Polycyclic aromatic compound

Abstract

To provide an organic EL element that has a narrow half value width of emission spectrum and an excellent color purity, and further to provide a novel polycyclic aromatic compound that yields an organic EL element having excellent quantum efficiency and element life.SOLUTION: A polycyclic aromatic compound represented by formula (1A) or formula (1B) is provided. (In formula (1A) or formula (1B), B ring, C ring, D ring, E ring, F ring or G ring is an aryl ring or a heteroaryl ring, Y1, Y2, and Y3 are each independently >B- or the like, X1 and X2 are each independently >N-R, >O or the like, L is each independently a single bond or a linking group.).SELECTED DRAWING: None

Description

[Technical field]

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

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

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

[0004] Currently, three types of materials are used for the light-emitting layer: fluorescent materials, phosphorescent materials, and thermally activated delayed fluorescence (TADF) materials. For example, benzofluorene-based compounds have been developed as fluorescent materials (WO 2004 / 061047), and noble metal complexes with multidentate ligands have been developed as phosphorescent materials (JP 2014-239225 A).

[0005] In recent years, materials that improve on azaborine derivatives have also been reported (WO 2015 / 102118). They have a single peak and a narrow emission half-width, and the singlet energy (S 1) and triplet energy (T 1 ) energy difference (ΔS 1 T 1 Compounds with a conjugated structure with a small triplet energy (T ) are useful as materials for blue and green light-emitting layers because they can provide high color purity and high efficiency due to thermally activated delayed fluorescence (TADF). They are also useful as electron transport materials or hole transport materials that sandwich the light-emitting layer. 1 There is a demand for compounds having novel conjugated structures with large .

[0006] However, fluorescent materials have the problem of low luminous efficiency, while phosphorescent and TADF materials have the problem of high luminous efficiency but wide half-width of the emission spectrum and low color purity of the emitted light. Furthermore, phosphorescent materials have the problem of being expensive because they contain precious metals (Nature Vol. 492 13 December 2012, Applied Physics Letters 75, 4 (1999)). [Prior art documents] [Patent documents]

[0007] [Patent Document 1] International Publication No. 2004 / 061047 [Patent Document 2] JP 2014-239225 A [Patent Document 3] International Publication No. 2015 / 102118 [Non-patent literature]

[0008] [Non-Patent Document 1] Nature Vol.492 13 December 2012 [Non-Patent Document 2] Applied Physics Letters 75, 4 (1999) Summary of the Invention [Problem to be solved by the invention]

[0009] As described above, various materials have been developed for use in organic EL devices, but in order to increase the options of materials for organic EL devices, it is desirable to develop materials made of compounds different from conventional ones. In addition, Patent Document 3 reports a polycyclic aromatic compound containing boron and an organic EL device using the same, but in order to further improve the device characteristics, a material for the light-emitting layer, particularly a dopant material, that can improve color purity, luminous efficiency, and device life is required. In addition, as shown in Non-Patent Documents 1 and 2, thermally activated delayed fluorescent materials and phosphorescent materials utilizing the heavy atom effect have a wide half-width of the emission spectrum, which is a problem in terms of improving color purity.

[0010] In addition, as a method for forming the organic layers constituting an organic EL element, a wet film formation method is also used at present in addition to a vacuum deposition method. Therefore, ink materials for wet film formation, particularly for forming a hole injection layer, a hole transport layer, and a light emitting layer, have been actively developed, and it is also beneficial to seek such ink materials. [Means for solving the problem]

[0011] The present inventors have conducted intensive research to solve the above problems, and have succeeded in producing a novel polycyclic aromatic compound, and have found that this compound is effective as a material with a small difference between the singlet energy and triplet energy required for thermally activated delayed fluorescence.Then, for example, by using such a polycyclic aromatic compound as a dopant material and disposing an emission layer in which a compound having a triplet energy larger than that of the dopant material is used as a host material between a pair of electrodes to form an organic EL device, it has been found that an excellent thermally activated delayed fluorescence type organic EL device can be obtained, and the present invention has been completed.

[0012] In this specification, the chemical structure or the substituent may be expressed by the number of carbon atoms, but the number of carbon atoms in the case where a substituent is substituted on the chemical structure or where a substituent is further substituted on the substituent means the number of carbon atoms in each of the chemical structure and the substituent, and does not mean the total number of carbon atoms in the chemical structure and the substituent, or the total number of carbon atoms in the substituent and the substituent. For example, "substituent B of carbon number Y substituted with substituent A of carbon number X" means that "substituent B of carbon number Y" is substituted with "substituent A of carbon number X", and the carbon number Y is not the total number of carbon atoms in the substituent A and the substituent B. Also, for example, "substituent B of carbon number Y substituted with substituent A" means that "substituent B of carbon number Y" is substituted with "substituent A (without carbon number limit)", and the carbon number Y is not the total number of carbon atoms in the substituent A and the substituent B.

[0013] Since the chemical structural formulas described herein (including the general formulas depicted in the Markush structural formula) are planar structural formulas, various isomeric structures such as enantiomers, diastereoisomers, and rotational isomers may actually exist. In this specification, unless otherwise specified, the compounds described may be any isomeric structure conceivable from the planar structural formula, or may be a mixture of possible isomers in any ratio.

[0014] This specification describes many structural formulas of aromatic compounds. Aromatic compounds are described by combining double bonds and single bonds, but in reality, because π electrons resonate, a single substance can have multiple equivalent resonance structures in which double bonds and single bonds alternate. This specification describes only one resonance structural formula for each substance, but unless otherwise specified, other resonance structural formulas that are organically equivalent are also included. This is referred to later in descriptions such as "any '-C(-R)=' may be replaced with '-N='" (R is replaced with R each time). a , R b , R c , R d , R e , R f , or R g(E.g., as defined below). For example, the following is an example of "-C(-R)=" in formula (2A) described below. However, this is not limited to this, and it naturally applies not only to the one resonance structure shown, but also to other possible equivalent resonance structures. [ka]

[0015] The statement that "any "-C(-R)=" may be replaced with "-N="" applies to all structural formulas in this specification unless otherwise specified. In addition, R in the above-mentioned -C(-R)= is to be read as a substituent defined for the ring structure in each case.

[0016] In this specification, the two expressions "may" and "is not, or has been", are used, but both have the same meaning.

[0017] <1> A polycyclic aromatic compound represented by the following general formula (1A) or general formula (1B): [ka] In the above formula (1A) or formula (1B), R a is hydrogen or a substituent, and "-C(-R a )=" is not replaced by "-N=" or is replaced by "-N=", ring B, ring C, ring D, ring E, ring F, and ring G are each independently an aryl ring or a heteroaryl ring, and at least one hydrogen atom in these rings is unsubstituted or substituted; Y 1 , Y 2 , and Y 3are each independently >B-, >P-, >P(=O)-, >P(=S)-, >Al-, >Ga-, >As-, >C(-R)-, >Si(-R)-, or >Ge(-R)-, and R of >C(-R)-, R of >Si(-R)-, and R of >Ge(-R)- are each independently substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl; In formula (1A), X 1 and X 2 are, independently, >NR, >O, >S, >C(-R) 2、 >Si(-R)2 or >Se, R of >NR, R of >C(-R)2, and R of >Si(-R)2 are each independently hydrogen, or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl, and at least one of the two R of >C(-R)2 and the two R of >Si(-R)2 is not bonded to each other or is bonded to each other by a single bond or a linking group, X 1 R of >NR, R of >C(-R)2, or R of >Si(-R)2 as X is bonded to at least one of the a ring and the B ring by a single bond or a linking group; 2 R of >NR, R of >C(-R)2, or R of >Si(-R)2 as the above is bonded to at least one of the a ring and the E ring via a single bond or a linking group, and each of the multiple linking groups is the same or different; In the above formula (1A) or formula (1B), L's are each independently a single bond or a linking group, with the proviso that at least one of L's is a substituted or unsubstituted alkylene, a substituted or unsubstituted cycloalkylene, a substituted or unsubstituted alkenylene, a substituted or unsubstituted alkynylene, a substituted or unsubstituted arylene, or a substituted or unsubstituted heteroarylene; in the compound represented by the above formula (1A) or formula (1B), at least one of ring B, ring C, ring D, ring E, ring F, ring G, aryl, and heteroaryl is not condensed with or is condensed with at least one cycloalkane, at least one hydrogen in the cycloalkane is not substituted or is substituted, and at least one -CH2- in the cycloalkane is not substituted or is substituted with -O-; At least one hydrogen atom in the compound represented by the above formula (1A) or formula (1B) is not substituted or is substituted with deuterium, cyano, or halogen.

[0018] <2> In the above formula (1A) or formula (1B), R a is hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted diarylamino, substituted or unsubstituted diheteroarylamino, substituted or unsubstituted arylheteroarylamino, substituted or unsubstituted diarylboryl, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryloxy, substituted or unsubstituted arylthio, or substituted silyl, wherein the two aryls of the diarylamino are not bonded to each other or are bonded to each other via a linking group, the two heteroaryls of the diheteroarylamino are not bonded to each other or are bonded to each other via a linking group, the aryl and heteroaryl of the arylheteroarylamino are not bonded to each other or are bonded to each other via a linking group, and the two aryls of the diarylboryl are not bonded to each other or are bonded to each other via a single bond or a linking group; -C(-R a )=" is not replaced by "-N=" or is replaced by "-N=", ring B, ring C, ring D, ring E, ring F, and ring G are each independently an aryl ring or a heteroaryl ring, at least one hydrogen atom in these rings may be replaced by a substituted or unsubstituted aryl, a substituted or unsubstituted heteroaryl, a substituted or unsubstituted diarylamino, a substituted or unsubstituted diheteroarylamino, a substituted or unsubstituted arylheteroarylamino, a substituted or unsubstituted diarylboryl, a substituted or unsubstituted alkyl, a substituted or unsubstituted cycloalkyl, a substituted or unsubstituted alkenyl, a substituted or unsubstituted alkoxy, a substituted or unsubstituted aryloxy, a substituted or unsubstituted arylthio, or a substituted silyl, two aryls in the diarylamino are not bonded to each other or are bonded to each other via a linking group, two heteroaryls in the diheteroarylamino are not bonded to each other or are bonded to each other via a linking group, the aryl and heteroaryl in the arylheteroarylamino are not bonded to each other or are bonded to each other via a linking group, and two aryls in the diarylboryl are not bonded to each other or are bonded to each other via a single bond or a linking group; Y 1 , Y 2 , and Y 3 are each independently >B-, >P-, >P(=O)-, >P(=S)-, >Al-, >Ga-, >As-, >C(-R)-, >Si(-R)-, or >Ge(-R)-, and 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 these may be substituted by alkyl or cycloalkyl; In formula (1A), X 1 and X 2 are, independently, >NR, >O, >S, >C(-R) 2、>Si(-R)2 or >Se, R of the >NR, R of the >C(-R)2, and R of the >Si(-R)2 are each independently hydrogen, aryl, heteroaryl, alkyl, or cycloalkyl, at least one hydrogen in these is not substituted or is substituted with alkyl or cycloalkyl, two R of the >C(-R)2 and two R of the >Si(-R)2 are not bonded together or are bonded together by a single bond or a linking group, and multiple linking groups are each the same or different, X 1 R of >NR, R of >C(-R)2, or R of >Si(-R)2 as X is bonded to at least one of the a ring and the B ring by a single bond or a linking group; 2 R of >NR, R of >C(-R)2, or R of >Si(-R)2 as the above is bonded to at least one of the a ring and the E ring via a single bond or a linking group, and each of the multiple linking groups is the same or different; In the above formula (1A) or formula (1B), each L is independently a single bond or a linking group, provided that at least one L is a substituted or unsubstituted alkylene, a substituted or unsubstituted cycloalkylene, a substituted or unsubstituted alkenylene, a substituted or unsubstituted alkynylene, a substituted or unsubstituted arylene, or a substituted or unsubstituted heteroarylene; the linking group is -N(-R)-, -O-, -S-, -C(-R)2-, -Si(-R)2-, -Se-, a substituted or unsubstituted cycloalkylene, a substituted or unsubstituted alkylene, a substituted or unsubstituted alkenylene, a substituted or unsubstituted alkynylene, a substituted or unsubstituted arylene, or a substituted or unsubstituted heteroarylene, R of the -N(-R)-, R of the -C(-R)2-, and R of the -Si(-R)2- each independently represent a hydrogen atom, an aryl, a heteroaryl, an alkyl, or a cycloalkyl, and at least one hydrogen atom in these is not substituted or is substituted by an alkyl or a cycloalkyl; In the compound represented by the above formula (1A) or formula (1B), at least one of ring B, ring C, ring D, ring E, ring F, ring G, aryl, and heteroaryl is not condensed with or is condensed with at least one cycloalkane, at least one hydrogen in the cycloalkane is not substituted or is substituted, and at least one -CH2- in the cycloalkane is not substituted or is substituted with -O-, At least one hydrogen atom in the compound represented by the above formula (1A) or formula (1B) is not substituted or is substituted with deuterium, cyano, or halogen. <1> 2. The polycyclic aromatic compound according to claim 1 .

