Polycyclic aromatic compound

Abstract

To provide a novel compound useful as a material for an organic device such as an organic EL element.SOLUTION: There is provided a polycyclic aromatic compound represented by the formula (1) or a multimer of a polycyclic aromatic compound having a plurality of structures represented by the following formula (1). (In the formula, the A ring, the B ring, and the C ring are aryl rings or heteroaryl rings, and at least one hydrogen in these rings may be substituted; Y1 is B or the like; X1 and X2 are >O, >N-R (R may be substituted aryl or the like); at least one of the aryl rings or heteroaryl rings in the compound represented by the formula (1) or a multimer thereof is substituted with at least one L-Cy, and L is a linking group such as a linear alkylene having 1 to 6 carbon atoms or a branched chain alkylene having 2 to 6 carbon atoms, -O- or the like; Cy is a cycloalkyl.)SELECTED DRAWING: None

Description

[Technical field]

[0001] The present invention relates to a polycyclic aromatic compound, and an organic electroluminescent device, an organic field effect transistor, an organic thin-film solar cell, a display device, and a lighting device, all using the same. In this specification, the term "organic electroluminescent device" may be referred to as "organic EL device" or simply as "device". [Background technology]

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

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

[0004] 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 Document 1). Furthermore, polycyclic aromatic compounds in which cycloalkyl has been introduced into the aromatic rings of the compounds have been developed, and organic EL devices using them have been reported (Patent Documents 2 and 3). [Prior art documents] [Patent documents]

[0005] [Patent Document 1] International Publication No. 2015 / 102118 [Patent Document 2] International Publication No. 2018 / 216990 [Patent Document 3] International Publication No. 2019 / 198699 Summary of the Invention [Problem to be solved by the invention]

[0006] As described above, various materials have been developed for use in organic EL elements. However, 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 compound useful as a material for organic devices such as organic EL elements. [Means for solving the problem]

[0007] As a result of intensive research to solve the above problems, the present inventors have found that an excellent organic EL element can be obtained by, for example, constructing an organic EL element by disposing, between a pair of electrodes, a layer containing a polycyclic aromatic compound in which a linking group is introduced between the aromatic ring and cycloalkyl of the compound as described in Patent Document 2 or 3, and have completed the present invention. That is, the present invention provides a polycyclic aromatic compound or a multimer thereof having a structure in which a cycloalkyl is bonded to an aromatic ring via a linking group as shown below, and further provides a material for an organic device, such as a material for an organic EL element, which contains such a polycyclic aromatic compound or a multimer thereof.

[0008] <1> A polycyclic aromatic compound represented by the following formula (1), or a multimer of a polycyclic aromatic compound having a plurality of structures represented by the following formula (1). [ka]

[0009] (In formula (1), ring A, ring B, and ring C are each independently an aryl ring or a heteroaryl ring, at least one hydrogen atom in these rings may be substituted, and ring B and ring C may be bonded via a single bond or a linking group; Y 1 is B, P, P=O, P=S, Al, Ga, As, Si-R, or Ge-R, wherein R of Si-R and Ge-R is aryl or alkyl; X 1 and X 2 are independently >O, >NR, >C(-R) 2 , >S, or >Se, and R of the >NR is optionally substituted aryl, optionally substituted heteroaryl, optionally substituted alkyl, or optionally substituted cycloalkyl, and the >C(-R) 2 R is hydrogen, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted alkyl, or optionally substituted cycloalkyl, and R in >NR and / or >C(-R) 2 R may be bonded to the ring A, ring B, and / or ring C via a linking group or a single bond; At least one of the aryl or heteroaryl rings in the compound represented by formula (1) or a multimer thereof may be fused with at least one cycloalkane, at least one hydrogen in the cycloalkane may be substituted, and at least one -CH 2 - may be replaced by -O-; At least one of the aryl rings or heteroaryl rings in the compound represented by formula (1) or a multimer thereof is substituted with at least one L-Cy, and L is a linear alkylene having 1 to 6 carbon atoms or a branched alkylene having 2 to 6 carbon atoms, or at least one -CH 2A linking group in which - is replaced by -O-, -S-, -CO-, -COO-, -OCO-, or -OCOO-, or a linear alkylene having 2 to 6 carbon atoms having at least one -(CH 2 ) 2 - is a linking group replaced by -CH=CH- or -C≡C-, and Cy is cycloalkyl; At least one hydrogen atom in the compound represented by formula (1) or a polymer thereof may be substituted with deuterium, cyano, or halogen. <2> Cy is a cycloalkyl having 3 to 20 carbon atoms; <1> 2. The polycyclic aromatic compound or a multimer thereof according to claim 1 . <3> L is -CH 2 -, -CH 2 CH 2 -, -CH 2 CH 2 CH 2 -, -C(CH 3 ) 2 -, -C(CH 3 ) 2 CH 2 - or -C(CH 3 ) 2 CH 2 CH 2 - is, <1> or <2> 2. The polycyclic aromatic compound or a multimer thereof according to claim 1 .

[0010] <4> The polycyclic aromatic compound is represented by the following formula (1-a), (1-b), (1-c), (1-d), (1-e), or (1-f), or a multimer of a polycyclic aromatic compound having a plurality of structures represented by the following formula (1-a), (1-b), (1-c), (1-d), (1-e), or (1-f): <1> ~ <3> 2. The polycyclic aromatic compound or a multimer thereof according to claim 1 . [ka]

[0011] (In formula (1-a), formula (1-b), formula (1-c), formula (1-d), formula (1-e), and formula (1-f), R 1 ~R11 are each independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl (two aryls may be bonded via a single bond or a linking group), alkyl, cycloalkyl, alkoxy, aryloxy, or substituted silyl, in which at least one hydrogen may be replaced by an aryl, heteroaryl, alkyl, cycloalkyl, or substituted silyl; R 1 ~R 11 Adjacent groups among may be bonded to each other to form an aryl ring or a heteroaryl ring together with the a ring, the b ring, or the c ring, and at least one hydrogen atom in the formed ring may be replaced by an aryl, a heteroaryl, a diarylamino, a diheteroarylamino, an arylheteroarylamino, a diarylboryl (two aryls may be bonded via a single bond or a linking group), an alkyl, a cycloalkyl, an alkoxy, an aryloxy, or a substituted silyl, and at least one hydrogen atom in these may be replaced by an aryl, a heteroaryl, an alkyl, a cycloalkyl, or a substituted silyl, provided that in formula (1-a), R 7 and R 8 may be bonded to each other to form a single bond or a linking group, X X are each independently >O, >S, >NR, or >C(-R) 2 R of the >NR is an optionally substituted aryl, an optionally substituted heteroaryl, an optionally substituted alkyl, or an optionally substituted cycloalkyl, and the >C(-R) 2 R is each independently hydrogen, aryl optionally substituted with alkyl or cycloalkyl, heteroaryl optionally substituted with alkyl or cycloalkyl, alkyl, or cycloalkyl; 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 or alkyl; X1 and X 2 are, independently, >O, >C(-R) 2 or >NR, R of the >NR is an aryl having 6 to 12 carbon atoms, a heteroaryl having 2 to 15 carbon atoms, an alkyl having 1 to 6 carbon atoms, or a cycloalkyl having 3 to 14 carbon atoms, and the aryl having 6 to 12 carbon atoms and the heteroaryl having 2 to 15 carbon atoms in R of the >NR may each be substituted with an alkyl having 1 to 6 carbon atoms, a cycloalkyl having 3 to 14 carbon atoms, or a substituted silyl, and R of the >NR is -O-, -S-, -C(-R) 2 may be bonded to at least one of the a ring, the b ring, and the c ring via a bond; Above>C(-R) 2 R is independently hydrogen, an aryl having 6 to 12 carbon atoms, a heteroaryl having 2 to 15 carbon atoms, an alkyl having 1 to 6 carbon atoms, or a cycloalkyl having 3 to 14 carbon atoms, and the >C(-R) 2 The aryl having 6 to 12 carbon atoms and the heteroaryl having 2 to 15 carbon atoms in R may each be substituted with an alkyl having 1 to 6 carbon atoms, a cycloalkyl having 3 to 14 carbon atoms, or a substituted silyl, and the above >C(-R) 2 Two R's may be bonded to each other to form a ring, At least one of the aryl rings or heteroaryl rings in the compounds represented by each of formulas (1-a), (1-b), (1-c), (1-d), (1-e), and (1-f) or the multimers thereof may be condensed with at least one cycloalkane having 3 to 24 carbon atoms, at least one hydrogen in the cycloalkane may be substituted with an aryl having 6 to 30 carbon atoms, a heteroaryl having 2 to 30 carbon atoms, an alkyl having 1 to 24 carbon atoms, or a cycloalkyl having 3 to 24 carbon atoms, and at least one -CH in the cycloalkane 2 - may be replaced by -O-; At least one of the aryl rings or heteroaryl rings in the compounds or multimers thereof represented by each of formulas (1-a), (1-b), (1-c), (1-d), (1-e), and (1-f) is substituted with at least one L-Cy, and L is a linear alkylene having 1 to 6 carbon atoms or a branched alkylene having 2 to 6 carbon atoms, or at least one -CH in the linear alkylene having 1 to 6 carbon atoms or the branched alkylene having 2 to 6 carbon atoms. 2 A linking group in which - is replaced by -O-, -S-, -CO-, -COO-, -OCO-, or -OCOO-, or a linear alkylene having 2 to 6 carbon atoms having at least one -(CH 2 ) 2 - is a linking group replaced by -CH=CH- or -C≡C-, and Cy is cycloalkyl; At least one hydrogen atom in the compound or multimer thereof represented by each of formulas (1-a), (1-b), (1-c), (1-d), (1-e), and (1-f) may be substituted with cyano, halogen, or deuterium, and In the case of a multimer, it is a dimer or trimer having two or three structures represented by formula (1-a), formula (1-b), formula (1-c), formula (1-d), formula (1-e), or formula (1-f).

[0012] <5> A polycyclic aromatic compound represented by formula (1-a) or a multimer of a polycyclic aromatic compound having a plurality of structures represented by formula (1-a), <4> 2. The polycyclic aromatic compound or a multimer thereof according to claim 1 .

[0013] <6> Represented by any of the following structural formulas: <5> 2. The polycyclic aromatic compound or a multimer thereof according to claim 1 . [ka] (In the above structural formulas, "Me" stands for methyl and "tBu" stands for t-butyl.)

[0014] <7> A polycyclic aromatic compound represented by formula (1-b) or a multimer of a polycyclic aromatic compound having a plurality of structures represented by formula (1-b). <4> 2. The polycyclic aromatic compound or a multimer thereof according to claim 1 .

[0015] <8> Represented by the following structural formula: <7> 2. The polycyclic aromatic compound or a multimer thereof according to claim 1 . [ka] (In the above structural formula, "Me" represents methyl.)

[0016] <9> <1> ~ <8> 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. <10> <9> 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. <11> Main chain polymer <9> or a pendant-type crosslinked polymer obtained by further crosslinking the pendant-type polymer compound. <12> <1> ~ <8> The polycyclic aromatic compound or a multimer thereof according to any one of the above items. <9> The reactive compound according to <10> or <11> 2. A material for an organic device, comprising the pendant type polymer compound or the pendant type crosslinked polymer according to claim 1. <13> 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. <12> The material for an organic device according to claim 1. <14> The material for an organic electroluminescent device is a material for a light-emitting layer. <13> The material for an organic device according to claim 1.

[0017] <15> <1> ~ <8> The polycyclic aromatic compound or a multimer thereof according to any one of the above items. <9> The reactive compound according to <10> or <11> 2. A composition comprising the pendant type polymer compound or the pendant type crosslinked polymer according to claim 1, and an organic solvent.

[0018] <16> A pair of electrodes consisting of an anode and a cathode, and a gas sensor disposed between the pair of electrodes, <1> ~ <8> The polycyclic aromatic compound or a multimer thereof according to any one of the above items. <9> The reactive compound according to <10> or <11> and an organic layer containing the pendant type polymer compound or the pendant type crosslinked polymer according to claim 1. <17> A pair of electrodes consisting of an anode and a cathode, and a gas sensor disposed between the pair of electrodes, <1> ~ <8> The polycyclic aromatic compound or a multimer thereof according to any one of the above items. <9> The reactive compound according to <10> or <11> and a light-emitting layer containing the pendant type polymer compound or the pendant type crosslinked polymer according to claim 1. <18> the light-emitting layer contains a host and, as a dopant, the polycyclic aromatic compound or a multimer thereof, the reactive compound, the polymer compound or a crosslinked polymer, or the pendant polymer compound or a pendant crosslinked polymer; <17> The organic electroluminescent device according to claim 1. <19> The host is an anthracene-based compound, a fluorene-based compound, or a dibenzochrysene-based compound; <18> The organic electroluminescent device according to claim 1. <20> 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; <16> ~ <19> 13. The organic electroluminescent device according to claim 12,

[0019] <21> 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; <20> The organic electroluminescent device according to claim 1. <22> At least one layer of the organic layer disposed between the pair of electrodes contains a polymer compound obtained by polymerizing a low molecular weight compound capable of forming each layer as a monomer, or a polymer crosslinked product obtained by further crosslinking the polymer compound, or a pendant polymer compound obtained by reacting a low molecular weight compound capable of forming each layer with a main chain polymer, or a pendant polymer crosslinked product obtained by further crosslinking the pendant polymer compound, <16> ~ <21> 13. The organic electroluminescent device according to claim 12, <23> <16> ~ <22> 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

[0020] The present invention provides a novel polycyclic aromatic compound. The polycyclic aromatic compound of the present invention can be used as a material for organic devices such as a material for an organic EL device. [Brief description of the drawings]

[0021] [Figure 1] FIG. 1 is a schematic cross-sectional view showing an organic EL element according to an embodiment of the present invention. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0022] 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)".

[0023] 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.

[0024] 1. Polycyclic aromatic compounds and their polymers The present invention relates to a polycyclic aromatic compound represented by the following formula (1) or a multimer of a polycyclic aromatic compound having a plurality of structures represented by the following formula (1).

[0025] The polycyclic aromatic compound represented by formula (1) is a polycyclic aromatic compound having a basic skeleton in which aromatic rings are linked by heteroatoms such as boron, phosphorus, oxygen, nitrogen, and sulfur. Compounds having such a basic skeleton have a large HOMO-LUMO gap (band gap in a thin film, Eg) and a high triplet excitation energy (E T). This is thought to be because the six-membered ring containing a heteroatom has low aromaticity, which suppresses the decrease in the HOMO-LUMO gap associated with the expansion of the conjugated system, and because the SOMO1 and SOMO2 in the triplet excited state (T1) are localized due to electronic perturbation of the heteroatom. In addition, in polycyclic aromatic compounds having the above basic skeleton portion, the exchange interaction between the two orbitals is reduced due to the localization of SOMO1 and SOMO2 in the triplet excited state (T1), so the energy difference (ΔE S1T1 ) and exhibits thermally activated delayed fluorescence, making it useful as a fluorescent material for organic electroluminescence (EL) devices. T Materials having the above property 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, the HOMO and LUMO energies of these polycyclic aromatic compounds (basic skeleton parts) can be arbitrarily shifted by introducing substituents, so that the ionization potential and electron affinity can be optimized according to the surrounding materials.

[0026] In addition to the characteristics of the basic skeleton part, the compound of the present invention is expected to have a lower melting point and sublimation temperature by introducing a cycloalkyl. This means that in the sublimation purification, which is almost indispensable as a purification method for materials for organic devices such as organic EL elements that require high purity, purification can be performed at a relatively low temperature, so that thermal decomposition of the material can be avoided. This is also true for the vacuum deposition process, which is a powerful means for producing organic devices such as organic EL elements, and since the process can be performed at a relatively low temperature, thermal decomposition of the material can be avoided, and as a result, a high-performance material for organic devices can be obtained. In addition, since many of the multimers of polycyclic aromatic compounds have a high sublimation temperature due to their molecular weight and high planarity, the reduction in sublimation temperature by introducing a cycloalkyl is more effective. In addition, since the introduction of a cycloalkyl improves the solubility in organic solvents, it can also be applied to the production of elements using a coating process. Furthermore, in the compound of the present invention, the cycloalkyl is bonded to the basic skeleton part of the polycyclic aromatic compound via a linking group, and thus the solubility in organic solvents is improved compared to when the cycloalkyl is directly bonded, and a coating film with fewer film defects and excellent smoothness can be provided in the coating process. Furthermore, by using the compound of the present invention having such a structure as a device material, it is possible to provide a device having higher efficiency and a longer life.

[0027] The polycyclic aromatic compound represented by formula (1) or a multimer of a polycyclic aromatic compound having a plurality of structures represented by the following formula (1) is preferably a polycyclic aromatic compound or a multimer thereof represented by the following formula (1-a), formula (1-b), formula (1-c), formula (1-d), formula (1-e), or formula (1-f).

[0028] [ka]

[0029] In each structural formula, "A" to "C" and "a" to "c" are symbols indicating a ring, a benzene ring, or a ring structure represented by a five-membered ring, and the other symbols are the same as defined above.

[0030] At least one of the aryl or heteroaryl rings in the polycyclic aromatic compound represented by formula (1) or the multimer or structure of the polycyclic aromatic compound having a plurality of structures represented by formula (1) is bonded to a cycloalkyl via a linking group. Specifically, at least one of the aryl or heteroaryl rings is substituted with at least one L-Cy. Here, L is a linking group and Cy is a cycloalkyl.

