Polycyclic aromatic compounds

Abstract

To provide a novel polycyclic aromatic compound and an organic EL device including the same.SOLUTION: A polycyclic aromatic compound represented by general formula (1) allows for a broader range of choices of materials for organic devices. Using the novel material to make e.g. an organic EL device can provide an excellent element. The A ring and the B ring are each an aryl ring or a heteroaryl ring, Rc is hydrogen or a substituent, Y1, Y2, and Y3 are each >B- or the like, X1, X2, X3, and X4 are each >N-R or the like, the compound may be condensed with a cycloalkane, or may be substituted with deuterium or the like.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] The host materials for organic EL devices are generally molecules in which multiple existing aromatic rings, such as benzene and carbazole, are linked by single bonds or phosphorus or silicon atoms. This is because linking many relatively small conjugated aromatic rings ensures the large HOMO-LUMO gap (band gap Eg in thin films) required for the host material. Furthermore, host materials for organic EL devices using phosphorescent materials or thermally activated delayed fluorescence materials have high triplet excitation energies (E). T Although this is also necessary, by linking donor or acceptor aromatic rings or substituents to the molecule, the SOMO1 and SOMO2 in the triplet excited state (T1) are localized, and the exchange interaction between the two orbitals is reduced, thereby increasing the triplet excitation energy (E T This makes it possible to improve the redox stability of small aromatic rings in conjugated systems. However, devices using molecules formed by linking existing aromatic rings as host materials do not have sufficient lifespan. On the other hand, polycyclic aromatic compounds with extended π-conjugated systems generally have excellent redox stability, but the HOMO-LUMO gap (band gap Eg in thin films) and triplet excitation energy (E) are not as good. T Because of its low ) ratio, it has been considered unsuitable as a host material.

[0006] 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 an organic EL device using such a compound with multiple aromatic rings fused together as a dopant material for the light-emitting layer. Furthermore, examples of using 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 Published Patent No. 10-2020-0121228, International Publication No. 2020 / 217229). [Prior art documents] [Patent Documents]

[0007] [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]

[0008] 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.

[0009] 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, it is beneficial to explore materials for light-emitting layers, particularly dopant materials, that can improve organic EL characteristics such as luminous efficiency and device lifetime in order to further enhance the device characteristics.

[0010] 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 hole injection layers, hole transport layers, and light-emitting layers, is being actively pursued, and exploring such ink materials is also beneficial. [Means for solving the problem]

[0011] 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.

[0012] 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.

[0013] Section 1. A polycyclic aromatic compound represented by the following general formula (1).

Chemical formula

[0014] Section 2. In the above equation (1), Rings A and B are each independently an aryl ring or a heteroaryl ring, and at least one hydrogen in these rings may be substituted with an optionally substituted aryl, optionally substituted heteroaryl, optionally substituted diarylamino, optionally substituted diheteroarylamino, optionally substituted arylheteroarylamino, optionally substituted diarylboryl (the two aryls may be linked by a single bond or a linking group), optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted alkoxy, optionally substituted aryloxy, optionally substituted diarylphosphoryl, or substituted silyl. R cis hydrogen, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted diarylamino, optionally substituted diheteroarylamino, optionally substituted arylheteroarylamino, optionally substituted diarylboryl (the two aryls may be linked by a single bond or a linking group), optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted alkoxy, optionally substituted aryloxy, optionally substituted diarylphosphoryl, or substituted silyl. "-C(-R)" in the c ring c )=" can be replaced with "-N=". Y 1 , Y 2 , and Y 3 Each of these is independently >B-, >P-, >P(=O)-, >P(=S)-, >Al-, >Ga-, >As-, >C(-R)-, >Si(-R)-, or >Ge(-R)-, where R in >C(-R)-, R in >Si(-R)-, and R in >Ge(-R)- are independently aryl, heteroaryl, alkyl, or cycloalkyl, and at least one hydrogen in R may be substituted with alkyl or cycloalkyl. X 1 , X 2 , X 3 , and X 4 Each of these is independently >NR, >O, >S, >C(-R)2, >Si(-R)2, or >Se, where R in >NR, R in >C(-R)2, and R in >Si(-R)2 are independently hydrogen, aryl, heteroaryl, alkyl, or cycloalkyl, and at least one hydrogen in R may be substituted with alkyl or cycloalkyl. Also, the X 1 ~X 4The two Rs in ">C(-R)2" and the two Rs in ">Si(-R)2" may be independently bonded by single bonds, -CH=CH-, -CR=CR-, -C≡C-, =C(-R)-, =N-, -N(-R)-, -O-, -S-, -C(-R)2-, -Si(-R)2-, or -Se-, and the Rs in "-CR=CR-", "=C(-R)-", "-N(-R)-", and "- The R in "C(-R)2-" and the R in "-Si(-R)2-" are independently hydrogen, aryl, heteroaryl, alkyl, alkenyl, alkynyl, or cycloalkyl, and at least one hydrogen in the R may be substituted with an alkyl or cycloalkyl, and two adjacent Rs may be bonded together to form a cycloalkylene ring, an arylene ring, or a heteroarylene ring. Also, the X 1 or X 3 The R in ">NR", the R in ">C(-R)2", and the R in ">Si(-R)2" are, independently of each other, at least one ring of the A ring and the B ring, and the X 2 or X 4 The R in ">NR", the R in ">C(-R)2", and the R in ">Si(-R)2" may each be independently bonded to at least one of the A and c rings by a single bond, -CH=CH-, -CR=CR-, -C≡C-, =C(-R)-, =N-, -N(-R)-, -O-, -S-, -C(-R)2-, -Si(-R)2-, or -Se-, and the R in ">-CR=CR-", the R in ">C(-R)-", and the R in ">N( The R in "-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 each R may be substituted with an alkyl or cycloalkyl, and two adjacent Rs may be bonded together to form a cycloalkylene ring, an arylene ring, or a heteroarylene ring. In the compound represented by formula (1) above, at least one of the A ring, B ring, c ring, the aryl group, and the heteroaryl group may be condensed with at least one cycloalkane, and at least one hydrogen atom in the cycloalkane may be substituted with an aryl group, a heteroaryl group, an alkyl group, or a cycloalkyl group, and at least one "-CH2-" in the cycloalkane may be substituted with "-O-", 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 3. A polycyclic aromatic compound as described in item 1, represented by the following general formula (2). [ka] In the above equation (2), R a , R b , and R c Each 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, aryloxy, diarylphosphoryl, triarylsilyl, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, or alkyldicycloalkylsilyl, and the R a , R b , and R c At least one hydrogen in may be substituted with an aryl, heteroaryl, alkyl, or cycloalkyl group, and R a and R bAdjacent groups among them may bond together with ring a and ring b to form an aryl ring or a heteroaryl 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, aryloxy, diarylphosphoryl, triarylsilyl, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, or alkyldicycloalkylsilyl, and at least one hydrogen in these substituents may be substituted with aryl, heteroaryl, alkyl, or cycloalkyl. "-C(-R)" in the c ring c )=" can be replaced with "-N=". In ring a and ring b, any "-C(-R)=" (where R is R a or R b The part "-N=" may be replaced with any "-C(-R)=C(-R)-" (where R is R a or R bThe R in "-N(-R)-", "-O-", "-S-", "-C(-R)2-", "-Si(-R)2-", or "-Se-" may be replaced by "-N(-R)-", "-C(-R)2-", and "-Si(-R)2-", and the R in "-N(-R)-", "-C(-R)2-", and the R in "-Si(-R)2-" may be hydrogen, aryl, heteroaryl, alkyl, or cycloalkyl, and at least one hydrogen in the R may be substituted with alkyl or cycloalkyl, and the two Rs in "-C(-R)2-" and the two Rs in "-Si(-R)2-" may be independently single bonds, -CH=CH-, -CR=CR-, -C≡C-, =C(-R)-, The R in "-CR=CR-", "-C(-R)-", "-N(-R)-", "-N(-R)-", "-C(-R)2-", and "-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, and two adjacent Rs may be bonded together to form a cycloalkylene ring, an arylene ring, or a heteroarylene ring. Y 1 , Y 2 , and Y 3 These are, independently, >B-, >P-, >P(=O)-, or >P(=S)-, X 1 , X 2 , X 3 , and X 4 Each of these is independently >NR, >O, >S, or >C(-R)2, where R in ">NR" and R in ">C(-R)2" are independently hydrogen, aryl, heteroaryl, alkyl, or cycloalkyl, and at least one hydrogen in R may be substituted with alkyl or cycloalkyl. Also, the X 1 ~X 4The two Rs in ">C(-R)2" may be bonded by a single bond, -CH=CH-, -CR=CR-, -C≡C-, =C(-R)-, =N-, -N(-R)-, -O-, -S-, -C(-R)2-, -Si(-R)2-, or -Se-, and the Rs in "-CR=CR-", "=C(-R)-", "-N(-R)-", "-C(-R)2-", and "-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, and two adjacent Rs may be bonded together to form a cycloalkylene ring, an arylene ring, or a heteroarylene ring. Also, the X 1 or X 3 The R in ">NR" and the R in ">C(-R)2" are, independently of each other, at least one of the a-ring and b-ring, and the X 2 or X 4 The R in ">NR" and the R in ">C(-R)2" may each be independently bonded to at least one of the a-ring and c-ring by a single bond, -CH=CH-, -CR=CR-, -C≡C-, =C(-R)-, =N-, -N(-R)-, -O-, -S-, -C(-R)2-, -Si(-R)2-, or -Se-, and the R in "-CR=CR-", the R in "=C(-R)-", and the R in "-N(-R)-" The R in "-C(-R)2-" and the R in "-Si(-R)2-" are independently hydrogen, aryl, heteroaryl, alkyl, alkenyl, alkynyl, or cycloalkyl, and at least one hydrogen in the R may be substituted with an alkyl or cycloalkyl, and two adjacent Rs may be bonded together to form a cycloalkylene ring, an arylene ring, or a heteroarylene ring. In the compound represented by formula (2) above, at least one of the a-ring, b-ring, c-ring, the formed ring, the aryl, and the heteroaryl may be condensed with at least one cycloalkane, and at least one hydrogen in the cycloalkane may be substituted with an aryl, heteroaryl, alkyl, or cycloalkyl, and at least one "-CH2-" in the cycloalkane may be substituted with "-O-", At least one hydrogen atom in the compound represented by formula (2) above may be substituted with deuterium, cyano, or halogen.

[0016] Section 4. In the above equation (2), R a , R b , and R c Each of these is independently hydrogen, a carbon-6 to carbon-30 aryl group, a carbon-2 to carbon-30 heteroaryl group, a diarylamino group (where the aryl group is a carbon-6 to carbon-12 aryl group), a diarylboryl group (where the aryl group is a carbon-6 to carbon-12 aryl group, and the two aryl groups may be linked by a single bond or a linking group), a carbon-1 to carbon-24 alkyl group, or a carbon-3 to carbon-24 cycloalkyl group, and the R a , R b , and R c At least one hydrogen in may be substituted with an aryl group having 6 to 12 carbon atoms, a heteroaryl group having 2 to 15 carbon atoms, an alkyl group having 1 to 6 carbon atoms, or a cycloalkyl group having 3 to 14 carbon atoms, and R a and R bAdjacent groups among them may bond together to form a C9-C16 aryl ring or a C6-C15 heteroaryl ring with rings a and b, 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 diarylboryl (where the aryl is a C6-C12 aryl, and the two aryls may be bonded via a single bond or a linking group), a C1-C24 alkyl, or a C3-C24 cycloalkyl, and at least one hydrogen in these substituents may be substituted with a C6-C12 aryl, a C2-C15 heteroaryl, a C1-C6 alkyl, or a C3-C14 cycloalkyl. "-C(-R)" in the c ring c )=" can be replaced with "-N=". In ring a and ring b, any "-C(-R)=" (where R is R a or R b The part "-N=" may be replaced with any "-C(-R)=C(-R)-" (where R is R a or R bThe R in "-N(-R)-", "-O-", "-S-", "-C(-R)2-", "-Si(-R)2-", or "-Se-" may be replaced by "-N(-R)-", "-C(-R)2-", and "-Si(-R)2-", where R is hydrogen, an aryl with 6 to 12 carbon atoms, a heteroaryl with 2 to 15 carbon atoms, an alkyl with 1 to 6 carbon atoms, or a silicone with 3 to 14 carbon atoms. It is a chloroalkyl group, and at least one hydrogen atom in R may be substituted with an alkyl group having 1 to 6 carbon atoms or a cycloalkyl group having 3 to 14 carbon atoms, and the two R groups in "-C(-R)2-" and the two R groups in "-Si(-R)2-" are independently single bonds, -CH=CH-, -CR=CR-, -C≡C-, =C(-R)-, =N-, -N(-R)-, -O-, -S- The R in "-CR=CR-", "=C(-R)-", "-N(-R)-", "-C(-R)2-", and "-Si(-R)2-" are each independently hydrogen, a carbon 6-10 aryl, a carbon 2-10 heteroaryl, a carbon 1-5 alkyl, a carbon 1-5 alkenyl, a carbon 1-5 alkynyl, or a carbon 5-10 cycloalkyl, and at least one hydrogen in the R may be substituted with a carbon 1-6 alkyl or a carbon 3-14 cycloalkyl, and two adjacent Rs may be bonded together to form a carbon 3-14 cycloalkylene ring, a carbon 6-12 arylene ring, or a carbon 2-15 heteroarylene ring. Y 1 , Y 2 , and Y 3 These are, independently, >B-, >P-, >P(=O)-, or >P(=S)-, X 1 , X 2 , X 3 , and X 4Each of these is independently >NR, >O, or >S, where R in >NR is hydrogen, a C6-C12 aryl, a C2-C15 heteroaryl, a C1-C6 alkyl, or a C3-C14 cycloalkyl, and at least one hydrogen in R may be substituted with a C1-C6 alkyl or a C3-C14 cycloalkyl. Also, the X 1 or X 3 As "NR", R represents at least one of the a-ring and b-ring, and X 2 or X 4 The R in ">NR" may be bonded to at least one of the a-ring and c-ring by a single bond, -CH=CH-, -CR=CR-, -C≡C-, =C(-R)-, =N-, -N(-R)-, -O-, -S-, -C(-R)2-, -Si(-R)2-, or -Se-, and the R in "-CR=CR-", "=C(-R)-", "-N(-R)-", "-C(-R)2-", and "-Si(-R)2-" may be independently bonded to hydrogen, or an atom having 6 to 12 carbon atoms. R is a heteroaryl group having 2 to 15 carbon atoms, an alkyl group having 1 to 6 carbon atoms, an alkenyl group having 1 to 6 carbon atoms, an alkynyl group having 1 to 6 carbon atoms, or a cycloalkyl group having 3 to 14 carbon atoms, and at least one hydrogen atom in R may be substituted with an alkyl group having 1 to 6 carbon atoms or a cycloalkyl group having 3 to 14 carbon atoms, and two adjacent R groups may be bonded together to form a cycloalkylene ring having 3 to 14 carbon atoms, an arylene ring having 6 to 12 carbon atoms, or a heteroarylene ring having 2 to 15 carbon atoms. In the compound represented by formula (2) above, at least one of the a-ring, b-ring, c-ring, the formed ring, the aryl, and the heteroaryl may be condensed with at least one cycloalkane having 3 to 24 carbon atoms, and at least one hydrogen atom in the cycloalkane may be substituted with an aryl having 6 to 16 carbon atoms, a heteroaryl having 2 to 15 carbon atoms, an alkyl having 1 to 12 carbon atoms, or a cycloalkyl having 3 to 16 carbon atoms. At least one hydrogen in the compound represented by the above formula (2) may be substituted with deuterium, cyano, or halogen. The polycyclic aromatic compound according to item 3.