[0019] <3> Represented by the following general formula (2A) or the following general formula (2B): <1> The polycyclic aromatic compound according to claim 1. [ka] In the above formula (2A) or (2B), R a is hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl, alkyl, cycloalkyl, alkenyl, alkoxy, aryloxy, arylthio, triarylsilyl, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, or alkyldicycloalkylsilyl, in which at least one hydrogen is unsubstituted or substituted with aryl, heteroaryl, alkyl, or cycloalkyl; the two aryls of the diarylamino are not bonded to each other or are bonded via a linking group; the two heteroaryls of the diheteroarylamino are not bonded to each other or are bonded via a linking group; the aryl and heteroaryl of the arylheteroarylamino are not bonded to each other or are bonded via a linking group; the two aryls of the diarylboryl are not bonded to each other or are bonded via a single bond or a linking group; -C(-R a )=" may be replaced with "-N=", R b , R c , R d , R e , R f , and R g are each independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl, alkyl, cycloalkyl, alkenyl, alkoxy, aryloxy, arylthio, triarylsilyl, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, or alkyldicycloalkylsilyl, in which at least one hydrogen is unsubstituted or substituted with an aryl, heteroaryl, alkyl, or cycloalkyl, and in which at least one hydrogen is unsubstituted or substituted with an aryl, heteroaryl, alkyl, or cycloalkyl, the two aryls of the diarylamino are not bonded to each other or are bonded via a linking group, the two heteroaryls of the diheteroarylamino are not bonded to each other or are bonded via a linking group, the aryl and heteroaryl of the arylheteroarylamino are not bonded to each other or are bonded via a linking group, and the two aryls of the diarylboryl are not bonded to each other or are bonded via a single bond or a linking group; Also, R b , R c , R d , R e , R f , and R gadjacent groups among the above may be bonded to each other to form an aryl ring or a heteroaryl ring together with the b ring, the c ring, the d ring, the e ring, the f ring, and the g ring, respectively, and at least one hydrogen atom in the formed ring is not substituted or is substituted with an aryl, a heteroaryl, a diarylamino, a diheteroarylamino, an arylheteroarylamino, a diarylboryl, an alkyl, a cycloalkyl, an alkenyl, an alkoxy, an aryloxy, an arylthio, a triarylsilyl, a trialkylsilyl, a tricycloalkylsilyl, a dialkylcycloalkylsilyl, or an alkyldicycloalkylsilyl, at least one hydrogen atom in said diarylamino is unbonded to each other or is bonded to each other through a linking group; said two heteroaryls in said diheteroarylamino are unbonded to each other or are bonded to each other through a linking group; said aryls and heteroaryls in said arylheteroarylamino are unbonded to each other or are bonded to each other through a linking group; said two aryls in said diarylboryl are unbonded to each other or are bonded to each other through a single bond or a linking group; In rings b, c, d, e, f, and g, any "-C(-R)=" (where R is R b , R c , R d , R e , R f , or R g ) is not replaced by "-N=" or is replaced by "-C(-R)=C(-R)-" (where R is R b , R c , R d , R e , R f , or R gis not replaced or 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, at least one hydrogen therein is not replaced or is substituted by alkyl or cycloalkyl, two R of the "-C(-R)2-" and two R of the "-Si(-R)2-" may be bonded to each other via a single bond or a linking group, L is each independently a single bond or a linking group, provided that at least one L is alkylene, cycloalkylene, alkylene, alkenylene, alkynylene, aryleneheteroarylene, and at least one hydrogen atom of the cycloalkylene, the alkenylene, the alkynylene, the arylene, and the heteroarylene is unsubstituted or substituted with an aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl, alkyl, cycloalkyl, alkenyl, alkoxy, aryloxy, arylthio, triarylsilyl, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, or alkyldicycloalkylsilyl, and at least one hydrogen atom in each of the above is unsubstituted or substituted with an aryl, heteroaryl, alkyl, or cycloalkyl, at least one hydrogen atom in each of the above is unsubstituted or substituted with an aryl, heteroaryl, alkyl, or cycloalkyl, the two aryls in the diarylamino are not bonded to each other or are bonded via a linking group, the two heteroaryls in the diheteroarylamino are not bonded to each other or are bonded via a linking group, the aryl and heteroaryl in the arylheteroarylamino are not bonded to each other or are bonded via a linking group, and the two aryls in the diarylboryl are not bonded to each other or are bonded via a single bond or a linking group; The linking group is -N(-R)-, -O-, -S-, -C(-R)2-, -Si(-R)2-, -Se-, cycloalkylene, alkylene, alkenylene, alkynylene, arylene, or heteroarylene, in which R of -N(-R)-, R of -C(-R)2-, and R of -Si(-R)2- are each independently hydrogen, aryl, heteroaryl, alkyl, or cycloalkyl, at least one hydrogen atom of which is not substituted or is substituted with an alkyl or cycloalkyl, and at least one hydrogen atom of the cycloalkylene, the alkylene, the alkenylene, the alkynylene, the arylene, and the heteroarylene is aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl, alkyl, cycloalkyl, alkenyl, alkoxy, aryloxy, arylthio, triarylsilyl, or trialkylsilyl. , tricycloalkylsilyl, dialkylcycloalkylsilyl, or alkyldicycloalkylsilyl, at least one hydrogen atom in each of these is unsubstituted or substituted with an aryl, heteroaryl, alkyl, or cycloalkyl, at least one hydrogen atom in each of these is unsubstituted or substituted with an aryl, heteroaryl, alkyl, or cycloalkyl, the two aryls of the diarylamino are not bonded to each other or are bonded via a linking group, the two heteroaryls of the diheteroarylamino are not bonded to each other or are bonded via a linking group, the aryl and heteroaryl of the arylheteroarylamino are not bonded to each other or are bonded via a linking group, and the two aryls of the diarylboryl are not bonded to each other or are bonded via a single bond or a linking group, Y 1 , Y 2 , and Y 3are each independently >B-, >P-, >P(=O)-, >P(=S)-, >Al-, >Ga-, >As-, >C(-R)-, >Si(-R)-, or >Ge(-R)-, and 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 these may be substituted by alkyl or cycloalkyl; In formula (2A) X 1 and X 2 are, independently, >NR, >O, >S, >C(-R) 2、 >Si(-R)2 or >Se, R of >NR, R of >C(-R)2, and R of >Si(-R)2 are each independently hydrogen, aryl, heteroaryl, alkyl, or cycloalkyl, at least one hydrogen in these is not substituted or is substituted with alkyl or cycloalkyl, two R of >C(-R)2 and two R of >Si(-R)2 are not bonded together or are bonded together by a single bond or a linking group, and multiple linking groups are different or the same, X 1 R of >NR, R of >C(-R)2, or R of >Si(-R)2 as X is bonded to at least one of the a ring and the b ring by a single bond or a linking group; 2 R of >NR, R of >C(-R)2, or R of >Si(-R)2 as the above is bonded to at least one of the a ring and the e ring via a single bond or a linking group, and the multiple linking groups are different or the same; In the compound represented by the above formula (2A) or (2B), at least one of the ring b, the ring c, the ring d, the ring e, the ring f, the ring g, the formed ring, the aryl, and the heteroaryl is not condensed with or is condensed with at least one cycloalkane having 3 to 24 carbon atoms, at least one hydrogen atom in the cycloalkane is not substituted or is substituted with an aryl having 6 to 30 carbon atoms, a heteroaryl having 2 to 30 carbon atoms, an alkyl having 1 to 24 carbon atoms, or a cycloalkyl having 3 to 24 carbon atoms, and at least one -CH2- in the cycloalkane is not substituted or is substituted with -O-, At least one hydrogen atom in the compound represented by the above formula (2A) or formula (2B) is not substituted or is substituted with deuterium, cyano, or halogen.

[0020] <4> Represented by any of the following structural formulas: <1> ~ <3> 2. The polycyclic aromatic compound according to claim 1 . [ka] TIFF0007622941000005.tif59113 TIFF0007622941000006.tif54170In each expression, R's 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), an alkyl having 1 to 12 carbon atoms, or a cycloalkyl having 3 to 16 carbon atoms, in which at least one hydrogen may be substituted with an alkyl having 1 to 5 carbon atoms or a cycloalkyl having 5 to 10 carbon atoms; the two aryls of the diarylamino are not bonded to each other or are bonded via a linking group; and the two aryls of the diarylboryl are not bonded to each other or are bonded via a single bond or a linking group. Each o is independently an integer from 1 to 3; Each p is independently an integer of 1 to 4; Each q is independently an integer of 1 to 5, At least one hydrogen in the compounds represented by the above formulas may be substituted with deuterium, cyano, or halogen.

[0021] <5> Represented by any of the following structural formulas: <1> The polycyclic aromatic compound according to claim 1. [ka]

[0022] <6> <1> ~ <5> 2. A reactive compound in which the polycyclic aromatic compound according to any one of the above items 1 to 10 is substituted with a reactive substituent.

[0023] <7> <6> A polymer compound obtained by polymerizing the reactive compound described in the above as a monomer, or a polymer crosslinked body obtained by further crosslinking the polymer compound.

[0024] <8> Main chain polymer <6> or a pendant-type crosslinked polymer obtained by further crosslinking the pendant-type polymer compound.

[0025] <9> <1> ~ <5> 1. A material for an organic device, comprising the polycyclic aromatic compound according to any one of claims 1 to 9.

[0026] <10> <6> A material for organic devices comprising the reactive compound described in 1.

[0027] <11> <7> 2. A material for an organic device, comprising the polymer compound or crosslinked polymer described in 1.

[0028] <12> <8> 2. A material for an organic device, comprising the pendant type polymer compound or the pendant type crosslinked polymer described in 1.

[0029] <13> The organic device material is a material for an organic electroluminescent element, a material for an organic field effect transistor, or a material for an organic thin-film solar cell. <9> ~ <12> 1. A material for an organic device according to any one of claims 1 to 9.

[0030] <14> The material for an organic electroluminescent device is a material for a light-emitting layer. <13> 2. A material for organic devices according to claim 1.

[0031] <15> <1> ~ <5> 13. An ink composition comprising the polycyclic aromatic compound according to any one of claims 1 to 12 and an organic solvent.

[0032] <16> <6> and an organic solvent.

[0033] <17> A main chain polymer, <6> and an organic solvent.

[0034] <18> <7> 1. An ink composition comprising the polymer compound or crosslinked polymer described in 1. and an organic solvent.

[0035] <19> <8> 2. An ink composition comprising the pendant type polymer compound or the pendant type crosslinked polymer described in 1. above and an organic solvent.

[0036] <20> A pair of electrodes consisting of an anode and a cathode, and a gas sensor disposed between the pair of electrodes, <1> ~ <5> 2. A polycyclic aromatic compound according to claim 1 , <6> 2. A reactive compound according to claim 1, <7> or <8> and an organic layer containing the pendant type polymer compound or the pendant type crosslinked polymer according to 1.

[0037] <21> The organic layer is an emitting layer. <20> 2. The organic electroluminescent device according to claim 1 .

[0038] <22> the light-emitting layer contains a host and the polycyclic aromatic compound, reactive compound, polymer compound, crosslinked polymer, pendant polymer compound, or pendant crosslinked polymer as a dopant; <21> 2. The organic electroluminescent device according to claim 1 .

