Polycyclic aromatic compounds

Abstract

To provide a novel polycyclic aromatic compound, and an organic EL element based thereon.SOLUTION: The polycyclic aromatic compound is represented by general formula (1A) or general formula (1B). [The A ring and the B ring are each an aryl ring or the like; Rc is H or a substituent; Y1 and Y2 are each >B- or the like; X1, X2, X3 and X4 are each >N-R or the like; and the compound may be condensed with a cycloalkane, and may be substituted with deuterium or the like.]SELECTED DRAWING: None

Description

[Technical Field]

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

[0002] In the past, display devices using electroluminescent light-emitting elements have been extensively studied because they can be made thinner and more energy-efficient, and organic electroluminescent devices made from organic materials have been actively studied because they can be easily made lighter and larger. In particular, there has been active research into the development of organic materials that have the ability to emit light such as blue, one of the three primary colors of light, and organic materials that have the ability to transport charges such as holes and electrons (potentially becoming semiconductors or superconductors), regardless of whether they are polymer compounds or low-molecular-weight compounds.

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

[0004] For example, an improved triphenylamine derivative has been reported for use in organic light-emitting diode (OLED) devices and organic thin-film solar cells (WO 2012 / 118164). Based on the already commercially available N,N'-diphenyl-N,N'-bis(3-methylphenyl)-1,1'-biphenyl-4,4'-diamine (TPD), this material is characterized by linking the aromatic rings that make up the triphenylamine, placing nitrogen at the center of the ring structure while enhancing its planarity. While this document evaluates the charge transport properties of, for example, an NO-linked compound (Compound 1 on page 63), it does not describe methods for producing materials other than NO-linked compounds. Furthermore, because different linking elements result in different electronic states for the entire compound, the properties obtainable from materials other than NO-linked compounds were unknown.

[0005] The host material for organic EL devices is generally a molecule in which multiple existing aromatic rings such as benzene or carbazole are linked together with single bonds or phosphorus or silicon atoms. This is because linking a large number of relatively small aromatic rings in a conjugated system ensures the large HOMO-LUMO gap (band gap Eg in a thin film) required for the host material. Furthermore, host materials for organic EL devices using phosphorescent materials or thermally activated delayed fluorescent materials require high triplet excitation energy (E T ) is also required, but by connecting 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, which increases the triplet excitation energy (E T However, small aromatic rings in the conjugated system do not have sufficient redox stability, and devices using molecules formed by linking existing aromatic rings as host materials do not have sufficient life spans. On the other hand, polycyclic aromatic compounds with extended π-conjugated systems generally have excellent redox stability, but they have poor HOMO-LUMO gaps (band gaps in thin films, Eg) and triplet excitation energies (E T ) has been considered unsuitable as a host material.

[0006] In recent years, compounds in which multiple aromatic rings are fused with a central atom such as boron have been reported (WO 2015 / 102118). This document evaluates organic electroluminescent devices using such compounds as dopant materials in the emissive layer. Other examples include further polymerization of such compounds (WO 2018 / 212169) and the extension of conjugated systems within molecules using linking groups (Korean Patent Publication No. 10-2020-0121228 and WO 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 Patent Publication No. 10-2020-0121228 [Patent Document 5] International Publication No. 2020 / 217229 Summary of the Invention [Problem to be solved by the invention]

[0008] As reported in Patent Documents 1 to 5, various materials have been developed for use in organic EL devices, but the development of materials made from unconventional compounds is desired to increase the options for materials for organic EL devices. In particular, it would be beneficial to explore the organic EL properties and manufacturing methods obtainable from materials other than NO-linked compounds in which nitrogen is located at the center of the ring structure.

[0009] Furthermore, Patent Documents 2 to 5 report boron-containing polycyclic aromatic compounds and organic EL devices using the same. However, these documents disclose an extremely large number of compounds, and it would be beneficial to explore light-emitting layer materials, particularly dopant materials, that can improve organic EL properties such as luminous efficiency and device life, in order to further improve device properties.

[0010] Furthermore, as a method for forming the organic layers constituting an organic EL device, a wet film-forming method is also currently used in addition to a vacuum deposition method. Therefore, ink materials for wet film-forming, particularly for forming a hole injection layer, a hole transport layer, and a light-emitting layer, are being actively developed, and it is also beneficial to explore such ink materials. [Means for solving the problem]

[0011] As a result of intensive research aimed at solving the above-mentioned problems, the present inventors have found that an excellent organic EL device can be obtained by, for example, constructing an organic EL device by disposing a layer containing a polycyclic aromatic compound having a novel structure between a pair of electrodes, and have thus completed the present invention. That is, the present invention provides the following polycyclic aromatic compounds, and further provides materials for organic devices, such as materials for organic EL devices, containing the following polycyclic aromatic compounds.

[0012] In this specification, chemical structures and substituents are sometimes represented by the number of carbon atoms. However, when a chemical structure is substituted with a substituent or when a substituent is further substituted with a substituent, the number of carbon atoms refers to the number of carbon atoms in each of the chemical structure and the substituent, and does not refer to the total number of carbon atoms in the chemical structure and the substituent, or the total number of carbon atoms in the substituent and the substituent. For example, "substituent B of carbon number Y substituted with substituent A of carbon number X" means that "substituent B of carbon number Y" is substituted with "substituent A of carbon number X," and the carbon number Y is not the total number of carbon atoms in substituents A and B. Furthermore, for example, "substituent B of carbon number Y substituted with substituent A" means that "substituent B of carbon number Y" is substituted with "substituent A (with no carbon number restriction)," and the carbon number Y is not the total number of carbon atoms in substituents A and B.

[0013] Section 1. A polycyclic aromatic compound represented by the following general formula (1A) or (1B): [ka] In the above formula (1A) or formula (1B), ring A and ring B are each independently an aryl ring or a heteroaryl ring, and at least one hydrogen atom in these rings may be substituted; R c are each independently hydrogen or a substituent; -C(-R c )=" may be replaced with "-N=", Y 1 and Y 2 are each independently >B-, >P-, >P(=O)-, >P(=S)-, >Al-, >Ga-, >As-, >C(-R)-, >Si(-R)-, or >Ge(-R)-, and the R of ">C(-R)-", R of ">Si(-R)-", and R of ">Ge(-R)-" are each independently an optionally substituted aryl, an optionally substituted heteroaryl, an optionally substituted alkyl, or an optionally substituted cycloalkyl, X 1 , X 2 , X 3 , and X 4 are each independently >NR, >O, >S, >C(-R)2, >Si(-R)2, or >Se, and R of >NR, R of >C(-R)2, and R of >Si(-R)2 are each independently hydrogen, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted alkyl, or optionally substituted cycloalkyl; In addition, the X 1 ~X 4 two Rs in ">C(-R)" and two Rs in ">Si(-R)" may be bonded to each other independently via a single bond or a linking group, In addition, the X 1 or the aforementioned X 3R of “>NR”, R of “>C(—R)2”, and R of “>Si(—R)2” each independently represent at least one ring of the A ring and the B ring and at least one ring of the X ring. 2 or the aforementioned X 4 R of ">NR", R of ">C(-R)2", and R of ">Si(-R)2" may each independently be bonded to at least one of the ring A and ring c via a single bond or a linking group, However, the above X 1 ~X 4 at least one of the above is bonded to the A ring, B ring, or c ring via "-CR=CR-" as a linking group, and R in the "-CR=CR-" is 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 are bonded to form a cycloalkylene ring, an arylene ring, or a heteroarylene ring; In the compound represented by the above formula (1A) or (1B), at least one of ring A, ring B, ring c, the aryl, and the heteroaryl may be fused with at least one cycloalkane, at least one hydrogen in the cycloalkane may be substituted, and at least one "-CH2-" in the cycloalkane may be substituted with "-O-", At least one hydrogen atom in the compound represented by the above formula (1A) or (1B) may be substituted with deuterium, cyano, or halogen.

[0014] Section 2. In the above formula (1A) or formula (1B), ring A and ring B are each independently an aryl ring or a heteroaryl ring, and at least one hydrogen atom in these rings may be substituted with an optionally substituted aryl, an optionally substituted heteroaryl, an optionally substituted diarylamino, an optionally substituted diheteroarylamino, an optionally substituted arylheteroarylamino, an optionally substituted diarylboryl (two aryls may be bonded via a single bond or a linking group), an optionally substituted alkyl, an optionally substituted cycloalkyl, an optionally substituted alkoxy, an optionally substituted aryloxy, or a substituted silyl; R c are each independently hydrogen, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted diarylamino, optionally substituted diheteroarylamino, optionally substituted arylheteroarylamino, optionally substituted diarylboryl (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, or substituted silyl; -C(-R c )=" may be replaced with "-N=", Y 1 and Y 2 are each independently >B-, >P-, >P(=O)-, >P(=S)-, >Al-, >Ga-, >As-, >C(-R)-, >Si(-R)-, or >Ge(-R)-, and the R of ">C(-R)-", R of ">Si(-R)-", and R of ">Ge(-R)-" are each independently aryl, heteroaryl, alkyl, or cycloalkyl, and at least one hydrogen in the R may be substituted by alkyl or cycloalkyl, X 1 , X 2 , X 3 , and X 4are each independently >NR, >O, >S, >C(—R)2, >Si(—R)2, or >Se, and R of >NR, R of >C(—R)2, and R of >Si(—R)2 are each independently hydrogen, aryl, heteroaryl, alkyl, or cycloalkyl, and at least one hydrogen in the R may be substituted with alkyl or cycloalkyl; In addition, the X 1 ~X 4 two Rs in ">C(-R)2" and two Rs in ">Si(-R)2" may each independently be bonded to each other by a single bond, -CH=CH-, -CR=CR-, -C≡C-, -N(-R)-, -O-, -S-, -C(-R)2-, -Si(-R)2-, or -Se-; R in "-CR=CR-", R in "-N(-R)-", R in "-C(-R)2-", and R in "-Si(-R)2-" are each independently hydrogen, aryl, heteroaryl, alkyl, alkenyl, alkynyl, or cycloalkyl; at least one hydrogen in the R may be substituted by alkyl or cycloalkyl; two adjacent Rs may be bonded to each other to form a cycloalkylene ring, an arylene ring, or a heteroarylene ring; In addition, the X 1 or the aforementioned X 3 R of “>NR”, R of “>C(—R)2”, and R of “>Si(—R)2” each independently represent at least one ring of the A ring and the B ring and at least one ring of the X ring. 2 or the aforementioned X 4R of ">NR", R of ">C(-R)2", and R of ">Si(-R)2" as the above may each independently be bonded to at least one of the ring A and ring c via a single bond, -CH=CH-, -CR=CR-, -C≡C-, -N(-R)-, -O-, -S-, -C(-R)2-, -Si(-R)2-, or -Se-; R of ">CR=CR-", R of ">N(-R)-", R of ">C(-R)2-", and R of ">Si(-R)2-" are each independently hydrogen, aryl, heteroaryl, alkyl, alkenyl, alkynyl, or cycloalkyl, at least one hydrogen in the R may be substituted with alkyl or cycloalkyl, and two adjacent Rs may be bonded to form a cycloalkylene ring, an arylene ring, or a heteroarylene ring; However, the above X 1 ~X 4 at least one of the above is bonded to the ring A, ring B, or ring c via the "-CR=CR-" as a linking group, and two adjacent Rs in the "-CR=CR-" are bonded to each other to form a cycloalkylene ring, an arylene ring, or a heteroarylene ring; In the compound represented by the above formula (1A) or formula (1B), at least one of ring A, ring B, ring c, the aryl, and the heteroaryl may be fused with at least one cycloalkane, 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 the above formula (1A) or formula (1B) may be substituted with deuterium, cyano, or halogen. Item 1. The polycyclic aromatic compound according to item 1.

[0015] Section 3. Item 1. The polycyclic aromatic compound according to item 1, which is represented by the following general formula (2A) or (2B): [ka] In the above formula (2A) or formula (2B), R a , R b , and R c are each independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl (two aryls may be bonded via a single bond or a linking group), alkyl, cycloalkyl, alkoxy, aryloxy, triarylsilyl, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, or alkyldicycloalkylsilyl, and the R a , R b , and R c At least one hydrogen atom in R may be substituted with an aryl, heteroaryl, alkyl, or cycloalkyl. a and R b adjacent groups among the above may be bonded to each other to form an aryl ring or a heteroaryl ring together with the ring a and the ring b, and at least one hydrogen atom in the formed ring may be substituted with an aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl (the two aryls may be bonded via a single bond or a linking group), alkyl, cycloalkyl, alkoxy, aryloxy, triarylsilyl, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, or alkyldicycloalkylsilyl, and at least one hydrogen atom in these substituents may be substituted with an aryl, heteroaryl, alkyl, or cycloalkyl; -C(-R c )=" 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 with "-N=", and any "-C(-R)=C(-R)-" (where R is R a or R bmay be replaced by "-N(-R)-", "-O-", "-S-", "-C(-R)2-", "-Si(-R)2-", or "-Se-", R of the "-N(-R)-", R of the "-C(-R)2-", and R of the "-Si(-R)2-" are hydrogen, aryl, heteroaryl, alkyl, or cycloalkyl, and at least one hydrogen in the R may be substituted by alkyl or cycloalkyl, and the two Rs of the "-C(-R)2-" and the two Rs of the "-Si(-R)2-" are each independently a single bond, -CH=CH-, -CR=CR-, -C R of "-CR=CR-", R of "-N(-R)-", R of "-C(-R)-", and R of "-Si(-R)-" are each independently hydrogen, aryl, heteroaryl, alkyl, alkenyl, alkynyl, or cycloalkyl, at least one hydrogen atom in the R may be substituted with alkyl or cycloalkyl, and two adjacent Rs may be bonded to each other to form a cycloalkylene ring, an arylene ring, or a heteroarylene ring; Y 1 and Y 2 are each independently >B-, >P-, >P(=O)-, or >P(=S)-; X 1 , X 2 , X 3 , and X 4 are each independently >NR, >O, >S, or >C(—R)2, and R of the “>NR” and R of the “>C(—R)2” are each independently hydrogen, aryl, heteroaryl, alkyl, or cycloalkyl, and at least one hydrogen in the R may be substituted with alkyl or cycloalkyl; In addition, the X 1 ~X 4two Rs in ">C(-R)" as the formula may be bonded to each other by a single bond, -CH=CH-, -CR=CR-, -C≡C-, -N(-R)-, -O-, -S-, -C(-R)-, -Si(-R)-, or -Se-; R in "-CR=CR-", R in "-N(-R)-", R in "-C(-R)-", and R in "-Si(-R)-" are each independently hydrogen, aryl, heteroaryl, alkyl, alkenyl, alkynyl, or cycloalkyl; at least one hydrogen in the R may be substituted by alkyl or cycloalkyl; two adjacent Rs may be bonded to each other to form a cycloalkylene ring, an arylene ring, or a heteroarylene ring; In addition, the X 1 or the aforementioned X 3 R of ">NR" and R of ">C(-R)2" each independently represent at least one of the ring a and ring b and the ring X 2 or the aforementioned X 4 R of ">NR" and R of ">C(-R)2" as the above may each independently be bonded to at least one of the a ring and the c ring via a single bond, -CH=CH-, -CR=CR-, -C≡C-, -N(-R)-, -O-, -S-, -C(-R)2-, -Si(-R)2-, or -Se-; R of ">CR=CR-", R of ">N(-R)-", R of ">C(-R)2-", and R of ">Si(-R)2-" are each independently hydrogen, aryl, heteroaryl, alkyl, alkenyl, alkynyl, or cycloalkyl, at least one hydrogen in the R may be substituted with alkyl or cycloalkyl, and two adjacent Rs may be bonded to form a cycloalkylene ring, an arylene ring, or a heteroarylene ring; However, the above X 1 ~X 4 at least one of the above is bonded to the ring a, ring b, or ring c via the "-CR=CR-" as a linking group, and two adjacent Rs in the "-CR=CR-" are bonded to each other to form a cycloalkylene ring, an arylene ring, or a heteroarylene ring; In the compound represented by the above formula (2A) or formula (2B), at least one of the ring a, ring b, ring c, the formed ring, the aryl, and the heteroaryl may be condensed with at least one cycloalkane, 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 the above formula (2A) or (2B) may be substituted with deuterium, cyano, or halogen.

[0016] Section 4. In the above formula (2A) or formula (2B), R a , R b , and R c are each independently hydrogen, an aryl having 6 to 30 carbon atoms, a heteroaryl having 2 to 30 carbon atoms, a diarylamino (wherein the aryl is an aryl having 6 to 12 carbon atoms), a diarylboryl (wherein the aryl is an aryl having 6 to 12 carbon atoms, and the two aryls may be bonded via a single bond or a linking group), an alkyl having 1 to 24 carbon atoms, or a cycloalkyl having 3 to 24 carbon atoms, and the R a , R b , and R c At least one hydrogen atom in R may be substituted with an aryl having 6 to 12 carbon atoms, a heteroaryl having 2 to 15 carbon atoms, an alkyl having 1 to 6 carbon atoms, or a cycloalkyl having 3 to 14 carbon atoms. a and R badjacent groups among the above may be bonded to each other to form, together with ring a and ring b, an aryl ring having 9 to 16 carbon atoms or a heteroaryl ring having 6 to 15 carbon atoms, and at least one hydrogen atom in the formed ring may be substituted with an aryl having 6 to 30 carbon atoms, a heteroaryl having 2 to 30 carbon atoms, diarylamino (provided that the aryl is an aryl having 6 to 12 carbon atoms), diarylboryl (provided that the aryl is an aryl having 6 to 12 carbon atoms, and the two aryls may be bonded via a single bond or a linking group), an alkyl having 1 to 24 carbon atoms, or a cycloalkyl having 3 to 24 carbon atoms, and at least one hydrogen atom in these substituents may be substituted with an aryl having 6 to 12 carbon atoms, a heteroaryl having 2 to 15 carbon atoms, an alkyl having 1 to 6 carbon atoms, or a cycloalkyl having 3 to 14 carbon atoms; -C(-R c )=" 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 with "-N=", and any "-C(-R)=C(-R)-" (where R is R a or R bR of the "-N(-R)-", R of the "-C(-R)-" and R of the "-Si(-R)-" 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, and at least one hydrogen atom in the R may be substituted with alkyl having 1 to 6 carbon atoms or cycloalkyl having 3 to 14 carbon atoms, and the two Rs of the "-C(-R)-" and the two Rs of the "-Si(-R)-" are each independently a single bond, -CH=CH-, -CR=CR-, -C≡C-, -N(-R)-, -O-, -S- R of the "-CR=CR-", R of "-N(-R)-", R of "-C(-R)-", and R of "-Si(-R)-" each independently represent a hydrogen atom, an aryl having 6 to 10 carbon atoms, a heteroaryl having 2 to 10 carbon atoms, an alkyl having 1 to 5 carbon atoms, an alkenyl having 1 to 5 carbon atoms, an alkynyl having 1 to 5 carbon atoms, or a cycloalkyl having 5 to 10 carbon atoms, and at least one hydrogen atom in the R may be substituted by an alkyl having 1 to 6 carbon atoms or a cycloalkyl having 3 to 14 carbon atoms; two adjacent Rs may be bonded to each other 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; Y 1 and Y 2 are each independently >B-, >P-, >P(=O)-, or >P(=S)-; X 1 , X 2 , X 3 , and X 4 are each independently >NR, >O, or >S, and R in the ">NR" 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, and at least one hydrogen in the R is optionally substituted with alkyl having 1 to 6 carbon atoms or cycloalkyl having 3 to 14 carbon atoms; In addition, the X 1 or the aforementioned X 3 R in ">NR" as the formula is at least one of the ring a and the ring b, and the ring X 2 or the aforementioned X 4 R of ">NR" as the above may be bonded to at least one of the a ring and the c ring via a single bond, -CH=CH-, -CR=CR-, -C≡C-, -N(-R)-, -O-, -S-, -C(-R)2-, -Si(-R)2-, or -Se-, and R of the above "-CR=CR-", R of "-N(-R)-", R of "-C(-R)2-", and R of "-Si(-R)2-" each independently represent hydrogen, an aryl having 6 to 12 carbon atoms, a heteroaryl having 2 to 15 carbon atoms, R is a heteroaryl, an alkyl having 1 to 6 carbon atoms, an alkenyl having 1 to 6 carbon atoms, an alkynyl having 1 to 6 carbon atoms, or a cycloalkyl having 3 to 14 carbon atoms, and at least one hydrogen atom in the R may be substituted with an alkyl having 1 to 6 carbon atoms or a cycloalkyl having 3 to 14 carbon atoms; two adjacent Rs may be bonded 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; However, the above X 1 ~X 4 at least one of the above is bonded to the ring a, ring b, or ring c via the "-CR=CR-" as a linking group, and two adjacent Rs in the "-CR=CR-" are bonded to each other 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 the above formula (2A) or (2B), at least one of the ring a, ring b, ring c, 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 atom in the compound represented by the above formula (2A) or formula (2B) may be substituted with deuterium, cyano, or halogen. Item 3. The polycyclic aromatic compound according to item 3.

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

[0018] Section 6. In the above formula (2A) or formula (2B), R a , R b , and R care each independently hydrogen, an aryl having 6 to 16 carbon atoms, a heteroaryl having 2 to 20 carbon atoms, a diarylamino (wherein the aryl is an aryl having 6 to 10 carbon atoms), a diarylboryl (wherein the aryl is an aryl having 6 to 10 carbon atoms, and the two aryls may be bonded via a single bond or a linking group), an alkyl having 1 to 12 carbon atoms, or a cycloalkyl having 3 to 16 carbon atoms, and the R a , R b , and R c at least one hydrogen atom in the formula (I) may be substituted with alkyl having 1 to 5 carbon atoms or cycloalkyl having 5 to 10 carbon atoms; -C(-R c )=" 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 with "-N=", and any "-C(-R)=C(-R)-" (where R is R a or R b (which is) may be replaced with "-N(-R)-", "-O-", or "-S-", and R of the "-N(-R)-" is 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, Y 1 and Y 2 is >B-, X 1 , X 2 , X 3 , and X 4 are each independently >NR or >O, and R in the ">NR" is 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, and at least one hydrogen atom in the R may be substituted with an alkyl having 1 to 5 carbon atoms or a cycloalkyl having 5 to 10 carbon atoms, In addition, the X 1 or the aforementioned X 3 R in ">NR" as the ring b and the ring X 2 or the aforementioned X4 R in ">NR" as the formula may be bonded to the ring a via a single bond or -CR=CR-, and R in the "-CR=CR-" are each independently hydrogen, aryl having 6 to 10 carbon atoms, heteroaryl having 2 to 10 carbon atoms, alkyl having 1 to 5 carbon atoms, alkenyl having 1 to 5 carbon atoms, alkynyl having 1 to 5 carbon atoms, or cycloalkyl having 5 to 10 carbon atoms, and at least one hydrogen in the R may be substituted with alkyl having 1 to 5 carbon atoms or cycloalkyl having 5 to 10 carbon atoms, and two adjacent R may be bonded to form an arylene ring having 6 to 10 carbon atoms or a heteroarylene ring having 2 to 10 carbon atoms, However, the above X 1 and X 3 at least one of is bonded to the ring b via the "-CR=CR-" as a linking group, and two adjacent Rs in the "-CR=CR-" are bonded to each other to form an arylene ring having 6 to 10 carbon atoms or a heteroarylene ring having 2 to 10 carbon atoms; At least one hydrogen atom in the compound represented by the above formula (2A) or formula (2B) may be substituted with deuterium, cyano, or halogen. Item 3. The polycyclic aromatic compound according to item 3.

[0019] Section 7. Item 1. The polycyclic aromatic compound according to item 1, which is represented by any one of the following structural formulas: [ka] The benzene rings in the above structural formula may each independently be substituted with an aryl having 6 to 16 carbon atoms, a heteroaryl having 2 to 20 carbon atoms, a diarylamino (wherein the aryl is an aryl having 6 to 10 carbon atoms), a diarylboryl (wherein the aryl is an aryl having 6 to 10 carbon atoms, and two aryls may be bonded via a single bond or a linking group), an alkyl having 1 to 12 carbon atoms, or a cycloalkyl having 3 to 16 carbon atoms, and at least one hydrogen atom in the substituent may be substituted with an alkyl having 1 to 5 carbon atoms or a cycloalkyl having 5 to 10 carbon atoms; 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. Item 1. The polycyclic aromatic compound according to item 1, which is represented by any one of the following structural formulas: [ka]

[0021] Section 9. A reactive compound in which the polycyclic aromatic compound according to any one of items 1 to 8 is substituted with a reactive substituent.

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

[0023] Section 11. Item 9. A pendant polymer compound in which a reactive compound described in Item 9 is substituted on a main chain polymer, or a pendant polymer crosslinked product in which the pendant polymer compound is further crosslinked.

[0024] Section 12. Item 9. A material for an organic device, comprising the polycyclic aromatic compound according to any one of Items 1 to 8.

[0025] Section 13. Item 10. A material for an organic device, comprising the reactive compound according to item 9.

[0026] Section 14. Item 11. A material for an organic device, comprising the polymer compound or crosslinked polymer according to item 10.

[0027] Section 15. Item 12. A material for organic devices, comprising the pendant polymer compound or pendant polymer crosslinked body according to item 11.

[0028] Section 16. Item 16. The material for an organic device according to any one of Items 12 to 15, wherein the material for an organic device is a material for an organic electroluminescent element, 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. Item 17. The material for an organic device according to item 16, wherein the material for an organic electroluminescent element is a material for an emitting layer.

[0030] Section 18. Item 9. An ink composition comprising the polycyclic aromatic compound according to any one of Items 1 to 8 and an organic solvent.

[0031] Section 19. Item 10. An ink composition comprising the reactive compound according to item 9 and an organic solvent.

[0032] Section 20. Item 10. An ink composition comprising a main chain polymer, the reactive compound according to item 9, and an organic solvent.

[0033] Section 21. Item 11. An ink composition comprising the polymer compound or crosslinked polymer according to item 10 and an organic solvent.

[0034] Section 22. Item 12. An ink composition comprising the pendant polymer compound or pendant polymer crosslinked product according to item 11 and an organic solvent.

[0035] Section 23. An organic electroluminescence device comprising a pair of electrodes consisting of an anode and a cathode, and an organic layer disposed between the pair of electrodes and containing the polycyclic aromatic compound described in any one of items 1 to 8, the reactive compound described in item 9, the polymer compound or crosslinked polymer described in item 10, or the pendant polymer compound or crosslinked pendant polymer described in item 11.

[0036] Section 24. Item 24. The organic electroluminescent device according to item 23, wherein the organic layer is a light-emitting layer.

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

[0038] Section 26. Item 26. The organic electroluminescent device according to item 25, 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 having 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: [ka] In the above general formula (H1), L 1 is an arylene having 6 to 30 carbon atoms or a heteroarylene having 2 to 30 carbon atoms, In the above general formula (H2), L 2 and L 3 are each independently an aryl having 6 to 30 carbon atoms or a heteroaryl having 2 to 30 carbon atoms, In the general formula (H3), each MU is independently a divalent group represented by removing any two hydrogen atoms from an aromatic compound, each EC is independently a monovalent group represented by removing any one hydrogen atom from an aromatic compound, and two hydrogen atoms in MU are replaced by EC or MU, and k is an integer of 2 to 50,000. In the general formula (H4), each G is independently =C(-H)- or =N-, and H in the =C(-H)- may be substituted with a substituent or another structure represented by formula (H4), In the above general formula (H5), R 1 ~R 11 are each independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, alkyl, or cycloalkyl, and the R 1~R 11 at least one hydrogen atom in the formula (I) may be further substituted with an aryl, heteroaryl, diarylamino, alkyl, or cycloalkyl; R 1 ~R 11 adjacent groups among these may be bonded to each other to form an aryl ring or a heteroaryl ring together with ring a, ring b or ring c, and at least one hydrogen atom in the formed ring may be substituted with aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, alkyl or cycloalkyl, and at least one hydrogen atom 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 ) may be replaced with "-N=", In the above general formula (H6), R 1 ~R 16 are each independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, alkyl, or cycloalkyl, and the R 1 ~R 16 at least one hydrogen atom in the formula (I) may be further substituted with an aryl, heteroaryl, diarylamino, alkyl, or cycloalkyl; R 1 ~R 16 adjacent groups among may be bonded to each other to form an aryl ring or a heteroaryl ring together with the a ring, the b ring, the c ring, or the d ring, and at least one hydrogen atom in the formed ring may be substituted with an aryl, a heteroaryl, a diarylamino, a diheteroarylamino, an arylheteroarylamino, an alkyl, or a cycloalkyl, and at least one hydrogen atom in these substituents may be further substituted with an aryl, a heteroaryl, a diarylamino, an alkyl, or a cycloalkyl, and At least one hydrogen atom in the compound or structure represented by each of 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] Section 27. Item 27. The organic electroluminescence device according to any one of items 23 to 26, further comprising at least one of an electron transport layer and an electron injection layer disposed between the cathode and the light-emitting layer, wherein at least one of the electron transport layer and the electron injection layer contains at least one selected from the group consisting of borane derivatives, pyridine derivatives, fluoranthene derivatives, BO-based 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. Item 28. The organic electroluminescent device according to item 27, wherein at least one of the electron transport layer and the electron injection layer further contains at least one selected from the group consisting of alkali metals, alkaline earth metals, rare earth metals, 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. Item 29. The organic electroluminescence device according to any one of items 23 to 28, wherein at least one layer of the hole injection layer, the hole transport layer, the light-emitting layer, the electron transport layer, and the electron injection layer comprises a polymer compound obtained by polymerizing a low-molecular-weight compound capable of forming each layer as a monomer, or a crosslinked polymer obtained by further crosslinking the polymer compound, or a pendant-type polymer compound obtained by reacting a low-molecular-weight compound capable of forming each layer with a main-chain polymer, or a pendant-type crosslinked polymer obtained by further crosslinking the pendant-type polymer compound.

[0042] Section 30. 30. A display or lighting device comprising the organic electroluminescent device according to any one of items 23 to 29.

[0043] Section 31. Item 17. A wavelength conversion filter comprising the wavelength conversion filter material according to Item 16. [Effects of the Invention]

[0044] According to a preferred embodiment of the present invention, it is possible to provide a polycyclic aromatic compound having a novel structure that can be used as a material for organic devices such as a material for an organic EL element, and by using this polycyclic aromatic compound, it is possible to provide an excellent organic device such as an organic EL element.

