1), when explained in terms of formula (3-1), is a multimeric compound (dimer) having two unit structures represented by formula (3-1) in one compound, with the benzene ring (a-ring) being shared between them. The multimeric compound represented by formula (3-1-4-2), when explained in terms of formula (3-1), is a multimeric compound (trimer) having three unit structures represented by formula (3-1) in one compound, with the benzene ring (a-ring) being shared between them. Furthermore, the multimeric compounds represented by formulas (3-1-5-1) to (3-1-5-5), when explained in terms of formula (3-1), are multimeric compounds (formula (3-1-5-4) is a trimer, and the others are dimers) having a plurality of unit structures represented by formula (3-1) in one compound, with the benzene ring being the b ring (or c ring) in common. Furthermore, the multimeric compound represented by formula (3-1-6), when explained in terms of formula (3-1), is a multimeric compound (dimer) having a plurality of unit structures represented by formula (3-1) in one compound, with the benzene ring being the b ring (or a ring, c ring) of a certain unit structure fused with the benzene ring being the b ring (or a ring, c ring) of a certain unit structure. Furthermore, the polymeric compound represented by formula (3-1-7), when explained in terms of formula (3-1), is a polymeric compound (trimer) having a plurality of unit structures represented by formula (3-1) in one compound, in such a way that they share a benzene ring, which is a b ring or a c ring.

[0084] 1-3. Substructures within the structural unit The rings A and B in formula (1) and the rings A, B, and C in formula (2) are each independently an aryl ring or a heteroaryl ring. At least one hydrogen atom in these rings may be substituted with a substituent.

[0085] The "aryl ring" which is ring A and ring B in formula (1) and ring A, ring B and ring C in formula (2) 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.

[0086] 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.

[0087] Examples of the "heteroaryl ring" which is ring A and ring B in formula (1) and ring A, ring B, and ring C in formula (2) 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, still more preferably heteroaryl rings having 2 to 15 carbon atoms, and particularly preferably heteroaryl rings having 2 to 10 carbon atoms. Furthermore, 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.

[0088] 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 naphthyridine ring, a purine ring, and 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, a dibenzazepine ring, a tribenzazepine ring, an iminodibenzyl ring, etc. Furthermore, as for the dihydroacridine ring, the xanthene ring, and the thioxanthene ring, two of the two hydrogen atoms of the methylene are preferably substituted with alkyl such as methyl as the first substituent described below, to form 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.

[0089] When at least one hydrogen atom in the above-mentioned aryl ring or heteroaryl ring is substituted with a substituent, the substituent is preferably substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted diarylamino, substituted or unsubstituted alkylarylamino, substituted or unsubstituted diheteroarylamino, substituted or unsubstituted arylheteroarylamino (amino having aryl and heteroaryl), 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.When these groups have a substituent, the substituent may be aryl, heteroaryl, alkyl or cycloalkyl, or diarylamino.

[0090] At least one hydrogen atom in the above-mentioned "aryl ring" or "heteroaryl ring" may be substituted by a first substituent, which is a substituted or unsubstituted "aryl," a substituted or unsubstituted "heteroaryl," a substituted or unsubstituted "diarylamino," a substituted or unsubstituted "alkylarylamino," a substituted or unsubstituted "diheteroarylamino," a substituted or unsubstituted "arylheteroarylamino," a substituted or unsubstituted "diarylboryl (two aryls may be bonded via a single bond or a linking group)," a substituted or unsubstituted "alkyl," a substituted or unsubstituted "cycloalkyl," a substituted or unsubstituted "alkoxy," a substituted or unsubstituted "aryloxy," or a substituted "silyl." Examples of the "aryl" or "heteroaryl" as the first substituent include the aryl in "diarylamino," the aryl in "alkylarylamino," the heteroaryl in "diheteroarylamino," the aryl and heteroaryl in "arylheteroarylamino," the aryl in "diarylboryl," and the aryl in "aryloxy" are monovalent groups of the "aryl ring" or "heteroaryl ring" described above.

[0091] 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.

[0092] 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.

[0093] 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.

[0094] 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.

[0095] 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.

[0096] 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.

[0097] 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.

[0098] As the substituent containing the above-mentioned "alkyl," a tertiary alkyl represented by the following formula (tR) is particularly preferred as a substituent when at least one hydrogen atom in the above-mentioned aryl ring or heteroaryl ring is substituted with a substituent. This is because such a bulky substituent increases the intermolecular distance, thereby improving the luminescence quantum yield (PLQY). Substituents in which the tertiary alkyl represented by formula (tR) is substituted with another substituent as a second substituent are also preferred. Specific examples include a diarylamino substituted with a tertiary alkyl represented by (tR), a carbazolyl (preferably N-carbazolyl) substituted with a tertiary alkyl represented by (tR), or a benzocarbazolyl (preferably N-benzocarbazolyl) substituted with a tertiary alkyl represented by (tR). Examples of the "diarylamino" include the groups described below as the "first substituent." Substitution of the group of formula (tR) on diarylamino, carbazolyl and benzocarbazolyl includes examples in which some or all of the hydrogen atoms on the aryl ring or benzene ring in these groups are substituted with the group of formula (tR).

[0099] [ka]

[0100] 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 *.

[0101] R a , R b and R cThe "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).

[0102] 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.

[0103] R a , R b , and R c Specific examples of alkyl include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, t-butyl, n-pentyl, isopentyl, neopentyl, t-pentyl, n-hexyl, 1-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, n-heptyl, 1-methylhexyl, n-octyl, t-octyl, 1-methylheptyl, 2 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.

[0104] 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.

[0105] As "alkylarylamino", methylphenylamino is preferred.

[0106] 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.

[0107] 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 norbornyl (bicyclo[2.2.1]heptyl), bicyclo[1.1.0]butyl, bicyclo[1.1.1]pentyl, bicyclo[2.1.0]pentyl, bicyclo[2.1.1]hexyl, bicyclo[3.1.0]hexyl, bicyclo[2.2.2]octyl, adamantyl, diamantyl, decahydronaphthalenyl, and decahydroazulenyl.

[0108] 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.

[0109] Specific examples of alkoxy include methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, s-butoxy, t-butoxy, t-amyloxy, pentyloxy, hexyloxy, heptyloxy, and octyloxy.

[0110] 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.

[0111] 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.

[0112] 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.

[0113] 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[2.1.0]pentyl, bicyclo[2.1.1]hexyl, bicyclo[3.1.0]hexyl, bicyclo[2.2.1]heptyl, bicyclo[2.2.2]octyl, adamantyl, decahydronaphthalenyl, and decahydroazulenyl.

[0114] Specific examples of tricycloalkylsilyl include tricyclopentylsilyl and tricyclohexylsilyl.

[0115] 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.

[0116] 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.

[0117] 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.

[0118] As described above, at least one hydrogen atom in the first substituent, substituted or unsubstituted "aryl," substituted or unsubstituted "heteroaryl," substituted or unsubstituted "diarylamino," substituted or unsubstituted "alkylarylamino," 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," may be substituted with a second substituent. Examples of this second substituent include aryl, heteroaryl, alkyl, or cycloalkyl. For specific examples, 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.

[0119] 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 (particularly N-carbazolyl), and 3,6-dimethylcarbazolyl. Preferred are 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. 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.

[0120] 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]

[0121] [ka]

[0122] [ka]

[0123]

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[0124]

change

[0125]

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[0126]

change

[0127]

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[0128]

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[0129]

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[0130]

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[0131]

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[0132]

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[0133]

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[0134] [ka]

[0135] In formula (2-1) to formula (2-9), Z is C(-R Z ) when R Z is hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted diarylamino, substituted or unsubstituted alkylarylamino, 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 each of formulas (2-1) to (2-9), R Z The group R includes a group bonded to two adjacent atoms to form a partial structure represented by formula (A). Z may bond to adjacent atoms to form a ring, and together with ring a, ring b, or ring c, form an aryl ring or a heteroaryl ring, and these rings may be substituted with a substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted diarylamino, substituted or unsubstituted alkylarylamino, 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.

[0136] For details and preferred ranges thereof, the explanations of the first and second substituents can be referred to. Specifically, when each of the above substituents is substituted, the substituent (second substituent) includes aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl (two aryls may be bonded via a single bond or a linking group), alkyl, cycloalkyl, alkoxy, aryloxy, triarylsilyl, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, or alkyldicycloalkylsilyl, and at least one hydrogen atom in these may be substituted with aryl, heteroaryl, alkyl, or cycloalkyl.

[0137] In formula (2-1) to formula (2-9), Z is C(-R Z ) when R Z 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, a triarylsilyl (wherein the aryl is an aryl having 6 to 12 carbon atoms), or a trialkylsilyl (wherein the alkyl is an alkyl having 1 to 6 carbon atoms), provided that adjacent R Z may be bonded to each other to form, together with ring a, ring b or ring c, 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 aryl having 6 to 10 carbon atoms, alkyl having 1 to 12 carbon atoms, cycloalkyl having 3 to 16 carbon atoms, triarylsilyl (provided that aryl is aryl having 6 to 12 carbon atoms), or trialkylsilyl (provided that alkyl is alkyl having 1 to 5 carbon atoms); More preferably, they are each independently hydrogen, aryl having 6 to 16 carbon atoms, heteroaryl having 2 to 20 carbon atoms, diarylamino (wherein the aryl is aryl having 6 to 10 carbon atoms), alkyl having 1 to 12 carbon atoms, or cycloalkyl having 3 to 16 carbon atoms; More preferably, they are each independently hydrogen, aryl having 6 to 16 carbon atoms, diarylamino (wherein aryl is aryl having 6 to 10 carbon atoms), alkyl having 1 to 12 carbon atoms or cycloalkyl having 3 to 16 carbon atoms.

[0138] Of the rings a, b, and c in each of formulas (2-1) to (2-9), in the rings bonded to the partial structure represented by formula (A), Z other than the bonding site is preferably CH.

[0139] In formulas (3-1) to (3-11), formulas (3-21), and formulas (3-22), R 1 ~R 12are each independently hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted diarylamino, substituted or unsubstituted alkylarylamino, 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. For details and preferred ranges of these, please refer to the explanations of the first substituent and the second substituent above. Specifically, when each of the above substituents is substituted, examples of the substituent (second substituent) include aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl (two aryls may be bonded via a single bond or a linking group), alkyl, cycloalkyl, alkoxy, aryloxy, triarylsilyl, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, and alkyldicycloalkylsilyl, and at least one hydrogen atom in these may be substituted with aryl, heteroaryl, alkyl, or cycloalkyl.

[0140] Specifically, in the formulas (3-1) to (3-11), (3-21), and (3-22), R 1 ~R 12 are preferably each independently hydrogen, an aryl having 6 to 30 carbon atoms, a heteroaryl having 2 to 30 carbon atoms, a diarylamino (provided that the aryl is an aryl having 6 to 12 carbon atoms), a 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), an alkyl having 1 to 24 carbon atoms, a cycloalkyl having 3 to 24 carbon atoms, a triarylsilyl (provided that the aryl is an aryl having 6 to 12 carbon atoms), or a trialkylsilyl (provided that the alkyl is an alkyl having 1 to 6 carbon atoms); More preferably, they are each independently hydrogen, aryl having 6 to 16 carbon atoms, heteroaryl having 2 to 20 carbon atoms, diarylamino (wherein the aryl is aryl having 6 to 10 carbon atoms), alkyl having 1 to 12 carbon atoms, or cycloalkyl having 3 to 16 carbon atoms; More preferably, they are each independently hydrogen, aryl having 6 to 16 carbon atoms, diarylamino (wherein aryl is aryl having 6 to 10 carbon atoms), alkyl having 1 to 12 carbon atoms or cycloalkyl having 3 to 16 carbon atoms.

[0141] In equation (1), Y 1 is B, P, P=O or P=S, preferably B or P=O, more preferably B. This explanation applies to Y in formula (2), formulas (2-1) to (2-9), formulas (3-1) to (3-11), formula (3-21) and formula (3-22). 1 The same applies to.

[0142] X in formula (1) 1 and X in formula (2) 1 and X 2 are independently >C(-R) 2、 and R of the >NR is an optionally substituted aryl, an optionally substituted heteroaryl, an optionally substituted alkyl, or an optionally substituted cycloalkyl, and R of the >C(-R) and >Si(-R) is hydrogen, an optionally substituted aryl, an optionally substituted alkyl, or an optionally substituted cycloalkyl, and two R are preferably the same and may be bonded to each other by a linking group, and at least one of R of the >NR, the >C(-R), and the >Si(-R) is connected to the A ring, the B ring, and R by a linking group or a single bond. XC This explanation applies to X in formula (2), formulas (2-1) to (2-9), formula (3-1) to (3-11), formula (3-21), and formula (3-22). 1 and X 2 The same applies to "A ring, B ring and RXC In formula (2), "at least one selected from the group consisting of ring A, ring B, and ring C" is read as "at least one selected from the group consisting of ring a, ring b, and ring c" in formulas (2-1) to (2-9), (3-1) to (3-11), (3-21), and (3-22).

[0143] X in formula (1), formulas (2-7) to (2-9), formula (3-21), and formula (3-22) 1 are each independently preferably >O or >NR, more preferably >NR. X in formula (2), formulas (2-1) to (2-6), and formulas (3-1) to (3-11) 1 and X 2 At least one of the groups is preferably >NR, and it is more preferable that all of the groups are >NR.

[0144] X 1 and X 2 For the aryl, heteroaryl, alkyl, and cycloalkyl in R of >NR in the above, the description thereof as the first substituent can be referred to. 1 and X 2 In the formula (tR), R is preferably an optionally substituted aryl, an optionally substituted heteroaryl, or an optionally substituted cycloalkyl, and more preferably an optionally substituted aryl. Here, the aryl is preferably phenyl, biphenylyl (particularly 2-biphenylyl), or terphenylyl (particularly terphenyl-2'-yl), and more preferably phenyl or biphenylyl. When the aryl is substituted, the substituent is preferably a tertiary alkyl (particularly t-butyl) or methyl represented by the formula (tR) described below. The number of substituents in the aryl is preferably 0 to 3, more preferably 1 to 3. It is also preferred that the aryl ring in the above aryl is condensed with a cycloalkane as described below.

[0145] X 1 and X2 In the formula (I), R in >NR is particularly preferably unsubstituted phenyl, phenyl having t-butyl bonded to the para position, phenyl having t-butyl bonded to the para position and methyl bonded to one or two ortho positions, or 2-(5,4'-ditertiarybutyl)biphenylyl.

[0146] X 1 and X 2 In the formula (1-3-1), 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. The linking group is preferably -O-, -S-, or -C(-R)2-. R in the "-C(-R)2-" is hydrogen, alkyl, or cycloalkyl. Examples of such structures include X represented by the following formula (1-3-1): 1 a compound having a ring structure in which X is incorporated into a fused ring B', represented by the following formula (1-3-2): 1 is incorporated into the fused ring A', a compound represented by the following formula (2-3-1), 2 is incorporated into the fused ring C', and X in formula (2) represented by the following formula (2-3-2) 2 is incorporated into fused ring A'. The formed fused ring A' (fused ring B' or fused ring C') is, for example, a carbazole ring, a phenoxazine ring, a phenothiazine ring, or an acridine ring.

[0147] [ka]

[0148] X 1 and X 2 When R in >NR is bonded to at least one of rings A, B, and C by a linking group or a single bond, X 1 or X 2 may form the following partial structure (A10):

[0149] [ka]

[0150] In formula (A10), R B are each independently hydrogen, optionally substituted alkyl, or optionally substituted cycloalkyl; R B Any two to four of these may be bonded to each other via a linking group or a single bond, and may be bonded to ring A at two * positions and ring B or ring C at ** position, or may be bonded to ring B or ring C at two * positions and ring A at ** position. That is, N in formula (A10) is X 1 or X 2 The atoms on the ring bonded at the two * positions may be adjacent atoms (preferably carbon atoms). Although the partial structure represented by formula (A10) contains an N-C bond with a weak bond dissociation energy (BDE), the presence of another bond forming a ring promotes the reverse reaction (recombination reaction) even when the N-C bond is broken, making polycyclic aromatic compounds with the partial structure represented by formula (A10) a more stable structure. Therefore, organic EL devices manufactured using polycyclic aromatic compounds with the partial structure represented by formula (A10) are expected to have a longer device life. The number of partial structures represented by formula (A10) formed by the above-mentioned linkage contained in the polycyclic aromatic compound is preferably one or two.