[0031] The linking group L is a linear alkylene having 1 to 6 carbon atoms or a branched alkylene having 2 to 6 carbon atoms, or at least one -CH 2 A linking group in which - is replaced by -O-, -S-, -CO-, -COO-, -OCO-, or -OCOO-, or a linear alkylene having 2 to 6 carbon atoms having at least one -(CH 2 ) 2 is a linking group in which - is replaced by -CH=CH- or -C≡C-.

[0032] The cycloalkyl is preferably a cycloalkyl having 3 to 24 carbon atoms, more preferably a cycloalkyl having 3 to 20 carbon atoms, further preferably a cycloalkyl having 3 to 16 carbon atoms, and particularly preferably a cycloalkyl having 3 to 14 carbon atoms. The cycloalkyl may be a cycloalkyl having 5 to 10 carbon atoms, a cycloalkyl having 5 to 8 carbon atoms, a cycloalkyl having 5 to 6 carbon atoms, a cycloalkyl having 5 carbon atoms, or the like. In this specification, "cycloalkyl" includes not only monocyclic ones such as cyclohexyl, but also polycyclic ones such as adamantyl.

[0033] Specific examples of cycloalkyl include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, and alkyl (particularly methyl) substituted derivatives of these having 1 to 5 carbon atoms, as well as norbornyl (bicyclo[2.2.1]heptyl), bicyclo[1.1.0]butyl, bicyclo[1.1.1]pentyl, bicyclo[2.1.0]pentyl, bicyclo[2.1.1]hexyl, bicyclo[3.1.0]hexyl, bicyclo[2.2.2]octyl, adamantyl, diamantyl, decahydronaphthalenyl, and decahydroazulenyl. Among these, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, and alkyl (particularly methyl) substituted derivatives of these having 1 to 5 carbon atoms, norbornyl, bicyclo[1.1.0]butyl, bicyclo[1.1.1]pentyl, bicyclo[2.1.0]pentyl, bicyclo[2.1.1]hexyl, bicyclo[3.1.0]hexyl, bicyclo[2.2.2]octyl, and adamantyl are preferred, with cyclohexyl, norbornyl, bicyclo[2.2.2]octyl, adamantyl, and diamantyl being particularly preferred.

[0034] The linking group L is a linear alkylene having 1 to 6 carbon atoms or a branched alkylene having 2 to 6 carbon atoms, or at least one -CH 2 A linking group in which - is replaced by -O-, -S-, -CO-, -COO-, -OCO-, or -OCOO-, or a linear alkylene having 2 to 6 carbon atoms having at least one -(CH 2 ) 2 It is a linking group in which - is replaced by -CH=CH- or -C≡C-. Among them, a straight chain alkylene having 1 to 6 carbon atoms, a branched chain alkylene having 3 to 6 carbon atoms, or -O- is preferable, and a straight chain alkylene having 1 to 3 carbon atoms or a branched chain alkylene having 3 to 5 carbon atoms is particularly preferable. Specifically, -CH 2 -, -CH 2 CH 2 -, -CH 2 CH 2 CH 2 -, -C(CH3 ) 2 -, -C(CH 3 ) 2 CH 2 - or -C(CH 3 ) 2 CH 2 CH 2 - is preferred. In addition, -C(CH 3 ) 2 CH 2 - and -C(CH 3 ) 2 CH 2 CH 2 - is bonded to Cy on the right side, that is, L-Cy is -C(CH 3 ) 2 CH 2 -Cy and -C(CH 3 ) 2 CH 2 CH 2 Preferably, the linking group L is -CH 2 -, -C(CH 3 ) 2 - or -C(CH 3 ) 2 CH 2 CH 2 Such a linking group structure can further improve the solubility in an organic solvent, and the use of a compound having such a structure as a device material can provide a device with higher efficiency and longer life.

[0035] In addition, a linking group having a structure in which at least one hydrogen atom bonded to a carbon atom adjacent to a carbon atom of an aromatic ring in a linear alkylene bonded to an aromatic ring (aryl ring or heteroaryl ring) in a polycyclic aromatic compound represented by formula (1) or a multimer of a polycyclic aromatic compound having a plurality of structures represented by formula (1) is substituted, and a linking group in which two hydrogen atoms are substituted is more preferable. Examples of this substituent include an alkyl group having 1 to 5 carbon atoms (particularly methyl), a halogen atom (particularly fluorine), and deuterium.

[0036] In formula (1), ring A, ring B, and ring C are each independently an aryl ring or a heteroaryl ring. At least one hydrogen atom in these rings may be substituted.

[0037] At least any one of ring A, ring B, and ring C is preferably an aryl ring having at least one substituent or a heteroaryl ring having at least one substituent, more preferably ring A, ring B, and ring C are all aryl rings having at least one substituent or heteroaryl rings having at least one substituent, and further preferably ring A, ring B, and ring C are each an aryl ring having one substituent or a heteroaryl ring having one substituent.

[0038] In this case, the substituent is preferably L-Cy, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted diarylamino, substituted or unsubstituted diheteroarylamino, substituted or unsubstituted arylheteroarylamino (amino having aryl and heteroaryl), substituted or unsubstituted diarylboryl (two aryls may be bonded via a single bond or a linking group), substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryloxy, or substituted silyl. When these groups have a substituent, the substituent is preferably L-Cy, aryl, heteroaryl, alkyl, cycloalkyl, diarylamino, or substituted silyl.

[0039] As the substituent other than L-Cy, a substituted or unsubstituted alkyl (especially neopentyl) or a cycloalkyl such as adamantyl is particularly preferred. Also, a tertiary alkyl (tR) is preferred. This is because such a bulky substituent increases the intermolecular distance, thereby improving the luminescence quantum yield (PLQY).

[0040] The tertiary alkyl is represented by the following formula (tR): [ka]

[0041] In the formula (tR), R a , R b , and R c are each independently an alkyl group having 1 to 24 carbon atoms, and any -CH 2 - may be replaced by -O-, and the group represented by formula (tR) replaces at least one hydrogen in the compound or structure represented by formula (1) at *.

[0042] R a , R b , and R c The "alkyl having 1 to 24 carbon atoms" may be either linear or branched, and examples thereof include linear alkyl having 1 to 24 carbon atoms or branched alkyl having 3 to 24 carbon atoms, alkyl having 1 to 18 carbon atoms (branched alkyl having 3 to 18 carbon atoms), alkyl having 1 to 12 carbon atoms (branched alkyl having 3 to 12 carbon atoms), alkyl having 1 to 6 carbon atoms (branched alkyl having 3 to 6 carbon atoms), and alkyl having 1 to 4 carbon atoms (branched alkyl having 3 to 4 carbon atoms).

[0043] R in formula (tR) of formula (1) a , R b , and R c The total number of carbon atoms is preferably 3 to 20, and particularly preferably 3 to 10.

[0044] R a , R b , and R cSpecific examples of alkyl include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, t-butyl, n-pentyl, isopentyl, neopentyl, t-pentyl, n-hexyl, 1-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, n-heptyl, 1-methylhexyl, n-octyl, t-octyl, 1-methylheptyl, 2 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.

[0045] Examples of the group represented by the formula (tR) include t-butyl, t-amyl, 1-ethyl-1-methylpropyl, 1,1-diethylpropyl, 1,1-dimethylbutyl, 1-ethyl-1-methylbutyl, 1,1,3,3-tetramethylbutyl, 1,1,4-trimethylpentyl, 1,1,2-trimethylpropyl, 1,1-dimethyloctyl, 1,1-dimethylpentyl, 1,1-dimethylheptyl, 1,1,5-trimethylhexyl, 1-ethyl- Examples include 1-methylhexyl, 1-ethyl-1,3-dimethylbutyl, 1,1,2,2-tetramethylpropyl, 1-butyl-1-methylpentyl, 1,1-diethylbutyl, 1-ethyl-1-methylpentyl, 1,1,3-trimethylbutyl, 1-propyl-1-methylpentyl, 1,1,2-trimethylpropyl, 1-ethyl-1,2,2-trimethylpropyl, 1-propyl-1-methylbutyl, 1,1-dimethylhexyl, etc. Among these, t-butyl and t-amyl are preferred.

[0046] Substituted or unsubstituted diarylamino is also preferred as the substituent. This is because such bulky substituents increase the intermolecular distance, thereby improving the luminescence quantum yield (PLQY). For example, R in the polycyclic aromatic compound represented by formula (1-a) and its multimer is 2is a substituted or unsubstituted diarylamino (preferably unsubstituted diarylamino).

[0047] Other preferred examples of the substituents in ring A, ring B, and ring C include, for example, diarylamino substituted with a group of formula (tR), carbazolyl substituted with a group of formula (tR), or benzocarbazolyl substituted with a group of formula (tR). For "diarylamino", the group described below as the "first substituent" is included. Examples of the substitution form of the group of formula (tR) on diarylamino, carbazolyl, and benzocarbazolyl include examples in which some or all of the hydrogen atoms on the aryl ring or benzene ring in these groups are substituted with the group of formula (tR).

[0048] The aryl or heteroaryl rings in the A, B and C rings are each independently selected from the group consisting of Y 1 , X 1 and X 2 The formula (1) may have a 5- or 6-membered ring sharing a bond with the central fused two-ring structure. Here, the "fused two-ring structure" refers to the Y 1 , X 1 and X 2 means a structure in which two saturated hydrocarbon rings are fused together. In addition, "a six-membered ring sharing a bond with the fused two-ring structure" means a six-membered ring (e.g., a benzene ring) fused to the fused two-ring structure. In addition, "an aryl ring or heteroaryl ring (which is ring A) has this six-membered ring" means that ring A is formed only from this six-membered ring, or that ring A is formed by further condensing other rings to this six-membered ring so as to include this six-membered ring. In other words, "an aryl ring or heteroaryl ring (which is ring A) having a six-membered ring" means that the six-membered ring constituting all or part of ring A is fused to the fused two-ring structure. The same explanation applies to "ring B", "ring C" and "five-membered ring".

[0049] The A ring in formula (1) is the same as the a ring and its substituent R in formulas (1-a), (1-b), (1-c), (1-d), (1-e), and (1-f). 1 ~R 3 The B ring in formula (1) corresponds to the b ring and its substituent R in formulas (1-a), (1-b), and (1-c). 8 ~R 11 , the ring b in formula (1-d) and its substituent R 10 and R 11 and the ring b and its substituent R in formula (1-e) and formula (1-f). 8 and R 9 The C ring in formula (1) corresponds to the c ring and its substituent R in formula (1-a). 4 ~R 7 , the ring c and its substituent R in formula (1-b), formula (1-d), and formula (1-f) 4 and R 5 and the ring c and its substituent R in formula (1-c) and formula (1-e). 6 and R 7 That is, formula (1-a) corresponds to a structure in which rings having at least a 6-membered ring structure are selected as rings A to C of formula (1), and formulas (1-b), (1-c), (1-d), (1-e), and (1-f) correspond to structures in which rings having at least a 6-membered ring structure and rings having at least a 5-membered ring structure are selected as rings A to C of formula (1), respectively. In this sense, each ring in formula (1-a) is represented by lowercase letters a to c.

[0050] X in formula (1-b), formula (1-c), formula (1-d), formula (1-e), and formula (1-f) X are each independently >O, >S, >NR, or >C(-R) 2 Here, R in the >NR is an optionally substituted aryl, an optionally substituted heteroaryl, an optionally substituted alkyl, or an optionally substituted cycloalkyl, preferably an optionally substituted aryl, and more preferably an unsubstituted aryl. 2R is each independently hydrogen, aryl which may be substituted with alkyl or cycloalkyl, heteroaryl which may be substituted with alkyl or cycloalkyl, alkyl, or cycloalkyl, preferably alkyl, and more preferably methyl. >C(-R) 2 In the above formula, it is preferable that the two R's are the same. 2 It is also preferred that the two R's are bonded to each other to form a ring.

[0051] In formula (1-a), formula (1-b), formula (1-c), formula (1-d), formula (1-e), and formula (1-f), R 1 ~R 11 are each independently L-Cy, hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl (two aryls may be bonded via a single bond or a linking group), alkyl, cycloalkyl, alkoxy, aryloxy, or substituted silyl. At least one hydrogen in these may be substituted with aryl, heteroaryl, alkyl, cycloalkyl, or substituted silyl. The aryl and heteroaryl in these groups may be substituted with L-Cy.

[0052] R 1 ~R 11 are preferably each independently L-Cy, hydrogen, alkyl (particularly the above-mentioned tertiary alkyl (tR), neopentyl, etc.), cycloalkyl (e.g., adamantyl, etc.), substituted or unsubstituted diarylamino, or substituted silyl (triphenylsilyl, trimethylsilyl, etc.).

[0053] R in formula (1-a), formula (1-b), formula (1-c), formula (1-d), formula (1-e), and formula (1-f) 1 ~R 3 Among them, 0 to 1 are other than hydrogen (particularly the above-mentioned preferred substituents), and the rest are hydrogen; R 4 ~R 7Among them, 0 to 1 are other than hydrogen (particularly the above-mentioned preferred substituents), and the rest are hydrogen; R 8 ~R 11 Among these, it is preferred that 0 to 1 of them is other than hydrogen (particularly the above-mentioned preferred substituents) and the rest are hydrogen; R 1 ~R 3 Among them, one is other than hydrogen (particularly the above-mentioned preferred substituents) and the others are hydrogen; R 4 ~R 7 Among them, one is other than hydrogen (particularly the above-mentioned preferred substituents) and the others are hydrogen; R 8 ~R 11 It is more preferable that one of them is other than hydrogen (particularly the above-mentioned preferred substituents) and the others are hydrogen.

[0054] In the formulae (1-a), (1-b), (1-c), (1-d), (1-e), and (1-f), the substituents R 1 ~R 11 Adjacent groups among may be bonded together 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 L-Cy, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl (two aryls may be bonded via a single bond or a linking group), alkyl, cycloalkyl, alkoxy, aryloxy, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, or alkyldicycloalkylsilyl. At least one hydrogen atom in these may be substituted with aryl, heteroaryl, alkyl, or cycloalkyl. The aryl and heteroaryl in these groups may be substituted with L-Cy.

[0055] Therefore, the polycyclic aromatic compounds represented by formula (1-a), formula (1-b), formula (1-c), formula (1-d), formula (1-e), and formula (1-f) have ring structures that change depending on the mutual bonding forms of the substituents in the a ring, the b ring, and the c ring. For example, the polycyclic aromatic compound represented by formula (1-a) has ring structures that change as shown in the following formulas (1-a-1) and (1-a-2). 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.

[0056] [ka]

[0057] The A' ring, B' ring, and C' ring in the above formula (1-a-1) and formula (1-a-2) are each independently a substituent R 1 ~R 11 Adjacent groups among these are bonded to each other to form an aryl or heteroaryl ring together with the ring a, ring b, and ring c, respectively (they may also be considered as fused rings formed by fusing other ring structures to the ring a, ring b, or ring c). Although not shown in the formula, there are also compounds in which the ring a, ring b, and ring c are all changed to ring A', ring B', and ring C'. As can be seen from the above formulas (1-a-1) and (1-a-2), for example, R of ring b in formula (1-a) 8 and R in c-ring 7 , R in ring b 11 and a-ring R 1 , R in ring c 4 and a-ring R 3 etc. are not considered to be "adjacent groups" and are not bonded to each other unless otherwise specified. In other words, "adjacent groups" refers to groups that are adjacent on the same ring.

[0058] The compounds represented by the above formula (1-a-1) or formula (1-a-2) are compounds having ring A' (or ring B' or ring C') formed by condensing a benzene ring, which is ring a (or ring b or ring c) in formula (1-a), with a benzene ring, an indole ring, a pyrrole ring, a furan ring, a thiophene ring, a benzofuran ring, a benzothiophene ring, a cyclopentadiene ring, or an indene ring, and the condensed ring A' (or condensed ring B' or condensed ring C') thus formed is a naphthalene ring, a carbazole ring, an indole ring, a benzofuran ring, a benzothiophene ring, a dibenzofuran ring, a dibenzothiophene ring, an indene ring, or a fluorene ring, respectively.

[0059] Similarly, in formula (1-b), formula (1-c), formula (1-d), formula (1-e), and formula (1-f), a fused ring may be formed by condensing another ring structure to ring a, ring b, or ring c. For example, the benzene ring which is ring a or ring b may be condensed to another ring structure to form a fused ring, similar to the benzene ring in formula (1-a).

[0060] In the formulae (1-b), (1-c), (1-d), (1-e), and (1-f), in the 5-membered ring which is the b ring or the c ring, R 4 ~R 11 It is particularly preferred that adjacent groups among the above are bonded to each other to form a ring to form a condensed ring. For example, in the ring c of formula (1-b) and formula (1-c), and the rings b and c of formula (1-d), formula (1-e), and formula (1-f), R 3 ~R 11 Adjacent groups among these can be bonded to each other to form a ring, thereby forming a fused ring, ring B' or ring C'. Examples of the fused ring when the ring formed is a benzene ring include an indole ring, a benzofuran ring, and a benzothiophene ring.

