Polycyclic aromatic compound

Abstract

To provide a novel material useful as an organic device material such as an organic EL element.SOLUTION: The present disclosure provides a polycyclic aromatic compound having aromatic rings coupled with a hetero element such as boron, nitrogen, phosphorus, oxygen and sulfur, or a multimer of polycyclic aromatic compounds having a plurality of the structures: for example, compounds of formula (4-37). These compounds have large HOMO-LUMO gap (band gap Eg in a thin film) and high triplet excitation energy (ET).SELECTED DRAWING: None

Description

[Technical field]

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

[0002] Conventionally, display devices using electroluminescent light-emitting elements have been extensively studied because they can be made more energy-efficient and thinner, and organic electroluminescent elements (hereinafter sometimes referred to as "organic EL 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. Among them, in recent years, polycyclic aromatic compounds containing boron have been developed as materials for the light-emitting layer, and organic EL devices using them have been reported (Patent Documents 1 and 2). [Prior art documents] [Patent documents]

[0004] [Patent Document 1] International Publication No. 2015 / 102118 [Patent Document 2] JP 2018-43984 A Summary of the Invention [Problem to be solved by the invention]

[0005] As described above, various materials have been developed as materials for use in organic EL elements, but in order to increase the options for materials for organic EL elements, it is desirable to develop materials made of compounds different from conventional ones. An object of the present invention is to provide a novel material useful as a material for organic devices such as organic EL elements. [Means for solving the problem]

[0006] The present inventors have conducted extensive research to solve the above problems, and have succeeded in producing a novel polycyclic aromatic compound having a structure in which multiple aromatic rings are linked by boron atoms, nitrogen atoms, etc., similar to the compounds described in Patent Documents 1 and 2. They have also found that an excellent organic EL device can be obtained by constructing an organic EL device by disposing a layer containing this polycyclic aromatic compound between a pair of electrodes, and have completed the present invention. That is, the present invention provides the following polycyclic aromatic compound or a multimer thereof, and further provides a material for an organic EL device containing the following polycyclic aromatic compound or a multimer thereof.

[0007] <1> A polycyclic aromatic compound represented by formula (1), or a polymer of a polycyclic aromatic compound having a plurality of structures represented by formula (1). [ka]

[0008] (In formula (1), ring A, ring B and ring C are each independently an aryl ring or a heteroaryl ring, and at least one hydrogen atom in these rings may be substituted; provided that at least one ring selected from the group consisting of ring A, ring B, and ring C is a fused ring composed of two or more rings selected from the group consisting of a monocyclic aryl ring, a monocyclic heteroaryl ring, and a cyclopentadiene ring, and at least one hydrogen atom in this fused ring is optionally substituted; Y 1is B, P, P=O, P=S, Al, Ga, As, Si-R, or Ge-R, wherein R of Si-R and Ge-R is aryl, alkyl, or cycloalkyl; X 1 , X 2 , and X 3 are each independently >O, >NR, >C(-R)2, >S, >Si(-R)2, >S(=O)2, or >Se; R in the >NR is each independently an optionally substituted aryl, an optionally substituted heteroaryl, an optionally substituted alkyl, or an optionally substituted cycloalkyl; R in the >C(-R)2 and >Si(-R)2 is each independently hydrogen, an optionally substituted aryl, an optionally substituted alkyl, or an optionally substituted cycloalkyl; R in the >NR, >C(-R)2, and >Si(-R)2 may be bonded to at least one ring selected from the group consisting of ring A, ring B, and ring C via a linking group or a single bond; In the compound or structure represented by formula (1), at least one of the aryl ring and the heteroaryl ring may be fused with at least one cycloalkane, at least one hydrogen in the cycloalkane may be substituted, and at least one -CH2- in the cycloalkane may be substituted with -O-; At least one hydrogen atom in the compound represented by formula (1) or a polymer thereof may be substituted with deuterium, cyano, or halogen.

[0009] <2> the fused ring comprises a heteroaryl ring containing a sulfur atom or an oxygen atom, or the fused ring is a naphthalene; <1> 2. The polycyclic aromatic compound or a multimer thereof according to claim 1 . <3> The fused ring is a ring represented by formula (1a) or formula (1b). <1> 2. The polycyclic aromatic compound or a multimer thereof according to claim 1 .

[0010] [ka]

[0011] (In formula (1a), X 4 and X 5 are each independently >O, >NR, >C(-R)2, >S, >Si(-R)2, >S(=O)2, or >Se; R in the >NR is each independently an optionally substituted aryl, an optionally substituted heteroaryl, an optionally substituted alkyl, or an optionally substituted cycloalkyl; R in the >C(-R)2 and >Si(-R)2 is each independently hydrogen, an optionally substituted aryl, an optionally substituted alkyl, or an optionally substituted cycloalkyl; R a1 ~R a8 are each independently hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted diarylamino, substituted or unsubstituted diheteroarylamino, substituted or unsubstituted arylheteroarylamino, substituted or unsubstituted diarylboryl (two aryls may be bonded via a single bond or a linking group), substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryloxy, substituted or unsubstituted arylsulfonyl, substituted or unsubstituted diarylphosphine, substituted or unsubstituted diarylphosphine oxide, substituted or unsubstituted diarylphosphine sulfide, or substituted silyl, with the proviso that R a1 ~R a8 The three adjacent ones are Y in formula (1). 1 , X 1 , X 2 , or X 3 It becomes a bond with R other than the above three. a1 ~R a8 Any two adjacent ones of the above may be bonded to each other to form a benzene ring which may have a substituent, n1 and n2 are each independently 0 or 1, and are not both 0; In formula (1b), R a9 ~R a16 are each independently hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted diarylamino, substituted or unsubstituted diheteroarylamino, substituted or unsubstituted arylheteroarylamino, substituted or unsubstituted diarylboryl (two aryls may be bonded via a single bond or a linking group), substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryloxy, substituted or unsubstituted arylsulfonyl, substituted or unsubstituted diarylphosphine, substituted or unsubstituted diarylphosphine oxide, substituted or unsubstituted diarylphosphine sulfide, or substituted silyl, provided that at least one pair of adjacent three R a9 ~R a16 is Y in formula (1). 1 , X 1 , X 2 , or X 3 It becomes a bond with .)

[0012] <4> The ring represented by formula (1a) is any one of the rings represented by formulas (1a-1) to (1a-14). <3> 2. The polycyclic aromatic compound or a multimer thereof according to claim 1 . [ka]

[0013] [ka]

[0014] In formula (1a-3), formula (1a-9), formula (1a-13), and formula (1a-14), R in NR is each independently an optionally substituted aryl, an optionally substituted heteroaryl, an optionally substituted alkyl, or an optionally substituted cycloalkyl; In formulas (1a-4), (1a-5), and (1a-11) to (1a-13), R in >C(-R)2 and >Si(-R)2 is each independently hydrogen, an optionally substituted aryl, an optionally substituted alkyl, or an optionally substituted cycloalkyl; In formulas (1a-1) to (1a-14), R a1 ~R a8 and R aa1 ~R aa4 are each independently hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted diarylamino, substituted or unsubstituted diheteroarylamino, substituted or unsubstituted arylheteroarylamino, substituted or unsubstituted diarylboryl (two aryls may be bonded via a single bond or a linking group), substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryloxy, substituted or unsubstituted arylsulfonyl, substituted or unsubstituted diarylphosphine, substituted or unsubstituted diarylphosphine oxide, substituted or unsubstituted diarylphosphine sulfide, or substituted silyl, with the proviso that R a1 ~R a8 and R aa1 ~R aa4 The three adjacent ones are Y in formula (1). 1 , X 1 , X 2 , or X 3 It becomes a combination with.

[0015] <5> The ring represented by formula (1a) is a ring represented by formula (1a-1) or formula (1a-2). <4> 2. The polycyclic aromatic compound or a multimer thereof according to claim 1 . <6> A polycyclic aromatic compound represented by any one selected from the group consisting of formula (3), formula (4), formula (5), formula (6), formula (7), formula (8), formula (9), formula (10), formula (11), formula (12), formula (13), formula (14), and formula (15), or having a plurality of structures represented by any one selected from the group consisting of formula (3), formula (4), formula (5), formula (6), formula (7), formula (8), formula (9), formula (10), formula (11), formula (12), formula (13), formula (14), and formula (15); <1> 2. The polycyclic aromatic compound or a multimer thereof according to claim 1 .

[0016] [ka]

[0017] [ka]

[0018] [ka]

[0019] (Equation (3), Equation (4), Equation (5), Equation (6), Equation (7), Equation (8), Equation (9), Equation (10), Equation (11), Equation (12), Equation (13), Equation (14), and Equation (15), Y 1 is B, P, P=O, P=S, Al, Ga, As, Si-R, or Ge-R, wherein R of Si-R and Ge-R is aryl, alkyl, or cycloalkyl; X 1 , X 2 , X 3 , X 4 , X 5 , X 6 , and X 7 are each independently >O, >NR, >C(-R)2, >S, >Si(-R)2, >S(=O)2, or >Se; R in the >NR is each independently an optionally substituted aryl, an optionally substituted heteroaryl, an optionally substituted alkyl, or an optionally substituted cycloalkyl; R in the >C(-R)2 and >Si(-R)2 is each independently hydrogen, an optionally substituted aryl, an optionally substituted alkyl, or an optionally substituted cycloalkyl; R in the >NR, >C(-R)2, and >Si(-R)2 may be bonded to the ring via a linking group or a single bond; At least one of the rings may be fused with at least one cycloalkane, at least one hydrogen in the cycloalkane may be replaced, and at least one -CH2- in the cycloalkane may be replaced with -O-; R b1 ~R b13 is hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted diarylamino, substituted or unsubstituted diheteroarylamino, substituted or unsubstituted arylheteroarylamino, substituted or unsubstituted diarylboryl (two aryls may be bonded via a single bond or a linking group), substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryloxy, substituted or unsubstituted arylsulfonyl, substituted or unsubstituted diarylphosphine, substituted or unsubstituted diarylphosphine oxide, substituted or unsubstituted diarylphosphine sulfide, or substituted silyl; At least one hydrogen atom in the compounds represented by formula (3), formula (4), formula (5), formula (6), formula (7), formula (8), formula (9), formula (10), formula (11), formula (12), formula (13), formula (14), and formula (15) or multimers thereof may be substituted with deuterium, cyano, or halogen.

[0020] <7> Y 1 is B and X 2 and X 3are both C(-R)2, <1> ~ <6> 2. The polycyclic aromatic compound or a multimer thereof according to claim 1 . <8> Y 1 is B and X 2 is C(-R)2, and X 3 is >NR, <1> ~ <6> 2. The polycyclic aromatic compound or a multimer thereof according to claim 1 .

[0021] <9> Represented by any of the following structural formulas: <1> The polycyclic aromatic compound according to claim 1. [ka]

[0022] [ka]

[0023] [ka]

[0024] [ka]

[0025] <10> <1> ~ <9> 2. A reactive compound in which the polycyclic aromatic compound or a multimer thereof according to any one of claims 1 to 11 is substituted with a reactive substituent. <11> <10> 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. <12> Main chain polymer <10> or a pendant-type crosslinked polymer obtained by further crosslinking the pendant-type polymer compound. <13> <1> ~ <9> 2. A material for an organic device, comprising the polycyclic aromatic compound or a multimer thereof according to claim 1. <14> <10> 2. A material for an organic device, comprising the reactive compound according to claim 1. <15> <11> 2. A material for an organic device, comprising the polymer compound or crosslinked polymer described in 1. <16> <12> 2. A material for an organic device, comprising the pendant type polymer compound or the pendant type crosslinked polymer according to claim 1. <17> The organic device material is a material for an organic electroluminescent element, a material for an organic field effect transistor, or a material for an organic thin-film solar cell. <13> ~ <16> 2. The material for an organic device according to claim 1 . <18> The material for an organic electroluminescent device is a material for a light-emitting layer. <17> The material for an organic device according to claim 1.

[0026] <19> <1> ~ <9> 2. A composition comprising the polycyclic aromatic compound or a multimer thereof according to claim 1, and an organic solvent. <20> <10> A composition comprising the reactive compound according to claim 1 and an organic solvent. <21> Main chain polymers and <10> A composition comprising the reactive compound according to claim 1 and an organic solvent. <22> <11> 2. A composition comprising the polymer compound or crosslinked polymer according to claim 1 and an organic solvent. <23> <12> 2. A composition comprising the pendant type polymer compound or the pendant type crosslinked polymer according to claim 1 and an organic solvent.

[0027] <24> A pair of electrodes consisting of an anode and a cathode, and a gas sensor disposed between the pair of electrodes, <1> ~ <9> The polycyclic aromatic compound or a multimer thereof according to any one of the above items. <10> The reactive compound according to <11> or <12> and an organic layer containing the pendant type polymer compound or the pendant type crosslinked polymer according to claim 1. <25> A pair of electrodes consisting of an anode and a cathode, and a gas sensor disposed between the pair of electrodes, <1> ~ <9> The polycyclic aromatic compound or a multimer thereof according to any one of the above items. <10> The reactive compound according to <11> or <12> and a light-emitting layer containing the pendant type polymer compound or the pendant type crosslinked polymer according to claim 1. <26> the light-emitting layer contains a host and the polycyclic aromatic compound, its multimer, reactive compound, polymer compound, crosslinked polymer, pendant polymer compound, or pendant crosslinked polymer as a dopant; <25> The organic electroluminescent device according to claim 1. <27> The host is an anthracene-based compound, a fluorene-based compound, or a dibenzochrysene-based compound; <26> The organic electroluminescent device according to claim 1.

[0028] <28> an electron transport layer and / or an electron injection layer disposed between the cathode and the light emitting layer, at least one of the electron transport layer and the electron injection layer containing at least one selected from the group consisting of borane derivatives, pyridine derivatives, fluoranthene derivatives, BO derivatives, anthracene derivatives, benzofluorene derivatives, phosphine oxide derivatives, pyrimidine derivatives, arylnitrile derivatives, triazine derivatives, benzimidazole derivatives, phenanthroline derivatives, quinolinol metal complexes, thiazole derivatives, benzothiazole derivatives, silole derivatives, and azoline derivatives; <24> ~ <27> 13. The organic electroluminescent device according to claim 12,

[0029] <29> the electron transport layer and / or 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; <28> The organic electroluminescent device according to claim 1. <30> 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, <24> ~ <29> 13. The organic electroluminescent device according to claim 12, <31> <24> ~ <29> 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

[0030] According to a preferred embodiment of the present invention, it is possible to provide a novel polycyclic aromatic compound that can be used, for example, as a material for an organic EL device, and by using this polycyclic aromatic compound, it is possible to provide an excellent organic EL device. [Brief description of the drawings]

[0031] [Figure 1] FIG. 1 is a schematic cross-sectional view showing an organic EL element. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0032] 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)".

[0033] 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.

[0034] 1. Polycyclic aromatic compounds and their polymers The present inventors have discovered that a polycyclic aromatic compound represented by formula (1) in which aromatic rings are linked by heteroatoms such as boron, nitrogen, phosphorus, oxygen, and sulfur, or a multimer of a polycyclic aromatic compound having a plurality of structures represented by formula (1), has a large HOMO-LUMO gap (band gap Eg in a thin film) and a high triplet excitation energy (E T ). This is believed to be due to the fact that the six-membered ring containing a hetero element has low aromaticity, which suppresses the decrease in the HOMO-LUMO gap accompanying the expansion of the conjugated system, and that the SOMO1 and SOMO2 in the triplet excited state (T1) are localized due to electronic perturbation of the hetero element. In addition, the hetero element-containing polycyclic aromatic compound according to the present invention has a small energy difference between the triplet excited state (T1) and the singlet excited state (S1), and exhibits thermally activated delayed fluorescence, making it useful as a fluorescent material for organic EL devices. In addition, the high triplet excitation energy (E T) are also useful as electron transport layers or hole transport layers in phosphorescent organic EL devices and organic EL devices that use thermally activated delayed fluorescence. Furthermore, these polycyclic aromatic compounds can be used to arbitrarily change the HOMO and LUMO energies by introducing substituents, so that the ionization potential and electron affinity can be optimized according to the surrounding materials.

[0035] The polycyclic aromatic compound represented by formula (1) or a multimer thereof is preferably a polycyclic aromatic compound represented by the following formula (2) or a multimer of a polycyclic aromatic compound having a plurality of structures represented by the following formula (2). [ka]

[0036] In formula (1), ring A, ring B and ring C are each independently an aryl ring or a heteroaryl ring, and at least one hydrogen atom in these rings may be replaced by a substituent, provided that at least one ring selected from the group consisting of ring A, ring B and ring C is a fused ring composed of two or more rings selected from the group consisting of a monocyclic aryl ring, a monocyclic heteroaryl ring and a cyclopentadiene ring, and at least one hydrogen atom in this fused ring may be replaced. The substituent is preferably a substituted or unsubstituted aryl, a substituted or unsubstituted heteroaryl, a substituted or unsubstituted diarylamino, a substituted or unsubstituted diheteroarylamino, a substituted or unsubstituted arylheteroarylamino (an amino group having an aryl and a heteroaryl), a substituted or unsubstituted diarylboryl (two aryls may be bonded via a single bond or a linking group), a substituted or unsubstituted alkyl, a substituted or unsubstituted cycloalkyl, a substituted or unsubstituted alkoxy, a substituted or unsubstituted aryloxy, a substituted or unsubstituted arylsulfonyl, a substituted or unsubstituted diarylphosphine, a substituted or unsubstituted diarylphosphine oxide, a substituted or unsubstituted diarylphosphine sulfide, or a substituted silyl. When these groups have a substituent, the substituent may be an aryl, a heteroaryl, an alkyl, a cycloalkyl, or a diarylamino.

[0037] The aryl or heteroaryl ring may also be Y 1 , X 1 , X 2 and X 3 It is preferable that the fused three-ring structure in the center of formula (1) composed of the following formula (1) has a five- or six-membered ring sharing a bond with the structure (hereinafter, this structure is also referred to as "D structure").

[0038] Here, the "condensed three-ring structure (D structure)" refers to the Y 1 , X 1 , X 2 and X 3means a structure in which three saturated hydrocarbon rings, each including the ring A, are condensed. In addition, the term "six-membered ring sharing a bond with the condensed three-ring structure" means, for example, the a ring (benzene ring (six-membered ring)) condensed to the D structure as shown in the above formula (2). In addition, "an aryl ring or heteroaryl ring (which is the A ring) has this six-membered ring" means that the A ring is formed only from this six-membered ring, or that the A ring is formed by further condensing other rings to this six-membered ring so as to include this six-membered ring. In other words, the term "an aryl ring or heteroaryl ring (which is the A ring) having a six-membered ring" means that the six-membered ring constituting all or part of the A ring is condensed to the D structure. The same explanation applies to "ring B (ring b)", "ring C (ring c)" and "five-membered ring".

[0039] In formula (1), at least one ring selected from the group consisting of ring A, ring B, and ring C is a fused ring composed of two or more rings selected from the group consisting of a monocyclic aryl ring, a monocyclic heteroaryl ring, and a cyclopentadiene ring. The present inventors have found that by constructing an organic EL device using a polycyclic aromatic compound having such a fused ring as a material for the light-emitting layer, it is possible to improve the luminous efficiency and the device life.

[0040] The number of rings constituting the fused ring is not particularly limited, but is preferably 2 to 5, more preferably 2 or 4, even more preferably 3 or 4, and particularly preferably 3. Examples of the fused ring include a fused ring of two monocyclic aryl rings and one monocyclic heteroaryl ring, a fused ring of two monocyclic aryl rings and one cyclopentadiene ring, a fused ring of two monocyclic aryl rings and one monocyclic heteroaryl ring, and a fused ring of two monocyclic aryl rings and one cyclopentadiene ring. In this case, the monocyclic aryl ring is preferably a benzene ring. Examples of the monocyclic heteroaryl ring include a furan ring, a thiophene ring, a pyrrole ring, an oxazole ring, an isoxazole ring, a thiazole ring, an isothiazole ring, an imidazole ring, a thiadiazole ring, a pyridine ring, and a pyrimidine ring. In addition, the central ring of a thianthrene ring and a phenoxathiin ring are also examples of the monocyclic heteroaryl ring.

