Polycyclic aromatic compounds

Abstract

To provide a novel compound as a material for an organic device, such as an organic electroluminescent element.SOLUTION: Specifically, a polycyclic aromatic compound (1-7) can be presented which includes nitrogen and boron synthesized, for example, as in the following formula.SELECTED DRAWING: None

Description

[Technical Field]

[0001] The present invention relates to a polycyclic aromatic compound. In particular, the present invention relates to a polycyclic aromatic compound containing nitrogen and boron. The present invention also relates to a material for an organic device, an organic electroluminescent element, 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 the subject of extensive research because of their potential for power saving and thinning, and organic electroluminescent devices made from organic materials have also been actively investigated 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 in 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 electroluminescent 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 these, Patent Documents 1 and 2 disclose that boron-containing polycyclic aromatic compounds are useful as materials for organic electroluminescent devices, etc. It has been reported that organic electroluminescent devices containing these polycyclic aromatic compounds have good external quantum efficiency. [Prior art documents] [Patent documents]

[0005] [Patent Document 1] Chinese Patent Application Publication No. 106467554 [Patent Document 2] International Publication No. 2015 / 102118 Summary of the Invention [Problem to be solved by the invention]

[0006] As mentioned above, various materials have been developed for use in organic EL devices. However, 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 ones. An object of the present invention is to provide a novel compound 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 novel polycyclic aromatic compound having superior light-emitting properties among polycyclic aromatic compounds having a structure similar to that of the compound described in Patent Document 1. Furthermore, they discovered that an excellent organic EL device can be obtained by constructing an organic EL device 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):

[0009] [ka]

[0010] In formula (1), Ring A, ring B, and ring C are each independently an optionally substituted aryl ring or an optionally substituted heteroaryl ring, provided that at least one ring selected from the group consisting of ring A, ring B, and ring C in the structure is a ring represented by formula (Het); Y 1is B, P, P═O, P═S, Al, Ga, As, Si—R, or Ge—R, and R of the Si—R and Ge—R is a substituted or unsubstituted aryl, a substituted or unsubstituted alkyl, or a substituted or unsubstituted cycloalkyl; X 1 and X 2 are each independently >O, >NR, >C(-R)2, >Si(-R)2, >S, or >Se, R of the >NR is hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl, R of the >C(-R)2 and >Si(-R)2 are each independently hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl, the two R of the >C(-R)2 and the >Si(-R)2 may be bonded to each other to form a ring, and R of the >NR and / or R of the >C(-R)2 may be bonded to ring A and / or ring B, or ring A and / or ring C via a linking group or a single bond, In the formula (Het), X 3 and X 4 are each independently >O, >NR, >C(-R)2, >S, >Si(-R)2, >C=O, >S=O, >S(=O)2, or >Se, R of the >NR is hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl, R of the >C(-R)2 and R of the >Si(-R)2 are each independently hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl, two R may be bonded to each other to form a ring, and R of the >NR and / or R of the >C(-R)2 may be bonded to one or two Zs via a linking group or a single bond, Any pair of two or three consecutive Zs is Y 1 and X 1 and / or X 2and each of the other Zs is independently N or CR. Z and the CR Z R Z is a hydrogen or a substituent, and two adjacent CR Z R Z may be bonded to each other to form an aryl or heteroaryl ring, which ring may be substituted; Z=Z may each independently be >O, >NR, >C(-R)2, >Si(-R)2, >S, >CO, >SO, >SO2, or >Se, and R in the >NR, the >C(-R)2, and the >Si(-R)2 each independently is hydrogen, a substituted or unsubstituted aryl, a substituted or unsubstituted heteroaryl, a substituted or unsubstituted alkyl, or a substituted or unsubstituted cycloalkyl, and two R in the >C(-R)2 and the >Si(-R)2 may be bonded to each other to form a ring, At least one of the aryl or heteroaryl rings 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 -CH2- in the cycloalkane may be substituted with -O-; At least one hydrogen in the above structure may be replaced with cyano, halogen, or deuterium.

[0011] <2> Represented by the following formula (1-a), formula (1-b), formula (1-c), formula (1-d), formula (1-e), or formula (1-f): <1> the polycyclic aromatic compound according to [ka]

[0012] In formula (1-a), formula (1-b), formula (1-c), formula (1-d) and formula (1-e), Each Z is independently N or CR Z and the CR Z R Zare each independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl (two aryls may be bonded via a single bond or a linking group), alkyl, cycloalkyl, alkoxy, aryloxy, or substituted silyl, in which at least one hydrogen may be substituted with aryl, heteroaryl, alkyl, cycloalkyl, or substituted silyl; Two adjacent CRs Z R Z may be bonded to each other to form a ring, and the formed ring may be substituted with hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl (two aryls may be bonded via a single bond or a linking group), alkyl, cycloalkyl, alkoxy, aryloxy, or substituted silyl, and at least one hydrogen in these may be substituted with alkyl, cycloalkyl, or substituted silyl; X 1 and X 2 are each independently >O, >NR, >C(-R)2, >Si(-R)2, >S, or >Se, R of the >NR is hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl, R of the >C(-R)2 and >Si(-R)2 are each independently hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl, two R of the >C(-R)2 and the >Si(-R)2 may be bonded to each other to form a ring, and R of the >NR and / or R of the >C(-R)2 are / is connected to CR by a linking group or a single bond. Z is Z in R Z may be bonded to one or two of X 3 , X 4 , X 5 and X 6are each independently >O, >NR, >C(-R)2, >S, >Si(-R)2, >C=O, >S=O, >S(=O)2 or >Se, R of the >NR is hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, R of the >C(-R)2 is each independently hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl, and two R's may be bonded to each other to form a ring, Z=Z are independently >O, >NR, >C(-R)2, >Si(-R)2, R in the >NR, the >C(-R)2 and the >Si(-R)2 each independently represents hydrogen, a substituted or unsubstituted aryl, a substituted or unsubstituted heteroaryl, a substituted or unsubstituted alkyl, or a substituted or unsubstituted cycloalkyl, and two R in the >C(-R)2 and the >Si(-R)2 may be bonded to each other to form a ring; In the compound represented by formula (1-a), formula (1-b), formula (1-c), formula (1-d) or formula (1-e), at least one of the aryl rings or heteroaryl rings may be fused with at least one cycloalkane, at least one hydrogen in the cycloalkane may be substituted, and at least one -CH2- in the cycloalkane may be substituted with -O-; At least one hydrogen atom in the compound represented by formula (1-a), formula (1-b), formula (1-c), formula (1-d) or formula (1-e) may be substituted with cyano, halogen or deuterium.

[0013] <3> Represented by formula (1-b), <2> The polycyclic aromatic compound according to claim 1. <4> Both Z are CR Z That is, <3> The polycyclic aromatic compound according to claim 1. <5> X 3 is >NR and X 3R in NR is substituted or unsubstituted aryl; <1> ~ <4> 1. The polycyclic aromatic compound according to any one of claims 1 to 9. <6> X 3 R is phenyl substituted with tertiary alkyl; <5> The polycyclic aromatic compound according to claim 1. <7> X 4 is >C(-R)2 and X 4 >All R in C(-R)2 are methyl; <1> ~ <6> 1. The polycyclic aromatic compound according to any one of claims 1 to 9. <8> Y 1 is B <1> ~ <7> 1. The polycyclic aromatic compound according to any one of claims 1 to 9. <9> X 1 and X 2 are all >NR <1> ~ <8> 1. The polycyclic aromatic compound according to any one of claims 1 to 9.

[0014] <10> Represented by the formula (1-b-Z): <4> the polycyclic aromatic compound according to [ka]

[0015] In formula (1-b-Z), R X1 and R X2 are each independently substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl; R X1 is connected to R by a linking group or a single bond. X1 may be bonded to any of the rings to which the N bonded is directly bonded, and R X2 is connected to R by a linking group or a single bond. X1 and R X2 may be bonded to any ring to which the N to which is bonded is directly bonded, X 13are each independently >O, >NR, or >C(—R)2, R of the >NR is a substituted or unsubstituted aryl or a substituted or unsubstituted heteroaryl, R of the >C(—R)2 is each independently an unsubstituted alkyl, and two Rs may be bonded to each other to form a cycloalkane ring; R X4 are each independently unsubstituted alkyl, and two R X4 may be bonded to each other to form a cycloalkane ring, R Z1 is unsubstituted alkyl, R Z2 each independently represents an unsubstituted alkyl; m represents an integer of 0 to 2; R Z3 are each independently an unsubstituted alkyl, and n is an integer of 0 to 2, In the structure represented by formula (1-b-Z), at least one of the aryl rings or heteroaryl rings may have a structure in which a partial structure represented by formula (B) is bonded to an adjacent carbon atom,

[0016] [ka]

[0017] In formula (B), Me represents methyl, * represents the bonding position, At least one hydrogen atom in the structure represented by formula (1-b-Z) may be substituted with cyano, halogen, or deuterium.

[0018] <11> Represented by one of the following formulas <10> the polycyclic aromatic compound according to [ka] In the formula, Me is methyl and tBu is t-butyl.

[0019] <12> Represented by the formula (1-b―T), <3> the polycyclic aromatic compound according to [ka]

[0020] In formula (1-b-T), R X1 and R X2 are each independently substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl; R X1 is connected to R by a linking group or a single bond. X1 may be bonded to any of the rings to which the N bonded is directly bonded, and R X2 is connected to R by a linking group or a single bond. X1 and R X2 may be bonded to any ring to which the N to which is bonded is directly bonded, X 13 are each independently >O, >NR, or >C(—R)2, R of the >NR is a substituted or unsubstituted aryl or a substituted or unsubstituted heteroaryl, R of the >C(—R)2 is each independently an unsubstituted alkyl, and two Rs may be bonded to each other to form a cycloalkane ring; R X4 are each independently unsubstituted alkyl, and two R X4 may be bonded to each other to form a cycloalkane ring, R Z1 is unsubstituted alkyl, R Z2 each independently represents an unsubstituted alkyl; m represents an integer of 0 to 2; R Z3 are each independently an unsubstituted alkyl, and n is an integer of 0 to 2, In the structure represented by formula (1-b-T), at least one of the aryl rings or heteroaryl rings may have a structure in which a partial structure represented by the following formula (B) is bonded to an adjacent carbon atom:

[0021] [ka]

[0022] In formula (B), Me represents methyl, * represents the bonding position, At least one hydrogen atom in the structure represented by formula (1-b-T) may be substituted with cyano, halogen, or deuterium.

[0023] <13> Represented by one of the following formulas <12> the polycyclic aromatic compound according to [ka] In the formula, Me is methyl and tBu is t-butyl.

[0024] <14> <1> ~ <13> 10. A material for an organic device, comprising the polycyclic aromatic compound according to any one of claims 1 to 9. <15> A pair of electrodes consisting of an anode and a cathode, and a light-emitting layer disposed between the pair of electrodes. The light-emitting layer <1> ~ <13> 10. An organic electroluminescent device comprising the polycyclic aromatic compound according to any one of claims 1 to 9. <16> the light-emitting layer contains a host and the polycyclic aromatic compound as a dopant; <15> The organic electroluminescent device according to claim 1. <17> the host is an anthracene-based compound, a fluorene-based compound, or a dibenzochrysene-based compound; <16> The organic electroluminescent device according to claim 1. <18> <15> ~ <17> A display device or a lighting device comprising the organic electroluminescent device according to any one of the preceding claims. [Effects of the Invention]

[0025] The present invention provides a novel polycyclic aromatic compound useful as a material for organic devices such as organic electroluminescent elements. The polycyclic aromatic compound of the present invention can be used in the production of organic devices such as organic electroluminescent elements. [Brief explanation of the drawings]

[0026] [Figure 1] 1 is a schematic cross-sectional view showing an example of an organic electroluminescent device. [Figure 2]FIG. 1 is an energy level diagram showing the energy relationship among the host, assisting dopant, and emitting dopant of a TAF element using a common fluorescent dopant. [Figure 3] 1 is an energy level diagram showing an example of the energy relationship between a host, an assisting dopant, and an emitting dopant in an organic electroluminescent element according to one embodiment of the present invention. DETAILED DESCRIPTION OF THE INVENTION

[0027] 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)." In this specification, the organic electroluminescent device may be referred to as an organic EL device.

[0028] 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.

[0029] This specification describes many structural formulas for aromatic compounds. Although aromatic compounds are depicted as combining double and single bonds, in reality, due to π electron resonance, a single substance may have multiple equivalent resonance structures, such as those in which double and single bonds alternate. While only one resonance structure is depicted for each substance in this specification, other organically equivalent resonance structures are also included unless otherwise specified. This is referenced in notations such as "Z=Z" below. In other words, when "Z=Z" is used in this specification, it includes not only those structures shown as "Z=Z" but also those shown as "ZZ" in resonance structures. For example, the "Z=Z" in formula (1-b) below is shown below as an example. However, this is not limited to this, and naturally applies not only to the single resonance structure depicted but also to other possible equivalent resonance structures.

[0030] [ka]

[0031] In this specification, unless otherwise specified, "adjacent" means that atoms are directly bonded to each other on the same ring, and "adjacent groups" means groups that are directly bonded to atoms that are directly bonded to each other on the same ring.

[0032] 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 formula (1). The polycyclic aromatic compound of the present invention has at least one ring represented by formula (Het) as ring A, ring B, or ring C in formula (1). The polycyclic aromatic compound of the present invention has a high luminescence quantum yield (PLQY), a narrow luminescence half-width, and excellent color purity.

[0033] [ka]

[0034] At least one ring selected from the group consisting of ring A, ring B, and ring C in the structure consisting of one or more structural units represented by formula (1) is a ring represented by formula (Het). In a structure consisting of one of the structural units represented by formula (1), it is preferred that one or two rings selected from the group consisting of ring A, ring B, and ring C are rings represented by formula (Het). When one ring is a ring represented by formula (Het), the ring is not particularly limited, but is preferably ring B or ring C. When two rings are rings represented by formula (Het), the rings are not particularly limited, but are preferably ring B and ring C. In a structure consisting of one of the structural units represented by formula (1), it is more preferred that one ring is a ring represented by formula (Het). In a structure consisting of two or more structural units represented by formula (1), each structural unit represented by formula (1) may or may not contain at least one ring represented by formula (Het). That is, even when there are two or more of at least one of ring A, ring B, or ring C, it is sufficient that at least one ring in the structure consisting of one or two or more structural units represented by formula (1) is a ring represented by formula (Het).

[0035] In the formula (Het), X 3 and X 4 are each independently >O, >NR, >C(-R)2, >S, >Si(-R)2, >C=O, >S=O, >S(=O)2, or >Se. 3 or X 4 In the formula >NR, R is hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl. X 3 or X 4 R in >C(-R)2 and >Si(-R)2 is independently hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl, and two R may be bonded to each other to form a ring.

[0036] In formula (Het), X 3 and X 4 are preferably each independently >O, >NR, >C(-R)2, >S, >Si(-R)2, or >Se, and more preferably each independently >O, >C(-R)2, or >NR. 3 and X 4 may be the same or different. X 3 is >NR, >C(-R)2, or >O, and X 4 It is particularly preferred that >C(-R)2.

[0037] X 3 or X 4 In the formula >NR, R is preferably an optionally substituted aryl, more preferably an unsubstituted aryl or an aryl substituted with alkyl, and even more preferably a phenyl or a phenyl substituted with tertiary alkyl. 3 or X 4 Preferably, R in >C(—R)2 and >Si(—R)2 is optionally substituted alkyl, more preferably both are unsubstituted alkyl, and even more preferably both are unsubstituted methyl.

[0038] In formula (Het), any pair of consecutive two or three Z's is Y 1 and X 1 and / or X 2 and C (carbon atoms) directly bonded to each other. In other words, when ring B is a ring represented by formula (Het), any pair of consecutive two is Y 1 and X 1 and C are directly bonded to each other, and when the C ring is a ring represented by the formula (Het), any pair of consecutive two is Y 1 and X 2 and C are directly bonded to each other, and when ring A is a ring represented by formula (Het), any pair of three consecutive rings is Y 1 , X 1 and X 2and C directly bonded to each other. Other Zs are independently N or CR Z and the CR Z R Z is hydrogen or a substituent. In this case, the substituent is preferably a substituted or unsubstituted aryl, a substituted or unsubstituted heteroaryl, a substituted or unsubstituted diarylamino, a substituted or unsubstituted diheteroarylamino, a substituted or unsubstituted arylheteroarylamino (an amino having an aryl and a heteroaryl), a substituted or unsubstituted diarylboryl (the two aryls may be bonded via a single bond or a linking group), a substituted or unsubstituted alkyl, a substituted or unsubstituted cycloalkyl, a substituted or unsubstituted alkoxy, a substituted or unsubstituted aryloxy, or a substituted silyl. Two adjacent CR Z R in Z may bond to each other to form an aryl ring or a heteroaryl ring, and the formed ring may be substituted. The substituent is preferably a substituted or unsubstituted aryl, a substituted or unsubstituted heteroaryl, a substituted or unsubstituted diarylamino, a substituted or unsubstituted diheteroarylamino, a substituted or unsubstituted arylheteroarylamino (an amino having an aryl and a heteroaryl), a substituted or unsubstituted diarylboryl (the two aryls may be bonded via a single bond or a linking group), a substituted or unsubstituted alkyl, a substituted or unsubstituted cycloalkyl, a substituted or unsubstituted alkoxy, a substituted or unsubstituted aryloxy, or a substituted silyl.

[0039] For details of these substituents, reference can be made to the descriptions of the first and second substituents given below.

[0040] Furthermore, in formula (Het), Z=Z may each independently be >O, >NR, >C(-R)2, >Si(-R)2, >S, or >Se. Of these, >O, >NR, >C(-R)2, or >S is preferred. R in the >NR, >C(-R)2, and >Si(-R)2 each independently represents hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl, and the two R in the >C(-R)2 and >Si(-R)2 may be bonded to each other to form a ring. For one ring (monocycle) in formula (Het), there are examples where one Z=Z is >NR, >O, or >S and the remaining Z is CH, and examples where one Z=Z is >NR, >O, or >S and the remaining Zs are adjacent and both are CR. Z And these R Z The following is an example of a benzene ring formed by bonding together:

[0041] [ka]

[0042] In formula (Het), X 3 and X 4 Of the two rings other than the ring containing Y, at least one is preferably a six-membered ring. 1 and X 1 and / or X 2 The ring bonded to is preferably a six-membered ring.

[0043] In formula (Het), the number of rings (monocyclic rings) containing Z as N is 0 to 2, and more preferably 0 to 1. 1 and X 1 and / or X 2 All Zs except for Z which is C (carbon atom) having a bond with CR Z It is also preferable that:

[0044] In formula (Het), 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, a pyrimidine ring, a pyridazine ring, or a 1,2,3-triazine ring, and more preferably a pyridine ring or a pyrimidine ring. A pair of Z=Z is >O, >NR, >C(-R)2, >Si(-R)2, Examples of a ring containing Z as N in a five-membered ring that is >S or >Se include a thiazole ring and an oxazole ring.

[0045] In formula (Het), X 3 or X 4 R and / or X in >NR when is >NR 3 or X 4 When R is C(-R)2, R in >C(-R)2 may be bonded to one or two Z's via a linking group or a single bond. 3 or X 4 Preferably, Z is adjacent to the atom to which X is bonded. In addition, the bonded Z may be a carbon atom having a bond. Examples of such a linking group include X 1 , X 2 Examples of the linking group connecting the ring B and the ring C can be seen in X. 3 or X 4 Examples of structures in which R in >NR forms the above bond include structures represented by the following formulas.

[0046] [ka]

[0047] In the above formula, Me is methyl and X is at the two * positions. 3 or X 4 is attached to one of the two rings and to the other ring at the ** position. Examples of such structures include the structures of compounds represented by any of formulas (1-182) to (1-204) and formulas (1-319) to (1-333) described below.

[0048] In the structure consisting of one or more structural units represented by formula (1), rings A, B, and C other than the ring represented by formula (Het) are each independently an optionally substituted aryl ring or an optionally substituted heteroaryl ring.

[0049] The aryl or heteroaryl rings in rings A, B and C are each independently selected from Y 1 and X 1 and / or X 2 and preferably bonded to each other via a 5- or 6-membered ring. 1 and X 1 and / or X 2 The phrase "bonded to Y via a 5- or 6-membered ring" means that the ring is formed by only this 5- or 6-membered ring, or that the ring is formed by further condensing another ring to include this 5- or 6-membered ring. In other words, the 5- or 6-membered ring that constitutes all or part of the ring is bonded to Y 1 and X 1 and / or X 2 In the aryl or heteroaryl rings in rings A, B, and C, two or three consecutive ring atoms (carbon atoms) are bonded to Y. 1 and X 1 and / or X 2 That is, any pair of two consecutive ring-constituting atoms (carbon atoms) in the aryl ring or heteroaryl ring in ring B may be directly bonded to Y. 1 and X 1 and any pair of consecutive ring atoms (carbon atoms) in the aryl or heteroaryl ring of ring C is directly bonded to Y 1 and X 2and any pair of three consecutive ring atoms (carbon atoms) in the aryl or heteroaryl ring of ring A is directly bonded to Y. 1 , X 1 and X 2 is directly bonded to

[0050] The "aryl ring" in ring A, ring B, and ring C of formula (1) includes, for example, an aryl ring having 6 to 30 carbon atoms, preferably an aryl ring having 6 to 16 carbon atoms, more preferably an aryl ring having 6 to 12 carbon atoms, and particularly preferably an aryl ring having 6 to 10 carbon atoms.