[0061] For example, in the formulas (1-b), (1-c), (1-d), (1-e), and (1-f), for example, X XWhen is >O, ring b or ring c is a furan ring, and the ring corresponding to ring B' or ring C' in formula (1-a-1) formed by condensing a benzene ring to this furan ring is a benzofuran ring. In addition, for example, in the formulas (1-b), (1-c), (1-d), (1-e), and (1-f), for example, X X When is >S, ring b or ring c is a thiophene ring, and the ring corresponding to ring B' or ring C' in formula (1-a-1) formed by condensing a benzene ring to this thiophene ring is a benzothiophene ring.

[0062] As an example, in the five-membered ring which is the ring c in formula (1-b), R 4 and R 5 The following is an example of a fused ring formed by bonding together to form a benzene ring. [ka]

[0063] In formula (1-b-1), R 1 , R 2 , R 3 , R 8 , R 9 , R 10 , R 11 , X X , Y 1 , X 1 and X 2 R has the same meaning as in formula (1-b), and the preferred ranges are also the same. 4b , R 5b , R 6b , R 7bis a substituent selected from the group consisting of L-Cy, hydrogen, or aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl (two aryls may be bonded via a single bond or a linking group), alkyl, cycloalkyl, alkoxy, aryloxy, and substituted silyl, and at least one hydrogen in these substituents may be substituted with aryl, heteroaryl, alkyl, cycloalkyl, or substituted silyl. In addition, the aryl and heteroaryl in these groups may be substituted with L-Cy. R 4b , R 5b , R 6b , R 7b Among them, it is preferable that 0 to 2 are substituents other than hydrogen and the rest are hydrogen, and it is more preferable that one is a substituent other than hydrogen and the rest are hydrogen. For the preferable range of the substituent other than hydrogen, the description of the substituent described below as the first substituent (which may have a second substituent) can be referred to. As the substituent other than hydrogen, it is particularly preferable that it is alkyl (particularly the above tertiary alkyl (tR), neopentyl, etc.), cycloalkyl (for example, adamantyl, etc.), or substituted or unsubstituted diarylamino.

[0064] Y in formula (1) 1 is B, P, P=O, P=S, Al, Ga, As, Si-R, or Ge-R. 1 In the formula, R in Si-R and Ge-R is independently aryl or alkyl. 1 When Y is P=O, P=S, Si-R, or Ge-R, the atom bonded to the A ring, B ring, or C ring is P, Si, or Ge. 1is preferably B, P, P=O, P=S, or Si-R, more preferably B, P, or P=O, and particularly preferably B. This explanation applies to Y in formulas (1-a), (1-b), (1-c), (1-d), (1-e), (1-f), (1-a-3-1) to (1-a-3-3), (1-a-7-1), (1-a-7-2), (1-a-4), (1-a-4-1), (1-a-4-2), (1-a-5-1), (1-a-5-2), (1-a-5-3), (1-a-5-4), and (1-a-6). 1 But it's the same.

[0065] X in formula (1) 1 and X 2 are independently >O, >NR, >C(-R) 2 , >S, or >Se, >O, >C(-R) 2 or >NR. 1 and X 2 At least one of X is preferably >NR, and all of X are preferably >NR or X is preferably >NR. 1 and X 2 One of them is >NR and the other is >C(-R) 2 It is more preferable that both are >NR. X 1 and X 2 >C(-R) in 2R is each independently hydrogen, an aryl which may be substituted, a heteroaryl which may be substituted, an alkyl which may be substituted, or a cycloalkyl which may be substituted, and is preferably L-Cy, an aryl which may be substituted with an alkyl or a cycloalkyl, an optionally substituted heteroaryl which may be substituted with an alkyl or a cycloalkyl, an alkyl, or a cycloalkyl. Here, the aryl is particularly preferably an aryl having 6 to 10 carbon atoms (e.g., phenyl, naphthyl, etc.), the heteroaryl is particularly preferably a heteroaryl having 2 to 15 carbon atoms (e.g., carbazolyl, etc.), the alkyl is particularly preferably an alkyl having 1 to 5 carbon atoms (e.g., methyl, ethyl, etc.), and the cycloalkyl is particularly preferably a cycloalkyl having 5 to 10 carbon atoms (preferably cyclohexyl or adamantyl). >C(-R) 2 In the above, the two R's are preferably the same, and the two R's may be bonded to form a ring. 2 It is preferable that both of the two R's are methyl. Examples of compounds in which two R's are bonded to form a ring include compounds such as the following compound (1-303).

[0066] [ka]

[0067] X 1 and X 2In the above, R in >NR is an aryl which may be substituted (but preferably excluding amino as a substituent), a heteroaryl which may be substituted, an alkyl which may be substituted, or a cycloalkyl which may be substituted. Examples of the aryl, heteroaryl, alkyl, or cycloalkyl include the groups described below, and in particular, the aryl is preferably an aryl having 6 to 10 carbon atoms (e.g., phenyl, naphthyl, etc.), the heteroaryl is preferably a heteroaryl having 2 to 15 carbon atoms (e.g., carbazolyl, etc.), the alkyl is preferably an alkyl having 1 to 5 carbon atoms (e.g., methyl, ethyl, etc.), and the cycloalkyl is preferably a cycloalkyl having 5 to 10 carbon atoms (preferably cyclohexyl or adamantyl). In addition, the second substituent in this case is preferably, for example, an alkyl such as L-Cy, methyl, tertiary butyl, and amyl, or a substituted silyl such as p-tertiary butylphenyl or trimethylsilyl. The substitution position of the alkyl is preferably the para position with respect to the substitution position of the above N.

[0068] Specifically, X 1 and X 2 R in >NR in is preferably L-Cy, an aryl having 6 to 12 carbon atoms which may be substituted with an alkyl having 1 to 5 carbon atoms or a cycloalkyl having 5 to 10 carbon atoms, or an alkyl having 1 to 6 carbon atoms, preferably L-Cy or an aryl having 6 to 12 carbon atoms which may be substituted with an alkyl having 1 to 5 carbon atoms, more preferably L-Cy or a phenyl which may be substituted with an alkyl having 1 to 5 carbon atoms, and even more preferably an ortho-biphenyl (phenyl having a phenyl at the ortho position relative to N, 2-biphenyl) which may be substituted with an alkyl having 1 to 5 carbon atoms, or L-Cy or an alkyl having 1 to 5 carbon atoms. X 1 and X 2 It is particularly preferred that only one of the >NR in is ortho-biphenyl. An example is a compound represented by the following formula (1-221).

[0069] [ka]

[0070] X 1 and X 2 R in >NR may be bonded to at least one of the rings A, B, and C through a linking group or a single bond. The linking group may be -O-, -S-, or -C(-R) 2 In addition, the above-mentioned "-C(-R) 2 R in "-" is hydrogen, alkyl, or cycloalkyl. This definition is applicable, for example, to X represented by the following formula (1-a-3-1): 1 Or X 2 can be expressed as a compound having a ring structure in which X is incorporated into the fused ring B' and the fused ring C'. That is, for example, the compound having X in the benzene ring which is the b ring (or the c ring) in formula (1-a) 1 (or X 2 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 carbazole ring, a phenoxazine ring, a phenothiazine ring, or an acridine ring.

[0071] In addition, the above provision is based on the following formula (1-a-3-2) or formula (1-a-3-3), 1 and / or X 2 In other words, for example, the a-ring in formula (1-a) is a benzene ring, and X 1 (and / or X 2 The compound has a ring A' formed by condensing another ring so as to incorporate the ring A'. The condensed ring A' formed is, for example, a carbazole ring, a phenoxazine ring, a phenothiazine ring, or an acridine ring.

[0072] [ka]

[0073] X in formula (1-a), formula (1-b), formula (1-c), formula (1-d), formula (1-e), and formula (1-f)1 and X 2 are independently >O, >C(-R) 2 or >NR. For preferred ranges and specific examples of R, see X in formula (1) above. 1 and X 2 is the same as:

[0074] The rings B and C in formula (1), or the rings b and c in formula (1-a) may be bonded to each other via a single bond or a linking group. Such a form is represented by formula (1-a-7-1) or formula (1-a-7-2). In formula (1-a-7-1) and formula (1-a-7-2), the single bond or linking group is represented by Xz. The linking group may be -O-, -S-, or -C(-R). 2 In addition, the above "-C(-R) 2 R in "-" is hydrogen, alkyl, or cycloalkyl, and two R may form a ring.

[0075] [ka]

[0076] The "aryl ring" which is ring A, ring B, and ring C in formula (1) can be, 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.

[0077] Specific examples of the "aryl ring" include a monocyclic benzene ring, a bicyclic bicyclic ring, a naphthalene ring and an indene ring, a tricyclic terphenyl ring (m-terphenyl, o-terphenyl, p-terphenyl), a fused tricyclic ring, an acenaphthylene ring, a fluorene ring, a phenalene ring, and a phenanthrene ring, a fused tetracyclic ring, a triphenylene ring, a pyrene ring, and a naphthacene ring, and a fused pentacyclic ring, a perylene ring, a pentacene ring, and the like.

[0078] 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, as ring-constituting atoms other than carbon, 1 to 5 heteroatoms selected from oxygen, sulfur, and nitrogen. The "heteroaryl ring" refers to X in formulas (1-b), (1-c), (1-d), (1-e), and (1-f). x or the "R" defined in formula (1-a), formula (1-b), formula (1-c), formula (1-d), formula (1-e), and formula (1-f). 1 ~R 11 adjacent groups among these are bonded to form a heteroaryl ring together with ring a, ring b, or ring c.

[0079] Specific examples of the "heteroaryl ring" include a pyrrole ring, an oxazole ring, an isoxazole ring, a thiazole ring, an isothiazole ring, an imidazole ring, an oxadiazole ring, a thiadiazole ring, a triazole ring, a tetrazole ring, a pyrazole ring, a pyridine ring, a pyrimidine ring, a pyridazine ring, a pyrazine ring, a triazine ring, an indole ring, an isoindole ring, a 1H-indazole ring, a benzimidazole ring, a benzoxazole ring, a benzothiazole ring, a 1H-benzotriazole ring, a quinoline ring, an isoquinoline ring, a cinnoline ring, a quinazoline ring, and the like. Examples of such rings include a phosphorus 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, a phenazasiline ring, an indolizine ring, a furan ring, a benzofuran ring, an isobenzofuran ring, a dibenzofuran ring, a thiophene ring, a benzothiophene ring, a dibenzothiophene ring, a furazan ring, a thianthrene ring, an indolocarbazole ring, a benzoindolocarbazole ring, a benzobenzoindolocarbazole ring, and a naphthobenzofuran ring.

[0080] At least one hydrogen atom in the above-mentioned "aryl ring" or "heteroaryl ring" may be substituted with a first substituent, which is a substituted or unsubstituted "aryl", a substituted or unsubstituted "heteroaryl", a substituted or unsubstituted "diarylamino", a substituted or unsubstituted "diheteroarylamino", a substituted or unsubstituted "arylheteroarylamino", a substituted or unsubstituted "diarylboryl (two aryls may be bonded via a single bond or a linking group)", a substituted or unsubstituted "alkyl", a substituted or unsubstituted "cycloalkyl", a substituted or unsubstituted "alkoxy", a substituted or unsubstituted "aryloxy", or a substituted "silyl". Examples of the first substituent, the "aryl" or "heteroaryl" in the "diarylamino", the heteroaryl in the "diheteroarylamino", the aryl and heteroaryl in the "arylheteroarylamino", the aryl in the "diarylboryl", and the aryl in the "aryloxy" include the monovalent groups of the above-mentioned "aryl ring" or "heteroaryl ring".

[0081] 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 8 carbon atoms (branched alkyl having 3 to 8 carbon atoms) is even more preferred, an alkyl having 1 to 6 carbon atoms (branched alkyl having 3 to 6 carbon atoms) is particularly preferred, and an alkyl having 1 to 5 carbon atoms (branched alkyl having 3 to 5 carbon atoms) is most preferred.

[0082] Specific examples of alkyl include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, t-butyl, n-pentyl, isopentyl, neopentyl, t-pentyl (t-amyl), n-hexyl, 1-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, n-heptyl, 1-methylhexyl, n-octyl, t-octyl (1,1,3,3-tetramethylbutyl), and the like. ), 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 2,6-dimethyl-4-heptyl, 3,5,5-trimethylhexyl, n-decyl, n-undecyl, 1-methyldecyl, n-dodecyl, n-tridecyl, 1-hexylheptyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, n-heptadecyl, n-octadecyl, and n-eicosyl. Further, for example, 1-ethyl-1-methylpropyl, 1,1-diethylpropyl, 1,1-dimethylbutyl, 1-ethyl-1-methylbutyl, 1,1,4-trimethylpentyl, 1,1,2-trimethylpropyl, 1,1-dimethyloctyl, 1,1-dimethylpentyl, 1,1-dimethylheptyl, 1,1,5-trimethylhexyl, 1-ethyl-1-methylhexyl, 1-ethyl-1,3-dimethylbutyl, 1,1,2,2-tetramethylpropyl, 1-butyl-1-methylpentyl, 1,1-diethylbutyl, 1-ethyl-1-methylpentyl, 1,1,3-trimethylbutyl, 1-propyl-1-methylpentyl, 1,1,2-trimethylpropyl, 1-ethyl-1,2,2-trimethylpropyl, 1-propyl-1-methylbutyl, and 1,1-dimethylhexyl.

[0083] Furthermore, examples of the "cycloalkyl" as the first substituent include cycloalkyl having 3 to 24 carbon atoms, cycloalkyl having 3 to 20 carbon atoms, cycloalkyl having 3 to 16 carbon atoms, cycloalkyl having 3 to 14 carbon atoms, cycloalkyl having 5 to 10 carbon atoms, cycloalkyl having 5 to 8 carbon atoms, cycloalkyl having 5 to 6 carbon atoms, and cycloalkyl having 5 carbon atoms.

[0084] Specific examples of cycloalkyl include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, and alkyl (particularly methyl) substituted derivatives of these having 1 to 5 carbon atoms, as well as norbornyl, bicyclo[1.1.0]butyl, bicyclo[1.1.1]pentyl, bicyclo[2.1.0]pentyl, bicyclo[2.1.1]hexyl, bicyclo[3.1.0]hexyl, bicyclo[2.2.2]octyl, adamantyl, diamantyl, decahydronaphthalenyl, and decahydroazulenyl.

[0085] 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 5 carbon atoms (branched alkoxy having 3 to 5 carbon atoms) is particularly preferred.

[0086] Specific alkoxy includes methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, s-butoxy, t-butoxy, t-amyloxy, pentyloxy, hexyloxy, heptyloxy, octyloxy, and the like.

[0087] 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.

[0088] An example of the "trialkylsilyl" is a group in which three hydrogen atoms in a silyl are each independently substituted with an alkyl, and the alkyl can be cited from the groups described as the "alkyl" in the first substituent above. Preferred alkyl groups for substitution are alkyl groups having 1 to 5 carbon atoms, and specific examples thereof include methyl, ethyl, propyl, i-propyl, butyl, sec-butyl, t-butyl, and t-amyl.

[0089] 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.

[0090] Examples of "tricycloalkylsilyl" include a group in which three hydrogen atoms in silyl are independently replaced by cycloalkyl, and the cycloalkyl can be cited as the group described as "cycloalkyl" in the first substituent above. Preferred cycloalkyl for substitution is a cycloalkyl having 5 to 10 carbon atoms, specifically, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, bicyclo[1.1.1]pentyl, bicyclo[2.1.0]pentyl, bicyclo[2.1.1]hexyl, bicyclo[3.1.0]hexyl, bicyclo[2.2.1]heptyl, bicyclo[2.2.2]octyl, adamantyl, decahydronaphthalenyl, decahydroazulenyl, and the like.

[0091] Specific examples of tricycloalkylsilyl include tricyclopentylsilyl and tricyclohexylsilyl.

[0092] 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.

[0093] Specific examples of dialkylarylsilyl substituted with two alkyls and one aryl, alkyldiarylsilyl substituted with one alkyl and two aryls, and triarylsilyl substituted with three aryls include silyl substituted with a group selected from the above-mentioned specific alkyls and aryls. Specific examples of triarylsilyl include triphenylsilyl.

[0094] The "aryl" in the first substituent "diarylboryl" can be quoted from the above description of the aryl. In addition, the two aryls are not bound by a single bond or a linking group (e.g., >C(-R) 2 , >O, >S or >NR), where >C(-R) 2And R in >NR is aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, alkoxy, or aryloxy (the above, first substituent), and the first substituent may be further substituted with aryl, heteroaryl, alkyl, or cycloalkyl (the above, second substituent). As specific examples of these groups, the above-mentioned explanations of aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, alkoxy, and aryloxy as the first substituent can be cited.