[0041] The fused ring is preferably a combination of a 6-membered ring and a 5-membered ring, or a combination of a plurality of 6-membered rings. In this case, the 6-membered ring may share a bond with the fused 3-ring structure, or the 5-membered ring may share a bond with the fused 3-ring structure, but it is preferable that the 6-membered ring share a bond with the fused 3-ring structure. The fused ring is not composed of only cyclopentadiene rings. The cyclopentadiene ring is preferably a 1,1-dimethyl-2,4-cyclopentadiene ring. In formula (1), among rings A, B and C, those which are not fused rings are preferably monocyclic aryl rings or monocyclic heteroaryl rings, more preferably benzene rings.

[0042] The ring A (or ring B or ring C) in formula (1) is the ring a and its substituent R in formula (2). 1 ~R 3 (or ring b and its substituent R 4 ~R 6 , ring c and its substituent R 7 ~R 9). In other words, formula (2) corresponds to a formula in which "rings A to C having 6 members" are selected as rings A to C of formula (1). In that sense, each ring in formula (2) is represented by lowercase letters a to c.

[0043] In formula (2), the substituents R 1 ~R 9 Adjacent groups among the above may be bonded to each other to form an aryl ring or a heteroaryl ring together with the a ring, the b ring, or the c ring, and at least one hydrogen atom in the formed ring may be replaced by an aryl, a heteroaryl, a diarylamino, a diheteroarylamino, an arylheteroarylamino, an alkyl, an alkoxy, or an aryloxy, and at least one hydrogen atom in these rings may be replaced by an aryl, a heteroaryl, or an alkyl, provided that at least one ring selected from the group consisting of the a ring, the b ring, and the c ring is not substituted with a substituent R 1 ~R 9 Adjacent groups among the above are bonded to each other to form a fused ring composed of two or more rings selected from the group consisting of a monocyclic aryl ring, a monocyclic heteroaryl ring, and a cyclopentadiene ring, and at least one hydrogen atom in the fused ring may be substituted. Therefore, in the polycyclic aromatic compound represented by formula (2), the ring structure constituting the compound changes as shown in the following formulas (2-1) and (2-2) depending on the mutual bonding form of the substituents in the a ring, the b ring, and the c ring. The A' ring, the B' ring, and the C' ring in each formula correspond to the A ring, the B ring, and the C ring in formula (1), respectively.

[0044] [ka]

[0045] The A' ring, B' ring and C' ring in the formula (2-1) and the formula (2-2) are each independently a substituent R 1 ~R 9In the formula (2-1) and the formula (2-2), adjacent groups in the formula (2-3) are bonded to each other to form fused rings with the ring a, the ring b, and the ring c, respectively. 3 and b-ring R 4 , R in ring b 6 and R in c-ring 7 , R in ring c 9 and a-ring R 1 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.

[0046] Although not shown in the formula, the structure may be such that only one of the ring a and the ring b is a fused ring (ring A' and ring B', respectively), or the structure may be such that all of the ring a, ring b, and ring c are fused rings (ring A', ring B', and ring C', respectively). Among these structures, a structure having at least one fused ring selected from ring B' and ring C' is preferred, and a structure represented by formula (2-1) is more preferred.

[0047] Examples of the "fused ring composed of two or more rings selected from the group consisting of a monocyclic aryl ring, a monocyclic heteroaryl ring, and a cyclopentadiene ring" in formula 1, or the fused rings which are ring A', ring B', and ring C', include fused rings represented by formula (1a) and formula (1b).

[0048] [ka]

[0049] In formula (1a), X 4 and X 5are each independently >O, >NR, >C(-R)2, >S, >Si(-R)2, >S(=O)2, or >Se, and R in the >NR is each independently an optionally substituted aryl, an optionally substituted heteroaryl, an optionally substituted alkyl, or an optionally substituted cycloalkyl, and R in the >C(-R)2 and >Si(-R)2 is each independently a hydrogen atom, an optionally substituted aryl, an optionally substituted alkyl, or an optionally substituted cycloalkyl, and R a1 ~R a8 are each independently hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted diarylamino, substituted or unsubstituted diheteroarylamino, substituted or unsubstituted arylheteroarylamino (an amino group having an aryl and a heteroaryl), substituted or unsubstituted diarylboryl (two aryls may be bonded via a single bond or a linking group), substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryloxy, substituted or unsubstituted arylsulfonyl, substituted or unsubstituted diarylphosphine, substituted or unsubstituted diarylphosphine oxide, substituted or unsubstituted diarylphosphine sulfide, or substituted silyl, provided that at least one pair of adjacent three R a1 ~R a8 represents Y in formula (1), formula (2-1), or formula (2-2). 1 , X 1 , X 2 or X 3 It becomes a bond with R other than the above three. a1 ~R a8 Any two adjacent groups of the substituents (formula (1a-8) and R aa1 ~R aa4 ) may form a benzene ring, and n1 and n2 are each independently 0 or 1, and cannot both be 0.

[0050] In formula (1b), R a9 ~R a16are each independently hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted diarylamino, substituted or unsubstituted diheteroarylamino, substituted or unsubstituted arylheteroarylamino (an amino group having an aryl and a heteroaryl), substituted or unsubstituted diarylboryl (two aryls may be bonded via a single bond or a linking group), substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryloxy, substituted or unsubstituted arylsulfonyl, substituted or unsubstituted diarylphosphine, substituted or unsubstituted diarylphosphine oxide, substituted or unsubstituted diarylphosphine sulfide, or substituted silyl, provided that at least one pair of adjacent three R a9 ~R a16 is Y in formula (1). 1 , X 1 , X 2 , or X 3 It becomes a combination with. R in formula (1a) a1 ~R a8 and R in formula (1b) a9 ~R a16 For specific examples, see the description of the first and second substituents in formula (1) below.

[0051] Specific examples of the structure represented by formula (1a) are shown below, but the invention is not limited to these structures. [ka]

[0052] [ka]

[0053] In formula (1a-3), formula (1a-9), formula (1a-13), and formula (1a-14), R in N-R is each independently an optionally substituted aryl, an optionally substituted heteroaryl, an optionally substituted alkyl, or an optionally substituted cycloalkyl; In formulas (1a-4), (1a-5), and (1a-11) to (1a-13), R in >C(-R)2 and >Si(-R)2 is each independently an optionally substituted aryl, an optionally substituted alkyl, or an optionally substituted cycloalkyl; In formulas (1a-1) to (1a-14), R a1 ~R a8 and R aa1 ~R aa4 are each independently hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted diarylamino, substituted or unsubstituted diheteroarylamino, substituted or unsubstituted arylheteroarylamino (an amino group having an aryl and a heteroaryl), substituted or unsubstituted diarylboryl (two aryls may be bonded via a single bond or a linking group), substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryloxy, substituted or unsubstituted arylsulfonyl, substituted or unsubstituted diarylphosphine, substituted or unsubstituted diarylphosphine oxide, substituted or unsubstituted diarylphosphine sulfide, or substituted silyl, provided that at least one pair of adjacent three R a1 ~R a8 and R aa1 ~R aa4 is Y in formula (1). 1 , X 1 , X 2 , or X 3 R in formula (1a-1) to formula (1a-14) a1 ~R a8 and R aa1 ~R aa4 For each substituent represented by, reference can be made to the description of the first and second substituents in formula (1) described below.

[0054] R a1 ~R a8 (and R aa1 ~R aa4 ) are hydrogen, R a1 ~R a8 (and R aa1 ~R aa4 From the viewpoint of stability during device operation, when the emitter in the light-emitting layer undergoes hole-trapping recombination, it is preferable that the emitter is stable against radical cations (holes), and X 4 and / or X 5 When is >O, >NR, >S, or >Se, R a1 ~R a8 (and R aa1 ~R aa4 ) is substituted with X 4 or X 5 Preferably, the aryl group is in the o-position or p-position relative to X. 4 and / or X 5 When >C(-R)2 or >Si(-R)2, R a1 ~R a8 (and R aa1 ~R aa4 ) is substituted with X 4 or X 5 It is preferable that it is located at the m position with respect to

[0055] From the viewpoint of synthesis, a high symmetry and / or a low molecular weight during synthesis is preferable because it allows for high reaction selectivity or a low sublimation temperature. High symmetry is preferable not only for the final step in the synthesis but also for the synthesis of partial structures, and a synthetic route with high symmetry can be selected.

[0056] From the viewpoint of reducing intermolecular interactions, it is preferable that the steric hindrance is large. a1 ~R a8 (and R aa1 ~R aa4), the substituent is preferably methyl, t-butyl, t-amyl, t-octyl, phenyl, o-tolyl, p-tolyl, 2,4-xylyl, 2,5-xylyl, 2,6-xylyl, 2,4,6-mesityl, diphenylamino, di-p-tolylamino, bis(p-(t-butyl)phenyl)amino, carbazolyl, 3,6-dimethylcarbazolyl, 3,6-di-t-butylcarbazolyl, phenoxy, cyclohexyl, and an alkyl (particularly methyl)-substituted cyclohexyl having 1 to 5 carbon atoms, norbornenyl, and adamantyl, and more preferably methyl, t-butyl, t-amyl, o-tolyl, 2,6-xylyl, or 2,4,6-mesityl.

[0057] Of the formulas (1a-1) to (1a-14), when they are used as a device material described below, formulas (1a-1) and (1a-2) are preferred from the viewpoint of improving the efficiency and life span.

[0058] Examples of the polycyclic aromatic compound represented by formula (1) and the polycyclic aromatic compound represented by formula (2), which contain the fused ring structures represented by formula (1a) and formula (1b), include the polycyclic aromatic compounds represented by formula (3), formula (4), formula (5), formula (6), formula (7), formula (8), formula (9), formula (10), formula (11), formula (12), formula (13), formula (14), and formula (15).

[0059] [ka]

[0060] [ka]

[0061] [ka]

[0062] In formula (3), formula (4), formula (5), formula (6), formula (7), formula (8), formula (9), formula (10), formula (11), formula (12), formula (13), formula (14), and formula (15), X 1 , X 2 , X 3 , X 4 , X 5 , X 6 , and X 7 are each independently >O, >NR, >C(-R)2, >S, >Si(-R)2, >S(=O)2, or >Se, and R in the >NR is each independently an optionally substituted aryl, an optionally substituted heteroaryl, an optionally substituted alkyl, or an optionally substituted cycloalkyl, and R in the >C(-R)2 and >Si(-R)2 is each independently a hydrogen atom, an optionally substituted aryl, an optionally substituted alkyl, or an optionally substituted cycloalkyl, and R in the >NR, >C(-R)2, and >Si(-R)2 may be bonded to the ring by a linking group or a single bond. X 1 , X 2 , X 3 , and X 4 More on this later. X 4 , X 5 , X 6 , and X 7 are preferably each independently >O, >NR, >C(-R)2, or >S; 4 and X 6 is more preferably each independently >O or >S.

[0063] In formula (3), formula (4), formula (5), formula (6), formula (7), formula (8), formula (9), formula (10), formula (11), formula (12), formula (13), formula (14), and formula (15), R b1 ~R b13is hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted diarylamino, substituted or unsubstituted diheteroarylamino, substituted or unsubstituted arylheteroarylamino (amino group having an aryl and a heteroaryl), substituted or unsubstituted diarylboryl (two aryls may be bonded via a single bond or a linking group), substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryloxy, substituted or unsubstituted arylsulfonyl, substituted or unsubstituted diarylphosphine, substituted or unsubstituted diarylphosphine oxide, substituted or unsubstituted diarylphosphine sulfide, substituted silyl, or cyano. R b1 ~R b13 For each substituent represented by, reference can be made to the description of the first and second substituents in formula (1) described below.

[0064] R a1 ~R a8 (and R aa1 ~R aa4 ) are hydrogen, R a1 ~R a8 (and R aa1 ~R aa4 From the viewpoint of stability during device operation, when the emitter in the light-emitting layer undergoes hole-trapping recombination, it is preferable that the emitter is stable against radical cations (holes), and X 4 and / or X 5 is O, NR, S or Se, R a1 ~R a8 (and R aa1 ~R aa4 ) is substituted with X 4 or X 5 Preferably, the aryl group is in the o-position or p-position relative to X. 4 and / or X 5 When is C(-R)2 or Si(-R)2, R a1 ~R a8 (and Raa1 ~R aa4 ) is substituted with X 4 or X 5 Similarly, it is preferable that Y 1 It is preferred that the substituent is at the p-position relative to the above.

[0065] From the viewpoint of synthesis, a high symmetry and / or a low molecular weight during synthesis is preferable because the reaction selectivity is high or the sublimation temperature is low. Not only in the final step of synthesis, but also in the synthesis of partial structures, a high symmetry is preferable, and a synthetic route with a high symmetry can be selected. In other words, from the viewpoint of the above-mentioned symmetry, formula (3), formula (4), formula (7), formula (8), formula (12), formula (13) or formula (15) is preferable, and formula (3), formula (4), formula (7), formula (12) or formula (13) is more preferable. Furthermore, the structure of these compounds can be adjusted according to the emission wavelength, and when the emission wavelength is shortened, it is preferable that X is in the m position, and when the emission wavelength is shortened, it is preferable that X is in the o position or p position.

[0066] From the viewpoint of reducing intermolecular interactions, it is preferable that the steric hindrance is large. a1 ~R a8 (and R aa1 ~R aa4 ) is methyl, t-butyl, t-amyl, t-octyl, phenyl, o-tolyl, p-tolyl, 2,4-xylyl, 2,5-xylyl, 2,6-xylyl, 2,4,6-mesityl, diphenylamino, di-p-tolylamino, bis(p-(t-butyl)phenyl)amino, carbazolyl, 3,6-dimethylcarbazolyl, 3,6-di-t-butylcarbazolyl, phenoxy, cyclohexyl, and alkyl (particularly methyl)-substituted cyclohexyl having 1 to 5 carbon atoms, norbornenyl, and adamantyl, and more preferably methyl, t-butyl, t-amyl, o-tolyl, 2,6-xylyl, and 2,4,6-mesityl.

[0067] In formula (1), formula (2), formula (3), formula (4), formula (5), formula (6), formula (7), formula (8), formula (9), formula (10), formula (11), formula (12), formula (13), formula (14), and formula (15), Y 1 is B, P, P=O, P=S, Al, Ga, As, Si-R, or Ge-R, where R in Si-R and Ge-R is aryl, alkyl, or cycloalkyl. 1 However, when P=O, P=S, Si-R, or Ge-R, the atom bonded to ring A, ring B, or ring C is P, Si, or Ge.

[0068] From the viewpoint of short wavelength emission, Y 1 is preferably P, P=O, or P=S, and from the viewpoint of emission at long wavelengths, Y 1 is preferably B. From the viewpoint of use as a light-emitting material, X 1 ~X 3 Depending on the combination with Y 1 is preferably B. From the viewpoint of charge transport, Y 1 is preferably B, P, P=O, or P=S, and for applications in the light-emitting layer or adjacent to the light-emitting layer, Y is preferably selected from the viewpoints of stability and energy gap. 1 is preferably B.

[0069] In formula (1), formula (2), formula (3), formula (4), formula (5), formula (6), formula (7), formula (8), formula (9), formula (10), formula (11), formula (12), formula (13), formula (14), and formula (15), X 1 , X 2 , and X 3are each independently >O, >NR, >C(-R)2, >S, >Si(-R)2, >S(=O)2, or >Se, and R in the >NR is each independently an optionally substituted aryl, an optionally substituted heteroaryl, an optionally substituted alkyl, or an optionally substituted cycloalkyl, and R in the >C(-R)2 and >Si(-R)2 is each independently a hydrogen atom, an optionally substituted aryl, an optionally substituted alkyl, or an optionally substituted cycloalkyl, and R in the >NR, >C(-R)2, and >Si(-R)2 may be bonded to the ring by a linking group or a single bond.

[0070] The linking group is preferably -O-, -S-, -C(-R)2-, >NR, or an arylene having 6 to 30 carbon atoms. In addition, R in the "-C(-R)2-" is hydrogen, alkyl, or aryl. In addition, R in the ">NR" is alkyl or aryl which may be substituted with alkyl.

[0071] From the viewpoint of short wavelength emission, X 1 , X 2 , and X 3 are each independently preferably >O, >NR, >C(-R)2 or >S, more preferably >O or >C(-R)2. Similarly, from the viewpoint of emission at a short wavelength, X 1 , X 2 , and X 3 From the viewpoint of high luminous efficiency, X 1 , X 2 , and X 3 is preferably at least two of >O, >NR, >C(-R)2, or >S, and more preferably at least two of >O, >NR, or >C(-R)2. From the viewpoint of the narrowness of the emission spectrum (narrowness of the half-width), it is preferable to strengthen the multiple resonance effect, and X 1 , X 2 , and X 3is preferably >O, >NR, >C(-R)2 or >S, more preferably >O, >NR or >C(-R)2, even more preferably >O or >NR, and still more preferably >NR. From the viewpoint of high triplet energy, X 1 , X 2 , and X 3 is preferably >NR, and from the same viewpoint, X 1 , X 2 , and X 3 On the other hand, from the viewpoint of low triplet energy, it is preferable that >O, >C(-R)2 or >S is selected. From the same viewpoint, X 1 , X 2 , and X 3 It is preferable that there are at least two kinds.

[0072] Also, X 1 , X 2 , and X 3 are preferably each independently >O, >NR, or >C(-R). 1 , X 2 , and X 3 It is preferable that one of X is >C(-R)2. 1 and X 2 It is more preferable that any one of X is >C(-R)2; 1 and X 2 It is more preferable that all of X are >C(-R)2. 1 and X 2 Any one of the above is >C(-R)2 and X 3 It is also preferred that >NR.

[0073] Here, the ring in the definition of "R of NR is bonded to a ring via a linking group or a single bond" in formula (1) is ring A, ring B, and / or ring C in formula (1), and ring a, ring b, and / or ring c in formula (2).

[0074] This provision is expressed by the following formula (2-3-1), X 2 Or X1 can be expressed as a compound having a ring structure in which X is incorporated into the fused ring B' and the fused ring C'. That is, for example, the compound having X in the benzene ring which is the b ring (or the c ring) in formula (2) 2 (or X 1 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, an acridine ring, or a phenophosphazine ring.

[0075] In addition, the above provision is expressed by the following formula (2-3-2) or formula (2-3-3), X 1 and / or X 2 In other words, for example, the a-ring in formula (2) is a benzene ring, and X 1 (and / or X 2 The compound has a ring A' formed by condensing another ring so as to incorporate the ring A'. The condensed ring A'' thus formed is, for example, a phenoxazine ring, a phenothiazine ring, an acridine ring, or a phenophosphazine ring.

[0076] [ka]

[0077] Although no specific explanation was given, the above provision states that X 3 The R of NR may be bonded to the B ring and / or the C ring (the b ring and / or the c ring) via a linking group or a single bond. For example, X 3 These are compounds having a ring B'' (or ring C'') formed by condensing another ring so as to incorporate the ring. For example, the condensed ring B' (or condensed ring C'') corresponds to a compound represented by formula (1-70) or formula (1-71) listed as specific compounds to be described later, and is, for example, a phenoxazine ring, a phenothiazine ring, an acridine ring, or a phenophosphazine ring.

[0078] In addition, the above provision states that 1 , X 2 , or X 3 Also included are complex forms in which the above is incorporated into any of the condensed rings.

[0079] The "aryl ring" which is the ring A, ring B, and ring C in formula (1) 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 9 In addition, since ring a (or ring b, ring c) is already composed of a benzene ring having six carbon atoms, the lower limit of the carbon number is the total carbon number of the fused rings formed by condensing the five-membered ring to this, which is nine.

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

[0081] Examples of the "heteroaryl ring" which is the ring A, ring B and ring C in formula (1) include heteroaryl rings having 2 to 30 carbon atoms, preferably heteroaryl rings having 2 to 25 carbon atoms, more preferably heteroaryl rings having 2 to 20 carbon atoms, further preferably heteroaryl rings having 2 to 15 carbon atoms, and particularly preferably heteroaryl rings having 2 to 10 carbon atoms. Examples of the "heteroaryl ring" include heterocycles containing, in addition to carbon, 1 to 5 heteroatoms selected from oxygen, sulfur and nitrogen as ring-constituting atoms. The "heteroaryl ring" can be a heterocyclic ring having "R" defined in formula (2). 1 ~R 9 In addition, since ring a (or ring b, ring c) is already composed of a benzene ring having 6 carbon atoms, the lower limit of the carbon number is the total carbon number of the fused rings fused to this 5-membered ring, which is 6.