[0151] In formula (A10), R B is hydrogen, optionally substituted alkyl, or optionally substituted cycloalkyl, and any R B is another R B and may be linked to each other via a linking group or a single bond. R B Any two of R are preferably bonded to each other via a linking group or a single bond, A1 and R A4are more preferably bonded to each other via a linking group or a single bond. An example of the divalent group formed by bonding to each other is alkylene. At least one hydrogen atom in the alkylene may be substituted with an alkyl or cycloalkyl, and at least one (preferably one) -CH2- in the alkylene may be substituted with -O- and -S-. The linking group is preferably a straight-chain alkylene having 2 to 5 carbon atoms, more preferably a straight-chain alkylene having 3 or 4 carbon atoms, and even more preferably a straight-chain alkylene having 4 carbon atoms (-(CH2)4-). It is particularly preferred that the straight-chain alkylene having 4 carbon atoms (-(CH2)4-) is unsubstituted.

[0152] The remaining R that is not involved in the linkage by the linking group B are each independently preferably hydrogen or an alkyl which may be substituted, more preferably an alkyl having 1 to 6 carbon atoms which may be substituted, further preferably an unsubstituted alkyl having 1 to 6 carbon atoms, and most preferably methyl. That is, the partial structure represented by formula (A10) is preferably a structure represented by the following formula (A11).

[0153] [ka]

[0154] In formula (A11), Me is methyl and is bonded to ring A at the two * positions and to ring B or C at the ** position, or is bonded to ring B or C at the two * positions and to ring A at the ** position.

[0155] In addition, X in formula (2) is expressed by formula (2-3-1). 2 is incorporated into the fused ring C', and X in formula (2) represented by the following formula (2-3-2) 2 A compound having a ring structure in which n is incorporated into the fused ring A' can also be considered to be a compound in which n is 0 in formula (2). Examples of the structure of the fused ring C' in formula (2-3-1) include structures represented by any of the following formulas (each structure may have a substituent).

[0156] [ka]

[0157] In each formula, Y is placed at the position of *. 1 and A ring (preferably Y) at position # 1 is bonded to the carbon atom adjacent to the carbon atom to which it is bonded. Examples of the structure of the fused ring A' in formula (2-3-1) include structures represented by any of the following formulas (each structure may have a substituent).

[0158] [ka]

[0159] In each formula, Y is placed at the position of *. 1 , ** at position X 1 , and binds to the C ring at position #.

[0160] The polycyclic aromatic compound of the present invention can be used as a material for organic devices. Examples of organic devices include organic electroluminescent devices, organic field-effect transistors, and organic thin-film solar cells. In particular, in organic electroluminescent devices, the compound represented by formula (2) where Y 1 is B, X 1 and X 2 Compounds where all of 1 is B, X 1 >O,X 2 Compounds where Y is >NR 1 is B, X 1 and X 2 Compounds in which all of 1 is B, X 1 and X 2 are preferably compounds in which all of Y are >C(-R)2, 1 is B, X1 and X 2 Compounds where all of 1 is B, X 1 and X 2 More preferred are compounds in which all of Y are >C(-R)2, 1 is B, X 1 and X 2 The most preferred compound is a compound in which all of the above are >NR. 1 is B, X 1 >O,X 2 Compounds where all of 1 is B, X 1 and X 2 As the electron transporting material, a compound in which all of 1 is B, X 1 and X 2 Compounds in which all of 1 P=O,X 1 and X 2 A compound in which all of are >O is preferably used.

[0161] X in equation (1) 1 And X in formula (2) 1 and X 2 R of >Si(-R)2 in the formula (2-1) and R of >Si(-R)2 as a linking group connecting ring B and ring C are aryl, heteroaryl, alkyl, or cycloalkyl, which may be substituted with the second substituent described above. Examples of the aryl, heteroaryl, alkyl, or cycloalkyl include the groups described above. In particular, aryl having 6 to 10 carbon atoms (e.g., phenyl, naphthyl, etc.), heteroaryl having 2 to 15 carbon atoms (e.g., carbazolyl, etc.), alkyl having 1 to 5 carbon atoms (e.g., methyl, ethyl, etc.), or cycloalkyl having 5 to 10 carbon atoms (preferably cyclohexyl or adamantyl) are preferred. This explanation applies to X in formulas (2-1) to (2-9), formulas (3-1) to (3-11), formula (3-21), and formula (3-22). 1 and X 2 The same applies to R in >Si(-R)2 as

[0162] X in equation (1) 1 And X in formula (2) 1 and X 2 R in >C(-R)2 in the formula (2-1) and R in >C(-R)2 as a linking group connecting the B ring and the C ring are hydrogen, aryl, heteroaryl, alkyl, or cycloalkyl, which may be substituted with the second substituent described above. Examples of the aryl, heteroaryl, alkyl, or cycloalkyl include the groups described above. In particular, aryl having 6 to 10 carbon atoms (e.g., phenyl, naphthyl, etc.), heteroaryl having 2 to 15 carbon atoms (e.g., carbazolyl, etc.), alkyl having 1 to 5 carbon atoms (e.g., methyl, ethyl, etc.), or cycloalkyl having 5 to 10 carbon atoms (preferably cyclohexyl or adamantyl) are preferred. This explanation applies to X in formulas (2-1) to (2-9), formulas (3-1) to (3-11), formula (3-21), and formula (3-22). 1 and X 2 The same applies to R in >C(-R)2 as

[0163] X in equation (1) 1 And X in formula (2) 1 and X 2 In the case where R in at least one of >NR, >Si(-R)2, and >C(-R)2 is bonded to at least one of the rings A, B, and C via a linking group or a single bond, examples of the linking group include -O-, -S-, -C(-R)2-, or 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 applies to X in formulas (2-1) to (2-9), formulas (3-1) to (3-11), formulas (3-21), and formula (3-22). 1 and X 2 The same applies to the linking group "-C(-R)2-" when it is bonded to at least one of the rings a, b, and c.

[0164] At least one selected from the group consisting of aryl rings and heteroaryl rings in a structure consisting of one or more structural units represented by formula (1) may be condensed with at least one cycloalkane, at least one hydrogen atom in the cycloalkane may be substituted, and at least one -CH2- in the cycloalkane may be substituted with -O- or -S-. The same applies to formulas (2), (2-1) to (2-9), (3-1) to (3-11), (3-21), and (3-22).

[0165] Examples of "cycloalkane" include cycloalkanes having 3 to 24 carbon atoms, cycloalkanes having 3 to 20 carbon atoms, cycloalkanes having 3 to 16 carbon atoms, cycloalkanes having 3 to 14 carbon atoms, cycloalkanes having 5 to 10 carbon atoms, cycloalkanes having 5 to 8 carbon atoms, cycloalkanes having 5 to 6 carbon atoms, and cycloalkanes having 5 carbon atoms.

[0166] Specific examples of the cycloalkane include cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclooctane, cyclononane, cyclodecane, norbornane (bicyclo[2.2.1]heptane), bicyclo[1.1.0]butane, bicyclo[1.1.1]pentane, bicyclo[2.1.0]pentane, bicyclo[2.1.1]hexane, bicyclo[3.1.0]hexane, 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.

[0167] Among these, a structure in which at least one hydrogen atom is substituted on the α-carbon atom of the 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 such a substituent include alkyl (particularly methyl) substituents having 1 to 5 carbon atoms, halogen (particularly fluorine) substituents, and deuterium substituents. In particular, a structure in which a partial structure represented by the following formula (B) is bonded to adjacent carbon atoms in an aryl ring or heteroaryl ring is preferred.

[0168] [ka] In formula (B), Me represents methyl, and * represents the bonding position.

[0169] All or part of the hydrogen atoms in the chemical structure of a polycyclic aromatic compound having a structure consisting of one or more structural units represented by formula (1) or formula (2) may be substituted with deuterium, cyano, or halogen. For example, in formula (1) or formula (2), the A ring, B ring, and C ring (A to C rings are aryl rings or heteroaryl rings), the substituents on A to C rings, 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 most preferably fluorine. From the viewpoint of durability, it is also preferable that all or some of the hydrogen atoms in the chemical structure of a polycyclic aromatic compound having a structure consisting of one or more structural units represented by formula (1) or formula (2) are deuterated. This explanation also applies to compounds in which formula (1) is any of formulas (2-1) to (2-9), formulas (3-1) to (3-11), formula (3-21), and formula (3-22).

[0170] 1-4. Preferred structure examples As the polycyclic aromatic compound of the present invention, when n is 1 in formula (2), preferred examples include compounds having a structure represented by formula (1-BA1), formula (1-BA2), formula (1-BA3), formula (1-BA4), formula (1-BA5), formula (1-BA6), formula (1-BA7), or formula (1-BA8).

[0171] [ka]

[0172] In formulas (1-BA1), (1-BA2), (1-BA3) and (1-BA4), ring c is an optionally substituted benzene ring, an optionally substituted benzofuran ring, or an optionally substituted benzothiophene ring; R is, independently, an optionally substituted phenyl; R 2 ' is hydrogen or alkyl having 1 to 6 carbon atoms, In at least one benzene ring in the above structure, hydrogen atoms bonded to adjacent carbon atoms may be substituted with a partial structure represented by formula (B). In formula (1-BA1), formula (1-BA2), formula (1-BA3) and formula (1-BA4), the benzofuran ring and the benzothiophene ring in the ring c are each a 6-membered ring (benzene ring), and B and X 2 and B and X may be bonded to a five-membered ring (furan ring or thiophene ring). 2 may be bound to

[0173] [ka]

[0174] In formulas (1-BA5), (1-BA6), (1-BA7) and (1-BA8), Ring D is an optionally substituted benzene ring or an optionally substituted cyclohexane ring, R is, independently, an optionally substituted phenyl; R d are each independently hydrogen, optionally substituted alkyl, optionally substituted aryl, optionally substituted heteroaryl, or optionally substituted diarylamino; In at least one benzene ring in the above structure, hydrogen atoms bonded to adjacent carbon atoms may be substituted with a partial structure represented by formula (B).

[0175] In formulas (1-BA5), (1-BA6), (1-BA7), and (1-BA8), ring D is preferably an unsubstituted benzene ring (bonded as 1,2-phenylene) or a 1,2-dimethylcyclohexane ring (bonded as a group with hydrogen atoms at positions 1 and 2 eliminated; forming a structure represented by formula (A11)). d are preferably each independently hydrogen or unsubstituted alkyl having 1 to 6 carbon atoms.

[0176] From another point of view, preferred examples include compounds having the following structures:

[0177] [ka]

[0178] [ka]

[0179] In each of the structural formulas above, the hydrogen atoms bonded to the benzene ring may be substituted with methyl, t-butyl, diphenylamino, or phenyl, and the hydrogen atoms bonded to adjacent carbon atoms on the benzene ring may be substituted with the partial structure represented by formula (B). Furthermore, the hydrogen atoms of the diphenylamino and phenyl may be substituted with methyl or t-butyl, and the two hydrogen atoms bonded to two adjacent carbon atoms may be substituted with the partial structure represented by formula (B).

[0180] As the polycyclic aromatic compound of the present invention, when n is 0 in formula (2), preferred examples include formula (1-BA11), formula (1-BA12), formula (1-BA13) and formula (1-BA14). [ka]

[0181] In formula (1-BA11), formula (1-BA12), formula (1-BA13) and formula (1-BA14), Z is C(-R Z ) or N, and R Z are each independently hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl; R are each independently an optionally substituted phenyl; R 2 ' is hydrogen or alkyl having 1 to 6 carbon atoms, In at least one benzene ring in the above structure, hydrogen atoms bonded to adjacent carbon atoms may be substituted with a partial structure represented by formula (B).

[0182] 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, "Ad" represents adamantyl, and "TMS" represents trimethylsilyl.

[0183] [ka]

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[0218] Polycyclic aromatic compounds having a structure consisting of one or more structural units represented by formula (1) can be used as materials for organic devices, such as materials for organic electroluminescent elements, materials for organic field-effect transistors, and materials for organic thin-film solar cells, in the form of polymer compounds obtained by polymerizing a reactive compound substituted with a reactive substituent on the polycyclic aromatic compound as a monomer (the monomer for obtaining this polymer compound has a polymerizable substituent), or a crosslinked polymer obtained by further crosslinking the polymer compound (the polymer compound for obtaining this crosslinked polymer has a crosslinkable substituent), or 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 polymer has a crosslinkable substituent).

[0219] 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, substituents capable of further crosslinking the polymer compound thus obtained, and substituents capable of pendant reaction 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.

[0220] [ka]

[0221] 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.

[0222] 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.

[0223] 2. Method for producing polycyclic aromatic compounds Polycyclic aromatic compounds having a structure consisting of one or more structural units represented by formula (1) are basically composed of ring A (a-ring), ring B (b-ring), and R XC (C ring, c ring) and a bonding group (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 1 The final product can be produced by bonding the two groups together with a group containing (a group containing (A)) (second reaction). In the first reaction, for example, common reactions such as nucleophilic substitution and the Ullmann reaction can be used for etherification, and common reactions such as the Buchwald-Hartwig reaction can be used for amination. Furthermore, in the second reaction, a tandem hetero-Friedel-Crafts reaction (sequential aromatic electrophilic substitution reaction, hereinafter the same) can be used. For these production methods, see prior art documents such as International Publication No. 2015 / 102118. Compounds having a partial structure represented by formula (A) can be produced by using a raw material having a partial structure represented by formula (A) somewhere in the reaction process or by adding a step to introduce a partial structure represented by formula (A).

[0224] 3. Organic Devices The 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.

[0225] 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.

[0226] 3-1-1. 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.

[0227] 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.

[0228] Not all of the above layers are essential, and the minimum structural unit is anode 102, light-emitting layer 105, and cathode 108, with hole injection layer 103, hole transport layer 104, electron transport layer 106, and electron injection layer 107 being optional layers. Each of the above layers may consist of a single layer or multiple layers. In this specification, layers such as the light-emitting layer, hole injection layer, hole transport layer, electron transport layer, and electron injection layer that constitute the organic EL device may be referred to as organic layers.

[0229] 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."

[0230] 3-1-2. 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.

[0231] 3-1-3. 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.

[0232] 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.

[0233] 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.

[0234] 3-1-4. 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.

[0235] 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.

[0236] 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, N 4 ,N 4’ -diphenyl-N 4 ,N 4 '-Bis(9-phenyl-9H-carbazol-3-yl)-[1,1'-biphenyl]-4,4'-diamine, N 4 ,N 4 ,N 4 ',N 4'-Tetra[1,1'-biphenyl]-4-yl)-[1,1'-biphenyl]-4,4'-diamine, 4,4',4"-tris(3-methylphenyl(phenyl)amino)triphenylamine, 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.

[0237] 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).

[0238] 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.

[0239] 3-1-5. 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.

[0240] 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.

[0241] 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.

[0242] 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.

[0243] Examples of host materials include fused ring derivatives such as anthracene, pyrene, dibenzochrysene, and fluorene, which have long been known as light emitters; bisstyryl derivatives such as bisstyryl anthracene derivatives and distyrylbenzene derivatives; tetraphenylbutadiene derivatives; cyclopentadiene derivatives; and carbazole compounds such as 3,3'-di(9H-carbazol-9-yl)-1,1'-biphenyl. Anthracene-based compounds, fluorene-based compounds, dibenzochrysene-based compounds, and carbazole compounds are preferred, with anthracene-based compounds and carbazole compounds 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.

[0244] 3-1-6. Electron injection layer and electron transport layer in organic electroluminescent devices 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.

[0245] 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.

[0246] 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.

[0247] 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.

[0248] 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.

[0249] Furthermore, metal complexes having an electron-accepting nitrogen atom can also be used, and examples thereof include hydroxyazole complexes such as quinolinol metal complexes and hydroxyphenyloxazole complexes, azomethine complexes, tropolone metal complexes, flavonol metal complexes, and benzoquinoline metal complexes.

[0250] The above-mentioned materials may be used alone or in combination with other materials.

[0251] 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.

[0252] <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.

[0253] 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]

[0254] In formula (ETM-1-1), R 11 and R12 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, 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; and 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.

[0255] [ka]

[0256] 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.

[0257] 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.

[0258] Specific examples of the borane derivative include the following compounds: [ka]

[0259] This borane derivative can be produced using known raw materials and known synthesis methods.

[0260] <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]

[0261] 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.

[0262] 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).

[0263] In formula (ETM-2-2), R 11 and R 12 are each independently hydrogen, alkyl (preferably alkyl having 1 to 24 carbon atoms), cycloalkyl (preferably cycloalkyl having 3 to 12 carbon atoms), or aryl (preferably aryl having 6 to 30 carbon atoms), and R 11 and R 12 may be bonded to form a ring.