[0095] As explained above, the first substituent, substituted or unsubstituted "aryl", substituted or unsubstituted "heteroaryl", substituted or unsubstituted "diarylamino", substituted or unsubstituted "diheteroarylamino", substituted or unsubstituted "arylheteroarylamino", substituted or unsubstituted "diarylboryl (two aryls may be bonded via a single bond or a linking group)", substituted or unsubstituted "alkyl", substituted or unsubstituted "cycloalkyl", substituted or unsubstituted "alkoxy", substituted or unsubstituted "aryloxy", or substituted "silyl" may have at least one hydrogen atom substituted with a second substituent. Examples of the second substituent include aryl, heteroaryl, alkyl, cycloalkyl, or substituted silyl, and specific examples thereof can be found in the above-mentioned monovalent group of the "aryl ring" or "heteroaryl ring", and the explanation of the "alkyl" or "cycloalkyl" as the first substituent. The aryl and heteroaryl as the second substituent also include structures in which at least one hydrogen atom in the aryl and heteroaryl as the second substituent is substituted with an aryl such as phenyl (specific examples are the groups mentioned above), an alkyl such as methyl and t-butyl (specific examples are the groups mentioned above), or a cycloalkyl such as cyclohexyl (specific examples are the groups mentioned above). As an example, when the second substituent is carbazolyl, the heteroaryl as the second substituent also includes a carbazolyl in which at least one hydrogen atom at the 9-position is substituted with an aryl such as phenyl, an alkyl such as methyl, or a cycloalkyl such as cyclohexyl.

[0096] The emission wavelength can be adjusted by the steric hindrance, electron donating property and electron withdrawing property of the structure of the first substituent. The groups represented by the following structural formulas are preferred, and more preferred are methyl, t-butyl, t-amyl, t-octyl, neopentyl, cyclohexyl, adamantyl, phenyl, o-tolyl, p-tolyl, 2,4-xylyl, 2,5-xylyl, 2,6-xylyl, 2,4,6-mesityl, diphenylamino, di-p-tolylamino, bis(p-(t-butyl)phenyl)amino, carbazolyl, 3,6-dimethylcarbazolyl, Preferred are 3,6-di-t-butylcarbazolyl and phenoxy, and more preferred are methyl, t-butyl, t-amyl, t-octyl, neopentyl, adamantyl, phenyl, o-tolyl, 2,6-xylyl, 2,4,6-mesityl, diphenylamino, di-p-tolylamino, bis(p-(t-butyl)phenyl)amino, carbazolyl, 3,6-dimethylcarbazolyl and 3,6-di-t-butylcarbazolyl. From the viewpoint of ease of synthesis, larger steric hindrance is preferred for selective synthesis, and specifically, t-butyl, t-amyl, t-octyl, adamantyl, o-tolyl, p-tolyl, 2,4-xylyl, 2,5-xylyl, 2,6-xylyl, 2,4,6-mesityl, di-p-tolylamino, bis(p-(t-butyl)phenyl)amino, 3,6-dimethylcarbazolyl and 3,6-di-t-butylcarbazolyl are preferred.

[0097] In the structural formula below, "Me" is methyl, "tBu" is t-butyl, "tAm" is t-amyl, "tOct" is t-octyl, and * indicates the bond position. [ka]

[0098] [ka]

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[0112] The present invention also relates to a multimer of a polycyclic aromatic compound having a plurality of unit structures represented by formula (1), preferably a multimer of a polycyclic aromatic compound having a plurality of unit structures represented by formula (1-a), (1-b), (1-c), (1-d), (1-e), or (1-f). The multimer is preferably a dimer to hexamer, more preferably a dimer to trimer, and particularly preferably a dimer. The multimer may have a form having a plurality of the above unit structures in one compound. For example, in addition to a form in which a plurality of the above unit structures are bonded together via a linking group such as a single bond, an alkylene having 1 to 3 carbon atoms, phenylene, or naphthylene (linked multimer), the multimer may also have a form in which any ring (ring A, ring B, or ring C, or ring a, ring b, or ring c, etc.) contained in the above unit structure is bonded so as to be shared by a plurality of unit structures (ring-shared multimer), or may have a form in which any ring (ring A, ring B, or ring C, or ring a, ring b, or ring c) contained in the above unit structure is bonded together so as to be condensed (ring-condensed multimer). However, ring-shared multimers and ring-condensed multimers are preferred, and ring-shared multimers are more preferred.

[0113] As such a multimer, for example, a multimer of a polycyclic aromatic compound having a plurality of unit structures represented by formula (1-a) includes a multimer compound represented by the following formula (1-a-4), formula (1-a-4-1), formula (1-a-4-2), formula (1-a-5-1) to formula (1-a-5-4), or formula (1-a-6). Each symbol in these formulas has the same meaning as each symbol in formula (1-a), and the preferred range is also the same. The multimer compound represented by the following formula (1-a-4) is a multimer compound having a plurality of unit structures represented by formula (1-a) in one compound, so as to share the benzene ring that is the a ring in formula (1-a). The multimer compound represented by the following formula (1-a-4-1) is a multimer compound having two unit structures represented by formula (1-a) in one compound, so as to share the benzene ring that is the a ring in formula (1-a). The multimeric compound represented by the following formula (1-a-4-2) is a multimeric compound having three unit structures represented by formula (1-a) in one compound, with the benzene ring being the a ring in formula (1-a) shared. The multimeric compound represented by the following formulas (1-a-5-1) to (1-a-5-4) is a multimeric compound having a plurality of unit structures represented by formula (1-a) in one compound, with the benzene ring being the b ring (or c ring) in formula (1-a) shared. The multimeric compound represented by the following formula (1-a-6), when explained using formula (1-a), is a multimeric compound having a plurality of unit structures represented by formula (1-a) in one compound, with the benzene ring being the b ring (or a ring, c ring) of a certain unit structure condensed with the benzene ring being the b ring (or a ring, c ring) of a certain unit structure. Furthermore, the multimeric compound represented by the following formula (1-a-7), when explained in terms of formula (1-a), is a multimeric compound having a plurality of unit structures represented by formula (1-a) in one compound, in which a benzene ring which is a b-ring and a benzene ring which is a c-ring of a certain unit structure are condensed with a benzene ring which is a c-ring (or a b-ring) of another unit structure.

[0114] [ka]

[0115] [ka]

[0116] The multimeric compound may be a multimer in which a multimerized form represented by formula (1-a-4), formula (1-a-4-1) or formula (1-a-4-2) is combined with a multimerized form represented by any one of formulas (1-a-5-1) to (1-a-5-4) or formula (1-a-6), and may be a multimer in which a multimerized form represented by any one of formulas (1-a-5-1) to (1-a-5-4) and It may be a multimer in which a multimerization form represented by formula (1-a-6) is combined with a multimerization form represented by formula (1-a-4), formula (1-a-4-1) or formula (1-a-4-2), a multimerization form represented by any of formulas (1-a-5-1) to (1-a-5-4), and a multimerization form represented by formula (1-a-6).

[0117] In addition, all or a part of the hydrogen atoms in the chemical structure of the polycyclic aromatic compound represented by formula (1) and its multimer may be deuterium, cyano, or halogen. For example, in formula (1), the A ring, the B ring, and the C ring (A to C rings are aryl rings or heteroaryl rings), the substituents on the A to C rings, and X 1 and X 2 >NR or >C(-R) 2 In the above formula, hydrogen in R (= alkyl, cycloalkyl, aryl) may be replaced by deuterium, cyano, or halogen, and among these, examples include an embodiment in which all or a part of hydrogen in aryl or heteroaryl is replaced by deuterium, cyano, or halogen. Halogen is fluorine, chlorine, bromine, or iodine, preferably fluorine, chlorine, or bromine, more preferably fluorine or chlorine, and most preferably fluorine. For example, as described above, it is preferred that at least one (preferably all) of the hydrogens in L of L-Cy be substituted with a halogen (preferably fluorine).

[0118] In addition, at least one of the aryl ring or heteroaryl ring in the chemical structure of the polycyclic aromatic compound and its multimer represented by formula (1) or formula (1-a), formula (1-b), formula (1-c), formula (1-d), formula (1-e), or formula (1-f) may be fused with at least one cycloalkane. In this specification, when L-Cy is bonded to any carbon on the cycloalkane ring of each of the aryl ring fused with the cycloalkane and the heteroaryl ring fused with the cycloalkane, L-Cy is also considered to be bonded to the aryl ring or heteroaryl ring.

[0119] For example, aryl and heteroaryl rings in the aryl and heteroaryl rings which are ring A, ring B, ring C, ring a, ring b, and ring c, aryl (aryl moiety in aryl, diarylamino, arylheteroarylamino, diarylboryl, or aryloxy) and heteroaryl (heteroaryl moiety in heteroaryl, diheteroarylamino, or arylheteroarylamino) as the first and second substituents in ring A to ring C, aryl (similar to above) and heteroaryl (similar to above) as the first and second substituents on ring a, ring b, and ring c, and X 1 , X 2 >NR, and >C(-R) 2 At least one of the aryl (as above) and heteroaryl (as above) as R in the formula (I) may be fused with at least one cycloalkane.

[0120] Preferably, the aryl and heteroaryl rings are ring A, ring B, ring C, ring a, ring b, and ring c; the aryl (aryl moiety in aryl, diarylamino, diarylboryl, or aryloxy) and the heteroaryl (heteroaryl moiety in heteroaryl or diheteroarylamino) as the first substituents in ring A to ring C; the aryl (similar to above) and the heteroaryl (similar to above) as the first substituents on ring a to ring c; and X 1 , X 2 >NR and >C(-R)2 At least one of the aryl (as above) and heteroaryl (as above) as R in the formula (I) may be fused with at least one cycloalkane.

[0121] More preferably, the aryl rings are ring A, ring B, ring C, ring a, ring b, and ring c; the aryl (aryl moiety in aryl or diarylamino) and heteroaryl (heteroaryl moiety in heteroaryl) as the first substituents in ring A to ring C; the aryl (similar to above) and heteroaryl (similar to above) as the first substituents on ring a, ring b, and ring c; and X 1 , X 2 >NR, and >C(-R) 2 At least one of the aryls (as above) as R may be condensed with at least one cycloalkane.

[0122] More preferably, the aryl rings are ring A, ring B, ring C, ring a, ring b, and ring c, the aryl as the first substituent in ring A to ring C (aryl or aryl moiety in diarylamino), the aryl as the first substituent on ring a, ring b, and ring c (similar to the above), and X 1 , X 2 >NR, and >C(-R) 2 At least one of the aryls (as above) as R may be condensed with at least one cycloalkane.

[0123] 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.

[0124] Specific examples of cycloalkanes include cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclooctane, cyclononane, cyclodecane, norbornene, bicyclo[1.1.0]butane, bicyclo[1.1.1]pentane, bicyclo[2.1.0]pentane, bicyclo[2.1.1]hexane, bicyclo[3.1.0]hexane, bicyclo[2.2.1]heptane, 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.

[0125] Among these, a structure in which at least one hydrogen atom is substituted on the α-position carbon atom of a cycloalkane (a carbon atom adjacent to the carbon atom at the condensation site in a cycloalkane fused to an aryl ring or heteroaryl ring) is preferred, a structure in which two hydrogen atoms are substituted on the α-position carbon atom is more preferred, and a structure in which a total of four hydrogen atoms are substituted on the two α-position carbon atoms 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.

[0126] In particular, it is preferable that the aryl ring or heteroaryl ring has a structure in which a partial structure represented by the following formula (B10) or (B11) is bonded to adjacent carbon atoms.

[0127] [ka]

[0128] In formula (B10) and formula (B11), Me represents methyl. * represents a bonding position, and is bonded to two adjacent elements on the aryl ring or heteroaryl ring to which the group represented by formula (B10) or formula (B11) is bonded, respectively. Examples of compounds having such structures include the following compounds:

[0129] [ka]

[0130] 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 aryl ring or heteroaryl ring other than a benzene ring (phenyl) or if the fused cycloalkane is a cycloalkane other than cyclopentane or cyclohexane.

[0131] [ka]

[0132] At least one -CH in the cycloalkane 2 - may be replaced by -O-. For example, one or more -CH 2 Examples in which - is replaced by -O- are shown below. The same applies even when the fused ring (group) is an aryl ring or heteroaryl ring other than a benzene ring (phenyl) or when the fused cycloalkane is a cycloalkane other than cyclopentane or cyclohexane.

[0133] [ka]

[0134] At least one hydrogen atom in the cycloalkane may be substituted, and examples of the substituent include L-Cy, 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 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.

[0135] [ka]

[0136] Other forms of cycloalkane condensation include polycyclic aromatic compounds and multimers thereof represented by formula (1) or formula (1-a), formula (1-b), formula (1-c), formula (1-d), formula (1-e), or formula (1-f), for example, R is an aryl condensed with a cycloalkane >NR, diarylamino condensed with a cycloalkane (condensed to this aryl portion), carbazolyl condensed with a cycloalkane (condensed to this benzene ring portion), or benzocarbazolyl condensed with a cycloalkane (condensed to this benzene ring portion). For "diarylamino", the group described above as the "first substituent" can be mentioned.

[0137] Further specific examples include R in polycyclic aromatic compounds and multimers thereof represented by formula (1) or formula (1-a), (1-b), (1-c), (1-d), (1-e), or (1-f). 2is a diarylamino fused to a cycloalkane (fused to the aryl moiety) or a carbazolyl fused to a cycloalkane (fused to the benzene ring moiety).

[0138] When the polycyclic aromatic compound represented by formula (1) or formula (1-a), (1-b), (1-c), (1-d), (1-e), or (1-f) and a polymer thereof are used as a dopant material in the light-emitting layer of an organic electroluminescent device, Y 1 B, X 1 and X 2 Compounds where Y is >NR 1 B, X 1 >O,X 2 Compounds where Y is >NR 1 B, X 1 and X 2 is preferably >O. When used as a host material in the light-emitting layer, 1 B, X 1 >O,X 2 Compounds where Y is >NR 1 B, X 1 and X 2 As the electron transport material, a compound in which Y 1 B, X 1 and X 2 Compounds in which Y is >O 1 P=O, X 1 and X 2 Compounds in which is >O are preferably used.

[0139] As described above, at least one of the aryl ring or heteroaryl ring in the chemical structure of the polycyclic aromatic compound represented by formula (1), formula (1-a), formula (1-b), formula (1-c), formula (1-d), formula (1-e) or formula (1-f) and its multimer is substituted with at least one L-Cy. All of the aryl rings and heteroaryl rings may be substituted with at least one L-Cy, some of the aryl rings and heteroaryl rings may be substituted with at least one L-Cy, or one of the multiple aryl rings or heteroaryl rings may be substituted with at least one L-Cy.

[0140] The aryl or heteroaryl ring substituted with L-Cy includes the aryl or heteroaryl ring which is the ring A, ring B, or ring C in formula (1), and X 1 and X 2 When R is >NR, an aryl ring or a heteroaryl ring contained in R is preferred. For example, in formula (1-a) and formula (1-b), R 2 and R 9 At least one selected from the group consisting of: 1 and X 2 or R 2 and R 9 At least one selected from the group consisting of is L-Cy, and X 1 and X 2 and n is 0 or 1; and n is 1 or 2; and n is 2 or 3; and n is 3 or 4; and n is 4 or 5; and n is 5 or 6;

[0141] Other examples of the form of substitution with L-Cy include polycyclic aromatic compounds represented by formula (1), formula (1-a), formula (1-b), formula (1-c), formula (1-d), formula (1-e), or formula (1-f) and their multimers, which are substituted with, for example, diarylamino substituted with at least one L-Cy, carbazolyl substituted with at least one L-Cy, or benzocarbazolyl substituted with at least one L-Cy. Examples of "diarylamino" include the groups described above as the "first substituent". Examples of the form of substitution of cycloalkyl on diarylamino, carbazolyl, and benzocarbazolyl include those in which some or all of the hydrogen atoms on the aryl ring or benzene ring in these groups are substituted with L-Cy.

[0142] Further, as a more specific example, R in the polycyclic aromatic compound and its multimer represented by the formula (1-a) 2 is diarylamino substituted with at least one L-Cy or carbazolyl substituted with at least one L-Cy.

[0143] An example of this is a polycyclic aromatic compound represented by the following formula (2-A), or a multimer of a polycyclic aromatic compound having a plurality of structures represented by the following formula (2-A). Each n is independently an integer of 1 to 5 (preferably 1), and the definition of each symbol in the structural formula is the same as the definition of each symbol in formula (1-a).

[0144] [ka]

[0145] Specific examples of the polycyclic aromatic compound and its multimer of the present invention include compounds in which one or more aromatic rings in the compound are substituted with, for example, 1 to 2 L-Cy.

[0146] Specifically, the compounds are represented by any of the following formulas: In the following formulas, n is each independently 0 to 2 (however, all n's cannot be 0), and is preferably 1. In the following structural formulas, "L" represents a linking group, "Cy" represents cycloalkyl, "OPh" represents phenoxy, and "Me" represents methyl, and in "L-Cy", L is the bonding position.

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[0157] More specific examples of the cycloalkyl-substituted polycyclic aromatic compounds of the present invention include compounds represented by the following structural formulas: In the structural formulas, "D" represents deuterium, "Me" represents methyl, "tBu" represents t-butyl, "Ph" represents phenyl, and "Mes" represents mesityl.

[0158] [ka]

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[0182] 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).

[0183] 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.

[0184] [ka]

[0185] 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.

[0186] 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.

[0187] 2. Method for producing polycyclic aromatic compounds and their polymers The polycyclic aromatic compound represented by formula (1) and its multimer, preferably the polycyclic aromatic compound represented by formulas (1-a), (1-b), (1-c), (1-d), (1-e), and (1-f) and its multimer, are basically prepared by first bonding the A ring (a ring) to the B ring (b ring) and the C ring (c ring) through bonding groups (X 1 Or X 2 (a) to produce an intermediate (first reaction), and then, the A ring (a ring), the B ring (b ring) and the C ring (c ring) are bonded with a bonding group (Y 1The final product can be produced by bonding with a group containing (second reaction). In the first reaction, for example, a general reaction such as a nucleophilic substitution reaction or an Ullmann reaction can be used for an etherification reaction, and a general reaction such as a Buchwald-Hartwig reaction can be used for an amination reaction. 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 addition, by using a raw material substituted with L-Cy somewhere in these reaction steps or adding a step of introducing L-Cy, the compound of the present invention in which the desired position is cycloalkyl substituted can be produced.