[0017] Item 5. In the above formula (2), R a 、R b 、and R c are each independently hydrogen, aryl having 6 to 16 carbon atoms, heteroaryl having 2 to 20 carbon atoms, diarylamino (where aryl is aryl having 6 to 10 carbon atoms), diarylboryl (where aryl is aryl having 6 to 10 carbon atoms and the two aryls may be bonded via a single bond or a linking group), alkyl having 1 to 12 carbon atoms, or cycloalkyl having 3 to 16 carbon atoms, and at least one hydrogen in the R a 、R b 、and R c may be substituted with aryl having 6 to 10 carbon atoms, heteroaryl having 2 to 10 carbon atoms, alkyl having 1 to 5 carbon atoms, or cycloalkyl having 5 to 10 carbon atoms. Also, adjacent groups among the R a and R b may be bonded to form an aryl ring having 9 to 16 carbon atoms or a heteroaryl ring having 6 to 15 carbon atoms together with the a-ring and the b-ring, and at least one hydrogen in the formed ring may be substituted with aryl having 6 to 16 carbon atoms, heteroaryl having 2 to 20 carbon atoms, diarylamino (where aryl is aryl having 6 to 10 carbon atoms), diarylboryl (where aryl is aryl having 6 to 10 carbon atoms and the two aryls may be bonded via a single bond or a linking group), alkyl having 1 to 12 carbon atoms, or cycloalkyl having 3 to 16 carbon atoms, and at least one hydrogen in these substituents may be substituted with aryl having 6 to 10 carbon atoms, heteroaryl having 2 to 10 carbon atoms, alkyl having 1 to 5 carbon atoms, or cycloalkyl having 5 to 10 carbon atoms. The “-C(−R c )=” in the c-ring may be replaced with “-N=”. In ring a and ring b, any “-C(-R)=” (where R is R a or R b may be replaced by “-N=”. Any “-C(-R)=C(-R)-” (where R is R a or R b may be replaced by “-N(-R)-”, “-O-”, “-S-”, or “-C(-R)2-”. The R in the “-N(-R)-” and the R in the “-C(-R)2-” are hydrogen, aryl having 6 to 12 carbon atoms, heteroaryl having 2 to 15 carbon atoms, alkyl having 1 to 6 carbon atoms, or cycloalkyl having 3 to 14 carbon atoms. At least one hydrogen in the R may be substituted by alkyl having 1 to 6 carbon atoms or cycloalkyl having 3 to 14 carbon atoms. Y 1 Y 2 and Y 3 are each independently >B-, >P-, >P(=O)-, or >P(=S)-. X 1 X 2 X 3 and X 4 are each independently >N-R, >O, or >S. The R in the “>N-R” is hydrogen, aryl having 6 to 12 carbon atoms, heteroaryl having 2 to 15 carbon atoms, alkyl having 1 to 6 carbon atoms, or cycloalkyl having 3 to 14 carbon atoms. At least one hydrogen in the R may be substituted by alkyl having 1 to 6 carbon atoms or cycloalkyl having 3 to 14 carbon atoms. Also, the R in the “>N-R” as the X 1 or the X 3 and the b ring, and the X 2 or the X 4The R in ">NR" may be bonded to the a-ring by a single bond, -CH=CH-, -CR=CR-, -N(-R)-, -O-, -S-, or -C(-R)2-, and the R in "-CR=CR-", "-N(-R)-", and "-C(-R)2-" may each be independently hydrogen, a carbon 6-10 aryl, a carbon 2-10 heteroaryl, a carbon 1-5 alkyl, a carbon 1-5 alkenyl, a carbon 1-5 alkynyl, or a carbon 5-10 cycloalkyl, and at least one hydrogen in the R may be substituted with a carbon 1-5 alkyl or a carbon 5-10 cycloalkyl, and two adjacent Rs may be bonded to each other to form a carbon 6-10 arylene ring or a carbon 2-10 heteroarylene ring. In the compound represented by formula (2) above, at least one of the a-ring, b-ring, c-ring, the formed ring, the aryl, and the heteroaryl may be condensed with at least one cycloalkane having 3 to 16 carbon atoms, and at least one hydrogen atom in the cycloalkane may be substituted with an aryl having 6 to 10 carbon atoms, a heteroaryl having 2 to 10 carbon atoms, an alkyl having 1 to 5 carbon atoms, or a cycloalkyl having 5 to 10 carbon atoms. In the compound represented by formula (2) above, at least one hydrogen atom may be substituted with deuterium, cyano, or halogen. Polycyclic aromatic compounds as described in item 3.

[0018] Section 6. In the above equation (2), R a , R b , and R c Each of these is independently hydrogen, a carbon-6 to carbon-16 aryl group, a carbon-2 to carbon-20 heteroaryl group, a diarylamino group (where the aryl group is a carbon-6 to carbon-10 aryl group), a diarylboryl group (where the aryl group is a carbon-6 to carbon-10 aryl group, and the two aryl groups may be linked by a single bond or a linking group), a carbon-1 to carbon-12 alkyl group, or a carbon-3 to carbon-16 cycloalkyl group, and the R a , R b , and R cAt least one hydrogen atom in may be substituted with an alkyl group having 1 to 5 carbon atoms, or a cycloalkyl group having 5 to 10 carbon atoms. "-C(-R)" in the c ring c )=" can be replaced with "-N=". In ring a and ring b, any "-C(-R)=" (where R is R a or R b The part "-N=" may be replaced with any "-C(-R)=C(-R)-" (where R is R a or R b The part (which is) may be replaced with "-N(-R)-", "-O-", or "-S-", where R in "-N(-R)-" is an aryl group having 6 to 10 carbon atoms, a heteroaryl group having 2 to 10 carbon atoms, an alkyl group having 1 to 5 carbon atoms, or a cycloalkyl group having 5 to 10 carbon atoms. Y 1 , Y 2 , and Y 3 It is >B-, X 1 , X 2 , X 3 , and X 4 Each of these is independently >NR or >O, where R in ">NR" is a C6-C10 aryl, a C2-C10 heteroaryl, a C1-C5 alkyl, or a C5-C10 cycloalkyl, and at least one hydrogen in R may be substituted with a C1-C5 alkyl or a C5-C10 cycloalkyl. Also, the X 1 or X 3 As for ">NR", R is the aforementioned b ring and the aforementioned X 2 or X 4The R in ">NR" may be bonded to the a-ring by a single bond or by -CR=CR-, and each of the R in "-CR=CR-" is independently a hydrogen, a carbon 6-10 aryl, a carbon 2-10 heteroaryl, a carbon 1-5 alkyl, a carbon 1-5 alkenyl, a carbon 1-5 alkynyl, or a carbon 5-10 cycloalkyl, and at least one hydrogen in the R may be substituted with a carbon 1-5 alkyl or a carbon 5-10 cycloalkyl, and two adjacent Rs may be bonded to each other to form a carbon 6-10 arylene ring or a carbon 2-10 heteroarylene ring. In the compound represented by formula (2) above, at least one hydrogen atom may be substituted with deuterium, cyano, or halogen. Polycyclic aromatic compounds as described in item 3.

[0019] Section 7. A polycyclic aromatic compound as described in item 1, represented by one of the following structural formulas. [ka] Each benzene ring in the above structural formula may be independently substituted with a C6-C16 aryl group, a C2-C20 heteroaryl group, a diarylamino group (where the aryl group is a C6-C10 aryl group), a diarylboryl group (where the aryl group is a C6-C10 aryl group, and the two aryl groups may be linked by a single bond or a linking group), a C1-C12 alkyl group, or a C3-C16 cycloalkyl group, and at least one hydrogen atom in the substituent may be substituted with a C1-C5 alkyl group or a C5-C10 cycloalkyl group. At least one hydrogen atom in the compound represented by the above structural formula may be substituted with deuterium, cyano, or halogen.

[0020] Section 8. A polycyclic aromatic compound as described in item 1, represented by one of the following structural formulas. [ka]

[0021] Section 9. A reactive compound obtained by substituting a reactive substituent onto a polycyclic aromatic compound as described in any of items 1 to 8.

[0022] Section 10. A polymer compound obtained by polymerizing the reactive compound described in item 9 as a monomer, or a polymer crosslinked product obtained by further crosslinking the polymer compound.

[0023] Section 11. A pendant-type polymer compound obtained by substituting a reactive compound described in item 9 into a main-chain polymer, or a pendant-type polymer crosslinked product obtained by further crosslinking the said pendant-type polymer compound.

[0024] Section 12. A material for organic devices containing a polycyclic aromatic compound as described in any of items 1 to 8.

[0025] Section 13. A material for organic devices containing the reactive compounds described in item 9.

[0026] Section 14. Materials for organic devices containing the polymer compounds or polymer crosslinks described in item 10.

[0027] Section 15. A material for organic devices containing a pendant-type polymer compound or a pendant-type polymer crosslinker as described in item 11.

[0028] Section 16. The organic device material described in any of items 12 to 15, wherein the organic device material is a material for an organic electroluminescent device, a material for an organic field-effect transistor, a material for an organic thin-film solar cell, or a material for a wavelength conversion filter.

[0029] Section 17. The organic device material according to item 16, wherein the aforementioned organic electroluminescent material is a material for the light-emitting layer.

[0030] Section 18. An ink composition comprising a polycyclic aromatic compound as described in any of items 1 to 8 and an organic solvent.

[0031] Section 19. An ink composition comprising the reactive compound described in item 9 and an organic solvent.

[0032] Section 20. An ink composition comprising a main-chain polymer, a reactive compound as described in item 9, and an organic solvent.

[0033] Section 21. An ink composition comprising a polymer compound or polymer crosslinker as described in item 10 and an organic solvent.

[0034] Section 22. An ink composition comprising a pendant-type polymer compound or pendant-type polymer crosslinker as described in item 11, and an organic solvent.

[0035] Section 23. An organic field light-emitting element comprising a pair of electrodes consisting of an anode and a cathode, and an organic layer disposed between the pair of electrodes, the organic layer containing a polycyclic aromatic compound as described in any of items 1 to 8, a reactive compound as described in item 9, a polymer compound or polymer crosslink as described in item 10, or a pendant-type polymer compound or pendant-type polymer crosslink as described in item 11.

[0036] Section 24. The organic electroluminescent element described in item 23, wherein the organic layer is a light-emitting layer.

[0037] Section 25. The organic field light-emitting element according to item 24, wherein the light-emitting layer comprises a host and the polycyclic aromatic compound, reactive compound, polymer compound, polymer crosslinker, pendant-type polymer compound, or pendant-type polymer crosslinker as a dopant.