[0264] 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.

[0265] [ka]

[0266] 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]

[0267] 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.

[0268] 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).

[0269] 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.

[0270] The above description of alkyl can be cited for the alkyl having 1 to 4 carbon atoms that substitutes the pyridine-based substituent.

[0271] 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.

[0272] 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.

[0273] 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.

[0274] 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.

[0275] 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.

[0276] Specific examples of this pyridine derivative include, for example, the following compounds.

Chemical formula

[0277] This pyridine derivative can be produced using known raw materials and known synthesis methods.

[0278] <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

[0279] 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, etc.

[0280] Specific examples of this fluoranthene derivative include, for example, the following compounds.

Chemical formula

[0281] <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

[0282] 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.

[0283] 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.

[0284] 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.

[0285] 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.

[0286] Specific examples of the BO derivative include the following compounds: [ka]

[0287] This BO derivative can be produced using known raw materials and known synthesis methods.

[0288] <Anthracene derivatives> One of the anthracene derivatives is, for example, a compound represented by the following formula (ETM-5). [ka]

[0289] Ar 1 are each independently a single bond, a divalent benzene, a divalent naphthalene, a divalent anthracene, a divalent fluorene, or a divalent phenalene.

[0290] 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.

[0291] 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.

[0292] 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.

[0293] 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.

[0294] Specific examples of these anthracene derivatives include the following compounds: [ka]

[0295] These anthracene derivatives can be produced using known raw materials and known synthesis methods.

[0296] <Benzofluorene derivatives> The benzofluorene derivative is, for example, a compound represented by the following formula (ETM-6). [ka]

[0297] 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.

[0298] 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.

[0299] 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.

[0300] 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.

[0301] 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.

[0302] Specific examples of the "aryl having 6 to 30 carbon atoms" include phenyl, naphthyl, acenaphthylenyl, fluorenyl, phenalenyl, phenanthryl, triphenylenyl, pyrenyl, naphthacenyl, perylenyl, and pentacenyl.

[0303] 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.

[0304] Specific examples of the benzofluorene derivative include the following compounds: [ka]

[0305] This benzofluorene derivative can be produced using known raw materials and known synthesis methods.

[0306] <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]

[0307] 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.

[0308] The phosphine oxide derivative may be, for example, a compound represented by the following formula (ETM-7-2). [ka]

[0309] 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, formyl, carbonyl, carboxyl, amino, nitro, silyl, and a fused ring formed between adjacent substituents.

[0310] 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.

[0311] 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.

[0312] 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.

[0313] 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.

[0314] 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.

[0315] 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.

[0316] 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.

[0317] 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.

[0318] Moreover, alkylthio is a group in which the oxygen atom of the ether bond of alkoxy is substituted with a sulfur atom.

[0319] Moreover, cycloalkylthio is a group in which the oxygen atom of the ether bond of cycloalkoxy is substituted with a sulfur atom.

[0320] 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.

[0321] 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.

[0322] 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.

[0323] 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.

[0324] Halogen refers to fluorine, chlorine, bromine, and iodine.

[0325] Formyl, carbonyl and amino may also include groups substituted with an aliphatic hydrocarbon, alicyclic hydrocarbon, aromatic hydrocarbon, heterocycle or the like.

[0326] The aliphatic hydrocarbons, alicyclic hydrocarbons, aromatic hydrocarbons and heterocyclic rings may be either unsubstituted or substituted.

[0327] 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.

[0328] 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.

[0329] Specific examples of the phosphine oxide derivative include the following compounds: [ka]

[0330] This phosphine oxide derivative can be produced using known raw materials and known synthesis methods.

[0331] <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]

[0332] 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.

[0333] 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.

[0334] 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.

[0335] 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.

[0336] 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.

[0337] The aryl and heteroaryl may be substituted, for example, by the above-mentioned aryl or heteroaryl, respectively.

[0338] Specific examples of the pyrimidine derivative include the following compounds: [ka]

[0339] This pyrimidine derivative can be produced using known raw materials and known synthesis methods.

[0340] <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]

[0341] 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.

[0342] 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.

[0343] 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.

[0344] 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.

[0345] 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.

[0346] 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.

[0347] The aryl and heteroaryl may be substituted, for example, by the above-mentioned aryl or heteroaryl, respectively.

[0348] 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.

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

[0350] The arylnitrile derivative can be produced using known raw materials and known synthesis methods.

[0351] <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]

[0352] 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.

[0353] 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.

[0354] 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.

[0355] 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.

[0356] 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.

[0357] The aryl and heteroaryl may be substituted, for example, by the above-mentioned aryl or heteroaryl, respectively.

[0358] Specific examples of the triazine derivative include the following compounds: [ka]

[0359] This triazine derivative can be produced using known raw materials and known synthesis methods.

[0360] <Benzimidazole derivatives> The benzimidazole derivative is, for example, a compound represented by the following formula (ETM-11). [ka]

[0361] 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 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.

[0362] [ka]

[0363] 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.

[0364] 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 .

[0365] 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.

[0366] [ka]

[0367] The benzimidazole derivative can be produced using known raw materials and known synthesis methods.

[0368] <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]

[0369] 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.

[0370] 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 becomes a bond to the aryl ring φ.

[0371] At least one hydrogen atom in each phenanthroline derivative may be substituted with deuterium.

[0372] 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.

[0373] [ka]

[0374] 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:

[0375] [ka]

[0376] This phenanthroline derivative can be produced using known raw materials and known synthesis methods.

[0377] <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, alkenyl, cyano, alkoxy, or aryl; M is Li, Al, Ga, Be, or Zn; and n is an integer of 1 to 3.

[0378] Specific examples of quinolinol-based metal complexes include 8-quinolinol lithium, tris(8-quinolinolato)aluminum, tris(4-methyl-8-quinolinolato)aluminum, tris(5-methyl-8-quinolinolato)aluminum, tris(3,4-dimethyl-8-quinolinolato)aluminum, tris(4,5-dimethyl-8-quinolinolato)aluminum, tris(4,6-dimethyl-8-quinolinolato)aluminum, bis(2-methyl-8-quinolinolato)(phenolate)aluminum, and bis(2-methyl-8-quinolinolato). Bis(2-methyl-8-quinolinolate)(2-methylphenolate)aluminum, bis(2-methyl-8-quinolinolate)(3-methylphenolate)aluminum, bis(2-methyl-8-quinolinolate)(4-methylphenolate)aluminum, bis(2-methyl-8-quinolinolate)(2-phenylphenolate)aluminum, bis(2-methyl-8-quinolinolate)(3-phenylphenolate)aluminum, bis(2-methyl-8-quinolinolate)(4-phenylphenolate)aluminum, bis(2-methyl-8-quinolinolate)(2,3 -dimethylphenolate)aluminum, bis(2-methyl-8-quinolinolate)(2,6-dimethylphenolate)aluminum, bis(2-methyl-8-quinolinolate)(3,4-dimethylphenolate)aluminum, bis(2-methyl-8-quinolinolate)(3,5-dimethylphenolate)aluminum, bis(2-methyl-8-quinolinolate)(3,5-di-t-butylphenolate)aluminum, bis(2-methyl-8-quinolinolate)(2,6-diphenylphenolate)aluminum, bis(2-methyl-8-quinolinolate)(3,5-di-t-butylphenolate)aluminum linolinolate)(2,4,6-triphenylphenolate)aluminum, bis(2-methyl-8-quinolinolate)(2,4,6-trimethylphenolate)aluminum, bis(2-methyl-8-quinolinolate)(2,4,5,6-tetramethylphenolate)aluminum, bis(2-methyl-8-quinolinolate)(1-naphtholate)aluminum, bis(2-methyl-8-quinolinolate)(2-naphtholate)aluminum, bis(2,4-dimethyl-8-quinolinolate)(2-phenylphenolate)aluminum, bis(2,4-dimethyl-8-quinolinolate)(3-phenylphenolate)aluminum, bis(2,4-dimethyl-8-quinolinolate)(4-phenylphenolate)aluminum, bis(2,4-dimethyl-8-quinolinolate)(3,5-dimethylphenolate)aluminum, bis(2,4-dimethyl-8-quinolinolate)(3,5-di-t-butylphenolate)aluminum, bis(2-methyl-8-quinolinolate)aluminum-μ-oxo-bis(2-methyl-8-quinolinolate)aluminum, bis(2,4-dimethyl-8-quinolinolate)aluminum-μ-oxo-bis(2,4-dimethyl-8-quinolinolate)aluminum, bis(2-methyl-4-ethyl-8- Examples include bis(2-methyl-4-ethyl-8-quinolinolate)aluminum, bis(2-methyl-4-methoxy-8-quinolinolate)aluminum-μ-oxo-bis(2-methyl-4-methoxy-8-quinolinolate)aluminum, bis(2-methyl-5-cyano-8-quinolinolate)aluminum-μ-oxo-bis(2-methyl-5-cyano-8-quinolinolate)aluminum, bis(2-methyl-5-trifluoromethyl-8-quinolinolate)aluminum-μ-oxo-bis(2-methyl-5-trifluoromethyl-8-quinolinolate)aluminum, and bis(10-hydroxybenzo[h]quinoline)beryllium.

[0379] This quinolinol-based metal complex can be produced using known raw materials and known synthesis methods.

[0380] <Thiazole Derivatives and Benzothiazole Derivatives> The thiazole derivative is, for example, a compound represented by the following formula (ETM-14-1). [ka] The benzothiazole derivative is, for example, a compound represented by the following formula (ETM-14-2). [ka]

[0381] In each formula, φ represents 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. A "thiazole-based substituent" or a "benzothiazole-based substituent" is a substituent in which the pyridyl in the "pyridine-based substituent" in formulae (ETM-2), (ETM-2-1), and (ETM-2-2) is replaced with the following thiazolyl or benzothiazolyl, and at least one hydrogen in the thiazole derivative or benzothiazole derivative may be replaced with deuterium.

[0382] [ka]

[0383] 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 a thiazole-based substituent (or a benzothiazole-based substituent), both pyridine-based substituents may be replaced with a thiazole-based substituent (or a benzothiazole-based substituent) (i.e., n=2), or one of the pyridine-based substituents may be replaced with a thiazole-based substituent (or a benzothiazole-based substituent) and the other pyridine-based substituent may be replaced with R 11 ~R 18 (i.e., n=1). Furthermore, for example, R in formula (ETM-2-1) 11 ~R 18 At least one of the substituents is replaced with a thiazole-based substituent (or a benzothiazole-based substituent) to form a "pyridine-based substituent" R 11 ~R 18 may be replaced with .

[0384] These thiazole or benzothiazole derivatives can be produced using known raw materials and known synthesis methods.

[0385] <Silole derivatives> The silole derivative is, for example, a compound represented by the following formula (ETM-15), the details of which are described in JP-A-9-194487. [ka]

[0386] X and Y are each independently alkyl, cycloalkyl, alkenyl, alkynyl, alkoxy, alkenyloxy, alkynyloxy, aryl, or heteroaryl, which may be substituted. For details of these groups, see the explanations for formula (1) and formula (2) and also the explanation for formula (ETM-7-2). Furthermore, alkenyloxy and alkynyloxy are groups in which the alkyl moiety in alkoxy is replaced with alkenyl or alkynyl, respectively, and for details of these alkenyls and alkynyls, see the explanation for formula (ETM-7-2). Furthermore, X and Y, both of which are alkyl, may be bonded to form a ring.

[0387] R 1 ~R 4are each independently hydrogen, halogen, alkyl, cycloalkyl, alkoxy, aryloxy, amino, alkylcarbonyl, arylcarbonyl, alkoxycarbonyl, aryloxycarbonyl, azo group, alkylcarbonyloxy, arylcarbonyloxy, alkoxycarbonyloxy, aryloxycarbonyloxy, sulfinyl, sulfonyl, sulfanyl, silyl, carbamoyl, aryl, heteroaryl, alkenyl, alkynyl, nitro, formyl, nitroso, formyloxy, isocyano, cyanate group, isocyanate group, thiocyanate group, isothiocyanate group, or cyano, which may be substituted with alkyl, cycloalkyl, aryl or halogen, and may form a fused ring with an adjacent substituent.

[0388] R 1 ~R 4 For details of halogen, alkyl, cycloalkyl, alkoxy, aryloxy, amino, aryl, heteroaryl, alkenyl and alkynyl in the formula (1) and formula (2), reference can be made to the explanations for the formula (1) and formula (2).

[0389] R 1 ~R 4 For details of alkyl, aryl and alkoxy in alkylcarbonyl, arylcarbonyl, alkoxycarbonyl, aryloxycarbonyl, alkylcarbonyloxy, arylcarbonyloxy, alkoxycarbonyloxy and aryloxycarbonyloxy in the above, the explanations in formula (1) and formula (2) can be cited.

[0390] Examples of silyl include a silyl group and a group in which at least one of the three hydrogen atoms of the silyl group is independently substituted with an aryl, alkyl, or cycloalkyl, and tri-substituted silyl is preferred, including triarylsilyl, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, alkyldicycloalkylsilyl, etc. For details of the aryl, alkyl, and cycloalkyl in these, the explanations in formula (1) and formula (2) can be cited.

[0391] The fused ring formed between adjacent substituents is, for example, R 1 and R 2 , R 2 and R 3 , R 3 and R 4 These fused rings may contain nitrogen, oxygen, or sulfur atoms in the ring structure, and may be fused with another ring.

[0392] However, preferably, R 1 and R 4 is phenyl, X and Y are not alkyl or phenyl. 1 and R 4 When R is thienyl, X and Y are alkyl, R is 2 and R 3 is alkyl, aryl, alkenyl or R 2 and R 3 and R are preferably cycloalkyl groups that do not simultaneously satisfy the condition that R 1 and R 4 When is a silyl group, R 2 , R 3 , X and Y are not each independently hydrogen or alkyl having 1 to 6 carbon atoms. 1 and R 2 In the case of a structure in which a benzene ring is fused with X, X and Y are not alkyl and phenyl.

[0393] These silole derivatives can be produced using known raw materials and known synthesis methods.

[0394] <Azoline derivatives> The azoline derivative is, for example, a compound represented by the following formula (ETM-16), details of which are described in WO 2017 / 014226. [ka]

[0395] In formula (ETM-16), φ is an m-valent group derived from an aromatic hydrocarbon having 6 to 40 carbon atoms or an m-valent group derived from an aromatic heterocycle having 2 to 40 carbon atoms, and at least one hydrogen atom of φ is optionally substituted by alkyl having 1 to 6 carbon atoms, cycloalkyl having 3 to 14 carbon atoms, aryl having 6 to 18 carbon atoms, or heteroaryl having 2 to 18 carbon atoms; Y's are each independently -O-, -S-, or >N-Ar, Ar is an aryl having 6 to 12 carbon atoms or a heteroaryl having 2 to 12 carbon atoms, and at least one hydrogen atom of Ar may be substituted with an alkyl having 1 to 4 carbon atoms, a cycloalkyl having 5 to 10 carbon atoms, an aryl having 6 to 12 carbon atoms, or a heteroaryl having 2 to 12 carbon atoms; R 1 ~R 5 are each independently hydrogen, alkyl having 1 to 4 carbon atoms, or cycloalkyl having 5 to 10 carbon atoms, provided that Ar in the >N-Ar and the R 1 ~R 5 one of which is a binding site for L, L's are each independently selected from the group consisting of a divalent group represented by the following formula (L-1) and a divalent group represented by the following formula (L-2):

[0396] [ka]

[0397] In formula (L-1), X 1 ~X 6are each independently =CR 6 - or =N- and X 1 ~X 6 At least two of them are =CR 6 - and X 1 ~X 6 Two of =CR 6 -R in 6 is the bonding site with φ or the azoline ring, and the other =CR 6 -R in 6 is hydrogen, In formula (L-2), X 7 ~X 14 are each independently =CR 6 - or =N- and X 7 ~X 14 At least two of them are =CR 6 - and X 7 ~X 14 Two of =CR 6 -R in 6 is the bonding site with φ or the azoline ring, and the other =CR 6 -R in 6 is hydrogen, at least one hydrogen atom in L may be substituted with alkyl having 1 to 4 carbon atoms, cycloalkyl having 5 to 10 carbon atoms, aryl having 6 to 10 carbon atoms, or heteroaryl having 2 to 10 carbon atoms; m is an integer of 1 to 4, and when m is 2 to 4, the groups formed by the azoline ring and L may be the same or different, and At least one hydrogen atom in the compound represented by formula (ETM-16) may be substituted with deuterium.