[0045] Specifically, the inventors discovered that polycyclic aromatic compounds in which aromatic rings are linked by heteroatoms such as boron, phosphorus, oxygen, nitrogen, and sulfur exhibit large or small HOMO-LUMO gaps (band gaps in thin films, Eg), depending on the linking method of the heteroatoms. This is thought to be due to the low aromaticity of six-membered rings containing heteroatoms, which suppresses or accelerates the reduction of the HOMO-LUMO gap associated with the expansion of the conjugated system and the localization or delocalization of each orbital. These polycyclic aromatic compounds possess a robust skeleton formed by fused or linked five- or six-membered rings, resulting in narrow half-widths of the fluorescence emission peaks and high color purity when used as emitters in organic light-emitting diode (OLED) devices. In addition, by selecting the linking method of the heteroatoms, they exhibit thermally activated delayed fluorescence, achieving high efficiency when used as emitters in OLED devices. Furthermore, the HOMO and LUMO energies can be adjusted by introducing substituents, allowing the ionization potential and electron affinity to be optimized depending on the surrounding materials. However, the present invention is not particularly limited to these principles. [Brief explanation of the drawings]

[0046]

Figure 1

Figure 2

[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 (1A) or general formula (1B), and preferably to a polycyclic aromatic compound represented by the following general formula (2A) or general formula (2B). The symbols in each structural formula are defined as above, and the symbols in all structural formulas shown in this paragraph and thereafter are also defined as above. [ka] [ka]

[0048] Each compound has two unit structures formed by condensing ring A, ring B, and ring c to a condensed bicyclic structure, and these two unit structures are condensed so as to share ring c, forming a ring-sharing condensed structure. The condensed bicyclic structure is a structure in which two 6-membered saturated hydrocarbon rings are condensed together, and in the above structural formula, Y 1 and X 1 and X 2 and a decahydronaphthalene structure on the left comprising Y 2 and X 3 and X 4 The decahydronaphthalene structure on the right is composed of

[0049] There are meta and para compounds, and the meta compound is Y 1 and Y 2 The para-type compound has a structure in which two unit structures are condensed so that Y is located at the meta position of the c ring. 1 and Y 2It has a structure in which two unit structures are condensed so that is located at the para position of the c-ring.

[0050] <Description of the ring structure and its substituents in the compound> In each formula, the ring A and the ring B are each independently an aryl ring or a heteroaryl ring, and at least one hydrogen atom in these rings may be substituted with a substituent. The substituent is preferably an optionally substituted aryl, an optionally substituted heteroaryl, an optionally substituted diarylamino, an optionally substituted diheteroarylamino, an optionally substituted arylheteroarylamino (an amino group having an aryl and a heteroaryl), an optionally substituted diarylboryl (the two aryls may be bonded via a single bond or a linking group), an optionally substituted alkyl, an optionally substituted cycloalkyl, an optionally substituted alkoxy, an optionally substituted aryloxy, or a substituted silyl. When these substituents further have a substituent, the substituent may be an aryl, a heteroaryl, a diarylamino, a diheteroarylamino, an arylheteroarylamino, a diarylboryl (the two aryls may be bonded via a single bond or a linking group), an alkyl, a cycloalkyl, an alkoxy, an aryloxy, or a substituted silyl. Details of the rings and substituents listed here will be summarized below.

[0051] R in each formula a , R b , and R cis hydrogen or a substituent, and specifically, hydrogen, 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 bonded via a single bond or a linking group), optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted alkoxy, optionally substituted aryloxy, or substituted silyl is preferred. When these substituents further have a substituent, examples of the substituent include aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl (the two aryls may be bonded via a single bond or a linking group), alkyl, cycloalkyl, alkoxy, aryloxy, or substituted silyl. Details of the rings and substituents listed here will be summarized below.

[0052] R in each formula a , R b , and R c Specific examples of R are each independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl (two aryls may be bonded via a single bond or a linking group), alkyl, cycloalkyl, alkoxy, aryloxy, triarylsilyl, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, or alkyldicycloalkylsilyl, and R a , R b , and R c At least one hydrogen atom in may be substituted with an aryl, heteroaryl, alkyl, or cycloalkyl. Details of the substituents listed here will be summarized below.

[0053] The aryl or heteroaryl ring as ring A and ring B preferably has a 5- or 6-membered ring that shares a bond with the above-mentioned fused bicyclic structure. Here, "a six-membered ring sharing a bond with the fused bicyclic structure" refers to rings a and b (benzene rings (six-membered rings)) fused to the fused bicyclic structure, as shown in formula (2A) and formula (2B), for example. Furthermore, "an aryl ring or heteroaryl ring (ring A and ring B) has this six-membered ring" means that rings A and B are formed solely from this six-membered ring, or that rings A and B are formed by further condensing other rings to this six-membered ring. In other words, "an aryl ring or heteroaryl ring (ring A and ring B) having a six-membered ring" means that the six-membered rings constituting all or part of ring A and ring B are fused to the fused bicyclic structure. The same explanation also applies to "five-membered ring."

[0054] The A ring and the B ring in the formula (1A) and the formula (1B) are respectively the a ring and its substituent R in the formula (2A) and the formula (2B). a , and the b ring and its substituent R b That is, formula (2A) and formula (2B) correspond to a structure in which "ring A and ring B having a 6-membered ring (a benzene ring)" are selected as ring A and ring B of formula (1A) and formula (1B), respectively. In this sense, each ring in formula (2A) and formula (2B) is represented by the lowercase letters "a" and "b."

[0055] <Description of the change in the ring structure due to the bond between substituents> Substituent R of ring a and ring b a and R bAdjacent groups among may be bonded to each other to form an aryl ring or a heteroaryl ring together with the a ring or the b ring, and at least one hydrogen atom in the formed ring may be substituted with an aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl (the two aryls may be bonded via a single bond or a linking group), alkyl, cycloalkyl, alkoxy, aryloxy, triarylsilyl, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, or alkyldicycloalkylsilyl, and at least one hydrogen atom in these substituents may be substituted with an aryl, heteroaryl, alkyl, or cycloalkyl. Details of the rings and substituents listed here will be described below.

[0056] Therefore, in the polycyclic aromatic compound of formula (2A) or formula (2B), the ring structure constituting the compound changes depending on the mutual bonding form of the substituents in ring a and ring b, as shown in the following formulas (2AB-fr1) to (2AB-fr3). Ring A' and ring B' in each formula correspond to ring A and ring B in formula (1A) and formula (1B), respectively. Note that each formula shows only the unit structure portion for simplification, and a compound is constituted by condensing two of these unit structures in a meta or para configuration.

[0057] [ka]

[0058] The A′ ring and the B′ ring in the above formulae (2AB-fr1) to (2AB-fr3) can be represented by a plurality of substituents R a and R b Adjacent groups in the formula (a) and (b) bond together to form an aryl or heteroaryl ring together with the ring a and the ring b, respectively (these may also be considered fused rings formed by fusing another ring structure to the ring a or the ring b). a and the substituent R of ring b bdoes not correspond to "adjacent groups" and these are not bonded to each other. In other words, "adjacent groups" means groups adjacent to each other on the same ring.

[0059] Specific examples of the above formulae (2AB-fr1) to (2AB-fr3) include structures having ring A' or ring B' formed by condensing a benzene ring, which is ring a, or ring b, with a benzene ring, for example, an indole ring, a pyrrole ring, a benzofuran ring, or a benzothiophene ring, and the condensed ring A' or condensed ring B' formed is a naphthalene ring, a carbazole ring, an indole ring, a dibenzofuran ring, or a dibenzothiophene ring, respectively.

[0060] For example, more specific examples of formulae (2AB-fr1) to (2AB-fr3) are shown below. [ka]

[0061] The above formula (2AB-fr1-ex) is a specific example of formula (2AB-fr1), and two adjacent R a This is an example in which an aryl ring (naphthalene ring) represented by A' is formed together with the a ring (benzene ring). The formed aryl ring has a six-membered ring (benzene ring a) that shares a bond with the above-mentioned fused two-ring structure. Note that an optional substituent on the aryl ring A' (ring A in formula (1A) or formula (1B)) can be R a In addition, n Rs are shown, and the upper limit of n is the maximum number of substitutions possible.

[0062] The above formula (2AB-fr2-ex) is a specific example of formula (2AB-fr2), and two adjacent R b is bonded to the b ring (benzene ring) to form a heteroaryl ring (carbazole ring) shown as B'. The formed heteroaryl ring has a six-membered ring (benzene ring b) that shares a bond with the above-mentioned fused two-ring structure. Note that an optional substituent on the aryl ring B' (ring B in formula (1A) or formula (1B)) can be added as Rb In addition, n Rs are shown, and the upper limit of n is the maximum number of substitutions possible.

[0063] The above formula (2AB-fr3-ex) is a specific example of formula (2AB-fr3), and two adjacent R a are bonded to form a heteroaryl ring (dibenzofuran ring) represented by A' together with the a ring (benzene ring), and the two adjacent R b is bonded to the b ring (benzene ring) to form an aryl ring (naphthalene ring) shown as B'. 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 above-mentioned fused two-ring structure. In addition, optional substituents on the heteroaryl ring A' (ring A in formula (1A) or formula (1B)) and the aryl ring B' (ring B in formula (1A) or formula (1B)) can be added as R a and R b In addition, n Rs are shown, and the upper limit of n is the maximum number of substitutions possible.

[0064] The above description can be similarly applied to any embodiment other than the above-mentioned specific example.

[0065] <Central element Y in the compound 1 and Y 2 description> Y in each formula 1 and Y 2is >B-, >P-, >P(=O)-, >P(=S)-, >Al-, >Ga-, >As-, >C(-R)-, >Si(-R)-, or >Ge(-R)-, and R of the ">C(-R)-", R of ">Si(-R)-", and R of ">Ge(-R)-" are each independently an optionally substituted aryl, an optionally substituted heteroaryl, an optionally substituted alkyl, or an optionally substituted cycloalkyl. In the case of >P(=O)-, >P(=S)-, >C(-R)-, >Si(-R)-, or >Ge(-R)-, the atoms bonding to ring A (ring a), ring B (ring b), and ring c are P, C, Si, or Ge. Y is 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 summarized later.

[0066] <Linking element X in the compound 1 、X 2 、X 3 , and X 4 description> X in each formula 1 , X 2 , X 3 , and X 4 are each independently >NR, >O, >S, >C(-R)2, >Si(-R)2, or >Se, and the R of >NR, the R of >C(-R)2, and the R of >Si(-R)2 are each independently hydrogen, an optionally substituted aryl, an optionally substituted heteroaryl, an optionally substituted alkyl, or an optionally substituted cycloalkyl. X 1 , X 2 , X 3 , and X 4From the viewpoint of stability, >NR, >O, >S, or >C(-R)2 is preferred, with >NR or >O being more preferred. From the viewpoint of short-wavelength emission, >NR, >O, or >C(-R)2 is preferred, with >O or >C(-R)2 being more preferred. The details of the substituents listed here will be described later.

[0067] In addition, the X 1 ~X 4 The two Rs in ">C(-R)" and the two Rs in ">Si(-R)" may each independently be bonded by a single bond or a linking group (collectively referred to as a bonding group). Examples of this linking group include -CH-CH-, -CHR-CHR-, -CR-CR-, -CH=CH-, -CR=CR-, -C≡C-, -N(-R)-, -O-, -S-, -C(-R)-, -Si(-R)-, or -Se-, and examples thereof include the following structures: The R of "-CHR-CHR-", the R of "-CR-CR-", the R of "-CR=CR-", the R of "-N(-R)-", the R of "-C(-R)-", and the R of "-Si(-R)-" are each independently hydrogen, aryl, heteroaryl, alkyl, alkenyl, alkynyl, or cycloalkyl, and at least one hydrogen in the R may be substituted with alkyl or cycloalkyl. Furthermore, adjacent Rs in "-CHR-CHR-", "-CR-CR-", "-CR=CR-", "-C(-R)-", and "-Si(-R)-" may be bonded to each other to form a cycloalkylene ring, an arylene ring, or a heteroarylene ring (see the rightmost structural formula in the structural formula below). Details of the substituents listed here will be summarized below. [ka]

[0068] As the linking group, a single bond, and -CR=CR-, -N(-R)-, -O-, -S-, -C(-R)2-, -Si(-R)2-, and -Se- as linking groups are preferred, a single bond, and -CR=CR-, -N(-R)-, -O-, -S-, and -C(-R)2- as linking groups are more preferred, a single bond, and -CR=CR-, -N(-R)-, -O-, and -S- as linking groups are still more preferred, and a single bond and -CR=CR- as a linking group are most preferred.

[0069] The position at which two Rs are bonded by the bonding group is not particularly limited as long as it is a position where bonding is possible, but it is preferable that they are bonded at the most adjacent positions. For example, when two Rs are phenyl groups, it is preferable that they are bonded at positions ortho (2nd position) relative to the bonding position (1st position) of "C" or "Si" in the phenyl group (see the structural formula above).

[0070] <X 1 ~X 4 <Description of the change in the ring structure due to the bond between the ring and [X]] X 1 or X 3 R in ">NR", R in ">C(-R)2", and R in ">Si(-R)2" may each independently be bonded to at least one of ring A (ring a) and ring B (ring b) via a single bond or a linking group, and X 2 or X 4 As the above, R in ">NR", R in ">C(-R)2", and R in ">Si(-R)2" may each independently be bonded to at least one of ring A (ring a) and ring c via a single bond or a linking group. X that can participate in binding 1 As the group, >NR and >C(-R)2 are preferred, and >NR is more preferred. The ring to be bonded is X 1 or X 3 For B-ring (b-ring), X 2 or X 4 For the above, ring A (a ring) is preferred. Examples of the linking group connecting R to the ring include -CH2-CH2-, -CHR-CHR-, -CR2-CR2-, -CH=CH-, -CR=CR-, -C≡C-, -N(-R)-, -O-, -S-, -C(-R)2-, -Si(-R)2-, and -Se-; -CH=CH-, -CR=CR-, -N(-R)-, -O-, -S-, and -C(-R)2- are preferred; -CH=CH-, -CR=CR-, -N(-R)-, -O-, and -S- are more preferred; -CR=CR-, -N(-R)-, -O-, and -S- are even more preferred; and -CR=CR- is particularly preferred. The R of "-CHR-CHR-", the R of "-CR-CR-", the R of "-CR=CR-", the R of "-N(-R)-", the R of "-C(-R)-", and the R of "-Si(-R)-" are each 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. Furthermore, two adjacent Rs may be bonded to form a cycloalkylene ring, an arylene ring, or a heteroarylene ring. At least one hydrogen in these rings may also be substituted with an alkyl or cycloalkyl. The details of the substituents listed here will be described later.

[0071] "The X" in formula (1A) and formula (1B) 1 or the aforementioned X 3 R of “>NR”, R of “>C(—R)2”, and R of “>Si(—R)2” each independently represent at least one ring of the A ring and the B ring and at least one ring of the X ring. 2 or the aforementioned X 4 The definition that R of “>NR”, R of “>C(—R)2”, and R of “>Si(—R)2” are each independently bonded to at least one of the A ring and the c ring via a single bond or a linking group” is not true in formula (2A) and formula (2B) of the formula (2A). 1 or the aforementioned X 3R of “>NR”, R of “>C(—R)2”, and R of “>Si(—R)2” each independently represent at least one ring of the a ring and the b ring, and 2 or the aforementioned X 4 R of ">NR", R of ">C(-R)2", and R of ">Si(-R)2 as the a-ring and c-ring are each independently bonded to at least one of the a-ring and c-ring via a single bond, -CH2-CH2-, -CHR-CHR-, -CR2-CR2-, -CH=CH-, -CR=CR-, -C≡C-, -N(-R)-, -O-, -S-, -C(-R)2-, -Si(-R)2-, or -Se-.

[0072] This rule can be expressed in the meta-type by the following structural formula: a , R b and R c Although it is not shown, it actually exists. The same can be said about the para type. [ka]

[0073] The structural formula on the left is the formula (2A), X 1 In the options (>NR, >C(-R)2, and >Si(-R)2), R is connected to the b ring (benzene ring) by a single bond or a linking group, forming X 1 While incorporating the ring b, another ring is fused to the ring b (benzene ring) to form ring B', X 2 In the options (>NR, >C(-R)2, and >Si(-R)2), R is connected to the left a ring (benzene ring) by a single bond or a linking group, forming X 2 While incorporating the ring, other rings are fused to the left a ring (benzene ring) to form the left A' ring, X 3 In the options (>NR, >C(-R)2, and >Si(-R)2), R is connected to the right a ring (benzene ring) by a single bond or a linking group, forming X 3This represents a compound in which the right a ring (benzene ring) is fused with another ring while incorporating the other ring to form the right A' ring. The formed fused ring B', the left fused ring A', and the right fused ring A' are, for example, a ring having an azepine structure, a phenoxazine ring, a phenothiazine ring, a carbazole ring, or an acridine ring. 4 There are also examples where the ring is bonded to the ring, and examples where the c ring is bonded.

[0074] The structural formula on the right is 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) via the linking group "-CR=CR-" (two adjacent Rs are bonded to form an aryl ring, which is a phenylene ring), forming ring B', which has an azepine structure, surrounded by a dashed line. X 2 The R (phenyl group) of >NR is bonded to the left a ring (benzene ring) via the linking group "-O-" to form the phenoxazine ring A' (left side) surrounded by a dashed line. X 3 This represents a compound in which the R (phenyl group) of >NR is bonded to the a ring (benzene ring) on ​​the right by a single bond to form the carbazole ring A' (right side) surrounded by a dashed line.

[0075] However, X in each formula 1 ~X 4 At least one of X is bonded to ring A (ring a), ring B (ring b), or ring c via "-CR=CR-" as a linking group. 1 and X 3 is bonded to ring B (ring b) via the "-CR=CR-". In addition, two adjacent Rs in the "-CR=CR-" are 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.

[0076] The explanation of the above-mentioned specific examples can be similarly applied to any other embodiments.

[0077] <Description of the structural changes of the a-ring, b-ring, and c-ring>

[0078] In the explanation so far, the ring c in formula (1A) and formula (1B), and the rings a, b, and c in formula (2A) and formula (2B) have basically been explained as benzene rings, but below, examples will be explained in which these rings are structurally changed to 5- or 6-membered aryl or heteroaryl rings other than benzene rings. Note that the explanation so far can be similarly understood when these rings undergo the following structural changes.

[0079] <Structural change of the c-ring> -C(-R c )=" can be replaced with "-N=", forming a pyridine ring or pyrazine ring. Note that the following structural formula is a formula that only shows the c ring and part of its surrounding structure. [ka]

[0080] <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 symbol "-N=" may be replaced with "-N=". Note that the following structural formula is a formula that extracts only the a-ring or b-ring and a part of the surrounding structure. [ka]

[0081] As shown above, the a-ring or b-ring shown as a benzene ring in formula (2A) and formula (2B) may be changed to a pyridine ring, a pyrimidine ring, a pyridazine ring, a pyrazine ring, or other nitrogen-containing heteroaryl ring. In addition, when adjacent groups are present on the a-ring or b-ring (as in the above structural formula, two R aTwo R b As described above, when the rings a and b are bonded to each other, they form a heteroaryl ring (a quinoline ring in the above structural formula) together with the ring a or b, and the formed ring may be further substituted (indicated by n Rs).

[0082] The same applies when other positions are replaced with "-N=" or when adjacent substituents are bonded to form another heteroaryl ring.

[0083] <Structural change of the a-ring (2)> In the a ring, any "-C(-R a )=C(-R a )-" may be replaced with "-N(-R)-", "-O-", "-S-", "-C(-R)2-", "-Si(-R)2-", or "-Se-", and R of "-N(-R)-", R of "-C(-R)2-", and R of "-Si(-R)2-" are hydrogen, aryl, heteroaryl, alkyl, or cycloalkyl, and at least one hydrogen in these may be substituted with alkyl or cycloalkyl. Details of the substituents listed here will be described below. [ka] The above structural formula is a formula that extracts only the a-ring and part of its surrounding structure, and to avoid complexity, the wavy lines that indicate partial structures have been omitted.

[0084] As shown above, the a-ring shown as a benzene ring in formula (2A) and formula (2B) may be changed to an R-substituted pyrrole ring, furan ring, thiophene ring, or other nitrogen-, oxygen-, sulfur-, silicon-, or selenium-containing heteroaryl ring (5-membered ring) or aryl ring (5-membered ring).

[0085] The same applies when other positions are replaced with "-N(-R)-", "-O-", "-S-", "-C(-R)2-", "-Si(-R)2-", or "-Se-".

[0086] The two Rs in "-C(-R)-" and the two Rs in "-Si(-R)-" may each independently be bonded by a single bond or a linking group (collectively referred to as a linking group). Examples of this linking group include -CH-CH-, -CHR-CHR-, -CR-CR-, -CH=CH-, -CR=CR-, -C≡C-, -N(-R)-, -O-, -S-, -C(-R)-, -Si(-R)-, or -Se-, and examples thereof include the following structures: The R of "-CHR-CHR-", the R of "-CR-CR-", the R of "-CR=CR-", the R of "-N(-R)-", the R of "-C(-R)-", and the R of "-Si(-R)-" are each independently hydrogen, aryl, heteroaryl, alkyl, alkenyl, alkynyl, or cycloalkyl, and at least one hydrogen in the R may be substituted with alkyl or cycloalkyl. Furthermore, adjacent Rs in "-CHR-CHR-", "-CR-CR-", "-CR=CR-", "-C(-R)-", and "-Si(-R)-" may be bonded to each other to form a cycloalkylene ring, an arylene ring, or a heteroarylene ring (see the rightmost structural formula in the structural formula below). Details of the substituents listed here will be summarized below. [ka]

[0087] As the linking group, a single bond, and -CR=CR-, -N(-R)-, -O-, -S-, -C(-R)2-, -Si(-R)2-, and -Se- as linking groups are preferred, a single bond, and -CR=CR-, -N(-R)-, -O-, -S-, and -C(-R)2- as linking groups are more preferred, a single bond, and -CR=CR-, -N(-R)-, -O-, and -S- as linking groups are still more preferred, and a single bond and -CR=CR- as a linking group are most preferred.

[0088] The position at which two Rs are bonded by the bonding group is not particularly limited as long as it is a position where bonding is possible, but it is preferable that they are bonded at the most adjacent positions. For example, when two Rs are phenyl groups, it is preferable that they are bonded at positions ortho (2nd position) relative to the bonding position (1st position) of "C" or "Si" in the phenyl group (see the structural formula above).

[0089] <Structural change of the b-ring (2)> In the b-ring, any "-C(-R b )=C(-R b )-" may be replaced with "-N(-R)-", "-O-", "-S-", "-C(-R)2-", "-Si(-R)2-", or "-Se-", and R of "-N(-R)-", R of "-C(-R)2-", and R of "-Si(-R)2-" are hydrogen, aryl, heteroaryl, alkyl, or cycloalkyl, and at least one hydrogen in these may be substituted with alkyl or cycloalkyl. Details of the substituents listed here will be described below. [ka] The above structural formula is a formula that extracts only the b ring and part of its surrounding structure.

[0090] As shown above, the b ring shown as a benzene ring in formula (2A) and formula (2B) may be changed to an R-substituted pyrrole ring, furan ring, thiophene ring, or other nitrogen-, oxygen-, sulfur-, silicon-, or selenium-containing heteroaryl ring (5-membered ring) or aryl ring (5-membered ring). Also, when adjacent groups are present on the b ring (in the above formula, the remaining two adjacent R b ) are bonded to ring b to form a heteroaryl ring (a ring such as an R-substituted indole ring, benzofuran ring, or benzothiophene ring in the above formula) or an aryl ring, and the formed ring may be further substituted (indicated by n Rs), as described above.

[0091] In addition, there are the following variations: [ka]

[0092] The same applies when other positions are replaced with "-N(-R)-", "-O-", "-S-", "-C(-R)2-", "-Si(-R)2-", or "-Se-".

[0093] The two Rs in "-C(-R)-" and the two Rs in "-Si(-R)-" may each independently be bonded by a single bond or a linking group (collectively referred to as a linking group). Examples of this linking group include -CH-CH-, -CHR-CHR-, -CR-CR-, -CH=CH-, -CR=CR-, -C≡C-, -N(-R)-, -O-, -S-, -C(-R)-, -Si(-R)-, or -Se-, and examples thereof include the following structures: The R of "-CHR-CHR-", the R of "-CR-CR-", the R of "-CR=CR-", the R of "-N(-R)-", the R of "-C(-R)-", and the R of "-Si(-R)-" are each independently hydrogen, aryl, heteroaryl, alkyl, alkenyl, alkynyl, or cycloalkyl, and at least one hydrogen in the R may be substituted with alkyl or cycloalkyl. Furthermore, adjacent Rs in "-CHR-CHR-", "-CR-CR-", "-CR=CR-", "-C(-R)-", and "-Si(-R)-" may be bonded to each other to form a cycloalkylene ring, an arylene ring, or a heteroarylene ring (see the rightmost structural formula in the structural formula below). Details of the substituents listed here will be summarized below. [ka]

[0094] As the linking group, a single bond, and -CR=CR-, -N(-R)-, -O-, -S-, -C(-R)2-, -Si(-R)2-, and -Se- as linking groups are preferred, a single bond, and -CR=CR-, -N(-R)-, -O-, -S-, and -C(-R)2- as linking groups are more preferred, a single bond, and -CR=CR-, -N(-R)-, -O-, and -S- as linking groups are still more preferred, and a single bond and -CR=CR- as a linking group are most preferred.

[0095] The position at which two Rs are bonded by the bonding group is not particularly limited as long as it is a position where bonding is possible, but it is preferable that they are bonded at the most adjacent positions. For example, when two Rs are phenyl groups, it is preferable that they are bonded at positions ortho (2nd position) relative to the bonding position (1st position) of "C" or "Si" in the phenyl group (see the structural formula above).

[0096] <Specific description of the ring and substituents> Next, the details of the rings and substituents (including the second substituents that further substitute the first substituents) enumerated in the above explanation will be explained together.

[0097] The "aryl ring" is, for example, an aryl ring having 6 to 30 carbon atoms, and 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. The "aryl ring" as the ring A and ring B in formula (1A) and formula (1B) is defined as "R a and R b The term "aryl ring" corresponds to "an aryl ring formed together with ring a and ring b by bonding adjacent groups among the above, but for this "formed aryl ring", since ring a or ring b is already composed of a benzene ring with six carbon atoms, the lower limit of the carbon number is the total carbon number of the fused ring formed by condensing this benzene ring with the smallest five-membered ring, which is nine carbon atoms.

[0098] Specific examples of the "aryl ring" include a monocyclic benzene ring, a fused bicyclic naphthalene ring, a fused tricyclic acenaphthylene ring, a fluorene ring, a phenalene ring, a phenanthrene ring, and an anthracene ring, a fused tetracyclic triphenylene ring, a pyrene ring, and a naphthacene ring, and a fused pentacyclic perylene ring and a pentacene ring.

[0099] The "heteroaryl ring" is, for example, a heteroaryl ring having 2 to 30 carbon atoms, and 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. The "heteroaryl ring" is, for example, a heterocyclic ring containing, in addition to carbon, 1 to 5 heteroatoms selected from oxygen, sulfur, and nitrogen as ring-constituting atoms. The "heteroaryl ring" as the ring A and ring B in formula (1A) and formula (1B) is defined as "R a and R b The term "a heteroaryl ring formed together with ring a and ring b by bonding adjacent groups among the above" corresponds to a "heteroaryl ring formed together with ring a and ring b." For this "formed aryl ring," since ring a or ring b is already composed of a benzene ring having six carbon atoms, the lower limit of the carbon number is the total carbon number of the fused ring formed by condensing this benzene ring with a minimum five-membered ring, which is six. However, as described above, ring a and ring b, which are benzene rings, may be changed to a nitrogen-containing heteroaryl ring (six- or five-membered ring) or an oxygen- or sulfur-containing heteroaryl ring (five-membered ring), etc., and in this case the lower limit of the carbon number changes accordingly.

[0100] Specific examples of the "heteroaryl ring" include a pyrrole ring, an oxazole ring, an isoxazole ring, a thiazole ring, an isothiazole ring, an imidazole ring, an oxadiazole ring, a thiadiazole ring, a triazole ring, a tetrazole ring, a pyrazole ring, a pyridine ring, a pyrimidine ring, a pyridazine ring, a pyrazine ring, a triazine ring, an indole ring, an isoindole ring, a 1H-indazole ring, a benzimidazole ring, a benzoxazole ring, a benzothiazole ring, a 1H-benzotriazole ring, a quinoline ring, an isoquinoline ring, a cinnoline ring, a quinazoline ring, a quinoxaline ring, a phenanthroline ring, a phthalazine ring, a naphthyridine ring, a purine ring, a pteridine ring, a carba ring, and Examples thereof include a zole ring, an acridine ring, a phenoxathiin ring, a phenoxazine ring, a phenothiazine ring, a phenazine ring, a phenazasiline ring, an indolizine ring, a furan ring, a benzofuran ring, an isobenzofuran ring, a dibenzofuran ring, a naphthobenzofuran ring, a thiophene ring, a benzothiophene ring, an isobenzothiophene ring, a dibenzothiophene ring, a naphthobenzothiophene ring, a benzophosphole ring, a dibenzophosphole ring, a benzophosphole oxide ring, a dibenzophosphole oxide ring, a furazan ring, a thianthrene ring, an indolocarbazole ring, a benzoindolocarbazole ring, a benzobenzoindolocarbazole ring, an imidazoline ring, and an oxazoline ring.

[0101] The "aryl" is, for example, an aryl having 6 to 30 carbon atoms, and preferably an aryl having 6 to 20 carbon atoms, an aryl having 6 to 16 carbon atoms, an aryl having 6 to 12 carbon atoms, or an aryl having 6 to 10 carbon atoms.

[0102] Specific examples of "aryl" include phenyl, a monocyclic ring system; biphenylyl (2-biphenylyl, 3-biphenylyl, or 4-biphenylyl), a fused bicyclic ring system, naphthyl (1-naphthyl or 2-naphthyl), a tricyclic ring system, 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), a fused tricyclic ring system, acenaphthyl, Examples of such ring systems include benzophenone-(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 ring system quaterphenylyl (5'-phenyl-m-terphenyl-2-yl, 5'-phenyl-m-terphenyl-3-yl, 5'-phenyl-m-terphenyl-4-yl, or m-quaterphenyl), the fused tetracyclic ring system triphenylene-(1- or 2-)yl, pyren-(1-, 2-, or 4-)yl, or naphthacene-(1-, 2-, or 5-)yl, or the fused pentacyclic ring system perylene-(1-, 2-, or 3-)yl, or pentacene-(1-, 2-, 5-, or 6-)yl.

[0103] The aryl as the second substituent, i.e., the aryl as the substituent (second substituent) that further substitutes the substituent (first substituent), also includes a structure in which at least one hydrogen atom in the aryl is substituted with an aryl such as phenyl (specific examples are the groups described above), an alkyl such as methyl (specific examples are groups described later), or a cycloalkyl such as cyclohexyl or adamantyl (specific examples are groups described later). For example, when the second substituent is a fluorenyl group, at least one hydrogen atom at the 9-position is substituted with an aryl such as phenyl, an alkyl such as methyl, or a cycloalkyl such as cyclohexyl or adamantyl, and such groups are also included in the aryl group as the second substituent.

[0104] The "arylene (ring)" is, for example, an arylene having 6 to 30 carbon atoms, and 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. Specific examples of "arylene" include structures in which one hydrogen atom is removed from the above-mentioned "aryl" (monovalent group) to form a divalent group.

[0105] "Heteroaryl" is, for example, a heteroaryl having 2 to 30 carbon atoms, and preferably a heteroaryl having 2 to 25 carbon atoms, a heteroaryl having 2 to 20 carbon atoms, a heteroaryl having 2 to 15 carbon atoms, or a heteroaryl having 2 to 10 carbon atoms. Furthermore, "heteroaryl" is, for example, a monovalent group such as a heterocycle containing, in addition to carbon, 1 to 5 heteroatoms selected from oxygen, sulfur, and nitrogen as ring-constituting atoms.