[0038] Section 26. The light-emitting layer further contains at least one selected from the group consisting of a compound represented by the following general formula (H1), a compound represented by the following general formula (H2), a compound represented by the following general formula (H3), a compound containing a structure represented by the following general formula (H4), a compound represented by the following general formula (H5), a compound represented by the following general formula (H6), and a TADF material, as described in item 25. [ka] In the above general formula (H1), L 1 These are arylenes with 6 to 30 carbon atoms or heteroarylenes with 2 to 30 carbon atoms. In the above general formula (H2), L 2 and L 3 These are, independently, aryl atoms with 6 to 30 carbon atoms or heteroaryl atoms with 2 to 30 carbon atoms. In the above general formula (H3), MU is a divalent group that can be independently represented by removing any two hydrogen atoms from an aromatic compound, EC is a monovalent group that can be independently represented by removing any one hydrogen atom from an aromatic compound, the two hydrogens in MU are substituted with EC or MU, and k is an integer between 2 and 50000. 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). In the above general formula (H5), R 1 ~R 11 Each of these is independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, alkyl, or cycloalkyl, and R 1 ~R 11 At least one hydrogen in may be further substituted with an aryl, heteroaryl, diarylamino, alkyl, or cycloalkyl group. R 1 ~R 11Among them, adjacent groups may combine with each other to form an aryl ring or a heteroaryl ring together with the a-ring, b-ring or c-ring, and at least one hydrogen in the formed ring may be substituted with aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, alkyl or cycloalkyl, and at least one hydrogen in these substituents may be further substituted with aryl, heteroaryl, diarylamino, alkyl or cycloalkyl. In the a-ring, b-ring, and c-ring, any “-C(−R)=” (where R is R 1 ~R 11 as defined) may be replaced by “-N=”. In the above general formula (H6), R 1 ~R 16 are each independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, alkyl or cycloalkyl, and at least one hydrogen in the R 1 ~R 16 may be further substituted with aryl, heteroaryl, diarylamino, alkyl or cycloalkyl. R 1 ~R 16 Among them, adjacent groups may combine with each other to form an aryl ring or a heteroaryl ring together with the a-ring, b-ring, c-ring or d-ring, and at least one hydrogen in the formed ring may be substituted with aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, alkyl or cycloalkyl, and at least one hydrogen in these substituents may be further substituted with aryl, heteroaryl, diarylamino, alkyl or cycloalkyl, and at least one hydrogen in the compound or structure represented by the above formulas may be substituted with alkyl having 1 to 6 carbon atoms, cycloalkyl having 3 to 14 carbon atoms, cyano, halogen or deuterium.

[0039] Item 27. An organic electroluminescent element according to any one of claims 23 to 26, comprising at least one electron transport layer and an electron injection layer disposed between the cathode and the light-emitting layer, wherein at least one of the electron transport layer and the electron injection layer contains at least one selected from the group consisting of borane derivatives, pyridine derivatives, fluorantene derivatives, BO derivatives, anthracene derivatives, benzofluorene derivatives, phosphine oxide derivatives, pyrimidine derivatives, carbazole derivatives, triazine derivatives, benzimidazole derivatives, phenanthroline derivatives, quinolinol-based metal complexes, thiazole derivatives, benzothiazole derivatives, silole derivatives, and azoline derivatives.

[0040] Section 28. The organic electroluminescent device according to claim 27, wherein at least one layer of the electron transport layer and electron injection layer further contains 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.

[0041] Section 29. An organic field light-emitting device according to any one of claims 23 to 28, wherein at least one of the hole injection layer, hole transport layer, light-emitting layer, electron transport layer, and electron injection layer comprises a polymer compound obtained by polymerizing a low molecular weight compound capable of forming each layer as a monomer, or a polymer crosslinked product obtained by further crosslinking said polymer compound, or a pendant-type polymer compound obtained by reacting a low molecular weight compound capable of forming each layer with a main-chain type polymer, or a pendant-type polymer crosslinked product obtained by further crosslinking said pendant-type polymer compound.

[0042] Section 30. A display device or lighting device equipped with an organic electroluminescent element as described in any of items 23 to 29.

[0043] Section 31. A wavelength conversion filter comprising the wavelength conversion filter material described in item 16. [Effects of the Invention]

[0044] 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, and by using this polycyclic aromatic compound, an excellent organic device such as an organic EL element can be provided.

[0045] Specifically, the inventors have found that polycyclic aromatic compounds, in which aromatic rings are linked by heteroatoms such as boron, phosphorus, oxygen, nitrogen, and sulfur, have a large HOMO-LUMO gap or a small HOMO-LUMO gap (band gap Eg in thin films) depending on the method of linking the heteroatoms. This is thought to be because the 6-membered ring containing the heteroatoms has low aromaticity, which suppresses or promotes the reduction of the HOMO-LUMO gap associated with the expansion of the conjugated system and the localization or delocalization of each orbital. Because these polycyclic aromatic compounds have a robust framework in which 5-membered or 6-membered rings are condensed or linked, the full width at half maximum of the fluorescence emission peak is narrow, and when used as an emitter for organic EL devices, high color purity emission can be obtained. In addition, by selecting the method of linking the heteroatoms, thermally activated delayed fluorescence can be observed, and high efficiency can be obtained when used as an emitter for organic EL devices. Furthermore, by introducing substituents, the energies of HOMO and LUMO can be arbitrarily moved, making it possible to optimize the ionization potential and electron affinity according to the surrounding material. However, the present invention is not limited to these principles. [Brief explanation of the drawing]

[0046]

Figure 1

[0047] 1. Polycyclic aromatic compound <Description of the overall structure of the compound> The present invention relates to a polycyclic aromatic compound represented by the following general formula (1), and more preferably, a polycyclic aromatic compound represented by the following general formula (2). The definitions of the symbols in each structural formula 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]

[0048] All compounds have a structure formed by the condensation of two A rings (a rings) and two B rings (b rings) into a condensed seven-ring structure. The condensed seven-ring structure is clearly shown in formula (1), Y 1 Centered on X 1 , X 2 , and Y 3 A condensate of three 6-membered rings, including Y 2 Centered on X 3 , X 4 , and Y 3 This is a condensate of three six-membered rings, which include the c ring, and a condensate of seven six-membered rings formed by the condensation of all of the c rings. The same applies to equation (2).

[0049] <Description of the ring structure and its substituents in the compound> In each formula, rings A and B are independently aryl or heteroaryl rings, and at least one hydrogen in these rings may be substituted with a substituent. Preferred substituents are optionally substituted aryl, optionally substituted heteroaryl, optionally substituted diarylamino, optionally substituted diheteroarylamino, optionally substituted arylheteroarylamino (an amino group having an aryl and a heteroaryl), optionally substituted diarylboryl (the two aryls may be linked by a single bond or a linking group), optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted alkoxy, optionally substituted aryloxy, optionally substituted diarylphosphoryl, or substituted silyl. If these substituents have further substituents, examples of such substituents include aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl (the two aryls may be linked by a single bond or a linking group), alkyl, cycloalkyl, alkoxy, aryloxy, diarylphosphoryl, or substituted silyl. Details of the rings and substituents listed here will be described in more detail later.

[0050] R in each equation a , R b , and R cis a hydrogen or a substituent, specifically, hydrogen, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted diarylamino, optionally substituted diheteroarylamino, optionally substituted arylheteroarylamino (an amino group having aryl and heteroaryl), optionally substituted diarylboril (the two aryls may be bonded via a single bond or a linking group), optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted alkoxy, optionally substituted aryloxy, optionally substituted diarylphosphoryl, or substituted silyl is preferred. When these substituents further have a substituent, examples of the substituent include aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboril (the two aryls may be bonded via a single bond or a linking group), alkyl, cycloalkyl, alkoxy, aryloxy, diarylphosphoryl, or substituted silyl. Details of the rings and substituents listed here will be summarized and described later.

[0051] R in each formula a 、R b 、and R c Specific examples of are, independently of each other, hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboril (the two aryls may be bonded via a single bond or a linking group), alkyl, cycloalkyl, alkoxy, aryloxy, diarylphosphoryl, triarylsilyl, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, or alkyldicycloalkylsilyl, and at least one hydrogen in the R a 、R b 、and R c may be substituted with aryl, heteroaryl, alkyl, or cycloalkyl. Details of the substituents listed here will be summarized and described later.

[0052] The aryl or heteroaryl rings as rings A and B preferably have a 5-membered or 6-membered ring that shares two bonds with the fused 7-ring structure described above. Here, "a six-membered ring sharing two bonds with a fused seven-ring structure" refers to the a-ring and b-ring (benzene ring (six-membered ring)) that are fused to the fused seven-ring structure, as shown in formula (2), for example. Furthermore, "an aryl ring or heteroaryl ring (which is the A-ring and B-ring) having this six-membered ring" means that the A-ring and B-ring are formed solely by this six-membered ring, or that the A-ring and B-ring are formed to include this six-membered ring through the fusion of other rings or other elements. In other words, "an aryl ring or heteroaryl ring (which is the A-ring and B-ring) having a six-membered ring" here means that the six-membered rings that constitute all or part of the A-ring and B-ring are fused to the fused seven-ring structure. The same explanation also applies to "five-membered rings."

[0053] The A ring and B ring in formula (1) correspond to the a ring and its substituent R in formula (2), respectively. a , and the β ring and its substituent R b This corresponds to the structure in which "a ring A and a ring B having a 6-membered ring (which is a benzene ring)" are selected as the A and B rings of formula (1). In that sense, each ring in formula (2) is represented by the lowercase letters "a" and "b".

[0054] <Description of the change in the ring structure due to the bonding between substituents> Substituents R of the a-ring and b-ring a and R bAdjacent groups among these may bond together with the a-ring or b-ring to form an aryl ring or a heteroaryl 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, aryloxy, diarylphosphoryl, triarylsilyl, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, or alkyldicycloalkylsilyl, and at least one hydrogen in these substituents may be substituted with aryl, heteroaryl, alkyl, or cycloalkyl. Details of the rings and substituents listed here will be described in more detail later.

[0055] Therefore, the ring structure of the polycyclic aromatic compound of formula (2) changes depending on the bonding configuration of the substituents in the a-ring and b-ring, as shown in formulas (2-fr1) to (2-fr3) below. The A'-ring and B'-ring in each formula correspond to the A-ring and B-ring in formula (1), respectively. Note that each formula is shown simply as a partial structure.

[0056] [ka]

[0057] The A' and B' rings in the above formulas (2-fr1) to (2-fr3) are, as explained in formula (2), multiple substituents R a and R b The adjacent groups among them are bonded together, forming an aryl ring or heteroaryl ring with the a-ring and b-ring, respectively (they can also be described as fused rings formed by the condensation of other ring structures with the a-ring or b-ring). Furthermore, as can be seen from the above formula, for example, the substituent R of the a-ring a and the substituent R of the β ring b This does not apply to "adjacent groups," and these groups will not bond. In other words, "adjacent groups" refers to groups adjacent to each other on the same ring.

[0058] Specific examples of the above formulas (2-fr1) to (2-fr3) include structures having an A' or B' ring formed by the condensation of a benzene ring (a or b ring) with, for example, a benzene ring, an indole ring, a pyrrole ring, a benzofuran ring, or a benzothiophene ring, where the formed condensed ring A' or B' is a naphthalene ring, a carbazole ring, an indole ring, a dibenzofuran ring, or a dibenzothiophene ring, respectively.

[0059] For example, more specific examples of equations (2-fr1) to (2-fr3) are shown below. [ka]

[0060] The above equation (2-fr1-ex) is a specific example of equation (2-fr1), and represents two adjacent Rs in ring a of equation (2). a This is an example where a bond is formed, creating an aryl ring (naphthalene ring) represented by A' along with the a ring (benzene ring). The formed aryl ring has a 6-membered ring (benzene ring a) that shares a bond with the fused 7-ring structure described above. Note that any substituent can be added to the aryl ring A' (ring A in formula (1)) R a In addition, it is shown for n Rs, where the upper limit of n is the maximum number of permutations.

[0061] The above equation (2-fr2-ex) is a specific example of equation (2-fr2), and the two adjacent Rs in ring b of equation (2) b This is an example where a heteroaryl ring (carbazole ring) represented by B' is formed together with the b ring (benzene ring). The formed heteroaryl ring has a 6-membered ring (benzene ring b) that shares a bond with the fused 7-ring structure described above. Note that any substituent can be added to the aryl ring B' (ring B in formula (1)) R b In addition, it is shown for n Rs, where the upper limit of n is the maximum number of permutations.

[0062] The above equation (2-fr3-ex) is a specific example of equation (2-fr3), and is a combination of two adjacent Rs in ring a of equation (2). a The two adjacent R's in the b ring form a heteroaryl ring (dibenzofuran ring) indicated by A', along with the a ring (benzene ring). b This is an example where a bond is formed, creating an aryl ring (naphthalene ring) represented by B' along with the b ring (benzene ring). The formed heteroaryl ring and aryl ring have a 6-membered ring (benzene ring a and benzene ring b) that shares a bond with the fused 7-ring structure described above. Note that any substituent can be added to the heteroaryl ring A' (ring A in formula (1)) and the aryl ring B' (ring B in formula (1)) a and R b In addition, it is shown for n Rs, where the upper limit of n is the maximum number of permutations.

[0063] The above explanation can be applied equally to all forms other than the specific examples mentioned above.