[0051] Specific examples of the "aryl ring" include a monocyclic benzene ring, a bicyclic bicyclic bicyclic naphthalene ring, a 5,6,7,8-tetrahydronaphthalene ring, an indene ring, a tricyclic terphenyl ring (m-terphenyl, o-terphenyl, p-terphenyl), a fused tricyclic acenaphthylene ring, a fluorene ring, a phenalene ring, a phenanthrene ring, an anthracene ring, a fused tetracyclic triphenylene ring, a pyrene ring, a naphthacene ring, a chrysene ring, a fused pentacyclic perylene ring, a pentacene ring, etc. Furthermore, the fluorene ring, the benzofluorene ring, and the indene ring each include a structure in which a fluorene ring, a benzofluorene ring, a cyclopentane ring, etc. are spiro-bonded. The tetrahydronaphthalene ring, 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 a first substituent described below, resulting in a 1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthalene ring, a dimethylfluorene ring, a dimethylbenzofluorene ring, a dimethylindene ring, and the like.

[0052] Examples of the "heteroaryl ring" which is ring A, ring B, and ring C in formula (1) include heteroaryl rings having 2 to 30 carbon atoms, preferably heteroaryl rings having 2 to 25 carbon atoms, more preferably heteroaryl rings having 2 to 20 carbon atoms, 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.

[0053] 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 fluorophenyl ... Examples include a thalazine ring, a naphthyridine ring, a purine ring, a pteridine ring, a carbazole ring, an acridine ring, a phenothiazine ring, a phenazine ring, a phenazasiline ring, an indolizine ring, a furan ring, a benzofuran ring, an isobenzofuran ring, a dibenzofuran ring, a thiophene ring, a benzothiophene ring, a dibenzothiophene ring, a furazan ring, a thianthrene ring, an indolocarbazole ring, a benzoindolocarbazole ring, a benzobenzoindolocarbazole ring, a naphthobenzofuran ring, a dioxin ring, a dihydroacridine ring, a xanthene ring, a thioxanthene ring, a dibenzodioxin ring, etc. Furthermore, dihydroacridine rings, xanthene rings, and thioxanthene rings are also preferred in which two of the two hydrogen atoms of the methylene are each substituted with an alkyl such as methyl as the first substituent described below, resulting in 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.

[0054] Further, examples of the heteroaryl ring include a ring represented by the following formula (BO).

[0055] [ka]

[0056] At least one hydrogen atom in the "aryl ring" or "heteroaryl ring" may be substituted with a first substituent, which is a substituted or unsubstituted "aryl," a substituted or unsubstituted "heteroaryl," a substituted or unsubstituted "diarylamino," a substituted or unsubstituted "diheteroarylamino," a substituted or unsubstituted "arylheteroarylamino," a substituted or unsubstituted "diarylboryl (the two aryls may be bonded via a single bond or a linking group)," a substituted or unsubstituted "alkyl," a substituted or unsubstituted "cycloalkyl," a substituted or unsubstituted "alkoxy," a substituted or unsubstituted "aryloxy," or a substituted "silyl." Examples of the "aryl" or "heteroaryl" as the first substituent, the aryl of "diarylamino," the heteroaryl of "diheteroarylamino," the aryl and heteroaryl of "arylheteroarylamino," the aryl of "diarylboryl," and the aryl of "aryloxy" include the monovalent groups of the "aryl ring" or "heteroaryl ring" described above.

[0057] 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.

[0058] Specific examples of the aryl include phenyl, which is a monocyclic aryl; (2-, 3-, 4-)biphenylyl, which is a bicyclic aryl; (1-, 2-)naphthyl, (1-, 2-)5,6,7,8-tetrahydronaphthyl, (2-, 3-, 4-, 5-, 6-, 7-)indenyl, which are fused bicyclic aryl; and terphenylyl (m-terphenyl-2'-yl, m-terphenyl-4 ... 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), Fused tricyclic aryls include anthracene-(1-, 2-, 3-, 4-, 5-, 6-, 7-, 8-, 9-, 10-)yl, acenaphthylene-(1-, 3-, 4-, 5-)yl, fluoren-(1-, 2-, 3-, 4-, 9-)yl, phenalen-(1-, 2-)yl, and (1-, 2-, 3-, 4-, 9-)phenanthryl; tetracyclic aryls include quaterphenylyl (5'-phenyl-m-terphenyl-2-yl); aryl, 5'-phenyl-m-terphenyl-3-yl, 5'-phenyl-m-terphenyl-4-yl, m-quaterphenylyl), fused tetracyclic aryls such as triphenylene-(1-, 2-)yl, pyrene-(1-, 2-, 4-)yl, naphthacene-(1-, 2-, 5-)yl, and fused pentacyclic aryls such as perylene-(1-, 2-, 3-)yl, pentacene-(1-, 2-, 5-, 6-)yl.

[0059] 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.

[0060] 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.

[0061] 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.

[0062] Specific alkyls include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, t-butyl, n-pentyl, isopentyl, neopentyl, t-pentyl (t-amyl), n-hexyl, 1-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, n-heptyl, 1-methylhexyl, n-octyl, t-octyl (1,1,3,3-tetramethylbutyl), and the like. ), 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 2,6-dimethyl-4-heptyl, 3,5,5-trimethylhexyl, n-decyl, n-undecyl, 1-methyldecyl, n-dodecyl, n-tridecyl, 1-hexylheptyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, n-heptadecyl, n-octadecyl, and n-eicosyl. Further examples include 1-ethyl-1-methylpropyl, 1,1-diethylpropyl, 1,1-dimethylbutyl, 1-ethyl-1-methylbutyl, 1,1,4-trimethylpentyl, 1,1,2-trimethylpropyl, 1,1-dimethyloctyl, 1,1-dimethylpentyl, 1,1-dimethylheptyl, 1,1,5-trimethylhexyl, 1-ethyl-1-methylhexyl, 1-ethyl-1,3-dimethylbutyl, 1,1,2,2-tetramethylpropyl, 1-butyl-1-methylpentyl, 1,1-diethylbutyl, 1-ethyl-1-methylpentyl, 1,1,3-trimethylbutyl, 1-propyl-1-methylpentyl, 1,1,2-trimethylpropyl, 1-ethyl-1,2,2-trimethylpropyl, 1-propyl-1-methylbutyl, and 1,1-dimethylhexyl.

[0063] 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).

[0064] [ka]

[0065] 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 *.

[0066] 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).

[0067] 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.

[0068] 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.

[0069] 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.

[0070] Furthermore, examples of the "cycloalkyl" as the first substituent include cycloalkyl having 3 to 24 carbon atoms, cycloalkyl having 3 to 20 carbon atoms, cycloalkyl having 3 to 16 carbon atoms, cycloalkyl having 3 to 14 carbon atoms, cycloalkyl having 5 to 10 carbon atoms, cycloalkyl having 5 to 8 carbon atoms, cycloalkyl having 5 to 6 carbon atoms, and cycloalkyl having 5 carbon atoms.

[0071] 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 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[2.2.1]heptyl (norbornyl), bicyclo[2.2.2]octyl, adamantyl, diamantyl, decahydronaphthalenyl, and decahydroazulenyl.

[0072] 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.

[0073] Specific examples of alkoxy include methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, s-butoxy, t-butoxy, t-amyloxy, pentyloxy, hexyloxy, heptyloxy, and octyloxy.

[0074] 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.

[0075] 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.

[0076] 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.

[0077] 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.

[0078] Specific examples of tricycloalkylsilyl include tricyclopentylsilyl and tricyclohexylsilyl.

[0079] 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.

[0080] 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.

[0081] 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.

[0082] 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 "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.

[0083] The above explanation of the second substituent can also be applied to the substituents when "substituted or unsubstituted" is used unless otherwise explained in this specification.

[0084] The emission wavelength can be adjusted by the steric hindrance, electron donating property, and electron withdrawing property of the structure of the first substituent. Preferred are groups represented by the following structural formulas, and more preferred are methyl, t-butyl, t-amyl, t-octyl, neopentyl, adamantyl, phenyl, o-tolyl, p-tolyl, 2,4-xylyl, 2,5-xylyl, 2,6-xylyl, 2,4,6-mesityl, diphenylamino, di-p-tolylamino, bis(p-(t-butyl)phenyl)amino, carbazolyl, 3,6-dimethylcarbazolyl, 3,6- Di-t-butylcarbazolyl and phenoxy are more preferred, and methyl, t-butyl, t-amyl, t-octyl, neopentyl, adamantyl, phenyl, o-tolyl, 2,6-xylyl, 2,4,6-mesityl, diphenylamino, di-p-tolylamino, bis(p-(t-butyl)phenyl)amino, carbazolyl, 3,6-dimethylcarbazolyl and 3,6-di-t-butylcarbazolyl are more preferred. From the viewpoint of ease of synthesis, a larger steric hindrance is preferred for selective synthesis, and specifically, t-butyl, t-amyl, t-octyl, adamantyl, o-tolyl, p-tolyl, 2,4-xylyl, 2,5-xylyl, 2,6-xylyl, 2,4,6-mesityl, di-p-tolylamino, bis(p-(t-butyl)phenyl)amino, 3,6-dimethylcarbazolyl, and 3,6-di-t-butylcarbazolyl are preferred.

[0085] 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]

[0086] [ka]

[0087] [ka]

[0088]

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[0089]

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[0090]

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[0091]

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[0092]

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[0093]

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[0094]

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[0095]

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[0096]

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[0097]

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[0098]

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[0099] [ka]

[0100] The polycyclic aromatic compound having a structure consisting of one or more structural units represented by formula (1) preferably has a structure containing at least one tertiary alkyl (such as t-butyl or t-amyl), neopentyl, or adamantyl group represented by formula (tR), and more preferably contains a tertiary alkyl (such as t-butyl or t-amyl) represented by formula (tR). This is because such bulky substituents increase the intermolecular distance, thereby improving the luminescence quantum yield (PLQY). Diarylamino is also a preferred substituent.

[0101] In formula (1), Y 1 are each independently B, P, P=O, P=S, Al, Ga, As, Si-R, or Ge-R, and R in the Si-R and Ge-R is a substituted or unsubstituted aryl, a substituted or unsubstituted alkyl, or a substituted or unsubstituted cycloalkyl. Examples of the aryl, alkyl, or cycloalkyl include the groups described above. Particularly preferred are aryls having 6 to 10 carbon atoms (e.g., phenyl, naphthyl, etc.), alkyls having 1 to 5 carbon atoms (e.g., methyl, ethyl, etc.), or cycloalkyls having 5 to 10 carbon atoms (preferably cyclohexyl or adamantyl). Y 1 is preferably B, P, P=O, P=S, or Si-R, and particularly preferably B. 1 The explanation regarding Y in formula (1-a), formula (1-b), formula (1-c), formula (1-d), formula (1-e), and formula (1-f) will be described later. 1 Also applies to.

[0102] X in formula (1) 1 and X 2are each independently >O, >NR, >Si(-R)2, >C(-R)2, >S, or >Se. X in formula (1) 1 and X 2 Preferably, at least one of the >NR groups is >NR, more preferably, both are >NR, or one is >NR and the other is >C(-R)2 or >O, and even more preferably, both are >NR. When it is written as "both are >NR," the Rs of the two >NR groups may be the same or different.

[0103] X 1 or X 2 R in >NR is hydrogen, optionally substituted aryl (excluding amino as a substituent), optionally substituted heteroaryl, optionally substituted alkyl, or optionally substituted cycloalkyl. 1 or X 2 Each R in >Si(-R)2 is independently hydrogen, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted alkyl, or optionally substituted cycloalkyl. 1 or X 2 Each R in >C(-R)2 is independently hydrogen, an optionally substituted aryl, an optionally substituted heteroaryl, an optionally substituted alkyl, or an optionally substituted cycloalkyl, and preferably, two R are the same, and two R may be bonded to form a ring. X 1 or X 2 For the aryl, heteroaryl, alkyl, and cycloalkyl in R of >NR, >Si(—R) 2 , or >C(—R) 2 , reference can be made to the explanation thereof as the first substituent above.

[0104] X 1 or X 2In 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 or an optionally substituted heteroaryl. Examples of cycloalkyl include those described below. Preferred aryls include phenyl, biphenylyl (particularly 2-biphenylyl), and terphenylyl (particularly terphenyl-2'-yl). Preferred heteroaryls include benzothienyl (e.g., 2-benzothienyl, 6-benzothienyl), benzofuranyl (e.g., 2-benzofuranyl, 3-benzofuranyl, 5-benzofuranyl), dibenzofuranyl (e.g., 4-dibenzofuranyl), dimethylxanthenyl (e.g., 2-dimethylxanthenyl), and dibenzodioxinyl. Preferred substituents are tertiary alkyls (e.g., t-butyl) or cycloalkyls (e.g., adamantyl) represented by the formula (tR). The number of substituents in the aryl and heteroaryl is preferably 0 to 2, more preferably 1 or 2, and even more preferably 1. It is also preferred that the aryl ring in the above aryl is condensed with a cycloalkane which may be substituted as described below. Specific examples of the cycloalkane include those described below.

[0105] X 1 or X 2 Particularly preferred examples of R in >NR include optionally substituted phenyl, optionally substituted 2-biphenylyl, optionally substituted terphenyl-2'-yl, optionally substituted terphenyl-4'-yl, and aryl (optionally substituted) fused with a cycloalkane. The optionally substituted phenyl, optionally substituted 2-biphenylyl, optionally substituted terphenyl-2'-yl, and optionally substituted terphenyl-4'-yl are preferably substituted with one to three t-butyl groups. The following are particularly preferred aryls fused with a cycloalkane:

[0106] [ka] (In the formula, Me is methyl, tBu is t-butyl, and * indicates the bonding position.)

[0107] X 1 or X 2 R in at least one of >NR, >Si(—R)2 and >C(—R)2 may be bonded to ring A and / or ring B, or ring A and / or ring C via a linking group or a single bond. That is, X 1 R in >NR, >Si(—R)2 or >C(—R)2 may be bonded to ring A and / or ring B via a linking group or a single bond, and X 2 In >NR, >Si(-R)2 or >C(-R)2, R may be bonded to ring A and / or ring C via a linking group or a single bond. As the linking group, -O-, -S- or -C(-R)2- is preferred. In addition, R in the above "-C(-R)2-" is hydrogen, alkyl or cycloalkyl. This definition applies to X represented by the following formula (1-3-1): 1 or X 2 can be expressed as a compound having a ring structure in which X is incorporated into the fused rings B' and C'. That is, for example, X is incorporated into the fused ring B' (or C) which is a benzene ring. 1 (or X 2 The compound has a ring B' (or ring C') formed by condensing another ring so as to incorporate the ring B'. The condensed ring B' (or condensed ring C') formed is, for example, a carbazole ring, a phenoxazine ring, a phenothiazine ring, or an acridine ring.

[0108] In addition, the above provisions are based on the following formulas (1-3-2) and (1-3-3): 1 and / or X 2 It can also be expressed as a compound having a ring structure in which X is incorporated into the fused ring A'. 1 (and / or X 2The compound has a ring A' formed by condensing another ring so as to incorporate the ring A'. The condensed ring A' formed is, for example, a carbazole ring, a phenoxazine ring, a phenothiazine ring, or an acridine ring.

[0109] [ka]

[0110] As one example, it is also preferred that R in the >NR is an optionally substituted cycloalkyl and is bonded via a single bond to ring A, ring B, or ring C. As the cycloalkyl, an optionally substituted cyclopentyl or an optionally substituted cyclohexyl is preferred.

[0111] A particularly preferred example is the structure represented by formula (A11).

[0112] [ka] In formula (A11), Me is methyl, and X is at the two * positions. 1 or X 2 is attached to one of the two rings and to the other ring at the ** position. Examples of such structures include the structures of compounds represented by any of formulas (1-7), (1-30), (1-53), (1-96), (1-112), (1-144), (1-174), (1-179) to (1-181), (1-202) to (1-204), (1-211), and (1-223) described below.

[0113] The preferred range of R is >NR, and X is 1 or X 2 By using the compound of the present invention having the formula (I) as a light-emitting material, the light-emitting efficiency and the life of the device can be further improved.

[0114] X in equation (1) 1 or X 2In the formula >Si(-R)2, R is an optionally substituted aryl, an optionally substituted heteroaryl, an optionally substituted alkyl, or an optionally substituted cycloalkyl. When substituted, examples of the substituent include the second substituent described above. The aryl, heteroaryl, alkyl, or cycloalkyl include the groups described above as the first substituent. Particularly preferred are aryls having 6 to 10 carbon atoms (e.g., phenyl, naphthyl, etc.), heteroaryls having 2 to 15 carbon atoms (e.g., carbazolyl, etc.), alkyls having 1 to 5 carbon atoms (e.g., methyl, ethyl, etc.), and cycloalkyls having 5 to 10 carbon atoms (preferably cyclohexyl or adamantyl).

[0115] X in equation (1) 1 or X 2 R in R of >C(-R)2 is hydrogen, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted alkyl, or optionally substituted cycloalkyl. When substituted, examples of the substituent include the second substituent described above. Examples of the aryl, heteroaryl, alkyl, or cycloalkyl include the groups described above as the first substituent. Particularly preferred are 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).

[0116] In formula (1), X 1 , X 2When "-C(-R)-" is bonded to at least one of the rings A, B, and C, examples of the linking group include -O-, -S-, -C(-R)-, and a single bond. Among these, R in "-C(-R)-" is hydrogen, alkyl, or cycloalkyl, and examples of the alkyl or cycloalkyl include the groups described above as the first substituent. 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.

[0117] X in the above formula (1) 1 , X 2 The explanation regarding X in formula (1-a), formula (1-b), formula (1-c), formula (1-d), formula (1-e), and formula (1-f) will be described later. 1 , X 2 Also applies to.

[0118] 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) 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) contained in the above unit structure is bonded together so that it is fused. Furthermore, the above unit structures may be bonded together by a linking group such as a single bond, alkylene having 1 to 3 carbon atoms, phenylene, naphthylene, etc. Among these, a bonded structure so as to share a ring is preferred.

[0119] In the polycyclic aromatic compound having a structure consisting of one or more structural units represented by formula (1), at least one selected from the group consisting of aryl rings and heteroaryl rings may be condensed with at least one cycloalkane. The same applies to the polycyclic aromatic compounds represented by formula (1-a), formula (1-b), formula (1-c), formula (1-d), formula (1-e), or formula (1-f) described below, and the following explanation also applies to the polycyclic aromatic compounds represented by formula (1-a), formula (1-b), formula (1-c), formula (1-d), formula (1-e), or formula (1-f).

[0120] The cycloalkane may be a cycloalkane having 3 to 24 carbon atoms. In this case, at least one hydrogen atom in the cycloalkane may be substituted with an aryl having 6 to 30 carbon atoms, a heteroaryl having 2 to 30 carbon atoms, an alkyl having 1 to 24 carbon atoms, or a cycloalkyl having 3 to 24 carbon atoms, and at least one -CH2- group in the cycloalkane may be substituted with -O-.

[0121] When 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) is condensed with at least one cycloalkane, the at least one cycloalkane is preferably a cycloalkane having 3 to 20 carbon atoms, in which at least one hydrogen atom may be substituted with an aryl having 6 to 16 carbon atoms, a heteroaryl having 2 to 22 carbon atoms, an alkyl having 1 to 12 carbon atoms, or a cycloalkyl having 3 to 16 carbon atoms.

[0122] As the "cycloalkane", a cycloalkane having 3 to 24 carbon atoms is preferred, and more preferred examples include, in order of decreasing order, a cycloalkane having 3 to 20 carbon atoms, a cycloalkane having 3 to 16 carbon atoms, a cycloalkane having 3 to 14 carbon atoms, a cycloalkane having 5 to 10 carbon atoms, a cycloalkane having 5 to 8 carbon atoms, and a cycloalkane having 5 to 6 carbon atoms.

[0123] Specific examples of the cycloalkane include cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclooctane, cyclononane, cyclodecane, 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[2.2.1]heptane (norbornane), 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.

[0124] Among these, for example, as shown in the structural formula below, a structure in which at least one hydrogen atom is substituted on the α-carbon atom of a cycloalkane (the carbon atom directly bonded to the carbon atom at the condensation site in a cycloalkyl fused to an aryl ring or heteroaryl ring), 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.

[0125] [ka]

[0126] In formula (B), Me represents methyl, and * represents the bonding position. Examples of such structures include the following formulae (1-10), (1-33), (1-56), (1-99), (1-115), (1-147), (1-188) to (1-190), (1-196) to (1-198), (1-226), (1-356), (1-357), (1-361), (1-365) to (1-376), and (1-380). to (1-385), (1-404), (1-406) to (1-408), (1-420), (1-422) to (1-424), (1-435), (1-436), (1-438), (1-439), (1-444), (1-450), (1-451), (1-456), and (1-457).

[0127] The number of cycloalkanes fused to one aryl ring or heteroaryl ring is preferably 1 to 3, more preferably 1 or 2, and even more preferably 1. For example, an example in which one or more cycloalkanes are fused to one benzene ring (phenyl) is shown below. * indicates the bonding position, and the position may be any carbon that constitutes the benzene ring but not the cycloalkane. Fused cycloalkanes such as those in formula (Cy-1-4) and formula (Cy-2-4) may also be fused together. The same applies when the fused ring (group) is an aryl ring or heteroaryl ring other than a benzene ring (phenyl), or when the fused cycloalkane is a cycloalkane other than cyclopentane or cyclohexane.

[0128] [ka]

[0129] At least one -CH2- in a cycloalkane may be replaced with -O-. For example, an example in which one or more -CH2- in a cycloalkane fused to a benzene ring (phenyl) are replaced with -O- is shown below. The same applies even when the fused ring (group) is an aromatic ring or heteroaromatic ring other than a benzene ring (phenyl), or when the fused cycloalkane is a cycloalkane other than cyclopentane or cyclohexane.