[0188] 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 and X 2 The case where X is an oxygen atom is shown below. First, 1 and X 2 The hydrogen atom between is orthometalated with n-butyllithium, sec-butyllithium, t-butyllithium, or the like. Then, boron trichloride, boron tribromide, or the like is added to carry out lithium-boron metal exchange, and then a tandem boron-Friedel-Crafts reaction can be carried out by adding a Bronsted base such as N,N-diisopropylethylamine to obtain the target compound. In the second reaction, a Lewis acid such as aluminum trichloride may be added to promote the reaction. The symbols in the structural formulae in the following schemes (1) and (2), and the subsequent schemes (3) to (28), are defined as above.

[0189] [ka]

[0190] The above schemes (1) and (2) mainly show the method for producing the polycyclic aromatic compounds represented by formula (1) and (1-a), but the multimers thereof 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) to (5). In this case, the target product can be obtained by doubling or tripling the amount of the reagent such as butyl lithium used.

[0191] [ka]

[0192] In the above scheme, lithium was introduced into the desired position by orthometalation. However, as in the following schemes (6) and (7), lithium can also be introduced into the desired position by introducing a bromine atom or the like into the desired position and then by halogen-metal exchange.

[0193] [ka]

[0194] In addition, in the method for producing a polymer explained in scheme (3), 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 (6) and (7), and then by halogen-metal exchange (the following schemes (8), (9), and (10)).

[0195] [ka]

[0196] 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.

[0197] By appropriately selecting the above synthesis method and the raw materials to be used, a cycloalkyl-substituted compound having a substituent at a desired position and having a substituent at a desired position, Y 1 is a boron atom, X 1 and X 2 It is possible to synthesize polycyclic aromatic compounds and polymers thereof in which the ring is an oxygen atom.

[0198] Next, as an example, Y 1 is a boron atom, X 1 and X 2 The case where X is a nitrogen atom is shown in the following schemes (11) and (12). 1 and X 2 As in the case where X is an oxygen atom, first 1 and X 2 The hydrogen atom between is orthometalated with n-butyllithium or the like. Then, 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 target compound. Here, a Lewis acid such as aluminum trichloride may be added to promote the reaction. In addition, by using a raw material substituted with L-Cy somewhere in these reaction steps or by adding a step of introducing L-Cy, the compound of the present invention in which the desired position is cycloalkyl-substituted can be produced.

[0199] [ka]

[0200] Also, Y 1 is a boron atom, X 1 and X 2 For the polymers in which is a nitrogen atom, lithium can also be introduced to 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 (6) and (7), and then by halogen-metal exchange (the following schemes (13), (14), and (15)).

[0201] [ka]

[0202] Next, as an example, Y 1 is phosphorus sulfide, phosphorus oxide or phosphorus atom, and X 1 and X 2 The cases where X is an oxygen atom are shown in the following schemes (16) to (19). 1 and X 2 The hydrogen atom between the two is orthometalated with n-butyllithium or the like. Next, phosphorus trichloride and sulfur are added in that order, and finally a Lewis acid such as aluminum trichloride and a Bronsted base such as N,N-diisopropylethylamine are added to carry out the 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 is a phosphorus oxide, and by treating with triethylphosphine, Y 1 In addition, by using a raw material substituted with L-Cy somewhere in these reaction steps or by adding a step of introducing L-Cy, the compound of the present invention in which the desired position is cycloalkyl-substituted can be produced.

[0203] [ka]

[0204] Also, Y 1 is phosphorus sulfide, X 1 and X 2 For the polymers in which Y is an oxygen atom, lithium can be introduced to the desired position by introducing halogens such as bromine and chlorine atoms to the desired position as in the above schemes (6) and (7), and then by halogen-metal exchange (see the following schemes (20), (21), and (22)). 1 is phosphorus sulfide, X 1 and X2 The polymers in which Y is an oxygen atom can also be obtained by treating Y with m-chloroperbenzoic acid (m-CPBA) as shown in schemes (18) and (19). 1 is a phosphorus oxide, and by treating with triethylphosphine, Y 1 It is possible to obtain a compound in which is a phosphorus atom.

[0205] [ka]

[0206] Here, Y 1 is B, P, P=O or P=S, and X 1 and X 2 Although the examples where is O or NR are described, by changing the raw material appropriately, Y 1 Compounds in which X is Al, Ga, As, Si-R or Ge-R, 1 and X 2 Compounds in which is S can also be synthesized.

[0207] Specific examples of solvents that can be used in the above reactions include t-butylbenzene and xylene.

[0208] In addition, in the formula (1-a), the substituents R 1 ~R 11Adjacent 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 (1-a) has a ring structure that constitutes the compound, as shown in formulas (1-a-1) and (1-a-2) in the following schemes (23) and (24), 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 (19) to the intermediates shown in the following schemes (23) and (24). In addition, the compound of the present invention in which the desired position is cycloalkyl-substituted can be produced by using a raw material substituted with L-Cy somewhere in these reaction steps or adding a step of introducing L-Cy.

[0209] [ka]

[0210] The rings A', B' and C' in the above formula (1-a-1) and formula (1-a-2) each independently represent a substituent R 1 ~R 11 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 rings 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.

[0211] In addition, in the formula (1-a), R of >NR and / or the >C(-R) 2 R is -O-, -S-, -C(-R) 2 The provision that "is bonded to the ring a, ring b, and / or ring c via a single bond" refers to X represented by formula (1-a-3-1) in the following scheme (25). 1 Or X 2Compounds having a ring structure in which X is incorporated into the fused ring B' and the fused ring C', and compounds represented by formula (1-a-3-2) or formula (1-a-3-3), 1 Or X 2 can be expressed as a compound having a ring structure in which is incorporated into the fused ring A'. These compounds can be synthesized by applying the synthesis methods shown in the above schemes (1) to (19) to the intermediates shown in the following scheme (25). In addition, by using a raw material substituted with L-Cy somewhere in these reaction steps or adding a step of introducing L-Cy, the compound of the present invention in which the desired position is cycloalkyl substituted can be produced.

[0212] [ka]

[0213] In the above synthesis schemes (1) to (17) and (20) to (25), before adding boron trichloride, boron tribromide, etc., X 1 and X 2 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.

[0214] Also, Y 1 In the case of phosphorus-based, X is as shown in the following schemes (26) and (27). 1 and X 2The hydrogen atom between (O in the following formula) is orthometalated with n-butyllithium, sec-butyllithium, t-butyllithium, or the like, and then 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 phosphine Friedel-Crafts reaction to obtain the target product. This reaction method is also described in International Publication No. 2010 / 104047 (e.g., page 27). In addition, by using a raw material substituted with L-Cy somewhere in these reaction steps or adding a step of introducing L-Cy, the compound of the present invention in which the desired position is cycloalkyl substituted can be produced.

[0215] [ka]

[0216] In the above schemes (26) and (27), a polymeric compound can be synthesized by using an orthometalation reagent such as butyllithium in a molar amount two or three times that of intermediate 1. In addition, 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 a metal can be introduced into the desired position by halogen-metal exchange.

[0217] In addition, for the polycyclic aromatic compound represented by formula (2-A), an intermediate substituted with L-Cy can be synthesized as shown in the following scheme (28), and the intermediate can be cyclized to synthesize a polycyclic aromatic compound substituted with L-Cy at a desired position. In scheme (28), Hal 1 , Hal 2 , Hal 3 , and Hal 4 Each of the symbols represents a halogen, X represents a halogen or hydrogen, and the other symbols are defined the same as in formula (1-a). The method for introducing L-Cy is as follows. An example will be explained using a compound in which the linking group L is alkylene.

[0218] First, a compound having rings A, B, and C is reacted with a carboxylic acid chloride having a corresponding cycloalkyl, and then, for example, a Friedel-Crafts reaction is used in the presence of a Lewis acid to induce a ketone (first reaction). Subsequently, a cycloalkyl having an alkylene as a linking group can be introduced by reducing the carbonyl, and a linking group having dimethylmethylene can be obtained by reacting two or more equivalents of methylmagnesium halide or methyllithium on the carbonyl, and a fluorinating agent such as dimethylaminosulfur fluoride (DAST) can be used to make a fluoroalkylene into a linking group (second reaction). In addition, a compound having rings A, B, and C is reacted with an alkyl halide having a corresponding cycloalkyl, and then a Friedel-Crafts reaction is performed in the presence of a Lewis acid to directly synthesize a compound having an alkylene as a linking group.

[0219] Next, a compound in which the linking group L is an ether will be described as an example. First, a phenol compound having rings A, B, and C is reacted with an alkyl halide having a corresponding cycloalkyl in the presence of a base such as potassium carbonate or sodium hydride to give a compound having an ether bond in the linking group.

[0220] Next, a compound in which the linking group L is an ester will be described as an example. First, a phenolic compound or a carboxylic acid having A ring, B ring, and C ring and a carboxylic acid or an alcohol having a corresponding cycloalkyl can be derived into a compound having an ester bond in the linking group by using a dehydrating agent such as N,N-dicyclohexylcarbodiimide (DCC) in the presence of a catalyst such as dimethylaminopyridine (DMAP).

[0221] [ka]

[0222] The intermediate before cyclization in scheme (28) can also be synthesized by the method shown in scheme (1) etc. In other words, by appropriately combining the Buchwald-Hartwig reaction, Suzuki coupling reaction, or etherification reaction by nucleophilic substitution reaction, Ullmann reaction etc., an intermediate having a desired substituent can be synthesized. In these reactions, the raw material that becomes the cycloalkyl-substituted precursor can be a commercially available product.

[0223] The compound of formula (2-A) having a diphenylamino group substituted with L-Cy can also be synthesized by the following method. That is, a bromobenzene group substituted with L-Cy and a trihalogenated aniline are subjected to an amination reaction such as the Buchwald-Hartwig reaction to introduce a diphenylamino group substituted with L-Cy, and then X 1 , X 2 When is NR, X can be used in an amination reaction such as the Buchwald-Hartwig reaction. 1 , X 2 When is O, the intermediate (M-3) can be derived by etherification with phenol, followed by transmetallation with a metallation reagent such as butyllithium, followed by a tandem boron-Friedel-Crafts reaction with a boron halide such as boron tribromide, followed by a Bronsted base such as diethylisopropylamine to synthesize the compound of formula (2-A). These reactions can also be applied to other compounds substituted with L-Cy.

[0224] Examples of the ortho-metallation reagent used in the above schemes (1) to (28) 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.

[0225] In addition, the metal-Y used in the above schemes (1) to (28) 1The metal exchange reagent for Y 1 trifluoride, Y 1 trichloride, Y 1 Tribromide of Y 1 of triiodide, etc. 1 Halide of CIPN(NEt 2 ) 2 Y etc. 1 Aminated halides of Y 1 Alkoxylated compounds of Y 1 and aryloxy compounds of the above.

[0226] The Bronsted bases used in the above schemes (1) to (28) 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, Ar 4 BNa, Ar 4 B.K., Ar 3 B, Ar 4 Si (wherein Ar is an aryl such as phenyl).

[0227] The Lewis acid used in the above schemes (1) to (28) is AlCl 3 , AlBr 3 , AlF 3 , B.F. 3 ·OEt 2 , BCl 3 , BBr 3 , GaCl 3 , GaBr 3 , InCl 3 , InBr 3 , In(OTf) 3 , SnCl 4 , SnBr 4 , AgOTf, ScCl 3 , Sc(OTf) 3 , ZnCl 2 , ZnBr 2 , Zn(OTf) 2 , MgCl2 , MgBr 2 , Mg(OTf) 2 , LiOTf, NaOTf, KOTf, Me 3 SiOTf, Cu(OTf) 2 , CuCl 2 , Y.C.L. 3 , Y(OTf) 3 , TiCl 4 , TiBr 4 , ZrCl 4 , ZrBr 4 , FeCl 3 , FeBr 3 , CoCl 3 , CoBr 3 Some examples include:

[0228] In the above schemes (1) to (28), 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 elimination ability, it is effective to use a Lewis acid that promotes their elimination.

[0229] 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 deuterium or cyano, or compounds in which hydrogen atoms are substituted with halogens such as fluorine or chlorine. Such compounds can be synthesized in the same manner as described above by using raw materials in which desired positions are deuterated, cyanated, fluorinated or chlorinated.

[0230] 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.

[0231] 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.

[0232] 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.

[0233] 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.

[0234] 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. In this specification, layers containing organic compounds in an organic EL element, such as a light-emitting layer, a hole injection layer, a hole transport layer, an electron transport layer, and an electron injection layer, are sometimes collectively referred to as an organic layer.

[0235] 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".

[0236] 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 non-alkali glass is used, and the thickness is sufficient to maintain mechanical strength, and may be, for example, 0.2 mm or more. The upper limit of the thickness is, for example, 2 mm or less, and preferably 1 mm or less. As for the material of the glass, it is preferable to use non-alkali glass because less ions are eluted from the glass, but SiO 2 Soda lime glass coated with a barrier coat such as a silicon oxide film is commercially available and can be used. In order to improve the gas barrier properties, a gas barrier film such as a dense silicon oxide film may be provided on at least one side of the substrate 101. In particular, when a synthetic resin plate, film, or sheet with low gas barrier properties is used as the substrate 101, it is preferable to provide a gas barrier film.

[0237] 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.

[0238] Materials for forming the anode 102 include inorganic compounds and organic compounds. Examples of inorganic compounds include metals (aluminum, gold, silver, nickel, palladium, chromium, etc.), metal oxides (indium oxide, tin oxide, indium-tin oxide (ITO), indium-zinc oxide (IZO), etc.), metal halides (copper iodide, etc.), copper sulfide, carbon black, ITO glass, and Nesa glass. Examples of organic compounds include polythiophenes such as poly(3-methylthiophene), polypyrrole, polyaniline, and other conductive polymers. In addition, materials that are used as anodes in organic EL elements can be appropriately selected and used.

[0239] The resistance of the transparent electrode is not limited as long as it can supply a sufficient current for the light emission of the light emitting element, but it is desirable that the resistance is low from the viewpoint of the power consumption of the light emitting element. For example, an ITO substrate of 300Ω / □ or less functions as an element electrode, but since it is now possible to supply substrates of about 10Ω / □, it is particularly desirable to use a low resistance product of, for example, 100 to 5Ω / □, preferably 50 to 5Ω / □. The thickness of the ITO can be selected arbitrarily according to the resistance value, but it is usually used in the range of 50 to 300 nm.

[0240] 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.

[0241] 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.

[0242] 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, N 4 ,N 4’ -Diphenyl-N 4 ,N 4’ -Bis(9-phenyl-9H-carbazol-3-yl)-[1,1'-biphenyl]-4,4'-diamine, N 4 ,N 4 ,N 4’ ,N 4’-Tetra[1,1'-biphenyl]-4-yl)-[1,1'-biphenyl]-4,4'-diamine, 4,4',4"-tris(3-methylphenyl(phenyl)amino)triphenylamine 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.

[0243] 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).

[0244] 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.

[0245] 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.

[0246] 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.

[0247] 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.

[0248] 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.

[0249] 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.

[0250] 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.

[0251] <Anthracene compounds> The anthracene compound as the host is, for example, a compound represented by the following formula (3). [ka]

[0252] In formula (3), 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 (3) may be substituted with halogen, cyano, deuterium or an optionally substituted heteroaryl.

[0253] In addition, a polymer (preferably a dimer) may be formed using the structure represented by formula (3) as a unit structure. In this case, for example, the unit structures represented by formula (3) 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 group having a divalent bond such as a pyridine ring, a dibenzofuran ring, a dibenzothiophene ring, a carbazole ring, a benzocarbazole ring, and a phenyl-substituted carbazole ring).

[0254] 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.

[0255] Preferred embodiments of the above anthracene-based compounds are described below. The symbols in the structures below are defined as above. [ka]

[0256] In formula (3), X is each independently a group represented by the above formula (3-X1), formula (3-X2) or formula (3-X3), and the group represented by formula (3-X1), formula (3-X2) or formula (3-X3) is bonded to the anthracene ring of formula (3) 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).

[0257] In addition, a polymer (preferably a dimer) may be formed using the structure represented by formula (3) as a unit structure. In this case, for example, the unit structures represented by formula (3) 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 group having a divalent bond such as a pyridine ring, a dibenzofuran ring, a dibenzothiophene ring, a carbazole ring, a benzocarbazole ring, and a phenyl-substituted carbazole ring).

[0258] 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]

[0259] 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 *.

[0260] 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 in formula (3) and the group represented by formula (A) are directly bonded.

[0261] 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.

[0262] 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.

[0263] 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.

[0264] 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.

[0265] Examples of the cycloalkyl having 5 to 10 carbon atoms substituting the silyl include cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, norbornyl, bicyclo[1.1.1]pentyl, bicyclo[2.1.0]pentyl, bicyclo[2.1.1]hexyl, bicyclo[3.1.0]hexyl, bicyclo[2.2.2]octyl, adamantyl, decahydronaphthalenyl, and decahydroazulenyl, and three hydrogen atoms in the silyl are each independently substituted with these cycloalkyls.