[0398] Specific azoline derivatives are compounds represented by the following formula (ETM-16-1) or (ETM-16-2). [ka]

[0399] In formula (ETM-16-1) and formula (ETM-16-2), φ is an m-valent group derived from an aromatic hydrocarbon having 6 to 40 carbon atoms or an m-valent group derived from an aromatic heterocycle having 2 to 40 carbon atoms, and at least one hydrogen atom of φ is optionally substituted by alkyl having 1 to 6 carbon atoms, cycloalkyl having 3 to 14 carbon atoms, aryl having 6 to 18 carbon atoms, or heteroaryl having 2 to 18 carbon atoms; In formula (ETM-16-1), each Y is independently -O-, -S-, or >N-Ar, Ar is an aryl having 6 to 12 carbon atoms or a heteroaryl having 2 to 12 carbon atoms, and at least one hydrogen atom of Ar is optionally substituted with an alkyl having 1 to 4 carbon atoms, a cycloalkyl having 5 to 10 carbon atoms, an aryl having 6 to 12 carbon atoms, or a heteroaryl having 2 to 12 carbon atoms; In formula (ETM-16-1), R 1 ~R 4 are each independently hydrogen, alkyl having 1 to 4 carbon atoms, or cycloalkyl having 5 to 10 carbon atoms, provided that R 1 and R 2 are identical, and R 3 and R 4 are identical, In formula (ETM-16-2), R 1 ~R 5 are each independently hydrogen, alkyl having 1 to 4 carbon atoms, or cycloalkyl having 5 to 10 carbon atoms, provided that R 1 and R 2 are identical, and R 3 and R 4 are identical, In formula (ETM-16-1) and formula (ETM-16-2), L's are each independently selected from the group consisting of a divalent group represented by the following formula (L-1) and a divalent group represented by the following formula (L-2):

[0400] [ka] In formula (L-1), X 1 ~X 6 are each independently =CR 6 - or =N- and X 1 ~X 6 At least two of them are =CR6 - and X 1 ~X 6 Two of =CR 6 -R in 6 is the bonding site with φ or the azoline ring, and the other =CR 6 -R in 6 is hydrogen, In formula (L-2), X 7 ~X 14 are each independently =CR 6 - or =N- and X 7 ~X 14 At least two of them are =CR 6 - and X 7 ~X 14 Two of =CR 6 -R in 6 is the bonding site with φ or the azoline ring, and the other =CR 6 -R in 6 is hydrogen, at least one hydrogen atom in L may be substituted with alkyl having 1 to 4 carbon atoms, cycloalkyl having 5 to 10 carbon atoms, aryl having 6 to 10 carbon atoms, or heteroaryl having 2 to 10 carbon atoms; m is an integer of 1 to 4, and when m is 2 to 4, the groups formed by the azoline ring and L may be the same or different, and At least one hydrogen atom in the compound represented by formula (ETM-16-1) or formula (ETM-16-2) may be substituted with deuterium.

[0401] Preferably, φ is selected from the group consisting of monovalent groups represented by the following formulas (φ1-1) to (φ1-18), divalent groups represented by the following formulas (φ2-1) to (φ2-34), trivalent groups represented by the following formulas (φ3-1) to (φ3-3), and tetravalent groups represented by the following formulas (φ4-1) to (φ4-2), and at least one hydrogen atom of φ may be substituted with alkyl having 1 to 6 carbon atoms, cycloalkyl having 3 to 14 carbon atoms, aryl having 6 to 18 carbon atoms, or heteroaryl having 2 to 18 carbon atoms.

[0402] [ka]

[0403] [ka]

[0404] [ka]

[0405] In the formula, Z is >CR2, >N-Ar, >NL, -O-, or -S-, and each R in >CR2 is independently alkyl having 1 to 4 carbon atoms, cycloalkyl having 5 to 10 carbon atoms, aryl having 6 to 12 carbon atoms, or heteroaryl having 2 to 12 carbon atoms, and the Rs may be bonded to each other to form a ring, Ar in >N-Ar is aryl having 6 to 12 carbon atoms or heteroaryl having 2 to 12 carbon atoms, and L in >NL is L in formula (ETM-16), formula (ETM-16-1), or formula (ETM-16-2). * in the formula indicates the bonding position.

[0406] Preferably, L is a divalent ring group selected from the group consisting of benzene, naphthalene, pyridine, pyrazine, pyrimidine, pyridazine, triazine, quinoline, isoquinoline, naphthyridine, phthalazine, quinoxaline, quinazoline, cinnoline, and pteridine, and at least one hydrogen atom of L may be substituted with alkyl having 1 to 4 carbon atoms, cycloalkyl having 5 to 10 carbon atoms, aryl having 6 to 10 carbon atoms, or heteroaryl having 2 to 10 carbon atoms.

[0407] Preferably, Ar in >N-Ar as Y or Z is selected from the group consisting of phenyl, naphthyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, naphthyridinyl, phthalazinyl, quinoxalinyl, quinazolinyl, cinnolinyl, and pteridinyl, and at least one hydrogen atom of Ar in >N-Ar as Y may be substituted with alkyl having 1 to 4 carbon atoms, cycloalkyl having 5 to 10 carbon atoms, or aryl having 6 to 10 carbon atoms.

[0408] Preferably, R 1 ~R 4 are each independently hydrogen, alkyl having 1 to 4 carbon atoms, or cycloalkyl having 5 to 10 carbon atoms, provided that R 1 and R 2 are identical, and R 3 and R 4 are identical, and R 1 ~R 4 are not all hydrogen atoms at the same time, and m is 1 or 2. When m is 2, the groups formed by the azoline ring and L are the same.

[0409] Specific examples of azoline derivatives include the following compounds: In the structural formula, "Me" represents methyl. [ka]

[0410] More preferably, φ is selected from the group consisting of divalent groups represented by the following formulas (φ2-1), (φ2-31), (φ2-32), (φ2-33), and (φ2-34), and at least one hydrogen of φ may be substituted with an aryl having 6 to 18 carbon atoms.

[0411] [ka]

[0412] L is a divalent ring group selected from the group consisting of benzene, pyridine, pyrazine, pyrimidine, pyridazine, and triazine, and at least one hydrogen atom of L is optionally substituted with alkyl having 1 to 4 carbon atoms, cycloalkyl having 5 to 10 carbon atoms, aryl having 6 to 10 carbon atoms, or heteroaryl having 2 to 14 carbon atoms; Ar in >N-Ar as Y is selected from the group consisting of phenyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, and triazinyl, and at least one hydrogen of Ar may be substituted with alkyl having 1 to 4 carbon atoms, cycloalkyl having 5 to 10 carbon atoms, or aryl having 6 to 10 carbon atoms; R 1 ~R 4 are each independently hydrogen, alkyl having 1 to 4 carbon atoms, or cycloalkyl having 5 to 10 carbon atoms, provided that R 1 and R 2 are identical, and R 3 and R 4 are identical, and R 1 ~R 4 cannot all become hydrogen at the same time, and m is 2, and the groups formed by the azoline ring and L are the same.

[0413] Other specific examples of azoline derivatives include the following compounds: In the structural formula, "Me" represents methyl. [ka]

[0414] For details of alkyl, cycloalkyl, aryl or heteroaryl in the above formulas defining this azoline derivative, the explanations for formula (1) and formula (2) can be cited.

[0415] This azoline derivative can be produced using known raw materials and known synthesis methods.

[0416] <Reducing substances> The electron transport layer or the electron injection layer may further contain a substance capable of reducing the material forming the electron transport layer or the electron injection layer. Various substances can be used as this reducing substance as long as they have a certain level of reducing ability. For example, 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 can be suitably used.

[0417] Preferred reducing substances include alkali metals such as Na (work function 2.36 eV), K (2.28 eV), Rb (2.16 eV), and Cs (1.95 eV), and alkaline earth metals such as Ca (2.9 eV), Sr (2.0-2.5 eV), and Ba (2.52 eV), with substances with a work function of 2.9 eV or less being particularly preferred. Among these, more preferred reducing substances are alkali metals such as K, Rb, and Cs, with Rb or Cs being even more preferred, and Cs being the most preferred. These alkali metals have particularly high reducing ability, and adding a relatively small amount of these metals to the material forming the electron transport layer or electron injection layer can improve the luminance and extend the life of the organic EL device. Furthermore, as a reducing substance having a work function of 2.9 eV or less, a combination of two or more of these alkali metals is also preferred, and in particular, a combination containing Cs is preferred, such as a combination of Cs and Na, Cs and K, Cs and Rb, or Cs, Na and K. By including Cs, the reducing ability can be efficiently exerted, and by adding Cs to the material forming the electron transport layer or electron injection layer, the luminance of the organic EL device can be improved and the lifetime can be extended.

[0418] The above-mentioned electron injection layer material and electron transport layer material can also be used as electron 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.

[0419] 3-1-7. Cathode in organic electroluminescent devices The cathode 108 serves to inject electrons into the light-emitting layer 105 through the electron injection layer 107 and the electron transport layer 106 .

[0420] The material for the cathode 108 is not particularly limited as long as it can efficiently inject electrons into the organic layer, but materials similar to those for the anode 102 can be used. Among these, metals such as tin, indium, calcium, aluminum, silver, copper, nickel, chromium, gold, platinum, iron, zinc, lithium, sodium, potassium, cesium, and magnesium, or alloys thereof (e.g., magnesium-silver alloys, magnesium-indium alloys, and aluminum-lithium alloys such as lithium fluoride / aluminum alloys), are preferred. To increase electron injection efficiency and improve device characteristics, lithium, sodium, potassium, cesium, calcium, magnesium, or alloys containing these low-work-function metals are effective. However, these low-work-function metals are generally unstable in air. To address this issue, a method has been proposed in which a trace amount of lithium, cesium, or magnesium is doped into the organic layer to create a highly stable electrode. Other dopants that can be used include inorganic salts such as lithium fluoride, cesium fluoride, lithium oxide, and cesium oxide. However, these are not limited to these.

[0421] Further, for electrode protection, preferred examples include lamination of metals such as platinum, gold, silver, copper, iron, tin, aluminum, and indium, or alloys using these metals, inorganic materials such as silica, titania, and silicon nitride, polyvinyl alcohol, vinyl chloride, hydrocarbon polymer compounds, etc. The method for producing these electrodes is not particularly limited as long as electrical conduction can be achieved, and may include resistance heating, electron beam evaporation, sputtering, ion plating, and coating.

[0422] 3-1-8. Binders that may be used in each layer The materials used for the hole injection layer, hole transport layer, light-emitting layer, electron transport layer, and electron injection layer can be used alone to form each layer, but they can also be dispersed as a polymer binder in solvent-soluble resins such as polyvinyl chloride, polycarbonate, polystyrene, poly(N-vinylcarbazole), polymethyl methacrylate, polybutyl methacrylate, polyester, polysulfone, polyphenylene oxide, polybutadiene, hydrocarbon resins, ketone resins, phenoxy resins, polyamide, ethyl cellulose, vinyl acetate resin, ABS resin, and polyurethane resin, or curable resins such as phenol resin, xylene resin, petroleum resin, urea resin, melamine resin, unsaturated polyester resin, alkyd resin, epoxy resin, and silicone resin.

[0423] 3-1-9. Method for producing organic electroluminescent device Each layer constituting an organic EL device can be formed by forming the material to be formed into a thin film using methods such as vapor deposition, resistance heating vapor deposition, electron beam vapor deposition, sputtering, molecular lamination, printing, spin coating or casting, and coating. There are no particular limitations on the film thickness of each layer formed in this way, and it can be set appropriately depending on the properties of the material, but it is usually in the range of 2 nm to 5000 nm. The film thickness can usually be measured with a quartz oscillator film thickness measuring device or the like. When forming a thin film using vapor deposition, the vapor deposition conditions vary depending on the type of material, the desired crystal structure and association structure of the film, etc. Vapor deposition conditions are generally a boat heating temperature of +50 to +400°C, a vacuum degree of 10 -6 ~10-3 It is preferable to appropriately set the pressure, the deposition rate, the substrate temperature, and the film thickness in the range of 0.01 to 50 nm / sec, -150 to +300° C., and 2 nm to 5 μm.

[0424] When applying a DC voltage to the organic EL element obtained in this way, the anode should be set to + and the cathode to -. When a voltage of about 2 to 40 V is applied, light emission can be observed from the transparent or semi-transparent electrode side (anode or cathode, or both). This organic EL element also emits light when a pulse current or an AC current is applied. The waveform of the applied AC current can be any waveform.

[0425] Next, as an example of a method for producing an organic EL element, a method for producing an organic EL element comprising an anode, a hole injection layer, a hole transport layer, an emitting layer composed of a host material and a dopant material, an electron transport layer, an electron injection layer, and a cathode will be described.

[0426] <Vapor deposition method> An anode is prepared by forming a thin film of an anode material on a suitable substrate by vapor deposition or the like, and then forming thin films of a hole injection layer and a hole transport layer on the anode. A host material and a dopant material are co-deposited on the anode to form a thin film to serve as an emissive layer. An electron transport layer and an electron injection layer are then formed on the emissive layer, and a thin film of a cathode material is then formed by vapor deposition or the like to serve as a cathode, thereby obtaining the desired organic EL device. It is also possible to reverse the order of fabrication of the organic EL device described above, by fabricating the layers in the order of cathode, electron injection layer, electron transport layer, emissive layer, hole transport layer, hole injection layer, and anode.

[0427] <Wet film formation method> The wet film formation method is carried out by preparing a liquid organic layer-forming composition from a low molecular weight compound capable of forming each organic layer of an organic EL device, and using this. If there is no suitable organic solvent that can dissolve this low molecular weight compound, the organic layer-forming composition may be prepared from a reactive compound obtained by substituting a reactive substituent on the low molecular weight compound, such as another monomer having a solubility function as a reactive compound, or a polymer compound polymerized together with a main-chain polymer.

[0428] In wet film formation methods, a coating film is generally formed through a coating step in which an organic layer-forming composition is applied to a substrate and a drying step in which the solvent is removed from the applied organic layer-forming composition. When the polymer compound has a crosslinkable substituent (also called a crosslinkable polymer compound), this drying step causes further crosslinking to form a crosslinked polymer. Depending on the coating step, a method using a spin coater is called a spin coating method; a method using a slit coater is called a slit coating method; a method using a plate is called a gravure, offset, reverse offset, or flexographic printing method; a method using an inkjet printer is called an inkjet method; and a method spraying in a mist is called a spray method.

[0429] As an example, referring to Figure 2, a method for forming a coating film using an inkjet method on a substrate having banks will be described. First, banks (200) are provided on electrodes (120) on a substrate (110). In this case, ink droplets (310) are dropped between the banks (200) from an inkjet head (300) and dried to form a coating film (130). This process is repeated to form the next coating film (140) and then the light-emitting layer (150). An electron transport layer, an electron injection layer, and electrodes are then formed using vacuum deposition, thereby producing an organic EL element in which the light-emitting region is separated by the bank material.

[0430] The drying process can be carried out by air drying, heating, drying under reduced pressure, etc. The drying process can be carried out once or multiple times using different methods and conditions. Also, different methods can be used in combination, such as calcination under reduced pressure.

[0431] Wet film formation methods are film formation methods that use solutions, such as some printing methods (inkjet methods), spin coating or casting methods, and coating methods. Unlike vacuum deposition methods, wet film formation methods do not require expensive vacuum deposition equipment and can form films under atmospheric pressure. In addition, wet film formation methods allow for large-area and continuous production, which leads to reduced manufacturing costs.

[0432] On the other hand, compared to vacuum deposition, wet deposition can be difficult to layer. When using wet deposition to create layered films, it is necessary to prevent the dissolution of the lower layer by the composition of the upper layer, and methods such as controlled solubility compositions, crosslinking of the lower layer, and orthogonal solvents (solvents that are not soluble in each other) are used. However, even with these techniques, it can be difficult to use wet deposition for all film application.

[0433] Therefore, a common method for producing organic EL elements is to use a wet film-forming method for only some layers and a vacuum deposition method for the remaining layers.

