Polycyclic aromatic compounds

Abstract

To provide a novel compound as a material used in an organic EL element.SOLUTION: A polycyclic aromatic compound represented by formula (1); X1 and X2 are>O;Y1 to Y6 are =C(-RY)- or =N-, and at least one is =N-; RY is at least one being a group represented by (A-1) or (A-2); W1 is >O or other; W2 is a single bond; Z is -N= or -CRZ=(RZ is hydrogen); Ar3 is aryl; W3 is Si; m is 3, and n is 0; L1 and L2 are a single bond or a linkage group; L1 is bonded to any one of -CRZ= with RZ as a bonding hand, and * represents a binding position, and at least one H in the structure of formula (1) may be substituted with cyano, halogen or deuterium.SELECTED DRAWING: None

Description

[Technical field]

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

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

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

[0004] There are three known types of light-emitting materials for organic EL elements: fluorescent materials, phosphorescent materials, and thermally activated delayed fluorescence (TADF) materials. The fluorescent materials that have been used traditionally have high color purity but low luminous efficiency. On the other hand, phosphorescent and TADF materials are expected to have luminous efficiency three to four times higher than fluorescent materials.

[0005] As phosphorescent materials, many studies have been reported, particularly on iridium complexes (for example, Patent Document 1). Moreover, Patent Document 2 reports that a compound in which multiple aromatic rings are condensed with a central atom such as boron is a TADF material with high color purity.

[0006] Generally, a host material is used together with a light-emitting material (dopant material) as a material for the light-emitting layer of an organic EL element to improve light-emitting efficiency. Generally, a molecule in which multiple existing aromatic rings such as benzene or carbazole are linked together with single bonds or phosphorus or silicon atoms is used as a host material. This is because linking a large number of relatively small aromatic rings in a conjugated system ensures a large HOMO-LUMO gap (band gap Eg in a thin film) required for a host material. Furthermore, host materials for organic EL elements that use phosphorescent or TADF materials have a high lowest excited triplet energy level (E T1 ) is also required, but by linking a donor or acceptor aromatic ring or substituent to the molecule, the SOMO1 and SOMO2 in the triplet excited state (T1) are localized, and the exchange interaction between the two orbitals is reduced, so that E T1 However, small aromatic rings in the conjugated system do not have sufficient redox stability, and devices using molecules formed by linking existing aromatic rings as host materials do not have sufficient life spans. On the other hand, polycyclic aromatic compounds with extended π-conjugated systems generally have excellent redox stability, but have poor HOMO-LUMO gaps (band gaps in thin films, Eg) and E T1 Because of its low molecular weight, it has been considered unsuitable as a host material. [Prior art documents] [Patent documents]

[0007] [Patent Document 1] International Publication No. 2001 / 41512 [Patent Document 2] International Publication No. 2015 / 102118 Summary of the Invention [Problem to be solved by the invention]

[0008] As described above, various materials have been developed as materials for use in organic EL elements. However, in order to further improve the organic EL characteristics such as the light-emitting characteristics, and to increase the options for organic EL materials such as materials for the light-emitting layer, there is a need for the development of compounds that were not previously specifically known. [Means for solving the problem]

[0009] As a result of intensive research to solve the above problems, the present inventors have succeeded in improving charge transport properties and amorphous stability in a polycyclic aromatic compound in which a plurality of aromatic rings are linked by boron atoms and nitrogen atoms or oxygen atoms, etc., by introducing pyridinic nitrogen into the aromatic ring and further forming a structure having a specific substituent. They have also found that an excellent organic EL device can be obtained using this polycyclic aromatic compound, and have completed the present invention. That is, the present invention provides the following polycyclic aromatic compound, and further provides an organic device material containing the following polycyclic aromatic compound.

[0010] <1> A polycyclic aromatic compound represented by the following formula (1): [ka]

[0011] In formula (1), X 1 and X 2 are each independently >NR, >O, >C(-R)2, >S or >Se, and X 1 and X 2 Both are never >C(-R)2, R in the >NR and >C(-R)2 is independently hydrogen or any substituent selected from the substituent group YZ, and R in the >NR and >C(-R)2 is independently connected to Y by a linking group or a single bond. 1 and / or Y 2 , or Y 5 and / or Y 6 and Y 1 , Y2 , Y 3 , Y 4 , Y 5 and Y 6 are each independently, =C(-R Y )- or =N-, with at least one being =N-, R Y are each independently a group represented by formula (A-1) or formula (A-2), a hydrogen atom or a substituent selected from the substituent group YZ excluding the group represented by formula (A-1), or a group represented by formula (21), R Y adjacent groups among these may be bonded to each other to form a ring, and at least one hydrogen atom in the formed ring may be substituted with a group represented by formula (A-1) or formula (A-2), a substituent selected from substituent group YZ excluding the group represented by formula (A-1), or a group represented by formula (21), R Y is a group represented by formula (A-1) or formula (A-2), provided that R Y When they are bonded to form a ring, the group replacing the hydrogen in the ring and R Y At least one selected from the group consisting of is a group represented by formula (A-1) or formula (A-2), In formula (A-1), W 1 and W 2 are each independently a single bond, >C(-R W )2, >NR W , >O, >Si(-R W )2, >S, >SO or >SO2; Previous >NR W R W represents any substituent selected from the substituent group YZ, a group represented by formula (A-2), or a group represented by formula (21), Above>C(-R W )2, >Si(-R W )2R Weach independently represents a hydrogen atom, a substituent selected from the substituent group YZ, a group represented by formula (A-2), or a group represented by formula (21), R bonded to the same element W may be bonded to each other, Previous >NR W ,>C(-R W )2, >Si(-R W ) each of R2 may independently be bonded to at least one Z; Z is -N= or -CR Z = R Z each independently represents a hydrogen atom, a substituent selected from the substituent group YZ, a group represented by formula (A-2), or a group represented by formula (21), R in adjacent Z Z may be bonded to each other to form an aryl ring or a heteroaryl ring, and the formed ring may have any substituent selected from the substituent group YZ, a group represented by formula (A-2), or a group represented by formula (21), L 1 is a single bond or a linking group, L 1 is R Z is used as a bond, and any -CR Z = R attached to C or Z Z are bonded to a ring member atom of a ring formed by bonding together, * indicates the bonding position of the group represented by formula (A-1), In formula (A-2), Ar 3 each independently represents an aryl (excluding the group represented by formula (A-1)) which may be substituted with at least one substituent selected from the substituent group YZ or a group represented by formula (21), a heteroaryl (excluding the group represented by formula (A-1)) which may be substituted with at least one substituent selected from the substituent group YZ or a group represented by formula (21), or a group represented by formula (A-1), W 3 is Si, P or S, W 3When is Si, m is 3 and n is 0; W 3 When is P, m is 2 and n is 0 or 1; 3 is S, m is 1 and n is an integer from 0 to 2; L 2 is a single bond or a linking group, * indicates the bonding position of the group represented by formula (A-2), In formula (21), X 21 and X 22 are each independently >NR X21 , >O, >C(-R X21 )2, >S or >Se; >NR X21 and >C(-R X21 )2 in R X21 are each independently hydrogen or a substituent selected from the substituent group YZ, and the >NR X21 and >C(-R X21 )2R X21 are each independently linked to Y 21 and / or Y 22 , or Y 25 and / or Y 26 and Y 21 , Y 22 , Y 23 , Y 24 , Y 25 and Y 26 are each independently, =C(-R 2Y )- or =N-, R 2Y each independently represents hydrogen or a substituent selected from the substituent group YZ; R 2Y adjacent groups among the above may be bonded to each other to form a ring, and at least one hydrogen atom in the formed ring may be substituted with a substituent selected from the substituent group YZ; L 3 is a single bond or a linking group, and L 3 is any R 2Yis bonded to C or adjacent to R 2Y are bonded to a ring member atom of a ring formed by bonding together, * indicates the bonding position of the group represented by formula (21), the number of groups represented by formula (21) in the polycyclic aromatic compound is 0 to 2, At least one hydrogen in the structure represented by formula (1) may be substituted with cyano, halogen or deuterium; Substituent group YZ: aryl, heteroaryl, aryl optionally substituted with alkyl or cycloalkyl; aryl, heteroaryl, heteroaryl optionally substituted with alkyl or cycloalkyl; diarylamino optionally substituted with aryl, heteroaryl, alkyl or cycloalkyl; diheteroarylamino optionally substituted with aryl, heteroaryl, alkyl or cycloalkyl; arylheteroarylamino optionally substituted with aryl, heteroaryl, alkyl or cycloalkyl; diarylboryl optionally substituted with aryl, heteroaryl, alkyl or cycloalkyl (two aryls may be bonded via a single bond or a linking group); alkyl optionally substituted with aryl, heteroaryl, or cycloalkyl; cycloalkyl optionally substituted with aryl, heteroaryl, alkyl or cycloalkyl; alkoxy optionally substituted with aryl, heteroaryl, or cycloalkyl; and Aryloxy optionally substituted with aryl, heteroaryl, alkyl or cycloalkyl.

[0012] <2> L 1 , L 2 and L 3each independently represents a single bond, an arylene which may be substituted with an aryl or heteroaryl, a heteroarylene which may be substituted with an aryl or heteroaryl, >NR L , >O, >C(-R L )2, >Si(-R L )2, >S, >Se, and combinations of two or more thereof; L 1 , L 2 or L 3 In >NR L ,>C(-R L )2 and >Si(-R L )2 in R L are each independently hydrogen, any substituent selected from the substituent group YZ, or a group represented by formula (A-2), and R L may be bonded to each other, <1> The polycyclic aromatic compound according to claim 1. <3> L 1 and L 2 are each independently a linking group selected from the group consisting of arylene which may be substituted with aryl or heteroaryl, heteroarylene which may be substituted with aryl or heteroaryl, and combinations of two or more thereof; L 3 is a single bond, <1> The polycyclic aromatic compound according to claim 1.

[0013] <4> X 1 and X 2 are each independently >NR or >O; <1> ~ <3> 2. The polycyclic aromatic compound according to claim 1 . <5> Y 2 , Y 3 , Y 4 and Y 5 However, each independently, =C(-R Y )- and Y 1 or Y 6 At least one of the following is =N-; <1> ~ <4> 2. The polycyclic aromatic compound according to claim 1 . <6> X 1and X 2 are all >O, Y 2 , Y 3 , Y 4 , Y 5 and Y 6 However, each independently, =C(-R Y )- and Y 1 is =N-, <5> The polycyclic aromatic compound according to claim 1.

[0014] <7> In formula (1), R Y is a group represented by formula (A-1) or formula (A-2), provided that R Y When they are bonded to form a ring, the group replacing the hydrogen in the ring and R Y and one or two selected from the group consisting of are groups represented by formula (A-1) or formula (A-2). <1> ~ <6> 2. The polycyclic aromatic compound according to claim 1 . <8> In formula (1), R Y is a group represented by formula (A-1), provided that R Y When they are bonded to form a ring, the group replacing the hydrogen in the ring and R Y At least one selected from the group consisting of is a group represented by formula (A-1), W 1 >C(-R W )2, >O, >Si(-R W )2 or >S, W 2 is a single bond, <1> ~ <7> 2. The polycyclic aromatic compound according to claim 1 . <9> In formula (1), R Y is a group represented by formula (A-2), provided that R Y When they are bonded to form a ring, the group replacing the hydrogen in the ring and R Y At least one selected from the group consisting of is a group represented by formula (A-2), W 3 is Si, <1> ~ <8> 2. The polycyclic aromatic compound according to claim 1 .

[0015] <10> In formula (1), Adjacent R's bonded to form a ring Y If there is no match, R other than the group represented by formula (A-1) or formula (A-2) Y is hydrogen, aryl optionally substituted with aryl or heteroaryl, or heteroaryl optionally substituted with aryl or heteroaryl; Adjacent R's bonded to form a ring Y If there is a match, R Y and adjacent R Y Among the groups substituting hydrogen in the ring formed by bonding together, a group other than the group represented by formula (A-1) or formula (A-2) is hydrogen, an aryl which may be substituted with an aryl or a heteroaryl, or a heteroaryl which may be substituted with an aryl or a heteroaryl. <1> ~ <9> 2. The polycyclic aromatic compound according to claim 1 .

[0016] <11> Represented by the following formula (1-11): <1> The polycyclic aromatic compound according to claim 1. [ka]

[0017] <12> Represented by the following formula (1-13): <1> The polycyclic aromatic compound according to claim 1. [ka]

[0018] <13> <1> ~ <12> 2. A reactive compound in which the polycyclic aromatic compound according to any one of claims 1 to 11 is substituted with a reactive substituent. <14> <13> A polymer compound obtained by polymerizing the reactive compound described above as a monomer, or a crosslinked polymer obtained by further crosslinking the polymer compound. <15> Main chain polymer <13> or a pendant-type crosslinked polymer obtained by further crosslinking the pendant-type polymer compound. <16> <1> ~ <12> 2. A material for an organic device, comprising the polycyclic aromatic compound according to claim 1. <17> <13> A material for an organic device, comprising the reactive compound according to claim 1. <18> <14> 2. A material for an organic device, comprising the polymer compound or crosslinked polymer described in 1. <19> <15> 2. A material for an organic device, comprising the pendant type polymer compound or the pendant type crosslinked polymer according to claim 1.

[0019] <20> A pair of electrodes consisting of an anode and a cathode, and a gas sensor disposed between the pair of electrodes, <1> ~ <12> The polycyclic aromatic compound according to any one of the above. <13> The reactive compound according to <14> or <15> and an organic layer containing the pendant type polymer compound or the pendant type crosslinked polymer according to claim 1. <21> The organic layer is an electron transport layer. <20> The organic electroluminescent device according to claim 1. <22> The organic layer is an emitting layer. <20> The organic electroluminescent device according to claim 1. <23> The light-emitting layer contains at least one selected from the group consisting of a light-emitting metal complex and a TADF material. <22> The organic electroluminescent device according to claim 1.

[0020] <24> The light-emitting layer contains a polycyclic aromatic compound which is a monomer represented by formula (2) or a polymer having a plurality of structural units represented by formula (2). <23> The organic electroluminescent device according to the present invention; [ka]

[0021] The A ring, the B ring and the C ring are each independently an optionally substituted aryl ring or an optionally substituted heteroaryl ring, provided that B and X in the A ring, the B ring and the C ring in the monomer are each independently an optionally substituted aryl ring or an optionally substituted heteroaryl ring. 11 and / or X 12 None of the rings bonded to are six-membered rings containing nitrogen. X 11 and X 12 are each independently >O or >NR, R of the >NR is an optionally substituted aryl, an optionally substituted heteroaryl, an optionally substituted alkyl, or an optionally substituted cycloalkyl, and R of the >NR is optionally 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 structure represented by formula (2) or the structure having a plurality of structural units represented by formula (2), at least one selected from the group consisting of an aryl ring and a heteroaryl ring may be condensed with at least one cycloalkane, at least one hydrogen in the cycloalkane may be substituted, and at least one -CH2- in the cycloalkane may be substituted with -O-; At least one hydrogen atom in the structure represented by formula (2) or the structure having a plurality of structural units represented by formula (2) may be substituted with deuterium, cyano or halogen.

[0022] <25> at least one of an electron transport layer and an electron injection layer disposed between the cathode and the light emitting layer, wherein at least one of the electron transport layer and the electron injection layer contains at least one selected from the group consisting of borane derivatives, pyridine derivatives, fluoranthene derivatives, BO derivatives, anthracene derivatives, benzofluorene derivatives, phosphine oxide derivatives, pyrimidine derivatives, arylnitrile derivatives, triazine derivatives, benzimidazole derivatives, phenanthroline derivatives, and quinolinol-based metal complexes; <22> ~ <24> 13. The organic electroluminescent device according to claim 12, <26> At least one of the electron transport layer and the electron injection layer further contains at least one selected from the group consisting of an alkali metal, an alkaline earth metal, a rare earth metal, an oxide of an alkali metal, a halide of an alkali metal, an oxide of an alkaline earth metal, a halide of an alkaline earth metal, an oxide of a rare earth metal, a halide of a rare earth metal, an organic complex of an alkali metal, an organic complex of an alkaline earth metal, and an organic complex of a rare earth metal. <25> The organic electroluminescent device according to claim 1.

[0023] <27> At least one of the hole injection layer, the hole transport layer, the light emitting layer, the electron transport layer and the electron injection layer comprises a polymer compound obtained by polymerizing a low molecular weight compound capable of forming each layer as a monomer, or a crosslinked polymer obtained by further crosslinking the polymer compound, or a pendant type polymer compound obtained by reacting a low molecular weight compound capable of forming each layer with a main chain polymer, or a pendant type crosslinked polymer obtained by further crosslinking the pendant type polymer compound, <22> ~ <25> 13. The organic electroluminescent device according to claim 12, <28> <21> ~ <27> A display device or a lighting device comprising the organic electroluminescent device according to any one of claims 1 to 4. Effect of the Invention

[0024] The present invention provides a novel compound that can be used as a material for organic devices such as organic electroluminescence (EL) elements. The polycyclic aromatic compound of the present invention can be used to increase the options for organic EL materials such as materials for light-emitting layers. The polycyclic aromatic compound of the present invention is expected to be used as an electron transport material, a phosphorescent material, or a host material for TADF materials. [Brief description of the drawings]

[0025] [Figure 1] FIG. 1 is a schematic cross-sectional view showing an organic EL element according to an embodiment of the present invention. [Diagram 2] FIG. 1 is a diagram illustrating a method for producing an organic EL element on a substrate having a bank by using an inkjet method. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0026] The present invention will be described in detail below. The following description 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 "~" means a range including the numerical values ​​before and after "~" as the lower and upper limits. In this specification, "hydrogen" in the explanation of the structural formula means "hydrogen atom (H)".

[0027] In this specification, the chemical structure or the substituent may be expressed by the number of carbon atoms, but the number of carbon atoms in the case where a substituent is substituted on the chemical structure or where a substituent is further substituted on the substituent means the number of carbon atoms in each of the chemical structure and the substituent, and does not mean the total number of carbon atoms in the chemical structure and the substituent, or the total number of carbon atoms in the substituent and the substituent. For example, "substituent B of carbon number Y substituted with substituent A of carbon number X" means that "substituent B of carbon number Y" is substituted with "substituent A of carbon number X", and the carbon number Y is not the total number of carbon atoms in the substituent A and the substituent B. Also, for example, "substituent B of carbon number Y substituted with substituent A" means that "substituent B of carbon number Y" is substituted with "substituent A (without carbon number limit)", and the carbon number Y is not the total number of carbon atoms in the substituent A and the substituent B.

[0028] 1. Polycyclic aromatic compound represented by formula (1) The present invention relates to a polycyclic aromatic compound represented by formula (1). The polycyclic aromatic compound represented by formula (1) has a group represented by formula (A-1) or formula (A-2).

[0029] [ka]

[0030] In the present invention, in the compound in which a plurality of aromatic rings are condensed with boron as the central atom as described in International Publication No. 2015 / 102118, the pyridinic nitrogen of the electron-accepting element is located at the meta position relative to the boron (i.e., the central element B and Y in the above formula (1) are located at the meta position relative to the boron). 1 ~Y6 By arranging the pyridine nitrogen at the position specified above, a stronger multiple resonance effect was obtained. In addition, by introducing pyridine nitrogen as described above, the LUMO becomes deeper, improving the electron-accepting ability and favoring electron injection. Furthermore, when pyridine nitrogen is included at the specified position above, E S1 (lowest excited singlet energy level), E T1 (the lowest excited triplet energy level) is high, and while maintaining a wide gap, it is possible to form a structure with a large number of rings constituting the fused ring as shown in formula (1). The multi-ring fused ring increases the orbital overlap with adjacent molecules, improving carrier transport properties.

[0031] Furthermore, in the present invention, a group represented by formula (A-1) or formula (A-2) is introduced as a substituent to an aromatic ring, thereby realizing a structure having excellent charge transport properties and excellent amorphous stability. The polycyclic aromatic compound represented by formula (1) has high electron transport properties and E S1 , E T1 Therefore, the polycyclic aromatic compound represented by formula (1) is suitable as a host material and an electron transport material for a phosphorescent device, a TADF device, or a TAF device.

[0032] (1) A group represented by formula (A-1) or formula (A-2) In formula (1), R Y and adjacent R Y At least one selected from the group consisting of groups replacing hydrogen in the ring formed by bonding together is a group represented by formula (A-1) or formula (A-2). In the compound of the present invention, the group represented by formula (A-1) or formula (A-2) imparts amorphous stability. In addition, the group represented by formula (A-1) or formula (A-2) can adjust carrier transportability.

[0033] R Y If there is no ring formed by bonding together, R Y At least one of R is a group represented by formula (A-1) or formula (A-2). Y If there is a ring formed by bonding together, R Y and adjacent RY At least one selected from the group consisting of groups substituting hydrogen in the ring formed by bonding together is a group represented by formula (A-1) or formula (A-2). The number of groups represented by formula (A-1) or formula (A-2) contained in formula (1) as described above (the number of groups represented by formula (A-1) or formula (A-2) directly bonded to ring a, ring b, ring c, or a fused ring containing any of these in formula (1)) is preferably 1 to 4, and more preferably 1 or 2.

[0034] [ka]

[0035] In formula (A-1), W 1 and W 2 are each independently a single bond, >C(-R W )2, >O, >NR W , >Si(-R W )2, >S, >SO or >SO2, and said >NR W R W represents any one of substituents selected from the substituent group YZ, a group represented by formula (A-2) or a group represented by formula (21), and the >C(-R W )2, >Si(-R W )2R W are each independently hydrogen, any substituent selected from the substituent group YZ, a group represented by formula (A-2), or a group represented by formula (21). W may be bonded to each other, >NR W ,>C(-R W )2, >Si(-R W )2R W may each independently be bonded to at least one Z. Z is -N= or -CR Z = R Z are each independently hydrogen, any substituent selected from the group YZ of substituents, a group represented by formula (A-2) or a group represented by formula (21).Z may be bonded to each other to form an aryl ring or a heteroaryl ring. In addition, the formed ring may have any substituent selected from the substituent group YZ, a group represented by formula (A-2), or a group represented by formula (21). L 1 is a single bond or a linking group. L 1 is R Z is used as a bond, and any -CR Z = R attached to C or Z Z are bonded to a ring atom of the ring formed by bonding together. * indicates the bonding position of the group represented by formula (A-1).

[0036] [ka]

[0037] In formula (A-2), Ar 3 are each independently an aryl (excluding the group represented by formula (A-1)) which may be substituted with at least one substituent selected from the substituent group YZ or a group represented by formula (21), a heteroaryl (excluding the group represented by formula (A-1)) which may be substituted with at least one substituent selected from the substituent group YZ or a group represented by formula (21), or a group represented by formula (A-1). W 3 is Si, P or S, and W 3 When is Si, m is 3 and n is 0; W 3 When is P, m is 2 and n is 0 or 1; 3 When is S, m is 1 and n is an integer from 0 to 2. L 2 is a single bond or a linking group. * indicates the bonding position of the group represented by formula (A-2).

[0038] In formula (A-1) or formula (A-2), L 1 and L 2are each independently a single bond or an arylene, heteroarylene, >NR L , >O, >C(-R L )2, >Si(-R L L is preferably a linking group selected from the group consisting of >S, >Se, and a combination of any two or more of these. 1 and L 2 each independently represents a single bond, an arylene which may be substituted with an aryl or heteroaryl, a heteroarylene which may be substituted with an aryl or heteroaryl, >NR L , >O, >C(-R L )2, >Si(-R L It is more preferred that the linking group is selected from the group consisting of )2, >S, >Se and combinations of two or more thereof.

[0039] L 1 or L 2 In >NR L ,>C(-R L )2 and >Si(-R L )2 in R L are each independently hydrogen, any substituent selected from the substituent group YZ (described later), or a group represented by formula (A-2), and R L may be bonded to each other.

[0040] L 1 or L 2 In >NR L R in L As L, aryl which may be substituted with aryl or heteroaryl, or heteroaryl which may be substituted with aryl or heteroaryl is preferable. 1 or L 2 In >C(- L R in 2 L Preferably, each of R is an alkyl group, and preferably, two R groups each of which is an alkyl group combine to form a cycloalkane such as cyclohexane. 1 or L 2>Si(-R L )2 in R L is preferably methyl.

[0041] L 1 and L 2 is preferably a linking group formed by linking two or more members selected from a single bond, an arylene which may be substituted with an aryl or heteroaryl, a heteroarylene which may be substituted with an aryl or heteroaryl, and an arylene which may be substituted with an aryl or heteroaryl, and a heteroarylene which may be substituted with an aryl or heteroaryl, More preferably, it is a linking group formed by linking two or more selected from an arylene which may be substituted with an aryl or heteroaryl, a heteroarylene which may be substituted with an aryl or heteroaryl, or an arylene which may be substituted with an aryl or heteroaryl and a heteroarylene which may be substituted with an aryl or heteroaryl.

[0042] L 1 or L 2 In the above, the arylene which may be substituted with an aryl or heteroaryl and the heteroarylene which may be substituted with an aryl or heteroaryl preferably have a bonding position so as to be cross-conjugated. For example, phenylene is preferably 1,3-phenylene.

[0043] L 1 and L 2 With regard to the arylene and heteroarylene in the above, examples of the first substituent include a divalent group formed by eliminating any hydrogen atom of the aryl and heteroaryl described below. L 1 and L 2 For the aryl and heteroaryl in the above, the description of the aryl and heteroaryl as the first substituent given below can be referred to. L 1 and L 2Examples of the linking group represented by the formula (A-1) include linking groups represented by the following formulas: In the following formulas, * indicates a bonding position, and one of the * bonds to the ring a, ring b or ring c, and the other is L in formula (A-1). 1 A partial structure other than L in formula (A-2) 2 It is assumed that the bond is bonded to a partial structure other than the above.

[0044] [ka]

[0045] In the group represented by formula (A-1), W 1 or W 2 >NR W R when W is preferably optionally substituted aryl or optionally substituted heteroaryl. In the group represented by formula (A-1), W 1 Or W 2 >C(-R W )2 when R W Preferably, each of R is an optionally substituted aryl or each of R is an optionally substituted heteroaryl. W The compound is preferably stable when bonded with a single bond. W It is more preferable that each of the phenyl groups is phenyl, and the phenyl groups are bonded to each other via a single bond. In the group represented by formula (A-1), W 1 Or W 2 >Si(-R W )2 when R W Preferably, each of R is an optionally substituted aryl or each of R is an optionally substituted heteroaryl. W The compound is preferably stable when bonded with a single bond. W It is more preferable that each of the phenyl groups is phenyl, and the phenyl groups are bonded to each other via a single bond.

[0046] In the group represented by formula (A-1), W 1 >NR W ,>C(-R W )2, >O, >Si(-R W )2 or >S and W 2 is preferably a single bond, because this provides excellent compound stability and carrier transport properties. 1 >NR W , >O or >S and W 2 is more preferably a single bond, and W 1 is >O and W 2 It is more preferable that is a single bond.

[0047] W 1 Or W 2 >NR W ,>C(-R W )2,>Si(-R W )2R W Each of W may be independently bonded to at least one Z. 1 Or W 2 >NR W Examples of structures in which is bound to Z include the following structures:

[0048] [ka]

[0049] In the group represented by formula (A-1), 0 to 2 Z are -N= and the rest are -CR Z =, 0 to 1 Z is -N=, and the rest are -CR Z = and all Z are -CR Z It is more preferable that R = . Zare each independently preferably hydrogen, aryl which may be substituted with aryl or heteroaryl, heteroaryl which may be substituted with aryl or heteroaryl, diheteroarylamino which may be substituted with aryl or heteroaryl, or arylheteroarylamino which may be substituted with aryl or heteroaryl. This is because they have good carrier transport properties. The aryl or heteroaryl which is a substituent may be further substituted with aryl or heteroaryl. In the group represented by formula (A-1), R Z is other than hydrogen -CR Z R = is preferably 0 to 3 because this provides good amorphous stability. Z is other than hydrogen -CR Z It is more preferable that the number of = is 0 to 2, and further preferably 0 to 1.

[0050] In the group represented by formula (A-1), adjacent -CR Z = 2 R in Z Z may be bonded to each other to form an aryl ring or a heteroaryl ring. Examples of the group represented by formula (A-1) thus forming an aryl ring or a heteroaryl ring include groups represented by any of the following formulas.

[0051] [ka] In the formula, Me is methyl and * indicates the position of attachment.

[0052] The formed ring may have a substituent. The number of the substituents is preferably 0 to 2, and more preferably 0 to 1. The substituent is preferably an aryl which may be substituted with an aryl or heteroaryl, a heteroaryl which may be substituted with an aryl or heteroaryl, a diheteroarylamino which may be substituted with an aryl or heteroaryl, or an arylheteroarylamino which may be substituted with an aryl or heteroaryl.

[0053] L 1 is R Z is used as a bond, and any -CR Z = R attached to C or Z Z are bonded directly to the ring atoms of the ring formed by bonding together. That is, L 1 W 1 Or W 2 does not bind to In the group represented by formula (A-1), W which is not a single bond 1 In either of the Zs in the para position, L 1 It is preferable that the W is bonded to a non-single bond. 1 Z in either para position is -CR Z = and this C is R Z With L as a bond 1 It is preferred that the aryl group is bonded to the

[0054] In the group represented by formula (A-2), Ar 3 are each preferably independently an aryl which may be substituted with an aryl or a heteroaryl (excluding the group represented by formula (A-1)), a heteroaryl which may be substituted with an aryl or a heteroaryl (excluding the group represented by formula (A-1)), or a group represented by formula (A-1), and are preferably unsubstituted aryl, unsubstituted heteroaryl, or a group represented by formula (A-1). In the group represented by formula (A-2), it is preferable that m is large because the electron transport property is excellent. In the group represented by formula (A-2), W 3 is preferably Si, since the compound has excellent stability. In the group represented by formula (A-2), W 3 It is most preferred that m is Si, m is 3 and n is 0.

[0055] (2)Y 1 ~Y 6 Y 1 ~Y 6are each independently, =C(-R Y )- or =N-, with at least one being =N-. 1 ~Y 6 Any of Y may be =N-. 1 and Y 6 =N-(a ring is a pyrimidine ring), Y 1 or Y 6 =N-(a ring is a pyridine ring), Y 2 and Y 5 =N- (ring b and ring c are pyridine rings), Y 3 and Y 4 =N- (ring b and ring c are pyridine rings), Y 2 ~Y 5 =N-(ring b and ring c are pyrimidine rings), Y 1 , Y 3 , Y 4 and Y 6 =N- (ring a is a pyrimidine ring, rings b and c are pyridine rings), Y 1 , Y 2 , Y 5 and Y 6 =N- (ring a is a pyrimidine ring, rings b and c are pyridine rings), Y 1 ~Y 6 =N-(ring a, ring b and ring c are pyrimidine rings), Y 2 or Y 5 is =N-(ring b or ring c is a pyridine ring).

[0056] Y 1 or Y 6 At least one of the following is =N- (Y 1 ~Y 6 The rest is =C(-R Y )-) is preferable. Y 1 When only =N-, the heights of the HOMO and LUMO are appropriate, which is most preferable.

[0057] In addition to the above =N- arrangement, X 1 and X 2 is preferably >O, and a polycyclic aromatic compound containing a partial structure represented by any one of the following formulas is preferred. [ka]

[0058] In particular, polycyclic aromatic compounds containing the partial structure represented by the formula (1-1601-R) have a higher E S1 , high E T1 , small ΔE S1T1 (E S1 and E T1 Since it has a large energy difference with the HOMO and LUMO, it is a promising material for blue TADF assist dopants, TADF hosts, and phosphorescent hosts. It also has a deep HOMO and deep LUMO, making it a promising material for hole blocking and electron transporting.

[0059] Each of the above formulas shows a "partial structure" of a polycyclic aromatic compound. Therefore, R defined in formula (1) Y ;Y 1 Equivalently, =C(-R Y )-R Y ;R Y and Y 1 ~Y 6 As =C(-R Y )-R Y an aryl ring or a heteroaryl ring that can be formed by bonding adjacent groups among the above, and further substituents thereon (first and second substituents); X 1 and X 2 The second substituent on R in >NR and the relationship between R and Y 1 and / or Y 2 , or Y 5 and / or Y 6 A linking group or single bond to the compound; and cyano, halogen or deuterium which may be substituted in the compound are omitted.

[0060] From a synthesis standpoint, polycyclic aromatic compounds having the partial structures represented by the above formulas (1-1601-R) and (1-841-R) are preferred because the aromatic rings (rings b and c) that undergo the Friedel-Crafts reaction on boron do not contain nitrogen and are not electron deficient.

[0061] (3)R Y (and adjacent R Y A group replacing a hydrogen atom in a ring formed by bonding together (other than the group represented by formula (A-1) or formula (A-2)) In this specification, R Y is R in formula (1). Y and Y 1 ~Y 6 At least one of =C(-R Y )-R Y Includes. R Y are each independently a group represented by formula (A-1) or formula (A-2), hydrogen, or any substituent selected from the group YZ of substituents other than the group represented by formula (A-1), or a group represented by formula (21). Y Adjacent groups among these may be bonded to each other to form a ring. At least one hydrogen atom in the formed ring may be substituted with a group represented by formula (A-1) or formula (A-2), a substituent selected from the substituent group YZ except for the group represented by formula (A-1), or a group represented by formula (21).

[0062] Adjacent R's bonded to form a ring Y If there is no match, R Y At least one of R is a group represented by formula (A-1) or formula (A-2), and the other R Y is hydrogen or any substituent selected from the substituent group YZ, excluding the group represented by formula (A-1). Y If there are matches, R Y and adjacent R Y At least one of the groups substituting hydrogen in the ring formed by bonding together is a group represented by formula (A-1) or formula (A-2), and other R Y and adjacent R Y The group substituting a hydrogen atom in the ring formed by bonding together is any substituent selected from the substituent group YZ, excluding the group represented by formula (A-1).

[0063] The substituent group YZ consists of the following: aryl, heteroaryl, aryl optionally substituted with alkyl or cycloalkyl; aryl, heteroaryl, heteroaryl optionally substituted with alkyl or cycloalkyl; diarylamino optionally substituted with aryl, heteroaryl, alkyl or cycloalkyl; diheteroarylamino optionally substituted with aryl, heteroaryl, alkyl or cycloalkyl; arylheteroarylamino optionally substituted with aryl, heteroaryl, alkyl or cycloalkyl; diarylboryl optionally substituted with aryl, heteroaryl, alkyl or cycloalkyl (two aryls may be bonded via a single bond or a linking group); alkyl optionally substituted with aryl, heteroaryl, or cycloalkyl; cycloalkyl optionally substituted with aryl, heteroaryl, alkyl or cycloalkyl; alkoxy optionally substituted with aryl, heteroaryl, or cycloalkyl; and Aryloxy optionally substituted with aryl, heteroaryl, alkyl or cycloalkyl.

