Polycyclic aromatic compounds

Abstract

To provide a novel polycyclic aromatic compound and an organic EL element based thereon.SOLUTION: The present invention provides, specifically as the polycyclic aromatic compound, a compound (1-16) represented by the formula in the figure, for example. An organic EL element is produced by using the novel polycyclic aromatic compound, e.g., as an electron transport material, so as to provide an organic EL element excellent in the driving voltage, luminous efficacy and element life, in particular, an organic EL element excellent in the luminous efficacy and element life.SELECTED DRAWING: None

Description

[Technical Field]

[0001] The present invention relates to polycyclic aromatic compounds, organic devices such as organic electroluminescent elements, organic field-effect transistors, organic thin-film solar cells, and wavelength conversion filters using the same, as well as display devices and lighting devices. In this specification, "organic electroluminescent elements" may be referred to as "organic EL elements" or simply "elements." [Background technology]

[0002] Conventionally, display devices using electroluminescent light-emitting elements have been studied extensively due to their potential for power saving and miniaturization. Furthermore, organic electroluminescent elements made from organic materials have been actively investigated because they are easily made lighter and larger. In particular, the development of organic materials with luminescence properties such as blue, one of the three primary colors of light, and the development of organic materials with charge transport capabilities (potentially becoming semiconductors or superconductors) have been actively researched, regardless of whether they are polymer compounds or low molecular weight compounds.

[0003] Organic light-emitting diodes (OLEDs) have a structure consisting of a pair of electrodes, an anode and a cathode, and one or more layers containing an organic compound, disposed between the pair of electrodes. The layers containing the organic compound include light-emitting layers and charge transport / injection layers that transport or inject charges such as holes and electrons, and various organic materials suitable for these layers have been developed.

[0004] For example, improved triphenylamine derivatives have been reported as materials used in organic EL elements and organic thin-film solar cells (International Publication No. 2012 / 118164). This material is based on N,N'-diphenyl-N,N'-bis(3-methylphenyl)-1,1'-biphenyl-4,4'-diamine (TPD), which had already been put into practical use, and is characterized by its improved planarity while positioning nitrogen at the center of the ring structure by linking the aromatic rings that make up triphenylamine. In this document, for example, the charge transport properties of NO-linked compounds (compound 1 on page 63) are evaluated, but the manufacturing methods of materials other than NO-linked compounds are not described, and since the electronic state of the entire compound differs depending on the linked elements, the properties obtained from materials other than NO-linked compounds were also unknown.

[0005] In this context, compounds in which multiple aromatic rings are fused around a central atom such as boron have recently been reported (International Publication No. 2015 / 102118). This document describes the evaluation of organic EL devices using such compounds with multiple aromatic rings fused together, not only as materials for light-emitting layers but also as materials for charge transport layers such as electrons. Furthermore, examples of larger quantities of such compounds (International Publication No. 2018 / 212169) and examples of expanding the conjugated system with linking groups within the molecule have also been reported (Korean Patent Publication No. 10-2020-0121228, International Publication No. 2020 / 217229). [Prior art documents] [Patent Documents]

[0006] [Patent Document 1] International Publication No. 2012 / 118164 [Patent Document 2] International Publication No. 2015 / 102118 [Patent Document 3] International Publication No. 2018 / 212169 [Patent Document 4] Korean Published Patent No. 10-2020-0121228 [Patent Document 5] International Publication No. 2020 / 217229 [Overview of the project] [Problems that the invention aims to solve]

[0007] As reported in Patent Documents 1-5, various materials have been developed for use in organic EL devices. However, in order to increase the range of materials for organic EL devices, the development of materials composed of compounds different from those used conventionally is desired. In particular, it is beneficial to explore organic EL properties and manufacturing methods obtained from materials other than NO-linked compounds in which nitrogen is positioned at the center of the ring structure.

[0008] Furthermore, while Patent Documents 2 to 5 report on polycyclic aromatic compounds containing boron and organic EL devices using them, these documents disclose a very large number of compounds. Therefore, in order to further improve the device characteristics, it would be beneficial to explore charge transport layer materials, particularly electron transport layer materials and electron injection layer materials, that can improve organic EL characteristics such as luminous efficiency and device lifetime.

[0009] Furthermore, in addition to vacuum deposition, wet deposition methods are now also used as a method for forming the organic layers that constitute organic EL elements. Therefore, the development of wet deposition ink materials, particularly for forming electron injection layers, electron transport layers, and light-emitting layers, is being actively pursued, and exploring such ink materials is also beneficial. [Means for solving the problem]

[0010] The present inventors, after diligent research to solve the above problems, discovered that an excellent organic EL element can be obtained by arranging a layer containing a polycyclic aromatic compound having a novel structure between a pair of electrodes to constitute an organic EL element, and thus completed the present invention. That is, the present invention provides polycyclic aromatic compounds such as those described below, and further, materials for organic devices such as materials for organic EL elements containing polycyclic aromatic compounds such as those described below.

[0011] In this specification, chemical structures and substituents may be expressed in terms of carbon number. However, when a substituent is substituted into a chemical structure, or when a substituent is further substituted into another substituent, the carbon number refers to the carbon number of the chemical structure and the substituent itself, and does not refer to the total carbon number of the chemical structure and substituent, or the total carbon number of the substituents. For example, "substituent B with carbon number Y substituted by substituent A with carbon number X" means that "substituent A with carbon number X" is substituted into "substituent B with carbon number Y," and carbon number Y is not the total carbon number of substituents A and B. Also, for example, "substituent B with carbon number Y substituted by substituent A" means that "substituent A (without carbon number limitation)" is substituted into "substituent B with carbon number Y," and carbon number Y is not the total carbon number of substituents A and B.

[0012] Section 1. A polycyclic aromatic compound represented by the following general formula (1). [ka] In the above equation (1), R 1 ~R 11 Each of these is independently hydrogen, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl, alkyl, cycloalkyl, alkenyl, alkoxy, aryloxy, arylthio, triarylsilyl, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, or alkyldicycloalkylsilyl, wherein the two aryls of the diarylamino may be linked via a linking group, the two heteroaryls of the diheteroarylamino may be linked via a linking group, the aryl and heteroaryl of the arylheteroarylamino may be linked via a linking group, and the two aryls of the diarylboryl may be linked via a linking group. R 1 ~R 11Adjacent groups among them may bond together to form a naphthalene ring, a phenanthrene ring, a dibenzothiophene ring, a dibenzofuran ring, or a carbazole ring together with at least one of the rings a, b, and c, and at least one hydrogen in the formed ring may be independently substituted with diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl, alkyl, cycloalkyl, alkenyl, alkoxy, aryloxy, arylthio, triarylsilyl, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, or alkyldicycloalkylsilyl, and the two aryls of the diarylamino may be bonded via a linking group, the two heteroaryls of the diheteroarylamino may be bonded via a linking group, the aryl and heteroaryl of the arylheteroarylamino may be bonded via a linking group, and the two aryls of the diarylboryl may be bonded via a linking group. However, at least one group represented by the above general formula (G) is bonded to the "a-ring" or "ring formed together with the a-ring," at least one group represented by the above general formula (G) is bonded to the "b-ring" or "ring formed together with the b-ring," and at least one group represented by the above general formula (G) is bonded to the "c-ring" or "ring formed together with the c-ring," and these groups represented by formula (G) may be the same or different. In the above formula (G), Cy 1 and Cy 2Each of these rings is independently a benzene ring, a naphthalene ring, a phenanthrene ring, a pyridine ring, a quinoline ring, a dibenzofuran ring, a dibenzothiophene ring, or a carbazole ring whose N position may be substituted with phenyl, and each of these rings is independently substituted with diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl, alkyl, cycloalkyl, alkenyl, alkoxy, aryloxy, arylthio, triarylsilyl, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, alkyldicycloalkylsilyl, or cyano, and the two aryls of the diarylamino may be linked via a linking group, the two heteroaryls of the diheteroarylamino may be linked via a linking group, the aryl and heteroaryl of the arylheteroarylamino may be linked via a linking group, and the two aryls of the diarylboryl may be linked via a linking group, and * is the bond position to the a ring, b ring, c ring, and the ring formed together with these rings, and At least one hydrogen atom in the compound represented by formula (1) above may be substituted with deuterium, cyano, or halogen.

[0013] Section 2. In the above equation (1), R 1 ~R 11is, independently of each other, hydrogen, diarylamino (where aryl is aryl having 6 to 12 carbon atoms), diheteroarylamino (where heteroaryl is heteroaryl having 2 to 15 carbon atoms), arylheteroarylamino (where aryl is aryl having 6 to 12 carbon atoms and heteroaryl is heteroaryl having 2 to 15 carbon atoms), diarylboril (where aryl is aryl having 6 to 12 carbon atoms), alkyl having 1 to 24 carbon atoms, cycloalkyl having 3 to 24 carbon atoms, alkenyl having 1 to 24 carbon atoms, alkoxy having 1 to 24 carbon atoms, aryloxy having 6 to 30 carbon atoms, arylthio having 6 to 30 carbon atoms, triarylsilyl (where aryl is aryl having 6 to 12 carbon atoms), trialkylsilyl (where alkyl is alkyl having 1 to 12 carbon atoms), tricycloalkylsilyl (where cycloalkyl is cycloalkyl having 3 to 12 carbon atoms), dialkylcycloalkylsilyl (where alkyl is alkyl having 1 to 12 carbon atoms and cycloalkyl is cycloalkyl having 3 to 12 carbon atoms), or alkyldicycloalkylsilyl (where alkyl is alkyl having 1 to 12 carbon atoms and cycloalkyl is cycloalkyl having 3 to 12 carbon atoms), and the two aryls of the diarylamino may be bonded via a linking group, the two heteroaryls of the diheteroarylamino may be bonded via a linking group, the aryl and heteroaryl of the arylheteroarylamino may be bonded via a linking group, the two aryls of the diarylboril may be bonded via a linking group, and the linking group is a single bond, -CH2-CH2-, -CHR-CHR-, -CR2-CR2-, -CH=CH-, -CR=CR-, -C≡C-, -N(-R)-, -O-, -S-, -C(-R)2-, -Si(-R)2-, or -Se-. R 1 ~R 11Adjacent groups among them may bond together to form a naphthalene ring, a phenanthrene ring, a dibenzothiophene ring, a dibenzofuran ring, or a carbazole ring, and at least one hydrogen in the formed ring may independently be a diarylamino (where aryl has 6 to 12 carbon atoms), a diheteroarylamino (where heteroaryl has 2 to 15 carbon atoms), or an arylheteroarylamino (where aryl has 6 to 12 carbon atoms). (aryl is a C6-C12 aryl, heteroaryl is a C2-C15 heteroaryl), diarylboryl (where aryl is a C6-C12 aryl), alkyl (C1-C24 alkyl), cycloalkyl (C3-C24 cycloalkyl), alkenyl (C1-C24 alkenyl), alkoxy (C1-C24 alkoxy), aryloxy (C6-C30 arylthio), triarylsilyl (where aryl is a C6-C12 aryl), trialkylsilyl (where alkyl is an alkyl with C1-C12), It may be substituted with lycycloalkylsilyl (where cycloalkyl is a cycloalkyl having 3 to 12 carbon atoms), dialkylcycloalkylsilyl (where alkyl is an alkyl having 1 to 12 carbon atoms, and cycloalkyl is a cycloalkyl having 3 to 12 carbon atoms), or alkyldicycloalkylsilyl (where alkyl is an alkyl having 1 to 12 carbon atoms, and cycloalkyl is a cycloalkyl having 3 to 12 carbon atoms), and the two aryl groups of the diarylamino may be linked via a linking group, and the diheteroaryl The two heteroaryls of the amino may be linked via a linking group, the aryl and heteroaryl of the aryl heteroarylamino may be linked via a linking group, and the two aryls of the diarylboryl may be linked via a linking group, the linking group being a single bond, -CH2-CH2-, -CHR-CHR-, -CR2-CR2-, -CH=CH-, -CR=CR-, -C≡C-, -N(-R)-, -O-, -S-, -C(-R)2-, -Si(-R)2-, or -Se- However, at least one group represented by the above general formula (G) is bonded to the "a-ring" or "ring formed together with the a-ring," at least one group represented by the above general formula (G) is bonded to the "b-ring" or "ring formed together with the b-ring," and at least one group represented by the above general formula (G) is bonded to the "c-ring" or "ring formed together with the c-ring," and these groups represented by formula (G) may be the same or different. In the above formula (G), Cy 1 and Cy 2Each of these rings is independently a benzene ring, a naphthalene ring, a phenanthrene ring, a pyridine ring, a quinoline ring, a dibenzofuran ring, a dibenzothiophene ring, or a carbazole ring whose N position may be substituted with phenyl, and each of these rings is independently a diarylamino (where aryl is an aryl having 6 to 12 carbon atoms), a diheteroarylamino (where heteroaryl is a heteroaryl having 2 to 15 carbon atoms), or an arylheteroarylamino (where aryl is an aryl having 6 to 12 carbon atoms). Telloaryls are heteroaryls with 2 to 15 carbon atoms, diarylboryls (where aryl is aryl with 6 to 12 carbon atoms), alkyls with 1 to 24 carbon atoms, cycloalkyls with 3 to 24 carbon atoms, alkenyls with 1 to 24 carbon atoms, alkoxys with 1 to 24 carbon atoms, aryloxys with 6 to 30 carbon atoms, arylthios with 6 to 30 carbon atoms, triarylsilyls (where aryl is aryl with 6 to 12 carbon atoms), trialkylsilyls (where alkyl is alkyl with 1 to 12 carbon atoms), tricycloalkylsilyls (where cycloalkyl is C6 They may be substituted with cycloalkyl groups (3-12 carbon atoms), dialkylcycloalkylsilyl groups (where alkyl is an alkyl group having 1-12 carbon atoms, and cycloalkyl is a cycloalkyl group having 3-12 carbon atoms), alkyldicycloalkylsilyl groups (where alkyl is an alkyl group having 1-12 carbon atoms, and cycloalkyl is a cycloalkyl group having 3-12 carbon atoms), or cyano groups, and the two aryl groups of the diarylamino may be linked via a linking group, and the two heteroaryl groups of the diheteroarylamino may be linked via a linking group, The aryl and heteroaryl in the aryl heteroarylamino may be linked via a linking group, and the two aryls in the diarylboryl may be linked via a linking group, the linking group being a single bond, -CH2-CH2-, -CHR-CHR-, -CR2-CR2-, -CH=CH-, -CR=CR-, -C≡C-, -N(-R)-, -O-, -S-, -C(-R)2-, -Si(-R)2-, or -Se-, where * is the bond position to the a ring, b ring, c ring, and the ring formed together with those rings, and, In the compound represented by formula (1) above, at least one hydrogen atom may be substituted with deuterium, cyano, or halogen. A polycyclic aromatic compound as described in item 1.

[0014] Section 3. In the above equation (1), R 1 ~R 11 Each of these is independently hydrogen, diarylamino (where the aryl is an aryl having 6 to 12 carbon atoms), alkyl having 1 to 24 carbon atoms, cycloalkyl having 3 to 24 carbon atoms, alkoxy having 1 to 24 carbon atoms, aryloxy having 6 to 30 carbon atoms, or arylthio having 6 to 30 carbon atoms, and the two aryls of the diarylamino may be linked via a linking group, and such linking group is a single bond, -CH2-CH2-, -CHR-CHR-, -CR2-CR2-, -CH=CH-, -CR=CR-, -C≡C-, -N(-R)-, -O-, -S-, -C(-R)2-, -Si(-R)2-, or -Se-. R 1 ~R 11 Adjacent groups among them may bond together to form a naphthalene ring, a phenanthrene ring, a dibenzothiophene ring, a dibenzofuran ring, or a carbazole ring, and at least one hydrogen atom in the formed ring may independently be a diarylamino (where aryl has 6 to 12 carbon atoms), an alkyl group with 1 to 24 carbon atoms, a cycloalkyl group with 3 to 24 carbon atoms, or a group with 1 to 2 carbon atoms. It may be substituted with alkoxy of 4, aryloxy having 6 to 30 carbon atoms, or arylthio having 6 to 30 carbon atoms, and the two aryls of the diarylamino may be linked via a linking group, the linking group being a single bond, -CH2-CH2-, -CHR-CHR-, -CR2-CR2-, -CH=CH-, -CR=CR-, -C≡C-, -N(-R)-, -O-, -S-, -C(-R)2-, -Si(-R)2-, or -Se- However, at least one group represented by the above general formula (G) is bonded to the "a-ring" or "ring formed together with the a-ring," at least one group represented by the above general formula (G) is bonded to the "b-ring" or "ring formed together with the b-ring," and at least one group represented by the above general formula (G) is bonded to the "c-ring" or "ring formed together with the c-ring," and these groups represented by formula (G) may be the same or different. In the above formula (G), Cy 1 and Cy 2 Each of these rings is independently a benzene ring, a naphthalene ring, a phenanthrene ring, a pyridine ring, a quinoline ring, a dibenzofuran ring, a dibenzothiophene ring, or a carbazole ring whose N position may be substituted with phenyl, and each of these rings is independently a diarylamino (where aryl is an aryl having 6 to 12 carbon atoms), an alkyl having 1 to 24 carbon atoms, a cycloalkyl having 3 to 24 carbon atoms, an alkoxy having 1 to 24 carbon atoms, an aryloxy having 6 to 30 carbon atoms, or a carbon atom. The diarylamino may be substituted with arylthio or cyano groups numbered 6 to 30, and the two aryl groups of the diarylamino may be linked via a linking group, which is a single bond, -CH2-CH2-, -CHR-CHR-, -CR2-CR2-, -CH=CH-, -CR=CR-, -C≡C-, -N(-R)-, -O-, -S-, -C(-R)2-, -Si(-R)2-, or -Se-, where * is the bond position to the a-ring, b-ring, c-ring, and the ring formed together with those rings, and, In the compound represented by formula (1) above, at least one hydrogen atom may be substituted with deuterium, cyano, or halogen. A polycyclic aromatic compound as described in item 1.

[0015] Section 4. In the above equation (1), R 1 ~R 11 Each of these is independently hydrogen, diarylamino (where aryl has 6 to 12 carbon atoms), alkyl with 1 to 24 carbon atoms, or cycloalkyl with 3 to 24 carbon atoms. R 1~R 11 Adjacent groups among them may bond together to form a naphthalene ring, a phenanthrene ring, a dibenzothiophene ring, a dibenzofuran ring, or a carbazole ring, and at least one hydrogen atom in the formed ring may be independently substituted with a diarylamino (where the aryl is an aryl having 6 to 12 carbon atoms), an alkyl having 1 to 24 carbon atoms, or a cycloalkyl having 3 to 24 carbon atoms. However, at least one group represented by the above general formula (G) is bonded to the "a-ring" or "ring formed together with the a-ring," at least one group represented by the above general formula (G) is bonded to the "b-ring" or "ring formed together with the b-ring," and at least one group represented by the above general formula (G) is bonded to the "c-ring" or "ring formed together with the c-ring," and these groups represented by formula (G) may be the same or different. In the above formula (G), Cy 1 and Cy 2 Each of these rings is independently a benzene ring, a naphthalene ring, a phenanthrene ring, a pyridine ring, a quinoline ring, a dibenzofuran ring, a dibenzothiophene ring, or a carbazole ring whose N position may be substituted with phenyl, and each of these rings may independently be substituted with a diarylamino (where the aryl is a C6-C12 aryl), a C1-C24 alkyl, a C3-C24 cycloalkyl, or a cyano, and * is the bond position to the a ring, b ring, c ring, and the ring formed together with these rings, and, In the compound represented by formula (1) above, at least one hydrogen atom may be substituted with deuterium, cyano, or halogen. A polycyclic aromatic compound as described in item 1.

[0016] Section 5. In the above equation (1), R 1 ~R 11 Each of these is independently hydrogen or an alkyl group having 1 to 24 carbon atoms. However, R in ring a1 ~R 3 At least one of the R in the b ring 4 ~R 7 At least one of the and R in the c ring 8 ~R 11 At least one of these is a group represented by the general formula (G) above, and these groups represented by formula (G) may be the same or different. In the above formula (G), Cy 1 and Cy 2 Each of these rings is independently a benzene ring, a naphthalene ring, a phenanthrene ring, a pyridine ring, a quinoline ring, a dibenzofuran ring, a dibenzothiophene ring, or a carbazole ring whose N-position may be substituted with phenyl, and each of these rings may independently be substituted with an alkyl or cyano having 1 to 24 carbon atoms, and * is the bond position to the a, b, and c rings, and, In the compound represented by formula (1) above, at least one hydrogen atom may be substituted with deuterium, cyano, or halogen. A polycyclic aromatic compound as described in item 1.

[0017] Section 6. A polycyclic aromatic compound as described in item 1, represented by one of the following structural formulas. [ka] [ka] [ka]

[0018] Section 7. A polycyclic aromatic compound as described in item 1, represented by one of the following structural formulas. [ka]

[0019] Section 8. An organic electroluminescent element comprising a pair of electrodes consisting of an anode and a cathode, a light-emitting layer disposed between the pair of electrodes, and at least one electron transport layer and electron injection layer disposed between the cathode and the light-emitting layer and containing a polycyclic aromatic compound as described in any one of items 1 to 7.

[0020] Section 9. A display device or lighting device equipped with an organic electroluminescent element as described in item 8. [Effects of the Invention]

[0021] According to a preferred embodiment of the present invention, a novel polycyclic aromatic compound having a unique structure can be provided, which can be used as a material for organic devices such as organic EL elements. By using this polycyclic aromatic compound, it is possible to provide organic devices such as organic EL elements that exhibit excellent driving voltage, luminous efficiency, and element lifetime, particularly those with excellent luminous efficiency and element lifetime. [Brief explanation of the drawing]

[0022]

Figure 1

[0023] 1. Polycyclic aromatic compound <Explanation of the overall structure of the compound> The present invention relates to a polycyclic aromatic compound represented by the following general formula (1), characterized by having a group represented by the following general formula (G). The definitions of the symbols in the following structural formulas are the same as those described above, and furthermore, the definitions of the symbols in all structural formulas shown in this paragraph and thereafter are the same as those described above. [ka]

[0024] The compound of formula (1) has a structure in which an a-ring, a b-ring, and a c-ring are fused to a condensed biring structure. A condensed biring structure is a structure in which two 6-membered saturated hydrocarbon rings are fused together, and in the above structural formula, it is a decahydronaphthalene-type structure composed of B (boron) and two O (oxygen) atoms.

[0025] The group represented by formula (G) is a Cy having a specific ring structure. 1 and Cy 2 It is a group to which Cy 1 and Cy 2 These are, independently, a benzene ring, a naphthalene ring, a phenanthrene ring, a pyridine ring, a quinoline ring, a dibenzofuran ring, a dibenzothiophene ring, or a carbazole ring whose N-position may be substituted with phenyl. The group represented by formula (G) is bonded to the structure of formula (1) at *. The bonding configuration of the group represented by formula (G) will be described in detail later.

[0026] <Explanation of the substituents R on the a-ring, b-ring, and c-ring> 1 ~R 11 <Explanation of the change in the ring structure due to the bonding between substituents> In equation (1), the a, b, and c rings are, respectively, R 1 ~R 3 , R 4 ~R 7 , and R 8 ~R 11 It has this R 1 ~R 11These are, independently, hydrogen, diarylamino (the two aryls may be linked via a linking group), diheteroarylamino (the two heteroaryls may be linked via a linking group), arylheteroarylamino (the aryl and heteroaryl may be linked via a linking group), diarylboryl (the two aryls may be linked via a linking group), alkyl, cycloalkyl, alkenyl, alkoxy, aryloxy, arylthio, triarylsilyl, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, or alkyldicycloalkylsilyl. Details of the substituents listed here will be discussed later.

[0027] <Explanation of the substituents on the changed ring structure> R on the a-ring 1 ~R 3 Adjacent groups among these may bond together with the a-ring to form a naphthalene ring, phenanthrene ring, dibenzothiophene ring, dibenzofuran ring, or carbazole ring (including carbazole rings in which the N-position is substituted with a phenyl group) (these rings are referred to as "rings formed together with the a-ring"). R on ring b 4 ~R 7 Adjacent groups among these may bond together with the b-ring to form a naphthalene ring, phenanthrene ring, dibenzothiophene ring, dibenzofuran ring, or carbazole ring (including a carbazole ring in which the N-position is substituted with a phenyl group) (these rings are referred to as "rings formed together with the b-ring"). R on the c ring 8 ~R 11 Adjacent groups among these may bond together with the c ring to form a naphthalene ring, phenanthrene ring, dibenzothiophene ring, dibenzofuran ring, or carbazole ring (including a carbazole ring in which the N position is substituted with a phenyl group) (these rings are referred to as "rings formed together with the c ring").

[0028] R 1 ~R 3 (or R 4 ~R 7 or R8 ~R 11 A benzene ring, naphthalene ring, benzothiophene ring, benzofuran ring, or indole ring, formed by the bonding of adjacent groups among these rings, condenses with the benzene ring, which is the a ring (or b ring or c ring), to form a naphthalene ring, phenanthrene ring, dibenzothiophene ring, dibenzofuran ring, or carbazole ring, respectively.

[0029] The following are specific examples of ring structure changes. R for rings that remain unchanged. 1 ~R 11 It has been omitted. [ka]

[0030] The above equation (1-fr1-ex) is derived from the two adjacent R rings in the a ring in equation (1). 1 and R 2 This is an example where the atoms bond to form a benzene ring, and this benzene ring, together with the benzene ring of ring a, forms the naphthalene ring indicated by a'. Any substituent on the naphthalene ring a' is R 3 In addition, it is shown for n Rs, where the upper limit of n is the maximum number of permutations.

[0031] The above equation (1-fr2-ex) is derived from the two adjacent R rings in the b ring in equation (1). 5 and R 6 This is an example where the atoms bond to form an indole ring, and this indole ring, together with the benzene ring of the b ring, forms the carbazole ring shown as b'. Any substituent on the carbazole ring b' is R 4 and R 7 In addition to the above, n R groups are shown, where the upper limit of n is the maximum number of substitutions possible. Note that this carbazole ring also includes carbazole rings in which the N position is substituted with a phenyl group.

[0032] The above equation (1-fr3-ex) is derived from the two adjacent R rings in the b ring in equation (1). 4 and R 5The two R groups bond to form a benzene ring, and this benzene ring, together with the benzene ring of the b ring, forms the naphthalene ring indicated by b', and the two adjacent R groups in the c ring 10 and R 11 This is an example where the atoms bond to form a benzofuran ring, and this benzofuran ring, together with the benzene ring of the c ring, forms a dibenzofuran ring indicated by c'. Any substituents on the naphthalene ring b' and the dibenzofuran ring c' are R 6 ~R 9 In addition, each is shown with n Rs, where the upper limit of n is the maximum number of permutations.

[0033] The above explanation can be applied equally to all forms other than the specific examples mentioned above.

[0034] <Explanation of the group represented by formula (G)> At least one hydrogen atom in the ring formed with the a, b, or c ring (the a', b', and c' rings mentioned above) may be independently substituted with diarylamino (the two aryls may be linked via a linking group), diheteroarylamino (the two heteroaryls may be linked via a linking group), arylheteroarylamino (the aryl and heteroaryl may be linked via a linking group), diarylboryl (the two aryls may be linked via a linking group), alkyl, cycloalkyl, alkenyl, alkoxy, aryloxy, arylthio, triarylsilyl, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, or alkyldicycloalkylsilyl. Details of the substituents listed here will be described later.

[0035] <Explanation of the substituents on the group represented by formula (G)> The group represented by formula (G) is a Cy having a specific ring structure. 1 and Cy 2 It is a group to which Cy 1 and Cy 2Each of these is independently a benzene ring, a naphthalene ring, a phenanthrene ring, a pyridine ring, a quinoline ring, a dibenzofuran ring, a dibenzothiophene ring, or a carbazole ring whose N-position may be substituted with phenyl.

[0036] Cy 1 and Cy 2 In that order, A group to which a benzene ring is bonded is a benzene ring, a naphthalene ring, a phenanthrene ring, a pyridine ring, a quinoline ring, a dibenzofuran ring, a dibenzothiophene ring, or a carbazole ring whose N position may be substituted with phenyl. A group to which a benzene ring, naphthalene ring, phenanthrene ring, pyridine ring, quinoline ring, dibenzofuran ring, dibenzothiophene ring, or a carbazole ring whose N position may be substituted with phenyl is bonded, A group to which a phenanthrene ring is bonded is a benzene ring, a naphthalene ring, a phenanthrene ring, a pyridine ring, a quinoline ring, a dibenzofuran ring, a dibenzothiophene ring, or a carbazole ring whose N position may be substituted with phenyl. A group to which a pyridine ring is bonded is a benzene ring, naphthalene ring, phenanthrene ring, pyridine ring, quinoline ring, dibenzofuran ring, dibenzothiophene ring, or a carbazole ring which may have a phenyl substitution at the N position. A group to which a benzene ring, naphthalene ring, phenanthrene ring, pyridine ring, quinoline ring, dibenzofuran ring, dibenzothiophene ring, or a carbazole ring whose N position may be substituted with phenyl is bonded, A group to which a benzene ring, naphthalene ring, phenanthrene ring, pyridine ring, quinoline ring, dibenzofuran ring, dibenzothiophene ring, or a carbazole ring (which may have a phenyl substitution at the N position) is bonded, A group to which a benzene ring, naphthalene ring, phenanthrene ring, pyridine ring, quinoline ring, dibenzofuran ring, dibenzothiophene ring, or a carbazole ring (which may have a phenyl substitution at the N position) is bonded, Examples of groups to which a carbazole ring may have a phenyl substitution at the N position is bonded include a benzene ring, naphthalene ring, phenanthrene ring, pyridine ring, quinoline ring, dibenzofuran ring, dibenzothiophene ring, or a carbazole ring which may have a phenyl substitution at the N position.

[0037] Preferably, Cy 1 and Cy 2 In that order, examples include a group with two benzene rings bonded together, a group with a benzene ring and a naphthalene ring bonded together, a group with a pyridine ring and a benzene ring bonded together, a group with two pyridine rings bonded together, a group with a benzene ring and a carbazole ring (which may have a phenyl group substituted at the N position), a group with a benzene ring and a dibenzofuran ring bonded together, a group with a dibenzofuran ring and a benzene ring bonded together, a group with a benzene ring and a quinoline ring bonded together, a group with a benzene ring and a dibenzothiophene ring bonded together, a group with a benzene ring and a phenanthrene ring bonded together, and a group with two carbazole rings (which may have a phenyl group substituted at the N position).

[0038] <Explanation of the bonding of the group of formula (G) to the structure of formula (1)> Cy 1 and Cy 2 At least one hydrogen atom in each of these may be independently substituted with a diarylamino (the two aryl atoms may be linked via a linking group), a diheteroarylamino (the two heteroaryl atoms may be linked via a linking group), an arylheteroarylamino (the aryl and heteroaryl atoms may be linked via a linking group), a diarylboryl (the two aryl atoms may be linked via a linking group), an alkyl (preferably a C1-C4 alkyl, more preferably methyl), a cycloalkyl, an alkenyl, an alkoxy, an aryloxy, an arylthio, a triarylsilyl, a trialkylsilyl, a tricycloalkylsilyl, a dialkylcycloalkylsilyl, an alkyldicycloalkylsilyl, or a cyano. Preferred substituents are C1-C4 alkyls (more preferably methyl) and cyanos. Details of the substituents listed here will be described in more detail later.

[0039] <Specific explanation of the substituents> The group represented by formula (G) is bonded to the structure of formula (1) at *. Specifically, in formula (1), the a-ring or R on the a-ring as described above 1 ~R 3 at least one group represented by formula (G) is bonded to a naphthalene ring, a phenanthrene ring, a dibenzothiophene ring, a dibenzofuran ring, or a carbazole ring (i.e., the "ring formed together with the a-ring") formed by the bonding of adjacent groups among them together with the a-ring. When there are a plurality of groups represented by formula (G), they may be the same or different from each other. the b-ring or R on the b-ring as described above 4 ~R 7 at least one group represented by formula (G) is bonded to a naphthalene ring, a phenanthrene ring, a dibenzothiophene ring, a dibenzofuran ring, or a carbazole ring (i.e., the "ring formed together with the b-ring") formed by the bonding of adjacent groups among them together with the b-ring. When there are a plurality of groups represented by formula (G), they may be the same or different from each other, and the c-ring or R on the c-ring as described above 8 ~R 11 at least one group represented by formula (G) is bonded to a naphthalene ring, a phenanthrene ring, a dibenzothiophene ring, a dibenzofuran ring, or a carbazole ring (i.e., the "ring formed together with the c-ring") formed by the bonding of adjacent groups among them together with the c-ring. When there are a plurality of groups represented by formula (G), they may be the same or different from each other. Therefore, the compound of formula (1) is characterized by having at least three groups of formula (G). The plurality of groups represented by formula (G) may be the same or different from each other, and preferably have the same structure.

[0040] That the group represented by formula (G) is bonded to the a-ring, the b-ring, or the c-ring means that at least one of R 1 ~R 3 of the a-ring is R 4 ~R7 at least one of which, or R of the c-ring 8 ~R 11 at least one of which is the same as the group represented by formula (G).

[0041] The number of groups represented by formula (G) attached to each ring is 1 to 4, preferably 1 to 3, more preferably 1 to 2, and even more preferably 1.