[0434] For example, the procedure for producing an organic EL element by partially applying a wet film formation method is shown below. (Step 1) Formation of the anode by vacuum deposition (Step 2) Forming a film by a wet film formation method using a composition for forming a hole injection layer containing a material for the hole injection layer (Step 3) Forming a film by a wet film formation method using a composition for forming a hole transport layer containing a material for the hole transport layer (Step 4) Forming a film by a wet film formation method using a composition for forming an emitting layer containing a host material and a dopant material (Step 5) Formation of the electron transport layer by vacuum deposition (Step 6) Formation of the electron injection layer by vacuum deposition (Step 7) Cathode deposition by vacuum evaporation Through this procedure, an organic EL element consisting of an anode, a hole injection layer, a hole transport layer, a light-emitting layer made of a host material and a dopant material, an electron transport layer, an electron injection layer, and a cathode is obtained. Of course, if there is a means for preventing dissolution of the underlying light-emitting layer, or if a means for forming a film from the cathode side in the reverse of the above procedure is used, a layer-forming composition containing a material for the electron transport layer and a material for the electron injection layer can be prepared, and the layer can be formed by a wet film-forming method.

[0435] <Other film formation methods> The organic layer-forming composition can be formed into a film by laser thermal imaging (LITI), a method in which a compound attached to a substrate is heated and vapor-deposited with a laser, and the organic layer-forming composition can be used as the material applied to the substrate.

[0436] <Optional process> Before and after each film-forming step, appropriate treatment steps, cleaning steps, and drying steps may be added as appropriate. Examples of treatment steps include exposure treatment, plasma surface treatment, ultrasonic treatment, ozone treatment, cleaning treatment using an appropriate solvent, and heat treatment. Furthermore, a series of steps for preparing a bank may also be included.

[0437] Photolithography can be used to fabricate the banks. Positive and negative resist materials can be used as bank materials for photolithography. Patternable printing methods such as inkjet printing, gravure offset printing, reverse offset printing, and screen printing can also be used. In these cases, permanent resist materials can also be used.

[0438] Materials that can be used for banks include, but are not limited to, polysaccharides and their derivatives, homopolymers and copolymers of hydroxyl-containing ethylenic monomers, biopolymers, polyacryloyl compounds, polyesters, polystyrenes, polyimides, polyamideimides, polyetherimides, polysulfides, polysulfones, polyphenylenes, polyphenyl ethers, polyurethanes, epoxy (meth)acrylates, melamine (meth)acrylates, polyolefins, cyclic polyolefins, acrylonitrile-butadiene-styrene copolymers (ABS), silicone resins, polyvinyl chloride, chlorinated polyethylene, chlorinated polypropylene, polyacetate, polynorbornene, synthetic rubbers, fluorinated polymers such as polyfluorovinylidene, polytetrafluoroethylene, and polyhexafluoropropylene, fluoroolefin-hydrocarbonolefin copolymers, and fluorocarbon polymers.

[0439] <Composition for forming organic layer used in wet film formation method> The organic layer-forming composition is obtained by dissolving a low-molecular-weight compound capable of forming each organic layer of an organic EL device, or a polymer compound obtained by polymerizing such a low-molecular-weight compound, in an organic solvent. For example, the light-emitting layer-forming composition contains at least one polycyclic aromatic compound (or a polymer compound thereof) as a dopant material as a first component, at least one host material as a second component, and at least one organic solvent as a third component. The first component functions as a dopant component for the light-emitting layer obtained from the composition, and the second component functions as a host component for the light-emitting layer. The third component functions as a solvent that dissolves the first and second components in the composition, and upon application, the controlled evaporation rate of the third component itself provides a smooth and uniform surface profile.

[0440] <Organic solvents> The organic layer-forming composition contains at least one organic solvent. By controlling the evaporation rate of the organic solvent during film formation, it is possible to control and improve film-forming properties, the presence or absence of defects in the coating film, surface roughness, and smoothness. Furthermore, when forming a film using an inkjet method, it is possible to control meniscus stability at the pinhole of the inkjet head and control and improve ejection properties. In addition, by controlling the drying rate of the film and the orientation of the derivative molecules, it is possible to improve the electrical properties, luminescence properties, efficiency, and lifespan of an organic EL device having an organic layer obtained from the organic layer-forming composition.

[0441] (1) Physical properties of organic solvents The boiling point of the at least one organic solvent is 130°C to 300°C, more preferably 140°C to 270°C, and even more preferably 150°C to 250°C. A boiling point higher than 130°C is preferred from the viewpoint of inkjet dischargeability. A boiling point lower than 300°C is preferred from the viewpoints of coating film defects, surface roughness, residual solvent, and smoothness. From the viewpoints of good inkjet dischargeability, film-forming properties, smoothness, and low residual solvent, it is more preferred that the organic solvent contains two or more organic solvents. Meanwhile, in some cases, taking into consideration transportability, etc., the composition may be in a solid state obtained by removing the solvent from the composition for forming the organic layer.

[0442] Furthermore, the organic solvent contains a good solvent (GS) and a poor solvent (PS) for at least one of the solutes, and the boiling point (BP) of the good solvent (GS) is GS ) is the boiling point (BP) of the poor solvent (PS) PS ) is particularly preferred. By adding a high-boiling poor solvent, the low-boiling good solvent evaporates first during film formation, increasing the concentration of the ingredients in the composition and the concentration of the poor solvent, facilitating rapid film formation. This results in a coating with few defects, minimal surface roughness, and high smoothness.

[0443] Difference in solubility (S GS -S PS The difference in boiling point (BP) is preferably 1% or more, more preferably 3% or more, and even more preferably 5% or more. PS -BP GS ) is preferably 10°C or higher, more preferably 30°C or higher, and even more preferably 50°C or higher.

[0444] After film formation, the organic solvent is removed from the coating film by a drying process such as vacuum, reduced pressure, or heating. When heating is performed, from the viewpoint of improving coating film-forming properties, it is preferable to perform the heating at a temperature not higher than 30°C above the glass transition temperature (Tg) of at least one of the solutes. Furthermore, from the viewpoint of reducing residual solvent, it is preferable to perform the heating at a temperature not lower than 30°C below the glass transition temperature (Tg) of at least one of the solutes. Even if the heating temperature is lower than the boiling point of the organic solvent, the organic solvent can be sufficiently removed because the film is thin. Furthermore, drying may be performed multiple times at different temperatures, or multiple drying methods may be used in combination.

[0445] (2) Specific examples of organic solvents Examples of organic solvents used in the organic layer-forming composition include alkylbenzene solvents, phenyl ether solvents, alkyl ether solvents, cyclic ketone solvents, aliphatic ketone solvents, monocyclic ketone solvents, solvents having a diester skeleton, and fluorine-containing solvents. Specific examples include pentanol, hexanol, heptanol, octanol, nonanol, decanol, undecanol, dodecanol, tetradecanol, hexane-2-ol, heptan-2-ol, octan-2-ol, decan-2-ol, dodecan-2-ol, cyclohexanol, Sanol, α-terpineol, β-terpineol, γ-terpineol, δ-terpineol, terpineol (mixture), ethylene glycol monomethyl ether acetate, propylene glycol monomethyl ether acetate, diethylene glycol dimethyl ether, dipropylene glycol dimethyl ether, diethylene glycol ethyl methyl ether, diethylene glycol isopropyl methyl ether, dipropylene glycol monomethyl ether, diethylene glycol diethyl ether, diethylene glycol monomethyl ether , diethylene glycol butyl methyl ether, tripropylene glycol dimethyl ether, triethylene glycol dimethyl ether, diethylene glycol monobutyl ether, ethylene glycol monophenyl ether, triethylene glycol monomethyl ether, diethylene glycol dibutyl ether, triethylene glycol butyl methyl ether, polyethylene glycol dimethyl ether, tetraethylene glycol dimethyl ether, p-xylene, m-xylene, o-xylene, 2,6-lutidine, 2-fluoro-m-xylene, 3-fluoro-o-xylene, 2-chlorobenzotrifluoride, cumene, toluene, 2-chloro-6-fluorotoluene, 2-fluoroanisole, anisole, 2,3-dimethylpyrazine, bromobenzene, 4-fluoroanisole, 3-fluoroanisole, 3-trifluoromethylanisole, mesitylene, 1,2,4-trimethylbenzene, t-butylbenzene, 2-methylanisole, phenetole, benzodioxole, 4-methylanisole, s-butylbenzene, 3-methylanisole, 4-fluoro-3-methylanisole, cymene, 1,2,3-Trimethylbenzene, 1,2-dichlorobenzene, 2-fluorobenzonitrile, 4-fluoroveratrol, 2,6-dimethylanisole, n-butylbenzene, 3-fluorobenzonitrile, decalin (decahydronaphthalene), neopentylbenzene, 2,5-dimethylanisole, 2,4-dimethylanisole, benzonitrile, 3,5-dimethylanisole, diphenyl ether, 1-fluoro-3,5-dimethoxybenzene, methyl benzoate, isopentylbenzene, 3,4-dimethylanisole, o-tolunitrile, n-amylbenzene, veratrol, 1,2,3,4-tetrahydronaphthalene, ethyl benzoate, n-hexylbenzene, propyl benzoate, cyclohexylbenzene, 1- Examples of the solvent include, but are not limited to, methylnaphthalene, butyl benzoate, 2-methylbiphenyl, 3-phenoxytoluene, 2,2'-bitolyl, dodecylbenzene, dipentylbenzene, tetramethylbenzene, trimethoxybenzene, trimethoxytoluene, 2,3-dihydrobenzofuran, 1-methyl-4-(propoxymethyl)benzene, 1-methyl-4-(butyloxymethyl)benzene, 1-methyl-4-(pentyloxymethyl)benzene, 1-methyl-4-(hexyloxymethyl)benzene, 1-methyl-4-(heptyloxymethyl)benzene, benzyl butyl ether, benzyl pentyl ether, benzyl hexyl ether, benzyl heptyl ether, and benzyl octyl ether. The solvent may be used alone or in combination.

[0446] <Optional ingredients> The composition for forming the organic layer may contain optional components, such as a binder and a surfactant, to the extent that the properties of the composition are not impaired.

[0447] (1) Binder The organic layer-forming composition may contain a binder. The binder not only forms a film during film formation but also bonds the resulting film to a substrate. The binder also plays a role in dissolving, dispersing, and binding other components in the organic layer-forming composition.

[0448] Examples of binders used in the organic layer-forming composition include, but are not limited to, acrylic resins, polyethylene terephthalate, ethylene-vinyl acetate copolymers, ethylene-vinyl alcohol copolymers, acrylonitrile-ethylene-styrene copolymer (AES) resins, ionomers, chlorinated polyethers, diallyl phthalate resins, unsaturated polyester resins, polyethylene, polypropylene, polyvinyl chloride, polyvinylidene chloride, polystyrene, polyvinyl acetate, Teflon, acrylonitrile-butadiene-styrene copolymer (ABS) resins, acrylonitrile-styrene copolymer (AS) resins, phenolic resins, epoxy resins, melamine resins, urea resins, alkyd resins, polyurethanes, and copolymers of the above resins and polymers.

[0449] The binder used in the organic layer-forming composition may be one type only, or a mixture of two or more types may be used.

[0450] (2) Surfactants The organic layer-forming composition may contain a surfactant, for example, to control the film surface uniformity, solvent affinity, and liquid repellency of the organic layer-forming composition. Surfactants are classified into ionic and nonionic based on the structure of their hydrophilic group, and further classified into alkyl, silicone, and fluorine-based based on the structure of their hydrophobic group. Furthermore, based on their molecular structure, they are classified into monomolecular systems with relatively small molecular weights and simple structures, and polymer systems with large molecular weights and side chains or branches. Based on their composition, they are classified into single systems and mixed systems containing two or more surfactants and base materials. All types of surfactants can be used in the organic layer-forming composition.

[0451] Examples of surfactants include Polyflow No. 45, Polyflow KL-245, Polyflow No. 75, Polyflow No. 90, and Polyflow No. 95 (trade names, manufactured by Kyoeisha Chemical Industry Co., Ltd.), Disperbyk 161, Disperbyk 162, Disperbyk 163, Disperbyk 164, Disperbyk 166, Disperbyk 170, Disperbyk 180, Disperbyk 181, Disperbyk 182, BYK300, and BYK 306, BYK310, BYK320, BYK330, BYK342, BYK344, BYK346 (trade names, manufactured by BYK Japan Co., Ltd.), KP-341, KP-358, KP-368, KF-96-50CS, KF-50-100CS (trade names, manufactured by Shin-Etsu Chemical Co., Ltd.), Surflon SC-101, Surflon KH-40 (trade names, manufactured by Seimi Chemical Co., Ltd.), Ftergent 222F, Ftergent 251, FTX-218 (trade names, manufactured by Neos Co., Ltd.), EFTOP EF-351, EFTOP EF-352, EFTOP EF-601, EFTOP EF-801, EFTOPEF-802 (trade name, manufactured by Mitsubishi Materials Corporation), Megafac F-470, Megafac F-471, Megafac F-475, Megafac R-08, Megafac F-477, Megafac F-479, Megafac F-553, Megafac F-554 (trade name, manufactured by DIC Corporation), fluoroalkylbenzenesulfonates, fluoroalkylcarboxylates, fluoroalkylpolyoxyethylene ethers, fluoroalkylammonium iodides, fluoroalkylbetaines, fluoroalkylsulfonates, diglycerin tetrakis(fluoroalkylpolyoxyethylene ether), fluoroalkyltrimethylammonium salts, fluoroalkylaminosulfonates, polyoxyethylene nonyl phenyl ether, polyoxyethylene octylphenyl ether, polyoxyethylene alkyl ether, polyoxyethylene laurate, polyoxyethylene oleate, polyoxyethylene stearate, polyoxyethylene laurylamine, sorbitan laurate, sorbitan palmitate, sorbitan stearate, sorbitan oleate, sorbitan fatty acid ester, polyoxyethylene sorbitan laurate, polyoxyethylene sorbitan palmitate, polyoxyethylene sorbitan stearate, polyoxyethylene sorbitan oleate, polyoxyethylene naphthyl ether, alkyl benzene sulfonate, and alkyl diphenyl ether disulfonate.

[0452] The surfactant may be used alone or in combination of two or more.

[0453] <Composition and Properties of the Organic Layer-Forming Composition> The content of each component in the composition for forming an organic layer is determined taking into consideration the good solubility, storage stability, and film-forming properties of each component in the composition for forming an organic layer, the good film quality of the coating film obtained from the composition for forming an organic layer, the good dischargeability when using an inkjet method, and the good electrical properties, light-emitting properties, efficiency, and lifespan of an organic EL device having an organic layer produced using the composition. For example, in the case of a composition for forming an emitting layer, it is preferable that the first component be 0.0001% to 2.0% by mass, the second component be 0.0999% to 8.0% by mass, and the third component be 90.0% to 99.9% by mass, relative to the total mass of the composition for forming an emitting layer.

[0454] More preferably, the first component is 0.005% by mass to 1.0% by mass, the second component is 0.095% by mass to 4.0% by mass, and the third component is 95.0% by mass to 99.9% by mass, relative to the total mass of the composition for forming the light-emitting layer. Even more preferably, the first component is 0.05% by mass to 0.5% by mass, the second component is 0.25% by mass to 2.5% by mass, and the third component is 97.0% by mass to 99.7% by mass, relative to the total mass of the composition for forming the light-emitting layer.

[0455] The composition for forming an organic layer can be produced by appropriately selecting the above-mentioned components by a known method, such as stirring, mixing, heating, cooling, dissolving, dispersing, etc. After preparation, the composition may be appropriately subjected to filtration, degassing (also called degassing), ion exchange treatment, inert gas substitution / filling treatment, etc.

[0456] The higher the viscosity of the composition for forming an organic layer, the better the film-forming properties and the better the ejection properties when using an inkjet method. On the other hand, the lower the viscosity, the easier it is to form a thin film. For this reason, the viscosity of the composition for forming an organic layer at 25°C is preferably 0.3 to 3 mPa·s, and more preferably 1 to 3 mPa·s. In the present invention, the viscosity is a value measured using a cone-plate type rotational viscometer (cone-plate type).

[0457] The lower the surface tension of the composition for forming an organic layer, the better the film-forming properties and the more defect-free the coating film will be. On the other hand, the higher the surface tension, the better the ink-jet ejection properties will be. For this reason, the surface tension of the composition for forming an organic layer at 25°C is preferably 20 to 40 mN / m, and more preferably 20 to 30 mN / m. In the present invention, the surface tension is a value measured using the hanging drop method.

[0458] <Crosslinkable polymer compound: Compound represented by formula (XLP-1)> Next, the case where the above-mentioned polymer compound has a crosslinkable substituent will be described. Such a crosslinkable polymer compound is, for example, a compound represented by the following formula (XLP-1).