[0130] [ka]

[0131] At least one hydrogen atom in the cycloalkane may be substituted. Examples of the substituent include aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl (the two aryls may be bonded via a single bond or a linking group), alkyl, cycloalkyl, alkoxy, aryloxy, substituted silyl, deuterium, cyano, and halogen. For details, see the description of the first substituent above. Among these substituents, alkyl (e.g., alkyl having 1 to 6 carbon atoms), cycloalkyl (e.g., cycloalkyl having 3 to 14 carbon atoms), halogen (e.g., fluorine), and deuterium are preferred. Furthermore, when cycloalkyl is substituted, it may be substituted to form a spiro structure, examples of which are shown below.

[0132] [ka]

[0133] Examples of cycloalkane condensation include cycloalkane condensation of one or more aryl or heteroaryl rings in the A, B, and C rings of polycyclic aromatic compounds having a structure consisting of one or more structural units represented by formula (1), and aryl or heteroaryl rings in the a, b, c, a11, b11, c11, a13, b13, and c13 rings in formulas (1-a), (1-b), (1-c), (1-d), (1-e), and (1-f)), or condensation rings. Examples of condensation rings of this type include tetralin rings and tetrahydronaphthothiophene rings.

[0134] Other forms of cycloalkane condensation include polycyclic aromatic compounds having a structure consisting of one or more structural units represented by formula (1), or polycyclic aromatic compounds represented by formula (1-a), formula (1-b), formula (1-c), formula (1-d), formula (1-e), or formula (1-f) having an aryl condensed with a cycloalkane or a heteroaryl condensed with a cycloalkane as a substituent or as a part of a substituent. For example, X 1 ~X 4In the >NR group, R is an aryl fused with a cycloalkane or a heteroaryl fused with a cycloalkane. Other examples include diarylamino fused with a cycloalkane (fused to the aryl portion), arylheteroarylamino fused with a cycloalkane (fused to the aryl portion and / or heteroaryl portion), diarylamino fused with a cycloalkane (fused to the heteroaryl portion), carbazolyl fused with a cycloalkane (fused to the benzene ring portion), or benzocarbazolyl fused with a cycloalkane (fused to the benzene ring portion), as well as an aryl fused with a cycloalkane or a heteroaryl fused with a cycloalkane as another substituent, or an aryl fused with a cycloalkane or a heteroaryl fused with a cycloalkane as a partial structure of a substituent (for example, the aryl portion of an aryloxy). Examples of "diarylamino" include the groups described above as the "first substituent."

[0135] Further, more specific examples include polycyclic aromatic compounds represented by formula (1-a), formula (1-b), formula (1-c), formula (1-d), formula (1-e), and formula (1-f) in which Y is present in the ring a. 1 R in the para position of Z is a diarylamino fused to a cycloalkane (fused to the aryl moiety) or a carbazolyl fused to a cycloalkane (fused to the benzene ring moiety).

[0136] All or part of the hydrogen atoms in the structure consisting of one or more structural units represented by formula (1) may be deuterium, cyano, or halogen. The same applies to the polycyclic aromatic compounds represented by formula (1-a), formula (1-b), formula (1-c), formula (1-d), formula (1-e), or formula (1-f) described below, and the following explanation also applies to the polycyclic aromatic compounds represented by formula (1-a), formula (1-b), formula (1-c), formula (1-d), formula (1-e), or formula (1-f).

[0137] For example, in a structure consisting of one or more structural units represented by formula (1), ring A, ring B, ring C (rings A to C are aryl rings or heteroaryl rings), substituents on rings A to C, Y 1 R when is Si—R or Ge—R (R is alkyl, cycloalkyl, or aryl), and X 1 and X 2 When is >NR, >C(—R)2, or >Si(—R)2, hydrogen atoms in R (R is alkyl, cycloalkyl, or aryl) can be substituted with deuterium, cyano, or halogen. Among these, hydrogen atoms in the 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 the aryl or heteroaryl are substituted with deuterium, cyano, or halogen. The halogen atom is fluorine, chlorine, bromine, or iodine, preferably fluorine, chlorine, or bromine, more preferably fluorine or chlorine, and even more preferably fluorine. From the viewpoint of durability, it is also preferred that all or some of the hydrogen atoms in the structure consisting of one or more structural units represented by formula (1) are deuterated. More preferred are those in which all hydrogen atoms directly bonded to aromatic rings are deuterated, or those in which all hydrogen atoms are deuterated. Most preferred are those in which all hydrogen atoms directly bonded to aromatic rings are deuterated.

[0138] Preferred examples of polycyclic aromatic compounds having a structure consisting of one or more structural units represented by formula (1) include polycyclic aromatic compounds represented by any of the following formulas (1-a), (1-b), (1-c), (1-d), (1-e), and (1-f). Note that for the substituents and ring structures and preferred ranges in formulas (1-a), (1-b), (1-c), (1-d), (1-e), and (1-f), reference can be made to the respective descriptions of the corresponding formulas (1).

[0139] [ka]

[0140] In formula (1-a), formula (1-b), formula (1-c), formula (1-d), formula (1-e) and formula (1-f), Y1 , X 1 and X 2 is Y in Eq. (1) 1 , X 1 and X 2 In addition, X in formula (1-a), formula (1-b), formula (1-c), formula (1-d), formula (1-e) and formula (1-f) have the same meanings and preferred ranges. 3 and X 4 is X in formula (Het) 3 and X 4 Furthermore, X in formula (1-d) and formula (1-e) have the same meaning as those in formula (1-d) and formula (1-e), and the preferred ranges are also the same. 5 and X 6 is X in formula (Het) 4 and X 3 and the preferred ranges are also the same.

[0141] Here, X in formula (1) 1 and X 2 The provision that "R in at least one of said >NR, >Si(-R)2 and >C(-R)2 is bonded to ring A and / or ring B, or ring A and / or ring C by a linking group or a single bond" in formula (1-a), formula (1-b), formula (1-c), formula (1-d), formula (1-e), and formula (1-f) is replaced by "R in at least one of said >NR, >Si(-R)2 and >C(-R)2 is bonded to ring A and / or ring B by -O-, -S-, -C(-R)2- or a single bond, Z is Z in R Z Specifically, the above R corresponds to the spatially closest CR in each ring shown below. Z It may be attached to Z, which is Formula (1-a):X 1 R in the middle is a ring, X 2 The R in the formula is the a-ring and / or the c-ring. Formula (1-b):X 1 R in the formula is a ring and / or b11 ring, X 2 The R in the formula is the a-ring and / or the c-ring. Formula (1-c):X 1R in the formula is a ring and / or b11 ring, X 2 The R in the formula is the a-ring and / or the c-ring. Formula (1-d):X 1 R in the formula is a ring and / or b11 ring, X 2 R in the formula is an a-ring and / or a c11-ring. Formula (1-e):X 1 R in the middle is a ring, X 2 The R in the middle is an a ring. Formula (1-f):X 1 R in the formula is a11 ring and / or b ring, X 2 The R in the middle is a c-ring.

[0142] In formula (1-a), formula (1-b), formula (1-c), formula (1-d), formula (1-e), and formula (1-f), Z is independently N or CR Z and the CR Z R Z is R in the above formula (Het) Z Please refer to the explanation of Z. Z In each formula, the plurality of R Z may be the same or different.

[0143] Furthermore, Z=Z independently represents >O, >NR, >C(-R)2, >Si(-R)2, It may be >S or >Se. Of these, >O, >NR, >C(-R)2, or >S is preferred. R in the >NR, the >C(-R)2, and the >Si(-R)2 are each independently hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl, and the two R in the >C(-R)2 and the >Si(-R)2 may be bonded to each other to form a ring. For example, when one Z=Z is >NR, >O, or >S, a pyrrole ring, a furan ring, or a thiophene ring is formed in the same manner as described above for one ring (monocycle) in formula (Het). The remaining Zs are adjacent and all are CR Z If these are R Zare joined to form a benzene ring, an indole ring, a benzofuran ring, or a benzothiophene ring is formed in the same manner as described above for one ring (monocyclic ring) in formula (Het).

[0144] In each of formulas (1-a), (1-b), (1-c), (1-d), (1-e), and (1-f), the number of rings (monocycles) containing Z as N is 0 to 4, preferably 0 to 3, more preferably 0 to 2, and particularly preferably 0 to 1. In each of formulas (1-a), (1-b), (1-c), (1-d), and (1-e), Z is all CR Z It is also preferable that:

[0145] In the formulas (1-a), (1-b), (1-c), (1-d), (1-e), and (1-f), 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, a pyrimidine ring, a pyridazine ring, or a 1,2,3-triazine ring, and more preferably a pyridine ring or a pyrimidine ring. When the 5-membered ring is a ring containing Z as N, it is preferably a thiazole ring or an oxazole ring.

[0146] Among the formulas (1-a), (1-b), (1-c), (1-d), (1-e) and (1-f), formula (1-a), (1-b), (1-c) or (1-d) is preferred, formula (1-a), (1-b) or (1-c) is more preferred, and formula (1-b) is most preferred.

[0147] In the formula (1-a), formula (1-b), formula (1-c), formula (1-d) and formula (1-e), Z in each of the ring a11, ring a13, ring b, ring b11, ring b13, ring c11 and ring c13 is CR Z In ring c, each Z is preferably CR Z or one Z=Z is >O, >NR, >C(-R)2, >Si(-R)2, >S or >Se (for embodiments and preferred examples thereof, see the description in the specification), and the remaining Z is CR Z and R Z are preferably bonded to each other to form an aryl ring (preferably a benzene ring) or a heteroaryl ring, and ring c is more preferably a benzene ring, a benzothiophene ring, a benzofuran ring, an indole ring or an indene ring, and most preferably a benzene ring or a benzothiophene ring.

[0148] As the polycyclic aromatic compound represented by formula (1-b), a polycyclic aromatic compound represented by the following formula (1-b-Z) or formula (1-b-T) is particularly preferred.

[0149] [ka]

[0150] In formula (1-b-Z) and formula (1-b-T), R X1 and R X2 are each independently substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl; R X1 is connected to R by a linking group or a single bond. X1 may be bonded to any of the rings to which the N bonded is directly bonded, and R X2 is connected to R by a linking group or a single bond. X1 and R X2 may be bonded to any of the rings to which the N bonded is directly bonded, 13 are each independently >O, >NR, or >C(—R)2, R of the >NR is a substituted or unsubstituted aryl or a substituted or unsubstituted heteroaryl, R of the >C(—R)2 is each independently an unsubstituted alkyl, and two Rs may be bonded to each other to form a cycloalkane ring; R X4 are each independently unsubstituted alkyl, and two R X4may be bonded to each other to form a cycloalkane ring, R Z1 each independently represents an unsubstituted alkyl; R Z2 are each independently an unsubstituted alkyl, m is an integer of 0 to 2, and R Z3 are each independently an unsubstituted alkyl, n is an integer of 0 to 2, and at least one of the aryl rings or heteroaryl rings in the structure represented by formula (1-b-Z) or formula (1-b-T) may have a structure in which a partial structure represented by the following formula (B) is bonded to an adjacent carbon atom:

[0151] [ka]

[0152] In formula (B), Me represents methyl, * represents the bonding position, At least one hydrogen atom in the structure represented by formula (1-b-Z) or formula (1-b-T) may be substituted with cyano, halogen, or deuterium.

[0153] In formula (1-b-Z) and formula (1-b-T), R X1 and R X2 are each a substituted or unsubstituted aryl, a substituted or unsubstituted heteroaryl, or NR X1 or NR X2 It is preferable that R forms a structure represented by formula (A11). X1 and R X2 The preferred range of X in the above formula (1) 1 or X 2 Reference can be made to the description of the preferred range of R in >NR.

[0154] X 13R in >NR is preferably aryl which may be substituted with alkyl or aryl, or heteroaryl which may be substituted with alkyl or aryl, and more preferably phenyl which may be substituted with alkyl having 1 to 6 carbon atoms (preferably t-butyl). X 13 It is preferable that all R in >C(-R)2 are methyl. R X4 is preferably methyl. R Z1 are each preferably independently alkyl having 1 to 6 carbon atoms, more preferably methyl or t-butyl. Z2 are each independently preferably alkyl having 1 to 6 carbon atoms, more preferably methyl or t-butyl. m is preferably 0 or 1. R Z3 are each independently preferably alkyl having 1 to 6 carbon atoms, more preferably methyl or t-butyl. n is preferably 0 or 1. When n is 1, R Z3 is X 13 It is preferably in the para position relative to In addition, in the structures represented by formula (1-b-Z) and formula (1-b-T), it is preferable that 0 to 2 of the aryl rings or heteroaryl rings have a structure in which a partial structure represented by formula (B) is bonded to adjacent carbon atoms in the ring. When the structures represented by formula (1-b-Z) and formula (1-b-T) each contain a partial structure represented by formula (B), the ring to which the partial structure represented by formula (B) is bonded is preferably R Z2 is attached to the benzene ring or R X1 Or R X2 Preferably, the aryl ring is any one of the aryl rings in the following formula:

[0155] Further specific examples of the polycyclic aromatic compound represented by formula (1) of the present invention include the following compounds. In the following structural formula, "Me" represents methyl, "tBu" represents t-butyl, "tAm" represents t-amyl, and "D" represents deuterium. Note that the following structure is an example.

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[0185] [ka]

[0186] The polycyclic aromatic compounds of the present invention may exist as enantiomers or diastereomers depending on the type of substituents, etc., but regardless of the structural formula shown, any pure stereoisomer, any mixture of stereoisomers, racemate, etc. are all intended to be encompassed within the scope of the present invention.

[0187] 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).

[0188] 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.

[0189] [ka]

[0190] 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.

[0191] 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.

[0192] Method for producing polycyclic aromatic compounds Polycyclic aromatic compounds having a structure consisting of one or more structural units represented by formula (1) or polycyclic aromatic compounds represented by formula (1-a), formula (1-b), formula (1-c), formula (1-d), formula (1-e), or formula (1-f) are basically prepared by first bonding ring A (ring a), ring B (ring b), and ring C (ring c) together through bonding groups (X 1 or X 2 A ring A (ring a), a ring B (ring b) and a ring C (ring c) are bonded together with a bonding group (Y 1 The final product can be produced by bonding the two rings together with a group containing (Het) (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, the same applies below) can be used. By using a raw material with the desired fused ring somewhere in the reaction process or by adding a ring condensation step, it is possible to produce a compound in which at least one ring selected from the group consisting of ring A, ring B, and ring C is a ring represented by formula (Het).

[0193] Manufacturing method via intermediate-1 The polycyclic aromatic compound of the present invention can be produced by a production method including the following steps. For each of the steps, reference can be made to the description in WO 2015 / 102118. In the above-mentioned production method, X in the following Intermediate-1 is obtained by using an organic alkali compound. 1 and X 2 a reaction step of metallating the halogen atom (Hal) between Y 1 Halides of Y 1 Aminated halides of Y 1 Alkoxylated compounds of Y 1 and Y are reacted with a reagent selected from the group consisting of aryl oxy compounds of the formula 1 and a reaction step of exchanging Y with a Bronsted base by successive electrophilic aromatic substitution reactions. 1 and a reaction step of bonding the B ring and the C ring together.

[0194] [ka]

[0195] Manufacturing method via intermediate-2 The polycyclic aromatic compound of the present invention is also preferably produced by a production method including a reaction step of reacting the following intermediate-2 with an acid. For details, see the description in JP 2018-76281 A and the like. [ka] (In Intermediate-2, Z is -B(OH)2 which may be esterified.)

[0196] Z in Intermediate-2 is -B(OH)2 which may be esterified. 1 is the group to which -B(OH)2 has been esterified.

[0197] The group (-B(OR)2) obtained by esterifying -B(OH)2 is not particularly limited, and examples thereof include groups obtained by reacting alcohols including diols or carboxylic acids with boronic acids. R in -B(OR)2 includes optionally substituted alkyls having 1 to 4 carbon atoms (branched alkyls having 3 to 4 carbon atoms), and R groups may be bonded to each other to form a ring, or the formed ring may contain an aromatic ring such as benzene. Specific examples include groups with the following structures. In the following structures, "Me" represents methyl, "Et" represents ethyl, "iPr" represents isopropyl, and * represents the bonding position.

[0198] [ka]

[0199] For details of the method for producing boronic acids or boronic acid esters such as Intermediate-2, reference can be made to JP 2018-76281 A.

[0200] 2. Organic Devices The polycyclic aromatic compound of 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.

[0201] 2-1. Organic electroluminescent device 2-1-1. Structure of organic electroluminescent device FIG. 1 is a schematic cross-sectional view showing an example of an organic EL element. 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.

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

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

[0204] 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."

[0205] 2-1-2. Light-emitting layer in organic electroluminescent device The polycyclic aromatic compound of the present invention is preferably used as a material for forming one or more organic layers in an organic electroluminescent device, and more preferably used as a material for forming a light-emitting layer. 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 that emits light when excited by the recombination of holes and electrons (a light-emitting compound), and is preferably a compound that can be formed into a stable thin film and that exhibits strong luminescence (fluorescence) efficiency in a solid state. The polycyclic aromatic compound of the present invention can be used as a material for a light-emitting layer, and may be used as a dopant material or as a host material.

[0206] The polycyclic aromatic compound of the present invention is preferably a material for a light-emitting layer, and more preferably a dopant material.

[0207] Although there are cases where the dopant is used in combination with an assisting dopant and an emitting dopant, in this specification, when the term "dopant" is simply used, it refers to a light-emitting dopant used alone.

[0208] The light-emitting layer may be a single layer or may consist of multiple layers, each formed from materials for the light-emitting layer (host material, dopant material). The host material and dopant material may each be one type, or a combination of multiple types. The dopant material may be contained entirely in the host material, or may be contained partially in the host material. As a doping method, the dopant material can be formed by co-evaporation with the host material, but it may also be mixed with the host material in advance and then co-evaporated. It is also preferable to mix multiple host materials in advance and then co-evaporate them with the dopant material. Specific examples of dopants to be combined with the compound of the present invention when multiple dopants are combined are shown below. In the structural formula below, "Me" represents methyl, "tBu" represents t-butyl, and "D" represents deuterium.

[0209] [ka]

[0210] [ka]

[0211] [ka]

[0212] [ka]

[0213] [ka]

[0214] 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.

[0215] 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 materials for the light-emitting layer. The above range is preferable in that, for example, concentration quenching can be prevented.

[0216] host material Examples of the host material include fused ring derivatives of anthracene, pyrene, dibenzochrysene, fluorene, and the like, which have long been known as light-emitting materials; bisstyryl derivatives such as bisstyrylanthracene derivatives and distyrylbenzene derivatives; tetraphenylbutadiene derivatives; cyclopentadiene derivatives; fluorene derivatives; benzofluorene derivatives; and dibenzochrysene-based compounds.

[0217] As the host material, for example, a compound represented by any one of the following formulae (H1), (H2) and (H3) can be used. [ka]

[0218] In formulas (H1), (H2) and (H3), L 1 represents an arylene having 6 to 24 carbon atoms, a heteroarylene having 2 to 24 carbon atoms, a heteroarylenearylene having 6 to 24 carbon atoms, or an aryleneheteroarylenearylene having 6 to 24 carbon atoms, preferably an arylene having 6 to 16 carbon atoms, more preferably an arylene having 6 to 12 carbon atoms, and particularly preferably an arylene having 6 to 10 carbon atoms, and specific examples thereof include divalent groups such as a benzene ring, a biphenyl ring, a terphenyl ring, and a fluorene ring. The heteroarylene is preferably a heteroarylene having 2 to 24 carbon atoms, more preferably a heteroarylene having 2 to 20 carbon atoms, still more preferably a heteroarylene having 2 to 15 carbon atoms, and particularly preferably a heteroarylene having 2 to 10 carbon atoms. Specific examples thereof include a pyrrole ring, an oxazole ring, an isoxazole ring, a thiazole ring, an isothiazole ring, an imidazole ring, an oxadiazole ring, a thiadiazole ring, a triazole ring, a tetrazole ring, a pyrazole ring, a pyridine ring, a pyrimidine ring, a pyridazine ring, a pyrazine ring, a triazine ring, an indole ring, an isoindole ring, a 1H-indazole ring, a benzophenone ... and divalent groups such as a benzoimidazole ring, a benzoxazole ring, a benzothiazole ring, a 1H-benzotriazole ring, a quinoline ring, an isoquinoline ring, a cinnoline ring, a quinazoline ring, a quinoxaline ring, a phthalazine ring, a naphthyridine ring, a purine ring, a pteridine ring, a carbazole ring, an acridine ring, a phenoxathiin ring, a phenoxazine ring, a phenothiazine ring, a phenazine ring, an indolizine ring, a furan ring, a benzofuran ring, an isobenzofuran ring, a dibenzofuran ring, a thiophene ring, a benzothiophene ring, a dibenzothiophene ring, a furazan ring, an oxadiazole ring, and a thianthrene ring. At least one hydrogen atom in the compounds represented by the above formulas may be substituted with alkyl having 1 to 6 carbon atoms, cyano, halogen, or deuterium.

[0219] Preferred specific examples include compounds represented by any of the structural formulas listed below. In the structural formulas listed below, at least one hydrogen may be substituted with halogen, cyano, alkyl having 1 to 4 carbon atoms (e.g., methyl or t-butyl), phenyl, naphthyl, or the like.

[0220] [ka]

[0221] [ka]

[0222] [ka]

[0223] [ka]

[0224] <Anthracene compounds> Examples of anthracene compounds as hosts include compounds represented by the following formula (3-H) and (3-H2). [ka]

[0225] In formula (3-H), X and Ar 4are each independently hydrogen, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted diarylamino, optionally substituted diheteroarylamino, optionally substituted arylheteroarylamino, optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted alkenyl, optionally substituted alkoxy, optionally substituted aryloxy, optionally substituted arylthio or optionally substituted silyl, and all X and Ar 4 cannot simultaneously become hydrogen, At least one hydrogen atom in the compound represented by formula (3-H) may be substituted with halogen, cyano, deuterium, or an optionally substituted heteroaryl.