[0266] Specific examples of the "silyl substituted with cycloalkyl having 5 to 10 carbon atoms" include tricyclopentylsilyl and tricyclohexylsilyl.

[0267] 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.

[0268] In addition, hydrogen in the chemical structure of the anthracene compound represented by formula (3) 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 (3) at the *.

[0269] The group represented by formula (A) is one of the substituents that the anthracene compound represented by formula (3) can have. [ka]

[0270] 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.

[0271] 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.

[0272] 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.

[0273] 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.

[0274] 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 norbornyl, bicyclo[1.1.0]butyl, bicyclo[1.1.1]pentyl, bicyclo[2.1.0]pentyl, bicyclo[2.1.1]hexyl, bicyclo[3.1.0]hexyl, bicyclo[2.2.2]octyl, adamantyl, diamantyl, decahydronaphthalenyl, and decahydroazulenyl.

[0275] 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.

[0276] 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.

[0277] 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.

[0278] 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.

[0279] 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.

[0280] Specific examples of "alkoxy" include methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, s-butoxy, t-butoxy, pentyloxy, hexyloxy, heptyloxy, octyloxy, and the like.

[0281] 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.

[0282] 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.

[0283] 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.

[0284] 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.

[0285] 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, specifically cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, bicyclo[1.1.1]pentyl, bicyclo[2.1.0]pentyl, bicyclo[2.1.1]hexyl, bicyclo[3.1.0]hexyl, bicyclo[2.2.1]heptyl, bicyclo[2.2.2]octyl, adamantyl, decahydronaphthalenyl, decahydroazulenyl, and the like.

[0286] Specific examples of the "tricycloalkylsilyl" include tricyclopentylsilyl, tricyclohexylsilyl, and the like.

[0287] 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.

[0288] R 21 ~R 28 The "substituted amino" in the "optionally substituted amino" in the above is, for example, an amino in which two hydrogen atoms are substituted with aryl or heteroaryl. An amino in which two hydrogen atoms are substituted with aryl is a diaryl-substituted amino, an amino in which two hydrogen atoms are substituted with heteroaryl is a diheteroaryl-substituted amino, and an amino 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.

[0289] Specific examples of the "substituted amino" include diphenylamino, dinaphthylamino, phenylnaphthylamino, dipyridylamino, phenylpyridylamino, naphthylpyridylamino, and the like.

[0290] R 21 ~R 28 "Halogen" in the above formula includes fluorine, chlorine, bromine, and iodine.

[0291] 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".

[0292] 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.

[0293] 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.

[0294] [ka]

[0295] 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).

[0296] 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.

[0297] 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 bonded to the naphthalene ring in formula (3-X1) or formula (3-X2), and are substituted with at least one hydrogen atom in the compound represented by formula (3). 3 The form in which it is bound to is preferred.

[0298] In addition, in the structure of the group represented by formula (A), the naphthalene ring in formula (3-X1) or formula (3-X2), the single bond in formula (3-X3), Ar in formula (3-X3), 3 The position at which R is bonded, and the position at which at least one hydrogen atom in the compound represented by formula (3) is substituted in the structure of the group represented by formula (A), may be any position in the structure of formula (A), 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

[0299] Examples of the group represented by formula (A) include the following groups: In the formula, Y and * are defined as above. [ka]

[0300] All or a part of the hydrogen atoms in the chemical structure of the anthracene compound represented by formula (3) may be deuterium atoms.

[0301] Specific examples of the anthracene-based compound include compounds represented by the following formulae (3-1) to (3-72): In the following structural formulae, "Me" represents methyl, "D" represents deuterium, and "tBu" represents t-butyl.

[0302] [ka]

[0303] [ka]

[0304] [ka]

[0305] [ka]

[0306] The anthracene compound represented by formula (3) 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 referred to.

[0307] <Fluorene-based compounds> The compound represented by formula (4) basically functions as a host. [ka]

[0308] In the above formula (4), 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 (4) 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 (4) may be substituted with halogen, cyano or deuterium.

[0309] For details of each group in the definition of the above formula (4), the explanation for the polycyclic aromatic compound of the above formula (1) can be cited.

[0310] 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.

[0311] 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.

[0312] These heteroaryls may be bonded to the fluorene skeleton in the above formula (4) via a linking group. That is, the fluorene skeleton and the above heteroaryls in the formula (4) 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, -OCH 2 CH 2 -, -CH 2 CH 2O- or -OCH 2 CH 2 Examples include O-.

[0313] In addition, R in formula (4) 1 and R 2 , R 2 and R 3 , R 3 and R 4 , R 5 and R 6 , R 6 and R 7 or R 7 and R 8 are each independently bonded to form a fused ring, R 9 and R 10 may be bonded to form a spiro ring. 1 From R 8 The fused ring formed by is a ring fused to the benzene ring in formula (4), 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 (4) include a naphthalene ring and a phenanthrene ring. 9 and R 10 The spiro ring formed by the formula (4) is a ring that is spiro-bonded to the five-membered ring in the formula (4), and is an aliphatic ring or an aromatic ring. An aromatic ring, such as a fluorene ring, is preferred.

[0314] The compound represented by formula (4) 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 with 1 From R 8 is a compound in which none of the above is bound.

[0315] [ka]

[0316] R in formula (4-1), formula (4-2) and formula (4-3) 1 From R 10 The definition of R in Eq. (4) 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 Eq. (4) 1 From R 10 is the same as:

[0317] The compound represented by formula (4) 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.

[0318] [ka]

[0319] 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:

[0320] In addition, all or a part of the hydrogen atoms in the compound represented by formula (4) may be substituted with halogen, cyano or deuterium.

[0321] <Dibenzochrysene compounds> The dibenzochrysene compound as the host is, for example, a compound represented by the following formula (5). [ka]

[0322] In the above formula (5), R 1 From R 16 are each independently a hydrogen atom, an aryl, a heteroaryl (wherein the heteroaryl may be bonded to the dibenzochrysene skeleton in the above formula (5) 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 (5) may be substituted with halogen, cyano or deuterium.

[0323] 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.

[0324] The alkenyl in the definition of the above formula (5) 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.

[0325] 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).

[0326] [ka]

[0327] 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.

[0328] These heteroaryls may be bonded to the dibenzochrysene skeleton in the above formula (5) via a linking group. That is, the dibenzochrysene skeleton and the above heteroaryl in the formula (5) may be bonded directly or via a linking group. Examples of the linking group include phenylene, biphenylene, naphthylene, anthracenylene, methylene, ethylene, -OCH 2 CH 2 -, -CH 2 CH2 O- or -OCH 2 CH 2 Examples include O-.

[0329] The compound represented by formula (5) is preferably R 1 , R 4 , R 5 , R 8 , R 9 , R 12 , R 13 and R 16 is hydrogen. In this case, R in formula (5) 2 , R 3 , R 6 , R 7 , R 10 , R 11 , R 14 and R 15 each independently represents hydrogen, phenyl, biphenylyl, naphthyl, anthracenyl, phenanthrenyl, or a monovalent group having the structure of the above formula (5-Ar1), formula (5-Ar2), formula (5-Ar3), formula (5-Ar4), or formula (5-Ar5) (the monovalent group having the structure is phenylene, biphenylene, naphthylene, anthracenylene, methylene, ethylene, -OCH 2 CH 2 -, -CH 2 CH 2 O- or -OCH 2 CH 2 (which may be bonded to the dibenzochrysene skeleton in the above formula (5) via O-), methyl, ethyl, propyl, or butyl is preferred.

[0330] The compound represented by formula (5) is more preferably 1 , R 2 , R 4 , R 5 , R 7 , R 8 , R 9 , R 10 , R 12 , R 13 , R 15 and R 16 is hydrogen. In this case, R in formula (5) 3 , R6 , R 11 and R 14 At least one (preferably one or two, more preferably one) of the above is a single bond, phenylene, biphenylene, naphthylene, anthracenylene, methylene, ethylene, -OCH 2 CH 2 -, -CH 2 CH 2 O- or -OCH 2 CH 2 a monovalent group having the structure of the above formula (5-Ar1), formula (5-Ar2), formula (5-Ar3), formula (5-Ar4) or formula (5-Ar5) via O-; 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.

[0331] In addition, R in formula (5) 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.

[0332] 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.

[0333] <Example of polymer host material> [ka]

[0334] 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.

[0335] 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.

[0336] 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. 2 - is -O- or -Si(CH 3 ) 2 -, and -CH directly bonded to EC in formula (SPH-1) in the alkyl 2 Any -CH except 2 - may be substituted with an arylene having 6 to 24 carbon atoms, and any hydrogen in the alkyl may be substituted with a fluorine.

[0337] Examples of MU include a divalent group represented by removing any two hydrogen atoms from any of the following compounds: [ka]

[0338] More specifically, the divalent group may be any of the following structures: In these, MU bonds to another MU or EC at *.

[0339] [ka]

[0340] [ka]

[0341] [ka]

[0342] [ka]

[0343] Examples of EC include a monovalent group represented by any of the following structures: In these, EC is bonded to MU at *.

[0344] [ka]

[0345] [ka]

[0346] 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.

[0347] 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.

[0348] 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.

[0349] 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.

[0350] 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.

[0351] 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.

[0352] 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.

[0353] The above-mentioned materials may be used alone or in combination with different materials.

[0354] 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.

[0355] <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]

[0356] 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.

[0357] Among the compounds represented by formula (ETM-1), a compound represented by the following formula (ETM-1-1) or a compound represented by the following formula (ETM-1-2) is preferred.

[0358] [ka]

[0359] 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.

[0360] [ka]

[0361] 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.

[0362] 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.

[0363] Specific examples of the borane derivative include the following compounds: [ka]

[0364] The borane derivative can be produced using known raw materials and known synthesis methods.

[0365] <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]

[0366] 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.

[0367] 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).

[0368] 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.

[0369] 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.

[0370] [ka]

[0371] 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]

[0372] 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.

[0373] 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).

[0374] 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.

[0375] 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.

[0376] 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.

[0377] 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.

[0378] 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.

[0379] 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.

[0380] 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.

[0381] Specific examples of this pyridine derivative include, for example, the following compounds.

Chemical formula

[0382] This pyridine derivative can be produced using known raw materials and known synthesis methods.

[0383] <Fluoranthene derivative> The fluoranthene derivative is, for example, a compound represented by the following formula (ETM-3), and details are disclosed in International Publication No. 2010 / 134352.

Chemical formula

[0384] In formula (ETM-3), X 12 ~X 21 represents hydrogen, halogen, linear, branched or cyclic alkyl, linear, branched or cyclic alkoxy, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl. Here, examples of the substituent when it is substituted include aryl, heteroaryl, alkyl or cycloalkyl, etc.

[0385] Specific examples of this fluoranthene derivative include, for example, the following compounds.

Chemical formula

[0386] <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]

[0387] 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.

[0388] 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.

[0389] In addition, at least one hydrogen in the compound or structure represented by formula (ETM-4) may be substituted with a halogen or deuterium.

[0390] For an explanation of the substituents and the form of ring formation in formula (ETM-4), the explanation of the polycyclic aromatic compound represented by formula (1) or formula (1-a) etc. can be cited.

[0391] Specific examples of the BO derivative include the following compounds: [ka]

[0392] The BO derivative can be produced using known raw materials and known synthesis methods.

[0393] <Anthracene derivatives> One of the anthracene derivatives is, for example, a compound represented by the following formula (ETM-5). [ka]

[0394] Ar 1 are each independently a single bond, or a divalent benzene, naphthalene, anthracene, fluorene, or phenalene.

[0395] 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.

[0396] 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.

[0397] 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.

[0398] 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.

[0399] Specific examples of these anthracene derivatives include the following compounds. [ka]

[0400] These anthracene derivatives can be produced using known raw materials and known synthesis methods.

[0401] <Benzofluorene derivatives> The benzofluorene derivative is, for example, a compound represented by the following formula (ETM-6). [ka]

[0402] 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.

[0403] 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.

[0404] 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.

[0405] 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.

[0406] 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.

[0407] Specific examples of the "aryl having 6 to 30 carbon atoms" include phenyl, naphthyl, acenaphthylenyl, fluorenyl, phenalenyl, phenanthryl, triphenylenyl, pyrenyl, naphthacenyl, perylenyl, and pentacenyl.

[0408] 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.

[0409] Specific examples of the benzofluorene derivative include the following compounds: [ka]

[0410] The benzofluorene derivative can be produced using known raw materials and known synthesis methods.

[0411] <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]

[0412] 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.

[0413] The phosphine oxide derivative may be, for example, a compound represented by the following formula (ETM-7-2). [ka]

[0414] R 1 ~R 3 may be the same or different and are selected from hydrogen, alkyl, cycloalkyl, aralkyl, alkenyl, cycloalkenyl, alkynyl, alkoxy, alkylthio, cycloalkylthio, aryl ether (aryl ether group), aryl thioether (aryl thioether group), aryl, heterocyclic group, halogen, cyano, formyl, carbonyl, carboxyl, amino, nitro, silyl, and a fused ring formed between adjacent substituents.

[0415] 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.

[0416] 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.

[0417] 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.

[0418] 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.

[0419] 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.

[0420] Furthermore, cycloalkenyl refers to an unsaturated alicyclic hydrocarbon group containing a double bond, such as cyclopentenyl, cyclopentadienyl, cyclohexenyl, etc., which may be unsubstituted or substituted.

[0421] 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.

[0422] 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.

[0423] Moreover, alkylthio is a group in which the oxygen atom of the ether bond of alkoxy is replaced with a sulfur atom.

[0424] Moreover, cycloalkylthio is a group in which the oxygen atom of the ether bond of cycloalkoxy is replaced with a sulfur atom.

[0425] 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.

[0426] 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.

[0427] 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.

[0428] The heterocyclic group refers to a cyclic structure group having atoms other than carbon, such as furanyl, thienyl, oxazolyl, pyridyl, quinolinyl, carbazolyl, etc., which may be unsubstituted or substituted. The number of carbon atoms in the heterocyclic group is not particularly limited, but is usually in the range of 2 to 30.

[0429] Halogen refers to fluorine, chlorine, bromine and iodine.

[0430] Formyl, carbonyl and amino may also include groups substituted with aliphatic hydrocarbons, alicyclic hydrocarbons, aromatic hydrocarbons, heterocycles and the like.

[0431] Furthermore, the aliphatic hydrocarbons, alicyclic hydrocarbons, aromatic hydrocarbons and heterocycles may be either unsubstituted or substituted.

[0432] 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.

[0433] 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.

[0434] Specific examples of the phosphine oxide derivative include the following compounds: [ka]

[0435] The phosphine oxide derivative can be produced using known raw materials and known synthesis methods.

[0436] <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]

[0437] 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.

[0438] 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.

[0439] 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.

[0440] 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.

[0441] 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.

[0442] The above aryl and heteroaryl may be substituted, for example, by the above aryl or heteroaryl, respectively.

[0443] Specific examples of the pyrimidine derivative include the following compounds: [ka]

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

[0445] <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]

[0446] 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.

[0447] 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.

[0448] 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.

[0449] 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.

[0450] 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.

[0451] 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.

[0452] The above aryl and heteroaryl may be substituted, for example, by the above aryl or heteroaryl, respectively.

[0453] 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.

[0454] Specific examples of the arylnitrile derivative include the following compounds: [ka]

[0455] The arylnitrile derivatives can be produced using known raw materials and known synthesis methods.

[0456] <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]

[0457] 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.

[0458] 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.

[0459] 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.

[0460] 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.

[0461] 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.

[0462] The above aryl and heteroaryl may be substituted, for example, by the above aryl or heteroaryl, respectively.

[0463] Specific examples of the triazine derivative include the following compounds: [ka]

[0464] The triazine derivative can be produced using known raw materials and known synthesis methods.

[0465] <Benzimidazole derivatives> The benzimidazole derivative is, for example, a compound represented by the following formula (ETM-11). [ka]

[0466] 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]

[0467] 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.

[0468] 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.

[0469] 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]

[0470] The benzimidazole derivative can be produced using known raw materials and known synthesis methods.

[0471] <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]

[0472] 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.

[0473] R of each formula 11 ~R 18 are each independently hydrogen, alkyl (preferably alkyl having 1 to 24 carbon atoms), cycloalkyl (preferably cycloalkyl having 3 to 12 carbon atoms), or aryl (preferably aryl having 6 to 30 carbon atoms). 11 ~R 18 Either one of these bonds becomes a bond to the aryl ring φ.

[0474] At least one hydrogen atom in each of the phenanthroline derivatives may be replaced with deuterium.

[0475] 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.

[0476] [ka]

[0477] 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]

[0478] The phenanthroline derivative can be produced using known raw materials and known synthesis methods.

[0479] <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.

[0480] 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.

[0481] The quinolinol metal complex can be produced using known raw materials and known synthesis methods.

[0482] <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]

[0483] 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]

[0484] 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 substituents is replaced with a thiazole-based substituent (or a benzothiazole-based substituent) to form a "pyridine-based substituent" R 11 ~R 18 may be substituted.

[0485] These thiazole or benzothiazole derivatives can be produced using known raw materials and known synthesis methods.

[0486] <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]

[0487] 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.