[0459] [ka]

[0460] In formula (XLP-1), each MUx is independently a divalent group obtained by removing two hydrogen atoms from any aromatic compound, each ECx is independently a monovalent group obtained by removing one hydrogen atom from any aromatic compound, and k is an integer of 2 to 50,000. For details about MUx, ECx, and k, please refer to the descriptions of MU, EC, and k in formula (SPH-1) in paragraphs 0269 to 0285 of WO 2020 / 162600. However, the compound represented by formula (XLP-1) has at least one crosslinkable substituent (XLS), and preferably the content of the monovalent or divalent aromatic group having a crosslinkable substituent is 0.1 to 80 mass% in the molecule.

[0461] The content of the monovalent or divalent aromatic group having a crosslinkable substituent in the molecule is preferably 0.5 to 50 mass %, more preferably 1 to 20 mass %.

[0462] The crosslinkable substituent (XLS) is not particularly limited as long as it is a group that can further crosslink the above-mentioned polymer compound, but substituents having the following structures are preferred: * in each structural formula indicates the bonding position. [ka]

[0463] 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.

[0464] Examples of the divalent aromatic compound having a crosslinkable substituent include compounds having the following partial structure: [ka]

[0465] [ka]

[0466] [ka]

[0467] [ka]

[0468] <Methods of producing polymer compounds and crosslinkable polymer compounds> The methods for producing the polymer compound and the crosslinkable polymer compound will be described below using the compound represented by the formula (XLP-1) as an example. These compounds can be synthesized by appropriately combining known production methods.

[0469] Examples of the solvent used in the reaction include aromatic solvents, saturated / unsaturated hydrocarbon solvents, alcohol solvents, and ether solvents, such as dimethoxyethane, 2-(2-methoxyethoxy)ethane, and 2-(2-ethoxyethoxy)ethane.

[0470] The reaction may also be carried out in a two-phase system, in which case a phase transfer catalyst such as a quaternary ammonium salt may be added as necessary.

[0471] The compound (XLP-1) can be produced in a single step or multiple steps. Furthermore, it can be produced by batch polymerization, in which all raw materials are placed in a reaction vessel and the reaction is initiated; by dropwise polymerization, in which raw materials are added dropwise to a reaction vessel; or by precipitation polymerization, in which the product precipitates as the reaction progresses. These methods can be combined as appropriate. For example, when synthesizing a compound represented by formula (XLP-1) in a single step, the target product is obtained by adding a monomer having a polymerizable group bonded to a monomer unit (MUx) and a monomer having a polymerizable group bonded to an end-capping unit (ECx) to a reaction vessel and then reacting them. Furthermore, when synthesizing a compound represented by formula (XLP-1) in multiple steps, the target product is obtained by polymerizing a monomer having a polymerizable group bonded to a monomer unit (MUx) to the target molecular weight, and then adding a monomer having a polymerizable group bonded to an end-capping unit (ECx) and reacting them. By adding different types of monomers having a polymerizable group bonded to the monomer unit (MUx) and reacting them in multiple steps, a polymer with a concentration gradient of the monomer unit structure can be produced. Furthermore, after preparing a precursor polymer, the target polymer can be obtained by a post-reaction.

[0472] Furthermore, the primary structure of the polymer can be controlled by selecting the polymerizable group of the monomer. For example, as shown in Synthesis Schemes 1 to 3, it is possible to synthesize a polymer with a random primary structure (Synthetic Scheme 1) or a polymer with a regular primary structure (Synthetic Schemes 2 and 3), and these can be used in appropriate combinations depending on the target product. Furthermore, if a monomer with three or more polymerizable groups is used, it is possible to synthesize a hyperbranched polymer or a dendrimer.

[0473] [ka]

[0474] Monomers that can be used in the present invention include those described in JP 2010-189630 A, WO 2012 / 086671 A, WO 2013 / 191088 A, WO 2002 / 045184 A, WO 2011 / 049241 A, WO 2013 / 146806 A, WO 2005 / 049546 A, WO 2015 / 1458 A, 71, JP 2010-215886, JP 2008-106241, JP 2010-215886, WO 2016 / 031639, JP 2011-174062, WO 2016 / 031639, WO 2016 / 031639, and WO 2002 / 045184.

[0475] Specific polymer synthesis procedures are described in JP 2012-036388 A, WO 2015 / 008851 A, JP 2012-36381 A, JP 2012-144722 A, WO 2015 / 194448 A, WO 2013 / 146806 A, WO 2015 / 145871 A, WO 2016 / It can be synthesized in accordance with the methods described in WO 2016 / 031639, WO 2016 / 125560, WO 2016 / 031639, WO 2016 / 031639, WO 2016 / 125560, WO 2015 / 145871, WO 2011 / 049241, and JP 2012-144722 A.

[0476] 3-1-10.Application examples of organic electroluminescent devices The present invention can also be applied to a display device equipped with an organic EL element or a lighting device equipped with an organic EL element. A display device or lighting device including an organic EL element can be manufactured by a known method, for example, by connecting the organic EL element according to this embodiment to a known driving device, and can be driven appropriately using a known driving method such as DC driving, pulse driving, or AC driving.

[0477] Examples of display devices include panel displays such as color flat panel displays, and flexible displays such as flexible color organic electroluminescent (EL) displays (see, for example, JP-A-10-335066, JP-A-2003-321546, and JP-A-2004-281086). Examples of display methods include matrix and / or segment methods. Note that matrix display and segment display may coexist in the same panel.

[0478] In a matrix display, pixels are arranged two-dimensionally, such as in a grid or mosaic pattern, and a collection of pixels displays characters and images. The shape and size of the pixels are determined by the application. For example, images and text displayed on computers, monitors, and televisions typically use square pixels with sides of 300 μm or less. Large displays such as display panels use pixels on the order of millimeters. For monochrome displays, pixels of the same color are simply arranged, while for color displays, red, green, and blue pixels are displayed side by side. These types are typically known as delta and stripe types. The matrix can be driven by either line-sequential or active matrix methods. While line-sequential driving has the advantage of being simpler, active matrix methods can sometimes be superior in terms of operating characteristics, so the choice must be made based on the application.

[0479] In the segment type, a pattern is formed to display predetermined information, and a predetermined area is illuminated. Examples include the time and temperature displays on digital clocks and thermometers, the operating status displays on audio equipment and induction cookers, and panel displays on automobiles.

[0480] Examples of lighting devices include lighting devices for indoor lighting and backlights for liquid crystal display devices (see, for example, JP 2003-257621 A, JP 2003-277741 A, JP 2004-119211 A, etc.). Backlights are primarily used to improve the visibility of non-self-luminous display devices, and are used in liquid crystal display devices, clocks, audio devices, automobile panels, display boards, signs, etc. In particular, for backlights for liquid crystal display devices, particularly for personal computers where thinning is an issue, considering that conventional systems use fluorescent lamps and light guide plates and therefore make thinning difficult, backlights using the light-emitting elements according to this embodiment are characterized by their thinness and light weight.

[0481] 3-2. Other organic devices The polycyclic aromatic compound according to the present invention can be used to produce not only the above-mentioned organic electroluminescent device but also an organic field effect transistor or an organic thin-film solar cell.

[0482] An organic field-effect transistor is a transistor that controls current by generating an electric field through voltage input, and has a gate electrode in addition to a source electrode and a drain electrode. When a voltage is applied to the gate electrode, an electric field is generated, and the transistor can control the current by arbitrarily blocking the flow of electrons (or holes) flowing between the source and drain electrodes. Field-effect transistors are easier to miniaturize than simple transistors (bipolar transistors), and are often used as elements that make up integrated circuits.

[0483] The structure of an organic field effect transistor is usually such that a source electrode and a drain electrode are provided in contact with an organic semiconductor active layer formed using the polycyclic aromatic compound according to the present invention, and a gate electrode is provided sandwiching an insulating layer (dielectric layer) in contact with the organic semiconductor active layer. Examples of the device structure include the following structure. (1) Substrate / gate electrode / insulating layer / source and drain electrodes / organic semiconductor active layer (2) Substrate / gate electrode / insulating layer / organic semiconductor active layer / source electrode / drain electrode (3) Substrate / organic semiconductor active layer / source electrode / drain electrode / insulator layer / gate electrode (4) Substrate / source electrode / drain electrode / organic semiconductor active layer / insulator layer / gate electrode The organic field effect transistor configured in this manner can be used as a pixel driving switching element for an active matrix driving liquid crystal display or an organic electroluminescence display.

[0484] An organic thin-film solar cell has a structure in which an anode such as ITO, a hole transport layer, a photoelectric conversion layer, an electron transport layer, and a cathode are laminated on a transparent substrate such as glass. The photoelectric conversion layer has a p-type semiconductor layer on the anode side and an n-type semiconductor layer on the cathode side. The polycyclic aromatic compound according to the present invention can be used as a material for the hole transport layer, p-type semiconductor layer, n-type semiconductor layer, or electron transport layer depending on its physical properties. The polycyclic aromatic compound according to the present invention can function as a hole transport material or electron transport material in an organic thin-film solar cell. In addition to the above, the organic thin-film solar cell may also include a hole blocking layer, electron blocking layer, electron injection layer, hole injection layer, smoothing layer, etc. as appropriate. Known materials used in organic thin-film solar cells can be appropriately selected and combined for use in the organic thin-film solar cell. [Example]

[0485] The present invention will be described in more detail below with reference to examples, but the present invention is not limited to these. First, synthesis examples of polycyclic aromatic compounds will be described below.

[0486] Synthesis example (1) Synthesis Example (1): Synthesis of Compound (1-363) [ka]

[0487] A 1.53 M tert-butyllithium pentane solution (15.2 ml) was added to a flask containing intermediate (I-1) (10.2 g) and tert-butylbenzene (80 ml) under a nitrogen atmosphere at 0°C. After the dropwise addition, the mixture was heated to 60°C and stirred for 0.5 hours. Components with boiling points lower than tert-butylbenzene were then distilled off under reduced pressure. The mixture was cooled to -50°C, boron tribromide (5.8 g) was added, and the mixture was warmed to room temperature and stirred for 0.5 hours. The mixture was then cooled again to 0°C, N,N-diisopropylethylamine (2.6 g) was added, and the mixture was stirred at room temperature until the heat generation subsided. The mixture was then heated to 100°C and stirred for 1 hour. The reaction mixture was cooled to room temperature, and an aqueous sodium acetate solution cooled in an ice bath, followed by ethyl acetate, was added and stirred for 1 hour. The yellow suspension was filtered, and the precipitate was washed with methanol. The yellow crystals were dissolved in toluene by heating and purified using a silica gel short column (eluent: toluene). Toluene was added to the obtained crude product, and the mixture was concentrated, followed by the addition of Solmix (A-11) (manufactured by Japan Alcohol Sales Co., Ltd.) The precipitated crystals were filtered and further washed with methanol to obtain compound (1-363) (3.0 g).

[0488] [ka]

[0489] The compound was confirmed to have been obtained by MS measurement. 64 H 78 BN3:899.629

[0490] Synthesis Example (2): Synthesis of Compound (1-370) [ka]

[0491] A 1.53 M tert-butyllithium pentane solution (15.2 ml) was added to a flask containing intermediate (I-2) (12.4 g) and tert-butylbenzene (80 ml) under a nitrogen atmosphere at 0°C. After the dropwise addition, the mixture was heated to 60°C and stirred for 0.5 hours. Components with boiling points lower than tert-butylbenzene were then distilled off under reduced pressure. The mixture was cooled to -50°C, boron tribromide (5.8 g) was added, and the mixture was warmed to room temperature and stirred for 0.5 hours. The mixture was then cooled again to 0°C, N,N-diisopropylethylamine (2.6 g) was added, and the mixture was stirred at room temperature until the heat generation subsided. The mixture was then heated to 100°C and stirred for 1 hour. The reaction mixture was cooled to room temperature, and an aqueous sodium acetate solution cooled in an ice bath, followed by ethyl acetate, was added and stirred for 1 hour. The yellow suspension was filtered, and the precipitate was washed with methanol. The yellow crystals were dissolved in toluene by heating and purified using a silica gel short column (eluent: toluene). Toluene was added to the obtained crude product, and the mixture was concentrated, followed by addition of Solmix (A-11). The precipitated crystals were filtered and washed with methanol to obtain compound (1-370) (3.4 g).

[0492] [ka]

[0493] The compound was confirmed to have been obtained by MS measurement. 78 H 95 BN4:1098.765

[0494] Synthesis Example (3): Synthesis of Compound (1-383) [ka]

[0495] A 1.53 M tert-butyllithium pentane solution (15.2 ml) was added to a flask containing intermediate (I-3) (10.8 g) and tert-butylbenzene (80 ml) under a nitrogen atmosphere at 0°C. After the dropwise addition, the mixture was heated to 60°C and stirred for 0.5 hours. Components with boiling points lower than that of tert-butylbenzene were then removed by distillation under reduced pressure. The mixture was cooled to -50°C, and boron tribromide (5.8 g) was added. The mixture was then heated to room temperature and stirred for 0.5 hours. The mixture was then cooled again to 0°C, and N,N-diisopropylethylamine (2.6 g) was added. The mixture was stirred at room temperature until the heat generation subsided, then heated to 100°C and stirred for 1 hour. The reaction mixture was cooled to room temperature, and an aqueous solution of sodium acetate cooled in an ice bath, followed by ethyl acetate, was added and stirred for 1 hour. The yellow suspension was filtered, and the precipitate was washed with methanol. The yellow crystals were dissolved in toluene by heating and purified using a silica gel short column (eluent: toluene). Toluene was added to the obtained crude product, and the mixture was concentrated, followed by addition of Solmix (A-11). The precipitated crystals were filtered and washed with methanol to obtain compound (1-383) (2.6 g).

[0496] [ka]

[0497] The compound was confirmed to have been obtained by MS measurement. 66 H 78 BN3S:955.601

[0498] Synthesis Example (4): Synthesis of Compound (1-517) [ka]

[0499] A 1.53 M tert-butyllithium pentane solution (15.2 ml) was added to a flask containing intermediate (I-4) (9.3 g) and tert-butylbenzene (80 ml) under a nitrogen atmosphere at 0 °C. After the dropwise addition, the mixture was heated to 60 °C and stirred for 0.5 hours. Components with boiling points lower than that of tert-butylbenzene were then distilled off under reduced pressure. The mixture was cooled to -50 °C, boron tribromide (5.8 g) was added, and the mixture was warmed to room temperature and stirred for 0.5 hours. The mixture was then cooled again to 0 °C, N,N-diisopropylethylamine (2.6 g) was added, and the mixture was stirred at room temperature until the heat generation subsided. The mixture was then heated to 100 °C and stirred for 1 hour. The reaction mixture was cooled to room temperature, and an aqueous sodium acetate solution cooled in an ice bath, followed by ethyl acetate, was added and stirred for 1 hour. The yellow suspension was filtered, and the precipitate was washed with methanol. The yellow crystals were dissolved in toluene by heating and purified using a silica gel short column (eluent: toluene). Toluene was added to the obtained crude product, and the mixture was concentrated, followed by addition of Solmix (A-11). The precipitated crystals were filtered and washed with methanol to obtain compound (1-517) (2.6 g).

[0500] [ka]

[0501] The compound was confirmed to have been obtained by MS measurement. 58 H 72 BN3:821.582

[0502] Synthesis Example (5): Synthesis of Compound (1-532) [ka]

[0503] A 1.53 M tert-butyllithium pentane solution (15.2 ml) was added to a flask containing intermediate (I-5) (10.1 g) and tert-butylbenzene (80 ml) under a nitrogen atmosphere at 0°C. After the dropwise addition, the mixture was heated to 60°C and stirred for 0.5 hours. Components with boiling points lower than tert-butylbenzene were then distilled off under reduced pressure. The mixture was cooled to -50°C, boron tribromide (5.8 g) was added, and the mixture was warmed to room temperature and stirred for 0.5 hours. The mixture was then cooled again to 0°C, N,N-diisopropylethylamine (2.6 g) was added, and the mixture was stirred at room temperature until the heat generation subsided. The mixture was then heated to 100°C and stirred for 1 hour. The reaction mixture was cooled to room temperature, and an aqueous sodium acetate solution cooled in an ice bath, followed by ethyl acetate, was added and stirred for 1 hour. The yellow suspension was filtered, and the precipitate was washed with methanol. The yellow crystals were dissolved in toluene by heating and purified using a silica gel short column (eluent: toluene). Toluene was added to the obtained crude product, and the mixture was concentrated, followed by addition of Solmix (A-11). The precipitated crystals were filtered and washed with methanol to obtain compound (1-532) (1.2 g).