[0042] <Explanation of substitution with deuterium, cyano, or halogen> Next, the details of the substituents listed in the previous explanations will be summarized and explained.

[0043] "Diaryl amino" is an amino group substituted with two aryls, and the two aryls may be bonded via a linking group. "Diheteroaryl amino" is an amino group substituted with two heteroaryls, and the two heteroaryls may be bonded via a linking group. "Aryl heteroaryl amino" is an amino group substituted with an aryl and a heteroaryl, and the aryl and the heteroaryl may be bonded via a linking group. "Diaryl boryl" is a boryl group substituted with two aryls, and the two aryls may be bonded via a linking group.

[0044] Details of these aryls, heteroaryls, and linking groups are as follows.

[0045] "Aryl" is, for example, aryl having 6 to 30 carbon atoms, preferably aryl having 6 to 20 carbon atoms, aryl having 6 to 16 carbon atoms, aryl having 6 to 12 carbon atoms, or aryl having 6 to 10 carbon atoms, etc.

[0046] Specific examples of "aryl" include monocyclic phenyl, condensed bicyclic naphthyl (1-naphthyl or 2-naphthyl), condensed tricyclic acenaphthylene-(1-,3-,4-, or 5-)yl, fluoren-(1-,2-,3-,4-, or 9-)yl, phenalen-(1- or 2-)yl, or phenanthrene-(1-,2-,3-,4-, or 9-)yl, condensed tetracyclic triphenylene-(1- or 2-)yl, pyren-(1-,2-, or 4-)yl, or naphthacene-(1-,2-, or 5-)yl, or condensed pentacyclic perylene-(1-,2-, or 3-)yl, or pentacene-(1-,2-,5-, or 6-)yl.

[0047] The "arylene (ring)" is, for example, an arylene having 6 to 30 carbon atoms, preferably an arylene having 6 to 20 carbon atoms, an arylene having 6 to 16 carbon atoms, an arylene having 6 to 12 carbon atoms, or an arylene having 6 to 10 carbon atoms. A specific example of "arylene" is a structure in which one hydrogen atom is removed from the aforementioned "aryl" (monovalent group) to create a divalent group.

[0048] A "heteroaryl" is, for example, a heteroaryl with 2 to 30 carbon atoms, preferably a heteroaryl with 2 to 25 carbon atoms, a heteroaryl with 2 to 20 carbon atoms, a heteroaryl with 2 to 15 carbon atoms, or a heteroaryl with 2 to 10 carbon atoms. A "heteroaryl" is also a monovalent group such as a heterocycle containing 1 to 5 heteroatoms selected from oxygen, sulfur, and nitrogen in addition to carbon as ring constituent atoms.

[0049] Specific examples of "heteroaryls" include pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, oxadiazolyl, thiadiazolyl, triazolyl, tetrazolyl, pyrazolyl, pyridinyl, pyrimidinyl, pyridadinyl, pyrazinyl, triazinyl, indolyl, isoindolyl, 1H-indazolyl, benzimidazolyl, benzoxazolyl, benzothiazolyl, 1H-benzotriazolyl, quinolinyl, isoquinolinyl, cinnolinyl, quinazolinyl, quinoxalinyl, phenanthrolinyl, phthalazinyl, naphthyridinyl, prinyl, pteridinyl, carbazolyl, acridinyl, and phenoxathiini. These include phenoxazinil, phenothiazinil, phenazinil, phenazacylinil, indolidinil, furanil, benzofuranil, isobenzofuranil, dibenzofuranil, naphthobenzofuranil, thiophenyl, benzothiophenyl, isobenzothiophenyl, dibenzothiophenyl, naphthobenzothiophenyl, benzophosphoryl, dibenzophosphoryl, monovalent group of the benzophosphorus oxide ring, monovalent group of the dibenzophosphorus oxide ring, furazanil, thianthrenil, indolocarbazolyl, benzoindolocabozolyl, benzobenzoindolocabozolyl, imidazolinil, oxazolinil, or dibenzosilacyclopentadienyl.

[0050] "Heteroarylene (ring)" refers to, for example, heteroarylenes having 2 to 30 carbon atoms, preferably heteroarylenes having 2 to 25 carbon atoms, 2 to 20 carbon atoms, 2 to 15 carbon atoms, or 2 to 10 carbon atoms. Furthermore, "heteroarylene" is a divalent group such as a heterocycle containing, for example, 1 to 5 heteroatoms selected from oxygen, sulfur, and nitrogen in addition to carbon as ring constituent atoms. A specific example of a "heteroarylene" is a structure in which one hydrogen atom is removed from the aforementioned "heteroaryl" (monovalent group) to create a divalent group.

[0051] Examples of "linking groups" include single bonds, -CH2-CH2-, -CHR-CHR-, -CR2-CR2-, -CH=CH-, -CR=CR-, -C≡C-, -N(-R)-, -O-, -S-, -C(-R)2-, -Si(-R)2-, or -Se-, and the following structures are examples. Note that the R in "-CHR-CHR-", the R in "-CR2-CR2-", the R in "-CR=CR-", the R in "-N(-R)-", the R in "-C(-R)2-", and the R in "-Si(-R)2-" are each independently hydrogen, aryl, heteroaryl, alkyl, alkenyl, alkynyl, or cycloalkyl, and at least one hydrogen in the R may be substituted with alkyl or cycloalkyl. Furthermore, in "-CHR-CHR-", "-CR2-CR2-", "-CR=CR-", "-C(-R)2-", and "-Si(-R)2-", two adjacent R atoms may bond to form a cycloalkylene ring, an arylene ring, and a heteroarylene ring (see the rightmost structural formula in the structural formulas below). Details of the substituents listed here will be described collectively above or below. [ka]

[0052] Preferred linking groups include single bonds, -CR=CR-, -N(-R)-, -O-, -S-, -C(-R)2-, -Si(-R)2-, and -Se-; more preferably single bonds, -CR=CR-, -N(-R)-, -O-, -S-, and -C(-R)2-; even more preferably single bonds, -CR=CR-, -N(-R)-, -O-, and -S-; and most preferably single bonds and -CR=CR-.

[0053] The positions where the two R groups bond via the linking group are not particularly limited as long as they are bondable positions, but it is preferable that they bond at the most adjacent positions. For example, if the two R groups are phenyl groups, it is preferable that they bond at the ortho (position 2) relative to the bond position (position 1) of the "C" or "Si" in the phenyl group (see the structural formula above).

[0054] "Alkyl" can be either a linear or branched alkyl group, for example, a linear alkyl group having 1 to 24 carbon atoms or a branched alkyl group having 3 to 24 carbon atoms. Preferably, it is an alkyl group having 1 to 18 carbon atoms (branched alkyl group having 3 to 18 carbon atoms), an alkyl group having 1 to 12 carbon atoms (branched alkyl group having 3 to 12 carbon atoms), an alkyl group having 1 to 6 carbon atoms (branched alkyl group having 3 to 6 carbon atoms), an alkyl group having 1 to 5 carbon atoms (branched alkyl group having 3 to 5 carbon atoms), an alkyl group having 1 to 4 carbon atoms (branched alkyl group having 3 to 4 carbon atoms), and so on.

[0055] Specific examples of "alkyl" include methyl, ethyl, n-propyl, isopropyl, 1-ethyl-1-methylpropyl, 1,1-diethylpropyl, 1,1,2-trimethylpropyl, 1,1,2,2-tetramethylpropyl, 1-ethyl-1,2,2-trimethylpropyl, n-butyl, isobutyl, s-butyl, t-butyl, 2-ethylbutyl, 1,1-dimethylbutyl, 3,3-dimethylbutyl, 1,1-diethylbutyl, 1-ethyl-1-methylbutyl, 1-propyl-1-methylbutyl, 1,1,3-trimethylbutyl, 1-ethyl-1,3-dimethylbutyl, n-pentyl, isopentyl, neopentyl, t-pentyl (t-amyl), 1-methylpentyl, 2-propylpentyl, 1,1-dimethylpentyl, 1-ethyl-1-methylpentyl, 1-propyl-1 -Methylpentyl, 1-butyl-1-methylpentyl, 1,1,4-trimethylpentyl, n-hexyl, 1-methylhexyl, 2-ethylhexyl, 1,1-dimethylhexyl, 1-ethyl-1-methylhexyl, 1,1,5-trimethylhexyl, 3,5,5-trimethylhexyl, n-heptyl, 1-methylheptyl, 1-hexylheptyl, 1,1-dimethylheptyl, 2,2-di Examples include methylheptyl, 2,6-dimethyl-4-heptyl, n-octyl, t-octyl (1,1,3,3-tetramethylbutyl), 1,1-dimethyloctyl, n-nonyl, n-decyl, 1-methyldecyl, n-undecyl, n-dodecyl, n-tridecyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, n-heptadecyl, n-octadecyl, or n-eicosyl.

[0056] Regarding "alkenyl," you can refer to the explanation of "alkyl" above. It is a group in which a single C=C bond in the structure of "alkyl" is replaced with a C=C double bond, and it includes not just one but two or more single bonds that are replaced with double bonds (also called alkadiene-yl or alkatriene-yl).

[0057] Regarding "alkynyl," you can refer to the explanation of "alkyl" above. It is a group in which a single C≡C bond in the structure of "alkyl" is replaced with a triple C≡C bond, and it includes not just one but two or more single bonds that are replaced with triple bonds (also called alkadiyne-yl or alkatriyne-yl).

[0058] "Cycloalkyl" refers to, for example, a cycloalkyl group having 3 to 24 carbon atoms, preferably a cycloalkyl group having 3 to 20 carbon atoms, 3 to 16 carbon atoms, 3 to 14 carbon atoms, 3 to 12 carbon atoms, 5 to 10 carbon atoms, 5 to 8 carbon atoms, 5 to 6 carbon atoms, or a cycloalkyl group having 5 carbon atoms.

[0059] Specific examples of "cycloalkyl" include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, or alkyl (especially methyl) substituted derivatives of these with 1-5 or 1-4 carbon atoms, norborneyl, bicyclo[1.1.0]butyl, bicyclo[1.1.1]pentyl, bicyclo[2.1.0]pentyl, bicyclo[2.1.1]hexyl, bicyclo[3.1.0]hexyl, bicyclo[2.2.1]heptyl, bicyclo[2.2.2]octyl, adamantyl, diamantyl, decahydronaphthalenyl, or decahydroazlenyl.

[0060] The "cycloalkylene (ring)" is, for example, a cycloalkylene having 3 to 24 carbon atoms, preferably a cycloalkylene having 3 to 20 carbon atoms, a cycloalkylene having 3 to 16 carbon atoms, a cycloalkylene having 3 to 14 carbon atoms, a cycloalkylene having 3 to 12 carbon atoms, a cycloalkylene having 5 to 10 carbon atoms, a cycloalkylene having 5 to 8 carbon atoms, a cycloalkylene having 5 to 6 carbon atoms, or a cycloalkylene having 5 carbon atoms. A specific example of a "cycloalkylene" is a structure in which one hydrogen atom is removed from the aforementioned "cycloalkyl" (monovalent group) to create a divalent group.

[0061] For "cycloalkenyl," please refer to the explanation of "cycloalkyl" above. It is a group in which the single C=C bond in the structure of "cycloalkyl" is replaced with a C=C double bond, and includes not just one, but two or more single bonds that are replaced with double bonds (also called cycloalkadienyl or cycloalkantrienyl).

[0062] "Alkoxy" can be either linear or branched, for example, a linear alkoxy having 1 to 24 carbon atoms or a branched alkoxy having 3 to 24 carbon atoms. Preferably, it is an alkoxy having 1 to 18 carbon atoms (branched alkoxy having 3 to 18 carbon atoms), an alkoxy having 1 to 12 carbon atoms (branched alkoxy having 3 to 12 carbon atoms), an alkoxy having 1 to 6 carbon atoms (branched alkoxy having 3 to 6 carbon atoms), an alkoxy having 1 to 5 carbon atoms (branched alkoxy having 3 to 5 carbon atoms), an alkoxy having 1 to 4 carbon atoms (branched alkoxy having 3 to 4 carbon atoms), and so on.

[0063] Specific examples of "alkoxy" include methoxy, ethoxy, n-propoxy, isopropoxy, 1-ethyl-1-methylpropoxy, 1,1-diethylpropoxy, 1,1,2-trimethylpropoxy, 1,1,2,2-tetramethylpropoxy, 1-ethyl-1,2,2-trimethylpropoxy, n-butoxy, isobutoxy, s-butoxy, t-butoxy, 2-ethylbutoxy, 1,1-dimethylbutoxy, 3,3-dimethylbutoxy, 1,1-diethylbutoxy, 1-Ethyl-1-methylbutoxy, 1-Propyl-1-methylbutoxy, 1,1,3-trimethylbutoxy, 1-Ethyl-1,3-dimethylbutoxy, n-pentyloxy, isopentyloxy, neopentyloxy, t-pentyloxy (t-amyloxy), 1-methylpentyloxy, 2-propylpentyloxy, 1,1-dimethylpentyloxy, 1-ethyl-1-methylpentyloxy, 1-propyl-1-methylpentyloxy, 1-butyl-1-methyl Pentyloxy, 1,1,4-trimethylpentyloxy, n-hexyloxy, 1-methylhexyloxy, 2-ethylhexyloxy, 1,1-dimethylhexyloxy, 1-ethyl-1-methylhexyloxy, 1,1,5-trimethylhexyloxy, 3,5,5-trimethylhexyloxy, n-heptyloxy, 1-methylheptyloxy, 1-hexylheptyloxy, 1,1-dimethylheptyloxy, 2,2-dimethylheptyloxy, 2,6-dimethylheptyloxy These include tyl-4-heptyloxy, n-octyloxy, t-octyloxy (1,1,3,3-tetramethylbutyloxy), 1,1-dimethyloctyloxy, n-nonyloxy, n-decyloxy, 1-methyldecyloxy, n-undecyloxy, n-dodecyloxy, n-tridecyloxy, n-tetradecyloxy, n-pentadecyloxy, n-hexadecyloxy, n-heptadecyloxy, n-octadecyloxy, or n-eicosyloxy.

[0064] An "aryloxy" is a group represented as "Ar-O-" (where Ar is an aryl group), and for details about this aryl group, please refer to the explanation of "aryl" mentioned above.

[0065] "Arylthio" is a group represented as "Ar-S- (Ar is an aryl group)," and for details about this aryl group, please refer to the explanation of "aryl" mentioned above.

[0066] A "triarylsilyl" is a silyl group substituted with three aryl groups. For details about these aryl groups, please refer to the explanation of "aryl" mentioned above. Specific examples of "triarylsilyls" include triphenylsilyl, diphenylmononaphthylsilyl, monophenyldinaphthylsilyl, or trinaphthylsilyl.

[0067] "Trialkylsilyl" refers to a silyl group substituted with three alkyl groups. For details about these alkyl groups, please refer to the explanation of "alkyl" mentioned above. Specific examples of "trialkylsilyls" include trimethylsilyl, triethylsilyl, tri-n-propylsilyl, triisopropylsilyl, tri-n-butylsilyl, triisobutylsilyl, tri-s-butylsilyl, tri-t-butylsilyl, ethyldimethylsilyl, n-propyldimethylsilyl, isopropyldimethylsilyl, n-butyldimethylsilyl, isobutyldimethylsilyl, s-butyldimethylsilyl, t-butyldimethylsilyl, methyldiethylsilyl, n-propyldiethylsilyl, isopropyldiethylsilyl, n-butyldiethylsilyl, s-butyldiethylsilyl, t-butyldiethylsilyl, methyldi-n-propylsilyl, ethyldi-n-propylsilyl, n-butyldi-n-propylsilyl, s-butyldi-n-propylsilyl, t-butyldi-n-propylsilyl, methyldiisopropylsilyl, ethyldiisopropylsilyl, n-butyldiisopropylsilyl, s-butyldiisopropylsilyl, or t-butyldiisopropylsilyl.

[0068] "Tricycloalkylsilyl" is a silyl group substituted with three cycloalkyl groups. For details on these cycloalkyl groups, please refer to the explanation of "cycloalkyl" mentioned above. Specific examples of "tricycloalkylsilyls" include tricyclopentylsilyl or tricyclohexylsilyl.

[0069] A "dialkylcycloalkylsilyl" is a silyl group substituted with two alkyl groups and one cycloalkyl group. For details on these alkyl and cycloalkyl groups, please refer to the explanations of "alkyl" and "cycloalkyl" above.

[0070] "Alkyldicycloalkylsilyl" refers to a silyl group substituted with one alkyl and two cycloalkyl groups. For details on these alkyl and cycloalkyl groups, please refer to the explanations of "alkyl" and "cycloalkyl" above.

[0071] Substituents affect the emission wavelength of polycyclic aromatic compounds due to their steric hindrance, electron-donating, and electron-withdrawing properties; therefore, the emission wavelength can be adjusted by selecting the substituent. Preferably, the group is represented by the following structural formula, and more preferably, methyl, t-butyl, bicyclooctyl, 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, diphenylboryl, dimesitylboryl, dibenzoxaborinyl, phenyldibenzodiborinyl These are nyl, carbazolyl, 3,6-dimethylcarbazolyl, 3,6-di-t-butylcarbazolyl, and phenoxy, and more preferably methyl, t-butyl, phenyl, o-tolyl, 2,6-xylyl, 2,4,6-mesityl, diphenylamino, di-p-tolylamino, bis(p-(t-butyl)phenyl)amino, carbazolyl, 3,6-dimethylcarbazolyl, 3,6-di-t-butylcarbazolyl, and tribenzoazepinyl. From the viewpoint of ease of synthesis, greater steric hindrance is preferable for selective synthesis, and specifically, t-butyl, 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.

[0072] In the structural formula below, "Me" represents methyl, "tBu" represents t-butyl, "tAm" represents t-amyl, and "tOct" represents t-octyl, and * represents the bond position. [ka] [ka] [ka] [ka]

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[0073] <Explanation of specific examples of the polycyclic aromatic compound of the present invention> At least one hydrogen in the polycyclic aromatic compound of the present invention (the hydrogen in the group represented by formula (G) and the hydrogen in the part other than the group represented by formula (G)) may be substituted with deuterium, cyano, or halogen. Further, at least one hydrogen in the part other than the group represented by formula (G) in the polycyclic aromatic compound of the present invention may be substituted with deuterium, cyano, or halogen. Halogen is fluorine, chlorine, bromine, or iodine, fluorine, chlorine, or bromine is preferable, and fluorine or chlorine is more preferable.

[0074] <Application of the polycyclic aromatic compound to polymers> Specific examples of the polycyclic aromatic compound include compounds represented by the following structural formulas. In the following structural formulas, "Me" represents a methyl group, "CN" represents a cyano group, and "D" represents deuterium.

[0075]

Chemical formula

[0076]

Chemical formula

[0077]

Chemical formula

[0078]

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[0079]

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[0080]

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[0081]

Chemical formula

[0082]

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[0083]

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[0084]

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[0085]

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[0086]

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[0087]

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[0088]

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[0091]

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[0092] [ka]

[0093] [ka]

[0094] [ka]

[0095] [ka]

[0096] 2. Method for producing a polycyclic aromatic compound represented by formula (1) The polycyclic aromatic compounds according to the present invention can be used as materials for organic devices, such as materials for organic field-effect light-emitting devices, materials for organic field-effect transistors, or materials for organic thin-film solar cells, whether as polymer compounds obtained by polymerizing reactive compounds in which reactive substituents are substituted thereon (the monomers for obtaining this polymer compound have polymerizable substituents), or as crosslinked polymers obtained by further crosslinking the polymer compound (the polymer compound for obtaining this crosslinked polymer has crosslinkable substituents), or as pendant-type polymer compounds obtained by reacting a main-chain polymer with the reactive compound (the reactive compound for obtaining this pendant-type polymer compound has reactive substituents), or as crosslinked pendant-type polymers obtained by further crosslinking the pendant-type polymer compound (the pendant-type polymer compound for obtaining this crosslinked polymer has crosslinkable substituents).

[0097] The reactive substituents described above (including the polymerizable substituents, the crosslinkable substituents, and the reactive substituents for obtaining a pendant-type polymer, and hereinafter simply referred to as "reactive substituents") are not particularly limited as substituents that can increase the molecular weight of the polycyclic aromatic compound, substituents that can further crosslink the polymer compound obtained in this way, and substituents that can undergo a pendant reaction with the main chain polymer, but substituents with the following structures are preferred. * in each structural formula indicates the bond position. [ka]

[0098] L is independently a single bond, -O-, -S-, >C=O, -OC(=O)-, a C1-C12 alkylene, a C1-C12 oxyalkylene, and a C1-C12 polyoxyalkylene. Among the above substituents, groups represented by formula (XLS-1), (XLS-2), (XLS-3), (XLS-9), (XLS-10), or (XLS-17) are preferred, and groups represented by formula (XLS-1), (XLS-3), or (XLS-17) are more preferred.

[0099] Such polymer compounds, polymer crosslinks, pendant-type polymer compounds, and pendant-type polymer crosslinks may also contain, in addition to the repeating units of the polycyclic aromatic compounds according to the present invention, at least one compound selected from the group consisting of substituted or unsubstituted triarylamines, substituted or unsubstituted fluorenes, substituted or unsubstituted anthracenes, substituted or unsubstituted tetracenes, substituted or unsubstituted triazines, substituted or unsubstituted carbazoles, substituted or unsubstituted tetraphenylsilanes, substituted or unsubstituted spirofluorenes, substituted or unsubstituted triphenylphosphines, substituted or unsubstituted dibenzothiophenes, and substituted or unsubstituted dibenzofurans as a repeating unit.

[0100] Examples of substituents in these repeating units include aryl, heteroaryl, diarylamino (the two aryls may be linked via a linking group), diheteroarylamino (the two heteroaryls may be linked via a linking group), arylheteroarylamino (the aryl and heteroaryl may be linked via a linking group), diarylboryl (the two aryls may be linked via a linking group), alkyl, cycloalkyl, alkoxy, aryloxy, triarylsilyl, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, or alkyldicycloalkylsilyl. Details regarding the "aryl" in triarylamine and these substituents can be referenced from the description of polycyclic aromatic compounds according to the present invention.

[0101] Details of the applications of such polymer compounds, polymer crosslinks, pendant-type polymer compounds, and pendant-type polymer crosslinks (hereinafter also simply referred to as "polymer compounds and polymer crosslinks") will be described later.

[0102] 3. Organic device Polycyclic aromatic compounds represented by general formula (1) can be produced according to methods described in many publicly available documents, including International Publication No. 2015 / 102118.

[0103] Basically, an intermediate is first produced by bonding the a, b, and c rings with an ether group (first reaction), and then the final product is produced by bonding the a, b, and c rings with a group containing the central element B (boron) (second reaction). In the first reaction, general etherification reactions such as nucleophilic substitution and Ullmann reactions can be used. In the second reaction, a tandem hetero-Friedel-Crafts reaction (a series of aromatic electrophilic substitution reactions, the same applies below) can be used.

[0104] Furthermore, by using a starting material having a group represented by formula (G) at any point in these reaction steps, or by adding a step to introduce a group represented by formula (G), a compound in which the group represented by formula (G) is bonded at a desired position can be produced. Additionally, by using a starting material that has been deuterated, cyanated, or halogenated at any point in these reaction steps, or by adding a step of deuteration, cyanation, or halogenation, a compound in which the desired position is deuterated, cyanated, or halogenated can be produced.

[0105] The second reaction, as shown in scheme (1) below, is a reaction to introduce a central element B (boron) that connects the a, b, and c rings. First, the hydrogen atom between the two ether bonds is orthometalated with n-butyllithium, sec-butyllithium, or t-butyllithium, etc. Next, boron trichloride or boron tribromide, etc., is added to perform a lithium-boron metal exchange, and then a Brønsted base such as N,N-diisopropylethylamine is added to carry out a tandem bora-Friedel-Crafts reaction to obtain the target product. In the second reaction, a Lewis acid such as aluminum trichloride may be added to accelerate the reaction. [ka]

[0106] Specific examples of solvents used in the above reactions include t-butylbenzene and xylene.

[0107] Examples of orthometalation reagents include alkyllithium compounds such as methyllithium, n-butyllithium, sec-butyllithium, and t-butyllithium, as well as organic alkali compounds such as lithium diisopropylamide, lithium tetramethylpiperidide, lithium hexamethyldisilazide, and potassium hexamethyldisilazide.

[0108] Furthermore, examples of metal exchange reagents for metal-B (boron) include boron halides such as boron trifluoride, boron trichloride, boron tribromide, and boron triiodide, boron amination halides such as CIPN(NEt2)2, boron alkoxylated compounds, and boron aryl oxylated compounds.

[0109] Examples of Brønsted bases include N,N-diisopropylethylamine, triethylamine, 2,2,6,6-tetramethylpiperidine, 1,2,2,6,6-pentamethylpiperidine, N,N-dimethylaniline, N,N-dimethyltoluidine, 2,6-lutidine, sodium tetraphenylborate, potassium tetraphenylborate, triphenylborane, tetraphenylsilane, Ar4BNa, Ar4BK, Ar3B, and Ar4Si (where Ar is an aryl such as phenyl).

[0110] Examples of Lewis acids include AlCl3, AlBr3, AlF3, BF3·OEt2, BCl3, BBr3, GaCl3, GaBr3, InCl3, InBr3, In(OTf)3, SnCl4, SnBr4, AgOTf, ScCl3, Sc(OTf)3, ZnCl2, ZnBr2, Zn(OTf)2, MgCl2, MgBr2, Mg(OTf)2, LiOTf, NaOTf, KOTf, Me3SiOTf, Cu(OTf)2, CuCl2, YCl3, Y(OTf)3, TiCl4, TiBr4, ZrCl4, ZrBr4, FeCl3, FeBr3, CoCl3, and CoBr3.

[0111] In each of the above schemes, a Brønsted base or Lewis acid may be used to accelerate the tandem hetero-Friedel-Crafts reaction. However, when using boron halides such as boron trifluoride, boron trichloride, boron tribromide, and boron triiodide, acids such as hydrogen fluoride, hydrogen chloride, hydrogen bromide, and hydrogen iodide are generated as the aromatic electrophilic substitution reaction progresses, so the use of a Brønsted base to capture the acid is effective. On the other hand, when using boron amination halides or boron alkoxyides, amines and alcohols are generated as the aromatic electrophilic substitution reaction progresses, so in most cases, it is not necessary to use a Brønsted base. However, because the leaving ability of amino and alkoxy groups is low, the use of a Lewis acid to promote their elimination is effective.

[0112] 3-1. Organic electroluminescent device In the chemical structural formulas exemplified from this point forward, "Me" represents a methyl group and "tBu" represents a t-butyl group. The polycyclic aromatic compounds according to the present invention can be used as materials for organic devices. Examples of organic devices include organic field-light-emitting devices, organic field-effect transistors, organic thin-film solar cells, and wavelength conversion filters.

[0113] 3-2. Other organic devices The polycyclic aromatic compounds according to the present invention can be used, for example, as materials for organic electroluminescent devices. Below, an organic EL element according to this embodiment will be described in detail with reference to the drawings. Figure 1 is a schematic cross-sectional view showing an organic EL element according to this embodiment.

[0114] <Structure of Organic Field-Emitting Light> The organic EL element 100 shown in Figure 1 comprises 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, a light-emitting layer 105 provided on the hole transport layer 104, an electron transport layer 106 provided on the light-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.

[0115] The organic EL element 100 may also be configured by reversing the manufacturing order, for example, by having 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 emissive layer 105 provided on the electron transport layer 106, a hole transport layer 104 provided on the emissive 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.

[0116] Not all of the above layers are necessarily required; the minimum configuration unit consists of an anode 102, a light-emitting layer 105, and a cathode 108, and the hole injection layer 103, hole transport layer 104, electron transport layer 106, and electron injection layer 107 are optional layers. Furthermore, each of the above layers may consist of a single layer or multiple layers.

[0117] In addition to the above-mentioned "substrate / anode / hole injection layer / hole transport layer / emissive layer / electron transport layer / electron injection layer / cathode" configurations, other configurations of layers constituting an organic EL element include "substrate / anode / hole transport layer / emissive layer / electron transport layer / electron injection layer / cathode", "substrate / anode / hole injection layer / emissive layer / electron transport layer / electron injection layer / cathode", "substrate / anode / hole injection layer / hole transport layer / emissive layer / electron injection layer / cathode", and "substrate / anode / hole injection layer / hole transport layer / emissive layer / electron transport The configuration may also be "transport layer / cathode", "substrate / anodode / emissive layer / electron transport layer / electron injection layer / cathode", "substrate / anodode / hole transport layer / emissive layer / electron injection layer / cathode", "substrate / anodode / hole transport layer / emissive layer / electron transport layer / cathode", "substrate / anodode / hole injection layer / emissive layer / electron injection layer / cathode", "substrate / anodode / hole injection layer / emissive layer / electron transport layer / cathode", "substrate / anodode / emissive layer / electron transport layer / cathode", or "substrate / anodode / emissive layer / electron injection layer / cathode".

[0118] <Substrates for organic electroluminescent devices> The substrate 101 is a support for the organic EL element 100, and is typically made of quartz, glass, metal, or plastic. The substrate 101 is formed in the form of a plate, film, or sheet depending on the purpose, and can be made of glass, metal, metal foil, plastic film, or plastic sheet, for example. Among these, glass plates and transparent synthetic resin plates such as polyester, polymethacrylate, polycarbonate, or polysulfone are preferred. If a glass substrate is used, soda-lime glass or alkali-free glass can be used, and the thickness only needs to be sufficient to maintain mechanical strength, for example, 0.2 mm or more is sufficient. The upper limit of the thickness is, for example, 2 mm or less, preferably 1 mm or less. Regarding the glass material, alkali-free glass is preferred because it is better to have fewer ions eluted from the glass, but soda-lime glass with a barrier coating such as SiO2 is also commercially available and can be used. Furthermore, to enhance the gas barrier properties, the substrate 101 may be provided with a gas barrier film, such as a dense silicon oxide film, on at least one side. It is particularly preferable to provide a gas barrier film when using a synthetic resin plate, film, or sheet with low gas barrier properties as the substrate 101.

[0119] <Anode in an organic electroluminescent element> The anode 102 plays the role of injecting holes into the light-emitting layer 105. If at least one of the hole injection layer 103 and hole transport layer 104 is provided between the anode 102 and the light-emitting layer 105, holes will be injected into the light-emitting layer 105 via these layers.

[0120] 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), conductive polymers such as polypyrrole and polyaniline. In addition, other materials used as anodes in organic EL elements can be appropriately selected and used.

[0121] The resistance of the transparent electrode is not limited as long as it can supply sufficient current for the light-emitting element to emit light, but from the viewpoint of the power consumption of the light-emitting element, low resistance is desirable. For example, an ITO substrate with a resistance of 300 Ω / □ or less will function as an element electrode, but since substrates of about 10 Ω / □ are now available, it is particularly desirable to use a low-resistance product of, for example, 100 to 5 Ω / □, preferably 50 to 5 Ω / □. The thickness of the ITO can be arbitrarily selected according to the resistance value, but it is usually used between 50 and 300 nm.

[0122] <Hole injection layer and hole transport layer in organic electroluminescent devices> The hole injection layer 103 plays the 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 the 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 hole injection / transport materials and a polymer binder. Alternatively, an inorganic salt such as iron(III) chloride may be added to the hole injection / transport material to form a layer.

[0123] For hole-injecting and transporting materials, it is necessary to efficiently inject and transport holes from the positive electrode between electrodes under an applied electric field. Therefore, it is desirable to have high hole injection efficiency and efficient transport of the injected holes. To achieve this, it is preferable to have a low ionization potential, high hole mobility, excellent stability, and a material that does not easily generate trapping impurities during manufacturing and use.

[0124] As the material for forming the hole injection layer 103 and the hole transport layer 104 (hole transport material), any compound can be selected and used from among compounds conventionally used as charge transport materials for holes in photoconductive materials, p-type semiconductors, and known compounds used in the hole injection layer and hole transport layer of organic EL elements. In the present invention, a polycyclic aromatic compound represented by the above general formula (1) can be used as this hole transport material.

[0125] Specific examples include carbazole derivatives (N-phenylcarbazole, polyvinylcarbazole, etc.), biscarbazole derivatives such as bis(N-arylcarbazole) or bis(N-alkylcarbazole), and triarylamine derivatives (polymers having aromatic tertiary amino acids 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-carbazole-3-yl)-[1,1'-biphenyl]-4,4'-diamine, N 4 ,N 4 ,N 4’ ,N 4’ Triphenylamine derivatives such as -tetra([1,1'-biphenyl]-4-yl)-[1,1'-biphenyl]-4,4'-diamine, 4,4',4”-tris(3-methylphenyl(phenyl)amino)triphenylamine, starburstamine derivatives, etc., stilbene derivatives, phthalocyanine derivatives (metal-free, copper phthalocyanine, etc.), pyrazoline derivatives, hydrazone compounds, benzofuran derivatives and thiophene derivatives, oxadiazole derivatives, quinoxaline derivatives Examples include conductors (e.g., 1,4,5,8,9,12-hexaazatriphenylene-2,3,6,7,10,11-hexacarbonitrine), heterocyclic compounds such as porphyrin derivatives, and polysilanes. Among polymer systems, polycarbonates, styrene derivatives, polyvinylcarbazoles, and polysilanes having the monomers in their side chains are preferred, but the compound is not particularly limited as long as it can form a thin film necessary for fabricating a light-emitting device, allow holes to be injected from the anode, and transport holes.