[0064] <Central element Y in the compound 1 、Y 2 and the description of Y 3 > Y in each equation 1 , Y 2 , and Y 3 The R in ">C(-R)-", the R in ">Si(-R)-", and the R in ">Ge(-R)-" are each independently an optionally substituted aryl, an optionally substituted heteroaryl, an optionally substituted alkyl, or an optionally substituted cycloalkyl. 1 , Y 2 , and Y 3 However, in the case of >P(=O)-, >P(=S)-, >C(-R)-, >Si(-R)-, or >Ge(-R)-, the atoms bonded to the A ring (a ring), B ring (b ring), and c ring are P, C, Si, or Ge. 1 , Y 2, and Y 3 The substituents are preferably >B-, >P-, >P(=O)-, >P(=S)-, >C(-R)-, or >Si(-R)-, more preferably >B-, >P-, >P(=O)-, or >P(=S)-, and particularly preferably >B-. Details of the substituents listed here will be discussed later.

[0065] <Linking element X in the compound 1 、X 2 、X 3 and the description of X 4 > X in each equation 1 , X 2 , X 3 , and X 4 Each of these is independently >NR, >O, >S, >C(-R)2, >Si(-R)2, or >Se, where R in >NR, R in >C(-R)2, and R in >Si(-R)2 are independently hydrogen, an optionally substituted aryl, an optionally substituted heteroaryl, an optionally substituted alkyl, an optionally substituted alkenyl, an optionally substituted cycloalkyl, or an optionally substituted cycloalkenyl. X 1 , X 2 , X 3 , and X 4 From the viewpoint of stability, >NR, >O, >S, or >C(-R)2 are preferred, with >NR or >O being more preferred. Also, from the viewpoint of short-wavelength emission, >NR, >O, or >C(-R)2 are preferred, with >O or >C(-R)2 being more preferred. Details of the substituents listed here will be explained in more detail later.

[0066] Also, the X 1 ~X 4The two R groups in ">C(-R)2" and the two R groups in ">Si(-R)2" may be independently bonded by single bonds or linking groups (collectively called bonding groups). Examples of such linking groups include -CH2-CH2-, -CHR-CHR-, -CR2-CR2-, -CH=CH-, -CR=CR-, -C≡C-, =C(-R)-, =N-, -N(-R)-, -O-, -S-, -C(-R)2-, -Si(-R)2-, or -Se-, and the following structure is an example. Furthermore, the R in "-CHR-CHR-", "-CR2-CR2-", "-CR=CR-", "=C(-R)-", "-N(-R)-", "-C(-R)2-", and "-Si(-R)2-" are each independently hydrogen, aryl, heteroaryl, alkyl, alkenyl, alkynyl, or cycloalkyl, and at least one hydrogen in each R may be substituted with an alkyl or cycloalkyl. In addition, two adjacent Rs in "-CHR-CHR-", "-CR2-CR2-", "-CR=CR-", "-C(-R)2-", and "-Si(-R)2-" 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 later. [ka]

[0067] Preferred bonding groups are single bonds and linking groups -CR=CR-, -N(-R)-, -O-, -S-, -C(-R)2-, -Si(-R)2-, and -Se-; more preferred are single bonds and linking groups -CR=CR-, -N(-R)-, -O-, -S-, and -C(-R)2-; even more preferred are single bonds and linking groups -CR=CR-, -N(-R)-, -O-, and -S-; and most preferred is single bond and linking group -CR=CR-.

[0068] The positions where the two R groups bond via the bonding 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).

[0069] <X 1 ~X 4 <Description of the change in the ring structure due to the bonding between the ring and X> X 1 or X 3 As such, R in ">NR", R in ">C(-R)2", and R in ">Si(-R)2" may each be independently bonded to at least one ring of the A ring (a ring) and B ring (b ring) by a single bond or linking group, X 2 or X 4 The R in ">NR", the R in ">C(-R)2", and the R in ">Si(-R)2" may each be independently bonded to at least one of the A (a) and c rings by a single bond or a linking group. X that may be involved in the bond 1 Of these, >NR and >C(-R)2 are preferred, and >NR is more preferred. The rings that join together are, X 1 or X 3 For X, the B ring (b ring), X 2 or X 4 For this, ring A (ring a) is preferred. Examples of linking groups that bond R to the ring include -CH2-CH2-, -CHR-CHR-, -CR2-CR2-, -CH=CH-, -CR=CR-, -C≡C-, =C(-R)-, =N-, -N(-R)-, -O-, -S-, -C(-R)2-, -Si(-R)2-, and -Se-, with -CH=CH-, -CR=CR-, -N(-R)-, -O-, -S-, and -C(-R)2- being preferred, -CH=CH-, -CR=CR-, -N(-R)-, -O-, and -S- being more preferred, -CR=CR-, -N(-R)-, -O-, and -S- being even more preferred, and -CR=CR- being particularly preferred. Furthermore, the R in "-CHR-CHR-", "-CR2-CR2-", "-CR=CR-", "=C(-R)-", "-N(-R)-", "-C(-R)2-", and "-Si(-R)2-" are each independently hydrogen, aryl, heteroaryl, alkyl, alkenyl, alkynyl, or cycloalkyl, and at least one hydrogen in each R may be substituted with alkyl or cycloalkyl. Also, two adjacent Rs may bond together to form a cycloalkylene ring, an arylene ring, and a heteroarylene ring. At least one hydrogen in these rings may also be substituted with alkyl or cycloalkyl. Details of the substituents listed here will be explained in more detail later.

[0070] In equation (1), "the X 1 or X 3 The R in ">NR", the R in ">C(-R)2", and the R in ">Si(-R)2" are, independently of each other, at least one ring of the A ring and the B ring, and the X 2 or X 4 The provision that "R in '>NR', R in '>C(-R)2', and R in '>Si(-R)2' are each independently bonded to at least one of the A and c rings by a single bond or a linking group" is used in formula (2) as "the X 1 or X 3The R in ">NR", the R in ">C(-R)2", and the R in ">Si(-R)2" are, independently of each other, at least one of the a-ring and b-ring, and the X 2 or X 4 The R in ">NR", the R in ">C(-R)2", and the R in ">Si(-R)2" each independently correspond to the provision that "they are bonded to at least one of the a-ring and c-ring by single bonds, -CH2-CH2-, -CHR-CHR-, -CR2-CR2-, -CH=CH-, -CR=CR-, -C≡C-, =C(-R)-, =N-, -N(-R)-, -O-, -S-, -C(-R)2-, -Si(-R)2-, and -Se-".

[0071] This regulation can be represented, for example, by the following structural formula. Note that substituent R in the structural formula a , R b and R c It was hidden, but it actually exists. [ka]

[0072] The structural formula on the left is, in formula (2), X 1 In the options (>NR, >C(-R)2, and >Si(-R)2), R is bonded to the b-ring (benzene ring) by a single bond or a linking group, X 1 While incorporating the benzene ring, other rings condense around the b-ring (benzene ring) to form a B' ring. X 2 In the options (>NR, >C(-R)2, and >Si(-R)2), R is bonded to the left a-ring (benzene ring) by a single bond or a linking group, X 2 While incorporating the other rings, the left a-ring (benzene ring) condenses with the other rings to form the left A'-ring. X 3 In the options (>NR, >C(-R)2, and >Si(-R)2), R is bonded to the right a-ring (benzene ring) by a single bond or a linking group, X 3This represents a compound in which another ring condenses with the right-hand a-ring (benzene ring) while incorporating the other ring, forming the right-hand A' ring. The formed fused ring B', the fused ring A' on the left, and the fused ring A' on the right are, for example, rings having an azepine structure, phenoxazine rings, phenothiazine rings, carbazole rings, or acridine rings. Note that X is not included in the above structural formula. 4 There are also examples where a ring is bonded to a chromosome, or where a c-ring is bonded.

[0073] The structural formula on the right represents a more specific example of the structural formula on the left. X 1 The R (phenyl group) of NR is bonded to the b ring (benzene ring) by the linking group "-CR=CR-" (two adjacent Rs are bonded together to form an aryl ring which is a phenylene ring), forming the ring B' which has an azepine structure, enclosed by the dashed line. X 2 The R (phenyl group) of NR is bonded to the left a ring (benzene ring) by the linking group "-O-", forming the phenoxazine ring A' (left side) enclosed by the dashed line. X 3 This represents a compound in which the R (phenyl group) of >NR is bonded to the right-hand a (benzene ring) ring via a single bond, forming the carbazole ring A' (right side) enclosed by the dashed line.

[0074] In one embodiment, X in each formula 1 ~X 4 At least one of these may be bonded to the A ring (a ring), B ring (b ring), or c ring by a linking group "-CR=CR-". Preferably, X 1 and X 3 At least one of these may be bonded to the B ring (b ring) by the "-CR=CR-" linkage. In addition, two adjacent R atoms in the "-CR=CR-" linkage may be bonded to each other to form a cycloalkylene ring, an arylene ring, or a heteroarylene ring, and at least one hydrogen atom in these rings may be substituted with an alkyl or cycloalkyl group.

[0075] Furthermore, the explanations of the specific examples mentioned above can be applied equally to all other forms as well.

[0076] <Description of the structural changes of the a-ring, b-ring, and c-ring>

[0077] In the explanations so far, we have basically described the c-ring in formula (1) and the a-ring, b-ring, and c-ring in formula (2) as benzene rings. Below, we will describe examples in which these rings undergo structural changes that are not benzene rings, but rather 5-membered or 6-membered aryl rings or heteroaryl rings. Note that the explanations so far can be understood similarly even when these rings undergo the following structural changes.

[0078] <Structural change of the c-ring> "-C(-R)" in the c ring c The )=" can be replaced with "-N=", and may be a pyridine ring or a pyrazine ring. Note that the following structural formulas are those in which only the c ring and a portion of its surrounding structure are extracted. [ka]

[0079] <Structural changes of the a-ring and b-ring (1)> In ring a and ring b, any "-C(-R)=" (where R is R a or R b The part "-N=" may be replaced with "-N=". Note that the following structural formulas are those in which only the a-ring or b-ring and a part of its surrounding structure are extracted. [ka]

[0080] As shown above, the a-ring or b-ring represented as a benzene ring in formula (2) may be changed to a pyridine ring, pyrimidine ring, pyridazine ring, pyrazine ring, or other nitrogen-containing heteroaryl ring. Also, if there are adjacent groups on the a-ring or b-ring (two R in the above structural formula) a Both and two R bAs mentioned above, these elements can combine with the a-ring or b-ring to form a heteroaryl ring (a quinoline ring in the above structural formula), and the formed ring may be further substituted (indicated by n Rs).

[0081] The same applies when other parts are replaced with "-N=" or when adjacent substituents bond to form other heteroaryl rings.

[0082] <Structural change of the a-ring (2)> In ring a, any "-C(-R a )=C(-R a The substituents "-N(-R)-", "-O-", "-S-", "-C(-R)2-", "-Si(-R)2-", or "-Se-", where R in "-N(-R)-", R in "-C(-R)2-", and R in "-Si(-R)2-" are hydrogen, aryl, heteroaryl, alkyl, or cycloalkyl, and at least one hydrogen in these substituents may be substituted with alkyl or cycloalkyl. Details of the substituents listed here will be described later. [ka] The structural formulas shown above represent only the a-ring and a portion of its surrounding structure; to avoid complexity, the wavy lines indicating the substructures have been omitted.

[0083] As shown above, the ring a, which is represented as a benzene ring in formula (2), may be changed to an R-substituted pyrrole ring, a furan ring, a thiophene ring, or other nitrogen-containing, oxygen-sulfur-silicon-selenium heteroaryl ring (5-membered ring) or aryl ring (5-membered ring).

[0084] The same applies when other parts are replaced with "-N(-R)-", "-O-", "-S-", "-C(-R)2-", "-Si(-R)2-", or "-Se-".

[0085] The two R atoms in "-C(-R)2-" and the two R atoms in "-Si(-R)2-" may be independently bonded by a single bond or a linking group (collectively called a bonding group). Examples of such linking groups include -CH2-CH2-, -CHR-CHR-, -CR2-CR2-, -CH=CH-, -CR=CR-, -C≡C-, =C(-R)-, =N-, -N(-R)-, -O-, -S-, -C(-R)2-, -Si(-R)2-, or -Se-, and the following structure is an example. Furthermore, the R in "-CHR-CHR-", "-CR2-CR2-", "-CR=CR-", "=C(-R)-", "-N(-R)-", "-C(-R)2-", and "-Si(-R)2-" are each independently hydrogen, aryl, heteroaryl, alkyl, alkenyl, alkynyl, or cycloalkyl, and at least one hydrogen in each R may be substituted with an alkyl or cycloalkyl. In addition, two adjacent Rs in "-CHR-CHR-", "-CR2-CR2-", "-CR=CR-", "-C(-R)2-", and "-Si(-R)2-" 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 later. [ka]

[0086] Preferred bonding groups are single bonds and linking groups -CR=CR-, -N(-R)-, -O-, -S-, -C(-R)2-, -Si(-R)2-, and -Se-; more preferred are single bonds and linking groups -CR=CR-, -N(-R)-, -O-, -S-, and -C(-R)2-; even more preferred are single bonds and linking groups -CR=CR-, -N(-R)-, -O-, and -S-; and most preferred is single bond and linking group -CR=CR-.

[0087] The positions where the two R groups bond via the bonding 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).