[0082] Specific examples of the "heteroaryl ring" include a pyrrole ring, an oxazole ring, an isoxazole ring, a thiazole ring, an isothiazole ring, an imidazole ring (unsubstituted, substituted with an alkyl group such as methyl, or substituted with an aryl group such as phenyl), 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, 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 synthon ring, and the like. Examples of the ring include a phosphorus 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 naphthobenzofuran ring, a thiophene ring, a benzothiophene ring, a dibenzothiophene ring, a naphthobenzothiophene ring, a benzophosphole ring, a dibenzophosphole ring, a benzophosphole oxide ring, a dibenzophosphole oxide ring, a furazan ring, an oxadiazole ring, and a thianthrene ring.

[0083] At least one hydrogen atom in each of the above-mentioned "aryl ring", "heteroaryl ring", and "fused ring composed of two or more rings selected from the group consisting of a monocyclic aryl ring, a monocyclic heteroaryl ring, and a cyclopentadiene ring" is a first substituent, which is a substituted or unsubstituted "aryl", a substituted or unsubstituted "heteroaryl", a substituted or unsubstituted "diarylamino", a substituted or unsubstituted "diheteroarylamino", a substituted or unsubstituted "arylheteroarylamino", a substituted or unsubstituted "diarylboryl", a substituted or unsubstituted "alkyl", a substituted or unsubstituted "cycloalkyl", a substituted or unsubstituted "alkoxy", a substituted or unsubstituted "aryloxy", a substituted or unsubstituted "arylsulfonyl ... It may be substituted with a substituted "diarylphosphine", a substituted or unsubstituted "diarylphosphine oxide", a substituted or unsubstituted "diarylphosphine sulfide" or a substituted silyl, and examples of the "aryl" or "heteroaryl" as the first substituent, the aryl of the "diarylamino", the heteroaryl of the "diheteroarylamino", the aryl and heteroaryl of the "arylheteroarylamino", the "aryl of the "diarylboryl", the aryl of the "aryloxy", the aryl of the "arylsulfonyl", the aryl of the "diarylphosphine", the aryl of the "diarylphosphine", the aryl of the "diarylphosphine oxide", and the aryl of the "diarylphosphine sulfide" include the monovalent groups of the "aryl ring" or "heteroaryl ring" described above.

[0084] The "alkyl" as the first substituent may be either linear or branched, and examples thereof include linear alkyl having 1 to 24 carbon atoms or branched alkyl having 3 to 24 carbon atoms. An alkyl having 1 to 18 carbon atoms (branched alkyl having 3 to 18 carbon atoms) is preferred, an alkyl having 1 to 12 carbon atoms (branched alkyl having 3 to 12 carbon atoms) is more preferred, an alkyl having 1 to 6 carbon atoms (branched alkyl having 3 to 6 carbon atoms) is even more preferred, and an alkyl having 1 to 4 carbon atoms (branched alkyl having 3 to 4 carbon atoms) is particularly preferred.

[0085] 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.

[0086] Furthermore, the "cycloalkyl" as the first substituent 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. This explanation can also be cited as an explanation of a cycloalkyl that can be fused to at least one of ring A, ring B, and ring C.

[0087] Specific examples of cycloalkyl include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, and alkyl (particularly methyl) substituted derivatives of these having 1 to 5 carbon atoms, as well as norbornenyl, bicyclo[1.0.1]butyl, bicyclo[1.1.1]pentyl, bicyclo[2.0.1]pentyl, bicyclo[1.2.1]hexyl, bicyclo[3.0.1]hexyl, bicyclo[2.1.2]heptyl, bicyclo[2.2.2]octyl, adamantyl, diamantyl, decahydronaphthalenyl, and decahydroazulenyl.

[0088] Furthermore, examples of the "alkoxy" as the first substituent include linear alkoxy having 1 to 24 carbon atoms or branched alkoxy having 3 to 24 carbon atoms. An alkoxy having 1 to 18 carbon atoms (branched alkoxy having 3 to 18 carbon atoms) is preferred, an alkoxy having 1 to 12 carbon atoms (branched alkoxy having 3 to 12 carbon atoms) is more preferred, an alkoxy having 1 to 6 carbon atoms (branched alkoxy having 3 to 6 carbon atoms) is even more preferred, and an alkoxy having 1 to 4 carbon atoms (branched alkoxy having 3 to 4 carbon atoms) is particularly preferred.

[0089] Specific alkoxy includes methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, s-butoxy, t-butoxy, pentyloxy, hexyloxy, heptyloxy, octyloxy, and the like.

[0090] The "substituted silyl" as the first substituent 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.

[0091] The "trialkylsilyl" refers to a group in which three hydrogen atoms in a silyl group are each independently substituted with an alkyl, and the alkyl can be cited from the groups described as the "alkyl" in the first substituent above. The alkyl preferably used for substitution is an alkyl having 1 to 5 carbon atoms, and specific examples thereof include methyl, ethyl, propyl, i-propyl, butyl, sec-butyl, t-butyl, and t-amyl.

[0092] 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.

[0093] Examples of "tricycloalkylsilyl" include groups in which three hydrogen atoms in a silyl group are independently replaced with cycloalkyl, and the cycloalkyl can be cited as the group described as "cycloalkyl" in the first substituent above. Preferred cycloalkyl groups for substitution are cycloalkyl groups having 5 to 10 carbon atoms, specifically cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, bicyclo[1.1.1]pentyl, bicyclo[2.0.1]pentyl, bicyclo[1.2.1]hexyl, bicyclo[3.0.1]hexyl, bicyclo[2.1.2]heptyl, bicyclo[2.2.2]octyl, adamantyl, decahydronaphthalenyl, and decahydroazulenyl.

[0094] Specific examples of tricycloalkylsilyl include tricyclopentylsilyl and tricyclohexylsilyl.

[0095] 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.

[0096] Specific examples of dialkylarylsilyl substituted with two alkyl groups and one aryl group, alkyldiarylsilyl substituted with one alkyl group and two aryl groups, and triarylsilyl substituted with three aryl groups include silyl substituted with a group selected from the specific alkyl and aryl groups mentioned above.

[0097] As explained as substituted or unsubstituted, at least one hydrogen atom in the first substituent, substituted or unsubstituted "aryl", substituted or unsubstituted "heteroaryl", substituted or unsubstituted "diarylamino", substituted or unsubstituted "diheteroarylamino", substituted or unsubstituted "arylheteroarylamino", substituted or unsubstituted "diarylboryl", substituted or unsubstituted "alkyl", substituted or unsubstituted "cycloalkyl", substituted or unsubstituted "alkoxy", substituted or unsubstituted "aryloxy", substituted or unsubstituted "arylsulfonyl", substituted or unsubstituted "diarylphosphine", substituted or unsubstituted "diarylphosphine oxide", and substituted or unsubstituted "diarylphosphine sulfide", may be substituted with a second substituent. Examples of the second substituent include aryl, heteroaryl, and alkyl, and specific examples thereof can be seen in the explanation of the monovalent group of the "aryl ring" or "heteroaryl ring" and the "alkyl" as the first substituent. The aryl and heteroaryl as the second substituent also include groups in which at least one hydrogen atom is substituted with an aryl such as phenyl (specific examples are the groups mentioned above) or an alkyl such as methyl (specific examples are the groups mentioned above).As an example, when the second substituent is carbazolyl, the carbazolyl in which at least one hydrogen atom at the 9-position is substituted with an aryl such as phenyl or an alkyl such as methyl is also included in the heteroaryl as the second substituent.

[0098] The emission wavelength can be tuned by the steric hindrance, electron donating and electron withdrawing properties of the structure of the substituents (first substituent, second substituent and combinations of first and second substituents). Preferred are groups represented by the following structural formulas, more preferred are methyl, t-butyl, t-amyl, t-octyl, phenyl, o-tolyl, p-tolyl, 2,4-xylyl, 2,5-xylyl, 2,6-xylyl, 2,4,6-mesityl, diphenylamino, di-p-tolylamino, bis(p-(t-butyl)phenyl)amino, carbazolyl, 3,6-dimethylcarbazolyl, 3,6-di-t-butylcarbazolyl, and phenoxy, and even more preferred are methyl, t-butyl, t-amyl, t-octyl, phenyl, o-tolyl, 2,6-xylyl, 2,4,6-mesityl, diphenylamino, di-p-tolylamino, bis(p-(t-butyl)phenyl)amino, carbazolyl, 3,6-dimethylcarbazolyl, and 3,6-di-t-butylcarbazolyl.

[0099] In the structural formula below, "Me" represents methyl, "tBu" represents t-butyl, "tAm" represents t-amyl, and "tOct" represents t-octyl. [ka]

[0100] [ka]

[0101] [ka]

[0102] [ka]

[0103] R in Equation (2) 1 ~R 9 , R and R in formula (1a), formula (1a-1) to formula (1a-15) a1 ~Ra8 , R aa1 ~R aa4 , and R and R in formula (1b) a9 ~R a16 , R in Eq. (3), Eq. (4), Eq. (5), Eq. (6), Eq. (7), Eq. (8), Eq. (9), Eq. (10), Eq. (11), Eq. (12), Eq. (13), Eq. (14) and Eq. (15) b1 ~R b13 The aryl, heteroaryl, aryl of diarylamino, heteroaryl of diheteroarylamino, aryl and heteroaryl of arylheteroarylamino, or aryl of aryloxy in the formula (2) include the monovalent groups of the "aryl ring" or "heteroaryl ring" described in the formula (1). 1 ~R 9 , R and R in formula (1a), formula (1a-1) to formula (1a-15) a1 ~R a8 , and R and R in formula (1b) a9 ~R a16 , R in Eq. (3), Eq. (4), Eq. (5), Eq. (6), Eq. (7), Eq. (8), Eq. (9), Eq. (10), Eq. (11), Eq. (12), Eq. (13), Eq. (14) and Eq. (15) b1 ~R b13 For the alkyl or alkoxy in, the explanation of "alkyl" or "alkoxy" as the first substituent in the explanation of formula (1) above can be referred to. Furthermore, the same applies to aryl, heteroaryl, or alkyl as a substituent to these groups.

[0104] Y in Equation (1) 1In the above formula, R in Si-R and Ge-R is aryl, alkyl, or cycloalkyl, and specific examples of the aryl, alkyl, and cycloalkyl include the groups described above. In particular, aryl having 6 to 12 carbon atoms, aryl having 6 to 10 carbon atoms (e.g., phenyl, naphthyl, etc.), alkyl having 1 to 6 carbon atoms, and alkyl having 1 to 4 carbon atoms (e.g., methyl, ethyl, etc.) are preferred. This explanation applies to Y in formula (2), formula (3), formula (4), formula (5), formula (6), formula (7), formula (8), formula (9), formula (10), formula (11), formula (12), formula (13), formula (14), and formula (15). 1 But it's the same.

[0105] X in formula (1) 1 , X 2 , and X 3 In the formula (1), R in >C(-R)2 and >Si(-R)2 is hydrogen, aryl which may be substituted with the above-mentioned second substituent, alkyl which may be substituted with the above-mentioned second substituent, or cycloalkyl which may be substituted with the second substituent. Specific examples of this aryl, heteroaryl, alkyl, or cycloalkyl include the groups described above. In particular, aryl having 6 to 10 carbon atoms (e.g., phenyl, naphthyl, etc.) and alkyl having 1 to 4 carbon atoms (e.g., methyl, ethyl, etc.) are preferred. X in formula (1) 1 , X 2 , and X 3 In the above formula (2), R in >C(-R)2 is preferably methyl. This explanation applies to X in formula (2), formula (3), formula (4), formula (5), formula (6), formula (7), formula (8), formula (9), formula (10), formula (11), formula (12), formula (13), formula (14), and formula (15). 1 , X 2 , and X 3 But it's the same.

[0106] X in formula (1) 1 , X 2 , and X 3In the formula, R of NR is an aryl which may be substituted with the second substituent, a heteroaryl which may be substituted with the second substituent, an alkyl which may be substituted with the second substituent, or a cycloalkyl which may be substituted with the second substituent. Specific examples of the aryl, heteroaryl, alkyl, or cycloalkyl include the groups described above. In particular, aryl having 6 to 10 carbon atoms (e.g., phenyl, naphthyl, etc.), heteroaryl having 2 to 15 carbon atoms (e.g., carbazolyl, etc.), and alkyl having 1 to 4 carbon atoms (e.g., methyl, ethyl, etc.) are preferred. X 1 , X 2 , and X 3 In the above formula, R of NR is preferably methyl, t-butyl, t-amyl, t-octyl, phenyl, o-tolyl, p-tolyl, 2,4-xylyl, 2,5-xylyl, 2,6-xylyl, or 2,4,6-mesityl. This explanation applies to X in formula (2), formula (3), formula (4), formula (5), formula (6), formula (7), formula (8), formula (9), formula (10), formula (11), formula (12), formula (13), formula (14), and formula (15). 1 , X 2 , and X 3 But it's the same.

[0107] In formula (1), R in "-C(-R)2-" which is a linking group is hydrogen, alkyl or aryl, and R in ">NR" is alkyl or aryl which may be substituted with alkyl, and specific examples of the alkyl and aryl include the groups described above. In particular, alkyl having 1 to 6 carbon atoms, alkyl having 1 to 4 carbon atoms (e.g., methyl, ethyl, etc.), and aryl having 6 to 12 carbon atoms (e.g., phenyl, naphthyl, etc.) which may be substituted with alkyl having 1 to 6 carbon atoms or alkyl having 1 to 4 carbon atoms (e.g., methyl, ethyl, etc.) are preferred. This explanation also applies to "-C(-R)2-" and ">NR" which are linking groups in formulas (2), (3), (4), (5), (6), (7), (8), (9), (10), (11), (12), (13), (14), and (15).

[0108] In addition, the linking group "arylene" or "arylene having 6 to 30 carbon atoms" in formula (1) can be a divalent group having the same structure as the above-mentioned aryl. This explanation also applies to the linking group "arylene having 6 to 12 carbon atoms" in formulas (2), (3), (4), (5), (6), (7), (8), (9), (10), (11), (12), (13), (14), and (15).

[0109] The multimer of the polycyclic aromatic compound having two unit structures represented by formula (1) is preferably a dimer. The dimer is preferably a dimer of a polycyclic aromatic compound having two unit structures represented by any one of formulas (3) to (15). The dimer may be in a form having two of the above unit structures in one compound, and may be in a form in which the above unit structures are bonded together by a linking group such as a single bond, an alkylene having 1 to 3 carbon atoms, phenylene, or naphthylene, or in which any ring (ring A, ring B, or ring C, etc.) contained in the above unit structures is shared by two unit structures, or in which any ring (ring A, ring B, or ring C) contained in the above unit structures is bonded together so as to be condensed.

[0110] Examples of such dimers include dimers represented by the following formula (2-4), formula (2-5), or formula (2-6). That is, when explained in terms of formula (2), it is a dimer having two unit structures represented by formula (2) in one compound, with the benzene ring being the a-ring being shared. Also, the dimer represented by the following formula (2-5) is, when explained in terms of formula (2), a dimer having a benzene ring being the a-ring and X 2 A dimer having two unit structures represented by formula (2) in one compound, with the two unit structures represented by formula (2) sharing the same ring. A dimer represented by formula (2-6) below, for example, is a dimer having two unit structures represented by formula (2) in one compound, with the benzene ring that is the a-ring (or b-ring, c-ring) of a certain unit structure condensed with the benzene ring that is the a-ring (or b-ring, c-ring) of a certain unit structure. Note that Y in the following formula 1 , X 1 , X 2 , X3 , R 1 and R 3 ~R 9 The definitions of are the same as those in equation (2).

[0111] [ka]

[0112] In addition, all or a part of hydrogen atoms in the chemical structure of the polycyclic aromatic compound represented by any one of formulas (1) and (2) to (15) and the multimer thereof may be cyano, halogen, or deuterium. For example, in formula (1), ring A, ring B, ring C (rings A to C are aryl rings or heteroaryl rings), substituents on rings A to C, Y 1 R when is Si-R or Ge-R, and X 1 , X 2 and X 3 In the case of >C(-R)2 or NR, hydrogen in R can be replaced by cyano, halogen, or deuterium, and among these, there is an embodiment in which all or a part of hydrogen in aryl or heteroaryl is replaced by cyano, halogen, or deuterium. Halogen is fluorine, chlorine, bromine, or iodine, preferably fluorine, chlorine, or bromine, and more preferably chlorine.

[0113] At least one selected from the group consisting of aryl rings and heteroaryl rings in the chemical structures of the polycyclic aromatic compounds and multimers thereof represented by formulas (1) to (15) may be condensed with at least one cycloalkane.

[0114] For example, aryl and heteroaryl rings in the A, B, C, a, b, c rings, and fused rings, 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, Y 1Aryl as R in Si-R and Ge-R (as above), and X 1 , X 2 , X 3 At least one of the aryl (as above) and heteroaryl (as above) as R in >NR, >Si(-R)2 and >C(-R)2 may be fused with at least one cycloalkane.

[0115] 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.

[0116] 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.

[0117] Among these, for example, 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 cycloalkyl condensed to an aromatic ring or a heteroaromatic ring) is preferred, a structure in which two hydrogen atoms are substituted on the carbon atom at the α-position is more preferred, and a structure in which a total of four hydrogen atoms are substituted on the two carbon atoms at the α-position is even more preferred. Examples of this substituent include an alkyl (particularly methyl) substituent having 1 to 5 carbon atoms, a halogen (particularly fluorine) substituent, and a deuterium substituent.

[0118] The number of cycloalkanes fused to one aryl ring or heteroaryl ring is preferably 1 to 3, more preferably 1 or 2, and even more preferably 1. For example, an example in which one or more cycloalkanes are fused to one benzene ring (phenyl) is shown below. Cycloalkanes fused to each other as in formula (Cy-1-4) and formula (Cy-2-4) may be fused. The same applies even if the fused ring (group) is an aromatic ring or heteroaromatic ring other than a benzene ring (phenyl), or even if the fused cycloalkane is a cycloalkane other than cyclopentane or cyclohexane. [ka]

[0119] 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.

[0120] [ka]

[0121] 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.

[0122] [ka]

[0123] Other forms of cycloalkane condensation include polycyclic aromatic compounds represented by formulas (1) to (15) and multimers thereof, such as >NR, where R is an aryl condensed with a cycloalkane, diarylamino condensed with a cycloalkane (condensed to the aryl portion), carbazolyl condensed with a cycloalkane (condensed to the benzene ring portion), or benzocarbazolyl condensed with a cycloalkane (condensed to the benzene ring portion). Examples of "diarylamino" include the groups described above as the "first substituent."

[0124] Further, as a more specific example, R in the polycyclic aromatic compound and its multimer represented by the formula (2) 2 is a diarylamino fused to a cycloalkane (fused to the aryl moiety) or a carbazolyl fused to a cycloalkane (fused to the benzene ring moiety).

[0125] The polycyclic aromatic compound and its multimer of the present invention can be used as a material for an organic device. Examples of the organic device include an organic electroluminescence device, an organic field effect transistor, and an organic thin-film solar cell. In particular, in an organic electroluminescence device, Y is preferably used as a dopant material for the light-emitting layer. 1 is B and X 1 , X 2 , and X 3 Compounds where Y is NR 1 is B and X 1 , X 2 , and X 3 Compounds in which one of the groups is O and the other is NR, Y 1 is B and X 1 , X 2 , and X 3 Compound Y, in which two of the groups are O and the others are NR. 1 is B and X 1 , X 2 , and X 3 Compound Y, in which two of the groups are >C(-R)2 and the others are NR. 1 is B and X 1 , X 2 and X 3 and the other is O. 1 is B or P=O, and X 1 , X 2 , and X 3 Compounds where Y is NR 1 is B or P=O, and X 1 , X 2 , and X 3 Compounds in which one of the groups is O and the other is NR, Y 1 is B or P=O, and X 1 , X 2 and X 3 A compound in which two of the groups are O and the other is NR is preferred. 1 is B or P=O, and X 1 , X 2 , and X 3 Compounds in which Y is O 1is B or P=O, and X 1 , X 2 , and X 3 Compounds in which Y is 1 is B or P=O, and X 1 , X 2 , and X 3 Compounds where Y is >C(-R)2 1 is B or P=O, and X 1 , X 2 , and X 3 A compound in which two of the groups are O and the remaining groups are NR is preferably used.