[0039] <23> 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 including 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: <22> 2. The organic electroluminescent device according to claim 1 . [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 each independently represents an aryl having 6 to 30 carbon atoms or a heteroaryl having 2 to 30 carbon atoms, In the above 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, two hydrogen atoms in MU are replaced by EC or MU, and k is an integer of 2 to 50,000, In the above 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 11are each independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, alkyl or cycloalkyl, at least one hydrogen of which may be further substituted with aryl, heteroaryl, diarylamino, alkyl or cycloalkyl, the two aryls of the diarylamino are not bonded to each other or are bonded via a linking group, the two heteroaryls of the diheteroarylamino are not bonded to each other or are bonded via a linking group, and the aryl and heteroaryl of the arylheteroarylamino are not bonded to each other or are bonded via a linking group; R 1 ~R 11 adjacent groups among the above may be bonded to each other to form an aryl ring or a heteroaryl ring together with the a ring, the b ring or the c ring, and at least one hydrogen in the formed ring may be replaced by an aryl, a heteroaryl, a diarylamino, a diheteroarylamino, an arylheteroarylamino, an alkyl or a cycloalkyl, and at least one hydrogen in these rings may be further replaced by an aryl, a heteroaryl, a diarylamino, an alkyl or a cycloalkyl, the two aryls in the diarylamino are not bonded to each other or are bonded to each other via a linking group, the two heteroaryls in the diheteroarylamino are not bonded to each other or are bonded to each other via a linking group, and the aryl and heteroaryl in the arylheteroarylamino are not bonded to each other or are bonded to each other via a linking group; In the a, b, and c rings, any "-C(-R)=" (where R is R 1 ~R 11 ) may be replaced with "-N=", In the above general formula (H6), R 1 ~R 16are each independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, alkyl or cycloalkyl, at least one hydrogen of which may be further substituted with aryl, heteroaryl, diarylamino, alkyl or cycloalkyl, the two aryls of the diarylamino are not bonded to each other or are bonded via a linking group, the two heteroaryls of the diheteroarylamino are not bonded to each other or are bonded via a linking group, and the aryl and heteroaryl of the arylheteroarylamino are not bonded to each other or are bonded via a linking group; 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, at least one hydrogen in the formed ring may be replaced by an aryl, a heteroaryl, a diarylamino, a diheteroarylamino, an arylheteroarylamino, an alkyl or a cycloalkyl, at least one hydrogen in these rings may be further replaced by an aryl, a heteroaryl, a diarylamino, an alkyl or a cycloalkyl, the two aryls of the diarylamino are not bonded to each other or are bonded to each other via a linking group, the two heteroaryls of the diheteroarylamino are not bonded to each other or are bonded to each other via a linking group, the aryl and heteroaryl of the arylheteroarylamino are not bonded to each other or are bonded to each other via a linking group, 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.

[0040] <24> <20> ~ <23> 2. A display device or a lighting device comprising the organic electroluminescent device according to any one of claims 1 to 11. Effect of the Invention

[0041] According to a preferred embodiment of the present invention, an organic EL device is produced using the novel polycyclic aromatic compound as, for example, a dopant material, thereby providing an organic EL device having a narrow half-width of the emission spectrum and excellent color purity, and further having excellent quantum efficiency and device life. In addition, since the novel polycyclic aromatic compound of the present invention has a rigid structure, many of the compounds have a sharper emission spectrum, a narrow half-width of the emission spectrum, and emit light with high color purity.

[0042] Specifically, the inventors have found that polycyclic aromatic compounds in which aromatic rings are linked by heteroatoms such as boron, phosphorus, oxygen, nitrogen, and sulfur have a large HOMO-LUMO gap (band gap Eg in thin films) and high triplet energy. This is believed to be because the six-membered rings containing heteroatoms have low aromaticity, which suppresses the decrease in the HOMO-LUMO gap associated with the expansion of the conjugated system, and because the SOMO1 and SOMO2 in the triplet excited states are localized due to electronic perturbation of the heteroatoms.

[0043] In addition, the hetero element-containing polycyclic aromatic compound according to the present invention has a small energy difference between the triplet excited state and the singlet excited state, and further has a large spin-orbit interaction and exhibits thermally activated delayed fluorescence, so it is also useful as a fluorescent material for an organic EL device. In addition, materials having high triplet energy are also useful as electron transport layers and hole transport layers for phosphorescent organic EL devices and organic EL devices using thermally activated delayed fluorescence. Furthermore, these polycyclic aromatic compounds can arbitrarily move the energies of HOMO and LUMO by introducing a substituent, so that it is possible to optimize the ionization potential and electron affinity according to the surrounding materials. [Brief description of the drawings]

[0044] [Figure 1] FIG. 1 is a schematic cross-sectional view showing an organic EL element according to an embodiment of the present invention. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0045] <Polycyclic aromatic compound of the present invention> <Explanation 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). In each of the above formulas, "B" to "G" in a circle are symbols indicating the ring structure represented by the circle, and "a" to "g" in the 6-membered aromatic ring are benzene rings or rings modified therefrom in some cases (such as 6- or 5-membered heteroaromatic rings), and the other symbols are the same as defined above. Furthermore, the symbols in all structural formulas shown in this paragraph and subsequent paragraphs are also defined as above. [ka] [ka]

[0046] The compound of the present invention has a linking group Q as L or X in the molecule. 1 or X 2 and at least one linking group Q is an alkylene, cycloalkylene, alkenylene, alkynylene, arylene, or heteroarylene. At least one hydrogen atom of the linking group Q is unsubstituted or substituted.

[0047] The linking groups Q may each be independently formed as L selected from a single bond and a linking group Q, or as X 1 or X 2 In the formula (1A), the linking group Q is, for example, L that links the C ring and the D ring, and in ... 1 or X 2 When R is >NR, it is formed as a linking group when it is linked to ring B or ring E, respectively. In formula (2A), for example, it is L linking ring c and ring d, and other than that, X 1 or X 2When R is >NR, R is a linking group linking ring b or ring e, respectively. In formula (1B), similarly, R is formed as L linking ring C and ring D, and is also L linking ring G and ring B, and is also L linking ring F and ring E. In formula (2B), similarly, for example, R is L linking ring c and ring d, and is also a linking group linking ring g and ring b, and is also L linking ring f and ring e.

[0048] <Explanation of ring structure and its substituents> R a is hydrogen or a substituent. The substituents include substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted diarylamino (two aryls are not bonded to each other or are bonded via a linking group), substituted or unsubstituted diheteroarylamino (two heteroaryls of diheteroarylamino are not bonded to each other or are bonded via a linking group), substituted or unsubstituted arylheteroarylamino (aryl and heteroaryl are not bonded to each other or are bonded via a linking group), substituted or unsubstituted diarylboryl (two aryls are not bonded to each other or are bonded via a single bond or a linking group), substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryloxy, substituted or unsubstituted arylthio, or substituted silyl. Examples of the substituents when these groups have a substituent include aryl, heteroaryl, alkyl, or cycloalkyl. Details of the substituents listed here will be described below.

[0049] Ring B, ring C, ring D, ring E, ring F, and ring G are each independently an aryl ring or a heteroaryl ring, and at least one hydrogen atom in these rings is not substituted or is substituted with a substituent. As the substituent, a substituted or unsubstituted aryl, a substituted or unsubstituted heteroaryl, a substituted or unsubstituted diarylamino (two aryls are not bonded to each other or are bonded via a linking group), a substituted or unsubstituted diheteroarylamino (two heteroaryls of diheteroarylamino are not bonded to each other or are bonded via a linking group), a substituted or unsubstituted arylheteroarylamino (aryls and heteroaryls are not bonded to each other or are bonded via a linking group), a substituted or unsubstituted diarylboryl (two aryls are not bonded to each other or are bonded via a single bond or a linking group), a substituted or unsubstituted alkyl, a substituted or unsubstituted cycloalkyl, a substituted or unsubstituted alkenyl, a substituted or unsubstituted alkoxy, a substituted or unsubstituted aryloxy, a substituted or unsubstituted arylthio, or a substituted silyl is preferred. In the case where these groups have a substituent, the substituent may be an aryl, heteroaryl, alkyl, or cycloalkyl. Details of the rings and substituents listed here will be described below.

[0050] R b , R c , R d , R e , R f , and R gare each independently hydrogen, aryl, heteroaryl, diarylamino (two aryls are not bonded to each other or are bonded via a linking group), diheteroarylamino (two heteroaryls of diheteroarylamino are not bonded to each other or are bonded via a linking group), arylheteroarylamino (aryl and heteroaryl are not bonded to each other or are bonded via a linking group), diarylboryl (two aryls are not bonded to each other or are bonded via a single bond or a linking group), alkyl, cycloalkyl, alkenyl, alkoxy, aryloxy, arylthio, triarylsilyl, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, or alkyldicycloalkylsilyl, and at least one hydrogen in these may be substituted with aryl, heteroaryl, alkyl, or cycloalkyl. Details of the substituents listed here will be described below.

[0051] The aryl ring or heteroaryl ring (i.e., rings B to G) in formula (1A) and formula (1B) preferably has a 5- or 6-membered ring that shares a bond with the fused bicyclic structure contained in each formula.

[0052] Here, the "fused bicyclic structure" refers to, in formula (1A), Y 1 , X 1 and a structure in which two saturated hydrocarbon rings containing N are fused together (the first fused bicyclic structure on the left side of the formula), and Y 2 , X 2 and N are fused together (the second fused bicyclic structure on the right side of the formula). Similarly, in formula (1B), Y 1 and a structure in which two saturated hydrocarbon rings containing two Ns are fused together (the first fused bicyclic structure on the left side of the formula), and Y 2 and a structure in which two saturated hydrocarbon rings containing two Ns are fused together (the second fused bicyclic structure on the right side of the formula), and Y 3and a structure in which two saturated hydrocarbon rings each containing two N are fused together (the third fused bicyclic structure at the bottom of the formula). Although not shown in the figures, fused bicyclic structures are present in similar positions in formulas (2A) and (2B).

[0053] In addition, the term "six-membered ring sharing a bond with a fused bicyclic structure" means a b ring (benzene ring (six-membered ring)) fused to a fused bicyclic structure, for example, as shown in formula (2A) or formula (2B). In addition, "an aryl ring or heteroaryl ring (which is a B ring) has this six-membered ring" means that the B ring is formed only from this six-membered ring, or that the B ring is formed by further condensing this six-membered ring to the six-membered ring so as to include this six-membered ring. In other words, the term "an aryl ring or heteroaryl ring (which is a B ring) having a six-membered ring" means that the six-membered ring constituting all or a part of the B ring is fused to a fused bicyclic structure. The same explanation applies to "C ring (c ring)", "D ring (d ring)", "E ring (e ring)", "F ring (f ring)", and "G ring (g ring)", and the same explanation also applies to "five-membered ring".

[0054] The rings B, C, D, and E in formula (1A) are each independently the ring b and its substituent R in formula (2A). b , ring c and its substituent R c , d ring and its substituent R d , and the e ring and its substituent R e That is, formula (2A) corresponds to a structure in which "rings B to E having six-membered rings" are selected as rings B to E of formula (1A). "Having" a six-membered ring means, as described later, that, for example, the six-membered ring b is a ring having four substituents R b This is because adjacent groups among the above may bond to form a ring, and the six-membered ring b may be condensed with another ring to correspond to ring B. In this sense, the rings in formula (1A) are represented by capital letters B to E, while the rings in formula (2A) are represented by lowercase letters b to e.

[0055] The rings B, C, D, E, F, and G in formula (1B) are each independently the ring b and its substituent R in formula (2B). b , ring c and its substituent R c , d ring and its substituent R d , e ring and its substituent R e , ring f and its substituent R f , and ring g and its substituent R g That is, formula (2B) corresponds to a structure in which "ring B to ring G having 6-membered rings" are selected as ring B to ring G of formula (1B). "Having" a 6-membered ring means, as described later, that, for example, the 6-membered ring b is a ring having four substituents R b This is because adjacent groups among the above may bond to each other to form a ring, and the six-membered ring b may be further condensed with another ring to correspond to ring B. In this sense, the rings in formula (1B) are represented by capital letters B to G, while the rings in formula (2B) are represented by lowercase letters b to g.

[0056] <Explanation of changes in ring structure due to bonding between substituents> Substituents R of rings b, c, d, e, f, and g b , R c , R d , R e , R f , and R gAdjacent groups among the above may be bonded to each other to form an aryl ring or a heteroaryl ring together with the b ring, the c ring, the d ring, the e ring, the f ring, and the g ring, respectively, and at least one hydrogen atom in the formed ring may be substituted with an aryl, a heteroaryl, a diarylamino (two aryls are not bonded to each other or are bonded via a linking group), a diheteroarylamino (two heteroaryls in the diheteroarylamino are not bonded to each other or are bonded via a linking group), an arylheteroarylamino (aryls and heteroaryls are not bonded to each other or are bonded via a linking group), a diarylboryl (two aryls are not bonded to each other or are bonded via a single bond or a linking group), an alkyl, a cycloalkyl, an alkenyl, an alkoxy, an aryloxy, an arylthio, a triarylsilyl, a trialkylsilyl, a tricycloalkylsilyl, a dialkylcycloalkylsilyl, or an alkyldicycloalkylsilyl, and at least one hydrogen atom in these may be substituted with an aryl, a heteroaryl, an alkyl, or a cycloalkyl. Details of the rings and substituents listed here will be described below.