[0088] <Structural change of the b-ring (2)> In ring b, any "-C(-R b )=C(-R b The substituents "-N(-R)-", "-O-", "-S-", "-C(-R)2-", "-Si(-R)2-", or "-Se-", where R in "-N(-R)-", R in "-C(-R)2-", and R in "-Si(-R)2-" are hydrogen, aryl, heteroaryl, alkyl, or cycloalkyl, and at least one hydrogen in these substituents may be substituted with alkyl or cycloalkyl. Details of the substituents listed here will be described later. [ka] The structural formulas shown above represent only the b-ring and a portion of its surrounding structure; to avoid complexity, the wavy lines indicating the substructures have been omitted.

[0089] As shown above, the b-ring represented as a benzene ring in formula (2) may be changed to an R-substituted pyrrole ring, a furan ring, a thiophene ring, or other nitrogen-containing, oxygen-sulfur-silicon-selenium heteroaryl ring (5-membered ring) or aryl ring (5-membered ring).

[0090] The same applies when other parts are replaced with "-N(-R)-", "-O-", "-S-", "-C(-R)2-", "-Si(-R)2-", or "-Se-".

[0091] The two R atoms in "-C(-R)2-" and the two R atoms in "-Si(-R)2-" may be independently bonded by a single bond or a linking group (collectively called a bonding group). Examples of such linking groups include -CH2-CH2-, -CHR-CHR-, -CR2-CR2-, -CH=CH-, -CR=CR-, -C≡C-, =C(-R)-, =N-, -N(-R)-, -O-, -S-, -C(-R)2-, -Si(-R)2-, or -Se-, and the following structure is an example. Furthermore, the R in "-CHR-CHR-", "-CR2-CR2-", "-CR=CR-", "=C(-R)-", "-N(-R)-", "-C(-R)2-", and "-Si(-R)2-" are each independently hydrogen, aryl, heteroaryl, alkyl, alkenyl, alkynyl, or cycloalkyl, and at least one hydrogen in each R may be substituted with an alkyl or cycloalkyl. In addition, two adjacent Rs in "-CHR-CHR-", "-CR2-CR2-", "-CR=CR-", "-C(-R)2-", and "-Si(-R)2-" 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 later. [ka]

[0092] Preferred bonding groups are single bonds and linking groups -CR=CR-, -N(-R)-, -O-, -S-, -C(-R)2-, -Si(-R)2-, and -Se-; more preferred are single bonds and linking groups -CR=CR-, -N(-R)-, -O-, -S-, and -C(-R)2-; even more preferred are single bonds and linking groups -CR=CR-, -N(-R)-, -O-, and -S-; and most preferred is single bond and linking group -CR=CR-.

[0093] The positions where the two R groups bond via the bonding 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).

[0094] <Specific description of the ring and substituents> Next, we will provide a detailed explanation of the rings and substituents listed in the previous explanation (including the second substituent that further substitutes for the first substituent).

[0095] The "aryl ring" is, for example, an aryl ring having 6 to 30 carbon atoms, preferably an aryl ring having 6 to 20 carbon atoms, an aryl ring having 6 to 16 carbon atoms, an aryl ring having 6 to 12 carbon atoms, or an aryl ring having 6 to 10 carbon atoms. Note that the "aryl rings" as rings A and B in formula (1) are defined as "R" in formula (2). a and R b This corresponds to "an aryl ring formed by the bonding of adjacent groups together with the a-ring and b-ring," but for this "formed aryl ring," since the a-ring or b-ring is already composed of a benzene ring with 6 carbon atoms, the lower limit of the carbon number is 9, which is the total carbon number of the fused ring formed by the fusion of the smallest 5-membered ring with this benzene ring.

[0096] Specific examples of "aryl rings" include, for example, the monocyclic benzene ring, the condensed bicyclic naphthalene ring, the condensed tricyclic acenaphthylene ring, fluorene ring, phenalene ring, or phenanthrene ring, anthracene ring, the condensed tetracyclic triphenylene ring, pyrene ring, or naphthacene ring, or the condensed pentacyclic perylene ring or pentacene ring.

[0097] A "heteroaryl ring" is, for example, a heteroaryl ring having 2 to 30 carbon atoms, preferably a heteroaryl ring having 2 to 25 carbon atoms, a heteroaryl ring having 2 to 20 carbon atoms, a heteroaryl ring having 2 to 15 carbon atoms, or a heteroaryl ring having 2 to 10 carbon atoms. A "heteroaryl ring" is also a heterocycle containing, for example, 1 to 5 heteroatoms selected from oxygen, sulfur, and nitrogen in addition to carbon as ring constituent atoms. Note that the "heteroaryl rings" as rings A and B in formula (1) are defined as "R" in formula (2). a and R b This corresponds to a heteroaryl ring formed by the bonding of adjacent groups to the a and b rings. However, for this "formed aryl ring," since the a or b ring is already composed of a benzene ring with 6 carbon atoms, the lower limit of the carbon number is 6, which is the total carbon number of the fused ring formed by the fusion of the smallest 5-membered ring with this benzene ring. However, as mentioned above, the a and b rings, which are benzene rings, may change to nitrogen-containing heteroaryl rings (6-membered or 5-membered rings) or oxygen-sulfur-containing heteroaryl rings (5-membered rings), etc., in which case the lower limit of the carbon number changes accordingly.

[0098] Specific examples of "heteroaryl rings" 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, quinoxaline rings, phenanthroline rings, phthalazine rings, naphthyridine rings, purine rings, pteridine rings, and carba These include zole rings, acridine rings, phenoxatiin rings, phenoxazine rings, phenothiazine rings, phenazine rings, phenazacillin rings, indoridine rings, furan rings, benzofuran rings, isobenzofuran rings, dibenzofuran rings, naphthobenzofuran rings, thiophene rings, benzothiophene rings, isobenzothiophene rings, dibenzothiophene rings, naphthobenzothiophene rings, benzophosphole rings, dibenzophosphole rings, benzophosphole oxide rings, dibenzophosphole oxide rings, furazan rings, thianthrene rings, indolocarbazole rings, benzoindocarbazole rings, benzobenzoindocarbazole rings, imidazoline rings, or oxazoline rings.

[0099] "Aryl" refers to, for example, an aryl with 6 to 30 carbon atoms, preferably an aryl with 6 to 20 carbon atoms, an aryl with 6 to 16 carbon atoms, an aryl with 6 to 12 carbon atoms, or an aryl with 6 to 10 carbon atoms.

[0100] Specific examples of "aryl" include, for example, the monocyclic phenyl, the bicyclic biphenylyl (2-biphenylyl, 3-biphenylyl, or 4-biphenylyl), the condensed bicyclic naphthyl (1-naphthyl or 2-naphthyl), the tricyclic 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, or p-terphenyl-4-yl), and the condensed tricyclic acenaphthyl These include len-(1-,3-,4-, or 5-)yl, fluoren-(1-,2-,3-,4-, or 9-)yl, phenalen-(1- or 2-)yl, or phenanthren-(1-,2-,3-,4-, or 9-)yl, the tetracyclic quaterphenylyl (5'-phenyl-m-terphenyl-2-yl, 5'-phenyl-m-terphenyl-3-yl, 5'-phenyl-m-terphenyl-4-yl, or m-quaterphenyl), the condensed tetracyclic triphenylene-(1- or 2-)yl, pyren-(1-,2-, or 4-)yl, or naphthacene-(1-,2-, or 5-)yl, or the condensed pentacyclic perylene-(1-,2-, or 3-)yl, or pentacene-(1-,2-, 5-, or 6-)yl.

[0101] Furthermore, an aryl as a second substituent, that is, an aryl as a substituent (second substituent) that is further substituted on a substituent (first substituent), also includes structures in which at least one hydrogen in the aryl is substituted with an aryl such as phenyl (specific examples are the groups mentioned above), an alkyl such as methyl (specific examples are the groups described later), or a cycloalkyl such as cyclohexyl or adamantyl (specific examples are the groups described later). One example is when the second substituent is a fluorenyl group, in which case at least one hydrogen at the 9-position is substituted with an aryl group such as phenyl, an alkyl group such as methyl, or a cycloalkyl group such as cyclohexyl or adamantyl, and such groups are also included in the aryl group as the second substituent.

[0102] 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.

[0103] 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.

[0104] 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.

[0105] Furthermore, a heteroaryl as a second substituent, that is, a heteroaryl as a substituent (second substituent) that is further substituted on a substituent (first substituent), includes structures in which at least one hydrogen in the heteroaryl is substituted with an aryl group such as phenyl (specific examples are the groups mentioned above), an alkyl group such as methyl (specific examples are the groups described later), or a cycloalkyl group such as cyclohexyl or adamantyl (specific examples are the groups described later). One example is when the second substituent is a carbazolyl group, in which case at least one hydrogen at the 9-position is substituted with an aryl group such as phenyl, an alkyl group such as methyl, or a cycloalkyl group such as cyclohexyl or adamantyl. Such groups are also included in heteroaryl groups as second substituents.

[0106] "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.

[0107] A "diarylamino" is an amino group substituted with two aryl groups. For details about these aryl groups, please refer to the explanation of "aryl" above. A "diheteroarylamino" is an amino group substituted with two heteroaryl groups. For details on these heteroaryl groups, please refer to the explanation of "heteroaryl" above. "Arylheteroarylamino" refers to an amino group substituted with aryl and heteroaryl groups. For details on these aryl and heteroaryl groups, please refer to the explanations of "aryl" and "heteroaryl" mentioned above.

[0108] A "diarylboryl" is a boryl group substituted with two aryl groups, and for details about these aryl groups, refer to the explanation of "aryl" above. These two aryl groups may also be bonded via a single bond or a linking group (e.g., -CH2-CH2-, -CHR-CHR-, -CR2-CR2-, -CH=CH-, -CR=CR-, -C≡C-, >NR, >O, >S, >C(-R)2, >Si(-R)2, or >Se). Here, the R in "-CHR-CHR-", "-CR2-CR2-", "-CR=CR-", ">NR", ">C(-R)2", and ">Si(-R)" are aryl, heteroaryl, diarylamino, alkyl, alkenyl, alkynyl, cycloalkyl, alkoxy, or aryloxy, and at least one hydrogen in the R may be further substituted with aryl, heteroaryl, alkyl, alkenyl, alkynyl, or cycloalkyl. Also, two adjacent Rs may form a ring to form cycloalkylene, arylene, and heteroarylene. For details of the substituents listed here, refer to the above-mentioned descriptions of "aryl", "arylene", "heteroaryl", "heteroarylene", and "diarylamino", as well as the later-described descriptions of "alkyl", "alkenyl", "alkynyl", "cycloalkyl", "cycloalkylene", "alkoxy", and "aryloxy".

[0109] "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.

[0110] 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.

[0111] 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 alkantriene-yl).

[0112] 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 also includes groups in which not just one but two or more single bonds are replaced with triple bonds (also called alkadiyne-yl or alkantriyne-yl).

[0113] "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.

[0114] 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.

[0115] 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.

[0116] 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).

[0117] "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.

[0118] 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.

[0119] 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.

[0120] "Diarylphosphoryl" is a group represented as "-P(=O)(-Ar)2" (where Ar is an aryl group), and for details about this aryl group, please refer to the explanation of "aryl" mentioned above.

[0121] A "substituted silyl" is, for example, a silyl substituted with at least one of aryl, alkyl, and cycloalkyl groups, preferably a triarylsilyl, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, or alkyldicycloalkylsilyl.

[0122] 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.

[0123] "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.

[0124] "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.

[0125] 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.

[0126] "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.

[0127] Substituents (including the first and second 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 substituents. 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.

[0128] 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] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka]

[0129] <Description of cycloalkane condensation> Furthermore, at least one of the aromatic rings and heteroaromatic rings in the chemical structure of the polycyclic aromatic compound of the present invention may be condensed with at least one cycloalkane.

[0130] For example, aryl rings and heteroaryl rings which are rings A and B, aryl groups (aryl moiety in aryl, diarylamino, arylheteroarylamino, diarylboryl, aryloxy, or triarylsilyl) and heteroaryl groups (heteroaryl moiety in heteroaryl, diheteroarylamino, or arylheteroarylamino) as first and second substituents on these rings, aryl rings and heteroaryl rings which are rings a and b, aryl rings or heteroaryl rings formed by the bonding of adjacent substituents on rings a and b, aryl groups (as above) and heteroaryl groups (as above) as first and second substituents on rings a and b, X 1 ~X 4 At least one of the aryl or heteroaryl groups, such as R in ">NR", R in ">C(-R)2", and R in ">Si(-R)2", may be condensed with at least one cycloalkane.

[0131] Preferably, an aryl ring and a heteroaryl ring which are rings A and B, an aryl group (the aryl group portion in aryl, diarylamino, diarylboryl, or aryloxy) and a heteroaryl group (the heteroaryl portion in heteroaryl or diheteroarylamino) as a first substituent on these rings, an aryl ring and a heteroaryl ring which are rings a and b, an aryl ring or heteroaryl ring formed by the bonding of adjacent substituents on rings a and b, an aryl group (as above) and a heteroaryl group (as above) as a first substituent on rings a and b, X 1 ~X 4 At least one of the aryl or heteroaryl groups, such as R in ">NR", R in ">C(-R)2", and R in ">Si(-R)2", may be condensed with at least one cycloalkane.