[0106] Specific examples of "heteroaryl" include pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, oxadiazolyl, thiadiazolyl, triazolyl, tetrazolyl, pyrazolyl, pyridinyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, indolyl, isoindolyl, 1H-indazolyl, benzimidazolyl, benzoxazolyl, benzothiazolyl, 1H-benzotriazolyl, quinolinyl, isoquinolinyl, cinnolinyl, quinazolinyl, quinoxalinyl, phenanthrolinyl, phthalazinyl, naphthyridinyl, purinyl, pteridinyl, carbazolyl, acridinyl, and phenoxathiinyl. phenyl, phenoxazinyl, phenothiazinyl, phenazinyl, phenazasilinyl, indolizinyl, furanyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, naphthobenzofuranyl, thiophenyl, benzothiophenyl, isobenzothiophenyl, dibenzothiophenyl, naphthobenzothiophenyl, benzophosphoryl, dibenzophosphoryl, a monovalent group of a benzophosphole oxide ring, a monovalent group of a dibenzophosphole oxide ring, furazanyl, thianthrenyl, indolocarbazolyl, benzindolocarbazolyl, benzobenzoindolocarbazolyl, imidazolinyl, oxazolinyl, or dibenzosilacyclopentadienyl.

[0107] The heteroaryl as the second substituent, i.e., the heteroaryl as the substituent (second substituent) that further substitutes the substituent (first substituent), also includes a structure in which at least one hydrogen atom in the heteroaryl is substituted with an aryl such as phenyl (specific examples are the groups described above), an alkyl such as methyl (specific examples are groups described later), or a cycloalkyl such as cyclohexyl or adamantyl (specific examples are groups described later). For example, when the second substituent is a carbazolyl group, at least one hydrogen atom at the 9-position is substituted with an aryl such as phenyl, an alkyl such as methyl, or a cycloalkyl such as cyclohexyl or adamantyl, and such groups are also included in the heteroaryl group as the second substituent.

[0108] The "heteroarylene (ring)" is, for example, a heteroarylene having 2 to 30 carbon atoms, and preferably a heteroarylene having 2 to 25 carbon atoms, a heteroarylene having 2 to 20 carbon atoms, a heteroarylene having 2 to 15 carbon atoms, or a heteroarylene having 2 to 10 carbon atoms. Furthermore, the "heteroarylene" is a divalent group such as a heterocycle containing, in addition to carbon, 1 to 5 heteroatoms selected from oxygen, sulfur, and nitrogen as ring-constituting atoms. Specific examples of "heteroarylene" include structures in which one hydrogen atom is removed from the above-mentioned "heteroaryl" (monovalent group) to form a divalent group.

[0109] "Diarylamino" refers to an amino group substituted with two aryl groups, and the details of the aryl group can be found in the above description of "aryl". "Diheteroarylamino" refers to an amino group substituted with two heteroaryls, and the details of this heteroaryl can be found in the above description of "heteroaryl". "Arylheteroarylamino" refers to an amino group substituted with an aryl and a heteroaryl, and the details of the aryl and heteroaryl can be found in the explanations of "aryl" and "heteroaryl" given above.

[0110] "Diarylboryl" refers to a boryl group substituted with two aryls, and the details of the aryls can be found in the above description of "aryl." The two aryls may 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, R of "-CHR-CHR-", R of "-CR-CR-", R of "-CR=CR-", R of ">NR", R of ">C(-R)", and R of ">Si(-R)" are aryl, heteroaryl, diarylamino, alkyl, alkenyl, alkynyl, cycloalkyl, alkoxy, or aryloxy, and at least one hydrogen atom in the R may be further substituted with an aryl, heteroaryl, alkyl, alkenyl, alkynyl, or cycloalkyl. Two adjacent Rs may form a ring, forming a cycloalkylene, arylene, or heteroarylene. For details of the substituents listed here, the above-mentioned descriptions of "aryl", "arylene", "heteroaryl", "heteroarylene", and "diarylamino" and the below-mentioned descriptions of "alkyl", "alkenyl", "alkynyl", "cycloalkyl", "cycloalkylene", "alkoxy", and "aryloxy" can be cited.

[0111] The "alkyl" may be either straight-chain or branched-chain, for example, a straight-chain alkyl having 1 to 24 carbon atoms or a branched-chain alkyl having 3 to 24 carbon atoms, and is preferably an alkyl having 1 to 18 carbon atoms (branched-chain alkyl having 3 to 18 carbon atoms), an alkyl having 1 to 12 carbon atoms (branched-chain alkyl having 3 to 12 carbon atoms), an alkyl having 1 to 6 carbon atoms (branched-chain alkyl having 3 to 6 carbon atoms), an alkyl having 1 to 5 carbon atoms (branched-chain alkyl having 3 to 5 carbon atoms), or an alkyl having 1 to 4 carbon atoms (branched-chain alkyl having 3 to 4 carbon atoms).

[0112] 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-dimethylhexyl Examples of the alkyl group 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, and n-eicosyl.

[0113] For "alkenyl," the explanation of "alkyl" above can be referred to. It is a group in which a C═C single bond in the "alkyl" structure is replaced with a C═C double bond, and also includes groups in which not only one but two or more single bonds are replaced with double bonds (also called alkadiene-yl or alkanetriene-yl).

[0114] For "alkynyl," the explanation of "alkyl" above can be referred to. It is a group in which a C≡C single bond in the "alkyl" structure is replaced with a C≡C triple bond, and also includes groups in which not only one but two or more single bonds are replaced with triple bonds (also called alkadiyn-yl or alkanetriyn-yl).

[0115] The "cycloalkyl" is, for example, a cycloalkyl having 3 to 24 carbon atoms, and preferably a cycloalkyl having 3 to 20 carbon atoms, a cycloalkyl having 3 to 16 carbon atoms, a cycloalkyl having 3 to 14 carbon atoms, a cycloalkyl having 3 to 12 carbon atoms, a cycloalkyl having 5 to 10 carbon atoms, a cycloalkyl having 5 to 8 carbon atoms, a cycloalkyl having 5 to 6 carbon atoms, or a cycloalkyl having 5 carbon atoms.

[0116] Specific examples of "cycloalkyl" include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, or alkyl (particularly methyl) substituted derivatives thereof having 1 to 5 carbon atoms or 1 to 4 carbon atoms, norbornenyl, 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 decahydroazulenyl.

[0117] The "cycloalkylene (ring)" is, for example, a cycloalkylene having 3 to 24 carbon atoms, and 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. Specific examples of "cycloalkylene" include structures in which one hydrogen atom is removed from the above-mentioned "cycloalkyl" (monovalent group) to form a divalent group.

[0118] The "alkoxy" may be either straight-chain or branched-chain, and is, for example, a straight-chain alkoxy having 1 to 24 carbon atoms or a branched-chain alkoxy having 3 to 24 carbon atoms, and is preferably an alkoxy having 1 to 18 carbon atoms (branched-chain alkoxy having 3 to 18 carbon atoms), an alkoxy having 1 to 12 carbon atoms (branched-chain alkoxy having 3 to 12 carbon atoms), an alkoxy having 1 to 6 carbon atoms (branched-chain alkoxy having 3 to 6 carbon atoms), an alkoxy having 1 to 5 carbon atoms (branched-chain alkoxy having 3 to 5 carbon atoms), or an alkoxy having 1 to 4 carbon atoms (branched-chain alkoxy having 3 to 4 carbon atoms).

[0119] 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-dimethyl Examples of the alkyl group include t-butyl-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, and n-eicosyloxy.

[0120] "Aryloxy" is a group represented by "Ar-O- (Ar is an aryl group)", and the above explanation of "aryl" can be cited for details of the aryl.

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

[0122] "Triarylsilyl" is a silyl group substituted with three aryl groups, and the details of the aryl groups can be found in the above description of "aryl." Specific examples of "triarylsilyl" include triphenylsilyl, diphenylmononaphthylsilyl, monophenyldinaphthylsilyl, and trinaphthylsilyl.

[0123] "Trialkylsilyl" is a silyl group substituted with three alkyl groups, and the details of this alkyl can be found in the above explanation of "alkyl". Specific examples of the "trialkylsilyl" 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, and t-butyldiisopropylsilyl.

[0124] "Tricycloalkylsilyl" is a silyl group substituted with three cycloalkyl groups, and the details of this cycloalkyl can be found in the above description of "cycloalkyl". Specific "tricycloalkylsilyl" includes, for example, tricyclopentylsilyl or tricyclohexylsilyl.

[0125] "Dialkylcycloalkylsilyl" is a silyl group substituted with two alkyls and one cycloalkyl, and the details of the alkyl and cycloalkyl can be found in the explanations of "alkyl" and "cycloalkyl" above.

[0126] "Alkyldicycloalkylsilyl" is a silyl group substituted with one alkyl and two cycloalkyl, and the details of the alkyl and cycloalkyl can be found in the explanations of "alkyl" and "cycloalkyl" above.

[0127] Substituents (including the first and second substituents) affect the emission wavelength of the polycyclic aromatic compound due to the steric hindrance, electron donating property, and electron withdrawing property of the structure, and therefore the emission wavelength can be adjusted by selecting the substituent. Preferred are groups represented by the following structural formulas, and more preferred are 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, dibenzoxaborininyl, phenyldibenzyl, and phenyldibenzyl. Preferred are benzodiborinyl, carbazolyl, 3,6-dimethylcarbazolyl, 3,6-di-t-butylcarbazolyl, and phenoxy, and more preferred are 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, and 3,6-di-t-butylcarbazolyl. From the viewpoint of ease of synthesis, a larger steric hindrance is preferred 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 formulas below, "Me" represents methyl, "tBu" represents t-butyl, "tAm" represents t-amyl, and "tOct" represents t-octyl, and * represents the bonding position. [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka]

[0129] <Description of cycloalkane condensation> In addition, 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 and heteroaryl rings as rings A and B, aryl groups (aryl moieties in aryl, diarylamino, arylheteroarylamino, diarylboryl, aryloxy, or triarylsilyl) and heteroaryl groups (heteroaryl moieties in heteroaryl, diheteroarylamino, or arylheteroarylamino) as the first and second substituents on these rings, aryl and heteroaryl rings as rings a and b, aryl or heteroaryl rings formed by bonding adjacent substituents on rings a and b, aryl groups (similar to above) and heteroaryl groups (similar to above) as the first and second substituents on rings a and b, X 1 ~X 4 At least one of the aryl or heteroaryl groups as R in >NR, R in >C(—R)2, and R in >Si(—R)2 may be fused with at least one cycloalkane.

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

[0132] More preferred are aryl rings which are rings A and B, aryl groups (aryl group moieties in aryl or diarylamino) and heteroaryl groups (heteroaryl moieties in heteroaryl) as first substituents on these rings, aryl rings which are rings a and b, aryl rings formed by bonding adjacent substituents on rings a and b, aryl groups (similar to above) and heteroaryl groups (similar to above) as first substituents on rings a and b, X 1 ~X 4 At least one of the aryl groups as R in “>NR” may be fused with at least one cycloalkane.

[0133] More preferably, the aryl rings are A and B rings, aryl groups as the first substituents on these rings (aryl group moieties in aryl or diarylamino), aryl rings are a and b rings, aryl groups as the first substituents on the a and b rings (similar to above), X 1 ~X 4 At least one of the aryl groups as R in “>NR” may be fused with at least one cycloalkane.

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

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

[0136] Among these, for example, as shown in the following structural formula, a structure in which at least one hydrogen atom is substituted on the α-carbon atom of a cycloalkane (in a cycloalkyl fused to an aromatic ring or heteroaromatic ring, the carbon atom adjacent to the fused carbon atom) is preferred, a structure in which two hydrogen atoms are substituted on the α-carbon atom is more preferred, and a structure in which a total of four hydrogen atoms are substituted on the two α-carbon atoms is even more preferred. Examples of this substituent include a C1-C5 alkyl (particularly methyl) substituent, a halogen (particularly fluorine) substituent, and a deuterium substituent. [ka]

[0137] The number of cycloalkanes fused to one aromatic ring or heteroaromatic ring is preferably 1 to 3, more preferably 1 or 2, and even more preferably 1. For example, examples in which one or more cycloalkanes are fused to one benzene ring (phenyl group) are shown below. In each structural formula, * means a benzene ring included in the skeletal structure of the compound when it is a benzene ring, and means a bond substituting the skeletal structure of the compound when it is a phenyl group. Fused cycloalkanes such as those in formula (Cy-1-4) and formula (Cy-2-4) may be fused together. This also applies when the fused ring (group) is an aromatic ring or heteroaromatic ring other than a benzene ring (phenyl group), or when the fused cycloalkane is a cycloalkane other than cyclopentane or cyclohexane. [ka]

[0138] At least one -CH2- in a cycloalkane may be replaced with -O-. However, when multiple -CH2- are replaced with -O-, adjacent -CH2- are not replaced with -O-. For example, the following examples show cycloalkanes fused to a single benzene ring (phenyl group) in which one or more -CH2- are replaced with -O-. In each structural formula, the * indicates a benzene ring included in the skeletal structure of the compound when it is a benzene ring, and indicates a bond substituting the skeletal structure of the compound when it is a phenyl group. The same applies when the fused ring (group) is an aromatic ring or heteroaromatic ring other than a benzene ring (phenyl group), and when the fused 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 a substituent include aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl (the two aryls may be bonded via a single bond or a linking group), alkyl, cycloalkyl, alkoxy, aryloxy, substituted silyl, deuterium, cyano, or halogen. For details, see the description of the first substituent above. Among these substituents, alkyl (e.g., alkyl having 1 to 6 carbon atoms), cycloalkyl (e.g., cycloalkyl having 3 to 14 carbon atoms), halogen (e.g., fluorine), and deuterium are preferred. Furthermore, when cycloalkyl is substituted, it may be a substitution form that forms a spiro structure. For example, an example of a spiro structure formed in a cycloalkane fused to one benzene ring (phenyl group) is shown below. In each structural formula, * indicates the benzene ring included in the skeletal structure of the compound when it is a benzene ring, and indicates a bond substituting the skeletal structure of the compound when it is a phenyl group. [ka]

[0140] Other forms of cycloalkane condensation include polycyclic aromatic compounds represented by formula (1A), formula (1B), formula (2A), or formula (2B), which are substituted with, for example, a diarylamino group fused with a cycloalkane (fused to the aryl group portion), a carbazolyl group fused with a cycloalkane (fused to the benzene ring portion), or a benzocarbazolyl group fused with a cycloalkane (fused to the benzene ring portion). Examples of the "diarylamino group" include the groups described above as the "first substituent."

[0141] Further, as a more specific example, R in the polycyclic aromatic compound represented by formula (2A) or formula (2B) a (Especially, Y 1 and Y 2 R in para position a) is a diarylamino group fused with a cycloalkane (fused to the aryl group portion) or a carbazolyl group fused with a cycloalkane (fused to the benzene ring portion).

[0142] <Deuterium, cyano, or halogen substitution explanation> At least one hydrogen atom in the polycyclic aromatic compound of the present invention may be substituted with deuterium, cyano, or a halogen atom. The halogen atom is fluorine, chlorine, bromine, or iodine, preferably fluorine, chlorine, or bromine, and more preferably fluorine or chlorine.

[0143] <Explanation 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] The benzene rings in the structural formula above may each independently be substituted with an aryl having 6 to 16 carbon atoms, a heteroaryl having 2 to 20 carbon atoms, a diarylamino (wherein the aryl is an aryl having 6 to 10 carbon atoms), a diarylboryl (wherein the aryl is an aryl having 6 to 10 carbon atoms, and two aryls may be bonded via a single bond or a linking group), an alkyl having 1 to 12 carbon atoms, or a cycloalkyl having 3 to 16 carbon atoms, and at least one hydrogen atom in the substituent may be substituted with an alkyl having 1 to 5 carbon atoms or a cycloalkyl having 5 to 10 carbon atoms. Specific examples of these substituents can be found in the above description. When substituted, the number of substituents ranges from 1 to the maximum number that can be substituted on each benzene ring, preferably 1 to 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 compounds represented by the following structural formula: In the structural formula, "Me" represents a methyl group, "tBu" represents a t-butyl group, and "D" represents deuterium.

[0147] [ka]

[0148] [ka]

[0149] [ka]

[0150] [ka]

[0151] [ka]

[0152] [ka]

[0153] [ka]

[0154] [ka]

[0155] [ka]

[0156] [ka]

[0157] [ka]

[0158] [ka]

[0159] [ka]

[0160] <Explanation of the high molecular weight of polycyclic aromatic compounds> The polycyclic aromatic compound represented by the general formula (1A) or (1B) can be used as a material for organic devices, such as a material for organic electroluminescent elements, a material for organic field-effect transistors, a material for organic thin-film solar cells, or a wavelength conversion filter, in the form of a polymer compound obtained by polymerizing a reactive compound substituted with the compound as a monomer (the monomer for obtaining this polymer compound has a polymerizable substituent), or a crosslinked polymer obtained by further crosslinking the polymer compound (the polymer compound for obtaining this crosslinked polymer has a crosslinkable substituent), or a pendant polymer compound obtained by reacting a main-chain polymer with the reactive compound (the reactive compound for obtaining this pendant polymer compound has a reactive substituent), or a pendant crosslinked polymer obtained by further crosslinking the pendant polymer compound (the pendant polymer compound for obtaining this crosslinked pendant polymer has a crosslinkable substituent).

[0161] The reactive substituents described above (including the polymerizable substituents, crosslinkable substituents, and reactive substituents for obtaining a pendant polymer, hereinafter simply referred to as "reactive substituents") are not particularly limited as long as they are substituents capable of increasing the molecular weight of the polycyclic aromatic compound, substituents capable of further crosslinking the polymer compound thus obtained, and substituents capable of pendant reaction with a main-chain polymer, but substituents having the following structures are preferred: * in each structural formula indicates a bonding position. [ka]

[0162] L's are each independently a single bond, -O-, -S-, >C=O, -OC(=O)-, alkylene having 1 to 12 carbon atoms, oxyalkylene having 1 to 12 carbon atoms, and polyoxyalkylene having 1 to 12 carbon atoms. Among the above substituents, groups represented by formula (XLS-1), formula (XLS-2), formula (XLS-3), formula (XLS-9), formula (XLS-10) or formula (XLS-17) are preferred, and groups represented by formula (XLS-1), formula (XLS-3) or formula (XLS-17) are more preferred.

[0163] In addition to the repeating unit of the polycyclic aromatic compound represented by Formula (1A) or Formula (1B), such polymer compounds, crosslinked polymers, pendant-type polymer compounds, and pendant-type crosslinked polymers may contain, as a repeating unit, at least one compound selected from the group consisting of substituted or unsubstituted triarylamine, substituted or unsubstituted fluorene, substituted or unsubstituted anthracene, substituted or unsubstituted tetracene, substituted or unsubstituted triazine, substituted or unsubstituted carbazole, substituted or unsubstituted tetraphenylsilane, substituted or unsubstituted spirofluorene, substituted or unsubstituted triphenylphosphine, substituted or unsubstituted dibenzothiophene, and substituted or unsubstituted dibenzofuran. Examples of the substituent in these repeating units include aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl (two aryls may be bonded via a single bond or a linking group), alkyl, cycloalkyl, alkoxy, aryloxy, triarylsilyl, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, or alkyldicycloalkylsilyl. For details of the "aryl" in triarylamine and these substituents, the explanation for the polycyclic aromatic compound represented by formula (1A) or formula (1B) can be cited.

[0164] The uses of such polymer compounds, crosslinked polymers, pendant polymer compounds, and pendant crosslinked polymers (hereinafter simply referred to as "polymer compounds and crosslinked polymers") will be described in detail below.

[0165] 2. Method for producing a polycyclic aromatic compound The polycyclic aromatic compound of the present invention is basically prepared by first connecting the A ring (a ring), the B ring (b ring), and the c ring with a bonding group (X 1 ~X 4 (a group containing the central element Y) to produce an intermediate (first reaction), and then, the A ring (a ring), the B ring (b ring), and the c ring are bonded to each other by a bonding group (a group containing the central element Y 1 and Y 2 A group containing Y 1 and Y 2 " is abbreviated as "Y") to produce the final product (second reaction). The production method described in WO 2015 / 102118 can be used as a reference.

[0166] For the first reaction, for example, etherification reactions can be performed using common reactions such as nucleophilic substitution and the Ullmann reaction, while amination reactions can be performed using common reactions such as the Buchwald-Hartwig reaction. For the second reaction, tandem hetero-Friedel-Crafts reactions (sequential aromatic electrophilic substitution reactions, hereinafter the same) can be used.

[0167] The second reaction is a reaction to introduce a central element Y that connects the A ring (a ring), the B ring (b ring), and the c ring, as shown in the following scheme (1). 1 and X 2 The hydrogen atoms between 3 and X 4 The hydrogen atom between the two is orthometalated with n-butyllithium, sec-butyllithium, or t-butyllithium. A halide of Y, such as boron trichloride or boron tribromide, is then added to perform lithium-boron metal exchange, followed by the addition of a Bronsted base, such as N,N-diisopropylethylamine, to carry out a tandem boron-Friedel-Crafts reaction to obtain the desired product. In the second reaction, a Lewis acid, such as aluminum trichloride, may be added to promote the reaction. The symbols in the structural formulae in the following scheme (1) and subsequent schemes are defined as above.

[0168] [ka]

[0169] In the above scheme, lithium was introduced into the desired position by orthometalation, but as shown in the following scheme (2), lithium can also be introduced into the desired position by introducing a bromine atom or the like into the desired position and then performing halogen-metal exchange. This method is useful because it allows the production of the target product even in cases where orthometalation is not possible due to the influence of substituents.

[0170] [ka]

[0171] The above schemes (1) and (2) are typical production methods when Y is boron (>B-) or the like.

[0172] Next, as an example, the case where Y is a phosphine sulfide, a phosphine oxide, or a phosphorus atom is shown in the following schemes (3) and (4).1 and X 2 The hydrogen atoms between 3 and X 4 The hydrogen atom between the two is orthometalated with n-butyllithium or the like. Next, phosphorus trichloride and sulfur are added, followed by a Lewis acid such as aluminum trichloride and a Bronsted base such as N,N-diisopropylethylamine, resulting in a tandem phosphine-Friedel-Crafts reaction to obtain a compound in which Y is a phosphine sulfide. Furthermore, treatment of the resulting phosphine sulfide compound with m-chloroperbenzoic acid (m-CPBA) yields a compound in which Y is a phosphine oxide, and treatment with triethylphosphine yields a compound in which Y is a phosphorus atom.

[0173] [ka]

[0174] [ka]

[0175] In the above scheme, examples where Y is >B-, >P-, >P(=O)-, or >P(=S)- are mainly described, but other compounds can also be produced by appropriately changing the raw materials.

[0176] In the above scheme, X is added before adding a halide of Y such as boron trichloride or boron tribromide. 1 and X 2 Hydrogen atoms (or halogen atoms) and X 3 and X 4 In the example shown, the hydrogen atom (or halogen atom) between the two is orthometalated with butyllithium or the like to perform a tandem hetero-Friedel-Crafts reaction. However, the reaction can also proceed by adding a halide of Y, such as boron trichloride or boron tribromide, without orthometalation using butyllithium or the like.

[0177] Examples of the solvent used in the above scheme include t-butylbenzene and xylene.

[0178] Examples of orthometalation reagents used in the above scheme include alkyllithiums 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 organic solvent-dispersed sodium.

[0179] Examples of the metal-Y metal exchange reagent used in the above scheme include halides of Y such as trifluoride of Y, trichloride of Y, tribromide of Y, and triiodide of Y; aminated halides of Y such as CIPN(NEt2)2; alkoxylated Y; and aryloxylated Y.

[0180] Examples of Bronsted 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, ArBNa, ArBK, ArB, and ArSi (wherein Ar is an aryl such as phenyl).

[0181] 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.

[0182] In the above scheme, a Brønsted base or Lewis acid may be used to promote the tandem hetero-Friedel-Crafts reaction. However, when a halide of Y, such as trifluoride of Y, trichloride of Y, tribromide of Y, or triiodide of Y, is used, acids such as hydrogen fluoride, hydrogen chloride, hydrogen bromide, and hydrogen iodide are generated as the aromatic electrophilic substitution reaction proceeds, so the use of a Brønsted base to capture the acid is effective. On the other hand, when an aminated halide of Y or an alkoxylated Y is used, amines and alcohols are generated as the aromatic electrophilic substitution reaction proceeds, so the use of a Brønsted base is often unnecessary. However, since the amino and alkoxy groups have low elimination ability, the use of a Lewis acid to promote their elimination is effective.

[0183] The polycyclic aromatic compound of the present invention also includes compounds in which at least a portion of hydrogen is substituted with deuterium, cyano, or halogen. Such compounds can be produced in the same manner as described above by using a raw material in which the desired position is halogenated, e.g., deuterated, cyanated, fluorinated, or chlorinated.

[0184] 3. Organic device In the chemical structural formulas exemplified below, "Me" represents a methyl group and "tBu" represents a t-butyl group. The polycyclic aromatic compound according to the present invention can be used as a material for organic devices, such as organic electroluminescent devices, organic field-effect transistors, organic thin-film solar cells, and wavelength conversion filters.

[0185] 3-1. Organic electroluminescent device The polycyclic aromatic compound according to the present invention can be used, for example, as a material for an organic electroluminescent device. The organic EL device according to this embodiment will be described in detail below with reference to the drawings. Figure 1 is a schematic cross-sectional view showing an organic EL device according to this embodiment.

[0186] <Structure of organic electroluminescent device> The organic EL device 100 shown in FIG. 1 includes a substrate 101, an anode 102 provided on the substrate 101, a hole injection layer 103 provided on the anode 102, a hole transport layer 104 provided on the hole injection layer 103, an emitting layer 105 provided on the hole transport layer 104, an electron transport layer 106 provided on the emitting layer 105, an electron injection layer 107 provided on the electron transport layer 106, and a cathode 108 provided on the electron injection layer 107.

[0187] The organic EL element 100 may be fabricated in the reverse order, for example, to have a substrate 101, a cathode 108 provided on the substrate 101, an electron injection layer 107 provided on the cathode 108, an electron transport layer 106 provided on the electron injection layer 107, an emitting layer 105 provided on the electron transport layer 106, a hole transport layer 104 provided on the emitting layer 105, a hole injection layer 103 provided on the hole transport layer 104, and an anode 102 provided on the hole injection layer 103.

[0188] Not all of the above layers are essential, and the minimum structural unit is a configuration consisting of an anode 102, an emitting layer 105, and a cathode 108. The hole injection layer 103, the hole transport layer 104, the electron transport layer 106, and the electron injection layer 107 are layers that may be optionally provided. Furthermore, each of the above layers may consist of a single layer or multiple layers.

[0189] The layers constituting the organic EL element may be configured as follows: "substrate / anode / hole injection layer / hole transport layer / light-emitting layer / electron transport layer / electron injection layer / cathode" as described above, as well as "substrate / anode / hole transport layer / light-emitting layer / electron transport layer / electron injection layer / cathode", "substrate / anode / hole injection layer / light-emitting layer / electron transport layer / electron injection layer / cathode", "substrate / anode / hole injection layer / hole transport layer / light-emitting ... transport The configuration may be, for example, "substrate / anode / light-emitting layer / electron transport layer / electron injection layer / cathode," "substrate / anode / hole transport layer / light-emitting layer / electron injection layer / cathode," "substrate / anode / hole transport layer / light-emitting layer / electron injection layer / cathode," "substrate / anode / hole transport layer / light-emitting layer / electron transport layer / cathode," "substrate / anode / hole injection layer / light-emitting layer / electron injection layer / cathode," "substrate / anode / hole injection layer / light-emitting layer / electron transport layer / cathode," "substrate / anode / light-emitting layer / electron transport layer / cathode," or "substrate / anode / light-emitting layer / electron injection layer / cathode."

[0190] <Substrate in organic electroluminescent device> The substrate 101 is a support for the organic EL device 100 and is typically made of quartz, glass, metal, plastic, or the like. The substrate 101 may be formed into a plate, film, or sheet shape depending on the purpose, and may be, for example, a glass plate, a metal plate, a metal foil, a plastic film, or a plastic sheet. Glass plates and plates made of transparent synthetic resins such as polyester, polymethacrylate, polycarbonate, and polysulfone are preferred. For glass substrates, soda-lime glass or alkali-free glass may be used. The thickness should be sufficient to maintain mechanical strength, e.g., 0.2 mm or more. 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 minimizes ion elution from the glass. However, commercially available soda-lime glass coated with a barrier coating such as SiO2 can also be used. In addition, in order to improve the gas barrier properties of the substrate 101, a gas barrier film such as a dense silicon oxide film may be provided on at least one side thereof, and it is particularly preferable to provide a gas barrier film when a synthetic resin plate, film, or sheet with poor gas barrier properties is used as the substrate 101.

[0191] <Anode in organic electroluminescent device> The anode 102 serves to inject holes into the light-emitting layer 105. When at least one of the hole injection layer 103 and the hole transport layer 104 is provided between the anode 102 and the light-emitting layer 105, holes are injected into the light-emitting layer 105 via these layers.

[0192] Materials for forming the anode 102 include inorganic 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. Other materials may be appropriately selected from those used as anodes in organic EL devices.

[0193] The resistance of the transparent electrode is not limited as long as it can supply sufficient current to light the light-emitting element, but low resistance is desirable from the perspective of the power consumption of the light-emitting element. For example, an ITO substrate with a resistance of 300 Ω / □ or less can function as an element electrode, but since substrates with a resistance of about 10 Ω / □ are now available, it is particularly desirable to use a low resistance product with a resistance of, for example, 100 to 5 Ω / □, preferably 50 to 5 Ω / □. The thickness of the ITO can be selected arbitrarily depending on the resistance value, but it is usually between 50 and 300 nm.

[0194] <Hole injection layer and hole transport layer in organic electroluminescent device> The hole injection layer 103 serves to efficiently inject holes migrating from the anode 102 into the light-emitting layer 105 or the hole transport layer 104. The hole transport layer 104 serves to efficiently transport 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 or mixing one or more hole injection / transport materials, or by a mixture of a hole injection / transport material and a polymer binder. Alternatively, a layer may be formed by adding an inorganic salt such as iron(III) chloride to the hole injection / transport material.

[0195] A hole injection / transport material is required to efficiently inject and transport holes from a positive electrode between electrodes to which an electric field is applied. It is desirable for the hole injection / transport material to have high hole injection efficiency and efficiently transport the injected holes. To achieve this, the material preferably has a low ionization potential, high hole mobility, and excellent stability, and is unlikely to generate impurities that act as traps during production or use. In the present invention, polycyclic aromatic compounds represented by the above general formula (1A) or general formula (1B) can be used as materials for the hole injection layer and hole transport layer.

[0196] As materials for forming the hole injection layer 103 and the hole transport layer 104, any compound can be selected from compounds conventionally used as charge transport materials for holes in photoconductive materials, p-type semiconductors, and known compounds used in hole injection layers and hole transport layers of organic EL devices.