[0064] In this specification, in the substituent group YZ, the above-mentioned aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl (two aryls may be bonded via a single bond or a linking group), alkyl, cycloalkyl, alkoxy, or aryloxy, which correspond to the portion directly bonded to the rings a to c in formula (1), may be referred to as the first substituent. The aryl, heteroaryl, alkyl, or cycloalkyl which replaces at least one hydrogen in these may be referred to as the second substituent.

[0065] The "aryl" as the first substituent is, for example, an aryl having 6 to 30 carbon atoms, preferably an aryl having 6 to 20 carbon atoms, more preferably an aryl having 6 to 16 carbon atoms, still more preferably an aryl having 6 to 12 carbon atoms, and particularly preferably an aryl having 6 to 10 carbon atoms.

[0066] Specific examples of the aryl include phenyl, which is a monocyclic ring; biphenylyl, which is a bicyclic ring; naphthyl, which is a condensed bicyclic ring; terphenylyl (m-terphenylyl, o-terphenylyl, p-terphenylyl), which is a tricyclic ring; acenaphthylenyl, fluorenyl, phenalenyl, phenanthrenyl, which are condensed tricyclic rings; triphenylenyl, pyrenyl, naphthacenyl, which are condensed tetracyclic rings; perylenyl, pentacenyl, etc., which are condensed pentacyclic rings. Examples of the aryl include a group represented by formula (A-1), in which L 1 is a single bond, and groups containing no heteroatoms are also included.

[0067] The "heteroaryl" as the first substituent is, for example, a heteroaryl having 2 to 30 carbon atoms, preferably a heteroaryl having 2 to 25 carbon atoms, more preferably a heteroaryl having 2 to 20 carbon atoms, still more preferably a heteroaryl having 2 to 15 carbon atoms, and particularly preferably a heteroaryl having 2 to 10 carbon atoms. In addition, the heteroaryl is, for example, a heterocycle containing, as a ring-constituting atom other than carbon, 1 to 5 heteroatoms selected from oxygen, sulfur, and nitrogen.

[0068] Specific examples of heteroaryl include pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, oxadiazolyl, thiadiazolyl, triazolyl, tetrazolyl, pyrazolyl, pyridinyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, indolyl, isoindolyl, 1H-indazolyl, benzimidazolyl, benzoxazolyl, benzothiazolyl, 1H-benzotriazolyl, quinolinyl, isoquinolinyl, cinnolinyl, quinazolinyl, quinoxalinyl, phthalazinyl, naphthyridinyl, purinyl, pteridinyl, carbazolyl, and acridinyl. Examples of heteroaryl include a group represented by formula (A-1), in which L is a monovalent group of a dibenzophosphoryl ring, a monovalent group of a dibenzophosphoryl ring, furazanyl, thianthrenyl, indolocarbazolyl, benzoindolocarbazolyl, and benzobenzoindolocarbazolyl. Examples of heteroaryl include a group represented by formula (A-1), in which L is a monovalent group of a dibenzophosphoryl ring, ... 1 is a single bond, and groups containing heteroatoms are also included.

[0069] For the "aryl" in "diarylamino" as the first substituent, the "heteroaryl" in "diheteroarylamino" (first substituent), the "aryl" and "heteroaryl" in "arylheteroarylamino" (first substituent), and the "aryl" in "aryloxy" (first substituent), the above-mentioned explanations of aryl and heteroaryl can be cited.

[0070] The "alkyl" as the first substituent may be either linear or branched, and is, for example, a linear alkyl having 1 to 24 carbon atoms or a branched alkyl having 3 to 24 carbon atoms. An alkyl having 1 to 18 carbon atoms (branched alkyl having 3 to 18 carbon atoms) is preferred, an alkyl having 1 to 12 carbon atoms (branched alkyl having 3 to 12 carbon atoms) is more preferred, an alkyl having 1 to 6 carbon atoms (branched alkyl having 3 to 6 carbon atoms) is even more preferred, and an alkyl having 1 to 5 carbon atoms (branched alkyl having 3 to 5 carbon atoms) or an alkyl having 1 to 4 carbon atoms (branched alkyl having 3 to 4 carbon atoms) is particularly preferred.

[0071] Specific examples of alkyl include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, t-butyl, n-pentyl, isopentyl, neopentyl, t-pentyl (t-amyl), n-hexyl, 1-methylpentyl, 3,3-dimethylbutyl, 2-ethylbutyl, n-heptyl, 1-methylhexyl, n-octyl, t-octyl (1,1,3,3-tetramethylbutyl), 1-methyl Examples include heptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 2,6-dimethyl-4-heptyl, 3,5,5-trimethylhexyl, n-decyl, n-undecyl, 1-methyldecyl, n-dodecyl, n-tridecyl, 1-hexylheptyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, n-heptadecyl, n-octadecyl, and n-eicosyl. Further, for example, 1-ethyl-1-methylpropyl, 1,1-diethylpropyl, 1,1-dimethylbutyl, 1-ethyl-1-methylbutyl, 1,1,4-trimethylpentyl, 1,1,2-trimethylpropyl, 1,1-dimethyloctyl, 1,1-dimethylpentyl, 1,1-dimethylheptyl, 1,1,5-trimethylhexyl, 1-ethyl-1-methylhexyl, 1-ethyl-1,3-dimethylbutyl, 1,1,2,2-tetramethylpropyl, 1-butyl-1-methylpentyl, 1,1-diethylbutyl, 1-ethyl-1-methylpentyl, 1,1,3-trimethylbutyl, 1-propyl-1-methylpentyl, 1,1,2-trimethylpropyl, 1-ethyl-1,2,2-trimethylpropyl, 1-propyl-1-methylbutyl, and 1,1-dimethylhexyl.

[0072] 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.

[0073] Specific examples of cycloalkyl include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, and alkyl (particularly methyl) substituted derivatives of these having 1 to 4 carbon atoms, as well as norbornenyl, bicyclo[1.0.1]butyl, bicyclo[1.1.1]pentyl, bicyclo[2.0.1]pentyl, bicyclo[1.2.1]hexyl, bicyclo[3.0.1]hexyl, bicyclo[2.1.2]heptyl, bicyclo[2.2.2]octyl, adamantyl, diamantyl, decahydronaphthalenyl, and decahydroazulenyl.

[0074] The "alkoxy" as the first substituent is, for example, a straight chain alkoxy having 1 to 24 carbon atoms or a branched chain alkoxy having 3 to 24 carbon atoms. An alkoxy having 1 to 18 carbon atoms (branched chain alkoxy having 3 to 18 carbon atoms) is preferable, an alkoxy having 1 to 12 carbon atoms (branched chain alkoxy having 3 to 12 carbon atoms) is more preferable, an alkoxy having 1 to 6 carbon atoms (branched chain alkoxy having 3 to 6 carbon atoms) is even more preferable, and an alkoxy having 1 to 5 carbon atoms (branched chain alkoxy having 3 to 5 carbon atoms) or an alkoxy having 1 to 4 carbon atoms (branched chain alkoxy having 3 to 4 carbon atoms) is particularly preferable.

[0075] Specific examples of alkoxy include methoxy, ethoxy, propoxy, isopropoxy, n-butoxy, isobutoxy, s-butoxy, t-butoxy, t-amyloxy, n-pentyloxy, isopentyloxy, neopentyloxy, t-pentyloxy, n-hexyloxy, 1-methylpentyloxy, 3,3-dimethylbutoxy, 2-ethylbutoxy, n-heptyloxy, 1-methylhexyloxy, n-octyloxy, t-octyloxy, 1-methylheptyloxy, and 2-ethylhexyl. Examples of the aryloxy group include oxy, 2-propylpentyloxy, n-nonyloxy, 2,2-dimethylheptyloxy, 2,6-dimethyl-4-heptyloxy, 3,5,5-trimethylhexyloxy, n-decyloxy, n-undecyloxy, 1-methyldecyloxy, n-dodecyloxy, n-tridecyloxy, 1-hexylheptyloxy, n-tetradecyloxy, n-pentadecyloxy, n-hexadecyloxy, n-heptadecyloxy, n-octadecyloxy, and n-eicosyloxy.

[0076] The "aryl" in the "diarylboryl" as the first substituent can be cited from the above description of the aryl. The two aryls may be bonded via a single bond or a linking group (e.g., >C(-R)2, >O, >S, or >NR). Here, R in >C(-R)2 and >NR is aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, alkyl, cycloalkyl, alkoxy, or aryloxy (above, the first substituent), and the first substituent may be further substituted with aryl, heteroaryl, alkyl, or cycloalkyl (above, the second substituent), and the above description of the aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, alkyl, cycloalkyl, alkoxy, or aryloxy as the first substituent can be cited from the above description of the aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, alkyl, cycloalkyl, alkoxy, or aryloxy as the first substituent.

[0077] As for the aryl, heteroaryl, alkyl, or cycloalkyl (above, the second substituent) substituting the first substituent, the above description of the aryl, heteroaryl, alkyl, or cycloalkyl as the first substituent can be cited.

[0078] Adjacent R's bonded to form a ring Y When there is no R, R is a group represented by formula (A-1) or formula (A-2). Y Other than R Y is preferably hydrogen, aryl which may be substituted with aryl or heteroaryl, or heteroaryl which may be substituted with aryl or heteroaryl. Y Other than R Y It is preferable that 0 to 2 of the groups are groups other than hydrogen, and it is preferable that 0 to 1 of the groups are groups other than hydrogen.

[0079] Adjacent R's bonded to form a ring Y If there are matches, R Y and adjacent R YAmong the groups replacing hydrogen in the ring formed by bonding together, R is a group represented by formula (A-1) or formula (A-2). Y Other than R Y is preferably hydrogen, aryl which may be substituted with aryl or heteroaryl, or heteroaryl which may be substituted with aryl or heteroaryl. Y Of the groups other than the above, preferably 0 to 2 are groups other than hydrogen, and more preferably 0 to 1 are groups other than hydrogen.

[0080] As described above as "0", R is a group represented by formula (A-1) or formula (A-2). Y Other than R Y are all hydrogen, and R Y and adjacent R Y It is also preferred that the hydrogen atoms in the ring formed by bonding together are not substituted with any group other than those represented by formula (A-1) or formula (A-2).

[0081] Specifically, R other than hydrogen Y and adjacent R Y Preferred groups (other than groups represented by formula (A-1) or (A-2)) for substituting hydrogen in the ring formed by bonding together include any of the following.

[0082] [ka]

[0083] (4)R Y Formation of condensed rings by bonding between In equation (1), R YAdjacent groups among may be bonded to each other to form a ring. It is preferable that the ring is formed to form an aryl ring or a heteroaryl ring together with at least one of the rings a, b, and c. In the polycyclic aromatic compound represented by formula (1), the ring structure constituting the compound changes as shown in the following formulas (1'-1) and (1'-2) depending on the mutual bonding form of the substituents in the ring a, ring b, and ring c. Note that R in each formula Y , Y 1 ~Y 6 , a, b, c, X 1 and X 2 The definition of is the same as that in formula (1).

[0084] [ka]

[0085] The ring a', ring b' and ring c' in the above formula (1'-1) and formula (1'-2) each independently represent a substituent R Y and Y 1 ~Y 6 As =C(-R Y )-R Y Adjacent groups in the above are bonded to form an aryl or heteroaryl ring together with the a, b, and c rings (they can also be considered condensed rings formed by condensing the a, b, or c ring with other ring structures). Although not shown in the formula, there are also compounds in which the a, b, and c rings are all changed to the a', b', and c' rings.

[0086] As can be seen from the above formulas (1'-1) and (1'-2), for example, Y in ring a 1 As =C(-R Y )-R Y and Y in b-algebras 2 As =C(-R Y )-R Y , R in ring b 3 and R in c-ring 4 , Y in the c-ring 5 As =C(-R Y )-R Y and Y in a-ring6 As =C(-R Y )-R Y In other words, "adjacent groups" refers to groups that are adjacent on the same ring, and more specifically, groups that are directly bonded to two elements that are adjacent (directly bonded) on the same ring.

[0087] The compounds represented by the above formula (1'-1) or (1'-2) can be, for example, a 6-membered ring (Y 1 and Y 6 =C(-R Y It is a compound having a ring a' (or ring b' or ring c') formed by condensing a benzene ring, indole ring, pyrrole ring, benzofuran ring, or benzothiophene ring to a ring a (in the case of )-, a benzene ring). The condensed ring a' (or condensed ring b' or condensed ring c') formed is a naphthalene ring, carbazole ring, indole ring, dibenzofuran ring, or dibenzothiophene ring, etc., when the ring a (or ring b or ring c) is a benzene ring. In addition, for example, the ring a (or ring b or ring c) is a pyridine ring (Y 1 and Y 6 In the case where either of Y is =N-, a benzene ring, an indole ring, a pyrrole ring, a benzofuran ring, a benzothiophene ring, or the like may be condensed. As described later, two Ys on one ring (for example, Y on the a ring) may be condensed. 1 and Y 6 When both of the formula (I) and (II) are =N-, no fused ring is formed.

[0088] Y 1 ~Y 6 =C(-R Y )- Y if and only if 1 ~Y 6 R other than part Y can be bonded to form a fused ring, Y 1 ~Y 6 When Y is =N-, a condensed ring originating from this =N- is not formed. For example, as shown in the example of the structural formula below, 1and Y 6 When both are =N-, the fused ring a' is not formed, and Y 1 and Y 6 At least one of =C(-R Y )-In some cases, a fused ring a' is formed.

[0089] [ka]

[0090] Examples of the "aryl ring" (ring a', ring b' or ring c') thus formed include an aryl ring having 9 to 30 carbon atoms, an aryl ring having 9 to 16 carbon atoms, an aryl ring having 9 to 12 carbon atoms and an aryl ring having 9 to 10 carbon atoms. The lower limit of the number of carbon atoms in the aryl ring is 9 when ring a, ring b or ring c is a benzene ring having 6 carbon atoms (Y 1 ~Y 6 =C(-R Y )-) is fused with a 5-membered ring (5 carbon atoms), resulting in a fused ring with a total of 9 carbon atoms.

[0091] Specific examples of the "aryl ring" include a fused bicyclic ring such as a naphthalene ring, a fused tricyclic ring such as an acenaphthylene ring, a fluorene ring, a phenalene ring, and a phenanthrene ring, a fused tetracyclic ring such as a triphenylene ring, a pyrene ring, and a naphthacene ring, and a fused pentacyclic ring such as a perylene ring and a pentacene ring.

[0092] Examples of the "heteroaryl ring" (ring a', ring b' or ring c') formed include a heteroaryl ring having 5 to 30 carbon atoms, a heteroaryl ring having 5 to 25 carbon atoms, a heteroaryl ring having 5 to 20 carbon atoms, a heteroaryl ring having 5 to 15 carbon atoms and a heteroaryl ring having 5 to 10 carbon atoms. Examples of the "heteroaryl ring" include a heterocycle containing, in addition to carbon, 1 to 5 heteroatoms selected from oxygen, sulfur and nitrogen as ring-constituting atoms. The lower limit of the number of carbon atoms in the heteroaryl ring is 5 when ring a, ring b or ring c is a pyridine ring (one Y on each ring). 1 ~Y 6This is the lower limit when the pyridine ring having 5 carbon atoms is fused with a 5-membered ring, and the total number of carbon atoms in the fused ring is 5. Therefore, for example, for the a ring, Y 1 and Y 6 If both are =C(-R)-, the lower limit is changed to 6 (Y 1 and Y 6 When both are =N-, no fused ring is formed.

[0093] Specific examples of the "heteroaryl ring" include an indole ring, an isoindole ring, a 1H-indazole ring, a benzimidazole ring, a benzoxazole ring, a benzothiazole ring, a 1H-benzotriazole ring, a quinoline ring, an isoquinoline ring, a cinnoline ring, a quinazoline ring, a quinoxaline ring, a phthalazine ring, a naphthyridine ring, a carbazole ring, an acridine ring, a phenoxathiin ring, a phenoxazine ring, a phenothiazine ring, a phenazine ring, a benzofuran ring, an isobenzofuran ring, a dibenzofuran ring, a benzothiophene ring, a dibenzothiophene ring, and a thianthrene ring.

[0094] The aryl ring or heteroaryl ring formed may be substituted with a group represented by formula (A-1) or formula (A-2) or a substituent selected from the substituent group YZ, excluding the group represented by formula (A-1). Y Please refer to the explanation in.

[0095] (5) A group represented by formula (21) [ka]

[0096] The polycyclic aromatic compound represented by formula (1) may have a group represented by formula (21). As described above, the group represented by formula (21) is R Y , adjacent R Y The substituent of the ring formed by bonding together, R W , R Z , adjacent R ZSubstituents of the ring formed by bonding together, or Ar 3 It can be contained in the structure of the polycyclic aromatic compound represented by formula (1) as a substituent of aryl or heteroaryl in the formula (1). The number of groups represented by formula (21) contained in the polycyclic aromatic compound represented by formula (1) is 0 to 2. That is, when the group represented by formula (21) is contained in the polycyclic aromatic compound represented by formula (1), the number is 1 or 2. Within this range, it can be produced in the same manner as the polycyclic aromatic compound represented by formula (1) that does not contain a group represented by formula (21), and can be used in the production of an organic EL device as a host material or a hole blocking layer forming material, etc., in the same manner as the polycyclic aromatic compound represented by formula (1) that does not contain a group represented by formula (21). The number of groups represented by formula (21) contained in the polycyclic aromatic compound represented by formula (1) is preferably 0 or 1, and more preferably 0.

[0097] The position of the group represented by formula (21) in the polycyclic aromatic compound represented by formula (1) containing one group represented by formula (21) is not particularly limited. Y or R Z It is preferable that any one of R is a group represented by formula (21). Y is preferably in the para position of boron. Z L 1 R, which is a bond with Z It is preferable that the sigma-based sigma-based 1 R, which is a bond with Z For example, in the group represented by formula (A-1), W which is not a single bond is preferably bonded to a ring different from the ring to which it is bonded. 1 In one of the para positions of Z, L 1 When bonded to W, it is not a single bond. 1 The other Z in the para position is -CR Z = and this R Z is preferably a group represented by formula (21). In the polycyclic aromatic compound represented by formula (1) containing two groups represented by formula (21), the position of the group represented by formula (21) is preferably R YEither two of the following or R Y and R Z It is preferable that R is present at one of two positions. Y R is attached to a different ring Y It is preferable that:

[0098] In formula (21), X 21 and X 22 are each independently >NR X21 , >O, >C(-R X21 )2, >S or >Se. >NR X21 and >C(-R X21 )2 in R X21 are each independently hydrogen or a substituent selected from the substituent group YZ, and the >NR X21 and >C(-R X21 )2R X21 are each independently linked to Y 21 and / or Y 22 , or Y 25 and / or Y 26 It may be bonded to X. 21 and X 22 For details, see "(6)X" below. 1 and X 2 」 Please refer to the description in the above. >NR X21 and >C(-R X21 )2R X21 Y 21 and / or Y 22 , or Y 25 and / or Y 26 When combining with X, see the following "(7) X 1 and X 2 and Y 1 and / or Y 2 , or Y 5 and / or Y 6 Please refer to the description under "Combination with

[0099] In formula (21), Y 21 , Y 22 , Y 23 , Y24 , Y 25 and Y 26 are each independently, =C(-R 2Y )- or =N-. R 2Y are each independently hydrogen or a substituent selected from the substituent group YZ; R 2Y Adjacent groups among these may be bonded to form a ring, and at least one hydrogen atom in the formed ring may be substituted with a substituent selected from the substituent group YZ.

[0100] Y 21 , Y 22 , Y 23 , Y 24 , Y 25 and Y 26 For details, see the above "(2) Y 1 ~Y 6 " However, Y 1 ~Y 6 There is no restriction that at least one is =N-, as in Y 21 , Y 22 , Y 23 , Y 24 , Y 25 and Y 26 are both C(-R 2Y That is, Y in the group represented by formula (21) may be 21 , Y 22 , Y 23 , Y 24 , Y 25 or Y 26 The three rings including any one of the rings may be benzene rings. 1 ~Y 6 For example, Y 2 , Y 3 , Y 4 , Y 5 and Y 6 However, each independently, =C(-R Y )- and Y 1 In the compound represented by formula (1), Y in the group represented by formula (21) is =N-. 22 , Y23 , Y 24 , Y 25 and Y 26 However, each independently, =C(-R 2Y )- and Y 21 It is also preferred that =N-.

[0101] R 2Y and adjacent R 2Y Regarding the ring formed by bonding with R, see above "(3) R 2Y " and "(4)R Y Please refer to the description of "Formation of a condensed ring by bonding between two rings."

[0102] In formula (21), L 3 is a single bond or a linking group. 3 For details and examples, see L above. 1 Please refer to the description of L 3 It is particularly preferable that L is a single bond. 3 is any R 2Y is used as a bond, and R 2Y is bonded to the C (carbon atom) to which it is bonded, or to the adjacent R 2Y are bonded to any ring-constituting atom of the ring formed by bonding together. * indicates the bonding position of the group represented by formula (21).

[0103] (6)X 1 and X 2 X 1 and X 2 are each independently >NR (amine nitrogen), >O, >C(-R)2, >S or >Se, and X 1 and X 2 Among these, >NR, >O or >C(-R)2 is preferred, and >NR or >O is particularly preferred. X 1 and X 2 are both >NR or >O, and most preferably X 1 and X 2 Both are >O. X1 and X 2 This is because when both are >O, the electron transport property is highest.

[0104] R in >NR and >C(-R)2 is hydrogen or any substituent selected from the substituent group YZ. The substituent selected from the substituent group YZ is R Y Please refer to the explanation in.

[0105] (7)X 1 and X 2 and Y 1 and / or Y 2 , or Y 5 and / or Y 6 Combination with In formula (1), "(X 1 and X 2 R in >NR and >C(-R)2 is independently linked to Y by a linking group or a single bond. 1 and / or Y 2 , or Y 5 and / or Y 6 The definition of "bonded to" refers to X represented by the following formula (1'-3) or formula (1'-4). 1 and X 2 In other words, for example, the compound having a ring structure in which X is a 6-membered ring that is the a ring in formula (1), 1 (or X 2 , or X 1 and X 2 ) to be condensed with another ring. More specifically, for example, X 1 R as >NR or >C(-R)2 and Y as 1 As =C(-R Y )-R Y An example of an embodiment in which X is bonded to X via a linking group or a single bond is given. 2 and Y 6The same applies to the bond with. The formed fused ring a' is, for example, a phenoxazine ring, a phenothiazine ring, or an acridine ring.

[0106] In addition, the above definition is based on the following formula (1'-5): 1 Or X 2 can be expressed as a compound having a ring structure in which X is incorporated into the fused ring b' and the fused ring c'. That is, for example, the six-membered ring b (or c, or b and c) in the formula (1) is 1 (or X 2 , or X 1 and X 2 ) to be condensed with another ring. More specifically, for example, X 1 R as >NR or >C(-R)2 and Y as 2 As =C(-R Y An example of the embodiment is where X is bonded to R via a linking group or a single bond. 2 and Y 5 The same applies to the bond with. The formed fused ring b' (or fused ring c') is, for example, a phenoxazine ring, a phenothiazine ring, or an acridine ring. In addition, R in the following formulas (1'-3), (1'-4) and (1'-5) Y , Y 1 ~Y 6 ,a,b,c,a',b',c',X 1 and X 2 The definition of is the same as that in formula (1).

[0107] [ka]

[0108] The linking group is preferably -O-, -S- or -C(-R)2-. In addition, R in the above "-C(-R)2-" is hydrogen, alkyl or cycloalkyl, and the details of these groups can be cited from the explanation of alkyl or cycloalkyl as the first substituent of the above-mentioned substituent group YZ. In particular, alkyl having 1 to 4 carbon atoms (e.g., methyl, ethyl, etc.) is preferable.

[0109] (8) Description of other substituents The hydrogen atoms in the chemical structure of the polycyclic aromatic compound represented by formula (1) may be entirely or partially substituted with cyano, halogen, or deuterium. The halogen atom is fluorine, chlorine, bromine, or iodine, preferably fluorine, chlorine, or bromine, and more preferably fluorine.

[0110] (9) Preferred Structure A preferred example of the polycyclic aromatic compound represented by formula (1) is the compound represented by the following formula (1-YZ-1). [ka]

[0111] In formula (1-YZ-1), X W are each independently >NR, >O or >S, and R in the >NR is an aryl having 6 to 12 carbon atoms or a heteroaryl having 2 to 12 carbon atoms; YZ However, there is at least one X W R is L YZ Instead of the bond >NR, L YZ each independently represents a single bond, an arylene having 6 to 12 carbon atoms, a heteroarylene having 2 to 12 carbon atoms, or >NR, wherein R in the >NR represents an aryl having 6 to 12 carbon atoms or a heteroaryl having 2 to 12 carbon atoms; R YZ is hydrogen, an aryl having 6 to 12 carbon atoms, or a heteroaryl having 2 to 12 carbon atoms, i is 2 to 4; At least one hydrogen atom in the chemical structure of the compound represented by formula (2) may be replaced with deuterium. X W is preferably >NR or >O. YZ is preferably a single bond. YZ is preferably hydrogen.

[0112] More specific examples of the polycyclic aromatic compound of the present invention include compounds represented by the following structural formulas. [ka]

[0113] [ka]

[0114] [ka]

[0115] [ka]

[0116] [ka]

[0117] [ka]

[0118] [ka]

[0119] [ka]

[0120] (10) Polymer compounds, etc. The polycyclic aromatic compound represented by formula (1) can also be used as a material for organic devices, for example, a material for organic electroluminescent elements, a material for organic field effect transistors, or a material for organic thin-film solar cells, in the form of a polymer compound obtained by polymerizing a reactive compound substituted with a reactive substituent as a monomer (the monomer for obtaining this polymer compound has a polymerizable substituent), 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 polymer crosslinked polymer obtained by further crosslinking the pendant polymer compound (the pendant polymer compound for obtaining this pendant polymer crosslinked polymer has a crosslinkable substituent).

[0121] The reactive substituents mentioned above (including the polymerizable substituents, the crosslinkable substituents, and the reactive substituents for obtaining a pendant polymer, hereinafter also referred to simply as "reactive substituents") are not particularly limited as long as they are substituents capable of increasing the molecular weight of the polycyclic aromatic compound, substituents capable of further crosslinking the polymer compound thus obtained, and substituents capable of pendant reaction with the main chain polymer, but are preferably those having the following structures: * in each structural formula indicates a bond position.

[0122] [ka]

[0123] Each L is independently a single bond, -O-, -S-, >C=O, -OC(=O)-, an alkylene having 1 to 12 carbon atoms, an oxyalkylene having 1 to 12 carbon atoms, or a polyoxyalkylene having 1 to 12 carbon atoms. Among the above substituents, a group represented by formula (XLS-1), formula (XLS-2), formula (XLS-3), formula (XLS-9), formula (XLS-10) or formula (XLS-17) is preferred, and a group represented by formula (XLS-1), formula (XLS-3) or formula (XLS-17) is more preferred.

[0124] The uses of such polymer compounds, crosslinked polymers, pendant type polymer compounds and pendant type crosslinked polymers (hereinafter sometimes simply referred to as "polymer compounds and crosslinked polymers") will be described later in detail.

[0125] 2. Method for producing polycyclic aromatic compounds The polycyclic aromatic compound of the present invention can be synthesized by applying the method disclosed in, for example, International Publication No. 2015 / 102118. That is, as shown in the following scheme, an intermediate in which rings a to c are bonded is synthesized, and the intermediate is cyclized by a tandem hetero Friedel-Crafts reaction (successive aromatic electrophilic substitution reaction) to synthesize a desired polycyclic aromatic compound. In the following scheme, the definitions of the symbols in each formula are the same as those described above. A compound having a group represented by formula (A-1) or formula (A-2) can be produced by using a raw material having a group represented by formula (A-1) or formula (A-2) somewhere in the reaction process, or by adding a process of introducing a group represented by formula (A-1) or formula (A-2).

[0126] [ka]

[0127] The intermediate before cyclization in the above scheme can also be synthesized by the method shown in WO 2015 / 102118 etc. That is, an intermediate having a desired substituent can be synthesized by appropriately combining the Buchwald-Hartwig reaction, Suzuki coupling reaction, or etherification reaction such as nucleophilic substitution reaction or Ullmann reaction.

[0128] The tandem hetero Friedel-Crafts cyclization shown in the above scheme is a reaction to introduce B (boron) which connects the a, b and c rings. 1 and X 2 The hydrogen atom (-H) on the a-ring between the two is ortho-metallated with n-butyllithium, sec-butyllithium, or t-butyllithium. Then, boron trichloride or boron tribromide is added to carry out lithium-boron metal exchange, and a tandem boron-Friedel-Crafts reaction is carried out by adding a Brønsted base such as N,N-diisopropylethylamine to obtain the desired product. Here, a Lewis acid such as aluminum trichloride may be added to promote the reaction.

[0129] In addition to the method of introducing lithium into the desired position by orthometalation, lithium can also be introduced into the desired position by introducing a halogen such as a bromine atom into the position where lithium is to be introduced and then carrying out halogen-metal exchange.

[0130] 3. Organic Devices The polycyclic aromatic compound according to the present invention can be used as a material for an organic device, such as an organic electroluminescent element, an organic field effect transistor, or an organic thin-film solar cell.

[0131] 3-1. Organic electroluminescent device The organic EL element according to the present embodiment will be described in detail below with reference to the drawings. Fig. 1 is a schematic cross-sectional view showing the organic EL element according to the present embodiment.

[0132] 3-1-1. Structure of organic electroluminescent device The organic EL element 100 shown in FIG. 1 has a substrate 101, an anode 102 provided on the substrate 101, a hole injection layer 103 provided on the anode 102, a hole transport layer 104 provided on the hole injection layer 103, an emitting layer 105 provided on the hole transport layer 104, an electron transport layer 106 provided on the emitting layer 105, an electron injection layer 107 provided on the electron transport layer 106, and a cathode 108 provided on the electron injection layer 107.

[0133] 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.

[0134] Not all of the above layers are essential, and the minimum structural unit is a structure consisting of an anode 102, an emitting layer 105, and a cathode 108. The hole injection layer 103, the hole transport layer 104, the electron transport layer 106, and the electron injection layer 107 are layers that may be provided optionally. Each of the above layers may consist of a single layer or multiple layers.

[0135] In addition to the above-mentioned "substrate / anode / hole injection layer / hole transport layer / light-emitting layer / electron transport layer / electron injection layer / cathode" configuration, the layers constituting the organic EL element may be configured as "substrate / anode / hole transport layer / light-emitting layer / electron transport layer / electron injection layer / cathode", "substrate / anode / hole injection ...hole transport layer / light-emitting layer / electron injection layer / cathode", "substrate / anode / hole injection layer / hole transport layer / light-emitting layer / electron injection layer / cathode", or "substrate / anode / hole injection layer / hole transport layer / light-emitting layer / electron transport The configuration may be, for example, "substrate / anode / light-emitting layer / electron transport layer / electron injection layer / cathode", "substrate / anode / hole transport layer / light-emitting layer / electron injection layer / cathode", "substrate / anode / hole transport layer / light-emitting layer / electron transport layer / cathode", "substrate / anode / hole transport layer / light-emitting layer / electron injection layer / cathode", "substrate / anode / hole injection layer / light-emitting layer / electron injection layer / cathode", "substrate / anode / hole injection layer / light-emitting layer / electron transport layer / cathode", "substrate / anode / hole injection layer / light-emitting layer / electron transport layer / cathode", "substrate / anode / light-emitting layer / electron transport layer / cathode", or "substrate / anode / light-emitting layer / electron injection layer / cathode".

[0136] 3-1-2. Substrate in organic electroluminescent device The substrate 101 is a support for the organic EL element 100, and is usually made of quartz, glass, metal, plastic, or the like. The substrate 101 is formed into a plate, film, or sheet shape depending on the purpose, and for example, a glass plate, a metal plate, a metal foil, a plastic film, a plastic sheet, or the like is used. Among them, a glass plate and a plate made of a transparent synthetic resin such as polyester, polymethacrylate, polycarbonate, or polysulfone are preferable. For a glass substrate, soda-lime glass or alkali-free glass is used, and the thickness is sufficient to maintain mechanical strength, so that it may be, for example, 0.2 mm or more. The upper limit of the thickness is, for example, 2 mm or less, preferably 1 mm or less. As for the material of the glass, it is preferable that the amount of ions eluted from the glass is small, so alkali-free glass is preferable, but soda-lime glass with a barrier coat such as SiO2 is also commercially available, and this can be used. In addition, in order to improve the gas barrier properties of the substrate 101, a gas barrier film such as a dense silicon oxide film may be provided on at least one side thereof. It is particularly preferable to provide a gas barrier film when a synthetic resin plate, film or sheet having poor gas barrier properties is used as the substrate 101.

[0137] 3-1-3. Anode in organic electroluminescent device The anode 102 plays a role in injecting 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, the holes are injected into the light-emitting layer 105 through these layers.

[0138] Materials for forming the anode 102 include inorganic compounds and organic compounds. Examples of inorganic compounds include metals (aluminum, gold, silver, nickel, palladium, chromium, etc.), metal oxides (indium oxide, tin oxide, indium-tin oxide (ITO), indium-zinc oxide (IZO), etc.), metal halides (copper iodide, etc.), copper sulfide, carbon black, ITO glass, and Nesa glass. Examples of organic compounds include polythiophenes such as poly(3-methylthiophene), polypyrrole, polyaniline, and other conductive polymers. In addition, materials that are used as anodes in organic EL elements can be appropriately selected and used.

[0139] The resistance of the transparent electrode is not limited as long as it can supply a sufficient current for the light emission of the light emitting element, but it is desirable that the resistance is low from the viewpoint of the power consumption of the light emitting element. For example, an ITO substrate of 300Ω / □ or less functions as an element electrode, but since it is now possible to supply substrates of about 10Ω / □, it is particularly desirable to use a low resistance product of, for example, 100 to 5Ω / □, preferably 50 to 5Ω / □. The thickness of the ITO can be selected arbitrarily according to the resistance value, but it is usually used in the range of 50 to 300 nm.