[0126] Furthermore, the conductivity of organic semiconductors is known to be strongly influenced by doping. Such organic semiconductor matrix materials are composed of compounds with good electron-donating properties or compounds with good electron-accepting properties. Strong electron acceptors such as tetracyanoquinone dimethane (TCNQ) or 2,3,5,6-tetrafluorotetracyano-1,4-benzoquinone dimethane (F4TCNQ) are known for doping with electron-donating substances (see, for example, "M. Pfeiffer, A. Beyer, T. Fritz, K. Leo, Appl. Phys. Lett., 73(22), 3202-3204 (1998)" and "J. Blochwitz, M. Pfeiffer, T. Fritz, K. Leo, Appl. Phys. Lett., 73(6), 729-731 (1998)"). These generate so-called holes through an electron transfer process in the electron-donating base material (hole transporter). The conductivity of the base material changes considerably depending on the number and mobility of holes. Examples of matrix materials having hole transport properties include benzidine derivatives (such as TPD) or starburst amine derivatives (such as TDATA), or certain metal phthalocyanines (especially zinc phthalocyanine (ZnPc)) (Japanese Patent Publication No. 2005-167175).

[0127] The hole injection layer material and hole transport layer material described above can also be used as a hole layer material as a polymer compound obtained by polymerizing a reactive compound in which a reactive substituent is substituted as a monomer, or as a polymer crosslink thereof, or as a pendant-type polymer compound obtained by reacting a main-chain polymer with the reactive compound, or as a pendant-type polymer crosslink thereof. In this case, the explanation for the polycyclic aromatic compound represented by the general formula (1) above can be referenced for the reactive substituent. Details of the applications of such polymer compounds and polymer crosslinks will be described later.

[0128] <Emitting layer in organic electroluminescent element> 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 forming the light-emitting layer 105 can be any compound that emits light when excited by the recombination of holes and electrons (luminescent compound), and it is preferable that the compound can form a stable thin film shape and exhibits strong luminescence (fluorescence) efficiency in the solid state. In the present invention, a polycyclic aromatic compound represented by the above general formula (1) can be used as the material for this light-emitting layer.

[0129] The light-emitting layer may consist of a single layer or multiple layers, each formed from a light-emitting layer material (host material, dopant material). The host material and dopant material may each be one type or a combination of multiple types. The host material may also be mixed with a hole transport layer material or an electron transport layer material, or a combination thereof. The dopant material may be contained throughout the host material or partially contained within it. As for doping methods, it can be formed by co-evaporation with the host material, but it may also be pre-mixed with the host material and then deposited simultaneously, or pre-mixed with an organic solvent and the host material and then deposited by a wet deposition method.

[0130] The amount of host material used varies depending on the type of host material and should be determined according to the characteristics of that host material. Preferably, the amount of host material used is 50 to 99.999% by weight of the total material for the light-emitting layer, more preferably 80 to 99.95% by weight, and even more preferably 90 to 99.9% by weight.

[0131] The amount of dopant material used varies depending on the type of dopant material and should be determined according to the characteristics of that dopant material. A guideline for the amount of dopant used is preferably 0.001 to 50% by weight of the total material for the light-emitting layer, more preferably 0.05 to 20% by weight, and even more preferably 0.1 to 10% by weight. Within this range, for example, it is preferable that concentration quenching can be prevented. Furthermore, from the viewpoint of durability, it is preferable that some or all of the hydrogen atoms in the dopant material are deuterated.

[0132] On the other hand, in organic EL elements using thermally activated delayed fluorescence dopant materials, a lower concentration of dopant material is preferable in that it can prevent concentration quenching, but a higher concentration of dopant material is preferable in terms of the efficiency of the thermally activated delayed fluorescence mechanism. Furthermore, in organic EL elements using thermally activated delayed fluorescence assist dopant materials, a lower concentration of dopant material is preferable compared to the amount of assist dopant material in terms of the efficiency of the thermally activated delayed fluorescence mechanism of the assist dopant material.

[0133] When an assist dopant material is used, the approximate amounts of the host material, assist dopant material, and dopant material used are 40-99.999% by weight, 59-1% by weight, and 20-0.001% by weight, respectively, preferably 60-99.99% by weight, 39-5% by weight, and 10-0.01% by weight, respectively, and more preferably 70-99.95% by weight, 29-10% by weight, and 5-0.05% by weight.

[0134] Examples of host materials include condensed ring derivatives such as anthracene, pyrene, dibenzochrycene, or fluorene, which have been known as luminescent materials for some time; bisstyryl derivatives such as bisstyrylanthracene derivatives and distylylbenzene derivatives; tetraphenylbutadiene derivatives; and cyclopentadiene derivatives. Anthracene compounds, fluorene compounds, or dibenzochrycene compounds are particularly preferred. Furthermore, from the viewpoint of durability, it is also preferable that some or all of the hydrogen atoms in the host material are deuterated. Moreover, it is also preferable to construct the luminescent layer by combining a host compound in which some or all of the hydrogen atoms are deuterated with a dopant compound in which some or all of the hydrogen atoms are deuterated.

[0135] From the viewpoint of promoting rather than inhibiting the generation of TADF in the emissive layer, the triplet energy of the host material is preferably higher than the triplet energy of the dopant or assist dopant having the highest triplet energy in the emissive layer. Specifically, the triplet energy of the host material is preferably 0.01 eV or higher, more preferably 0.03 eV or higher, and even more preferably 0.1 eV or higher. In addition, a TADF-active compound may be used as the host material.

[0136] Examples of host materials include compounds represented by the following general formula (H1), compounds represented by the following general formula (H2), compounds represented by the following general formula (H3), compounds containing the structure represented by the following general formula (H4), compounds represented by the following general formula (H5), compounds represented by the following general formula (H6), and TADF materials. Preferably, the compound represented by general formula (H1) is used. [ka]

[0137] <Compounds represented by the general formula (H1)> [ka] In the above formula (H1), L 1The arylene is a C6-C30 arylene or a C2-C30 heteroarylene, with C6-C24 arylene being preferred, C6-C16 arylene being more preferred, C6-C12 arylene being even more preferred, C6-C10 arylene being particularly preferred, C2-C25 heteroarylene being preferred, C2-C20 heteroarylene being more preferred, C2-C15 heteroarylene being even more preferred, and C2-C10 heteroarylene being particularly preferred. Specific examples of arylene include divalent groups such as benzene rings, biphenyl rings, naphthalene rings, terphenyl rings, acenaphthylene rings, fluorene rings, phenalene rings, phenanthrene rings, triphenylene rings, pyrene rings, naphthacene rings, perylene rings, and pentacene rings. Furthermore, specific examples of heteroarylenes include pyrrole rings, oxazole rings, isoxazole rings, thiazole rings, isothiazole rings, imidazole rings, oxadiazole rings, thiadiazole rings, triazole rings, tetrazole rings, pyrazole rings, pyridine rings, pyrimidine rings, pyridazine rings, pyrazine rings, triazine rings, indole rings, isoindole rings, 1H-indazole rings, benzimidazole rings, benzoxazole rings, benzothiazole rings, 1H-benzotriazole rings, quinoline rings, isoquinoline rings, sinnoline rings, quinazoline rings, and quinoline rings. Examples of divalent groups include noxaline rings, phthalazine rings, naphthyridine rings, purine rings, pteridine rings, carbazole rings, acridine rings, phenoxatiin rings, phenoxazine rings, phenothiazine rings, phenazine rings, phenazacillin rings, indoridine rings, furan rings, benzofuran rings, isobenzofuran rings, dibenzofuran rings, thiophene rings, benzothiophene rings, dibenzothiophene rings, furazan rings, thianthrene rings, indolocarbazole rings, benzoindolocarbazole rings, benzobenzoindolocarbazole rings, and naphthobenzofuran rings. At least one hydrogen atom in the compound represented by formula (H1) may be substituted with an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 14 carbon atoms, a cyano group, a halogen group, or a deuterium group.

[0138] <Compounds represented by the general formula (H2)> [ka] In the above formula (H2), L 2 and L 3 Each of these is independently an aryl group having 6 to 30 carbon atoms or a heteroaryl group having 2 to 30 carbon atoms. Preferably, the aryl group has 6 to 24 carbon atoms, more preferably aryl groups having 6 to 16 carbon atoms, even more preferably aryl groups having 6 to 12 carbon atoms, and particularly preferably aryl groups having 6 to 10 carbon atoms. Specifically, examples include monovalent groups such as benzene rings, biphenyl rings, naphthalene rings, terphenyl rings, acenaphthylene rings, fluorene rings, phenalene rings, phenanthrene rings, triphenylene rings, pyrene rings, naphthacene rings, perylene rings, and pentacene rings. As heteroaryls, heteroaryls having 2 to 25 carbon atoms are preferred, heteroaryls having 2 to 20 carbon atoms are more preferred, heteroaryls having 2 to 15 carbon atoms are even more preferred, and heteroaryls having 2 to 10 carbon atoms are particularly preferred. Specifically, pyrrole ring, oxazole ring, isoxazole ring, thiazole ring, isothiazole ring, imidazole ring, oxadiazole ring, thiadiazole ring, triazole ring, tetrazole ring, pyrazole ring, pyridine ring, pyrimidine ring, pyridazine ring, pyrazine ring, triazine ring, indole ring, isoindole ring, 1H-indazole ring, benzimidazole ring, benzoxazole ring, benzothiazole ring Examples of monovalent groups include the 1H-benzotriazole ring, quinoline ring, isoquinoline ring, sinnoline ring, quinazoline ring, quinoxaline ring, phthalazine ring, naphthyridine ring, purine ring, pteridine ring, carbazole ring, acridine ring, phenoxatiin ring, phenoxazine ring, phenothiazine ring, phenazine ring, phenazacillin ring, indoridine ring, furan ring, benzofuran ring, isobenzofuran ring, dibenzofuran ring, thiophene ring, benzothiophene ring, dibenzothiophene ring, furazan ring, thiantrene ring, indolocarbazole ring, benzoindolocarbazole ring, benzobenzoindolocarbazole ring, and naphthobenzofuran ring. At least one hydrogen atom in the compound represented by formula (H2) may be substituted with an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 14 carbon atoms, a cyano group, a halogen group, or a deuterium group.

[0139] <Compounds represented by the general formula (H3) (an example of a polymer host material)> [ka]

[0140] In equation (H3), Each MU is a divalent group that can be independently represented by removing any two hydrogen atoms from an aromatic compound, and each EC is a monovalent group that can be independently represented by removing any one hydrogen atom from an aromatic compound, with two hydrogens in MU being substituted with either EC or MU, and k is an integer between 2 and 50000.

[0141] More specifically, MU is independently allylene, heteroarylene, dialylenearylamino, dialylenearylboryl, oxavorin-diyl, and azavorin-diyl. Each EC is independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, or aryloxy. At least one hydrogen in MU and EC may further be substituted with aryl, heteroaryl, diarylamino, alkyl, and cycloalkyl groups. k is an integer between 2 and 50000. k is preferably an integer between 20 and 50000, and more preferably an integer between 100 and 50000.

[0142] At least one hydrogen atom in MU and EC in formula (H3) may be substituted with an alkyl group having 1 to 24 carbon atoms, a cycloalkyl group having 3 to 24 carbon atoms, a halogen, or deuterium. Furthermore, any -CH2- in the alkyl group may be substituted with -O- or -Si(CH3)2-. Any -CH2- in the alkyl group, except for the -CH2- directly connected to EC in formula (H3), may be substituted with an arylene group having 6 to 24 carbon atoms. Any hydrogen atom in the alkyl group may be substituted with fluorine.

[0143] Examples of MU include divalent groups that can be represented by removing any two hydrogen atoms from any of the following compounds. [ka]

[0144] More specifically, divalent groups represented by one of the following structures are included. In these, MU bonds with another MU or EC at *.

[0145] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka]

[0146] Furthermore, EC can be a monovalent group represented by one of the following structures, for example. In these structures, EC binds to MU at *.

[0147] [ka] [ka]

[0148] From the viewpoint of solubility and coating film-forming properties, the compound represented by formula (H3) preferably has 10 to 100% of the total number of MU (k) in the molecule being alkyl groups with 1 to 24 carbon atoms, more preferably has 30 to 100% of the total number of MU (k) in the molecule being alkyl groups with 1 to 18 carbon atoms (branched alkyl groups with 3 to 18 carbon atoms), and even more preferably has 50 to 100% of the total number of MU (k) in the molecule being alkyl groups with 1 to 12 carbon atoms (branched alkyl groups with 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 MU (k) in the molecule be alkyl groups with 7 to 24 carbon atoms, and more preferably has 30 to 100% of the total number of MU (k) in the molecule being alkyl groups with 7 to 24 carbon atoms (branched alkyl groups with 7 to 24 carbon atoms).

[0149] <Compounds containing a structure represented by the general formula (H4)> The compound is a compound containing a structure represented by the following formula (H4), and contains multiple such structures, preferably 1 to 5, more preferably 1 to 3, even more preferably 1 to 2, and most preferably 1. When multiple such structures are present, they are directly bonded to each other by single bonds or by specific linking groups. [ka]

[0150] In the above general formula (H4), G is independently either "=C(-H)-" or "=N-", and the H in "=C(-H)-" may be substituted with a substituent or a structure represented by other formulas (H4).

[0151] Compounds containing the structure represented by general formula (H4) can be, for example, compounds described in International Publication No. 2012 / 153780 and International Publication No. 2013 / 038650, and can be produced according to the methods described in the aforementioned documents.

[0152] Examples of substituents when H in G, "=C(-H)-", is substituted are, but are not limited to, the following.

[0153] Specific examples of the substituted "aryl group" include phenyl, tolyl, xylyl, naphthyl, phenanthryl, pyrenyl, crisenyl, benzo[c]phenanthryl, benzo[g]crisenyl, benzoanthryl, triphenylenyl, fluorenyl, 9,9-dimethylfluorenyl, benzofluorenyl, dibenzofluorenyl, biphenylyl, terphenylyl, quaterphenylyl, fluoranthenyl, etc. Preferably, phenyl, biphenylyl, terphenylyl, quaterphenylyl, naphthyl, triphenylenyl, and fluorenyl. Examples of substituted aryl groups include tolyl, xylyl, and 9,9-dimethylfluorenyl. As the specific examples show, the aryl group includes both condensed aryl groups and uncondensed aryl groups.

[0154] Specific examples of the substituent "heteroaryl group" include pyrrolyl, pyrazolyl, pyrazinyl, pyrimidinyl, pyridadinyl, pyridyl, triazinyl, indolyl, isoindolyl, imidazolyl, benzimidazolyl, indazolyl, imidazo[1,2-a]pyridinyl, furyl, benzofuranil, isobenzofuranil, dibenzofuranil, azadibenzofuranil, thiophenyl, benzothienyl, dibenzothienyl, azadibenzothienyl, quinolyl, isoquinolyl, quinoxalinyl, quinazolinyl, naphthylidinyl Examples include carbazolyl, azacarbazolyl, phenanthrolinyl, acridinyl, phenanthrolinyl, phenazinyl, phenothiazinyl, phenoxazinyl, oxazolyl, oxadiazolyl, flazanil, benzoxazolyl, thienyl, thiazolyl, thiadiazolyl, benzthiazolyl, triazolyl, tetrazolyl, and the like. Preferably, examples include dibenzofuranil, dibenzothienyl, carbazolyl, pyridyl, pyrimidinyl, triazinyl, azadibenzofuranil, and azadibenzothienyl. Dibenzofuranil, dibenzothienyl, azadibenzofuranil, or azadibenzothienyl are even more preferred.

[0155] The substituent "substituted silyl group" is also preferably a group selected from the group consisting of substituted or unsubstituted trialkylsilyl groups, substituted or unsubstituted arylalkylsilyl groups, and substituted or unsubstituted triarylsilyl groups.

[0156] Specific examples of substituted or unsubstituted trialkylsilyl groups include trimethylsilyl and triethylsilyl. Specific examples of substituted or unsubstituted arylalkylsilyl groups include diphenylmethylsilyl, ditolylmethylsilyl, and phenyldimethylsilyl. Specific examples of substituted or unsubstituted triarylsilyl groups include triphenylsilyl and tritolylsilyl.

[0157] The substituent, the "substituted phosphine oxide group," may preferably be a substituted or unsubstituted diarylphosphine oxide group. Specific examples of substituted or unsubstituted diarylphosphine oxide groups include diphenylphosphine oxide and ditylphosphine oxide.

[0158] Examples of substituted carboxyl groups include benzoyloxy.

[0159] Examples of linking groups that combine multiple structures represented by formula (H4) include the 2- to 4-valent, 2- to 3-valent, or 2-valent derivatives of the aryl and heteroaryl compounds mentioned above.

[0160] Specific examples of compounds containing the structure represented by the general formula (H4) are shown below. [ka] [ka]

[0161] <Compounds represented by the general formula (H5)> [ka] In the above formula (H5), R 1 ~R 11 Each of these is independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, alkyl, or cycloalkyl (all of the above are first substituents), and the R 1 ~R 11 At least one hydrogen in may be further substituted with an aryl, heteroaryl, diarylamino, alkyl, or cycloalkyl (the above are secondary substituents). R 1 ~R 11Adjacent groups among them may bond together to form an aryl ring or heteroaryl ring with the a, b, or c ring, and at least one hydrogen in the formed ring may be substituted with aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, alkyl, or cycloalkyl (the above are first substituents), and at least one hydrogen in these substituents may be further substituted with aryl, heteroaryl, diarylamino, alkyl, or cycloalkyl (the above are second substituents). In ring a, ring b, and ring c, any "-C(-R)=" (where R is R 1 ~R 11 The part "-N=" may be replaced with "-N=". At least one hydrogen atom in the compound represented by formula (H5) may be independently substituted with a halogen or deuterium.

[0162] Any "-C(-R)=" in ring a, ring b, and ring c in equation (H5) (where R is R 1 ~R 11 The part "-N=" may be replaced with a pyridine ring, pyrimidine ring, pyridazine ring, pyrazine ring, or other nitrogen-containing heteroaryl ring.

[0163] Preferably, in the above formula (H5), R 1 ~R 11 Each of these is independently hydrogen, an aryl group having 6 to 30 carbon atoms, a heteroaryl group having 2 to 30 carbon atoms, a diarylamino group (where the aryl group has 6 to 12 carbon atoms), an alkyl group having 1 to 12 carbon atoms, or a cycloalkyl group having 3 to 16 carbon atoms, and the R 1 ~R 11 At least one hydrogen in may be further substituted with an aryl group having 6 to 30 carbon atoms, a heteroaryl group having 2 to 30 carbon atoms, a diarylamino group (where the aryl group has 6 to 12 carbon atoms), an alkyl group having 1 to 12 carbon atoms, or a cycloalkyl group having 3 to 16 carbon atoms. R 1 ~R 11Adjacent groups among these may bond together to form a C9-C16 aryl ring or a C6-C15 heteroaryl ring with the a, b, or c ring, and at least one hydrogen in the formed ring may be substituted with a C6-C30 aryl, a C2-C30 heteroaryl, a diarylamino (where the aryl is a C6-C12 aryl), a C1-C12 alkyl, or a C3-C16 cycloalkyl, and at least one hydrogen in these substituents may be further substituted with a C6-C30 aryl, a C2-C30 heteroaryl, a diarylamino (where the aryl is a C6-C12 aryl), a C1-C12 alkyl, or a C3-C16 cycloalkyl.

[0164] More preferably, in the above formula (H5), R 1 ~R 11 Each of these is independently hydrogen, an aryl group having 6 to 16 carbon atoms, a heteroaryl group having 2 to 15 carbon atoms, a diarylamino group (where the aryl group has 6 to 10 carbon atoms), an alkyl group having 1 to 6 carbon atoms, or a cycloalkyl group having 3 to 14 carbon atoms, and the R 1 ~R 11 At least one hydrogen in may be further substituted with an aryl group having 6 to 16 carbon atoms, a heteroaryl group having 2 to 15 carbon atoms, a diarylamino group (where the aryl group has 6 to 10 carbon atoms), an alkyl group having 1 to 6 carbon atoms, or a cycloalkyl group having 3 to 14 carbon atoms. R 1 ~R 11Adjacent groups among these may bond together to form a C9-C12 aryl ring or a C6-C12 heteroaryl ring with the a, b, or c ring, and at least one hydrogen in the formed ring may be substituted with a C6-C16 aryl, a C2-C15 heteroaryl, a diarylamino (where the aryl is a C6-C10 aryl), a C1-C6 alkyl, or a C3-C14 cycloalkyl, and at least one hydrogen in these substituents may be further substituted with a C6-C16 aryl, a C2-C15 heteroaryl, a diarylamino (where the aryl is a C6-C10 aryl), a C1-C6 alkyl, or a C3-C14 cycloalkyl.

[0165] Examples of "aryl" and "heteroaryl" in the first and second substituents described above include aryl, heteroaryl, diarylamino, diheteroarylamino, and arylheteroarylamino.

[0166] Specific examples of "aryls" include aryls having 6 to 30 carbon atoms, with aryls having 6 to 24 carbon atoms being preferred, aryls having 6 to 20 carbon atoms being more preferred, aryls having 6 to 16 carbon atoms being even more preferred, aryls having 6 to 12 carbon atoms being particularly preferred, and aryls having 6 to 10 carbon atoms being most preferred. For example, monocyclic aryls include phenyl, bicyclic aryls include (2-,3-,4-)biphenylyl, condensed bicyclic aryls include (1-,2-)naphthyl, tricyclic aryls include 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), and condensed tricyclic aryls include Examples include acenaphthylene-(1-,3-,4-,5-)yl, fluoren-(1-,2-,3-,4-,9-)yl, phenalen-(1-,2-)yl, (1-,2-,3-,4-,9-)phenanthryl, the tetracyclic aryl 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 triphenylene-(1-,2-)yl, pyren-(1-,2-,4-)yl, naphthacene-(1-,2-,5-)yl, and the condensed pentacyclic aryl perylene-(1-,2-,3-)yl, pentacene-(1-,2-,5-,6-)yl.

[0167] Specific examples of "heteroaryls" include heteroaryls having 2 to 30 carbon atoms, with heteroaryls having 2 to 25 carbon atoms being preferred, heteroaryls having 2 to 20 carbon atoms being more preferred, heteroaryls having 2 to 15 carbon atoms being even more preferred, and heteroaryls having 2 to 10 carbon atoms being particularly preferred. For example, pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, oxadiazolyl, thiadiazolyl, triazolyl, tetrazolyl, pyrazolyl, pyridinyl, pyrimidinyl, pyridadinyl, pyrazinyl, triazinyl, indolyl, isoindolyl, 1H-indazolyl, benzimidazolyl, benzoxazolyl, benzothiazolyl, 1H-benzotriazolyl, quinolinyl, isoquinolinyl, sinnolinyl, quinazolinyl, quinoxalinyl, phthalazinyl, naphthilidinyl, prinyl, pteridinyl, carbazolyl, acridinyl, phenoxathili Examples include inyl, phenoxazinyl, phenothiazinyl, phenazinyl, phenazacylinyl, indolidinyl, furanil, benzofuranil, isobenzofuranil, dibenzofuranil, naphthobenzofuranil, thiophenyl, benzothiophenyl, isobenzothiophenyl, dibenzothiophenyl, naphthobenzothiophenyl, benzophosphoryl, dibenzophosphoryl, monovalent group of the benzophosphorus oxide ring, monovalent group of the dibenzophosphorus oxide ring, flazanil, thianthrenil, indolocarbazolyl, benzoindocarbazolyl, and benzobenzoindocarbazolyl.

[0168] In the first and second substituents described above, the "alkyl" can be either a linear or branched chain. Examples include a linear alkyl group having 1 to 24 carbon atoms or a branched alkyl group having 3 to 24 carbon atoms. A C1 to 18 alkyl group (a branched alkyl group having 3 to 18 carbon atoms) is preferred, a C1 to 12 alkyl group (a branched alkyl group having 3 to 12 carbon atoms) is more preferred, a C1 to 6 alkyl group (a branched alkyl group having 3 to 6 carbon atoms) is even more preferred, a C1 to 5 alkyl group (a branched alkyl group having 3 to 5 carbon atoms) or a C1 to 4 alkyl group (a branched alkyl group having 3 to 4 carbon atoms) is particularly preferred, and methyl is the most preferred. For example, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, t-butyl, n-pentyl, isopentyl, neopentyl, t-pentyl(t-amyl), n-hexyl, 1-methylpentyl, 3,3-dimethylbutyl, 2-ethylbutyl, n-heptyl, 1-methylhexyl, n-octyl, t-octyl(1,1,3,3-tetramethylbutyl), 1-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. Other examples include 1-ethyl-1-methylpropyl, 1,1-diethylpropyl, 1,1-dimethylbutyl, 1-ethyl-1-methylbutyl, 1,1,4-trimethylpentyl, 1,1,2-trimethylpropyl, 1,1-dimethyloctyl, 1,1-dimethylpentyl, 1,1-dimethylheptyl, 1,1,5-trimethylhexyl, 1-ethyl-1-methylhexyl, 1-ethyl-1,3-dimethylbutyl, 1,1,2,2-tetramethylpropyl, 1-butyl-1-methylpentyl, 1,1-diethylbutyl, 1-ethyl-1-methylpentyl, 1,1,3-trimethylbutyl, 1-propyl-1-methylpentyl, 1,1,2-trimethylpropyl, 1-ethyl-1,2,2-trimethylpropyl, 1-propyl-1-methylbutyl, and 1,1-dimethylhexyl.

[0169] In the first and second substituents described above, "cycloalkyl" can be defined as cycloalkyl groups with 3 to 24 carbon atoms, 3 to 20 carbon atoms, 3 to 16 carbon atoms, 3 to 14 carbon atoms, 5 to 10 carbon atoms, 5 to 8 carbon atoms, 5 to 6 carbon atoms, or 5 carbon atoms. Examples include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, and their C1-C4 alkyl (especially methyl) substituted derivatives, as well as bicyclo[1.1.0]butyl, bicyclo[1.1.1]pentyl, bicyclo[2.1.0]pentyl, bicyclo[2.1.1]hexyl, bicyclo[3.1.0]hexyl, bicyclo[2.2.1]heptyl, bicyclo[2.2.2]octyl, adamantyl, diamantyl, decahydronaphthalenyl, and decahydroazlenyl.

[0170] When the first substituent is aryl, the substitution position is R 1 , R 3 , R 4 , R 5 , R 10 and R 11 Preferably, R 1 and R 3 Substitution to R 5 and R 10 Substitution to R 4 and R 11 Substitution to is more preferable, and the aryl group is preferably a phenyl group.

[0171] When the first substituent is a heteroaryl compound, the substitution site is R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 9 , R 10 and R 11 Preferably, R 1 Substitution to R 2 Substitution to R3 Substitution to R 1 and R 3 Substitution to R 4 and R 11 Substitution to R 5 and R 10 Substitution to R 6 and R 9 Substitution to is more preferable, and the heteroaryl group is preferably a carbazolyl group. This heteroaryl group (e.g., carbazolyl) may be substituted at the above position via a phenylene group.

[0172] A specific example of a compound represented by formula (H5) is the compound shown in the following structural formula. Note that "Me" in the formula represents a methyl group.

[0173] [ka] [ka]

[0174] The compound represented by formula (H5) can be synthesized by first bonding the a-c rings with a (-O-) bond to produce an intermediate (first reaction), and then bonding the a-c rings with B (boron) to produce the final product (second reaction). In the first reaction, general etherification reactions such as nucleophilic substitution reactions and Ullmann reactions can be used. In the second reaction, a tandem hetero-Friedel-Crafts reaction (a series of aromatic electrophilic substitution reactions) can be used. Details of the first and second reactions can be found in the explanation in International Publication No. 2015 / 102118.

[0175] <Compounds represented by the general formula (H6)> [ka] In the above formula (H6), R 1 ~R 16Each of these is independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, alkyl, or cycloalkyl (all of the above are first substituents), and the R 1 ~R 16 At least one hydrogen in may be further substituted with an aryl, heteroaryl, diarylamino, alkyl, or cycloalkyl (the above are secondary substituents). R 1 ~R 16 Adjacent groups among them may bond together to form an aryl ring or heteroaryl ring with the a, b, c, or d ring, and at least one hydrogen in the formed ring may be substituted with aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, alkyl, or cycloalkyl (the above are first substituents), and at least one hydrogen in these substituents may be further substituted with aryl, heteroaryl, diarylamino, alkyl, or cycloalkyl (the above are second substituents). At least one hydrogen atom in the compound represented by formula (H6) may be independently substituted with a halogen or deuterium.

[0176] Preferably, in the above formula (H6), R 1 ~R 16 Each of these is independently hydrogen, an aryl group having 6 to 30 carbon atoms, a heteroaryl group having 2 to 30 carbon atoms, a diarylamino group (where the aryl group has 6 to 12 carbon atoms), an alkyl group having 1 to 12 carbon atoms, or a cycloalkyl group having 3 to 16 carbon atoms, and the R 1 ~R 16 At least one hydrogen in may be further substituted with an aryl group having 6 to 30 carbon atoms, a heteroaryl group having 2 to 30 carbon atoms, a diarylamino group (where the aryl group has 6 to 12 carbon atoms), an alkyl group having 1 to 12 carbon atoms, or a cycloalkyl group having 3 to 16 carbon atoms. R 1 ~R 16Adjacent groups among these may bond together to form a C9-C16 aryl ring or a C6-C15 heteroaryl ring with the a, b, c, or d ring, and at least one hydrogen in the formed ring may be substituted with a C6-C30 aryl, a C2-C30 heteroaryl, a diarylamino (where the aryl is a C6-C12 aryl), a C1-C12 alkyl, or a C3-C16 cycloalkyl, and at least one hydrogen in these substituents may be further substituted with a C6-C30 aryl, a C2-C30 heteroaryl, a diarylamino (where the aryl is a C6-C12 aryl), a C1-C12 alkyl, or a C3-C16 cycloalkyl.

[0177] More preferably, in the above formula (H6), R 1 ~R 16 Each of these is independently hydrogen, an aryl group having 6 to 16 carbon atoms, a heteroaryl group having 2 to 15 carbon atoms, a diarylamino group (where the aryl group has 6 to 10 carbon atoms), an alkyl group having 1 to 6 carbon atoms, or a cycloalkyl group having 3 to 14 carbon atoms, and the R 1 ~R 16 At least one hydrogen in may be further substituted with an aryl group having 6 to 16 carbon atoms, a heteroaryl group having 2 to 15 carbon atoms, a diarylamino group (where the aryl group has 6 to 10 carbon atoms), an alkyl group having 1 to 6 carbon atoms, or a cycloalkyl group having 3 to 14 carbon atoms. R 1 ~R 16Adjacent groups among these may bond together to form a C9-C12 aryl ring or a C6-C12 heteroaryl ring with the a, b, c, or d ring, and at least one hydrogen in the formed ring may be substituted with a C6-C16 aryl, a C2-C15 heteroaryl, a diarylamino (where the aryl is a C6-C10 aryl), a C1-C6 alkyl, or a C3-C14 cycloalkyl, and at least one hydrogen in these substituents may be further substituted with a C6-C16 aryl, a C2-C15 heteroaryl, a diarylamino (where the aryl is a C6-C10 aryl), a C1-C6 alkyl, or a C3-C14 cycloalkyl.

[0178] Examples of "aryl" and "heteroaryl" in the first and second substituents described above include aryl, heteroaryl, diarylamino, diheteroarylamino, and arylheteroarylamino.

[0179] Specific examples of "aryls" include aryls having 6 to 30 carbon atoms, with aryls having 6 to 24 carbon atoms being preferred, aryls having 6 to 20 carbon atoms being more preferred, aryls having 6 to 16 carbon atoms being even more preferred, aryls having 6 to 12 carbon atoms being particularly preferred, and aryls having 6 to 10 carbon atoms being most preferred. For example, monocyclic aryls include phenyl, bicyclic aryls include (2-,3-,4-)biphenylyl, condensed bicyclic aryls include (1-,2-)naphthyl, tricyclic aryls include 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), and condensed tricyclic aryls include Examples include acenaphthylene-(1-,3-,4-,5-)yl, fluoren-(1-,2-,3-,4-,9-)yl, phenalen-(1-,2-)yl, (1-,2-,3-,4-,9-)phenanthryl, the tetracyclic aryl 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 triphenylene-(1-,2-)yl, pyren-(1-,2-,4-)yl, naphthacene-(1-,2-,5-)yl, and the condensed pentacyclic aryl perylene-(1-,2-,3-)yl, pentacene-(1-,2-,5-,6-)yl.