[0197] Specific examples thereof include carbazole derivatives (N-phenylcarbazole, polyvinylcarbazole, etc.), biscarbazole derivatives such as bis(N-arylcarbazole) or bis(N-alkylcarbazole), triarylamine derivatives (polymers having an aromatic tertiary amino group in the main chain or side chain, 1,1-bis(4-di-p-tolylaminophenyl)cyclohexane, N,N'-diphenyl-N,N'-di(3-methylphenyl)-4,4'-diaminobiphenyl, N,N'-diphenyl-N,N'-dinaphthyl-4,4'-diaminobiphenyl, N,N'-diphenyl-N,N'-di(3-methylphenyl)-4,4'-diphenyl-1,1'-diamine, N,N'-dinaphthyl-N,N'-diphenyl-4,4'-diphenyl-1,1'-diamine, N 4 ,N 4’ -diphenyl-N 4 ,N 4’ -bis(9-phenyl-9H-carbazol-3-yl)-[1,1'-biphenyl]-4,4'-diamine, N 4 ,N 4 ,N 4’ ,N 4’-tetra[1,1'-biphenyl]-4-yl)-[1,1'-biphenyl]-4,4'-diamine, triphenylamine derivatives such as 4,4',4"-tris(3-methylphenyl(phenyl)amino)triphenylamine, starburst amine derivatives, etc.), stilbene derivatives, phthalocyanine derivatives (metal-free, copper phthalocyanine, etc.), pyrazoline derivatives, hydrazone compounds, benzofuran derivatives, thiophene derivatives, oxadiazole derivatives, quinoxaline derivatives Examples of the material include conductors (for example, 1,4,5,8,9,12-hexaazatriphenylene-2,3,6,7,10,11-hexacarbonitrile), heterocyclic compounds such as porphyrin derivatives, polysilanes, etc. Among polymers, polycarbonates and styrene derivatives having the above-mentioned monomers in their side chains, polyvinylcarbazole, and polysilanes are preferred, but there are no particular limitations on the material as long as it is a compound that can form a thin film required for fabricating a light-emitting device, can inject holes from the anode, and can transport holes.

[0198] It is also known that the conductivity of organic semiconductors is strongly influenced by their doping. Such organic semiconductor matrix materials consist of compounds with good electron-donating or 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. Pheiffer, T. Fritz, K. Leo, Appl. Phys. Lett., 73(6), 729-731 (1998)). These generate so-called holes via an electron transfer process in the electron-donating base material (hole-transporting material). The conductivity of the base material varies considerably depending on the number and mobility of holes. Known matrix materials with hole transport properties include benzidine derivatives (such as TPD) or starburst amine derivatives (such as TDATA), as well as certain metal phthalocyanines (e.g., zinc phthalocyanine (ZnPc)) (see JP 2005-167175 A).

[0199] The hole injection layer material and hole transport layer material described above can also be used as hole layer materials in the form of polymer compounds obtained by polymerizing a reactive compound substituted with a reactive substituent as a monomer, or a crosslinked polymer thereof, or a pendant polymer compound obtained by reacting a main-chain polymer with the reactive compound, or a crosslinked pendant polymer thereof. Regarding the reactive substituent in this case, the explanation for the polycyclic aromatic compound represented by the general formula (1A) or (1B) above can be cited. The uses of such polymer compounds and crosslinked polymers will be described in detail below.

[0200] <Light-emitting layer in organic electroluminescent device> The light-emitting layer 105 is a layer that emits light by recombining holes injected from the anode 102 and electrons injected from the cathode 108 between electrodes to which an electric field is applied. The material for the light-emitting layer 105 may be a compound (light-emitting compound) that is excited and emits light by the recombination of holes and electrons, and is preferably a compound that can be formed into a stable thin film and exhibits strong light-emitting (fluorescence) efficiency in a solid state. In the present invention, the material for the light-emitting layer can be a host material and, for example, a polycyclic aromatic compound represented by the above general formula (1A) or general formula (1B) as a dopant material.

[0201] The light-emitting layer may be a single layer or multiple layers, each formed from materials for the light-emitting layer (host material, dopant material). The host material and the dopant material may each be one type or a combination of multiple types. The host material may be mixed with a material for the hole transport layer or a material for the electron transport layer, or a combination thereof. The dopant material may be contained entirely or partially in the host material. As a doping method, the dopant material can be formed by co-evaporation with the host material, but it may also be mixed with the host material in advance and then vapor-deposited simultaneously, or mixed with the host material together with an organic solvent and then formed into a film by a wet film-forming method.

[0202] The amount of the host material used varies depending on the type of host material and may be determined according to the properties of the host material. The amount of the host material used is preferably 50 to 99.999% by weight, more preferably 80 to 99.95% by weight, and even more preferably 90 to 99.9% by weight of the total materials for the light-emitting layer.

[0203] The amount of dopant material used varies depending on the type of dopant material and may be determined according to the properties of the dopant material. The amount of dopant used is preferably 0.001 to 50% by weight, more preferably 0.05 to 20% by weight, and even more preferably 0.1 to 10% by weight, of the total material for the light-emitting layer. The above ranges are preferable in that, for example, concentration quenching can be prevented. Furthermore, from the viewpoint of durability, it is also preferable that some or all of the hydrogen atoms of the dopant material are deuterated.

[0204] On the other hand, in an organic EL device using a thermally activated delayed fluorescence dopant material, it is preferable that the amount of the dopant material used is low in terms of preventing concentration quenching, but it is preferable that the amount of the dopant material used is high in terms of the efficiency of the thermally activated delayed fluorescence mechanism.Furthermore, in an organic EL device using a thermally activated delayed fluorescence assist dopant material, it is preferable that the amount of the dopant material used is low in terms of the efficiency of the thermally activated delayed fluorescence mechanism of the assist dopant material.

[0205] When an assist dopant material is used, the amounts of the host material, assist dopant material, and dopant material used are approximately 40 to 99.999% by weight, 59 to 1% by weight, and 20 to 0.001% by weight, respectively, of the total materials for the light-emitting layer, preferably 60 to 99.99% by weight, 39 to 5% by weight, and 10 to 0.01% by weight, respectively, and more preferably 70 to 99.95% by weight, 29 to 10% by weight, and 5 to 0.05% by weight. The polycyclic aromatic compounds represented by the above general formula (1A) or general formula (1B) and polymer compounds thereof can also be used as assist dopant materials.

[0206] Examples of host materials include fused ring derivatives of anthracene, pyrene, dibenzochrysene, fluorene, and the like, which have long been known as light emitters; bisstyryl derivatives such as bisstyryl anthracene derivatives and distyrylbenzene derivatives; tetraphenylbutadiene derivatives; and cyclopentadiene derivatives. Anthracene-based compounds, fluorene-based compounds, and dibenzochrysene-based compounds are particularly preferred. From the viewpoint of durability, it is also preferred that some or all of the hydrogen atoms in the host material are deuterated. Furthermore, it is also preferred to form an emitting 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.

[0207] From the viewpoint of promoting TADF generation in the light-emitting layer without inhibiting it, the triplet energy of the host material is preferably higher than that of the dopant or assist dopant having the highest triplet energy in the light-emitting layer. Specifically, the triplet energy of the host material is preferably 0.01 eV or more, more preferably 0.03 eV or more, and even more preferably 0.1 eV or more. A TADF-active compound may also be used as the host material.

[0208] Examples of the host material include 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. The compound represented by general formula (H1) is preferred. [ka]

[0209] <Compound represented by general formula (H1)> [ka] In the above formula (H1), L 1is an arylene having 6 to 30 carbon atoms or a heteroarylene having 2 to 30 carbon atoms, preferably an arylene having 6 to 24 carbon atoms, more preferably an arylene having 6 to 16 carbon atoms, still more preferably an arylene having 6 to 12 carbon atoms, particularly preferably an arylene having 6 to 10 carbon atoms, and also preferably a heteroarylene having 2 to 25 carbon atoms, more preferably a heteroarylene having 2 to 20 carbon atoms, still more preferably a heteroarylene having 2 to 15 carbon atoms, particularly preferably a heteroarylene having 2 to 10 carbon atoms. Specific examples of arylene include divalent groups such as a benzene ring, a biphenyl ring, a naphthalene ring, a terphenyl ring, an acenaphthylene ring, a fluorene ring, a phenalene ring, a phenanthrene ring, a triphenylene ring, a pyrene ring, a naphthacene ring, a perylene ring, and a pentacene ring. Specific examples of heteroarylene include a pyrrole ring, an oxazole ring, an isoxazole ring, a thiazole ring, an isothiazole ring, an imidazole ring, an oxadiazole ring, a thiadiazole ring, a triazole ring, a tetrazole ring, a pyrazole ring, a pyridine ring, a pyrimidine ring, a pyridazine ring, a pyrazine ring, a triazine ring, an indole ring, an isoindole ring, a 1H-indazole ring, a benzimidazole ring, a benzoxazole ring, a benzothiazole ring, a 1H-benzotriazole ring, a quinoline ring, an isoquinoline ring, a cinnoline ring, a quinazoline ring, and a quinoxaline ring. Examples of divalent groups include a phthalazine ring, a naphthyridine ring, a purine ring, a pteridine ring, a carbazole ring, an acridine ring, a phenoxathiin ring, a phenoxazine ring, a phenothiazine ring, a phenazine ring, a phenazasiline ring, an indolizine ring, a furan ring, a benzofuran ring, an isobenzofuran ring, a dibenzofuran ring, a thiophene ring, a benzothiophene ring, a dibenzothiophene ring, a furazan ring, an oxadiazole ring, a thianthrene ring, an indolocarbazole ring, a benzoindolocarbazole ring, a benzobenzoindolocarbazole ring, and a naphthobenzofuran ring. At least one hydrogen atom in the compound represented by formula (H1) may be substituted with alkyl having 1 to 6 carbon atoms, cycloalkyl having 3 to 14 carbon atoms, cyano, halogen, or deuterium.

[0210] <Compound represented by general formula (H2)> [ka] In the above formula (H2), L 2 and L 3 are each independently an aryl having 6 to 30 carbon atoms or a heteroaryl having 2 to 30 carbon atoms. The aryl is preferably an aryl having 6 to 24 carbon atoms, more preferably an aryl having 6 to 16 carbon atoms, still more preferably an aryl having 6 to 12 carbon atoms, and particularly preferably an aryl having 6 to 10 carbon atoms, and specific examples thereof include monovalent groups such as a benzene ring, a biphenyl ring, a naphthalene ring, a terphenyl ring, an acenaphthylene ring, a fluorene ring, a phenalene ring, a phenanthrene ring, a triphenylene ring, a pyrene ring, a naphthacene ring, a perylene ring, and a pentacene ring. The heteroaryl is preferably a heteroaryl having 2 to 25 carbon atoms, more preferably a heteroaryl having 2 to 20 carbon atoms, still more preferably a heteroaryl having 2 to 15 carbon atoms, and particularly preferably a heteroaryl having 2 to 10 carbon atoms. Specific examples thereof include a pyrrole ring, an oxazole ring, an isoxazole ring, a thiazole ring, an isothiazole ring, an imidazole ring, an oxadiazole ring, a thiadiazole ring, a triazole ring, a tetrazole ring, a pyrazole ring, a pyridine ring, a pyrimidine ring, a pyridazine ring, a pyrazine ring, a triazine ring, an indole ring, an isoindole ring, a 1H-indazole ring, a benzimidazole ring, a benzoxazole ring, a benzothiazole ring, a 1H-benzyl ring, a benzophenone ... and monovalent groups such as a benzotriazole ring, quinoline ring, isoquinoline ring, cinnoline ring, quinazoline ring, quinoxaline ring, phthalazine ring, naphthyridine ring, purine ring, pteridine ring, carbazole ring, acridine ring, phenoxathiin ring, phenoxazine ring, phenothiazine ring, phenazine ring, phenazasiline ring, indolizine ring, furan ring, benzofuran ring, isobenzofuran ring, dibenzofuran ring, thiophene ring, benzothiophene ring, dibenzothiophene ring, furazan ring, oxadiazole ring, thianthrene ring, indolocarbazole ring, benzoindolocarbazole ring, benzobenzoindolocarbazole ring, and naphthobenzofuran ring. At least one hydrogen atom in the compound represented by formula (H2) may be substituted with alkyl having 1 to 6 carbon atoms, cycloalkyl having 3 to 14 carbon atoms, cyano, halogen, or deuterium.

[0211] <Compound represented by general formula (H3) (an example of a polymer host material)> [ka]

[0212] In formula (H3), Each MU is independently a divalent group represented by removing any two hydrogen atoms from an aromatic compound, and each EC is independently a monovalent group represented by removing any one hydrogen atom from an aromatic compound, in which two hydrogen atoms in MU are replaced with EC or MU, and k is an integer of 2 to 50,000.

[0213] More specifically, Each MU is independently arylene, heteroarylene, diarylylenearylamino, diarylylenearylboryl, oxaborine-diyl, or azaborine-diyl; each EC is independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, or aryloxy; At least one hydrogen atom in MU and EC may be further substituted with aryl, heteroaryl, diarylamino, alkyl, and cycloalkyl; k is an integer from 2 to 50,000. k is preferably an integer of 20 to 50,000, and more preferably an integer of 100 to 50,000.

[0214] At least one hydrogen atom in MU and EC in formula (H3) may be substituted with alkyl having 1 to 24 carbon atoms, cycloalkyl having 3 to 24 carbon atoms, halogen, or deuterium; further, any -CH2- in the alkyl may be substituted with -O- or -Si(CH3)2-; any -CH2- in the alkyl except for the -CH2- directly bonded to EC in formula (H3) may be substituted with arylene having 6 to 24 carbon atoms; and any hydrogen atom in the alkyl may be substituted with fluorine.

[0215] Examples of MU include a divalent group represented by removing any two hydrogen atoms from any of the following compounds: [ka]

[0216] More specifically, examples include divalent groups represented by any of the following structures: In these, MU bonds to another MU or EC at *.

[0217] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka]

[0218] Examples of EC include monovalent groups represented by any of the following structures: In these, EC is bonded to MU at *.

[0219] [ka] [ka]

[0220] From the viewpoints of solubility and film-forming properties, the compound represented by formula (H3) preferably has 10 to 100% of the total number of MUs (k) in the molecule having alkyls of 1 to 24 carbon atoms, more preferably 30 to 100% of the total number of MUs (k) in the molecule having alkyls of 1 to 18 carbon atoms (branched-chain alkyls of 3 to 18 carbon atoms), and even more preferably 50 to 100% of the total number of MUs (k) in the molecule having alkyls of 1 to 12 carbon atoms (branched-chain alkyls of 3 to 12 carbon atoms). On the other hand, from the viewpoints of in-plane alignment and charge transport, preferably has 10 to 100% of the total number of MUs (k) in the molecule having alkyls of 7 to 24 carbon atoms, and more preferably 30 to 100% of the total number of MUs (k) in the molecule having alkyls of 7 to 24 carbon atoms (branched-chain alkyls of 7 to 24 carbon atoms).

[0221] <Compound containing a structure represented by general formula (H4)> The compound is a compound containing a structure represented by the following formula (H4), and contains a plurality of such structures, preferably 1 to 5, more preferably 1 to 3, even more preferably 1 or 2, and most preferably 1; when containing a plurality of such structures, the structures are directly bonded to each other via a single bond or via a specific linking group. [ka]

[0222] In the above general formula (H4), each G is independently "=C(-H)-" or "=N-", and the H in the "=C(-H)-" may be substituted with a substituent or a structure represented by another formula (H4).

[0223] Compounds containing a structure represented by general formula (H4) can be, for example, compounds described in WO 2012 / 153780 and WO 2013 / 038650, and can be produced according to the methods described in the above documents.

[0224] Examples of the substituent when H in "=C(-H)-" which is G is substituted include, but are not limited to, the following.

[0225] Specific examples of the "aryl group" substituent include phenyl, tolyl, xylyl, naphthyl, phenanthryl, pyrenyl, chrysenyl, benzo[c]phenanthryl, benzo[g]chrysenyl, benzanthryl, triphenylenyl, fluorenyl, 9,9-dimethylfluorenyl, benzofluorenyl, dibenzofluorenyl, biphenylyl, terphenylyl, quaterphenylyl, fluoranthenyl, etc., with phenyl, biphenylyl, terphenylyl, quaterphenylyl, naphthyl, triphenylenyl, and fluorenyl being preferred. Examples of substituted aryl groups include tolyl, xylyl, and 9,9-dimethylfluorenyl. As shown in the specific examples, aryl groups include both fused and non-fused aryl groups.

[0226] Specific examples of the "heteroaryl group" as a substituent include pyrrolyl, pyrazolyl, pyrazinyl, pyrimidinyl, pyridazinyl, pyridyl, triazinyl, indolyl, isoindolyl, imidazolyl, benzimidazolyl, indazolyl, imidazo[1,2-a]pyridinyl, furyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, azadibenzofuranyl, thiophenyl, benzothienyl, dibenzothienyl, azadibenzothienyl, quinolyl, isoquinolyl, quinoxalinyl, quinazolinyl, and naphthyridinyl. , carbazolyl, azacarbazolyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, phenothiazinyl, phenoxazinyl, oxazolyl, oxadiazolyl, furazanyl, benzoxazolyl, thienyl, thiazolyl, thiadiazolyl, benzthiazolyl, triazolyl, tetrazolyl, etc., preferably dibenzofuranyl, dibenzothienyl, carbazolyl, pyridyl, pyrimidinyl, triazinyl, azadibenzofuranyl, azadibenzothienyl, etc. Dibenzofuranyl, dibenzothienyl, azadibenzofuranyl, or azadibenzothienyl is more preferred.

[0227] The "substituted silyl group" as the substituent is also preferably a group selected from the group consisting of a substituted or unsubstituted trialkylsilyl group, a substituted or unsubstituted arylalkylsilyl group, and a substituted or unsubstituted triarylsilyl group.

[0228] 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.

[0229] The "substituted phosphine oxide group" as a substituent is also preferably a substituted or unsubstituted diarylphosphine oxide group. Specific examples of the substituted or unsubstituted diarylphosphine oxide group include diphenylphosphine oxide and ditolylphosphine oxide.

[0230] Examples of the "substituted carboxy group" as a substituent include benzoyloxy and the like.

[0231] Examples of the linking group that bonds a plurality of structures represented by formula (H4) include divalent to tetravalent, divalent to trivalent, and divalent derivatives of the above-mentioned aryl and heteroaryl.

[0232] Specific examples of the compound containing the structure represented by general formula (H4) are shown below. [ka] [ka]

[0233] <Compound represented by general formula (H5)> [ka] In the above formula (H5), R 1 ~R 11 are each independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, alkyl, or cycloalkyl (all of which are first substituents), and the R 1 ~R 11 wherein at least one hydrogen atom may be further substituted with an aryl, heteroaryl, diarylamino, alkyl, or cycloalkyl (these are all second substituents); R 1 ~R 11adjacent groups among these may be bonded to each other to form an aryl ring or a heteroaryl ring together with the a ring, the b ring or the c ring, and at least one hydrogen atom in the formed ring may be substituted with an aryl, a heteroaryl, a diarylamino, a diheteroarylamino, an arylheteroarylamino, an alkyl or a cycloalkyl (all of which are first substituents), and at least one hydrogen atom in these substituents may be further substituted with an aryl, a heteroaryl, a diarylamino, an alkyl or a cycloalkyl (all of which are second substituents); In the a-ring, b-ring, and c-ring, any "-C(-R)=" (where R is R 1 ~R 11 ) may be replaced with "-N=", At least one hydrogen atom in the compound represented by formula (H5) may be independently substituted with a halogen atom or deuterium atom.

[0234] In formula (H5), any "-C(-R)=" (where R is R 1 ~R 11 ) is replaced with "-N=" and may be changed to a pyridine ring, a pyrimidine ring, a pyridazine ring, a pyrazine ring, or other nitrogen-containing heteroaryl ring. For details of this explanation, please refer to the explanations for the above general formula (2A) and formula (2B).

[0235] Preferably, in the above formula (H5), R 1 ~R 11 are each independently hydrogen, an aryl having 6 to 30 carbon atoms, a heteroaryl having 2 to 30 carbon atoms, a diarylamino (wherein the aryl has 6 to 12 carbon atoms), an alkyl having 1 to 12 carbon atoms, or a cycloalkyl having 3 to 16 carbon atoms, and the R 1 ~R 11 at least one hydrogen atom in the formula (I) may be further substituted by an aryl having 6 to 30 carbon atoms, a heteroaryl having 2 to 30 carbon atoms, a diarylamino (wherein the aryl has 6 to 12 carbon atoms), an alkyl having 1 to 12 carbon atoms, or a cycloalkyl having 3 to 16 carbon atoms; R 1 ~R 11 Adjacent groups among these may be bonded to each other to form, together with ring a, ring b or ring c, an aryl ring having 9 to 16 carbon atoms or a heteroaryl ring having 6 to 15 carbon atoms, and at least one hydrogen atom in the formed ring may be substituted with an aryl having 6 to 30 carbon atoms, a heteroaryl having 2 to 30 carbon atoms, diarylamino (provided that aryl is aryl having 6 to 12 carbon atoms), an alkyl having 1 to 12 carbon atoms or a cycloalkyl having 3 to 16 carbon atoms, and at least one hydrogen atom in these substituents may be further substituted with an aryl having 6 to 30 carbon atoms, a heteroaryl having 2 to 30 carbon atoms, diarylamino (provided that aryl is aryl having 6 to 12 carbon atoms), an alkyl having 1 to 12 carbon atoms or a cycloalkyl having 3 to 16 carbon atoms.

[0236] More preferably, in the above formula (H5), R 1 ~R 11 are each independently hydrogen, aryl having 6 to 16 carbon atoms, heteroaryl having 2 to 15 carbon atoms, diarylamino (wherein the aryl has 6 to 10 carbon atoms), alkyl having 1 to 6 carbon atoms, or cycloalkyl having 3 to 14 carbon atoms, and the R 1 ~R 11 at least one hydrogen atom in the formula (I) may be further substituted by an aryl having 6 to 16 carbon atoms, a heteroaryl having 2 to 15 carbon atoms, a diarylamino (wherein the aryl has 6 to 10 carbon atoms), an alkyl having 1 to 6 carbon atoms, or a cycloalkyl having 3 to 14 carbon atoms; R 1 ~R 11Adjacent groups among these may be bonded to each other to form, together with ring a, ring b or ring c, an aryl ring having 9 to 12 carbon atoms or a heteroaryl ring having 6 to 12 carbon atoms, and at least one hydrogen atom in the formed ring may be substituted with an aryl having 6 to 16 carbon atoms, a heteroaryl having 2 to 15 carbon atoms, diarylamino (provided that aryl is aryl having 6 to 10 carbon atoms), an alkyl having 1 to 6 carbon atoms or a cycloalkyl having 3 to 14 carbon atoms, and at least one hydrogen atom in these substituents may be further substituted with an aryl having 6 to 16 carbon atoms, a heteroaryl having 2 to 15 carbon atoms, diarylamino (provided that aryl is aryl having 6 to 10 carbon atoms), an alkyl having 1 to 6 carbon atoms or a cycloalkyl having 3 to 14 carbon atoms.

[0237] In the above first and second substituents, examples of "aryl" and "heteroaryl" in aryl, heteroaryl, diarylamino, diheteroarylamino, and arylheteroarylamino include the following.

[0238] Specific examples of "aryl" include aryl having 6 to 30 carbon atoms, preferably aryl having 6 to 24 carbon atoms, more preferably aryl having 6 to 20 carbon atoms, still more preferably aryl having 6 to 16 carbon atoms, particularly preferably aryl having 6 to 12 carbon atoms, and most preferably aryl having 6 to 10 carbon atoms. For example, phenyl is a monocyclic aryl, (2-, 3-, 4-)biphenylyl is a bicyclic aryl, (1-, 2-)naphthyl is a fused bicyclic aryl, terphenylyl (m-terphenyl-2'-yl, m-terphenyl-4'-yl, m-terphenyl-5'-yl, o-terphenyl-3'-yl, o-terphenyl-4'-yl, p-terphenyl-2'-yl, m-terphenyl-2-yl, m-terphenyl-3-yl, m-terphenyl-4-yl, o-terphenyl-2-yl, o-terphenyl-3-yl, o-terphenyl-4-yl, p-terphenyl-2-yl, p-terphenyl-3-yl, p-terphenyl-4-yl) is a tricyclic aryl, and Examples of such aryl groups include acenaphthylene-(1-, 3-, 4-, 5-)yl, fluoren-(1-, 2-, 3-, 4-, 9-)yl, phenalene-(1-, 2-)yl, (1-, 2-, 3-, 4-, 9-)phenanthryl, tetracyclic aryl groups such as quaterphenylyl (5'-phenyl-m-terphenyl-2-yl, 5'-phenyl-m-terphenyl-3-yl, 5'-phenyl-m-terphenyl-4-yl, m-quaterphenylyl), fused tetracyclic aryl groups such as triphenylene-(1-, 2-)yl, pyren-(1-, 2-, 4-)yl, and naphthacene-(1-, 2-, 5-)yl, and fused pentacyclic aryl groups such as perylene-(1-, 2-, 3-)yl and pentacene-(1-, 2-, 5-, 6-)yl.

[0239] Specific examples of "heteroaryl" include heteroaryls having 2 to 30 carbon atoms, preferably heteroaryls having 2 to 25 carbon atoms, more preferably heteroaryls having 2 to 20 carbon atoms, still more preferably heteroaryls having 2 to 15 carbon atoms, and particularly preferably heteroaryls having 2 to 10 carbon atoms. For example, pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, oxadiazolyl, thiadiazolyl, triazolyl, tetrazolyl, pyrazolyl, pyridinyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, indolyl, isoindolyl, 1H-indazolyl, benzimidazolyl, benzoxazolyl, benzothiazolyl, 1H-benzotriazolyl, quinolinyl, isoquinolinyl, cinnolinyl, quinazolinyl, quinoxalinyl, phthalazinyl, naphthyridinyl, purinyl, pteridinyl, carbazolyl, acridinyl, phenoxazinyl indolidinyl, phenoxazinyl, phenothiazinyl, phenazinyl, phenazasilinyl, indolizinyl, furanyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, naphthobenzofuranyl, thiophenyl, benzothiophenyl, isobenzothiophenyl, dibenzothiophenyl, naphthobenzothiophenyl, benzophosphoryl, dibenzophosphoryl, a monovalent group of a benzophosphole oxide ring, a monovalent group of a dibenzophosphole oxide ring, furazanyl, thianthrenyl, indolocarbazolyl, benzoindolocarbazolyl, and benzobenzoindolocarbazolyl.

[0240] In the first and second substituents, the "alkyl" may be either linear or branched, and examples thereof include linear alkyl having 1 to 24 carbon atoms or branched alkyl having 3 to 24 carbon atoms; alkyl having 1 to 18 carbon atoms (branched alkyl having 3 to 18 carbon atoms) is preferred, alkyl having 1 to 12 carbon atoms (branched alkyl having 3 to 12 carbon atoms) is more preferred, alkyl having 1 to 6 carbon atoms (branched alkyl having 3 to 6 carbon atoms) is even more preferred, alkyl having 1 to 5 carbon atoms (branched alkyl having 3 to 5 carbon atoms) or alkyl having 1 to 4 carbon atoms (branched alkyl having 3 to 4 carbon atoms) is particularly preferred, and methyl is 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 , 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, n-eicosyl, and the like. Further 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.

[0241] In the above first and second substituents, examples of "cycloalkyl" include cycloalkyl having 3 to 24 carbon atoms, cycloalkyl having 3 to 20 carbon atoms, cycloalkyl having 3 to 16 carbon atoms, cycloalkyl having 3 to 14 carbon atoms, cycloalkyl having 5 to 10 carbon atoms, cycloalkyl having 5 to 8 carbon atoms, cycloalkyl having 5 to 6 carbon atoms, and cycloalkyl having 5 carbon atoms. Examples include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, and alkyl (especially methyl) substituted derivatives of these having 1 to 4 carbon atoms, as well as 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 decahydroazulenyl.

[0242] When the first substituent is aryl, the substitution position is R 1 , R 3 , R 4 , R 5 , R 10 and R 11 is preferred, for example, R 1 and R 3 Substitution to R 5 and R 10 Substitution to R 4 and R 11 The aryl is preferably a phenyl group.

[0243] When the first substituent is heteroaryl, the substitution position is R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 9 , R 10 and R 11 is preferred, for example, 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 The heteroaryl is preferably a carbazolyl group. The heteroaryl (for example, carbazolyl) may be substituted at the above position via a phenylene group.

[0244] Specific examples of the compound represented by formula (H5) include compounds represented by the following structural formula: In the formula, "Me" is a methyl group.

[0245] [ka] [ka]

[0246] The compound represented by formula (H5) can be prepared by first bonding rings a to c with a bonding group (-O-) to produce an intermediate (reaction 1), and then bonding rings a to c with B (boron) to produce the final product (reaction 2). Reaction 1 can be a general etherification reaction, such as a nucleophilic substitution reaction or the Ullmann reaction. Reaction 2 can be a tandem hetero-Friedel-Crafts reaction (sequential aromatic electrophilic substitution reaction). For details of reactions 1 and 2, please refer to the explanations in International Publication No. 2015 / 102118.

[0247] <Compound represented by general formula (H6)> [ka] In the above formula (H6), R 1 ~R 16are each independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, alkyl, or cycloalkyl (all of which are first substituents), and the R 1 ~R 16 wherein at least one hydrogen atom may be further substituted with an aryl, heteroaryl, diarylamino, alkyl, or cycloalkyl (these are all second substituents); R 1 ~R 16 adjacent groups among these may be bonded to each other to form an aryl ring or a heteroaryl ring together with ring a, ring b, ring c, or ring d, and at least one hydrogen atom in the formed ring may be substituted with aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, alkyl, or cycloalkyl (all of which are first substituents), and at least one hydrogen atom in these substituents may be further substituted with aryl, heteroaryl, diarylamino, alkyl, or cycloalkyl (all of which are second substituents); At least one hydrogen atom in the compound represented by formula (H6) may be independently substituted with a halogen atom or deuterium atom.

[0248] Preferably, in the above formula (H6), R 1 ~R 16 are each independently hydrogen, an aryl having 6 to 30 carbon atoms, a heteroaryl having 2 to 30 carbon atoms, a diarylamino (wherein the aryl has 6 to 12 carbon atoms), an alkyl having 1 to 12 carbon atoms, or a cycloalkyl having 3 to 16 carbon atoms, and the R 1 ~R 16 at least one hydrogen atom in the formula (I) may be further substituted by an aryl having 6 to 30 carbon atoms, a heteroaryl having 2 to 30 carbon atoms, a diarylamino (wherein the aryl has 6 to 12 carbon atoms), an alkyl having 1 to 12 carbon atoms, or a cycloalkyl having 3 to 16 carbon atoms; R 1 ~R 16Adjacent groups among these may be bonded to each other to form, together with ring a, ring b, ring c, or ring d, an aryl ring having 9 to 16 carbon atoms or a heteroaryl ring having 6 to 15 carbon atoms, and at least one hydrogen atom in the formed ring may be substituted with an aryl ring having 6 to 30 carbon atoms, a heteroaryl ring having 2 to 30 carbon atoms, a diarylamino (provided that aryl is aryl having 6 to 12 carbon atoms), an alkyl ring having 1 to 12 carbon atoms, or a cycloalkyl ring having 3 to 16 carbon atoms, and at least one hydrogen atom in these substituents may be further substituted with an aryl ring having 6 to 30 carbon atoms, a heteroaryl ring having 2 to 30 carbon atoms, a diarylamino (provided that aryl is aryl having 6 to 12 carbon atoms), an alkyl ring having 1 to 12 carbon atoms, or a cycloalkyl ring having 3 to 16 carbon atoms.