[0057] Therefore, the polycyclic aromatic compound of formula (2A) or formula (2B) has a ring structure that changes depending on the mutual bonding form of the substituents in rings b to g, as shown in the following formulas (2A-fr) and (2B-fr). Rings B' and C' in the following formulas correspond to rings B and C in formulas (1A) and (1B), respectively. Rings d to g can also change in the same way. [ka]

[0058] The B′ ring and the C′ ring in the above formula (2A-fr) and formula (2B-fr) are each, as explained in formula (2A) and formula (2B), a plurality of substituents R b and R cAdjacent groups in the above are bonded to each other to form an aryl or heteroaryl ring together with the b and c rings (the rings may also be considered fused rings formed by condensing other ring structures to the b or c ring). Also, as can be seen from the above formula, for example, R in the b ring b and R in c-ring c In other words, the substituents in different rings do not fall under the category of "adjacent groups" and are not basically bonded to each other. In other words, "adjacent groups" means groups adjacent to each other on the same ring.

[0059] The above formula (2A-fr) and formula (2B-fr) have a ring B' or C' formed by condensing, for example, a benzene ring, an indole ring, a pyrrole ring, a benzofuran ring, or a benzothiophene ring to a benzene ring which is ring b or ring c, and the formed condensed ring B' or condensed ring C' is a naphthalene ring, a carbazole ring, an indole ring, a dibenzofuran ring, a dibenzothiophene ring, or the like, respectively.

[0060] More specific examples of formula (2A-fr) and formula (2B-fr) are shown below. [ka]

[0061] The above formulae (2A-fr-ex) and (2B-fr-ex) are specific examples of formulae (2A-fr) and (2B-fr), respectively. In formulae (2A) and (2B), two adjacent R b are bonded to the b ring (benzene ring) to form an aryl ring (naphthalene ring) represented by B', and the two adjacent R c is bonded to the ring b (benzene ring) to form an aryl ring (dibenzofuran ring) represented by C'. The aryl ring formed has a six-membered ring (benzene ring b or c) that shares a bond with the above-mentioned fused bicyclic structure. Optional substituents on the aryl rings B' and C' (rings B and C in formula (1A) and formula (1B)) are R b and R cIn addition, n R's are also shown, and the upper limit of n is the maximum number of substitutions possible. These explanations can be similarly applied to any form other than the above-mentioned specific examples, for example, when rings d to g are changed or when other aryl rings or heteroaryl rings are formed.

[0062] <Central element Y in the compound 1 ~Y 3 Description of > Y 1 , Y 2 , and Y 3 are each independently >B-, >P-, >P(=O)-, >P(=S)-, >Al-, >Ga-, >As-, >C(-R)-, >Si(-R)-, or >Ge(-R)-, and R of >C(-R)-, R of >Si(-R)-, and R of >Ge(-R)- are each independently optionally substituted aryl, optionally substituted heteroaryl, optionally substituted alkyl, or optionally substituted cycloalkyl. Y 1 , Y 2 , and Y 3 is preferably >B-, >P-, >P(=O)-, or >P(=S)-, and more preferably >B-. Details of the substituents listed here will be described later.

[0063] <Explanation of changes in ring structure due to the linking group L between rings> In formula (1A) and formula (1B), rings C and D are bonded via L. In formula (1B), rings G and B, and rings F and E are also bonded independently via L. The bond between rings C and D via L is also called a CLD bond, the bond between rings G and B via GLB bond, and the bond between rings F and E via L via FLE bond.

[0064] <Explanation of Linking Group> The linking group is an atom or a functional group that connects two carbon atoms, and is preferably the linking group Q. The linking group Q is -N(-R)-, -O-, -S-, -C(-R)2-, -Si(-R)2-, -Se-, a substituted or unsubstituted cycloalkylene, a substituted or unsubstituted alkylene, a substituted or unsubstituted alkenylene, a substituted or unsubstituted alkynylene, a substituted or unsubstituted arylene, or a substituted or unsubstituted heteroarylene, and R of the -N(-R)-, R of the -C(-R)2-, and R of the -Si(-R)2- are each independently hydrogen, an aryl, a heteroaryl, an alkyl, or a cycloalkyl, and preferably hydrogen, an aryl having 6 to 12 carbon atoms, a heteroaryl having 2 to 15 carbon atoms, an alkyl having 1 to 6 carbon atoms, or a cycloalkyl having 3 to 14 carbon atoms. At least one hydrogen in these is unsubstituted or substituted with alkyl (preferably alkyl having 1 to 6 carbon atoms, more preferably alkyl having 2 to 4 carbon atoms) or cycloalkyl (preferably cycloalkyl having 3 to 14 carbon atoms, more preferably cycloalkyl having 3 to 10 carbon atoms). In addition, the cycloalkylene, alkenylene, alkynylene, arylene, and heteroarylene are preferably alkenylene having 2 to 6 carbon atoms, alkylene having 2 to 6 carbon atoms, cycloalkylene having 3 to 14 carbon atoms, arylene having 6 to 12 carbon atoms, or heteroarylene having 2 to 15 carbon atoms, and more preferably alkenylene having 2 to 6 carbon atoms, alkylene having 2 to 4 carbon atoms, cycloalkylene having 3 to 10 carbon atoms, arylene having 6 to 10 carbon atoms, or heteroarylene having 2 to 12 carbon atoms. At least one hydrogen atom in these is not substituted or is substituted with alkyl (preferably alkyl having 1 to 6 carbon atoms, more preferably alkyl having 2 to 4 carbon atoms) or cycloalkyl (preferably cycloalkyl having 3 to 14 carbon atoms, more preferably cycloalkyl having 3 to 10 carbon atoms). As the alkenylene, the form -CR=CR- is most preferable, and as the alkylene, the form -CR2-CR2- is most preferable, where R is hydrogen or a substituent, and the preferred range of the substituent can be found in the above description of alkenylene and alkylene. The details of the substituents listed here will be described later.

[0065] Examples of L include a single bond and a linking group Q, and preferably, a single bond, -N(-R)-, -O-, -S-, -C(-R)2-, alkenylene, arylene, and heteroarylene are more preferable, a single bond, arylene, -N(-R)-, -O-, and -S- are further preferable, and a single bond and arylene are most preferable. The above description can be referred to for the preferable ranges of these. Phenylene is most preferable as the arylene. At least one hydrogen of these is unsubstituted or substituted, and the above description can be referred to for the preferable range of the substituent.

[0066] At least one L is alkylene, cycloalkylene, alkenylene, alkynylene, arylene or heteroarylene, preferably alkenylene or arylene, and most preferably phenylene. The above description can be referred to for the preferred ranges. At least one hydrogen of these is unsubstituted or substituted, and the above description can be referred to for the preferred ranges.

[0067] The position at which the two rings are bonded by the bonding group is not particularly limited as long as it is a bondable position, but it is preferable that they are bonded at the most adjacent positions, and for example, it is preferable that they are bonded at ortho (2-position) positions based on the bonding position (1-position) of "N" in each ring (see the structural formulas of formula (1A) and formula (1B)).

[0068] In the sub-formulas (2A) and (2B), the rings c and d are also bonded by L in the same manner as in the superordinate formula. In the sub-formula (2B), the rings g and b, and the rings f and e are also bonded independently by L in the same manner as in the superordinate formula. They may be bonded by a single bond or a linking group (collectively also referred to as a linking group). The bond between the rings c and d via L consisting of a single bond or a linking group Q is also referred to as a cLd bond, the bond between the rings g and b is also referred to as a gLb bond, and the bond between the rings f and e is also referred to as an fLe bond. The type and bonding position of the linking group Q can be found in the explanation of the superordinate formula.

[0069] <Explanation of Bond L (1)> In the compound of the present invention, as described above, the C ring and the D ring (c ring and d ring), the G ring and the B ring (g ring and b ring), and the F ring and the E ring (f ring and e ring) can be bonded by L, so that the first bridged structure can be formed in the formula (1A) and the formula (2A), and the first, second and third bridged structures can be formed in the formula (1B) and the formula (2B). L in the following structural formula means a bonding group (single bond and linking group). However, the compound of the present invention is characterized in that one or two of the three bridged structures that can be formed in the molecule are formed. [ka] [ka]

[0070] As described above, L includes a single bond and a linking group as a bonding group, and the bonding positions between rings are not limited. In addition, as described elsewhere, the ring structure of each ring such as ring c changes due to bonding between adjacent substituents.

[0071] The position at which the two rings are bonded by L is not particularly limited as long as it is a bondable position, but it is preferable that they are bonded at the most adjacent positions, and for example, it is preferable that they are bonded at the ortho (2-position) positions based on the bonding position (1-position) of "N" in each ring (see the structural formulas of formula (1A), formula (1B), formula (2A), and formula (2B)). When L is formed, the two rings which it bonds to are both preferably benzene rings.

[0072] < Linking element X in compound 1 and X 2 Description of > X in formula (1A) and formula (2A) 1 and X 2 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. Details of the substituents listed here will be described below.

[0073] X 1 and X 2 is preferably >NR, >O, >S, or >C(-R)2, more preferably >NR or >O, and even more preferably >NR. From the viewpoint of good TADF properties, >NR, >O, and >S are preferred, and more specifically, from the viewpoint of orbital localization due to the multiple resonance effect, >NR is preferred, and from the viewpoint of the heavy atom effect, >S is preferred. From the viewpoint of emission wavelength, >O is preferred for short wavelength emission, and >NR or >S is preferred for long wavelength emission.

[0074] A preferred embodiment of formula (1A) and formula (1B) is the following formula (1A-a), formula (1A-b), formula (1A-c), formula (1B-a), formula (1B-b), or formula (1B-c). 1 R of >NR, R of >C(-R)2, or R of >Si(-R)2 as X is bonded to at least one of the a ring and the B ring by a single bond or a linking group; 2R of >NR, R of >C(-R)2, or R of >Si(-R)2 as the above is bonded to at least one of the a ring and the E ring via a single bond or a linking group. In formula (1A) and formula (1B), X 1 or X 2 is >NR, and R is a single bond to ring B or ring E (ring b or ring e), or a linking group (L Q For each symbol and its preferred range, see the explanation of formula (1A) and formula (1B). In formula (1A-a), formula (1A-b), formula (1A-c), formula (1B-a), formula (1B-b), or formula (1B-c), X 1 or X 2 is not >NR. Also, L Q For details, please refer to the description of L. [ka]

[0075] At least one of the two Rs in >C(-R)2 and the two Rs in >Si(-R)2 may be bonded to each other via a single bond or a linking group (collectively referred to as a linking group). An example of this linking group is the linking group Q. Details of the substituents listed here will be described below. [ka]

[0076] As the bonding group, a single bond, alkenylene as a linking group, -N(-R)-, -O-, -S-, -C(-R)2-, -Si(-R)2-, and -Se- are preferred, a single bond, alkenylene (particularly, -CR=CR-), -N(-R)-, -O-, -S-, and -C(-R)2- are more preferred, a single bond, and -CR=CR-, -N(-R)-, -O-, and -S- as a linking group are further preferred, and a single bond is most preferred.

[0077] The position at which two R are bonded by a bonding group is not particularly limited as long as it is a bondable position, but it is preferable that they are bonded at the most adjacent positions. For example, when two R are phenyl groups, it is preferable that they are bonded at the ortho (2nd) positions based on the bonding position (1st position) of "C" or "Si" in the phenyl group (see the above structural formula).

[0078] <X 1 or X 2 Explanation of the change in ring structure due to bonding with the ring> X in formula (1A) and formula (2A) 1 R of >NR as the substituent, R of >C(-R)2, or R of >Si(-R)2 as the substituent is not bonded to or is bonded to at least one of the a ring and the B ring (b ring) by a single bond or a linking group (preferably a linking group Q, which are also collectively referred to as a linking group). X in formula (1A) and formula (2A) 2 R of >NR, R of >C(-R)2, or R of >Si(-R)2 as a substituent is not bonded to or is bonded to at least one of the a ring and the E ring (e ring) by a single bond or a linking group (collectively also referred to as a bonding group).