[0140] 3-1-4. Hole injection layer and hole transport layer in organic electroluminescent device The hole injection layer 103 plays a role of efficiently injecting holes moving from the anode 102 into the light emitting layer 105 or the hole transport layer 104. The hole transport layer 104 plays a role of efficiently transporting holes injected from the anode 102 or holes injected from the anode 102 via the hole injection layer 103 to the light emitting layer 105. The hole injection layer 103 and the hole transport layer 104 are each formed by laminating and mixing one or more types of hole injection / transport materials, or by a mixture of a hole injection / transport material and a polymer binder. Alternatively, a layer may be formed by adding an inorganic salt such as iron (III) chloride to the hole injection / transport material.

[0141] A hole injection / transport material is required to efficiently inject / transport holes from the positive electrode between electrodes to which an electric field is applied, and it is desirable for the material to have high hole injection efficiency and efficiently transport the injected holes. For this purpose, it is preferable for the material to have a small ionization potential, a large hole mobility, excellent stability, and a low probability of generating impurities that act as traps during manufacture and use.

[0142] As the material for forming the hole injection layer 103 and the hole transport layer 104, any compound can be selected from compounds conventionally used as charge transport materials for holes in photoconductive materials, p-type semiconductors, and known compounds used in hole injection layers and hole transport layers of organic EL elements. Specific examples of such compounds include carbazole derivatives (N-phenylcarbazole, polyvinylcarbazole, etc.), biscarbazole derivatives such as bis(N-arylcarbazole) or bis(N-alkylcarbazole), triarylamine derivatives (polymers having an aromatic tertiary amino in the main chain or side chain, 1,1-bis(4-di-p-tolylaminophenyl)cyclohexane, N,N'-diphenyl-N,N'-di(3-methylphenyl)-4,4'-diaminobiphenyl, N,N'-diphenyl-N,N'-dinaphthyl-4,4'-diaminobiphenyl, N,N'-diphenyl-N,N'-di(3-methylphenyl)-4,4'-diphenyl-1,1'-diamine, N,N'-dinaphthyl-N,N'-diphenyl-4,4'-diphenyl-1,1'-diamine, N4 ,N 4’ -Diphenyl-N 4 ,N 4 '-Bis(9-phenyl-9H-carbazol-3-yl)-[1,1'-biphenyl]-4,4'-diamine, N 4 ,N 4 ,N 4 ',N 4 '-Tetra[1,1'-biphenyl]-4-yl)-[1,1'-biphenyl]-4,4'-diamine, 4,4',4"-tris(3-methylphenyl(phenyl)amino)triphenylamine, N-([1,1'-biphenyl]-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluoren-2-amine, N,N-bis(4-(dibenzo[b,d]furan-4-yl)phenyl)-[1,1':4',1"-terphenyl]- triphenylamine derivatives such as 4-amine, 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 (for example, 1,4,5,8,9,12-hexaazatriphenylene-2,3,6,7,10,11-hexacarbonitrile, etc.), heterocyclic compounds such as porphyrin derivatives, polysilanes, etc. As for polymers, polycarbonates and styrene derivatives having the above-mentioned monomers in the side chains, polyvinylcarbazole, polysilanes, etc. are preferable, but there is no particular limitation as long as the compound can form a thin film necessary for the production of a light-emitting element, can inject holes from the anode, and can transport holes.

[0143] It is also known that the electrical conductivity of organic semiconductors is strongly influenced by doping. Organic semiconductor matrix substances consist of compounds with good electron donating or accepting properties. For doping with electron donating substances, strong electron acceptors such as tetracyanoquinone dimethane (TCNQ) or 2,3,5,6-tetrafluorotetracyano-1,4-benzoquinone dimethane (F4TCNQ) are known (see, for example, the references "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 by an electron transfer process in the electron donating base substance (hole transport substance). The conductivity of the base material varies considerably depending on the number and mobility of holes. Matrix materials having hole transport properties are known, for example, benzidine derivatives (TPD, etc.) or starburst amine derivatives (TDATA, etc.), or certain metal phthalocyanines (especially zinc phthalocyanine (ZnPc) and the like) (JP 2005-167175 A).

[0144] The above-mentioned hole injection layer material and hole transport layer material can be used as a hole layer material in the form of a polymer compound obtained by polymerizing a reactive compound substituted with a reactive substituent as a monomer, or a crosslinked polymer thereof, or a pendant polymer compound obtained by reacting a main chain polymer with the reactive compound, or a crosslinked pendant polymer thereof. In this case, the reactive substituent can be quoted from the description of the polycyclic aromatic compound consisting of a partial structure represented by formula (1A) and at least two partial structures represented by formula (1B). The applications of such polymer compounds and crosslinked polymers will be described in detail below.

[0145] 3-1-5. Light-emitting layer in organic electroluminescent device The light-emitting layer 105 emits light by recombining holes injected from the anode 102 and electrons injected from the cathode 108 between electrodes to which an electric field is applied. The material for forming the light-emitting layer 105 may be a compound (light-emitting compound) that is excited by the recombination of holes and electrons to emit light, and is preferably a compound that can form a stable thin film shape and shows strong light-emitting (fluorescence) efficiency in a solid state. The light-emitting layer may be a single layer or multiple layers, each of which is formed from a material for the light-emitting layer (host material, dopant material). The host material and the dopant material may each be one type or a combination of multiple types. For example, an emitting dopant and an assisting dopant may be used as the dopant material. The dopant material may be contained in the entire host material or may be contained partially in the host material. As a doping method, the light-emitting layer may be formed by co-evaporation with the host material, but it may also be mixed with the host material in advance and then evaporated at the same time. The light-emitting layer can also be formed by a wet film-forming method using a composition for forming a light-emitting layer prepared by dissolving materials in an organic solvent.

[0146] The polycyclic aromatic compound of the present invention can be preferably used as a material for forming the light-emitting layer of an organic electroluminescent device.

[0147] The light-emitting layer containing the polycyclic aromatic compound of the present invention may contain a host compound. The polycyclic aromatic compound of the present invention is preferably used as a host compound in the light-emitting layer. Here, the host compound may be one type or two or more types. The light-emitting layer may be a single layer or multiple layers. The host compound, the emitting dopant material, and the assisting dopant material may be contained in the same layer, or at least one component may be contained in each of multiple layers. The host compound and the dopant material (emitting dopant or assisting dopant) contained in the light-emitting layer may each be one type or a combination of multiple types. The assisting dopant and the emitting dopant may be entirely or partially contained in the host compound as a matrix.

[0148] The amount of the host material used varies depending on the type of the host material and may be determined according to the properties of the host material. The amount of the host material used is preferably 50 to 99.999% by mass, more preferably 80 to 99.95% by mass, and even more preferably 90 to 99.9% by mass, of the total material for the light-emitting layer.

[0149] The amount of the dopant material used varies depending on the type of the dopant material, and may be determined according to the characteristics of the dopant material. The amount of the 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, based on the total material for the light-emitting layer. The above range is preferable in that, for example, concentration quenching can be prevented.

[0150] On the other hand, in an organic electroluminescent device using a TADF material as a dopant material, a low concentration of the dopant material is preferable in terms of preventing concentration quenching, but a high concentration of the dopant material is preferable in terms of the efficiency of the thermally activated delayed fluorescence mechanism. Furthermore, in an organic electroluminescent device using a TADF material as an assisting dopant, a low concentration of the emitting dopant is preferable compared to the assisting dopant in terms of the efficiency of the thermally activated delayed fluorescence mechanism of the assisting dopant.

[0151] When an assisting dopant material is used, the amounts of the host material, the assisting dopant, and the emitting dopant used are approximately 40 to 99 mass%, 59 to 1 mass%, and 20 to 0.001 mass%, respectively, of the total material for the light-emitting layer, preferably 60 to 95 mass%, 39 to 5 mass%, and 10 to 0.01 mass%, respectively, and more preferably 70 to 90 mass%, 29 to 10 mass%, and 5 to 0.05 mass%, respectively.

[0152] 3-1-5-1. Host compound The polycyclic aromatic compound of the present invention is preferably used as a host compound in the light-emitting layer.

[0153] E of the host material T1 In order to promote TADF generation in the light-emitting layer without inhibiting it, the highest E T1 E of a dopant or assisting dopant having T1 It is preferable that the E T1 The electron transport coefficient is preferably 0.01 eV or more, more preferably 0.03 eV or more, and even more preferably 0.1 eV or more. In addition, a TADF active compound may be used as the host material.

[0154] Examples of the host material include, in addition to the polycyclic aromatic compound of the present invention, condensed ring derivatives such as anthracene and pyrene, which have been known as light emitters, bisstyryl derivatives such as bisstyryl anthracene derivatives and distyrylbenzene derivatives, tetraphenylbutadiene derivatives, cyclopentadiene derivatives, fluorene derivatives, and benzofluorene derivatives. Examples of the host material include, for example, a compound represented by the following formula (H1), a compound represented by the following formula (H2), a compound represented by the following formula (H3), a compound containing a structure represented by the following formula (H4), a compound represented by the following formula (H5), and a compound represented by the following formula (H6). Any one or more of these compounds may be used in combination with the polycyclic aromatic compound of the present invention.

[0155] [ka]

[0156] 3-1-5-1-1. Compound represented by formula (H1) [ka]

[0157] In formula (H1), L 1 is an arylene 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. Specific examples thereof include divalent groups such as a benzene ring, a biphenyl ring, a naphthalene ring, a terphenyl ring, an acenaphthylene ring, a fluorene ring, a phenalene ring, a phenanthrene ring, a triphenylene ring, a pyrene ring, a naphthacene ring, a perylene ring, and a pentacene ring. At least one hydrogen atom in the compound represented by formula (H1) may be substituted with alkyl having 1 to 6 carbon atoms, cycloalkyl having 3 to 14 carbon atoms, cyano, halogen or deuterium.

[0158] 3-1-5-1-2. Compound represented by formula (H2) [ka]

[0159] In formula (H2), L 2 and L 3are each independently an aryl having 6 to 30 carbon atoms or a heteroaryl having 2 to 30 carbon atoms. The aryl is preferably an aryl having 6 to 24 carbon atoms, more preferably an aryl having 6 to 16 carbon atoms, further preferably an aryl having 6 to 12 carbon atoms, and particularly preferably an aryl having 6 to 10 carbon atoms, and specific examples thereof include monovalent groups such as a benzene ring, a biphenyl ring, a naphthalene ring, a terphenyl ring, an acenaphthylene ring, a fluorene ring, a phenalene ring, a phenanthrene ring, a triphenylene ring, a pyrene ring, a naphthacene ring, a perylene ring, and a pentacene ring. The heteroaryl is preferably a heteroaryl having 2 to 25 carbon atoms, more preferably a heteroaryl having 2 to 20 carbon atoms, still more preferably a heteroaryl having 2 to 15 carbon atoms, and particularly preferably a heteroaryl having 2 to 10 carbon atoms. 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 benzo Examples of monovalent groups include an imidazole 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 compound represented by formula (H2) may be substituted with alkyl having 1 to 6 carbon atoms, cycloalkyl having 3 to 14 carbon atoms, cyano, halogen or deuterium.

[0160] 3-1-5-1-3. Compound represented by formula (H3) [ka]

[0161] In formula (H3), Each MU is independently a divalent aromatic group, each EC is independently a monovalent aromatic group, and k is an integer of 2 to 50,000.

[0162] More specifically, Each MU is independently arylene, heteroarylene, diarylenarylamino, diarylenarylboryl, oxaborine-diyl, or azaborine-diyl; each E C is independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, or aryloxy; At least one hydrogen in MU and EC may be further substituted with aryl, heteroaryl, diarylamino, alkyl, and cycloalkyl; k is an integer from 2 to 50,000. k is preferably an integer from 20 to 50,000, and more preferably an integer from 100 to 50,000.

[0163] At least one hydrogen atom in MU and EC in formula (H3) may be substituted with an alkyl group having 1 to 24 carbon atoms, a cycloalkyl group having 3 to 24 carbon atoms, a halogen atom or a deuterium atom; further, any -CH2- in the alkyl group may be substituted with -O- or -Si(CH3)2-; any -CH2- in the alkyl group except for the -CH2- directly bonded to EC in formula (H3) may be substituted with an arylene group having 6 to 24 carbon atoms; and any hydrogen atom in the alkyl group may be substituted with a fluorine atom.

[0164] 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 in such a group is substituted with an alkyl or the like).

[0165] [ka]

[0166] More specifically, the divalent group may have any one of the following structures: In these, MU bonds to another MU or EC at *.

[0167] [ka]

[0168] [ka]

[0169] [ka]

[0170] [ka]

[0171] [ka]

[0172] [ka]

[0173] [ka]

[0174] [ka]

[0175] [ka]

[0176] Examples of EC include groups represented by the following formulas: In these, EC is bonded to MU at *.

[0177] [ka]

[0178] [ka]

[0179] From the viewpoint of solubility and coating film-forming property, the compound represented by formula (H3) is preferably such that 10 to 100% of the total number of MUs (k) in the molecule have an alkyl having a carbon number of 1 to 24, more preferably 30 to 100% of the total number of MUs (k) in the molecule have an alkyl having a carbon number of 1 to 18 (branched chain alkyl having a carbon number of 3 to 18), and even more preferably 50 to 100% of the total number of MUs (k) in the molecule have an alkyl having a carbon number of 1 to 12 (branched chain alkyl having a carbon number of 3 to 12). On the other hand, from the viewpoint of in-plane orientation and charge transport, it is preferable that 10 to 100% of the total number of MUs (k) in the molecule have an alkyl having a carbon number of 7 to 24, and more preferably 30 to 100% of the total number of MUs (k) in the molecule have an alkyl having a carbon number of 7 to 24 (branched chain alkyl having a carbon number of 7 to 24).

[0180] 3-1-5-1-4. Compounds containing the structure represented by formula (H4) The compound containing a structure represented by formula (H4) contains a plurality of structures represented by formula (H4), preferably 1 to 5 structures, more preferably 1 to 3 structures, even more preferably 1 to 2 structures, and most preferably 1 structure. When a plurality of structures are contained, the structures are directly bonded to each other via a single bond or are bonded to each other via a specific linking group.

[0181] [ka]

[0182] In formula (H4), G is "=C(-H)-" or "=N-", and the H in the "=C(-H)-" may be substituted with a substituent or another structure represented by formula (H4).

[0183] As the compound containing the structure represented by formula (H4), for example, the compounds described in WO 2012 / 153780 and WO 2013 / 038650 can be used, and can be produced according to the methods described in the above-mentioned documents.

[0184] Examples of the substituent when H in "=C(-H)-" of G is substituted include aryl, heteroaryl, substituted silyl, substituted phosphine oxide group, and substituted carboxy.

[0185] Specific examples of the "aryl" substituent include phenyl, tolyl, xylyl, naphthyl, phenanthryl, pyrenyl, chrysenyl, benzo[c]phenanthryl, benzo[g]chrysenyl, benzanthryl, triphenylenyl, fluorenyl, 9,9-dimethylfluorenyl, benzofluorenyl, dibenzofluorenyl, biphenylyl, terphenylyl, quaterphenylyl, fluoranthenyl, etc., and preferably phenyl, biphenylyl, terphenylyl, quaterphenylyl, naphthyl, triphenylenyl, and fluorenyl. Examples of aryl having a substituent include tolyl, xylyl, and 9,9-dimethylfluorenyl. As shown in the specific examples, aryl includes both fused and non-fused aryl.

[0186] Specific examples of the substituent "heteroaryl" include pyrrolyl, pyrazolyl, pyrazinyl, pyrimidinyl, pyridazinyl, pyridyl, triazinyl, indolyl, isoindolyl, imidazolyl, benzimidazolyl, indazolyl, imidazo[1,2-a]pyridinyl, furyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, azadibenzofuranyl, thienyl, benzothienyl, dibenzothienyl, azadibenzothienyl, quinolyl, isoquinolyl, quinoxalinyl, quinazolinyl, and naphthyridinyl. Examples of the aryl include carbazolyl, azacarbazolyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, phenothiazinyl, phenoxazinyl, oxazolyl, oxadiazolyl, furazanyl, benzoxazolyl, thiazolyl, thiadiazolyl, benzothiazolyl, triazolyl, and tetrazolyl. Preferred examples include dibenzofuranyl, dibenzothienyl, carbazolyl, pyridyl, pyrimidinyl, triazinyl, azadibenzofuranyl, and azadibenzothienyl. Dibenzofuranyl, dibenzothienyl, azadibenzofuranyl, and azadibenzothienyl are more preferred.

[0187] The substituent "substituted silyl" is also preferably a group selected from the group consisting of substituted or unsubstituted trialkylsilyl, substituted or unsubstituted arylalkylsilyl, and substituted or unsubstituted triarylsilyl.

[0188] Specific examples of the substituted or unsubstituted trialkylsilyl include trimethylsilyl and triethylsilyl. Specific examples of the substituted or unsubstituted arylalkylsilyl include diphenylmethylsilyl, ditolylmethylsilyl, and phenyldimethylsilyl. Specific examples of the substituted or unsubstituted triarylsilyl include triphenylsilyl and tritolylsilyl.

[0189] The "substituted phosphine oxide group" as a substituent is also preferably a substituted or unsubstituted diarylphosphine oxide group. Specific examples of the substituted or unsubstituted diarylphosphine oxide group include diphenylphosphine oxide and ditolylphosphine oxide.

[0190] The substituent "substituted carboxy" includes, for example, benzoyloxy and the like.

[0191] Examples of the linking group that bonds a plurality of structures represented by formula (H4) include divalent to tetravalent, divalent to trivalent, or divalent derivatives of the above-mentioned aryl or heteroaryl.

[0192] Specific examples of the compound containing the structure represented by formula (H4) are shown below. [ka]

[0193] 3-1-5-1-5. Compounds represented by formula (H5) and compounds represented by formula (H6) 3-1-5-1-5-1. Compound represented by formula (H5) [ka]

[0194] In formula (H5), R 1 ~R 11 are each independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino or aryloxy, in which at least one hydrogen may be further substituted with aryl, heteroaryl or diarylamino; R 1 ~R 11Adjacent groups among these may be bonded to each other to form an aryl ring or a heteroaryl ring together with the a ring, the b ring or the c ring, and at least one hydrogen atom in the formed ring may be replaced by an aryl, a heteroaryl, a diarylamino, a diheteroarylamino, an arylheteroarylamino or an aryloxy, and at least one hydrogen atom in these rings may be further replaced by an aryl, a heteroaryl or a diarylamino. In addition, at least one (preferably 1 to 3) of any -C(R n )= (n is 1 to 11) may be substituted with -N=. Furthermore, at least one hydrogen in the compound represented by formula (H5) may be substituted with a group represented by formula (FG-1), a group represented by formula (FG-2), or an alkyl having 1 to 24 carbon atoms, and 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 the compound represented by formula (H5) may be substituted with an arylene having 6 to 24 carbon atoms, and any hydrogen in the alkyl may be substituted with fluorine. In addition, at least one hydrogen in the compound represented by formula (H5) may be substituted with a halogen or deuterium.

[0195] In formula (H5), the substituents R 1 ~R 11Adjacent groups among the above may be bonded to each other to form an aryl ring or a heteroaryl ring together with the a ring, the b ring, or the c ring, and at least one hydrogen in the formed ring may be substituted with an aryl, a heteroaryl, a diarylamino, a diheteroarylamino, an arylheteroarylamino, or an aryloxy, and at least one hydrogen in these may be further substituted with an aryl, a heteroaryl, or a diarylamino. However, here, "adjacent groups" refers to groups adjacent to each other on the same ring, and a compound in which "adjacent groups are bonded to each other to form an aryl ring or a heteroaryl ring together with the a ring, the b ring, or the c ring" corresponds to, for example, compounds represented by formulas (H5-2) to (H5-17) listed as specific compounds to be described later. That is, for example, it is a compound formed by condensing a benzene ring, an indole ring, a pyrrole ring, a benzofuran ring, or a benzothiophene ring to the a ring (or the b ring or the c ring), and the condensed ring formed is a naphthalene ring, a carbazole ring, an indole ring, a dibenzofuran ring, or a dibenzothiophene ring, respectively.

[0196] 3-1-5-1-5-2. Compound represented by formula (H6) [ka]

[0197] In formula (H6), R 1 ~R 16 are each independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino or aryloxy, in which at least one hydrogen may be further substituted with aryl, heteroaryl or diarylamino; R 1 ~R 16Adjacent groups among these may be bonded to each other to form an aryl ring or a heteroaryl ring together with the a ring, the b ring, the c ring or the d ring, and at least one hydrogen atom in the formed ring may be substituted by an aryl, a heteroaryl, a diarylamino, a diheteroarylamino, an arylheteroarylamino or an aryloxy, and at least one hydrogen atom in these rings may be further substituted by an aryl, a heteroaryl or a diarylamino. Furthermore, at least one hydrogen in the compound represented by formula (H-6) may be substituted with an alkyl having 1 to 24 carbon atoms, and 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 the compound represented by formula (H6) may be substituted with an arylene having 6 to 24 carbon atoms, and any hydrogen in the alkyl may be substituted with fluorine. In addition, at least one hydrogen in the compound represented by formula (H6) may be substituted with a halogen or deuterium.

[0198] In formula (H6), the substituents R 1 ~R 16Adjacent groups among may be bonded to each other to form an aryl or heteroaryl ring together with the a, b, c or c ring, and at least one hydrogen in the formed ring may be substituted with an aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino or aryloxy, and at least one hydrogen in these may be further substituted with an aryl, heteroaryl or diarylamino. However, here, "adjacent groups" refers to groups adjacent to each other on the same ring, and a compound in which "adjacent groups are bonded to each other to form an aryl or heteroaryl ring together with the a, b, c or d ring" can be explained with reference to, for example, compounds represented by formulas (H6-2) to (H6-5) listed below as specific compounds of formula (H6). That is, for example, it is a compound formed by condensing a benzene ring, an indole ring, a pyrrole ring, a benzofuran ring, or a benzothiophene ring to ring a (or ring b, ring c, or ring d), and the condensed ring formed is a naphthalene ring, a carbazole ring, an indole ring, a dibenzofuran ring, or a dibenzothiophene ring, respectively.

[0199] 3-1-5-1-5-3. R in formula (H5) 1 ~R 11 " and "R in formula (H6) 1 ~R 16 」 "R in formula (H5) 1 ~R 11 " and "R in formula (H6) 1 ~R 16" are each independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino or aryloxy, and are preferably an aryl having 6 to 30 carbon atoms, a heteroaryl having 2 to 30 carbon atoms, diarylamino (amino having two aryl groups having 6 to 30 carbon atoms), diheteroarylamino (amino having two heteroaryl groups having 2 to 30 carbon atoms), arylheteroarylamino (amino having an aryl group having 6 to 30 carbon atoms and a heteroaryl group having 2 to 30 carbon atoms) or aryloxy having 6 to 30 carbon atoms.

[0200] Examples of the aryl of "aryl", "diarylamino", the aryl of "arylheteroarylamino", and the aryl of "aryloxy" include a monocyclic benzene ring, a bicyclic bicyclic bicyclic naphthalene 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, a fused tetracyclic tricyclic triphenylene ring, a pyrene ring, a naphthacene ring, a fused pentacyclic perylene ring, a pentacene ring, and the like. Furthermore, as described below, those aryls substituted with a heteroaryl as defined below are also defined as aryls in formula (H5) and formula (H6).

[0201] Examples of the heteroaryl in "heteroaryl" and "diheteroarylamino" and the heteroaryl in "arylheteroarylamino" 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, quinoline ring, isoquinoline ring, cinnoline ring, quinazoline ring, quinoxaline ring, phthalazine ring, naphthyridine ring, purine ring, pteridine ring, carbazole ring, acridine ring, phenoxathiin ring, phenoxazine ring, phenothiazine ring, phenazine ring, indolizine ring, furan ring, benzofuran ring, isobenzofuran ring, dibenzofuran ring, thiophene ring, benzothiophene ring, dibenzothiophene ring, furazan ring, oxadiazole ring, thianthrene ring, and monovalent groups such as the heteroaryl substituted with N-aryl.Furthermore, as described below, those heteroaryl substituted with the aryl defined above are also defined as heteroaryl in formula (H5) and formula (H6).

[0202] In addition, R in formula (H5) 1 ~R 11 and R in formula (H6) 1 ~R 16 At least one hydrogen atom in the aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, or aryloxy described above may be further substituted with an aryl, heteroaryl, or diarylamino. The aryl, heteroaryl, or diarylamino to be substituted in this manner includes R 1 ~R 11 Or R 1 ~R 16 The same items as those explained in the previous section can be mentioned.

[0203] R 1 ~R11 Or R 1 ~R 16 Specific examples of the groups include groups represented by the following formulae (RG-1) to (RG-10). The groups represented by the following formulae (RG-1) to (RG-10) are bonded to the groups represented by the formulae (H5) and (H6) at *.

[0204] [ka]

[0205] The definitions of "aryl" and "heteroaryl" in formulae (H5) and (H6) are explained with reference to the above-mentioned specific groups. Formulae (RG-1), (RG-4) and (RG-7) are aryl, formulae (RG-2), (RG-3) and (RG-6) are heteroaryl, formula (RG-9) is heteroaryl substituted with heteroaryl, and formula (RG-10) is aryl substituted with heteroaryl. Formula (RG-5) is aryl (phenyl) substituted with diarylamino (diphenylamino), and formula (RG-8) is diarylamino (diphenylamino).

[0206] [ka]

[0207] 3-1-5-1-5-4. In formula (H5), a ring formed by bonding adjacent groups of ring a, ring b, or ring c, and in formula (H6), a ring formed by bonding adjacent groups of ring a, ring b, ring c, or ring d In formula (H5), "R 1 ~R 11 "An aryl ring formed together with the ring a, ring b or ring c by bonding adjacent groups among these" and "R 1 ~R 16 Examples of the aryl ring formed together with ring a, ring b, ring c or ring d by bonding adjacent groups among the above include aryl rings having 6 to 30 carbon atoms, preferably aryl rings having 6 to 16 carbon atoms, more preferably aryl rings having 6 to 12 carbon atoms, and particularly preferably aryl rings having 6 to 10 carbon atoms. However, the number of carbon atoms in the formed aryl ring includes the 6 carbon atom in ring a, ring b, ring c or d.

[0208] Specific examples of the aryl ring formed include a naphthalene ring which is a fused bicyclic ring; an acenaphthylene ring, a fluorene ring, a phenalene ring, a phenanthrene ring which is a fused tricyclic ring; a triphenylene ring, a pyrene ring, a naphthacene ring which is a fused tetracyclic ring; a perylene ring and a pentacene ring which are fused pentacyclic rings.

[0209] In formula (H5), "R 1 ~R 11 and "a heteroaryl ring formed together with ring a, ring b or ring c by bonding adjacent groups among the above" in formula (H6). 1 ~R 16 Examples of the "aryl ring formed together with ring a, ring b, ring c, or ring d by bonding adjacent groups among the above" include heteroaryl rings having 6 to 30 carbon atoms, preferably heteroaryl rings having 6 to 25 carbon atoms, more preferably heteroaryl rings having 6 to 20 carbon atoms, further preferably heteroaryl rings having 6 to 15 carbon atoms, and particularly preferably heteroaryls having 6 to 10 carbon atoms. Examples of the "heteroaryl ring" include heterocycles containing, in addition to carbon, 1 to 5 heteroatoms selected from oxygen, sulfur, and nitrogen as ring-constituting atoms. However, the number of carbon atoms in the formed heteroaryl ring includes the 6 carbon atoms in ring a, ring b, ring c, or ring d.

[0210] Specific examples of the formed heteroaryl ring include, for example, an indole ring, an isoindole ring, a 1H-indazole ring, a benzimidazole ring, a benzoxazole ring, a benzothiazole ring, a 1H-benzotriazole ring, a quinoline ring, an isoquinoline ring, a cinnoline ring, a quinazoline ring, a quinoxaline ring, a phthalazine ring, a carbazole ring, an acridine ring, a phenoxathiin ring, a phenoxazine ring, a phenothiazine ring, a phenazine ring, a benzofuran ring, an isobenzofuran ring, a dibenzofuran ring, a benzothiophene ring, a dibenzothiophene ring, and a thianthrene ring.

[0211] At least one hydrogen atom in the ring formed may be replaced by aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, or aryloxy, and at least one hydrogen atom in each of these may be further replaced by aryl, heteroaryl, or diarylamino. For this explanation, R 1 ~R 11 and R in formula (H6) 1 ~R 16 The explanation in the above can be cited.

[0212] 3-1-5-1-5-5. Specific examples of compounds A more specific structure of the compound represented by formula (H5) or formula (H6) is shown below. The specific structure of the compound represented by the following formula (H5) or formula (H6) may be substituted with alkyl having 1 to 24 carbon atoms.

[0213] [ka]

[0214] [ka]

[0215] [ka]

[0216] [ka]

[0217] [ka]

[0218] [ka]

[0219]

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[0220]

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[0221]

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[0222]

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[0223]

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[0224]

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[0225]

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[0226]

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[0227]

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[0228]

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[0229]

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[0230]

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[0231]

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[0232]

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[0233]

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[0234]

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[0235]

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[0236]

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[0237]

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[0238]

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[0239]

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[0240]

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[0241]

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[0242]

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[0243]

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[0244]

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[0245]

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[0246]

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[0247] 3-1-5-1-5-6. Method for producing a compound represented by formula (H5) or formula (H6) For the compound represented by formula (H5), first, the rings a to c are bonded with a bonding group (-O-) to produce an intermediate (first reaction), and then the rings a to c are bonded with a bonding group (group containing B) to produce the final product (second reaction). For the compound represented by formula (H6), first, the rings a to d are bonded with a bonding group (>NH or single bond) to produce an intermediate (first reaction), and then the rings a to d are bonded with a bonding group (group containing B) to produce the final product (second reaction). For the first reaction, for example, if it is an etherification reaction, a general reaction such as a nucleophilic substitution reaction or an Ullmann reaction can be used, and if it is an amination reaction, a general reaction such as a Buchwald-Hartwig reaction can be used. For the second reaction, a tandem hetero Friedel-Crafts reaction (successive aromatic electrophilic substitution reaction, the same applies below) can be used.

[0248] <Production method: Example of the second reaction of the compound represented by formula (H5)> The second reaction is a reaction to introduce B (boron) that bonds the a, b and c rings, as shown in the following scheme (1). For example, the case of the compound represented by formula (H5) is shown below. First, the hydrogen atom between the two Os is orthometalated with n-butyllithium, sec-butyllithium or t-butyllithium. Next, boron trichloride, boron tribromide or the like is added to carry out lithium-boron metal exchange, and then a tandem boron-Friedel-Crafts reaction is carried out by adding a Bronsted base such as N,N-diisopropylethylamine to obtain the target product. In the second reaction, a Lewis acid such as aluminum trichloride may be added to promote the reaction.

[0249] [ka]

[0250] In the above scheme, lithium was introduced into the desired position by orthometalation. However, as shown in the following scheme (2), lithium can also be introduced into the desired position by introducing a bromine atom or the like into the desired position and then by halogen-metal exchange.

[0251] [ka]

[0252] By appropriately selecting the above-mentioned synthesis method and the raw materials to be used, a compound having a substituent at a desired position and represented by formula (H-5) can be synthesized.

[0253] <Production method: Example of a method for producing the compound represented by formula (H6)> The first and second reactions in the method for producing the compound represented by formula (H5) described above can also be applied to the method for producing the compound represented by formula (H6). In other words, the second reaction is a reaction for introducing B (boron) which bonds NH to the c and d rings, and the hydrogen atom of NH is orthometalated with n-butyllithium, sec-butyllithium, t-butyllithium, or the like, and then boron trichloride, boron tribromide, or the like is added to carry out lithium-boron metal exchange, and then a tandem boron-Friedel-Crafts reaction is carried out by adding a Bronsted base such as N,N-diisopropylethylamine, to obtain the target product. Here too, a Lewis acid such as aluminum trichloride may be added in the second reaction to promote the reaction.

[0254] 3-1-5-2.Dopant materials The dopant material is not particularly limited, and may be any known compound, and may be selected from a variety of materials depending on the desired emission color. The polycyclic aromatic compound of the present invention may be used as the dopant material. Specific examples of such compounds include condensed ring derivatives of phenanthrene, anthracene, pyrene, tetracene, pentacene, perylene, naphthopyrene, dibenzopyrene, rubrene, and chrysene, benzoxazole derivatives, benzothiazole derivatives, benzimidazole derivatives, benzotriazole derivatives, oxazole derivatives, oxadiazole derivatives, thiazole derivatives, imidazole derivatives, thiadiazole derivatives, triazole derivatives, pyrazoline derivatives, stilbene derivatives, thiophene derivatives, and tetraphenylbutadiene. derivatives, cyclopentadiene derivatives, bisstyryl derivatives such as bisstyrylanthracene derivatives and distyrylbenzene derivatives (JP Patent Publication No. 245087 / 1999), bisstyrylarylene derivatives (JP Patent Publication No. 247278 / 1990), diazaindacene derivatives, furan derivatives, benzofuran derivatives, isobenzofuran derivatives such as phenylisobenzofuran, dimesitylisobenzofuran, di(2-methylphenyl)isobenzofuran, di(2-trifluoromethylphenyl)isobenzofuran, and phenylisobenzofuran coumarin derivatives such as dibenzofuran derivatives, 7-dialkylaminocoumarin derivatives, 7-piperidinocoumarin derivatives, 7-hydroxycoumarin derivatives, 7-methoxycoumarin derivatives, 7-acetoxycoumarin derivatives, 3-benzothiazolylcoumarin derivatives, 3-benzimidazolylcoumarin derivatives, and 3-benzoxazolylcoumarin derivatives, dicyanomethylenepyran derivatives, dicyanomethylenethiopyran derivatives, polymethine derivatives, cyanine derivatives, oxobenzoanthracene derivatives, xanthene derivatives, and rhodamine derivatives. conductors, fluorescein derivatives, pyrylium derivatives, carbostyril derivatives, acridine derivatives, oxazine derivatives, phenylene oxide derivatives, quinacridone derivatives, quinazoline derivatives, pyrrolopyridine derivatives, furopyridine derivatives, 1,2,5-thiadiazolopyrene derivatives, pyrromethene derivatives, perinone derivatives, pyrrolopyrrole derivatives, squarylium derivatives, violanthrone derivatives, phenazine derivatives, acridone derivatives, deazaflavin derivatives, fluorene derivatives and benzofluorene derivatives.