[0249] More preferably, in the above formula (H6), R 1 ~R 16 are each independently hydrogen, aryl having 6 to 16 carbon atoms, heteroaryl having 2 to 15 carbon atoms, diarylamino (wherein the aryl has 6 to 10 carbon atoms), alkyl having 1 to 6 carbon atoms, or cycloalkyl having 3 to 14 carbon atoms, and the R 1 ~R 16 at least one hydrogen atom in the formula (I) may be further substituted by an aryl having 6 to 16 carbon atoms, a heteroaryl having 2 to 15 carbon atoms, a diarylamino (wherein the aryl has 6 to 10 carbon atoms), an alkyl having 1 to 6 carbon atoms, or a cycloalkyl having 3 to 14 carbon atoms; R 1 ~R 16Adjacent groups among these may be bonded to each other to form, together with ring a, ring b, ring c, or ring d, an aryl ring having 9 to 12 carbon atoms or a heteroaryl ring having 6 to 12 carbon atoms, and at least one hydrogen atom in the formed ring may be substituted with an aryl having 6 to 16 carbon atoms, a heteroaryl having 2 to 15 carbon atoms, diarylamino (provided that aryl is aryl having 6 to 10 carbon atoms), an alkyl having 1 to 6 carbon atoms, or a cycloalkyl having 3 to 14 carbon atoms, and at least one hydrogen atom in these substituents may be further substituted with an aryl having 6 to 16 carbon atoms, a heteroaryl having 2 to 15 carbon atoms, diarylamino (provided that aryl is aryl having 6 to 10 carbon atoms), an alkyl having 1 to 6 carbon atoms, or a cycloalkyl having 3 to 14 carbon atoms.

[0250] In the above first and second substituents, examples of "aryl" and "heteroaryl" in aryl, heteroaryl, diarylamino, diheteroarylamino, and arylheteroarylamino include the following.

[0251] Specific examples of "aryl" include aryl having 6 to 30 carbon atoms, preferably aryl having 6 to 24 carbon atoms, more preferably aryl having 6 to 20 carbon atoms, still more preferably aryl having 6 to 16 carbon atoms, particularly preferably aryl having 6 to 12 carbon atoms, and most preferably aryl having 6 to 10 carbon atoms. For example, phenyl is a monocyclic aryl, (2-, 3-, 4-)biphenylyl is a bicyclic aryl, (1-, 2-)naphthyl is a fused bicyclic aryl, terphenylyl (m-terphenyl-2'-yl, m-terphenyl-4'-yl, m-terphenyl-5'-yl, o-terphenyl-3'-yl, o-terphenyl-4'-yl, p-terphenyl-2'-yl, m-terphenyl-2-yl, m-terphenyl-3-yl, m-terphenyl-4-yl, o-terphenyl-2-yl, o-terphenyl-3-yl, o-terphenyl-4-yl, p-terphenyl-2-yl, p-terphenyl-3-yl, p-terphenyl-4-yl) is a tricyclic aryl, and Examples of such aryl groups include acenaphthylene-(1-, 3-, 4-, 5-)yl, fluoren-(1-, 2-, 3-, 4-, 9-)yl, phenalene-(1-, 2-)yl, (1-, 2-, 3-, 4-, 9-)phenanthryl, tetracyclic aryl groups such as quaterphenylyl (5'-phenyl-m-terphenyl-2-yl, 5'-phenyl-m-terphenyl-3-yl, 5'-phenyl-m-terphenyl-4-yl, m-quaterphenylyl), fused tetracyclic aryl groups such as triphenylene-(1-, 2-)yl, pyren-(1-, 2-, 4-)yl, and naphthacene-(1-, 2-, 5-)yl, and fused pentacyclic aryl groups such as perylene-(1-, 2-, 3-)yl and pentacene-(1-, 2-, 5-, 6-)yl.

[0252] Specific examples of "heteroaryl" include heteroaryls having 2 to 30 carbon atoms, preferably heteroaryls having 2 to 25 carbon atoms, more preferably heteroaryls having 2 to 20 carbon atoms, still more preferably heteroaryls having 2 to 15 carbon atoms, and particularly preferably heteroaryls having 2 to 10 carbon atoms. For example, pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, oxadiazolyl, thiadiazolyl, triazolyl, tetrazolyl, pyrazolyl, pyridinyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, indolyl, isoindolyl, 1H-indazolyl, benzimidazolyl, benzoxazolyl, benzothiazolyl, 1H-benzotriazolyl, quinolinyl, isoquinolinyl, cinnolinyl, quinazolinyl, quinoxalinyl, phthalazinyl, naphthyridinyl, purinyl, pteridinyl, carbazolyl, acridinyl, phenoxazinyl indolidinyl, phenoxazinyl, phenothiazinyl, phenazinyl, phenazasilinyl, indolizinyl, furanyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, naphthobenzofuranyl, thiophenyl, benzothiophenyl, isobenzothiophenyl, dibenzothiophenyl, naphthobenzothiophenyl, benzophosphoryl, dibenzophosphoryl, a monovalent group of a benzophosphole oxide ring, a monovalent group of a dibenzophosphole oxide ring, furazanyl, thianthrenyl, indolocarbazolyl, benzoindolocarbazolyl, and benzobenzoindolocarbazolyl.

[0253] In the first and second substituents, the "alkyl" may be either linear or branched, and examples thereof include linear alkyl having 1 to 24 carbon atoms or branched alkyl having 3 to 24 carbon atoms; alkyl having 1 to 18 carbon atoms (branched alkyl having 3 to 18 carbon atoms) is preferred, alkyl having 1 to 12 carbon atoms (branched alkyl having 3 to 12 carbon atoms) is more preferred, alkyl having 1 to 6 carbon atoms (branched alkyl having 3 to 6 carbon atoms) is even more preferred, alkyl having 1 to 5 carbon atoms (branched alkyl having 3 to 5 carbon atoms) or alkyl having 1 to 4 carbon atoms (branched alkyl having 3 to 4 carbon atoms) is particularly preferred, and methyl is 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 , 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, n-eicosyl, and the like. Further 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.

[0254] In the above 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 C1-C4 alkyl (especially methyl) substituents, 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.

[0255] The compound represented by formula (H6) can be produced by referring to the description described in International Publication No. 2014 / 042197.

[0256] <TADF material> By reducing the energy difference between the singlet excited state and the triplet excited state, reverse energy transfer from the triplet excited state, which usually has a low transition probability, to the singlet excited state occurs with high efficiency, and thus luminescence from the singlet state (thermally activated delayed fluorescence, TADF) is exhibited. In ordinary 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.

[0257] Examples of the TADF material that can be used for such an object include a compound represented by the following general formula (H7), or a compound having the following general formula (H7) as a partial structure.

Chemical formula

[0258] TADF materials are preferably donor-acceptor type TADF compounds (DA type TADF compounds), which are designed to localize the HOMO and LUMO within the molecule using electron-donating substituents called donors and electron-accepting substituents called acceptors, thereby allowing efficient reverse intersystem crossing to occur.

[0259] In this specification, the term "electron-donating substituent" (donor) refers to a substituent or partial structure in which the LUMO orbital is localized in a TADF compound molecule, and the term "electron-accepting substituent" (acceptor) refers to a substituent or partial structure in which the HOMO orbital is localized in a TADF compound molecule.

[0260] In general, TADF compounds using donors or acceptors have large spin-orbit coupling (SOC) due to their structure, and small exchange interaction between the HOMO and LUMO, resulting in a small ΔE(ST), resulting in a very fast reverse intersystem crossing rate. On the other hand, TADF compounds using donors or acceptors exhibit large structural relaxation in the excited state (in some molecules, the stable structures differ between the ground state and the excited state, so when an external stimulus causes a transition from the ground state to the excited state, the structure then changes to the stable structure in the excited state), resulting in a broad emission spectrum, which may reduce color purity when used as an emitting material.

[0261] If the color purity is reduced by the TADF material, a fluorescent compound can be added as another component to the light-emitting layer or a layer adjacent to the light-emitting layer. The TADF material acts as an assisting dopant, and the other component acts as an emitting dopant. The other component may be a compound whose absorption spectrum at least partially overlaps with the emission peak of the assisting dopant.

[0262] As the donor and acceptor structures used in the TADF material, for example, the structures described in Chemistry of Materials, 2017, 29, 1946-1963 can be used. 3Examples of the functional group include nitrogen-containing functional groups, and more specifically, groups derived from carbazole, dimethylcarbazole, di-t-butylcarbazole, dimethoxycarbazole, tetramethylcarbazole, benzofluorocarbazole, benzothienocarbazole, phenyldihydroindolocarbazole, phenylbicarbazole, bicarbazole, tercarbazole, diphenylcarbazolylamine, tetraphenylcarbazolyldiamine, phenoxazine, dihydrophenazine, phenothiazine, dimethyldihydroacridine, diphenylamine, bis(tert-butylphenyl)amine, N1-(4-(diphenylamino)phenyl)-N4,N4-diphenylbenzene-1,4-diamine, dimethyltetraphenyldihydroacridinediamine, tetramethyl-dihydro-indenoacridine, and diphenyl-dihydrodibenzazasiline. Examples of the EA include, for example, sp 2Nitrogen-containing aromatic rings, CN-substituted aromatic rings, rings having ketones and cyano groups, more specifically sulfonyldibenzene, benzophenone, phenylenebis(phenylmethanone), benzonitrile, isonicotinonitrile, phthalonitrile, isophthalonitrile, paraphthalonitrile, triazole, oxazole, thiadiazole, benzothiazole, benzobis(thiazole), benzoxazole, benzobis(oxazole), quinoline, benzimidazole, dibenzoquinoxaline, heptaazaphenalene, thioxanthone dioxide, dimethylanthone, Examples of Ln include groups derived from thracenone, anthracenedione, pyridine, 5H-cyclopenta[1,2-b:5,4-b']dipyridine, benzenetricarbonitrile, fluorenedicarbonitrile, pyrazinedicarbonitrile, pyridinedicarbonitrile, dibenzoquinoxalinedicarbonitrile, pyrimidine, phenylpyrimidine, methylpyrimidine, triazine, triphenyltriazine, bis(phenylsulfonyl)benzene, dimethylthioxanthene dioxide, thianthrene tetraoxide, and tris(dimethylphenyl)borane. Examples of Ln include a single bond and an arylene, more specifically, phenylene, biphenylene, and naphthylene. In any of the structures, hydrogen may be substituted with an alkyl, cycloalkyl, or aryl. In particular, compounds having at least one partial structure selected from carbazole, phenoxazine, acridine, triazine, pyrimidine, pyrazine, thioxanthene, benzonitrile, phthalonitrile, isophthalonitrile, diphenylsulfone, triazole, oxadiazole, thiadiazole, and benzophenone are preferred.

[0263] The compound represented by general formula (H7) is more specifically a compound represented by any one of the following general formulas (H7-1), (H7-2) and (H7-3). [ka]

[0264] In the above general formulas (H7-1), (H7-2) and (H7-3), M each independently represents a single bond, -O-, >N-Ar, or >C(-Ar)2, and is preferably a single bond, -O-, or >N-Ar from the viewpoint of the HOMO depth and the heights of the excited singlet energy level and excited triplet energy level of the partial structure to be formed; J is a spacer structure separating the donor partial structure and the acceptor partial structure, and each J is independently an arylene having 6 to 18 carbon atoms. From the viewpoint of the magnitude of conjugation exuded from the donor partial structure and the acceptor partial structure, an arylene having 6 to 12 carbon atoms is preferred, and more specific examples thereof include phenylene, methylphenylene, and dimethylphenylene. Q each independently represents ═C(—H)— or ═N—, and is preferably ═N— in view of the shallowness of the LUMO of the partial structure to be formed and the heights of the excited singlet energy level and the excited triplet energy level, Ar each independently represents hydrogen, an aryl having 6 to 24 carbon atoms, a heteroaryl having 2 to 24 carbon atoms, an alkyl having 1 to 12 carbon atoms, or a cycloalkyl having 3 to 18 carbon atoms; from the viewpoint of the HOMO depth and the heights of the excited singlet energy level and the excited triplet energy level of the partial structure to be formed, Ar is preferably hydrogen, an aryl having 6 to 12 carbon atoms, a heteroaryl having 2 to 14 carbon atoms, an alkyl having 1 to 4 carbon atoms, or a cycloalkyl having 6 to 10 carbon atoms, more preferably hydrogen, phenyl, tolyl, xylyl, mesityl, biphenyl, pyridyl, bipyridyl, triazyl, carbazolyl, dimethylcarbazolyl, di-t-butylcarbazolyl, benzimidazole, or phenylbenzimidazole, and still more preferably hydrogen, phenyl, or carbazolyl; m is 1 or 2; n is an integer of 2 to (6-m), and from the viewpoint of steric hindrance, is preferably an integer of 4 to (6-m). Furthermore, at least one hydrogen atom in the compounds represented by the above formulas may be substituted with a halogen or deuterium.

[0265] Examples of compounds represented by formula (H7) include compounds represented by the following structures: In the structural formula, * indicates a bonding position, "Me" indicates a methyl group, and "tBu" indicates a t-butyl group.

[0266] [ka]

[0267] [ka]

[0268] [ka]

[0269] [ka]

[0270] [ka]

[0271] [ka]

[0272] [ka]

[0273] [ka]

[0274] [ka]

[0275] Of 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 the compound represented by general formula (H7).

[0276] In addition, as the dopant material, known compounds other than the polycyclic aromatic compounds represented by the above general formula (1A) or general formula (1B) can also be used, and a dopant material can be selected from a variety of materials depending on the desired emission color.Specific examples include fused ring derivatives of phenanthrene, anthracene, pyrene, tetracene, pentacene, perylene, naphthopyrene, dibenzopyrene, rubrene, and chrysene, benzoxazole derivatives, benzothiazole derivatives, benzimidazole derivatives, benzotriazole derivatives, oxazole derivatives, oxadiazole derivatives, thiazole derivatives, imidazole derivatives, thiadiazole derivatives, triazole derivatives, pyrazoline derivatives, stilbene derivatives, thiophene derivatives, and tetraphenylbutadiene. derivatives, cyclopentadiene derivatives, bisstyryl derivatives such as bisstyryl anthracene derivatives and distyrylbenzene derivatives (JP Patent Publication No. 245087 / 1999), bisstyrylarylene derivatives (JP Patent Publication No. 247278 / 1990), diazaindacene derivatives, furan derivatives, benzofuran derivatives, isobenzofuran derivatives such as phenylisobenzofuran, dimesitylisobenzofuran, di(2-methylphenyl)isobenzofuran, di(2-trifluoromethylphenyl)isobenzofuran, and phenylisobenzofuran Coumarin derivatives such as dibenzofuran derivatives, 7-dialkylaminocoumarin derivatives, 7-piperidinocoumarin derivatives, 7-hydroxycoumarin derivatives, 7-methoxycoumarin derivatives, 7-acetoxycoumarin derivatives, 3-benzothiazolylcoumarin derivatives, 3-benzimidazolylcoumarin derivatives, and 3-benzoxazolylcoumarin derivatives, dicyanomethylenepyran derivatives, dicyanomethylenethiopyran derivatives, polymethine derivatives, cyanine derivatives, oxobenzoanthracene derivatives, xanthene derivatives, and rhodamine derivatives. conductors, fluorescein derivatives, pyrylium derivatives, carbostyril derivatives, acridine derivatives, oxazine derivatives, phenylene oxide derivatives, quinacridone derivatives, quinazoline derivatives, pyrrolopyridine derivatives, furopyridine derivatives, 1,2,5-thiadiazolopyrene derivatives, pyrromethene derivatives, perinone derivatives, pyrrolopyrrole derivatives, squarylium derivatives, violanthrone derivatives, phenazine derivatives, acridone derivatives, deazaflavin derivatives, fluorene derivatives, and benzofluorene derivatives.

[0277] Examples of blue to blue-green dopant materials include aromatic hydrocarbon compounds such as naphthalene, anthracene, phenanthrene, pyrene, triphenylene, perylene, fluorene, indene, and chrysene, and derivatives thereof; furan, pyrrole, thiophene, silole, 9-silafluorene, 9,9'-spirobisilafluorene, benzothiophene, benzofuran, indole, dibenzothiophene, dibenzofuran, imidazopyridine, phenanthroline, pyrazine, naphthyridine, quinoxaline, and pyrrolopyridine; Examples include aromatic heterocyclic compounds such as lysine and thioxanthene and their derivatives, distyrylbenzene derivatives, tetraphenylbutadiene derivatives, stilbene derivatives, aldazine derivatives, coumarin derivatives, azole derivatives such as imidazole, thiazole, thiadiazole, carbazole, oxazole, oxadiazole, and triazole, and metal complexes thereof, and aromatic amine derivatives typified by N,N'-diphenyl-N,N'-di(3-methylphenyl)-4,4'-diphenyl-1,1'-diamine.

[0278] Examples of the green to yellow dopant material include coumarin derivatives, phthalimide derivatives, naphthalimide derivatives, perinone derivatives, pyrrolopyrrole derivatives, cyclopentadiene derivatives, acridone derivatives, quinacridone derivatives, and naphthacene derivatives such as rubrene. Further, suitable examples include compounds obtained by introducing a substituent that enables a longer wavelength, such as aryl, heteroaryl, arylvinyl, amino, or cyano, into the compounds exemplified above as the blue to blue-green dopant material.

[0279] Further examples of orange to red dopant materials include naphthalimide derivatives such as bis(diisopropylphenyl)perylenetetracarboxylic acid imide, perinone derivatives, rare earth complexes such as Eu complexes having acetylacetone, benzoylacetone, and phenanthroline as ligands, 4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran and 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, violanthrone derivatives, phenazine derivatives, phenoxazone derivatives, and thiadiazolopyrene derivatives. Further preferred examples include compounds obtained by introducing a substituent that enables a longer wavelength, such as aryl, heteroaryl, arylvinyl, amino, or cyano, into the compounds exemplified above as blue to blue-green and green to yellow dopant materials.

[0280] In addition, the dopant can be appropriately selected from the compounds described in Chemical Industry, June 2004, page 13 and the references cited therein.

[0281] Among the above-mentioned dopant materials, amines having a stilbene structure, perylene derivatives, borane derivatives, aromatic amine derivatives, coumarin derivatives, pyran derivatives, or pyrene derivatives are particularly preferred.

[0282] The amine having a stilbene structure is represented by, for example, the following formula: [ka] In the formula, Ar 1 is an m-valent group derived from an aryl having 6 to 30 carbon atoms, and Ar 2 and Ar 3 are each independently an aryl having 6 to 30 carbon atoms, and Ar 1 ~Ar 3 At least one of the groups has a stilbene structure, and Ar1 ~Ar 3 may be substituted with aryl, heteroaryl, alkyl, cycloalkyl, trisubstituted silyl (silyl trisubstituted with at least one of aryl, alkyl, and cycloalkyl) or cyano, and m is an integer of 1 to 4.

[0283] The amine having a stilbene structure is more preferably diaminostilbene represented by the following formula: [ka] In the formula, Ar 2 and Ar 3 are each independently an aryl having 6 to 30 carbon atoms, and Ar 2 and Ar 3 may be substituted with aryl, heteroaryl, alkyl, cycloalkyl, trisubstituted silyl (silyl trisubstituted with at least one of aryl, alkyl, and cycloalkyl), or cyano.

[0284] Specific examples of the aryl having 6 to 30 carbon atoms include phenyl, naphthyl, acenaphthylenyl, fluorenyl, phenalenyl, phenanthrenyl, anthryl, fluoranthenyl, triphenylenyl, pyrenyl, chrysenyl, naphthacenyl, perylenyl, stilbenyl, distyrylphenyl, distyrylbiphenylyl, and distyrylfluorenyl.

[0285] Specific examples of the amine having a stilbene structure include N,N,N',N'-tetra(4-biphenylyl)-4,4'-diaminostilbene, N,N,N',N'-tetra(1-naphthyl)-4,4'-diaminostilbene, N,N,N',N'-tetra(2-naphthyl)-4,4'-diaminostilbene, N,N'-di(2-naphthyl)-N,N'-diphenyl-4,4'-diaminostilbene, N,N'-di(9-phenanthr ... 4,4'-bis(9-ethyl-3-carbazovinylene)-biphenyl, 4,4'-bis(9-phenyl-3-carbazovinylene)-biphenyl, and the like. Furthermore, amines having a stilbene structure, such as those described in JP-A Nos. 2003-347056 and 2001-307884, may also be used.

[0286] Examples of perylene derivatives include 3,10-bis(2,6-dimethylphenyl)perylene, 3,10-bis(2,4,6-trimethylphenyl)perylene, 3,10-diphenylperylene, 3,4-diphenylperylene, 2,5,8,11-tetra-t-butylperylene, 3,4,9,10-tetraphenylperylene, 3-(1'-pyrenyl)-8,11-di(t-butyl)perylene, 3-(9'-anthryl)-8,11-di(t-butyl)perylene, and 3,3'-bis(8,11-di(t-butyl)perylenyl). Furthermore, perylene derivatives described in JP-A Nos. 11-97178, 2000-133457, 2000-26324, 2001-267079, 2001-267078, 2001-267076, 2000-34234, 2001-267075, and 2001-217077 may also be used.

[0287] Examples of borane derivatives include 1,8-diphenyl-10-(dimesitylboryl)anthracene, 9-phenyl-10-(dimesitylboryl)anthracene, 4-(9'-anthryl)dimesitylborylnaphthalene, 4-(10'-phenyl-9'-anthryl)dimesitylborylnaphthalene, 9-(dimesitylboryl)anthracene, 9-(4'-biphenylyl)-10-(dimesitylboryl)anthracene, and 9-(4'-(N-carbazolyl)phenyl)-10-(dimesitylboryl)anthracene. Furthermore, borane derivatives described in WO 2000 / 40586 and the like may also be used.

[0288] The aromatic amine derivative is represented by, for example, the following formula: [ka] In the formula, Ar 4 is an n-valent group derived from an aryl having 6 to 30 carbon atoms, and Ar 5 and Ar 6 are each independently an aryl having 6 to 30 carbon atoms, and Ar 4 ~Ar 6 may be substituted with aryl, heteroaryl, alkyl, cycloalkyl, trisubstituted silyl (silyl trisubstituted with at least one of aryl, alkyl, and cycloalkyl) or cyano, and n is an integer of 1 to 4.

[0289] In particular, Ar 4 is a divalent group derived from anthracene, chrysene, fluorene, benzofluorene, or pyrene, and Ar 5 and Ar 6 are each independently an aryl having 6 to 30 carbon atoms, and Ar 4 ~Ar 6 is optionally substituted with aryl, heteroaryl, alkyl, cycloalkyl, trisubstituted silyl (silyl trisubstituted with at least one of aryl, alkyl, and cycloalkyl) or cyano, and n is 2.

[0290] Specific examples of the aryl having 6 to 30 carbon atoms include phenyl, naphthyl, acenaphthylenyl, fluorenyl, phenalenyl, phenanthrenyl, anthryl, fluoranthenyl, triphenylenyl, pyrenyl, chrysenyl, naphthacenyl, perylenyl, and pentacenyl.

[0291] Examples of aromatic amine derivatives include chrysene derivatives such as N,N,N',N'-tetraphenylchrysene-6,12-diamine, N,N,N',N'-tetra(p-tolyl)chrysene-6,12-diamine, N,N,N',N'-tetra(m-tolyl)chrysene-6,12-diamine, N,N,N',N'-tetrakis(4-isopropylphenyl)chrysene-6,12-diamine, N,N,N',N'-tetra(naphthalen-2-yl)chrysene-6,12-diamine, and N,N'-diphenyl -N,N'-di(p-tolyl)chrysene-6,12-diamine, N,N'-diphenyl-N,N'-bis(4-ethylphenyl)chrysene-6,12-diamine, N,N'-diphenyl-N,N'-bis(4-isopropylphenyl)chrysene-6,12-diamine, N,N'-diphenyl-N,N'-bis(4-t-butylphenyl)chrysene-6,12-diamine, and N,N'-bis(4-isopropylphenyl)-N,N'-di(p-tolyl)chrysene-6,12-diamine.

[0292] Examples of pyrene-based compounds include N,N,N',N'-tetraphenylpyrene-1,6-diamine, N,N,N',N'-tetra(p-tolyl)pyrene-1,6-diamine, N,N,N',N'-tetra(m-tolyl)pyrene-1,6-diamine, N,N,N',N'-tetrakis(4-isopropylphenyl)pyrene-1,6-diamine, N,N,N',N'-tetrakis(3,4-dimethylphenyl)pyrene-1,6-diamine, N,N'-diphenyl-N,N'-di(p-tolyl)pyrene-1,6-diamine, and N,N'-diphenyl-N,N'-bis(4-ethylphenyl)pyrene-1, 6-diamine, N,N'-diphenyl-N,N'-bis(4-isopropylphenyl)pyrene-1,6-diamine, N,N'-diphenyl-N,N'-bis(4-t-butylphenyl)pyrene-1,6-diamine, N,N'-bis(4-isopropylphenyl)-N,N'-di(p-tolyl)pyrene-1,6-diamine, N,N,N',N'-tetrakis(3,4-dimethylphenyl)-3,8-diphenylpyrene-1,6-diamine, N,N,N,N-tetraphenylpyrene-1,8-diamine, N,N'-bis(biphenyl-4-yl)-N,N'-diphenylpyrene-1,8-diamine, N 1 ,N 6 -diphenyl-N 1 ,N 6 -bis-(4-trimethylsilanyl-phenyl)-1H,8H-pyrene-1,6-diamine.

[0293] Examples of anthracene compounds include N,N,N,N-tetraphenylanthracene-9,10-diamine, N,N,N',N'-tetra(p-tolyl)anthracene-9,10-diamine, N,N,N',N'-tetra(m-tolyl)anthracene-9,10-diamine, N,N,N',N'-tetrakis(4-isopropylphenyl)anthracene-9,10-diamine, N,N'-diphenyl-N,N'-di(p-tolyl)anthracene-9,10-diamine, and N,N'-diphenyl-N,N'-di(m-tolyl)anthracene-9,10-diamine. -diamine, N,N'-diphenyl-N,N'-bis(4-ethylphenyl)anthracene-9,10-diamine, N,N'-diphenyl-N,N'-bis(4-isopropylphenyl)anthracene-9,10-diamine, N,N'-diphenyl-N,N'-bis(4-t-butylphenyl)anthracene-9,10-diamine, N,N'-bis(4-isopropylphenyl)-N,N'-di(p-tolyl)anthracene-9,10-diamine, 2,6-di-t-butyl-N,N,N',N'-tetra(p-tolyl)anthracene-9,10-diamine 2,6-di-t-butyl-N,N'-diphenyl-N,N'-bis(4-isopropylphenyl)anthracene-9,10-diamine, 2,6-di-t-butyl-N,N'-bis(4-isopropylphenyl)-N,N'-di(p-tolyl)anthracene-9,10-diamine, 2,6-dicyclohexyl-N,N'-bis(4-isopropylphenyl)-N,N'-di(p-tolyl)anthracene-9,10-diamine, 2,6-dicyclohexyl-N,N'-bis(4-isopropylphenyl)-N,N'-di(p-tolyl)anthracene-9,10-diamine, 2,6-dicyclohexyl-N,N'-bis(4-isopropylphenyl)-N,N'-bis(4-t-butylphenyl) Examples 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.

[0294] Other examples include [4-(4-diphenylamino-phenyl)naphthalen-1-yl]-diphenylamine, [6-(4-diphenylamino-phenyl)naphthalen-2-yl]-diphenylamine, 4,4'-bis[4-diphenylaminonaphthalen-1-yl]biphenyl, 4,4'-bis[6-diphenylaminonaphthalen-2-yl]biphenyl, 4,4"-bis[4-diphenylaminonaphthalen-1-yl]-p-terphenyl, and 4,4"-bis[6-diphenylaminonaphthalen-2-yl]-p-terphenyl. Alternatively, aromatic amine derivatives such as those described in JP-A-2006-156888 may be used.

[0295] Coumarin derivatives include coumarin-6 and coumarin-334. Coumarin derivatives described in JP-A Nos. 2004-43646, 2001-76876, and 6-298758 may also be used.

[0296] Examples of pyran derivatives include DCM and DCJTB shown below. [ka] Furthermore, pyran derivatives described in JP-A Nos. 2005-126399, 2005-097283, 2002-234892, 2001-220577, 2001-081090, and 2001-052869 may also be used.

[0297] The above-mentioned light-emitting layer materials (host materials and dopant materials) can also be used as light-emitting layer materials in the form of polymer compounds obtained by polymerizing a reactive compound substituted with a reactive substituent as a monomer, or a crosslinked polymer thereof, or a pendant-type polymer compound obtained by reacting a main-chain polymer with the reactive compound, or a crosslinked pendant-type polymer thereof. Regarding the reactive substituent in this case, the explanation for the polycyclic aromatic compound represented by the above general formula (1A) or (1B) can be cited. The uses of such polymer compounds and crosslinked polymers will be described in detail below.

[0298] <Electron injection layer and electron transport layer in organic electroluminescent device> The electron injection layer 107 plays a role of efficiently injecting electrons moving from the cathode 108 into the light-emitting layer 105 or the electron transport layer 106. The electron transport layer 106 plays a role of efficiently transporting electrons injected from the cathode 108 or electrons injected from the cathode 108 via the electron injection layer 107 to the light-emitting layer 105. The electron transport layer 106 and the electron injection layer 107 are each formed by laminating or mixing one or more electron transport / injection materials, or by a mixture of an electron transport / injection material and a polymer binder.

[0299] The electron injection / transport layer is a layer responsible for injecting electrons from the cathode and transporting them. It is desirable for the layer to have high electron injection efficiency and 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 be less likely to generate trapping impurities during manufacture and use. However, considering the balance between hole and electron transport, if a material primarily serves to efficiently block holes from the anode from flowing to the cathode without recombining, it can have the same effect of improving luminous efficiency as a material with high electron transport ability, even if it does not have a particularly high electron transport ability. Therefore, the electron injection / transport layer in this embodiment may also function as a layer that can efficiently block the movement of holes.

[0300] The material (electron transport material) forming the electron transport layer 106 or the electron injection layer 107 can be arbitrarily selected from compounds conventionally used as electron transport compounds in photoconductive materials and known compounds used in the electron injection layer and electron transport layer of organic EL devices. In the present invention, the polycyclic aromatic compound represented by the above general formula (1A) or (1B) can be used as the electron transport material.

[0301] Materials used in the electron transport layer or electron injection layer preferably contain at least one selected from the group consisting of aromatic or heteroaromatic ring compounds 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 containing electron-accepting nitrogen. Specific examples include fused ring aromatic derivatives such as naphthalene and anthracene; styryl aromatic derivatives such as 4,4'-bis(diphenylethenyl)biphenyl; perinone derivatives; coumarin derivatives; naphthalimide derivatives; quinone derivatives such as anthraquinone and diphenoquinone; phosphine oxide derivatives; carbazole derivatives; and indole derivatives. Metal complexes containing electron-accepting nitrogen include, for example, hydroxyazole complexes such as hydroxyphenyloxazole complexes, azomethine complexes, tropolone metal complexes, flavonol metal complexes, and benzoquinoline metal complexes. These materials can be used alone or in combination with other materials.

[0302] Specific examples of other electron transport 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 (e.g., 1,3-bis[(4-t-butylphenyl)1,3,4-oxadiazolyl]phenylene), thiophene derivatives, triazole derivatives (e.g., 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, pyrazine derivatives, and the like. Examples of suitable amine derivatives include benzoquinolin-2-yl (2,2'-bis(benzo[h]quinolin-2-yl)-9,9'-spirobifluorene, imidazopyridine derivatives, borane derivatives, benzimidazole derivatives (tris(N-phenylbenzimidazol-2-yl)benzene, benzoxazole derivatives, benzothiazole derivatives, quinoline derivatives, oligopyridine derivatives such as terpyridine, bipyridine derivatives, terpyridine derivatives (1,3-bis(4'-(2,2':6',2"-terpyridinyl))benzene, etc.), naphthyridine derivatives (bis(1-naphthyl)-4-(1,8-naphthyridin-2-yl)phenylphosphine oxide, etc.), aldazine derivatives, carbazole derivatives, indole derivatives, phosphine oxide derivatives, and bisstyryl derivatives.