[0132] More preferably, an aryl ring which is an A ring and a B ring, an aryl group (the aryl group portion in aryl or diarylamino) and a heteroaryl group (the heteroaryl portion in heteroaryl) as a first substituent on these rings, an aryl ring which is an a ring and a b ring, an aryl ring formed by the bonding of adjacent substituents on the a ring and the b ring, an aryl group (as above) and a heteroaryl group (as above) as a first substituent on the a ring and the b ring, X 1 ~X 4 At least one of the aryl groups as R in ">NR" may be condensed with at least one cycloalkane.

[0133] More preferably, an aryl ring which is ring A and ring B, an aryl group as a first substituent on these rings (the aryl group portion in an aryl or diarylamino), an aryl ring which is ring a and ring b, an aryl group as a first substituent on ring a and ring b (as above), X 1 ~X 4 At least one of the aryl groups as R in ">NR" may be condensed with at least one cycloalkane.

[0134] Examples of "cycloalkanes" include cycloalkanes with 3 to 24 carbon atoms, cycloalkanes with 3 to 20 carbon atoms, cycloalkanes with 3 to 16 carbon atoms, cycloalkanes with 3 to 14 carbon atoms, cycloalkanes with 5 to 10 carbon atoms, cycloalkanes with 5 to 8 carbon atoms, cycloalkanes with 5 to 6 carbon atoms, and cycloalkanes with 5 carbon atoms.

[0135] Specific examples of cycloalkanes include cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclooctane, cyclononane, cyclodecane, norbornene, bicyclo[1.1.0]butane, bicyclo[1.1.1]pentane, bicyclo[2.1.0]pentane, bicyclo[2.1.1]hexane, bicyclo[3.1.0]hexane, bicyclo[2.2.1]heptane, bicyclo[2.2.2]octane, adamantane, diamantane, decahydronaphthalene, and decahydroazulene, as well as alkyl (especially methyl), halogen (especially fluorine), and deuterium-substituted compounds of these compounds having 1 to 5 carbon atoms.

[0136] Among these, a structure in which at least one hydrogen is substituted at the α-carbon of the cycloalkane (in a cycloalkyl condensed to an aromatic ring or heteroaromatic ring, the carbon adjacent to the carbon at the condensation site) is preferred, as shown in the structural formula below; a structure in which two hydrogens are substituted at the α-carbon is more preferred; and a structure in which a total of four hydrogens are substituted at two α-carbons is even more preferred. Examples of substituents include alkyl (especially methyl) substituted compounds having 1 to 5 carbon atoms, halogen (especially fluorine) substituted compounds, and deuterium substituted compounds. [ka]

[0137] The number of cycloalkanes condensed to a single aromatic ring or heteroaromatic ring is preferably 1 to 3, more preferably 1 or 2, and even more preferably 1. For example, examples of condensation of one or more cycloalkanes to a single benzene ring (phenyl group) are shown below. In each structural formula, * means that if it is a benzene ring, it is a benzene ring included in the skeletal structure of the compound, and if it is a phenyl group, it means a bond that substitutes on the skeletal structure of the compound. Condensed cycloalkanes may also be condensed with each other, as in formulas (Cy-1-4) and (Cy-2-4). The same applies even if the ring (group) to be condensed is an aromatic ring or heteroaromatic ring other than a benzene ring (phenyl group), and even if the cycloalkane to be condensed is a cycloalkane other than cyclopentane or cyclohexane. [ka]

[0138] At least one -CH2- in a cycloalkane may be substituted with -O-. However, if multiple -CH2- are substituted with -O-, adjacent -CH2- will not be substituted with -O-. For example, the following shows a cycloalkane condensed to a single benzene ring (phenyl group) in which one or more -CH2- are substituted with -O-. In each structural formula, * means a benzene ring included in the skeletal structure of the compound if it is a benzene ring, and a bond that substitutes on the skeletal structure of the compound if it is a phenyl group. The same applies even if the condensed ring (group) is an aromatic ring or heteroaromatic ring other than a benzene ring (phenyl group), and even if the condensed cycloalkane is a cycloalkane other than cyclopentane or cyclohexane. [ka]

[0139] At least one hydrogen atom in the cycloalkane may be substituted. Examples of such substituents include aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl (the two aryls may be linked by a single bond or a linking group), alkyl, cycloalkyl, alkoxy, aryloxy, diarylphosphoryl, substituted silyl, deuterium, cyano, or halogen. Details of these substituents can be found in the description of the first substituent above. Among these substituents, alkyl (e.g., alkyls with 1 to 6 carbon atoms), cycloalkyl (e.g., cycloalkyls with 3 to 14 carbon atoms), halogen (e.g., fluorine), and deuterium are preferred. Furthermore, when a cycloalkyl group is substituted, it may be in a form that forms a spiro structure. For example, an example of a spiro structure formed in a cycloalkane condensed with one benzene ring (phenyl group) is shown below. In each structural formula, * means that if it is a benzene ring, it is a benzene ring included in the skeletal structure of the compound, and if it is a phenyl group, it means a bond that substitutes on the skeletal structure of the compound. [ka]

[0140] Other forms of cycloalkane condensation include cases in which a polycyclic aromatic compound represented by formula (1) or formula (2) is substituted with, for example, a diarylamino group condensed with a cycloalkane (condensed on the aryl group portion), a carbazolyl group condensed with a cycloalkane (condensed on the benzene ring portion), or a benzocarbazolyl group condensed with a cycloalkane (condensed on the benzene ring portion). The "diarylamino group" is the group described above as the "first substituent."

[0141] Furthermore, as a more specific example, consider the R in polycyclic aromatic compounds represented by formula (2). a (Especially, Y 1 and Y 2 R of the para-order aExamples include a diarylamino group condensed with a cycloalkane (condensation to the aryl group portion) or a carbazolyl group condensed with a cycloalkane (condensation to the benzene ring portion).

[0142] <Explanation of substitution with deuterium, cyanoside, or halogen> At least one hydrogen atom in the polycyclic aromatic compound of the present invention may be substituted with deuterium, cyanopropyl alcohol, or halogen. The halogen is fluorine, chlorine, bromine, or iodine, with fluorine, chlorine, or bromine being preferred, and fluorine or chlorine being more preferred.

[0143] <Description of specific examples of polycyclic aromatic compounds of the present invention> Specific examples of polycyclic aromatic compounds include compounds represented by the following structural formulas. [ka]

[0144] Each benzene ring in the above structural formula may be independently substituted with a C6-C16 aryl group, a C2-C20 heteroaryl group, a diarylamino group (where the aryl group is a C6-C10 aryl group), a diarylboryl group (where the aryl group is a C6-C10 aryl group, and the two aryl groups may be linked by a single bond or a linking group), a C1-C12 alkyl group, or a C3-C16 cycloalkyl group, and at least one hydrogen atom in the substituent may be substituted with a C1-C5 alkyl group or a C5-C10 cycloalkyl group. Specific examples of these substituents can be found in the description above. The number of substituents, when substituted, ranges from one to the maximum number that can be substituted on each benzene ring, preferably 1-2, and more preferably 1.

[0145] Furthermore, at least one hydrogen atom in the compound represented by the above structural formula may be substituted with deuterium, cyano, or halogen.

[0146] More specific examples of polycyclic aromatic compounds include the compounds represented by the following structural formulas. In the structural formulas below, "Me" represents a methyl group, "tBu" represents a t-butyl group, "D" represents deuterium, and "Ad" represents 1-adamantyl or 2-adamantyl (more preferably 1-adamantyl).

[0147] [ka]

[0148] [ka]

[0149] [ka]

[0150] [ka]

[0151] [ka]

[0152] [ka]

[0153] [ka]

[0154] [ka]

[0155] [ka]

[0156]

change

[0157]

change

[0158]

change

[0159]

change

[0160]

change

[0161]

change

[0162]

change

[0163]

change

[0164]

change

[0165]

change

[0166]

change

[0167] [ka]

[0168] [ka]

[0169] [ka]

[0170] [ka]

[0171] [ka]

[0172] <Explanation of the high molecular weight of polycyclic aromatic compounds> The polycyclic aromatic compound represented by the above general formula (1) can be used as a polymer compound obtained by polymerizing a reactive compound substituted with a reactive substituent thereon (the monomer for obtaining this polymer compound has a polymerizable substituent), or as a polymer crosslinked product obtained by further crosslinking the polymer compound (the polymer compound for obtaining this polymer crosslinked product has a crosslinkable substituent), or as a pendant-type polymer compound obtained by reacting a main-chain polymer with the reactive compound (the reactive compound for obtaining this pendant-type polymer compound has a reactive substituent), or as a pendant-type polymer crosslinked product obtained by further crosslinking the pendant-type polymer compound (the pendant-type polymer compound for obtaining this pendant-type polymer crosslinked product has a crosslinkable substituent), and can be used as a material for organic devices, such as a material for organic field-light-emitting devices, a material for organic field-effect transistors, a material for organic thin-film solar cells, or a wavelength conversion filter.

[0173] 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]

[0174] 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.

[0175] 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 compound represented by formula (1), at least one selected from 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 repeating units. Substituents in these repeating units include, for example, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl (the two aryls may be linked by a single bond or a linking group), alkyl, cycloalkyl, alkoxy, aryloxy, triarylsilyl, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, or alkyldicycloalkylsilyl. For details on the "aryl" in triarylamine and these substituents, refer to the explanation for polycyclic aromatic compounds represented by formula (1).

[0176] 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.

[0177] 2. Method for producing a polycyclic aromatic compound The polycyclic aromatic compounds of the present invention are basically formed by first bonding the A ring (a ring), the B ring (b ring), and the c ring with a bonding group (X 1 ~X 4 An intermediate is produced by bonding the rings (including the group containing Y) (first reaction), and then the A ring (a ring), B ring (b ring), and c ring are bonded together by the bonding group (central element Y). 1 , Y 2 , and Y 3 A base including, hereinafter referred to as "Y 1 , Y 2 , and Y 3 The final product can be produced by bonding (abbreviating "" as "Y") (second reaction). The manufacturing method described in International Publication No. 2015 / 102118 can be used as a reference.

[0178] For the first reaction, for example, if it is an etherification reaction, general reactions such as nucleophilic substitution reactions and Ullmann reactions can be used, and if it is an amination reaction, general reactions such as the Buchwald-Hartwig reaction can be used. In the second reaction, the tandem hetero-Friedel-Crafts reaction (sequential aromatic electrophilic substitution reaction, hereafter the same) can be used.

[0179] The second reaction is a reaction that introduces the central element Y that connects the A ring (a ring), the B ring (b ring), and the c ring, as shown in scheme (1) below. First, X 1 and X 2 Hydrogen atoms between them, hydrogen atoms in the c ring, and X 3 and X 4 The hydrogen atom between the two atoms is orthometalated with n-butyllithium, sec-butyllithium, or t-butyllithium, etc. Then, a Y halide such as boron trichloride or boron tribromide 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. Note that the definition of the signs in each structural formula in scheme (1) below and in subsequent schemes is the same as the definition described above.

[0180] [ka]

[0181] In the scheme described above, lithium was introduced to the desired position by orthometallation. However, as shown in scheme (2) below, bromine atoms or the like can be introduced to the desired position, and lithium can also be introduced to the desired position by halogen-metal exchange. This method is useful because it allows the production of the target product even in cases where orthometallation is not possible due to the influence of substituents.

[0182] [ka]

[0183] The above schemes (1) and (2) are typical production methods where Y is boron (>B-).

[0184] Next, as an example, schemes (3) and (4) below show the case where Y is a phosphorus sulfide, phosphorus oxide, or phosphorus atom. As before, first X 1 and X 2 Hydrogen atoms between them, hydrogen atoms in the c ring, and X 3 and X 4 The hydrogen atom between the two atoms is orthometalated with n-butyllithium or the like. Then, phosphorus trichloride and sulfur are added in that order, and finally a Lewis acid such as aluminum trichloride and a Brønsted base such as N,N-diisopropylethylamine are added to carry out a tandem phosphat Friedel-Crafts reaction, yielding a compound in which Y is phosphorus sulfide. Alternatively, the obtained phosphorus sulfide compound can be treated with m-chloroperbenzoic acid (m-CPBA) to obtain a compound in which Y is phosphorus oxide, and can be treated with triethylphosphine to obtain a compound in which Y is a phosphorus atom.

[0185] [ka]

[0186] [ka]

[0187] The above scheme mainly describes examples where Y is >B-, >P-, >P(=O)-, or >P(=S)-, but other compounds can also be produced by appropriately changing the raw materials.

[0188] In the above scheme, before adding a Y halide such as boron trichloride or boron tribromide, X 1 and X 2 Hydrogen atoms (or halogen atoms) between them, hydrogen atoms (or halogen atoms) in the c ring, and X 3 and X 4An example of a tandem hetero-Friedel-Crafts reaction was shown, in which the hydrogen atom (or halogen atom) between the atoms was orthometalated with butyllithium or the like. However, the reaction can also be carried out by adding a Y halide such as boron trichloride or boron tribromide without orthometalation using butyllithium or the like.

[0189] Examples of solvents used in the above scheme include t-butylbenzene and xylene.

[0190] Examples of orthometalating reagents used in the above scheme include alkyllithium compounds such as methyllithium, n-butyllithium, sec-butyllithium, and t-butyllithium; organic alkali compounds such as lithium diisopropylamide, lithium tetramethylpiperidide, lithium hexamethyldisilazide, and potassium hexamethyldisilazide; and dispersed alkali metals such as Na dispersed in an organic solvent.