[0126] More specific examples of the polycyclic aromatic compound of the present invention include compounds represented by the following chemical structural formulas: In the chemical structural formula, Me is methyl, tBu is tert-butyl, and tAm is t-amyl.

[0127] [ka]

[0128] [ka]

[0129] [ka]

[0130] [ka]

[0131] [ka]

[0132] [ka]

[0133] [ka]

[0134] [ka]

[0135] [ka]

[0136] [ka]

[0137] [ka]

[0138] [ka]

[0139] The polycyclic aromatic compound represented by formula (1) according to the present invention and its multimer can also be used as a material for organic devices, for example, a material for organic electroluminescent elements, a material for organic field effect transistors, or a material for organic thin-film solar cells, in the form of a polymer compound obtained by polymerizing a reactive compound substituted with a reactive substituent as a monomer (the monomer for obtaining this polymer compound has a polymerizable substituent), a crosslinked polymer obtained by further crosslinking the polymer compound (the polymer compound for obtaining this crosslinked polymer has a crosslinkable substituent), a pendant polymer compound obtained by reacting a main-chain polymer with the reactive compound (the reactive compound for obtaining this pendant polymer compound has a reactive substituent), or a pendant crosslinked polymer obtained by further crosslinking the pendant polymer compound (the pendant polymer compound for obtaining this crosslinked pendant polymer has a crosslinkable substituent).

[0140] 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 or its multimer, 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.

[0141] [ka]

[0142] L X are each 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, and 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.

[0143] 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.

[0144] 2. Method for producing polycyclic aromatic compounds and their polymers The polycyclic aromatic compounds and their dimers represented by formula (1) and (2) are basically produced by first bonding ring A (ring a) to ring B (ring b) and ring C (ring c) through bonding groups (X 1 , X 2 , X 3 A ring (a ring), a ring (b ring) and a ring (c ring) are bonded with a bonding group (Y 1The final product can be produced by bonding with a group containing Y (second reaction). In the first reaction, for example, for etherification, general reactions such as nucleophilic substitution and Ullmann reaction can be used, and for amination, general reactions such as Buchwald-Hartwig reaction can be used. In addition, in the second reaction, a tandem hetero Friedel-Crafts reaction (sequential aromatic electrophilic substitution reaction, the same applies below) can be used. In the following scheme, Y 1 , X 1 , X 2 , X 3 , R 1 ~R 9 and the definitions of R are the same as those in formula (1) or formula (2).

[0145] The second reaction is, as shown in the following schemes (1) and (2), a Y bond that bonds the A ring (ring a), the B ring (ring b), and the C ring (ring c). 1 This is a reaction that introduces Y 1 is a boron atom, X 1 , X 2 , X 3 The case where is >NR is shown below. First, X 1 , X 2 , X 3 The hydrogen atom 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, followed by the addition of a Brønsted base such as N,N-diisopropylethylamine to carry out a tandem boron-Friedel-Crafts reaction to obtain the desired product. In the second reaction, a Lewis acid such as aluminum trichloride may be added to promote the reaction.

[0146] [ka]

[0147] The above schemes (1) and (2) mainly show the method for producing the polycyclic aromatic compounds represented by formulas (1) and (2), but the dimers can be produced by using intermediates having multiple A rings (a rings), B rings (b rings) and C rings (c rings). Details are explained in the following schemes (3) and (4). In this case, the target product can be obtained by doubling the amount of the reagent such as butyl lithium used.

[0148] [ka]

[0149] In the above scheme, lithium was introduced into the desired position by orthometalation. However, as in the following schemes (5) and (6), lithium can also be introduced into the desired position by introducing a halogen atom (Hal) into the desired position and then by halogen-metal exchange.

[0150] [ka]

[0151] In addition, in the method for producing a dimer explained in Scheme (3) or Scheme (4), lithium can also be introduced into the desired position by introducing a halogen such as a bromine atom or a chlorine atom into the position where lithium is to be introduced as in Schemes (5) and (6) above, and then by halogen-metal exchange (Schemes (7) and (8) below).

[0152] [ka]

[0153] This method is useful because it allows the synthesis of the target compound even in cases where ortho-metallation is not possible due to the influence of substituents.

[0154] By appropriately selecting the above synthesis method and the raw materials to be used, it is possible to obtain a compound having a substituent at a desired position, Y 1is a boron atom, X 1 , X 2 and X 3 It is possible to synthesize polycyclic aromatic compounds and dimers thereof in which the ring is a nitrogen atom.

[0155] Next, as an example, Y 1 is a boron atom, X 1 and X 2 is a nitrogen atom, and X 3 The case where X is an oxygen atom is shown in the following schemes (9) and (10). 1 , X 2 , X 3 As in the case where all atoms are nitrogen atoms, halogens such as bromine atoms or chlorine atoms are introduced to the desired position for lithium introduction, and n-butyllithium or the like is reacted to metallize the compound by halogen-metal exchange. Next, boron tribromide or the like is added to carry out lithium-boron metal exchange, and then a tandem boron-Friedel-Crafts reaction can be carried out by adding a Bronsted base such as N,N-diisopropylethylamine to obtain the desired compound. Here, a Lewis acid such as aluminum trichloride may be added to promote the reaction.

[0156] [ka]

[0157] Also, Y 1 is a boron atom, X 1 and X 2 is a nitrogen atom, and X 3 For the dimer in which is an oxygen atom, lithium can also be introduced into the desired position by introducing a halogen such as a bromine atom or a chlorine atom into the position where lithium is to be introduced as in the above schemes (7) and (8), and then by halogen-metal exchange (the following schemes (11) and (12)).

[0158] [ka]

[0159] Next, as an example, Y 1is phosphorus sulfide, phosphorus oxide or phosphorus atom, and X 1 , X 2 , X 3 The cases where all atoms are nitrogen atoms are shown in the following schemes (13) to (16). As in the previous schemes, first, a halogen atom such as a bromine atom or a chlorine atom is introduced at the position where lithium is to be introduced, and metallation is performed by halogen-metal exchange. Next, phosphorus trichloride and sulfur are added in this order, and finally, a Lewis acid such as aluminum trichloride and a Brønsted base such as N,N-diisopropylethylamine are added to carry out a tandem phospha-Friedel-Crafts reaction to give Y 1 A compound in which Y is a phosphorus sulfide can be obtained. In addition, by treating the obtained phosphorus sulfide compound with m-chloroperbenzoic acid (m-CPBA), Y can be obtained. 1 The resulting phosphorus oxide compound can be treated with triethylphosphine to give Y 1 It is possible to obtain a compound in which is a phosphorus atom.

[0160] [ka]

[0161] [ka]

[0162] Also, Y 1 is phosphorus sulfide, X 1 , X 2 , X 3 For dimers in which all atoms are nitrogen atoms, lithium can also be introduced to the desired position by halogen-metal exchange, by introducing halogens such as bromine and chlorine atoms to the position where lithium is to be introduced, as in the above schemes (7) and (8) (see below schemes (17) and (18)). 1 is phosphorus sulfide, X 1 , X 2 , X 3The dimer in which all the atoms are nitrogen can also be obtained by treating the phosphorus sulfide compound with m-chloroperbenzoic acid (m-CPBA) as shown in schemes (15) and (16) above. 1 The resulting phosphorus oxide compound can be treated with triethylphosphine to give Y 1 It is possible to obtain a compound in which is a phosphorus atom.

[0163] [ka]

[0164] Here, Y 1 is B, P, P=O or P=S, and X 1 , X 2 and X 3 Although the examples where is NR or O are described, by appropriately changing the raw material, Y 1 is P(-R)2, Al, Ga, As, Si-R, Ge-R, Sn-R, Sb, Sb=O, Sb=S, Sb(-R)2, Sb with ortho-chloranil, Bi, Bi=O, Bi=S, Bi(-R)2 or Bi with ortho-chloranil, or X 1 , X 2 and X 3 Compounds in which Y is S can also be synthesized. 1 However, it is also possible to convert Sn from Sn-R compounds to other transition metals.

[0165] Specific examples of solvents that can be used in the above reactions include t-butylbenzene and xylene.

[0166] In addition, in formula (2), the substituents R 1 ~R 9Adjacent groups among may be bonded together to form an aryl or 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 or heteroaryl. Therefore, the polycyclic aromatic compound represented by formula (2) has a ring structure that constitutes the compound that changes as shown in formulas (2-1) and (2-2) in the following schemes (19) and (20) depending on the mutual bonding form of the substituents in the a ring, the b ring, and the c ring. These compounds can be synthesized by applying the synthetic methods shown in the above schemes (1) to (18) to the intermediates shown in the following schemes (19) and (20).

[0167] [ka]

[0168] The A' ring, the B' ring and the C' ring in the above formula (2-1) and formula (2-2) each independently represent a substituent R 1 ~R 9 Adjacent groups in the above are bonded to form an aryl or heteroaryl ring together with the a, b, and c rings (they can also be considered condensed rings formed by condensing the a, b, or c ring with other ring structures). Although not shown in the formula, there are also compounds in which the a, b, and c rings are all changed to A', B', and C' rings.

[0169] In addition, the provision in formula (2) that "R of NR is bonded to the ring a, ring b and / or ring c by -O-, -S-, -C(-R)2-, >NR, arylene, a single bond or condensation" is intended to mean X represented by formula (2-3-1) in the following scheme (21). 1 Or X 2 Compounds having a ring structure in which X is incorporated into the fused ring B' and the fused ring C', and compounds represented by formula (2-3-2) or formula (2-3-3), 1 Or X 2 can be expressed as a compound having a ring structure in which is incorporated into a fused ring A'. These compounds can be synthesized by applying the synthetic methods shown in the above schemes (1) to (18) to the intermediates shown in the following scheme (21).

[0170] [ka]

[0171] In the above synthesis schemes (1) to (14) and (17) to (21), before adding boron trichloride, boron tribromide, etc., X 1 , X 2 , X 3 In the example shown here, the hydrogen atom (or halogen atom) between the rings was ortho-metallated with butyllithium or the like to perform the tandem hetero Friedel-Crafts reaction. However, the reaction can also be carried out by adding boron trichloride, boron tribromide, or the like without ortho-metallation using butyllithium or the like.

[0172] Also, Y 1 In the case of phosphorus-based, X is as shown in the following schemes (22) and (23). 1 and X 2 and X 3 The hydrogen atom (or halogen atom) between (>NR in the following formula) is orthometalated with n-butyllithium, sec-butyllithium, t-butyllithium, or the like, and then bisdiethylaminochlorophosphine is added to carry out lithium-phosphorus metal exchange, followed by adding a Lewis acid such as aluminum trichloride to carry out a tandem phospha Friedel-Crafts reaction to obtain the target product. This reaction method is also described in WO 2010 / 104047 (e.g., page 27).

[0173] [ka]

[0174] [ka]

[0175] In the above schemes (22) and (23), a dimer can be synthesized by using an orthometalation reagent such as butyllithium in a molar amount twice that of intermediate 1. Moreover, a halogen such as a bromine atom or a chlorine atom is first introduced into the position where a metal such as lithium is to be introduced, and then the metal can be introduced into the desired position by halogen-metal exchange.

[0176] Examples of the ortho-metallation reagent used in the above schemes (1) to (23) include alkyllithium such as methyllithium, n-butyllithium, sec-butyllithium, and t-butyllithium, and organic alkali compounds such as lithium diisopropylamide, lithium tetramethylpiperidide, lithium hexamethyldisilazide, and potassium hexamethyldisilazide.

[0177] The metal-Y used in the above schemes (1) to (23) 1 The metal exchange reagent for Y 1 trifluoride, Y 1 trichloride, Y 1 Tribromide of Y 1 of triiodide, etc. 1 Halides of Y such as CIPN(NEt2)2 1 Aminated halides of Y 1 Alkoxylated compounds of Y 1 and aryloxy compounds of the above.

[0178] Examples of the Bronsted base used in the above schemes (1) to (23) include N,N-diisopropylethylamine, triethylamine, 2,2,6,6-tetramethylpiperidine, 1,2,2,6,6-pentamethylpiperidine, N,N-dimethylaniline, N,N-dimethyltoluidine, 2,6-lutidine, sodium tetraphenylborate, potassium tetraphenylborate, triphenylborane, tetraphenylsilane, Ar4BNa, Ar4BK, Ar3B, and Ar4Si (Ar is an aryl such as phenyl).

[0179] Examples of Lewis acids used in the above schemes (1) to (23) include AlCl3, AlBr3, AlF3, BF3·OEt2, BCl3, BBr3, GaCl3, GaBr3, InCl3, InBr3, In(OTf)3, SnCl4, SnBr4, AgOTf, ScCl3, Sc(OTf)3, ZnCl2, ZnBr2, Zn(OTf)2, MgCl2, MgBr2, Mg(OTf)2, LiOTf, NaOTf, KOTf, Me3SiOTf, Cu(OTf)2, CuCl2, YCl3, Y(OTf)3, TiCl4, TiBr4, ZrCl4, ZrBr4, FeCl3, FeBr3, CoCl3, and CoBr3.

[0180] In the above schemes (1) to (23), a Brønsted base or Lewis acid may be used to promote the tandem hetero Friedel-Crafts reaction. 1 trifluoride, Y 1 trichloride, Y 1 Tribromide of Y 1 of triiodide, etc. 1 When using halides of Y, acids such as hydrogen fluoride, hydrogen chloride, hydrogen bromide, and hydrogen iodide are generated as the aromatic electrophilic substitution reaction proceeds, so the use of a Brønsted base to capture the acid is effective. 1 Aminated halides of Y 1 When an alkoxylated compound of the above is used, since amines and alcohols are produced as the aromatic electrophilic substitution reaction proceeds, it is often not necessary to use a Brønsted base. However, since the amino and alkoxy groups have low ability to be eliminated, it is effective to use a Lewis acid that promotes their elimination.

[0181] In the above, X 1 , X 2 , X 3 We have mainly shown the cases where >NR, but 1 , X 2 , X 3For compounds where >C(-R)2, the starting compound can be changed and synthesized by the method described in Organic & Biomolecular Chemistry, 2019, 17, 5500-5504 by Yamaguchi et al.

[0182] The polycyclic aromatic compound and its multimer of the present invention also include compounds in which at least a portion of hydrogen atoms is substituted with cyano, deuterium, or halogen such as fluorine or chlorine. Such compounds can be synthesized in the same manner as described above by using a raw material in which the desired site is cyanated, deuterized, fluorinated, or chlorinated.

[0183] 3. Organic Devices The compound of the present invention (polycyclic aromatic compound represented by formula (1) and its multimer, reactive compound in which any of the above is substituted with a reactive substituent, polymer compound in which any of the above is polymerized, crosslinked polymer, pendant-type polymer compound, or crosslinked pendant-type polymer) can be used as a material for an organic device. Examples of the organic device include an organic electroluminescent element, an organic field effect transistor, and an organic thin-film solar cell.

[0184] 3-1. Organic electroluminescent device The compound of the present invention can be used, for example, as a material for an organic electroluminescent device. The organic EL device according to this embodiment will be described in detail below with reference to the drawings. Figure 1 is a schematic cross-sectional view showing an organic EL device according to this embodiment.

[0185] 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.

[0186] 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.

[0187] 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.

[0188] 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".

[0189] 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.

[0190] 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.

[0191] 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 can be appropriately selected from those used as anodes in organic EL elements.

[0192] 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 can function 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.

[0193] 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.

[0194] 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.

[0195] 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 and other triphenylamine derivatives, starburst amine derivatives, etc.), stilbene derivatives, phthalocyanine derivatives (metal-free, copper phthalocyanine, etc.), pyrazoline derivatives, hydrazone compounds, benzofuran derivatives, thiophene derivatives, oxadiazole derivatives, quinoxaline derivatives Conductors (e.g., 1,4,5,8,9,12-hexaazatriphenylene-2,3,6,7,10,11-hexacarbonitrile, etc.), heterocyclic compounds such as porphyrin derivatives, polysilanes, etc. As polymers, polycarbonates and styrene derivatives having the above-mentioned monomers in their side chains, polyvinylcarbazole, polysilanes, etc. are preferred, but there are no particular limitations on the compounds as long as they can form a thin film required for fabricating a light-emitting device, can inject holes from the anode, and can transport holes.

[0196] It is also known that the electrical conductivity of organic semiconductors is strongly influenced by their doping. Such organic semiconductor matrix substances consist of compounds with good electron donating or accepting properties. For doping with electron donating substances, strong electron acceptors such as tetracyanoquinone dimethane (TCNQ) or 2,3,5,6-tetrafluorotetracyano-1,4-benzoquinone dimethane (F4TCNQ) are known (see, for example, the 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).

[0197] 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 explanation of the polycyclic aromatic compound represented by formula (1) can be cited as the reactive substituent. The applications of such polymer compounds and crosslinked polymers will be described in detail below.

[0198] 3-1-5. Light-emitting layer in organic electroluminescent device The light-emitting layer 105 is a layer that emits light by recombining holes injected from the anode 102 and electrons injected from the cathode 108 between electrodes to which an electric field is applied. The material for the light-emitting layer 105 may be a compound (light-emitting compound) that is excited and emits light by the recombination of holes and electrons, and is preferably a compound that can be formed into a stable thin film shape and exhibits strong luminescence (fluorescence) efficiency in a solid state.

[0199] The light-emitting layer may be a single layer or multiple layers, each of which is formed from materials for the light-emitting layer (host material, dopant material). The host material and the dopant material may each be one type or a combination of multiple types. The dopant material may be contained in the entire host material or may be contained partially in the host material. As a doping method, the dopant material may be formed by co-evaporation with the host material, but it may also be mixed with the host material in advance and then vapor-deposited at the same time.

[0200] The compound of the present invention is preferably used as a material for a light-emitting layer, and particularly preferably used as a dopant material.

[0201] 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.

[0202] 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.

[0203] Examples of the host material include condensed ring derivatives such as anthracene, pyrene, dibenzochrysene, and fluorene, which have been known as light emitters, bisstyryl derivatives such as bisstyrylanthracene derivatives and distyrylbenzene derivatives, tetraphenylbutadiene derivatives, and cyclopentadiene derivatives. In particular, anthracene-based compounds, fluorene-based compounds, and dibenzochrysene-based compounds are preferred.

[0204] <<Host material>> <Anthracene compounds> The anthracene compound as the host is, for example, a compound represented by the following formula (H3). [ka]

[0205] In formula (H3), X and Ar 4 are each independently hydrogen, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted diarylamino, optionally substituted diheteroarylamino, optionally substituted arylheteroarylamino, optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted alkenyl, optionally substituted alkoxy, optionally substituted aryloxy, optionally substituted arylthio or optionally substituted silyl; and all X and Ar 4 cannot simultaneously become hydrogen, At least one hydrogen in the compound represented by formula (H3) may be substituted with halogen, cyano, deuterium or an optionally substituted heteroaryl.

[0206] In addition, a polymer (preferably a dimer) may be formed using the structure represented by formula (H3) as a unit structure. In this case, for example, the unit structures represented by formula (H3) may be bonded to each other via X, and examples of X include a single bond, an arylene (phenylene, biphenylene, naphthylene, etc.), and a heteroarylene (a pyridine ring, a dibenzofuran ring, a dibenzothiophene ring, a carbazole ring, a benzocarbazole ring, and a phenyl-substituted carbazole ring, etc., each having a divalent bond).

[0207] The details of the above aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, alkyl, cycloalkyl, alkenyl, alkoxy, aryloxy, arylthio, or silyl will be described in the following preferred embodiment section. The substituents on these include aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, alkyl, cycloalkyl, alkenyl, alkoxy, aryloxy, arylthio, or silyl, and the details of these are also described in the following preferred embodiment section.

[0208] Preferred embodiments of the above anthracene-based compounds are described below. The symbols in the structures below are defined as above. [ka]

[0209] In formula (H3), X is each independently a group represented by formula (3-X1), formula (3-X2) or formula (3-X3), and the group represented by formula (3-X1), formula (3-X2) or formula (3-X3) is bonded to the anthracene ring of formula (H3) at *. Preferably, two Xs are not simultaneously a group represented by formula (3-X3). More preferably, two Xs are not simultaneously a group represented by formula (3-X2).