[0255] Examples of dopant materials for each color of light emitted include aromatic hydrocarbon compounds such as naphthalene, anthracene, phenanthrene, pyrene, triphenylene, perylene, fluorene, indene, and chrysene, and derivatives thereof, furan, pyrrole, thiophene, silole, 9-silafluorene, 9,9'-spirobisilafluorene, benzothiophene, benzofuran, indole, dibenzothiophene, dibenzofuran, imidazopyridine, phenanthroline, pyrazine, naphthyridine, quinoxaline, pyrrolopyridine, and pyrrolopyridine. Examples include aromatic heterocyclic compounds such as lysine and thioxanthene and their derivatives, distyrylbenzene derivatives, tetraphenylbutadiene derivatives, stilbene derivatives, aldazine derivatives, coumarin derivatives, azole derivatives such as imidazole, thiazole, thiadiazole, carbazole, oxazole, oxadiazole, and triazole and their metal complexes, and aromatic amine derivatives typified by N,N'-diphenyl-N,N'-di(3-methylphenyl)-4,4'-diphenyl-1,1'-diamine.

[0256] In addition, examples of the green to yellow dopant material include coumarin derivatives, phthalimide derivatives, naphthalimide derivatives, perinone derivatives, pyrrolopyrrole derivatives, cyclopentadiene derivatives, acridone derivatives, quinacridone derivatives, and naphthacene derivatives such as rubrene. Further, preferred examples of the compounds exemplified as the above blue to blue-green dopant materials include compounds in which a substituent that enables a longer wavelength, such as aryl, heteroaryl, arylvinyl, amino, or cyano, has been introduced.

[0257] Further examples of orange to red dopant materials include naphthalimide derivatives such as bis(diisopropylphenyl)perylenetetracarboxylic acid imide, perinone derivatives, rare earth complexes such as Eu complexes having acetylacetone, benzoylacetone, and phenanthroline as ligands, 4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran and analogs thereof, metal phthalocyanine derivatives such as magnesium phthalocyanine and aluminum chlorophthalocyanine, rhodamine compounds, deazaflavin derivatives, coumarin derivatives, quinacridone derivatives, phenoxazine derivatives, oxazine derivatives, quinazoline derivatives, pyrrolopyridine derivatives, squarylium derivatives, violanthrone derivatives, phenazine derivatives, phenoxazone derivatives, and thiadiazolopyrene derivatives. Further preferred examples of the compounds exemplified above as the blue to blue-green and green to yellow dopant materials include compounds obtained by introducing a substituent that enables a longer wavelength, such as aryl, heteroaryl, arylvinyl, amino, or cyano.

[0258] In addition, the dopant may be appropriately selected from the compounds described in Chemical Industry, June 2004, p. 13 and the references cited therein.

[0259] Among the above-mentioned dopant materials, amines having a stilbene structure, perylene derivatives, borane derivatives, aromatic amine derivatives, coumarin derivatives, pyran derivatives, or pyrene derivatives are particularly preferred.

[0260] The amine having a stilbene structure is represented, for example, by the following formula. [ka] In the formula, Ar 1 is an m-valent group derived from an aryl having 6 to 30 carbon atoms, and Ar 2 and Ar 3 are each independently an aryl having 6 to 30 carbon atoms, 1 ~Ar 3 At least one of the groups has a stilbene structure, and Ar1 ~Ar 3 may be substituted with aryl, heteroaryl, alkyl, cycloalkyl, trisubstituted silyl (silyl trisubstituted with aryl, alkyl and / or cycloalkyl) or cyano, and m is an integer from 1 to 4.

[0261] The amine having a stilbene structure is more preferably a diaminostilbene represented by the following formula. [ka] In the formula, Ar 2 and Ar 3 are each independently an aryl having 6 to 30 carbon atoms, and Ar 2 and Ar 3 may be substituted with aryl, heteroaryl, alkyl, cycloalkyl, trisubstituted silyl (silyl trisubstituted with aryl, alkyl and / or cycloalkyl) or cyano.

[0262] Specific examples of the aryl having 6 to 30 carbon atoms include phenyl, naphthyl, acenaphthylenyl, fluorenyl, phenalenyl, phenanthrenyl, anthryl, fluoranthenyl, triphenylenyl, pyrenyl, chrysenyl, naphthacenyl, perylenyl, stilbenyl, distyrylphenyl, distyrylbiphenylyl, and distyrylfluorenyl.

[0263] Specific examples of the amine having a stilbene structure include N,N,N',N'-tetra(4-biphenylyl)-4,4'-diaminostilbene, N,N,N',N'-tetra(1-naphthyl)-4,4'-diaminostilbene, N,N,N',N'-tetra(2-naphthyl)-4,4'-diaminostilbene, N,N'-di(2-naphthyl)-N,N'-diphenyl-4,4'-diaminostilbene, and N,N'-di(9-phenanthryl)-N,N'-diphenyl-4,4'-diaminostilbene. Examples of such aryl-4,4'-diaminostilbene include 4,4'-bis[4"-bis(diphenylamino)styryl]-biphenyl, 1,4-bis[4'-bis(diphenylamino)styryl]-benzene, 2,7-bis[4'-bis(diphenylamino)styryl]-9,9-dimethylfluorene, 4,4'-bis(9-ethyl-3-carbazovinylene)-biphenyl, and 4,4'-bis(9-phenyl-3-carbazovinylene)-biphenyl. Furthermore, amines having a stilbene structure, such as those described in JP-A Nos. 2003-347056 and 2001-307884, may also be used.

[0264] Examples of perylene derivatives include 3,10-bis(2,6-dimethylphenyl)perylene, 3,10-bis(2,4,6-trimethylphenyl)perylene, 3,10-diphenylperylene, 3,4-diphenylperylene, 2,5,8,11-tetra-t-butylperylene, 3,4,9,10-tetraphenylperylene, 3-(1'-pyrenyl)-8,11-di(t-butyl)perylene, 3-(9'-anthryl)-8,11-di(t-butyl)perylene, and 3,3'-bis(8,11-di(t-butyl)perylenyl). Also usable are perylene derivatives described in JP-A-11-97178, JP-A-2000-133457, JP-A-2000-26324, JP-A-2001-267079, JP-A-2001-267078, JP-A-2001-267076, JP-A-2000-34234, JP-A-2001-267075, and JP-A-2001-217077.

[0265] Examples of borane derivatives include 1,8-diphenyl-10-(dimesitylboryl)anthracene, 9-phenyl-10-(dimesitylboryl)anthracene, 4-(9'-anthryl)dimesitylborylnaphthalene, 4-(10'-phenyl-9'-anthryl)dimesitylborylnaphthalene, 9-(dimesitylboryl)anthracene, 9-(4'-biphenylyl)-10-(dimesitylboryl)anthracene, and 9-(4'-(N-carbazolyl)phenyl)-10-(dimesitylboryl)anthracene. Also, borane derivatives described in, for example, International Publication No. 2000 / 40586 may be used.

[0266] The aromatic amine derivative is represented, for example, by the following formula: [ka] In the formula, Ar 4 is an n-valent group derived from an aryl having 6 to 30 carbon atoms, and Ar 5 and Ar 6 are each independently an aryl having 6 to 30 carbon atoms, and Ar 4 ~Ar 6 may be substituted with aryl, heteroaryl, alkyl, cycloalkyl, trisubstituted silyl (silyl trisubstituted with aryl, alkyl and / or cycloalkyl) or cyano, and n is an integer from 1 to 4.

[0267] In particular, Ar 4 is a divalent group derived from anthracene, chrysene, fluorene, benzofluorene, or pyrene, and Ar 5 and Ar 6 are each independently an aryl having 6 to 30 carbon atoms, and Ar 4 ~Ar 6 is optionally substituted with aryl, heteroaryl, alkyl, cycloalkyl, trisubstituted silyl (silyl trisubstituted with aryl, alkyl and / or cycloalkyl) or cyano, and n is 2.

[0268] Specific examples of the aryl having 6 to 30 carbon atoms include phenyl, naphthyl, acenaphthylenyl, fluorenyl, phenalenyl, phenanthrenyl, anthryl, fluoranthenyl, triphenylenyl, pyrenyl, chrysenyl, naphthacenyl, perylenyl, and pentacenyl.

[0269] Examples of aromatic amine derivatives include chrysene derivatives such as N,N,N',N'-tetraphenylchrysene-6,12-diamine, N,N,N',N'-tetra(p-tolyl)chrysene-6,12-diamine, N,N,N',N'-tetra(m-tolyl)chrysene-6,12-diamine, N,N,N',N'-tetrakis(4-isopropylphenyl)chrysene-6,12-diamine, N,N,N',N'-tetra(naphthalen-2-yl)chrysene-6,12-diamine, and N,N'-diphenyl -N,N'-di(p-tolyl)chrysene-6,12-diamine, N,N'-diphenyl-N,N'-bis(4-ethylphenyl)chrysene-6,12-diamine, N,N'-diphenyl-N,N'-bis(4-isopropylphenyl)chrysene-6,12-diamine, N,N'-diphenyl-N,N'-bis(4-t-butylphenyl)chrysene-6,12-diamine, N,N'-bis(4-isopropylphenyl)-N,N'-di(p-tolyl)chrysene-6,12-diamine and the like.

[0270] Examples of pyrene-based compounds include N,N,N',N'-tetraphenylpyrene-1,6-diamine, N,N,N',N'-tetra(p-tolyl)pyrene-1,6-diamine, N,N,N',N'-tetra(m-tolyl)pyrene-1,6-diamine, N,N,N',N'-tetrakis(4-isopropylphenyl)pyrene-1,6-diamine, N,N,N',N'-tetrakis(3,4-dimethylphenyl)pyrene-1,6-diamine, N,N'-diphenyl-N,N'-di(p-tolyl)pyrene-1,6-diamine, N,N'-diphenyl-N,N'-bis(4-ethylphenyl)pyrene-1, 6-diamine, N,N'-diphenyl-N,N'-bis(4-isopropylphenyl)pyrene-1,6-diamine, N,N'-diphenyl-N,N'-bis(4-t-butylphenyl)pyrene-1,6-diamine, N,N'-bis(4-isopropylphenyl)-N,N'-di(p-tolyl)pyrene-1,6-diamine, N,N,N',N'-tetrakis(3,4-dimethylphenyl)-3,8-diphenylpyrene-1,6-diamine, N,N,N,N-tetraphenylpyrene-1,8-diamine, N,N'-bis(biphenyl-4-yl)-N,N'-diphenylpyrene-1,8-diamine, N 1 ,N 6 -Diphenyl-N 1 ,N 6 -bis-(4-trimethylsilanyl-phenyl)-1H,8H-pyrene-1,6-diamine.

[0271] Examples of anthracene-based compounds include N,N,N,N-tetraphenylanthracene-9,10-diamine, N,N,N',N'-tetra(p-tolyl)anthracene-9,10-diamine, N,N,N',N'-tetra(m-tolyl)anthracene-9,10-diamine, N,N,N',N'-tetrakis(4-isopropylphenyl)anthracene-9,10-diamine, N,N'-diphenyl-N,N'-di(p-tolyl)anthracene-9,10-diamine, N,N'-diphenyl-N,N'-di(m-tolyl)anthracene-9,10 -diamine, N,N'-diphenyl-N,N'-bis(4-ethylphenyl)anthracene-9,10-diamine, N,N'-diphenyl-N,N'-bis(4-isopropylphenyl)anthracene-9,10-diamine, N,N'-diphenyl-N,N'-bis(4-t-butylphenyl)anthracene-9,10-diamine, N,N'-bis(4-isopropylphenyl)-N,N'-di(p-tolyl)anthracene-9,10-diamine, 2,6-di-t-butyl-N,N,N',N'-tetra(p-tolyl)anthracene-9,10-diamine , 2,6-di-t-butyl-N,N'-diphenyl-N,N'-bis(4-isopropylphenyl)anthracene-9,10-diamine, 2,6-di-t-butyl-N,N'-bis(4-isopropylphenyl)-N,N'-di(p-tolyl)anthracene-9,10-diamine, 2,6-dicyclohexyl-N,N'-bis(4-isopropylphenyl)-N,N'-di(p-tolyl)anthracene-9,10-diamine, 2,6-dicyclohexyl-N,N'-bis(4-isopropylphenyl)-N,N'-di(p-tolyl)anthracene-9,10-diamine, 2,6-dicyclohexyl-N,N'-bis(4-isopropylphenyl)-N,N'-bis(4-t-butylphenyl) Examples of the anthracene-9,10-diamine include 9,10-bis(4-diphenylamino-phenyl)anthracene, 9,10-bis(4-di(1-naphthylamino)phenyl)anthracene, 9,10-bis(4-di(2-naphthylamino)phenyl)anthracene, 10-di-p-tolylamino-9-(4-di-p-tolylamino-1-naphthyl)anthracene, 10-diphenylamino-9-(4-diphenylamino-1-naphthyl)anthracene, and 10-diphenylamino-9-(6-diphenylamino-2-naphthyl)anthracene.

[0272] Other examples include [4-(4-diphenylamino-phenyl)naphthalen-1-yl]-diphenylamine, [6-(4-diphenylamino-phenyl)naphthalen-2-yl]-diphenylamine, 4,4'-bis[4-diphenylaminonaphthalen-1-yl]biphenyl, 4,4'-bis[6-diphenylaminonaphthalen-2-yl]biphenyl, 4,4"-bis[4-diphenylaminonaphthalen-1-yl]-p-terphenyl, and 4,4"-bis[6-diphenylaminonaphthalen-2-yl]-p-terphenyl. Furthermore, aromatic amine derivatives described in, for example, JP-A-2006-156888 may also be used.

[0273] Coumarin derivatives include coumarin-6 and coumarin-334. Furthermore, coumarin derivatives described in JP-A-2004-43646, JP-A-2001-76876, JP-A-6-298758, and the like may also be used.

[0274] Examples of pyran derivatives include DCM and DCJTB shown below. [ka]

[0275] Furthermore, pyran derivatives described in JP-A-2005-126399, JP-A-2005-097283, JP-A-2002-234892, JP-A-2001-220577, JP-A-2001-081090, JP-A-2001-052869, and the like may also be used.

[0276] In particular, in the light-emitting layer, it is preferable to use the polycyclic aromatic compound of the present invention as a host material and a phosphorescent material or a TADF material (thermally activated delayed fluorescent material) as a dopant material.

[0277] 3-1-5-2-1.Phosphorescent materials Phosphorescent materials utilize the intramolecular spin-orbit interaction (heavy atom effect) of metal atoms to emit light from triplets. For example, a luminescent metal complex can be used as such a phosphorescent material. For example, a luminescent metal complex can be a compound represented by the following formula (B-1). [ka]

[0278] In formula (B-1), M is at least one selected from the group consisting of Ir, Pt, Au, Eu, Ru, Re, Ag, and Cu, n is an integer of 1 to 3, and each "XY" is independently a bidentate monoanionic ligand. Examples of the compound represented by formula (B-1) include compounds represented by the following formula (B-10) or formula (B-15).

[0279] [ka]

[0280] In formula (B-10) and formula (B-15), X' is an aromatic ring containing carbon (C) bonded to M, and Y' is a heterocycle containing nitrogen (N) that is coordinately bonded to M. X' and Y' are bonded, and X' and Y' may form a new ring. In addition, in formula (B-15), Z is a bidentate ligand having two oxygen atoms. In formula (B-10) and formula (B-15), M is preferably Ir from the viewpoint of high efficiency and long life.

[0281] Examples of the compound represented by formula (B-10) include Ir(ppy)3, Ir(ppy)2(acac), Ir(mppy)3, Ir(PPy)2(m-bppy), BtpIr(acac), Ir(btp)2(acac), Ir(2-phq)3, Hex-Ir(phq), Ir(fbi)2(acac), and fac-Tris(2-(3-p-xylyl)phenyl)pyridine. iridium(III), Eu(dbm)3(Phen), Ir(piq)3, Ir(piq)2(acac), Ir(Fliq)2(acac), Ir(Flq)2(acac), Ru(dtb-bpy)3·2(PF6), Ir(2-phq)3, Ir(BT)2(acac), Ir(DMP)3 , Ir(Mphq)3IR(phq)2tpy, fac-Ir(ppy)2Pc, Ir(dp)PQ2, Ir(Dpm)(Piq)2, Hex-Ir(piq)2(acac), Hex-Ir(piq)3, Ir(dmpq)3, Ir(dmpq)2(acac), FPQIrpic, etc.

[0282] Other examples of the compound represented by formula (B-10) include compounds represented by the following formulae (B-10-1) to (B-10-31). [ka]

[0283] Other examples of the compound represented by formula (B-15) include compounds represented by the following formulae (B-15-1) to (B-15-6). [ka]

[0284] In addition, iridium complexes described in JP 2006-089398 A, JP 2006-080419 A, JP 2005-298483 A, JP 2005-097263 A, and JP 2004-111379 A, ​​U.S. Patent Application Publication No. 2019 / 0051845, and the like, may be used.

[0285] 3-1-5-2-2.TADF material In this specification, TADF material means a material that is a "thermally activated delayed fluorescent material." In "thermally activated delayed fluorescent material," the energy difference between the excited singlet state and the excited triplet state is reduced, thereby efficiently transferring energy from the excited triplet state, which usually has a low transition probability, to the excited singlet state, and light emission from the singlet state (thermally activated delayed fluorescence, TADF) is generated. In normal fluorescent emission, 75% of the triplet excitons generated by electric current excitation pass through a thermal deactivation pathway and cannot be extracted as fluorescent light. On the other hand, in TADF, all excitons can be used for fluorescent emission, making it possible to realize highly efficient organic electroluminescence devices.

[0286] TADF materials are preferably donor-acceptor type TADF compounds (DA type TADF compounds) designed to localize the HOMO and LUMO within a molecule using electron-donating substituents called donors and electron-accepting substituents called acceptors, thereby allowing efficient reverse intersystem crossing to occur.

[0287] In this specification, the term "electron-donating substituent" (donor) refers to a substituent or partial structure in which the HOMO orbital is localized in a TADF compound molecule, and the term "electron-accepting substituent" (acceptor) refers to a substituent or partial structure in which the LUMO orbital is localized in a TADF compound molecule.

[0288] Examples of TADF materials that can be used include polycyclic aromatic compounds that are monomers represented by the following formula (2) or polymers having a plurality of structural units represented by formula (2) (hereinafter, sometimes referred to as "polycyclic aromatic compounds of formula (2)"), and combinations of polycyclic aromatic compounds of formula (2) with other TADF materials.

[0289] <Polycyclic aromatic compound of formula (2)> A polycyclic aromatic compound which is a monomer represented by the following formula (2) or a polymer having a plurality of structural units represented by formula (2) can provide high color purity as a TADF material (see WO 2015 / 102118, WO 2020 / 162600, etc.).

[0290] [ka]

[0291] Ring A, ring B and ring C are each independently an optionally substituted aryl ring or an optionally substituted heteroaryl ring, provided that B and X in ring A, ring B and ring C in the polycyclic aromatic compound represented by formula (2) are 11 and / or X 12 None of the rings bonded to are six-membered rings containing nitrogen. X 11 and X 12 are each independently >O or >NR, R of the >NR is an optionally substituted aryl, an optionally substituted heteroaryl, an optionally substituted alkyl, or an optionally substituted cycloalkyl, and R of the >NR is optionally 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 structure represented by formula (2) or the structure having a plurality of structural units represented by formula (2), at least one selected from the group consisting of an aryl ring and a heteroaryl ring may be condensed with at least one cycloalkane, at least one hydrogen in the cycloalkane may be substituted, and at least one -CH2- in the cycloalkane may be substituted with -O-; At least one hydrogen atom in the structure represented by formula (2) or in a structure having a plurality of structural units represented by formula (2) may be substituted with deuterium, cyano or halogen.

[0292] The polycyclic aromatic compound of formula (2) is preferably a polycyclic aromatic compound which is a monomer represented by formula (2-a), (2-b), (2-c), (2-d), (2-e), or (2-f) below, or a polycyclic aromatic compound which is a polymer having a plurality of structural units represented by formula (2-a), (2-b), (2-c), (2-d), (2-e), or (2-f) below.

[0293] [ka]

[0294] In each structural formula, "A" to "C" and "a" to "c" are symbols indicating a ring, a benzene ring, or a ring structure represented by a five-membered ring, and the other symbols are the same as defined above.

[0295] The rings A, B and C in formula (2) are each independently an aryl ring or a heteroaryl ring, and at least one hydrogen atom in these rings may be substituted with a substituent. The substituent is preferably a substituent selected from the above-mentioned substituent group YZ, or a substituted silyl. In the rings A, B and C in the polycyclic aromatic compound, which is a monomer represented by formula (2), B (boron) and X 11 and / or X 12 None of the rings bonded to the ring A are six-membered rings containing nitrogen. In other words, the polycyclic aromatic compound of formula (2) that is not a polymer does not have a six-membered ring containing nitrogen in the ring A, ring B, or ring C as a ring that shares a bond with the fused two-ring structure described below.

[0296] At least any one of ring A, ring B, and ring C is preferably an aryl ring having at least one substituent or a heteroaryl ring having at least one substituent, more preferably ring A, ring B, and ring C are all aryl rings having at least one substituent or heteroaryl rings having at least one substituent, and further preferably ring A, ring B, and ring C are each an aryl ring having one substituent or a heteroaryl ring having one substituent.

[0297] In particular, the substituent is preferably a substituted or unsubstituted alkyl (particularly, neopentyl) or a cycloalkyl such as adamantyl. Also, a tertiary alkyl (tR) is preferred. This is because such a bulky substituent prevents inactivation due to aggregation of molecules, and improves the luminescence quantum yield (PLQY). Also, a substituted or unsubstituted diarylamino is preferred.

[0298] The tertiary alkyl is represented by the following formula (tR): [ka]

[0299] In the formula (tR), R a , R b , and R c are each independently an alkyl group having 1 to 24 carbon atoms, any -CH2- in the alkyl group may be replaced with -O-, and the group represented by formula (tR) replaces at least one hydrogen atom in the polycyclic aromatic compound of formula (2) at *.

[0300] R a , R b , and R cThe "alkyl having 1 to 24 carbon atoms" 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), alkyl having 1 to 12 carbon atoms (branched alkyl having 3 to 12 carbon atoms), alkyl having 1 to 6 carbon atoms (branched alkyl having 3 to 6 carbon atoms), and alkyl having 1 to 4 carbon atoms (branched alkyl having 3 to 4 carbon atoms).

[0301] R in formula (tR) of formula (2) a , R b , and R c The total number of carbon atoms is preferably 3 to 20, and particularly preferably 3 to 10.

[0302] 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 Examples of the aryl group include n-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.

[0303] Examples of the group represented by the 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.

[0304] Other preferred examples of the substituents in ring A, ring B, and ring C include, for example, diarylamino substituted with a group of formula (tR), carbazolyl substituted with a group of formula (tR), or benzocarbazolyl substituted with a group of formula (tR). For "diarylamino", the group described below as the "first substituent" is included. Examples of the substitution form of the group of formula (tR) on diarylamino, carbazolyl, and benzocarbazolyl include examples in which some or all of the hydrogen atoms on the aryl ring or benzene ring in these groups are substituted with the group of formula (tR).

[0305] The aryl or heteroaryl rings in the A, B and C rings are each defined as "B", "X", 1 " and "X 2 It is preferable that the formula (2) has a 5- or 6-membered ring sharing a bond with the central fused two-ring structure.

[0306] Here, the "fused two-ring structure" refers to the "B" and "X" shown in the center of formula (2). 11 " and "X 12" means a structure in which two saturated hydrocarbon rings are fused together. In addition, "a six-membered ring sharing a bond with the fused two-ring structure" means, for example, an a-ring (a benzene ring (six-membered ring)) fused to the fused two-ring structure as shown in formula (2-a), formula (2-b), formula (2-c), formula (2-d), formula (2-e), and formula (2-f). In addition, "an aryl ring or heteroaryl ring (A-ring) has this six-membered ring" means that the A-ring is formed only from this six-membered ring, or that the A-ring is formed by further condensing other rings to this six-membered ring so as to include this six-membered ring. In other words, "an aryl ring or heteroaryl ring (A-ring) having a six-membered ring" means that the six-membered ring constituting all or a part of the A-ring is fused to the fused two-ring structure. The same explanation applies to "a five-membered ring". In addition, the same explanation applies to "a B-ring (b-ring)" and "a C-ring (c-ring)".

[0307] The A ring in formula (2) is the same as the a ring and its substituent R in formulae (2-a), (2-b), (2-c), (2-d), (2-e), and (2-f). 1 ~R 3 The B ring in formula (2) corresponds to the b ring and its substituent R in formulas (2-a), (2-b), and (2-c). 8 ~R 11 , the ring b in formula (2-d) and its substituent R 10 and R 11 and the ring b and its substituent R in the formula (2-e) and the formula (2-f). 8 and R 9 The ring C in formula (2) corresponds to the ring c and its substituent R in formula (2-a). 4 ~R 7 , the ring c and its substituent R in formula (2-b), formula (2-d), and formula (2-f) 4 and R 5 and the ring c and its substituent R in formula (2-c) and formula (2-e) 6 and R 7That is, formula (2-a) corresponds to a structure in which rings having at least a 6-membered ring structure are selected as rings A to C of formula (2), and formulas (2-b), (2-c), (2-d), (2-e), and (2-f) correspond to structures in which rings having at least a 6-membered ring structure and rings having at least a 5-membered ring structure are selected as rings A to C of formula (2), respectively. In this sense, each ring in formula (2-a) etc. is represented by lowercase letters a to c.

[0308] X in formulas (2-b), (2-c), (2-d), (2-e), and (2-f) X are each independently >O, >S, >NR, or >C(-R)2. Here, R in the >NR is an aryl which may be substituted, a heteroaryl which may be substituted, an alkyl which may be substituted, or a cycloalkyl which may be substituted, preferably an aryl which may be substituted, and more preferably an unsubstituted aryl. In addition, R in the >C(-R)2 is each independently hydrogen, an aryl which may be substituted with an alkyl or cycloalkyl, a heteroaryl which may be substituted with an alkyl or cycloalkyl, an alkyl, or a cycloalkyl, preferably an alkyl, and more preferably a methyl. It is preferable that the two R in >C(-R)2 are the same. It is also preferable that the two R in >C(-R)2 form a ring together. X X are each independently preferably >O, >S, or >NR, more preferably >O or >S, and even more preferably >S.

[0309] In formulas (2-a), (2-b), (2-c), (2-d), (2-e), and (2-f), R 1 ~R 11 are each independently a substituent selected from the substituent group YZ, or a substituted silyl.

[0310] R in each of formulas (2-a), (2-b), (2-c), (2-d), (2-e), and (2-f) 1 ~R3 In R, 0 to 1 are substituents other than hydrogen and the rest are hydrogen. 4 ~R 7 In R, 0 to 1 are substituents other than hydrogen and the rest are hydrogen. 8 ~R 11 Among them, it is preferred that 0 to 1 of them are a substituent other than hydrogen and the rest are hydrogen. R 1 ~R 3 Among them, one is a substituent other than hydrogen and the others are hydrogen; R 4 ~R 7 Among them, one is a substituent other than hydrogen and the others are hydrogen; R 8 ~R 11 Among them, it is more preferable that one of them is a substituent other than hydrogen and the others are hydrogen. For the preferable range of the substituent other than hydrogen, the description of the substituent described below as the first substituent (which may have a second substituent) can be referred to. As the substituent other than hydrogen, it is particularly preferable that it is alkyl (particularly the above tertiary alkyl (tR), neopentyl, etc.), cycloalkyl (for example, adamantyl, etc.), or substituted or unsubstituted diarylamino.

[0311] In the formulae (2-a), (2-b), (2-c), (2-d), (2-e), and (2-f), the substituents R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , and R 11Adjacent groups among these may be bonded to each other to form an aryl ring or a heteroaryl ring together with the a ring, the b ring, or the c ring, and at least one hydrogen atom in the formed ring may be replaced by an aryl, a heteroaryl, a diarylamino, a diheteroarylamino, an arylheteroarylamino, a diarylboryl (two aryls may be bonded via a single bond or a linking group), an alkyl, a cycloalkyl, an alkoxy, an aryloxy, or a substituted silyl, and at least one hydrogen atom in these may be replaced by an aryl, a heteroaryl, an alkyl, a cycloalkyl, or a substituted silyl.

[0312] For example, in the compound represented by formula (2-a), the ring structure constituting the compound changes depending on the mutual bonding form of the substituents in ring a, ring b, and ring c, as shown in the following formulas (2-a-1) and (2-a-2). Ring A', ring B', and ring C' in each formula correspond to ring A, ring B, and ring C in formula (2), respectively. In addition, R in each formula 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , a, b, c, X 11 and X 12 is the same as in formula (2-a).

[0313] [ka]

[0314] The A' ring, B' ring and C' ring in the formula (2-a-1) and the formula (2-a-2) are each independently a substituent R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R9 , R 10 , and R 11 Adjacent groups among these are bonded to each other to form an aryl or heteroaryl ring together with the ring a, ring b, and ring c, respectively (they may also be considered as fused rings formed by fusing other ring structures to the ring a, ring b, or ring c). Although not shown in the formula, there are also compounds in which the ring a, ring b, and ring c are all changed to ring A', ring B', and ring C'. As can be seen from formula (2-a-1) and formula (2-a-2), for example, R in ring b 8 and R in c-ring 7 , R in ring b 11 and a-ring R 1 , R in ring c 4 and a-ring R 3 etc. are not considered to be "adjacent groups" and are not bonded to each other. In other words, "adjacent groups" refers to groups adjacent to each other on the same ring.

[0315] The compounds represented by formula (2-a-1) or (2-a-2) correspond to, for example, the compounds represented by formulae (2-67) to (2-74), (2-76) to (2-83), (2-273) to (2-276), (2-290) to (2-295), and (2-350) to (2-355), which are listed below as specific compounds. That is, for example, it is a compound having ring A' (or ring B' or ring C') formed by condensing a benzene ring, which is ring a (or ring b or ring c), with a benzene ring, an indole ring, a pyrrole ring, a furan ring, a thiophene ring, a benzofuran ring, a benzothiophene ring, a cyclopentadiene ring, or an indene ring, and the condensed ring A' (or condensed ring B' or condensed ring C') thus formed is a naphthalene ring, a carbazole ring, an indole ring, a benzofuran ring, a benzothiophene ring, a dibenzofuran ring, a dibenzothiophene ring, an indene ring, or a fluorene ring, respectively.

[0316] Similarly, in formula (2-b), formula (2-c), formula (2-d), formula (2-e), and formula (2-f), a fused ring may be formed by condensing another ring structure to ring a, ring b, or ring c. For example, the benzene ring of ring a or ring b may be condensed to another ring structure to form a fused ring, similar to the benzene ring in formula (2-a). In the formulae (2-b), (2-c), (2-d), (2-e), and (2-f), R 4 ~R 11 It is particularly preferred that adjacent groups among the above are bonded to each other to form a ring to form a condensed ring. For example, in the ring c of formula (2-b) and formula (2-c), and the rings b and c of formula (2-d), formula (2-e), and formula (2-f), R 3 ~R 11 Adjacent groups among these can be bonded to each other to form a ring, thereby forming a fused ring, ring B' or ring C'. Examples of the fused ring when the ring formed is a benzene ring include an indole ring, a benzofuran ring, and a benzothiophene ring.

[0317] As an example, in the five-membered ring which is the ring c in formula (2-b), R 4 and R 5 The following is an example of a fused ring formed by bonding together to form a benzene ring. [ka]

[0318] In formula (2-b-1), R 1 , R 2 , R 3 , R 8 , R 9 , R 10 , R 11 , X X , X 11 and X 12 R has the same meaning as in formula (2-b), and the preferred ranges are also the same. 4b , R 5b , R 6b , R 7bis hydrogen, a substituent selected from the substituent group YZ, or a substituted silyl. 4b , R 5b , R 6b , R 7b Among them, it is preferable that 0 to 2 are substituents other than hydrogen and the rest are hydrogen, and it is more preferable that one is a substituent other than hydrogen and the rest are hydrogen. For the preferable range of the substituent other than hydrogen, the description of the substituents described below can be referred to. As the substituent other than hydrogen, it is particularly preferable that it is alkyl (particularly the above tertiary alkyl (tR), neopentyl, etc.), cycloalkyl (for example, adamantyl, etc.), or substituted or unsubstituted diarylamino.

[0319] For example, in (2-b), (2-c), (2-d), (2-e), and (2-f), X X When is >O, ring b and / or ring c are furan rings, and the rings corresponding to ring B' and / or ring C' in formula (2-a-1) formed by condensing a benzene ring to this furan ring are benzofuran rings. Also, for example, in (2-b), formula (2-c), formula (2-d), formula (2-e), and formula (2-f), X X When is >S, ring b and / or ring c are thiophene rings, and the rings corresponding to ring B' and / or ring C' in formula (2-a-1) formed by condensing a benzene ring to this thiophene ring are benzothiophene rings. Examples of such a structure include compounds represented by any of formulas (2-572) to (1-588) described below.

[0320] X in formula (2) 11 and X 12are each independently >O or >NR, R of the >NR is an optionally substituted aryl, an optionally substituted heteroaryl, an optionally substituted alkyl, or an optionally substituted cycloalkyl, R of the >NR may be bonded to the B ring and / or the C ring via a linking group or a single bond, and the linking group is preferably -O-, -S-, or -C(-R)2-. Note that R of the "-C(-R)2-" is hydrogen, alkyl, or cycloalkyl. This explanation applies to X in formula (2-a), formula (2-b), formula (2-c), formula (2-d), formula (2-e), and formula (2-f). 11 and X 12 But it's the same.

[0321] In the formula (2) and the formulas (2-a), (2-b), (2-c), (2-d), (2-e), and (2-f), X 11 and X 12 is more preferably >NR, in which R is optionally substituted phenyl, further preferably >NR, in which at least one R is phenyl substituted with one or two t-butyl, t-amyl, methyl or phenyl, and particularly preferably >NR, in which at least one R is phenyl substituted with one t-butyl or t-amyl. 12 and X 12 may be the same group or different groups.

[0322] Here, the provision in formula (2) that "R of >NR is bonded to ring A and / or ring B, or ring A and / or ring C through a linking group or a single bond" corresponds to the provision in formulas (2-a), (2-b), (2-c), (2-d), (2-e), and (2-f) that "R of >NR is bonded to ring a and / or ring b, or ring a and / or ring c through -O-, -S-, -C(-R)2-, or a single bond."