[0488] R 1 ~R 4are each independently hydrogen, halogen, alkyl, cycloalkyl, alkoxy, aryloxy, amino, alkylcarbonyl, arylcarbonyl, alkoxycarbonyl, aryloxycarbonyl, azo group, alkylcarbonyloxy, arylcarbonyloxy, alkoxycarbonyloxy, aryloxycarbonyloxy, sulfinyl, sulfonyl, sulfanyl, silyl, carbamoyl, aryl, heteroaryl, alkenyl, alkynyl, nitro, formyl, nitroso, formyloxy, isocyano, cyanate group, isocyanate group, thiocyanate group, isothiocyanate group, or cyano, which may be substituted with alkyl, cycloalkyl, aryl or halogen, and may form a condensed ring with an adjacent substituent.

[0489] 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.

[0490] 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.

[0491] 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.

[0492] 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.

[0493] 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 not each independently hydrogen or an alkyl group 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.

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

[0495] <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]

[0496] 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):

[0497] [ka]

[0498] 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.

[0499] Specific azoline derivatives are compounds represented by the following formula (ETM-16-1) or formula (ETM-16-2). [ka]

[0500] 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):

[0501] [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.

[0502] 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.

[0503] [ka]

[0504] [ka]

[0505] [ka]

[0506] In the formula, Z is >CR 2 , >N-Ar, >NL, -O- or -S-, >CR 2 R in the formula (1) is independently an alkyl group having 1 to 4 carbon atoms, a cycloalkyl group having 5 to 10 carbon atoms, an aryl group having 6 to 12 carbon atoms, or a heteroaryl group 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 group having 6 to 12 carbon atoms or a heteroaryl group 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.

[0507] 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.

[0508] 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.

[0509] 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.

[0510] Specific examples of azoline derivatives include the following compounds: In the structural formula, "Me" represents methyl. [ka]

[0511] [ka]

[0512] 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:

[0513] [ka]

[0514] 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.

[0515] Other specific examples of azoline derivatives include the following compounds: In the structural formula, "Me" represents methyl. [ka]

[0516] 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.

[0517] The azoline derivative can be produced using known raw materials and known synthesis methods.

[0518] <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.

[0519] 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.

[0520] <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.

[0521] 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 .

[0522] 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.

[0523] 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.

[0524] 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.

[0525] 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.

[0526] 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.

[0527] 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.

[0528] <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.

[0529] <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.

[0530] 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.

[0531] 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.

[0532] 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.

[0533] 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.

[0534] For example, the procedure for producing an organic EL element by partially applying a wet film formation method will be described below. (Step 1) Formation of the anode by vacuum deposition (Step 2) Forming a film by a wet film formation method using a composition for forming a hole injection layer containing a material for the hole injection layer (Step 3) Forming a film by a wet film formation method using a composition for forming a hole transport layer containing a material for the hole transport layer (Step 4) Formation of a film by a wet film formation method using a composition for forming an emitting layer containing a host material and a dopant material (Step 5) Formation of the electron transport layer by vacuum deposition (Step 6) Formation of the electron injection layer by vacuum deposition (Step 7) Cathode deposition by vacuum deposition Through this procedure, an organic EL element consisting of an anode, a hole injection layer, a hole transport layer, an emitting layer made of a host material and a dopant material, an electron transport layer, an electron injection layer, and a cathode is obtained. Of course, the electron transport layer and the electron injection layer may also be formed by a wet film formation method using a layer-forming composition containing the material for the electron transport layer and the material for the electron injection layer, respectively. In this case, it is preferable to use a means for preventing dissolution of the lower light-emitting layer, or a means for forming the film from the cathode side in the reverse order to the above procedure.

[0535] <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.

[0536] <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.

[0537] 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.

[0538] 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.

[0539] <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.

[0540] <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.

[0541] (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.

[0542] 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.

[0543] 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.

[0544] 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.

[0545] (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.

[0546] <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.

[0547] (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.

[0548] 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.

[0549] The binder used in the organic layer-forming composition may be of one type or a mixture of two or more types.

[0550] (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.

[0551] Examples of surfactants include Polyflow No. 45, Polyflow KL-245, Polyflow No. 75, Polyflow No. 90, Polyflow No. 95 (trade names, manufactured by Kyoeisha Chemical Industry Co., Ltd.), Disperbyk 161, Disperbyk 162, Disperbyk 163, Disperbyk 164, Disperbyk 166, Disperbyk 170, Disperbyk 180, Disperbyk 181, Disperbyk 182, BYK300, BYK 306, BYK310, BYK320, BYK330, BYK342, BYK344, BYK346 (trade name, manufactured by BYK Japan Co., Ltd.), KP-341, KP-358, KP-368, KF-96-50CS, KF-50-100CS (trade name, manufactured by Shin-Etsu Chemical Co., Ltd.), Surflon SC-101, Surflon KH-40 (trade name, manufactured by Seimi Chemical Co., Ltd.), Ftergent 222F, Ftergent 251, FTX-218 (trade name, manufactured by Neos Co., Ltd.), EFTOP EF-351, EFTOP EF-352, EFTOP EF-601, EFTOP EF-801, EFTOPEF-802 (product name, manufactured by Mitsubishi Materials Corporation), Megafac F-470, Megafac F-471, Megafac F-475, Megafac R-08, Megafac F-477, Megafac F-479, Megafac F-553, Megafac F-554 (product name, manufactured by DIC Corporation), fluoroalkylbenzenesulfonate, fluoroalkylcarboxylate, fluoroalkylpolyoxyethyleneether, fluoroalkylammonium iodide, fluoroalkylbetaine, fluoroalkylsulfonate, diglycerol tetrakis(fluoroalkylpolyoxyethyleneether), fluoroalkyltrimethylammonium salt, fluoroalkylaminosulfonate, polyoxyethylenenonyl Examples of the alkyl ethers include polyoxyethylene octylphenyl ether, polyoxyethylene alkyl ethers, polyoxyethylene laurate, polyoxyethylene oleate, polyoxyethylene stearate, polyoxyethylene laurylamine, sorbitan laurate, sorbitan palmitate, sorbitan stearate, sorbitan oleate, sorbitan fatty acid esters, polyoxyethylene sorbitan laurate, polyoxyethylene sorbitan palmitate, polyoxyethylene sorbitan stearate, polyoxyethylene sorbitan oleate, polyoxyethylene naphthyl ether, alkylbenzene sulfonates, and alkyldiphenyl ether disulfonates.

[0552] The surfactant may be used alone or in combination of two or more kinds.

[0553] <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.

[0554] 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.

[0555] 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.

[0556] 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).

[0557] The lower the surface tension of the composition for forming an organic layer, the better the film-forming properties and the more defect-free the coating film will be. On the other hand, the higher the surface tension, the better the ink-jet ejection properties will be. For this reason, the surface tension of the composition for forming an organic layer at 25° C. is preferably 20 to 40 mN / m, and more preferably 20 to 30 mN / m. In the present invention, the surface tension is a value measured using the hanging drop method.

[0558] <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).

[0559] [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.

[0560] 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 %.

[0561] 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.

[0562] [ka]

[0563] 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.

[0564] Examples of the divalent aromatic compound having a crosslinkable substituent include compounds having the following partial structures:

[0565] [ka]

[0566] [ka]

[0567] [ka]

[0568] <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.

[0569] 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.

[0570] 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.

[0571] 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 adding a monomer having a polymerizable group bonded to the monomer unit (MU) and a monomer having a polymerizable group bonded to the end cap unit (EC) to a reaction vessel and then reacting the monomer. When the compound of formula (SPH-1) is synthesized in multiple steps, the target product is obtained by polymerizing the monomer having a polymerizable group bonded to the monomer unit (MU) to the target molecular weight, and then adding and reacting the monomer having a polymerizable group bonded to the end cap unit (EC). By adding monomers with polymerizable groups to different types of monomer units (MU) in multiple stages and carrying out the reaction, it is possible to create a polymer with a concentration gradient in terms of the monomer unit structure. Also, after preparing a precursor polymer, the target polymer can be obtained by post-reaction.

[0572] In addition, the primary structure of the polymer can be controlled by selecting the polymerizable group of the monomer. For example, as shown in synthesis schemes 1 to 3, it is possible to synthesize a polymer having a random primary structure (synthetic scheme 1) or a polymer having a regular primary structure (synthetic schemes 2 and 3), and these can be used in appropriate combinations depending on the target object. Furthermore, if a monomer having three or more polymerizable groups is used, a hyperbranched polymer or a dendrimer can be synthesized.

[0573] [ka]

[0574] Monomers that can be used in the present invention include those described in JP2010-189630A, WO2012 / 086671A, WO2013 / 191088A, WO2002 / 045184A, WO2011 / 049241A, WO2013 / 146806A, WO2005 / 049546A, WO2015 / 1458 ...B, WO2015 / 1458B, WO2015 / 1458B, WO2015 / 1458B, WO2015 / 1458B, WO2015 / 1458B, WO2015 / 1458B, WO2015 / 1458B, W It can be synthesized in accordance with the methods described in JP-A-2002 / 045184, JP-A-2010-215886, JP-A-2008-106241, JP-A-2010-215886, WO 2016 / 031639, JP-A-2011-174062, WO 2016 / 031639, WO 2016 / 031639, and WO 2002 / 045184.

[0575] 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.

[0576] 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.

[0577] 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.

[0578] 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.

[0579] 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.

[0580] Examples of the lighting device include lighting devices for indoor lighting, backlights for liquid crystal display devices, etc. (see, for example, JP-A-2003-257621, JP-A-2003-277741, JP-A-2004-119211, 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.

[0581] 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.

[0582] 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.

[0583] 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.

[0584] 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

[0585] The present invention will be described in more detail below with reference to examples, but the present invention is not limited thereto. First, synthesis examples of polycyclic aromatic compounds will be described below.

[0586] Synthesis Example (1): Synthesis of Compound (1-25) [ka]

[0587] Under a nitrogen atmosphere, compound (IA) was dissolved in acetonitrile (300 ml), and bromine was added dropwise to the solution while cooling with ice and stirred. After the reaction, water and ethyl acetate were added to the reaction solution and stirred, and then toluene was added, 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 short column to obtain compound (IB).

[0588] [ka]

[0589] Under a nitrogen atmosphere, t-butyl nitrite and copper (II) chloride were suspended in acetonitrile, and intermediate (IB) dissolved in acetonitrile at 60°C was added dropwise and stirred at the same temperature. After the reaction, dilute hydrochloric acid and ethyl acetate were added to the reaction solution and stirred, and then 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 short column to obtain compound (IC).

[0590] [ka]

[0591] Under a nitrogen atmosphere, intermediate (IC), N-(3-tertbutylphenyl)-3,5-ditertbutylaniline, dichlorobis(di-t-butyl(4-dimethylaminophenyl)phosphino)palladium (Pd-132) as a palladium catalyst, sodium-t-butoxide (NaOtBu) and xylene were placed in a flask and heated with stirring at 100°C. After the reaction, water and ethyl acetate were added to the reaction solution and stirred, and then 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 short column to obtain compound (ID) (26.0 g).

[0592] [ka]

[0593] A 1.56M pentane solution of tert-butyllithium was added to a flask containing compound (ID) and tert-butylbenzene under a nitrogen atmosphere at 0°C. After the dropwise addition, the temperature was raised to 60°C and stirred for 1 hour, and then components with a boiling point lower than that of tert-butylbenzene were distilled off under reduced pressure. The mixture was cooled to -50°C, boron tribromide was added, and the mixture was heated to room temperature and stirred for 0.5 hours. The mixture was then cooled again to 0°C, N,N-diisopropylethylamine was added, and the mixture was stirred at room temperature until the heat generation subsided, and then the mixture was heated to 100°C and stirred for 1 hour. The reaction solution was cooled to room temperature, and an aqueous sodium acetate solution cooled in an ice bath was added, followed by ethyl acetate, and the mixture was separated. The organic layer was concentrated and purified using a silica gel short column. The crude product obtained was dissolved in toluene and reprecipitated with methanol to obtain compound (1-25). Mass spectrometry confirmed that the compound obtained was compound (1-25). EI-MS: m / z=933.

[0594] [ka]

[0595] Synthesis Example (2): Synthesis of Compound (1-327) [ka]

[0596] The compound represented by formula (1-327) was synthesized by the same method as in the above-mentioned Synthesis Example (1). [ka]

[0597] The structure of the obtained compound was confirmed by NMR measurement. 1 H-NMR (CDCl 3):σ=1.46(s, 9H), 1.47(s, 9H), 1.59~1.76(m, 24H), 2.00(br, 3H), 2.01(br, 3H), 2.52(s, 2H), 2.53(s, 2H), 6.12(d, 1H), 6.13(d, 1H), 6.67(d , 1H), 6.73(d, 1H), 7.18(dd, 1H), 7.25(t, 1H), 7.26(d, 2H), 7.29(d, 2H), 7.37(d, 2H), 7.51(dd, 1H), 7.67(d, 2H), 8.64(d, 1H), 8.95(d, 1H).

[0598] Synthesis Example (3): Synthesis of Compound (1-416) [ka]

[0599] The compound represented by formula (1-416) was synthesized by the same method as in the above-mentioned Synthesis Example (1). [ka]

[0600] The structure of the obtained compound was confirmed by NMR measurement. 1 H-NMR (CDCl 3 ):σ=1.60~1.76(m, 24H), 1.97(br, 3H), 2.02(br, 3H), 2.54(s, 2H), 2.58(s, 2H), 6.06(d, 1H), 6.16(d, 1H), 6.33(d, 1H), 6.57(d, 1H), 6.95(t, 1H), 7.17(dd, 1H), 7.25~7.30(m, 3H), 7.32(t, 1H), 7.39(d, 2H), 7.53(dd, 2H), 7.69~7.76(m, 3H), 8.00(d, 1H), 8.50(d, 1H).

[0601] Synthesis Example (4): Synthesis of Compound (1-417) [ka]

[0602] The compound represented by formula (1-417) was synthesized by the same method as in the above-mentioned Synthesis Example (1). [ka]

[0603] The structure of the obtained compound was confirmed by NMR measurement. 1 H-NMR (CDCl 3 ):σ=1.15(s, 9H), 1.31(s, 9H), 1.35(s, 9H), 1.44(s, 9H), 1.53~1.67(m, 12H), 1.92(br, 3H)), 2.48(m, 2H), 5.50(s, 1H), 5.65(s, 1H), 6.73(d, 2H), 6.87~6.92(m, 6H), 6.99~7.15(m, 12H), 7.38~7.47(m, 5H), 8.55(d, 1H), 8.89(d, 1H).

[0604] Synthesis Example (5): Synthesis of Compound (1-418) [ka]

[0605] The compound represented by formula (1-418) was synthesized by the same method as in the above-mentioned Synthesis Example (1). [ka]

[0606] The structure of the obtained compound was confirmed by NMR measurement. 1 H-NMR (CDCl 3):σ=1.10(s, 9H), 1.45(s, 18H), 1.47(s, 9H), 1.54~1.69(m, 12H), 1.93(br, 3H)), 2.49(m, 2H), 6.08(d, 1H), 6.25(d, 1H), 6.72(d, 2H), 6.97(d, 2H), 7.05(d, 2H), 7.13(dd, 1H), 7.23~7.30(m, 4H), 7.49(dd, 1H), 7.60(dd, 1H), 7.65~7.68(m, 3H), 8.56(d, 1H), 8.91(d, 1H).

[0607] Synthesis Example (6): Synthesis of Compound (1-419) [ka]

[0608] The compound represented by formula (1-419) was synthesized by the same method as in the above-mentioned Synthesis Example (1). [ka]

[0609] The structure of the obtained compound was confirmed by NMR measurement. 1 H-NMR (CDCl 3 ):σ=0.73~0.92(m, 4H), 1.00~1.27(m, 12H), 1.41(s, 6H), 1.44(s, 6H), 1 .46(s, 9H), 1.48(s, 9H), 1.56~1.74(m, 14H), 6.12(d, 1H), 6.13(d, 1H), 6 .73(d, 1H), 6.75(d, 1H), 7.24(t, 1H), 7.29(d, 2H), 7.30(d, 2H), 7.43(dd , 1H), 7.52(dd, 1H), 7.61(d, 2H), 7.67(d, 2H), 8.90(d, 1H), 8.97(d, 1H).

[0610] Synthesis Example (7): Synthesis of Compound (1-420) [ka]

[0611] The compound represented by formula (1-420) was synthesized by the same method as in the above-mentioned Synthesis Example (1). [ka]

[0612] The structure of the obtained compound was confirmed by NMR measurement. 1 H-NMR (CDCl 3 ):σ=0.78~0.92(m, 4H), 1.06~1.26(m, 12H), 1.41(s, 6H), 1.48(s, 6H), 1.57~ 1.74(m, 12H), 1.76~1.80(m, 2H), 6.06(d, 1H), 6.17(d, 1H), 6.33(d, 1H), 6.6 3(d, 1H), 6.96(t, 1H), 7.27(t, 1H), 7.29(d, 2H), 7.33(t, 1H), 7.41(dd, 1H), 7.53~7.55(m, 2H), 7.62(d, 2H), 7.69~7.75(m, 3H), 7.99(d, 1H), 8.74(d, 1H).