[0210] In addition, a polymer (preferably a dimer) may be formed using the structure represented by formula (H3) as a unit structure. In this case, for example, the unit structures represented by formula (H3) may be bonded to each other via X, and examples of X include a single bond, an arylene (phenylene, biphenylene, naphthylene, etc.), and a heteroarylene (a pyridine ring, a dibenzofuran ring, a dibenzothiophene ring, a carbazole ring, a benzocarbazole ring, and a phenyl-substituted carbazole ring, etc., each having a divalent bond).

[0211] The naphthylene moieties in formula (3-X1) and formula (3-X2) may be condensed with one benzene ring. The condensed structures are as follows: [ka]

[0212] Ar 1 and Ar 2 are each independently hydrogen, phenyl, biphenylyl, terphenylyl, quaterphenylyl, naphthyl, phenanthryl, fluorenyl, benzofluorenyl, chrysenyl, triphenylenyl, pyrenylyl, or a group represented by the above formula (A) (including carbazolyl, benzocarbazolyl, and phenyl-substituted carbazolyl). 1 or Ar 2 is a group represented by formula (A), the group represented by formula (A) is bonded to the naphthalene ring in formula (3-X1) or formula (3-X2) at the *.

[0213] Ar 3 is phenyl, biphenylyl, terphenylyl, quaterphenylyl, naphthyl, phenanthryl, fluorenyl, benzofluorenyl, chrysenyl, triphenylenyl, pyrenylyl, or a group represented by the above formula (A) (including carbazolyl, benzocarbazolyl, and phenyl-substituted carbazolyl). 3is a group represented by formula (A), the group represented by formula (A) is bonded to the single bond represented by a straight line in formula (3-X3) at the *. That is, the anthracene ring of formula (H3) and the group represented by formula (A) are directly bonded.

[0214] Also, Ar 3 may have a substituent, and Ar 3 At least one hydrogen atom in may be further substituted with an alkyl group having 1 to 4 carbon atoms, a cycloalkyl group having 5 to 10 carbon atoms, phenyl, biphenylyl, terphenylyl, naphthyl, phenanthryl, fluorenyl, chrysenyl, triphenylenyl, pyrenylyl, or a group represented by the above formula (A) (including carbazolyl and phenyl-substituted carbazolyl). 3 is a group represented by formula (A), the group represented by formula (A) is Ar 3 and combine.

[0215] Ar 4 are each independently hydrogen, phenyl, biphenylyl, terphenylyl, naphthyl, or silyl substituted with alkyl having 1 to 4 carbon atoms (eg, methyl, ethyl, t-butyl) and / or cycloalkyl having 5 to 10 carbon atoms.

[0216] Examples of the alkyl group having 1 to 4 carbon atoms that substitutes for the silyl include methyl, ethyl, propyl, i-propyl, butyl, sec-butyl, t-butyl, and cyclobutyl, and three hydrogen atoms in the silyl are each independently substituted with these alkyl groups.

[0217] Specific examples of "silyl substituted with alkyl having 1 to 4 carbon atoms" include trimethylsilyl, triethylsilyl, tripropylsilyl, tri-i-propylsilyl, tributylsilyl, tri-sec-butylsilyl, tri-t-butylsilyl, ethyldimethylsilyl, propyldimethylsilyl, i-propyldimethylsilyl, butyldimethylsilyl, sec-butyldimethylsilyl, t-butyldimethylsilyl, methyldiethylsilyl, propyldiethylsilyl, i-propyldiethylsilyl, butyldiethylsilyl, sec-butyldiethylsilyl, t-butyldiethylsilyl, methyldipropylsilyl, ethyldipropylsilyl, butyldipropylsilyl, sec-butyldipropylsilyl, t-butyldipropylsilyl, methyldi-i-propylsilyl, ethyldi-i-propylsilyl, butyldi-i-propylsilyl, sec-butyldi-i-propylsilyl, and t-butyldi-i-propylsilyl.

[0218] Examples of the cycloalkyl having 5 to 10 carbon atoms substituting the silyl include cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, norbornenyl, bicyclo[1.1.1]pentyl, bicyclo[2.0.1]pentyl, bicyclo[1.2.1]hexyl, bicyclo[3.0.1]hexyl, bicyclo[2.1.2]heptyl, bicyclo[2.2.2]octyl, adamantyl, decahydronaphthalenyl, and decahydroazulenyl, and three hydrogen atoms in the silyl are each independently substituted with these cycloalkyls.

[0219] Specific examples of the "silyl substituted with cycloalkyl having 5 to 10 carbon atoms" include tricyclopentylsilyl and tricyclohexylsilyl.

[0220] Substituted silyls include dialkylcycloalkylsilyls, which are substituted with two alkyl groups and one cycloalkyl group, and alkyldicycloalkylsilyls, which are substituted with one alkyl group and two cycloalkyl groups. Specific examples of the alkyl and cycloalkyl groups are as described above.

[0221] In addition, hydrogen in the chemical structure of the anthracene compound represented by formula (H3) may be substituted with a group represented by formula (A) above. When substituted with a group represented by formula (A), the group represented by formula (A) replaces at least one hydrogen in the compound represented by formula (H3) at the *.

[0222] The group represented by formula (A) is one of the substituents that the anthracene compound represented by formula (H3) may have. [ka]

[0223] In the above formula (A), Y is -O-, -S- or >NR 29 and R 21 ~R 28 are each independently hydrogen, optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted alkoxy, optionally substituted aryloxy, optionally substituted arylthio, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, alkyldicycloalkylsilyl, optionally substituted amino, halogen, hydroxy or cyano; R 21 ~R 28 adjacent groups among R may be bonded to each other to form a hydrocarbon ring, an aryl ring, or a heteroaryl ring; 29 is hydrogen or optionally substituted aryl.

[0224] R 21 ~R 28The "alkyl" in the "optionally substituted alkyl" may be either linear or branched, and examples thereof include linear alkyl having 1 to 24 carbon atoms or branched alkyl having 3 to 24 carbon atoms. An alkyl having 1 to 18 carbon atoms (branched alkyl having 3 to 18 carbon atoms) is preferred, an alkyl having 1 to 12 carbon atoms (branched alkyl having 3 to 12 carbon atoms) is more preferred, an alkyl having 1 to 6 carbon atoms (branched alkyl having 3 to 6 carbon atoms) is even more preferred, and an alkyl having 1 to 4 carbon atoms (branched alkyl having 3 to 4 carbon atoms) is particularly preferred.

[0225] 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.

[0226] R 21 ~R 28 Examples of the "cycloalkyl" in the "optionally substituted cycloalkyl" include cycloalkyl having 3 to 24 carbon atoms, cycloalkyl having 3 to 20 carbon atoms, cycloalkyl having 3 to 16 carbon atoms, cycloalkyl having 3 to 14 carbon atoms, cycloalkyl having 5 to 10 carbon atoms, cycloalkyl having 5 to 8 carbon atoms, cycloalkyl having 5 to 6 carbon atoms, and cycloalkyl having 5 carbon atoms.

[0227] Specific examples of "cycloalkyl" include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, and alkyl (especially methyl) substituted derivatives of these having 1 to 4 carbon atoms, as well as norbornenyl, bicyclo[1.0.1]butyl, bicyclo[1.1.1]pentyl, bicyclo[2.0.1]pentyl, bicyclo[1.2.1]hexyl, bicyclo[3.0.1]hexyl, bicyclo[2.1.2]heptyl, bicyclo[2.2.2]octyl, adamantyl, diamantyl, decahydronaphthalenyl, and decahydroazulenyl.

[0228] R 21 ~R 28 In the above, the "aryl" in the "optionally substituted aryl" includes, for example, aryl having 6 to 30 carbon atoms, preferably aryl having 6 to 16 carbon atoms, more preferably aryl having 6 to 12 carbon atoms, and particularly preferably aryl having 6 to 10 carbon atoms.

[0229] Specific examples of "aryl" include a monocyclic ring system such as phenyl, a bicyclic ring system such as biphenylyl, a fused bicyclic ring system such as naphthyl, a tricyclic ring system such as terphenylyl (m-terphenylyl, o-terphenylyl, p-terphenylyl), a fused tricyclic ring system such as acenaphthylenyl, fluorenyl, phenalenyl, and phenanthrenyl, a fused tetracyclic ring system such as triphenylenyl, pyrenyl, and naphthacenyl, and a fused pentacyclic ring system such as perylenyl and pentacenyl.

[0230] R 21 ~R 28 Examples of the "heteroaryl" in the "optionally substituted heteroaryl" include heteroaryl having 2 to 30 carbon atoms, preferably heteroaryl having 2 to 25 carbon atoms, more preferably heteroaryl having 2 to 20 carbon atoms, further preferably heteroaryl having 2 to 15 carbon atoms, and particularly preferably heteroaryl having 2 to 10 carbon atoms. Examples of the heteroaryl include heterocycles containing, as ring-constituting atoms other than carbon, 1 to 5 heteroatoms selected from oxygen, sulfur, and nitrogen.

[0231] Specific examples of "heteroaryl" include pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, oxadiazolyl, thiadiazolyl, triazolyl, tetrazolyl, pyrazolyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, indolyl, isoindolyl, 1H-indazolyl, benzimidazolyl, benzoxazolyl, benzothiazolyl, 1H-benzotriazolyl, quinolyl, isoquinolyl, cyclohex ... Examples of such aryl groups include aryl, aryloxy, aryloxy, aryloxy, and aryloxy groups. Examples of such aryl groups include aryloxy, aryloxy, aryloxy, and aryloxy groups include aryloxy, aryloxy, and aryloxy groups. Examples of such aryl groups include aryloxy, aryloxy, and aryloxy groups include aryloxy, aryloxy, and aryloxy groups. Examples of such aryl groups include aryloxy, aryloxy, and aryloxy groups include aryloxy, aryloxy, and aryloxy groups.

[0232] R 21 ~R 28 Examples of the "alkoxy" in the "optionally substituted alkoxy" include linear alkoxy having 1 to 24 carbon atoms or branched alkoxy having 3 to 24 carbon atoms. An alkoxy having 1 to 18 carbon atoms (branched alkoxy having 3 to 18 carbon atoms) is preferred, an alkoxy having 1 to 12 carbon atoms (branched alkoxy having 3 to 12 carbon atoms) is more preferred, an alkoxy having 1 to 6 carbon atoms (branched alkoxy having 3 to 6 carbon atoms) is even more preferred, and an alkoxy having 1 to 4 carbon atoms (branched alkoxy having 3 to 4 carbon atoms) is particularly preferred.

[0233] Specific examples of "alkoxy" include methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, s-butoxy, t-butoxy, pentyloxy, hexyloxy, heptyloxy, octyloxy, and the like.

[0234] R 21 ~R 28The "aryloxy" in the "optionally substituted aryloxy" is a group in which the hydrogen of the -OH group is replaced by an aryl, and this aryl is one of the above-mentioned R 21 ~R 28 The group described as "aryl" in the above formula can be used.

[0235] R 21 ~R 28 The "arylthio" in the "optionally substituted arylthio" is a group in which the hydrogen of the -SH group is replaced by an aryl, and this aryl is the same as R 21 ~R 28 The group described as "aryl" in the above formula can be used.

[0236] R 21 ~R 28 The "trialkylsilyl" in the above formula is a silyl group in which each of the three hydrogen atoms is independently replaced by an alkyl group, and the alkyl group is the same as R 21 ~R 28 The groups described as "alkyl" in the above can be cited. Preferred alkyl groups for substitution are alkyl groups having 1 to 4 carbon atoms, and specific examples thereof include methyl, ethyl, propyl, i-propyl, butyl, sec-butyl, t-butyl, and cyclobutyl.

[0237] Specific examples of the "trialkylsilyl" include trimethylsilyl, triethylsilyl, tripropylsilyl, tri-i-propylsilyl, tributylsilyl, tri-sec-butylsilyl, tri-t-butylsilyl, ethyldimethylsilyl, propyldimethylsilyl, i-propyldimethylsilyl, butyldimethylsilyl, sec-butyldimethylsilyl, t-butyldimethylsilyl, methyldiethylsilyl, propyldiethylsilyl, i-propyldiethylsilyl, butyldiethylsilyl, sec-butyldiethylsilyl, t-butyldiethylsilyl, methyldipropylsilyl, ethyldipropylsilyl, butyldipropylsilyl, sec-butyldipropylsilyl, t-butyldipropylsilyl, methyldi-i-propylsilyl, ethyldi-i-propylsilyl, butyldi-i-propylsilyl, sec-butyldi-i-propylsilyl, and t-butyldi-i-propylsilyl.

[0238] R 21 ~R 28 The "tricycloalkylsilyl" in the above formula is a silyl group in which each of the three hydrogen atoms is independently replaced by a cycloalkyl, and the cycloalkyl is the same as R 21 ~R 28 The groups described as "cycloalkyl" in the above can be cited. Preferred cycloalkyl for substitution is cycloalkyl having 5 to 10 carbon atoms, and specific examples thereof include cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, bicyclo[1.1.1]pentyl, bicyclo[2.0.1]pentyl, bicyclo[1.2.1]hexyl, bicyclo[3.0.1]hexyl, bicyclo[2.1.2]heptyl, bicyclo[2.2.2]octyl, adamantyl, decahydronaphthalenyl, and decahydroazulenyl.

[0239] Specific examples of the "tricycloalkylsilyl" include tricyclopentylsilyl, tricyclohexylsilyl, and the like.

[0240] 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.

[0241] R 21 ~R 28 The "substituted amino" in the "optionally substituted amino" in the above is, for example, an amino group in which two hydrogen atoms are substituted with aryl or heteroaryl. An amino group in which two hydrogen atoms are substituted with aryl is a diaryl-substituted amino, an amino group in which two hydrogen atoms are substituted with heteroaryl is a diheteroaryl-substituted amino, and an amino group in which two hydrogen atoms are substituted with an aryl and a heteroaryl is an arylheteroaryl-substituted amino. The aryl and heteroaryl are as defined above in R 21 ~R 28 The groups described above as "aryl" and "heteroaryl" can be cited.

[0242] Specific examples of the "substituted amino" include diphenylamino, dinaphthylamino, phenylnaphthylamino, dipyridylamino, phenylpyridylamino, naphthylpyridylamino, and the like.

[0243] R 21 ~R 28 "Halogen" in the above formula includes fluorine, chlorine, bromine, and iodine.

[0244] R 21 ~R 28 Some of the groups described as may be substituted as described above, in which case the substituents include alkyl, cycloalkyl, aryl, or heteroaryl. The alkyl, cycloalkyl, aryl, or heteroaryl may be any of the groups described above as R 21 ~R 28 In the above, reference can be made to a group described as "alkyl", "cycloalkyl", "aryl" or "heteroaryl".

[0245] Y as 'NR' 29 " R in 29 is hydrogen or an optionally substituted aryl, and the aryl is as defined above in R 21 ~R 28 The group described as "aryl" in the above formula can be cited, and the substituents thereof include R 21 ~R 28 The groups described above as substituents for the above can be cited.

[0246] R 21 ~R 28 Among these, adjacent groups may be bonded to each other to form a hydrocarbon ring, an aryl ring, or a heteroaryl ring. The group represented by the following formula (A-1) does not form a ring, and the group represented by the following formulas (A-2) to (A-14) may be exemplified as the group formed with a ring. At least one hydrogen atom in the group represented by any of formulas (A-1) to (A-14) may be substituted with alkyl, cycloalkyl, aryl, heteroaryl, alkoxy, aryloxy, arylthio, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, alkyldicycloalkylsilyl, diaryl-substituted amino, diheteroaryl-substituted amino, arylheteroaryl-substituted amino, halogen, hydroxy, or cyano.

[0247] [ka]

[0248] Examples of rings formed by bonding adjacent groups to each other include a hydrocarbon ring such as a cyclohexane ring, and examples of aryl and heteroaryl rings include the above-mentioned R 21 ~R 28 Examples of the ring structures include those described for "aryl" and "heteroaryl" in the above formula (A-1), and these rings are formed so as to be condensed with one or two benzene rings in the above formula (A-1).

[0249] Examples of the group represented by formula (A) include groups represented by any of the above formulas (A-1) to (A-14). Groups represented by any of the above formulas (A-1) to (A-5) and (A-12) to (A-14) are preferred. Groups represented by any of the above formulas (A-1) to (A-4) are more preferred. Groups represented by any of the above formulas (A-1), (A-3) and (A-4) are even more preferred. Groups represented by the above formula (A-1) are particularly preferred.

[0250] The group represented by formula (A) is a naphthalene ring in formula (3-X1) or formula (3-X2), a single bond in formula (3-X3), Ar in formula (3-X3), 3 As described above, the naphthalene ring in formula (3-X1) or formula (3-X2), the single bond in formula (3-X3), and / or Ar in formula (3-X3) are substituted with at least one hydrogen atom in the compound represented by formula (H3). 3 The form in which it is bound to is preferred.

[0251] In addition, in the structure of the group represented by formula (A), a naphthalene ring in formula (3-X1) or formula (3-X2), a single bond in formula (3-X3), Ar in formula (3-X3), 3 The position at which R is bonded, and the position at which at least one hydrogen atom in the compound represented by formula (H3) is substituted in the structure of the group represented by formula (A), may be any position in the structure of formula (A), and may be, for example, any of the two benzene rings in the structure of formula (A) or R 21 ~R 28 Any of the rings formed by bonding adjacent groups to each other, or ">NR 29 " R in 29 The bond can be at any position within the

[0252] Examples of the group represented by formula (A) include the following groups: In the formula, Y and * are defined as above. [ka]

[0253] All or a part of the hydrogen atoms in the chemical structure of the anthracene compound represented by formula (H3) may be deuterium atoms.

[0254] Specific examples of the anthracene-based compound include compounds represented by the following formulae (H3-1) to (H3-72): In the following structural formulae, "Me" represents methyl, "D" represents deuterium, and "tBu" represents t-butyl.

[0255] [ka]

[0256] [ka]

[0257] [ka]

[0258] [ka]

[0259] The anthracene compound represented by formula (H3) is a compound having a reactive group at a desired position of an anthracene skeleton, and X, Ar 4 The compound having a reactive group in a partial structure such as the structure of formula (A) can be used as a starting material to produce the compound by applying Suzuki coupling, Negishi coupling, or other known coupling reactions. Examples of reactive groups in these reactive compounds include halogens and boronic acids. As a specific production method, for example, the synthesis methods in paragraphs

[0089] to

[0175] of International Publication No. 2014 / 141725 can be used as a reference.

[0260] <Fluorene-based compounds> The compound represented by formula (H4) basically functions as a host. [ka]

[0261] In the above formula (H4), R 1 From R 10 are each independently a hydrogen atom, an aryl atom, a heteroaryl atom (wherein the heteroaryl atom may be bonded to the fluorene skeleton in the above formula (H4) via a linking group), a diarylamino atom, a diheteroarylamino atom, an arylheteroarylamino atom, an alkyl atom, a cycloalkyl atom, an alkenyl atom, an alkoxy atom, or an aryloxy atom, in which at least one hydrogen atom may be substituted with an aryl atom, a heteroaryl atom, an alkyl atom, or a cycloalkyl atom; Also, R 1 and R 2 , R 2 and R 3 , R 3 and R 4 , R 5 and R 6 , R 6 and R 7 , R 7 and R 8 or R 9 and R 10 may each independently bond to form a fused ring or a spiro ring, at least one hydrogen in the formed ring may be replaced with an aryl, a heteroaryl (the heteroaryl may be bonded to the formed ring via a linking group), a diarylamino, a diheteroarylamino, an arylheteroarylamino, an alkyl, a cycloalkyl, an alkenyl, an alkoxy, or an aryloxy, at least one hydrogen in these may be replaced with an aryl, a heteroaryl, an alkyl, or a cycloalkyl, and At least one hydrogen in the compound represented by formula (H4) may be substituted with halogen, cyano or deuterium.

[0262] For details of each group in the definition of the above formula (H4), the explanation for the polycyclic aromatic compound of the above formula (1) can be cited.

[0263] R 1 From R 10 Examples of the alkenyl in the above formula include alkenyl having 2 to 30 carbon atoms, preferably alkenyl having 2 to 20 carbon atoms, more preferably alkenyl having 2 to 10 carbon atoms, further preferably alkenyl having 2 to 6 carbon atoms, and particularly preferably alkenyl having 2 to 4 carbon atoms. Preferred alkenyls are vinyl, 1-propenyl, 2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, or 5-hexenyl.