[0180] Specific examples of "heteroaryls" include heteroaryls having 2 to 30 carbon atoms, with heteroaryls having 2 to 25 carbon atoms being preferred, heteroaryls having 2 to 20 carbon atoms being more preferred, heteroaryls having 2 to 15 carbon atoms being even more preferred, and heteroaryls having 2 to 10 carbon atoms being particularly preferred. For example, pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, oxadiazolyl, thiadiazolyl, triazolyl, tetrazolyl, pyrazolyl, pyridinyl, pyrimidinyl, pyridadinyl, pyrazinyl, triazinyl, indolyl, isoindolyl, 1H-indazolyl, benzimidazolyl, benzoxazolyl, benzothiazolyl, 1H-benzotriazolyl, quinolinyl, isoquinolinyl, sinnolinyl, quinazolinyl, quinoxalinyl, phthalazinyl, naphthilidinyl, prinyl, pteridinyl, carbazolyl, acridinyl, phenoxathili Examples include inyl, phenoxazinyl, phenothiazinyl, phenazinyl, phenazacylinyl, indolidinyl, furanil, benzofuranil, isobenzofuranil, dibenzofuranil, naphthobenzofuranil, thiophenyl, benzothiophenyl, isobenzothiophenyl, dibenzothiophenyl, naphthobenzothiophenyl, benzophosphoryl, dibenzophosphoryl, monovalent group of the benzophosphorus oxide ring, monovalent group of the dibenzophosphorus oxide ring, flazanil, thianthrenil, indolocarbazolyl, benzoindocarbazolyl, and benzobenzoindocarbazolyl.

[0181] In the first and second substituents described above, the "alkyl" can be either a linear or branched chain. Examples include a linear alkyl group having 1 to 24 carbon atoms or a branched alkyl group having 3 to 24 carbon atoms. A C1 to 18 alkyl group (a branched alkyl group having 3 to 18 carbon atoms) is preferred, a C1 to 12 alkyl group (a branched alkyl group having 3 to 12 carbon atoms) is more preferred, a C1 to 6 alkyl group (a branched alkyl group having 3 to 6 carbon atoms) is even more preferred, a C1 to 5 alkyl group (a branched alkyl group having 3 to 5 carbon atoms) or a C1 to 4 alkyl group (a branched alkyl group having 3 to 4 carbon atoms) is particularly preferred, and methyl is the most preferred. For example, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, t-butyl, n-pentyl, isopentyl, neopentyl, t-pentyl(t-amyl), n-hexyl, 1-methylpentyl, 3,3-dimethylbutyl, 2-ethylbutyl, n-heptyl, 1-methylhexyl, n-octyl, t-octyl(1,1,3,3-tetramethylbutyl), 1-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. Other examples include 1-ethyl-1-methylpropyl, 1,1-diethylpropyl, 1,1-dimethylbutyl, 1-ethyl-1-methylbutyl, 1,1,4-trimethylpentyl, 1,1,2-trimethylpropyl, 1,1-dimethyloctyl, 1,1-dimethylpentyl, 1,1-dimethylheptyl, 1,1,5-trimethylhexyl, 1-ethyl-1-methylhexyl, 1-ethyl-1,3-dimethylbutyl, 1,1,2,2-tetramethylpropyl, 1-butyl-1-methylpentyl, 1,1-diethylbutyl, 1-ethyl-1-methylpentyl, 1,1,3-trimethylbutyl, 1-propyl-1-methylpentyl, 1,1,2-trimethylpropyl, 1-ethyl-1,2,2-trimethylpropyl, 1-propyl-1-methylbutyl, and 1,1-dimethylhexyl.

[0182] In the above-mentioned first substituent and second substituent, examples of the "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, cycloalkyl having 5 carbon atoms, and the like. For example, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, and their alkyl (especially methyl) substituents having 1 to 4 carbon atoms, bicyclo[1.1.0]butyl, bicyclo[1.1.1]pentyl, bicyclo[2.1.0]pentyl, bicyclo[2.1.1]hexyl, bicyclo[3.1.0]hexyl, bicyclo[2.2.1]heptyl, bicyclo[2.2.2]octyl, adamantyl, diamantyl, decahydronaphthalenyl, decahydroazulenyl, and the like can be mentioned.

[0183] The compound represented by formula (H6) can be produced by referring to the description described in International Publication No. 2014 / 042197.

[0184] <TADF material> By reducing the energy difference between the singlet excited state and the triplet excited state, reverse energy transfer from the triplet excited state, which usually has a low transition probability, to the singlet excited state occurs with high efficiency, and thus luminescence from the singlet state (thermally activated delayed fluorescence, TADF) is exhibited. In normal fluorescence emission, 75% of the triplet excitons generated by current excitation pass through the thermal deactivation path and thus cannot contribute to fluorescence. On the other hand, in TADF, all excitons can be utilized for fluorescence emission, and a highly efficient organic EL device can be realized.

[0185] Examples of the TADF material that can be used for such an object include a compound represented by the following general formula (H7) or a compound having the following general formula (H7) as a partial structure.

Chemical formula

[0186] Preferably, the TADF material is a donor-acceptor type TADF compound (DA type TADF compound) designed to enable efficient reverse intersystem crossing by localizing the intramolecular HOMO and LUMO using electron-donating substituents called donors and electron-accepting substituents called acceptors.

[0187] Herein, in this specification, "electron-donating substituent" (donor) means substituents and substructures in which the LUMO orbital is localized in a TADF compound molecule, and "electron-accepting substituent" (acceptor) means substituents and substructures in which the HOMO orbital is localized in a TADF compound molecule.

[0188] Generally, TADF compounds using donors and acceptors exhibit large spin-orbit coupling (SOC) due to their structure, and the exchange interaction between the HOMO and LUMO is small, resulting in a small ΔE(ST), which leads to very fast reverse intersystem crossing velocities. On the other hand, TADF compounds using donors and acceptors exhibit large structural relaxation in the excited state (in some molecules, the stable structure differs between the ground state and the excited state; therefore, when a conversion from the ground state to the excited state occurs due to an external stimulus, the structure subsequently changes to the stable structure in the excited state), resulting in a broad emission spectrum. Therefore, using them as luminescent materials may reduce color purity.

[0189] If the TADF material reduces color purity, a fluorescent compound can be added as another component to the emissive layer or a layer adjacent to the emissive layer. The TADF material acts as an assisting dopant, and the other component acts as an emitting dopant. The other component should be a compound whose absorption spectrum overlaps at least partially with the emission peak of the assisting dopant.

[0190] For donor and acceptor structures used in TADF materials, for example, structures described in Chemistry of Materials, 2017, 29, 1946-1963 can be used. As for ED, for example, sp 3 Examples of nitrogen-containing functional groups include carbazole, dimethylcarbazole, di-t-butylcarbazole, dimethoxycarbazole, tetramethylcarbazole, benzofluorocarbazole, benzothienocarbazole, phenyldihydroindocarbazole, phenylbicarbazole, bicarbazole, tercarbazole, diphenylcarbazolylamine, tetraphenylcarbazolyldiamine, phenoxazine, dihydrophenazine, phenothiazine, dimethyldihydroacridine, diphenylamine, bis(t-butylphenyl)amine, N 1 -(4-(diphenylamino)phenyl)-N 4 ,N 4Examples of groups derived from -diphenylbenzene-1,4-diamine, dimethyltetraphenyldihydroacridinediamine, tetramethyl-dihydro-indenoacridine, and diphenyl-dihydrodibenzoazacillin are also included. Furthermore, as EA, for example, sp 2 Nitrogen-containing aromatic rings, CN-substituted aromatic rings, rings containing ketones and cyano groups, more specifically, sulfonyl dibenzene, benzophenone, phenylenebis(phenylmethanone), benzonitrile, isonicotinonitrile, phthalonitrile, isophthalonitrile, paraphthalonitrile, triazole, oxazole, thiadiazole, benzothiazole, benzobis(thiazole), benzoxazole, benzobis(oxazole), quinoline, benzimidazole, dibenzoquinoxaline, heptazaphenalene, thioxanthone dioxide, dimethylamine Examples of groups derived from tracenone, anthracendione, pyridine, 5H-cyclopenta[1,2-b:5,4-b']dipyridine, benzenetricarbonitrate, fluorangecarbonitrate, pyrazinedicarbonitrate, pyridinedicarbonitrate, dibenzoquinoxalinedicarbonitrate, pyrimidine, phenylpyrimidine, methylpyrimidine, triazine, triphenyltriazine, bis(phenylsulfonyl)benzene, dimethylthioxanthenedioxide, thianthrenetetraoxide, and tris(dimethylphenyl)borane are examples. Examples of Ln include single bonds and arylenes, more specifically phenylene, biphenylene, and naphthylene. Furthermore, hydrogen may be substituted with alkyl, cycloalkyl, and aryl groups in any of the structures. In particular, it is preferable that the compound has at least one selected from carbazole, phenoxazine, acridine, triazine, pyrimidine, pyrazine, thioxanthene, benzonitrile, phthalonitrile, isophthalonitrile, diphenylsulfone, triazole, oxadiazole, thiadiazole, and benzophenone as a substructure.

[0191] More specifically, compounds represented by general formula (H7) are compounds represented by any of the following general formulas (H7-1), (H7-2), and (H7-3). [ka]

[0192] In the above general formulas (H7-1), (H7-2), and (H7-3), M is independently a single bond, -O-, >N-Ar, or >C(-Ar)2, and is preferably a single bond, -O-, or >N-Ar in terms of the depth of the HOMO of the formed substructure and the height of the excited singlet energy level and excited triplet energy level. J is a spacer structure that separates the donor substructure and the acceptor substructure, and each is independently an arylene having 6 to 18 carbon atoms. From the viewpoint of the magnitude of conjugation that leachs from the donor substructure and the acceptor substructure, an arylene having 6 to 12 carbon atoms is preferred, and more specifically, phenylene, methylphenylene, and dimethylphenylene are examples. Q is independently =C(-H)- or =N-, and from the viewpoint of the shallowness of the LUMO of the formed substructure and the height of the excited singlet energy level and excited triplet energy level, it is preferably =N-. Ar is independently hydrogen, a C6-C24 aryl, a C2-C24 heteroaryl, a C1-C12 alkyl, or a C3-C18 cycloalkyl, and from the viewpoint of the depth of the HOMO of the formed substructure and the height of the excited singlet energy level and excited triplet energy level, preferably hydrogen, a C6-C12 aryl, a C2-C14 heteroaryl, a C1-C4 alkyl, or a C6-C10 cycloalkyl, more preferably hydrogen, phenyl, tolyl, xylyl, mesityl, biphenyl, pyridyl, bipyridyl, triazinyl, carbazolyl, dimethylcarbazol, di-t-butylcarbazol, benzimidazole, or phenylbenzimidazole, and even more preferably hydrogen, phenyl, or carbazolyl. m is either 1 or 2. n is an integer between 2 and (6-m), and is preferably an integer between 4 and (6-m) from the viewpoint of steric hindrance. Furthermore, at least one hydrogen atom in each of the above formulas may be substituted with a halogen or deuterium.

[0193] Examples of compounds represented by formula (H7) include those shown in the following structure. In the structural formula, * indicates a bond position, "Me" indicates a methyl group, and "tBu" indicates a t-butyl group.

[0194] [ka]

[0195] [ka]

[0196] [ka]

[0197] [ka]

[0198] [ka]

[0199] [ka]

[0200] [ka]

[0201] [ka]

[0202] [ka]

[0203] Among the specific compounds listed above, 4CzBN, 4CzBN-Ph, 5CzBN, 3Cz2DPhCzBN, 4CzIPN, 2PXZ-TAZ, Cz-TRZ3, BDPCC-TPTA, MA-TA, PA-TA, FA-TA, PXZ-TRZ, DMAC-TRZ, BCzT, DCzTrz, DDCzTrz, spiroAC-TRZ, Ac-HPM, Ac-PPM, Ac-MPM, TCzTrz, TmCzTrz, and DCzmCzTrz are particularly preferred as compounds represented by the general formula (H7).

[0204] Furthermore, known compounds can be used as dopant materials, and a variety of materials can be selected according to the desired emission color. Specifically, for example, condensed ring derivatives such as phenanthrene, anthracene, pyrene, tetracene, pentacene, perylene, naphthopyrene, dibenzopyrene, rubrene, and chrysene, benzoxazole derivatives, benzothiazole derivatives, benzimidazole derivatives, benzotriazole derivatives, oxazole derivatives, oxadiazole derivatives, thiazole derivatives, imidazole derivatives, thiadiazole derivatives, triazole derivatives, pyrazoline derivatives, stilbene derivatives, thiophene derivatives, and tetraphenylbutadiene Derivatives, cyclopentadiene derivatives, bisstyryl derivatives such as bisstyrylanthracene derivatives and distyrylbenzene derivatives (Japanese Patent Publication No. 1-245087), bisstyrylarylene derivatives (Japanese Patent Publication No. 2-247278), diazindacene derivatives, furan derivatives, benzofuran derivatives, phenylisobenzofuran, dimesitylisobenzofuran, di(2-methylphenyl)isobenzofuran, di(2-trifluoromethylphenyl)isobenzofuran, phenylisobenzofuran, and other isobenzofuran derivatives. Coumarin derivatives such as dibenzofuran derivatives, 7-dialkylaminocoumarin derivatives, 7-piperidinocoumarin derivatives, 7-hydroxycoumarin derivatives, 7-methoxycoumarin derivatives, 7-acetoxycoumarin derivatives, 3-benzothiazolylcoumarin derivatives, 3-benzimidazolylcoumarin derivatives, 3-benzoxazolylcoumarin derivatives, dicyanomethylenepyran derivatives, dicyanomethylenethiopyran derivatives, polymethine derivatives, cyanine derivatives, oxobenzoanthracene derivatives, xanthene derivatives, and rhodamine derivatives. Examples include conductors, fluorescein derivatives, pyririum derivatives, carbostyryl derivatives, acridine derivatives, oxazine derivatives, phenylene oxide derivatives, quinacridone derivatives, quinazoline derivatives, pyrrolopyridine derivatives, phlopyridine derivatives, 1,2,5-thiadiazolopyrene derivatives, pyromethene derivatives, perinone derivatives, pyrrolopyrrole derivatives, squarylium derivatives, biolantron derivatives, phenazine derivatives, acridone derivatives, deazaflavin derivatives, fluorene derivatives, and benzofluorene derivatives.

[0205] Examples of dopant materials for each color light include blue to blue-green compounds such as naphthalene, anthracene, phenanthrene, pyrene, triphenylene, perylene, fluorene, indene, chrysene, aromatic hydrocarbon compounds and their derivatives, furan, pyrrole, thiophene, silole, 9-silafluorene, 9,9'-spirobicilafluorene, benzothiophene, benzofuran, indole, dibenzothiophene, dibenzofuran, imidazopyridine, phenanthroline, pyrazine, naphthyridine, quinoxaline, and pyrrolopy Examples include aromatic heterocyclic compounds such as lysine and thioxanthenes and their derivatives, distylylbenzene derivatives, tetraphenylbutadiene derivatives, stilbene derivatives, aldazine derivatives, coumarin derivatives, azole derivatives such as imidazole, thiazole, thiadiazole, carbazole, oxazole, oxadiazole, and triazole, and their metal complexes, as well as aromatic amine derivatives represented by N,N'-diphenyl-N,N'-di(3-methylphenyl)-4,4'-diphenyl-1,1'-diamine.

[0206] Furthermore, examples of green to yellow dopant materials include coumarin derivatives, phthalimide derivatives, naphthalimide derivatives, perinone derivatives, pyrrolopyrrole derivatives, cyclopentadiene derivatives, acridone derivatives, quinacridone derivatives, and naphthacene derivatives such as rubrene. In addition, compounds obtained by introducing substituents that enable longer wavelengths, such as aryl, heteroaryl, arylvinyl, amino, and cyano, into the compounds exemplified above as blue to blue-green dopant materials are also suitable examples.

[0207] Furthermore, examples of orange to red dopant materials include naphthalimide derivatives such as bis(diisopropylphenyl)perylenetetracarboxylic acid imide, perinone derivatives, rare earth complexes such as Eu complexes with ligands such as acetylacetone or benzoylacetone and phenanthroline, 4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran and its analogs, metal phthalocyanine derivatives such as magnesium phthalocyanine and aluminum chlorophthalocyanine, rhodamine compounds, deazaflavin derivatives, coumarin derivatives, quinacridone derivatives, phenoxazine derivatives, oxazine derivatives, quinazoline derivatives, pyrrolopyridine derivatives, squarylium derivatives, biolantron derivatives, phenazine derivatives, phenoxazone derivatives, and thiadiazolopyrene derivatives. In addition, compounds to which substituents that enable longer wavelengths, such as aryl, heteroaryl, arylvinyl, amino, and cyano, are introduced into the compounds exemplified above as blue to blue-green and green to yellow dopant materials are also suitable examples.

[0208] In addition, dopants can be appropriately selected and used from compounds listed on page 13 of the June 2004 issue of Chemical Industry and the references cited therein.

[0209] Among the dopant materials described above, amines, perylene derivatives, borane derivatives, aromatic amine derivatives, coumarin derivatives, pyran derivatives, or pyrene derivatives having a stilbene structure are particularly preferred.

[0210] Amines having a stilbene structure can be represented, for example, by the following formula. [ka] In the said formula, Ar 1 It is an m-valent group derived from aryls with 6 to 30 carbon atoms, Ar 2 and Ar 3 These are each independently aryl atoms with 6 to 30 carbon atoms, but Ar 1 ~Ar 3 At least one of them has a stilbene structure, Ar1 ~Ar 3 m may be substituted with an aryl, heteroaryl, alkyl, cycloalkyl, trisubstituted silyl (a silyl trisubstituted with at least one aryl, alkyl, or cycloalkyl) or cyano, and m is an integer from 1 to 4.

[0211] Among amines having a stilbene structure, diaminostilbene represented by the following formula is more preferred. [ka] In the said formula, Ar 2 and Ar 3 These are each independently aryl atoms with 6 to 30 carbon atoms, and Ar 2 and Ar 3 It may be substituted with an aryl, heteroaryl, alkyl, cycloalkyl, trisubstituted silyl (a silyl trisubstituted with at least one of aryl, alkyl, and cycloalkyl) or cyano.

[0212] Specific examples of aryl compounds with 6 to 30 carbon atoms include phenyl, naphthyl, acenaphthirenyl, fluorenyl, phenalenyl, phenantrenyl, anthryl, fluoranthenyl, triphenylenyl, pyrenyl, crisenyl, naphthacenyl, perilenyl, stilbenyl, distyrylphenyl, distyrylbiphenyl, and distyrylfluorenyl.

[0213] Specific examples of amines having a stilbene structure include N,N,N',N'-tetra(4-biphenylyl)-4,4'-diaminostilbene, N,N,N',N'-tetra(1-naphthyl)-4,4'-diaminostilbene, N,N,N',N'-tetra(2-naphthyl)-4,4'-diaminostilbene, N,N'-di(2-naphthyl)-N,N'-diphenyl-4,4'-diaminostilbene, and N,N'-di(9-phenanthryl)-N,N'-diphenyl Examples include nyl-4,4'-diaminostilbene, 4,4'-bis[4”-bis(diphenylamino)styryl]-biphenyl, 1,4-bis[4'-bis(diphenylamino)styryl]-benzene, 2,7-bis[4'-bis(diphenylamino)styryl]-9,9-dimethylfluorene, 4,4'-bis(9-ethyl-3-carbazovinylene)-biphenyl, and 4,4'-bis(9-phenyl-3-carbazovinylene)-biphenyl. Alternatively, amines having a stilbene structure as described in Japanese Patent Publication No. 2003-347056 and Japanese Patent Publication No. 2001-307884 may be used.

[0214] Examples of perylene derivatives include 3,10-bis(2,6-dimethylphenyl)perylene, 3,10-bis(2,4,6-trimethylphenyl)perylene, 3,10-diphenylperylene, 3,4-diphenylperylene, 2,5,8,11-tetra-t-butylperylene, 3,4,9,10-tetraphenylperylene, 3-(1'-pyrenyl)-8,11-di(t-butyl)perylene, 3-(9'-anthryl)-8,11-di(t-butyl)perylene, and 3,3'-bis(8,11-di(t-butyl)peryleneyl). Furthermore, perylene derivatives described in Japanese Patent Publication No. 11-97178, Japanese Patent Publication No. 2000-133457, Japanese Patent Publication No. 2000-26324, Japanese Patent Publication No. 2001-267079, Japanese Patent Publication No. 2001-267078, Japanese Patent Publication No. 2001-267076, Japanese Patent Publication No. 2000-34234, Japanese Patent Publication No. 2001-267075, and Japanese Patent Publication No. 2001-217077 may also be used.

[0215] Examples of borane derivatives include 1,8-diphenyl-10-(dimethylboryl)anthracene, 9-phenyl-10-(dimethylboryl)anthracene, 4-(9'-anthryl)dimethylborylnaphthalene, 4-(10'-phenyl-9'-anthryl)dimethylborylnaphthalene, 9-(dimethylboryl)anthracene, 9-(4'-biphenylyl)-10-(dimethylboryl)anthracene, and 9-(4'-(N-carbazolyl)phenyl)-10-(dimethylboryl)anthracene. Alternatively, borane derivatives described in International Publication No. 2000 / 40586, etc., may be used.

[0216] Aromatic amine derivatives can be represented, for example, by the following formula. [ka] In the said formula, Ar 4 Ar is an n-valent group derived from aryl atoms with 6 to 30 carbon atoms, 5 and Ar 6 Each of these is an aryl group with 6 to 30 carbon atoms, and Ar 4 ~Ar 6 n may be substituted with an aryl, heteroaryl, alkyl, cycloalkyl, trisubstituted silyl (a silyl trisubstituted with at least one aryl, alkyl, or cycloalkyl) or cyano, and n is an integer from 1 to 4.

[0217] In particular, Ar 4 is a divalent group derived from anthracene, chrysene, fluorene, benzofluorene, or pyrene, and Ar 5 and Ar 6 Each of these is an aryl group with 6 to 30 carbon atoms, and Ar 4 ~Ar 6 Aromatic amine derivatives are more preferred, where n may be substituted with an aryl, heteroaryl, alkyl, cycloalkyl, trisubstituted silyl (a silyl trisubstituted with at least one of aryl, alkyl, and cycloalkyl) or cyano, and n is 2.

[0218] Specific examples of aryl compounds with 6 to 30 carbon atoms include phenyl, naphthyl, acenaphthirenyl, fluorenyl, phenalenyl, phenantrenyl, anthryl, fluoranthenyl, triphenylenyl, pyrenyl, crisenyl, naphthacenyl, perilenyl, and pentacenyl.

[0219] Examples of aromatic amine derivatives include chrysene derivatives such as N,N,N',N'-tetraphenylchrysene-6,12-diamine, N,N,N',N'-tetra(p-tolyl)chrysene-6,12-diamine, N,N,N',N'-tetra(m-tolyl)chrysene-6,12-diamine, N,N,N',N'-tetrakis(4-isopropylphenyl)chrysene-6,12-diamine, N,N,N',N'-tetra(naphthalene-2-yl)chrysene-6,12-diamine, and N,N'-diphenyl Examples include -N,N'-di(p-tolyl)chrysene-6,12-diamine, N,N'-diphenyl-N,N'-bis(4-ethylphenyl)chrysene-6,12-diamine, N,N'-diphenyl-N,N'-bis(4-isopropylphenyl)chrysene-6,12-diamine, N,N'-diphenyl-N,N'-bis(4-t-butylphenyl)chrysene-6,12-diamine, and N,N'-bis(4-isopropylphenyl)-N,N'-di(p-tolyl)chrysene-6,12-diamine.

[0220] Furthermore, pyrene-based compounds include, for example, N,N,N',N'-tetraphenylpyrene-1,6-diamine, N,N,N',N'-tetra(p-tolyl)pyrene-1,6-diamine, N,N,N',N'-tetra(m-tolyl)pyrene-1,6-diamine, N,N,N',N'-tetrakis(4-isopropylphenyl)pyrene-1,6-diamine, N,N',N'-tetrakis(3,4-dimethylphenyl)pyrene-1,6-diamine, N,N'-diphenyl-N,N'-di(p-tolyl)pyrene-1,6-diamine, N,N'-diphenyl-N,N'-bis(4-ethylphenyl)pyrene-1, 6-diamine, N,N'-diphenyl-N,N'-bis(4-isopropylphenyl)pyrene-1,6-diamine, N,N'-diphenyl-N,N'-bis(4-t-butylphenyl)pyrene-1,6-diamine, N,N'-bis(4-isopropylphenyl)-N,N'-di(p-tolyl)pyrene-1,6-diamine, N,N,N',N'-tetrakis(3,4-dimethylphenyl)-3,8-diphenylpyrene-1,6-diamine, N,N,N,N-tetraphenylpyrene-1,8-diamine, N,N'-bis(biphenyl-4-yl)-N,N'-diphenylpyrene-1,8-diamine, N 1 ,N 6 -diphenyl-N 1 ,N 6 Examples include -bis-(4-trimethylsilanylphenyl)-1H,8H-pyrene-1,6-diamine.

[0221] Furthermore, anthracene-based compounds include, for example, N,N,N,N-tetraphenylanthracene-9,10-diamine, N,N,N',N'-tetra(p-tolyl)anthracene-9,10-diamine, N,N,N',N'-tetra(m-tolyl)anthracene-9,10-diamine, N,N,N',N'-tetrakis(4-isopropylphenyl)anthracene-9,10-diamine, N,N'-diphenyl-N,N'-di(p-tolyl)anthracene-9,10-diamine, and N,N'-diphenyl-N,N'-di(m-tolyl)anthracene-9,10 -Diamine, N,N'-diphenyl-N,N'-bis(4-ethylphenyl)anthracene-9,10-diamine, N,N'-diphenyl-N,N'-bis(4-isopropylphenyl)anthracene-9,10-diamine, N,N'-diphenyl-N,N'-bis(4-t-butylphenyl)anthracene-9,10-diamine, N,N'-bis(4-isopropylphenyl)-N,N'-di(p-tolyl)anthracene-9,10-diamine, 2,6-di-t-butyl-N,N,N',N'-tetra(p-tolyl)anthracene-9,10-diamine N,6-di-t-butyl-N,N'-diphenyl-N,N'-bis(4-isopropylphenyl)anthracene-9,10-diamine, 2,6-di-t-butyl-N,N'-bis(4-isopropylphenyl)-N,N'-di(p-tolyl)anthracene-9,10-diamine, 2,6-dicyclohexyl-N,N'-bis(4-isopropylphenyl)-N,N'-di(p-tolyl)anthracene-9,10-diamine, 2,6-dicyclohexyl-N,N'-bis(4-isopropylphenyl)-N,N'-bis(4-t-butylphenyl) Examples include anthracene-9,10-diamine, 9,10-bis(4-diphenylamino-phenyl)anthracene, 9,10-bis(4-di(1-naphthylamino)phenyl)anthracene, 9,10-bis(4-di(2-naphthylamino)phenyl)anthracene, 10-di-p-tolylamino-9-(4-di-p-tolylamino-1-naphthyl)anthracene, 10-diphenylamino-9-(4-diphenylamino-1-naphthyl)anthracene, and 10-diphenylamino-9-(6-diphenylamino-2-naphthyl)anthracene.

[0222] Other examples include [4-(4-diphenylaminophenyl)naphthalen-1-yl]-diphenylamine, [6-(4-diphenylaminophenyl)naphthalen-2-yl]-diphenylamine, 4,4'-bis[4-diphenylaminonaphthalen-1-yl]biphenyl, 4,4'-bis[6-diphenylaminonaphthalen-2-yl]biphenyl, 4,4”-bis[4-diphenylaminonaphthalen-1-yl]-p-terphenyl, and 4,4”-bis[6-diphenylaminonaphthalen-2-yl]-p-terphenyl. Alternatively, aromatic amine derivatives described in Japanese Patent Publication No. 2006-156888, etc., may be used.

[0223] Examples of coumarin derivatives include coumarin-6 and coumarin-334. Furthermore, coumarin derivatives described in Japanese Patent Publication No. 2004-43646, Japanese Patent Publication No. 2001-76876, and Japanese Patent Publication No. Hei 6-298758 may also be used.

[0224] Examples of pyran derivatives include DCM and DCJTB, listed below. [ka] Furthermore, pyran derivatives described in Japanese Patent Publication No. 2005-126399, Japanese Patent Publication No. 2005-097283, Japanese Patent Publication No. 2002-234892, Japanese Patent Publication No. 2001-220577, Japanese Patent Publication No. 2001-081090, and Japanese Patent Publication No. 2001-052869 may also be used.

[0225] The above-mentioned materials for the light-emitting layer (host material and dopant material) can also be used as materials for the light-emitting layer as polymer compounds obtained by polymerizing reactive compounds in which reactive substituents are substituted as monomers, or as polymer crosslinks thereof, or as pendant-type polymer compounds obtained by reacting a main-chain polymer with the reactive compound, or as pendant-type polymer crosslinks thereof. In this case, the explanation for the polycyclic aromatic compound represented by the general formula (1) above can be referenced for the reactive substituent. Details of the applications of such polymer compounds and polymer crosslinks will be described later.

[0226] <Electron injection layer and electron transport layer in organic electroluminescent devices> The electron injection layer 107 plays the 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 the 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 and mixing one or more types of electron transport / injection materials, or by a mixture of electron transport / injection materials and a polymer binder.

[0227] The electron injection and transport layer is responsible for injecting electrons from the cathode and transporting them. It is desirable for this layer to have high electron injection efficiency and to efficiently transport the injected electrons. To achieve this, it is preferable for the material to have high electron affinity, high electron mobility, excellent stability, and to be a material that does not easily generate trapping impurities during manufacturing and use. However, when considering the balance between hole and electron transport, if the main role is to efficiently prevent holes from the anode from flowing to the cathode side without recombining, then even if the electron transport capacity is not very high, the effect of improving luminescence efficiency will be equivalent to that of a material with high electron transport capacity. Therefore, the electron injection and transport layer in this embodiment may also include the function of a layer that can efficiently prevent the movement of holes.

[0228] As the material for forming the electron transport layer 106 or the electron injection layer 107 (electron transport material), any compound conventionally used as an electron transfer compound in photoconductive materials, or any known compound used in the electron injection layer and electron transport layer of an organic EL element, can be arbitrarily selected and used. In the present invention, a polycyclic aromatic compound represented by the above general formula (1) can be used as this electron transport material.

[0229] The 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 fused ring derivatives, and metal complexes having electron-accepting nitrogen. Specifically, examples include fused ring aromatic ring derivatives such as naphthalene and anthracene, styryl aromatic ring derivatives represented by 4,4'-bis(diphenylethenyl)biphenyl, perinone derivatives, coumarin derivatives, naphthalimide derivatives, quinone derivatives such as anthraquinone and diphenoquinone, phosphorus oxide derivatives, carbazole 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 individually or in combination with different materials.

[0230] Furthermore, specific examples of other electron transfer compounds include pyridine derivatives, naphthalene derivatives, anthracene derivatives, phenanthroline derivatives, perinone derivatives, coumarin derivatives, naphthalimide derivatives, anthraquinone derivatives, diphenoquinone derivatives, diphenylquinone derivatives, perylene derivatives, oxadiazole derivatives (such as 1,3-bis[(4-t-butylphenyl)1,3,4-oxadiazolyl]phenylene), thiophene derivatives, triazole derivatives (such as N-naphthyl-2,5-diphenyl-1,3,4-triazole), thiadiazole derivatives, metal complexes of oxine derivatives, quinolinol-based metal complexes, quinoxaline derivatives, polymers of quinoxaline derivatives, benzazole compounds, gallium complexes, pyrazole derivatives, perfluorinated phenylene derivatives, triazine derivatives, and pyrazole derivatives. Examples include radin derivatives, benzoquinoline derivatives (such as 2,2'-bis(benzo[h]quinoline-2-yl)-9,9'-spirobifluorene), imidazopyridine derivatives, borane derivatives, benzimidazole derivatives (such as tris(N-phenylbenzimidazole-2-yl)benzene), benzoxazole derivatives, benzothiazole derivatives, quinoline derivatives, oligopyridine derivatives such as terpyridine, bipyridine derivatives, terpyridine derivatives (such as 1,3-bis(4'-(2,2':6'2"-terpyridinyl))benzene), naphthyridine derivatives (such as bis(1-naphthyl)-4-(1,8-naphthyridine-2-yl)phenylphosphine oxide), aldazine derivatives, carbazole derivatives, indole derivatives, phosphorus oxide derivatives, and bisstyryl derivatives.

[0231] Furthermore, metal complexes having electron-accepting nitrogen can also be used, such as quinolinol-based metal complexes, hydroxyazole complexes such as hydroxyphenyl oxazole complexes, azomethine complexes, tropolone metal complexes, flavonol metal complexes, and benzoquinoline metal complexes.

[0232] The materials mentioned above can be used individually, but they can also be used in combination with other materials.

[0233] Among the materials mentioned above, borane derivatives, pyridine derivatives, fluorantene derivatives, BO derivatives, anthracene derivatives, benzofluorene derivatives, phosphine oxide derivatives, pyrimidine derivatives, carbazole derivatives, triazine derivatives, benzimidazole derivatives, phenanthroline derivatives, and quinolinol-based metal complexes are preferred.

[0234] <Bolan derivatives> Borane derivatives are compounds represented by the following general formula (ETM-1), for example, and are disclosed in detail in Japanese Patent Application Publication No. 2007-27587. [ka] In the above formula (ETM-1), R 11 and R 12 Each is independently at least one of hydrogen, alkyl, cycloalkyl, optionally substituted aryl, substituted silyl, optionally substituted nitrogen-containing heterocycle, or cyano, and R 13 ~R 16 Each of the following is independently an optionally substituted alkyl, optionally substituted cycloalkyl, or optionally substituted aryl; X is an optionally substituted arylene; Y is an optionally substituted aryl, substituted boryl, or optionally substituted carbazolyl, and each of the following is independently an integer from 0 to 3. Examples of substituents that may or may be substituted include aryl, heteroaryl, alkyl, or cycloalkyl groups.