[0303] Furthermore, metal complexes having an electron-accepting nitrogen atom can also be used, and examples thereof include hydroxyazole complexes such as quinolinol metal complexes and hydroxyphenyloxazole complexes, azomethine complexes, tropolone metal complexes, flavonol metal complexes, and benzoquinoline metal complexes.

[0304] The above-mentioned materials may be used alone or in combination with other materials.

[0305] Among the above-mentioned materials, borane derivatives, pyridine derivatives, fluoranthene derivatives, BO-based 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.

[0306] <Borane derivatives> The borane derivative is, for example, a compound represented by the following general formula (ETM-1), and is disclosed in detail in JP-A-2007-27587. [ka] In the above formula (ETM-1), R 11 and R 12 are each independently at least one of hydrogen, alkyl, cycloalkyl, optionally substituted aryl, substituted silyl, optionally substituted nitrogen-containing heterocycle, or cyano; R 13 ~R 16 are each independently an optionally substituted alkyl, an optionally substituted cycloalkyl, or an optionally substituted aryl, X is an optionally substituted arylene, Y is an optionally substituted aryl having 16 or fewer carbon atoms, a substituted boryl, or an optionally substituted carbazolyl, and each n is independently an integer of 0 to 3. In addition, examples of the substituent in the case of "optionally substituted" or "substituted" include aryl, heteroaryl, alkyl, and cycloalkyl.

[0307] 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 12are each independently at least one of hydrogen, alkyl, cycloalkyl, optionally substituted aryl, substituted silyl, optionally substituted nitrogen-containing heterocycle, or cyano; R 13 ~R 16 are each independently an optionally substituted alkyl, an optionally substituted cycloalkyl, or an optionally substituted aryl, and R 21 and R 22 are each independently at least one of hydrogen, alkyl, cycloalkyl, optionally substituted aryl, substituted silyl, optionally substituted nitrogen-containing heterocycle, or cyano; and X 1 is an optionally substituted arylene having 20 or less carbon atoms, each n is independently an integer of 0 to 3, and each m is independently an integer of 0 to 4. In addition, examples of the substituent in the case of "optionally substituted" or "substituted" include aryl, heteroaryl, alkyl, and cycloalkyl. [ka] In formula (ETM-1-2), R 11 and R 12 are each independently at least one of hydrogen, alkyl, cycloalkyl, optionally substituted aryl, substituted silyl, optionally substituted nitrogen-containing heterocycle, or cyano; R 13 ~R 16 are each independently an optionally substituted alkyl, an optionally substituted cycloalkyl, or an optionally substituted aryl; X 1 is an arylene having 20 or less carbon atoms which may be substituted, and each n is independently an integer of 0 to 3. In addition, examples of the substituent in the case of "optionally substituted" or "substituted" include aryl, heteroaryl, alkyl, and cycloalkyl.

[0308] X 1Specific examples of include divalent groups represented by any of the following formulae (X-1) to (X-9): * in each structural formula represents the bonding position. [ka] (In each formula, R a are each independently an alkyl group, a cycloalkyl group, or an optionally substituted phenyl group.

[0309] Specific examples of the borane derivative include the following compounds: [ka]

[0310] This borane derivative can be produced using known raw materials and known synthesis methods.

[0311] <Pyridine derivatives> The pyridine derivative is, for example, a compound represented by the following formula (ETM-2), and is preferably a compound represented by formula (ETM-2-1) or formula (ETM-2-2). [ka]

[0312] φ is an n-valent aryl ring (preferably an n-valent benzene ring, naphthalene ring, anthracene ring, fluorene ring, benzofluorene ring, phenalene ring, phenanthrene ring, or triphenylene ring), and n is an integer of 1 to 4.

[0313] In the above formula (ETM-2-1), R 11 ~R 18 are each independently hydrogen, alkyl (preferably alkyl having 1 to 24 carbon atoms), cycloalkyl (preferably cycloalkyl having 3 to 12 carbon atoms), or aryl (preferably aryl having 6 to 30 carbon atoms).

[0314] In the above formula (ETM-2-2), R11 and R 12 are each independently hydrogen, alkyl (preferably alkyl having 1 to 24 carbon atoms), cycloalkyl (preferably cycloalkyl having 3 to 12 carbon atoms), or aryl (preferably aryl having 6 to 30 carbon atoms), and R 11 and R 12 may be bonded to form a ring.

[0315] In each formula, the "pyridine-based substituent" is any of the following formulae (Py-1) to (Py-15), and each pyridine-based substituent may be independently substituted with alkyl having 1 to 4 carbon atoms or cycloalkyl having 5 to 10 carbon atoms. In addition, the pyridine-based substituent may be bonded to φ, an anthracene ring, or a fluorene ring in each formula via a phenylene group or a naphthylene group. * in each structural formula indicates a bonding position. [ka]

[0316] The pyridine-based substituent is any of the above formulae (Py-1) to (Py-15), and among these, any of the following formulae (Py-21) to (Py-44) is preferred. In each structural formula, * indicates a bonding position. [ka]

[0317] At least one hydrogen atom in each pyridine derivative may be replaced with deuterium, and one of the two "pyridine-based substituents" in the above formulas (ETM-2-1) and (ETM-2-2) may be replaced with aryl.

[0318] R 11 ~R 18The "alkyl" in the above may be either linear or branched, and examples thereof include linear alkyl having 1 to 24 carbon atoms and branched alkyl having 3 to 24 carbon atoms. A preferred "alkyl" is an alkyl having 1 to 18 carbon atoms (branched alkyl having 3 to 18 carbon atoms). A more preferred "alkyl" is an alkyl having 1 to 12 carbon atoms (branched alkyl having 3 to 12 carbon atoms). An even more preferred "alkyl" is an alkyl having 1 to 6 carbon atoms (branched alkyl having 3 to 6 carbon atoms). An especially preferred "alkyl" is an alkyl having 1 to 4 carbon atoms (branched alkyl having 3 to 4 carbon atoms).

[0319] Specific examples of "alkyl" include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, t-butyl, n-pentyl, isopentyl, neopentyl, t-pentyl (t-amyl), n-hexyl, 1-methylpentyl, 3,3-dimethylbutyl, 2-ethylbutyl, n-heptyl, 1-methylhexyl, n-octyl, t-octyl (1,1,3,3-tetramethylbutyl), 1-methylpentyl, 2-ethylbutyl, n-heptyl, 1-methylhexyl, n-octyl, t-octyl (1,1,3,3-tetramethylbutyl), 1-methylpentyl, 2-ethylbutyl, 2-methylpentyl, 2-methylpentyl, 2-methylhexyl, 2-methylpent ... Examples of the alkyl esters include 1-hexylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 2,6-dimethyl-4-heptyl, 3,5,5-trimethylhexyl, n-decyl, n-undecyl, 1-methyldecyl, n-dodecyl, n-tridecyl, 1-hexylheptyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, n-heptadecyl, n-octadecyl, and n-eicosyl. Further 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.

[0320] The above description of alkyl can be cited for the alkyl having 1 to 4 carbon atoms that substitutes the pyridine-based substituent.

[0321] R 11 ~R 18 In the above, examples of the "cycloalkyl" include cycloalkyl having 3 to 12 carbon atoms. A preferred "cycloalkyl" is cycloalkyl having 3 to 10 carbon atoms. A more preferred "cycloalkyl" is cycloalkyl having 3 to 8 carbon atoms. An even more preferred "cycloalkyl" is cycloalkyl having 3 to 6 carbon atoms. Specific examples of "cycloalkyl" include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, methylcyclopentyl, cycloheptyl, methylcyclohexyl, cyclooctyl, and dimethylcyclohexyl.

[0322] As for the cycloalkyl having 5 to 10 carbon atoms that substitutes the pyridine-based substituent, the above description of the cycloalkyl can be cited.

[0323] R 11 ~R 18As for the "aryl" in the above, preferred aryl is aryl having 6 to 30 carbon atoms, more preferred aryl is aryl having 6 to 18 carbon atoms, still more preferred aryl is aryl having 6 to 14 carbon atoms, and particularly preferred is aryl having 6 to 12 carbon atoms.

[0324] Specific examples of the "aryl having 6 to 30 carbon atoms" include phenyl, which is a monocyclic aryl; (1-, 2-)naphthyl, which is a fused bicyclic aryl; acenaphthylene-(1-, 3-, 4-, 5-)yl, fluoren-(1-, 2-, 3-, 4-, 9-)yl, phenalene-(1-, 2-)yl, and (1-, 2-, 3-, 4-, 9-)phenanthryl, which are fused tricyclic aryl; triphenylene-(1-, 2-)yl, pyren-(1-, 2-, 4-)yl, and naphthacene-(1-, 2-, 5-)yl, which are fused tetracyclic aryl; and perylene-(1-, 2-, 3-)yl and pentacene-(1-, 2-, 5-, 6-)yl, which are fused pentacyclic aryl.

[0325] Preferred examples of the "aryl having 6 to 30 carbon atoms" include phenyl, naphthyl, phenanthryl, chrysenyl, and triphenylenyl, more preferably phenyl, 1-naphthyl, 2-naphthyl, and phenanthryl, and particularly preferably phenyl, 1-naphthyl, and 2-naphthyl.

[0326] R in the above formula (ETM-2-2) 11 and R 12 may be bonded to form a ring, and as a result, cyclobutane, cyclopentane, cyclopentene, cyclopentadiene, cyclohexane, fluorene, indene, or the like may be spiro-bonded to the five-membered ring of the fluorene skeleton.

[0327] Specific examples of the pyridine derivative include the following compounds: [ka]

[0328] This pyridine derivative can be produced using known raw materials and known synthesis methods.

[0329] <Fluoranthene derivative> The fluoranthene derivative is, for example, a compound represented by the following general formula (ETM-3), and is specifically disclosed in International Publication No. 2010 / 134352.

Chemical formula

[0330] In the above formula (ETM-3), X 12 ~X 21 represents hydrogen, halogen, linear, branched or cyclic alkyl, linear, branched or cyclic alkoxy, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl. Here, examples of the substituent when it is substituted include aryl, heteroaryl, alkyl or cycloalkyl, etc.

[0331] Specific examples of this fluoranthene derivative include, for example, the following compounds.

Chemical formula

[0332] <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

[0333] R 1 ~R 11are each independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl (two aryls may be bonded via a single bond or a linking group), alkyl, cycloalkyl, alkoxy, or aryloxy, and the R 1 ~R 11 At least one hydrogen atom in may be substituted with an aryl, heteroaryl, alkyl, or cycloalkyl.

[0334] Also, R 1 ~R 11 Adjacent groups among these may be bonded to each other to form an aryl ring or a heteroaryl ring together with ring a, ring b, or ring c, and at least one hydrogen atom in the formed ring may be substituted with an 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 atom in these substituents may be substituted with an aryl, heteroaryl, alkyl, or cycloalkyl.

[0335] In addition, at least one hydrogen atom in the compound or structure represented by formula (ETM-4) may be substituted with a halogen or deuterium atom.

[0336] For an explanation of the substituents and ring formation form in formula (ETM-4), as well as the multimer formed by combining multiple structures of formula (ETM-4), the explanations in WO 2015 / 102118 and the explanation of the polycyclic aromatic compounds represented by formula (1A) or formula (1B) above can be cited.

[0337] Specific examples of the BO derivative include the following compounds: [ka]

[0338] This BO derivative can be produced using known raw materials and known synthesis methods.

[0339] <Anthracene derivatives> One of the anthracene derivatives is, for example, a compound represented by the following formula (ETM-5-1). [ka]

[0340] Ar are each independently a divalent benzene or naphthalene; R 1 ~R 4 are each independently hydrogen, alkyl having 1 to 6 carbon atoms, cycloalkyl having 3 to 6 carbon atoms, or aryl having 6 to 20 carbon atoms.

[0341] Each Ar can be independently selected from divalent benzene or naphthalene, and the two Ar may be different or the same, but are preferably the same from the viewpoint of ease of synthesis of the anthracene derivative. Ar is bonded to pyridine to form a "moiety consisting of Ar and pyridine," and this moiety is bonded to anthracene as a group represented by, for example, any of the following formulas (Py-1) to (Py-12). * in each structural formula indicates the bonding position. [ka]

[0342] Among these groups, groups represented by any of the above formulas (Py-1) to (Py-9) are preferred, and groups represented by any of the above formulas (Py-1) to (Py-6) are more preferred. The two "moieties consisting of Ar and pyridine" 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 characteristics, it is preferable that the structures of the two "moieties consisting of Ar and pyridine" be the same or different.

[0343] R 1 ~R 4 The alkyl having 1 to 6 carbon atoms in the formula (I) may be either linear or branched. That is, it is a linear alkyl having 1 to 6 carbon atoms or a branched alkyl having 3 to 6 carbon atoms. It is more preferably an alkyl having 1 to 4 carbon atoms (branched alkyl having 3 to 4 carbon atoms). Specific examples include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, t-butyl, n-pentyl, isopentyl, neopentyl, t-pentyl (t-amyl), n-hexyl, 1-methylpentyl, 3,3-dimethylbutyl, and 2-ethylbutyl. Methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, or t-butyl is preferred, and methyl, ethyl, or t-butyl is more preferred.

[0344] R 1 ~R 4 Specific examples of the cycloalkyl having 3 to 6 carbon atoms in the formula include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, methylcyclopentyl, cycloheptyl, methylcyclohexyl, cyclooctyl, and dimethylcyclohexyl.

[0345] R 1 ~R 4 In the above, the aryl having 6 to 20 carbon atoms is preferably an aryl having 6 to 16 carbon atoms, more preferably an aryl having 6 to 12 carbon atoms, and particularly preferably an aryl having 6 to 10 carbon atoms.

[0346] Specific examples of "aryl having 6 to 20 carbon atoms" include monocyclic aryls such as phenyl, (o-, m-, p-)tolyl, (2,3-, 2,4-, 2,5-, 2,6-, 3,4-, 3,5-)xylyl, mesityl (2,4,6-trimethylphenyl), and (o-, m-, p-)cumenyl; bicyclic aryls such as (2-, 3-, 4-)biphenylyl; fused 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, p-terphenyl-2 ...4'-yl, p-terphenyl-2-yl, m-ter phenyl-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), fused tricyclic aryls such as anthracene-(1-, 2-, 9-)yl, acenaphthylene-(1-, 3-, 4-, 5-)yl, fluorene-(1-, 2-, 3-, 4-, 9-)yl, phenalene-(1-, 2-)yl, (1-, 2-, 3-, 4-, 9-)phenanthryl, fused tetracyclic aryls such as triphenylene-(1-, 2-)yl, pyrene-(1-, 2-, 4-)yl, tetracene-(1-, 2-, 5-)yl, and fused pentacyclic aryls such as perylene-(1-, 2-, 3-)yl.

[0347] The "aryl having 6 to 20 carbon atoms" is preferably 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.

[0348] One of the anthracene derivatives is, for example, a compound represented by the following formula (ETM-5-2). [ka]

[0349] Ar 1 are each independently a single bond, a divalent benzene, a divalent naphthalene, a divalent anthracene, a divalent fluorene, or a divalent phenalene.

[0350] Ar 2 are each independently an aryl having 6 to 20 carbon atoms, and the same explanation as for "aryl having 6 to 20 carbon atoms" in the above formula (ETM-5-1) can be cited. An aryl having 6 to 16 carbon atoms is preferred, an aryl having 6 to 12 carbon atoms is more preferred, and an aryl having 6 to 10 carbon atoms is particularly preferred. Specific examples include phenyl, biphenylyl, naphthyl, terphenylyl, anthracenyl, acenaphthylenyl, fluorenyl, phenalenyl, phenanthryl, triphenylenyl, pyrenyl, tetracenyl, perylenyl, etc.

[0351] R 1 ~R 4 are each independently hydrogen, alkyl having 1 to 6 carbon atoms, cycloalkyl having 3 to 6 carbon atoms, or aryl having 6 to 20 carbon atoms, and the explanation for the above formula (ETM-5-1) can be cited.

[0352] Specific examples of these anthracene derivatives include the following compounds: [ka]

[0353] These anthracene derivatives can be produced using known raw materials and known synthesis methods.

[0354] <Benzofluorene derivatives> The benzofluorene derivative is, for example, a compound represented by the following formula (ETM-6). [ka]

[0355] Ar 1are each independently an aryl having 6 to 20 carbon atoms, and the same explanation as for "aryl having 6 to 20 carbon atoms" in the above formula (ETM-5-1) can be cited. An aryl having 6 to 16 carbon atoms is preferred, an aryl having 6 to 12 carbon atoms is more preferred, and an aryl having 6 to 10 carbon atoms is particularly preferred. Specific examples include phenyl, biphenylyl, naphthyl, terphenylyl, anthracenyl, acenaphthylenyl, fluorenyl, phenalenyl, phenanthryl, triphenylenyl, pyrenyl, tetracenyl, perylenyl, etc.

[0356] Ar 2 are each independently hydrogen, alkyl (preferably alkyl having 1 to 24 carbon atoms), cycloalkyl (preferably cycloalkyl having 3 to 12 carbon atoms), or aryl (preferably aryl having 6 to 30 carbon atoms), and two Ar 2 may be bonded to form a ring.

[0357] Ar 2 The "alkyl" in the above may be either linear or branched, and examples thereof include linear alkyl having 1 to 24 carbon atoms and branched alkyl having 3 to 24 carbon atoms. A preferred "alkyl" is an alkyl having 1 to 18 carbon atoms (branched alkyl having 3 to 18 carbon atoms). A more preferred "alkyl" is an alkyl having 1 to 12 carbon atoms (branched alkyl having 3 to 12 carbon atoms). An even more preferred "alkyl" is an alkyl having 1 to 6 carbon atoms (branched alkyl having 3 to 6 carbon atoms). An especially preferred "alkyl" is an alkyl having 1 to 4 carbon atoms (branched alkyl having 3 to 4 carbon atoms). Specific examples of "alkyl" include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, t-butyl, n-pentyl, isopentyl, neopentyl, t-pentyl (t-amyl), n-hexyl, 1-methylpentyl, 3,3-dimethylbutyl, 2-ethylbutyl, n-heptyl, 1-methylhexyl, and the like.

[0358] Ar 2In the above, examples of the "cycloalkyl" include cycloalkyl having 3 to 12 carbon atoms. A preferred "cycloalkyl" is cycloalkyl having 3 to 10 carbon atoms. A more preferred "cycloalkyl" is cycloalkyl having 3 to 8 carbon atoms. An even more preferred "cycloalkyl" is cycloalkyl having 3 to 6 carbon atoms. Specific examples of the "cycloalkyl" include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, methylcyclopentyl, cycloheptyl, methylcyclohexyl, cyclooctyl, and dimethylcyclohexyl.

[0359] Ar 2 As for the "aryl" in the above, preferred aryl is aryl having 6 to 30 carbon atoms, more preferred aryl is aryl having 6 to 18 carbon atoms, still more preferred aryl is aryl having 6 to 14 carbon atoms, and particularly preferred is aryl having 6 to 12 carbon atoms.

[0360] Specific examples of the "aryl having 6 to 30 carbon atoms" include phenyl, naphthyl, acenaphthylenyl, fluorenyl, phenalenyl, phenanthryl, triphenylenyl, pyrenyl, naphthacenyl, perylenyl, and pentacenyl.

[0361] Two Ar 2 may be bonded to form a ring, and as a result, cyclobutane, cyclopentane, cyclopentene, cyclopentadiene, cyclohexane, fluorene, indene, or the like may be spiro-bonded to the five-membered ring of the fluorene skeleton.

[0362] Specific examples of the benzofluorene derivative include the following compounds: [ka]

[0363] This benzofluorene derivative can be produced using known raw materials and known synthesis methods.

[0364] <Phosphine oxide derivatives> The phosphine oxide derivative is, for example, a compound represented by the following formula (ETM-7-1), the details of which are also described in WO 2013 / 079217. [ka] R 5 is a substituted or unsubstituted alkyl having 1 to 20 carbon atoms, cycloalkyl having 3 to 20 carbon atoms, aryl having 6 to 20 carbon atoms, or heteroaryl having 5 to 20 carbon atoms, R 6 is CN, a substituted or unsubstituted alkyl having 1 to 20 carbon atoms, cycloalkyl having 3 to 20 carbon atoms, heteroalkyl having 1 to 20 carbon atoms, aryl having 6 to 20 carbon atoms, heteroaryl having 5 to 20 carbon atoms, alkoxy having 1 to 20 carbon atoms, or aryloxy having 6 to 20 carbon atoms, R 7 and R 8 are each independently a substituted or unsubstituted aryl having 6 to 20 carbon atoms or a heteroaryl having 5 to 20 carbon atoms, R 9 is oxygen or sulfur, j is 0 or 1, k is 0 or 1, r is an integer of 0 to 4, and q is an integer of 1 to 3. When substituted, the substituent may be an aryl, heteroaryl, alkyl, or cycloalkyl.

[0365] The phosphine oxide derivative may be, for example, a compound represented by the following formula (ETM-7-2). [ka]

[0366] R 1 ~R 3may be the same or different and are selected from hydrogen, an alkyl group, a cycloalkyl group, an aralkyl group, an alkenyl group, a cycloalkenyl group, an alkynyl group, an alkoxy group, an alkylthio group, a cycloalkylthio group, an aryl ether group, an aryl thioether group, an aryl group, a heterocyclic group, a halogen atom, a cyano group, an aldehyde group, a carbonyl group, a carboxyl group, an amino group, a nitro group, a silyl group, and a fused ring formed between adjacent substituents.

[0367] Ar 1 may be the same or different and are arylene or heteroarylene groups. 2 may be the same or different and are aryl or heteroaryl groups, provided that Ar 1 and Ar 2 At least one of R has a substituent or forms a condensed ring with the adjacent substituent. n is an integer of 0 to 3. When n is 0, there is no unsaturated structural portion, and when n is 3, R 1 does not exist.

[0368] Among these substituents, the alkyl group refers to a saturated aliphatic hydrocarbon group such as a methyl group, an ethyl group, a propyl group, or a butyl group, which may be unsubstituted or substituted. When substituted, the substituent is not particularly limited, and examples thereof include an alkyl group, an aryl group, and a heterocyclic group, which also applies to the following description. The number of carbon atoms in the alkyl group is not particularly limited, but is usually in the range of 1 to 20 from the viewpoints of availability and cost.

[0369] The cycloalkyl group refers to a saturated alicyclic hydrocarbon group, such as cyclopropyl, cyclohexyl, norbornyl, adamantyl, etc., which may be unsubstituted or substituted. The number of carbon atoms in the alkyl group is not particularly limited, but is usually in the range of 3 to 20.

[0370] The aralkyl group refers to an aromatic hydrocarbon group connected via an aliphatic hydrocarbon, such as a benzyl group or a phenylethyl group, and both the aliphatic hydrocarbon and the aromatic hydrocarbon may be substituted or unsubstituted. The number of carbon atoms in the aliphatic portion is not particularly limited, but is usually in the range of 1 to 20.

[0371] The alkenyl group refers to an unsaturated aliphatic hydrocarbon group containing a double bond, such as a vinyl group, an allyl group, or a butadienyl group, which may be substituted or unsubstituted. The number of carbon atoms in the alkenyl group is not particularly limited, but is usually in the range of 2 to 20.

[0372] Furthermore, the cycloalkenyl group refers to an unsaturated alicyclic hydrocarbon group containing a double bond, such as a cyclopentenyl group, a cyclopentadienyl group, or a cyclohexene group, which may be substituted or unsubstituted.

[0373] The alkynyl group refers to an unsaturated aliphatic hydrocarbon group containing a triple bond, such as an acetylenyl group, which may be substituted or unsubstituted. The number of carbon atoms in the alkynyl group is not particularly limited, but is usually in the range of 2 to 20.

[0374] The alkoxy group refers to an aliphatic hydrocarbon group such as a methoxy group, which is bonded via an ether bond, and the aliphatic hydrocarbon group may be substituted or unsubstituted. The number of carbon atoms in the alkoxy group is not particularly limited, but is usually in the range of 1 to 20.

[0375] An alkylthio group is a group in which the oxygen atom of the ether bond of an alkoxy group is substituted with a sulfur atom.

[0376] A cycloalkylthio group is a group in which the oxygen atom of the ether bond of a cycloalkoxy group is substituted with a sulfur atom.

[0377] The aryl ether group refers to an aromatic hydrocarbon group such as a phenoxy group that is bonded to an ether bond, and the aromatic hydrocarbon group may be substituted or unsubstituted. The number of carbon atoms in the aryl ether group is not particularly limited, but is usually in the range of 6 to 40.

[0378] An aryl thioether group is a group in which the oxygen atom of the ether bond of an aryl ether group is substituted with a sulfur atom.

[0379] The aryl group refers to an aromatic hydrocarbon group such as a phenyl group, a naphthyl group, a biphenyl group, a phenanthryl group, a terphenyl group, or a pyrenyl group. The aryl group may be unsubstituted or substituted. The number of carbon atoms in the aryl group is not particularly limited, but is usually in the range of 6 to 40.

[0380] The heterocyclic group refers to a cyclic structural group having atoms other than carbon, such as a furanyl group, a thiophenyl group, an oxazolyl group, a pyridyl group, a quinolinyl group, or a carbazolyl group, which may be unsubstituted or substituted. The number of carbon atoms in the heterocyclic group is not particularly limited, but is usually in the range of 2 to 30.

[0381] Halogen refers to fluorine, chlorine, bromine, and iodine.

[0382] The aldehyde group, carbonyl group and amino group may also include groups substituted with an aliphatic hydrocarbon, an alicyclic hydrocarbon, an aromatic hydrocarbon, a heterocycle or the like.

[0383] The aliphatic hydrocarbons, alicyclic hydrocarbons, aromatic hydrocarbons and heterocyclic rings may be either unsubstituted or substituted.

[0384] The silyl group refers to a silicon compound group such as a trimethylsilyl group, which may be substituted or unsubstituted. The number of carbon atoms in the silyl group is not particularly limited, but is usually in the range of 3 to 20. The number of silicon atoms is usually 1 to 6.

[0385] 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 etc., where n is 1, two R 1 They may form conjugated or non-conjugated fused rings with each other. These fused rings may contain nitrogen, oxygen, or sulfur atoms in the ring structure, and may be fused with another ring.

[0386] Specific examples of the phosphine oxide derivative include the following compounds: [ka]

[0387] This phosphine oxide derivative can be produced using known raw materials and known synthesis methods.

[0388] <Pyrimidine derivatives> The pyrimidine derivative is, for example, a compound represented by the following formula (ETM-8), preferably a compound represented by the following formula (ETM-8-1). Details are also described in WO 2011 / 021689. [ka]

[0389] Each Ar is independently an optionally substituted aryl or an optionally substituted heteroaryl, and n is an integer of 1 to 4, preferably an integer of 1 to 3, and more preferably 2 or 3.

[0390] Examples of the "aryl" in "optionally substituted aryl" include aryl having 6 to 30 carbon atoms, preferably aryl having 6 to 24 carbon atoms, more preferably aryl having 6 to 20 carbon atoms, and even more preferably aryl having 6 to 12 carbon atoms.

[0391] Specific examples of "aryl" include phenyl, which is a monocyclic aryl; (2-, 3-, 4-)biphenylyl, which is a bicyclic aryl; (1-, 2-)naphthyl, which is a fused bicyclic aryl; terphenylyl, which is a tricyclic aryl (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 fused tricyclic aryl. Examples of the aryl include acenaphthylene-(1-, 3-, 4-, 5-)yl, fluoren-(1-, 2-, 3-, 4-, 9-)yl, phenalene-(1-, 2-)yl, and (1-, 2-, 3-, 4-, 9-)phenanthryl; the tetracyclic aryl group is quaterphenylyl (5'-phenyl-m-terphenyl-2-yl, 5'-phenyl-m-terphenyl-3-yl, 5'-phenyl-m-terphenyl-4-yl, and m-quaterphenylyl); the fused tetracyclic aryl group is triphenylene-(1-, 2-)yl, pyren-(1-, 2-, 4-)yl, and naphthacene-(1-, 2-, 5-)yl; and the fused pentacyclic aryl group is perylene-(1-, 2-, 3-)yl and pentacene-(1-, 2-, 5-, 6-)yl.

[0392] Examples of the "heteroaryl" in "optionally substituted heteroaryl" include heteroaryl having 2 to 30 carbon atoms, preferably heteroaryl having 2 to 25 carbon atoms, more preferably heteroaryl having 2 to 20 carbon atoms, still more preferably heteroaryl having 2 to 15 carbon atoms, and particularly preferably heteroaryl having 2 to 10 carbon atoms. Examples of heteroaryl include heterocycles containing, in addition to carbon, 1 to 5 heteroatoms selected from oxygen, sulfur, and nitrogen as ring-constituting atoms.

[0393] Specific examples of heteroaryl include pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, oxadiazolyl, thiadiazolyl, triazolyl, tetrazolyl, pyrazolyl, pyridinyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, indolyl, isoindolyl, 1H-indazolyl, benzimidazolyl, benzoxazolyl, benzothiazolyl, 1H-benzotriazolyl, quinolinyl, isoquinolinyl, cinnolinyl, quinazolinyl, quinoxalinyl, phthalazinyl, naphthyridinyl, purinyl, pteridinyl, carbazolyl, Examples include acridinyl, phenoxathiinyl, phenoxazinyl, phenothiazinyl, phenazinyl, phenazasilinyl, indolizinyl, furanyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, naphthobenzofuranyl, thiophenyl, benzothiophenyl, dibenzothiophenyl, naphthobenzothiophenyl, benzophosphoryl, dibenzophosphoryl, a monovalent group of a benzophosphole oxide ring, a monovalent group of a dibenzophosphole oxide ring, furazanyl, thianthrenyl, indolocarbazolyl, benzoindolocarbazolyl, and benzobenzoindolocarbazolyl.

[0394] Furthermore, at least one hydrogen atom in the above aryl and heteroaryl may be substituted, and may be substituted with, for example, the above aryl or heteroaryl, respectively.

[0395] Specific examples of the pyrimidine derivative include the following compounds: [ka]

[0396] This pyrimidine derivative can be produced using known raw materials and known synthesis methods.

[0397] <Carbazole derivatives> The carbazole derivative is, for example, a compound represented by the following formula (ETM-9), or a multimer in which a plurality of such compounds are bonded via single bonds, etc. Details are described in U.S. Publication No. 2014 / 0197386. [ka]

[0398] Each Ar is independently an optionally substituted aryl or an optionally substituted heteroaryl, and each n is independently an integer of 0 to 4, preferably an integer of 0 to 3, and more preferably 0 or 1.

[0399] Examples of the "aryl" in "optionally substituted aryl" include aryl having 6 to 30 carbon atoms, preferably aryl having 6 to 24 carbon atoms, more preferably aryl having 6 to 20 carbon atoms, and even more preferably aryl having 6 to 12 carbon atoms.