[0264] Specific examples of heteroaryl include monovalent groups represented by removing any one hydrogen atom from a compound of the following formula (4-Ar1), formula (4-Ar2), formula (4-Ar3), formula (4-Ar4), or formula (4-Ar5). [ka] In formulas (4-Ar1) to (4-Ar5), Y 1 are each independently O, S or NR, R is phenyl, biphenylyl, naphthyl, anthracenyl or hydrogen; At least one hydrogen atom in the structures of the above formulae (4-Ar1) to (4-Ar5) may be substituted with phenyl, biphenylyl, naphthyl, anthracenyl, phenanthrenyl, methyl, ethyl, propyl, or butyl.

[0265] These heteroaryls may be bonded to the fluorene skeleton in the above formula (H4) via a linking group. That is, the fluorene skeleton in the formula (H4) and the above heteroaryls may be bonded directly, or may be bonded to each other via a linking group. Examples of the linking group include phenylene, biphenylene, naphthylene, anthracenylene, methylene, ethylene, -OCH2CH2-, -CH2CH2O-, or -OCH2CH2O-.

[0266] In addition, R in formula (H4) 1 and R 2 , R 2 and R 3 , R 3 and R 4 , R 5 and R 6 , R 6 and R 7 or R 7 and R 8 are each independently bonded to form a fused ring, R 9 and R 10 may be bonded to form a spiro ring. 1 From R 8 The fused ring formed by is a ring fused to the benzene ring in formula (H4), and is an aliphatic ring or an aromatic ring. An aromatic ring is preferable, and examples of the structure including the benzene ring in formula (H4) include a naphthalene ring and a phenanthrene ring. 9 and R 10 The spiro ring formed by the formula (H4) is a ring that is spiro-bonded to the five-membered ring in formula (H4), and is an aliphatic ring or an aromatic ring. An aromatic ring, such as a fluorene ring, is preferred.

[0267] The compound represented by formula (H4) is preferably a compound represented by the following formula (4-1), formula (4-2) or formula (4-3), 1 and R 2 A compound having a condensed benzene ring formed by bonding with 3 and R 4 A compound having a condensed benzene ring formed by bonding with1 From R 8 is a compound in which none of the above is bound.

[0268] [ka]

[0269] R in formula (4-1), formula (4-2) and formula (4-3) 1 From R 10 The definition of R in formula (H4) corresponds to 1 From R 10 is the same as R in formula (4-1) and formula (4-2). 11 From R 14 The definition of R in formula (H4) 1 From R 10 is the same as:

[0270] The compound represented by formula (H4) is more preferably a compound represented by the following formula (4-1A), formula (4-2A) or formula (4-3A), in which R 9 and R 10 is a compound in which a spiro-fluorene ring is formed by bonding.

[0271] [ka]

[0272] R in formula (4-1A), formula (4-2A) and formula (4-3A) 2 From R 7 The definition of is the corresponding R in formula (4-1), formula (4-2) and formula (4-3). 2 From R 7 and R in formula (4-1A) and formula (4-2A) 11 From R 14 The definition of R in formula (4-1) and formula (4-2) 11 From R 14 is the same as:

[0273] In addition, all or a part of the hydrogen atoms in the compound represented by formula (H4) may be substituted with halogen, cyano or deuterium.

[0274] <Dibenzochrysene compounds> The dibenzochrysene compound as the host is, for example, a compound represented by the following formula (H5).

[0275] [ka]

[0276] In the above formula (H5), R 1 From R 16 each independently represents a hydrogen atom, an aryl, a heteroaryl (wherein the heteroaryl may be bonded to the dibenzochrysene skeleton in the above formula (H5) via a linking group), a diarylamino, a diheteroarylamino, an arylheteroarylamino, an alkyl, a cycloalkyl, an alkenyl, an alkoxy, or an aryloxy, in which at least one hydrogen atom may be substituted with an aryl, a heteroaryl, an alkyl, or a cycloalkyl; Also, R 1 From R 16 adjacent groups among these may be bonded to each other to form a condensed ring, at least one hydrogen atom in the formed ring may be substituted with an aryl, a heteroaryl (the heteroaryl may be bonded to the formed ring via a linking group), a diarylamino, a diheteroarylamino, an arylheteroarylamino, an alkyl, a cycloalkyl, an alkenyl, an alkoxy, or an aryloxy, at least one hydrogen atom in these may be substituted with an aryl, a heteroaryl, an alkyl, or a cycloalkyl, and At least one hydrogen in the compound represented by formula (H5) may be substituted with halogen, cyano or deuterium.

[0277] For details of each group in the definition of the above formula (5), the explanation for the polycyclic aromatic compound of the above formula (1) can be cited.

[0278] The alkenyl in the definition of the above formula (H5) is, for example, an alkenyl having 2 to 30 carbon atoms, preferably an alkenyl having 2 to 20 carbon atoms, more preferably an alkenyl having 2 to 10 carbon atoms, further preferably an alkenyl having 2 to 6 carbon atoms, and particularly preferably an alkenyl having 2 to 4 carbon atoms. Preferred alkenyls are vinyl, 1-propenyl, 2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, or 5-hexenyl.

[0279] Specific examples of heteroaryl include monovalent groups represented by removing any one hydrogen atom from a compound of the following formula (5-Ar1), formula (5-Ar2), formula (5-Ar3), formula (5-Ar4), or formula (5-Ar5).

[0280] [ka]

[0281] In formula (5-Ar1) to formula (5-Ar5), Y 1 are each independently O, S or NR, R is phenyl, biphenylyl, naphthyl, anthracenyl or hydrogen; At least one hydrogen atom in the structures of the above formulae (5-Ar1) to (5-Ar5) may be substituted with phenyl, biphenylyl, naphthyl, anthracenyl, phenanthrenyl, methyl, ethyl, propyl, or butyl.

[0282] These heteroaryls may be bonded to the dibenzochrysene skeleton in the above formula (H5) via a linking group. That is, the dibenzochrysene skeleton and the above heteroaryls in the formula (H5) may be bonded directly, or may be bonded to each other via a linking group. Examples of the linking group include phenylene, biphenylene, naphthylene, anthracenylene, methylene, ethylene, -OCH2CH2-, -CH2CH2O-, or -OCH2CH2O-.

[0283] The compound represented by formula (H5) is preferably R 1 , R 4 , R 5 , R 8 , R 9 , R 12 , R 13 and R 16 is hydrogen. In this case, R in formula (H5) 2 , R 3 , R 6 , R 7 , R 10 , R 11 , R 14 and R 15 are preferably each independently hydrogen, phenyl, biphenylyl, naphthyl, anthracenyl, phenanthrenyl, a monovalent group having the structure of the above formula (5-Ar1), (5-Ar2), (5-Ar3), (5-Ar4) or (5-Ar5) (the monovalent group having the structure may be bonded to the dibenzochrysene skeleton in the above formula (H5) via phenylene, biphenylene, naphthylene, anthracenylene, methylene, ethylene, -OCHCH-, -CHCHO- or -OCHCHO-), methyl, ethyl, propyl or butyl.

[0284] The compound represented by formula (H5) is more preferably 1 , R 2 , R 4 , R 5 , R 7 , R 8 , R 9 , R 10 , R 12 , R13 , R 15 and R 16 is hydrogen. In this case, R in formula (H5) 3 , R 6 , R 11 and R 14 at least one (preferably one or two, more preferably one) of the formulae (5-Ar1), (5-Ar2), (5-Ar3), (5-Ar4) or (5-Ar5) is a monovalent group having a structure represented by the formula (5-Ar1), (5-Ar2), (5-Ar3), (5-Ar4) or (5-Ar5) via a single bond, phenylene, biphenylene, naphthylene, anthracenylene, methylene, ethylene, -OCHCH-, -CHCHO-, or -OCHCHO-; The other than the at least one (i.e., other than the position substituted by the monovalent group having the structure) is hydrogen, phenyl, biphenylyl, naphthyl, anthracenyl, methyl, ethyl, propyl, or butyl, and at least one hydrogen in these may be substituted with phenyl, biphenylyl, naphthyl, anthracenyl, methyl, ethyl, propyl, or butyl.

[0285] In addition, R in formula (H5) 2 , R 3 , R 6 , R 7 , R 10 , R 11 , R 14 and R 15 When a monovalent group having a structure represented by the above formula (5-Ar1) to formula (5-Ar5) is selected as the aryl group, at least one hydrogen atom in the structure is R 1 From R 16 may be bonded to any one of the following to form a single bond.

[0286] The above-mentioned light-emitting layer materials (host material and dopant material) can be used as light-emitting layer materials as polymer compounds obtained by polymerizing a reactive compound substituted with a reactive substituent as a monomer, or as crosslinked polymers thereof, or as pendant polymer compounds obtained by reacting a main chain polymer with the reactive compound, or as crosslinked pendant polymers thereof. In this case, the explanation of the polycyclic aromatic compound represented by formula (1) can be cited as the reactive substituent. The applications of such polymer compounds and crosslinked polymers will be described in detail below.

[0287] <Example of polymer host material> [ka]

[0288] In formula (SPH-1), Each MU is independently a divalent aromatic compound, each EC is independently a monovalent aromatic compound, two hydrogens in MU are replaced by EC or MU, and k is an integer of 2 to 50,000.

[0289] 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.

[0290] At least one hydrogen atom in MU and EC in formula (SPH-1) may be substituted with an alkyl group having 1 to 24 carbon atoms, a cycloalkyl group having 3 to 24 carbon atoms, a halogen atom or a deuterium atom; 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 (SPH-1) 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.

[0291] Examples of MU include a divalent group represented by removing any two hydrogen atoms from any of the following compounds:

[0292] [ka]

[0293] More specifically, the divalent group may be any of the following structures: In these, MU bonds to another MU or EC at *.

[0294] [ka]

[0295] [ka]

[0296] [ka]

[0297] [ka]

[0298] [ka]

[0299] [ka]

[0300] Examples of EC include a monovalent group represented by any of the following structures: In these, EC is bonded to MU at *.

[0301] [ka]

[0302] [ka]

[0303] From the viewpoint of solubility and coating film-forming property, the compound represented by formula (SPH-1) is preferably such that 10 to 100% of the total number of MUs (k) in the molecule have an alkyl having 1 to 24 carbon atoms, more preferably 30 to 100% of the total number of MUs (k) in the molecule have an alkyl having 1 to 18 carbon atoms (branched chain alkyl having 3 to 18 carbon atoms), and even more preferably 50 to 100% of the total number of MUs (k) in the molecule have an alkyl having 1 to 12 carbon atoms (branched chain alkyl having 3 to 12 carbon atoms). On the other hand, from the viewpoint of in-plane 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 7 to 24 carbon atoms, and more preferably 30 to 100% of the total number of MUs (k) in the molecule have an alkyl having 7 to 24 carbon atoms (branched chain alkyl having 7 to 24 carbon atoms). The applications of such polymer compounds and crosslinked polymers will be described in detail below.

[0304] <<Assisting dopant>> The light-emitting layer may further contain an assisting dopant. In this case, the compound of the present invention functions as the emitting dopant. Examples of the assisting dopant include the following compounds. In the following formula, Me represents methyl, tBu represents t-butyl, Ph represents phenyl, and the wavy line represents a bonding position.

[0305] [ka]

[0306] [ka]

[0307] [ka]

[0308] [ka]

[0309] [ka]

[0310] [ka]

[0311] [ka]

[0312] [ka]

[0313] [ka]

[0314] 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.

[0315] The electron injection / transport layer is a layer that is responsible for injecting electrons from the cathode and transporting the electrons. It is desirable that the electron injection efficiency is high and that the injected electrons are efficiently transported. For this purpose, it is preferable that the material has a large electron affinity, a large electron mobility, and excellent stability, and impurities that become traps are unlikely to occur during manufacture and use. However, when considering the balance of transport of holes and electrons, if the material mainly plays a role of efficiently preventing holes from flowing from the anode to the cathode without recombining, even if the electron transport ability is not so high, it has the effect of improving the luminous efficiency equivalent to a material with a high electron transport ability. Therefore, the electron injection / transport layer in this embodiment may also include the function of a layer that can efficiently block the movement of holes.

[0316] The material (electron transport material) for forming the electron transport layer 106 or the electron injection layer 107 can be arbitrarily selected from compounds conventionally used as electron transport compounds in photoconductive materials and known compounds used in the electron injection layer and electron transport layer of organic EL elements.

[0317] Materials used in the electron transport layer or electron injection layer preferably contain at least one selected from compounds consisting of aromatic rings or heteroaromatic rings composed of one or more atoms selected from carbon, hydrogen, oxygen, sulfur, silicon, and phosphorus, pyrrole derivatives and their condensed ring derivatives, and metal complexes having electron-accepting nitrogen. Specific examples include condensed ring aromatic ring derivatives such as naphthalene and anthracene, styryl aromatic ring derivatives such as 4,4'-bis(diphenylethenyl)biphenyl, perinone derivatives, coumarin derivatives, naphthalimide derivatives, quinone derivatives such as anthraquinone and diphenoquinone, phosphorus oxide derivatives, 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 can be used alone or in combination with different materials.

[0318] 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.

[0319] Furthermore, metal complexes having an electron-accepting nitrogen atom can also be used, and examples thereof include hydroxyazole complexes such as quinolinol metal complexes and hydroxyphenyloxazole complexes, azomethine complexes, tropolone metal complexes, flavonol metal complexes, and benzoquinoline metal complexes.

[0320] The above-mentioned materials may be used alone or in combination with different materials.

[0321] 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.

[0322] <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]

[0323] 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.

[0324] 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.

[0325] [ka]

[0326] In formula (ETM-1-1), 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 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.

[0327] [ka]

[0328] 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 1is 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.

[0329] X 1 Specific 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.

[0330] Specific examples of the borane derivative include the following compounds: [ka]

[0331] The borane derivative can be produced using known raw materials and known synthesis methods.

[0332] <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]

[0333] 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.

[0334] In formula (ETM-2-1), R 11 ~R18 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).

[0335] In formula (ETM-2-2), R 11 and R 12 are each independently hydrogen, alkyl (preferably alkyl having 1 to 24 carbon atoms), cycloalkyl (preferably cycloalkyl having 3 to 12 carbon atoms) or aryl (preferably aryl having 6 to 30 carbon atoms); R 11 and R 12 may be bonded to form a ring.

[0336] 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.

[0337] [ka]

[0338] 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]

[0339] 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.

[0340] R 11 ~R 18 The "alkyl" in the above may be either linear or branched, and examples thereof include linear alkyl having 1 to 24 carbon atoms or branched alkyl having 3 to 24 carbon atoms. A preferred "alkyl" is an alkyl having 1 to 18 carbon atoms (branched alkyl having 3 to 18 carbon atoms). A more preferred "alkyl" is an alkyl having 1 to 12 carbon atoms (branched alkyl having 3 to 12 carbon atoms). An even more preferred "alkyl" is an alkyl having 1 to 6 carbon atoms (branched alkyl having 3 to 6 carbon atoms). An especially preferred "alkyl" is an alkyl having 1 to 4 carbon atoms (branched alkyl having 3 to 4 carbon atoms).

[0341] 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.

[0342] 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.

[0343] R 11 ~R 18In 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.

[0344] 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.

[0345] 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.

[0346] 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.

[0347] R in formula (ETM-2-2) 11 and R 12 may combine to form a ring. As a result, a cyclobutane, cyclopentane, cyclopentene, cyclopentadiene, cyclohexane, fluorene, indene, etc. may be spiro-bonded to the 5-membered ring of the fluorene skeleton.

[0348] Specific examples of this pyridine derivative include, for example, the following compounds. [Chemical formula]

[0349] This pyridine derivative can be produced using known raw materials and known synthesis methods.

[0350] [Fluoranthene derivative] The fluoranthene derivative is a compound represented by, for example, the following formula (ETM-3), and is specifically disclosed in International Publication No. 2010 / 134352. [Chemical formula]

[0351] 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 substituted include aryl, heteroaryl, alkyl or cycloalkyl, etc.

[0352] Specific examples of this fluoranthene derivative include, for example, the following compounds. [Chemical formula]

[0353] [BO-based derivative] The BO derivative is, for example, a polycyclic aromatic compound represented by the following formula (ETM-4), or a polymer of a polycyclic aromatic compound having a plurality of structures represented by the following formula (ETM-4). [ka]

[0354] 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.

[0355] 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.

[0356] In addition, at least one hydrogen in the compound or structure represented by formula (ETM-4) may be substituted with a halogen or deuterium.

[0357] 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 formula (1) or formula (1-a) etc. can be cited.

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

[0359] The BO derivative can be produced using known raw materials and known synthesis methods.

[0360] <Anthracene derivatives> One of the anthracene derivatives is, for example, a compound represented by the following formula (ETM-5). [ka]

[0361] Ar 1 are each independently a single bond, or a divalent benzene, naphthalene, anthracene, fluorene, or phenalene.

[0362] 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.

[0363] 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.

[0364] 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.

[0365] 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.

[0366] Specific examples of these anthracene derivatives include the following compounds. [ka]

[0367] These anthracene derivatives can be produced using known raw materials and known synthesis methods.

[0368] <Benzofluorene derivatives> The benzofluorene derivative is, for example, a compound represented by the following formula (ETM-6). [ka]

[0369] 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.

[0370] 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.

[0371] 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.

[0372] 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.

[0373] 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.

[0374] Specific examples of the "aryl having 6 to 30 carbon atoms" include phenyl, naphthyl, acenaphthylenyl, fluorenyl, phenalenyl, phenanthryl, triphenylenyl, pyrenyl, naphthacenyl, perylenyl, and pentacenyl.

[0375] 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.

[0376] Specific examples of the benzofluorene derivative include the following compounds: [ka]

[0377] The benzofluorene derivative can be produced using known raw materials and known synthesis methods.

[0378] <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]

[0379] 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.

[0380] The phosphine oxide derivative may be, for example, a compound represented by the following formula (ETM-7-2). [ka]

[0381] R 1 ~R 3 may be the same or different and are selected from hydrogen, alkyl, cycloalkyl, aralkyl, alkenyl, cycloalkenyl, alkynyl, alkoxy, alkylthio, cycloalkylthio, aryl ether (aryl ether group), aryl thioether (aryl thioether group), aryl, heterocyclic group, halogen, cyano, aldehyde, carbonyl, carboxyl, amino, nitro, silyl, and a fused ring formed between adjacent substituents.

[0382] 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.

[0383] 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.

[0384] 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.

[0385] 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.

[0386] 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.

[0387] Moreover, cycloalkenyl refers to an unsaturated alicyclic hydrocarbon group containing a double bond, such as cyclopentenyl, cyclopentadienyl, cyclohexene, etc., which may be unsubstituted or substituted.

[0388] 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.

[0389] 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.

[0390] Moreover, alkylthio is a group in which the oxygen atom of the ether bond of alkoxy is replaced with a sulfur atom.

[0391] Moreover, cycloalkylthio is a group in which the oxygen atom of the ether bond of cycloalkoxy is replaced with a sulfur atom.

[0392] 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.

[0393] 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.

[0394] The aryl group refers to an aromatic hydrocarbon group such as phenyl, naphthyl, biphenylyl, phenanthryl, terphenylyl, and pyrenyl. The aryl group may be unsubstituted or substituted. The number of carbon atoms in the aryl group is not particularly limited, but is usually in the range of 6 to 40.

[0395] The heterocyclic group refers to a cyclic structure group having atoms other than carbon, such as furanyl, thiophenyl, 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.

[0396] Halogen refers to fluorine, chlorine, bromine and iodine.

[0397] The aldehyde, carbonyl and amino groups may also include groups substituted with aliphatic hydrocarbons, alicyclic hydrocarbons, aromatic hydrocarbons, heterocycles and the like.

[0398] Furthermore, the aliphatic hydrocarbons, alicyclic hydrocarbons, aromatic hydrocarbons and heterocycles may be either unsubstituted or substituted.

[0399] 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.

[0400] 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.

[0401] Specific examples of the phosphine oxide derivative include the following compounds: [ka]

[0402] The phosphine oxide derivative can be produced using known raw materials and known synthesis methods.

[0403] <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]

[0404] 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.

[0405] 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.

[0406] 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.

[0407] 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.

[0408] 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.

[0409] The above aryl and heteroaryl may be substituted, for example, by the above aryl or heteroaryl, respectively.

[0410] Specific examples of the pyrimidine derivative include the following compounds: [ka]

[0411] The pyrimidine derivative can be produced using known raw materials and known synthesis methods.