[0613] Synthesis Example (8): Synthesis of Compound (1-423) [ka]

[0614] The compound represented by formula (1-423) was synthesized by the same method as in the above-mentioned Synthesis Example (1). [ka]

[0615] The structure of the obtained compound was confirmed by NMR measurement. 1 H-NMR (CDCl 3):σ=0.74~0.90(m, 8H), 1.00~1.26(m, 24H), 1.42(s, 12H), 1.44(s, 12H), 1.56~1.74(m, 28H), 2.14(s, 3H), 5.91(s, 2H), 6.70(dd, 2H), 7.29(d, 4H), 7.41(d, 2H), 7.61(d, 4H), 8.88(d, 2H).

[0616] Synthesis Example (9): Synthesis of Compound (1-424) [ka]

[0617] The compound represented by formula (1-424) was synthesized by the same method as in the above-mentioned Synthesis Example (1). [ka]

[0618] The structure of the obtained compound was confirmed by NMR measurement. 1 H-NMR (CDCl 3 ):σ=0.73~0.91(m, 4H), 0.98~1.24(m, 12H), 1.27(s, 6H), 1.33(s, 9H), 1.43(s, 6H), 1.47(s, 9H), 1.56~1.73(m, 14H), 5.55(s, 1H), 5.63(s, 3H), 6.70(d, 1H), 6 .76(d, 1H), 6.88(t, 2H), 6.94(d, 4H), 7.06(t, 4H), 7.13(d, 2H), 7.14(d, 2H), 7 .37(dd, 1H), 7.39(d, 2H), 7.44(d, 2H), 7.45(dd, 1H), 8.87(d, 1H), 8.94(d, 1H).

[0619] Comparative Synthesis Example (1): Synthesis of Compound (BD-1) [ka]

[0620] Compound (BD-1) was synthesized in accordance with the production method for compound (1-25) described in WO 2019 / 198699.

[0621] Comparative Synthesis Example (2): Synthesis of Compound (BD-2) [ka]

[0622] Compound (BD-2) was synthesized in accordance with the production method for compound (1-327) described in WO 2019 / 198699.

[0623] Comparative Synthesis Example (3): Synthesis of Compound (BD-3) [ka]

[0624] Compound (BD-3) was synthesized in accordance with the production method for compound (1-334) described in WO 2019 / 198699.

[0625] Comparative Synthesis Example (4): Synthesis of Compound (BD-4) [ka]

[0626] Compound (BD-4) was synthesized in accordance with the production method for compound (1-321) described in WO 2019 / 198699.

[0627] Comparative Synthesis Example (5): Synthesis of Compound (BD-5) [ka]

[0628] Compound (BD-5) was synthesized according to the production method for compound (1-401) described in WO 2015 / 102118.

[0629] Comparative Synthesis Example (6): Synthesis of Compound (BD-6) [ka]

[0630] Compound (BD-6) was synthesized in accordance with the production method for compound (1-339) described in WO 2019 / 198699.

[0631] Comparative Synthesis Example (7): Synthesis of Compound (BD-7) [ka]

[0632] Compound (BD-7) was synthesized in accordance with the production method for compound (2-1A-18) described in WO 2020 / 054676.

[0633] Next, in order to explain the present invention in more detail, examples of organic EL devices using the compounds of the present invention will be shown, but the present invention is not limited to these.

[0634] <Evaluation of deposition-type organic EL elements> The organic EL devices of Examples 1 to 13 and Comparative Examples 1 to 8 were prepared and were measured to obtain a luminance of 1000 cd / m 2 The characteristics of the light emission, such as voltage (V), emission wavelength (nm), and external quantum efficiency (%), were measured, and then the current was set at 10 mA / cm 2 The time for which the luminance was maintained at 90% or more of the initial luminance when the device was driven at a constant current density of 1000 Hz was measured.

[0635] The quantum efficiency of a light-emitting element includes internal quantum efficiency and external quantum efficiency, and the internal quantum efficiency indicates the ratio at which the external energy injected as electrons (or holes) into the light-emitting layer of the light-emitting element is converted purely into photons. On the other hand, the external quantum efficiency is calculated based on the amount of these photons that are emitted to the outside of the light-emitting element, and since some of the photons generated in the light-emitting layer are absorbed or continue to be reflected inside the light-emitting element and are not emitted to the outside of the light-emitting element, the external quantum efficiency is lower than the internal quantum efficiency.

[0636] The external quantum efficiency was measured as follows: The luminance of the element was 1000 cd / m using an Advantest voltage / current generator R6144. 2 The element was made to emit light by applying a voltage that would result in a value of 10 ...

[0637] <Examples 1 to 13 and Comparative Examples 1 to 8> The material configurations of the layers in the organic EL devices according to Examples 1 to 13 and Comparative Examples 1 to 8, and the EL characteristic data are shown in the following Tables 1A and 1B.

[0638] [Table 1A]

[0639] [Table 1B]

[0640] In Table 1A, "HI" stands for N 4 ,N 4’ -Diphenyl-N 4 ,N 4’-bis(9-phenyl-9H-carbazol-3-yl)-[1,1'-biphenyl]-4,4'-diamine, "HAT-CN" is 1,4,5,8,9,12-hexaazatriphenylene hexacarbonitrile, "HT-1" is N-([1,1'-biphenyl]-4-yl-9,9-dimethyl-N-[4-(9-phenyl-9H-carbazol-3-yl)phenyl]-9H-fluoren-2-amine, "HT-2" is N,N-bis(4-(dibenzo[b,d]furan-4-yl)phenyl)-[1,1':4',1"-terphenyl]-4-amine, and "HT-3" is N-([1,1'-biphenyl]-2-yl)-N-(9,9-dimethyl-9H-fluoren-2-yl) "BH-1" is 2-(10-phenylanthracen-9-yl)naphtho[2,3-b]benzofuran, "BH-2" is 2-(10-phenylanthracen-9-yl)dibenzo[b,d]furan, "BH-3" 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-phenylanthracen-9,10-diyl)bis(4,1-phenylene))bis(4-methylpyridine). The chemical structures are shown below along with "Liq".

[0641] [ka]

[0642] <Example 1> A 26 mm × 28 mm × 0.7 mm glass substrate (manufactured by Optoscience Co., Ltd.) on which an ITO film having a thickness of 180 nm was formed by sputtering and polished to 150 nm was used as a transparent support substrate. This transparent support substrate was fixed to a substrate holder of a commercially available deposition apparatus (manufactured by Showa Vacuum Co., Ltd.), and a molybdenum deposition boat containing HI, HAT-CN, HT-1, HT-2, BH-1, compound (1-25), ET-1, and ET-2, and an aluminum nitride deposition boat containing Liq, LiF, and aluminum, were attached.

[0643] The following layers were formed in order on the ITO film of the transparent support substrate. -4 The pressure was reduced to 10 Pa, and first, HI was heated and evaporated to a thickness of 40 nm, then HAT-CN was heated and evaporated to a thickness of 5 nm, then HT-1 was heated and evaporated to a thickness of 45 nm, and then HT-2 was heated and evaporated to a thickness of 10 nm to form a hole layer consisting of four layers. Next, BH-1 and compound (1-25) were heated simultaneously and evaporated to a thickness of 25 nm to form an emitting layer. The evaporation rate was adjusted so that the mass ratio of BH-1 to compound (1-25) was approximately 98:2. Furthermore, ET-1 was heated and evaporated to a thickness of 5 nm, and then ET-2 and Liq were heated simultaneously and evaporated to a thickness of 25 nm to form an electron layer consisting of two layers. The evaporation rate was adjusted so that the mass ratio of ET-2 to Liq was approximately 50:50. The evaporation rate of each layer was 0.01 to 1 nm / sec. Thereafter, LiF was heated and evaporated at a deposition rate of 0.01 to 0.1 nm / sec to a thickness of 1 nm, and then aluminum was heated and evaporated to a thickness of 100 nm to form a cathode, thereby obtaining an organic EL device.

[0644] A DC voltage of 1000 cd / m was applied to the ITO electrode as the anode and the LiF / aluminum electrode as the cathode. 2 When the light-emitting characteristics were measured, blue light was emitted at a wavelength of 458 nm, the driving voltage was 3.68 V, and the external quantum efficiency was 8.35%. In addition, the time during which the brightness was maintained at 90% or more of the initial brightness was 365 hours.

[0645] <Examples 2 to 13> According to Example 1, each organic EL device was produced with the layer structure shown in Table 1A, and the EL characteristic data was measured (Table 1B).

[0646] <Comparative Examples 1 to 8> According to Example 1, each organic EL device was produced with the layer structure shown in Table 1A, and the EL characteristic data was measured (Table 1B). For example, compound (1-327) has the same structure as compound (BD-2) except for the presence or absence of a linking group to the cycloalkyl. When Example 2 and Comparative Example 3, which use these compounds, are compared, it is found that Example 2 provides a higher external quantum efficiency and a longer luminance retention time than Comparative Example 3.

[0647] <Example 14 and Comparative Examples 9 to 10> A dissolution test was carried out to evaluate the solubility of the compound of the present invention in organic solvents. 1.0 g of the test compound was added to 30 mL of toluene and stirred at 100°C, after which it was verified whether the test compound was dissolved or not. The case in which the compound was completely dissolved in toluene and a homogeneous solution was obtained was rated as "soluble", and the case in which insoluble matter remained was rated as "hardly soluble". The results are shown in Table 2A.

[0648] [Table 2A]

[0649] <Examples 15 to 17 and Comparative Examples 11 to 12> A dissolution test of the compound was performed. 0.5 g of the test compound was added to 30 mL of toluene and stirred at 100° C., and then it was verified whether the test compound was dissolved. The results are shown in Table 2B.

[0650] [Table 2B]

[0651] <Examples 18 to 21 and Comparative Examples 13 to 17> A dissolution test of the compound was performed. 0.5 g of the test compound was added to 30 mL of toluene and stirred at 60° C., and then it was verified whether the test compound was dissolved. The results are shown in Table 2C.

[0652] [Table 2C]

[0653] <Example 22 and Comparative Example 18> A dissolution test of the compound was performed. 0.3 g of the test compound was added to 30 mL of toluene and stirred at 80° C., and then it was verified whether the test compound was dissolved. The results are shown in Table 2D.

[0654] [Table 2D]

[0655] The solubility tests of the compounds shown in Tables 2A to 2D above reveal that the compounds of the present invention having a linking group with a cycloalkyl have high solubility in organic solvents. [Industrial Applicability]

[0656] In the present invention, by providing a novel polycyclic aromatic compound, it is possible to increase the options of materials for organic devices, such as materials for organic EL elements. In addition, by using a novel cycloalkyl-substituted polycyclic aromatic compound as a material for an organic EL element, it is possible to provide, for example, an organic EL element having excellent luminous efficiency and element life, a display device including the same, and a lighting device including the same. [Explanation of symbols]

[0657] 100 Organic electroluminescent device 101 Substrate 102 Anode 103 Hole injection layer 104 Hole transport layer 105 Light-emitting layer 106 Electron transport layer 107 Electron injection layer 108 cathode

Claims

1. A polycyclic aromatic compound represented by the following formula (1): 【Chemistry 1】 (In formula (1), ring A, ring B, and ring C are each independently an aryl ring or a heteroaryl ring, and at least one hydrogen atom in these rings may be substituted; Y 1 is B; X 1 and X 2 are each independently >N-R, wherein R of the >N-R is an optionally substituted aryl, an optionally substituted heteroaryl, an optionally substituted alkyl, or an optionally substituted cycloalkyl; At least one of the aryl or heteroaryl rings in the compound represented by formula (1) may be condensed with at least one cycloalkane, at least one hydrogen in the cycloalkane may be substituted, and at least one -CH 2 - may be replaced by -O-; At least one of the aryl rings or heteroaryl rings in the compound represented by formula (1) is substituted with at least one L-Cy, and L is a linear alkylene having 1 to 6 carbon atoms or a branched alkylene having 2 to 6 carbon atoms, or at least one -CH 2 a linking group in which - is replaced by -O-, -S-, -CO-, -COO-, -OCO-, or -OCOO-, or a linear alkylene having 2 to 6 carbon atoms having at least one -(CH 2 ) 2 - is a linking group in which - is replaced by -CH=CH- or -C≡C-, and Cy is cycloalkyl; At least one hydrogen atom in the compound represented by formula (1) may be substituted with deuterium, cyano, or halogen.

2. The polycyclic aromatic compound according to claim 1, wherein Cy is a cycloalkyl having 3 to 20 carbon atoms.

3. L is -CH 2 --, --CH 2 CH 2 --, --CH 2 CH 2 CH 2 -, -C(CH 3 ) 2 -, -C(CH 3 ) 2 CH 2 - or -C(CH 3 ) 2 CH 2 CH 2 The polycyclic aromatic compound according to claim 1 or 2,

4. The polycyclic aromatic compound according to any one of claims 1 to 3, represented by the following formula (1-a), formula (1-b), formula (1-c), formula (1-d), formula (1-e), or formula (1-f). 【Chemistry 2】 (In formula (1-a), formula (1-b), formula (1-c), formula (1-d), formula (1-e), and formula (1-f), R 1 ~R 11 are each independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl, alkyl, cycloalkyl, alkoxy, aryloxy, or substituted silyl, in which at least one hydrogen may be substituted with an aryl, heteroaryl, alkyl, cycloalkyl, or substituted silyl; R 1 ~R 11 adjacent groups among may be bonded to each other to form an aryl ring or a heteroaryl ring together with the a ring, the b ring, or the c ring, and at least one hydrogen atom in the formed ring may be replaced by an aryl, a heteroaryl, a diarylamino, a diheteroarylamino, an arylheteroarylamino, a diarylboryl, an alkyl, a cycloalkyl, an alkoxy, an aryloxy, or a substituted silyl, and at least one hydrogen atom in these rings may be replaced by an aryl, a heteroaryl, an alkyl, a cycloalkyl, or a substituted silyl, X X are each independently >O, >S, >N-R, or >C(-R) 2 R of the >N-R is an optionally substituted aryl, an optionally substituted heteroaryl, an optionally substituted alkyl, or an optionally substituted cycloalkyl, and the >C(-R) 2 R is each independently hydrogen, aryl optionally substituted with alkyl or cycloalkyl, heteroaryl optionally substituted with alkyl or cycloalkyl, alkyl, or cycloalkyl; Y 1 is B; X 1 and X 2 are each independently >N-R, R of the >N-R is an aryl having 6 to 12 carbon atoms, a heteroaryl having 2 to 15 carbon atoms, an alkyl having 1 to 6 carbon atoms, or a cycloalkyl having 3 to 14 carbon atoms, and each of the aryl having 6 to 12 carbon atoms and the heteroaryl having 2 to 15 carbon atoms in R of the >N-R is optionally substituted with an alkyl having 1 to 6 carbon atoms, a cycloalkyl having 3 to 14 carbon atoms, or a substituted silyl, At least one of the aryl rings or heteroaryl rings in the compounds represented by each of formulas (1-a), (1-b), (1-c), (1-d), (1-e), and (1-f) may be condensed with at least one cycloalkane having 3 to 24 carbon atoms, at least one hydrogen in the cycloalkane may be substituted with an aryl having 6 to 30 carbon atoms, a heteroaryl having 2 to 30 carbon atoms, an alkyl having 1 to 24 carbon atoms, or a cycloalkyl having 3 to 24 carbon atoms, and at least one —CH 2 - may be replaced by -O-; At least one of the aryl rings or heteroaryl rings in the compounds represented by each of formulas (1-a), (1-b), (1-c), (1-d), (1-e), and (1-f) is substituted with at least one L-Cy, and L is a linear alkylene having 1 to 6 carbon atoms or a branched alkylene having 2 to 6 carbon atoms, or at least one -CH 2 a linking group in which - is replaced by -O-, -S-, -CO-, -COO-, -OCO-, or -OCOO-, or a linear alkylene having 2 to 6 carbon atoms having at least one -(CH 2 ) 2 - is a linking group in which - is replaced by -CH=CH- or -C≡C-, and Cy is cycloalkyl; At least one hydrogen atom in each of the compounds represented by formula (1-a), formula (1-b), formula (1-c), formula (1-d), formula (1-e), and formula (1-f) may be substituted with cyano, halogen, or deuterium.

5. The polycyclic aromatic compound according to claim 4, represented by formula (1-a):

6. The polycyclic aromatic compound according to claim 5 , which is represented by any one of the following structural formulas: 【Chemistry 3】 (In the above structural formulas, "Me" represents methyl and "tBu" represents t-butyl.)

7. The polycyclic aromatic compound according to claim 4, represented by formula (1-b):

8. The polycyclic aromatic compound according to claim 7, which is represented by the following structural formula: 【Chemistry 4】 (In the above structural formula, "Me" represents methyl.)

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

10. The material for an organic device according to claim 9 , 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.

11. The material for an organic device according to claim 10 , wherein the material for an organic electroluminescent element is a material for a light-emitting layer.

12. A composition comprising the polycyclic aromatic compound according to any one of claims 1 to 8 and an organic solvent.

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

14. 9. 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.

15. The organic electroluminescent device according to claim 14 , wherein the light-emitting layer comprises a host and the polycyclic aromatic compound as a dopant.

16. The organic electroluminescent device according to claim 15, wherein the host is an anthracene-based compound, a fluorene-based compound, or a dibenzochrysene-based compound.

17. The organic electroluminescence device according to any one of claims 14 to 16, 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.

18. 18. The organic electroluminescent device according to claim 17, 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.

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

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