[0226] Furthermore, a multimer (preferably a dimer) may be formed using the structure represented by formula (3-H) as a unit structure. In this case, for example, the unit structures represented by formula (3-H) may be bonded to each other via X, where X may be a single bond, an arylene (such as phenylene, biphenylene, or naphthylene), or a heteroarylene (a divalent group such as a pyridine ring, a dibenzofuran ring, a dibenzothiophene ring, a carbazole ring, a benzocarbazole ring, or a phenyl-substituted carbazole ring).

[0227] For details of each group in the compound represented by formula (3-H), the explanation for formula (1) above can be cited, and further explanation will be given in the section on preferred embodiments below.

[0228] Preferred embodiments of the above anthracene-based compounds are described below. The symbols in the following structures are defined as above. [ka]

[0229] In formula (3-H), X's are each independently a group represented by formula (3-X1), formula (3-X2), or formula (3-X3), and the group represented by formula (3-X1), formula (3-X2), or formula (3-X3) is bonded to the anthracene ring of formula (3-H) at *. Preferably, no two X's are simultaneously a group represented by formula (3-X3). More preferably, no two X's are simultaneously a group represented by formula (3-X2).

[0230] Furthermore, a multimer (preferably a dimer) may be formed using the structure represented by formula (3-H) as a unit structure. In this case, for example, the unit structures represented by formula (3-H) may be bonded to each other via X, where X may be a single bond, an arylene (such as phenylene, biphenylene, or naphthylene), or a heteroarylene (a divalent group such as a pyridine ring, a dibenzofuran ring, a dibenzothiophene ring, a carbazole ring, a benzocarbazole ring, or a phenyl-substituted carbazole ring).

[0231] The naphthylene moieties in formula (3-X1) and formula (3-X2) may be fused with one benzene ring. The fused structures are as follows: [ka]

[0232] Ar 1 and Ar 2 are each independently hydrogen, phenyl, biphenylyl, terphenylyl, quaterphenylyl, naphthyl, phenanthryl, fluorenyl, benzofluorenyl, chrysenyl, triphenylenyl, pyrenylyl, or a group represented by the formula (A) described below (including carbazolyl, benzocarbazolyl, and phenyl-substituted carbazolyl). 1 or Ar 2 is a group represented by formula (A) described below, the group represented by formula (A) is bonded to the naphthalene ring in formula (3-X1) or formula (3-X2) at the *.

[0233] Ar3 is phenyl, biphenylyl, terphenylyl, quaterphenylyl, naphthyl, phenanthryl, fluorenyl, benzofluorenyl, chrysenyl, triphenylenyl, pyrenylyl, or a group represented by formula (A) (including carbazolyl, benzocarbazolyl, and phenyl-substituted carbazolyl). 3 is a group represented by formula (A), the group represented by formula (A) is bonded to the single bond represented by a straight line in formula (3-X3) at the *. That is, the anthracene ring of formula (3-H) and the group represented by formula (A) are directly bonded.

[0234] Also, Ar 3 may have a substituent, and Ar 3 At least one hydrogen atom in the formula (A) may be further substituted with an alkyl group having 1 to 4 carbon atoms, a cycloalkyl group having 5 to 10 carbon atoms, phenyl, biphenylyl, terphenylyl, naphthyl, phenanthryl, fluorenyl, chrysenyl, triphenylenyl, pyrenylyl, or a group represented by formula (A) (including carbazolyl and phenyl-substituted carbazolyl). 3 When the substituent of is a group represented by formula (A), the group represented by formula (A) is Ar in formula (3-X3) at *. 3 and combine.

[0235] Ar 4 are each independently hydrogen, phenyl, biphenylyl, terphenylyl, naphthyl, or silyl substituted with alkyl having 1 to 4 carbon atoms (such as methyl, ethyl, and t-butyl) and / or cycloalkyl having 5 to 10 carbon atoms.

[0236] Examples of the alkyl having 1 to 4 carbon atoms that substitutes on the silyl include methyl, ethyl, propyl, i-propyl, butyl, sec-butyl, t-butyl, and cyclobutyl, and three hydrogen atoms on the silyl are each independently substituted with these alkyls.

[0237] Specific examples of "silyl substituted with alkyl having 1 to 4 carbon atoms" include trimethylsilyl, triethylsilyl, tripropylsilyl, tri-i-propylsilyl, tributylsilyl, tri-sec-butylsilyl, tri-t-butylsilyl, ethyldimethylsilyl, propyldimethylsilyl, i-propyldimethylsilyl, butyldimethylsilyl, sec-butyldimethylsilyl, t-butyldimethylsilyl, methyldiethylsilyl, propyldiethylsilyl, i-propyldiethylsilyl, butyldiethylsilyl, sec-butyldiethylsilyl, t-butyldiethylsilyl, methyldipropylsilyl, ethyldipropylsilyl, butyldipropylsilyl, sec-butyldipropylsilyl, t-butyldipropylsilyl, methyldi-i-propylsilyl, ethyldi-i-propylsilyl, butyldi-i-propylsilyl, sec-butyldi-i-propylsilyl, and t-butyldi-i-propylsilyl.

[0238] Examples of the cycloalkyl having 5 to 10 carbon atoms substituting the silyl 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 (norbornyl), bicyclo[2.2.2]octyl, adamantyl, decahydronaphthalenyl, and decahydroazulenyl, and three hydrogen atoms in the silyl are each independently substituted with one of these cycloalkyls.

[0239] Specific examples of "silyl substituted with cycloalkyl having 5 to 10 carbon atoms" include tricyclopentylsilyl and tricyclohexylsilyl.

[0240] Substituted silyls include dialkylcycloalkylsilyls, which are substituted with two alkyls and one cycloalkyl, and alkyldicycloalkylsilyls, which are substituted with one alkyl and two cycloalkyls. Specific examples of the alkyl and cycloalkyl substituents are the groups described above.

[0241] Furthermore, hydrogen atoms in the chemical structure of the anthracene-based compound represented by formula (3-H) may be substituted with a group represented by formula (A). When substituted with a group represented by formula (A), the group represented by formula (A) replaces at least one hydrogen atom in the compound represented by formula (3-H) at the *.

[0242] The group represented by formula (A) is one of the substituents that can be possessed by the anthracene compound represented by formula (3-H) and the anthracene compound represented by formula (3-H2) described below. [ka]

[0243] In formula (A), Y is —O—, —S—, or >NR 29 and R 21 ~R 28 are each independently hydrogen, optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted alkoxy, optionally substituted aryloxy, optionally substituted arylthio, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, alkyldicycloalkylsilyl, optionally substituted amino, halogen, hydroxy or cyano; R 21 ~R 28 adjacent groups may be bonded to each other to form a hydrocarbon ring, an aryl ring, or a heteroaryl ring; 29 is hydrogen or optionally substituted aryl. Y in formula (A) is preferably —O—.

[0244] R 21 ~R 28The "alkyl" in the "optionally substituted alkyl" may be either a straight chain or a branched chain, and examples thereof include a straight chain alkyl having 1 to 24 carbon atoms or a branched chain alkyl having 3 to 24 carbon atoms. An alkyl having 1 to 18 carbon atoms (branched chain alkyl having 3 to 18 carbon atoms) is preferred, an alkyl having 1 to 12 carbon atoms (branched chain alkyl having 3 to 12 carbon atoms) is more preferred, an alkyl having 1 to 6 carbon atoms (branched chain alkyl having 3 to 6 carbon atoms) is even more preferred, and an alkyl having 1 to 4 carbon atoms (branched chain alkyl having 3 to 4 carbon atoms) is particularly preferred.

[0245] 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.

[0246] R 21 ~R 28 Examples of the "cycloalkyl" in the "optionally substituted cycloalkyl" include cycloalkyl having 3 to 24 carbon atoms, cycloalkyl having 3 to 20 carbon atoms, cycloalkyl having 3 to 16 carbon atoms, cycloalkyl having 3 to 14 carbon atoms, cycloalkyl having 5 to 10 carbon atoms, cycloalkyl having 5 to 8 carbon atoms, cycloalkyl having 5 to 6 carbon atoms, and cycloalkyl having 5 carbon atoms.

[0247] Specific examples of "cycloalkyl" include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, and alkyl (especially methyl) substituted derivatives of these having 1 to 4 carbon atoms, as well as 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[2.2.1]heptyl (norbornyl), bicyclo[2.2.2]octyl, adamantyl, diamantyl, decahydronaphthalenyl, and decahydroazulenyl.

[0248] R 21 ~R 28 Examples of the "aryl" in the "optionally substituted aryl" include aryl having 6 to 30 carbon atoms, preferably aryl having 6 to 16 carbon atoms, more preferably aryl having 6 to 12 carbon atoms, and particularly preferably aryl having 6 to 10 carbon atoms.

[0249] Specific examples of "aryl" include phenyl, which is a monocyclic ring system; biphenylyl, which is a bicyclic ring system; naphthyl, which is a fused bicyclic ring system; terphenylyl (m-terphenylyl, o-terphenylyl, p-terphenylyl), which is a tricyclic ring system; acenaphthylenyl, fluorenyl, phenalenyl, phenanthrenyl, which are fused tricyclic ring systems; triphenylenyl, pyrenyl, naphthacenyl, which are fused tetracyclic ring systems; perylenyl, pentacenyl, etc.

[0250] R 21 ~R 28 Examples of the "heteroaryl" in the "optionally substituted heteroaryl" include heteroaryl having 2 to 30 carbon atoms, preferably heteroaryl having 2 to 25 carbon atoms, more preferably heteroaryl having 2 to 20 carbon atoms, still more preferably heteroaryl having 2 to 15 carbon atoms, and particularly preferably heteroaryl having 2 to 10 carbon atoms. Examples of heteroaryl include heterocycles containing, as ring-constituting atoms other than carbon, 1 to 5 heteroatoms selected from oxygen, sulfur, and nitrogen.

[0251] Specific examples of "heteroaryl" include pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, oxadiazolyl, thiadiazolyl, triazolyl, tetrazolyl, pyrazolyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, indolyl, isoindolyl, 1H-indazolyl, benzimidazolyl, benzoxazolyl, benzothiazolyl, 1H-benzotriazolyl, quinolyl, isoquinolyl, cyclohex ... Examples thereof include benzoyl, quinazolyl, quinoxalinyl, phthalazinyl, naphthyridinyl, purinyl, pteridinyl, carbazolyl, acridinyl, phenoxathiinyl, phenoxazinyl, phenothiazinyl, phenazinyl, indolizinyl, furyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, thienyl, benzo[b]thienyl, dibenzothienyl, furazanyl, oxadiazolyl, thianthrenyl, naphthobenzofuranyl, and naphthobenzothienyl.

[0252] R 21 ~R 28 Examples of the "alkoxy" in "optionally substituted alkoxy" include straight-chain alkoxy having 1 to 24 carbon atoms or branched-chain alkoxy having 3 to 24 carbon atoms. Alkoxy having 1 to 18 carbon atoms (branched-chain alkoxy having 3 to 18 carbon atoms) is preferred, alkoxy having 1 to 12 carbon atoms (branched-chain alkoxy having 3 to 12 carbon atoms) is more preferred, alkoxy having 1 to 6 carbon atoms (branched-chain alkoxy having 3 to 6 carbon atoms) is even more preferred, and alkoxy having 1 to 4 carbon atoms (branched-chain alkoxy having 3 to 4 carbon atoms) is particularly preferred.

[0253] Specific examples of "alkoxy" include methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, s-butoxy, t-butoxy, pentyloxy, hexyloxy, heptyloxy, octyloxy, and the like.

[0254] R 21 ~R 28The "aryloxy" in the "optionally substituted aryloxy" is a group in which the hydrogen of the -OH group is substituted with an aryl, and this aryl is one of the above-mentioned R 21 ~R 28 The group described as "aryl" in the above formula can be used.

[0255] R 21 ~R 28 The "arylthio" in the "optionally substituted arylthio" is a group in which the hydrogen of the -SH group is substituted with an aryl, and this aryl is one of the above-mentioned R 21 ~R 28 The group described as "aryl" in the above formula can be used.

[0256] R 21 ~R 28 The "trialkylsilyl" in the above formula is a group in which three hydrogen atoms in the silyl group are each independently substituted with an alkyl, and this alkyl is the same as the above-mentioned R 21 ~R 28 Examples of the alkyl group include those described as "alkyl" in the above. Preferred alkyl groups for substitution are alkyl groups having 1 to 4 carbon atoms, and specific examples thereof include methyl, ethyl, propyl, i-propyl, butyl, sec-butyl, t-butyl, and cyclobutyl.

[0257] Specific examples of the "trialkylsilyl" include trimethylsilyl, triethylsilyl, tripropylsilyl, tri-i-propylsilyl, tributylsilyl, tri-sec-butylsilyl, tri-t-butylsilyl, ethyldimethylsilyl, propyldimethylsilyl, i-propyldimethylsilyl, butyldimethylsilyl, sec-butyldimethylsilyl, t-butyldimethylsilyl, methyldiethylsilyl, propyldiethylsilyl, i-propyldiethylsilyl, butyldiethylsilyl, sec-butyldiethylsilyl, t-butyldiethylsilyl, methyldipropylsilyl, ethyldipropylsilyl, butyldipropylsilyl, sec-butyldipropylsilyl, t-butyldipropylsilyl, methyldi-i-propylsilyl, ethyldi-i-propylsilyl, butyldi-i-propylsilyl, sec-butyldi-i-propylsilyl, and t-butyldi-i-propylsilyl.

[0258] R 21 ~R 28 The "tricycloalkylsilyl" in the above formula is a group in which three hydrogen atoms in the silyl group are each independently substituted with a cycloalkyl, and this cycloalkyl is one of the above-mentioned R 21 ~R 28 Examples of the cycloalkyl groups described above as "cycloalkyl" include those described above. Preferred cycloalkyl groups for substitution are cycloalkyl groups having 5 to 10 carbon atoms, and specific examples include cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, bicyclo[1.1.1]pentyl, bicyclo[2.1.0]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.

[0259] Specific examples of "tricycloalkylsilyl" include tricyclopentylsilyl, tricyclohexylsilyl, and the like.

[0260] 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.

[0261] R 21 ~R 28 The "substituted amino" in the "optionally substituted amino" includes, for example, amino in which two hydrogen atoms are substituted with aryl or heteroaryl. An amino in which two hydrogen atoms are substituted with aryl atoms is a diaryl-substituted amino, an amino in which two hydrogen atoms are substituted with heteroaryl atoms is a diheteroaryl-substituted amino, and an amino in which two hydrogen atoms are substituted with an aryl and a heteroaryl atom is an arylheteroaryl-substituted amino. The aryl and heteroaryl atoms are substituted with the R 21 ~R 28 The groups described as "aryl" and "heteroaryl" in the above can be cited.

[0262] Specific examples of the "substituted amino" include diphenylamino, dinaphthylamino, phenylnaphthylamino, dipyridylamino, phenylpyridylamino, naphthylpyridylamino, and the like.

[0263] R 21 ~R 28 The "halogen" in the above formula includes fluorine, chlorine, bromine, and iodine.

[0264] R 21 ~R 28 Some of the groups described as may be substituted as described above, and in this case, the substituents include alkyl, cycloalkyl, aryl, or heteroaryl. The alkyl, cycloalkyl, aryl, or heteroaryl may be any of the groups described above as R 21 ~R 28 Reference can be made to groups described as "alkyl", "cycloalkyl", "aryl" or "heteroaryl" in the above.

[0265] Y as 'NR' 29 "R" 29 is hydrogen or an optionally substituted aryl, and the aryl is the same as R 21 ~R 28 The groups described as "aryl" in the above formula can be cited, and the substituents thereof include R 21 ~R 28 The groups described as substituents for the following can be cited.

[0266] R 21 ~R 28 Among these, adjacent groups may be bonded to each other to form a hydrocarbon ring, an aryl ring, or a heteroaryl ring. The group represented by formula (A-1) below does not form a ring, and examples of the group represented by formulas (A-2) to (A-14) below include groups represented by formulas (A-1) to (A-14). At least one hydrogen atom in the group represented by any of formulas (A-1) to (A-14) may be substituted with alkyl, cycloalkyl, aryl, heteroaryl, alkoxy, aryloxy, arylthio, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, alkyldicycloalkylsilyl, diaryl-substituted amino, diheteroaryl-substituted amino, arylheteroaryl-substituted amino, halogen, hydroxy, or cyano.

[0267] [ka]

[0268] Examples of rings formed by bonding adjacent groups to each other include hydrocarbon rings such as cyclohexane rings, and examples of aryl and heteroaryl rings include the above-mentioned R 21 ~R 28 These rings are formed so as to be fused with one or two benzene rings in formula (A-1).

[0269] The group represented by formula (A) is a group obtained by removing one hydrogen atom from any position of formula (A), and * indicates the position. That is, the group represented by formula (A) may have any position as a bonding position. For example, any carbon atom on the two benzene rings in the structure of formula (A), R 21 ~R 28 An atom on any ring formed by bonding adjacent groups to each other, or ">NR 29 "R" 29 Any position in the 29 " in N(R 29 The same applies to the groups represented by any of formulae (A-1) to (A-14).

[0270] Examples of the group represented by formula (A) include groups represented by any of formulas (A-1) to (A-14), preferably groups represented by any of formulas (A-1) to (A-5) and formulas (A-12) to (A-14), more preferably groups represented by any of formulas (A-1) to (A-4), still more preferably groups represented by any of formulas (A-1), (A-3) and (A-4), and particularly preferably groups represented by formula (A-1).

[0271] Examples of the group represented by formula (A) include the following groups: In the formula, Y and * are defined as above. [ka]

[0272] [ka]

[0273] In the compound represented by formula (3-H), the group represented by formula (A) is a naphthalene ring in formula (3-X1) or formula (3-X2), a single bond in formula (3-X3), and / or Ar in formula (3-X3). 3 The form in which it is bound to is preferred.

[0274] In addition, all or part of the hydrogen atoms in the chemical structure of the anthracene-based compound represented by formula (3-H) may be deuterium atoms.

[0275] The anthracene-based compound as the host may be, for example, a compound represented by the following formula (3-H2). [ka]

[0276] In formula (3-H2), Ar c is an optionally substituted aryl or an optionally substituted heteroaryl, and R c is hydrogen, alkyl, or cycloalkyl, and Ar 11 , Ar 12 , Ar 13 , Ar 14 , Ar 15 , Ar 16 , Ar 17 , and Ar 18 are each independently hydrogen, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted diarylamino, optionally substituted diheteroarylamino, optionally substituted arylheteroarylamino, optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted alkenyl, optionally substituted alkoxy, optionally substituted aryloxy, optionally substituted arylthio, or optionally substituted silyl, and at least one hydrogen in the compound represented by formula (3-H-2) may be substituted with halogen, cyano, or deuterium.

[0277] In formula (3-H2), the definition of "optionally substituted aryl," "optionally substituted heteroaryl," "optionally substituted diarylamino," "optionally substituted diheteroarylamino," "optionally substituted arylheteroarylamino," "optionally substituted alkyl," "optionally substituted cycloalkyl," "optionally substituted alkenyl," "optionally substituted alkoxy," "optionally substituted aryloxy," "optionally substituted arylthio," or "optionally substituted silyl" is the same as that in formula (3-H) above, and the explanation in formula (1) can be cited.

[0278] The "optionally substituted aryl" is also preferably a group represented by any one of the following formulae (3-H2-X1) to (3-H2-X7).

[0279] [ka]

[0280] In the formulae (3-H2-X1) to (3-H2-X7), * indicates the bonding position. In the formulas (3-H2-X1) to (3-H2-X3), Ar 21 , Ar 22 , and Ar 23 are each independently hydrogen, phenyl, biphenylyl, terphenylyl, quaterphenylyl, naphthyl, phenanthryl, fluorenyl, benzofluorenyl, chrysenyl, triphenylenyl, pyrenyl, anthracenyl, or a group represented by formula (A). In the description of formula (3-H2), the group represented by formula (A) is the same as that described in the anthracene-based compound represented by formula (3-H).

[0281] In the formulas (3-H2-X4) to (3-H2-X7), Ar 24 , Ar 25 , Ar 26 , Ar 27 and Ar 28are each independently hydrogen, phenyl, biphenylyl, terphenylyl, naphthyl, phenanthryl, fluorenyl, chrysenyl, triphenylenyl, pyrenyl, or a group represented by formula (A) described below. In addition, any one or more hydrogen atoms in each of the groups represented by formulae (3-H2-X1) to (3-H2-X7) may be substituted with alkyl having 1 to 6 carbon atoms (preferably methyl or t-butyl).

[0282] Furthermore, preferred examples of the "optionally substituted aryl" include terphenylyl (particularly m-terphenyl-5'-yl) which may be substituted with one or more substituents selected from the group consisting of phenyl, biphenylyl, terphenylyl, naphthyl, phenanthryl, fluorenyl, chrysenyl, triphenylenyl, pyrenyl, and groups represented by formula (A).

[0283] The "optionally substituted heteroaryl" also includes a group represented by formula (A). Other specific examples of "optionally substituted aryl" and "optionally substituted heteroaryl" include dibenzofuryl, naphthobenzofuryl, phenyl-substituted dibenzofuryl, and the like.

[0284] At least one hydrogen atom in the compound represented by formula (3-H) may be substituted with a halogen atom, cyano atom, or deuterium atom. In this case, "halogen" includes fluorine, chlorine, bromine, and iodine. In particular, a compound in which all hydrogen atoms in the compound represented by formula (3-H) are substituted with deuterium atoms is preferred.

[0285] In formula (3-H2), R c is hydrogen, alkyl, or cycloalkyl, preferably hydrogen, methyl, or t-butyl, and more preferably hydrogen. In formula (3-H2), Ar 11 ~Ar 18It is preferable that at least two of the substituents be optionally substituted aryl or optionally substituted heteroaryl. That is, the anthracene compound represented by formula (3-H2) preferably has a structure in which at least three substituents selected from the group consisting of optionally substituted aryl and optionally substituted heteroaryl are bonded to the anthracene ring.