[0235] Among the compounds represented by the above general formula (ETM-1), compounds represented by the following general formula (ETM-1-1) and compounds represented by the following general formula (ETM-1-2) are preferred. [ka] In formula (ETM-1-1), R 11 and R 12Each is independently at least one of hydrogen, alkyl, cycloalkyl, optionally substituted aryl, substituted silyl, optionally substituted nitrogen-containing heterocycle, or cyano, and R 13 ~R 16 Each of these is independently an optionally substituted alkyl, an optionally substituted cycloalkyl, or an optionally substituted aryl, and R 21 and R 22 Each is independently at least one of hydrogen, alkyl, cycloalkyl, optionally substituted aryl, substituted silyl, optionally substituted nitrogen-containing heterocycle, or cyano, and X 1 is an arylene with 20 or fewer carbon atoms, which may be substituted, where n is an independent integer between 0 and 3, and m is an independent integer between 0 and 4. Examples of substituents that may or may be substituted include aryl, heteroaryl, alkyl, or cycloalkyl groups. [ka] In formula (ETM-1-2), R 11 and R 12 Each is independently at least one of hydrogen, alkyl, cycloalkyl, optionally substituted aryl, substituted silyl, optionally substituted nitrogen-containing heterocycle, or cyano, and R 13 ~R 16 Each of these is independently an optionally substituted alkyl, an optionally substituted cycloalkyl, or an optionally substituted aryl, and X 1 is an arylene with 20 or fewer carbon atoms, which may be substituted, and n is an independent integer between 0 and 3. Examples of substituents that may or may be substituted include aryl, heteroaryl, alkyl, or cycloalkyl groups.

[0236] X 1Specific examples include divalent groups represented by any of the following formulas (X-1) to (X-9). The asterisk (*) in each structural formula indicates a bond position. [ka] (In each formula, R a These are, independently, alkyl groups, cycloalkyl groups, or optionally substituted phenyl groups.

[0237] Specific examples of these borane derivatives include the following compounds. [ka]

[0238] This borane derivative can be produced using known raw materials and known synthesis methods.

[0239] <Pyridine derivatives> The pyridine derivative is, for example, a compound represented by the following formula (ETM-2), and preferably a compound represented by formula (ETM-2-1) or formula (ETM-2-2). [ka]

[0240] 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.

[0241] In the above formula (ETM-2-1), R 11 ~R 18 Each of these is 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).

[0242] In the above formula (ETM-2-2), R11 and R 12 Each of these is independently hydrogen, alkyl (preferably alkyl with 1 to 24 carbon atoms), cycloalkyl (preferably cycloalkyl with 3 to 12 carbon atoms), or aryl (preferably aryl with 6 to 30 carbon atoms), and R 11 and R 12 They may be joined together to form a ring.

[0243] In each formula, the "pyridine substituent" is one of the following formulas (Py-1) to (Py-15), and each pyridine substituent may be independently substituted with an alkyl group having 1 to 4 carbon atoms or a cycloalkyl group having 5 to 10 carbon atoms. Furthermore, the pyridine substituent may be bonded to the φ, anthracene ring, or fluorene ring in each formula via a phenylene group or naphthylene group. The asterisk (*) in each structural formula indicates the bond position. [ka]

[0244] The pyridine substituent is one of the above formulas (Py-1) to (Py-15), but among these, it is preferably one of the following formulas (Py-21) to (Py-44). The asterisk (*) in each structural formula indicates the bond position. [ka]

[0245] At least one hydrogen atom in each pyridine derivative may be substituted with deuterium, and one of the two "pyridine substituents" in formulas (ETM-2-1) and (ETM-2-2) may be substituted with an aryl atom.

[0246] R 11 ~R 18The "alkyl" in this context can be either linear or branched, for example, a linear alkyl group having 1 to 24 carbon atoms or a branched alkyl group having 3 to 24 carbon atoms. A preferred "alkyl" is an alkyl group having 1 to 18 carbon atoms (a branched alkyl group having 3 to 18 carbon atoms). A more preferred "alkyl" is an alkyl group having 1 to 12 carbon atoms (a branched alkyl group having 3 to 12 carbon atoms). A still preferred "alkyl" is an alkyl group having 1 to 6 carbon atoms (a branched alkyl group having 3 to 6 carbon atoms). A particularly preferred "alkyl" is an alkyl group having 1 to 4 carbon atoms (a branched alkyl group having 3 to 4 carbon atoms).

[0247] Specific examples of "alkyl" include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, t-butyl, n-pentyl, isopentyl, neopentyl, t-pentyl(t-amyl), n-hexyl, 1-methylpentyl, 3,3-dimethylbutyl, 2-ethylbutyl, n-heptyl, 1-methylhexyl, n-octyl, t-octyl(1,1,3,3-tetramethylbutyl), and 1-methylbutyl. Examples include hepheptyl, 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. Other examples include 1-ethyl-1-methylpropyl, 1,1-diethylpropyl, 1,1-dimethylbutyl, 1-ethyl-1-methylbutyl, 1,1,4-trimethylpentyl, 1,1,2-trimethylpropyl, 1,1-dimethyloctyl, 1,1-dimethylpentyl, 1,1-dimethylheptyl, 1,1,5-trimethylhexyl, 1-ethyl-1-methylhexyl, 1-ethyl-1,3-dimethylbutyl, 1,1,2,2-tetramethylpropyl, 1-butyl-1-methylpentyl, 1,1-diethylbutyl, 1-ethyl-1-methylpentyl, 1,1,3-trimethylbutyl, 1-propyl-1-methylpentyl, 1,1,2-trimethylpropyl, 1-ethyl-1,2,2-trimethylpropyl, 1-propyl-1-methylbutyl, and 1,1-dimethylhexyl.

[0248] For alkyl groups with 1 to 4 carbon atoms to be substituted for pyridine substituents, the above description of alkyl groups can be referenced.

[0249] R 11 ~R 18 Examples of "cycloalkyl" in this context include cycloalkyls having 3 to 12 carbon atoms. Preferred "cycloalkyl" are cycloalkyls having 3 to 10 carbon atoms. More preferred "cycloalkyl" are cycloalkyls having 3 to 8 carbon atoms. Even more preferred "cycloalkyl" are cycloalkyls having 3 to 6 carbon atoms. Specific examples of "cycloalkyl" compounds include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, methylcyclopentyl, cycloheptyl, methylcyclohexyl, cyclooctyl, or dimethylcyclohexyl.

[0250] For cycloalkyl groups with 5 to 10 carbon atoms to be substituted with pyridine substituents, the above description of cycloalkyl groups can be referenced.

[0251] R 11 ~R 18In this context, the preferred aryl is an aryl having 6 to 30 carbon atoms, a more preferred aryl is an aryl having 6 to 18 carbon atoms, an even more preferred aryl is an aryl having 6 to 14 carbon atoms, and a particularly preferred aryl is an aryl having 6 to 12 carbon atoms.

[0252] Specific examples of "aryl compounds with 6 to 30 carbon atoms" include the monocyclic aryl phenyl, the condensed bicyclic aryl (1-,2-)naphthyl, the condensed tricyclic aryls acenaphthylene-(1-,3-,4-,5-)yl, fluoren-(1-,2-,3-,4-,9-)yl, phenalen-(1-,2-)yl, (1-,2-,3-,4-,9-)phenanthryl, the condensed tetracyclic aryls triphenylene-(1-,2-)yl, pyren-(1-,2-,4-)yl, naphthacene-(1-,2-,5-)yl, and the condensed pentacyclic aryls perylene-(1-,2-,3-)yl, pentacene-(1-,2-,5-,6-)yl.

[0253] Preferred "aryls having 6 to 30 carbon atoms" include phenyl, naphthyl, phenanthryl, crisenyl, or triphenylenyl, more preferably phenyl, 1-naphthyl, 2-naphthyl, or phenanthryl, and particularly preferably phenyl, 1-naphthyl, or 2-naphthyl.

[0254] In the above formula (ETM-2-2), R 11 and R 12 These may be bonded together to form a ring, and as a result, cyclobutane, cyclopentane, cyclopentene, cyclopentadiene, cyclohexane, fluorene, or indene may be spirobonded to the five-membered ring of the fluorene skeleton.

[0255] Specific examples of pyridine derivatives include the following compounds. [ka]

[0256] This pyridine derivative can be produced using known raw materials and known synthesis methods.

[0257] <Fluoranthene derivative> The fluoranthene derivative is, for example, a compound represented by the following general formula (ETM-3), and specifically, it is disclosed in International Publication No. 2010 / 134352.

Chemical formula

[0258] In the above 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.

[0259] Specific examples of this fluoranthene derivative include, for example, the following compounds.

Chemical formula

[0260] <BO-based derivative> The BO-based derivative is, for example, a polycyclic aromatic compound represented by the following formula (ETM-4), or a multimer of a polycyclic aromatic compound having a plurality of structures represented by the following formula (ETM-4).

Chemical formula

[0261] R 1 ~R 11Each of these is independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl (the two aryls may be linked by a single bond or a linking group), alkyl, cycloalkyl, alkoxy, or aryloxy, and the R 1 ~R 11 At least one hydrogen in may be substituted with an aryl, heteroaryl, alkyl, or cycloalkyl group.

[0262] Also, R 1 ~R 11 Adjacent groups among them may bond together to form an aryl ring or heteroaryl ring with the a, b, or c ring, and at least one hydrogen in the formed ring may be substituted with aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl (the two aryls may be bonded via a single bond or a linking group), alkyl, cycloalkyl, alkoxy, or aryloxy, and at least one hydrogen in these substituents may be substituted with aryl, heteroaryl, alkyl, or cycloalkyl.

[0263] Furthermore, at least one hydrogen atom in the compound or structure represented by formula (ETM-4) may be substituted with a halogen or deuterium.

[0264] For explanations regarding the substituents and ring formation morphology in formula (ETM-4), as well as the polymers formed by the combination of multiple structures of formula (ETM-4), please refer to the explanations contained in International Publication No. 2015 / 102118.

[0265] Specific examples of these BO derivatives include the following compounds. [ka]

[0266] This BO derivative can be produced using known raw materials and known synthesis methods.

[0267] <Anthracene derivatives> One example of anthracene derivatives is the compound represented by the following formula (ETM-5-1). [ka]

[0268] Ar is independently either divalent benzene or naphthalene, and R 1 ~R 4 These are, independently, hydrogen, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, or an aryl group having 6 to 20 carbon atoms.

[0269] Each Ar can be independently selected from divalent benzene or naphthalene as appropriate, and the two Ars may be different or the same, but from the viewpoint of ease of synthesis of anthracene derivatives, it is preferable that they be the same. The Ar is bonded to pyridine to form an "Ar and pyridine moiety," and this moiety is bonded to anthracene as a group represented by, for example, one of the following formulas (Py-1) to (Py-12). The asterisk (*) in each structural formula indicates the bond position. [ka]

[0270] Among these groups, the group represented by any of the above formulas (Py-1) to (Py-9) is preferred, and the group represented by any of the above formulas (Py-1) to (Py-6) is more preferred. The two "Ar and pyridine moieties" bonded to anthracene may have the same or different structures, but from the viewpoint of ease of synthesis of the anthracene derivative, it is preferable that they have the same structure. However, from the viewpoint of device properties, it is preferable that the structures of the two "Ar and pyridine moieties" be the same or different.

[0271] R1 ~R 4 The C1-C6 alkyl group in the formula may be either linear or branched. That is, it may be a linear alkyl group with C1-C6 or a branched alkyl group with C3-C6. More preferably, it may be an alkyl group with C1-C4 (a branched alkyl group with C3-C4). Specific examples include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, t-butyl, n-pentyl, isopentyl, neopentyl, t-pentyl (t-amyl), n-hexyl, 1-methylpentyl, 3,3-dimethylbutyl, or 2-ethylbutyl, with methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, or t-butyl being preferred, and methyl, ethyl, or t-butyl being more preferred.

[0272] R 1 ~R 4 Specific examples of cycloalkyl compounds having 3 to 6 carbon atoms include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, methylcyclopentyl, cycloheptyl, methylcyclohexyl, cyclooctyl, or dimethylcyclohexyl.

[0273] R 1 ~R 4 Regarding the aryl compounds having 6 to 20 carbon atoms, aryl compounds having 6 to 16 carbon atoms are preferred, aryl compounds having 6 to 12 carbon atoms are more preferred, and aryl compounds having 6 to 10 carbon atoms are particularly preferred.

[0274] Specific examples of "aryls with 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), (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 Examples include nyl-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), the condensed tricyclic aryls anthracene-(1-,2-,9-)yl, acenaphthylene-(1-,3-,4-,5-)yl, fluoren-(1-,2-,3-,4-,9-)yl, phenalen-(1-,2-)yl, (1-,2-,3-,4-,9-)phenanthryl, the condensed tetracyclic aryls triphenylene-(1-,2-)yl, pyren-(1-,2-,4-)yl, tetracene-(1-,2-,5-)yl, and the condensed pentacyclic aryl perylene-(1-,2-,3-)yl.

[0275] Preferred "aryls 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, even more preferably phenyl, biphenylyl, 1-naphthyl, or 2-naphthyl, and most preferably phenyl.

[0276] One example of anthracene derivatives is the compound represented by the following formula (ETM-5-2). [ka]

[0277] Ar 1 These are, independently, single-bonded, divalent benzene, naphthalene, anthracene, fluorene, or phenalene.

[0278] Ar 2 Each of these is an aryl compound having 6 to 20 carbon atoms, and the same explanation as for "aryl compounds having 6 to 20 carbon atoms" in the above formula (ETM-5-1) can be cited. Aryl compounds having 6 to 16 carbon atoms are preferred, aryl compounds having 6 to 12 carbon atoms are more preferred, and aryl compounds having 6 to 10 carbon atoms are particularly preferred. Specific examples include phenyl, biphenylyl, naphthyl, terphenylyl, anthracenyl, acenaphthirenyl, fluorenyl, phenalenyl, phenanthryl, triphenylenyl, pyrenyl, tetracenyl, and perilenyl.

[0279] R 1 ~R 4 Each of these is independently hydrogen, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, or an aryl group having 6 to 20 carbon atoms, and the explanation in formula (ETM-5-1) above can be referenced.

[0280] Specific examples of these anthracene derivatives include the following compounds, for example. [ka]

[0281] These anthracene derivatives can be produced using known raw materials and known synthesis methods.

[0282] <Benzofluorene derivatives> Benzofluorene derivatives are compounds represented by the following formula (ETM-6), for example. [ka]

[0283] Ar 1Each of these is an aryl compound having 6 to 20 carbon atoms, and the same explanation as for "aryl compounds having 6 to 20 carbon atoms" in the above formula (ETM-5-1) can be cited. Aryl compounds having 6 to 16 carbon atoms are preferred, aryl compounds having 6 to 12 carbon atoms are more preferred, and aryl compounds having 6 to 10 carbon atoms are particularly preferred. Specific examples include phenyl, biphenylyl, naphthyl, terphenylyl, anthracenyl, acenaphthirenyl, fluorenyl, phenalenyl, phenanthryl, triphenylenyl, pyrenyl, tetracenyl, and perilenyl.

[0284] Ar 2 Each of these is independently hydrogen, alkyl (preferably alkyl with 1 to 24 carbon atoms), cycloalkyl (preferably cycloalkyl with 3 to 12 carbon atoms), or aryl (preferably aryl with 6 to 30 carbon atoms), and two Ar 2 They may be joined together to form a ring.

[0285] Ar 2 The "alkyl" in this context can be either linear or branched, for example, a linear alkyl group having 1 to 24 carbon atoms or a branched alkyl group having 3 to 24 carbon atoms. A preferred "alkyl" is an alkyl group having 1 to 18 carbon atoms (a branched alkyl group having 3 to 18 carbon atoms). A more preferred "alkyl" is an alkyl group having 1 to 12 carbon atoms (a branched alkyl group having 3 to 12 carbon atoms). A still preferred "alkyl" is an alkyl group having 1 to 6 carbon atoms (a branched alkyl group having 3 to 6 carbon atoms). A particularly preferred "alkyl" is an alkyl group having 1 to 4 carbon atoms (a branched alkyl group 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 (t-amyl), n-hexyl, 1-methylpentyl, 3,3-dimethylbutyl, 2-ethylbutyl, n-heptyl, and 1-methylhexyl.

[0286] Ar 2Examples of "cycloalkyl" in this context include cycloalkyls having 3 to 12 carbon atoms. Preferred "cycloalkyls" are those having 3 to 10 carbon atoms. More preferred "cycloalkyls" are those having 3 to 8 carbon atoms. Even more preferred "cycloalkyls" are those having 3 to 6 carbon atoms. Specific examples of "cycloalkyls" include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, methylcyclopentyl, cycloheptyl, methylcyclohexyl, cyclooctyl, or dimethylcyclohexyl.

[0287] Ar 2 In this context, the preferred aryl is an aryl having 6 to 30 carbon atoms, a more preferred aryl is an aryl having 6 to 18 carbon atoms, an even more preferred aryl is an aryl having 6 to 14 carbon atoms, and a particularly preferred aryl is an aryl having 6 to 12 carbon atoms.

[0288] Specific examples of "aryl compounds with 6 to 30 carbon atoms" include phenyl, naphthyl, acenaphthirenyl, fluorenyl, phenalenyl, phenanthryl, triphenylenyl, pyrenyl, naphthacenyl, perilenyl, and pentacenyl.

[0289] Two Ar 2 These may be bonded together to form a ring, and as a result, cyclobutane, cyclopentane, cyclopentene, cyclopentadiene, cyclohexane, fluorene, or indene may be spirobonded to the five-membered ring of the fluorene skeleton.

[0290] Specific examples of these benzofluorene derivatives include the following compounds. [ka]

[0291] This benzofluorene derivative can be produced using known raw materials and known synthesis methods.

[0292] <Phosphine oxide derivatives> Phosphine oxide derivatives are compounds represented by formula (ETM-7-1) below, for example. Further details are also described in International Publication No. 2013 / 079217. [ka] R 5 These are substituted or unsubstituted alkyl groups with 1 to 20 carbon atoms, cycloalkyl groups with 3 to 20 carbon atoms, aryl groups with 6 to 20 carbon atoms, or heteroaryl groups with 5 to 20 carbon atoms. R 6 These are CN, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, cycloalkyl groups having 3 to 20 carbon atoms, heteroalkyl groups having 1 to 20 carbon atoms, aryl groups having 6 to 20 carbon atoms, heteroaryl groups having 5 to 20 carbon atoms, alkoxy groups having 1 to 20 carbon atoms, or aryloxy groups having 6 to 20 carbon atoms. R 7 and R 8 These are, independently, substituted or unsubstituted aryls with 6 to 20 carbon atoms or heteroaryls with 5 to 20 carbon atoms. R 9 It is oxygen or sulfur, j is 0 or 1, k is 0 or 1, r is an integer between 0 and 4, and q is an integer between 1 and 3. Examples of substituents that may be substituted include aryl, heteroaryl, alkyl, or cycloalkyl compounds.

[0293] The phosphine oxide derivative may be, for example, a compound represented by the following formula (ETM-7-2). [ka]

[0294] R 1 ~R 3These may be the same or different, and are selected from hydrogen, alkyl groups, cycloalkyl groups, aralkyl groups, alkenyl groups, cycloalkenyl groups, alkynyl groups, alkoxy groups, alkylthio groups, cycloalkylthio groups, aryl ether groups, arylthioether groups, aryl groups, heterocyclic groups, halogens, cyano groups, aldehyde groups, carbonyl groups, carboxyl groups, amino groups, nitro groups, silyl groups, and condensed rings formed between adjacent substituents.

[0295] Ar 1 These may be the same or different, and are either an arylene group or a heteroarylene group. 2 These may be the same or different, and are either an aryl group or a heteroaryl group. However, Ar 1 and Ar 2 At least one of them has a substituent or forms a fused ring with an adjacent substituent. n is an integer from 0 to 3, when n is 0 there is no unsaturated structural part, and when n is 3 there is R 1 It does not exist.

[0296] Of these substituents, alkyl groups refer to saturated aliphatic hydrocarbon groups such as methyl, ethyl, propyl, and butyl groups, and may be unsubstituted or substituted. There are no particular restrictions on the substituents when substituted; for example, alkyl groups, aryl groups, heterocyclic groups, etc., are examples, and this point is also common to the following description. Furthermore, the number of carbon atoms in alkyl groups is not particularly limited, but for reasons of availability and cost, it is usually in the range of 1 to 20.

[0297] Furthermore, cycloalkyl groups refer to saturated alicyclic hydrocarbon groups such as cyclopropyl, cyclohexyl, norbornyl, and adamantyl, which may be unsubstituted or substituted. The number of carbon atoms in the alkyl group is not particularly limited, but is usually in the range of 3 to 20.

[0298] Furthermore, an aralkyl group refers to an aromatic hydrocarbon group mediated by an aliphatic hydrocarbon such as a benzyl group or a phenylethyl group, and both the aliphatic hydrocarbon and the aromatic hydrocarbon may be unsubstituted or substituted. The number of carbon atoms in the aliphatic part is not particularly limited, but is usually in the range of 1 to 20.

[0299] Furthermore, an alkenyl group refers to an unsaturated aliphatic hydrocarbon group containing a double bond, such as a vinyl group, allyl group, or butadienyl group, which may be unsubstituted or substituted. The number of carbon atoms in an alkenyl group is not particularly limited, but is usually in the range of 2 to 20.

[0300] Furthermore, a cycloalkenyl group refers to an unsaturated alicyclic hydrocarbon group containing a double bond, such as a cyclopentenyl group, cyclopentadienyl group, or cyclohexene group, and can be either unsubstituted or substituted.

[0301] Furthermore, an alkynyl group refers to an unsaturated aliphatic hydrocarbon group containing a triple bond, such as an acetylenyl group, and can be either unsubstituted or substituted. The number of carbon atoms in an alkynyl group is not particularly limited, but is usually in the range of 2 to 20.

[0302] Furthermore, an alkoxy group refers to an aliphatic hydrocarbon group mediated by an ether bond, such as a methoxy group, and the aliphatic hydrocarbon group may be unsubstituted or substituted. The number of carbon atoms in an alkoxy group is not particularly limited, but is usually in the range of 1 to 20.

[0303] Furthermore, an alkylthio group is a group in which the oxygen atom in the ether bond of an alkoxy group is replaced by a sulfur atom.

[0304] Furthermore, a cycloalkylthio group is a group in which the oxygen atom in the ether bond of a cycloalkoxy group is replaced by a sulfur atom.

[0305] Furthermore, an aryl ether group refers to an aromatic hydrocarbon group mediated by an ether bond, such as a phenoxy group, and the aromatic hydrocarbon group may be unsubstituted or substituted. The number of carbon atoms in an aryl ether group is not particularly limited, but is usually in the range of 6 to 40.

[0306] Furthermore, an arylthioether group is a group in which the oxygen atom in the ether bond of an aryl ether group is replaced by a sulfur atom.

[0307] Furthermore, aryl groups refer to aromatic hydrocarbon groups such as phenyl, naphthyl, biphenyl, phenanthryl, terphenyl, and pyrenyl groups. Aryl groups can be unsubstituted or substituted. The number of carbon atoms in an aryl group is not particularly limited, but is usually in the range of 6 to 40.

[0308] Furthermore, heterocyclic groups refer to cyclic structural groups that have atoms other than carbon, such as furanyl groups, thiophenyl groups, oxazolyl groups, pyridyl groups, quinolinyl groups, and carbazolyl groups, and these can be unsubstituted or substituted. The number of carbon atoms in a heterocyclic group is not particularly limited, but it is usually in the range of 2 to 30.

[0309] Halogens refer to fluorine, chlorine, bromine, and iodine.

[0310] Aldehyde groups, carbonyl groups, and amino groups may also include groups substituted with aliphatic hydrocarbons, alicyclic hydrocarbons, aromatic hydrocarbons, heterocyclic groups, etc.

[0311] Furthermore, aliphatic hydrocarbons, alicyclic hydrocarbons, aromatic hydrocarbons, and heterocyclic hydrocarbons may be unsubstituted or substituted.

[0312] A silyl group refers to a silicon compound group, such as a trimethylsilyl group, which can be unsubstituted or substituted. The number of carbon atoms in a silyl group is not particularly limited, but is usually in the range of 3 to 20. The number of silicon atoms is usually between 1 and 6.

[0313] The fused ring formed between adjacent substituents is, for example, Ar 1 and R 2 Ar 1 and R 3 Ar 2 and R 2 Ar 2 and R 3 , R 2 and R 3 Ar 1 and Ar 2 It is a conjugated or unconjugated fused ring formed between the following elements. Here, when n is 1, two R 1 These rings may form conjugated or non-conjugated fused rings. These fused rings may contain nitrogen, oxygen, and sulfur atoms in their intraring structure, and may also be fused with other rings.

[0314] Specific examples of these phosphine oxide derivatives include the following compounds. [ka]

[0315] This phosphine oxide derivative can be produced using known raw materials and known synthesis methods.

[0316] <Pyrimidine derivatives> The pyrimidine derivative is, for example, a compound represented by the following formula (ETM-8), and preferably a compound represented by the following formula (ETM-8-1). Further details are also described in International Publication No. 2011 / 021689. [ka]

[0317] Each Ar is independently an optionally substituted aryl or optionally substituted heteroaryl. n is an integer from 1 to 4, preferably an integer from 1 to 3, and more preferably 2 or 3.

[0318] Examples of the "aryl" in "aryl which may be substituted" include aryls having 6 to 30 carbon atoms, preferably aryls having 6 to 24 carbon atoms, more preferably aryls having 6 to 20 carbon atoms, and even more preferably aryls having 6 to 12 carbon atoms.

[0319] Specific examples of "aryl" include monocyclic aryls such as phenyl, bicyclic aryls such as (2-,3-,4-)biphenylyl, condensed bicyclic aryls such as (1-,2-)naphthyl, tricyclic aryls such as terphenylyl (m-terphenyl-2'-yl, m-terphenyl-4'-yl, m-terphenyl-5'-yl, o-terphenyl-3'-yl, o-terphenyl-4'-yl, p-terphenyl-2'-yl, m-terphenyl-2-yl, m-terphenyl-3-yl, m-terphenyl-4-yl, o-terphenyl-2-yl, o-terphenyl-3-yl, o-terphenyl-4-yl, p-terphenyl-2-yl, p-terphenyl-3-yl, p-terphenyl-4-yl), and condensed tricyclic aryls. Examples of aryl compounds include acenaphthylene-(1-,3-,4-,5-)yl, fluoren-(1-,2-,3-,4-,9-)yl, phenalen-(1-,2-)yl, (1-,2-,3-,4-,9-)phenanthryl; tetracyclic aryl compounds include quaterphenylyl (5'-phenyl-m-terphenyl-2-yl, 5'-phenyl-m-terphenyl-3-yl, 5'-phenyl-m-terphenyl-4-yl, m-quaterphenylyl); condensed tetracyclic aryl compounds include triphenylene-(1-,2-)yl, pyren-(1-,2-,4-)yl, naphthacene-(1-,2-,5-)yl; and condensed pentacyclic aryl compounds include perylene-(1-,2-,3-)yl, pentacene-(1-,2-,5-,6-)yl.

[0320] Examples of "heteroaryls that may be substituted" include heteroaryls having 2 to 30 carbon atoms, with heteroaryls having 2 to 25 carbon atoms being preferred, heteroaryls having 2 to 20 carbon atoms being more preferred, heteroaryls having 2 to 15 carbon atoms being even more preferred, and heteroaryls having 2 to 10 carbon atoms being particularly preferred. Examples of heteroaryls include heterocycles containing 1 to 5 heteroatoms selected from oxygen, sulfur, and nitrogen in addition to carbon as ring constituent atoms.

[0321] Specific heteroaryls include, for example, pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, oxadiazolyl, thiadiazolyl, triazolyl, tetrazolyl, pyrazolyl, pyridinyl, pyrimidinyl, pyridadinyl, pyrazinyl, triazinyl, indolyl, isoindolyl, 1H-indazolyl, benzimidazolyl, benzoxazolyl, benzothiazolyl, 1H-benzotriazolyl, quinolinyl, isoquinolinyl, cinnolinyl, quinazolinyl, quinoxalinyl, phthalazinyl, naphthilidinyl, prinyl, pteridinyl, carbazolyl, Examples include acridinyl, phenoxathiinyl, phenoxazinyl, phenothiazinyl, phenazinyl, phenazacylinyl, indolidinyl, furanil, benzofuranil, isobenzofuranil, dibenzofuranil, naphthobenzofuranil, thiophenyl, benzothiophenyl, dibenzothiophenyl, naphthobenzothiophenyl, benzophosphoryl, dibenzophosphoryl, monovalent group of the benzophosphorus oxide ring, monovalent group of the dibenzophosphorus oxide ring, flazanil, thianthrenil, indolocarbazolyl, benzoindorocarbazolyl, and benzobenzoindorocarbazolyl.

[0322] Furthermore, at least one hydrogen atom in the above-mentioned aryl and heteroaryl compounds may be substituted, for example, with the above-mentioned aryl or heteroaryl compounds.

[0323] Specific examples of these pyrimidine derivatives include the following compounds. [ka]

[0324] This pyrimidine derivative can be produced using known raw materials and known synthesis methods.

[0325] <Carbazole derivatives> Carbazole derivatives are compounds represented by formula (ETM-9) below, for example, or polymers formed by the linkage of multiple such compounds via single bonds or other means. Further details are described in U.S. Patent Application Publication No. 2014 / 0197386. [ka]

[0326] Each Ar is independently an optionally substituted aryl or optionally substituted heteroaryl. Each n is independently an integer between 0 and 4, preferably an integer between 0 and 3, and more preferably 0 or 1.

[0327] Examples of the "aryl" in "aryl which may be substituted" include aryls having 6 to 30 carbon atoms, preferably aryls having 6 to 24 carbon atoms, more preferably aryls having 6 to 20 carbon atoms, and even more preferably aryls having 6 to 12 carbon atoms.

[0328] Specific examples of "aryl" include monocyclic aryls such as phenyl, bicyclic aryls such as (2-,3-,4-)biphenylyl, condensed bicyclic aryls such as (1-,2-)naphthyl, tricyclic aryls such as terphenylyl (m-terphenyl-2'-yl, m-terphenyl-4'-yl, m-terphenyl-5'-yl, o-terphenyl-3'-yl, o-terphenyl-4'-yl, p-terphenyl-2'-yl, m-terphenyl-2-yl, m-terphenyl-3-yl, m-terphenyl-4-yl, o-terphenyl-2-yl, o-terphenyl-3-yl, o-terphenyl-4-yl, p-terphenyl-2-yl, p-terphenyl-3-yl, p-terphenyl-4-yl), and condensed tricyclic aryls. Examples of aryl compounds include acenaphthylene-(1-,3-,4-,5-)yl, fluoren-(1-,2-,3-,4-,9-)yl, phenalen-(1-,2-)yl, (1-,2-,3-,4-,9-)phenanthryl; tetracyclic aryl compounds include quaterphenylyl (5'-phenyl-m-terphenyl-2-yl, 5'-phenyl-m-terphenyl-3-yl, 5'-phenyl-m-terphenyl-4-yl, m-quaterphenylyl); condensed tetracyclic aryl compounds include triphenylene-(1-,2-)yl, pyren-(1-,2-,4-)yl, naphthacene-(1-,2-,5-)yl; and condensed pentacyclic aryl compounds include perylene-(1-,2-,3-)yl, pentacene-(1-,2-,5-,6-)yl.

[0329] Examples of "heteroaryls that may be substituted" include heteroaryls having 2 to 30 carbon atoms, with heteroaryls having 2 to 25 carbon atoms being preferred, heteroaryls having 2 to 20 carbon atoms being more preferred, heteroaryls having 2 to 15 carbon atoms being even more preferred, and heteroaryls having 2 to 10 carbon atoms being particularly preferred. Examples of heteroaryls include heterocycles containing 1 to 5 heteroatoms selected from oxygen, sulfur, and nitrogen in addition to carbon as ring constituent atoms.

[0330] Specific heteroaryls include, for example, pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, oxadiazolyl, thiadiazolyl, triazolyl, tetrazolyl, pyrazolyl, pyridinyl, pyrimidinyl, pyridadinyl, pyrazinyl, triazinyl, indolyl, isoindolyl, 1H-indazolyl, benzimidazolyl, benzoxazolyl, benzothiazolyl, 1H-benzotriazolyl, quinolinyl, isoquinolinyl, cinnolinyl, quinazolinyl, quinoxalinyl, phthalazinyl, naphthilidinyl, prinyl, pteridinyl, carbazolyl, Examples include acridinyl, phenoxathiinyl, phenoxazinyl, phenothiazinyl, phenazinyl, phenazacylinyl, indolidinyl, furanil, benzofuranil, isobenzofuranil, dibenzofuranil, naphthobenzofuranil, thiophenyl, benzothiophenyl, dibenzothiophenyl, naphthobenzothiophenyl, benzophosphoryl, dibenzophosphoryl, monovalent group of the benzophosphorus oxide ring, monovalent group of the dibenzophosphorus oxide ring, flazanil, thianthrenil, indolocarbazolyl, benzoindorocarbazolyl, and benzobenzoindorocarbazolyl.