[0079] X involved in binding 1 or X 2 As the group, >NR and >C(-R)2 are preferred, and >NR is more preferred.

[0080] As the linking group, a single bond and -CR=CR-, -N(-R)-, -O-, -S-, -C(-R)2-, -Si(-R)2-, and -Se- are preferred, a single bond and -CR=CR-, -N(-R)-, -O-, -S-, and -C(-R)2- are more preferred, a single bond and -CR=CR-, -N(-R)-, -O-, and -S- are further more preferred, and a single bond and -CR=CR- are most preferred as the linking group Q.

[0081] The ring to be bonded is X. 1 With respect to X, ring B (ring b) is preferred. 2With regard to the above, ring E (e ring) is preferred.

[0082] The provision in formula (1A) of the higher-level formula that "R of >NR, R of >C(-R)2, or R of >Si(-R)2 is bonded to at least one of ring a and ring B (or ring E) through a single bond or a linking group Q" corresponds to the provision in formula (2A) of the lower-level formula that "R of >NR, R of >C(-R)2, or R of >Si(-R)2 is bonded to at least one of ring a and ring b (or ring e) through a single bond or a linking group Q that is -CR=CR-, -C≡C-, -N(-R)-, -O-, -S-, -C(-R)2-, -Si(-R)2-, or -Se-."

[0083] This definition can be expressed, for example, by the following structural formula. In the structural formula, the substituent R a , R b , R c , R d , and R e is hidden but actually exists. [ka]

[0084] In the structural formula on the left, X 1 and X 2 In the options (>NR, >C(-R)2, and >Si(-R)2), R is bonded to the b ring and e ring, respectively, and X is bonded to the b ring (benzene ring) and e ring (benzene ring). 1 or X 2 The fused ring B' and the fused ring E' are, for example, a dihydrodibenzoazepine ring, a dibenzoazepine ring, a tribenzoazepine, a phenoxazine ring, a phenothiazine ring, a carbazole ring, or an acridine ring.

[0085] The structure in the center shows a more specific example of the structure on the left, X 1 and X 2In this example, R (phenyl group) of >NR is bonded to the b ring (benzene ring) via the linking group Q, o-phenylene, to form a tribenzoazepine ring B', and is bonded to the e ring (benzene ring) via a single bond to form a carbazole ring E', as shown in the dashed line.

[0086] The structural formula on the right is a more specific example of the structural formula on the left, X 1 and X 2 In this example, R (phenyl group) of >NR is bonded to the b ring (benzene ring) via the linking group -O- to form a phenoxazine ring B' surrounded by a dashed line, and R is bonded to the e ring (benzene ring) via the linking group -S- to form a phenothiazine ring E' surrounded by a dashed line.

[0087] X 1 and X 2 In the options (>NR, >C(-R)2, and >Si(-R)2), the position where R is bonded to the ring (ring B, ring E, ring b, and ring e) via the bonding group is not particularly limited as long as it is a bondable position, but it is preferable that R is bonded to the most adjacent position. For example, when R is a phenyl group, the "X" in the ring and phenyl group to be bonded is 1 " or "X 2 It is preferable that the bonds are formed between the ortho (2-position) bonds relative to the bonding position (1-position) of " (see the structural formula above).

[0088] The above description of the specific examples does not apply to any other specific examples, such as X 1 and X 2 The same applies to the cases where either one of is bonded to a ring, is bonded to ring a, or is bonded via another linking group.

[0089] <Explanation on the number of bridge structures via single bonds or linking group Q in carbazole-like structures> As described above, in Formula (1A) and Formula (2A), the first cross-linked structure is formed from a C-ring and a D-ring bond cross-linked by a single bond or a linking group, or a c-ring d-bond and a d-ring cross-linked by an L composed of a single bond and a linking group Q, and the second cross-linked structure is X 1 B bond, X 1 QB bond, or X 1 b bond or X 1 Qb bond, and the third cross-linked structure is X 2 E bond, X 2 QE bond, X 2 e bond or X 2 Qe bond. Further, in Formula (1B) and Formula (2B), the first cross-linked similar structure is formed from a CLD bond or a cLd bond, and the second structure is GL Q B bond or gL Q b bond, and the third structure is FL Q E bond or fL Q e bond. The compound of the present invention is characterized in that at least one of these three cross-linked similar structures that can be formed in the molecule is formed, and at least one in the linking group Q is alkylene, cycloalkylene, alkenylene, alkynylene, arylene, and heteroarylene.

[0090] <Explanation of the structural changes of the a-ring, b~g rings> In the previous explanations, the a-ring, b-ring, c-ring, d-ring, e-ring, f-ring, and g-ring have been illustrated and described as benzene rings. Hereinafter, examples of structural changes to 5-membered or 6-membered aryl rings or heteroaryl rings where the a-ring, b-ring~g-ring are not benzene rings will be described. Note that the previous explanations are similarly understood even when these rings undergo the following structural changes.

[0091] <Structural change of the a-ring> In the a-ring in Formula (1A) and Formula (2A), "-C(-R a )=" may be replaced by "-N=", and it may be a pyridine ring. The following structural diagrams are diagrams showing only a part of the a-ring and its peripheral structure. [Chemical formula]

[0092] <Structural changes of the b-g rings> Any "-C(-R)=" (where R is R b , R c , R d , R e , R f , or R g ) in the b ring, c ring, d ring, e ring, f ring, and g ring in Formula (2A) and Formula (2B) may be replaced by "-N=". [Chemical formula] As shown above, for example, the position of "-C(-R d )=" in the d ring may be replaced by "-N=", and in this way, the d ring shown as a benzene ring in each formula may be changed to a pyridine ring, pyrimidine ring, pyridazine ring, pyrazine ring, or other nitrogen-containing heteroaryl ring. Also, when groups adjacent to each other exist on the d ring (the remaining two adjacent R d in the above formula), they may combine to form a heteroaryl ring (quinoline ring in the above formula) together with the d ring, and the formed ring may be further substituted (indicated by n Rs), as described above.

[0093] In addition, there are also the following modification examples. [Chemical formula]

[0094] X 1 X 2 , or the "-C(-R d )=" at the ortho or para position to the carbon to which >N- is bonded is preferably replaced by "-N=".

[0095] The same applies when other positions are replaced by "-N=" or when the b ring, c ring, e ring, f ring, and g ring other than the d ring change.

[0096] Note that all "-C(-R)=" (where R is R a If R b , R c , R d , R e , R f , or R g

[0046] In the case where the ring structure is a substituent, and in the case where the ring structure is a substituent, the substituent is preferably not "-N=".

[0097] In the formula (2A) and the formula (2B), any of "-C(-R)=C(-R)-" (wherein R is R b , R c , R d , R e , R f , or R g (which is a group represented by the formula (I)) 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] As shown above, for example, the d-ring "-C(-R d )=C(-R d In this way, the d ring shown as a benzene ring in each formula may be changed to an R-substituted pyrrole ring, furan ring, thiophene ring, or other nitrogen-oxygen-sulfur-containing heteroaryl ring (5-membered ring) or aryl ring (5-membered ring). In addition, when adjacent groups are present on the d ring (the remaining two adjacent R d) are bonded to ring d to form a heteroaryl ring (such as an indole ring, a benzofuran ring, or a benzothiophene ring substituted with R in the above formula) or an aryl ring, and the ring formed may be further substituted (represented by n Rs), as described above.

[0098] In addition, there are the following variations: [ka]

[0099] The same applies when other positions are replaced with "-N(-R)-", "-O-", "-S-", "-C(-R)2-", "-Si(-R)2-", or "-Se-", or when the b, c, e, f, and g rings other than the d ring are changed.

[0100] At least one of the two Rs in "-C(-R)2-" and at least one of the two Rs in "-Si(-R)2-" may be bonded to each other via a single bond or a linking group (collectively also referred to as a linking group). Examples of this linking group include -CH2-CH2-, -CHR-CHR-, -CR2-CR2-, -CH=CH-, -CR=CR-, -C≡C-, -N(-R)-, -O-, -S-, -C(-R)2-, -Si(-R)2-, or -Se-, and examples of the structure include the following: In addition, R of the -CHR-CHR-, R of -CR2-CR2-, 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, and at least one hydrogen in the R may be substituted with alkyl or cycloalkyl. In addition, two adjacent R may form a ring to form a cycloalkylene, arylene, or heteroarylene. Details of the substituents listed here will be described below. [ka]

[0101] As the bonding 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 even more preferred, and a single bond is most preferred.

[0102] The position at which two R are bonded by a bonding group is not particularly limited as long as it is a bondable position, but it is preferable that they are bonded at the most adjacent positions. For example, when two R are phenyl groups, it is preferable that they are bonded at the ortho (2nd) positions based on the bonding position (1st position) of "C" or "Si" in the phenyl group (see the above structural formula).

[0103] <Specific explanation of rings and substituents> Next, the details of the rings and substituents (including the second substituent which further substitutes the first substituent) enumerated in the above description will be explained together.

[0104] 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. In addition, the "aryl ring" as ring B to ring G in formula (1A) and formula (1B) is defined as "R b , R c , R d , R e , R f , and R g The term "aryl ring" corresponds to "an aryl ring formed by bonding adjacent groups among the above together with ring b, ring c, ring d, ring e, ring f, and ring g," but for this "formed aryl ring," since ring b to ring g are 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 the smallest five-membered ring, which is nine. However, rings b to g, which are benzene rings, may be changed to nitrogen-containing heteroaryl rings (six- or five-membered rings) or oxygen- and sulfur-containing heteroaryl rings (five-membered rings) as described above, and in this case, the lower limit of the number of carbon atoms changes accordingly.

[0105] Specific examples of the "aryl ring" include a monocyclic ring such as a benzene ring, a fused bicyclic ring such as a naphthalene ring, a fused tricyclic ring such as an acenaphthylene ring, a fluorene ring, a phenalene ring, or a phenanthrene ring, or an anthracene ring, a fused tetracyclic ring such as a triphenylene ring, a pyrene ring, or a naphthacene ring, or a fused pentacyclic ring such as a perylene ring or a pentacene ring.

[0106] 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. In addition, the "heteroaryl ring" is, for example, a heterocycle containing, as ring-constituting atoms other than carbon, 1 to 5 heteroatoms selected from oxygen, sulfur, and nitrogen. In addition, the "heteroaryl ring" as ring B to ring G in formula (1A) and formula (1B) is the "R b , R c , R d , R e , R f , and R g The term "heteroaryl ring" corresponds to "a heteroaryl ring formed by bonding adjacent groups among the above together with ring b, ring c, ring d, ring e, ring f, and ring g, respectively." However, for this "formed heteroaryl ring," since ring b to ring g are already composed of a benzene ring having 6 carbon atoms, the lower limit of the carbon number is the total carbon number of the fused ring formed by condensing this benzene ring with the smallest 5-membered ring, which is 6. However, rings b to g, which are benzene rings, may be changed to nitrogen-containing heteroaryl rings (six- or five-membered rings) or oxygen- and sulfur-containing heteroaryl rings (five-membered rings) as described above, and in this case, the lower limit of the number of carbon atoms changes accordingly.

[0107] 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, Examples of the ring 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.

[0108] The following formula (BO) is also included in the heteroaryl ring. [ka]

[0109] 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.

[0110] Specific examples of "aryl" include, for example, the monocyclic ring system phenyl, the bicyclic ring system biphenylyl (2-biphenylyl, 3-biphenylyl, or 4-biphenylyl), the fused bicyclic ring system naphthyl (1-naphthyl or 2-naphthyl), the 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), the fused tricyclic ring system acenaphthylene-(1-, 3-, 4- , or 5-)yl, fluoren-(1-, 2-, 3-, 4-, or 9-)yl, phenalen-(1- or 2-)yl, phenanthrene-(1-, 2-, 3-, 4-, or 9-)yl, or anthracene-(1-, 2-, or 9-)yl, the tetracyclic ring system quaterphenylyl (5'-phenyl-m-terphenyl-2-yl, 5'-phenyl-m-terphenyl-3-yl, 5'-furanyl, and the like. Examples of such ring systems include the fused tetracyclic ring systems, triphenylene-(1- or 2-)yl, pyrene-(1-, 2-, or 4-)yl, or naphthacene-(1-, 2-, or 5-)yl, and the fused pentacyclic ring systems, perylene-(1-, 2-, or 3-)yl, or pentacene-(1-, 2-, 5-, or 6-)yl.