[0286] The anthracene compound represented by formula (3-H2) is Ar 11 ~Ar 18 It is more preferred that two of the groups are optionally substituted aryl or optionally substituted heteroaryl, and the other six are hydrogen, optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted alkenyl, or optionally substituted alkoxy. That is, it is more preferred that the anthracene compound represented by formula (3-H2) has a structure in which three substituents selected from the group consisting of optionally substituted aryl and optionally substituted heteroaryl are bonded to the anthracene ring.

[0287] The anthracene compound represented by formula (3-H) is Ar 11 ~Ar 18 It is more preferred that any two of are optionally substituted aryl or optionally substituted heteroaryl, and the other six are hydrogen, methyl, or t-butyl.

[0288] Furthermore, in formula (3-H2), R c is hydrogen and Ar 11 ~Ar 18 It is preferred that any six of these are hydrogen.

[0289] The anthracene compound represented by formula (3-H2) is preferably an anthracene compound represented by the following formula (3-HA), (3-HB), (3-H2-C), (3-H2-D), or (3-H2-E). [ka]

[0290] In formula (3-H2-A), (3-H2-B), (3-H2-C), (3-H2-D) or (3-H2-E), Ar c ', Ar 11 ', Ar 12 ', Ar 13 ', Ar 14 ', Ar 15 ', Ar 17 ', and Ar 18 Each of the ' is independently phenyl, biphenylyl, terphenylyl, quaterphenylyl, naphthyl, phenanthryl, fluorenyl, benzofluorenyl, chrysenyl, triphenylenyl, pyrenyl, or a group represented by formula (A), and at least one hydrogen atom in these groups may be substituted with phenyl, biphenylyl, terphenylyl, quaterphenylyl, naphthyl, phenanthryl, fluorenyl, benzofluorenyl, chrysenyl, triphenylenyl, pyrenyl, or a group represented by formula (A). When both hydrogen atoms of the methylenes in the fluorenyl and benzofluorenyl are substituted with phenyl, these phenyls may be bonded to each other via a single bond. Ar c ', Ar 11 ', Ar 12 ', Ar 13 ', Ar 14 ', Ar 15 ', Ar 17 ', and Ar 18 The carbon atoms of the anthracene ring to which ' is not attached may have methyl or t-butyl attached instead of hydrogen.

[0291] Ar c ', Ar 11 ', Ar 12 ', Ar 13 ', Ar 14 ', Ar 15 ', Ar 17 ', and Ar 18When each of "3-H2-X1" and "3-H2-X7" is a substituted or unsubstituted phenyl or a substituted or unsubstituted naphthyl, it is preferably a group represented by any one of the above formulae (3-H2-X1) to (3-H2-X7).

[0292] Ar c ', Ar 11 ', Ar 12 ', Ar 13 ', Ar 14 ', Ar 15 ', Ar 17 ', and Ar 18 It is more preferable that each of the ' is independently phenyl, biphenylyl (particularly biphenyl-2-yl or biphenyl-4-yl), terphenylyl (particularly m-terphenyl-5'-yl), naphthyl, phenanthryl, fluorenyl, or a group represented by any one of the above formulas (A-1) to (A-4), and in this case, at least one hydrogen atom in these groups may be substituted by phenyl, biphenylyl, naphthyl, phenanthryl, fluorenyl, or a group represented by any one of the above formulas (A-1) to (A-4).

[0293] In addition, at least one hydrogen atom in the compound represented by formula (3-H2-A), (3-H2-B), (3-H2-C), (3-H2-D), or (3-H2-E) may be substituted with halogen, cyano, or deuterium.

[0294] Particularly preferred anthracene compounds represented by formula (3-H2) include anthracene compounds represented by formula (3-H2-Aa) below. [ka]

[0295] In formula (3-H2-Aa), Ar c ', Ar 14 ', and Ar 15Each of the ' is independently phenyl, biphenylyl, terphenylyl, naphthyl, phenanthryl, fluorenyl, benzofluorenyl, chrysenyl, triphenylenyl, pyrenyl, or a group represented by any one of the above formulas (A-1) to (A-11), and at least one hydrogen atom in these groups may be substituted with phenyl, biphenylyl, terphenylyl, naphthyl, phenanthryl, fluorenyl, benzofluorenyl, chrysenyl, triphenylenyl, pyrenyl, or a group represented by any one of the formulas (A-1) to (A-11). When both hydrogen atoms of the methylenes in the fluorenyl and benzofluorenyl are substituted with phenyl, these phenyls may be bonded to each other via a single bond. In addition, Ar c ', Ar 14 ', and Ar 15 A carbon atom on the anthracene ring to which "'" is not bonded may be substituted with methyl or t-butyl in place of hydrogen. At least one hydrogen in the compound represented by formula (3-H2-Aa) may be substituted with halogen or cyano, and at least one hydrogen in the compound represented by formula (3-H2-Aa) is substituted with deuterium.

[0296] In formula (3-H2-Aa), Ar c ', Ar 14 ', and Ar 15 It is preferable that each of the ' is independently phenyl, biphenylyl, terphenylyl, naphthyl, phenanthryl, fluorenyl, or a group represented by any one of the above formulas (A-1) to (A-4), and at least one hydrogen in these groups may be substituted by phenyl, naphthyl, phenanthryl, fluorenyl, or a group represented by any one of the above formulas (A-1) to (A-4).

[0297] In the compound represented by formula (3-H2-Aa), at least the carbon atom at the 10-position of the anthracene ring (Ar cIt is preferable that the hydrogen bonded to the carbon atom (the carbon atom to which Ar′ is bonded is the 9th position) is replaced with deuterium. That is, the compound represented by formula (3-H2-Aa) is preferably a compound represented by the following formula (3-H2-Ab). In formula (3-H2-Ab), D is deuterium, and Ar c ', Ar 14 ', and Ar 15 ' is the same as defined in formula (3-H2-Aa). D in formula (3-H2-Ab) indicates that at least this position is deuterium, and any one or more other hydrogens in formula (3-H2-Aa) may also be deuterium, and it is also preferred that all hydrogens in formula (3-H2-Aa) are deuterium.

[0298] [ka]

[0299] Specific examples of anthracene compounds include the following compounds: In the structural formulas below, "Me" represents methyl, "D" represents deuterium, and "tBu" represents t-butyl.

[0300] [ka]

[0301] [ka]

[0302] [ka]

[0303] [ka]

[0304] [ka]

[0305] [ka]

[0306] [ka]

[0307] [ka]

[0308] Other specific examples of the anthracene compounds include compounds represented by the following formulae (3-131-Y) to (3-179-Y), compounds represented by the following formulae (3-180-Y) to (3-182-Y), compounds represented by the following formulae (3-183-N), compounds represented by the following formulae (3-184-Y) to (3-254-Y), compounds represented by the following formulae (3-254-Y) to (3-269-Y), and compounds represented by the following formulae (3-500) to (3-557). In the compounds represented by the following formulae (3-131-Y) to (3-179-Y), the compounds represented by the following formulae (3-180-Y) to (3-182-Y), the following formula (3-183-N), the following formulae (3-184-Y) to (3-254-Y), the formulae (3-254-Y) to (3-269-Y), and the following formulae (3-500) to (3-557), hydrogen atoms may be partially or completely substituted with deuterium. In the formulae, Y represents -O-, -S-, >NR 29 (R 29 is defined as above) or >C(-R 30 )2(R 30 may be either an optionally linked aryl or alkyl, and R 29 is, for example, phenyl, R 30 For example, when Y is O, the formula (3-131-Y) becomes the formula (3-131-O), and when Y is -S- or >NR 29 In the case of (3-131-S) or (3-131-N), respectively.

[0309]

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[0310]

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[0311]

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[0312]

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[0313]

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[0314]

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[0315]

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[0316]

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[0317]

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[0318]

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[0319]

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[0320]

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[0321]

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[0322]

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[0323]

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[0324]

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[0325]

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[0326]

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[0327]

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[0328] Among these compounds, the following are particularly well known: (3-131-Y) to (3-134-Y), (3-138-Y), (3-140-Y) to (3-143-Y), (3-150-Y), (3-153-Y) to (3-156-Y), (3-166-Y), (3-168-Y), (3-173-Y), (3-177-Y), (3-180-Y) to (3-183-N), (3-185-Y), and (3-19 Compounds represented by formula (3-0-Y), formula (3-223-Y), formula (3-241-Y), formula (3-250-Y), formula (3-252-Y) to formula (3-254-Y), formula (3-501), formula (3-507), formula (3-508), formula (3-509), formula (3-513), formula (3-514), formula (3-519), formula (3-521), formula (3-538) to formula (3-547), or formula (3-600) to (3-620) are preferred. Y is preferably -O-.

[0329] The anthracene compound represented by formula (3-H) is a compound having a reactive group at a desired position of the anthracene skeleton, and X, Ar 4 The compound can be produced by applying Suzuki coupling, Negishi coupling, or other known coupling reactions using a compound having a reactive group in a partial structure such as the structure of formula (A) as a starting material. Examples of reactive groups in these reactive compounds include halogens and boronic acids. For specific production methods, reference can be made to the synthesis methods described in paragraphs

[0089] to

[0175] of International Publication No. 2014 / 141725.

[0330] <Fluorene-based compounds> The compound represented by formula (4-H) basically functions as a host. [ka]

[0331] In formula (4-H), R 1 From R 10are each independently a hydrogen atom, an aryl atom, a heteroaryl atom (the heteroaryl atom may be bonded to the fluorene skeleton in Formula (4-H) via a linking group), a diarylamino atom, a diheteroarylamino atom, an arylheteroarylamino atom, an alkyl atom, a cycloalkyl atom, an alkenyl atom, an alkoxy atom, or an aryloxy atom, wherein at least one hydrogen atom in each of these groups may be substituted with an aryl atom, a heteroaryl atom, an alkyl atom, or a cycloalkyl atom; Also, R 1 and R 2 , R 2 and R 3 , R 3 and R 4 , R 5 and R 6 , R 6 and R 7 , R 7 and R 8 or R 9 and R 10 may each independently bond to form a fused ring or a spiro ring, and at least one hydrogen atom in the formed ring may be substituted with an aryl, a heteroaryl (the heteroaryl may be bonded to the formed ring via a linking group), a diarylamino, a diheteroarylamino, an arylheteroarylamino, an alkyl, a cycloalkyl, an alkenyl, an alkoxy, or an aryloxy, and at least one hydrogen atom in these may be substituted with an aryl, a heteroaryl, an alkyl, or a cycloalkyl; At least one hydrogen atom in the compound represented by formula (4-H) may be substituted with halogen, cyano, or deuterium.

[0332] For details of each group in the definition of formula (4-H), the explanation for the polycyclic aromatic compound of formula (1) can be cited.

[0333] R 1 From R 10Examples of the alkenyl in the formula include alkenyl having 2 to 30 carbon atoms, preferably alkenyl having 2 to 20 carbon atoms, more preferably alkenyl having 2 to 10 carbon atoms, still more preferably alkenyl having 2 to 6 carbon atoms, and particularly preferably alkenyl having 2 to 4 carbon atoms. Preferred alkenyls include vinyl, 1-propenyl, 2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, and 5-hexenyl.

[0334] Specific examples of heteroaryl include monovalent groups represented by removing any one hydrogen atom from a compound of the following formula (4-Ar1), formula (4-Ar2), formula (4-Ar3), formula (4-Ar4), or formula (4-Ar5).

[0335] [ka]

[0336] In formulas (4-Ar1) to (4-Ar5), Y 1 are each independently O, S, or NR, and R is phenyl, biphenylyl, naphthyl, anthracenyl, or hydrogen; At least one hydrogen atom in the structures of formulae (4-Ar1) to (4-Ar5) may be substituted with phenyl, biphenylyl, naphthyl, anthracenyl, phenanthrenyl, methyl, ethyl, propyl, or butyl.

[0337] These heteroaryls may be bonded to the fluorene skeleton in formula (4-H) via a linking group. That is, the fluorene skeleton and the heteroaryl in formula (4-H) may not only be bonded directly, but also may be bonded therebetween via a linking group. Examples of such linking groups include phenylene, biphenylene, naphthylene, anthracenylene, methylene, ethylene, -OCH2CH2-, -CH2CHO-, or -OCH2CHO-.

[0338] Furthermore, R in formula (4-H) 1 and R 2 , R 2 and R 3 , R 3 and R 4 , R 5 and R 6 , R 6 and R 7 or R 7 and R 8 are each independently bonded to form a fused ring, R 9 and R 10 may be bonded to form a spiro ring. 1 From R 8 The fused ring formed by is a ring fused to the benzene ring in formula (4-H), and is an aliphatic ring or an aromatic ring. An aromatic ring is preferable, and examples of the structure containing the benzene ring in formula (4-H) include a naphthalene ring and a phenanthrene ring. 9 and R 10 The spiro ring formed by the formula (4-H) is a ring spiro-bonded to the five-membered ring in formula (4-H), and is an aliphatic ring or an aromatic ring. An aromatic ring, such as a fluorene ring, is preferred.

[0339] The compound represented by formula (4-H) is preferably a compound represented by the following formula (4-H-1), formula (4-H-2), or formula (4-H-3), and in formula (4-H), R 1 and R 2 In formula (4-H), R 3 and R 4 In formula (4-H), R 1 From R 8 is a compound in which none of the above is bound.

[0340] [ka]

[0341] R in formula (4-H-1), formula (4-H-2) and formula (4-H-3) 1From R 10 The definition of R in formula (4-H) corresponds to 1 From R 10 and R in formula (4-H-1) and formula (4-H-2) 11 From R 14 The definition of R in formula (4-H) 1 From R 10 is the same as

[0342] The compound represented by formula (4-H) is more preferably a compound represented by the following formula (4-H-1A), formula (4-H-2A), or formula (4-H-3A), and in formula (4-H-1), formula (4-H-1), or formula (4-H-3), R 9 and R 10 is a compound in which a spiro-fluorene ring is formed by bonding.

[0343] [ka]

[0344] R in formula (4-1A), formula (4-2A) and formula (4-3A) 2 From R 7 The definition of is the corresponding R in formula (4-1), formula (4-2) and formula (4-3). 2 From R 7 and R in formula (4-1A) and formula (4-2A) 11 From R 14 The definition of R in formula (4-1) and formula (4-2) 11 From R 14 is the same as

[0345] In addition, all or part of the hydrogen atoms in the compound represented by formula (4-H) may be substituted with halogen, cyano, or deuterium.

[0346] More specific examples of fluorene-based compounds as hosts include compounds represented by the following structural formulas: where "Me" represents methyl. [ka]

[0347] <Dibenzochrysene compounds> The dibenzochrysene compound as the host is, for example, a compound represented by the following formula (5-H). [ka]

[0348] In formula (5-H), R 1 From R 16 are each independently a hydrogen atom, an aryl group, a heteroaryl group (the heteroaryl group may be bonded to the dibenzochrysene skeleton in Formula (5-H) via a linking group), a diarylamino group, a diheteroarylamino group, an arylheteroarylamino group, an alkyl group, a cycloalkyl group, an alkenyl group, an alkoxy group, or an aryloxy group, wherein at least one hydrogen atom in each of these groups may be substituted with an aryl group, a heteroaryl group, an alkyl group, or a cycloalkyl group; Also, R 1 From R 16 adjacent groups among these may be bonded to each other to form a fused ring, and at least one hydrogen atom in the formed ring may be substituted with an aryl, a heteroaryl (the heteroaryl may be bonded to the formed ring via a linking group), a diarylamino, a diheteroarylamino, an arylheteroarylamino, an alkyl, a cycloalkyl, an alkenyl, an alkoxy, or an aryloxy, and at least one hydrogen atom in these may be substituted with an aryl, a heteroaryl, an alkyl, or a cycloalkyl; At least one hydrogen atom in the compound represented by formula (5-H) may be substituted with halogen, cyano, or deuterium.

[0349] For details of each group in the definition of formula (5-H), the explanation for the polycyclic aromatic compound of formula (1) can be cited.

[0350] Examples of alkenyl in the definition of formula (5-H) include alkenyl having 2 to 30 carbon atoms, preferably alkenyl having 2 to 20 carbon atoms, more preferably alkenyl having 2 to 10 carbon atoms, still more preferably alkenyl having 2 to 6 carbon atoms, and particularly preferably alkenyl having 2 to 4 carbon atoms. Preferred alkenyls include vinyl, 1-propenyl, 2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, and 5-hexenyl.

[0351] Specific examples of heteroaryl include monovalent groups represented by removing any one hydrogen atom from a compound of the following formula (5-Ar1), formula (5-Ar2), formula (5-Ar3), formula (5-Ar4), or formula (5-Ar5).

[0352] [ka]

[0353] In formula (5-Ar1) to formula (5-Ar5), Y 1 are each independently O, S, or NR, and R is phenyl, biphenylyl, naphthyl, anthracenyl, or hydrogen; At least one hydrogen atom in the structures of formulae (5-Ar1) to (5-Ar5) may be substituted with phenyl, biphenylyl, naphthyl, anthracenyl, phenanthrenyl, methyl, ethyl, propyl, or butyl.

[0354] These heteroaryls may be bonded to the dibenzochrysene skeleton in formula (5-H) via a linking group. That is, the dibenzochrysene skeleton and the heteroaryl in formula (5-H) may be bonded not only directly but also via a linking group. Examples of the linking group include phenylene, biphenylene, naphthylene, anthracenylene, methylene, ethylene, -OCH2CH2-, -CH2CHO-, and -OCH2CHO-.

[0355] The compound represented by formula (5-H) is preferably R 1 , R 4 , R 5 , R 8 , R 9 , R 12 , R 13 and R 16 is hydrogen. In this case, R in formula (5-H) 2 , R 3 , R 6 , R 7 , R 10 , R 11 , R 14 and R 15 are preferably each independently hydrogen, phenyl, biphenylyl, naphthyl, anthracenyl, phenanthrenyl, a monovalent group having a structure of formula (5-Ar1), formula (5-Ar2), formula (5-Ar3), formula (5-Ar4), or formula (5-Ar5) (the monovalent group having such a structure may be bonded to the dibenzochrysene skeleton in formula (5-H) via phenylene, biphenylene, naphthylene, anthracenylene, methylene, ethylene, -OCHCH-, -CHCHO-, or -OCHCHO-), methyl, ethyl, propyl, or butyl.

[0356] The compound represented by formula (5-H) is more preferably R 1 , R 2 , R 4 , R 5 , R 7 , R 8 , R 9 , R 10 , R 12 , R 13 , R 15 and R 16 is hydrogen. In this case, R in formula (5-H) 3 , R 6 , R 11 and R 14at least one (preferably one or two, more preferably one) of the formulas (5-Ar1), (5-Ar2), (5-Ar3), (5-Ar4) or (5-Ar5) is a monovalent group having a structure represented by formula (5-Ar1), (5-Ar2), (5-Ar3), (5-Ar4) or (5-Ar5) via a single bond, phenylene, biphenylene, naphthylene, anthracenylene, methylene, ethylene, -OCHCH-, -CHCHO- or -OCHCHO-; The positions other than the at least one (i.e., positions other than the position substituted by the monovalent group having the structure) are hydrogen, phenyl, biphenylyl, naphthyl, anthracenyl, methyl, ethyl, propyl, or butyl, and at least one hydrogen in these may be substituted with phenyl, biphenylyl, naphthyl, anthracenyl, methyl, ethyl, propyl, or butyl.

[0357] Furthermore, R in formula (5-H) 2 , R 3 , R 6 , R 7 , R 10 , R 11 , R 14 and R 15 When a monovalent group having a structure represented by formula (5-Ar1) to formula (5-Ar5) is selected as the group, at least one hydrogen atom in the structure is selected from the group represented by R 1 From R 16 may be bonded to any one of the following to form a single bond.

[0358] More specific examples of dibenzochrysene compounds as hosts include compounds represented by the following structural formula: where "tBu" represents t-butyl. [ka]

[0359] [ka]

[0360] The above-mentioned light-emitting layer materials (host materials and dopant materials) can also be used as light-emitting layer materials in the form of polymer compounds obtained by polymerizing a reactive compound substituted with a reactive substituent as a monomer, or a crosslinked polymer thereof, or a pendant-type polymer compound obtained by reacting a main-chain polymer with the reactive compound, or a crosslinked pendant-type polymer thereof. Regarding the reactive substituent in this case, the same explanation as for the polycyclic aromatic compound represented by formula (1) can be cited. The uses of such polymer compounds and crosslinked polymers will be described in detail below.

[0361] <Example of polymer host material> [ka]

[0362] In formula (SPH-1), Each MU is independently a divalent aromatic group, each EC is independently a monovalent aromatic group, two hydrogen atoms in MU are replaced by EC or MU, and k is an integer of 2 to 50,000.

[0363] More specifically, Each MU is independently arylene, heteroarylene, diarylylenearylamino, diarylylenearylboryl, oxaborine-diyl, or azaborine-diyl; each EC is independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, or aryloxy; At least one hydrogen atom in MU and EC may be further substituted with aryl, heteroaryl, diarylamino, alkyl, and cycloalkyl; k is an integer from 2 to 50,000. k is preferably an integer of 20 to 50,000, and more preferably an integer of 100 to 50,000.

[0364] At least one hydrogen atom in MU and EC in formula (SPH-1) may be substituted with alkyl having 1 to 24 carbon atoms, cycloalkyl having 3 to 24 carbon atoms, halogen, or deuterium; further, any -CH2- in the alkyl may be substituted with -O- or -Si(CH3)2-; any -CH2- in the alkyl except for the -CH2- directly bonded to EC in formula (SPH-1) may be substituted with arylene having 6 to 24 carbon atoms; and any hydrogen atom in the alkyl may be substituted with fluorine.