[0412] <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]

[0413] Ar niFrom the viewpoint of fast electron transport property, it is preferable that the number of carbon atoms is large, and from the viewpoint of high T1, it is preferable that the number of carbon atoms is small. ni Specifically, it is preferable that the aryl group has a high T1 when used in a layer adjacent to the light-emitting layer, and is an aryl group having 6 to 20 carbon atoms, preferably an aryl group having 6 to 14 carbon atoms, and more preferably an aryl group having 6 to 10 carbon atoms. In addition, the number of nitrile group substitutions, n, is preferably large from the viewpoint of high T1, and is preferably small from the viewpoint of high S1. Specifically, the number of nitrile group substitutions, n, is an integer of 1 to 4, preferably an integer of 1 to 3, more preferably an integer of 1 to 2, and even more preferably 1.

[0414] Each Ar is independently an aryl which may be substituted or a heteroaryl which may be substituted. From the viewpoint of high S1 and high T1, it is preferable that the heteroaryl has donor properties, and it is preferable that the heteroaryl has few donor properties because it is used as an electron transport layer. From the viewpoint of charge transportability, it is preferable that the aryl or heteroaryl has many 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.

[0415] 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.

[0416] 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.

[0417] 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.

[0418] 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.

[0419] The above aryl and heteroaryl may be substituted, for example, by the above aryl or heteroaryl, respectively.

[0420] 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.

[0421] Specific examples of the arylnitrile derivative include the following compounds: [ka]

[0422] The arylnitrile derivatives can be produced using known raw materials and known synthesis methods.

[0423] <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]

[0424] 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.

[0425] 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.

[0426] 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.

[0427] 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.

[0428] 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.

[0429] The above aryl and heteroaryl may be substituted, for example, by the above aryl or heteroaryl, respectively.

[0430] Specific examples of the triazine derivative include the following compounds: [ka]

[0431] The triazine derivative can be produced using known raw materials and known synthesis methods.

[0432] <Benzimidazole derivatives> The benzimidazole derivative is, for example, a compound represented by the following formula (ETM-11). [ka]

[0433] 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. [ka]

[0434] 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.

[0435] 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 18 At 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.

[0436] Specific examples of the benzimidazole derivative include 1-phenyl-2-(4-(10-phenylanthracen-9-yl)phenyl)-1H-benzo[d]imidazole, 2-(4-(10-(naphthalen-2-yl)anthracen-9-yl)phenyl)-1-phenyl-1H-benzo[d]imidazole, 2-(3-(10-(naphthalen-2-yl)anthracen-9-yl)phenyl)-1-phenyl-1H-benzo[d]imidazole, and 5-(10-(naphthalen-2-yl)anthracen-9-yl)-1,2-diphenyl-1H-benzo[d]imidazole. , 1-(4-(10-(naphthalene-2-yl)anthracen-9-yl)phenyl)-2-phenyl-1H-benzo[d]imidazole, 2-(4-(9,10-di(naphthalene-2-yl)anthracen-2-yl)phenyl)-1-phenyl-1H-benzo[d]imidazole, 1-(4-(9,10-di(naphthalene-2-yl)anthracen-2-yl)phenyl)-2-phenyl-1H-benzo[d]imidazole, 5-(9,10-di(naphthalene-2-yl)anthracen-2-yl)-1,2-diphenyl-1H-benzo[d]imidazole, and the like. [ka]

[0437] The benzimidazole derivative can be produced using known raw materials and known synthesis methods.

[0438] <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]

[0439] 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.

[0440] R of each formula 11 ~R 18 are each independently hydrogen, alkyl (preferably alkyl having 1 to 24 carbon atoms), cycloalkyl (preferably cycloalkyl having 3 to 12 carbon atoms), or aryl (preferably aryl having 6 to 30 carbon atoms). 11 ~R 18 Either one of the rings is bonded to φ, which is an aryl ring.

[0441] At least one hydrogen atom in each of the phenanthroline derivatives may be replaced with deuterium.

[0442] 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. [ka]

[0443] 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]

[0444] The phenanthroline derivative can be produced using known raw materials and known synthesis methods.

[0445] <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.

[0446] 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.

[0447] The quinolinol metal complex can be produced using known raw materials and known synthesis methods.

[0448] <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]

[0449] 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. [ka]

[0450] 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), 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 above 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.

[0451] These thiazole or benzothiazole derivatives can be produced using known raw materials and known synthesis methods.

[0452] <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]

[0453] 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 (1) and formula (1-a) and the like, 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 explanation in formula (ETM-7-2) can be cited. In addition, X and Y may be bonded to form a cycloalkyl ring (or a ring in which a part of the ring is unsaturated), and for details of this cycloalkyl ring, the explanation of cycloalkyl in formula (1) and formula (1-a) etc. can be referred to.

[0454] 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, isocyanate, thiocyanate, isothiocyanate, or cyano, which may be substituted with alkyl, cycloalkyl, aryl, or halogen, and may form a condensed ring with an adjacent substituent.

[0455] R 1 ~R 4 For details of halogen, alkyl, cycloalkyl, alkoxy, aryloxy, amino, aryl, heteroaryl, alkenyl and alkynyl in the formula (1) and the formula (1-a) can be cited.

[0456] 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 (1) and the formula (1-a) can be cited.

[0457] Examples of silyl include silyl and groups in which at least one of the three hydrogen atoms of silyl is independently substituted with an aryl, alkyl, or 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 (1) and formula (1-a) can be cited.

[0458] 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.

[0459] 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 If is Cyril, then 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.

[0460] These silole derivatives can be produced using known raw materials and known synthesis methods.

[0461] <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]

[0462] 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):

[0463] [ka]

[0464] In formula (L-1), X 1 ~X 6are 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.

[0465] Specific azoline derivatives are compounds represented by the following formula (ETM-16-1) or formula (ETM-16-2). [ka]

[0466] 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):

[0467] [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.

[0468] 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.

[0469] [ka]

[0470] [ka] [ka]

[0471] 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.

[0472] 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.

[0473] 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.

[0474] 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.

[0475] Specific examples of azoline derivatives include the following compounds: In the structural formula, "Me" represents methyl. [ka]

[0476] [ka]

[0477] 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:

[0478] [ka]

[0479] 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.

[0480] Other specific examples of azoline derivatives include the following compounds: In the structural formula, "Me" represents methyl. [ka]

[0481] For details of the alkyl, cycloalkyl, aryl or heteroaryl in the above formulas defining this azoline derivative, the explanations in formula (1) and formula (1-a) can be cited.

[0482] The azoline derivative can be produced using known raw materials and known synthesis methods.

[0483] <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.

[0484] 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.

[0485] <Other> The above-mentioned electron injection layer material and electron transport layer material can be used as an electron 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 explanation of the polycyclic aromatic compound represented by formula (1) can be cited as the reactive substituent. The applications of such polymer compounds and crosslinked polymers will be described in detail below.

[0486] 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 .

[0487] 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.

[0488] 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.

[0489] 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.

[0490] 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.

[0491] 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.

[0492] 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.

[0493] <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.

[0494] <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.

[0495] 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 form is called a spray method. The drying step includes air drying, heating, drying under reduced pressure, and the like. The drying step may be performed only once, or may be performed multiple times using different methods or conditions. In addition, different methods may be used in combination, such as baking under reduced pressure.

[0496] 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.

[0497] 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.

[0498] 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.

[0499] 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, if there is a means for preventing dissolution of the lower light-emitting layer, or if a means for forming a film from the cathode side is used in the opposite procedure to the above, a layer-forming composition containing a material for the electron transport layer and a material for the electron injection layer can be prepared and then the layer can be formed by a wet film formation method.

[0500] <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.

[0501] <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.

[0502] 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.

[0503] 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.

[0504] <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.

[0505] <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.

[0506] (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.

[0507] 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.

[0508] 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.

[0509] 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.

[0510] (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.

[0511] <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.

[0512] (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.

[0513] 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.

[0514] The binder used in the organic layer-forming composition may be of one type or a mixture of two or more types.

[0515] (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.

[0516] 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), fluoroalkylbenzenesulfonates, fluoroalkylcarboxylates, fluoroalkylpolyoxyethyleneethers, fluoroalkylammonium iodides, fluoroalkylbetaines, fluoroalkylsulfonates, diglycerol tetrakis (fluoroalkylpolyoxyethyleneether), fluoroalkyltrimethylammonium salts, fluoroalkylaminosulfonates, polyoxyethylene nonyl 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.

[0517] The surfactant may be used alone or in combination of two or more kinds.

[0518] <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.

[0519] 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.

[0520] 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.

[0521] 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).

[0522] 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.

[0523] <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). [ka] In formula (XLP-1), MUx, ECx, and k are defined the same as MU, EC, and k in the above formula (SPH-1), except 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 compound having a crosslinkable substituent is 0.1 to 80 mass% in the molecule.

[0524] 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 %.

[0525] 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]

[0526] L Y are each 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, and 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.

[0527] Examples of the divalent aromatic compound having a crosslinkable substituent include compounds having the following partial structures: [ka] [ka] [ka] [ka]

[0528] <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 (SPH-1) and the compound represented by the above formula (XLP-1). These compounds can be synthesized by appropriately combining known manufacturing methods.

[0529] 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.

[0530] 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.

[0531] The compound of formula (SPH-1) 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, and 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 carrying out the reaction in a state in which the monomer unit (MU) and the end cap unit (EC) are added to a reaction vessel. When the compound of formula (SPH-1) is synthesized in multiple steps, the target product is obtained by polymerizing the monomer unit (MU) to the target molecular weight, and then adding the end cap unit (EC) and reacting it. If different types of monomer units (MU) are added and reacted in multiple steps, a polymer having a concentration gradient in the structure of the monomer unit can be produced. After preparing a precursor polymer, the target polymer can be obtained by a subsequent reaction.

[0532] In addition, the primary structure of the polymer can be controlled by selecting the polymerizable group of the monomer unit (MU). 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 combination depending on the target object. Furthermore, by using a monomer unit having three or more polymerizable groups, it is possible to synthesize a hyperbranched polymer or a dendrimer.

[0533] [ka]

[0534] Examples of monomer units 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 / 14 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.

[0535] 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.

[0536] 3-1-10.Application examples of organic electroluminescent devices The organic EL element can also be applied to a display device having the organic EL element, a lighting device having the organic EL element, and the like. 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.

[0537] 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.

[0538] 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.

[0539] 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.

[0540] 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.

[0541] 3-2. Other organic devices The compound of the present invention can be used for producing the organic electroluminescent device described above, as well as an organic field effect transistor or an organic thin-film solar cell.

[0542] An organic field-effect transistor is a transistor that controls current by an electric field generated by voltage input, and has a gate electrode in addition to a source electrode and a drain electrode. When a voltage is applied to the gate electrode, an electric field is generated, and the flow of electrons (or holes) flowing between the source electrode and the drain electrode can be arbitrarily blocked to control the current. Field-effect transistors are easier to miniaturize than simple transistors (bipolar transistors), and are often used as elements that make up integrated circuits.

[0543] The structure of an organic field effect transistor is usually such that a source electrode and a drain electrode are provided in contact with an organic semiconductor active layer formed using the polycyclic aromatic compound according to the present invention, and a gate electrode is provided sandwiching an insulating layer (dielectric layer) in contact with the organic semiconductor active layer. Examples of the element structure include the following structure. (1) Substrate / gate electrode / insulating layer / source and drain electrodes / organic semiconductor active layer (2) Substrate / gate electrode / insulating layer / organic semiconductor active layer / source electrode and drain electrode (3) Substrate / organic semiconductor active layer / source electrode / drain electrode / insulator layer / gate electrode (4) Substrate / source electrode / drain electrode / organic semiconductor active layer / insulator layer / gate electrode The organic field effect transistor thus configured can be used as a pixel driving switching element for an active matrix driving type liquid crystal display or an organic electroluminescence display.

[0544] The organic thin-film solar cell has a structure in which an anode such as ITO, a hole transport layer, a photoelectric conversion layer, an electron transport layer, and a cathode are laminated on a transparent substrate such as glass. The photoelectric conversion layer has a p-type semiconductor layer on the anode side and an n-type semiconductor layer on the cathode side. The polycyclic aromatic compound according to the present invention can be used as a material for a hole transport layer, a p-type semiconductor layer, an n-type semiconductor layer, and an electron transport layer depending on its physical properties. The polycyclic aromatic compound according to the present invention can function as a hole transport material or an electron transport material in an organic thin-film solar cell. In addition to the above, the organic thin-film solar cell may appropriately include a hole blocking layer, an electron blocking layer, an electron injection layer, a hole injection layer, a smoothing layer, and the like. The organic thin-film solar cell can be used by appropriately selecting and combining known materials used in organic thin-film solar cells. EXAMPLES

[0545] The present invention will be described in detail below with reference to examples, but the present invention is not limited to these examples in any way.

[0546] Synthesis example (1): Compound (4-37) [ka]

[0547] [1st stage] 3-Bromodibenzo[b,d]furan[r-1] (24.7g, 100mmol), 2,6-dimethylaniline[r-2] (29.6g, 308mmol), cesium carbonate (65.1g), copper(I) chloride (0.99g) and xylene (200ml) were placed in a flask and refluxed for 24 hours. After the reaction, water and toluene were added to the reaction solution and stirred, and the organic layer was separated and washed with water. The organic layer was then concentrated to obtain a crude product. The crude product was purified using a silica gel column (eluent: ethyl acetate / toluene = 1 / 5 (volume ratio)), and the fraction containing the target product was concentrated to obtain oily N-(dibenzo[b,d]furan-3-yl)-N-(2,6-dimethylphenyl)dibenzo[b,d]furan-3-amine[r-3] (19.2g).

[0548] [ka]

[0549] [2nd~3rd stage] The compound [r-3] (19.2 g, 42.3 mmol) obtained in the first step was dissolved in chlorobenzene (50 mL), and boron tribromide (31.8 g, 127 mmol) was added and stirred at room temperature for 8 hours. The temperature was raised to 100°C and the pressure was reduced to remove volatiles. The reaction mixture containing the target product [r-4] was not purified and was carried to the next step. 2,6-di(propen-2-yl)phenyllithium (6.3 g, 38 mmol) and N-butyllithium (30 mL, 1.1 mmol) dissolved in chlorobenzene (100 mL) were added to the reaction mixture and stirred at 100°C for 24 hours. A saturated aqueous solution of ammonium chloride was added to the reaction liquid, stirred, and extracted with toluene. The reaction mixture was purified by silica gel column chromatography (eluent: toluene) to recover only the fractions containing the target compound, yielding 15-(2,6-di(propan-1-en-2-yl)phenyl)-7-(2,6-dimethylphenyl)-7,15-dihydrobenzo[2,3]benzofuro[6,5-b]benzo[2,3]benzofuro[5,6-e][1,4]azaborinine[r-5] (10.7 g).

[0550] [ka]

[0551] [4th stage] 15-(2,6-di(propan-1-en-2-yl)phenyl)-7-(2,6-dimethylphenyl)-7,15-dihydrobenzo[2,3]benzofuro[6,5-b]benzo[2,3]benzofuro[5,6-e][1,4]azaborinine[r-5] (10.7g, 17.3mmol) and scandium triflate (8.5g, 17.3mmol) synthesized in the third step were dissolved in chlorobenzene (200ml) and heated and stirred at 100°C for 7 hours. Saturated sodium bicarbonate was added and the mixture was extracted with toluene. After concentration under reduced pressure, the resulting crude product was purified by silica gel column chromatography (eluent: toluene / hexane = 1 / 4 (volume ratio)) to obtain 11-(2,6-dimethylphenyl)-4,4,18,18-tetramethyl-11,18-dihydro-4H-9,13-dioxa-11-aza-3a2-borabenzo[jk]fluoreno[2,3,4-fg]indeno[1,2-a]pyrene [compound (4-37)] (6.4 g, yield 60%).

[0552] [ka]

[0553] The structure of the compound obtained was confirmed by NMR spectrum. 1 H-NMR (400MHz, CDCl3): δ=1.70(s,12H),2.11(s,6H),6.68-6.74(m,6H),6.82(dd,2H),7.04(m,2H),7.27(m,2H),7.81(m,2H).

[0554] By appropriately changing the raw material compounds, other compounds of the present invention can be synthesized by referring to the methods according to the above-mentioned synthesis examples and Yamaguchi et al., Organic & Biomolecular Chemistry, 2019, 17, 5500-5504.

[0555] Next, evaluation of the basic physical properties of the compound of the present invention and preparation and evaluation of an organic EL device using the compound of the present invention will be described.

[0556] (1) Preparation and evaluation of evaporated organic electroluminescence devices Organic EL elements according to the examples and comparative examples are prepared, and voltage is applied to measure current density, luminance, chromaticity, and external quantum efficiency. The following four configurations, Configuration A (Table 1), Configuration B (Table 2), Configuration C (Table 3), and Configuration D (Table 4), are selected as the configurations of the prepared organic EL elements and evaluated. Configurations A, C, and D are configurations suitable for thermally activated delayed fluorescence materials, and Configuration B is a general configuration using TTF. Configuration A is an element configuration that can be expected to have high efficiency as shown in the literature (Adv. Mater. 2016, 28, 2777-2781). Configuration C is an element configuration that can be expected to have relatively high efficiency and long-term driving stability as shown in the literature (Scientific Reports, 6, 2016, 22463). Configuration D is an element that uses thermally activated delayed fluorescence as an assisting dopant. However, the application of the compound of the present invention is not limited to these configurations, and the film thickness and constituent materials of each layer can be appropriately changed depending on the basic physical properties of the compound of the present invention.

[0557] <Example 1> [Table 1]

[0558] In Table 1, "NPD" is N,N'-diphenyl-N,N'-dinaphthyl-4,4'-diaminobiphenyl, "TcTa" is 4,4',4"-tris(N-carbazolyl)triphenylamine, "mCP" is 1,3-bis(N-carbazolyl)benzene, "mCBP" is 3,3'-bis(N-carbazolyl)-1,1'-biphenyl, and "TSPO1" is diphenyl[4-(triphenylsilyl)phenyl]phosphine oxide. The chemical structures are shown below.

[0559] [ka]

[0560] <Configuration A: Device using compound (4-37) as a dopant> A 26 mm × 28 mm × 0.7 mm glass substrate (manufactured by Optoscience Co., Ltd.) on which an ITO film having a thickness of 200 nm was formed by sputtering and polished to 50 nm was used as a transparent support substrate. This transparent support substrate was fixed to the substrate holder of a commercially available deposition apparatus (manufactured by Showa Vacuum Co., Ltd.), and a molybdenum deposition boat containing NPD, TcTa, mCP, mCBP, compound (4-37), and TSPO1, and a tungsten deposition boat containing LiF and aluminum were attached.

[0561] The following layers are formed in order on the ITO film of the transparent support substrate. -4 The pressure is reduced to 100 Pa, and first, NPD is heated and evaporated to a thickness of 40 nm to form a hole injection layer. Next, TcTa is heated and evaporated to a thickness of 15 nm to form a hole transport layer. Next, mCP is heated and evaporated to a thickness of 15 nm to form an electron blocking layer. Next, mCBP and compound (4-37) are heated simultaneously and evaporated to a thickness of 20 nm to form an emitting layer. The evaporation rate is adjusted so that the mass ratio of mCBP to compound (4-37) is approximately 99:1. Next, TSPO1 is heated and evaporated to a thickness of 40 nm to form an electron transport layer. The evaporation rate of each layer is 0.01 to 1 nm / sec. Thereafter, LiF is heated and evaporated at a evaporation rate of 0.01 to 0.1 nm / sec to form a thickness of 1 nm, and then aluminum is heated and evaporated to a thickness of 100 nm to form a cathode, thereby obtaining an organic EL device. At this time, the evaporation rate of aluminum is adjusted to be 1 to 10 nm / sec.

[0562] The ITO electrode is the anode and the aluminum electrode is the cathode, and a DC voltage is applied to measure the luminance, chromaticity, and external quantum efficiency.