[0400] Specific examples of "aryl" include phenyl, which is a monocyclic aryl; (2-, 3-, 4-)biphenylyl, which is a bicyclic aryl; (1-, 2-)naphthyl, which is a fused bicyclic aryl; terphenylyl, which is a tricyclic aryl (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 fused tricyclic aryl. Examples of the aryl include acenaphthylene-(1-, 3-, 4-, 5-)yl, fluoren-(1-, 2-, 3-, 4-, 9-)yl, phenalene-(1-, 2-)yl, and (1-, 2-, 3-, 4-, 9-)phenanthryl; the tetracyclic aryl group is quaterphenylyl (5'-phenyl-m-terphenyl-2-yl, 5'-phenyl-m-terphenyl-3-yl, 5'-phenyl-m-terphenyl-4-yl, and m-quaterphenylyl); the fused tetracyclic aryl group is triphenylene-(1-, 2-)yl, pyren-(1-, 2-, 4-)yl, and naphthacene-(1-, 2-, 5-)yl; and the fused pentacyclic aryl group is perylene-(1-, 2-, 3-)yl and pentacene-(1-, 2-, 5-, 6-)yl.

[0401] Examples of the "heteroaryl" in "optionally substituted heteroaryl" include heteroaryl having 2 to 30 carbon atoms, preferably heteroaryl having 2 to 25 carbon atoms, more preferably heteroaryl having 2 to 20 carbon atoms, still more preferably heteroaryl having 2 to 15 carbon atoms, and particularly preferably heteroaryl having 2 to 10 carbon atoms. Examples of heteroaryl include heterocycles containing, in addition to carbon, 1 to 5 heteroatoms selected from oxygen, sulfur, and nitrogen as ring-constituting atoms.

[0402] Specific examples of heteroaryl include pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, oxadiazolyl, thiadiazolyl, triazolyl, tetrazolyl, pyrazolyl, pyridinyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, indolyl, isoindolyl, 1H-indazolyl, benzimidazolyl, benzoxazolyl, benzothiazolyl, 1H-benzotriazolyl, quinolinyl, isoquinolinyl, cinnolinyl, quinazolinyl, quinoxalinyl, phthalazinyl, naphthyridinyl, purinyl, pteridinyl, carbazolyl, Examples include acridinyl, phenoxathiinyl, phenoxazinyl, phenothiazinyl, phenazinyl, phenazasilinyl, indolizinyl, furanyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, naphthobenzofuranyl, thiophenyl, benzothiophenyl, dibenzothiophenyl, naphthobenzothiophenyl, benzophosphoryl, dibenzophosphoryl, a monovalent group of a benzophosphole oxide ring, a monovalent group of a dibenzophosphole oxide ring, furazanyl, thianthrenyl, indolocarbazolyl, benzoindolocarbazolyl, and benzobenzoindolocarbazolyl.

[0403] Furthermore, at least one hydrogen atom in the above aryl and heteroaryl may be substituted, and may be substituted with, for example, the above aryl or heteroaryl, respectively.

[0404] The carbazole derivative may be a polymer in which a plurality of compounds represented by the above formula (ETM-9) are bonded together via single bonds, etc. In this case, they may be bonded together via an aryl ring (preferably a polyvalent benzene ring, naphthalene ring, anthracene ring, fluorene ring, benzofluorene ring, phenalene ring, phenanthrene ring, or triphenylene ring) in addition to a single bond.

[0405] Specific examples of the carbazole derivative include the following compounds. [ka]

[0406] This carbazole derivative can be produced using known raw materials and known synthesis methods.

[0407] <Triazine derivatives> The triazine derivative is, for example, a compound represented by the following formula (ETM-10), preferably a compound represented by the following formula (ETM-10-1), the details of which are described in U.S. Patent Publication No. 2011 / 0156013. [ka]

[0408] Each Ar is independently an optionally substituted aryl or an optionally substituted heteroaryl, and n is an integer of 1 to 3, preferably 2 or 3.

[0409] Examples of the "aryl" in "optionally substituted aryl" include aryl having 6 to 30 carbon atoms, preferably aryl having 6 to 24 carbon atoms, more preferably aryl having 6 to 20 carbon atoms, and even more preferably aryl having 6 to 12 carbon atoms.

[0410] Specific examples of "aryl" include phenyl, which is a monocyclic aryl; (2-, 3-, 4-)biphenylyl, which is a bicyclic aryl; (1-, 2-)naphthyl, which is a fused bicyclic aryl; terphenylyl, which is a tricyclic aryl (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 fused tricyclic aryl. Examples of the aryl include acenaphthylene-(1-, 3-, 4-, 5-)yl, fluoren-(1-, 2-, 3-, 4-, 9-)yl, phenalene-(1-, 2-)yl, and (1-, 2-, 3-, 4-, 9-)phenanthryl; the tetracyclic aryl group is quaterphenylyl (5'-phenyl-m-terphenyl-2-yl, 5'-phenyl-m-terphenyl-3-yl, 5'-phenyl-m-terphenyl-4-yl, and m-quaterphenylyl); the fused tetracyclic aryl group is triphenylene-(1-, 2-)yl, pyren-(1-, 2-, 4-)yl, and naphthacene-(1-, 2-, 5-)yl; and the fused pentacyclic aryl group is perylene-(1-, 2-, 3-)yl and pentacene-(1-, 2-, 5-, 6-)yl.

[0411] Examples of the "heteroaryl" in "optionally substituted heteroaryl" include heteroaryl having 2 to 30 carbon atoms, preferably heteroaryl having 2 to 25 carbon atoms, more preferably heteroaryl having 2 to 20 carbon atoms, still more preferably heteroaryl having 2 to 15 carbon atoms, and particularly preferably heteroaryl having 2 to 10 carbon atoms. Examples of heteroaryl include heterocycles containing, in addition to carbon, 1 to 5 heteroatoms selected from oxygen, sulfur, and nitrogen as ring-constituting atoms.

[0412] Specific examples of heteroaryl include pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, oxadiazolyl, thiadiazolyl, triazolyl, tetrazolyl, pyrazolyl, pyridinyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, indolyl, isoindolyl, 1H-indazolyl, benzimidazolyl, benzoxazolyl, benzothiazolyl, 1H-benzotriazolyl, quinolinyl, isoquinolinyl, cinnolinyl, quinazolinyl, quinoxalinyl, phthalazinyl, naphthyridinyl, purinyl, pteridinyl, carbazolyl, Examples include acridinyl, phenoxathiinyl, phenoxazinyl, phenothiazinyl, phenazinyl, phenazasilinyl, indolizinyl, furanyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, naphthobenzofuranyl, thiophenyl, benzothiophenyl, dibenzothiophenyl, naphthobenzothiophenyl, benzophosphoryl, dibenzophosphoryl, a monovalent group of a benzophosphole oxide ring, a monovalent group of a dibenzophosphole oxide ring, furazanyl, thianthrenyl, indolocarbazolyl, benzoindolocarbazolyl, and benzobenzoindolocarbazolyl.

[0413] Furthermore, at least one hydrogen atom in the above aryl and heteroaryl may be substituted, and may be substituted with, for example, the above aryl or heteroaryl, respectively.

[0414] Specific examples of the triazine derivative include the following compounds: [ka]

[0415] This triazine derivative can be produced using known raw materials and known synthesis methods.

[0416] <Benzimidazole derivatives> The benzimidazole derivative is, for example, a compound represented by the following formula (ETM-11). [ka]

[0417] 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-based substituent" is a substituent in which the pyridyl group in the "pyridine-based substituent" in the above formulas (ETM-2), (ETM-2-1), and (ETM-2-2) is replaced with a benzimidazole group, and at least one hydrogen atom in the benzimidazole derivative may be replaced with a deuterium atom. In the following structural formulas, * indicates a bonding position. [ka]

[0418] R in the benzimidazole group 11 is hydrogen, alkyl having 1 to 24 carbon atoms, cycloalkyl having 3 to 12 carbon atoms, or aryl having 6 to 30 carbon atoms, and R in the above formula (ETM-2-1) and formula (ETM-2-2) 11 The explanation can be cited.

[0419] φ is preferably an anthracene ring or a fluorene ring, and in this case, the structure can be as described in the above formula (ETM-2-1) or formula (ETM-2-2), and R 11 ~R 18 The explanation for the above formula (ETM-2-1) or formula (ETM-2-2) can be cited. In addition, in the above formula (ETM-2-1) or formula (ETM-2-2), two pyridine-based substituents are explained as being bonded together, but when these are replaced with benzimidazole-based substituents, both pyridine-based substituents may be replaced with benzimidazole-based substituents (i.e., n=2), or one of the pyridine-based substituents may be replaced with a benzimidazole-based substituent and the other pyridine-based substituent may be replaced with R 11 ~R 18(i.e., n=1). Furthermore, for example, R in the above formula (ETM-2-1) 11 ~R 18 At least one of the above is replaced with a benzimidazole-based substituent to form a "pyridine-based substituent" R 11 ~R 18 may be replaced with .

[0420] Specific examples of the benzimidazole derivative include 1-phenyl-2-(4-(10-phenylanthracen-9-yl)phenyl)-1H-benzo[d]imidazole, 2-(4-(10-(naphthalen-2-yl)anthracen-9-yl)phenyl)-1-phenyl-1H-benzo[d]imidazole, 2-(3-(10-(naphthalen-2-yl)anthracen-9-yl)phenyl)-1-phenyl-1H-benzo[d]imidazole, and 5-(10-(naphthalen-2-yl)anthracen-9-yl)-1,2-diphenyl-1H-benzo[d]imidazole. , 1-(4-(10-(naphthalen-2-yl)anthracen-9-yl)phenyl)-2-phenyl-1H-benzo[d]imidazole, 2-(4-(9,10-di(naphthalen-2-yl)anthracen-2-yl)phenyl)-1-phenyl-1H-benzo[d]imidazole, 1-(4-(9,10-di(naphthalen-2-yl)anthracen-2-yl)phenyl)-2-phenyl-1H-benzo[d]imidazole, 5-(9,10-di(naphthalen-2-yl)anthracen-2-yl)-1,2-diphenyl-1H-benzo[d]imidazole, and the like. [ka]

[0421] The benzimidazole derivative can be produced using known raw materials and known synthesis methods.

[0422] <Phenanthroline derivatives> The phenanthroline derivative is, for example, a compound represented by the following formula (ETM-12) or formula (ETM-12-1), the details of which are described in WO 2006 / 021982. [ka]

[0423] φ is an n-valent aryl ring (preferably an n-valent benzene ring, naphthalene ring, anthracene ring, fluorene ring, benzofluorene ring, phenalene ring, phenanthrene ring, or triphenylene ring), and n is an integer of 1 to 4.

[0424] R in each formula 11 ~R 18 are each independently hydrogen, alkyl (preferably alkyl having 1 to 24 carbon atoms), cycloalkyl (preferably cycloalkyl having 3 to 12 carbon atoms), or aryl (preferably aryl having 6 to 30 carbon atoms). 11 ~R 18 Either of these bonds to φ, an aryl ring.

[0425] At least one hydrogen atom in each phenanthroline derivative may be substituted with deuterium.

[0426] R 11 ~R 18 The alkyl, cycloalkyl and aryl in the above formula (ETM-2) are R 11 ~R 18 The explanation of the formula (1) can be cited. In addition to the examples given above, φ can also be represented by the following structural formulas. In the structural formulas below, R is independently hydrogen, methyl, ethyl, isopropyl, cyclohexyl, phenyl, 1-naphthyl, 2-naphthyl, biphenylyl, or terphenylyl. In each structural formula, * indicates a bonding position. [ka]

[0427] Specific examples of the phenanthroline derivative include 4,7-diphenyl-1,10-phenanthroline, 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline, 9,10-di(1,10-phenanthrolin-2-yl)anthracene, 2,6-di(1,10-phenanthrolin-5-yl)pyridine, 1,3,5-tri(1,10-phenanthrolin-5-yl)benzene, 9,9'-difluoro-bi(1,10-phenanthrolin-5-yl), bathocuproine, 1,3-bis(2-phenyl-1,10-phenanthrolin-9-yl)benzene, and compounds represented by the following structural formula: [ka]

[0428] This phenanthroline derivative can be produced using known raw materials and known synthesis methods.

[0429] <Quinolinol-based metal complexes> The quinolinol metal complex is, for example, a compound represented by the following general formula (ETM-13). [ka] In the formula, R 1 ~R 6 are each independently hydrogen, fluorine, alkyl, cycloalkyl, aralkyl, alkenyl, cyano, alkoxy, or aryl; M is Li, Al, Ga, Be, or Zn; and n is an integer of 1 to 3.

[0430] Specific examples of quinolinol-based metal complexes include 8-quinolinol lithium, tris(8-quinolinolato)aluminum, tris(4-methyl-8-quinolinolato)aluminum, tris(5-methyl-8-quinolinolato)aluminum, tris(3,4-dimethyl-8-quinolinolato)aluminum, tris(4,5-dimethyl-8-quinolinolato)aluminum, tris(4,6-dimethyl-8-quinolinolato)aluminum, bis(2-methyl-8-quinolinolato)(phenolate)aluminum, and bis(2-methyl-8-quinolinolato). 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)(3,5-di-t-butylphenolate)aluminum linolinolate)(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 of suitable bis(2-methyl-4-ethyl-8-quinolinolate)aluminum include 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.

[0431] This quinolinol-based metal complex can be produced using known raw materials and known synthesis methods.

[0432] <Thiazole Derivatives and Benzothiazole Derivatives> The thiazole derivative is, for example, a compound represented by the following formula (ETM-14-1). [ka] The benzothiazole derivative is, for example, a compound represented by the following formula (ETM-14-2). [ka]

[0433] In each formula, φ represents 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-based substituent" and "benzothiazole-based substituent" are substituents in which the pyridyl group in the "pyridine-based substituent" in the above formulae (ETM-2), (ETM-2-1), and (ETM-2-2) is replaced with the below-described thiazole group or benzothiazole group, and at least one hydrogen atom in the thiazole derivative or benzothiazole derivative may be replaced with a deuterium atom. In the following structural formulae, * represents a bonding position. [ka]

[0434] φ is preferably an anthracene ring or a fluorene ring, and in this case, the structure can be as described in the above formula (ETM-2-1) or formula (ETM-2-2), and R 11 ~R 18 The explanation for the above formula (ETM-2-1) or formula (ETM-2-2) can be cited. In addition, in the above formula (ETM-2-1) or formula (ETM-2-2), two pyridine-based substituents are explained as being bonded together, but when these are replaced with a thiazole-based substituent (or a benzothiazole-based substituent), both pyridine-based substituents may be replaced with a thiazole-based substituent (or a benzothiazole-based substituent) (i.e., n=2), or one of the pyridine-based substituents may be replaced with a thiazole-based substituent (or a benzothiazole-based substituent) and the other pyridine-based substituent may be replaced with R 11 ~R 18 (i.e., n=1). Furthermore, for example, R in the above formula (ETM-2-1) 11 ~R 18 At least one of the substituents is replaced with a thiazole-based substituent (or a benzothiazole-based substituent) to form a "pyridine-based substituent" R 11 ~R 18 may be replaced with .

[0435] These thiazole or benzothiazole derivatives can be produced using known raw materials and known synthesis methods.

[0436] <Silole derivatives> The silole derivative is, for example, a compound represented by the following formula (ETM-15), the details of which are described in JP-A-9-194487. [ka]

[0437] X and Y are each independently alkyl, cycloalkyl, alkenyl, alkynyl, alkoxy, alkenyloxy, alkynyloxy, aryl, or heteroaryl, which may be substituted. For details of these groups, the explanations for the above general formulas (1A) and (1B) and the explanation for the above formula (ETM-7-2) can be cited. Furthermore, alkenyloxy and alkynyloxy are groups in which the alkyl moiety in alkoxy is replaced with alkenyl or alkynyl, respectively, and for details of these alkenyls and alkynyls, the explanation for the above formula (ETM-7-2) can be cited. Furthermore, X and Y may be bonded to form a cycloalkyl ring (or a ring in which a portion is unsaturated), and for details of this cycloalkyl ring, the explanation of cycloalkyl in the above general formula (1A) and general formula (1B) can be referred to.

[0438] R 1 ~R 4are each independently hydrogen, halogen, alkyl, cycloalkyl, alkoxy, aryloxy, amino, alkylcarbonyl, arylcarbonyl, alkoxycarbonyl, aryloxycarbonyl, azo group, alkylcarbonyloxy, arylcarbonyloxy, alkoxycarbonyloxy, aryloxycarbonyloxy, sulfinyl, sulfonyl, sulfanyl, silyl, carbamoyl, aryl, heteroaryl, alkenyl, alkynyl, nitro, formyl, nitroso, formyloxy, isocyano, cyanate group, isocyanate group, thiocyanate group, isothiocyanate group, or cyano, which may be substituted with alkyl, cycloalkyl, aryl or halogen, and may form a fused ring with an adjacent substituent.

[0439] R 1 ~R 4 For details of halogen, alkyl, cycloalkyl, alkoxy, aryloxy, amino, aryl, heteroaryl, alkenyl and alkynyl in the above, the explanations for the general formula (1A) and the general formula (1B) can be cited.

[0440] R 1 ~R 4 For details of alkyl, aryl and alkoxy in alkylcarbonyl, arylcarbonyl, alkoxycarbonyl, aryloxycarbonyl, alkylcarbonyloxy, arylcarbonyloxy, alkoxycarbonyloxy and aryloxycarbonyloxy in the above, the explanations in the general formula (1A) and the general formula (1B) can be cited.

[0441] Examples of silyl include a silyl group and a group in which at least one of three hydrogen atoms of the silyl group is independently substituted with an aryl, alkyl, or cycloalkyl, and tri-substituted silyl is preferred, including triarylsilyl, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, alkyldicycloalkylsilyl, etc. For details of the aryl, alkyl, and cycloalkyl in these groups, the explanations for the above general formula (1A) and general formula (1B) can be cited.

[0442] 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 fused rings may contain nitrogen, oxygen, or sulfur atoms in the ring structure, and may be fused with another ring.

[0443] However, preferably, R 1 and R 4 is a phenyl group, X and Y are not alkyl or phenyl. 1 and R 4 When R is a thienyl group, X and Y are alkyl groups, R 2 and R 3 is alkyl, aryl, alkenyl or R 2 and R 3 and R are preferably cycloalkyl groups that do not simultaneously satisfy the condition that R 1 and R 4 When is a silyl group, R 2 , R 3 , X and Y are not each independently hydrogen or alkyl having 1 to 6 carbon atoms. 1 and R 2 In the case of a structure in which a benzene ring is fused with X, X and Y are not alkyl and phenyl.

[0444] These silole derivatives can be produced using known raw materials and known synthesis methods.

[0445] <Azoline derivatives> The azoline derivative is, for example, a compound represented by the following formula (ETM-16), details of which are described in WO 2017 / 014226. [ka]

[0446] 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 is optionally substituted by alkyl having 1 to 6 carbon atoms, cycloalkyl having 3 to 14 carbon atoms, aryl having 6 to 18 carbon atoms, or heteroaryl having 2 to 18 carbon atoms; Y's are each independently -O-, -S-, or >N-Ar, Ar is an aryl having 6 to 12 carbon atoms or a heteroaryl having 2 to 12 carbon atoms, and at least one hydrogen atom of Ar may be substituted with an alkyl having 1 to 4 carbon atoms, a cycloalkyl having 5 to 10 carbon atoms, an aryl having 6 to 12 carbon atoms, or a heteroaryl having 2 to 12 carbon atoms; R 1 ~R 5 are each independently hydrogen, alkyl having 1 to 4 carbon atoms, or cycloalkyl having 5 to 10 carbon atoms, provided that Ar in the >N-Ar and the R 1 ~R 5 one of which is a binding site for L, L's are each 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 are each independently =CR 6 - or =N- and X 1 ~X 6At least two of them are =CR 6 - and X 1 ~X 6 Two of =CR 6 -R in 6 is the bonding site with φ or the azoline ring, and the other =CR 6 -R in 6 is hydrogen, In formula (L-2), X 7 ~X 14 are each independently =CR 6 - or =N- and X 7 ~X 14 At least two of them are =CR 6 - and X 7 ~X 14 Two of =CR 6 -R in 6 is the bonding site with φ or the azoline ring, and the other =CR 6 -R in 6 is hydrogen, at least one hydrogen atom in L may be substituted with alkyl having 1 to 4 carbon atoms, cycloalkyl having 5 to 10 carbon atoms, aryl having 6 to 10 carbon atoms, or heteroaryl having 2 to 10 carbon atoms; m is an integer of 1 to 4, and when m is 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.

[0447] Specific azoline derivatives are compounds represented by the following general formula (ETM-16-1) or (ETM-16-2). [ka] In formula (ETM-16-1) and formula (ETM-16-2), φ is an m-valent group derived from an aromatic hydrocarbon having 6 to 40 carbon atoms or an m-valent group derived from an aromatic heterocycle having 2 to 40 carbon atoms, and at least one hydrogen atom of φ is optionally substituted by alkyl having 1 to 6 carbon atoms, cycloalkyl having 3 to 14 carbon atoms, aryl having 6 to 18 carbon atoms, or heteroaryl having 2 to 18 carbon atoms; In formula (ETM-16-1), each Y is independently -O-, -S-, or >N-Ar, Ar is an aryl having 6 to 12 carbon atoms or a heteroaryl having 2 to 12 carbon atoms, and at least one hydrogen atom of Ar is optionally substituted with an alkyl having 1 to 4 carbon atoms, a cycloalkyl having 5 to 10 carbon atoms, an aryl having 6 to 12 carbon atoms, or a heteroaryl having 2 to 12 carbon atoms; In formula (ETM-16-1), R 1 ~R 4 are each independently hydrogen, alkyl having 1 to 4 carbon atoms, or cycloalkyl having 5 to 10 carbon atoms, provided that R 1 and R 2 are identical, and R 3 and R 4 are identical, In formula (ETM-16-2), R 1 ~R 5 are each independently hydrogen, alkyl having 1 to 4 carbon atoms, or cycloalkyl having 5 to 10 carbon atoms, provided that R 1 and R 2 are identical, and R 3 and R 4 are identical, In formula (ETM-16-1) and formula (ETM-16-2), L's are each 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 are each independently =CR 6 - or =N- and X 1 ~X 6 At least two of them are =CR 6 - and X1 ~X 6 Two of =CR 6 -R in 6 is the bonding site with φ or the azoline ring, and the other =CR 6 -R in 6 is hydrogen, In formula (L-2), X 7 ~X 14 are each independently =CR 6 - or =N- and X 7 ~X 14 At least two of them are =CR 6 - and X 7 ~X 14 Two of =CR 6 -R in 6 is the bonding site with φ or the azoline ring, and the other =CR 6 -R in 6 is hydrogen, at least one hydrogen atom in L may be substituted with alkyl having 1 to 4 carbon atoms, cycloalkyl having 5 to 10 carbon atoms, aryl having 6 to 10 carbon atoms, or heteroaryl having 2 to 10 carbon atoms; m is an integer of 1 to 4, and when m is 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.

[0448] Preferably, φ is selected from the group consisting of monovalent groups represented by the following formulas (φ1-1) to (φ1-18), divalent groups represented by the following formulas (φ2-1) to (φ2-34), trivalent groups represented by the following formulas (φ3-1) to (φ3-3), and tetravalent groups represented by the following formulas (φ4-1) to (φ4-2), and at least one hydrogen atom of φ may be substituted with alkyl having 1 to 6 carbon atoms, cycloalkyl having 3 to 14 carbon atoms, aryl having 6 to 18 carbon atoms, or heteroaryl having 2 to 18 carbon atoms. * in the following structural formulas indicates a bonding position. [ka] [ka] [ka] Z in the above formula is >CR2, >N-Ar, >NL, -O-, or -S-; each R in >CR2 is independently alkyl having 1 to 4 carbon atoms, cycloalkyl having 5 to 10 carbon atoms, aryl having 6 to 12 carbon atoms, or heteroaryl having 2 to 12 carbon atoms; R may be bonded to each other to form a ring; Ar in >N-Ar is aryl having 6 to 12 carbon atoms or heteroaryl having 2 to 12 carbon atoms; and L in >NL is L in the above general formula (ETM-16), formula (ETM-16-1), or general formula (ETM-16-2).

[0449] Preferably, L is a divalent ring group selected from the group consisting of benzene, naphthalene, pyridine, pyrazine, pyrimidine, pyridazine, triazine, quinoline, isoquinoline, naphthyridine, phthalazine, quinoxaline, quinazoline, cinnoline, and pteridine, and at least one hydrogen atom of L may be substituted with alkyl having 1 to 4 carbon atoms, cycloalkyl having 5 to 10 carbon atoms, aryl having 6 to 10 carbon atoms, or heteroaryl having 2 to 10 carbon atoms.

[0450] Preferably, Ar in >N-Ar as Y or Z is selected from the group consisting of phenyl, naphthyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, naphthyridinyl, phthalazinyl, quinoxalinyl, quinazolinyl, cinnolinyl, and pteridinyl, and at least one hydrogen atom of Ar in >N-Ar as Y may be substituted with alkyl having 1 to 4 carbon atoms, cycloalkyl having 5 to 10 carbon atoms, or aryl having 6 to 10 carbon atoms.

[0451] Preferably, R 1 ~R 4 are each independently hydrogen, alkyl having 1 to 4 carbon atoms, or cycloalkyl having 5 to 10 carbon atoms, provided that R1 and R 2 are identical, and R 3 and R 4 are identical, and R 1 ~R 4 are not all hydrogen atoms at the same time, and m is 1 or 2. When m is 2, the groups formed by the azoline ring and L are the same.

[0452] Specific examples of azoline derivatives include the following compounds: In the structural formula, "Me" represents a methyl group. [ka] [ka]

[0453] More preferably, φ is selected from the group consisting of divalent groups represented by the following formulae (φ2-1), (φ2-31), (φ2-32), (φ2-33), and (φ2-34), wherein at least one hydrogen atom of φ may be substituted with an aryl having 6 to 18 carbon atoms, and * in each structural formula represents a bonding 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 atom of L is optionally substituted with alkyl having 1 to 4 carbon atoms, cycloalkyl having 5 to 10 carbon atoms, aryl having 6 to 10 carbon atoms, or heteroaryl having 2 to 14 carbon atoms; Ar in >N-Ar as Y is selected from the group consisting of phenyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, and triazinyl, and at least one hydrogen of Ar may be substituted with alkyl having 1 to 4 carbon atoms, cycloalkyl having 5 to 10 carbon atoms, or aryl having 6 to 10 carbon atoms; R 1 ~R 4are each independently hydrogen, alkyl having 1 to 4 carbon atoms, or cycloalkyl having 5 to 10 carbon atoms, provided that R 1 and R 2 are identical, and R 3 and R 4 are identical, and R 1 ~R 4 cannot all become hydrogen at the same time, and m is 2, and the groups formed by the azoline ring and L are the same.

[0454] Other specific examples of azoline derivatives include the following compounds: In the structural formula, "Me" represents a methyl group. [ka]

[0455] For details of the alkyl, cycloalkyl, aryl or heteroaryl in the above formulas defining this azoline derivative, the explanations for the above general formula (1A) and general formula (1B) can be cited.

[0456] This azoline derivative can be produced using known raw materials and known synthesis methods.

[0457] The electron transport layer or the electron injection layer may further contain a substance capable of reducing the material forming the electron transport layer or the electron injection layer. Various substances can be used as this reducing substance as long as they have a certain level of reducing ability. 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.

[0458] Preferred reducing substances include alkali metals such as Na (work function 2.36 eV), K (2.28 eV), Rb (2.16 eV), and Cs (1.95 eV), and alkaline earth metals such as Ca (2.9 eV), Sr (2.0-2.5 eV), and Ba (2.52 eV), with substances with a work function of 2.9 eV or less being particularly preferred. Among these, more preferred reducing substances are alkali metals such as K, Rb, and Cs, with Rb or Cs being even more preferred, and Cs being the most preferred. These alkali metals have particularly high reducing ability, and adding a relatively small amount of these to the material forming the electron transport layer or electron injection layer can improve the luminance and extend the life of the organic EL device. Furthermore, as a reducing substance having a work function of 2.9 eV or less, a combination of two or more of these alkali metals is also preferred, and in particular, a combination containing Cs is preferred, such as a combination of Cs and Na, Cs and K, Cs and Rb, or Cs, Na and K. By including Cs, the reducing ability can be efficiently exerted, and by adding Cs to the material forming the electron transport layer or electron injection layer, the luminance of the organic EL device can be improved and the lifetime can be extended.

[0459] The above-mentioned electron injection layer material and electron transport layer material can also be used as electron layer materials in the form of polymer compounds obtained by polymerizing a reactive compound substituted with a reactive substituent as a monomer, or a crosslinked polymer thereof, or a pendant polymer compound obtained by reacting a main-chain polymer with the reactive compound, or a crosslinked pendant polymer thereof. Regarding the reactive substituent in this case, the explanation for the polycyclic aromatic compound represented by the above general formula (1A) or (1B) can be cited. The uses of such polymer compounds and crosslinked polymers will be described in detail below.

[0460] <Cathode in organic electroluminescent device> The cathode 108 serves to inject electrons into the light-emitting layer 105 through the electron injection layer 107 and the electron transport layer 106 .

[0461] The material for the cathode 108 is not particularly limited as long as it can efficiently inject electrons into the organic layer, but materials similar to those for 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 alloys thereof (e.g., magnesium-silver alloys, magnesium-indium alloys, and aluminum-lithium alloys such as lithium fluoride / aluminum alloys), are preferred. To increase electron injection efficiency and improve device characteristics, lithium, sodium, potassium, cesium, calcium, magnesium, or alloys containing these low-work-function metals are effective. However, these low-work-function metals are generally unstable in air. To address this issue, a method has been proposed in which a trace amount of lithium, cesium, or magnesium is doped into the organic layer to create a highly stable electrode. Other dopants that can be used include inorganic salts such as lithium fluoride, cesium fluoride, lithium oxide, and cesium oxide. However, these are not limited to these.

[0462] Further, for electrode protection, preferred examples include lamination of metals such as platinum, gold, silver, copper, iron, tin, aluminum, and indium, or alloys using these metals, inorganic substances such as silica, titania, and silicon nitride, polyvinyl alcohol, vinyl chloride, hydrocarbon polymer compounds, etc. The method for producing these electrodes is not particularly limited as long as electrical conduction can be achieved, and may be resistance heating, electron beam evaporation, sputtering, ion plating, coating, or the like.

[0463] <Binders that may be used in each layer> The materials used for the hole injection layer, hole transport layer, light-emitting layer, electron transport layer, and electron injection layer can be used alone to form each layer, but they can also be dispersed as a polymer binder 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, polyamide, ethyl cellulose, vinyl acetate resin, ABS resin, and polyurethane resin, or curable resins such as phenol resin, xylene resin, petroleum resin, urea resin, melamine resin, unsaturated polyester resin, alkyd resin, epoxy resin, and silicone resin.

[0464] <Method for producing organic electroluminescent device> Each layer constituting an organic EL device can be formed by forming the material to be formed into a thin film using methods such as vapor deposition, resistance heating vapor deposition, electron beam vapor deposition, sputtering, molecular lamination, printing, spin coating or casting, and coating. There are no particular limitations on the film thickness of each layer formed in this way, and it can be set appropriately depending on the properties of the material, but it is usually in the range of 2 nm to 5000 nm. The film thickness can usually be measured with a quartz oscillator film thickness measuring device or the like. When forming a thin film using vapor deposition, the vapor deposition conditions vary depending on the type of material, the desired crystal structure and association structure of the film, etc. Vapor deposition conditions are generally a boat heating temperature of +50 to +400°C, a vacuum degree of 10 -6 ~10 -3 It is preferable to appropriately set the pressure, the deposition rate, the substrate temperature, and the film thickness in the range of 0.01 to 50 nm / sec, -150 to +300° C., and 2 nm to 5 μm.