[0365] Examples of MU include divalent derivatives of the following structures (e.g., a divalent group represented by removing any two hydrogen atoms from any of the compounds of the following structures, a divalent group composed of a combination of two or more divalent groups represented by removing any two hydrogen atoms from any of the compounds of the following structures, and a divalent group in which at least one hydrogen atom in such a group has been substituted with an alkyl or the like).

[0366] [ka]

[0367] More specifically, the divalent group may be any of the following structures: In these, MU is bonded to another MU or EC at *.

[0368] [ka]

[0369] [ka]

[0370] [ka]

[0371] [ka]

[0372] [ka]

[0373] [ka]

[0374] [ka]

[0375] [ka]

[0376] [ka]

[0377] Examples of EC include monovalent groups represented by any of the following structures: In these, EC is bonded to MU at *.

[0378] [ka]

[0379] [ka]

[0380] From the viewpoints of solubility and film-forming properties, the compound represented by formula (SPH-1) preferably has 10 to 100% of the total number of MUs (k) in the molecule having alkyls of 1 to 24 carbon atoms, more preferably 30 to 100% of the total number of MUs (k) in the molecule having alkyls of 1 to 18 carbon atoms (branched-chain alkyls of 3 to 18 carbon atoms), and even more preferably 50 to 100% of the total number of MUs (k) in the molecule having alkyls of 1 to 12 carbon atoms (branched-chain alkyls of 3 to 12 carbon atoms). On the other hand, from the viewpoints of in-plane alignment and charge transport, preferably has 10 to 100% of the total number of MUs (k) in the molecule having alkyls of 7 to 24 carbon atoms, and more preferably 30 to 100% of the total number of MUs (k) in the molecule having alkyls of 7 to 24 carbon atoms (branched-chain alkyls of 7 to 24 carbon atoms).

[0381] Light-emitting layer containing an assisting dopant and an emitting dopant The light-emitting layer in the organic electroluminescent device may contain a host compound as a first component, an assisting dopant (compound) as a second component, and an emitting dopant (compound) as a third component. The polycyclic aromatic compound of the present invention is also preferably used as an emitting dopant. As the assisting dopant (compound), a thermally activated delayed fluorescent material can be used.

[0382] In the following description, an organic electroluminescent device that uses a thermally activated delayed fluorescent substance as an assisting dopant may be referred to as a "TAF device" (TADF Assisting Fluorescence device). The "host compound" in a TAF element refers to a compound whose excited singlet energy level, determined from the shoulder on the short-wavelength side of the peak of the fluorescence spectrum, is higher than that of the thermally activated delayed fluorescent substance as the second component and the emitting dopant as the third component. The term "thermally activated delayed fluorescent substance" refers to a compound that can absorb thermal energy to undergo reverse intersystem crossing from an excited triplet state to an excited singlet state, and then radiatively deactivate from the excited singlet state to emit delayed fluorescence. However, the term "thermally activated delayed fluorescent substance" also includes compounds that undergo a higher-order triplet state during the excitation process from the excited triplet state to the excited singlet state. Examples include a paper by Monkman et al. of Durham University (NATURE COMMUNICATIONS,7:13680,DOI: 10.1038 / ncomms13680), a paper by Hosokai et al. of the National Institute of Advanced Industrial Science and Technology (Hosokai et al., Sci. Adv. 2017;3: e1603282), a paper by Sato et al. of Kyoto University (Scientific Reports,7:4820,DOI:10.1038 / s41598-017-05007-7), and an academic presentation by Sato et al., also of Kyoto University (98th Annual Meeting of the Chemical Society of Japan, presentation number: 2I4-15, Mechanism of highly efficient light emission in organic electroluminescence using DABNA as the emissive molecule, Kyoto University Graduate School of Engineering). In the present invention, when a sample containing a target compound is measured for its fluorescence lifetime at 300 K, if a slow fluorescent component is observed, the target compound is determined to be a "thermally activated delayed fluorescent substance." Here, a slow fluorescent component refers to a component with a fluorescence lifetime of 0.1 μsec or longer. The fluorescence lifetime can be measured using, for example, a fluorescence lifetime measurement device (manufactured by Hamamatsu Photonics, C11367-01). The polycyclic aromatic compound of the present invention can function as an emitting dopant, and the "thermally activated delayed fluorescent substance" can function as an assisting dopant that assists the emission of the polycyclic aromatic compound of the present invention.

[0383] Figure 2 shows the energy level diagram of the emitting layer of a TAF device using a common fluorescent dopant as the emitting dopant (ED). In the diagram, the ground state energy level of the host is E(1,G), the excited singlet energy level obtained from the shoulder on the short wavelength side of the fluorescence spectrum of the host is E(1,S,Sh), the excited triplet energy level obtained from the shoulder on the short wavelength side of the phosphorescence spectrum of the host is E(1,T,Sh), the ground state energy level of the assisting dopant, which is the second component, is E(2,G), the excited singlet energy level obtained from the shoulder on the short wavelength side of the fluorescence spectrum of the assisting dopant, which is the second component, is E(2,S,Sh), and the excited triplet energy level obtained from the shoulder on the short wavelength side of the fluorescence spectrum of the assisting dopant, which is the second component, is E(2,G). The excited triplet energy level obtained from the shoulder on the short wavelength side of the phosphorescence spectrum of the assisting dopant is E(2,T,Sh), the ground state energy level of the emitting dopant, which is the third component, is E(3,G), the excited singlet energy level obtained from the shoulder on the short wavelength side of the fluorescence spectrum of the emitting dopant, which is the third component, is E(3,S,Sh), and the excited triplet energy level obtained from the shoulder on the short wavelength side of the phosphorescence spectrum of the emitting dopant, which is the third component, is E(3,T,Sh). In a TAF element, when a general fluorescent dopant is used as the emitting dopant (ED), the energy upconverted by the assisting dopant is transferred to the excited singlet energy level E(3,S,Sh) of the emitting dopant and emits light. However, some of the excited triplet energy E(2,T,Sh) on the assisting dopant transfers to the excited triplet energy level E(3,T,Sh) of the emitting dopant, or intersystem crossing occurs on the emitting dopant from the excited singlet energy level E(3,S,Sh) to the excited triplet energy level E(3,T,Sh), followed by thermal decay to the ground state E(3,G). This pathway results in a waste of energy, as some of the energy is not used for light emission.

[0384] In contrast, in the organic electroluminescent device of this embodiment, the energy transferred from the assisting dopant to the emitting dopant can be efficiently utilized for light emission, thereby achieving high light-emitting efficiency. This is presumably due to the following light-emitting mechanism. A preferred energy relationship in the organic electroluminescent device of this embodiment is shown in Figure 3. In the organic electroluminescent device of this embodiment, the compound having a boron atom as the emitting dopant has a high excited triplet energy level E(3,T,Sh). Therefore, even if the excited singlet energy upconverted by the assisting dopant undergoes intersystem crossing to the excited triplet energy level E(3,T,Sh) in the emitting dopant, it is either upconverted on the emitting dopant or recovered to the excited triplet energy level E(2,T,Sh) on the assisting dopant (thermally activated delayed fluorescent material). Therefore, the generated excited energy can be used for emission without waste. Furthermore, by dividing the upconversion and emission functions into two types of molecules each specializing in each function, the residence time of the high energy is reduced, which is expected to reduce the burden on the compound. In this embodiment, known host compounds can be used, such as compounds having at least one of a carbazole ring and a furan ring. Among them, it is preferable to use a compound in which at least one of a furanyl group and a carbazolyl group is bonded to at least one of an arylene group and a heteroarylene group. Specific examples include mCP and mCBP.

[0385] The triplet energy level E(1,T,Sh), determined from the shoulder on the short-wavelength side of the peak of the phosphorescence spectrum of the host compound, is preferably higher than the triplet energy levels E(2,T,Sh) and E(3,T,Sh) of the emitting dopant or assisting dopant having the highest triplet energy level in the emitting layer, from the viewpoint of promoting TADF generation without inhibiting it. Specifically, the triplet energy level E(1,T,Sh) of the host compound is preferably 0.01 eV or higher, more preferably 0.03 eV or higher, and even more preferably 0.1 eV or higher, relative to E(2,T,Sh) and E(3,T,Sh). A TADF-active compound may also be used as the host compound.

[0386] The host compound may be, for example, a compound represented by any one of the above formulas (H1), (H2) and (H3).

[0387] <Thermally activated delayed phosphor (assisting dopant)> The thermally activated delayed phosphor (TADF compound) used in the TAF element is preferably a donor-acceptor type thermally activated delayed phosphor (DA type TADF compound) designed to localize the HOMO (highest occupied molecular orbital) and LUMO (lowest unoccupied molecular orbital) within the molecule using an electron-donating substituent called a donor and an electron-accepting substituent called an acceptor, thereby causing efficient reverse intersystem crossing. In this specification, the term "electron-donating substituent" (donor) refers to a substituent or partial structure in which the HOMO orbital is localized in the thermally activated delayed fluorescent substance molecule, and the term "electron-accepting substituent" (acceptor) refers to a substituent or partial structure in which the LUMO orbital is localized in the thermally activated delayed fluorescent substance molecule. In general, thermally activated delayed fluorescent materials using donors and acceptors have large spin-orbit coupling (SOC) due to their structure, and small exchange interaction between HOMO and LUMO, resulting in a low ΔE ST On the other hand, thermally activated delayed fluorescent materials using donors or acceptors exhibit large structural relaxation in the excited state (in some molecules, the stable structure differs between the ground state and the excited state, so when an external stimulus causes a transition from the ground state to the excited state, the structure subsequently changes to the stable structure in the excited state), giving a wide emission spectrum, which may reduce color purity when used as a light-emitting material.

[0388] As the thermally activated delayed phosphor in the TAF element, for example, a compound in which a donor and an acceptor are bonded directly or via a spacer can be used.As the electron donating group (donor structure) and electron accepting group (acceptor structure) used in the thermally activated delayed phosphor of the present invention, for example, the structure described in Chemistry of Materials, 2017, 29, 1946-1963 can be used. Examples of donor structures include carbazole, dimethylcarbazole, di-tert-butylcarbazole, dimethoxycarbazole, tetramethylcarbazole, benzofluorocarbazole, benzothienocarbazole, phenyldihydroindolocarbazole, phenylbicarbazole, bicarbazole, tercarbazole, diphenylcarbazolylamine, tetraphenylcarbazolyldiamine, phenoxazine, dihydrophenazine, phenothiazine, dimethyldihydroacridine, diphenylamine, bis(tert-butyl)phenylamine, (diphenylamino)phenyl)diphenylbenzenediamine, dimethyltetraphenyldihydroacridinediamine, tetramethyldihydroindenoacridine, and diphenyldihydrodibenzazasiline. Acceptor structures include sulfonyldibenzene, benzophenone, phenylenebis(phenylmethanone), benzonitrile, isonicotinonitrile, phthalonitrile, isophthalonitrile, paraphthalonitrile, benzenetricarbonitrile, triazole, oxazole, thiadiazole, benzothiazole, benzobis(thiazole), benzoxazole, benzobis(oxazole), quinoline, benzimidazole, dibenzoquinoxaline, heptaazaphenalene, thioxanthone dioxide, dimethylanthracenone, anthracenedione, cycloheptabipyridine, fluorene dicarbonitrile, triphenyltriazine, pyrazine dicarbonitrile, pyrimidine, phenylpyrimidine, methylpyrimidine, pyridine dicarbonitrile, dibenzoquinoxaline dicarbonitrile, bis(phenylsulfonyl)benzene, dimethylthioxanthene dioxide, thianthrene tetraoxide, and tris(dimethylphenyl)borane.In particular, the compound having thermally activated delayed fluorescence in the TAF element is preferably a compound having at least one partial structure selected from carbazole, phenoxazine, acridine, triazine, pyrimidine, pyrazine, thioxanthene, benzonitrile, phthalonitrile, isophthalonitrile, diphenylsulfone, triazole, oxadiazole, thiadiazole, and benzophenone.

[0389] The compound used as the second component of the light-emitting layer in the TAF element is preferably a thermally activated delayed phosphor, and is a compound whose emission spectrum at least partially overlaps with the absorption peak of the emitting dopant. Below, examples of compounds that can be used as the second component (thermally activated delayed phosphor) of the light-emitting layer in the TAF element are given. However, compounds that can be used as the thermally activated delayed phosphor in the TAF element are not limited to the following example compounds. In the following formula, Me represents methyl, tBu represents t-butyl, Ph represents phenyl, and the wavy line represents a bonding position.

[0390] [ka]

[0391] [ka]

[0392] [ka]

[0393] [ka]

[0394] [ka]

[0395]

change

[0396]

change

[0397]

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[0398]

change

[0399]

change

[0400]

change

[0401]

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[0402]

change

[0403]

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[0404]

change

[0405]

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[0406] [ka]

[0407] [ka]

[0408] [ka]

[0409] Furthermore, as the thermally activated delayed fluorescent substance, a compound represented by any one of the following formulae (AD1), (AD2) and (AD3) can also be used. [ka]

[0410] In the above formulas (AD1), (AD2) and (AD3), Each M is independently a single bond, -O-, >N-Ar, or >CAr2, and is preferably a single bond, -O-, or >N-Ar from the viewpoint of the HOMO depth and the height of the excited singlet and triplet energy levels of the partial structure to be formed. Each J is a spacer structure separating the donor partial structure and the acceptor partial structure, and is independently an arylene having 6 to 18 carbon atoms. From the viewpoint of the strength of the conjugation exuded from the donor partial structure and the acceptor partial structure, an arylene having 6 to 12 carbon atoms is preferred. More specific examples include phenylene, methylphenylene, and dimethylphenylene. Each Q is independently =C(-H)- or =N-, and is preferably =N- from the viewpoint of the shallowness of the LUMO and the height of the excited singlet and triplet energy levels of the partial structure to be formed. Each Ar is independently hydrogen, an aryl having 6 to 24 carbon atoms, a heteroaryl having 2 to 24 carbon atoms, an alkyl having 1 to 12 carbon atoms, or a cycloalkyl having 3 to 18 carbon atoms. From the viewpoint of the HOMO depth and the height of the excited singlet energy level and the excited triplet energy level of the partial structure to be formed, it is preferably hydrogen, an aryl having 6 to 12 carbon atoms, a heteroaryl having 2 to 14 carbon atoms, an alkyl having 1 to 4 carbon atoms, or a cycloalkyl having 6 to 10 carbon atoms, more preferably hydrogen, phenyl, tolyl, xylyl, mesityl, biphenyl, pyridyl, bipyridyl, triazyl, carbazolyl, dimethylcarbazolyl, di-tert-butylcarbazolyl, benzimidazole, or phenylbenzimidazole, and even more preferably hydrogen, phenyl, or carbazolyl. m is 1 or 2. n is an integer of 1 to (6-m), and from the viewpoint of steric hindrance, it is preferably an integer of 4 to (6-m). Furthermore, at least one hydrogen atom in the compounds represented by the above formulas may be substituted with a halogen or deuterium.

[0411] More specifically, the compounds used as the second component in this embodiment are preferably 4CzBN, 4CzBN-Ph, 5CzBN, 3Cz2DPhCzBN, 4CzIPN, 2PXZ-TAZ, Cz-TRZ3, BDPCC-TPTA, MA-TA, PA-TA, FA-TA, PXZ-TRZ, DMAC-TRZ, BCzT, DCzTrz, DDCzTRz, spiroAC-TRZ, Ac-HPM, Ac-PPM, Ac-MPM, TCzTrz, TmCzTrz, and DCzmCzTrz.

[0412] The compound used as the second component in this embodiment may be a donor-acceptor TADF compound represented by DA, in which one donor D and one acceptor A are bonded directly or via a linking group. However, a compound having a structure represented by the following formula (DAD1), in which multiple donors D are bonded to one acceptor A directly or via a linking group, is preferred because it will result in better properties for the organic electroluminescent device. (D 1 -L 1 )nA 1 (DAD1) Formula (DAD1) includes compounds represented by the following formula (DAD2). D 2 -L 2 -A 2 -L 3 -D 3 (DAD2) In the formula (DAD1) and the formula (DAD2), D 1 , D 2 and D 3 A each independently represents a donor group. As the donor group, the above-mentioned donor structure can be used. 1 and A 2 each independently represents an acceptor group, and the acceptor group may have the acceptor structure described above. 1 , L 2 and L 3each independently represents a single bond or a conjugated linking group. The conjugated linking group is a spacer structure that separates the donor group and the acceptor group, and is preferably an arylene having 6 to 18 carbon atoms, more preferably an arylene having 6 to 12 carbon atoms. L 1 , L 2 and L 3 It is more preferable that each of A is independently phenylene, methylphenylene or dimethylphenylene. 1 represents an integer equal to or less than the maximum number of substitutions that can be made. For example, n may be selected within the range of 2 to 10, or within the range of 2 to 6. When n is 2, the compound is represented by formula (DAD2). 1 may be the same or different, and n L 1 and may be the same or different. Preferred specific examples of the compounds represented by formula (DAD1) and formula (DAD2) include 2PXZ-TAZ and the following compounds, but the second component that can be used in the present invention is not limited to these compounds.

[0413] [ka]

[0414] In this embodiment, the light-emitting layer may be composed of either a single layer or multiple layers. The host compound, the thermally activated delayed phosphor, and the polycyclic aromatic compound of the present invention may be contained in the same layer, or at least one component may be contained in multiple layers. The host compound, the thermally activated delayed phosphor, and the polycyclic aromatic compound of the present invention contained in the light-emitting layer may each be a single type or a combination of multiple types. The assisting dopant and the emitting dopant may be contained entirely or partially in the host compound as a matrix. The light-emitting layer doped with the assisting dopant and the emitting dopant can be formed by a method of forming a film by ternary co-evaporation of the host compound, the assisting dopant, and the emitting dopant, a method of premixing the host compound, the assisting dopant, and the emitting dopant and then simultaneously evaporating them, or a wet film-forming method in which a composition for forming an light-emitting layer (paint) prepared by dissolving the host compound, the assisting dopant, and the emitting dopant in an organic solvent is applied.

[0415] The amount of the host compound used varies depending on the type of host compound and may be determined according to the properties of the host compound. The amount of the host compound used is preferably 40 to 99.999% by mass, more preferably 50 to 99.99% by mass, and even more preferably 60 to 99.9% by mass of the total materials for the light-emitting layer. The above ranges are preferable in terms of, for example, efficient charge transport and efficient energy transfer to the dopant.

[0416] The amount of the assisting dopant (thermally activated delayed phosphor) used varies depending on the type of the assisting dopant, and may be determined according to the properties of the assisting dopant. The amount of the assisting dopant used is preferably 1 to 60 mass % of the total material for the light-emitting layer, more preferably 2 to 50 mass %, and even more preferably 5 to 30 mass %. The above range is preferable, for example, in that energy can be efficiently transferred to the emitting dopant.

[0417] The amount of emitting dopant (a compound having a boron atom) used varies depending on the type of emitting dopant, and may be determined according to the characteristics of the emitting dopant. The amount of emitting dopant used is preferably 0.001 to 30% by mass, more preferably 0.01 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 range is preferable in that, for example, concentration quenching can be prevented.

[0418] A low concentration of the emitting dopant is preferable in terms of preventing concentration quenching. A high concentration of the assisting dopant is preferable in terms of the efficiency of the thermally activated delayed fluorescence mechanism. Furthermore, from the viewpoint of the efficiency of the thermally activated delayed fluorescence mechanism of the assisting dopant, it is preferable that the concentration of the emitting dopant is lower than that of the assisting dopant.

[0419] 2-1-3. 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.

[0420] 2-1-4. 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.

[0421] 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.

[0422] 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.

[0423] 2-1-5. 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.

[0424] 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 the material 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 be less likely to generate impurities that act as traps during production and use.

[0425] 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 (4,4',4"-tris(N-carbazolyl)triphenylamine, 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, triphenylamine derivatives such as 4,4',4"-tris(3-methylphenyl(phenyl)amino)triphenylamine, starburst amine derivatives, etc.), stilbene derivatives, phthalocyanine derivatives (metal-free, copper phthalocyanine, etc.), pyrazoline derivatives, hydrazone compounds, benzofuran derivatives, thiophene derivatives, oxadiazole derivatives, quinoxaline derivatives Examples of the material include conductors (for example, 1,4,5,8,9,12-hexaazatriphenylene-2,3,6,7,10,11-hexacarbonitrile), heterocyclic compounds such as porphyrin derivatives, polysilanes, etc. Among polymers, polycarbonates and styrene derivatives having the above-mentioned monomers in their side chains, polyvinylcarbazole, and polysilanes are preferred, but there are no particular limitations on the material as long as it is a compound that can form a thin film required for fabricating a light-emitting device, can inject holes from the anode, and can transport holes.

[0426] It is also known that the conductivity of organic semiconductors is strongly influenced by their doping. Such 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). The polycyclic aromatic compound of the present invention may be used as a material for forming a hole injection layer or a material for forming a hole transport layer.

[0427] 2-1-6. Electron blocking layer in organic electroluminescent devices An electron blocking layer may be provided between the hole injection / transport layer and the light-emitting layer to prevent electrons from diffusing from the light-emitting layer. The electron blocking layer can be formed from a compound represented by any of the above formulas (H1), (H2), and (H3). The polycyclic aromatic compound of the present invention may be used as a material for forming an electron blocking layer.

[0428] 2-1-7. 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.

[0429] 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.

[0430] 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.

[0431] 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.