[0323] This provision is expressed by the following formula (2-a-3-1), X 11 Or X 12can be expressed as a compound having a ring structure in which X is incorporated into the fused ring B' and the fused ring C'. That is, for example, the compound having X in the benzene ring which is the b ring (or the c ring) in the formula (2-a) 11 (or X 12 The compound has a ring B' (or ring C') formed by condensing another ring so as to incorporate the ring A. The condensed ring B' (or condensed ring C') formed is, for example, a phenoxazine ring, a phenothiazine ring, or an acridine ring.

[0324] In addition, the above provision is based on the following formula (2-a-3-2) or formula (2-a-3-3), X 11 and / or X 12 In other words, for example, the a-ring in formula (2-a) is a benzene ring, and X 11 (and / or X 12 The compound has a ring A' formed by condensing another ring so as to incorporate the ring A'. The condensed ring A' formed is, for example, a phenoxazine ring, a phenothiazine ring, or an acridine ring.

[0325] [ka]

[0326] The "aryl ring" which is the ring A, ring B and ring C in formula (2) is, for example, an aryl ring having 6 to 30 carbon atoms, preferably an aryl ring having 6 to 16 carbon atoms, more preferably an aryl ring having 6 to 12 carbon atoms, and particularly preferably an aryl ring having 6 to 10 carbon atoms. The "aryl ring" is defined as "R 1 ~R 11 In addition, since ring a (or ring b, ring c) is already composed of a benzene ring having six carbon atoms, the lower limit of the carbon number is the total carbon number of the fused rings formed by condensing the five-membered ring to this, which is nine.

[0327] Specific examples of the "aryl ring" include a monocyclic benzene ring, a bicyclic bicyclic ring, a naphthalene ring, an indene ring, and a tetralin ring, a tricyclic terphenyl ring (m-terphenyl, o-terphenyl, and p-terphenyl), a fused tricyclic ring, an acenaphthylene ring, a fluorene ring, a phenalene ring, a phenanthrene ring, and an anthracene ring, a fused tetracyclic ring, a triphenylene ring, a pyrene ring, a naphthacene ring, and a chrysene ring, and a fused pentacyclic ring, a perylene ring, and a pentacene ring.

[0328] Examples of the "heteroaryl ring" which is the ring A, ring B and ring C in formula (2) include heteroaryl rings having 2 to 30 carbon atoms, preferably heteroaryl rings having 2 to 25 carbon atoms, more preferably heteroaryl rings having 2 to 20 carbon atoms, further preferably heteroaryl rings having 2 to 15 carbon atoms, and particularly preferably heteroaryl rings having 2 to 10 carbon atoms. Examples of the "heteroaryl ring" include heterocycles containing, in addition to carbon, 1 to 5 heteroatoms selected from oxygen, sulfur and nitrogen as ring-constituting atoms. The "heteroaryl ring" is defined as "R" as defined in formula (2-a), formula (2-b), formula (2-c), formula (2-d), formula (2-e) and formula (2-f). 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 and R 11 In addition, since ring a (or ring b, ring c) is already composed of a benzene ring having 6 carbon atoms, the lower limit of the carbon number is the total carbon number of the fused rings fused to this 5-membered ring, which is 6.

[0329] 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, and 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, 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, and a dibenzodioxin ring.

[0330] The "aryl ring" and "heteroaryl ring" of the A ring, B ring, and C ring each have B (boron) and X at any position. 11 or X 12 That is, the "aryl ring" and "heteroaryl ring" of ring A, ring B, and ring C may share a bond with the central fused two-ring structure of formula (2) at any position. For example, when the "aryl ring" and "heteroaryl ring" are fused rings of two or more rings, any ring may share a bond with the central fused two-ring structure of formula (2). Of these, as described above, ring A, ring B, and ring C may be bonded to B (boron), X 11 , and X 12 It is preferable that the fused two-ring structure in the center of the formula (2) has a 5-membered or 6-membered ring sharing a bond therewith. That is, for example, in the formula (2-a), R 1 ~R 3Adjacent groups among these are bonded together to form ring a, R 4 ~R 7 Adjacent groups among these are bonded together to form ring c, and R 8 ~R 11 In the case where adjacent groups among the above are bonded to each other to form an aryl ring or a heteroaryl ring together with the b ring, the benzene ring, which is a six-membered ring, shares a bond with the central fused two-ring structure of formula (2), which is preferable. 4 and R 5 When R in (2-c) forms an aryl or heteroaryl ring together with ring c, 6 and R 7 When R and R c together with ring c form an aryl ring or a heteroaryl ring, R 4 and R 5 and c ring together with R 10 and R 11 When R and b form an aryl or heteroaryl ring together with ring b, R 6 and R 7 and c ring together with R 8 and R 9 and b form an aryl or heteroaryl ring together with ring b, or R 4 and R 5 and c ring together with R 8 and R 9 When R and R form an aryl or heteroaryl ring together with ring b, R is a 5-membered ring that shares a bond with the central fused 2-ring structure of formula (2), and is preferred. Examples of the 5-membered ring in this case include a pyrrole ring, a furan ring, and a thiophene ring.

[0331] For the substituents selected from the substituent group YZ, the description of the substituents selected from the substituent group YZ in the polycyclic aromatic compound represented by formula (1) can be referred to.

[0332] The "substituted silyl" includes, for example, 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.

[0333] An example of the "trialkylsilyl" is a group in which three hydrogen atoms in a silyl are each independently substituted with an alkyl, and the alkyl can be cited from the groups described as the "alkyl" in the first substituent above. Preferred alkyl groups for substitution are alkyl groups having 1 to 5 carbon atoms, and specific examples thereof include methyl, ethyl, propyl, i-propyl, butyl, sec-butyl, t-butyl, and t-amyl.

[0334] Specific examples of trialkylsilyl include trimethylsilyl, triethylsilyl, tripropylsilyl, tri-i-propylsilyl, tributylsilyl, trisec-butylsilyl, tri-t-butylsilyl, tri-t-amylsilyl, ethyldimethylsilyl, propyldimethylsilyl, i-propyldimethylsilyl, butyldimethylsilyl, sec-butyldimethylsilyl, t-butyldimethylsilyl, t-amyldimethylsilyl, methyldiethylsilyl, propyldiethylsilyl, i-propyldiethylsilyl, and butyldiethylsilyl. Examples of the silyl group include butyldiethylsilyl, sec-butyldiethylsilyl, t-butyldiethylsilyl, t-amyldiethylsilyl, methyldipropylsilyl, ethyldipropylsilyl, butyldipropylsilyl, sec-butyldipropylsilyl, t-butyldipropylsilyl, t-amyldipropylsilyl, methyldi-i-propylsilyl, ethyldi-i-propylsilyl, butyldi-i-propylsilyl, sec-butyldi-i-propylsilyl, t-butyldi-i-propylsilyl, and t-amyldi-i-propylsilyl.

[0335] Examples of "tricycloalkylsilyl" include a group in which three hydrogen atoms in silyl are independently replaced by cycloalkyl, and the cycloalkyl can be cited as the group described as "cycloalkyl" in the first substituent above. Preferred cycloalkyl for substitution is a cycloalkyl having 5 to 10 carbon atoms, specifically cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, bicyclo[1.1.1]pentyl, bicyclo[2.0.1]pentyl, bicyclo[1.2.1]hexyl, bicyclo[3.0.1]hexyl, bicyclo[2.1.2]heptyl, bicyclo[2.2.2]octyl, adamantyl, decahydronaphthalenyl, decahydroazulenyl, and the like.

[0336] Specific examples of tricycloalkylsilyl include tricyclopentylsilyl and tricyclohexylsilyl.

[0337] Specific examples of dialkylcycloalkylsilyl substituted with two alkyls and one cycloalkyl and alkyldicycloalkylsilyl substituted with one alkyl and two cycloalkyls include silyl substituted with a group selected from the specific alkyls and cycloalkyls mentioned above.

[0338] 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.

[0339] In the polycyclic aromatic compound of formula (2), the emission wavelength can be adjusted by the steric hindrance, electron donating property and electron withdrawing property of the structure of the first substituent. The first substituent is preferably a group represented by the following structural formula, and more preferably methyl, t-butyl, t-pentyl (t-amyl), t-octyl, neopentyl, cyclohexyl, 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-dimethyl carbazolyl, 3,6-di-t-butylcarbazolyl and phenoxy, and more preferably methyl, t-butyl, t-octyl, neopentyl, cyclohexyl, adamantyl, phenyl, o-tolyl, 2,6-xylyl, 2,4,6-mesityl, diphenylamino, di-p-tolylamino, bis(p-(t-butyl)phenyl)amino, carbazolyl, 3,6-dimethylcarbazolyl and 3,6-di-t-butylcarbazolyl. From the viewpoint of ease of synthesis, larger steric hindrance is preferred for selective synthesis, and specifically, t-butyl, t-pentyl (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.

[0340] In the structural formula below, "Me" is methyl, "tBu" is t-butyl, "tAm" is t-amyl, "tOct" is t-octyl, and * indicates the bond position. [ka]

[0341] [ka]

[0342] [ka]

[0343]

change

[0344]

change

[0345]

change

[0346]

change

[0347]

change

[0348]

change

[0349]

change

[0350]

change

[0351]

change

[0352]

change

[0353] R in formula (2-a), formula (2-b), formula (2-c), formula (2-d), formula (2-e), and formula (2-f) 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , and R 11 The aryl, heteroaryl, aryl of diarylamino, heteroaryl of diheteroarylamino, aryl and heteroaryl of arylheteroarylamino, aryl of diarylboryl, and aryl of aryloxy in the formula (1) include the monovalent groups of "aryl ring" or "heteroaryl ring" described in formula (2). 1 ~R 11 For the alkyl, cycloalkyl, or alkoxy in R, the explanation of "alkyl," "cycloalkyl," or "alkoxy" as the first substituent in the explanation of formula (2) above can be referred to. Furthermore, the same applies to aryl, heteroaryl, alkyl, or cycloalkyl as substituents to these groups. 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , and R 11 When adjacent groups among these are bonded to form an aryl ring or a heteroaryl ring together with the a ring, the b ring, or the c ring, the same applies to the heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl, alkyl, cycloalkyl, alkoxy, or aryloxy as substituents on these rings, and the aryl, heteroaryl, alkyl, or cycloalkyl as further substituents.

[0354] X in Equation (2) 11 and X12 In the formula (2), R in >NR is aryl, heteroaryl, alkyl, or cycloalkyl, and at least one hydrogen atom in the aryl or heteroaryl may be substituted with, for example, alkyl, cycloalkyl, or substituted silyl. Examples of the aryl, heteroaryl, alkyl, and cycloalkyl include the groups described above. In particular, aryl having 6 to 10 carbon atoms (e.g., phenyl, naphthyl, etc.), heteroaryl having 2 to 15 carbon atoms (e.g., carbazolyl, etc.), alkyl having 1 to 5 carbon atoms (e.g., methyl, ethyl, etc.), or cycloalkyl having 5 to 10 carbon atoms (preferably cyclohexyl or adamantyl) are preferred. This explanation applies to X in formulas (2-a), (2-b), (2-c), (2-d), (2-e), and (2-f). 1 and X 2 The same is true for X in formulas (2-a), (2-b), (2-c), (2-d), (2-e), and (2-f). 1 and X 2 R in >NR is an aryl having 6 to 12 carbon atoms which may be substituted with an alkyl having 1 to 6 carbon atoms or a cycloalkyl having 3 to 14 carbon atoms, a heteroaryl having 2 to 15 carbon atoms which may be substituted with an alkyl having 1 to 6 carbon atoms or a cycloalkyl having 3 to 14 carbon atoms, an alkyl having 1 to 6 carbon atoms, or a cycloalkyl having 3 to 14 carbon atoms, and is preferably an aryl having 6 to 10 carbon atoms which may be substituted with an alkyl having 1 to 4 carbon atoms or a cycloalkyl having 5 to 10 carbon atoms, an alkyl having 1 to 4 carbon atoms, or a cycloalkyl having 5 to 10 carbon atoms.

[0355] R in "-C(-R)2-" which is the linking group in formula (2) is hydrogen, alkyl or cycloalkyl, and examples of the alkyl and cycloalkyl include the groups described above. In particular, alkyl having 1 to 5 carbon atoms (e.g., methyl, ethyl, etc.) or cycloalkyl having 5 to 10 carbon atoms (preferably cyclohexyl or adamantyl) is preferred. This explanation also applies to "-C(-R)2-" which is the linking group in formulas (2-a), (2-b), (2-c), (2-d), (2-e), and (2-f).

[0356] The dopant material may be a polycyclic aromatic compound which is a polymer having a plurality of structural units represented by formula (2). The polymer is preferably a polycyclic aromatic compound which is a polymer having a plurality of structural units represented by formula (2-a), formula (2-b), formula (2-c), formula (2-d), formula (2-e), and formula (2-f). The polymer is preferably a dimer to hexamer, more preferably a dimer to trimer, and particularly preferably a dimer. The multimer may have a form having a plurality of the above structural units in one compound. For example, in addition to a form in which a plurality of the above structural units are bonded together via a linking group such as a single bond, an alkylene having 1 to 3 carbon atoms, phenylene, or naphthylene, the multimer may have a form in which any ring (ring A, ring B or ring C, ring a, ring b or ring c) contained in the above structural unit is bonded so as to be shared by a plurality of structural units, or may have a form in which any ring (ring A, ring B or ring C, ring a, ring b or ring c) contained in the above structural unit is bonded so as to be condensed with each other.

[0357] Examples of such multimers include multimer compounds represented by the following formula (2-4), formula (2-4-1), formula (2-4-2), formula (2-5-1) to formula (2-5-4), formula (2-6) or formula (2-7). The multimer compound represented by the following formula (2-4) is a multimer compound having a plurality of structural units represented by formula (2-a) in one compound, with the benzene ring being the a-ring shared, as explained by formula (2-a). The multimer compound represented by the following formula (2-4-1) is a multimer compound having two structural units represented by formula (2-a) in one compound, with the benzene ring being the a-ring shared, as explained by formula (2-a). Moreover, the multimeric compound represented by the following formula (2-4-2) is a multimeric compound having three structural units represented by formula (2-a) in one compound, with the benzene ring being the a ring shared, when explained by formula (2-a). Moreover, the multimeric compound represented by the following formula (2-5-1) to formula (2-5-4) is a multimeric compound having a plurality of structural units represented by formula (2-a) in one compound, with the benzene ring being the b ring (or the c ring) shared, when explained by formula (2-a). Moreover, the multimeric compound represented by the following formula (2-6) is a multimeric compound having a plurality of structural units represented by formula (2-a) in one compound, with the benzene ring being the b ring (or the a ring, the c ring) of a certain structural unit condensed with the benzene ring being the b ring (or the a ring, the c ring) of a certain structural unit. Furthermore, the polymeric compound represented by the following formula (2-7), when explained using formula (2-a), is a polymeric compound having three structural units represented by formula (2-a) in one compound, for example, such that the benzene rings which are the b ring and the c ring of a certain structural unit are condensed with the benzene rings which are the b ring and the c ring of another structural unit, respectively. In the following formulas (2-4), (2-4-1), (2-4-2), (2-5-1) to (2-5-4), (2-6) and (2-7), R 1 ~R 11 , and X 11 and X 12 is R in formula (2-a) 1 ~R 11 , and X 11 and X12 are synonymous with each other.

[0358] [ka]

[0359] The multimeric compound may be a multimer in which a multimerization form represented by formula (2-4), formula (2-4-1) or formula (2-4-2) is combined with a multimerization form represented by any one of formulas (2-5-1) to (2-5-4) or formula (2-6), a multimer in which a multimerization form represented by any one of formulas (2-5-1) to (2-5-4) is combined with a multimerization form represented by formula (2-6), or a multimer in which a multimerization form represented by formula (2-4), formula (2-4-1) or formula (2-4-2), a multimerization form represented by any one of formulas (2-5-1) to (2-5-4), and a multimerization form represented by formula (2-6).

[0360] As the polycyclic aromatic compound, which is a polymer having a plurality of structural units represented by formula (2), a compound represented by the following formula (D2) or formula (D3) is preferable, which includes the compounds represented by formula (2-5-3) and formula (2-7), respectively, in the case described in formula (2-a).

[0361] [ka]

[0362] In formula (D2) or formula (D3), A to C and X 11 and X 12 A to C and R in formula (2-a) 1 ~R 11 , and X 11 and X 12 The polycyclic aromatic compounds represented by formula (D2) or (D3) have the same meaning as those represented by formula (2), except that B (boron) and X are not present in the A ring, B ring, and C ring. 11 and / or X 12The ring attached to may be a six-membered ring containing nitrogen.

[0363] At least one selected from the group consisting of aryl rings and heteroaryl rings in the chemical structure of a polycyclic aromatic compound which is a monomer represented by formula (2), formula (2-a), formula (2-b), formula (2-c), formula (2-d), formula (2-e), or formula (2-f) or a polymer having a plurality of structural units represented by any of these may be condensed with at least one cycloalkane.

[0364] For example, aryl and heteroaryl rings in the aryl and heteroaryl rings which are ring A, ring B, ring C, ring a, ring b, and ring c, aryl (aryl moiety in aryl, diarylamino, arylheteroarylamino, diarylboryl, or aryloxy) and heteroaryl (heteroaryl moiety in heteroaryl, diheteroarylamino, or arylheteroarylamino) as the first and second substituents in ring A to ring C, aryl (similar to above) and heteroaryl (similar to above) as the first and second substituents on ring a, ring b, and ring c, and X 11 , X 12 At least one of the aryl (as above) and heteroaryl (as above) as >NR may be fused with at least one cycloalkane.

[0365] Preferably, the aryl and heteroaryl rings are ring A, ring B, ring C, ring a, ring b, and ring c; the aryl (aryl moiety in aryl, diarylamino, diarylboryl, or aryloxy) and the heteroaryl (heteroaryl moiety in heteroaryl or diheteroarylamino) as the first substituents in ring A to ring C; the aryl (similar to above) and the heteroaryl (similar to above) as the first substituents on ring a to ring c; and X 1 , X 2 At least one of the aryl (as above) and heteroaryl (as above) as >NR may be fused with at least one cycloalkane.

[0366] More preferably, the aryl rings are ring A, ring B, ring C, ring a, ring b, and ring c; the aryl (aryl moiety in aryl or diarylamino) and heteroaryl (heteroaryl moiety in heteroaryl) as the first substituents in ring A to ring C; the aryl (similar to above) and heteroaryl (similar to above) as the first substituents on ring a, ring b, and ring c; and X 11 , X 2 At least one of the aryls (as above) as R in >NR may be fused with at least one cycloalkane.

[0367] More preferably, the aryl rings are ring A, ring B, ring C, ring a, ring b, and ring c, the aryl as the first substituent in ring A to ring C (aryl or aryl moiety in diarylamino), the aryl as the first substituent on ring a, ring b, and ring c (similar to the above), and X 11 , X 12 At least one of the aryls (as above) as R in >NR may be fused with at least one cycloalkane.

[0368] Examples of "cycloalkane" include cycloalkanes having 3 to 24 carbon atoms, cycloalkanes having 3 to 20 carbon atoms, cycloalkanes having 3 to 16 carbon atoms, cycloalkanes having 3 to 14 carbon atoms, cycloalkanes having 5 to 10 carbon atoms, cycloalkanes having 5 to 8 carbon atoms, cycloalkanes having 5 to 6 carbon atoms, and cycloalkanes having 5 carbon atoms.

[0369] Specific examples of cycloalkanes include cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclooctane, cyclononane, cyclodecane, norbornene, bicyclo[1.0.1]butane, bicyclo[1.1.1]pentane, bicyclo[2.0.1]pentane, bicyclo[1.2.1]hexane, bicyclo[3.0.1]hexane, bicyclo[2.1.2]heptane, bicyclo[2.2.2]octane, adamantane, diamantane, decahydronaphthalene, and decahydroazulene, as well as alkyl (particularly methyl) substituted, halogen (particularly fluorine) substituted, and deuterium substituted derivatives of these having 1 to 5 carbon atoms.

[0370] Among these, for example, as shown in the following structural formula, a structure in which at least one hydrogen atom is substituted on the carbon atom at the α-position of a cycloalkane (a carbon atom at a position adjacent to the carbon atom at the condensation site in a cycloalkane fused to an aryl ring or heteroaryl ring) is preferred, a structure in which two hydrogen atoms are substituted on the carbon atom at the α-position is more preferred, and a structure in which a total of four hydrogen atoms are substituted on the two carbon atoms at the α-position is even more preferred. Examples of this substituent include an alkyl (particularly methyl) substituent having 1 to 5 carbon atoms, a halogen (particularly fluorine) substituent, and a deuterium substituent. 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.

[0371] [ka]

[0372] In formula (B), Me represents methyl, and * represents a bonding position, which is bonded to two adjacent elements on the aryl ring or heteroaryl ring to which the group represented by formula (B) is bonded. Examples of such structures include the structures of compounds represented by any of formulas (2-559) to (2-563) and (2-580) described below.

[0373] The number of cycloalkanes condensed to one aromatic ring or heteroaromatic ring is preferably 1 to 3, more preferably 1 or 2, and even more preferably 1. For example, an example in which one or more cycloalkanes are condensed to one benzene ring (phenyl) is shown below. Cycloalkanes condensed to each other as in formula (Cy-1-4) and formula (Cy-2-4) may be condensed. The same applies when the condensed ring (group) is an aromatic ring or heteroaromatic ring other than a benzene ring (phenyl), or when the condensed cycloalkane is a cycloalkane other than cyclopentane or cyclohexane. [ka]

[0374] At least one -CH2- in the cycloalkane may be replaced with -O-. For example, the following shows an example in which one or more -CH2- in a cycloalkane fused to one benzene ring (phenyl) are replaced with -O-. 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.

[0375] [ka]

[0376] At least one hydrogen atom in the cycloalkane may be substituted, and examples of the substituent include aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl (two aryls may be bonded via a single bond or a linking group), alkyl, cycloalkyl, alkoxy, aryloxy, substituted silyl, deuterium, cyano, and halogen. For details, the description of the first substituent mentioned above can be cited. Among these substituents, alkyl (e.g., alkyl having 1 to 6 carbon atoms), cycloalkyl (e.g., cycloalkyl having 3 to 14 carbon atoms), halogen (e.g., fluorine), and deuterium are preferred. In addition, when cycloalkyl is substituted, it may be substituted to form a spiro structure, and examples of this are shown below.

[0377] [ka]

[0378] Other forms of cycloalkane condensation include polycyclic aromatic compounds represented by formula (2), formula (2-a), formula (2-b), formula (2-c), formula (2-d), formula (2-e), or formula (2-f), or polymers having a plurality of structural units represented by any of these, such as >NR, where R is an aryl condensed with a cycloalkane, diarylamino condensed with a cycloalkane (condensed to this aryl portion), carbazolyl condensed with a cycloalkane (condensed to this benzene ring portion), or benzocarbazolyl condensed with a cycloalkane (condensed to this benzene ring portion). For "diarylamino", the groups described above as "first substituent" are included.

[0379] Further, as a more specific example, R in a polycyclic aromatic compound which is a polymer having a plurality of structural units represented by formula (2-a), formula (2-b), formula (2-c), formula (2-d), formula (2-e), or formula (2-f), or any of these structural units, 2is a diarylamino fused to a cycloalkane (fused to the aryl moiety) or a carbazolyl fused to a cycloalkane (fused to the benzene ring moiety).

[0380] In addition, all or a part of hydrogen atoms in the chemical structure of a polycyclic aromatic compound represented by formula (2), formula (2-a), formula (2-b), formula (2-c), formula (2-d), formula (2-e), or formula (2-f), or a polymer having a plurality of structural units represented by any of these, may be deuterium, cyano, or halogen. For example, in formula (2), the A ring, the B ring, the C ring (A to C rings are aryl rings or heteroaryl rings), the substituents on the A to C rings, and X 11 and X 12 When R is >NR, hydrogen in R (=alkyl, cycloalkyl, aryl) can be replaced with deuterium, cyano, or halogen, and among these, there is an embodiment in which all or a part of hydrogen in aryl or heteroaryl is replaced with deuterium, cyano, or halogen. Halogen is fluorine, chlorine, bromine, or iodine, preferably fluorine, chlorine, or bromine, and more preferably fluorine or chlorine.

[0381] More specific examples of the polycyclic aromatic compound of formula (2) include compounds represented by the following formula: In the following formula, "Me" is methyl, "tBu" is tertiary butyl, "iPr" is isopropyl, "Ph" is phenyl, "tAm" is tertiary amyl (tertiary pentyl), and "D" is deuterium.

[0382] [ka]

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[0426] The polycyclic aromatic compound of formula (2) can be synthesized, for example, by the method disclosed in International Publication No. 2019 / 009052 as “Method for Producing Polycyclic Aromatic Compound Represented by Formula (2) and Its Multimer.”

[0427] <Other TADF materials: Compounds of formula (H7)> The polycyclic aromatic compound of the above formula (2) is preferably used in combination with a TADF material whose emission spectrum at least partially overlaps with the absorption spectrum of the polycyclic aromatic compound of the formula (2) used. Examples of such TADF materials include a compound represented by the following formula (H7) or a compound having the following formula (H7) as a partial structure (hereinafter, may be referred to as "a compound of formula (H7)." By using the polycyclic aromatic compound of formula (2) and the compound of formula (H7) simultaneously, the polycyclic aromatic compound of formula (2) functions as an emitting dopant, and the compound of formula (H7) functions as an assisting dopant, thereby providing high color purity. The polycyclic aromatic compound of formula (2) and the compound of formula (H7) may be contained in the same layer or in adjacent layers. When the polycyclic aromatic compound of formula (1), the compound of formula (H7), and the polycyclic aromatic compound of formula (2) are contained in the same light-emitting layer, their contents are preferably 60 to 95 mass%, 39 to 5 mass%, and 10 to 0.01 mass%, respectively, and more preferably 70 to 90 mass%, 29 to 10 mass%, and 5 to 0.05 mass%, respectively.

[0428] [ka]

[0429] In formula (H7), ED is an electron donating group, Ln is a linking group, and EA is an electron accepting group. The lowest excited singlet energy level (E S1 ) and the lowest excited triplet energy level (E T1 ) and the energy difference (ΔE S1T1 ) is less than 0.2 eV (Hiroki Uoyama, Kenichi Goushi, Katsuyuki Shizu, Hiroko Nomura, Chihaya Adachi, Nature, 492, 234-238 (2012)). The energy difference (ΔE S1T1) is preferably 0.15 eV or less, more preferably 0.10 eV or less, and further preferably 0.08 eV or less.

[0430] As the electron donating group (donor structure) and the electron accepting group (acceptor structure) used in the TADF material, for example, the structures described in Chemistry of Materials, 2017, 29, 1946-1963 can be used. 3 Examples of functional groups containing nitrogen include groups derived from carbazole, dimethylcarbazole, di-tert-butylcarbazole, dimethoxycarbazole, tetramethylcarbazole, benzofluorocarbazole, benzothienocarbazole, phenyldihydroindolocarbazole, phenylbicarbazole, bicarbazole, tercarbazole, diphenylcarbazolylamine, tetraphenylcarbazolyldiamine, phenoxazine, dihydrophenazine, phenothiazine, dimethyldihydroacridine, diphenylamine, bis(tert-butyl)phenyl)amine, (diphenylamino)phenyl)diphenylbenzenediamine, dimethyltetraphenyldihydroacridinediamine, tetramethyl-dihydro-indenoacridine, and diphenyl-dihydrodibenzoazasiline. Examples of EA include, for example, sp 2Nitrogen-containing aromatic rings, CN-substituted aromatic rings, rings with ketones and cyano, more specifically sulfonyldibenzene, benzophenone, phenylenebis(phenylmethanone), benzonitrile, isonicotinonitrile, phthalonitrile, isophthalonitrile, paraphthalonitrile, triazole, oxazole, thiadiazole, benzothiazole, benzobis(thiazole), benzoxazole, benzobis(oxazole), quinoline, benzimidazole, dibenzoquinoxaline, heptaazaphenalene, thioxanthone dioxane, Examples of Ln include groups derived from phenyl, dimethylanthracenone, anthracenedione, pyridine, cycloheptabipyridine, benzenetricarbonitrile, fluorene dicarbonitrile, pyrazine dicarbonitrile, pyridine dicarbonitrile, dibenzoquinoxaline dicarbonitrile, pyrimidine, phenylpyrimidine, methylpyrimidine, triazine, triphenyltriazine, bis(phenylsulfonyl)benzene, dimethylthioxanthene dioxide, thianthrene tetraoxide, and tris(dimethylphenyl)borane. Examples of Ln include single bonds and arylenes, more specifically, phenylene, biphenylene, naphthylene, and the like. In addition, in any of the structures, hydrogen may be substituted with alkyl, cycloalkyl, and aryl. In particular, it is preferable that the compound has at least one partial structure selected from carbazole, phenoxazine, acridine, triazine, pyrimidine, pyrazine, thioxanthene, benzonitrile, phthalonitrile, isophthalonitrile, diphenylsulfone, triazole, oxadiazole, thiadiazole, and benzophenone. In formula (H7), the linking group Ln functions as a spacer structure that separates the donor partial structure and the acceptor partial structure.

[0431] More specifically, the compound represented by formula (H7) may be any of the compounds represented by formulas (H7-1), (H7-2) and (H7-3). [ka]

[0432] In formula (H7-1), formula (H7-2) and formula (H7-3), M is each independently a single bond, -O-, >N-Ar or >C(-Ar)2, and is preferably a single bond, -O- or >N-Ar 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; J is a linking group corresponding to Ln in formula (H7), and each J is independently an arylene having 6 to 18 carbon atoms. From the viewpoint of the magnitude of conjugation exuded from the donor partial structure and the acceptor partial structure, an arylene having 6 to 12 carbon atoms is preferable, and more specific examples thereof include phenylene, methylphenylene, and dimethylphenylene. Q is each independently =C(-H)- or =N-, and is preferably =N- from the viewpoint of shallowness of the LUMO of the partial structure to be formed and height of the excited singlet energy level and the excited triplet energy level, Ar each independently represents 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, Ar 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 further preferably hydrogen, phenyl, or carbazolyl; m is 1 or 2; n is an integer of 2 to (6-m), and from the viewpoint of steric hindrance, is preferably an integer of 4 to (6-m). Furthermore, at least one hydrogen in the compounds represented by the above formulas may be substituted with a halogen or deuterium.

[0433] Examples of the compound represented by formula (H7) include compounds represented by the following structures: In the structural formula, * denotes a bond position, "Me" denotes methyl, and "tBu" denotes t-butyl.

[0434] [ka]

[0435] [ka]

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[0438] [ka]

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[0441] [ka]

[0442] [ka]

[0443] Among the specific compounds represented by formula (H7), PIC-TRZ, TXO-TPA, TXO-PhCz, PXZD SO2, ACRD SO2, DTC-DBT, DTAO, 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 are preferred.

[0444] 3-1-6. Electron injection layer and electron transport layer in organic electroluminescent device The electron injection layer 107 plays a role of efficiently injecting electrons moving from the cathode 108 into the light-emitting layer 105 or the electron transport layer 106. The electron transport layer 106 plays a role of efficiently transporting electrons injected from the cathode 108 or electrons injected from the cathode 108 via the electron injection layer 107 to the light-emitting layer 105. The electron transport layer 106 and the electron injection layer 107 are each formed by laminating or mixing one or more types of electron transport / injection materials, or by a mixture of an electron transport / injection material and a polymer binder.

[0445] The electron injection / transport layer is a layer that is responsible for injecting electrons from the cathode and transporting the electrons. It is desirable that the electron injection efficiency is high and that the injected electrons are transported efficiently. For this purpose, it is preferable that the material has a large electron affinity, a large electron mobility, excellent stability, and is unlikely to generate impurities that become traps during manufacture and use. However, when considering the balance between the transport of holes and electrons, if the material mainly plays a role of efficiently blocking the flow of holes from the anode to the cathode without recombining, even if the electron transport ability is not so high, it has the effect of improving the luminous efficiency equivalent to a material with a high electron transport ability. Therefore, the electron injection / transport layer in this embodiment may also include the function of a layer that can efficiently block the movement of holes (hole blocking layer).

[0446] The material (electron transport material) forming the electron transport layer 106 or the electron injection layer 107 can be arbitrarily selected from compounds conventionally used as electron transport compounds in photoconductive materials and known compounds used in the electron injection layer and electron transport layer of organic EL devices. Since the polycyclic aromatic compound of the present invention has a deep HOMO and deep LUMO, it is also preferable to use it as an electron transport material or a hole blocking material (hole blocking material) in the electron injection / transport layer.

[0447] In addition to the polycyclic aromatic compound of the present invention, the material used in the electron transport layer or electron injection layer preferably contains at least one selected from compounds consisting of aromatic rings or heteroaromatic rings composed of one or more atoms selected from carbon, hydrogen, oxygen, sulfur, silicon, and phosphorus, pyrrole derivatives and their condensed ring derivatives, and metal complexes having electron-accepting nitrogen.Specific examples include condensed ring aromatic ring derivatives such as naphthalene and anthracene, styryl aromatic ring derivatives represented by 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 having electron-accepting nitrogen include hydroxyazole complexes such as hydroxyphenyloxazole complexes, azomethine complexes, tropolone metal complexes, flavonol metal complexes, and benzoquinoline metal complexes.These materials may be used alone or in combination with different materials.

[0448] Specific examples of other electron transport compounds include pyridine derivatives, naphthalene derivatives, anthracene derivatives, benzofluorene derivatives, phenanthroline derivatives, perinone derivatives, coumarin derivatives, naphthalimide derivatives, anthraquinone derivatives, diphenoquinone derivatives, diphenylquinone derivatives, perylene derivatives, oxadiazole derivatives (1,3-bis[(4-t-butylphenyl)1,3,4-oxadiazolyl]phenylene, etc.), thiophene derivatives, triazole derivatives (N-naphthyl-2,5-diphenyl-1,3,4-triazole, etc.), thiadiazole derivatives, metal complexes of oxine derivatives, quinolinol-based metal complexes, quinoxaline derivatives, polymers of quinoxaline derivatives, benzazole compounds, gallium complexes, pyrazole derivatives, perfluorinated phenylene derivatives, triazine derivatives, etc. Examples of the compound include pyrazine derivatives, benzoquinoline derivatives (2,2'-bis(benzo[h]quinolin-2-yl)-9,9'-spirobifluorene, etc.), imidazopyridine derivatives, borane derivatives, benzimidazole derivatives (tris(N-phenylbenzimidazol-2-yl)benzene, etc.), benzoxazole derivatives, benzothiazole derivatives, quinoline derivatives, oligopyridine derivatives such as terpyridine, bipyridine derivatives, terpyridine derivatives (1,3-bis(4'-(2,2':6'2"-terpyridinyl))benzene, etc.), naphthyridine derivatives (bis(1-naphthyl)-4-(1,8-naphthyridin-2-yl)phenylphosphine oxide, etc.), aldazine derivatives, arylnitrile derivatives, indole derivatives, phosphine oxide derivatives, and bisstyryl derivatives.