[0465] When applying a DC voltage to the organic EL element obtained in this way, the anode should be set to + and the cathode to -. When a voltage of about 2 to 40 V is applied, light emission can be observed from the transparent or semi-transparent electrode side (anode or cathode, or both). This organic EL element also emits light when a pulse current or an AC current is applied. The waveform of the applied AC current can be any waveform.

[0466] Next, as an example of a method for producing an organic EL element, a method for producing an organic EL element comprising an anode, a hole injection layer, a hole transport layer, an emitting layer composed of a host material and a dopant material, an electron transport layer, an electron injection layer, and a cathode will be described.

[0467] <Vapor deposition method> An anode is prepared by forming a thin film of an anode material on a suitable substrate by vapor deposition or the like, and then forming thin films of a hole injection layer and a hole transport layer on the anode. A host material and a dopant material are co-deposited on the anode to form a thin film to serve as an emissive layer. An electron transport layer and an electron injection layer are then formed on the emissive layer, and a thin film of a cathode material is then formed by vapor deposition or the like to serve as a cathode, thereby obtaining the desired organic EL device. It is also possible to reverse the order of fabrication of the organic EL device described above, by fabricating the layers in the order of cathode, electron injection layer, electron transport layer, emissive layer, hole transport layer, hole injection layer, and anode.

[0468] <Wet film formation method> The wet film formation method is carried out by preparing a liquid organic layer-forming composition from a low molecular weight compound capable of forming each organic layer of an organic EL device, and using this. If there is no suitable organic solvent that can dissolve this low molecular weight compound, the organic layer-forming composition may be prepared from a reactive compound obtained by substituting a reactive substituent on the low molecular weight compound, such as another monomer having a solubility function as a reactive compound, or a polymer compound polymerized together with a main-chain polymer.

[0469] In wet film formation, a coating film is generally formed through a coating step in which an organic layer-forming composition is applied to a substrate and a drying step in which the solvent is removed from the applied organic layer-forming composition. When the polymer compound has a crosslinkable substituent (also called a crosslinkable polymer compound), the drying step further crosslinks the polymer to form a crosslinked polymer. Depending on the coating process, methods using a spin coater are called spin coating methods; methods using a slit coater are called slit coating methods; methods using a printing plate are called gravure, offset, reverse offset, or flexographic printing methods; methods using an inkjet printer are called inkjet methods; and methods spraying the composition in a mist are called spray methods. Drying methods include air drying, heating, and vacuum drying. The drying process may be performed once or multiple times using different methods and conditions. Different methods, such as baking under reduced pressure, may also be used in combination.

[0470] Wet film formation methods are film formation methods that use solutions, such as some printing methods (inkjet methods), spin coating or casting methods, and coating methods. Unlike vacuum deposition methods, wet film formation methods do not require expensive vacuum deposition equipment and can form films under atmospheric pressure. In addition, wet film formation methods allow for large-area and continuous production, which leads to reduced manufacturing costs.

[0471] On the other hand, compared to vacuum deposition, wet deposition can be difficult to layer. When using wet deposition to create layered films, it is necessary to prevent the dissolution of the lower layer by the composition of the upper layer, and methods such as controlled solubility compositions, crosslinking of the lower layer, and orthogonal solvents (solvents that are not soluble in each other) are used. However, even with these techniques, it can be difficult to use wet deposition for all film application.

[0472] Therefore, a common method for fabricating organic EL devices is to use a wet film-forming method for only some layers and a vacuum deposition method for the remaining layers.

[0473] For example, the procedure for producing an organic EL element by partially applying a wet film formation method is shown below. (Step 1) Formation of the anode by vacuum deposition (Step 2) Forming a film by a wet film formation method using a composition for forming a hole injection layer containing a material for the hole injection layer (Step 3) Forming a film by a wet film formation method using a composition for forming a hole transport layer containing a material for the hole transport layer (Step 4) Forming a film by a wet film formation method using a composition for forming an emitting layer containing a host material and a dopant material (Step 5) Formation of the electron transport layer by vacuum deposition (Step 6) Formation of the electron injection layer by vacuum deposition (Step 7) Cathode deposition by vacuum evaporation Through this procedure, an organic EL element consisting of an anode, a hole injection layer, a hole transport layer, a light-emitting layer made of a host material and a dopant material, an electron transport layer, an electron injection layer, and a cathode is obtained. Of course, if there is a means for preventing dissolution of the underlying light-emitting layer, or if a means for forming a film from the cathode side in the reverse of the above procedure is used, a layer-forming composition containing a material for the electron transport layer and a material for the electron injection layer can be prepared, and the layer can be formed by a wet film-forming method.

[0474] <Other film formation methods> The organic layer-forming composition can be formed into a film by laser thermal imaging (LITI), a method in which a compound attached to a substrate is heated and vapor-deposited with a laser, and the organic layer-forming composition can be used as the material applied to the substrate.

[0475] <Optional process> Before and after each film-forming step, appropriate treatment steps, cleaning steps, and drying steps may be added as appropriate. Examples of treatment steps include exposure treatment, plasma surface treatment, ultrasonic treatment, ozone treatment, cleaning treatment using an appropriate solvent, and heat treatment. Furthermore, a series of steps for preparing a bank may also be included.

[0476] Photolithography can be used to fabricate the banks. Positive and negative resist materials can be used as bank materials for photolithography. Patternable printing methods such as inkjet printing, gravure offset printing, reverse offset printing, and screen printing can also be used. In these cases, permanent resist materials can also be used.

[0477] Materials that can be used for banks include, but are not limited to, polysaccharides and their derivatives, homopolymers and copolymers of hydroxyl-containing ethylenic monomers, biopolymers, polyacryloyl compounds, polyesters, polystyrenes, polyimides, polyamideimides, polyetherimides, polysulfides, polysulfones, polyphenylenes, polyphenyl ethers, polyurethanes, epoxy (meth)acrylates, melamine (meth)acrylates, polyolefins, cyclic polyolefins, acrylonitrile-butadiene-styrene copolymers (ABS), silicone resins, polyvinyl chloride, chlorinated polyethylene, chlorinated polypropylene, polyacetate, polynorbornene, synthetic rubbers, fluorinated polymers such as polyfluorovinylidene, polytetrafluoroethylene, and polyhexafluoropropylene, copolymers of fluoroolefins and hydrocarbonolefins, and fluorocarbon polymers.

[0478] <Composition for forming organic layer used in wet film formation method> The organic layer-forming composition is obtained by dissolving a low-molecular-weight compound capable of forming each organic layer of an organic EL device, or a polymer compound obtained by polymerizing such a low-molecular-weight compound, in an organic solvent. For example, the light-emitting layer-forming composition contains at least one polycyclic aromatic compound (or a polymer compound thereof) as a dopant material as a first component, at least one host material as a second component, and at least one organic solvent as a third component. The first component functions as a dopant component for the light-emitting layer obtained from the composition, and the second component functions as a host component for the light-emitting layer. The third component functions as a solvent that dissolves the first and second components in the composition, and upon application, the controlled evaporation rate of the third component itself provides a smooth and uniform surface profile.

[0479] <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, it is possible to control and improve film-forming properties, the presence or absence of defects in the coating film, surface roughness, and smoothness. Furthermore, when forming a film using an inkjet method, it is possible to control meniscus stability at the pinhole of the inkjet head and control and improve ejection properties. In addition, by controlling the drying rate of the film and the orientation of the derivative molecules, it is possible to improve the electrical properties, luminescence properties, efficiency, and lifespan of an organic EL device having an organic layer obtained from the organic layer-forming composition.

[0480] (1) Physical properties of organic solvents The boiling point of the 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 preferred from the viewpoint of inkjet dischargeability. A boiling point lower than 300°C is preferred from the viewpoints of coating film defects, surface roughness, residual solvent, and smoothness. From the viewpoints of good inkjet dischargeability, film-forming properties, smoothness, and low residual solvent, it is more preferred that the organic solvent contains two or more organic solvents. Meanwhile, in some cases, taking into consideration transportability, etc., the composition may be in a solid state obtained by removing the solvent from the composition for forming the organic layer.

[0481] Furthermore, the organic solvent contains a good solvent (GS) and a poor solvent (PS) for at least one of the solutes, and the boiling point (BP) of the good solvent (GS) is GS ) is the boiling point (BP) of the poor solvent (PS) PS ) is particularly preferred. By adding a high-boiling poor solvent, the low-boiling good solvent evaporates first during film formation, increasing the concentration of the ingredients in the composition and the concentration of the poor solvent, facilitating rapid film formation. This results in a coating with few defects, minimal surface roughness, and high smoothness.

[0482] Difference in solubility (S GS -S PS The difference in boiling point (BP) is preferably 1% or more, more preferably 3% or more, and even more preferably 5% or more. PS -BP GS ) is preferably 10°C or higher, more preferably 30°C or higher, and even more preferably 50°C or higher.

[0483] After film formation, the organic solvent is removed from the coating film by a drying process such as vacuum, reduced pressure, or heating. When heating is performed, from the viewpoint of improving coating film-forming properties, it is preferable to perform the heating at a temperature not higher than 30°C above the glass transition temperature (Tg) of at least one of the solutes. Furthermore, from the viewpoint of reducing residual solvent, it is preferable to perform the heating at a temperature not lower than 30°C below the glass transition temperature (Tg) of at least one of the solutes. Even if the heating temperature is lower than the boiling point of the organic solvent, the organic solvent can be sufficiently removed because the film is thin. Furthermore, drying may be performed multiple times at different temperatures, or multiple drying methods may be used in combination.

[0484] (2) Specific examples of organic solvents Examples of organic solvents used in the organic layer-forming composition include alkylbenzene solvents, phenyl ether solvents, alkyl ether solvents, cyclic ketone solvents, aliphatic ketone solvents, monocyclic ketone solvents, solvents having a diester skeleton, and fluorine-containing solvents. Specific examples include pentanol, hexanol, heptanol, octanol, nonanol, decanol, undecanol, dodecanol, tetradecanol, hexane-2-ol, heptan-2-ol, octan-2-ol, decan-2-ol, dodecan-2-ol, cyclohexanol, Sanol, α-terpineol, β-terpineol, γ-terpineol, δ-terpineol, terpineol (mixture), ethylene glycol monomethyl ether acetate, propylene glycol monomethyl ether acetate, diethylene glycol dimethyl ether, dipropylene glycol dimethyl ether, diethylene glycol ethyl methyl ether, diethylene glycol isopropyl methyl ether, dipropylene glycol monomethyl ether, diethylene glycol diethyl ether, diethylene glycol monomethyl ether , diethylene glycol butyl methyl ether, tripropylene glycol dimethyl ether, triethylene glycol dimethyl ether, diethylene glycol monobutyl ether, ethylene glycol monophenyl ether, triethylene glycol monomethyl ether, diethylene glycol dibutyl ether, triethylene glycol butyl methyl ether, polyethylene glycol dimethyl ether, tetraethylene glycol dimethyl ether, p-xylene, m-xylene, o-xylene, 2,6-lutidine, 2-fluoro-m-xylene, 3-fluoro-o-xylene, 2-chlorobenzotrifluoride, cumene, toluene, 2-chloro-6-fluorotoluene, 2-fluoroanisole, anisole, 2,3-dimethylpyrazine, bromobenzene, 4-fluoroanisole, 3-fluoroanisole, 3-trifluoromethylanisole, mesitylene, 1,2,4-trimethylbenzene, t-butylbenzene, 2-methylanisole, phenetole, benzodioxole, 4-methylanisole, s-butylbenzene, 3-methylanisole, 4-fluoro-3-methylanisole, cymene, 1,2,3-Trimethylbenzene, 1,2-dichlorobenzene, 2-fluorobenzonitrile, 4-fluoroveratrol, 2,6-dimethylanisole, n-butylbenzene, 3-fluorobenzonitrile, decalin (decahydronaphthalene), neopentylbenzene, 2,5-dimethylanisole, 2,4-dimethylanisole, benzonitrile, 3,5-dimethylanisole, diphenyl ether, 1-fluoro-3,5-dimethoxybenzene, methyl benzoate, isopentylbenzene, 3,4-dimethylanisole, o-tolunitrile, n-amylbenzene, veratrol, 1,2,3,4-tetrahydronaphthalene, ethyl benzoate, n-hexylbenzene, propyl benzoate, cyclohexylbenzene, 1-methyl Examples of the solvent include, but are not limited to, methylnaphthalene, butyl benzoate, 2-methylbiphenyl, 3-phenoxytoluene, 2,2'-bitolyl, dodecylbenzene, dipentylbenzene, tetramethylbenzene, trimethoxybenzene, trimethoxytoluene, 2,3-dihydrobenzofuran, 1-methyl-4-(propoxymethyl)benzene, 1-methyl-4-(butyloxymethyl)benzene, 1-methyl-4-(pentyloxymethyl)benzene, 1-methyl-4-(hexyloxymethyl)benzene, 1-methyl-4-(heptyloxymethyl)benzene, benzyl butyl ether, benzyl pentyl ether, benzyl hexyl ether, benzyl heptyl ether, and benzyl octyl ether. The solvent may be used alone or in combination.

[0485] <Optional ingredients> The organic layer-forming composition may contain optional components such as a binder and a surfactant, provided that the optional components do not impair the properties of the organic layer-forming composition.

[0486] (1) Binder The organic layer-forming composition may contain a binder. The binder not only forms a film during film formation but also bonds the resulting film to a substrate. The binder also plays a role in dissolving, dispersing, and binding other components in the organic layer-forming composition.

[0487] Examples of binders used in the organic layer-forming composition include, but are not limited to, acrylic resins, polyethylene terephthalate, ethylene-vinyl acetate copolymers, ethylene-vinyl alcohol copolymers, acrylonitrile-ethylene-styrene copolymer (AES) resins, ionomers, chlorinated polyethers, diallyl phthalate resins, unsaturated polyester resins, polyethylene, polypropylene, polyvinyl chloride, polyvinylidene chloride, polystyrene, polyvinyl acetate, Teflon, acrylonitrile-butadiene-styrene copolymer (ABS) resins, acrylonitrile-styrene copolymer (AS) resins, phenolic resins, epoxy resins, melamine resins, urea resins, alkyd resins, polyurethanes, and copolymers of the above resins and polymers.

[0488] The binder used in the organic layer-forming composition may be one type only, or a mixture of two or more types may be used.

[0489] (2) Surfactants The organic layer-forming composition may contain a surfactant, for example, to control the film surface uniformity, solvent affinity, and liquid repellency of the organic layer-forming composition. Surfactants are classified into ionic and nonionic based on the structure of their hydrophilic group, and further classified into alkyl, silicon, and fluorine-based based on the structure of their hydrophobic group. Furthermore, based on their molecular structure, they are classified into monomolecular systems with relatively small and simple molecular weights and polymer systems with large molecular weights and side chains or branches. Based on their composition, they are classified into single systems and mixed systems containing two or more surfactants and base materials. All types of surfactants can be used in the organic layer-forming composition.

[0490] Examples of surfactants include Polyflow No. 45, Polyflow KL-245, Polyflow No. 75, Polyflow No. 90, and Polyflow No. 95 (trade names, manufactured by Kyoeisha Chemical Industry Co., Ltd.), Disperbyk 161, Disperbyk 162, Disperbyk 163, Disperbyk 164, Disperbyk 166, Disperbyk 170, Disperbyk 180, Disperbyk 181, Disperbyk 182, BYK300, and BYK 306, BYK310, BYK320, BYK330, BYK342, BYK344, BYK346 (trade names, manufactured by BYK Japan Co., Ltd.), KP-341, KP-358, KP-368, KF-96-50CS, KF-50-100CS (trade names, manufactured by Shin-Etsu Chemical Co., Ltd.), Surflon SC-101, Surflon KH-40 (trade names, manufactured by Seimi Chemical Co., Ltd.), Ftergent 222F, Ftergent 251, FTX-218 (trade names, manufactured by Neos Co., Ltd.), EFTOP EF-351, EFTOP EF-352, EFTOP EF-601, EFTOP EF-801, EFTOPEF-802 (trade 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 (trade name, manufactured by DIC Corporation), fluoroalkylbenzenesulfonates, fluoroalkylcarboxylates, fluoroalkylpolyoxyethylene ethers, fluoroalkylammonium iodides, fluoroalkylbetaines, fluoroalkylsulfonates, diglycerin tetrakis(fluoroalkylpolyoxyethylene ether), fluoroalkyltrimethylammonium salts, fluoroalkylaminosulfonates, polyoxyethylene nonyl phenyl 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, alkyl benzene sulfonate and alkyl diphenyl ether disulfonate can be mentioned.

[0491] The surfactant may be used alone or in combination of two or more.

[0492] <Composition and Properties of the Organic Layer-Forming Composition> The content of each component in the composition for forming an organic layer is determined taking into consideration the good solubility, storage stability, and film-forming properties of each component in the composition for forming an organic layer, the good film quality of the coating film obtained from the composition for forming an organic layer, the good dischargeability when using an inkjet method, and the good electrical properties, light-emitting properties, efficiency, and lifespan of an organic EL device having an organic layer produced using the composition. For example, in the case of a composition for forming an emitting layer, the first component is preferably 0.0001% to 2.0% by weight, the second component is preferably 0.0999% to 8.0% by weight, and the third component is preferably 90.0% to 99.9% by weight, based on the total weight of the composition for forming an emitting layer.

[0493] More preferably, the first component is 0.005% by weight to 1.0% by weight, the second component is 0.095% by weight to 4.0% by weight, and the third component is 95.0% by weight to 99.9% by weight, based on the total weight of the composition for forming the light-emitting layer. Even more preferably, the first component is 0.05% by weight to 0.5% by weight, the second component is 0.25% by weight to 2.5% by weight, and the third component is 97.0% by weight to 99.7% by weight, based on the total weight of the composition for forming the light-emitting layer.

[0494] The composition for forming an organic layer can be produced by appropriately selecting the above-mentioned components by a known method, such as stirring, mixing, heating, cooling, dissolving, dispersing, etc. After preparation, the composition may be appropriately subjected to filtration, degassing (also called degassing), ion exchange treatment, inert gas substitution / filling treatment, etc.

[0495] The higher the viscosity of the composition for forming an organic layer, the better the film-forming properties and the better the ejection properties when using an inkjet method. On the other hand, the lower the viscosity, the easier it is to form a thin film. For this reason, the viscosity of the composition for forming an organic layer at 25°C is preferably 0.3 to 3 mPa·s, and more preferably 1 to 3 mPa·s. In the present invention, the viscosity is a value measured using a cone-plate type rotational viscometer (cone-plate type).

[0496] The lower the surface tension of the composition for forming an organic layer, the better the film-forming properties and the defect-free coating film will be. On the other hand, the higher the surface tension, the better the ink-jet ejection properties will be. For this reason, the viscosity of the composition for forming an organic layer is such that the surface tension at 25°C is preferably 20 to 40 mN / m, more preferably 20 to 30 mN / m. In the present invention, the surface tension is a value measured using the hanging drop method.

[0497] <Crosslinkable polymer compound: Compound represented by general formula (XLP-1)> Next, the case where the above-mentioned polymer compound has a crosslinkable substituent will be described. Such a crosslinkable polymer compound is, for example, a compound represented by the following general formula (XLP-1). [ka] In formula (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 the monovalent or divalent aromatic compound having a crosslinkable substituent is 0.1 to 80 wt % in the molecule.

[0498] The content of the monovalent or divalent aromatic compound having a crosslinkable substituent is preferably 0.5 to 50% by weight, more preferably 1 to 20% by weight.

[0499] The crosslinkable substituent (XLS) is not particularly limited as long as it is a group that can further crosslink the above-mentioned polymer compound, but substituents having the following structures are preferred: * in each structural formula indicates the bonding position. [ka]

[0500] L's are each independently a single bond, -O-, -S-, >C=O, -OC(=O)-, alkylene having 1 to 12 carbon atoms, oxyalkylene having 1 to 12 carbon atoms, and polyoxyalkylene having 1 to 12 carbon atoms. Among the above substituents, groups represented by formula (XLS-1), formula (XLS-2), formula (XLS-3), formula (XLS-9), formula (XLS-10) or formula (XLS-17) are preferred, and groups represented by formula (XLS-1), formula (XLS-3) or formula (XLS-17) are more preferred.

[0501] Examples of divalent aromatic compounds having a crosslinkable substituent include compounds having the following partial structures: In the following structural formula, * represents a bonding position. [ka] [ka] [ka] [ka]

[0502] <Methods of producing polymer compounds and crosslinkable polymer compounds> The methods for producing the polymer compound and the crosslinkable polymer compound will be described using the compound represented by the above formula (H3) and the compound represented by formula (XLP-1) as examples. These compounds can be synthesized by appropriately combining known production methods.

[0503] Examples of the solvent used in the reaction include aromatic solvents, saturated / unsaturated hydrocarbon solvents, alcohol solvents, and ether solvents, such as dimethoxyethane, 2-(2-methoxyethoxy)ethane, and 2-(2-ethoxyethoxy)ethane.

[0504] The reaction may also be carried out in a two-phase system, in which case a phase transfer catalyst such as a quaternary ammonium salt may be added as necessary.

[0505] The compounds of formula (H3) and formula (XLP-1) can be produced in a single step or multiple steps. Furthermore, they can be produced by batch polymerization, in which all raw materials are placed in a reaction vessel and the reaction is initiated; by dropwise addition of raw materials to a reaction vessel; or by precipitation polymerization, in which the product precipitates as the reaction progresses. These methods can be combined as appropriate. For example, when synthesizing a compound represented by formula (H3) in a single step, the target product is obtained by adding a monomer unit (MU) and an end-capping unit (EC) to a reaction vessel and then carrying out the reaction. Furthermore, when synthesizing a 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, then adding the end-capping unit (EC) and carrying out the reaction. By adding different types of monomer units (MU) and carrying out the reaction in multiple steps, a polymer with a concentration gradient of the monomer unit structure can be produced. Furthermore, after preparing a precursor polymer, the target polymer can be obtained by subsequent reaction.

[0506] Furthermore, the primary structure of the polymer can be controlled by selecting the polymerizable group of the monomer unit (MU). For example, as shown in Synthesis Schemes 1 to 3, it is possible to synthesize a polymer with a random primary structure (Synthetic Scheme 1) or a polymer with a regular primary structure (Synthetic Schemes 2 and 3), and these can be combined appropriately depending on the target product. Furthermore, by using a monomer unit with three or more polymerizable groups, it is possible to synthesize hyperbranched polymers and dendrimers. [ka]

[0507] The monomer unit that can be used in the present invention is described in JP 2010-189630 A, WO 2012 / 086671, WO 2013 / 191088, WO 2002 / 045184, WO 2011 / 049241, WO 2013 / 146806, WO 2005 / 049546, WO 2015 / 145871, JP 2010-215886 A, JP 2008-106241 A, WO 2016 / 031639, and JP 2011-174062 A. It can be synthesized in accordance with the method described therein.

[0508] Further, specific polymer synthesis procedures are described in JP 2012-036388 A, WO 2015 / 008851 A, JP 2012-36381 A, JP 2012-144722 A, WO 2015 / 194448 A, WO 2013 / 146806 A, WO 2015 / 145871 A, WO 2016 / 031639 A, WO 2016 / 125560 A, and WO 2011 / 049241 A. It can be synthesized in accordance with the methods described therein.

[0509] <Application examples of organic electroluminescent devices> The present invention can also be applied to a display device equipped with an organic EL element or a lighting device equipped with an organic EL element. A display device or lighting device including an organic EL element can be manufactured by a known method, for example, by connecting the organic EL element according to this embodiment to a known driving device, and can be driven appropriately using a known driving method such as DC driving, pulse driving, or AC driving.

[0510] 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, JP-A-10-335066, JP-A-2003-321546, and JP-A-2004-281086). Examples of display methods include matrix and segment methods. Note that matrix display and segment display may coexist on the same panel.

[0511] In a matrix display, pixels are arranged two-dimensionally, such as in a grid or mosaic pattern, and a collection of pixels displays characters and images. The shape and size of the pixels are determined by the application. For example, images and text displayed on computers, monitors, and televisions typically use square pixels with sides of 300 μm or less. Large displays such as display panels use pixels on the order of millimeters. For monochrome displays, pixels of the same color are simply arranged, while for color displays, red, green, and blue pixels are displayed side by side. These types are typically known as delta and stripe types. The matrix can be driven by either line-sequential or active matrix methods. While line-sequential driving has the advantage of being simpler, active matrix methods can sometimes be superior in terms of operating characteristics, so the choice must be made based on the application.

[0512] In the segment type, a pattern is formed to display predetermined information, and a predetermined area is illuminated. Examples include the time and temperature displays on digital clocks and thermometers, the operating status displays on audio equipment and induction cookers, and panel displays on automobiles.

[0513] Examples of lighting devices include lighting devices for indoor lighting and backlights for liquid crystal display devices (see, for example, JP 2003-257621 A, JP 2003-277741 A, JP 2004-119211 A, etc.). Backlights are primarily used to improve the visibility of non-self-luminous display devices, and are used in liquid crystal display devices, clocks, audio devices, automobile panels, display boards, signs, etc. In particular, for backlights of liquid crystal display devices, particularly those used for personal computers, where thinning is an issue, considering that conventional methods use fluorescent lamps and light guide plates and therefore make thinning difficult, backlights using the light-emitting elements according to this embodiment are characterized by their thinness and light weight.

[0514] 3-2. Other organic devices The polycyclic aromatic compound according to the present invention can be used to produce not only the above-mentioned organic electroluminescent device but also an organic field effect transistor, an organic thin-film solar cell, a wavelength conversion filter, or the like.

[0515] An organic field-effect transistor is a transistor that controls current by an electric field generated by voltage input, and has a gate electrode in addition to a source electrode and a drain electrode. When a voltage is applied to the gate electrode, an electric field is generated, and the transistor can control the current by arbitrarily blocking the flow of electrons (or holes) flowing between the source and drain electrodes. Field-effect transistors are easier to miniaturize than simple transistors (bipolar transistors), and are often used as elements that make up integrated circuits.

[0516] The structure of an organic field effect transistor is usually such that a source electrode and a drain electrode are provided in contact with an organic semiconductor active layer formed using the polycyclic aromatic compound according to the present invention, and a gate electrode is provided sandwiching an insulating layer (dielectric layer) in contact with the organic semiconductor active layer. Examples of the device structure include the following structures. (1) Substrate / gate electrode / insulating layer / source and drain electrodes / organic semiconductor active layer (2) Substrate / gate electrode / insulating layer / organic semiconductor active layer / source electrode / drain electrode (3) Substrate / organic semiconductor active layer / source electrode / drain electrode / insulator layer / gate electrode (4) Substrate / source electrode / drain electrode / organic semiconductor active layer / insulator layer / gate electrode The organic field effect transistor configured in this manner can be used as a pixel driving switching element for an active matrix driving liquid crystal display or an organic electroluminescence display.

[0517] An organic thin-film solar cell has a structure in which an anode such as ITO, a hole transport layer, a photoelectric conversion layer, an electron transport layer, and a cathode are laminated on a transparent substrate such as glass. The photoelectric conversion layer has a p-type semiconductor layer on the anode side and an n-type semiconductor layer on the cathode side. The polycyclic aromatic compound according to the present invention can be used as a material for the hole transport layer, p-type semiconductor layer, n-type semiconductor layer, or 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 electron transport material in an organic thin-film solar cell. In addition to the above, the organic thin-film solar cell may also include a hole blocking layer, electron blocking layer, electron injection layer, hole injection layer, smoothing layer, etc. as appropriate. Known materials used in organic thin-film solar cells can be appropriately selected and combined for use in the organic thin-film solar cell.

[0518] Quantum dots with narrow emission half-widths are used as phosphors in wavelength conversion filters...

Claims

1. A polycyclic aromatic compound represented by the following general formula (2A): 【Chemistry 2】 In the above formula (2A), R ａ , R ｂ , and R ｃ are each independently hydrogen, an aryl having 6 to 16 carbon atoms, a heteroaryl having 2 to 20 carbon atoms, a diarylamino (wherein the aryl is an aryl having 6 to 10 carbon atoms), a diarylboryl (wherein the aryl is an aryl having 6 to 10 carbon atoms, and two aryls may be bonded via a single bond), an alkyl having 1 to 12 carbon atoms, or a cycloalkyl having 3 to 16 carbon atoms, and the R ａ , R ｂ , and R ｃ at least one hydrogen atom in the formula (I) may be substituted with alkyl having 1 to 5 carbon atoms or cycloalkyl having 5 to 10 carbon atoms; Y １ and Y ２ is >B-, X １ , X ２ , X ３ , and X ４ are each independently >N-R or >O, and R in the ">N-R" is an aryl having 6 to 10 carbon atoms or a heteroaryl having 2 to 10 carbon atoms, and at least one hydrogen atom in the R is optionally substituted with an alkyl having 1 to 5 carbon atoms or a cycloalkyl having 5 to 10 carbon atoms; In addition, the X １ Or the X ３ R in the “>N—R” as the ring b and the ring X ２ Or the X ４ R in ">N-R" as the above may be bonded to the ring a via a single bond or an arylene ring having 6 to 10 carbon atoms, and at least one hydrogen atom in the arylene ring may be substituted with alkyl having 1 to 5 carbon atoms or cycloalkyl having 5 to 10 carbon atoms, However, the X １ and X ３ at least one R in ">N-R" is bonded to the ring b via an arylene ring having 6 to 10 carbon atoms, and at least one hydrogen atom in the arylene ring is optionally substituted with alkyl having 1 to 5 carbon atoms or cycloalkyl having 5 to 10 carbon atoms; A polycyclic aromatic compound in which at least one hydrogen atom in the compound represented by the formula (2A) may be substituted with deuterium, cyano, or halogen.

2. A polycyclic aromatic compound represented by any of the following structural formulas: 【Transformation 3】 The benzene rings in the above structural formula are each independently optionally substituted with an aryl having 6 to 16 carbon atoms, a heteroaryl having 2 to 20 carbon atoms, a diarylamino (wherein the aryl is an aryl having 6 to 10 carbon atoms), a diarylboryl (wherein the aryl is an aryl having 6 to 10 carbon atoms, and two aryls may be bonded by a single bond), an alkyl having 1 to 12 carbon atoms, or a cycloalkyl having 3 to 16 carbon atoms, and at least one hydrogen atom in the substituent is optionally substituted with an alkyl having 1 to 5 carbon atoms or a cycloalkyl having 5 to 10 carbon atoms; 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 any of the following structural formulas: 【Chemistry 4】

4. A material for organic devices, comprising the polycyclic aromatic compound described in any one of claims 1 to 3.

5. The material for an organic device according to claim 4 , which is a material for an organic electroluminescent element, 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 material for an organic device according to claim 5 , wherein the material for an organic electroluminescent device is a material for a light-emitting layer.

7. An organic electroluminescence device comprising a pair of electrodes consisting of an anode and a cathode, and an organic layer disposed between the pair of electrodes and containing the polycyclic aromatic compound according to any one of claims 1 to 3.

8. The organic electroluminescent device according to claim 7 , wherein the organic layer is a light-emitting layer.

9. The organic electroluminescent device according to claim 8 , wherein the light-emitting layer contains a host and the polycyclic aromatic compound as a dopant.

10. An organic electroluminescent device according to claim 8 or 9, having at least one of an electron transport layer and an electron injection layer disposed between the cathode and the light-emitting layer, wherein at least one of the electron transport layer and the electron injection layer contains at least one selected from the group consisting of 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.

11. A display device or lighting device comprising the organic electroluminescent device according to any one of claims 7 to 10.

12. A wavelength conversion filter comprising the wavelength conversion filter material described in claim 5.

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