[0563] <Example 2> [Table 2]

[0564] In Table 2, "HI-1" is N 4 ,N 4' -Diphenyl-N 4 ,N 4' -bis(9-phenyl-9H-carbazol-3-yl)-[1,1'-biphenyl]-4,4'-diamine, "HAT-CN" is 1,4,5,8,9,12-hexaazatriphenylene hexacarbonitrile, "HT-1" is N-([1,1'-biphenyl]-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluoren-2-amine, and "HT-2" is N,N-bis(4-(dibenzo[b,d]furan-4-yl) "EMH1" is 9-phenyl-10-(4-phenylnaphthalen-1-yl)anthracene, "ET-1" is 4,6,8,10-tetraphenyl[1,4]benzoxaborinino[2,3,4-kl]phenoxaborinine, and "ET-2" is 3,3'-((2-phenylanthracene-9,10-diyl)bis(4,1-phenylene))bis(4-methylpyridine), the chemical structures of which are shown below along with "Liq."

[0565] [ka]

[0566] <Configuration B: Element using compound (4-37) as a dopant> An EL element of configuration B is obtained according to the constituent materials and film thicknesses in Table 2 using the same procedures as for configuration A. However, the deposition rate is adjusted so that the mass ratio of EMH2 to compound (4-37) in the emitting layer is approximately 99:1, and the mass ratio of ET-2 to Liq in the electron transport layer 2 is approximately 1:1. In addition, the deposition rate is adjusted so that the mass ratio of silver to magnesium is 1:9. The ITO electrode is the anode and the silver-magnesium alloy electrode is the cathode, and a DC voltage is applied to measure the luminance, chromaticity, and external quantum efficiency.

[0567] <Example 3> [Table 3]

[0568] In Table 3, "Tris-PCz" is 9,9',9"-triphenyl-9H,9H',9H"-3,3',6',3"-tert-carbazole, "T2T" is 2,4,6-tri[[1,1'-biphenyl]-3-yl]-1,3,5-triazine, and "BPy-TP2" is 2,7-di([2,2'-bipyridine]-5-yl)triphenylene. The chemical structures are shown below.

[0569] [ka]

[0570] <Configuration C: Device using compound (4-37) as a dopant> A 26 mm × 28 mm × 0.7 mm glass substrate (Optoscience Co., Ltd.) on which an ITO film formed by sputtering was polished to 50 nm was used as a transparent support substrate. This transparent support substrate was fixed to the substrate holder of a commercially available deposition device (Choshu Sangyo Co., Ltd.), and tantalum deposition crucibles containing HAT-CN, Tris-PCz, mCBP, compound (4-37), T2T, and BPy-TP2, and aluminum nitride deposition crucibles containing LiF and aluminum were attached.

[0571] The following layers are formed in order on the ITO film of the transparent support substrate. -4The pressure is reduced to 1 Pa, and first, HAT-CN is heated and evaporated to a thickness of 10 nm, and then Tris-PCz is heated and evaporated to a thickness of 30 nm to form a hole layer consisting of two layers. Next, mCBP and compound (4-37) are heated simultaneously and evaporated to a thickness of 30 nm to form an emitting layer. The evaporation rate is adjusted so that the mass ratio of mCBP to compound (4-37) is approximately 90:10. Next, T2T is heated and evaporated to a thickness of 10 nm, and BPy-TP2 is evaporated to a thickness of 30 nm to form an electron transport layer consisting of two layers. The evaporation rate of each layer is 0.01 to 1 nm / sec. Thereafter, LiF is heated and evaporated at a evaporation rate of 0.01 to 0.1 nm / sec to a thickness of 1 nm, and then aluminum is heated and evaporated at a evaporation rate of 0.1 to 2 nm / sec to form a cathode, thereby obtaining an organic EL device.

[0572] The ITO electrode is the anode and the aluminum electrode is the cathode, and a DC voltage is applied to measure the luminance, chromaticity, and external quantum efficiency.

[0573] <Example 4> [Table 4]

[0574] In Table 4, "3Cz2DPhCzBN" is 2,4,6-tri(9H-carbazol-9-yl)-3,5-bis(3,6-diphenyl-9H-carbazol-9-yl)benzonitrile. The chemical structure is shown below. [ka]

[0575] <Configuration D: Element using 3Cz2DPhCzBN as the assisting dopant and compound (4-37) as the emitting dopant> A 26 mm x 28 mm x 0.7 mm glass substrate (manufactured by Optoscience Co., Ltd.) on which an ITO film formed to a thickness of 200 nm by sputtering was polished to 50 nm was used as a transparent support substrate. This transparent support substrate was fixed to the substrate holder of a commercially available deposition device (manufactured by Choshu Sangyo Co., Ltd.), and a tantalum deposition boat containing HAT-CN, Tris-PCz, mCBP, 3Cz2DPhCzBN, compound (4-37), T2T, and BPy-TP2, and an aluminum nitride deposition boat containing Liq, LiF, and aluminum, were attached.

[0576] The following layers are formed in order on the ITO film of the transparent support substrate. -4 The pressure is reduced to 10 Pa, and first, HAT-CN is heated and evaporated to a thickness of 10 nm, and then Tris-PCz is heated and evaporated to a thickness of 30 nm to form a hole layer consisting of two layers. Next, mCBP as a host, 3Cz2DPhCzBN as an assisting dopant, and compound (4-37) as an emitting dopant are simultaneously heated and co-evaporated to a thickness of 30 nm to form an emitting layer. The evaporation rate is adjusted so that the mass ratio of the host, assisting dopant, and emitting dopant is approximately 80:19:1. Next, T2T is heated and evaporated to a thickness of 10 nm, and then BPy-TP2 and Liq are heated and evaporated to a thickness of 30 nm to form electron transport layers 1 and 2. The evaporation rate of each of the above layers is 0.01 to 1 nm / sec. Then, LiF is heated and evaporated at a deposition rate of 0.01 to 0.1 nm / sec to a thickness of 1 nm, and then aluminum is heated and evaporated to a thickness of 100 nm to form a cathode, thereby obtaining an organic EL device. At this time, the evaporation rate of aluminum is adjusted to 1 to 10 nm / sec.

[0577] The ITO electrode is the anode and the aluminum electrode is the cathode, and a DC voltage is applied to measure the luminance, chromaticity, and external quantum efficiency.

[0578] <Example 5, Comparative Example 1> (Structure B1 of Organic EL Element) The organic EL element having the structure B1 has a structure in which the host and cathode materials in the organic EL element having the structure B described above are changed. [Table 5]

[0579] In Table 5, "EMH3" is 2-(10-phenylanthracen-9-yl)dibenzo[b,d]furan and "BD1" is 4,8,12-triphenyl-8,12-dihydro-4H-4,8,12-triaza-3a2-boradibenzo[cd,mn]pyrene. The chemical structures are shown below.

[0580] [ka]

[0581] <Constitution B1: Element using compound (4-37) as a dopant (Example 5)> A 26 mm × 28 mm × 0.7 mm glass substrate (manufactured by Optoscience Co., Ltd.) on which an ITO film having a thickness of 200 nm was formed by sputtering and polished to 50 nm was used as a transparent support substrate. This transparent support substrate was fixed to a substrate holder of a commercially available deposition apparatus (manufactured by Showa Vacuum Co., Ltd.), and a molybdenum deposition boat containing HI-1, HAT-CN, HT-1, HT-2, EMH3, compound (4-37), ET-1, ET-2, and Liq, and a tungsten deposition boat containing LiF and aluminum were attached.

[0582] The following layers were formed in order on the ITO film of the transparent support substrate. -4The pressure was reduced to 10 Pa, and HI-1 was heated and evaporated to a thickness of 40 nm, and HAT-CN was heated and evaporated to a thickness of 5 nm to form a two-layer hole injection layer. HT-1 was then heated and evaporated to a thickness of 15 nm, and HT-2 was then heated and evaporated to a thickness of 10 nm to form a two-layer hole transport layer. EMH3 and compound (4-37) were then simultaneously heated and evaporated to a thickness of 25 nm to form an emitting layer. The evaporation rate was adjusted so that the mass ratio of EMH3 to compound (4-37) was approximately 99:1. ET-1 was then heated and evaporated to a thickness of 5 nm, and ET-2 and Liq were then heated and evaporated to a thickness of 25 nm to form a two-layer electron transport layer. The evaporation rate was adjusted so that the mass ratio of ET-2 to Liq was approximately 1:1. The evaporation rate of each layer was 0.01 to 1 nm / sec. Then, LiF was heated and evaporated at a deposition rate of 0.01 to 0.1 nm / sec to a thickness of 1 nm, and then aluminum was heated and evaporated to a thickness of 100 nm to form a cathode, thereby obtaining an organic EL device. At this time, the evaporation rate of aluminum was adjusted to 1 to 10 nm / sec.

[0583] When a DC voltage was applied to the ITO electrode as the anode and the aluminum electrode as the cathode, the brightness was 1000 cd / m 2 At this time, the emission peak wavelength was 450 nm, the emission half-width was 30 nm, and the external quantum efficiency was 5.5%. 2 LT90 when continuously driven at 900cd / m 2 The time it took to reach maturity (time to completion of the reaction) was 32 hours.

[0584] <Constitution B1: Element using compound (BD1) as a dopant (Comparative Example 1)> Except for using compound (BD1) instead of compound (4-37) as the dopant, an organic EL device was obtained in the same manner as in Example 5. When a direct current voltage was applied between the ITO electrode as the anode and the aluminum electrode as the cathode, the luminance was 1000 cd / m 2At this time, the emission peak wavelength was 405 nm, the emission half-width was 24 nm, and the external quantum efficiency was 1.5%. 2 When operated continuously, the LT90 was less than one hour.

[0585] The characteristics of Example 5 and Comparative Example 1 are summarized below. The organic EL device using the compound of the present invention was superior to the comparative examples in external quantum efficiency and device life. [Table 6]

[0586] (2) Preparation and evaluation of compositions for forming light-emitting layers <Examples S-1 to S-3 and Comparative Example S-1> As shown in Table 7, 0.99% by mass of the first component host, 0.01% by mass of the second component dopant, and 99% by mass of the third component solvent were mixed to prepare compositions for forming an emission layer with a solids concentration of 1% by mass.

[0587] [Table 7]

[0588] In Table 7 above, "EMH4" is 9-(7-([1,1':3',1":3",1'"-quatrophenyl]-3-yl)naphthalen-2-yl)-10-phenylanthracene. The chemical structure is shown below.

[0589] [ka]

[0590] The solvents used in preparing the composition for forming the light-emitting layer are as follows. "Tol / DHNp (9 / 1)" Mixture of toluene and decahydronaphthalene (volume ratio: 9 / 1) "3PxT / c6B (7 / 3)" Mixture of 3-phenoxytoluene / cyclohexylbenzene = 7 / 3 (volume ratio)

[0591] The prepared compositions for forming a light-emitting layer were evaluated as follows. The results are shown in Table 8.

[0592] <Evaluation of solubility> The solubility of the prepared compositions for forming a light-emitting layer was evaluated by checking for the presence or absence of turbidity and precipitation. Compositions without turbidity and precipitation were rated as "A," and compositions with turbidity or precipitation were rated as "F."

[0593] <Evaluation of film-forming properties> For compositions for forming an emitting layer that were rated "A" for solubility, the films obtained after spin-coating or inkjet printing were observed according to the procedure described below. Films that had either pinholes, compound precipitation, or unevenness were rated "C." Films that were free of pinholes, compound precipitation, and unevenness were rated "B." Films that were rated "B" and also had high smoothness (Ra<5 nm) were rated "A."

[0594] (Film formation method by spin coating) A clean glass substrate with a thickness of 0.5 mm and a size of 28 × 26 mm was used, and the irradiation energy was 1000 mJ / cm 2 A UV-O3 treatment was carried out by irradiating the glass with a low-pressure mercury lamp (254 nanometers). Next, 0.3 to 0.6 ml of the composition for forming the light-emitting layer was dropped onto the glass, and spin-coated (slope (increase the rotation speed to a specified speed in 5 seconds) → apply at 500 to 5000 rpm (maintain at the specified rotation speed for 10 seconds) → slope (decrease the rotation speed in 5 seconds, and set the rotation speed to 0 rpm)). Furthermore, the film was formed by drying for 10 minutes on a hot plate at 120°C.

[0595] (Inkjet film formation method) The composition for forming the light-emitting layer was discharged into a pixel of 100 ppi using an inkjet printer and dried at 120° C. to form a film.

[0596] <Evaluation of inkjet ejection stability> For compositions for forming light-emitting layers that were rated "A" for solubility, the compositions for forming light-emitting layers were discharged into a pixel of 100 ppi using an inkjet, and the discharge stability of each inkjet was evaluated immediately after the start of discharge and after 24 hours of continuous operation. In the evaluation, if the composition could be discharged from less than 50% of the discharge holes (including cases where it could not be discharged), it was rated "C," if the composition could be discharged from 50% to less than 90% of the discharge holes, it was rated "B," and if the composition could be discharged from 90% or more of the discharge holes, it was rated "A."

[0597] [Table 8]

[0598] (3) Preparation and evaluation of solution-type organic electroluminescence devices Next, an organic EL device obtained by forming an organic layer by coating will be described.

[0599] <Synthesis of polymer hole transport compound: XLP-101> XLP-101 was synthesized according to the method described in JP 2018-61028 A. A copolymer in which M5 or M6 is bonded next to M4 was obtained, and it is estimated that each unit is 40:10:50 (molar ratio) based on the charge ratio. In the following formula, Bpin is pinacolatoboryl. [ka]

[0600] <Polymer hole transport compound: Preparation of XLP-101 solution> XLP-101 synthesized according to the method described in JP 2018-61028 A was dissolved in a mixed solution of 3-phenoxytoluene / cyclohexylbenzene = 7 / 3 (volume ratio) to a concentration of 0.7 mass%.

[0601] <Preparation of Organic EL Devices of Example SD-1 and Comparative Example SD-1> Table 9 shows the material composition of each layer in the organic EL element. [Table 9]

[0602] As the "PEDOT:PSS" which is the material for forming the hole injection layer in Table 9 above, a commercially available PEDOT:PSS solution (Clevios(TM) P VP AI4083, an aqueous dispersion of PEDOT:PSS represented by the following formula, manufactured by Heraeus Holdings) was used.

[0603] [ka]

[0604] <Example SD-1> A PEDOT:PSS solution was spin-coated on a glass substrate on which ITO was deposited to a thickness of 50 nm, and baked on a hot plate at 200 ° C. for 1 hour to form a hole injection layer with a thickness of 40 nm. Next, an XLP-101 solution was spin-coated, dried on a hot plate at 80 ° C. for 10 minutes, and then baked on a hot plate at 200 ° C. for 1 hour to form a hole transport layer with a thickness of 30 nm that is insoluble in the composition for forming an emitting layer. Next, the composition for forming an emitting layer prepared in Example S-3 was spin-coated, and baked on a hot plate at 120 ° C. for 1 hour to form a emitting layer with a thickness of 20 nm.

[0605] The multilayer film thus prepared was fixed to a substrate holder of a commercially available deposition apparatus (Showa Vacuum Co., Ltd.), and a molybdenum deposition boat containing ET-1, ET-2, Liq, and LiF, and a tungsten deposition boat containing aluminum were attached. The vacuum chamber was filled with 5×10 -4After the pressure was reduced to 1 Pa, ET-1 was heated and evaporated to a thickness of 10 nm to form an electron transport layer 1. Next, ET-2 and Liq were heated and evaporated to a thickness of 20 nm to form an electron transport layer 2. The evaporation rate was adjusted so that the mass ratio of ET-2 and Liq was approximately 1:1. The evaporation rate when forming the electron transport layer was 1 nm / sec. Then, LiF was heated and evaporated at an evaporation rate of 0.01 to 0.1 nm / sec to a thickness of 1 nm. Next, aluminum was heated and evaporated to a thickness of 100 nm to form a cathode. In this manner, an organic EL device was obtained.

[0606] A DC voltage of 1000 cd / m was applied to the ITO electrode as the anode and the aluminum electrode as the cathode. 2 When the characteristics of the light emission were measured, the light-emitting surface was found to be uniform, and the emission spectrum had a peak wavelength of 452 nm and a half-width of 38 nm. 2 The external quantum efficiency during light emission was 2.1%.

[0607] <Comparative Example SD-1> An organic EL device was obtained in the same manner as in Example SD-1, except that Comparative Example S-1 was formed instead of Example S-2. A DC voltage of 1000 cd / m was applied between the ITO electrode as the anode and the aluminum electrode as the cathode. 2 When the characteristics of the light emission were measured, bright spots were observed on the light-emitting surface, suggesting that crystallization of the compound had occurred. The emission spectrum had a peak wavelength of 425 nm and a half-width of 67 nm. The emission spectrum also had a peak wavelength of 1000 cd / m 2 The external quantum efficiency during light emission was 0.2%.

[0608] The results of Example SD-1 and Comparative Example SD-1 are summarized in Table 10. Higher efficiency was obtained in Example SD-1, which used the compound of the present invention. [Table 10] [Industrial Applicability]

[0609] In the present invention, by providing a novel polycyclic aromatic compound, it is possible to increase the options of materials for organic electroluminescence devices. In addition, by using the novel polycyclic aromatic compound as a material for organic electroluminescence devices, it is possible to provide an excellent organic electroluminescence device, a display device including the same, and a lighting device including the same. [Explanation of symbols]

[0610] 100 Organic electroluminescent device 101 Substrate 102 Anode 103 Hole injection layer 104 Hole transport layer 105 Light-emitting layer 106 Electron transport layer 107 Electron injection layer 108 Cathode

Claims

1. A polycyclic aromatic compound represented by formula (4) or formula (12). 【Chemistry 1】 (In formula (4) and formula (12), Y 1 is B; X 1 is >O, >N—R, or >C(—R) 2 ; X2 is >O, >C(-R)2, or >S; X 3 is >O, >N—R, >C(—R) 2 , or >S; X 4 and X 6 are each independently >O, >N—R, or >S; R in the >N-R is each independently phenyl (which may be substituted with alkyl having 1 to 6 carbon atoms or phenyl which may be substituted with alkyl having 1 to 6 carbon atoms); R in the >C(-R) 2 is methyl; R b1 ~R b13 is hydrogen or any substituent selected from methyl, t-butyl, t-amyl, t-octyl, phenyl, o-tolyl, p-tolyl, 2,4-xylyl, 2,5-xylyl, 2,6-xylyl, 2,4,6-mesityl, diphenylamino, di-p-tolylamino, bis(p-(t-butyl)phenyl)amino, carbazolyl, 3,6-dimethylcarbazolyl, 3,6-di-t-butylcarbazolyl, and phenoxy; At least one hydrogen atom in each of the compounds represented by formula (4) and formula (12) may be replaced with deuterium.

2. The polycyclic aromatic compound according to claim 1, wherein X 1 is >N--R.

3. The polycyclic aromatic compound according to claim 1, wherein X 2 and X 3 are both >C(—R) 2 .

4. The polycyclic aromatic compound according to claim 1 , which is represented by any one of the following structural formulas: 【Chemistry 2】 【Chemistry 3】 【Chemistry 4】 【Chemistry 5】

5. A material for an organic device, comprising the polycyclic aromatic compound according to any one of claims 1 to 4.

6. The material for an organic device according to claim 5 , which is a material for an organic electroluminescent element, a material for an organic field effect transistor, or a material for an organic thin-film solar cell.

7. The material for an organic device according to claim 6 , wherein the material for an organic electroluminescent element is a material for a light-emitting layer.

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

9. 5. 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.

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

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

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

13. The organic electroluminescence device according to any one of claims 10 to 12, further comprising an electron transport layer and / or an electron injection layer disposed between the cathode and the light emitting layer, and at least one of the electron transport layer and the electron injection layer contains at least one selected from the group consisting of borane derivatives, pyridine derivatives, fluoranthene derivatives, BO-based derivatives, anthracene derivatives, benzofluorene derivatives, phosphine oxide derivatives, pyrimidine derivatives, arylnitrile derivatives, triazine derivatives, benzimidazole derivatives, phenanthroline derivatives, quinolinol-based metal complexes, thiazole derivatives, benzothiazole derivatives, silole derivatives, and azoline derivatives.

14. 14. The organic electroluminescent device according to claim 13, wherein the electron transport layer and / or the electron injection layer further contains at least one selected from the group consisting of alkali metals, alkaline earth metals, rare earth metals, oxides of alkali metals, halides of alkali metals, oxides of alkaline earth metals, halides of alkaline earth metals, oxides of rare earth metals, halides of rare earth metals, organic complexes of alkali metals, organic complexes of alkaline earth metals, and organic complexes of rare earth metals.

15. A display device or lighting device comprising the organic electroluminescent element according to claim 9.

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