[0504] [ka]

[0505] The compound was confirmed to have been obtained by MS measurement. 63 H 73 BN4:896.593

[0506] Synthesis Example (6): Synthesis of Compound (1-544) [ka]

[0507] A 1.53 M tert-butyllithium pentane solution (15.2 ml) was added to a flask containing intermediate (I-6) (9.3 g) and tert-butylbenzene (80 ml) under a nitrogen atmosphere at 0 °C. After the dropwise addition, the mixture was heated to 60 °C and stirred for 0.5 hours. Components with boiling points lower than tert-butylbenzene were then distilled off under reduced pressure. The mixture was cooled to -50 °C, boron tribromide (5.8 g) was added, and the mixture was warmed to room temperature and stirred for 0.5 hours. The mixture was then cooled again to 0 °C, N,N-diisopropylethylamine (2.6 g) was added, and the mixture was stirred at room temperature until the heat generation subsided. The mixture was then heated to 100 °C and stirred for 1 hour. The reaction mixture was cooled to room temperature, and an aqueous sodium acetate solution cooled in an ice bath, followed by ethyl acetate, was added and stirred for 1 hour. The yellow suspension was filtered, and the precipitate was washed with methanol. The yellow crystals were dissolved in toluene by heating and purified using a silica gel short column (eluent: toluene). Toluene was added to the obtained crude product, and the mixture was concentrated, followed by addition of Solmix (A-11). The precipitated crystals were filtered and washed with methanol to obtain compound (1-544) (0.9 g).

[0508] [ka]

[0509] The compound was confirmed to have been obtained by MS measurement. 57 H 67 BN4:818.546

[0510] Synthesis Example (7): Synthesis of Compound (1-551) [ka]

[0511] A 1.53 M tert-butyllithium pentane solution (15.2 ml) was added to a flask containing intermediate (I-7) (10.2 g) and tert-butylbenzene (80 ml) under a nitrogen atmosphere at 0°C. After the dropwise addition, the mixture was heated to 60°C and stirred for 0.5 hours. Components with boiling points lower than that of tert-butylbenzene were then removed by distillation under reduced pressure. The mixture was cooled to -50°C, and boron tribromide (5.8 g) was added. The mixture was then heated to room temperature and stirred for 0.5 hours. The mixture was then cooled again to 0°C, and N,N-diisopropylethylamine (2.6 g) was added. The mixture was stirred at room temperature until the heat generation subsided, then heated to 100°C and stirred for 1 hour. The reaction mixture was cooled to room temperature, and an aqueous solution of sodium acetate cooled in an ice bath was added, followed by ethyl acetate, and the mixture was stirred for 1 hour. The yellow suspension was filtered, and the precipitate was washed with methanol. The yellow crystals were dissolved in toluene by heating and purified using a silica gel short column (eluent: toluene). Toluene was added to the obtained crude product, and the mixture was concentrated, followed by addition of Solmix (A-11). The precipitated crystals were filtered and washed with methanol to obtain compound (1-551) (2.3 g).

[0512] [ka]

[0513] The compound was confirmed to have been obtained by MS measurement. 64 H 80 BN3:901.645

[0514] Synthesis Example (8): Synthesis of Compound (1-555) [ka]

[0515] A 1.53 M tert-butyllithium pentane solution (15.2 ml) was added to a flask containing intermediate (I-8) (9.3 g) and tert-butylbenzene (80 ml) under a nitrogen atmosphere at 0 °C. After the dropwise addition, the mixture was heated to 60 °C and stirred for 0.5 hours. Components with boiling points lower than tert-butylbenzene were then distilled off under reduced pressure. The mixture was cooled to -50 °C, boron tribromide (5.8 g) was added, and the mixture was warmed to room temperature and stirred for 0.5 hours. The mixture was then cooled again to 0 °C, N,N-diisopropylethylamine (2.6 g) was added, and the mixture was stirred at room temperature until the heat generation subsided. The mixture was then heated to 100 °C and stirred for 1 hour. The reaction mixture was cooled to room temperature, and an aqueous sodium acetate solution cooled in an ice bath, followed by ethyl acetate, was added and stirred for 1 hour. The yellow suspension was filtered, and the precipitate was washed with methanol. The yellow crystals were dissolved in toluene by heating and purified using a silica gel short column (eluent: toluene). Toluene was added to the obtained crude product, and the mixture was concentrated, followed by addition of Solmix (A-11). The precipitated crystals were filtered and washed with methanol to obtain compound (1-555) (2.1 g).

[0516] [ka]

[0517] The compound was confirmed to have been obtained by MS measurement. 58 H 74 BN3:823.598

[0518] Synthesis Example (9): Synthesis of Compound (1-221) [ka]

[0519] A 1.53 M tert-butyllithium pentane solution (15.2 ml) was added to a flask containing intermediate (I-9) (9.3 g) and tert-butylbenzene (80 ml) under a nitrogen atmosphere at 0 °C. After the dropwise addition, the mixture was heated to 60 °C and stirred for 0.5 hours. Components with boiling points lower than tert-butylbenzene were then removed by distillation under reduced pressure. The mixture was cooled to -50 °C, and boron tribromide (5.8 g) was added. The mixture was then heated to room temperature and stirred for 0.5 hours. The mixture was then cooled again to 0 °C, and N,N-diisopropylethylamine (2.6 g) was added. The mixture was stirred at room temperature until the heat generation subsided, then heated to 100 °C and stirred for 1 hour. The reaction mixture was cooled to room temperature, and an aqueous sodium acetate solution cooled in an ice bath, followed by ethyl acetate, was added and stirred for 1 hour. The yellow suspension was filtered, and the precipitate was washed with methanol. The yellow crystals were dissolved in toluene by heating and purified using a silica gel short column (eluent: toluene). Toluene was added to the obtained crude product, and the mixture was concentrated, followed by addition of Solmix (A-11). The precipitated crystals were filtered and washed with methanol to obtain compound (1-221) (2.0 g).

[0520] [ka]

[0521] The compound was confirmed to have been obtained by MS measurement. 58 H 70 BN3:819.566

[0522] Synthesis Example (10): Synthesis of Compound (1-222) [ka]

[0523] A 1.53 M tert-butyllithium pentane solution (15.2 ml) was added to a flask containing intermediate (I-10) (9.3 g) and tert-butylbenzene (80 ml) under a nitrogen atmosphere at 0 °C. After the dropwise addition, the mixture was heated to 60 °C and stirred for 0.5 hours. Components with boiling points lower than tert-butylbenzene were then removed by distillation under reduced pressure. The mixture was cooled to -50 °C, and boron tribromide (5.8 g) was added. The mixture was then heated to room temperature and stirred for 0.5 hours. The mixture was then cooled again to 0 °C, and N,N-diisopropylethylamine (2.6 g) was added. The mixture was stirred at room temperature until the heat generation subsided, then heated to 100 °C and stirred for 1 hour. The reaction mixture was cooled to room temperature, and an aqueous solution of sodium acetate cooled in an ice bath was added, followed by ethyl acetate, and the mixture was stirred for 1 hour. The yellow suspension was filtered, and the precipitate was washed with methanol. The yellow crystals were dissolved in toluene by heating and purified using a silica gel short column (eluent: toluene). Toluene was added to the obtained crude product, and the mixture was concentrated, followed by addition of Solmix (A-11). The precipitated crystals were filtered and washed with methanol to obtain compound (1-222) (2.2 g).

[0524] [ka]

[0525] The compound was confirmed to have been obtained by MS measurement. 58 H 70 BN3:819.566

[0526] Synthesis Example (11): Synthesis of Compound (1-241) [ka]

[0527] A 1.53 M tert-butyllithium pentane solution (15.2 ml) was added to a flask containing intermediate (I-11) (9.5 g) and tert-butylbenzene (80 ml) under a nitrogen atmosphere at 0°C. After the dropwise addition, the mixture was heated to 60°C and stirred for 0.5 hours. Components with boiling points lower than that of tert-butylbenzene were then distilled off under reduced pressure. The mixture was cooled to -50°C, and boron tribromide (5.8 g) was added. The mixture was then heated to room temperature and stirred for 0.5 hours. The mixture was then cooled again to 0°C, and N,N-diisopropylethylamine (2.6 g) was added. The mixture was stirred at room temperature until the heat generation subsided, then heated to 100°C and stirred for 1 hour. The reaction mixture was cooled to room temperature, and an aqueous solution of sodium acetate cooled in an ice bath, followed by ethyl acetate, was added and stirred for 1 hour. The yellow suspension was filtered, and the precipitate was washed with methanol. The yellow crystals were dissolved in toluene by heating and purified using a silica gel short column (eluent: toluene). Toluene was added to the obtained crude product, and the mixture was concentrated, followed by addition of Solmix (A-11). The precipitated crystals were filtered and washed with methanol to obtain compound (1-241) (2.1 g).

[0528] [ka]

[0529] The compound was confirmed to have been obtained by MS measurement. 60 H 68 BN3:841.551

[0530] Synthesis Example (12): Synthesis of Compound (1-402) [ka]

[0531] A 1.53 M tert-butyllithium pentane solution (15.2 ml) was added to a flask containing intermediate (I-12) (9.6 g) and tert-butylbenzene (80 ml) under a nitrogen atmosphere at 0 °C. After the dropwise addition, the mixture was heated to 60 °C and stirred for 0.5 hours. Components with boiling points lower than tert-butylbenzene were then distilled off under reduced pressure. The mixture was cooled to -50 °C, boron tribromide (5.8 g) was added, and the mixture was warmed to room temperature and stirred for 0.5 hours. The mixture was then cooled again to 0 °C, N,N-diisopropylethylamine (2.6 g) was added, and the mixture was stirred at room temperature until the heat generation subsided. The mixture was then heated to 100 °C and stirred for 1 hour. The reaction mixture was cooled to room temperature, and an aqueous solution of sodium acetate cooled in an ice bath, followed by ethyl acetate, was added and stirred for 1 hour. The yellow suspension was filtered, and the precipitate was washed with methanol. The yellow crystals were dissolved in toluene by heating and purified using a silica gel short column (eluent: toluene). Toluene was added to the obtained crude product, and the mixture was concentrated, followed by addition of Solmix (A-11). The precipitated crystals were filtered and washed with methanol to obtain compound (1-402) (2.4 g).

[0532] [ka]

[0533] The compound was confirmed to have been obtained by MS measurement. 61 H 70 BN3:855.566

[0534] Synthesis Example (13): Synthesis of Compound (1-518) [ka]

[0535] A 1.53 M tert-butyllithium pentane solution (15.2 ml) was added to a flask containing intermediate (I-13) (9.9 g) and tert-butylbenzene (80 ml) under a nitrogen atmosphere at 0°C. After the dropwise addition, the mixture was heated to 60°C and stirred for 0.5 hours. Components with boiling points lower than tert-butylbenzene were then distilled off under reduced pressure. The mixture was cooled to -50°C, boron tribromide (5.8 g) was added, and the mixture was warmed to room temperature and stirred for 0.5 hours. The mixture was then cooled again to 0°C, N,N-diisopropylethylamine (2.6 g) was added, and the mixture was stirred at room temperature until the heat generation subsided. The mixture was then heated to 100°C and stirred for 1 hour. The reaction mixture was cooled to room temperature, and an aqueous sodium acetate solution cooled in an ice bath, followed by ethyl acetate, was added and stirred for 1 hour. The yellow suspension was filtered, and the precipitate was washed with methanol. The yellow crystals were dissolved in toluene by heating and purified using a silica gel short column (eluent: toluene). Toluene was added to the obtained crude product, and the mixture was concentrated, followed by addition of Solmix (A-11). The precipitated crystals were filtered and washed with methanol to obtain compound (1-518) (2.5 g).

[0536] [ka]

[0537] The compound was confirmed to have been obtained by MS measurement. 60 H 772 BN3S:877.554

[0538] By appropriately changing the raw material compounds, other polycyclic aromatic compounds of the present invention can be synthesized according to the methods of the above synthesis examples.

[0539] In order to explain the present invention in more detail, examples of organic EL devices using the compounds of the present invention will be shown below, but the present invention is not limited to these.

[0540] Organic EL devices of Examples 1 to 3 and Comparative Example 1 were fabricated, and each had a luminance of 1000 cd / m 2The maximum wavelength (EL wavelength) (nm) and full width at half maximum (FWHM) (nm) of the emission spectrum during light emission, the driving voltage (V), and the external quantum efficiency (EQE) (%) were measured.

[0541] The quantum efficiency of a light-emitting element can be classified into internal quantum efficiency and external quantum efficiency, and the internal quantum efficiency indicates the rate at which external energy injected as electrons (or holes) into the light-emitting layer of the light-emitting element is converted purely into photons. On the other hand, the external quantum efficiency is calculated based on the amount of these photons that are emitted to the outside of the light-emitting element, and since some of the photons generated in the light-emitting layer are absorbed or continuously reflected inside the light-emitting element and are not emitted to the outside of the light-emitting element, the external quantum efficiency is lower than the internal quantum efficiency.

[0542] The spectral radiance (emission spectrum) and external quantum efficiency were measured as follows: Using an Advantest voltage / current generator R6144, the luminance of the element was measured at 1000 cd / m 2 The device was made to emit light by applying a voltage equal to the wavelength of the light emitted. The spectral radiance in the visible light region was measured perpendicular to the light-emitting surface using a TOPCON SR-3AR spectroradiometer. Assuming the light-emitting surface is a perfectly diffusing surface, the measured spectral radiance value for each wavelength component was divided by the wavelength energy and multiplied by π to obtain the number of photons at each wavelength. The number of photons was then integrated over the entire wavelength range observed to obtain the total number of photons emitted from the device. The applied current value divided by the elementary charge was used to obtain the number of carriers injected into the device, and the total number of photons emitted from the device divided by the number of carriers injected into the device was used to obtain the external quantum efficiency. The half-width of the emission spectrum was calculated as the width between the wavelengths above and below the maximum emission wavelength at which the intensity was 50%.

[0543] The materials of each layer in the fabricated organic EL device are shown below. "HI" (hole injection layer 1 material) is N 4 ,N 4 '-Diphenyl-N 4 ,N 4"HAT-CN" (hole injection layer 2 material) is 1,4,5,8,9,12-hexaazatriphenylene hexacarbonitrile; "HT-1" (hole transport layer 1 material) is N-([1,1'-biphenyl]-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluoren-2-amine; and "HT "Host-2" (hole transport layer 2 material) is N,N-di([1,1'-biphenyl]-4-yl)-3'-(9H-carbazol-9-yl)-[1,1'-biphenyl]-4-amine, "Host-1" is 2-(10-phenylanthracen-9-yl)dibenzo[b,d]furan, and "ET-1" (electron transport layer 1 material) is 2-(3'-(9,9-dimethyl-9H-fluoren-2-yl)-[1,1'-biphenyl]-3-yl)-4,6-diphenyl-1,3,5-triazine. "ET-2" (electron transport layer 2 material) is 4'-(4-(4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)naphthalen-1-yl)-[1,1'-biphenyl]-4-carbonitrile. The chemical structures of the compounds "0-1" and "Liq," which are dopants in Comparative Example 1, are shown below.

[0544] [ka]

[0545] Example 1 <Device using compound (1-363) as a dopant> A 26 mm × 28 mm × 0.7 mm glass substrate (manufactured by Optoscience Co., Ltd.) was used as a transparent support substrate. An ITO film was formed to a thickness of 180 nm by sputtering and polished to 120 nm. This transparent support substrate was fixed to the substrate holder of a commercially available vapor deposition apparatus (manufactured by Nagasu Sangyo Co., Ltd.). A tantalum vapor deposition boat containing HI, HAT-CN, HT-1, HT-2, compound (Host-1), compound (1-363), ET-1, and ET-2, and an aluminum nitride vapor deposition boat containing Liq, magnesium, and silver, respectively, were attached.