[0432] Specific examples of other electron transport compounds include pyridine derivatives, naphthalene derivatives, fluoranthene derivatives, BO derivatives, anthracene derivatives, phenanthroline derivatives, perinone derivatives, coumarin derivatives, naphthalimide derivatives, anthraquinone derivatives, diphenoquinone derivatives, diphenylquinone derivatives, perylene derivatives, oxadiazole derivatives (e.g., 1,3-bis[(4-t-butylphenyl)1,3,4-oxadiazolyl]phenylene), thiophene derivatives, triazole derivatives (e.g., N-naphthyl-2,5-diphenyl-1,3,4-triazole), thiadiazole derivatives, metal complexes of oxine derivatives, quinolinol metal complexes, quinoxaline derivatives, polymers of quinoxaline derivatives, benzazole compounds, gallium complexes, pyrazole derivatives, perfluorinated phenylene derivatives, triazine derivatives, pyrazine derivatives, benzoxazole compounds ... Examples of the compound include quinolin derivatives (such as 2,2'-bis(benzo[h]quinolin-2-yl)-9,9'-spirobifluorene), imidazopyridine derivatives, borane derivatives, benzimidazole derivatives (such as tris(N-phenylbenzimidazol-2-yl)benzene), benzoxazole derivatives, thiazole derivatives, benzothiazole derivatives, quinoline derivatives, oligopyridine derivatives such as terpyridine, bipyridine derivatives, terpyridine derivatives (such as 1,3-bis(4'-(2,2':6',2"-terpyridinyl))benzene), naphthyridine derivatives (such as bis(1-naphthyl)-4-(1,8-naphthyridin-2-yl)phenylphosphine oxide), aldazine derivatives, pyrimidine derivatives, arylnitrile derivatives, indole derivatives, phosphorus oxide derivatives, bisstyryl derivatives, silole derivatives, and azoline derivatives.

[0433] 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.

[0434] The above-mentioned materials may be used alone or in combination with other materials.

[0435] 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, quinolinol-based metal complexes, thiazole derivatives, benzothiazole derivatives, silole derivatives, and azoline derivatives are preferred.

[0436] The polycyclic aromatic compound of the present invention may be used as a material for forming an electron injection layer or an electron transport layer.

[0437] 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.

[0438] 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.

[0439] 2-1-8. 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 .

[0440] 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.

[0441] 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.

[0442] 2-1-9. 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.

[0443] 2-1-10.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, inkjet 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. 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.

[0444] Next, as an example of a method for fabricating an organic EL device, we will explain a method for fabricating an organic EL device consisting of 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. A thin film of an anode material is formed on a suitable substrate by vapor deposition or other methods to form an anode, and then a thin film of a hole injection layer and a hole transport layer is formed on the anode. A thin film of a host material and a dopant material is co-deposited on the anode to form an emitting layer. An electron transport layer and an electron injection layer are then formed on the emitting layer, and a thin film of a cathode material is further formed by vapor deposition or other methods to form a cathode, thereby obtaining the desired organic EL device. It should be noted that the above-described organic EL device can also be fabricated in the reverse order: cathode, electron injection layer, electron transport layer, emitting layer, hole transport layer, hole injection layer, and anode.

[0445] 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.

[0446] 2-1-11.Application examples of organic electroluminescent devices The organic EL element can also be applied to a display device or a lighting device. A display device or lighting device including an organic EL element can be manufactured by a known method, such as by connecting the organic EL element to a known driving device, and can be driven appropriately using a known driving method such as DC driving, pulse driving, or AC driving.

[0447] 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.

[0448] 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.

[0449] 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.

[0450] 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 equipment, automobile panels, display boards, signs, etc. In particular, for backlights for liquid crystal display devices, especially for personal computers, where thinning is an issue, considering that conventional methods use fluorescent lamps and light guide plates and therefore are difficult to achieve, backlights using organic EL elements are characterized by their thinness and light weight.

[0451] 2-2. Other organic devices The polycyclic aromatic compound according to the present invention can be used to produce not only the organic electroluminescent device described above, but also an organic field effect transistor or an organic thin-film solar cell.

[0452] An organic field-effect transistor is a transistor that controls current by an electric field generated by voltage input, and has a gate electrode in addition to a source electrode and a drain electrode. When a voltage is applied to the gate electrode, an electric field is generated, and the 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.

[0453] 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.

[0454] 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.

[0455] 3. Wavelength conversion materials The polycyclic aromatic compound of the present invention can be used as a wavelength converting material. Currently, the application of color conversion technology to multicolor displays, organic light-emitting diode (OLED) displays, and lighting is being actively investigated. Color conversion refers to the wavelength conversion of light emitted from a light emitter to light of a longer wavelength, such as converting ultraviolet or blue light to green or red light. By fabricating a film of wavelength conversion materials with this color conversion function and combining it with a blue light source, for example, it is possible to extract the three primary colors of blue, green, and red from the blue light source, i.e., white light. A white light source combining such a blue light source with a wavelength conversion film with color conversion functionality can be used as a light source unit, and combined with a liquid crystal driver and color filters, it is possible to create a full-color display. Furthermore, if the liquid crystal driver is not required, the white light source can be used as is, for example, in LED lighting. Furthermore, by combining a blue organic light-emitting diode (OLED) element as a light source with a wavelength conversion film that converts blue light to green and red, it is possible to fabricate a full-color OLED display without using a metal mask. Furthermore, by using blue microLEDs as a light source in combination with wavelength conversion films that convert blue light into green and red light, it becomes possible to create low-cost full-color microLED displays.

[0456] The polycyclic aromatic compound of the present invention can be used as this wavelength converting material. Using a wavelength converting material containing the polycyclic aromatic compound of the present invention, light from a light source or light-emitting element that generates ultraviolet light or a shorter wavelength blue light can be converted into blue light or green light with high color purity suitable for use in display devices (display devices using organic EL elements and liquid crystal display devices). The converted color can be adjusted by appropriately selecting the substituents of the polycyclic aromatic compound of the present invention, the binder resin used in the wavelength converting composition described below, and the like. The wavelength converting material can be prepared as a wavelength converting composition containing the polycyclic aromatic compound of the present invention. Furthermore, this wavelength converting composition may be used to form a wavelength conversion film.

[0457] The wavelength-converting composition may contain, in addition to the polycyclic aromatic compound of the present invention, a binder resin, other additives, and a solvent. Examples of binder resins that can be used include those described in paragraphs 0173 to 0176 of International Publication No. 2016 / 190283. Examples of other additives that can be used include compounds described in paragraphs 0177 to 0181 of International Publication No. 2016 / 190283. For the solvent, the description of the solvent contained in the composition for forming an emitting layer can be referenced.

[0458] The wavelength conversion film includes a wavelength converting layer formed by curing a wavelength converting composition. Known film formation methods can be referred to as a method for producing a wavelength converting layer from a wavelength converting composition. The wavelength conversion film may consist solely of a wavelength converting layer formed from a composition containing the polycyclic aromatic compound of the present invention, or may also include other wavelength converting layers (e.g., a wavelength converting layer that converts blue light to green light or red light, or a wavelength converting layer that converts blue light or green light to red light). The wavelength conversion film may further include a substrate layer and a barrier layer to prevent deterioration of the color converting layer due to oxygen, moisture, or heat. [Example]

[0459] The present invention will be explained in more detail below with reference to examples, but the present invention is not limited to these examples. In the reaction schemes in the examples, Me represents methyl, Et represents ethyl, tBu represents t-butyl, and iPr represents isopropyl.

[0460] Synthesis example (1): Synthesis of compound (1-1) [ka]

[0461] 1st step Under a nitrogen atmosphere, compound (T-1) (13.0 g), compound (T-2) (17.8 g), sodium tert-butoxide (NaOtBu, 4.8 g), Pd-132 (trade name: dichlorobis(di-t-butyl(4-dimethylaminophenyl)phosphino)palladium, 0.41 g), and xylene (140 ml) were placed in a reactor and heated to reflux for 3 hours. After the reaction mixture was cooled to room temperature, the aqueous layer was extracted with toluene. The combined organic layers were washed with water and dried over anhydrous magnesium sulfate. The solution was concentrated under reduced pressure, and the residue was purified by silica gel chromatography (toluene) to obtain compound (T-3) (25.6 g).

[0462] Synthesis of compound (1-1) Compound (T-3) (8.0 g) and tert-butylbenzene ( t A 1.6 M tert-butyllithium pentane solution (tBuLi, 10 ml) was added to a flask containing 60 ml of tert-butylbenzene under a nitrogen atmosphere at -30°C. After the dropwise addition, the temperature was raised to 60°C and the mixture was stirred for 2 hours, after which components with a boiling point lower than that of tert-butylbenzene were distilled off under reduced pressure. The mixture was cooled to -30°C, and boron tribromide (4.0 g) was added. The mixture was then warmed to room temperature and stirred for 0.5 hours. The mixture was then cooled again to 0°C, and N,N-diisopropylethylamine (EtN(iPr)2, 2.8 ml) was added. The mixture was stirred at room temperature until the heat generation subsided, and then heated to 120°C and stirred for 3 hours. The reaction mixture was cooled to room temperature, and an aqueous sodium acetate solution cooled in an ice bath, followed by heptane, was added and the mixture was separated. Next, after purifying with a silica gel short-path column (developing liquid: toluene), the solvent was distilled off under reduced pressure, and the resulting solid was dissolved in toluene and reprecipitated by adding heptane to obtain the compound represented by formula (1-1).

[0463] 1H-NMR(CDCl3):δ=9.04 (s,1H), 8.99 (s,1H), 7.66 (d,2H), 7.53 (d,1H), 7.48 (dd,1H), 7.35 (d,2H), 7.29 (t,1H), 7.27-7.25 (m,2H), 7.02 (d,2H), 7.00 (d,2H), 6.93 (dd,1H), 6.65 (d,1H), 5.91 (s,1H), 5.89 (s,1H), 5.73 (s,2H), 2.09 (s,3H), 1.90 (s,6H), 1.51 (s,9H), 1.46 (s,9H), 1.38 (s,9H), 1.30 (s,9H), 1.26 (s,18H).

[0464] Synthesis Example (2): Synthesis of Compound (1-7) Compound (1-7) was obtained in the same manner as in Synthesis Example 1, except that compound (T-3) was changed to compound (T-3-7). MS measurement (MALDI-TOFMS) showed m / z (M+H) = 940.67

[0465] [ka]

[0466] Synthesis Example (3): Synthesis of Compound (1-10) Compound (1-10) was obtained in the same manner as in Synthesis Example 1, except that compound (T-3) was changed to compound (T-3-10). MS measurement (MALDI-TOFMS) showed m / z (M+H) = 1072.76

[0467] [ka]

[0468] Synthesis Example (4): Synthesis of Compound (1-42) Compound (1-42) was obtained in the same manner as in Synthesis Example 1, except that compound (T-3) was changed to compound (T-3-42). MS measurement (MALDI-TOFMS) showed m / z (M+H) = 1054.72

[0469] [ka]

[0470] Synthesis Example (5): Synthesis of Compound (1-350) Compound (1-350) was obtained in the same manner as in Synthesis Example 1, except that compound (T-3) was changed to compound (T-3-350). MS (MALDI-TOFMS) showed m / z (M+H) = 1152.73 1 H-NMR (CDCl3): δ=8.7(s, 1H), 7.9(d, 1H), 7.7(d, 2H), 7.5(d, 1H), 7.5~7.4(m , 7H), 7.1~7.0(m, 2H), 7.0(m, 3H), 7.0(dd, 1H), 6.9~6.8(m, 2H), 6.6(d, 1H), 6 .2(d, 1H), 6.0(d, 1H), 6.0(d, 1H), 5.9(s, 1H), 1.9(s, 3H), 1.9(s, 3H), 1.5(s , 9H), 1.4(s, 9H), 1.4(s, 9H), 1.3(s, 9H), 1.1(s, 9H), 1.1(s, 9H), 1.0(s, 9H).

[0471] [ka]

[0472] Synthesis Example (6): Synthesis of Compound (1-365) Compound (1-365) was obtained in the same manner as in Synthesis Example 1, except that compound (T-3) was changed to compound (T-3-365). MS measurement (MALDI-TOFMS) showed m / z (M+H) = 1148.79

[0473] [ka]

[0474] Synthesis Example (7): Synthesis of Compound (1-367) Compound (1-367) was obtained in the same manner as in Synthesis Example 1, except that compound (T-3) was changed to compound (T-3-367). MS measurement (MALDI-TOFMS) showed m / z (M+H) = 1038.68

[0475] [ka]

[0476] Synthesis Example (8): Synthesis of Compound (1-369) Compound (1-369) was obtained in the same manner as in Synthesis Example 1, except that compound (T-3) was changed to compound (T-3-369). 1 H-NMR (CDCl3): δ=9.00(br,1H), 8.89(br,1H), 7.60-7.50(m,2H), 7.39(d,1H), 7.37(d,1H) ), 7.33-7.27(m,2H), 7.11(d,2H), 7.07(d,1H), 6.99(br,2H), 6.96-6.89(m,2H), 6.60(br, 1H), 6.23(dd,1H), 6.09(br,1H), 5.87(br,1H), 5.48(br,1H), 2.21-2.15(m,3H), 1.97(dd, 6H), 1.91-1.68(m,26H), 1.53(s,6H), 1.40(s,6H), 1.25(s,6H), 1.09(s,6H), 0.93(s,9H).

[0477] [ka]

[0478] Synthesis Example (9): Synthesis of Compound (1-370) Compound (1-370) was obtained in the same manner as in Synthesis Example 1, except that compound (T-3) was changed to compound (T-3-370). MS measurement (MALDI-TOFMS) showed m / z (M+H) = 1148.79

[0479] [ka]

[0480] Synthesis Example (10): Synthesis of Compound (1-374) Compound (1-374) was obtained in the same manner as in Synthesis Example 1, except that compound (T-3) was changed to compound (T-3-374). MS measurement (MALDI-TOFMS) showed m / z (M+H) = 1116.73 1 H-NMR (CDCl3): δ=8.97(br,1H), 8.79(br,1H), 7.70(br,1H), 7.61-7.48(m,2H), 7 .42-7.26(m,5H), 7.17(d,1H), 7.14-7.08(m,4H), 7.05-6.96(m,4H), 6.95-6.88(m ,2H), 6.61(br,1H), 6.26-5.47(m,4H), 2.22-2.16(m,3H), 1.97(d,6H), 1.91-1.61 (m,16H), 1.48-1.42(m,15H), 1.11(s,9H), 1.09(s,3H), 1.07(s,3H), 0.92(s,9H).

[0481] [ka]

[0482] Synthesis Example (11): Synthesis of Compound (1-380) Compound (1-380) was obtained in the same manner as in Synthesis Example 1, except that compound (T-3) was changed to compound (T-3-380). MS measurement (MALDI-TOFMS) showed m / z (M+H) = 1128.82

[0483] [ka]

[0484] Synthesis Example (12): Synthesis of Compound (1-381) Compound (1-381) was obtained in the same manner as in Synthesis Example 1, except that compound (T-3) was changed to compound (T-3-381). MS measurement (MALDI-TOFMS) showed m / z (M+H) = 960.64 1 H-NMR (CDCl3): δ=9.00(br,1H), 8.89(br,1H), 7.64-7.49(m,2H), 7.44-7.32(m,4H), 7.31-7.27(m ,2H), 7.14(d,2H), 7.06(d,1H), 7.01(d,2H), 6.96-6.89(m,2H), 6.60(br,1H), 6.26-5.50(m,4H), 1.87(br,6H), 1.82-1.68(m,8H), 1.57-1.47(m,6H), 1.40(s,9H), 1.40(s,6H), 1.24(s,6H), 1.10(s,6H), 0.93(s,9H).

[0485] [ka]

[0486] Synthesis Example (13): Synthesis of Compound (1-382) Compound (1-382) was obtained in the same manner as in Synthesis Example 1, except that compound (T-3) was changed to compound (T-3-382). MS measurement (MALDI-TOFMS) showed m / z (M+H) = 1092.73 1H-NMR (CDCl3): δ=8.87(br,1H), 8.82(br,1H), 7.57(d,1H), 7.51(m,1H), 7.47-7.40(m,3H), 7 .38-7.32(m,2H), 7.29(br,1H), 7.15(dd,2H), 7.07(br,1H), 7.01(d,1H), 6.99-6.87(m,6H), 6.61(br,1H), 6.22-6.17(m,1H), 6.01(br,2H), 5.59(br,1H), 1.92-1.64(m,14H), 1.53(s,6H) ), 1.42(s,9H), 1.40(s,6H), 1.25(s,6H), 1.11(s,9H), 1.10(s,3H), 1.09(s,3H), 0.94(s,9H).

[0487] [ka]

[0488] Synthesis Example (14): Synthesis of Compound (1-383) Compound (1-383) was obtained in the same manner as in Synthesis Example 1, except that compound (T-3) was changed to compound (T-3-383). MS measurement (MALDI-TOFMS) showed m / z (M+H) = 1128.82

[0489] [ka]

[0490] Synthesis Example (15): Synthesis of Compound (1-386) Compound (1-386) was obtained in the same manner as in Synthesis Example 1, except that compound (T-3) was changed to compound (T-3-386). MS measurement (MALDI-TOFMS) showed m / z (M+H) = 1062.68

[0491] [ka]

[0492] Synthesis Example (16): Synthesis of Compound (1-435) Compound (1-435) was obtained in the same manner as in Synthesis Example 1, except that compound (T-3) was changed to compound (T-3-435). MS measurement (MALDI-TOFMS) showed m / z (M+H) = 991.54

[0493] [ka]

[0494] Synthesis Example (17): Synthesis of Compound (1-436) Compound (1-436) was obtained in the same manner as in Synthesis Example 1, except that compound (T-3) was changed to compound (T-3-436). 1 H-NMR (CDCl3): δ=8.85(s,1H),8.19(d,1H),8.07(t,1H),7.95(d,1H),7.67(dd,1H),7. 56(dq,2H),7.49(d,1H),7.45(dd,1H),7.38-7.36(m,3H),7.24(q,1H),7.15(dd,1H),6 .82(d,1H),6.76(s,1H),6.31(s,1H),6.27(s,1H),6.15(s,1H),1.89(dd,6H),1.83(d, 4H),1.48(s,9H),1.44(d,6H),1.33(s,9H),1.30-1.27(m,6H),1.13(s,9H),0.90(s,9H)

[0495] [ka]

[0496] Synthesis Example (18): Synthesis of Compound (1-450) Compound (1-450) was obtained in the same manner as in Synthesis Example 1, except that compound (T-3) was changed to compound (T-3-450). MS measurement (MALDI-TOFMS) showed m / z (M+H) = 961.53

[0497] [ka]

[0498] Synthesis Example (19): Synthesis of Compound (1-456) Compound (1-456) was obtained in the same manner as in Synthesis Example 1, except that compound (T-3) was changed to compound (T-3-456). MS measurement (MALDI-TOFMS) showed m / z (M+H) = 1017.59

[0499] [ka]

[0500] Synthesis Example (20): Synthesis of Compound (1-465) Compound (1-465) was obtained in the same manner as in Synthesis Example 1, except that compound (T-3) was changed to compound (T-3-465). MS measurement (MALDI-TOFMS) showed m / z (M+H) = 1289.88

[0501] [ka]

[0502] Synthesis Example (21): Synthesis of Compound (1-466) Compound (1-466) was obtained in the same manner as in Synthesis Example 1, except that compound (T-3) was changed to compound (T-3-466). MS measurement (MALDI-TOFMS) showed m / z (M+H) = 1315.90

[0503] [ka]

[0504] Synthesis Example (22): Synthesis of Compound (1-467) Compound (1-467) was obtained in the same manner as in Synthesis Example 1, except that compound (T-3) was changed to compound (T-3-467). MS measurement (MALDI-TOFMS) showed m / z (M+H) = 1341.91

[0505] [ka]

[0506] Synthesis Example (23): Synthesis of Compound (1-480) Compound (1-480) was obtained in the same manner as in Synthesis Example 1, except that compound (T-3) was changed to compound (T-3-480). MS measurement (MALDI-TOFMS) showed m / z (M+H) = 1080.60

[0507] [ka]

[0508] By appropriately changing the starting compounds, other compounds of the present invention can be synthesized in accordance with the methods of the above synthesis examples.

[0509] <Evaluation methods for basic physical properties> Sample preparation When evaluating the absorption and emission characteristics (fluorescence and phosphorescence) of a compound to be evaluated, the compound can be dissolved in a solvent and evaluated in the solvent, or evaluated in the form of a thin film. Furthermore, when evaluating in the form of a thin film, depending on the manner in which the compound to be evaluated will be used in an organic EL device, the compound to be evaluated alone can be evaluated as a thin film, or the compound to be evaluated can be dispersed in an appropriate matrix material and evaluated as a thin film. Here, a thin film obtained by vapor-depositing only the compound to be evaluated is referred to as a "single film," and a thin film obtained by applying and drying a coating liquid containing the compound to be evaluated and a matrix material is referred to as a "coated film."

[0510] The matrix material can be commercially available PMMA (polymethyl methacrylate), etc. In this example, PMMA and the compound to be evaluated were dissolved in toluene, and then a thin film was formed on a transparent quartz substrate (10 mm × 10 mm) by spin coating to prepare a sample.

[0511] Fluorescence spectra were measured for the compounds represented by formulas (1-1), (1-7), (1-10), (1-350), (1-369), and (1-380). Each compound (1% by mass relative to PMMA) and PMMA were dissolved in toluene, then spin-coated onto a substrate (quartz substrate, 10 mm x 10 mm) and dried to form a thin film. The emission wavelength and half-width of the emission spectrum (calculated as the width between the wavelengths above and below the maximum emission wavelength at which the intensity is 50%) were measured. The results are shown in Table 1.

[0512] [Table 1]

[0513] The results in Table 1 show that the compounds of the present invention emit light with a narrow half-value width and high color purity.