[0111] 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 in the aryl is replaced by 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). As an example, when the second substituent is a fluorenyl group, at least one hydrogen atom at the 9-position is substituted with an aryl group such as phenyl, an alkyl group such as methyl, or a cycloalkyl group such as cyclohexyl or adamantyl, and such groups are also included in the aryl group as the second substituent.

[0112] The "arylene" 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 is removed from the above-mentioned "aryl" (monovalent group) to form a divalent group.

[0113] The "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. In addition, the "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.

[0114] 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, carbolyl, acryloyl, and the like. diphenyl, phenoxathiinyl, 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, benzobenzoindolocarbazolyl, imidazolinyl, or oxazolinyl.

[0115] Moreover, a monovalent group obtained by removing one hydrogen from the following formula (BO) is also included in heteroaryl. [ka]

[0116] In addition, 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 in the heteroaryl is replaced by 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). An example of such a case is 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 a group is also included in the heteroaryl as the second substituent.

[0117] The "heteroarylene" 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. In addition, the "heteroarylene" is, for example, 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.

[0118] The term "diarylamino" refers to an amino group substituted with two aryl groups. For details of the aryl group, see the above description of the "aryl". The term "diheteroarylamino" refers to an amino group substituted with two heteroaryls. For details of this heteroaryl, the above description of "heteroaryl" can be cited. The "arylheteroarylamino" is an amino group substituted with an aryl and a heteroaryl, and the details of the aryl and the heteroaryl can be found in the above descriptions of the "aryl" and the "heteroaryl".

[0119] The description "two heteroaryls are bonded via a linking group or are not bonded" in diarylamino (two aryls are bonded via a linking group or are not bonded), diheteroarylamino (two heteroaryls are bonded via a linking group or are not bonded), and arylheteroarylamino (aryl and heteroaryl are bonded via a linking group or are not bonded) means that, for example, two phenyl groups of a diphenylamino group form a bond with a linking group as shown below. This explanation also applies to diheteroarylamino and arylheteroarylamino formed by aryls and heteroaryls. As the linking group, a linking group Q is preferred, and the description in the specification can be referred to for its preferred range (including the preferred range of the substituent). [ka]

[0120] In addition, when the term "diarylamino", "diheteroarylamino" or "arylheteroarylamino" is used simply in this specification, unless otherwise specified, it is assumed that the following explanation is added: "two aryls are bonded to each other via a linking group or are not bonded to each other", "two heteroaryls are bonded to each other via a linking group or are not bonded to each other", and "an aryl and a heteroaryl are bonded to each other via a linking group or are not bonded to each other", respectively.

[0121] "Diarylboryl" is 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 are not bonded to each other or are bonded to each other via a single bond or a linking group (preferably a linking group Q). The definition of the linking group Q and the preferred range thereof can be found in the description of this specification.

[0122] The "alkyl" may be either straight chain or branched chain, for example, straight chain alkyl having 1 to 24 carbon atoms or branched chain alkyl having 3 to 24 carbon atoms, and preferably alkyl having 1 to 18 carbon atoms (branched chain alkyl having 3 to 18 carbon atoms), alkyl having 1 to 12 carbon atoms (branched chain alkyl having 3 to 12 carbon atoms), alkyl having 1 to 6 carbon atoms (branched chain alkyl having 3 to 6 carbon atoms), alkyl having 1 to 5 carbon atoms (branched chain alkyl having 3 to 5 carbon atoms), alkyl having 1 to 4 carbon atoms (branched chain alkyl having 3 to 4 carbon atoms), etc.

[0123] 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 groups 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.

[0124] The "alkylene" includes a divalent group in which one hydrogen atom has been removed from the above-mentioned "alkyl". For example, it is a linear alkylene having 1 to 24 carbon atoms or a branched alkylene having 3 to 24 carbon atoms, and preferably, it is an alkylene having 1 to 18 carbon atoms (branched alkylene having 3 to 18 carbon atoms), an alkylene having 1 to 12 carbon atoms (branched alkylene having 3 to 12 carbon atoms), an alkylene having 1 to 6 carbon atoms (branched alkylene having 3 to 6 carbon atoms), an alkylene having 1 to 5 carbon atoms (branched alkylene having 3 to 5 carbon atoms), an alkylene having 1 to 4 carbon atoms (branched alkylene having 3 to 4 carbon atoms), etc.

[0125] For "alkenyl", the above explanation of "alkyl" can be referred to, and it is a group in which a CC single bond in the structure of "alkyl" is replaced with a C=C double bond, and 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). "Alkenyl" includes linear alkenyl having 2 to 24 carbon atoms or branched alkenyl having 4 to 24 carbon atoms. Alkenyl having 2 to 18 carbon atoms is preferable, alkenyl having 2 to 12 carbon atoms is more preferable, alkenyl having 2 to 6 carbon atoms is further preferable, and alkenyl having 2 to 4 carbon atoms is particularly preferable. Specific examples of "alkenyl" include vinyl, allyl, butadienyl, etc.

[0126] The term "alkenylene" refers to a divalent group obtained by removing one hydrogen from the above-mentioned "alkenyl".

[0127] For "alkynyl", the explanation of "alkyl" above can be referred to. It is a group in which the 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).

[0128] The term "alkynylene" refers to a divalent group obtained by removing one hydrogen from the above-mentioned "alkynyl".

[0129] The "cycloalkyl" is, for example, cycloalkyl having 3 to 24 carbon atoms, and preferably cycloalkyl having 3 to 20 carbon atoms, cycloalkyl having 3 to 16 carbon atoms, cycloalkyl having 3 to 14 carbon atoms, cycloalkyl having 3 to 12 carbon atoms, cycloalkyl having 5 to 10 carbon atoms, cycloalkyl having 5 to 8 carbon atoms, cycloalkyl having 5 to 6 carbon atoms, or cycloalkyl having 5 carbon atoms.

[0130] Specific examples of "cycloalkyl" include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, or alkyl (particularly methyl) substituted derivatives of these having 1 to 5 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.

[0131] "Cycloalkylene" is, for example, cycloalkylene having 3 to 24 carbon atoms, and preferably cycloalkylene having 3 to 20 carbon atoms, cycloalkylene having 3 to 16 carbon atoms, cycloalkylene having 3 to 14 carbon atoms, cycloalkylene having 3 to 12 carbon atoms, cycloalkylene having 5 to 10 carbon atoms, cycloalkylene having 5 to 8 carbon atoms, cycloalkylene having 5 to 6 carbon atoms, cycloalkylene having 5 carbon atoms, or the like. Specific examples of "cycloalkylene" include structures obtained by removing one hydrogen from the above-mentioned "cycloalkyl" (monovalent group) to form a divalent group.

[0132] The "alkoxy" may be either straight chain or branched chain, for example, straight chain alkoxy having 1 to 24 carbon atoms or branched chain alkoxy having 3 to 24 carbon atoms, and preferably alkoxy having 1 to 18 carbon atoms (branched chain alkoxy having 3 to 18 carbon atoms), alkoxy having 1 to 12 carbon atoms (branched chain alkoxy having 3 to 12 carbon atoms), alkoxy having 1 to 6 carbon atoms (branched chain alkoxy having 3 to 6 carbon atoms), alkoxy having 1 to 5 carbon atoms (branched chain alkoxy having 3 to 5 carbon atoms), alkoxy having 1 to 4 carbon atoms (branched chain alkoxy having 3 to 4 carbon atoms), etc.

[0133] 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 aryloxy group include n-tyl-4-heptyloxy, n-octyloxy, t-octyloxy (1,1,3,3-tetramethylbutyloxy), 1,1-dimethyloctyloxy, n-nonyloxy, n-decyloxy, 1-methyldecyloxy, n-undecyloxy, n-dodecyloxy, n-tridecyloxy, n-tetradecyloxy, n-pentadecyloxy, n-hexadecyloxy, n-heptadecyloxy, n-octadecyloxy, and n-eicosyloxy.

[0134] "Aryloxy" is a group represented by "Ar-O- (Ar is an aryl group)". For details of the aryl, see the explanation of "aryl" above.

[0135] "Arylthio" is a group represented by "Ar-S-(Ar is an aryl group)", and the above explanation of "aryl" can be cited for details of the aryl.

[0136] The "substituted silyl" is, for example, a silyl substituted with at least one of an aryl, an alkyl, and a cycloalkyl, and is preferably a triarylsilyl, a trialkylsilyl, a tricycloalkylsilyl, a dialkylcycloalkylsilyl, or an alkyldicycloalkylsilyl.

[0137] The term "triarylsilyl" refers to a silyl group substituted with three aryl groups. For details of the aryl groups, see the above description of the "aryl". Specific "triarylsilyl" includes, for example, triphenylsilyl, diphenylmononaphthylsilyl, monophenyldinaphthylsilyl, trinaphthylsilyl, and the like.

[0138] The term "trialkylsilyl" refers to a silyl group substituted with three alkyl groups. For details of this alkyl, see the above description of "alkyl." Specific examples of "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.

[0139] The term "tricycloalkylsilyl" refers to a silyl group substituted with three cycloalkyl groups. For details of this cycloalkyl, see the above description of "cycloalkyl." Specific "tricycloalkylsilyl" includes, for example, tricyclopentylsilyl or tricyclohexylsilyl.

[0140] The "dialkylcycloalkylsilyl" is a silyl group substituted with two alkyls and one cycloalkyl. For details of the alkyl and cycloalkyl, see the above descriptions of "alkyl" and "cycloalkyl".

[0141] The term "alkyldicycloalkylsilyl" refers to a silyl group substituted with one alkyl and two cycloalkyl. For details of the alkyl and cycloalkyl, see the above descriptions of "alkyl" and "cycloalkyl".

[0142] Specifically, the emission wavelength can be adjusted by the steric hindrance, electron donating property and electron withdrawing property of the structure of the first and second substituents. The groups represented by the following structural formulas are preferred, and more preferred are methyl, t-butyl, t-amyl, t-octyl, neopentyl, 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, and bis(p-(t-butyl)phenyl)amino. Preferred are methyl, t-butyl, t-amyl, t-octyl, neopentyl, adamantyl, phenyl, o-tolyl, 2,6-xylyl, 2,4,6-mesityl, diphenylamino, di-p-tolylamino, bis(p-(t-butyl)phenyl)amino, carbazolyl, 3,6-dimethylcarbazolyl, and 3,6-di-t-butylcarbazolyl. From the viewpoint of ease of synthesis, larger steric hindrance is preferred for selective synthesis, and specifically, t-butyl, t-amyl, t-octyl, adamantyl, o-tolyl, p-tolyl, 2,4-xylyl, 2,5-xylyl, 2,6-xylyl, 2,4,6-mesityl, di-p-tolylamino, bis(p-(t-butyl)phenyl)amino, 3,6-dimethylcarbazolyl and 3,6-di-t-butylcarbazolyl are preferred.

[0143] In the structural formulas below, "Me" represents methyl, "tBu" represents t-butyl, "tAm" represents t-amyl, and "tOct" represents t-octyl, and * represents the bond position. [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka]

[0144] <Explanation 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.

[0145] For example, at least one of ring B, ring C, ring D, ring E, ring F, ring G, aryl, and heteroaryl in the compound represented by formula (1A) or formula (1B), and ring b, ring c, ring d, ring e, ring f, ring g, the "formed ring", aryl, and heteroaryl in the compound represented by formula (2A) or formula (2B) (including aryl and heteroaryl as part of each substituent listed above) may be fused with at least one cycloalkane.

[0146] 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.

[0147] Specific examples of cycloalkanes include cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclooctane, cyclononane, cyclodecane, norbornene, bicyclo[1.1.0]butane, bicyclo[1.1.1]pentane, bicyclo[2.1.0]pentane, bicyclo[2.1.1]hexane, bicyclo[3.1.0]hexane, bicyclo[2.2.1]heptane, bicyclo[2.2.2]octane, adamantane, diamantane, decahydronaphthalene, and decahydroazulene, as well as alkyl (particularly methyl) substituted, halogen (particularly fluorine) substituted, and deuterium substituted derivatives of these having 1 to 5 carbon atoms.