[0546] The following layers were formed in order on the ITO film of the transparent support substrate. -4 The pressure was reduced to 10 Pa, and HI was heated and evaporated to a thickness of 40 nm to form hole injection layer 1. HAT-CN was heated and evaporated to a thickness of 5 nm to form hole injection layer 2. HT-1 was heated and evaporated to a thickness of 45 nm to form hole transport layer 1. HT-2 was heated and evaporated to a thickness of 10 nm to form hole transport layer 2. Compound (Host-1) and compound (1-363) were then simultaneously heated and evaporated to a thickness of 20 nm to form an emitting layer. The evaporation rate was adjusted so that the mass ratio of compound (Host-1) as the host material to compound (1-363) as the dopant material was approximately 98:2. ET-1 was heated and evaporated to a thickness of 5 nm to form electron transport layer 1. ET-2 and Liq were simultaneously heated and evaporated to a thickness of 25 nm to form electron transport layer 2. The evaporation rate was adjusted so that the mass ratio of ET-2 to Liq was approximately 50:50. The deposition rate for each layer was 0.01 to 1 nm / sec. Liq was then heated and deposited at a deposition rate of 0.01 to 0.1 nm / sec to achieve a film thickness of 1 nm. Magnesium and silver were then simultaneously heated and deposited to a film thickness of 100 nm to form a cathode, yielding an organic EL device. The deposition rate was adjusted between 0.1 nm and 10 nm / sec to achieve a magnesium to silver atomic ratio of 10:1.

[0547] <Examples 2 to 13 and Comparative Example 1> Organic EL devices were fabricated in the same manner as in Example 1, except that the dopant material was changed to the compounds shown in Table 1.

[0548] A DC voltage of 1000 cd / m was applied to the ITO electrode as the anode and the magnesium / silver electrode as the cathode. 2 The light-emitting characteristics were measured, and the results are shown in Table 1.

[0549] [Table 1] [Industrial Applicability]

[0550] The polycyclic aromatic compound of the present invention is useful as a material for organic devices, particularly as a material for forming a light-emitting layer in an organic electroluminescent device. [Explanation of symbols]

[0551] 100 Organic electroluminescent device 101 Substrate 102 Anode 103 Hole injection layer 104 Hole transport layer 105 Light-emitting layer 106 Electron transport layer 107 Electron injection layer 108 Cathode 110 Substrate 120 electrodes 130 Paint film 140 Paint film 150 luminescent layer 200 banks 300 Inkjet Head 310 Ink Droplets

Claims

1. A polycyclic aromatic compound having a structure consisting of one or more structural units represented by the following formula (1): 【Chemistry 1】 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 may be substituted; Y １ is B, P, P=O or P=S, The aryl or heteroaryl rings in rings A, B, and C are each Y １ , X １ and X ２ Formula (1) having a 6-membered ring sharing a bond with the central fused bicyclic structure, X ２ is >C(-R) ２、 >NR, >O, >Si(-R) ２ or >S, wherein R of the >N-R is an optionally substituted aryl, an optionally substituted heteroaryl, an optionally substituted alkyl or an optionally substituted cycloalkyl, and the >C(-R) ２ and >Si(-R) ２ R is hydrogen, an optionally substituted aryl, an optionally substituted alkyl or an optionally substituted cycloalkyl, and the >N-R, the >C(-R) ２ , and the above >Si(—R) ２ At least one of R may be bonded to the C ring by —O—, —S—, —C(—R) 2 — or a single bond, and R in —C(—R) 2 — is hydrogen, alkyl or cycloalkyl; X １ is >C(-R) ２ , >N-R, >O, >Si(-R) ２ or >S, wherein R of the >N-R is an optionally substituted aryl, an optionally substituted heteroaryl, an optionally substituted alkyl or an optionally substituted cycloalkyl, and the >C(-R) ２ and >Si(-R) ２ R is hydrogen, an optionally substituted aryl, an optionally substituted alkyl, or an optionally substituted cycloalkyl, and the >N-R, the >C(-R) ２ , and the above >Si(—R) ２ at least one of R may be bonded to at least one of ring A or ring B via —O—, —S—, —C(—R) 2 — or a single bond, and R in —C(—R) 2 — is hydrogen, alkyl or cycloalkyl; In the above structure, at least one selected from the group consisting of ring A, ring B, and ring C contains at least one partial structure represented by formula (A), The partial structure represented by formula (A) is bonded to two adjacent atoms on an aryl ring or heteroaryl ring at two * marks, respectively. In formula (A), L is >NR, >O, >Si(-R) ２ or >S, wherein R of the >N-R is an optionally substituted aryl, an optionally substituted heteroaryl, an optionally substituted alkyl or an optionally substituted cycloalkyl, and the >Si(-R) ２ R is hydrogen, an optionally substituted aryl, an optionally substituted alkyl or an optionally substituted cycloalkyl, and the >N-R and the >Si(-R) ２ At least one of R is connected to the ring A, ring B, ring C, and R by a single bond. Ａ and optionally linked to at least one selected from the group consisting of: r is an integer from 1 to 4, R Ａ are each independently hydrogen, optionally substituted alkyl, or optionally substituted cycloalkyl, and any R Ａ is any other R Ａ and may be bonded to each other by a single bond, At least one selected from the group consisting of an aryl ring and a heteroaryl ring in the structure may be fused with at least one cycloalkane, at least one hydrogen in the cycloalkane may be substituted, and at least one —CH ２ - may be replaced by -O- or -S-; At least one hydrogen in the structure may be replaced with deuterium, cyano, or halogen.

2. 2. The polycyclic aromatic compound according to claim 1, wherein when at least one hydrogen atom in an aryl ring or heteroaryl ring in rings A, B, and C is replaced, the substituent is selected from the group consisting of substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted diarylamino, substituted or unsubstituted alkylarylamino, substituted or unsubstituted diheteroarylamino, substituted or unsubstituted arylheteroarylamino, substituted or unsubstituted diarylboryl (two aryls may be bonded via a single bond, >C(-R) 2 , >O, >S, or >N-R, and R in >C(-R) 2 and >N-R is aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, alkoxy, or aryloxy, which may be further substituted with an aryl, heteroaryl, alkyl, or cycloalkyl), substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryloxy, and substituted silyl.

3. Y １ The polycyclic aromatic compound according to claim 1 or 2, wherein

4. The polycyclic aromatic compound according to any one of claims 1 to 3, which contains at least one tertiary alkyl represented by the following formula (tR) in the structure: 【Chemistry 2】 In the formula (tR), R ａ , R ｂ and R ｃ are each independently an alkyl having 1 to 24 carbon atoms, and any —CH ２ - may be substituted with -O-, and * indicates the bonding position.

5. The polycyclic aromatic compound according to any one of claims 1 to 4, wherein the partial structure represented by formula (A) is bonded to an aryl ring or heteroaryl ring in ring B.

6. The partial structure represented by formula (A) is bonded to two adjacent carbon atoms on an aryl ring or heteroaryl ring at two * marks, r is 2, Two R's bonded to adjacent carbon atoms Ａ are bonded to each other, and other R Ａ and each independently represent hydrogen or an optionally substituted alkyl.

7. Two R's bonded to adjacent carbon atoms Ａ are bonded to each other to form -(CH ２ ) ４ -, and the remaining R Ａ and each of the groups is methyl.

8. The polycyclic aromatic compound according to any one of claims 1 to 7, wherein L is >N-R, and R of the >N-R is an optionally substituted aryl.

9. The polycyclic aromatic compound according to any one of claims 1 to 5, wherein the partial structure represented by (A) is the following structure: 【Transformation 3】 In the formula, two *'s are attached to two adjacent atoms on the aryl or heteroaryl ring, respectively, and Me is methyl.

10. X １ is >N-R, and X １ R of >N—R is optionally substituted aryl, optionally substituted heteroaryl, optionally substituted alkyl or optionally substituted cycloalkyl, and may be bonded to at least one of ring A or ring B via —O—, —S—, —C(—R) 2 — or a single bond; X ２ is >N-R, and X ２ The polycyclic aromatic compound according to any one of claims 1 to 9, wherein R in >N-R is optionally substituted aryl, optionally substituted heteroaryl, optionally substituted alkyl, or optionally substituted cycloalkyl, and is optionally bonded to at least one selected from the group consisting of ring A and ring C via -O-, -S-, -C(-R) 2 -, or a single bond.

11. A polycyclic aromatic compound represented by any one of the following formulas (2-7) to (2-9): 【Chemistry 4】 Y １ is B, P, P=O or P=S, X １ is >C(-R) ２ , >N-R, >O, >Si(-R) ２ or >S, wherein R of the >N-R is an optionally substituted aryl, an optionally substituted heteroaryl, an optionally substituted alkyl or an optionally substituted cycloalkyl, and the >C(-R) ２ and >Si(-R) ２ R is hydrogen, an optionally substituted aryl, an optionally substituted alkyl or an optionally substituted cycloalkyl, and the >N-R, the >C(-R) ２ , and the above >Si(—R) ２ at least one of R may be bonded to at least one of ring a or ring b via —O—, —S—, —C(—R) 2 — or a single bond, and R in —C(—R) 2 — is hydrogen, alkyl or cycloalkyl; Z is C(-R Ｚ ) or N, and R Ｚ are each independently hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted diarylamino, substituted or unsubstituted alkylarylamino, substituted or unsubstituted diheteroarylamino, substituted or unsubstituted arylheteroarylamino, substituted or unsubstituted diarylboryl (two aryls may be bonded via a single bond, >C(-R) 2 , >O, >S, or >N-R, and R in >C(-R) 2 and >N-R is aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, alkoxy, or aryloxy, which may be further substituted with aryl, heteroaryl, alkyl, or cycloalkyl), substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryloxy, or substituted silyl; and R bonded to adjacent C Ｚ may bond 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 by a substituted or unsubstituted aryl, a substituted or unsubstituted heteroaryl, a substituted or unsubstituted diarylamino, a substituted or unsubstituted diheteroarylamino, a substituted or unsubstituted arylheteroarylamino, a substituted or unsubstituted diarylboryl (two aryls may be bonded via a single bond, >C(-R) 2 , >O, >S, or >N-R, and R in >C(-R) 2 and >N-R is an aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, alkoxy, or aryloxy, which may be further substituted by an aryl, heteroaryl, alkyl, or cycloalkyl), a substituted or unsubstituted alkyl, a substituted or unsubstituted cycloalkyl, a substituted or unsubstituted alkoxy, a substituted or unsubstituted aryloxy, or a substituted silyl; X ３ are each independently >C(-R) ２ , >N-R, >O, >Si(-R) ２ or >S, wherein R of the >N-R is an aryl having 6 to 12 carbon atoms, a heteroaryl having 2 to 15 carbon atoms, an alkyl having 1 to 6 carbon atoms, or a cycloalkyl having 3 to 14 carbon atoms, and the >C(-R) ２ and >Si(-R) ２ R is hydrogen, aryl having 6 to 12 carbon atoms, alkyl having 1 to 6 carbon atoms, or cycloalkyl having 3 to 14 carbon atoms; In each of the formulas (2-7) to (2-9), the partial structure represented by formula (A) is a ring, a ring, a ring c, and R Ｚ and are bonded at two * positions to two adjacent carbon atoms on one or more rings selected from the group consisting of rings formed by bonding In formula (A), L is >NR, >O, >Si(-R) ２ or >S, wherein R of the >N-R is an optionally substituted aryl, an optionally substituted heteroaryl, an optionally substituted alkyl or an optionally substituted cycloalkyl, and the >Si(-R) ２ R is hydrogen, an optionally substituted aryl, an optionally substituted alkyl or an optionally substituted cycloalkyl, and the >N-R and the >Si(-R) ２ At least one of R's is connected to Z, X's by a single bond. ３ and R Ａ and optionally linked to at least one selected from the group consisting of: r is an integer from 1 to 4, R Ａ are each independently hydrogen, optionally substituted alkyl, or optionally substituted cycloalkyl, and any R Ａ is any other R Ａ and may be bonded to each other by a single bond, At least one selected from the group consisting of aryl rings and heteroaryl rings in each of formulas (2-7) to (2-9) may be condensed with at least one cycloalkane, at least one hydrogen in the cycloalkane may be substituted, and at least one -CH ２ - may be replaced by -O- or -S-; At least one hydrogen atom in each of formulas (2-7) to (2-9) may be substituted with deuterium, cyano or halogen.

12. A polycyclic aromatic compound having a structure represented by the following formula (1-BA1) or formula (1-BA2): 【Transformation 5】 In formula (1-BA1) and formula (1-BA2), ring c is an optionally substituted benzene ring, an optionally substituted benzofuran ring, or an optionally substituted benzothiophene ring; Each R is independently an optionally substituted phenyl; R ２ ' is hydrogen or alkyl having 1 to 6 carbon atoms, Me represents methyl; In at least one benzene ring in the structure, hydrogen atoms bonded to adjacent carbon atoms may be substituted with a partial structure represented by formula (B): 【Transformation 6】 In formula (B), Me represents methyl, and * represents the bonding position.

13. The polycyclic aromatic compound according to claim 12, having a structure represented by any one of the following formulas: 【Transformation 7】 In the formula, Me represents methyl, and tBu represents t-butyl.

14. A polycyclic aromatic compound having a structure represented by the following formula (1-BA3) or formula (1-BA4): 【Transformation 8】 In formula (1-BA3) and formula (1-BA4), ring c is an optionally substituted benzene ring, an optionally substituted benzofuran ring, or an optionally substituted benzothiophene ring; Each R is independently an optionally substituted phenyl; R ２ ' is hydrogen or alkyl having 1 to 6 carbon atoms, Me represents methyl; In at least one benzene ring in the structure, hydrogen atoms bonded to adjacent carbon atoms may be substituted with a partial structure represented by formula (B): 【Chemistry 9】 In formula (B), Me represents methyl, and * represents the bonding position.

15. The polycyclic aromatic compound according to claim 14, having a structure represented by any one of the following formulas: 【Chemistry 10】 In the formula, Me represents methyl, and tBu represents t-butyl.

16. A polycyclic aromatic compound having a structure represented by the following formula (1-BA5), (1-BA6), (1-BA7) or (1-BA8): 【Chemistry 11】 In formulas (1-BA5), (1-BA6), (1-BA7) and (1-BA8), Ring D is an optionally substituted benzene ring or an optionally substituted cyclohexane ring; Each R is independently an optionally substituted phenyl; R ｄ are each independently hydrogen, optionally substituted alkyl, optionally substituted aryl, optionally substituted heteroaryl, or optionally substituted diarylamino; Me represents methyl; In at least one benzene ring in the structure, hydrogen atoms bonded to adjacent carbon atoms may be substituted with a partial structure represented by formula (B): 【Chemistry 12】 In formula (B), Me represents methyl, and * represents the bonding position.

17. The polycyclic aromatic compound according to claim 16, having a structure represented by any one of the following formulas: 【Chemistry 13】 In the formula, Me represents methyl, and tBu represents t-butyl.

18. A polycyclic aromatic compound having a structure represented by any one of the following formulas: 【Chemistry 14】 In formula (1-BA11), formula (1-BA12), formula (1-BA13) and formula (1-BA14), Z is C(-R Ｚ ) or N, and R Ｚ are each independently hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl; Each R is independently an optionally substituted phenyl; R ２ ' is hydrogen or alkyl having 1 to 6 carbon atoms, Me represents methyl; In at least one benzene ring in the structure, hydrogen atoms bonded to adjacent carbon atoms may be substituted with a partial structure represented by formula (B): 【Chemistry 15】 In formula (B), Me represents methyl, and * represents the bonding position.

19. The polycyclic aromatic compound according to claim 18, having a structure represented by any one of the following formulas: 【Chemistry 16】 In the formula, Me represents methyl, and tBu represents t-butyl.

20. A material for an organic device, comprising the polycyclic aromatic compound according to any one of claims 1 to 19.

21. The material for an organic device according to claim 20 , 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.

22. The material for an organic device according to claim 21 , wherein the material for an organic electroluminescent element is a material for a light-emitting layer.

23. An ink composition comprising the polycyclic aromatic compound according to any one of claims 1 to 19 and an organic solvent.

24. An organic electroluminescent 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 any one of claims 1 to 19.

25. 25. The organic electroluminescent device according to claim 24, wherein the organic layer is a light-emitting layer.

26. 26. The organic electroluminescent device according to claim 25, wherein the light-emitting layer comprises a host and the polycyclic aromatic compound as a dopant.

27. 27. The organic electroluminescent device according to claim 26, wherein the host is an anthracene-based compound, a fluorene-based compound, or a dibenzochrysene-based compound.

28. The organic electroluminescent device according to any one of claims 25 to 27, comprising at least one of an electron transport layer and an electron injection layer disposed between the cathode and the light-emitting layer, and at least one of the electron transport layer and the electron injection layer contains a compound represented by formula (ETM-10). 【Chemistry 17】 In formula (ETM-10), each Ar is independently an optionally substituted aryl or an optionally substituted heteroaryl, and n is an integer of 1 to 3.

29. A display device or lighting device comprising the organic electroluminescent element described in any one of claims 24 to 28.

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