[0331] Furthermore, at least one hydrogen atom in the above-mentioned aryl and heteroaryl compounds may be substituted, for example, with the above-mentioned aryl or heteroaryl compounds.

[0332] Carbazole derivatives may be polymers in which multiple compounds represented by the above formula (ETM-9) are linked by single bonds or other means. In this case, in addition to single bonds, they may also be linked by aryl rings (preferably polyvalent benzene rings, naphthalene rings, anthracene rings, fluorene rings, benzofluorene rings, phenalene rings, phenanthrene rings, or triphenylene rings).

[0333] Specific examples of these carbazole derivatives include the following compounds. [ka]

[0334] This carbazole derivative can be produced using known raw materials and known synthesis methods.

[0335] <Triadine derivatives> The triazine derivative is, for example, a compound represented by the following formula (ETM-10), and preferably a compound represented by the following formula (ETM-10-1). Further details are described in U.S. Patent Application Publication No. 2011 / 0156013. [ka]

[0336] Each Ar is independently a substituted or substituted heteroaryl. n is an integer between 1 and 3, preferably 2 or 3.

[0337] Examples of the "aryl" in "aryl which may be substituted" include aryls having 6 to 30 carbon atoms, preferably aryls having 6 to 24 carbon atoms, more preferably aryls having 6 to 20 carbon atoms, and even more preferably aryls having 6 to 12 carbon atoms.

[0338] Specific examples of "aryl" include monocyclic aryls such as phenyl, bicyclic aryls such as (2-,3-,4-)biphenylyl, condensed bicyclic aryls such as (1-,2-)naphthyl, tricyclic aryls such as terphenylyl (m-terphenyl-2'-yl, m-terphenyl-4'-yl, m-terphenyl-5'-yl, o-terphenyl-3'-yl, o-terphenyl-4'-yl, p-terphenyl-2'-yl, m-terphenyl-2-yl, m-terphenyl-3-yl, m-terphenyl-4-yl, o-terphenyl-2-yl, o-terphenyl-3-yl, o-terphenyl-4-yl, p-terphenyl-2-yl, p-terphenyl-3-yl, p-terphenyl-4-yl), and condensed tricyclic aryls. Examples of aryl compounds include acenaphthylene-(1-,3-,4-,5-)yl, fluoren-(1-,2-,3-,4-,9-)yl, phenalen-(1-,2-)yl, (1-,2-,3-,4-,9-)phenanthryl; tetracyclic aryl compounds include quaterphenylyl (5'-phenyl-m-terphenyl-2-yl, 5'-phenyl-m-terphenyl-3-yl, 5'-phenyl-m-terphenyl-4-yl, m-quaterphenylyl); condensed tetracyclic aryl compounds include triphenylene-(1-,2-)yl, pyren-(1-,2-,4-)yl, naphthacene-(1-,2-,5-)yl; and condensed pentacyclic aryl compounds include perylene-(1-,2-,3-)yl, pentacene-(1-,2-,5-,6-)yl.

[0339] Examples of "heteroaryls that may be substituted" include heteroaryls having 2 to 30 carbon atoms, with heteroaryls having 2 to 25 carbon atoms being preferred, heteroaryls having 2 to 20 carbon atoms being more preferred, heteroaryls having 2 to 15 carbon atoms being even more preferred, and heteroaryls having 2 to 10 carbon atoms being particularly preferred. Examples of heteroaryls include heterocycles containing 1 to 5 heteroatoms selected from oxygen, sulfur, and nitrogen in addition to carbon as ring constituent atoms.

[0340] Specific heteroaryls include, for example, pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, oxadiazolyl, thiadiazolyl, triazolyl, tetrazolyl, pyrazolyl, pyridinyl, pyrimidinyl, pyridadinyl, pyrazinyl, triazinyl, indolyl, isoindolyl, 1H-indazolyl, benzimidazolyl, benzoxazolyl, benzothiazolyl, 1H-benzotriazolyl, quinolinyl, isoquinolinyl, cinnolinyl, quinazolinyl, quinoxalinyl, phthalazinyl, naphthilidinyl, prinyl, pteridinyl, carbazolyl, Examples include acridinyl, phenoxathiinyl, phenoxazinyl, phenothiazinyl, phenazinyl, phenazacylinyl, indolidinyl, furanil, benzofuranil, isobenzofuranil, dibenzofuranil, naphthobenzofuranil, thiophenyl, benzothiophenyl, dibenzothiophenyl, naphthobenzothiophenyl, benzophosphoryl, dibenzophosphoryl, monovalent group of the benzophosphorus oxide ring, monovalent group of the dibenzophosphorus oxide ring, flazanil, thianthrenil, indolocarbazolyl, benzoindorocarbazolyl, and benzobenzoindorocarbazolyl.

[0341] Furthermore, at least one hydrogen atom in the above-mentioned aryl and heteroaryl compounds may be substituted, for example, with the above-mentioned aryl or heteroaryl compounds.

[0342] Specific examples of these triazine derivatives include the following compounds. [ka]

[0343] This triazine derivative can be produced using known raw materials and known synthesis methods.

[0344] <Benzimidazole derivatives> Benzimidazole derivatives are compounds represented by, for example, the following formula (ETM-11). [ka]

[0345] 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 "benzimidazole substituent" is a substituent in which the pyridyl group in the "pyridine substituent" in formulas (ETM-2), (ETM-2-1), and (ETM-2-2) above is replaced with a benzimidazole group, and at least one hydrogen in the benzimidazole derivative may be substituted with deuterium. * in the following structural formulas indicates a bond position. [ka]

[0346] R in the above benzimidazole group 11 R is hydrogen, an alkyl group having 1 to 24 carbon atoms, a cycloalkyl group having 3 to 12 carbon atoms, or an aryl group having 6 to 30 carbon atoms, and R in the above formulas (ETM-2-1) and (ETM-2-2) is... 11 You can quote the explanation.

[0347] φ is further preferably an anthracene ring or a fluorene ring, and the structure in this case can be described by referring to the explanation in formula (ETM-2-1) or formula (ETM-2-2) above, where R in each formula 11 ~R 18 The explanation for formula (ETM-2-1) or formula (ETM-2-2) above can be cited. Also, although formula (ETM-2-1) or formula (ETM-2-2) above is explained in a form in which two pyridine substituents are bonded, when replacing these with benzimidazole substituents, both pyridine substituents may be replaced with benzimidazole substituents (i.e., n=2), or one of the pyridine substituents may be replaced with a benzimidazole substituent and the other pyridine substituent may be R 11 ~R 18It may also be replaced with (i.e., n=1). Furthermore, for example, in the above equation (ETM-2-1) R 11 ~R 18 Replace at least one of the "pyridine substituents" with a benzimidazole substituent and R 11 ~R 18 You can replace it with this.

[0348] Specific examples of these benzimidazole derivatives include, for example, 1-phenyl-2-(4-(10-phenylanthracene-9-yl)phenyl)-1H-benzo[d]imidazole, 2-(4-(10-(naphthalene-2-yl)anthracene-9-yl)phenyl)-1-phenyl-1H-benzo[d]imidazole, 2-(3-(10-(naphthalene-2-yl)anthracene-9-yl)phenyl)-1-phenyl-1H-benzo[d]imidazole, and 5-(10-(naphthalene-2-yl)anthracene-9-yl)-1,2-diphenyl-1H-benzo[d]imidazole Examples include 1-(4-(10-(naphthalene-2-yl)anthracene-9-yl)phenyl)-2-phenyl-1H-benzo[d]imidazole, 2-(4-(9,10-di(naphthalene-2-yl)anthracene-2-yl)phenyl)-1-phenyl-1H-benzo[d]imidazole, 1-(4-(9,10-di(naphthalene-2-yl)anthracene-2-yl)phenyl)-2-phenyl-1H-benzo[d]imidazole, and 5-(9,10-di(naphthalene-2-yl)anthracene-2-yl)-1,2-diphenyl-1H-benzo[d]imidazole. [ka]

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

[0350] <Phenanthroline derivatives> Phenanthroline derivatives are compounds represented, for example, by the following formulas (ETM-12) or (ETM-12-1). Further details are described in International Publication No. 2006 / 021982. [ka]

[0351] 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.

[0352] R in each formula 11 ~R 18 Each of these is 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). Also, in the above formula (ETM-12-1), R 11 ~R 18 One of these bonds with φ, which is an aryl ring.

[0353] At least one hydrogen atom in each phenanthroline derivative may be substituted with deuterium.

[0354] R 11 ~R 18 The alkyl, cycloalkyl, and aryl in the above formula (ETM-2) are R 11 ~R 18 The explanation can be quoted. In addition to the examples above, φ can also be represented by the following structural formulas. In the following structural formulas, R is independently hydrogen, methyl, ethyl, isopropyl, cyclohexyl, phenyl, 1-naphthyl, 2-naphthyl, biphenylyl, or terphenylyl. Also, * in each structural formula represents the bond position. [ka]

[0355] Specific examples of phenanthroline derivatives include, for example, 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), basocproine, 1,3-bis(2-phenyl-1,10-phenanthroline-9-yl)benzene, and compounds represented by the following structural formula. [ka]

[0356] This phenanthroline derivative can be produced using known raw materials and known synthesis methods.

[0357] <Quinolinol-based metal complexes> Quinolinol-based metal complexes are compounds represented by, for example, the following general formula (ETM-13). [ka] In the formula, R 1 ~R 6 Each of these elements is independently hydrogen, fluorine, alkyl, cycloalkyl, aralkyl, alkenyl, cyano, alkoxy, or aryl, M is Li, Al, Ga, Be, or Zn, and n is an integer from 1 to 3.

[0358] Specific examples of quinolinol-based metal complexes include 8-quinolinollithium, tris(8-quinolinolate)aluminum, tris(4-methyl-8-quinolinolate)aluminum, tris(5-methyl-8-quinolinolate)aluminum, tris(3,4-dimethyl-8-quinolinolate)aluminum, tris(4,5-dimethyl-8-quinolinolate)aluminum, tris(4,6-dimethyl-8-quinolinolate)aluminum, bis(2-methyl-8-quinolinolate)(phenolate)aluminum, and bis(2-methyl-8-quinolinolate) (2-methylphenolate)aluminum, bis(2-methyl-8-quinolinolate)(3-methylphenolate)aluminum, bis(2-methyl-8-quinolinolate)(4-methylphenolate)aluminum, bis(2-methyl-8-quinolinolate)(2-phenylphenolate)aluminum, bis(2-methyl-8-quinolinolate)(3-phenylphenolate)aluminum, bis(2-methyl-8-quinolinolate)(4-phenylphenolate)aluminum, bis(2-methyl-8-quinolinolate)(2,3 -Dimethylphenolate)aluminum, bis(2-methyl-8-quinolinolate)(2,6-dimethylphenolate)aluminum, bis(2-methyl-8-quinolinolate)(3,4-dimethylphenolate)aluminum, bis(2-methyl-8-quinolinolate)(3,5-dimethylphenolate)aluminum, bis(2-methyl-8-quinolinolate)(3,5-di-t-butylphenolate)aluminum, bis(2-methyl-8-quinolinolate)(2,6-diphenylphenolate)aluminum, bis(2-methyl-8-quinolinolate)(2,6-diphenylphenolate)aluminum, bis(2-methyl-8-quinolinolate) (2,4,6-triphenylphenolate)aluminum, bis(2-methyl-8-quinolinolate)(2,4,6-trimethylphenolate)aluminum, bis(2-methyl-8-quinolinolate)(2,4,5,6-tetramethylphenolate)aluminum, bis(2-methyl-8-quinolinolate)(1-naphtholate)aluminum, bis(2-methyl-8-quinolinolate)(2-naphtholate)aluminum, bis(2,4-dimethyl-8-quinolinolate)(2-phenylphenolate)aluminum, bis(2,4-dimethyl-8-quinolinolate)(3-phenylphenolate)aluminum, bis(2,4-dimethyl-8-quinolinolate)(4-phenylphenolate)aluminum, bis(2,4-dimethyl-8-quinolinolate)(3,5-dimethylphenolate)aluminum, bis(2,4-dimethyl-8-quinolinolate)(3,5-di-t-butylphenolate)aluminum, bis(2-methyl-8-quinolinolate)aluminum-μ-oxo-bis(2-methyl-8-quinolinolate)aluminum, bis(2,4-dimethyl-8-quinolinolate)aluminum-μ-oxo-bis(2,4-dimethyl-8-quinolinolate)aluminum, bis(2-methyl-4-ethyl-8- Examples include 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, and bis(10-hydroxybenzo[h]quinoline)beryllium.

[0359] This quinolinol-based metal complex can be produced using known raw materials and known synthesis methods.

[0360] <Thiazole derivatives and benzothiazole derivatives> Thiazole derivatives are compounds represented by the following formula (ETM-14-1), for example. [ka] Benzothiazole derivatives are compounds represented by, for example, the following formula (ETM-14-2). [ka]

[0361] 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. The "thiazole substituent" and "benzothiazole substituent" are substituents in which the pyridyl group in the "pyridine substituent" in formulas (ETM-2), (ETM-2-1), and (ETM-2-2) above is replaced with the thiazole group or benzothiazole group described below, and at least one hydrogen in the thiazole derivative and benzothiazole derivative may be substituted with deuterium. The * in the following structural formulas represents the bond position. [ka]

[0362] φ is further preferably an anthracene ring or a fluorene ring, and the structure in this case can be described by referring to the explanation in formula (ETM-2-1) or formula (ETM-2-2) above, where R in each formula 11 ~R 18 The explanation for formula (ETM-2-1) or formula (ETM-2-2) above can be cited. Also, although formula (ETM-2-1) or formula (ETM-2-2) above is explained as a form in which two pyridine substituents are bonded, when replacing these with thiazole substituents (or benzothiazole substituents), both pyridine substituents may be replaced with thiazole substituents (or benzothiazole substituents) (i.e., n=2), or one of the pyridine substituents may be replaced with a thiazole substituent (or benzothiazole substituent) and the other pyridine substituent may be R 11 ~R 18 It may also be replaced with (i.e., n=1). Furthermore, for example, in the above equation (ETM-2-1) R 11 ~R 18 Replace at least one of the "pyridine substituents" with a thiazole substituent (or benzothiazole substituent) 11 ~R 18 You can replace it with this.

[0363] These thiazole derivatives or benzothiazole derivatives can be produced using known raw materials and known synthesis methods.

[0364] <Silole derivatives> Silole derivatives are compounds represented by the following formula (ETM-15), for example. Further details are described in Japanese Patent Publication No. 9-194487. [ka]

[0365] X and Y are independently alkyl, cycloalkyl, alkenyl, alkynyl, alkoxy, alkenyloxy, alkynyloxy, aryl, and heteroaryl groups, which may be substituted. For details of these groups, refer to the explanation in general formula (1) above, and further to the explanation in formula (ETM-7-2) above. In addition, alkenyloxy and alkynyloxy are groups in which the alkyl portion of an alkoxy is replaced with an alkenyl or alkynyl, respectively, and for details of these alkenyl and alkynyl groups, refer to the explanation in formula (ETM-7-2) above. Furthermore, X and Y may be bonded to form a cycloalkyl ring (or a ring in which a portion is unsaturated), and details of this cycloalkyl ring can be found in the description of cycloalkyl in general formula (1) above.

[0366] R 1 ~R 4Each of these is 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.

[0367] R 1 ~R 4 For details regarding halogens, alkyls, cycloalkyls, alkoxys, aryloxys, aminos, aryls, heteroaryls, alkenyls, and alkynyls in the above formula (1), refer to the explanation in the above general formula (1).

[0368] R 1 ~R 4 The details of the alkyl, aryl, and alkoxy elements in alkylcarbonyl, arylcarbonyl, alkoxycarbonyl, aryloxy, arylcarbonyloxy, alkoxycarbonyloxy, and aryloxycarbonyloxy can also be referenced from the explanation in general formula (1) above.

[0369] Examples of silyls include a silyl group and a group in which at least one of the three hydrogen atoms of the silyl group is independently substituted with an aryl, alkyl, or cycloalkyl group. Trisubstituted silyls are preferred, and examples include triarylsilyls, trialkylsilyls, tricycloalkylsilyls, dialkylcycloalkylsilyls, and alkyldicycloalkylsilyls. Details of the aryl, alkyl, and cycloalkyl groups in these can be found in the explanation for general formula (1) above.

[0370] The fused ring formed between adjacent substituents is, for example, R 1 and R 2 , R 2 and R 3 , R 3 and R 4 These are conjugated or unconjugated fused rings formed between such rings. These fused rings may contain nitrogen, oxygen, and sulfur atoms in their intraring structure, or they may be further fused with other rings.

[0371] However, preferably, R 1 and R 4 If is a phenyl group, then X and Y are not alkyl or phenyl. Also, preferably R 1 and R 4 If is a thienyl group, then X and Y are alkyl groups, R 2 and R 3 is alkyl, aryl, alkenyl or R 2 and R 3 It is a structure that does not simultaneously satisfy the requirement of a cycloalkyl group that is bonded to form a ring. Furthermore, preferably, R 1 and R 4 If R is a silyl group, 2 , R 3 X and Y are, independently, not hydrogen or an alkyl group having 1 to 6 carbon atoms. Also, preferably, R 1 and R 2 In the case of a structure in which a benzene ring is fused, X and Y are not alkyl and phenyl.

[0372] These silole derivatives can be produced using known raw materials and known synthesis methods.

[0373] <Azoline derivatives> Azoline derivatives are compounds represented by formula (ETM-16) below, for example. Further details are described in International Publication No. 2017 / 014226. [ka]

[0374] In formula (ETM-16), φ is an m-valent group derived from an aromatic hydrocarbon having 6 to 40 carbon atoms or an m-valent group derived from an aromatic heterocycle having 2 to 40 carbon atoms, and at least one hydrogen atom of φ may be substituted with an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 14 carbon atoms, an aryl group having 6 to 18 carbon atoms, or a heteroaryl group having 2 to 18 carbon atoms. Y is independently -O-, -S-, or >N-Ar, where Ar is a C6-C12 aryl or C2-C12 heteroaryl, and at least one hydrogen of Ar may be substituted with a C1-C4 alkyl, a C5-C10 cycloalkyl, a C6-C12 aryl, or a C2-C12 heteroaryl, R 1 ~R 5 Each of these is independently hydrogen, an alkyl group having 1 to 4 carbon atoms, or a cycloalkyl group having 5 to 10 carbon atoms, provided that Ar and R in >N-Ar are different. 1 ~R 5 One of these is a site that binds to L, L is independently selected from the group consisting of a divalent group represented by the following formula (L-1) and a divalent group represented by the following formula (L-2). [ka] In formula (L-1), X 1 ~X 6 Each of them is independent of =CR 6 - or = N- and X 1 ~X 6 At least two of them are =CR 6 - and X 1 ~X 6 Two of the =CR 6 -R in 6 The φ or azoline ring is the site that binds to the ring, while the others are =CR. 6 -R in 6 It is hydrogen, In formula (L-2), X 7 ~X 14 Each of them is independent of =CR 6- or = N- and X 7 ~X 14 At least two of them are =CR 6 - and X 7 ~X 14 Two of the =CR 6 -R in 6 The φ or azoline ring is the site that binds to the ring, while the others are =CR. 6 -R in 6 It is hydrogen, At least one hydrogen atom 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. m is an integer from 1 to 4, and when m is from 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.

[0375] Specific azoline derivatives are compounds represented by the following general formulas (ETM-16-1) or (ETM-16-2). [ka] In equations (ETM-16-1) and (ETM-16-2), φ is an m-valent group derived from an aromatic hydrocarbon having 6 to 40 carbon atoms or an m-valent group derived from an aromatic heterocycle having 2 to 40 carbon atoms, and at least one hydrogen atom of φ may be substituted with an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 14 carbon atoms, an aryl group having 6 to 18 carbon atoms, or a heteroaryl group having 2 to 18 carbon atoms. In formula (ETM-16-1), Y is independently -O-, -S-, or >N-Ar, where Ar is a C6-C12 aryl or C2-C12 heteroaryl, and at least one hydrogen atom of Ar may be substituted with a C1-C4 alkyl, a C5-C10 cycloalkyl, a C6-C12 aryl, or a C2-C12 heteroaryl. In formula (ETM-16-1), R 1 ~R4 Each of these is independently hydrogen, an alkyl group having 1 to 4 carbon atoms, or a cycloalkyl group having 5 to 10 carbon atoms, where R 1 and R 2 They are identical, and R 3 and R 4 They are identical, In formula (ETM-16-2), R 1 ~R 5 Each of these is independently hydrogen, an alkyl group having 1 to 4 carbon atoms, or a cycloalkyl group having 5 to 10 carbon atoms, where R 1 and R 2 They are identical, and R 3 and R 4 They are identical, In equations (ETM-16-1) and (ETM-16-2), L is independently selected from the group consisting of a divalent group represented by the following formula (L-1) and a divalent group represented by the following formula (L-2). [ka] In formula (L-1), X 1 ~X 6 Each of them is independent of =CR 6 - or = N- and X 1 ~X 6 At least two of them are =CR 6 - and X 1 ~X 6 Two of the =CR 6 -R in 6 The φ or azoline ring is the site that binds to the ring, while the others are =CR. 6 -R in 6 It is hydrogen, In formula (L-2), X 7 ~X 14 Each of them is independent of =CR 6 - or = N- and X 7 ~X 14 At least two of them are =CR 6 - and X 7 ~X 14 Two of the =CR 6 -R in 6The φ or azoline ring is the site that binds to the ring, while the others are =CR. 6 -R in 6 It is hydrogen, At least one hydrogen atom 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. m is an integer from 1 to 4, and when m is from 2 to 4, the groups formed by the azoline ring and L may be the same or different, and At least one hydrogen atom in the compound represented by formula (ETM-16-1) or formula (ETM-16-2) may be substituted with deuterium.

[0376] Preferably, φ is selected from the group consisting of a monovalent group represented by formulas (φ1-1) to (φ1-18), a divalent group represented by formulas (φ2-1) to (φ2-34), a trivalent group represented by formulas (φ3-1) to (φ3-3), and a tetravalent group represented by formulas (φ4-1) to (φ4-2), and at least one hydrogen of φ may be substituted with an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 14 carbon atoms, an aryl group having 6 to 18 carbon atoms, or a heteroaryl group having 2 to 18 carbon atoms. * in the following structural formulas indicates a bond position. [ka] [ka] [ka] In the above formulas, Z is >CR2, >N-Ar, >NL, -O-, or -S-, where R in >CR2 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, where 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 where L in >NL is L in the above general formula (ETM-16), formula (ETM-16-1), or general formula (ETM-16-2).

[0377] 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, sinnoline, and pteridine, and at least one hydrogen of L may be substituted with a C1-C4 alkyl, a C5-C10 cycloalkyl, a C6-C10 aryl, or a C2-C10 heteroaryl.

[0378] Preferably, in >N-Ar as Y or Z, Ar is selected from the group consisting of phenyl, naphthyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridadinyl, triazinyl, quinolinyl, isoquinolinyl, naphthyridinyl, phthalazinyl, quinoxalinyl, quinazolinyl, synnolinyl, and pteridinyl, and at least one hydrogen of Ar in >N-Ar as Y may be substituted with a C1-C4 alkyl, a C5-C10 cycloalkyl, or a C6-C10 aryl.

[0379] Preferably, R 1 ~R 4 Each of these is independently hydrogen, an alkyl group having 1 to 4 carbon atoms, or a cycloalkyl group having 5 to 10 carbon atoms, where R 1 and R 2 They are identical, R 3 and R 4 They are identical, and R 1 ~R 4Not all of them become hydrogen at the same time, and m is either 1 or 2. When m is 2, the group formed by the azoline ring and L is the same.

[0380] Specific examples of azoline derivatives include the following compounds. Note that "Me" in the structural formula represents a methyl group. [ka] [ka]

[0381] More preferably, φ is selected from the group consisting of divalent groups represented by the following formulas (φ2-1), (φ2-31), (φ2-32), (φ2-33), and (φ2-34), and at least one hydrogen of φ may be substituted with an aryl group having 6 to 18 carbon atoms, and * in each structural formula represents a bond position. [ka] 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 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 14 carbon atoms. In >N-Ar as Y, Ar is selected from the group consisting of phenyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, and triazinyl, and at least one hydrogen of said Ar may be substituted with an alkyl group having 1 to 4 carbon atoms, a cycloalkyl group having 5 to 10 carbon atoms, or an aryl group having 6 to 10 carbon atoms. R 1 ~R 4 Each of these is independently hydrogen, an alkyl group having 1 to 4 carbon atoms, or a cycloalkyl group having 5 to 10 carbon atoms, where R 1 and R 2 They are identical, R 3 and R 4 They are identical, and R 1 ~R4 Not all of them will turn into hydrogen at the same time, and, m is 2, and the group formed by the azoline ring and L is the same.

[0382] Other specific examples of azoline derivatives include the following compounds. Note that "Me" in the structural formula represents a methyl group. [ka]

[0383] Details regarding the alkyl, cycloalkyl, aryl, or heteroaryl elements in each of the above formulas defining this azoline derivative can be referenced from the explanation in general formula (1) above.

[0384] This azoline derivative can be produced using known raw materials and known synthesis methods.

[0385] The electron transport layer or electron injection layer may further contain a substance capable of reducing the material forming the electron transport layer or electron injection layer. This reducing substance can be any substance having a certain reducing property; for example, at least one selected from the group consisting of alkali metals, alkaline earth metals, rare earth metals, alkali metal oxides, alkali metal halides, alkaline earth metal oxides, alkaline earth metal halides, rare earth metal oxides, rare earth metal halides, alkali metal organic complexes, alkaline earth metal organic complexes, and rare earth metal organic complexes can be suitably used.

[0386] 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 (2.0-2.5 eV), or Ba (2.52 eV), with substances having a work function of 2.9 eV or less being particularly preferred. Of these, alkali metals K, Rb, or Cs are more preferred reducing substances, Rb or Cs are even more preferred, and Cs is the most preferred. These alkali metals have particularly high reducing ability, and their addition in relatively small amounts to materials forming electron transport layers or electron injection layers can improve the luminescence brightness and extend the lifespan of organic EL devices. Furthermore, combinations of two or more alkali metals are also preferred as reducing substances with a work function of 2.9 eV or less, and combinations including Cs, such as Cs and Na, Cs and K, Cs and Rb, or Cs, Na, and K, are particularly preferred. By including Cs, the reducing ability can be efficiently exhibited, and by adding it to the material forming the electron transport layer or electron injection layer, improvements in luminescence brightness and extended lifespan can be achieved in organic EL devices.

[0387] The electron injection layer material and electron transport layer material described above can also be used as an electron layer material as a polymer compound obtained by polymerizing a reactive compound in which a reactive substituent is substituted as a monomer, or as a polymer crosslink thereof, or as a pendant-type polymer compound obtained by reacting a main-chain polymer with the reactive compound, or as a pendant-type polymer crosslink thereof. In this case, the explanation for the polycyclic aromatic compound represented by the general formula (1) above can be referenced for the reactive substituent. Details of the applications of such polymer compounds and polymer crosslinks will be described later.

[0388] <Cathode in an organic electroluminescent device> The cathode 108 plays the role of injecting electrons into the light-emitting layer 105 via the electron injection layer 107 and the electron transport layer 106.

[0389] The material forming the cathode 108 is not particularly limited as long as it can efficiently inject electrons into the organic layer, but the same material as that forming the anode 102 can be used. Among these, metals such as tin, indium, calcium, aluminum, silver, copper, nickel, chromium, gold, platinum, iron, zinc, lithium, sodium, potassium, cesium, and magnesium, or their alloys (such as magnesium-silver alloys, magnesium-indium alloys, and aluminum-lithium alloys such as lithium fluoride / aluminum), are preferred. To increase electron injection efficiency and improve device characteristics, alloys containing lithium, sodium, potassium, cesium, calcium, magnesium, or these low work function metals are effective. However, these low work function metals are generally unstable in the atmosphere. To improve this, for example, a method is known in which the organic layer is doped with trace amounts of lithium, cesium, or magnesium to use electrodes with high stability. Other dopants that can be used include inorganic salts such as lithium fluoride, cesium fluoride, lithium oxide, and cesium oxide. However, they are not limited to these.

[0390] Furthermore, preferred methods for electrode protection include laminating metals such as platinum, gold, silver, copper, iron, tin, aluminum, and indium, or alloys using these metals, as well as inorganic materials such as silica, titania, and silicon nitride, polyvinyl alcohol, vinyl chloride, and hydrocarbon polymer compounds. The method for fabricating these electrodes is not particularly limited as long as conductivity can be achieved, such as resistance heating, electron beam deposition, sputtering, ion plating, and coating.

[0391] <Binding agents that may be used in each layer> The materials used in the hole injection layer, hole transport layer, light emission layer, electron transport layer, and electron injection layer described above can form each layer individually, but they can also be dispersed in solvent-soluble resins such as polyvinyl chloride, polycarbonate, polystyrene, poly(N-vinylcarbazole), polymethyl methacrylate, polybutyl methacrylate, polyester, polysulfone, polyphenylene oxide, polybutadiene, hydrocarbon resins, ketone resins, phenoxy resins, polyamides, ethylcellulose, vinyl acetate resins, ABS resins, and polyurethane resins, or in curable resins such as phenolic resins, xylene resins, petroleum resins, urea resins, melamine resins, unsaturated polyester resins, alkyd resins, epoxy resins, and silicone resins as polymer binders.

[0392] <Method for fabricating organic electroluminescent devices> Each layer constituting an organic EL element can be formed by thinning the material to be composed of each layer using methods such as vapor deposition, resistance heating deposition, electron beam deposition, sputtering, molecular stacking, printing, spin coating or casting, or coating. There are no particular limitations on the thickness of each layer formed in this way, and it can be set appropriately according to the properties of the material, but it is usually in the range of 2 nm to 5000 nm. The thickness can usually be measured with a quartz crystal oscillating film thickness measuring device. When thinning using vapor deposition, the deposition conditions vary depending on the type of material, the desired crystal structure and association structure of the film, etc. Generally, the deposition conditions are a boat heating temperature of +50 to +400°C and a vacuum of 10°C. -6 ~10 -3 It is preferable to appropriately set the Pa, deposition rate to 0.01 to 50 nm / second, substrate temperature to -150 to +300°C, and film thickness to 2 nm to 5 μm.

[0393] When applying a DC voltage to the organic EL element obtained in this way, the voltage should be applied with the anode as + and the cathode as -. When a voltage of approximately 2 to 40V is applied, light emission can be observed from the transparent or semi-transparent electrode side (anode or cathode, or both). Furthermore, this organic EL element will also emit light when a pulsed current or alternating current is applied. The waveform of the applied AC current can be arbitrary.

[0394] Next, as an example of a method for fabricating an organic EL device, we will describe a method for fabricating an organic EL device consisting of an anode, a hole injection layer, a hole transport layer, an emissive layer made of a host material and a dopant material, an electron transport layer, an electron injection layer, and a cathode.

[0395] <Vapor deposition method> An anode is fabricated by forming a thin film of anode material on a suitable substrate using a vapor deposition method, and then thin films of a hole injection layer and a hole transport layer are formed on this anode. A host material and a dopant material are co-deposited on this to form a thin film that serves as the light-emitting layer, and then an electron transport layer and an electron injection layer are formed on this light-emitting layer. Finally, a thin film made of cathode material is formed using a vapor deposition method to form the cathode, thereby obtaining the desired organic EL element. In addition, in the fabrication of the organic EL element described above, it is also possible to reverse the fabrication order and fabricate the cathode, electron injection layer, electron transport layer, light-emitting layer, hole transport layer, hole injection layer, and anode in that order.

[0396] <Wet film formation method> The wet film deposition method is carried out by preparing a liquid organic layer-forming composition containing low-molecular-weight compounds capable of forming each organic layer of an organic EL device. If a suitable organic solvent for dissolving these low-molecular-weight compounds is not available, the organic layer-forming composition may be prepared from polymer compounds obtained by polymerizing the low-molecular-weight compounds with other monomers or main-chain polymers that have solubility properties, by substituting reactive substituents on the low-molecular-weight compounds.

[0397] Wet film formation generally involves a coating step of applying an organic layer-forming composition to a substrate and a drying step of removing the solvent from the applied organic layer-forming composition to form a coating film. If the polymer compound has a crosslinkable substituent (also called a crosslinkable polymer compound), this drying step further crosslinks it to form a polymer crosslinked body. Depending on the coating step, methods using a spin coater are called spin coating, methods using a slit coater are called slit coating, methods using a plate are called gravure, offset, reverse offset, and flexographic printing, methods using an inkjet printer are called inkjet printing, and methods spraying in a mist are called spraying. Drying methods include air drying, heating, and vacuum drying. The drying step may be performed only once, or multiple times using different methods and conditions. In addition, different methods may be used in combination, such as firing under reduced pressure.

[0398] Wet deposition is a method of forming thin films using a solution, such as certain printing methods (inkjet printing), spin coating or casting, and coating methods. Unlike vacuum deposition, wet deposition does not require expensive vacuum deposition equipment and can be performed under atmospheric pressure. In addition, wet deposition allows for large-area deposition and continuous production, leading to reduced manufacturing costs.