[0449] Further, a metal complex having an electron-accepting nitrogen 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.

[0450] The above-mentioned materials may be used alone or in combination with different materials.

[0451] Among the above-mentioned materials, borane derivatives, pyridine derivatives, fluoranthene derivatives, BO-based derivatives, anthracene derivatives, benzofluorene derivatives, phosphine oxide derivatives, pyrimidine derivatives, arylnitrile derivatives, triazine derivatives, benzimidazole derivatives, phenanthroline derivatives, and quinolinol-based metal complexes are preferable.

[0452] <Borane derivatives> The borane derivative is, for example, a compound represented by the following formula (ETM-1), and is disclosed in detail in JP-A-2007-27587. [ka] In formula (ETM-1), R 11 and R 12 are each independently at least one of hydrogen, alkyl, cycloalkyl, optionally substituted aryl, substituted silyl, optionally substituted nitrogen-containing heterocycle, or cyano; R 13 ~R 16 are each independently an optionally substituted alkyl, an optionally substituted cycloalkyl, or an optionally substituted aryl, X is an optionally substituted arylene, Y is an optionally substituted aryl having 16 or less carbon atoms, a substituted boryl, or an optionally substituted carbazolyl, and each n is independently an integer of 0 to 3. In addition, examples of the substituent in the case of "optionally substituted" or "substituted" include aryl, heteroaryl, alkyl, and cycloalkyl.

[0453] Among the compounds represented by formula (ETM-1), compounds represented by the following formula (ETM-1-1) and compounds represented by the following formula (ETM-1-2) are preferred. [ka]

[0454] In formula (ETM-1-1), R 11 and R12 are each independently at least one of hydrogen, alkyl, cycloalkyl, optionally substituted aryl, substituted silyl, optionally substituted nitrogen-containing heterocycle, or cyano; R 13 ~R 16 are each independently optionally substituted alkyl, optionally substituted cycloalkyl, or optionally substituted aryl; R 21 and R 22 are each independently at least one of hydrogen, alkyl, cycloalkyl, optionally substituted aryl, substituted silyl, optionally substituted nitrogen-containing heterocycle, or cyano; X 1 is an optionally substituted arylene having 20 or less carbon atoms, each n is independently an integer of 0 to 3, and each m is independently an integer of 0 to 4. In addition, examples of the substituent in the case where "optionally substituted" or "substituted" include aryl, heteroaryl, alkyl, and cycloalkyl. [ka]

[0455] In formula (ETM-1-2), R 11 and R 12 are each independently at least one of hydrogen, alkyl, cycloalkyl, optionally substituted aryl, substituted silyl, optionally substituted nitrogen-containing heterocycle, or cyano; R 13 ~R 16 are each independently an optionally substituted alkyl, an optionally substituted cycloalkyl, or an optionally substituted aryl; X 1 is an optionally substituted arylene having 20 or less carbon atoms, and each n is independently an integer of 0 to 3. Examples of the substituent in the case where it is "optionally substituted" or "substituted" include aryl, heteroaryl, alkyl, and cycloalkyl.

[0456] X 1Specific examples of the group include divalent groups represented by any of the following formulae (X-1) to (X-9). [ka] (In each formula, R a are each independently alkyl, cycloalkyl or optionally substituted phenyl, and * represents the bonding position.

[0457] Specific examples of the borane derivative include the following compounds: [ka]

[0458] The borane derivative can be produced using known raw materials and known synthesis methods.

[0459] <Pyridine derivatives> The pyridine derivative is, for example, a compound represented by the following formula (ETM-2), preferably a compound represented by formula (ETM-2-1) or formula (ETM-2-2). [ka]

[0460] φ is an n-valent aryl ring (preferably an n-valent benzene ring, naphthalene ring, anthracene ring, fluorene ring, benzofluorene ring, phenalene ring, phenanthrene ring or triphenylene ring), and n is an integer of 1 to 4.

[0461] In formula (ETM-2-1), R 11 ~R 18 are each independently hydrogen, alkyl (preferably alkyl having 1 to 24 carbon atoms), cycloalkyl (preferably cycloalkyl having 3 to 12 carbon atoms) or aryl (preferably aryl having 6 to 30 carbon atoms).

[0462] In formula (ETM-2-2), R 11 and R12 are each independently hydrogen, alkyl (preferably alkyl having 1 to 24 carbon atoms), cycloalkyl (preferably cycloalkyl having 3 to 12 carbon atoms) or aryl (preferably aryl having 6 to 30 carbon atoms); R 11 and R 12 may be bonded to form a ring.

[0463] In each formula, the "pyridine-based substituent" is any one of the following formulae (Py-1) to (Py-15) (in the formula, * indicates a bonding position), and each pyridine-based substituent may be independently substituted with an alkyl having 1 to 4 carbon atoms or a cycloalkyl having 5 to 10 carbon atoms. Specific examples include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, and t-butyl, and methyl is preferred. In addition, the pyridine-based substituent may be bonded to the φ, anthracene ring, or fluorene ring in each formula via phenylene or naphthylene.

[0464] [ka]

[0465] The pyridine-based substituent is any one of the formulae (Py-1) to (Py-15) (wherein * represents a bonding position), and among these, any one of the following formulae (Py-21) to (Py-44) is preferable. [ka]

[0466] At least one hydrogen atom in each pyridine derivative may be replaced by deuterium, and one of the two "pyridine-based substituents" in formulae (ETM-2-1) and (ETM-2-2) may be replaced by aryl.

[0467] R 11 ~R 18The "alkyl" in the above may be either linear or branched, and examples thereof include linear alkyl having 1 to 24 carbon atoms or branched alkyl having 3 to 24 carbon atoms. A preferred "alkyl" is an alkyl having 1 to 18 carbon atoms (branched alkyl having 3 to 18 carbon atoms). A more preferred "alkyl" is an alkyl having 1 to 12 carbon atoms (branched alkyl having 3 to 12 carbon atoms). An even more preferred "alkyl" is an alkyl having 1 to 6 carbon atoms (branched alkyl having 3 to 6 carbon atoms). An especially preferred "alkyl" is an alkyl having 1 to 4 carbon atoms (branched alkyl having 3 to 4 carbon atoms).

[0468] 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.

[0469] As for the alkyl having 1 to 4 carbon atoms with which the pyridine-based substituent is substituted, the above description of the alkyl can be cited.

[0470] R 11 ~R 18 In the above, the "cycloalkyl" is, for example, a cycloalkyl having 3 to 12 carbon atoms. A preferred "cycloalkyl" is a cycloalkyl having 3 to 10 carbon atoms. A more preferred "cycloalkyl" is a cycloalkyl having 3 to 8 carbon atoms. An even more preferred "cycloalkyl" is a cycloalkyl having 3 to 6 carbon atoms. Specific examples of "cycloalkyl" include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, methylcyclopentyl, cycloheptyl, methylcyclohexyl, cyclooctyl, and dimethylcyclohexyl.

[0471] R 11 ~R 18 As for the "aryl" in the above, a preferable aryl is an aryl having 6 to 30 carbon atoms, a more preferable aryl is an aryl having 6 to 18 carbon atoms, an even more preferable aryl is an aryl having 6 to 14 carbon atoms, and an especially preferable aryl is an aryl having 6 to 12 carbon atoms.

[0472] Specific examples of the "aryl having 6 to 30 carbon atoms" include monocyclic aryl phenyl, fused bicyclic aryl (1-, 2-)naphthyl, fused tricyclic aryl acenaphthylene-(1-, 3-, 4-, 5-)yl, fluoren-(1-, 2-, 3-, 4-, 9-)yl, phenalene-(1-, 2-)yl, (1-, 2-, 3-, 4-, 9-)phenanthryl, fused tetracyclic aryl triphenylene-(1-, 2-)yl, pyrene-(1-, 2-, 4-)yl, naphthacene-(1-, 2-, 5-)yl, fused pentacyclic aryl perylene-(1-, 2-, 3-)yl, pentacene-(1-, 2-, 5-, 6-)yl, and the like.

[0473] Preferred examples of the "aryl having 6 to 30 carbon atoms" include phenyl, naphthyl, phenanthryl, chrysenyl, and triphenylenyl, more preferably phenyl, 1-naphthyl, 2-naphthyl, and phenanthryl, and particularly preferably phenyl, 1-naphthyl, and 2-naphthyl.

[0474] R in formula (ETM-2-2) 11 and R 12 may be bonded to form a ring, and as a result, cyclobutane, cyclopentane, cyclopentene, cyclopentadiene, cyclohexane, fluorene, indene, or the like may be spiro-bonded to the five-membered ring of the fluorene skeleton.

[0475] Specific examples of this pyridine derivative include, for example, the following compounds.

Chemical formula

[0476] This pyridine derivative can be produced using known raw materials and known synthesis methods.

[0477] <Fluoranthene derivative> The fluoranthene derivative is, for example, a compound represented by the following formula (ETM-3), and in detail, it is disclosed in International Publication No. 2010 / 134352.

Chemical formula

[0478] In formula (ETM-3), X 12 ~X 21 represents hydrogen, halogen, linear, branched or cyclic alkyl, linear, branched or cyclic alkoxy, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl. Here, examples of the substituent when it is substituted include aryl, heteroaryl, alkyl or cycloalkyl.

[0479] Specific examples of this fluoranthene derivative include, for example, the following compounds.

Chemical formula

[0480] <BO-based derivative> The BO-based derivative is, for example, a polycyclic aromatic compound represented by the following formula (ETM-4), or a multimer of a polycyclic aromatic compound having a plurality of structures represented by the following formula (ETM-4).

Chemical formula

[0481] R 1 ~R 11 are each independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, alkyl, cycloalkyl, alkoxy, or aryloxy, in which at least one hydrogen may be substituted with aryl, heteroaryl, alkyl, or cycloalkyl.

[0482] Also, R 1 ~R 11 Adjacent groups among these may be bonded to each other to form an aryl ring or a heteroaryl ring together with the a ring, the b ring, or the c ring, and at least one hydrogen atom in the formed ring may be substituted with an aryl, a heteroaryl, a diarylamino, a diheteroarylamino, an arylheteroarylamino, an alkyl, a cycloalkyl, an alkoxy, or an aryloxy, and at least one hydrogen atom in these rings may be substituted with an aryl, a heteroaryl, an alkyl, or a cycloalkyl.

[0483] In addition, at least one hydrogen in the compound or structure represented by formula (ETM-4) may be substituted with a halogen or deuterium.

[0484] For an explanation of the substituents and the form of ring formation in formula (ETM-4), the explanation of the polycyclic aromatic compounds represented by formulas (1A) and (1B) can be cited.

[0485] Specific examples of the BO derivative include the following compounds: [ka]

[0486] The BO derivative can be produced using known raw materials and known synthesis methods.

[0487] <Anthracene derivatives> One of the anthracene derivatives is, for example, a compound represented by the following formula (ETM-5). [ka]

[0488] Ar 1 are each independently a single bond, or a divalent benzene, naphthalene, anthracene, fluorene, or phenalene.

[0489] Ar 2are each independently an aryl having 6 to 20 carbon atoms, preferably an aryl having 6 to 16 carbon atoms, more preferably an aryl having 6 to 12 carbon atoms, and particularly preferably an aryl having 6 to 10 carbon atoms. Specific examples of "aryl having 6 to 20 carbon atoms" include monocyclic aryls such as phenyl, (o-, m-, p-)tolyl, (2,3-, 2,4-, 2,5-, 2,6-, 3,4-, 3,5-)xylyl, mesityl (2,4,6-trimethylphenyl), and (o-, m-, p-)cumenyl, bicyclic aryls such as (2-, 3-, 4-)biphenylyl, condensed bicyclic aryls such as (1-, 2-)naphthyl, and tricyclic aryls such as terphenylyl (m-terphenyl-2'-yl, m-terphenyl-4'-yl, m-terphenyl-5'-yl, o-terphenyl-3'-yl, o-terphenyl-4'-yl, p-terphenyl-2'-yl, m-terphenyl-2-yl, m-terphenyl-3-yl, m-terphenyl-4'-yl, p-terphenyl-2 ...4'-yl, p-terphenyl-2-yl, m-terphenyl-2-yl, m-terphenyl-3-yl, m-terphenyl-4'-yl, p-terphenyl-2-yl, m-terphenyl-4'-yl, p-terphenyl-2-yl, m-terphenyl-2-yl, m-terphenyl-3-yl, m aryl, o-terphenyl-4-yl, o-terphenyl-2-yl, o-terphenyl-3-yl, o-terphenyl-4-yl, p-terphenyl-2-yl, p-terphenyl-3-yl, p-terphenyl-4-yl; condensed tricyclic aryls, anthracene-(1-,2-,9-)yl, acenaphthylene-(1-,3-,4-,5-)yl, fluorene-(1-,2-,3-,4-,9-)yl, phenalene-(1-,2-)yl, (1-,2-,3-,4-,9-)phenanthryl; condensed tetracyclic aryls, triphenylene-(1-,2-)yl, pyrene-(1-,2-,4-)yl, tetracene-(1-,2-,5-)yl; condensed pentacyclic aryls, perylene-(1-,2-,3-)yl, and the like. Specific examples of the "aryl having 6 to 10 carbon atoms" include phenyl, biphenylyl, naphthyl, terphenylyl, anthracenyl, acenaphthylenyl, fluorenyl, phenalenyl, phenanthryl, triphenylenyl, pyrenyl, tetracenyl, and perylenyl.

[0490] R 1 ~R 4 are each independently hydrogen, alkyl having 1 to 6 carbon atoms, cycloalkyl having 3 to 6 carbon atoms, or aryl having 6 to 20 carbon atoms. R 1 ~R4 The alkyl having 1 to 6 carbon atoms in the formula (I) may be either linear or branched. That is, it is a linear alkyl having 1 to 6 carbon atoms or a branched alkyl having 3 to 6 carbon atoms. More preferably, it is an alkyl having 1 to 4 carbon atoms (branched alkyl having 3 to 4 carbon atoms). Specific examples include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, t-butyl, n-pentyl, isopentyl, neopentyl, t-pentyl, n-hexyl, 1-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, and 2-ethylbutyl. Methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, and t-butyl are preferred, and methyl, ethyl, and t-butyl are more preferred.

[0491] R 1 ~R 4 Specific examples of the cycloalkyl having 3 to 6 carbon atoms include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, methylcyclopentyl, cycloheptyl, methylcyclohexyl, cyclooctyl, and dimethylcyclohexyl.

[0492] R 1 ~R 4 In the above, the aryl having 6 to 20 carbon atoms is preferably an aryl having 6 to 16 carbon atoms, more preferably an aryl having 6 to 12 carbon atoms, and particularly preferably an aryl having 6 to 10 carbon atoms. Specific examples of "aryl having 6 to 20 carbon atoms" include Ar 2 Specific examples of "aryl having 6 to 20 carbon atoms" in the above can be cited. Preferred "aryl having 6 to 20 carbon atoms" are phenyl, biphenylyl, terphenylyl, or naphthyl, more preferably phenyl, biphenylyl, 1-naphthyl, 2-naphthyl, or m-terphenyl-5'-yl, further preferably phenyl, biphenylyl, 1-naphthyl, or 2-naphthyl, and most preferably phenyl.

[0493] Specific examples of these anthracene derivatives include the following compounds. [ka]

[0494] These anthracene derivatives can be produced using known raw materials and known synthesis methods.

[0495] <Benzofluorene derivatives> The benzofluorene derivative is, for example, a compound represented by the following formula (ETM-6). [ka]

[0496] Ar 1 are each independently an aryl having 6 to 20 carbon atoms, and Ar 2 The same explanation as for "aryl having 6 to 20 carbon atoms" in the above can be cited. An aryl having 6 to 16 carbon atoms is preferable, an aryl having 6 to 12 carbon atoms is more preferable, and an aryl having 6 to 10 carbon atoms is particularly preferable. Specific examples include phenyl, biphenylyl, naphthyl, terphenylyl, anthracenyl, acenaphthylenyl, fluorenyl, phenalenyl, phenanthryl, triphenylenyl, pyrenyl, tetracenyl, perylenyl, etc.

[0497] Ar 2 are each independently hydrogen, alkyl (preferably alkyl having 1 to 24 carbon atoms), cycloalkyl (preferably cycloalkyl having 3 to 12 carbon atoms) or aryl (preferably aryl having 6 to 30 carbon atoms), and two Ar 2 may be bonded to form a ring.

[0498] Ar 2The "alkyl" in the above may be either linear or branched, and examples thereof include linear alkyl having 1 to 24 carbon atoms or branched alkyl having 3 to 24 carbon atoms. A preferred "alkyl" is an alkyl having 1 to 18 carbon atoms (branched alkyl having 3 to 18 carbon atoms). A more preferred "alkyl" is an alkyl having 1 to 12 carbon atoms (branched alkyl having 3 to 12 carbon atoms). An even more preferred "alkyl" is an alkyl having 1 to 6 carbon atoms (branched alkyl having 3 to 6 carbon atoms). An especially preferred "alkyl" is an alkyl having 1 to 4 carbon atoms (branched alkyl having 3 to 4 carbon atoms). Specific examples of "alkyl" include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, t-butyl, n-pentyl, isopentyl, neopentyl, t-pentyl, n-hexyl, 1-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, n-heptyl, 1-methylhexyl, and the like.

[0499] Ar 2 In the above, the "cycloalkyl" is, for example, a cycloalkyl having 3 to 12 carbon atoms. A preferred "cycloalkyl" is a cycloalkyl having 3 to 10 carbon atoms. A more preferred "cycloalkyl" is a cycloalkyl having 3 to 8 carbon atoms. An even more preferred "cycloalkyl" is a cycloalkyl having 3 to 6 carbon atoms. Specific examples of the "cycloalkyl" include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, methylcyclopentyl, cycloheptyl, methylcyclohexyl, cyclooctyl, and dimethylcyclohexyl.

[0500] Ar 2 As for the "aryl" in the above, a preferable aryl is an aryl having 6 to 30 carbon atoms, a more preferable aryl is an aryl having 6 to 18 carbon atoms, an even more preferable aryl is an aryl having 6 to 14 carbon atoms, and an especially preferable aryl is an aryl having 6 to 12 carbon atoms.

[0501] Specific examples of the "aryl having 6 to 30 carbon atoms" include phenyl, naphthyl, acenaphthylenyl, fluorenyl, phenalenyl, phenanthryl, triphenylenyl, pyrenyl, naphthacenyl, perylenyl, and pentacenyl.

[0502] Two Ar 2 may be bonded to form a ring, and as a result, cyclobutane, cyclopentane, cyclopentene, cyclopentadiene, cyclohexane, fluorene, indene, or the like may be spiro-bonded to the five-membered ring of the fluorene skeleton.

[0503] Specific examples of the benzofluorene derivative include the following compounds: [ka]

[0504] The benzofluorene derivative can be produced using known raw materials and known synthesis methods.

[0505] <Phosphine oxide derivatives> The phosphine oxide derivative is, for example, a compound represented by the following formula (ETM-7-1): The details are also described in WO 2013 / 079217 and WO 2013 / 079678. [ka]

[0506] R 5 is a substituted or unsubstituted alkyl having 1 to 20 carbon atoms, cycloalkyl having 3 to 16 carbon atoms, aryl having 6 to 20 carbon atoms, or heteroaryl having 5 to 20 carbon atoms, R 6 is CN, a substituted or unsubstituted alkyl having 1 to 20 carbon atoms, a cycloalkyl having 3 to 16 carbon atoms, a heteroalkyl having 1 to 20 carbon atoms, an aryl having 6 to 20 carbon atoms, a heteroaryl having 5 to 20 carbon atoms, an alkoxy having 1 to 20 carbon atoms, or an aryloxy having 6 to 20 carbon atoms, R 7 and R 8 each independently represents a substituted or unsubstituted aryl having 6 to 20 carbon atoms or a heteroaryl having 5 to 20 carbon atoms, R 9 is oxygen or sulfur, j is 0 or 1, k is 0 or 1, r is an integer of 0 to 4, and q is an integer of 1 to 3. When substituted, the substituent may be an aryl, heteroaryl, alkyl or cycloalkyl.

[0507] The phosphine oxide derivative may be, for example, a compound represented by the following formula (ETM-7-2). [ka]

[0508] R 1 ~R 3 may be the same or different and are selected from hydrogen, alkyl, cycloalkyl, aralkyl, alkenyl, cycloalkenyl, alkynyl, alkoxy, alkylthio, cycloalkylthio, aryl ether (aryl ether group), aryl thioether (aryl thioether group), aryl, heterocyclic group, halogen, cyano, formyl, carbonyl, carboxyl, amino, nitro, silyl, and a fused ring formed between adjacent substituents.

[0509] Ar 1 may be the same or different and are arylene or heteroarylene. Ar 2 may be the same or different and are aryl or heteroaryl, provided that Ar 1 and Ar 2 At least one of R has a substituent or forms a condensed ring with the adjacent substituent. n is an integer of 0 to 3. When n is 0, there is no unsaturated structural portion. When n is 3, R 1 does not exist.

[0510] Among these substituents, alkyl refers to saturated aliphatic hydrocarbon groups such as methyl, ethyl, propyl, and butyl, which may be unsubstituted or substituted. If substituted, the substituent is not particularly limited, and may be, for example, alkyl, aryl, or heterocyclic groups, which is also the case in the following description. The number of carbon atoms in the alkyl is not particularly limited, but is usually in the range of 1 to 20 in terms of availability and cost.

[0511] The term "cycloalkyl" refers to a saturated alicyclic hydrocarbon group, such as cyclopropyl, cyclohexyl, norbornyl, adamantyl, etc., which may be unsubstituted or substituted. The number of carbon atoms in the alkyl portion is not particularly limited, but is usually in the range of 3 to 20.

[0512] The term "aralkyl" refers to an aromatic hydrocarbon group mediated by an aliphatic hydrocarbon such as benzyl or phenylethyl, and both the aliphatic hydrocarbon and the aromatic hydrocarbon may be unsubstituted or substituted. The number of carbon atoms in the aliphatic portion is not particularly limited, but is usually in the range of 1 to 20.

[0513] The alkenyl refers to an unsaturated aliphatic hydrocarbon group containing a double bond, such as vinyl, allyl, butadienyl, which may be unsubstituted or substituted. The number of carbon atoms in the alkenyl is not particularly limited, but is usually in the range of 2 to 20.

[0514] Moreover, cycloalkenyl refers to an unsaturated alicyclic hydrocarbon group containing a double bond, such as cyclopentenyl, cyclopentadienyl, cyclohexenyl, etc., which may be unsubstituted or substituted.

[0515] The term "alkynyl" refers to an unsaturated aliphatic hydrocarbon group containing a triple bond, such as acetylenyl, which may be unsubstituted or substituted. The number of carbon atoms in the alkynyl is not particularly limited, but is usually within the range of 2 to 20.

[0516] The term "alkoxy" refers to an aliphatic hydrocarbon group, such as methoxy, which is bonded via an ether bond, and the aliphatic hydrocarbon group may be unsubstituted or substituted. The number of carbon atoms in the alkoxy is not particularly limited, but is usually in the range of 1 to 20.

[0517] Moreover, alkylthio is a group in which the oxygen atom of the ether bond of alkoxy is replaced with a sulfur atom.

[0518] Moreover, cycloalkylthio is a group in which the oxygen atom of the ether bond of cycloalkoxy is replaced with a sulfur atom.

[0519] The aryl ether refers to an aromatic hydrocarbon group, such as phenoxy, which is bonded via an ether bond, and the aromatic hydrocarbon group may be unsubstituted or substituted. The number of carbon atoms in the aryl ether is not particularly limited, but is usually in the range of 6 to 40.

[0520] An aryl thioether is a group in which the oxygen atom of the ether bond of an aryl ether is replaced with a sulfur atom.

[0521] The aryl group refers to an aromatic hydrocarbon group such as phenyl, naphthyl, biphenylyl, phenanthryl, terphenylyl, pyrenyl, etc. The aryl group may be unsubstituted or substituted. The number of carbon atoms in the aryl group is not particularly limited, but is usually in the range of 6 to 40.

[0522] The heterocyclic group refers to a cyclic structure group having atoms other than carbon, such as furanyl, thienyl, oxazolyl, pyridyl, quinolinyl, carbazolyl, etc., which may be unsubstituted or substituted. The number of carbon atoms in the heterocyclic group is not particularly limited, but is usually in the range of 2 to 30.

[0523] Halogen refers to fluorine, chlorine, bromine and iodine.

[0524] Formyl, carbonyl and amino may also include groups substituted with aliphatic hydrocarbons, alicyclic hydrocarbons, aromatic hydrocarbons, heterocycles and the like.

[0525] Furthermore, the aliphatic hydrocarbons, alicyclic hydrocarbons, aromatic hydrocarbons and heterocycles may be either unsubstituted or substituted.

[0526] Silyl refers to a silicon compound group such as trimethylsilyl, which may be unsubstituted or substituted. The number of carbon atoms in silyl is not particularly limited, but is usually in the range of 3 to 20. The number of silicon atoms is usually 1 to 6.

[0527] The condensed ring formed between adjacent substituents is, for example, Ar 1 and R 2 , Ar 1 and R 3 , Ar 2 and R 2 , Ar 2 and R 3 , R 2 and R 3 , Ar 1 and Ar 2 etc., where n is 1, two R 1 They may form conjugated or non-conjugated fused rings together. These fused rings may contain nitrogen, oxygen, or sulfur atoms in the ring structure, and may be fused to further rings.

[0528] Specific examples of the phosphine oxide derivative include the following compounds: [ka]

[0529] The phosphine oxide derivative can be produced using known raw materials and known synthesis methods.

[0530] <Pyrimidine derivatives> The pyrimidine derivative is, for example, a compound represented by the following formula (ETM-8), preferably a compound represented by the following formula (ETM-8-1). Details are also described in WO 2011 / 021689. [ka]

[0531] Each Ar is independently an optionally substituted aryl or an optionally substituted heteroaryl, and n is an integer of 1 to 4, preferably an integer of 1 to 3, and more preferably 2 or 3.

[0532] The "aryl" in the "optionally substituted aryl" includes, for example, an aryl having 6 to 30 carbon atoms, preferably an aryl having 6 to 24 carbon atoms, more preferably an aryl having 6 to 20 carbon atoms, and further preferably an aryl having 6 to 12 carbon atoms.

[0533] Specific examples of "aryl" include monocyclic aryl phenyl, bicyclic aryl (2-, 3-, 4-) biphenylyl, condensed bicyclic aryl (1-, 2-) naphthyl, tricyclic aryl terphenylyl (m-terphenyl-2'-yl, m-terphenyl-4'-yl, m-terphenyl-5'-yl, o-terphenyl-3'-yl, o-terphenyl-4'-yl, p-terphenyl-2'-yl, m-terphenyl-2-yl, m-terphenyl-3-yl, m-terphenyl-4-yl, o-terphenyl-2-yl, o-terphenyl-3-yl, o-terphenyl-4-yl, p-terphenyl-2-yl, p-terphenyl-3-yl, p-terphenyl-4-yl), condensed tricyclic aryl Examples of the aryl include acenaphthylene-(1-,3-,4-,5-)yl, fluorene-(1-,2-,3-,4-,9-)yl, phenalene-(1-,2-)yl, (1-,2-,3-,4-,9-)phenanthryl, the tetracyclic aryl group is quaterphenylyl (5'-phenyl-m-terphenyl-2-yl, 5'-phenyl-m-terphenyl-3-yl, 5'-phenyl-m-terphenyl-4-yl, m-quaterphenylyl), the condensed tetracyclic aryl group is triphenylene-(1-,2-)yl, pyrene-(1-,2-,4-)yl, naphthacene-(1-,2-,5-)yl, the condensed pentacyclic aryl group is perylene-(1-,2-,3-)yl, pentacene-(1-,2-,5-,6-)yl, and the like.

[0534] Examples of the "heteroaryl" in "optionally substituted heteroaryl" include heteroaryl having 2 to 30 carbon atoms, preferably heteroaryl having 2 to 25 carbon atoms, more preferably heteroaryl having 2 to 20 carbon atoms, further preferably heteroaryl having 2 to 15 carbon atoms, and particularly preferably heteroaryl having 2 to 10 carbon atoms. Examples of the heteroaryl include heterocycles containing, as ring-constituting atoms other than carbon, 1 to 5 heteroatoms selected from oxygen, sulfur, and nitrogen.

[0535] Specific examples of heteroaryl include furyl, thienyl, pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, pyrazolyl, oxadiazolyl, furazanyl, thiadiazolyl, triazolyl, tetrazolyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, benzofuranyl, isobenzofuranyl, benzo[b]thienyl, indolyl, isoindolyl, 1H-indazolyl, benzimidazolyl, benzoxazolyl, benzothiazolyl, 1H-benzotriazolyl, quinolyl, isoquinolyl, cinnolyl, quinazolyl, quinoxalinyl, phthalazinyl, naphthyridinyl, purinyl, pteridinyl, carbazolyl, acridinyl, phenoxazinyl, phenothiazinyl, phenazinyl, phenoxathiinyl, thianthrenyl, and indolizinyl.

[0536] The above aryl and heteroaryl may be substituted, for example, by the above aryl or heteroaryl, respectively.

[0537] Specific examples of the pyrimidine derivative include the following compounds: [ka]

[0538] The pyrimidine derivative can be produced using known raw materials and known synthesis methods.

[0539] <Aryl nitrile derivatives> The arylnitrile derivative is, for example, a compound represented by the following formula (ETM-9), or a multimer in which a plurality of such compounds are bonded together via single bonds, etc. Details are described in the specification of US Patent Publication No. 2014 / 0197386. [ka]

[0540] Ar niFrom the viewpoint of fast electron transport, it is preferable that the number of carbon atoms is large, and a high E T1 From the viewpoint of the above, it is preferable that the number of carbon atoms is small. ni Specifically, the E T1 It is preferably an aryl having 6 to 20 carbon atoms, more preferably an aryl having 6 to 14 carbon atoms, and even more preferably an aryl having 6 to 10 carbon atoms. In addition, the number of substitutions n of the nitrile group is preferably a high E T1 From the viewpoint of S1 From this viewpoint, it is preferable that the number of substituted nitrile groups, n, is specifically an integer of 1 to 4, preferably an integer of 1 to 3, more preferably an integer of 1 to 2, and further preferably 1.

[0541] Each Ar is independently an optionally substituted aryl or an optionally substituted heteroaryl. S1 and high E T1 From the viewpoint of charge transportability, it is preferable that the donor heteroaryl is used, and it is preferable that the donor heteroaryl is small because it is used as an electron transport layer. From the viewpoint of charge transportability, it is preferable that the aryl or heteroaryl has a large number of carbon atoms, and it is preferable that the aryl or heteroaryl has many substituents. The number of substitutions m of Ar is specifically an integer of 1 to 4, preferably an integer of 1 to 3, and more preferably 1 to 2.

[0542] The "aryl" in the "optionally substituted aryl" includes, for example, an aryl having 6 to 30 carbon atoms, preferably an aryl having 6 to 24 carbon atoms, more preferably an aryl having 6 to 20 carbon atoms, and further preferably an aryl having 6 to 12 carbon atoms.

[0543] Specific examples of "aryl" include monocyclic aryl phenyl, bicyclic aryl (2-, 3-, 4-) biphenylyl, condensed bicyclic aryl (1-, 2-) naphthyl, tricyclic aryl terphenylyl (m-terphenyl-2'-yl, m-terphenyl-4'-yl, m-terphenyl-5'-yl, o-terphenyl-3'-yl, o-terphenyl-4'-yl, p-terphenyl-2'-yl, m-terphenyl-2-yl, m-terphenyl-3-yl, m-terphenyl-4-yl, o-terphenyl-2-yl, o-terphenyl-3-yl, o-terphenyl-4-yl, p-terphenyl-2-yl, p-terphenyl-3-yl, p-terphenyl-4-yl), condensed tricyclic aryl Examples of the aryl include acenaphthylene-(1-,3-,4-,5-)yl, fluorene-(1-,2-,3-,4-,9-)yl, phenalene-(1-,2-)yl, (1-,2-,3-,4-,9-)phenanthryl, the tetracyclic aryl group is quaterphenylyl (5'-phenyl-m-terphenyl-2-yl, 5'-phenyl-m-terphenyl-3-yl, 5'-phenyl-m-terphenyl-4-yl, m-quaterphenylyl), the condensed tetracyclic aryl group is triphenylene-(1-,2-)yl, pyrene-(1-,2-,4-)yl, naphthacene-(1-,2-,5-)yl, the condensed pentacyclic aryl group is perylene-(1-,2-,3-)yl, pentacene-(1-,2-,5-,6-)yl, and the like.

[0544] Examples of the "heteroaryl" in "optionally substituted heteroaryl" include heteroaryl having 2 to 30 carbon atoms, preferably heteroaryl having 2 to 25 carbon atoms, more preferably heteroaryl having 2 to 20 carbon atoms, further preferably heteroaryl having 2 to 15 carbon atoms, and particularly preferably heteroaryl having 2 to 10 carbon atoms. Examples of the heteroaryl include heterocycles containing, as ring-constituting atoms other than carbon, 1 to 5 heteroatoms selected from oxygen, sulfur, and nitrogen.

[0545] Specific examples of heteroaryl include furyl, thienyl, pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, pyrazolyl, oxadiazolyl, furazanyl, thiadiazolyl, triazolyl, tetrazolyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, benzofuranyl, isobenzofuranyl, benzo[b]thienyl, indolyl, isoindolyl, 1H-indazolyl, benzimidazolyl, benzoxazolyl, benzothiazolyl, 1H-benzotriazolyl, quinolyl, isoquinolyl, cinnolyl, quinazolyl, quinoxalinyl, phthalazinyl, naphthyridinyl, purinyl, pteridinyl, carbazolyl, acridinyl, phenoxazinyl, phenothiazinyl, phenazinyl, phenoxathiinyl, thianthrenyl, and indolizinyl.

[0546] The above aryl and heteroaryl may be substituted, for example, by the above aryl or heteroaryl, respectively.