[0191] Examples of metal-Y exchange reagents used in the above scheme include Y halides such as Y trifluoride, Y trichloride, Y tribromide, and Y triiodide, Y amination halides such as CIPN(NEt2)2, Y alkoxyides, and Y aryl oxyides.

[0192] Examples of Brønsted bases used in the above scheme 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).

[0193] Examples of Lewis acids used in the above scheme 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.

[0194] In the above scheme, a Brønsted base or Lewis acid may be used to accelerate the tandem hetero-Friedel-Crafts reaction. However, when using halides of Y such as Y trifluoride, Y trichloride, Y tribromide, or Y 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 acids is effective. On the other hand, when using aminohalides of Y or alkoxyides of Y, 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.

[0195] Furthermore, the polycyclic aromatic compounds of the present invention also include compounds in which at least some of the hydrogen atoms are substituted with deuterium, cyanoside, or halogen. Such compounds can be produced in the same manner as described above by using halogenated raw materials in which the desired positions are deuterated, cyanated, fluorinated, or chlorinated.

[0196] 3. Organic 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.

[0197] 3-1. Organic electroluminescent device 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.

[0198] <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.

[0199] 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.

[0200] 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.

[0201] 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".

[0202] <Substrate for organic electroluminescent light-emitting 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.

[0203] <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.

[0204] 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.

[0205] 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.

[0206] <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.

[0207] For hole implantation and transport materials, it is necessary to efficiently implant and transport holes from the positive electrode between electrodes under an applied electric field. Therefore, high hole implantation efficiency and efficient transport of implanted holes are desirable. To achieve this, it is preferable to use a material with a low ionization potential, high hole mobility, excellent stability, and low generation of trapping impurities during manufacturing and use. In this invention, a polycyclic aromatic compound represented by the above general formula (1) can be used as the material for the hole implantation layer and the hole transport layer.

[0208] As the material for forming the hole injection layer 103 and the hole transport layer 104, any compound can be selected from among compounds conventionally used as charge transport materials for holes in photoconductive materials, p-type semiconductors, and known compounds used in hole injection layers and hole transport layers of organic EL devices.

[0209] 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.

[0210] 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).

[0211] 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.

[0212] <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 (luminescent compound) that emits light when excited by the recombination of holes and electrons, 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 host material and, for example, a polycyclic aromatic compound represented by the above general formula (1) as a dopant material can be used as the material for the light-emitting layer.

[0213] 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.

[0214] 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. The guideline for the amount of host material used is preferably 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.

[0215] 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.

[0216] 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.

[0217] When assist dopant materials are used, the approximate amounts of 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. The polycyclic aromatic compound represented by the above general formula (1) and its polymer compound can also be used as an assist dopant material.

[0218] 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.

[0219] 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.

[0220] 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]

[0221] <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 quinoxaline rings. Examples of divalent groups include 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, oxadiazole 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.

[0222] <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 for the heteroaryl, 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, pyridazine ring, pyrazine ring, triazine ring, indole ring, isoindole ring, 1H-indazole ring, benzimidazole ring, benzoxazole ring, benzothiazole ring, 1H-be Examples of monovalent groups include nzotriazole rings, quinoline rings, isoquinoline rings, sinnoline rings, quinazoline rings, quinoxaline 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, oxadiazole rings, thianthrene rings, indolocarbazole rings, benzoindolocarbazole rings, benzobenzoindolocarbazole rings, and naphthobenzofuran rings. 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.

[0223] <Compounds represented by the general formula (H3) (an example of a polymer host material)> [ka]

[0224] 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.

[0225] 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.

[0226] 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.

[0227] Examples of MU include divalent groups that can be represented by removing any two hydrogen atoms from any of the following compounds. [ka]

[0228] More specifically, divalent groups represented by one of the following structures are included. In these, MU bonds with another MU or EC at *.

[0229] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka]

[0230] Furthermore, EC can be a monovalent group represented by one of the following structures, for example. In these structures, EC binds to MU at *.

[0231] [ka] [ka]

[0232] 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).

[0233] <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]

[0234] 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).

[0235] 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.

[0236] Examples of substituents when H in G, "=C(-H)-", is substituted are, but are not limited to, the following.

[0237] 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.

[0238] 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.

[0239] 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.

[0240] 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.

[0241] 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.

[0242] Examples of substituted carboxyl groups include benzoyloxy.

[0243] 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.

[0244] Specific examples of compounds containing the structure represented by the general formula (H4) are shown below. [ka] [ka]

[0245] <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.

[0246] Any "-C(-R)=" in ring a, ring b, and ring c in equation (H5) (where R is R 1 ~R 11 The part (which is) can be replaced with "-N=" and may change to a pyridine ring, pyrimidine ring, pyridazine ring, pyrazine ring, or other nitrogen-containing heteroaryl ring. For further details of this explanation, refer to the explanation in general formula (2) above.

[0247] 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. R1 ~R 11 Adjacent 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.

[0248] 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.

[0249] Examples of "aryl" and "heteroaryl" in the first and second substituents described above include aryl, heteroaryl, diarylamino, diheteroarylamino, and arylheteroarylamino.

[0250] 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.

[0251] 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.

[0252] 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.

[0253] 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.

[0254] 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.

[0255] 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.

[0256] 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.

[0257] [ka] [ka]

[0258] 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.

[0259] <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.

[0260] 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.

[0261] 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.

[0262] Examples of "aryl" and "heteroaryl" in the first and second substituents described above include aryl, heteroaryl, diarylamino, diheteroarylamino, and arylheteroarylamino.

[0263] 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.

[0264] 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.

[0265] 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.

[0266] 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.

[0267] The compound represented by formula (H6) can be produced by referring to the description described in International Publication No. 2014 / 042197.

[0268] <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 manifested. In normal fluorescence emission, 75% of the triplet excitons generated by current excitation pass through the thermal deactivation pathway 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.

[0269] Examples of TADF materials that can be used for such purposes include compounds represented by the following general formula (H7) or compounds having the following general formula (H7) as a partial structure.

Chemical formula

[0270] 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.

[0271] 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.

[0272] 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.

[0273] 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.

[0274] 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 3Examples of nitrogen-containing functional groups include groups derived from carbazole, dimethylcarbazole, di-t-butylcarbazole, dimethoxycarbazole, tetramethylcarbazole, benzofluorocarbazole, benzothienocarbazole, phenyldihydroindocarbazole, phenylbicarbazole, bicarbazole, tercarbazole, diphenylcarbazolylamine, tetraphenylcarbazolyldiamine, phenoxazine, dihydrophenazine, phenothiazine, dimethyldihydroacridine, diphenylamine, bis(t-butyl)phenyl)amine, (diphenylamino)phenyl)diphenylbenzenediamine, dimethyltetraphenyldihydroacridinediamine, tetramethyl-dihydro-indenoacridine, and diphenyl-dihydrodibenzoazacillin. Furthermore, examples of EA include sp 2Nitrogen-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, heptazphenalene, thioxanthiox Examples of groups derived from sides, dimethylanthracenone, anthracendione, pyridine, cycloheptabipyridine, 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.

[0275] 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]

[0276] 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, triazyl, 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.

[0277] 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.

[0278] [ka]

[0279] [ka]

[0280] [ka]

[0281] [ka]

[0282] [ka]

[0283] [ka]

[0284] [ka]

[0285] [ka]

[0286] [ka]

[0287] 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).

[0288] Furthermore, in addition to the polycyclic aromatic compounds represented by the general formula (1) above, other known compounds can be used as dopant materials, and various materials can be selected according to the desired emission color.Specifically, for example, condensed ring derivatives such as phenanthrene, anthracene, pyrene, tetracene, pentacene, perylene, naphthyrene, 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.

[0289] 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.

[0290] 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.

[0291] 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.

[0292] 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.

[0293] 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.

[0294] 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 of aryl, alkyl, or cycloalkyl) or cyano, and m is an integer from 1 to 4.

[0295] 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.

[0296] 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.

[0297] 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.

[0298] 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.

[0299] 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.

[0300] 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.

[0301] 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.

[0302] 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.

[0303] 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.

[0304] 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.

[0305] 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.

[0306] 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.

[0307] 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.

[0308] 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.

[0309] 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.

[0310] <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.

[0311] 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.

[0312] 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.

[0313] 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.

[0314] 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.

[0315] 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.

[0316] The materials mentioned above can be used individually, but they can also be used in combination with other materials.

[0317] 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.

[0318] <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.

[0319] 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 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.

[0320] 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.

[0321] Specific examples of these borane derivatives include the following compounds. [ka]

[0322] This borane derivative can be produced using known raw materials and known synthesis methods.

[0323] <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]

[0324] 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.

[0325] 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).

[0326] 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.

[0327] 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]

[0328] 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]

[0329] 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 replaced with an aryl atom.

[0330] 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).

[0331] 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.

[0332] For alkyl groups with 1 to 4 carbon atoms to be substituted for pyridine substituents, the above description of alkyl groups can be referenced.

[0333] 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" include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, methylcyclopentyl, cycloheptyl, methylcyclohexyl, cyclooctyl, or dimethylcyclohexyl.

[0334] For cycloalkyl groups with 5 to 10 carbon atoms to be substituted for pyridine substituents, the above description of cycloalkyl groups can be referenced.

[0335] 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.

[0336] 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.

[0337] 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.

[0338] 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, the five-membered ring of the fluorene skeleton may be spirobonded to cyclobutane, cyclopentane, cyclopentene, cyclopentadiene, cyclohexane, fluorene, or indene.

[0339] Specific examples of pyridine derivatives include the following compounds. [ka]

[0340] This pyridine derivative can be produced using known raw materials and known synthesis methods.

[0341] <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]

[0342] 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 in the case of being substituted include aryl, heteroaryl, alkyl or cycloalkyl.

[0343] Specific examples of this fluoranthene derivative include, for example, the following compounds. [Chemical formula]

[0344] <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]

[0345] 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.

[0346] 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.

[0347] Furthermore, at least one hydrogen atom in the compound or structure represented by formula (ETM-4) may be substituted with a halogen or deuterium.

[0348] For explanations regarding the substituents and ring formation in formula (ETM-4), as well as the polymers formed by the combination of multiple structures of formula (ETM-4), refer to the explanations in International Publication No. 2015 / 102118 and the explanation of polycyclic aromatic compounds represented by the general formula (1) above.

[0349] Specific examples of these BO derivatives include the following compounds. [ka]

[0350] This BO derivative can be produced using known raw materials and known synthesis methods.

[0351] <Anthracene derivatives> One example of anthracene derivatives is the compound represented by the following formula (ETM-5-1). [ka]

[0352] 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.

[0353] 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]

[0354] 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.

[0355] 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.

[0356] 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.

[0357] 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.

[0358] 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.

[0359] 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.

[0360] One example of anthracene derivatives is the compound represented by the following formula (ETM-5-2). [ka]

[0361] Ar 1 These are, independently, single-bonded, divalent benzene, naphthalene, anthracene, fluorene, or phenalene.

[0362] 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.

[0363] 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.

[0364] Specific examples of these anthracene derivatives include the following compounds, for example. [ka]

[0365] These anthracene derivatives can be produced using known raw materials and known synthesis methods.

[0366] <Benzofluorene derivatives> Benzofluorene derivatives are compounds represented by the following formula (ETM-6), for example. [ka]

[0367] 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.

[0368] 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.

[0369] 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.

[0370] 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.

[0371] 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.

[0372] Specific examples of "aryl compounds with 6 to 30 carbon atoms" include phenyl, naphthyl, acenaphthirenyl, fluorenyl, phenalenyl, phenanthryl, triphenylenyl, pyrenyl, naphthacenyl, perilenyl, and pentacenyl.

[0373] Two Ar 2 These may be bonded together to form a ring, and as a result, the five-membered ring of the fluorene skeleton may be spirobonded to cyclobutane, cyclopentane, cyclopentene, cyclopentadiene, cyclohexane, fluorene, or indene.

[0374] Specific examples of these benzofluorene derivatives include the following compounds. [ka]

[0375] This benzofluorene derivative can be produced using known raw materials and known synthesis methods.

[0376] <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.

[0377] The phosphine oxide derivative may be, for example, a compound represented by the following formula (ETM-7-2). [ka]

[0378] 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.

[0379] 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 these molecules has a substituent or forms a fused ring with an adjacent substituent. n is an integer from 0 to 3, and when n is 0, there is no unsaturated structural part, and when n is 3, R 1 It does not exist.

[0380] 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.

[0381] 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.

[0382] 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.

[0383] 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.

[0384] 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.

[0385] 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.

[0386] 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.

[0387] 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.

[0388] 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.

[0389] 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.

[0390] 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.

[0391] 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.

[0392] 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.

[0393] Halogens refer to fluorine, chlorine, bromine, and iodine.

[0394] Aldehyde groups, carbonyl groups, and amino groups may also include groups substituted with aliphatic hydrocarbons, alicyclic hydrocarbons, aromatic hydrocarbons, heterocyclic groups, etc.

[0395] Furthermore, aliphatic hydrocarbons, alicyclic hydrocarbons, aromatic hydrocarbons, and heterocyclic hydrocarbons may be unsubstituted or substituted.

[0396] 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.

[0397] 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 with each other. These fused rings may contain nitrogen, oxygen, and sulfur atoms in their intraring structure, or they may be further fused with other rings.