[0399] On the other hand, compared to vacuum deposition, wet deposition can be difficult for layering. When fabricating layered films using wet deposition, it is necessary to prevent the upper layer's composition from dissolving the lower layer, and techniques such as controlled solubility of the composition, crosslinking of the lower layer, and orthogonal solvents (solvents that do not mix with each other) are employed. However, even with these techniques, it can be difficult to use wet deposition for coating all films.

[0400] Therefore, a common approach is to fabricate organic EL elements using a wet deposition method for only a few layers, and a vacuum deposition method for the rest.

[0401] For example, the procedure for fabricating an organic EL element by partially applying a wet film deposition method is shown below. (Step 1) Film deposition by vacuum deposition of the anode (Step 2) Wet deposition of a hole injection layer-forming composition containing hole injection layer material. (Step 3) Wet deposition of a hole transport layer forming composition containing a hole transport layer material. (Step 4) Wet deposition of a light-emitting layer-forming composition containing a host material and a dopant material. (Step 5) Deposition of electron transport layer by vacuum deposition (Step 6) Deposition of electron injection layer by vacuum deposition (Step 7) Film deposition by vacuum deposition of cathode By following this procedure, an organic EL element is obtained consisting of an anode, a hole injection layer, a hole transport layer, an emissive layer made of a host material and a dopant material, an electron transport layer, an electron injection layer, and a cathode. Of course, by using means to prevent the dissolution of the lower light-emitting layer, or by using means to deposit the film from the cathode side in the opposite direction to the above procedure, it is possible to prepare a layer-forming composition containing electron transport layer material and electron injection layer material, and then deposit them by a wet film deposition method.

[0402] <Other film formation methods> Laser heating and deposition (LITI) can be used to form organic layer-forming compositions. LITI is a method of heating and depositing a compound attached to a substrate using a laser, and organic layer-forming compositions can be used as the material coated onto the substrate.

[0403] <Optional steps> Appropriate processing steps, cleaning steps, and drying steps may be appropriately inserted before and after each film formation step. Examples of processing 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 creating a bank may also be included.

[0404] Photolithography can be used to create the resist bank. Positive and negative resist materials can be used as the resist bank material for photolithography. Patternable printing methods such as inkjet, gravure offset printing, reverse offset printing, and screen printing can also be used. Permanent resist materials can also be used in these cases.

[0405] Materials used in the bank include, but are not limited to, polysaccharides and their derivatives, homopolymers and copolymers of ethylenic monomers having hydroxyls, biopolymers, polyacryloyl compounds, polyesters, polystyrene, 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, polyacetates, polynorbornene, synthetic rubber, fluorinated polymers such as polyfluorovinylidene, polytetrafluoroethylene, and polyhexafluoropropylene, fluoroolefin-hydrocarbonolefin copolymers, and fluorocarbon polymers.

[0406] <Compositions for forming organic layers used in wet film deposition methods> The organic layer-forming composition is obtained by dissolving a low-molecular-weight compound capable of forming each organic layer of an organic EL element, or a high-molecular-weight compound obtained by polymerizing the low-molecular-weight compound, in an organic solvent. For example, the light-emitting layer-forming composition contains, as a first component, at least one polycyclic aromatic compound (or its high-molecular-weight compound) which is a dopant material, as a second component, at least one host material, and as a third component, at least one organic solvent. The first component functions as a dopant component of the light-emitting layer obtained from the composition, and the second component functions as a host component of the light-emitting layer. The third component functions as a solvent that dissolves the first and second components in the composition, and during application, the controlled evaporation rate of the third component itself provides a smooth and uniform surface shape.

[0407] <organic solvents> The organic layer-forming composition contains at least one organic solvent. By controlling the evaporation rate of the organic solvent during film formation, the film-forming properties, the presence or absence of defects in the coating film, surface roughness, and smoothness can be controlled and improved. Furthermore, when forming films using an inkjet method, the meniscus stability at the pinholes of the inkjet head can be controlled, thereby controlling and improving ejection performance. In addition, by controlling the drying rate of the film and the orientation of derivative molecules, the electrical properties, luminescence properties, efficiency, and lifespan of an organic EL element having an organic layer obtained from the organic layer-forming composition can be improved.

[0408] (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 even more preferably 150°C to 250°C. A boiling point higher than 130°C is preferable from the viewpoint of inkjet ejection performance. A boiling point lower than 300°C is preferable from the viewpoint of coating film defects, surface roughness, residual solvent, and smoothness. From the viewpoint of good inkjet ejection performance, film formation, smoothness, and low residual solvent, a composition containing two or more organic solvents is more preferable. On the other hand, depending on the circumstances, the composition may be in a solid state by removing the solvent from the organic layer-forming composition, taking into consideration transportability, etc.

[0409] 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) GS ) is the boiling point (BP) of a poor solvent (PS) PS A configuration that is lower than ) is particularly preferable. By adding a high-boiling-point poor solvent, the low-boiling-point good solvent volatilizes first during film formation, increasing the concentration of the constituents in the composition and the concentration of the poor solvent, thus promoting rapid film formation. As a result, a coating film with fewer defects, low surface roughness, and high smoothness can be obtained.

[0410] Difference in solubility (S GS -S PS The difference in boiling points (BP) is preferably 1% or more, more preferably 3% or more, and even more preferably 5% or more. PS -BP GS The temperature is preferably 10°C or higher, more preferably 30°C or higher, and even more preferably 50°C or higher.

[0411] The organic solvent is removed from the coating film after film formation by drying processes such as vacuum, reduced pressure, or heating. When heating is performed, it is preferable to heat at a temperature of at least one solute's glass transition temperature (Tg) + 30°C or lower from the viewpoint of improving coating film formation. Furthermore, from the viewpoint of reducing residual solvent, it is preferable to heat at a temperature of at least one solute's 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. In addition, drying may be performed multiple times at different temperatures, or multiple drying methods may be used in combination.

[0412] (2) Specific examples of organic solvents Organic solvents used in compositions for forming organic layers 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, decane-2-ol, dodecane-2-ol, and 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-chlorobenzo trifluoride, 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, phenethole, 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 solvents include, but are not limited to, methylnaphthalene, butyl benzoate, 2-methylbiphenyl, 3-phenoxytoluene, 2,2'-vitrill, 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, benzylpentyl ether, benzylhexyl ether, benzylheptyl ether, and benzyloctyl ether. Furthermore, the solvent may be used individually or in mixtures.

[0413] <Optional ingredients> The organic layer-forming composition may contain optional components as long as they do not impair its properties. Examples of optional components include binders and surfactants.

[0414] (1) Binder The organic layer-forming composition may contain a binder. The binder forms a film during film formation and also bonds the resulting film to the substrate. It also plays a role in dissolving, dispersing, and binding other components within the organic layer-forming composition.

[0415] Examples of binders used in organic layer-forming compositions 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.

[0416] The binder used in the organic layer-forming composition may be a single type or a mixture of multiple types.

[0417] (2) Surfactants The organic layer-forming composition may contain surfactants, for example, to control the uniformity of the film surface, the hydrophilicity and liquid repellency of the film surface. Surfactants are classified into ionic and nonionic based on the structure of their hydrophilic groups, and further classified into alkyl, silicon, and fluorine based on the structure of their hydrophobic groups. They are also classified into monomolecular systems with relatively small molecular weights and simple structures, and polymeric systems with large molecular weights and side chains or branching, based on their molecular structure. Furthermore, they are classified into single systems and mixed systems containing two or more surfactants and a substrate, based on their composition. All types of surfactants can be used in the organic layer-forming composition.

[0418] Examples of surfactants include Polyflow No. 45, Polyflow KL-245, Polyflow No. 75, Polyflow No. 90, Polyflow No. 95 (product name, manufactured by Kyoeisha Chemical Industry Co., Ltd.), Disperbyk 161, Disperbyk 162, Disperbyk 163, Disperbyk 164, Disperbyk 166, Disperbyk 170, Disperbyk 180, Disperbyk 181, Disperbyk 182, BYK300, and BYK. 306, BYK310, BYK320, BYK330, BYK342, BYK344, BYK346 (product name, manufactured by Big Chemie Japan Co., Ltd.), KP-341, KP-358, KP-368, KF-96-50CS, KF-50-100CS (product name, manufactured by Shin-Etsu Chemical Co., Ltd.), Surflon SC-101, Surflon KH-40 (product name, manufactured by Seimi Chemical Co., Ltd.), Futergent 222F, Futergent 251, FTX-218 (product 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), fluoroalkylbenzene sulfonate, fluoroalkyl carboxylate, fluoroalkyl polyoxyethylene ether, fluoroalkylammonium iodide, fluoroalkyl betaine, fluoroalkyl sulfonate, diglycerin tetrakis(fluoroalkyl polyoxyethylene ether), fluoroalkyltrimethylammonium salt, fluoroalkylaminosulfonate, polyoxyethylene noni Examples include tetraphenyl ether, polyoxyethylene octylphenyl ether, polyoxyethylene alkyl ether, polyoxyethylene laurate, polyoxyethylene oleate, polyoxyethylene stearate, polyoxyethylene laurylamine, sorbitan laurate, sorbitan palmitate, sorbitan stearate, sorbitan oleate, sorbitan fatty acid ester, polyoxyethylene sorbitan laurate, polyoxyethylene sorbitan palmitate, polyoxyethylene sorbitan stearate, polyoxyethylene sorbitan oleate, polyoxyethylene naphthyl ether, alkylbenzene sulfonate, and alkyldiphenyl ether disulfonate.

[0419] Furthermore, a single surfactant may be used, or two or more may be used in combination.

[0420] <Composition and physical properties of organic layer-forming compositions> The content of each component in the organic layer-forming composition is determined considering the good solubility, storage stability, and film-forming properties of each component in the organic layer-forming composition, as well as the good film quality of the coating obtained from the organic layer-forming composition, good ejection properties when using an inkjet method, and good electrical properties, luminescence properties, efficiency, and lifespan of the organic EL element having an organic layer made using the composition. For example, in the case of a light-emitting layer-forming composition, it is preferable that the first component is present in an amount of 0.0001% to 2.0% by weight of the total weight of the light-emitting layer-forming composition, the second component in an amount of 0.0999% to 8.0% by weight of the total weight of the light-emitting layer-forming composition, and the third component in an amount of 90.0% to 99.9% by weight of the total weight of the light-emitting layer-forming composition.

[0421] More preferably, the first component is present in an amount of 0.005% to 1.0% by weight of the total weight of the light-emitting layer forming composition, the second component in an amount of 0.095% to 4.0% by weight of the total weight of the light-emitting layer forming composition, and the third component in an amount of 95.0% to 99.9% by weight of the total weight of the light-emitting layer forming composition. Even more preferably, the first component is present in an amount of 0.05% to 0.5% by weight of the total weight of the light-emitting layer forming composition, the second component in an amount of 0.25% to 2.5% by weight of the total weight of the light-emitting layer forming composition, and the third component in an amount of 97.0% to 99.7% by weight of the total weight of the light-emitting layer forming composition.

[0422] The organic layer-forming composition can be produced by appropriately selecting and performing stirring, mixing, heating, cooling, dissolving, dispersion, etc., on the above-mentioned components using known methods. Furthermore, after preparation, filtration, degassing (also called degassing), ion exchange treatment, and inert gas replacement / sealing treatment may be performed as appropriate.

[0423] Regarding the viscosity of the organic layer-forming composition, a higher viscosity results in better film formation and good ejection when using an inkjet method. On the other hand, a lower viscosity makes it easier to form thin films. For this reason, the viscosity of the organic layer-forming composition is preferably 0.3 to 3 mPa·s at 25°C, and more preferably 1 to 3 mPa·s. In this invention, viscosity is a value measured using a cone-plate type rotational viscometer.

[0424] A lower surface tension in the organic layer-forming composition results in better film formation and a defect-free coating. On the other hand, a higher surface tension results in better inkjet ejection performance. For this reason, the surface tension of the organic layer-forming composition is preferably 20 to 40 mN / m at 25°C, and more preferably 20 to 30 mN / m. In this invention, the surface tension is a value measured using the suspension drop method.

[0425] <Cross-linkable polymer compounds: Compounds represented by the general formula (XLP-1)> Next, we will explain the case where the above-mentioned polymer compound has a crosslinkable substituent. Such a crosslinkable polymer compound is, for example, a compound represented by the following general formula (XLP-1). [ka] In equation (XLP-1), MUx, ECx, and k are defined the same as MU, EC, and k in formula (H3) above, except that the compound represented by formula (XLP-1) has at least one crosslinkable substituent (XLS), and preferably the content of a monovalent or divalent aromatic compound having a crosslinkable substituent is 0.1 to 80% by weight of the molecule.

[0426] The content of monovalent or divalent aromatic compounds having crosslinkable substituents is preferably 0.5 to 50% by weight, and more preferably 1 to 20% by weight.

[0427] The crosslinkable substituent (XLS) is not particularly limited as long as it is a group that can further crosslink the polymer compound described above, but substituents with the following structures are preferred. The asterisk (*) in each structural formula indicates the bond position. [ka]

[0428] L is independently a single bond, -O-, -S-, >C=O, -OC(=O)-, a C1-C12 alkylene, a C1-C12 oxyalkylene, and a C1-C12 polyoxyalkylene. Among the above substituents, groups represented by formula (XLS-1), (XLS-2), (XLS-3), (XLS-9), (XLS-10), or (XLS-17) are preferred, and groups represented by formula (XLS-1), (XLS-3), or (XLS-17) are more preferred.

[0429] Examples of divalent aromatic compounds having crosslinkable substituents include compounds having the following substructure. * in the following structural formula indicates a bond position. [ka] [ka] [ka] [ka]

[0430] <Method for producing polymer compounds and crosslinked polymer compounds> Methods for producing polymer compounds and crosslinkable polymer compounds will be explained using the compounds represented by formula (H3) and formula (XLP-1) described above as examples. These compounds can be synthesized by appropriately combining known production methods.

[0431] Solvents used in the reaction include aromatic solvents, saturated / unsaturated hydrocarbon solvents, alcohol solvents, and ether-based solvents, such as dimethoxyethane, 2-(2-methoxyethoxy)ethane, and 2-(2-ethoxyethoxy)ethane.

[0432] The reaction may also be carried out in a two-phase system. If the reaction is carried out in a two-phase system, a phase transfer catalyst such as a quaternary ammonium salt may be added as needed.

[0433] When producing the compounds of formula (H3) and formula (XLP-1), they may be produced in a single step or in multiple steps. Furthermore, the synthesis may be carried out by a batch polymerization method, where all the raw materials are placed in the reaction vessel before the reaction begins; by a dropwise polymerization method, where the raw materials are added dropwise to the reaction vessel; or by a precipitation polymerization method, where the product precipitates as the reaction progresses. These methods can be combined as appropriate. For example, when synthesizing the compound represented by formula (H3) in a single step, the target product is obtained by carrying out the reaction with the monomer unit (MU) and end-cap unit (EC) already added to the reaction vessel. Also, when synthesizing the compound represented by general formula (H3) in multiple steps, the target product is obtained by polymerizing the monomer unit (MU) to the desired molecular weight, and then adding the end-cap unit (EC) and reacting. By adding different types of monomer unit (MU) in multiple steps, a polymer with a concentration gradient in the monomer unit structure can be produced. Furthermore, after preparing a precursor polymer, the target polymer can be obtained by a post-reaction.

[0434] Furthermore, the primary structure of the polymer can be controlled by selecting the polymerizable groups of the monomer unit (MU). For example, as shown in synthesis schemes 1 to 3, it is possible to synthesize polymers with random primary structures (synthesis scheme 1), polymers with regular primary structures (synthesis schemes 2 and 3), and these can be used in appropriate combinations depending on the desired product. Moreover, by using monomer units having three or more polymerizable groups, hyperbranched polymers and dendrimers can be synthesized. [ka]

[0435] Monomer units that can be used in the present invention can be synthesized according to the methods described in Japanese Patent Publication No. 2010-189630, International Publication No. 2012 / 086671, International Publication No. 2013 / 191088, International Publication No. 2002 / 045184, International Publication No. 2011 / 049241, International Publication No. 2013 / 146806, International Publication No. 2005 / 049546, International Publication No. 2015 / 145871, Japanese Patent Publication No. 2010-215886, Japanese Patent Publication No. 2008-106241, International Publication No. 2016 / 031639, and Japanese Patent Publication No. 2011-174062.

[0436] Furthermore, specific polymer synthesis procedures can be described in accordance with the methods described in Japanese Patent Publication No. 2012-036388, International Publication No. 2015 / 008851, Japanese Patent Publication No. 2012-36381, Japanese Patent Publication No. 2012-144722, International Publication No. 2015 / 194448, International Publication No. 2013 / 146806, International Publication No. 2015 / 145871, International Publication No. 2016 / 031639, International Publication No. 2016 / 125560, and International Publication No. 2011 / 049241.

[0437] <Application examples of organic electroluminescent devices> Furthermore, the present invention can also be applied to display devices equipped with organic EL elements or lighting devices equipped with organic EL elements. A display device or lighting device equipped with an organic EL element can be manufactured by known methods, such as connecting the organic EL element according to this embodiment with a known driving device, and can be driven using known driving methods such as DC driving, pulse driving, or AC driving as appropriate.

[0438] Examples of display devices include panel displays such as color flat panel displays and flexible displays such as flexible color organic electroluminescent (EL) displays (see, for example, Japanese Patent Publication No. 10-335066, Japanese Patent Publication No. 2003-321546, and Japanese Patent Publication No. 2004-281086). Examples of display methods include matrix and segment methods. Matrix and segment displays may coexist on the same panel.

[0439] In a matrix display, pixels for display are arranged two-dimensionally, such as in a grid or mosaic pattern, and characters or images are displayed using a collection of pixels. The shape and size of the pixels are determined by the application. For example, for displaying images and characters on personal computers, monitors, and televisions, square pixels with sides of 300 μm or less are usually used, while for large displays such as display panels, pixels with sides on the order of millimeters are used. For monochrome displays, pixels of the same color can be arranged, but for color displays, red, green, and blue pixels are arranged side by side. In this case, there are typically delta type and stripe type displays. The matrix can be driven by either a line-sequential drive method or an active matrix. Line-sequential drive has the advantage of a simpler structure, but considering the operating characteristics, the active matrix may be superior in some cases, so it is necessary to choose the appropriate method depending on the application.

[0440] In segment-based displays, a pattern is formed to display predetermined information, and a designated area is illuminated. Examples include time and temperature displays in digital clocks and thermometers, operating status displays in audio equipment and induction cooktops, and panel displays in automobiles.

[0441] Examples of lighting devices include lighting devices such as indoor lighting and backlights for liquid crystal displays (see, for example, Japanese Patent Publication No. 2003-257621, Japanese Patent Publication No. 2003-277741, and Japanese Patent Publication No. 2004-119211). Backlights are mainly used to improve the visibility of non-self-illuminating display devices and are used in liquid crystal displays, clocks, audio equipment, automobile panels, display boards, and signs. In particular, for liquid crystal displays, especially backlights for personal computers where miniaturization is a challenge, conventional methods consist of fluorescent lamps and light guide plates, making miniaturization difficult. Therefore, the backlight using the light-emitting element according to this embodiment is characterized by being thin and lightweight.

[0442] ​ The polycyclic aromatic compounds according to the present invention can be used not only for the organic field-light-emitting device described above, but also for the fabrication of organic field-effect transistors, organic thin-film solar cells, or wavelength conversion filters.

[0443] An organic field-effect transistor (OCT) is a type of transistor that controls current using an electric field generated by a voltage input. In addition to source and drain electrodes, it has a gate electrode. When a voltage is applied to the gate electrode, an electric field is generated, allowing the current to be controlled by arbitrarily blocking the flow of electrons (or holes) between the source and drain electrodes. Compared to simple transistors (bipolar transistors), OTCs are easier to miniaturize and are frequently used as components in integrated circuits.

[0444] The structure of an organic field-effect transistor typically includes a source electrode and a drain electrode in contact with an organic semiconductor active layer formed using the polycyclic aromatic compound according to the present invention, and a gate electrode further separated by an insulating layer (dielectric layer) in contact with the organic semiconductor active layer. Examples of such device structures include the following: (1) Substrate / Gate electrode / Insulator layer / Source electrode / Drain electrode / Organic semiconductor active layer (2) Substrate / Gate electrode / Insulator layer / Organic semiconductor active layer / Source electrode / Drain electrode (3) Substrate / Organic semiconductor active layer / Source electrode / Drain electrode / Insulator layer / Gate electrode (4) Substrate / Source electrode / Drain electrode / Organic semiconductor active layer / Insulator layer / Gate electrode Organic field-effect transistors configured in this way can be applied as pixel driving switching elements in active-matrix driven liquid crystal displays and organic electroluminescent displays.

[0445] Organic thin-film solar cells have 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 stacked on a transparent substrate such as glass. The photoelectric conversion layer has a p-type semiconductor layer on the anode side and an n-type semiconductor layer on the cathode side. The polycyclic aromatic compound according to the present invention can be used as a material for the hole transport layer, p-type semiconductor layer, n-type semiconductor layer, and 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 organic thin-film solar cells. In addition to the above, organic thin-film solar cells may appropriately include a hole blocking layer, an electron blocking layer, an electron injection layer, a hole injection layer, a smoothing layer, etc. Organic thin-film solar cells can be appropriately selected and combined with known materials used in organic thin-film solar cells.

[0446] To widen the color gamut of displays, quantum dots with a narrow emission width at half maximum are used as phosphors in wavelength conversion filters. However, there are problems such as instability to oxidation, high aggregation due to being nano-sized particles, and the fact that the metals used are regulated as pollutants. The polycyclic aromatic compound according to the present invention can be used as a phosphor in a wavelength conversion filter. As a matrix for dispersing this polycyclic aromatic compound, a polymer material having high transparency, low water vapor permeability, low oxygen permeability, and high thermal stability is preferred. Examples include (meth)acrylic polymers such as polymethyl (meth)acrylate and cycloolefin polymers such as zeonex. [Examples]

[0447] The present invention will be described in more detail below with reference to examples, but the present invention is not limited to these examples. First, examples of the synthesis of polycyclic aromatic compounds will be described below.

[0448] Synthesis Example (1): Synthesis of Compounds (1-16) [ka]

[0449] Under a nitrogen atmosphere, intermediate (X-1) (75.0 g), intermediate (X-2) (178.7 g), cesium carbonate (429.8 g), and N-methyl-2-pyrrolidone (NMP, 750 ml) were placed in a flask and heated at 110°C for 8 hours. After the reaction was complete, water and toluene were added to the reaction mixture and stirred, and the organic layer was separated and washed with water. Subsequently, the organic layer was concentrated, and the resulting crude product was purified using a silica gel short column (eluent: toluene / heptane = 1 / 4 (volume ratio)) to obtain intermediate (X-3) (201.6 g). [ka]

[0450] Under a nitrogen atmosphere, intermediate (X-3) (190.6 g) and xylene (2 L) were placed in a flask and cooled to -5°C. Then, n-butyllithium hexane solution (197.6 ml) was added dropwise. After stirring for 30 minutes, the mixture was cooled again to -57°C, boron tribromide (84.3 g) was added, and the temperature was raised to 0°C and stirred for 0.5 hours. Then, N,N-diisopropylethylamine (DIEPA, 72.4 g) was added, and the mixture was stirred at room temperature until the exothermic reaction subsided. After that, the temperature was raised to 120°C and heated and stirred for 5 hours. The reaction mixture was cooled to room temperature, aqueous potassium acetate solution and heptane were added, and the precipitated crude product was purified using a silica gel short column (eluent: toluene) and washed with heptane to obtain intermediate (X-4) (59 g). [ka]

[0451] Under a nitrogen atmosphere, intermediate (X-4) (15.0 g), intermediate (X-5) (6.6 g), potassium phosphate (10.5 g), palladium acetate (0.28 g), 2-dicyclohexylphosphino-2'6'-dimethoxybiphenyl (SPhos, 1.0 g), toluene (200 ml), cyclopentyl methyl ether (CPME, 200 ml), ethanol (30 ml), and water (30 ml) were added, and the mixture was stirred under reflux for 1 hour. After the reaction was complete, water and toluene were added to the reaction mixture and stirred, and the organic layer was separated and washed with water. The organic layer was then concentrated, and the resulting crude product was purified using a silica gel short column (eluent: toluene / ethyl acetate = 1 / 1 (volume ratio)). The obtained crude product was recrystallized with toluene to obtain compound (1-16) (12.7 g). [ka]

[0452] The structure of the compound obtained was confirmed by mass spectrometry. EI-MS, M / Z = 751.

[0453] Synthesis Example (2): Synthesis of Compounds (1-17) Compounds (1-17) were synthesized using the same procedure as in the synthesis example (1) described above. [ka]

[0454] The structure of the compound obtained was confirmed by mass spectrometry. EI-MS, M / Z = 751.

[0455] Synthesis Example (3): Synthesis of Compounds (1-40) Compounds (1-40) were synthesized using the same procedure as in the synthesis example (1) described above. [ka]

[0456] The structure of the compound obtained was confirmed by mass spectrometry. EI-MS, M / Z = 751.

[0457] Synthesis Example (4): Synthesis of Compounds (1-3) Compounds (1-3) were synthesized using the same procedure as in the synthesis example (1) described above. [ka]

[0458] The structure of the compound obtained by NMR measurement was confirmed. 1 H-NMR (CDCl3): δ=8.29(d,2H), 7.51-7.45(m,12H), 7.37(d,2H), 7.22-7.17(m,15H), 6.95(s,2H), 6.94(dd,2H).

[0459] Synthesis Example (5): Synthesis of Compounds (1-2) Compound (1-2) was synthesized using the same procedure as in the synthesis example (1) described above. [ka]

[0460] The structure of the compound obtained was confirmed by mass spectrometry. EI-MS, M / Z = 726.

[0461] Synthesis Example (6): Synthesis of Compounds (1-7) Compounds (1-7) were synthesized using the same procedure as in the synthesis example (1) described above. [ka]

[0462] The structure of the compound obtained was confirmed by mass spectrometry. EI-MS, M / Z = 726.

[0463] Synthesis Example (7): Synthesis of Compounds (1-6) Compounds (1-6) were synthesized using the same procedure as in the synthesis example (1) described above. [ka]

[0464] The structure of the compound obtained by NMR measurement was confirmed. 1 H-NMR(CDCl3): δ=8.76(d,2H), 7.99-7.97(m,3H), 7.84(d,2H), 7.75-7.65(m ,14H), 7.60-7.57(m,3H), 7.54(s,2H), 7.51-7.47(m,6H), 7.41-7.38(m,3H).

[0465] Synthesis Example (8): Synthesis of Compounds (1-80) Compound (1-80) was synthesized using the same procedure as in the synthesis example (1) described above. [ka]

[0466] The structure of the compound obtained by NMR measurement was confirmed. 1 H-NMR (CDCl3): δ=8.62(d,2H), 8.29(d,2H), 7.94(s,1H), 7.80-7.79(m,1H), 7.60-7.38(m,16H), 7.25-7.14(m,10H), 7.00(d,2H).

[0467] Synthesis Example (9): Synthesis of Compounds (1-77) Compound (1-77) was synthesized using the same procedure as in the synthesis example (1) described above. [ka]

[0468] The structure of the compound obtained was confirmed by mass spectrometry. EI-MS, M / Z = 727.

[0469] Synthesis Example (10): Synthesis of Compounds (1-53) Compound (1-53) was synthesized using the same procedure as in the synthesis example (1) described above. [ka]

[0470] The structure of the compound obtained was confirmed by mass spectrometry. EI-MS, M / Z = 728.

[0471] Synthesis Example (11): Synthesis of Compounds (1-88) Compound (1-88) was synthesized using the same procedure as in the synthesis example (1) described above. [ka]

[0472] The structure of the compound obtained was confirmed by mass spectrometry. EI-MS, M / Z = 778.

[0473] Synthesis Example (12): Synthesis of Compounds (1-95) Compound (1-95) was synthesized using the same procedure as in the synthesis example (1) described above. [ka]

[0474] The structure of the compound obtained was confirmed by mass spectrometry. EI-MS, M / Z = 815.

[0475] Synthesis Example (13): Synthesis of Compounds (1-96) Compound (1-96) was synthesized using the same procedure as in the synthesis example (1) described above. [ka]

[0476] The structure of the compound obtained was confirmed by mass spectrometry. EI-MS, M / Z = 816.

[0477] Synthesis Example (14): Synthesis of Compounds (1-98) Compound (1-98) was synthesized using the same procedure as in the synthesis example (1) described above. [ka]

[0478] The structure of the compound obtained was confirmed by mass spectrometry. EI-MS, M / Z = 777.

[0479] Synthesis Example (15): Synthesis of Compounds (1-110) Compound (1-110) was synthesized using the same procedure as in the synthesis example (1) described above. [ka]

[0480] The structure of the compound obtained was confirmed by mass spectrometry. EI-MS, M / Z = 826.

[0481] Synthesis Example (16): Synthesis of Compounds (1-121) Compound (1-121) was synthesized using the same procedure as in the synthesis example (1) described above. [ka]

[0482] The structure of the compound obtained was confirmed by mass spectrometry. EI-MS, M / Z = 761.

[0483] Synthesis Example (17): Synthesis of Compounds (1-123) Compound (1-123) was synthesized using the same procedure as in the synthesis example (1) described above. [ka]

[0484] The structure of the compound obtained was confirmed by mass spectrometry. EI-MS, M / Z = 1056.

[0485] Synthesis Example (18): Synthesis of Compounds (1-125) Compound (1-125) was synthesized using the same procedure as in the synthesis example (1) described above. [ka]

[0486] The structure of the compound obtained was confirmed by mass spectrometry. EI-MS, M / Z = 726.

[0487] Synthesis Example (19): Synthesis of Compounds (1-132) Compound (1-132) was synthesized using the same procedure as in the synthesis example (1) described above. [ka]

[0488] The structure of the compound obtained was confirmed by mass spectrometry. EI-MS, M / Z = 751.

[0489] Synthesis Example (20): Synthesis of Compounds (1-135) Compound (1-135) was synthesized using the same procedure as in the synthesis example (1) described above. [ka]

[0490] The structure of the compound obtained was confirmed by mass spectrometry. EI-MS, M / Z = 726.

[0491] Synthesis Example (21): Synthesis of Compounds (1-154) Compound (1-154) was synthesized using the same procedure as in the synthesis example (1) described above. [ka]

[0492] The structure of the compound obtained was confirmed by mass spectrometry. EI-MS, M / Z = 728.

[0493] Synthesis Example (22): Synthesis of Compounds (1-178) Compound (1-178) was synthesized using the same procedure as in the synthesis example (1) described above. [ka]

[0494] The structure of the compound obtained was confirmed by mass spectrometry. EI-MS, M / Z = 727.

[0495] Synthesis Example (23): Synthesis of Compounds (1-184) Compound (1-184) was synthesized using the same procedure as in the synthesis example (1) described above. [ka]

[0496] The structure of the compound obtained was confirmed by mass spectrometry. EI-MS, M / Z = 727.

[0497] Synthesis Example (24): Synthesis of Compounds (1-204) Compound (1-204) was synthesized using the same procedure as in the synthesis example (1) described above. [ka]

[0498] The structure of the compound obtained was confirmed by mass spectrometry. EI-MS, M / Z = 728.

[0499] Synthesis Example (25): Synthesis of Compounds (1-224) Compound (1-224) was synthesized using the same procedure as in the synthesis example (1) described above. [ka]

[0500] The structure of the compound obtained was confirmed by mass spectrometry. EI-MS, M / Z = 728.

[0501] Synthesis Example (26): Synthesis of Compounds (1-233) Compound (1-233) was synthesized using the same procedure as in the synthesis example (1) described above. [ka]

[0502] The structure of the compound obtained was confirmed by mass spectrometry. EI-MS, M / Z = 729.

[0503] Synthesis Example (27): Synthesis of Compounds (1-271) Compound (1-271) was synthesized using the same procedure as in the synthesis example (1) described above. [ka]

[0504] The structure of the compound obtained was confirmed by mass spectrometry. EI-MS, M / Z = 729.

[0505] Synthesis Example (28): Synthesis of Compounds (1-276) Compound (1-276) was synthesized using the same procedure as in the synthesis example (1) described above. [ka]

[0506] The structure of the compound obtained was confirmed by mass spectrometry. EI-MS, M / Z = 729.

[0507] Synthesis Example (29): Synthesis of Compounds (1-287) Compound (1-287) was synthesized using the same procedure as in the synthesis example (1) described above. [ka]

[0508] The structure of the compound obtained was confirmed by mass spectrometry. EI-MS, M / Z = 730.

[0509] By appropriately changing the raw material compounds, other polycyclic aromatic compounds of the present invention can be synthesized by a method similar to the synthesis example described above.

[0510] Next, the fabrication and evaluation of organic EL elements using the compounds of the present invention will be described. However, the application of the compounds of the present invention is not limited to the examples shown below, and the film thickness and constituent materials of each layer can be appropriately changed depending on the basic physical properties of the compounds of the present invention.