[0148] Among these, for example, as shown in the following structural formula, a structure in which at least one hydrogen atom is substituted on the carbon atom at the α-position of a cycloalkane (a carbon atom at a position adjacent to the carbon atom at the condensation site in a cycloalkyl condensed to an aromatic ring or a heteroaromatic ring) is preferred, a structure in which two hydrogen atoms are substituted on the carbon atom at the α-position is more preferred, and a structure in which a total of four hydrogen atoms are substituted on the two carbon atoms at the α-position is even more preferred. Examples of this substituent include an alkyl (particularly methyl) substituent having 1 to 5 carbon atoms, a halogen (particularly fluorine) substituent, and a deuterium substituent. [ka]

[0149] The number of cycloalkanes condensed to one aromatic ring or heteroaromatic ring is preferably 1 to 3, more preferably 1 or 2, and even more preferably 1. For example, the following shows an example in which one or more cycloalkanes are condensed to one benzene ring (phenyl group). In each structural formula, * means a benzene ring contained in the skeleton structure of the compound when it is a benzene ring, and means a bond substituted on the skeleton structure of the compound when it is a phenyl group. Cycloalkanes condensed as in formula (Cy-1-4) and formula (Cy-2-4) may be condensed together. The same applies when the condensed ring (group) is an aromatic ring or heteroaromatic ring other than a benzene ring (phenyl group), or when the condensed cycloalkane is a cycloalkane other than cyclopentane or cyclohexane. [ka]

[0150] 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 shows an example in which one or more -CH2- in a cycloalkane fused to one benzene ring (phenyl group) are replaced with -O-. 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 that substitutes for 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]

[0151] At least one hydrogen atom in the cycloalkane may be substituted, and examples of the substituent include aryl, heteroaryl, diarylamino (two aryls are not bonded to each other or are bonded via a linking group), diheteroarylamino (two heteroaryls in diheteroarylamino are not bonded to each other or are bonded via a linking group), arylheteroarylamino (aryl and heteroaryl are not bonded to each other or are bonded via a linking group), diarylboryl (two aryls are not bonded to each other or are bonded via a single bond or a linking group), alkyl, cycloalkyl, alkoxy, aryloxy, substituted silyl, deuterium, cyano, and halogen, and the details of these can be cited from the explanation of the first substituent described 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. In addition, when cycloalkyl is substituted, it may be a substitution form that forms a spiro structure, and for example, an example in which a spiro structure is formed in a cycloalkane condensed to one benzene ring (phenyl group) is 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. [ka]

[0152] Other forms of cycloalkane condensation include, for example, the polycyclic aromatic compound of the present invention is substituted with a diarylamino group condensed with a cycloalkane (condensed to the aryl group portion), a carbazolyl group condensed with a cycloalkane (condensed to the benzene ring portion), or a benzocarbazolyl group condensed with a cycloalkane (condensed to the benzene ring portion). The above explanation of "diarylamino group" can be cited.

[0153] Further, as a more specific example, R in the polycyclic aromatic compound represented by formula (1A) or formula (2A) 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).

[0154] <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 halogen. The halogen atom is fluorine, chlorine, bromine, or iodine, preferably fluorine, chlorine, or bromine, and more preferably fluorine or chlorine.

[0155] <Explanation of specific examples of the polycyclic aromatic compound of the present invention> For example, a compound represented by any one of the following structural formulas is preferred. [ka] TIFF0007622941000050.tif59113 TIFF0007622941000051.tif54170In each expression, R each independently represents a hydrogen atom, 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 to each other 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, in which at least one hydrogen atom is optionally substituted by an alkyl having 1 to 5 carbon atoms or a cycloalkyl having 5 to 10 carbon atoms; Each o is independently an integer from 1 to 3; Each p is independently an integer of 1 to 4; Each q is independently an integer of 1 to 5, At least one hydrogen in the compounds represented by the above formulas may be substituted with deuterium, cyano, or halogen.

[0156] For a more specific description of R, the above description of aryl etc. can be cited. In addition, o, p and q are preferably 1 or 2, more preferably 1, and further preferably 0.

[0157] <Use as a thermally activated delayed fluorescence (TADF) material> The compound of the present invention can also be used as a TADF material. In particular, the compounds represented by formulae (1A) and (2A) are more preferable than the compounds represented by formulae (1B) and (2B), and the rings sharing a bond with the fused bicyclic structures in rings B to G and rings b to g are preferably six-membered rings, and more preferably six-membered aryl rings including ring a.

[0158] <Explanation of specific examples of the polycyclic aromatic compound of the present invention> 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.

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[0178] The polycyclic aromatic compound according to the present invention can also be used as a material for organic devices, for example, a material for organic electroluminescent elements, a material for organic field effect transistors, or a material for organic thin-film solar cells, in the form of a polymer compound obtained by polymerizing a reactive compound substituted with a reactive substituent as a monomer (the monomer for obtaining this polymer compound has a polymerizable substituent), 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 polymer crosslinked polymer obtained by further crosslinking the pendant polymer compound (the pendant polymer compound for obtaining this pendant polymer crosslinked polymer has a crosslinkable substituent).

[0179] The reactive substituents mentioned above (including the polymerizable substituents, the crosslinkable substituents, and the reactive substituents for obtaining a pendant polymer, hereinafter also referred to simply as "reactive substituents") are not particularly limited as long as they are substituents capable of increasing the molecular weight of the polycyclic aromatic compound, substituents capable of further crosslinking the polymer compound thus obtained, and substituents capable of pendant reaction with the main chain polymer, but are preferably those having the following structures: * in each structural formula indicates a bond position. [ka]

[0180] Each L is independently a single bond, -O-, -S-, >C=O, -OC(=O)-, an alkylene having 1 to 12 carbon atoms, an oxyalkylene having 1 to 12 carbon atoms, or a polyoxyalkylene having 1 to 12 carbon atoms. Among the above substituents, a group represented by formula (XLS-1), formula (XLS-2), formula (XLS-3), formula (XLS-9), formula (XLS-10) or formula (XLS-17) is preferred, and a group represented by formula (XLS-1), formula (XLS-3) or formula (XLS-17) is more preferred.

[0181] Such polymer compounds, crosslinked polymers, pendant-type polymer compounds, and pendant-type crosslinked polymers may contain, in addition to the repeating unit of the polycyclic aromatic compound according to the present invention, 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, as a repeating unit.

[0182] Examples of the substituents 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 in the polycyclic aromatic compound according to the present invention can be cited.

[0183] The uses of such polymer compounds, crosslinked polymers, pendant type polymer compounds and pendant type crosslinked polymers (hereinafter sometimes simply referred to as "polymer compounds and crosslinked polymers") will be described later in detail.

[0184] 2. Method for producing polycyclic aromatic compounds according to the present invention The polycyclic aromatic compound of the present invention is basically prepared by first bonding the a ring to the B ring to the G ring or the b ring to the g ring with a bonding group (such as “N” or X 1 or X 2 (a) is bonded to the rings B to G or the rings b to g via a bonding group (Y 1 ~Y 3 The final product can be produced by bonding via a group containing the following (second reaction). The production method described in WO 2015 / 102118 can be used as a reference.

[0185] In the first reaction, for example, etherification reactions can be carried out using common reactions such as nucleophilic substitution reactions and the Ullmann reaction, while amination reactions can be carried out using common reactions such as the Buchwald-Hartwig reaction, and in the second reaction, tandem hetero Friedel-Crafts reactions (sequential aromatic electrophilic substitution reactions, hereafter the same) can be used.

[0186] The second reaction is carried out by reacting ring a with rings B to G or rings b to g with Y 1 ~Y 3 This is a reaction that introduces "N" and X. 1 and X 2 The hydrogen atoms between the "N"s and between the "N"s are orthometalated with n-butyllithium, sec-butyllithium, or t-butyllithium, etc. Then, Y is reacted with boron trichloride or boron tribromide, etc. 1 ~Y 3 After performing lithium-boron metal exchange, a tandem boron-Friedel-Crafts reaction can be carried out by adding a Bronsted base such as N,N-diisopropylethylamine to obtain the target compound. In the second reaction, a Lewis acid such as aluminum trichloride can be added to promote the reaction. The symbols in the structural formulae in the following schemes (1) and (2) and the subsequent schemes are defined as above. In addition, the reaction step of metallizing a hydrogen atom (H) using an organic alkali compound described in Journal of The American Chemistry, 2018, 140, 1195-1198 can be omitted, and a reaction step of metalizing a hydrogen atom (H) using an organic alkali compound can be omitted, and a reaction step of metalizing a hydrogen atom (H) using an organic alkali compound can be carried out by adding a Lewis acid such as aluminum trichloride to obtain the target compound. 1 Alternatively, the compound can be reacted directly with a halogenide such as boron tribromide.

[0187] [ka] [ka]

[0188] In the above scheme, lithium was introduced to the desired position by ortho-metallation, but as shown in the following scheme (3), lithium can also be introduced to the desired position by introducing a bromine atom or the like to the desired position and then by halogen-metal exchange. This method is useful because it allows the production of the target product even in cases where ortho-metallation is not possible due to the influence of substituents. [ka]

[0189] The above schemes (1) to (3) are 1 ~Y 3 This is a typical method for producing a compound in which the atom is boron (B).

[0190] Next, as an example, Y 1 ~Y 3 The cases where X is a phosphorus sulfide, phosphorus oxide, or phosphorus atom are shown in the following schemes (4) and (5). As in the previous cases, first, "N" and X 1 and X 2 The hydrogen atoms between and between "N"s are orthometalated with n-butyllithium or the like. Next, phosphorus trichloride and sulfur are added in that order, and finally a Lewis acid such as aluminum trichloride and a Bronsted base such as N,N-diisopropylethylamine are added to carry out the tandem phospha-Friedel-Crafts reaction to give Y 1 ~Y 3 A compound in which Y is a phosphorus sulfide can be obtained. In addition, by treating the obtained phosphorus sulfide compound with m-chloroperbenzoic acid (m-CPBA), Y can be obtained. 1 ~Y 3 is a phosphorus oxide, and by treating with triethylphosphine, Y 1 ~Y 3 It is possible to obtain a compound in which is a phosphorus atom.

[0191] [ka] [ka]

[0192] In the above scheme, Y 1 ~Y 3 Although examples such as B, P, P=O, and P=S have been described, other compounds can also be produced by appropriately changing the raw materials.

[0193] In the above scheme, Y such as boron trichloride or boron tribromide is 1 ~Y 3 Before adding the halide, "N" and X 1 and X 2 In the example shown here, the hydrogen atom (or halogen atom) between the two N's and the hydrogen atom (or halogen atom) between the two N's were ortho-metallated with butyllithium or the like to perform a tandem hetero Friedel-Crafts reaction. However, it is also possible to perform a tandem hetero Friedel-Crafts reaction using boron trichloride or boron tribromide or the like without ortho-metallation using butyllithium or the like. 1 ~Y 3 The reaction can also be driven by the addition of a halide.

[0194] Solvents used in the above scheme include t-butylbenzene, xylene, and the like.

[0195] Examples of the ortho-metallation reagent 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 Na.

[0196] The metal-(Y 1 ~Y 3 ) as a metal exchange reagent, Y 1 ~Y 3 trifluoride, Y 1 ~Y 3 trichloride, Y 1 ~Y 3 Tribromide of Y 1 ~Y 3 of triiodide, etc. 1 ~Y 3 Halides of Y such as CIPN(NEt2)2 1 ~Y 3 Aminated halides of Y 1 ~Y 3 Alkoxylated compounds of Y 1 ~Y 3and aryloxy compounds of the above.

[0197] Examples of the Bronsted base used in the above scheme include N,N-diisopropylethylamine, triethylamine, 2,2,6,6-tetramethylpiperidine, 1,2,2,6,6-pentamethylpiperidine, N,N-dimethylaniline, N,N-dimethyltoluidine, 2,6-lutidine, sodium tetraphenylborate, potassium tetraphenylborate, triphenylborane, tetraphenylsilane, Ar4BNa, Ar4BK, Ar3B, and Ar4Si (Ar is an aryl such as phenyl).

[0198] 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, CoBr3, etc.

[0199] In the above scheme, a Brønsted base or Lewis acid may be used to promote the tandem hetero Friedel-Crafts reaction. 1 ~Y 3 trifluoride, Y 1 ~Y 3 trichloride, Y 1 ~Y 3 Tribromide of Y 1 ~Y 3 of triiodide, etc. 1 ~Y 3 When using halides of Y, acids such as hydrogen fluoride, hydrogen chloride, hydrogen bromide, and hydrogen iodide are generated as the aromatic electrophilic substitution reaction proceeds, so the use of a Brønsted base to capture the acid is effective. 1 ~Y3 Aminated halides of Y 1 ~Y 3 When an alkoxylated compound of the above is used, since amines and alcohols are produced as the aromatic electrophilic substitution reaction proceeds, it is often not necessary to use a Brønsted base. However, since the amino and alkoxy groups have low ability to be eliminated, it is effective to use a Lewis acid that promotes their elimination.