[0547] The arylnitrile derivative may be a polymer in which a plurality of compounds represented by formula (ETM-9) are bonded together via single bonds, etc. In this case, they may be bonded together via an aryl ring (preferably a polyvalent benzene ring, naphthalene ring, anthracene ring, fluorene ring, benzofluorene ring, phenalene ring, phenanthrene ring, or triphenylene ring) in addition to a single bond.

[0548] Specific examples of the arylnitrile derivative include the following compounds: [ka]

[0549] The arylnitrile derivatives can be produced using known raw materials and known synthesis methods.

[0550] <Triazine derivatives> The triazine derivative is, for example, a compound represented by the following formula (ETM-10), preferably a compound represented by the following formula (ETM-10-1), the details of which are described in the specification of US Patent Application Publication No. 2011 / 0156013. [ka]

[0551] Each Ar is independently an optionally substituted aryl or an optionally substituted heteroaryl, and n is an integer of 1 to 3, preferably 2 or 3.

[0552] The "aryl" in the "optionally substituted aryl" includes, for example, an aryl having 6 to 30 carbon atoms, preferably an aryl having 6 to 24 carbon atoms, more preferably an aryl having 6 to 20 carbon atoms, and further preferably an aryl having 6 to 12 carbon atoms.

[0553] Specific examples of "aryl" include monocyclic aryl phenyl, bicyclic aryl (2-, 3-, 4-) biphenylyl, condensed bicyclic aryl (1-, 2-) naphthyl, tricyclic aryl terphenylyl (m-terphenyl-2'-yl, m-terphenyl-4'-yl, m-terphenyl-5'-yl, o-terphenyl-3'-yl, o-terphenyl-4'-yl, p-terphenyl-2'-yl, m-terphenyl-2-yl, m-terphenyl-3-yl, m-terphenyl-4-yl, o-terphenyl-2-yl, o-terphenyl-3-yl, o-terphenyl-4-yl, p-terphenyl-2-yl, p-terphenyl-3-yl, p-terphenyl-4-yl), condensed tricyclic aryl Examples of the aryl include acenaphthylene-(1-,3-,4-,5-)yl, fluorene-(1-,2-,3-,4-,9-)yl, phenalene-(1-,2-)yl, (1-,2-,3-,4-,9-)phenanthryl, the tetracyclic aryl group is quaterphenylyl (5'-phenyl-m-terphenyl-2-yl, 5'-phenyl-m-terphenyl-3-yl, 5'-phenyl-m-terphenyl-4-yl, m-quaterphenylyl), the condensed tetracyclic aryl group is triphenylene-(1-,2-)yl, pyrene-(1-,2-,4-)yl, naphthacene-(1-,2-,5-)yl, the condensed pentacyclic aryl group is perylene-(1-,2-,3-)yl, pentacene-(1-,2-,5-,6-)yl, and the like.

[0554] Examples of the "heteroaryl" in "optionally substituted heteroaryl" include heteroaryl having 2 to 30 carbon atoms, preferably heteroaryl having 2 to 25 carbon atoms, more preferably heteroaryl having 2 to 20 carbon atoms, further preferably heteroaryl having 2 to 15 carbon atoms, and particularly preferably heteroaryl having 2 to 10 carbon atoms. Examples of the heteroaryl include heterocycles containing, as ring-constituting atoms other than carbon, 1 to 5 heteroatoms selected from oxygen, sulfur, and nitrogen.

[0555] Specific examples of heteroaryl include furyl, thienyl, pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, pyrazolyl, oxadiazolyl, furazanyl, thiadiazolyl, triazolyl, tetrazolyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, benzofuranyl, isobenzofuranyl, benzo[b]thienyl, indolyl, isoindolyl, 1H-indazolyl, benzimidazolyl, benzoxazolyl, benzothiazolyl, 1H-benzotriazolyl, quinolyl, isoquinolyl, cinnolyl, quinazolyl, quinoxalinyl, phthalazinyl, naphthyridinyl, purinyl, pteridinyl, carbazolyl, acridinyl, phenoxazinyl, phenothiazinyl, phenazinyl, phenoxathiinyl, thianthrenyl, and indolizinyl.

[0556] The above aryl and heteroaryl may be substituted, for example, by the above aryl or heteroaryl, respectively.

[0557] Specific examples of the triazine derivative include the following compounds: [ka]

[0558] The triazine derivative can be produced using known raw materials and known synthesis methods.

[0559] <Benzimidazole derivatives> The benzimidazole derivative is, for example, a compound represented by the following formula (ETM-11). [ka]

[0560] φ is an n-valent aryl ring (preferably an n-valent benzene ring, naphthalene ring, anthracene ring, fluorene ring, benzofluorene ring, phenalene ring, phenanthrene ring, or triphenylene ring), n is an integer from 1 to 4, and the "benzoimidazole-based substituent" is a substituent in which the pyridyl in the "pyridine-based substituent" in the formulae (ETM-2), (ETM-2-1), and (ETM-2-2) is replaced with benzimidazolyl, and at least one hydrogen in the benzimidazole derivative may be replaced with deuterium.

[0561] [ka]

[0562] R in the above benzimidazolyl 11 is hydrogen, alkyl having 1 to 24 carbon atoms, cycloalkyl having 3 to 12 carbon atoms, or aryl having 6 to 30 carbon atoms, and R in formula (ETM-2-1) and formula (ETM-2-2) 11 The explanation can be cited.

[0563] φ is preferably an anthracene ring or a fluorene ring. In this case, the structure can be as described in the formula (ETM-2-1) or the formula (ETM-2-2). R 11 ~R 18 The explanation for formula (ETM-2-1) or formula (ETM-2-2) can be cited. In addition, in formula (ETM-2-1) or formula (ETM-2-2), the two pyridine-based substituents are explained as being bonded, but when these are replaced with benzimidazole-based substituents, both pyridine-based substituents may be replaced with benzimidazole-based substituents (i.e., n=2), or one of the pyridine-based substituents may be replaced with a benzimidazole-based substituent and the other pyridine-based substituent may be replaced with R 11 ~R 18 (i.e., n=1). Furthermore, for example, R in formula (ETM-2-1) 11 ~R 18At least one of the above is replaced with a benzimidazole-based substituent to form a "pyridine-based substituent" R 11 ~R 18 may be substituted.

[0564] Specific examples of the benzimidazole derivative include 1-phenyl-2-(4-(10-phenylanthracen-9-yl)phenyl)-1H-benzo[d]imidazole, 2-(4-(10-(naphthalen-2-yl)anthracen-9-yl)phenyl)-1-phenyl-1H-benzo[d]imidazole, 2-(3-(10-(naphthalen-2-yl)anthracen-9-yl)phenyl)-1-phenyl-1H-benzo[d]imidazole, and 5-(10-(naphthalen-2-yl)anthracen-9-yl)-1,2-diphenyl-1H-benzo[d]imidazole. , 1-(4-(10-(naphthalene-2-yl)anthracen-9-yl)phenyl)-2-phenyl-1H-benzo[d]imidazole, 2-(4-(9,10-di(naphthalene-2-yl)anthracen-2-yl)phenyl)-1-phenyl-1H-benzo[d]imidazole, 1-(4-(9,10-di(naphthalene-2-yl)anthracen-2-yl)phenyl)-2-phenyl-1H-benzo[d]imidazole, 5-(9,10-di(naphthalene-2-yl)anthracen-2-yl)-1,2-diphenyl-1H-benzo[d]imidazole, and the like.

[0565] [ka]

[0566] The benzimidazole derivative can be produced using known raw materials and known synthesis methods.

[0567] <Phenanthroline derivatives> The phenanthroline derivative is, for example, a compound represented by the following formula (ETM-12) or formula (ETM-12-1), the details of which are described in WO 2006 / 021982. [ka]

[0568] φ is an n-valent aryl ring (preferably an n-valent benzene ring, naphthalene ring, anthracene ring, fluorene ring, benzofluorene ring, phenalene ring, phenanthrene ring or triphenylene ring), and n is an integer of 1 to 4.

[0569] R of each formula 11 ~R 18 are each independently hydrogen, alkyl (preferably alkyl having 1 to 24 carbon atoms), cycloalkyl (preferably cycloalkyl having 3 to 12 carbon atoms), or aryl (preferably aryl having 6 to 30 carbon atoms). 11 ~R 18 Either one of these bonds becomes a bond to the aryl ring φ.

[0570] At least one hydrogen atom in each of the phenanthroline derivatives may be replaced with deuterium.

[0571] R 11 ~R 18 As the alkyl, cycloalkyl and aryl in the formula (ETM-2), R 11 ~R 18 can be cited. In addition to the above examples, φ can have the following structural formula. In the structural formula, R is independently hydrogen, methyl, ethyl, isopropyl, cyclohexyl, phenyl, 1-naphthyl, 2-naphthyl, biphenylyl, or terphenylyl, and * indicates a bonding position.

[0572] [ka]

[0573] Specific examples of the phenanthroline derivative include 4,7-diphenyl-1,10-phenanthroline, 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline, 9,10-di(1,10-phenanthroline-2-yl)anthracene, 2,6-di(1,10-phenanthroline-5-yl)pyridine, 1,3,5-tri(1,10-phenanthroline-5-yl)benzene, 9,9'-difluoro-bi(1,10-phenanthroline-5-yl), bathocuproine, 1,3-bis(2-phenyl-1,10-phenanthroline-9-yl)benzene, and compounds represented by the following structural formula. [ka]

[0574] The phenanthroline derivative can be produced using known raw materials and known synthesis methods.

[0575] <Quinolinol metal complexes> The quinolinol metal complex is, for example, a compound represented by the following formula (ETM-13). [ka] In the formula, R 1 ~R 6 are each independently hydrogen, fluorine, alkyl, cycloalkyl, aralkyl, alkenyl, cyano, alkoxy, or aryl; M is Li, Al, Ga, Be, or Zn; and n is an integer of 1 to 3.

[0576] Specific examples of quinolinol-based metal complexes include 8-quinolinol lithium, tris(8-quinolinolato)aluminum, tris(4-methyl-8-quinolinolato)aluminum, tris(5-methyl-8-quinolinolato)aluminum, tris(3,4-dimethyl-8-quinolinolato)aluminum, tris(4,5-dimethyl-8-quinolinolato)aluminum, tris(4,6-dimethyl-8-quinolinolato)aluminum, bis(2-methyl-8-quinolinolato)(phenolate)aluminum, bis(2-methyl-8-quinolinolato)(phenolate), and bis(2-methyl-8-quinolinolato). Bis(2-methylphenolate)aluminum, bis(2-methyl-8-quinolinate)(3-methylphenolate)aluminum, bis(2-methyl-8-quinolinate)(4-methylphenolate)aluminum, bis(2-methyl-8-quinolinate)(2-phenylphenolate)aluminum, bis(2-methyl-8-quinolinate)(3-phenylphenolate)aluminum, bis(2-methyl-8-quinolinate)(4-phenylphenolate)aluminum, bis(2-methyl-8-quinolinate)(2,3 -dimethylphenolate)aluminum, bis(2-methyl-8-quinolinate)(2,6-dimethylphenolate)aluminum, bis(2-methyl-8-quinolinate)(3,4-dimethylphenolate)aluminum, bis(2-methyl-8-quinolinate)(3,5-dimethylphenolate)aluminum, bis(2-methyl-8-quinolinate)(3,5-di-t-butylphenolate)aluminum, bis(2-methyl-8-quinolinate)(2,6-diphenylphenolate)aluminum, bis(2-methyl-8-quinolinate)(3,5-di-t-butylphenolate)aluminum linolate)(2,4,6-triphenylphenolate)aluminum, bis(2-methyl-8-quinolinolate)(2,4,6-trimethylphenolate)aluminum, bis(2-methyl-8-quinolinolate)(2,4,5,6-tetramethylphenolate)aluminum, bis(2-methyl-8-quinolinolate)(1-naphtholate)aluminum, bis(2-methyl-8-quinolinolate)(2-naphtholate)aluminum, bis(2,4-dimethyl-8-quinolinolate)(2-phenylphenolate)aluminum, bis(2,4-Dimethyl-8-quinolinolate)(3-phenylphenolate)aluminum, bis(2,4-dimethyl-8-quinolinolate)(4-phenylphenolate)aluminum, bis(2,4-dimethyl-8-quinolinolate)(3,5-dimethylphenolate)aluminum, bis(2,4-dimethyl-8-quinolinolate)(3,5-di-t-butylphenolate)aluminum, bis(2-methyl-8-quinolinolate)aluminum-μ-oxo-bis(2-methyl-8-quinolinolate)aluminum, bis(2,4-dimethyl-8-quinolinolate)aluminum-μ-oxo-bis(2,4-dimethyl-8-quinolinolate)aluminum, bis(2-methyl-4-ethyl-8- quinolinolate)aluminum-μ-oxo-bis(2-methyl-4-ethyl-8-quinolinolate)aluminum, bis(2-methyl-4-methoxy-8-quinolinolate)aluminum-μ-oxo-bis(2-methyl-4-methoxy-8-quinolinolate)aluminum, bis(2-methyl-5-cyano-8-quinolinolate)aluminum-μ-oxo-bis(2-methyl-5-cyano-8-quinolinolate)aluminum, bis(2-methyl-5-trifluoromethyl-8-quinolinolate)aluminum-μ-oxo-bis(2-methyl-5-trifluoromethyl-8-quinolinolate)aluminum, bis(10-hydroxybenzo[h]quinoline)beryllium, etc.

[0577] The quinolinol metal complex can be produced using known raw materials and known synthesis methods.

[0578] <Thiazole derivatives and benzothiazole derivatives> The thiazole derivative is, for example, a compound represented by the following formula (ETM-14-1). [ka] The benzothiazole derivative is, for example, a compound represented by the following formula (ETM-14-2). [ka]

[0579] In each formula, φ is an n-valent aryl ring (preferably an n-valent benzene ring, naphthalene ring, anthracene ring, fluorene ring, benzofluorene ring, phenalene ring, phenanthrene ring, or triphenylene ring), and n is an integer from 1 to 4. A "thiazole-based substituent" or a "benzothiazole-based substituent" is a substituent in which the pyridyl in the "pyridine-based substituent" in the formulae (ETM-2), (ETM-2-1), and (ETM-2-2) is replaced with the below-mentioned thiazolyl or benzothiazolyl, and at least one hydrogen in the thiazole derivative and the benzothiazole derivative may be replaced with a deuterium.

[0580] [ka]

[0581] φ is preferably an anthracene ring or a fluorene ring. In this case, the structure can be as described in the formula (ETM-2-1) or the formula (ETM-2-2). 11 ~R 18 The explanation for formula (ETM-2-1) or formula (ETM-2-2) can be cited. In addition, in formula (ETM-2-1) or formula (ETM-2-2), two pyridine-based substituents are described as being bonded together, but when these are replaced with a thiazole-based substituent (or a benzothiazole-based substituent), both pyridine-based substituents may be replaced with a thiazole-based substituent (or a benzothiazole-based substituent) (i.e., n=2), or one of the pyridine-based substituents may be replaced with a thiazole-based substituent (or a benzothiazole-based substituent) and the other pyridine-based substituent may be replaced with R 11 ~R 18 (i.e., n=1). Furthermore, for example, R in formula (ETM-2-1) 11 ~R 18 At least one of the substituents is replaced with a thiazole-based substituent (or a benzothiazole-based substituent) to form a "pyridine-based substituent" R 11 ~R 18 may be substituted.

[0582] These thiazole or benzothiazole derivatives can be produced using known raw materials and known synthesis methods.

[0583] <Silole derivatives> The silole derivative is, for example, a compound represented by the following formula (ETM-15), the details of which are described in JP-A-9-194487. [ka]

[0584] X and Y are each independently alkyl, cycloalkyl, alkenyl, alkynyl, alkoxy, alkenyloxy, alkynyloxy, aryl, or heteroaryl, which may be substituted. For details of these groups, the explanations in formula (1A) and formula (1B) and further the explanation in formula (ETM-7-2) can be cited. In addition, alkenyloxy and alkynyloxy are groups in which the alkyl portion of alkoxy is replaced with alkenyl or alkynyl, respectively, and for details of these alkenyls and alkynyls, the explanations in formula (ETM-7-2) can be cited. Furthermore, X and Y, both of which are alkyl, may be bonded to form a ring.

[0585] R 1 ~R 4are each independently hydrogen, halogen, alkyl, cycloalkyl, alkoxy, aryloxy, amino, alkylcarbonyl, arylcarbonyl, alkoxycarbonyl, aryloxycarbonyl, azo group, alkylcarbonyloxy, arylcarbonyloxy, alkoxycarbonyloxy, aryloxycarbonyloxy, sulfinyl, sulfonyl, sulfanyl, silyl, carbamoyl, aryl, heteroaryl, alkenyl, alkynyl, nitro, formyl, nitroso, formyloxy, isocyano, cyanate group, isocyanate group, thiocyanate group, isothiocyanate group, or cyano, which may be substituted with alkyl, cycloalkyl, aryl or halogen, and may form a condensed ring with an adjacent substituent.

[0586] R 1 ~R 4 For details of halogen, alkyl, cycloalkyl, alkoxy, aryloxy, amino, aryl, heteroaryl, alkenyl and alkynyl in, the descriptions in formula (1A) and formula (1B) can be referred to.

[0587] R 1 ~R 4 For details of the alkyl, aryl and alkoxy in the alkylcarbonyl, arylcarbonyl, alkoxycarbonyl, aryloxycarbonyl, alkylcarbonyloxy, arylcarbonyloxy, alkoxycarbonyloxy and aryloxycarbonyloxy in the above, the explanations in the formula (1A) and the formula (1B) can be cited.

[0588] Examples of silyl include a silyl group and a group in which at least one of the three hydrogen atoms of the silyl group is independently substituted with an aryl, an alkyl, or a cycloalkyl, and tri-substituted silyl is preferable, such as triarylsilyl, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, and alkyldicycloalkylsilyl. For details of the aryl, alkyl, and cycloalkyl in these, the explanations in formula (1A) and formula (1B) can be cited.

[0589] The condensed ring formed between adjacent substituents is, for example, R 1 and R 2 , R 2 and R 3 , R 3 and R 4 etc. These fused rings may contain nitrogen, oxygen, or sulfur atoms in the ring structure, and may be fused with another ring.

[0590] However, preferably, R 1 and R 4 is phenyl, X and Y are not alkyl or phenyl. 1 and R 4 When R is thienyl, X and Y are alkyl, R is thienyl, 2 and R 3 is alkyl, aryl, alkenyl or R 2 and R 3 In addition, it is preferable that R 1 and R 4 When is a silyl group, R 2 , R 3 , X and Y are each independently not hydrogen or alkyl having 1 to 6 carbon atoms. 1 and R 2 In the case of a structure in which a benzene ring is condensed, X and Y are not alkyl and phenyl.

[0591] These silole derivatives can be produced using known raw materials and known synthesis methods.

[0592] <Azoline derivatives> The azoline derivative is, for example, a compound represented by the following formula (ETM-16), details of which are described in International Publication No. 2017 / 014226. [ka]

[0593] In formula (ETM-16), φ is an m-valent group derived from an aromatic hydrocarbon having 6 to 40 carbon atoms or an m-valent group derived from an aromatic heterocycle having 2 to 40 carbon atoms, and at least one hydrogen of φ is optionally substituted by alkyl having 1 to 6 carbon atoms, cycloalkyl having 3 to 14 carbon atoms, aryl having 6 to 18 carbon atoms, or heteroaryl having 2 to 18 carbon atoms; Y's are each independently -O-, -S- or >N-Ar, Ar is an aryl having 6 to 12 carbon atoms or a heteroaryl having 2 to 12 carbon atoms, at least one hydrogen of Ar may be substituted by an alkyl having 1 to 4 carbon atoms, a cycloalkyl having 5 to 10 carbon atoms, an aryl having 6 to 12 carbon atoms or a heteroaryl having 2 to 12 carbon atoms, R 1 ~R 5 are each independently hydrogen, alkyl having 1 to 4 carbon atoms, or cycloalkyl having 5 to 10 carbon atoms, provided that Ar in the >N-Ar and R 1 ~R 5 one of which is a site for binding to L; Each L is independently selected from the group consisting of a divalent group represented by the following formula (L-1) and a divalent group represented by the following formula (L-2): [ka]

[0594] In formula (L-1), X 1 ~X 6 are each independently =CR 6- or =N- and X 1 ~X 6 At least two of the =CR 6 - and X 1 ~X 6 Two of =CR 6 -R in 6 is the site of binding to φ or the azoline ring, and the other =CR 6 -R in 6 is hydrogen, In formula (L-2), X 7 ~X 14 are each independently =CR 6 - or =N- and X 7 ~X 14 At least two of the =CR 6 - and X 7 ~X 14 Two of =CR 6 -R in 6 is the site of binding to φ or the azoline ring, and the other =CR 6 -R in 6 is hydrogen, at least one hydrogen atom of L may be substituted with alkyl having 1 to 4 carbon atoms, cycloalkyl having 5 to 10 carbon atoms, aryl having 6 to 10 carbon atoms, or heteroaryl having 2 to 10 carbon atoms; m is an integer of 1 to 4, and when m is an integer of 2 to 4, the groups formed by the azoline ring and L may be the same or different, and At least one hydrogen atom in the compound represented by formula (ETM-16) may be substituted with deuterium.

[0595] Specific azoline derivatives are compounds represented by the following formula (ETM-16-1) or formula (ETM-16-2). [ka]

[0596] In formula (ETM-16-1) and formula (ETM-16-2), φ is an m-valent group derived from an aromatic hydrocarbon having 6 to 40 carbon atoms or an m-valent group derived from an aromatic heterocycle having 2 to 40 carbon atoms, and at least one hydrogen of φ is optionally substituted by alkyl having 1 to 6 carbon atoms, cycloalkyl having 3 to 14 carbon atoms, aryl having 6 to 18 carbon atoms, or heteroaryl having 2 to 18 carbon atoms; In formula (ETM-16-1), each Y is independently -O-, -S- or >N-Ar, Ar is an aryl having 6 to 12 carbon atoms or a heteroaryl having 2 to 12 carbon atoms, and at least one hydrogen of Ar is optionally substituted by an alkyl having 1 to 4 carbon atoms, a cycloalkyl having 5 to 10 carbon atoms, an aryl having 6 to 12 carbon atoms, or a heteroaryl having 2 to 12 carbon atoms; In formula (ETM-16-1), R 1 ~R 4 are each independently hydrogen, alkyl having 1 to 4 carbon atoms, or cycloalkyl having 5 to 10 carbon atoms, with the proviso that R 1 and R 2 are identical, and R 3 and R 4 are identical, In formula (ETM-16-2), R 1 ~R 5 are each independently hydrogen, alkyl having 1 to 4 carbon atoms, or cycloalkyl having 5 to 10 carbon atoms, with the proviso that R 1 and R 2 are identical, and R 3 and R 4 are identical, In formula (ETM-16-1) and formula (ETM-16-2), Each L is independently selected from the group consisting of a divalent group represented by the following formula (L-1) and a divalent group represented by the following formula (L-2):

[0597] [ka] In formula (L-1), X 1 ~X 6 are each independently =CR 6 - or =N- and X 1 ~X 6 At least two of the =CR6 - and X 1 ~X 6 Two of =CR 6 -R in 6 is the site of binding to φ or the azoline ring, and the other =CR 6 -R in 6 is hydrogen, In formula (L-2), X 7 ~X 14 are each independently =CR 6 - or =N- and X 7 ~X 14 At least two of the =CR 6 - and X 7 ~X 14 Two of =CR 6 -R in 6 is the site of binding to φ or the azoline ring, and the other =CR 6 -R in 6 is hydrogen, at least one hydrogen atom of L may be substituted with alkyl having 1 to 4 carbon atoms, cycloalkyl having 5 to 10 carbon atoms, aryl having 6 to 10 carbon atoms, or heteroaryl having 2 to 10 carbon atoms; m is an integer of 1 to 4, and when m is an integer of 2 to 4, the groups formed by the azoline ring and L may be the same or different, and At least one hydrogen atom in the compound represented by formula (ETM-16-1) or formula (ETM-16-2) may be replaced with deuterium.

[0598] Preferably, φ is selected from the group consisting of monovalent groups represented by the following formulas (φ1-1) to (φ1-18), divalent groups represented by the following formulas (φ2-1) to (φ2-34), trivalent groups represented by the following formulas (φ3-1) to (φ3-3), and tetravalent groups represented by the following formulas (φ4-1) to (φ4-2), and at least one hydrogen of φ may be substituted by alkyl having 1 to 6 carbon atoms, cycloalkyl having 3 to 14 carbon atoms, aryl having 6 to 18 carbon atoms, or heteroaryl having 2 to 18 carbon atoms.

[0599] [ka]

[0600] [ka] [ka]

[0601] In the formula, Z is >CR2, >N-Ar, >NL, -O- or -S-, R in >CR2 is each independently an alkyl having 1 to 4 carbon atoms, a cycloalkyl having 5 to 10 carbon atoms, an aryl having 6 to 12 carbon atoms or a heteroaryl having 2 to 12 carbon atoms, and R may be bonded to each other to form a ring, Ar in >N-Ar is an aryl having 6 to 12 carbon atoms or a heteroaryl having 2 to 12 carbon atoms, and L in >NL is L in formula (ETM-16), formula (ETM-16-1) or formula (ETM-16-2). * in the formula indicates a bonding position.

[0602] Preferably, L is a divalent ring group selected from the group consisting of benzene, naphthalene, pyridine, pyrazine, pyrimidine, pyridazine, triazine, quinoline, isoquinoline, naphthyridine, phthalazine, quinoxaline, quinazoline, cinnoline, and pteridine, and at least one hydrogen of L may be substituted with an alkyl group having 1 to 4 carbon atoms, a cycloalkyl group having 5 to 10 carbon atoms, an aryl group having 6 to 10 carbon atoms, or a heteroaryl group having 2 to 10 carbon atoms.

[0603] Preferably, Ar in >N-Ar as Y or Z is selected from the group consisting of phenyl, naphthyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, naphthyridinyl, phthalazinyl, quinoxalinyl, quinazolinyl, cinnolinyl, and pteridinyl, and at least one hydrogen of Ar in >N-Ar as Y may be substituted with alkyl having 1 to 4 carbon atoms, cycloalkyl having 5 to 10 carbon atoms, or aryl having 6 to 10 carbon atoms.

[0604] Preferably, R 1 ~R 4 are each independently hydrogen, alkyl having 1 to 4 carbon atoms, or cycloalkyl having 5 to 10 carbon atoms, with the proviso that R 1 and R 2 are identical, and R 3 and R 4 are identical, and R 1 ~R 4 are not all hydrogen at the same time, and m is 1 or 2. When m is 2, the groups formed by the azoline ring and L are the same.

[0605] Specific examples of azoline derivatives include the following compounds: In the structural formula, "Me" represents methyl. [ka]

[0606] More preferably, φ is selected from the group consisting of divalent groups represented by the following formulas (φ2-1), (φ2-31), (φ2-32), (φ2-33) and (φ2-34), and at least one hydrogen of φ may be substituted by an aryl having 6 to 18 carbon atoms.

[0607] [ka]

[0608] L is a divalent ring group selected from the group consisting of benzene, pyridine, pyrazine, pyrimidine, pyridazine, and triazine, and at least one hydrogen of L is optionally substituted by alkyl having 1 to 4 carbon atoms, cycloalkyl having 5 to 10 carbon atoms, aryl having 6 to 10 carbon atoms, or heteroaryl having 2 to 14 carbon atoms; Ar in >N-Ar as Y is selected from the group consisting of phenyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, and triazinyl, and at least one hydrogen of the Ar may be substituted by alkyl having 1 to 4 carbon atoms, cycloalkyl having 5 to 10 carbon atoms, or aryl having 6 to 10 carbon atoms; R 1 ~R 4 are each independently hydrogen, alkyl having 1 to 4 carbon atoms, or cycloalkyl having 5 to 10 carbon atoms, with the proviso that R 1 and R 2 are identical, and R 3 and R 4 are identical, and R 1 ~R 4 cannot all become hydrogen at the same time, and m is 2, and the groups formed by the azoline ring and L are the same.

[0609] Other specific examples of azoline derivatives include the following compounds: In the structural formula, "Me" represents methyl. [ka]

[0610] For details of alkyl, cycloalkyl, aryl or heteroaryl in the above formulas defining this azoline derivative, the explanations in formula (1A) and formula (1B) can be referred to.

[0611] The azoline derivative can be produced using known raw materials and known synthesis methods.

[0612] <Reducing substances> The electron transport layer or the electron injection layer may further contain a substance capable of reducing the material forming the electron transport layer or the electron injection layer. As the reducing substance, various substances can be used as long as they have a certain degree of reducing ability, and for example, at least one selected from the group consisting of alkali metals, alkaline earth metals, rare earth metals, oxides of alkali metals, halides of alkali metals, oxides of alkaline earth metals, halides of alkaline earth metals, oxides of rare earth metals, halides of rare earth metals, organic complexes of alkali metals, organic complexes of alkaline earth metals, and organic complexes of rare earth metals can be suitably used.

[0613] Preferred reducing substances include alkali metals such as Na (work function 2.36 eV), K (2.28 eV), Rb (2.16 eV) or Cs (1.95 eV) and alkaline earth metals such as Ca (2.9 eV), Sr (2.0 to 2.5 eV) or Ba (2.52 eV), and substances with a work function of 2.9 eV or less are particularly preferred. Among these, more preferred reducing substances are alkali metals such as K, Rb or Cs, more preferably Rb or Cs, and most preferably Cs. These alkali metals have particularly high reducing ability, and by adding a relatively small amount to the material forming the electron transport layer or electron injection layer, the luminance of the organic EL element can be improved and the life can be extended. Furthermore, as a reducing substance having a work function of 2.9 eV or less, a combination of two or more of these alkali metals is also preferred, and in particular, a combination containing Cs is preferred, for example, a combination of Cs and Na, Cs and K, Cs and Rb, or a combination of Cs, Na and K. By containing Cs, the reducing ability can be efficiently exhibited, and by adding it to a material forming an electron transport layer or an electron injection layer, the luminance of the organic EL element can be improved and the life span can be extended.

[0614] The above-mentioned electron injection layer material and electron transport layer material can be used as an electron layer material as a polymer compound obtained by polymerizing a reactive compound substituted with a reactive substituent as a monomer, or as a crosslinked polymer thereof, or as a pendant polymer compound obtained by reacting a main chain polymer with the reactive compound, or as a crosslinked pendant polymer thereof. In this case, the reactive substituent can be quoted from the explanation of the polycyclic aromatic compound consisting of a partial structure represented by formula (1A) and at least two partial structures represented by formula (1B). The applications of such polymer compounds and crosslinked polymers will be described in detail below.

[0615] 3-1-7. Cathode in organic electroluminescent device The cathode 108 serves to inject electrons into the light-emitting layer 105 through the electron injection layer 107 and the electron transport layer 106 .

[0616] The material for forming the cathode 108 is not particularly limited as long as it is a substance that can efficiently inject electrons into the organic layer, but the same material as the material for forming the anode 102 can be used. Among them, metals such as tin, indium, calcium, aluminum, silver, copper, nickel, chromium, gold, platinum, iron, zinc, lithium, sodium, potassium, cesium, and magnesium, or alloys thereof (magnesium-silver alloy, magnesium-indium alloy, aluminum-lithium alloy such as lithium fluoride / aluminum, etc.), etc. are preferable. In order to increase the electron injection efficiency and improve the device characteristics, lithium, sodium, potassium, cesium, calcium, magnesium, or alloys containing these low work function metals are effective. However, these low work function metals are generally unstable in the air. To improve this point, for example, a method is known in which a trace amount of lithium, cesium, or magnesium is doped into the organic layer to use a highly stable electrode. As other dopants, inorganic salts such as lithium fluoride, cesium fluoride, lithium oxide, and cesium oxide can also be used. However, they are not limited to these.

[0617] Further, for electrode protection, preferred examples include lamination of metals such as platinum, gold, silver, copper, iron, tin, aluminum, and indium, or alloys using these metals, inorganic substances such as silica, titania, and silicon nitride, polyvinyl alcohol, vinyl chloride, hydrocarbon polymer compounds, etc. The method of producing these electrodes is also not particularly limited as long as it can provide electrical continuity, and may be resistance heating, electron beam deposition, sputtering, ion plating, coating, or the like.

[0618] 3-1-8. Binders that may be used in each layer The materials used for the hole injection layer, hole transport layer, light emitting layer, electron transport layer and electron injection layer can form each layer alone, but they can also be used as a polymer binder by being dispersed in a solvent-soluble resin such as polyvinyl chloride, polycarbonate, polystyrene, poly(N-vinylcarbazole), polymethyl methacrylate, polybutyl methacrylate, polyester, polysulfone, polyphenylene oxide, polybutadiene, hydrocarbon resin, ketone resin, phenoxy resin, polyamide, ethyl cellulose, vinyl acetate resin, ABS resin, polyurethane resin, or a curable resin such as phenol resin, xylene resin, petroleum resin, urea resin, melamine resin, unsaturated polyester resin, alkyd resin, epoxy resin, silicone resin, or the like.

[0619] 3-1-9. Method for producing organic electroluminescent device Each layer constituting an organic EL element can be formed by forming the material to be formed into a thin film by a method such as vapor deposition, resistance heating vapor deposition, electron beam vapor deposition, sputtering, molecular lamination, printing, spin coating or casting, coating, etc. The thickness of each layer thus formed is not particularly limited and can be set appropriately according to the properties of the material, but is usually in the range of 2 nm to 5000 nm. The thickness of the film can usually be measured with a quartz crystal oscillation type film thickness measuring device, etc. When forming a thin film by vapor deposition, the vapor deposition conditions vary depending on the type of material, the desired crystal structure and association structure of the film, etc. The vapor deposition conditions are generally a boat heating temperature of +50 to +400°C, a vacuum degree of 10, and a vacuum of 10. -6 ~10-3 It is preferable to appropriately set the pressure, pressure Pa, deposition rate 0.01 to 50 nm / sec, substrate temperature -150 to +300°C, and film thickness 2 nm to 5 µm.

[0620] When applying a DC voltage to the organic EL element obtained in this way, the anode should be set to + and the cathode to -. When a voltage of about 2 to 40 V is applied, light emission can be observed from the transparent or semi-transparent electrode side (anode or cathode, or both). This organic EL element also emits light when a pulse current or an AC current is applied. The waveform of the AC current applied may be any waveform.

[0621] Next, as an example of a method for producing an organic EL element, a method for producing an organic EL element consisting of an anode, a hole injection layer, a hole transport layer, an emitting layer consisting of a host material and a dopant material, an electron transport layer, an electron injection layer, and a cathode will be described.