[0514] When the matrix material is a host compound, a thin film sample is prepared as follows. A transparent quartz support substrate (10 mm × 10 mm × 1.0 mm) was fixed to the substrate holder of a commercially available evaporation system (manufactured by Choshu Sangyo Co., Ltd.), and a molybdenum evaporation boat containing the host compound and a molybdenum evaporation boat containing the dopant material were installed. After that, the vacuum chamber was opened to 5 × 10 -4 The pressure is reduced to 100 Pa. Next, the evaporation boat containing the host compound and the evaporation boat containing the dopant material are heated simultaneously, and the host compound and the dopant material are co-evaporated to an appropriate film thickness to form a mixed thin film (sample) of the host compound and the dopant material. Here, the evaporation rate is controlled according to the set mass ratio of the host compound and the dopant material.

[0515] Absorption and emission properties The absorption spectrum of the sample is measured using an ultraviolet-visible-near-infrared spectrophotometer (Shimadzu Corporation, UV-2600), and the fluorescence spectrum or phosphorescence spectrum of the sample is measured using a spectrofluorometer (Hitachi High-Tech Corporation, F-7000).

[0516] For measuring fluorescence spectra, the sample is excited with an appropriate excitation wavelength at room temperature and photoluminescence is measured. For measuring phosphorescence spectra, the sample is immersed in liquid nitrogen (temperature 77 K) using an attached cooling unit. To observe phosphorescence spectra, an optical chopper is used to adjust the delay time from irradiation with excitation light to the start of measurement. The sample is excited with an appropriate excitation wavelength and photoluminescence is measured.

[0517] Furthermore, the luminescence quantum yield (PLQY) is measured using an absolute PL quantum yield measurement device (manufactured by Hamamatsu Photonics KK, C9920-02G).

[0518] Next, evaluation of the basic physical properties of the polycyclic aromatic compound of the present invention will be described.

[0519] Evaluation of fluorescence lifetime (delayed fluorescence) The fluorescence lifetime was measured at 300 K using a fluorescence lifetime measurement system (Hamamatsu Photonics K.K., C11367-01). Specifically, we observed both fast-lifetime and slow-lifetime emission components at the maximum emission wavelength measured at an appropriate excitation wavelength. When measuring the fluorescence lifetime of typical organic electroluminescent materials that emit fluorescence at room temperature, the slow-lifetime emission component, which involves the triplet component derived from phosphorescence, is rarely observed due to thermal deactivation of the triplet component. If a slow-lifetime emission component is observed in the compound being evaluated, it indicates that the triplet energy, which has a long excitation lifetime, has been transferred to singlet energy by thermal activation, resulting in the delayed fluorescence.

[0520] Calculation of energy gap (Eg) Calculate Eg = 1240 / A from the long wavelength end A (nm) of the absorption spectrum obtained by the above method.

[0521] Ionization potential (Ip) measurement A transparent support substrate (28 mm × 26 mm × 0.7 mm) on which ITO (indium tin oxide) was deposited was fixed to the substrate holder of a commercially available deposition device (manufactured by Choshu Sangyo Co., Ltd.), and a molybdenum deposition boat containing the target compound was attached. The vacuum chamber was then opened to 5 × 10 -4 The pressure is reduced to Pa. Next, the evaporation boat is heated to evaporate the target compound, forming a film of the target compound alone (neat film).

[0522] The obtained single film is used as a sample, and the ionization potential of the target compound is measured using a photoelectron spectrometer (Sumitomo Heavy Industries, Ltd. PYS-201).

[0523] Calculation of electron affinity (Ea) The electron affinity can be estimated from the difference between the ionization potential measured by the above-mentioned method and the energy gap calculated by the above-mentioned method.

[0524] Measurement of excited singlet energy level E(S,Sh) and excited triplet energy level E(T,Sh) For a single film of the target compound formed on a glass substrate, the fluorescence spectrum is observed at 77 K using excitation light at a peak on the long wavelength side so that the fluorescence peak of the absorption spectrum does not overlap, and the excited singlet energy level E(S, Sh) is determined from the shoulder on the short wavelength side of the peak of the fluorescence spectrum. In addition, a film of the target compound formed on a glass substrate is used to observe the phosphorescence spectrum at 77 K using excitation light with a peak on the long wavelength side of 1 nm, so that the fluorescence peak of the absorption spectrum does not overlap. The excited triplet energy level E(T, Sh) is determined from the shoulder on the short wavelength side of the peak of the phosphorescence spectrum.

[0525] <Evaluation of organic EL elements> The compounds of the present invention have an appropriate energy gap (Eg), a high triplet excitation energy (E T ) and small ΔE STTherefore, it is expected to be applicable to, for example, a light-emitting layer and a charge transport layer, and particularly to a light-emitting layer.

[0526] Evaluation items and evaluation methods Evaluation items include driving voltage (V), emission wavelength (nm), CIE chromaticity (x, y), external quantum efficiency (%), maximum wavelength (nm) and half-width (nm) of the emission spectrum, etc. For these evaluation items, values ​​at appropriate emission luminance can be used.

[0527] 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 continue to be reflected inside the light-emitting element and are not emitted to the outside of the light-emitting element, the external quantum efficiency is lower than the internal quantum efficiency.

[0528] The spectral radiance (emission spectrum) and external quantum efficiency were measured as follows. The device was irradiated by applying a voltage using an Advantest R6144 voltage / current generator. 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 observed wavelength range to obtain the total number of photons emitted from the device. The applied current value was divided by the elementary charge to obtain the number of carriers injected into the device. The external quantum efficiency was calculated by dividing the total number of photons emitted from the device by the number of carriers injected into the device. 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%.

[0529] Next, the preparation and evaluation of an organic EL device using the polycyclic aromatic compound of the present invention will be described.

[0530] Organic EL element structure Using the polycyclic aromatic compound of the present invention, organic EL devices having the following device configurations A and B were produced.

[0531] <Element configuration A> The material configuration of each layer in the organic EL devices according to Examples (A-1) to (A-23) and Comparative Example (1) is shown in Table 2 below. [Table 2] TIFF0007808800000191.tif137170

[0532] In Table 2, "HI" stands for N 4 ,N 4’ -diphenyl-N 4 ,N 4’ -bis(9-phenyl-9H-carbazol-3-yl)-[1,1'-biphenyl]-4,4'-diamine, "HAT-CN" is 1,4,5,8,9,12-hexaazatriphenylene hexacarbonitrile, "HT-1" is N-([1,1'-biphenyl]-4-yl-9,9-dimethyl-N-[4-(9-phenyl-9H-carbazol-3-yl)phenyl]-9H-fluoren-2-amine, and "HT-2" is N,N-bis(4-(dibenzo[b,d]furan-4-yl)phenyl)- "ET-1" is 9,9'-(5-(6-(1,1'-biphenyl)-4-yl)-2-phenylpyrimidin-4-yl)-1,3-phenylene]bis(9H-carbazole), and "ET-2" is 4,4'-((2-phenylanthracene-9,10-diyl)bis(4,1-phenylene))dipyridine. The chemical structures are shown below along with those of "Liq" and "Comparative Compound 1."

[0533] [ka]

[0534] Preparation of organic EL device of Example (A-1) A 26 mm × 28 mm × 0.7 mm glass substrate (manufactured by Optoscience Co., Ltd.) on which an ITO film having a thickness of 180 nm was formed by sputtering and polished to 150 nm was used as a transparent support substrate. This transparent support substrate was fixed to the substrate holder of a commercially available vapor deposition apparatus (manufactured by Showa Vacuum Co., Ltd.), and molybdenum vapor deposition boats containing HI, HAT-CN, HT-1, HT-2, BH, compound (1-1), ET-1, and ET-2, and aluminum nitride vapor deposition boats containing Liq, LiF, and aluminum, respectively, were attached.

[0535] The following layers are formed in order on the ITO film of the transparent support substrate. -4 The pressure was reduced to 10 Pa, and HI was first heated and evaporated to a thickness of 40 nm, followed by HAT-CN, which was heated and evaporated to a thickness of 5 nm, followed by HT-1, which was heated and evaporated to a thickness of 45 nm, and finally HT-2, which was heated and evaporated to a thickness of 10 nm, to form a hole layer consisting of four layers. Next, BH and compound (1-1) were simultaneously heated and evaporated to a thickness of 25 nm to form an emissive layer. The evaporation rate was adjusted so that the mass ratio of BH to compound (1-1) was approximately 97:3. Next, ET-1 was heated and evaporated to a thickness of 5 nm, followed by ET-2 and Liq, which were simultaneously heated and evaporated to a thickness of 25 nm to form a two-layer electron layer. The evaporation rate was adjusted so that the mass ratio of ET-2 to Liq was approximately 50:50. The evaporation rate for each layer was 0.01–1 nm / s. Thereafter, LiF was heated and evaporated at a deposition rate of 0.01 to 0.1 nm / sec to a thickness of 1 nm, and then aluminum was heated and evaporated to a thickness of 100 nm to form a cathode, thereby obtaining the organic EL element of Example (A-1).

[0536] Preparation of organic EL devices of Examples (A-2) to (A-23) and Comparative Example (1) The organic EL devices of Examples (A-2) to (A-23) and Comparative Example (1) were each prepared in the same manner as in Example (A-1), except that the compounds listed in Table 2 were used instead of Compound (1-1).

[0537] Evaluation items and evaluation methods The evaluation items include the driving voltage (V), emission wavelength (nm), CIE chromaticity (x, y), external quantum efficiency (%), maximum wavelength (nm) and half-width (nm) of the emission spectrum. 2 The value at the time of light emission can be used.

[0538] 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 continue to be reflected inside the light-emitting element and are not emitted to the outside of the light-emitting element, the external quantum efficiency is lower than the internal quantum efficiency.

[0539] The spectral radiance (emission spectrum) and external quantum efficiency were measured as follows: Using an Advantest voltage / current generator R6144, the device luminance was measured at 1000 cd / m 2 The device emits light by applying a voltage equal to the wavelength of the light emitted. Using a TOPCON SR-3AR spectroradiometer, the spectral radiance in the visible light region is measured perpendicular to the light-emitting surface. Assuming the light-emitting surface is a perfectly diffusing surface, the measured spectral radiance value for each wavelength component is divided by the wavelength energy and multiplied by π to obtain the number of photons at each wavelength. The number of photons is 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 is 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 is the external quantum efficiency. The half-width of the emission spectrum is calculated as the width between the wavelengths above and below the maximum emission wavelength at which the intensity is 50%.

[0540] For each organic EL device fabricated above, a DC voltage of 1000 cd / m was applied to the ITO electrode as the anode and the LiF / aluminum electrode as the cathode. 2 The driving voltage and external quantum efficiency during light emission were measured. 2 The device was continuously driven at the voltage required for light emission, and the time during which the brightness was maintained at 95% or more of the initial brightness was measured. The results are shown in Table 3.

[0541] [Table 3] TIFF0007808800000194.tif54170

[0542] <Element configuration B> The material configuration of each layer in the organic EL device according to Example (B-1) is shown in Table 4 below. [Table 4]

[0543] In Table 4, "NPD" is N,N'-diphenyl-N,N'-dinaphthyl-4,4'-diaminobiphenyl, "TcTa" is 4,4',4"-tris(N-carbazolyl)triphenylamine, "mCP" is 1,3-bis(N-carbazolyl)benzene, "mCBP" is 3,3'-bis(N-carbazolyl)-1,1'-biphenyl, "TSPO1" is diphenyl[4-(triphenylsilyl)phenyl]phosphine oxide, and "2PXZ-TAZ" is 10,10'-((4-phenyl-4H-1,2,4-triazole-3,5-diyl)bis(4,1-phenylene))bis(10H-phenoxazine). The chemical structures are shown below.

[0544] [ka]

[0545] [Device Configuration B: Device with mCBP as the host compound, 2PXZ-TAZ as the assisting dopant, and Compound (1-1) as the emitting dopant] A 26 mm × 28 mm × 0.7 mm glass substrate (manufactured by Optoscience Co., Ltd.) on which a 200 nm thick ITO film was formed by sputtering and polished to 50 nm was used as a transparent support substrate. This transparent support substrate was fixed to the substrate holder of a commercially available evaporation system (manufactured by Choshu Sangyo Co., Ltd.), and tantalum evaporation boats containing NPD, TcTa, mCP, mCBP, 2PXZ-TAZ, compound (1-1), and TSPO1, and aluminum nitride evaporation boats containing LiF and aluminum 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 100 Pa. First, NPD was heated and evaporated to a thickness of 40 nm. Next, TcTa was heated and evaporated to a thickness of 15 nm to form a two-layer hole injection / transport layer. Next, mCP was heated and evaporated to a thickness of 15 nm to form an electron blocking layer. Next, mCBP as the host, 2PXZ-TAZ as the assisting dopant, and compound (1-1) as the emitting dopant were simultaneously heated and co-evaporated to a thickness of 20 nm to form an emitting layer. The evaporation rate was adjusted so that the mass ratio of host to assisting dopant to emitting dopant was approximately 90:9:1. Next, TSPO1 was heated and evaporated to a thickness of 30 nm to form an electron transport layer. The evaporation rate for each of these layers was 0.01 to 1 nm / s. Next, LiF was heated and evaporated at a evaporation rate of 0.01 to 0.1 nm / s to a thickness of 1 nm. Next, aluminum was heated and evaporated to a thickness of 100 nm to form a cathode, and an organic EL device was obtained. At this time, the deposition rate of aluminum was adjusted to 1 nm to 10 nm / sec.

[0547] For the organic EL device according to Example (B-1), a DC voltage of 100 cd / m was applied between the ITO electrode as the anode and the LiF / aluminum electrode as the cathode. 2When the light-emitting characteristics were measured, the external quantum efficiency was 25.3%. 2 The time for which the device maintained 90% or more of its initial brightness when continuously driven at the voltage required for light emission was measured, and it was found to be 72 hours.

[0548] Device configuration A is characterized by a long luminance retention time at high luminance, while device configuration B is characterized by a high external quantum efficiency. In device configuration A, in an example in which the compound of the present invention was used as a dopant in the emitting layer, a device having a higher external quantum efficiency and a longer retention time than the comparative example was obtained. [Explanation of symbols]

[0549] 100 Organic electroluminescent device 101 Substrate 102 Anode 103 Hole injection layer 104 Hole transport layer 105 Light-emitting layer 106 Electron transport layer 107 Electron injection layer 108 Cathode

Claims

1. A polycyclic aromatic compound represented by the following formula (1-b): 【Chemistry 1】 In formula (1-b), Each Z is independently N or C-R Ｚ and the C-R Ｚ R Ｚ are each independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl (two aryls may be bonded via a single bond or a linking group), alkyl, cycloalkyl, alkoxy, aryloxy, or substituted silyl, in which at least one hydrogen may be substituted with aryl, heteroaryl, alkyl, cycloalkyl, or substituted silyl; Z = Z are each independently >O, >N-R, or >C(-R) ２ or >S, and R in the >N-R and the >C(-R) 2 are each independently hydrogen, an aryl which may be substituted with alkyl, a heteroaryl which may be substituted with alkyl, an alkyl, or a cycloalkyl, and the >C(-R) ２ two R's may be bonded to each other to form a ring, Two adjacent C-R Ｚ R Ｚ may be bonded to each other to form a ring, and the formed ring may be substituted with hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl (two aryls may be bonded via a single bond or a linking group), alkyl, cycloalkyl, alkoxy, aryloxy, or substituted silyl, and at least one hydrogen in these may be substituted with alkyl, cycloalkyl, or substituted silyl; In ring c, Z is C-R Ｚ or one Z = Z is >O, >N-R, >C(-R) ２ , or >S, and the remaining Z is C-R Ｚ and R Ｚ are bonded to each other to form a benzene ring, Y １ is B, X １ and X ２ are each independently >N-R, and R of the >N-R is aryl which may be substituted with alkyl or cycloalkyl, heteroaryl which may be substituted with alkyl or cycloalkyl, unsubstituted alkyl, or cycloalkyl which may be substituted with alkyl, and R of the >N-R is C-R via a linking group or a single bond. Ｚ R in Z is Ｚ may be linked to one or two of X ３ is >N—R, wherein R in the >N—R is an aryl optionally substituted with alkyl, and X ４ is >O or >C(-R) ２ and the >C(-R) ２ R's each independently represent an aryl which may be substituted with an alkyl, or an unsubstituted alkyl, and two R's may be bonded to each other to form a ring; In the compound represented by formula (1-b), at least one of the aryl rings or heteroaryl rings may be condensed with at least one cycloalkane, at least one hydrogen atom in the cycloalkane may be substituted, and at least one —CH ２ - may be replaced by -O-, The compound represented by formula (1-b) contains at least one substituent selected from tertiary alkyl, neopentyl, and adamantyl represented by formula (tR), 【Chemistry 2】 In formula (tR), Ra, Rb, and Rc each independently represent alkyl having 1 to 24 carbon atoms, and any —CH ２ - may be substituted with -O-, the group represented by formula (tR) replaces at least one hydrogen atom in the compound represented by formula (1-b) at *, At least one hydrogen atom in the compound represented by formula (1-b) may be substituted with cyano, halogen, or deuterium.

2. Both Z are C-R Ｚ The polycyclic aromatic compound according to claim 1, wherein

3. X ３ 3. The polycyclic aromatic compound according to claim 1, wherein R in N—R is phenyl substituted with tertiary alkyl.

4. X ４ > C (-R) ２ and X ４ >C(-R) ２ The polycyclic aromatic compound according to any one of claims 1 to 3, wherein each of R is methyl.

5. The polycyclic aromatic compound according to claim 1, represented by formula (1-b-Z): 【Transformation 3】 In formula (1-b-Z), R Ｘ１ and R Ｘ２ are each independently an aryl which may be substituted with alkyl or cycloalkyl, a heteroaryl which may be substituted with alkyl or cycloalkyl, an unsubstituted alkyl, or a cycloalkyl which may be substituted with alkyl; R Ｘ１ is connected to R by a linking group or a single bond. Ｘ１ may be bonded to any ring to which the N bonded to R Ｘ２ is connected to R by a linking group or a single bond. Ｘ１ and R Ｘ２ may be bonded to any ring to which the N to which is bonded is directly bonded, X １３ is >N—R, wherein R in the >N—R is an aryl optionally substituted with alkyl, R Ｘ４ are each independently an unsubstituted alkyl, and two R Ｘ４ may be bonded to each other to form a cycloalkane ring, R Ｚ１ is unsubstituted alkyl, R Ｚ２ each independently represents an unsubstituted alkyl; m represents an integer of 0 to 2; R Ｚ３ are each independently an unsubstituted alkyl, and n is an integer of 0 to 2; In the structure represented by formula (1-b-Z), at least one of the aryl rings or heteroaryl rings may have a structure in which a partial structure represented by formula (B) is bonded to an adjacent carbon atom, 【Chemistry 4】 In formula (B), Me represents methyl, * represents the bonding position, At least one hydrogen atom in the structure represented by formula (1-b-Z) may be substituted with cyano, halogen, or deuterium.

6. The polycyclic aromatic compound according to claim 5, which is represented by any one of the following formulas: 【Transformation 5】 In the formula, Me is methyl and tBu is t-butyl.

7. A polycyclic aromatic compound represented by formula (1-b-T): 【Transformation 6】 In formula (1-b-T), R Ｘ１ and R Ｘ２ are each independently an aryl which may be substituted with alkyl or cycloalkyl, a heteroaryl which may be substituted with alkyl or cycloalkyl, an unsubstituted alkyl, or a cycloalkyl which may be substituted with alkyl; R Ｘ１ is connected to R by a linking group or a single bond. Ｘ１ may be bonded to any ring to which the N bonded to R Ｘ２ is connected to R by a linking group or a single bond. Ｘ１ and R Ｘ２ may be bonded to any ring to which the N to which is bonded is directly bonded, X １３ are each independently >O, >N—R, or >C(—R) ２ wherein R in the >N—R is an aryl optionally substituted with an alkyl, and the >C(—R) ２ each R is independently an unsubstituted alkyl, and two Rs may be bonded to each other to form a cycloalkane ring; R Ｘ４ are each independently an unsubstituted alkyl, and two R Ｘ４ may be bonded to each other to form a cycloalkane ring, R Ｚ１ is unsubstituted alkyl, R Ｚ２ each independently represents an unsubstituted alkyl; m represents an integer of 0 to 2; R Ｚ３ are each independently an unsubstituted alkyl, and n is an integer of 0 to 2; In the structure represented by formula (1-b-T), at least one of the aryl rings or heteroaryl rings may have a structure in which a partial structure represented by the following formula (B) is bonded to an adjacent carbon atom: 【Transformation 7】 In formula (B), Me represents methyl, * represents the bonding position, The structure represented by formula (1-b-T) contains at least one substituent selected from tertiary alkyl, neopentyl, and adamantyl represented by formula (tR), 【Transformation 8】 In formula (tR), Ra, Rb, and Rc each independently represent alkyl having 1 to 24 carbon atoms, and any —CH ２ - may be substituted with -O-, the group represented by formula (tR) replaces at least one hydrogen atom in the structure represented by formula (1-b-T) at *, At least one hydrogen atom in the structure represented by formula (1-b-T) may be substituted with cyano, halogen, or deuterium.

8. The polycyclic aromatic compound according to claim 7, which is represented by any one of the following formulas: 【Chemistry 9】 In the formula, Me is methyl and tBu is t-butyl.

9. A material for an organic device, comprising the polycyclic aromatic compound according to any one of claims 1 to 8.

10. a pair of electrodes consisting of an anode and a cathode, and a light-emitting layer disposed between the pair of electrodes; An organic electroluminescent device, wherein the light-emitting layer contains the polycyclic aromatic compound according to any one of claims 1 to 8.

11. The organic electroluminescent device according to claim 10 , wherein the light-emitting layer contains a host and the polycyclic aromatic compound as a dopant.

12. The organic electroluminescent device according to claim 11, wherein the host is an anthracene-based compound, a fluorene-based compound, or a dibenzochrysene-based compound.

13. A display device or a lighting device comprising the organic electroluminescent device according to any one of claims 10 to 12.

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