[0511] <Evaluation of vapor-deposited organic EL elements> Organic EL elements according to Examples 1-1 to 1-17 and Comparative Examples 1-1 to 1-7 were fabricated, and a capacitance of 1000 cd / m² was achieved. 2 The characteristics of light emission, namely the driving voltage (V) and external quantum efficiency (%), were measured, followed by 10 mA / cm². 2 The time it took to maintain a brightness of 90% or more of the initial brightness when driven with a constant current at a given current density was measured.

[0512] The quantum efficiency of a light-emitting device has two components: internal quantum efficiency and external quantum efficiency. Internal quantum efficiency indicates the proportion of external energy injected into the light-emitting layer of the device as electrons (or holes) that is purely converted into photons. External quantum efficiency, on the other hand, is calculated based on the amount of these photons emitted to the outside of the device. Since some of the photons generated in the light-emitting layer are absorbed or reflected within the device and not emitted to the outside, external quantum efficiency is lower than internal quantum efficiency.

[0513] The external quantum efficiency measurement method is as follows: Using an Advantest R6144 voltage / current generator, the device's brightness is 1000 cd / m². 2 A voltage was applied to the element to cause it to emit light. Using a TOPCON SR-3AR spectroradiometer, the spectral radiance in the visible light region was measured perpendicular to the light-emitting surface. Assuming the light-emitting surface is a perfectly diffusive surface, the number of photons at each wavelength is obtained by dividing the measured spectral radiance value for each wavelength component by the wavelength energy and multiplying by π. Next, the number of photons was integrated across the entire observed wavelength range to obtain the total number of photons emitted from the element. The number of carriers injected into the element is obtained by dividing the applied current value by the elementary charge, and the external quantum efficiency is obtained by dividing the total number of photons emitted from the element by the number of carriers injected into the element.

[0514] The material composition of each layer and EL characteristic data for the organic EL elements fabricated in Examples 1-1 to 1-17, Examples 1-18 to 1-29, and Comparative Examples 1-1 to 1-7 are shown in the table below. Note that the electron transport layer 2 was formed by co-depositing the compounds listed in the table and Liq in a weight ratio of 1:1.

[0515] [Table 1A]

[0516] [Table 1B]

[0517] [Table 1C]

[0518] [Table 1D]

[0519] [Table 2A]

[0520] [Table 2B]

[0521] The chemical structures of "HI", "IL", "HT-1", "HT-2", "BH-1", "BD-1", "ET-1", "Liq", comparative compound (1), comparative compound (2), comparative compound (3), comparative compound (4), comparative compound (5), comparative compound (6), and comparative compound (7) in the above tables are shown below.

[0522] [ka]

[0523] [ka]

[0524] <Example 1-1> A 26mm x 28mm x 0.7mm glass substrate (manufactured by OptoScience Co., Ltd.), which had been polished to 150nm by sputtering an ITO film to a thickness of 180nm, was used as a transparent support substrate. This transparent support substrate was fixed to the substrate holder of a commercially available deposition apparatus (manufactured by Choshu Sangyo Co., Ltd.), and tantalum deposition boats containing HI, IL, HT-1, HT-2, BH-1, BD-1, ET-1, and compound (1-2), respectively, and aluminum nitride deposition boats containing Liq, Mg, and Ag, respectively, were attached.

[0525] The following layers were sequentially formed on the ITO film of the transparent support substrate. The vacuum chamber was 5 × 10 -4 The pressure was reduced to Pa. First, HI was heated and deposited to a thickness of 40 nm. Next, IL was heated and deposited to a thickness of 5 nm. Then, HT-1 was heated and deposited to a thickness of 15 nm. Next, HT-2 was heated and deposited to a thickness of 10 nm to form a hole layer consisting of four layers. Next, BH-1 and BD-1 were heated simultaneously and deposited to a thickness of 25 nm to form an emissive layer. The deposition rate was adjusted so that the weight ratio of BH-1 to BD-1 was approximately 98:2. Then, ET-1 was heated and deposited to a thickness of 5 nm to form electron transport layer 1. Furthermore, compound (1-2) and Liq were heated simultaneously and deposited to a thickness of 25 nm to form electron transport layer 2. The deposition rate was adjusted so that the weight ratio of compound (1-2) to Liq was approximately 50:50. The deposition rate for each layer was 0.01 to 1 nm / second. Subsequently, Liq was heated and deposited at a deposition rate of 0.01 to 0.1 nm / second to achieve a film thickness of 1 nm. Then, magnesium and silver were heated simultaneously and deposited to form a cathode with a film thickness of 100 nm, thereby obtaining an organic EL device. At this time, the deposition rate was adjusted between 0.1 nm and 10 nm / second so that the atomic ratio of magnesium to silver was 10:1.

[0526] The EL characteristics of each electrode were measured by applying a DC voltage with an ITO electrode as the anode and a magnesium / silver electrode as the cathode.

[0527] <Examples 1-2 to 1-17, Examples 1-18 to 1-29, Comparative Example 1-1 to 1-7> Organic EL elements for Examples 1-2 to 1-17, Examples 1-18 to 1-29, and Comparative Examples 1-1 to 1-7 were obtained using the same method as in Example 1-1, except that the material of the electron transport layer 2 was replaced with the materials listed in the tables above. The EL characteristics of each were measured by applying a DC voltage with the ITO electrode as the anode and the magnesium / silver electrode as the cathode.

[0528] <Evaluation of coated organic EL elements> Next, we will describe an organic EL element obtained by coating and forming an organic layer.

[0529] <Synthesis of polymer host compound: SPH-101> SPH-101 was synthesized according to the method described in International Publication No. 2015 / 008851. A copolymer was obtained in which M2 or M3 was bonded next to M1, and the molar ratio of each unit is estimated to be 50:26:24 based on the starting ratio. In the structural formula below, Me is a methyl group, Bpin is a pinacolate boryl group, and * indicates the linkage site of each unit. [ka]

[0530] <Synthesis of the polymer hole transport compound: XLP-101> XLP-101 was synthesized according to the method described in Japanese Patent Publication No. 2018-61028. A copolymer was obtained in which M5 or M6 was bonded next to M4, and it is estimated from the starting ratio that each unit is in a molar ratio of 40:10:50. In the structural formula below, Me is a methyl group, Bpin is a pinacolate boryl group, and * indicates the linkage site of each unit. [ka]

[0531] <Examples 2-1 to 2-9> A coating solution for each layer is prepared to fabricate a coated organic EL element.

[0532] <Fabrication of Organic EL Devices of Examples 2-1 to 2-3> The material compositions of each layer in the organic EL device are shown in Table 3.

Table 3

[0533] The structure of "ET1" in Table 3 is shown below.

Chemical formula

[0534] <Preparation of Composition (1) for Forming Light-Emitting Layer> Composition (1) for forming a light-emitting layer is prepared by stirring the following components until a homogeneous solution is obtained. The prepared composition for forming a light-emitting layer is spin-coated on a glass substrate and dried by heating under reduced pressure, whereby a coating film without film defects and excellent in smoothness can be obtained. Compound (A) 0.04 wt% SPH-101 1.96 wt% Xylene 69.00 wt% Decalin 29.00 wt%

[0535] Compound (A) is a polycyclic aromatic compound represented by the general formula (1) (for example, Compound (1-2)), a polymer compound obtained by polymerizing the polycyclic aromatic compound as a monomer (that is, the monomer has a reactive substituent), or a polymer crosslinked product obtained by further crosslinking the polymer compound. The polymer compound for obtaining the polymer crosslinked product has a crosslinkable substituent.

[0536] <PEDOT:PSS Solution> A commercially available PEDOT:PSS solution (Clevios(TM) P VP AI4083, an aqueous dispersion of PEDOT:PSS, manufactured by Heraeus Holdings) is used.

Chemical formula

[0537] <Preparation of OTPD Solution> Dissolve OTPD (LT-N159, manufactured by Luminescence Technology Corp) and IK-2 (photo cationic polymerization initiator, manufactured by San-Apro) in toluene to prepare an OTPD solution with an OTPD concentration of 0.7% by weight and an IK-2 concentration of 0.007% by weight.

Chemical formula

[0538] <Preparation of XLP-101 Solution> Dissolve XLP-101 in xylene at a concentration of 0.6% by weight to prepare a 0.6% by weight XLP-101 solution.

[0539] <Preparation of PCz Solution> Dissolve PCz (polyvinylcarbazole) in dichlorobenzene to prepare a 0.7% by weight PCz solution.

Chemical formula

[0540] <Example 2-1> ​​​​​​The fabricated multilayer film is fixed to the substrate holder of a commercially available deposition apparatus (manufactured by Showa Vacuum Co., Ltd.), and a molybdenum deposition boat containing ET1, a molybdenum deposition boat containing LiF, and a tungsten deposition boat containing aluminum are attached. The vacuum chamber is 5 × 10 -4 After reducing the pressure to Pa, ET1 is heated and deposited to a thickness of 30 nm to form an electron transport layer. The deposition rate for forming the electron transport layer is 1 nm / second. Then, LiF is heated and deposited at a deposition rate of 0.01 to 0.1 nm / second to a thickness of 1 nm. Next, aluminum is heated and deposited to a thickness of 100 nm to form a cathode. In this way, an organic EL device is obtained.

[0542] <Example 2-2> An organic EL element is obtained using the same method as in Example 2-1. The hole transport layer is formed by spin-coating with XLP-101 solution and firing on a hot plate at 200°C for 1 hour to create a film with a thickness of 30 nm.

[0543] <Example 2-3> An organic EL device is obtained using the same method as in Example 2-1. The hole transport layer is formed by spin-coating a PCz solution and firing it on a hot plate at 120°C for 1 hour to create a film with a thickness of 30 nm.

[0544] <Evaluation of Organic EL Devices in Examples 2-1 to 2-3> It can be expected that the solution-type organic EL elements obtained in the manner described above will have excellent driving voltage and external quantum efficiency, similar to the vapor-deposited organic EL elements.

[0545] <Fabrication of organic EL elements in Examples 2-4 to 2-6> Table 4 shows the material composition of each layer in an organic EL device. [Table 4]

[0546] <Preparation of compositions (2) to (4) for forming the light-emitting layer> A composition (2) for forming a light-emitting layer is prepared by stirring the following components until a uniform solution is formed. Compound (A) 0.02% by weight mCBP 1.98 wt% Toluene 98.00% by weight

[0547] A composition (3) for forming a light-emitting layer is prepared by stirring the following components until a uniform solution is formed. Compound (A) 0.02% by weight SPH-101 1.98% by weight Xylene 98.00% by weight

[0548] A composition (4) for forming an luminescent layer is prepared by stirring the following components until a homogeneous solution is formed. Compound (A) 0.02% by weight DOBNA 1.98% by weight Toluene 98.00% by weight

[0549] In Table 4, "mCBP" is 3,3'-bis(N-carbazolyl)-1,1'-biphenyl, "DOBNA" is 3,11-di-o-tolyl-5,9-dioxa-13b-boranaphtho[3,2,1-de]anthracene, and "TSPO1" is diphenyl[4-(triphenylsilyl)phenyl]phosphine oxide. The chemical structures are shown below. [ka]

[0550] <Example 2-4> On a glass substrate with a 45nm thick ITO film, an ND-3202 (manufactured by Nissan Chemical Industries) solution is spin-coated, and then heated in an air atmosphere at 50°C for 3 minutes, followed by heating at 230°C for 15 minutes to form a 50nm thick ND-3202 film (hole injection layer). Next, an XLP-101 solution is spin-coated and heated on a hot plate at 200°C for 30 minutes in a nitrogen gas atmosphere to form a 20nm thick XLP-101 film (hole transport layer). Then, a light-emitting layer formation composition (2) is spin-coated and heated at 130°C for 10 minutes in a nitrogen gas atmosphere to form a 20nm light-emitting layer.

[0551] The fabricated multilayer film is fixed to the substrate holder of a commercially available deposition apparatus (manufactured by Showa Vacuum Co., Ltd.), and a molybdenum deposition boat containing TSPO1, a molybdenum deposition boat containing LiF, and a tungsten deposition boat containing aluminum are attached. The vacuum chamber is 5 × 10 -4 After reducing the pressure to Pa, TSPO1 is heated and deposited to a thickness of 30 nm to form an electron transport layer. The deposition rate for forming the electron transport layer is 1 nm / second. Then, LiF is heated and deposited at a deposition rate of 0.01 to 0.1 nm / second to a thickness of 1 nm. Next, aluminum is heated and deposited to a thickness of 100 nm to form a cathode. In this way, an organic EL device is obtained.

[0552] <Examples 2-5 and 2-6> An organic EL element is obtained using the light-emitting layer forming composition (3) or (4) in the same manner as in Examples 2-4.

[0553] <Evaluation of Organic EL Devices in Examples 2-4 to 2-6> It can be expected that the solution-type organic EL elements obtained in the manner described above will have excellent driving voltage and external quantum efficiency, similar to the vapor-deposited organic EL elements.

[0554] <Fabrication of organic EL elements in Examples 2-7 to 2-9> Table 5 shows the material composition of each layer in an organic EL device. [Table 5]

[0555] <Preparation of compositions (5) to (7) for forming the light-emitting layer> A composition (5) for forming a light-emitting layer is prepared by stirring the following components until a uniform solution is formed. Compound (A) 0.02% by weight 2PXZ-TAZ 0.18% by weight mCBP 1.80% by weight Toluene 98.00% by weight

[0556] A composition (6) for forming an luminescent layer is prepared by stirring the following components until a uniform solution is formed. Compound (A) 0.02% by weight 2PXZ-TAZ 0.18% by weight SPH-101 1.80% by weight Xylene 98.00% by weight

[0557] A composition (7) for forming a light-emitting layer is prepared by stirring the following components until a uniform solution is formed. Compound (A) 0.02% by weight 2PXZ-TAZ 0.18% by weight DOBNA 1.80% by weight Toluene 98.00% by weight

[0558] In Table 5, "2PXZ-TAZ" is 10,10'-((4-phenyl-4H-1,2,4-triazole-3,5-diyl)bis(4,1-phenyl))bis(10H-phenoxazine). Its chemical structure is shown below. [ka]

[0559] <Example 2-7> On a glass substrate with a 45nm thick ITO film, an ND-3202 (manufactured by Nissan Chemical Industries) solution is spin-coated, and then heated in an air atmosphere at 50°C for 3 minutes, followed by heating at 230°C for 15 minutes to form a 50nm thick ND-3202 film (hole injection layer). Next, an XLP-101 solution is spin-coated and heated on a hot plate at 200°C for 30 minutes in a nitrogen gas atmosphere to form a 20nm thick XLP-101 film (hole transport layer). Then, a light-emitting layer formation composition (5) is spin-coated and heated at 130°C for 10 minutes in a nitrogen gas atmosphere to form a 20nm light-emitting layer.

[0560] The fabricated multilayer film is fixed to the substrate holder of a commercially available deposition apparatus (manufactured by Showa Vacuum Co., Ltd.), and a molybdenum deposition boat containing TSPO1, a molybdenum deposition boat containing LiF, and a tungsten deposition boat containing aluminum are attached. The vacuum chamber is 5 × 10 -4 After reducing the pressure to Pa, TSPO1 is heated and deposited to a thickness of 30 nm to form an electron transport layer. The deposition rate for forming the electron transport layer is 1 nm / second. Then, LiF is heated and deposited at a deposition rate of 0.01 to 0.1 nm / second to a thickness of 1 nm. Next, aluminum is heated and deposited to a thickness of 100 nm to form a cathode. In this way, an organic EL device is obtained.

[0561] <Examples 2-8 and 2-9> An organic EL element is obtained using the light-emitting layer forming composition (6) or (7) in the same manner as in Example 2-7.

[0562] <Evaluation of Organic EL Devices in Examples 2-7 to 2-9> It can be expected that the solution-type organic EL elements obtained in the manner described above will have excellent driving voltage and external quantum efficiency, similar to the vapor-deposited organic EL elements.

[0563] In summary, we have evaluated some of the compounds according to the present invention as materials for organic EL devices and demonstrated their excellent properties. However, the other compounds that were not evaluated also have the same basic framework and similar overall structures, and those skilled in the art will understand that they are equally excellent materials for organic EL devices. [Industrial applicability]

[0564] According to a preferred embodiment of the present invention, by fabricating an organic EL element using an electron transport material containing a polycyclic aromatic compound represented by general formula (1), it is possible to provide an organic EL element with excellent driving voltage, luminous efficiency, and element lifetime, particularly one with excellent luminous efficiency and element lifetime. [Explanation of Symbols]

[0565] 100 Organic Electroluminescent Devices 101 circuit board 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 general formula (1). 【Chemistry 1】 In the above formula (1), R １ ~R １１ Each of these is independently hydrogen, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl, alkyl, cycloalkyl, alkenyl, alkoxy, aryloxy, arylthio, triarylsilyl, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, or alkyldicycloalkylsilyl, wherein the two aryls of the diarylamino may be linked via a linking group, the two heteroaryls of the diheteroarylamino may be linked via a linking group, the aryl and heteroaryl of the arylheteroarylamino may be linked via a linking group, and the two aryls of the diarylboryl may be linked via a linking group. R １ ~R １１ Adjacent groups among them may bond together to form a naphthalene ring, a phenanthrene ring, a dibenzothiophene ring, a dibenzofuran ring, or a carbazole ring together with at least one of the rings a, b, and c, and at least one hydrogen in the formed ring may be independently substituted with diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl, alkyl, cycloalkyl, alkenyl, alkoxy, aryloxy, arylthio, triarylsilyl, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, or alkyldicycloalkylsilyl, and the two aryls of the diarylamino may be bonded via a linking group, the two heteroaryls of the diheteroarylamino may be bonded via a linking group, the aryl and heteroaryl of the arylheteroarylamino may be bonded via a linking group, and the two aryls of the diarylboryl may be bonded via a linking group. However, at least one group represented by the above general formula (G) is bonded to the "a-ring" or "ring formed together with the a-ring," at least one group represented by the above general formula (G) is bonded to the "b-ring" or "ring formed together with the b-ring," and at least one group represented by the above general formula (G) is bonded to the "c-ring" or "ring formed together with the c-ring," and these groups represented by formula (G) may be the same or different. In the above formula (G), Cy １ and Cy ２ Each of these rings is independently a benzene ring, a naphthalene ring, a phenanthrene ring, a pyridine ring, a quinoline ring, a dibenzofuran ring, a dibenzothiophene ring, or a carbazole ring whose N position may be substituted with phenyl, and each of these rings is independently substituted with diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl, alkyl, cycloalkyl, alkenyl, alkoxy, aryloxy, arylthio, triarylsilyl, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, alkyldicycloalkylsilyl, or cyano, and the two aryls of the diarylamino may be linked via a linking group, the two heteroaryls of the diheteroarylamino may be linked via a linking group, the aryl and heteroaryl of the arylheteroarylamino may be linked via a linking group, and the two aryls of the diarylboryl may be linked via a linking group, and * is the bond position to the a ring, b ring, c ring, and the ring formed together with these rings, and At least one hydrogen atom in the compound represented by formula (1) above may be substituted with deuterium, cyano, or halogen.

2. In the above formula (1), R １ ~R １１ are each independently hydrogen, diarylamino (where aryl is aryl having 6 to 12 carbon atoms), diheteroarylamino (where heteroaryl is heteroaryl having 2 to 15 carbon atoms), arylheteroarylamino (where aryl is aryl having 6 to 12 carbon atoms and heteroaryl is heteroaryl having 2 to 15 carbon atoms), diarylboryl (where aryl is aryl having 6 to 12 carbon atoms), alkyl having 1 to 24 carbon atoms, cycloalkyl having 3 to 24 carbon atoms, alkenyl having 1 to 24 carbon atoms, alkoxy having 1 to 24 carbon atoms, aryloxy having 6 to 30 carbon atoms, arylthio having 6 to 30 carbon atoms, triarylsilyl (where aryl is aryl having 6 to 12 carbon atoms), trialkylsilyl (where alkyl is alkyl having 1 to 12 carbon atoms), tricycloalkylsilyl (where cycloalkyl is cycloalkyl having 3 to 12 carbon atoms), dialkylcycloalkylsilyl (where alkyl is alkyl having 1 to 12 carbon atoms and cycloalkyl is cycloalkyl having 3 to 12 carbon atoms), or alkyldicycloalkylsilyl (where alkyl is alkyl having 1 to 12 carbon atoms and cycloalkyl is cycloalkyl having 3 to 12 carbon atoms), and the two aryls of the diarylamino may be bonded via a linking group, the two heteroaryls of the diheteroarylamino may be bonded via a linking group, the aryl and heteroaryl of the arylheteroarylamino may be bonded via a linking group, the two aryls of the diarylboryl may be bonded via a linking group, and the linking group is a single bond, -CH ２ -CH ２ -, -CHR-CHR-, -CR ２ -CR ２ -, -CH=CH-, -CR=CR-, -C≡C-, -N(-R)-, -O-, -S-, -C(-R) ２ -, -Si(-R) ２ R is - or -Se-, and each R is independently hydrogen, a C6-C12 aryl, a C2-C15 heteroaryl, a C1-C24 alkyl, a C1-C24 alkenyl, a C1-C24 alkynyl, or a C3-C24 cycloalkyl, and at least one hydrogen in R may be substituted with a C1-C24 alkyl or a C3-C24 cycloalkyl. R １ ~R １１ Adjacent groups among them may bond together to form a naphthalene ring, a phenanthrene ring, a dibenzothiophene ring, a dibenzofuran ring, or a carbazole ring together with at least one of the rings a, b, and c, and at least one hydrogen in the formed ring may independently be a diarylamino (where aryl is a C6-C12 aryl), a diheteroarylamino (where heteroaryl is a C2-C15 heteroaryl), an arylheteroarylamino (where aryl is a C6-C12 aryl, and heteroaryl is a C2-C15 heteroaryl), a diarylboryl (where aryl is a C6-C12 aryl), a C1-C24 alkyl, a C3-C24 cycloalkyl, a C1-C24 alkenyl, a C1-C24 alkoxy, a C6-C30 aryloxy, a C6-C30 arylthio, or a triarylsilyl (where aryl) The diarylamino may be substituted with an aryl group having 6 to 12 carbon atoms, a trialkylsilyl group (where alkyl is an alkyl group having 1 to 12 carbon atoms), a tricycloalkylsilyl group (where cycloalkyl is a cycloalkyl group having 3 to 12 carbon atoms), a dialkylcycloalkylsilyl group (where alkyl is an alkyl group having 1 to 12 carbon atoms, and cycloalkyl is a cycloalkyl group having 3 to 12 carbon atoms), or an alkyldicycloalkylsilyl group (where alkyl is an alkyl group having 1 to 12 carbon atoms, and cycloalkyl is a cycloalkyl group having 3 to 12 carbon atoms), the two aryls of the diarylamino may be linked via a linking group, the two heteroaryls of the diheteroarylamino may be linked via a linking group, the aryl and heteroaryls of the arylheteroarylamino may be linked via a linking group, and the two aryls of the diarylboryl may be linked via a linking group, the linking group may be a single bond, -CH ２ -CH ２ -, -CHR-CHR-, -CR ２ -CR ２ -, -CH=CH-, -CR=CR-, -C≡C-, -N(-R)-, -O-, -S-, -C(-R) ２ -, -Si(-R) ２ R is - or -Se-, and each R is independently hydrogen, a C6-C12 aryl, a C2-C15 heteroaryl, a C1-C24 alkyl, a C1-C24 alkenyl, a C1-C24 alkynyl, or a C3-C24 cycloalkyl, and at least one hydrogen in R may be substituted with a C1-C24 alkyl or a C3-C24 cycloalkyl. However, at least one group represented by the above general formula (G) is bonded to the "a-ring" or "ring formed together with the a-ring," at least one group represented by the above general formula (G) is bonded to the "b-ring" or "ring formed together with the b-ring," and at least one group represented by the above general formula (G) is bonded to the "c-ring" or "ring formed together with the c-ring," and these groups represented by formula (G) may be the same or different. In the above formula (G), Cy １ and Cy ２ Each of these rings is independently a benzene ring, a naphthalene ring, a phenanthrene ring, a pyridine ring, a quinoline ring, a dibenzofuran ring, a dibenzothiophene ring, or a carbazole ring whose N position may be substituted with phenyl, and each of these rings is independently a diarylamino (where aryl is a C6-C12 aryl), a diheteroarylamino (where heteroaryl is a C2-C15 heteroaryl), an arylheteroarylamino (where aryl is a C6-C12 aryl, and heteroaryl is a C2-C15 heteroaryl), a diarylboryl (where aryl is a C6-C12 aryl), an alkyl (C1-C24), a cycloalkyl (C3-C24), an alkenyl (C1-C24), an alkoxy (C1-C24), an aryloxy (C6-C30), an arylthio (C6-C30), or a triarylsilyl (where aryl is a C6 They may be substituted with aryls (up to 12), trialkylsilyls (where alkyl is an alkyl having 1 to 12 carbon atoms), tricycloalkylsilyls (where cycloalkyl is a cycloalkyl having 3 to 12 carbon atoms), dialkylcycloalkylsilyls (where alkyl is an alkyl having 1 to 12 carbon atoms, and cycloalkyl is a cycloalkyl having 3 to 12 carbon atoms), alkyldicycloalkylsilyls (where alkyl is an alkyl having 1 to 12 carbon atoms, and cycloalkyl is a cycloalkyl having 3 to 12 carbon atoms), or cyano, and the two aryls of the diarylamino may be linked via a linking group, the two heteroaryls of the diheteroarylamino may be linked via a linking group, the aryl and heteroaryl of the arylheteroarylamino may be linked via a linking group, and the two aryls of the diarylboryl may be linked via a linking group, and the linking group may be a single bond, -CH ２ -CH ２ -, -CHR-CHR-, -CR ２ -CR ２ -, -CH=CH-, -CR=CR-, -C≡C-, -N(-R)-, -O-, -S-, -C(-R) ２ -, -Si(-R) ２ R is - or -Se-, and each R is independently a hydrogen, a C6-C12 aryl, a C2-C15 heteroaryl, a C1-C24 alkyl, a C1-C24 alkenyl, a C1-C24 alkynyl, or a C3-C24 cycloalkyl, and at least one hydrogen in R may be substituted with a C1-C24 alkyl or a C3-C24 cycloalkyl, and * is the bond position to the a ring, b ring, c ring, and the ring formed together with those rings, and, In the compound represented by formula (1) above, at least one hydrogen atom may be substituted with deuterium, cyanopropyl alcohol, or halogen. The polycyclic aromatic compound according to claim 1.

3. In the above formula (1), R １ ~R １１ Each of these is independently hydrogen, diarylamino (where aryl has 6 to 12 carbon atoms), alkyl with 1 to 24 carbon atoms, cycloalkyl with 3 to 24 carbon atoms, alkoxy with 1 to 24 carbon atoms, aryloxy with 6 to 30 carbon atoms, or arylthio with 6 to 30 carbon atoms, and the two aryls of the diarylamino may be linked via a linking group, which can be a single bond, -CH ２ -CH ２ -, -CHR-CHR-, -CR ２ -CR ２ -, -CH=CH-, -CR=CR-, -C≡C-, -N(-R)-, -O-, -S-, -C(-R) ２ -, -Si(-R) ２ R is - or -Se-, and each R is independently hydrogen, a C6-C12 aryl, a C1-C24 alkyl, or a C3-C24 cycloalkyl, and at least one hydrogen in R may be substituted with a C1-C24 alkyl or a C3-C24 cycloalkyl. R １ ~R １１ Adjacent groups among them may bond together to form a naphthalene ring, a phenanthrene ring, a dibenzothiophene ring, a dibenzofuran ring, or a carbazole ring together with at least one of the rings a, b, and c, and at least one hydrogen in the formed ring may be independently substituted with a diarylamino (where the aryl is a C6-C12 aryl), a C1-C24 alkyl, a C3-C24 cycloalkyl, a C1-C24 alkoxy, a C6-C30 aryloxy, or a C6-C30 arylthio, and the two aryls of the diarylamino may be bonded via a linking group, the linking group being a single bond, -CH ２ -CH ２ -, -CHR-CHR-, -CR ２ -CR ２ -, -CH=CH-, -CR=CR-, -C≡C-, -N(-R)-, -O-, -S-, -C(-R) ２ -, -Si(-R) ２ R is - or -Se-, and each R is independently hydrogen, a C6-C12 aryl, a C1-C24 alkyl, or a C3-C24 cycloalkyl, and at least one hydrogen in R may be substituted with a C1-C24 alkyl or a C3-C24 cycloalkyl. However, at least one group represented by the above general formula (G) is bonded to the "a-ring" or "ring formed together with the a-ring," at least one group represented by the above general formula (G) is bonded to the "b-ring" or "ring formed together with the b-ring," and at least one group represented by the above general formula (G) is bonded to the "c-ring" or "ring formed together with the c-ring," and these groups represented by formula (G) may be the same or different. In the above formula (G), Cy １ and Cy ２ Each of these rings is independently a benzene ring, a naphthalene ring, a phenanthrene ring, a pyridine ring, a quinoline ring, a dibenzofuran ring, a dibenzothiophene ring, or a carbazole ring whose N position may be substituted with phenyl, and each of these rings may independently be substituted with a diarylamino (where the aryl is a C6-C12 aryl), a C1-C24 alkyl, a C3-C24 cycloalkyl, a C1-C24 alkoxy, a C6-C30 aryloxy, a C6-C30 arylthio, or a cyano, and the two aryls of the diarylamino may be linked via a linking group, the linking group being a single bond, -CH ２ -CH ２ -, -CHR-CHR-, -CR ２ -CR ２ -, -CH=CH-, -CR=CR-, -C≡C-, -N(-R)-, -O-, -S-, -C(-R) ２ -, -Si(-R) ２ R is - or -Se-, and each R is independently hydrogen, a C6-C12 aryl, a C1-C24 alkyl, or a C3-C24 cycloalkyl, and at least one hydrogen in R may be substituted with a C1-C24 alkyl or a C3-C24 cycloalkyl, and * is the bond position to the a ring, b ring, c ring, and the ring formed together with those rings, and, In the compound represented by formula (1) above, at least one hydrogen atom may be substituted with deuterium, cyanopropyl alcohol, or halogen. The polycyclic aromatic compound according to claim 1.

4. In the above formula (1), R １ ~R １１ Each of these is independently hydrogen, diarylamino (where aryl is an aryl with 6 to 12 carbon atoms), alkyl with 1 to 24 carbon atoms, or cycloalkyl with 3 to 24 carbon atoms. R １ ~R １１ Adjacent groups among them may bond together to form a naphthalene ring, a phenanthrene ring, a dibenzothiophene ring, a dibenzofuran ring, or a carbazole ring, and at least one hydrogen atom in the formed ring may be independently substituted with a diarylamino (where the aryl is a C6-C12 aryl), a C1-C24 alkyl, or a C3-C24 cycloalkyl. However, at least one group represented by the above general formula (G) is bonded to the "a-ring" or "ring formed together with the a-ring," at least one group represented by the above general formula (G) is bonded to the "b-ring" or "ring formed together with the b-ring," and at least one group represented by the above general formula (G) is bonded to the "c-ring" or "ring formed together with the c-ring," and these groups represented by formula (G) may be the same or different. In the above formula (G), Cy １ and Cy ２ Each of these rings is independently a benzene ring, a naphthalene ring, a phenanthrene ring, a pyridine ring, a quinoline ring, a dibenzofuran ring, a dibenzothiophene ring, or a carbazole ring whose N position may be substituted with phenyl, and each of these rings may independently be substituted with a diarylamino (where the aryl is a C6-C12 aryl), a C1-C24 alkyl, a C3-C24 cycloalkyl, or a cyano, and * is the bond position to the a ring, b ring, c ring, and the ring formed together with these rings, and, In the compound represented by formula (1) above, at least one hydrogen atom may be substituted with deuterium, cyanopropyl alcohol, or halogen. The polycyclic aromatic compound according to claim 1.

5. In the above formula (1), R １ ~R １１ Each of these is independently hydrogen or an alkyl group having 1 to 24 carbon atoms. However, R in ring a １ ~R ３ At least one of the R in the b ring ４ ~R ７ At least one of the and R in the c ring ８ ~R １１ At least one of these is a group represented by the general formula (G) above, and these groups represented by formula (G) may be the same or different. In the above formula (G), Cy １ and Cy ２ Each of these rings is independently a benzene ring, a naphthalene ring, a phenanthrene ring, a pyridine ring, a quinoline ring, a dibenzofuran ring, a dibenzothiophene ring, or a carbazole ring whose N position may be substituted with phenyl, and each of these rings may independently be substituted with an alkyl or cyano having 1 to 24 carbon atoms, and * is the bond position to the a ring, b ring, and c ring, and, In the compound represented by formula (1) above, at least one hydrogen atom may be substituted with deuterium, cyanopropyl alcohol, or halogen. The polycyclic aromatic compound according to claim 1.

6. A polycyclic aromatic compound as described in claim 1, represented by any of the following structural formulas. 【Chemistry 2】 【Transformation 3】 【Chemistry 4】

7. A polycyclic aromatic compound as described in claim 1, represented by any of the following structural formulas. 【Transformation 5】

8. An organic electroluminescent element comprising a pair of electrodes consisting of an anode and a cathode, a light-emitting layer disposed between the pair of electrodes, and at least one electron transport layer and electron injection layer disposed between the cathode and the light-emitting layer and containing a polycyclic aromatic compound as described in any one of claims 1 to 7.

9. A display device or lighting device comprising an organic electroluminescent element as described in claim 8.

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