[0622] <Vapor deposition method> A thin film of an anode material is formed on a suitable substrate by vapor deposition or the like to prepare an anode, and then a thin film of a hole injection layer and a hole transport layer is formed on the anode. A host material and a dopant material are co-deposited on the anode to form a thin film as a light-emitting layer, an electron transport layer and an electron injection layer are formed on the light-emitting layer, and a thin film of a cathode material is further formed by vapor deposition or the like to prepare a cathode, thereby obtaining a desired organic EL device. Note that in the preparation of the above-mentioned organic EL device, the preparation order can also be reversed, and the layers can be prepared in the order of cathode, electron injection layer, electron transport layer, light-emitting layer, hole transport layer, hole injection layer, and anode.

[0623] <Wet film formation method> The wet film formation method is carried out by preparing a low molecular weight compound capable of forming each organic layer of an organic EL element as a liquid composition for forming an organic layer, and using this. If there is no suitable organic solvent for dissolving this low molecular weight compound, the composition for forming an organic layer may be prepared from a polymer compound polymerized together with other monomers having a solubility function as a reactive compound obtained by substituting a reactive substituent on the low molecular weight compound or a main chain polymer.

[0624] In the wet film formation method, a coating film is generally formed through a coating step of coating a substrate with a composition for forming an organic layer and a drying step of removing the solvent from the coated composition for forming an organic layer. When the polymer compound has a crosslinkable substituent (also called a crosslinkable polymer compound), the polymer is further crosslinked by the drying step to form a crosslinked polymer. Depending on the difference in the coating step, a method using a spin coater is called a spin coat method, a method using a slit coater is called a slit coat method, a method using a plate is called a gravure, offset, reverse offset, or flexographic printing method, a method using an inkjet printer is called an inkjet method, and a method spraying in a mist is called a spray method.

[0625] As an example, a method of forming a coating film on a substrate having banks using an inkjet method will be described with reference to FIG. 2. First, banks (200) are provided on electrodes (120) on a substrate (110). In this case, ink droplets (310) are dropped between the banks (200) from an inkjet head (300) and dried to produce a coating film (130). This process is repeated to produce the next coating film (140) and then the light-emitting layer (150), and an electron transport layer, an electron injection layer, and electrodes are formed using a vacuum deposition method, making it possible to produce an organic EL element in which the light-emitting site is separated by the bank material.

[0626] The drying process may be carried out by air drying, heating, drying under reduced pressure, etc. The drying process may be carried out once or may be carried out multiple times using different methods and conditions. Also, different methods may be used in combination, such as calcination under reduced pressure.

[0627] The wet film formation method is a film formation method using a solution, for example, some printing methods (inkjet methods), spin coating methods or casting methods, coating methods, etc. Unlike the vacuum deposition method, the wet film formation method does not require the use of expensive vacuum deposition equipment, and can form a film under atmospheric pressure. In addition, the wet film formation method allows for large area and continuous production, which leads to reduced manufacturing costs.

[0628] On the other hand, compared to the vacuum deposition method, wet film formation can be difficult to laminate. When producing laminated films using the wet film formation method, it is necessary to prevent the dissolution of the lower layer by the composition of the upper layer, and compositions with controlled solubility, crosslinking of the lower layer, and orthogonal solvents (solvents that do not dissolve in each other) are used. However, even with these technologies, it can be difficult to use the wet film formation method to apply all films.

[0629] Therefore, a method is generally adopted in which only some layers are formed by a wet film formation method and the remaining layers are formed by a vacuum deposition method when manufacturing an organic EL element.

[0630] For example, the procedure for producing an organic EL element by partially applying a wet film formation method will be described below. (Step 1) Formation of the anode by vacuum deposition (Step 2) Forming a film by a wet film formation method using a composition for forming a hole injection layer containing a material for the hole injection layer (Step 3) Forming a film by a wet film formation method using a composition for forming a hole transport layer containing a material for the hole transport layer (Step 4) Formation of a film by a wet film formation method using a composition for forming an emitting layer containing a host material and a dopant material (Step 5) Formation of the electron transport layer by vacuum deposition (Step 6) Formation of the electron injection layer by vacuum deposition (Step 7) Cathode deposition by vacuum deposition Through this procedure, an organic EL element consisting of an anode, a hole injection layer, a hole transport layer, an emitting layer made of a host material and a dopant material, an electron transport layer, an electron injection layer, and a cathode is obtained. Of course, the electron transport layer and the electron injection layer may also be formed by a wet film formation method using a layer-forming composition containing the material for the electron transport layer and the material for the electron injection layer, respectively. In this case, it is preferable to use a means for preventing dissolution of the lower light-emitting layer, or a means for forming the film from the cathode side in the reverse order to the above procedure.

[0631] <Other film formation methods> The composition for forming an organic layer can be formed into a film by laser thermal imaging (LITI). LITI is a method in which a compound attached to a substrate is heated and evaporated by a laser, and the composition for forming an organic layer can be used as the material applied to the substrate.

[0632] <Optional process> Before and after each film-forming step, appropriate treatment steps, cleaning steps, and drying steps may be appropriately inserted. Examples of treatment steps include exposure treatment, plasma surface treatment, ultrasonic treatment, ozone treatment, cleaning treatment using an appropriate solvent, and heat treatment. Furthermore, a series of steps for preparing a bank may also be included.

[0633] Photolithography techniques can be used to fabricate the banks. Positive resist materials and negative resist materials can be used as bank materials that can be used in photolithography. In addition, patternable printing methods such as inkjet printing, gravure offset printing, reverse offset printing, and screen printing can also be used. In this case, permanent resist materials can also be used.

[0634] Materials that can be used for banks include, but are not limited to, polysaccharides and their derivatives, homopolymers and copolymers of hydroxyl-containing ethylenic monomers, biopolymers, polyacryloyl compounds, polyesters, polystyrenes, polyimides, polyamideimides, polyetherimides, polysulfides, polysulfones, polyphenylenes, polyphenyl ethers, polyurethanes, epoxy (meth)acrylates, melamine (meth)acrylates, polyolefins, cyclic polyolefins, acrylonitrile-butadiene-styrene copolymers (ABS), silicone resins, polyvinyl chloride, chlorinated polyethylene, chlorinated polypropylene, polyacetate, polynorbornene, synthetic rubber, fluorinated polymers such as polyfluorovinylidene, polytetrafluoroethylene, and polyhexafluoropropylene, fluoroolefin-hydrocarbonolefin copolymers, and fluorocarbon polymers.

[0635] <Composition for forming organic layer used in wet film formation method> The composition for forming an organic layer is obtained by dissolving a low molecular weight compound capable of forming each organic layer of an organic EL device, or a polymer compound obtained by polymerizing the low molecular weight compound, in an organic solvent. For example, the composition for forming an emitting layer contains at least one polycyclic aromatic compound (or a polymer compound thereof) as a first component, which is a dopant material, at least one host material as a second component, and at least one organic solvent as a third component. The first component functions as a dopant component of the emitting layer obtained from the composition, and the second component functions as a host component of the emitting layer. The third component functions as a solvent that dissolves the first and second components in the composition, and gives a smooth and uniform surface shape due to the controlled evaporation rate of the third component itself during application.

[0636] <Organic solvent> The organic layer forming composition contains at least one organic solvent. By controlling the evaporation rate of the organic solvent during film formation, it is possible to control and improve the film forming properties, the presence or absence of defects in the coating film, the surface roughness, and the smoothness. In addition, during film formation using the inkjet method, it is possible to control the meniscus stability at the pinhole of the inkjet head, and control and improve the ejection properties. In addition, by controlling the drying rate of the film and the orientation of the derivative molecules, it is possible to improve the electrical properties, light emitting properties, efficiency, and life of an organic EL element having an organic layer obtained from the organic layer forming composition.

[0637] (1) Physical properties of organic solvents The boiling point of at least one organic solvent is 130°C to 300°C, more preferably 140°C to 270°C, and further preferably 150°C to 250°C. When the boiling point is higher than 130°C, it is preferable from the viewpoint of inkjet dischargeability. Also, when the boiling point is lower than 300°C, it is preferable from the viewpoint of coating film defects, surface roughness, residual solvent, and smoothness. From the viewpoint of good inkjet dischargeability, film-forming property, smoothness, and low residual solvent, it is more preferable that the organic solvent contains two or more organic solvents. On the other hand, in some cases, the composition may be in a solid state by removing the solvent from the composition for forming the organic layer, taking into consideration transportability, etc.

[0638] Furthermore, the organic solvent contains a good solvent (GS) and a poor solvent (PS) for at least one of the solutes, and the boiling point (BP) of the good solvent (GS) is GS ) is the boiling point (BP PS ) is particularly preferred. By adding a poor solvent with a high boiling point, the good solvent with a low boiling point volatilizes first during film formation, increasing the concentration of the components in the composition and the concentration of the poor solvent, promoting rapid film formation. This results in a coating film with few defects, small surface roughness, and high smoothness.

[0639] Difference in solubility (S GS -S PS The boiling point difference (BP) is preferably 1% or more, more preferably 3% or more, and even more preferably 5% or more. PS -BP GS ) is preferably 10° C. or higher, more preferably 30° C. or higher, and even more preferably 50° C. or higher.

[0640] After the film is formed, the organic solvent is removed from the coating film by a drying process such as vacuum, reduced pressure, or heating. When heating is performed, from the viewpoint of improving the coating film-forming property, it is preferable to perform the heating at a temperature of at least one of the solutes at a glass transition temperature (Tg) +30°C or lower. From the viewpoint of reducing the residual solvent, it is preferable to heat at at least one of the solutes at a glass transition temperature (Tg) -30°C or higher. Even if the heating temperature is lower than the boiling point of the organic solvent, the organic solvent is sufficiently removed because the film is thin. Also, drying may be performed multiple times at different temperatures, and multiple drying methods may be used in combination.

[0641] (2) Specific examples of organic solvents Examples of the organic solvent used in the composition for forming the organic layer include alkylbenzene solvents, phenyl ether solvents, alkyl ether solvents, cyclic ketone solvents, aliphatic ketone solvents, monocyclic ketone solvents, solvents having a diester skeleton, and fluorine-containing solvents. Specific examples include pentanol, hexanol, heptanol, octanol, nonanol, decanol, undecanol, dodecanol, tetradecanol, hexane-2-ol, heptan-2-ol, octan-2-ol, decan-2-ol, dodecan-2-ol, cyclohexanol, Sanol, α-terpineol, β-terpineol, γ-terpineol, δ-terpineol, terpineol (mixture), ethylene glycol monomethyl ether acetate, propylene glycol monomethyl ether acetate, diethylene glycol dimethyl ether, dipropylene glycol dimethyl ether, diethylene glycol ethyl methyl ether, diethylene glycol isopropyl methyl ether, dipropylene glycol monomethyl ether, diethylene glycol diethyl ether, diethylene glycol monomethyl ether , diethylene glycol butyl methyl ether, tripropylene glycol dimethyl ether, triethylene glycol dimethyl ether, diethylene glycol monobutyl ether, ethylene glycol monophenyl ether, triethylene glycol monomethyl ether, diethylene glycol dibutyl ether, triethylene glycol butyl methyl ether, polyethylene glycol dimethyl ether, tetraethylene glycol dimethyl ether, p-xylene, m-xylene, o-xylene, 2,6-lutidine, 2-fluoro-m-xylene, 3-fluoro-o-xylene, 2-chlorobenzotrifluoride, cumene, toluene, 2-chloro-6-fluorotoluene, 2-fluoroanisole, anisole, 2,3-dimethylpyrazine, bromobenzene, 4-fluoroanisole, 3-fluoroanisole, 3-trifluoromethylanisole, mesitylene, 1,2,4-trimethylbenzene, t-butylbenzene, 2-methylanisole, phenetole, benzodioxole, 4-methylanisole, s-butylbenzene, 3-methylanisole, 4-fluoro-3-methylanisole, cymene, 1,2,3-Trimethylbenzene, 1,2-Dichlorobenzene, 2-Fluorobenzonitrile, 4-Fluoroveratrol, 2,6-Dimethylanisole, n-Butylbenzene, 3-Fluorobenzonitrile, Decalin (Decahydronaphthalene), Neopentylbenzene, 2,5-Dimethylanisole, 2,4-Dimethylanisole, Benzonitrile, 3,5-Dimethylanisole, Diphenyl ether, 1-Fluoro-3,5-dimethoxybenzene, Methyl benzoate, Isopentylbenzene, 3,4-Dimethylanisole, o-Tolunitrile, n-Amylbenzene, Veratrol, 1,2,3,4-Tetrahydronaphthalene, Ethyl benzoate, n-Hexylbenzene, Propyl benzoate, Cyclohexylbenzene, 1- Examples of the solvent include, but are not limited to, methylnaphthalene, butyl benzoate, 2-methylbiphenyl, 3-phenoxytoluene, 2,2'-bitolyl, dodecylbenzene, dipentylbenzene, tetramethylbenzene, trimethoxybenzene, trimethoxytoluene, 2,3-dihydrobenzofuran, 1-methyl-4-(propoxymethyl)benzene, 1-methyl-4-(butyloxymethyl)benzene, 1-methyl-4-(pentyloxymethyl)benzene, 1-methyl-4-(hexyloxymethyl)benzene, 1-methyl-4-(heptyloxymethyl)benzene, benzyl butyl ether, benzyl pentyl ether, benzyl hexyl ether, benzyl heptyl ether, and benzyl octyl ether. The solvent may be used alone or in a mixture.

[0642] <Optional ingredients> The composition for forming the organic layer may contain optional components, such as a binder and a surfactant, to the extent that the properties of the composition are not impaired.

[0643] (1) Binder The composition for forming an organic layer may contain a binder. The binder forms a film during film formation and bonds the resulting film to a substrate. The binder also plays a role in dissolving, dispersing, and binding other components in the composition for forming an organic layer.

[0644] Examples of binders used in the organic layer-forming composition include, but are not limited to, acrylic resins, polyethylene terephthalate, ethylene-vinyl acetate copolymers, ethylene-vinyl alcohol copolymers, acrylonitrile-ethylene-styrene copolymer (AES) resins, ionomers, chlorinated polyethers, diallyl phthalate resins, unsaturated polyester resins, polyethylene, polypropylene, polyvinyl chloride, polyvinylidene chloride, polystyrene, polyvinyl acetate, Teflon, acrylonitrile-butadiene-styrene copolymer (ABS) resins, acrylonitrile-styrene copolymer (AS) resins, phenolic resins, epoxy resins, melamine resins, urea resins, alkyd resins, polyurethanes, and copolymers of the above resins and polymers.

[0645] The binder used in the organic layer-forming composition may be of one type or a mixture of two or more types.

[0646] (2) Surfactants The organic layer forming composition may contain a surfactant, for example, to control the film surface uniformity, solvent affinity and liquid repellency of the organic layer forming composition. Surfactants are classified into ionic and nonionic based on the structure of the hydrophilic group, and further classified into alkyl, silicon and fluorine based on the structure of the hydrophobic group. In addition, based on the molecular structure, they are classified into monomolecular systems with relatively small molecular weight and simple structure, and polymer systems with large molecular weight and side chains or branches. In addition, based on the composition, they are classified into single systems and mixed systems in which two or more types of surfactants and base materials are mixed. All types of surfactants can be used as surfactants that can be used in the organic layer forming composition.

[0647] Examples of surfactants include Polyflow No. 45, Polyflow KL-245, Polyflow No. 75, Polyflow No. 90, Polyflow No. 95 (trade names, manufactured by Kyoeisha Chemical Industry Co., Ltd.), Disperbyk 161, Disperbyk 162, Disperbyk 163, Disperbyk 164, Disperbyk 166, Disperbyk 170, Disperbyk 180, Disperbyk 181, Disperbyk 182, BYK300, BYK 306, BYK310, BYK320, BYK330, BYK342, BYK344, BYK346 (trade name, manufactured by BYK Japan Co., Ltd.), KP-341, KP-358, KP-368, KF-96-50CS, KF-50-100CS (trade name, manufactured by Shin-Etsu Chemical Co., Ltd.), Surflon SC-101, Surflon KH-40 (trade name, manufactured by Seimi Chemical Co., Ltd.), Ftergent 222F, Ftergent 251, FTX-218 (trade name, manufactured by Neos Co., Ltd.), EFTOP EF-351, EFTOP EF-352, EFTOP EF-601, EFTOP EF-801, EFTOPEF-802 (product name, manufactured by Mitsubishi Materials Corporation), Megafac F-470, Megafac F-471, Megafac F-475, Megafac R-08, Megafac F-477, Megafac F-479, Megafac F-553, Megafac F-554 (product name, manufactured by DIC Corporation), fluoroalkylbenzenesulfonate, fluoroalkylcarboxylate, fluoroalkylpolyoxyethyleneether, fluoroalkylammonium iodide, fluoroalkylbetaine, fluoroalkylsulfonate, diglycerol tetrakis(fluoroalkylpolyoxyethyleneether), fluoroalkyltrimethylammonium salt, fluoroalkylaminosulfonate, polyoxyethylenenonyl Examples of the alkyl ethers include polyoxyethylene octylphenyl ether, polyoxyethylene alkyl ethers, polyoxyethylene laurate, polyoxyethylene oleate, polyoxyethylene stearate, polyoxyethylene laurylamine, sorbitan laurate, sorbitan palmitate, sorbitan stearate, sorbitan oleate, sorbitan fatty acid esters, polyoxyethylene sorbitan laurate, polyoxyethylene sorbitan palmitate, polyoxyethylene sorbitan stearate, polyoxyethylene sorbitan oleate, polyoxyethylene naphthyl ether, alkylbenzene sulfonates, and alkyldiphenyl ether disulfonates.

[0648] The surfactant may be used alone or in combination of two or more kinds.

[0649] <Composition and Properties of the Organic Layer-Forming Composition> The content of each component in the composition for forming an organic layer is determined in consideration of the good solubility, storage stability and film-forming property of each component in the composition for forming an organic layer, the good film quality of the coating film obtained from the composition for forming an organic layer, the good discharge property when using an inkjet method, and the good electrical properties, light-emitting properties, efficiency and life of an organic EL device having an organic layer produced using the composition. For example, in the case of a composition for forming an emitting layer, it is preferable that the first component is 0.0001% by mass to 2.0% by mass relative to the total mass of the composition for forming an emitting layer, the second component is 0.0999% by mass to 8.0% by mass relative to the total mass of the composition for forming an emitting layer, and the third component is 90.0% by mass to 99.9% by mass relative to the total mass of the composition for forming an emitting layer.

[0650] More preferably, the first component is 0.005% by mass to 1.0% by mass, the second component is 0.095% by mass to 4.0% by mass, and the third component is 95.0% by mass to 99.9% by mass, more preferably, the first component is 0.05% by mass to 0.5% by mass, the second component is 0.25% by mass to 2.5% by mass, and the third component is 97.0% by mass to 99.7% by mass, based on the total mass of the composition for forming the light-emitting layer.

[0651] The composition for forming an organic layer can be produced by appropriately selecting the above-mentioned components and subjecting them to stirring, mixing, heating, cooling, dissolving, dispersing, etc., by a known method. After preparation, filtration, degassing (also called degassing), ion exchange treatment, and inert gas replacement / filling treatment, etc. may be appropriately selected.

[0652] The higher the viscosity of the composition for forming an organic layer, the better the film-forming properties and the better the ejection properties when using an inkjet method. On the other hand, the lower the viscosity, the easier it is to form a thin film. For this reason, the viscosity of the composition for forming an organic layer at 25°C is preferably 0.3 to 3 mPa·s, and more preferably 1 to 3 mPa·s. In the present invention, the viscosity is a value measured using a cone-plate type rotational viscometer (cone-plate type).

[0653] The lower the surface tension of the composition for forming an organic layer, the better the film-forming properties and the more defect-free the coating film will be. On the other hand, the higher the surface tension, the better the ink-jet ejection properties will be. For this reason, the viscosity of the composition for forming an organic layer is preferably such that the surface tension at 25°C is 20 to 40 mN / m, more preferably 20 to 30 mN / m. In the present invention, the surface tension is a value measured using the hanging drop method.

[0654] <Crosslinkable polymer compound: Compound represented by formula (XLP-1)> Next, the case where the above-mentioned polymer compound has a crosslinkable substituent will be described. Such a crosslinkable polymer compound is, for example, a compound represented by the following formula (XLP-1).

[0655] [ka]

[0656] In formula (XLP-1), MUx, ECx, and k are defined the same as MU, EC, and k in formula (H3), with the proviso that the compound represented by formula (XLP-1) has at least one crosslinkable substituent (XLS), and preferably the content of the monovalent or divalent aromatic group having a crosslinkable substituent is 0.1 to 80 mass% in the molecule.

[0657] The content of the monovalent or divalent aromatic compound having a crosslinkable substituent is preferably from 0.5 to 50 mass %, more preferably from 1 to 20 mass %.

[0658] The crosslinkable substituent (XLS) is not particularly limited as long as it is a group that can further crosslink the above-mentioned polymer compound, but substituents having the following structures are preferred: In each structural formula, * indicates the bond position. [ka]

[0659] Each L is independently a single bond, -O-, -S-, >C=O, -OC(=O)-, an alkylene having 1 to 12 carbon atoms, an oxyalkylene having 1 to 12 carbon atoms, or a polyoxyalkylene having 1 to 12 carbon atoms. Among the above substituents, a group represented by formula (XLS-1), formula (XLS-2), formula (XLS-3), formula (XLS-9), formula (XLS-10) or formula (XLS-17) is preferred, and a group represented by formula (XLS-1), formula (XLS-3) or formula (XLS-17) is more preferred.

[0660] Examples of the divalent aromatic compound having a crosslinkable substituent include compounds having the following partial structures: [ka]

[0661] [ka]

[0662] [ka]

[0663] [ka]

[0664] <Methods of producing polymer compounds and crosslinkable polymer compounds> The manufacturing method of the polymer compound and the crosslinkable polymer compound will be described with reference to the compound represented by the above formula (H3) and the compound represented by (XLP-1). These compounds can be synthesized by appropriately combining known manufacturing methods.

[0665] The solvent used in the reaction includes aromatic solvents, saturated / unsaturated hydrocarbon solvents, alcohol solvents, ether solvents, and the like, such as dimethoxyethane, 2-(2-methoxyethoxy)ethane, 2-(2-ethoxyethoxy)ethane, and the like.

[0666] The reaction may be carried out in a two-phase system. When the reaction is carried out in a two-phase system, a phase transfer catalyst such as a quaternary ammonium salt may be added, if necessary.

[0667] The compound of formula (H3) and the compound of formula (XLP-1) may be produced in one step or in multiple steps. The compound may be produced by a batch polymerization method in which all the raw materials are put into a reaction vessel and then the reaction is started, a dropwise polymerization method in which the raw materials are added dropwise to a reaction vessel, or a precipitation polymerization method in which the product precipitates as the reaction proceeds. These methods can be combined appropriately to synthesize the compound. For example, when the compound of formula (SPH-1) is synthesized in one step, the target product is obtained by adding a monomer having a polymerizable group bonded to the monomer unit (MU) and a monomer having a polymerizable group bonded to the end cap unit (EC) to a reaction vessel and then reacting the monomer. When the compound of formula (SPH-1) is synthesized in multiple steps, the target product is obtained by polymerizing the monomer having a polymerizable group bonded to the monomer unit (MU) to the target molecular weight, and then adding a monomer having a polymerizable group bonded to the end cap unit (EC) and reacting the monomer. If a monomer having a polymerizable group bonded to different types of monomer units (MU) is added and reacted in multiple steps, a polymer having a concentration gradient in the structure of the monomer units can be produced. Also, after preparing a precursor polymer, the target polymer can be obtained by a post-reaction.

[0668] In addition, the primary structure of the polymer can be controlled by selecting the polymerizable group of the monomer. For example, as shown in synthesis schemes 1 to 3, it is possible to synthesize a polymer having a random primary structure (synthetic scheme 1) or a polymer having a regular primary structure (synthetic schemes 2 and 3), and these can be used in appropriate combinations depending on the target object. Furthermore, if a monomer having three or more polymerizable groups is used, a hyperbranched polymer or a dendrimer can be synthesized.

[0669] [ka]

[0670] Monomers that can be used in the present invention include those described in JP2010-189630A, WO2012 / 086671A, WO2013 / 191088A, WO2002 / 045184A, WO2011 / 049241A, WO2013 / 146806A, WO2005 / 049546A, WO2015 / 1458 ...B, WO2015 / 1458B, WO2015 / 1458B, WO2015 / 1458B, WO2015 / 1458B, WO2015 / 1458B, WO2015 / 1458B, WO2015 / 1458B, W It can be synthesized in accordance with the methods described in JP-A-2002 / 045184, JP-A-2010-215886, JP-A-2008-106241, JP-A-2010-215886, WO 2016 / 031639, JP-A-2011-174062, WO 2016 / 031639, WO 2016 / 031639, and WO 2002 / 045184.

[0671] In addition, specific polymer synthesis procedures are described in JP 2012-036388 A, WO 2015 / 008851 A, JP 2012-36381 A, JP 2012-144722 A, WO 2015 / 194448 A, WO 2013 / 146806 A, WO 2015 / 145871 A, WO 2016 / It can be synthesized in accordance with the methods described in WO 2016 / 031639, WO 2016 / 125560, WO 2016 / 031639, WO 2016 / 031639, WO 2016 / 125560, WO 2015 / 145871, WO 2011 / 049241, and JP 2012-144722 A.

[0672] 3-1-10.Application examples of organic electroluminescent devices The present invention can also be applied to a display device having an organic EL element or a lighting device having an organic EL element. A display device or lighting device including an organic EL element can be manufactured by a known method, for example by connecting the organic EL element according to this embodiment to a known driving device, and can be driven appropriately using a known driving method such as DC driving, pulse driving, or AC driving.

[0673] Examples of the display device include panel displays such as color flat panel displays, and flexible displays such as flexible color organic electroluminescent (EL) displays (see, for example, JP-A-10-335066, JP-A-2003-321546, JP-A-2004-281086, etc.). Examples of the display system include a matrix and / or segment system. Note that matrix display and segment display may coexist in the same panel.

[0674] In a matrix, pixels for display are arranged two-dimensionally, such as in a grid or mosaic pattern, and a collection of pixels displays characters and images. The shape and size of the pixels are determined by the application. For example, square pixels with sides of 300 μm or less are usually used to display images and characters on computers, monitors, and televisions, and pixels with sides of mm order are used for large displays such as display panels. For monochrome display, pixels of the same color are arranged, but for color display, red, green, and blue pixels are displayed side by side. In this case, there are typically delta type and stripe type. The driving method for this matrix can be either line sequential driving method or active matrix. Line sequential driving has the advantage of being simpler in structure, but when considering the operating characteristics, active matrix may be superior, so it is necessary to use it according to the application.

[0675] In the segment type, a pattern is formed to display predetermined information, and a predetermined area is illuminated. Examples include time and temperature displays in digital clocks and thermometers, operating status displays in audio equipment and induction cookers, and panel displays in automobiles.

[0676] Examples of the lighting device include lighting devices for indoor lighting, backlights for liquid crystal display devices, etc. (see, for example, JP 2003-257621 A, JP 2003-277741 A, JP 2004-119211 A, etc.). Backlights are mainly used for the purpose of improving the visibility of non-self-luminous display devices, and are used in liquid crystal display devices, clocks, audio devices, automobile panels, display boards, signs, etc. In particular, for liquid crystal display devices, particularly backlights for personal computers, where thinning is an issue, it is difficult to make them thin because conventional methods are made of fluorescent lamps and light guide plates, so the backlight using the light-emitting element according to this embodiment is characterized by its thinness and light weight.

[0677] 3-2. Other organic devices The polycyclic aromatic compound according to the present invention can be used for producing the above-mentioned organic electroluminescent device, as well as an organic field effect transistor or an organic thin-film solar cell.

[0678] 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 elect...

Claims

1. A polycyclic aromatic compound represented by the following formula (1): 【Chemistry 1】 In formula (1), X 1 and X 2 are >O, Y 1 , Y 2 , Y 3 , Y 4 , Y 5 and Y 6 are each independently =C(-R Y )- or ═N-, at least one of which is ═N-; at least one R Y is a group represented by formula (A-1) or formula (A-2), and the other R Y is hydrogen or any substituent selected from the substituent group YZ excluding the group represented by formula (A-1); In formula (A-1), W 1 and W. 2 are each independently a single bond, >C(-R W ) 2 , >N-R W , >O, >Si(-R W ) 2 , or >S, The above >N-R W R W represents any substituent selected from the substituent group YZ or a group represented by formula (A-2), Above>C(-R W ) 2 , >Si(-R W ) 2 R W each independently represents a hydrogen atom, a substituent selected from the substituent group YZ, or a group represented by formula (A-2), R that bonds to the same element W may be bonded to each other, Each R W in the >N-R W may be independently bonded to at least one Z; Z is -N= or -CR Z = and R Z each independently represents a hydrogen atom, a substituent selected from the substituent group YZ, or a group represented by formula (A-2), L 1 represents a single bond or any linking group selected from the group L of linking groups, L 1 is R Z With a bond, any of -CR Z = C, * indicates the bonding position of the group represented by formula (A-1), In formula (A-2), Ar 3 each independently represents an aryl which may be substituted with at least one substituent selected from the substituent group YZ (excluding the group represented by formula (A-1)), a heteroaryl which may be substituted with at least one substituent selected from the substituent group YZ (excluding the group represented by formula (A-1)), or a group represented by formula (A-1), W 3 is Si, m is 3 and n is 0; L 2 represents a single bond or any linking group selected from the group L of linking groups, * indicates the bonding position of the group represented by formula (A-2), At least one hydrogen atom in the structure represented by formula (1) may be substituted with cyano, halogen or deuterium; Substituent group YZ: aryl optionally substituted with aryl, heteroaryl, alkyl or cycloalkyl; Heteroaryl optionally substituted with aryl, heteroaryl, alkyl or cycloalkyl; and Diarylamino optionally substituted with aryl, heteroaryl, alkyl or cycloalkyl. Linking group group L: 【Chemistry 2】 2. The polycyclic aromatic compound according to claim 1, wherein L 1 and L 2 are each independently a single bond or a linking group represented by any one of the following formulas: 【Chemistry 3】

3. L 1 and L 2 The polycyclic aromatic compound according to claim 1 , wherein each of the groups independently represents a linking group represented by any one of the following formulas: 【Chemistry 4】

4. Y 2 , Y 3 , Y 4 and Y 5 Each independently represents =C(-R Y )-, and Y 1 Or Y 6 The polycyclic aromatic compound according to any one of claims 1 to 3, wherein at least one of the following is =N-.

5. Y 2 , Y 3 , Y 4 , Y 5 and Y 6 Each independently represents =C(-R Y )-, and Y 1 The polycyclic aromatic compound according to claim 4, wherein is =N-.

6. In formula (1), R Y The polycyclic aromatic compound according to any one of claims 1 to 5, wherein one or two of the above are groups represented by formula (A-1) or formula (A-2).

7. In formula (1), R Y At least one of the above is a group represented by formula (A-1), W 1 > C(-R W ) 2 , >O, >Si(-R W ) 2 Or >S and W 2 The polycyclic aromatic compound according to any one of claims 1 to 6, wherein is a single bond.

8. In formula (1), R Y At least one of the above is a group represented by formula (A-2).

9. In formula (1), R other than the group represented by formula (A-1) or formula (A-2) Y is hydrogen, an aryl which may be substituted with an aryl or a heteroaryl, or a heteroaryl which may be substituted with an aryl or a heteroaryl.

10. The polycyclic aromatic compound according to claim 1, represented by the following formula (1-11): 【Chemistry 5】

11. The polycyclic aromatic compound according to claim 1, represented by the following formula (1-13): 【Chemistry 6】

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

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

14. The organic electroluminescent device according to claim 13 , wherein the organic layer is an electron transport layer.

15. The organic electroluminescent device according to claim 13 , wherein the organic layer is a light-emitting layer.

16. The organic electroluminescent device according to claim 15 , wherein the light-emitting layer contains at least one selected from the group consisting of a light-emitting metal complex and a TADF material.

17. The organic electroluminescent device according to claim 16, wherein the light-emitting layer contains a polycyclic aromatic compound which is a monomer represented by formula (2) or a polymer having a plurality of structural units represented by formula (2). 【Chemistry 7】 Ring A, ring B and ring C are each independently an optionally substituted aryl ring or an optionally substituted heteroaryl ring, provided that B and X in ring A, ring B and ring C in the monomer are 11 and / or X 12 None of the rings bonded to the ring are six-membered rings containing nitrogen. X 11 and X 12 are each independently >O or >N-R, R of the >N-R is an optionally substituted aryl, an optionally substituted heteroaryl, an optionally substituted alkyl, or an optionally substituted cycloalkyl, R of the >N-R may be bonded to ring A and / or ring B or ring A and / or ring C via -O-, -S-, -C(-R) 2 - or a single bond, R of the -C(-R) 2 - is hydrogen, alkyl, or cycloalkyl, In the structure represented by formula (2) or the structure having a plurality of structural units represented by formula (2), at least one selected from the group consisting of an aryl ring and a heteroaryl ring may be condensed with at least one cycloalkane, at least one hydrogen in the cycloalkane may be substituted, and at least one -CH 2 - may be replaced by -O-; At least one hydrogen atom in the structure represented by formula (2) or the structure having a plurality of structural units represented by formula (2) may be substituted with deuterium, cyano or halogen.

18. The organic electroluminescence device according to any one of claims 15 to 17, comprising at least one of an electron transport layer and an electron injection layer disposed between the cathode and the light emitting layer, and at least one of the electron transport layer and the electron injection layer contains at least one selected from the group consisting of borane derivatives, pyridine derivatives, fluoranthene derivatives, BO-based derivatives, anthracene derivatives, benzofluorene derivatives, phosphine oxide derivatives, pyrimidine derivatives, arylnitrile derivatives, triazine derivatives, benzimidazole derivatives, phenanthroline derivatives, and quinolinol-based metal complexes.

19. 19. The organic electroluminescent device according to claim 18, wherein at least one of the electron transport layer and the electron injection layer further contains at least one selected from the group consisting of alkali metals, alkaline earth metals, rare earth metals, oxides of alkali metals, halides of alkali metals, oxides of alkaline earth metals, halides of alkaline earth metals, oxides of rare earth metals, halides of rare earth metals, organic complexes of alkali metals, organic complexes of alkaline earth metals, and organic complexes of rare earth metals.

20. A display device or lighting device comprising the organic electroluminescent element according to claim 13.

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