[0398] Specific examples of these phosphine oxide derivatives include the following compounds. [ka]

[0399] This phosphine oxide derivative can be produced using known raw materials and known synthesis methods.

[0400] <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]

[0401] Each Ar is independently a substituted or substituted heteroaryl. n is an integer from 1 to 4, preferably from 1 to 3, and more preferably 2 or 3.

[0402] 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.

[0403] 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.

[0404] 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.

[0405] 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.

[0406] 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.

[0407] Specific examples of these pyrimidine derivatives include the following compounds. [ka]

[0408] This pyrimidine derivative can be produced using known raw materials and known synthesis methods.

[0409] <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]

[0410] 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.

[0411] 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.

[0412] 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.

[0413] 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.

[0414] 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.

[0415] 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.

[0416] Carbazole derivatives may be polymers formed by the bonding of multiple compounds represented by the above formula (ETM-9) via single bonds or other means. In this case, in addition to single bonds, the compounds may also be bonded by aryl rings (preferably polyvalent benzene rings, naphthalene rings, anthracene rings, fluorene rings, benzofluorene rings, phenalene rings, phenanthrene rings, or triphenylene rings).

[0417] Specific examples of these carbazole derivatives include the following compounds. [ka]

[0418] This carbazole derivative can be produced using known raw materials and known synthesis methods.

[0419] <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]

[0420] Each Ar is independently a substituted or substituted heteroaryl. n is an integer between 1 and 3, preferably 2 or 3.

[0421] 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.

[0422] 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.

[0423] 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.

[0424] 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.

[0425] 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.

[0426] Specific examples of these triazine derivatives include the following compounds. [ka]

[0427] This triazine derivative can be produced using known raw materials and known synthesis methods.

[0428] <Benzimidazole derivatives> Benzimidazole derivatives are compounds represented by, for example, the following formula (ETM-11). [ka]

[0429] 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]

[0430] 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.

[0431] 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.

[0432] 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]

[0433] This benzimidazole derivative can be produced using known raw materials and known synthesis methods.

[0434] <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]

[0435] 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.

[0436] 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.

[0437] At least one hydrogen atom in each phenanthroline derivative may be substituted with deuterium.

[0438] 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]

[0439] 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), basocuproine, 1,3-bis(2-phenyl-1,10-phenanthroline-9-yl)benzene, and compounds represented by the following structural formula. [ka]

[0440] This phenanthroline derivative can be produced using known raw materials and known synthesis methods.

[0441] <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.

[0442] 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.

[0443] This quinolinol-based metal complex can be produced using known raw materials and known synthesis methods.

[0444] <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]

[0445] 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]

[0446] 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.

[0447] These thiazole derivatives or benzothiazole derivatives can be produced using known raw materials and known synthesis methods.

[0448] <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]

[0449] 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.

[0450] 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.

[0451] 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).

[0452] 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.

[0453] 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.

[0454] 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.

[0455] 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.

[0456] These silole derivatives can be produced using known raw materials and known synthesis methods.

[0457] <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]

[0458] 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.

[0459] 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.

[0460] 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).

[0461] 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.

[0462] 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.

[0463] 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.

[0464] Specific examples of azoline derivatives include the following compounds. Note that "Me" in the structural formula represents a methyl group. [ka] [ka]

[0465] 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.

[0466] Other specific examples of azoline derivatives include the following compounds. Note that "Me" in the structural formula represents a methyl group. [ka]

[0467] 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.

[0468] This azoline derivative can be produced using known raw materials and known synthesis methods.

[0469] 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.

[0470] 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.

[0471] 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.

[0472] <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.

[0473] 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.

[0474] 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.

[0475] <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.

[0476] <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.

[0477] 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.

[0478] 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.

[0479] <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.

[0480] <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.

[0481] 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.

[0482] 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.

[0483] 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.

[0484] 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 remaining layers.

[0485] 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) Deposition of film 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.

[0486] <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.

[0487] <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.

[0488] 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.

[0489] 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.

[0490] <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.

[0491] <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.

[0492] (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.

[0493] 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.

[0494] 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.

[0495] 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.

[0496] (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.

[0497] <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.

[0498] (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.

[0499] 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.

[0500] The binder used in the organic layer-forming composition may be a single type or a mixture of multiple types.

[0501] (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.

[0502] 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.

[0503] Furthermore, a single surfactant may be used, or two or more may be used in combination.

[0504] <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.

[0505] 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.

[0506] 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.

[0507] 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.

[0508] 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 viscosity of the organic layer-forming composition is preferably such that the surface tension at 25°C is 20 to 40 mN / m, and more preferably 20 to 30 mN / m. In this invention, the surface tension is a value measured using the suspension drop method.

[0509] <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.

[0510] 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.

[0511] 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]

[0512] 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.

[0513] 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]

[0514] <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.

[0515] 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.

[0516] 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.

[0517] 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.

[0518] 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]

[0519] Monomer units that can be used in the present invention can be synthesized in accordance with 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.

[0520] 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.

[0521] <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.

[0522] 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.

[0523] 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.

[0524] 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.

[0525] 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.

[0526] 3-2. Other organic devices 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.

[0527] 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.

[0528] 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 and 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.

[0529] 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.

[0530] 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]

[0531] 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.

[0532] Synthesis Example (1): Synthesis of Compounds (1-11) [ka]

[0533] To a flask containing compound (Int-1-11) (0.402 g, 0.50 mmol) and o-dichlorobenzene (5.0 ml), boron tribromide (0.760 ml, 8.0 mmol) was added under a nitrogen atmosphere at room temperature. After the addition was complete, the mixture was stirred at a reaction temperature of 200 °C for 20 hours. The mixture was then cooled to room temperature, diluted with dichloromethane (20 ml), and added to phosphate buffer solution (pH 6.8, 150 ml). The aqueous layer was separated and extracted with dichloromethane (10 ml, 3 times). The solvent was then removed to obtain the crude product. The crude product was purified using a silica gel column (eluent: hexane / dichloromethane = 5 / 1, 4 / 1, 3 / 1 (volume ratio)) to obtain compound (1-11) (31.7 mg, yield 8%). [ka]

[0534] The structure of the compound obtained by NMR measurement was confirmed. 1 H-NMR(500MHz,(CDCl2)2):δ=1.31(s,18H), 2.44(s,6H), 2.47(s,12H), 2.74(s,3 H), 6.45(s,2H), 6.80(d,2H), 7.09(s,4H), 7.23(s,2H), 7.25(s,2H), 8.32(s,2H). 13C-NMR(126MHz,(CDCl2)2):δ=8.82(1C), 21.4(4C), 23.2(2C), 31.4(6C), 35.9 (2C), 103.9(2C), 105.6(2C), 113.2(1C), 116.8(2C),...

Claims

1. A polycyclic aromatic compound represented by the following general formula (2). 【Chemistry 2】 In the above formula (2), R ａ , R ｂ , and R ｃ Each of these is independently hydrogen, a C6-C16 aryl group, a C2-C20 heteroaryl group, a diarylamino group (where the aryl group is a C6-C10 aryl group), a diarylboryl group (where the aryl group is a C6-C10 aryl group, and the two aryl groups may be linked by a single bond or a linking group), a C1-C12 alkyl group, or a C3-C16 cycloalkyl group, and the R ａ , R ｂ , and R ｃ At least one hydrogen atom in may be substituted with an alkyl group having 1 to 5 carbon atoms, or a cycloalkyl group having 5 to 10 carbon atoms. "-C(-R)" in the c ring ｃ )=" may be replaced with "-N=". In the a-ring and the b-ring, any "−C(−R)=“ (where R is R ａ or R ｂ ) may be replaced by "−N=“, and any "−C(−R)=C(−R)−“ (where R is R ａ or R ｂ ) may be replaced by "−N(−R)−“, "−O−“, or "−S−“, and R in the "−N(−R)−“ is aryl having 6 to 10 carbon atoms, heteroaryl having 2 to 10 carbon atoms, alkyl having 1 to 5 carbon atoms, or cycloalkyl having 5 to 10 carbon atoms, Y １ , Y ２ , and Y ３ It is >B-, X １ , X ２ , X ３ , and X ４ Each of these is independently >N-R or >O, where R in >N-R is a C6-C10 aryl, a C2-C10 heteroaryl, a C1-C5 alkyl, or a C5-C10 cycloalkyl, and at least one hydrogen in R may be substituted with a C1-C5 alkyl or a C5-C10 cycloalkyl. Also, the X １ or X ３ In ">N-R", R is the b ring and the X ２ or X ４ The R in ">N-R" may be bonded to the a-ring by a single bond or by -CR=CR-, and each of the R in "-CR=CR-" is independently a hydrogen, a carbon 6-10 aryl, a carbon 2-10 heteroaryl, a carbon 1-5 alkyl, a carbon 1-5 alkenyl, a carbon 1-5 alkynyl, or a carbon 5-10 cycloalkyl, and at least one hydrogen in the R may be substituted with a carbon 1-5 alkyl or a carbon 5-10 cycloalkyl, and two adjacent Rs may be bonded to each other to form a carbon 6-10 arylene ring or a carbon 2-10 heteroarylene ring. At least one hydrogen atom in the compound represented by formula (2) above may be substituted with deuterium, cyano, or halogen.

2. A polycyclic aromatic compound represented by one of the following structural formulas. 【Transformation 3】 Each benzene ring in the above structural formula may be independently substituted with a C6-C16 aryl group, a C2-C20 heteroaryl group, a diarylamino group (where the aryl group is a C6-C10 aryl group), a diarylboryl group (where the aryl group is a C6-C10 aryl group, and the two aryl groups may be linked by a single bond or a linking group), a C1-C12 alkyl group, or a C3-C16 cycloalkyl group, and at least one hydrogen atom in the substituent may be substituted with a C1-C5 alkyl group or a C5-C10 cycloalkyl group. At least one hydrogen atom in the compound represented by the above structural formula may be substituted with deuterium, cyano, or halogen.

3. A polycyclic aromatic compound represented by one of the following structural formulas. 【Chemistry 4】

4. A material for an organic device containing a polycyclic aromatic compound as described in any one of Claims 1 to 3.

5. The organic device material according to claim 4, wherein the organic device material is a material for an organic electroluminescent device, a material for an organic field-effect transistor, a material for an organic thin-film solar cell, or a material for a wavelength conversion filter.

6. The organic device material according to claim 5, wherein the aforementioned organic electroluminescent material is a material for a light-emitting layer.

7. An ink composition comprising a polycyclic aromatic compound as described in any one of Claims 1 to 3 and an organic solvent.

8. An organic electroluminescent element comprising a pair of electrodes consisting of an anode and a cathode, and an organic layer disposed between the pair of electrodes and containing a polycyclic aromatic compound as described in any one of claims 1 to 3.

9. The organic electroluminescent element according to claim 8, wherein the organic layer is a light-emitting layer.

10. The organic electroluminescent element according to claim 9, wherein the light-emitting layer comprises a host and the polycyclic aromatic compound as a dopant.

11. The organic electroluminescent element according to claim 10, wherein the light-emitting layer further contains at least one selected from the group consisting of a compound represented by the following general formula (H1), a compound represented by the following general formula (H2), a compound represented by the following general formula (H3), a compound containing a structure represented by the following general formula (H4), a compound represented by the following general formula (H5), a compound represented by the following general formula (H6), and a TADF material. 【Transformation 5】 In the above general formula (H1), L １ These are arylenes with 6 to 30 carbon atoms or heteroarylenes with 2 to 30 carbon atoms. In the above general 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. In the above general formula (H3), MU is a divalent group that can be independently represented by removing any two hydrogen atoms from an aromatic compound, EC is a monovalent group that can be independently represented by removing any one hydrogen atom from an aromatic compound, the two hydrogens in MU are substituted with EC or MU, and k is an integer between 2 and 50000. 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). In the above general formula (H5), R １ ~R １１ Each of these is independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, alkyl, or cycloalkyl, and R １ ~R １１ At least one hydrogen in may be further substituted with an aryl, heteroaryl, diarylamino, alkyl, or cycloalkyl group. 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, alkyl, or cycloalkyl, and at least one hydrogen in these substituents may be further substituted with aryl, heteroaryl, diarylamino, alkyl, or cycloalkyl. 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=". In the above general formula (H6), R １ ~R １６ Each of these is independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, alkyl, or cycloalkyl, and R １ ~R １６ At least one hydrogen in may be further substituted with an aryl, heteroaryl, diarylamino, alkyl, or cycloalkyl group. 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, and at least one hydrogen in these substituents may be further substituted with aryl, heteroaryl, diarylamino, alkyl, or cycloalkyl, and At least one hydrogen atom in the compounds or structures represented by the above formulas 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.

12. The organic electroluminescent element according to claim 8, further comprising at least one electron transport layer and electron injection layer disposed between the cathode and the light-emitting layer, wherein at least one of the electron transport layer and electron injection layer contains at least one selected from the group consisting of 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, quinolinol-based metal complexes, thiazole derivatives, benzothiazole derivatives, silole derivatives, and azoline derivatives.

13. The organic electroluminescent device according to claim 12, wherein at least one layer of the electron transport layer and electron injection layer further contains 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.

14. A display device comprising an organic electroluminescent element as described in Claim 8.

15. A lighting device comprising an organic electroluminescent element as described in Claim 8.

16. A wavelength conversion filter comprising the wavelength conversion filter material described in Claim 5.

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