[0200] 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.

[0201] 3. Organic Devices The polycyclic aromatic compound according to the present invention can be used as a material for an organic device, such as an organic electroluminescent element, an organic field effect transistor, or an organic thin-film solar cell.

[0202] 3-1. Organic electroluminescent device The organic EL element according to the present embodiment will be described in detail below with reference to the drawings. Fig. 1 is a schematic cross-sectional view showing the organic EL element according to the present embodiment.

[0203] <Structure of organic electroluminescent device> The organic EL element 100 shown in FIG. 1 has a substrate 101, an anode 102 provided on the substrate 101, a hole injection layer 103 provided on the anode 102, a hole transport layer 104 provided on the hole injection layer 103, an emitting layer 105 provided on the hole transport layer 104, an electron transport layer 106 provided on the emitting layer 105, an electron injection layer 107 provided on the electron transport layer 106, and a cathode 108 provided on the electron injection layer 107.

[0204] 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.

[0205] Not all of the above layers are essential, and the minimum structural unit is a structure consisting of an anode 102, an emitting layer 105, and a cathode 108. The hole injection layer 103, the hole transport layer 104, the electron transport layer 106, and the electron injection layer 107 are layers that may be provided optionally. Each of the above layers may consist of a single layer or multiple layers.

[0206] In addition to the above-mentioned "substrate / anode / hole injection layer / hole transport layer / light-emitting layer / electron transport layer / electron injection layer / cathode" configuration, the layers constituting the organic EL element may be configured as "substrate / anode / hole transport layer / light-emitting layer / electron transport layer / electron injection layer / cathode", "substrate / anode / hole injection ...hole transport layer / light-emitting layer / electron injection layer / cathode", "substrate / anode / hole injection layer / hole transport layer / light-emitting layer / electron injection layer / cathode", or "substrate / anode / hole injection layer / hole transport layer / light-emitting layer / electron transport The configuration may be, for example, "substrate / anode / light-emitting layer / electron transport layer / electron injection layer / cathode", "substrate / anode / hole transport layer / light-emitting layer / electron injection layer / cathode", "substrate / anode / hole transport layer / light-emitting layer / electron transport layer / cathode", "substrate / anode / hole transport layer / light-emitting layer / electron injection layer / cathode", "substrate / anode / hole injection layer / light-emitting layer / electron injection layer / cathode", "substrate / anode / hole injection layer / light-emitting layer / electron transport layer / cathode", "substrate / anode / hole injection layer / light-emitting layer / electron transport layer / cathode", "substrate / anode / light-emitting layer / electron transport layer / cathode", or "substrate / anode / light-emitting layer / electron injection layer / cathode".

[0207] <Substrate for organic electroluminescence device> The substrate 101 is a support for the organic EL element 100, and is usually made of quartz, glass, metal, plastic, or the like. The substrate 101 is formed into a plate, film, or sheet shape depending on the purpose, and for example, a glass plate, a metal plate, a metal foil, a plastic film, a plastic sheet, or the like is used. Among them, a glass plate and a plate made of a transparent synthetic resin such as polyester, polymethacrylate, polycarbonate, or polysulfone are preferable. For a glass substrate, soda-lime glass or alkali-free glass is used, and the thickness is sufficient to maintain mechanical strength, so that it may be, for example, 0.2 mm or more. The upper limit of the thickness is, for example, 2 mm or less, preferably 1 mm or less. As for the material of the glass, it is preferable that the amount of ions eluted from the glass is small, so alkali-free glass is preferable, but soda-lime glass with a barrier coat such as SiO2 is also commercially available, and this can be used. In addition, in order to improve the gas barrier properties of the substrate 101, a gas barrier film such as a dense silicon oxide film may be provided on at least one side thereof. It is particularly preferable to provide a gas barrier film when a synthetic resin plate, film or sheet having poor gas barrier properties is used as the substrate 101.

[0208] <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.

[0209] Materials for forming the anode 102 include inorganic compounds and organic compounds. Examples of inorganic compounds include metals (aluminum, gold, silver, nickel, palladium, chromium, etc.), metal oxides (indium oxide, tin oxide, indium-tin oxide (ITO), indium-zinc oxide (IZO), etc.), metal halides (copper iodide, etc.), copper sulfide, carbon black, ITO glass, and Nesa glass. Examples of organic compounds include polythiophenes such as poly(3-methylthiophene), polypyrrole, polyaniline, and other conductive polymers. In addition, materials that are used as anodes in organic EL elements can be appropriately selected and used.

[0210] The resistance of the transparent electrode is not limited as long as it can supply a sufficient current for the light emission of the light emitting element, but it is desirable that the resistance is low from the viewpoint of the power consumption of the light emitting element. For example, an ITO substrate of 300Ω / □ or less functions as an element electrode, but since it is now possible to supply substrates of about 10Ω / □, it is particularly desirable to use a low resistance product of, for example, 100 to 5Ω / □, preferably 50 to 5Ω / □. The thickness of the ITO can be selected arbitrarily according to the resistance value, but it is usually used in the range of 50 to 300 nm.

[0211] <Hole injection layer and hole transport layer in organic electroluminescence device> The hole injection layer 103 plays a role of efficiently injecting holes moving from the anode 102 into the light emitting layer 105 or the hole transport layer 104. The hole transport layer 104 plays a role of efficiently transporting holes injected from the anode 102 or holes injected from the anode 102 via the hole injection layer 103 to the light emitting layer 105. The hole injection layer 103 and the hole transport layer 104 are each formed by laminating and mixing one or more types of hole injection / transport materials, or by a mixture of a hole injection / transport material and a polymer binder. Alternatively, a layer may be formed by adding an inorganic salt such as iron (III) chloride to the hole injection / transport material.

[0212] The hole injection / transport material is required to efficiently inject / transport holes from the positive electrode between electrodes to which an electric field is applied, and it is desirable to have a high hole injection efficiency and efficiently transport the injected holes. For this purpose, it is preferable that the material has a small ionization potential, a large hole mobility, and excellent stability, and is unlikely to generate impurities that become traps during production and use. In the present invention, the polycyclic aromatic compound represented by the above general formula (1A) or general formula (1B) can be used as a material for the hole injection layer and the hole transport layer.

[0213] As the material for forming the hole injection layer 103 and the hole transport layer 104, any compound can be selected from compounds conventionally used as charge transport materials for holes in photoconductive materials, p-type semiconductors, and known compounds used in hole injection layers and hole transport layers of organic EL elements. Specific examples of such compounds include carbazole derivatives (N-phenylcarbazole, polyvinylcarbazole, etc.), biscarbazole derivatives such as bis(N-arylcarbazole) or bis(N-alkylcarbazole), triarylamine derivatives (polymers having an aromatic tertiary amino in the main chain or side chain, 1,1-bis(4-di-p-tolylaminophenyl)cyclohexane, N,N'-diphenyl-N,N'-di(3-methylphenyl)-4,4'-diaminobiphenyl, N,N'-diphenyl-N,N'-dinaphthyl-4,4'-diaminobiphenyl, N,N'-diphenyl-N,N'-di(3-methylphenyl)-4,4'-diphenyl-1,1'-diamine, N,N'-dinaphthyl-N,N'-diphenyl-4,4'-diphenyl-1,1'-diamine, N 4 ,N 4’ -Diphenyl-N 4 ,N 4’ -Bis(9-phenyl-9H-carbazol-3-yl)-[1,1'-biphenyl]-4,4'-diamine, N 4 ,N 4 ,N 4’ ,N 4’-Tetra[1,1'-biphenyl]-4-yl)-[1,1'-biphenyl]-4,4'-diamine, 4,4',4"-tris(3-methylphenyl(phenyl)amino)triphenylamine and other triphenylamine derivatives, starburst amine derivatives, etc.), stilbene derivatives, phthalocyanine derivatives (metal-free, copper phthalocyanine, etc.), pyrazoline derivatives, hydrazone compounds, benzofuran derivatives, thiophene derivatives, oxadiazole derivatives, quinoxaline derivatives Conductors (e.g., 1,4,5,8,9,12-hexaazatriphenylene-2,3,6,7,10,11-hexacarbonitrile, etc.), heterocyclic compounds such as porphyrin derivatives, polysilanes, etc. As polymers, polycarbonates and styrene derivatives having the above-mentioned monomers in their side chains, polyvinylcarbazole, polysilanes, etc. are preferred, but there are no particular limitations on the compounds as long as they can form a thin film required for fabricating a light-emitting device, can inject holes from the anode, and can transport holes.

[0214] It is also known that the electrical conductivity of organic semiconductors is strongly influenced by their doping. Such organic semiconductor matrix substances consist of compounds with good electron donating or accepting properties. For doping with electron donating substances, strong electron acceptors such as tetracyanoquinone dimethane (TCNQ) or 2,3,5,6-tetrafluorotetracyano-1,4-benzoquinone dimethane (F4TCNQ) are known (see, for example, the literature "M. Pfeiffer, A. Beyer, T. Fritz, K. Leo, Appl. Phys. Lett., 73(22), 3202-3204 (1998)" and the literature "J. Blochwitz, M. Pheiffer, T. Fritz, K. Leo, Appl. Phys. Lett., 73(6), 729-731 (1998)"). These generate so-called holes by an electron transfer process in the electron donating base substance (hole transport substance). The conductivity of the base material varies considerably depending on the number and mobility of holes. Matrix materials having hole transport properties are known, for example, benzidine derivatives (TPD, etc.) or starburst amine derivatives (TDATA, etc.), or certain metal phthalocyanines (especially zinc phthalocyanine (ZnPc) and the like) (JP 2005-167175 A).

[0215] The above-mentioned hole injection layer material and hole transport layer material can be used as a hole layer material in the form of a polymer compound obtained by polymerizing a reactive compound substituted with a reactive substituent as a monomer, or a crosslinked polymer thereof, or a pendant polymer compound obtained by reacting a main chain polymer with the reactive compound, or a crosslinked pendant polymer thereof. In this case, the reactive substituent can be quoted from the description of the polycyclic aromatic compound represented by the above general formula (1A) or general formula (1B). The applications of such polymer compounds and crosslinked polymers will be described in detail below.

[0216] <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 forming the light-emitting layer 105 may be a compound (light-emitting compound) that is excited and emits light by the recombination of holes and electrons, and is preferably a compound that can be formed into a stable thin film shape and exhibits strong light-emitting (fluorescence) efficiency in a solid state. In the present invention, the material for the light-emitting layer may 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.

[0217] The light-emitting layer may be a single layer or multiple layers, each of which is formed from materials for the light-emitting layer (host material, dopant material). The host material and the dopant material may each be one type or a combination of multiple types. The dopant material may be entirely contained in the host material or may be partially contained in the host material. As a doping method, the dopant material may be formed by co-evaporation with the host material, but it may also be mixed with the host material in advance and then simultaneously evaporated, or mixed with the host material together with an organic solvent in advance and then formed into a film by a wet film-forming method.

[0218] The amount of the host material used varies depending on the type of the host material and may be determined according to the properties of the host material. The amount of the host material used is preferably 50 to 99.999% by weight, more preferably 80 to 99.95% by weight, and even more preferably 90 to 99.9% by weight, of the total material for the light-emitting layer.

[0219] The amount of the 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 the dopant material 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, based on the total material for the light-emitting layer. The above range is preferable in that, for example, concentration quenching can be prevented. In addition, from the viewpoint of durability, it is also preferable that some or all of the hydrogen atoms of the dopant material are deuterated.

[0220] On the other hand, in the organic electroluminescence device using the thermally activated delayed fluorescence dopant material, the amount of the dopant material used is preferably low in terms of preventing concentration quenching phenomenon, but the amount of the dopant material used is preferably high in terms of the efficiency of the thermally activated delayed fluorescence mechanism.Furthermore, in the organic electroluminescence device using the thermally activated delayed fluorescence assist dopant material, the amount of the dopant material used is preferably low compared to the amount of the assist dopant material used in terms of the efficiency of the thermally activated delayed fluorescence mechanism of the assist dopant material.

[0221] In the case where an assist dopant material is used, the approximate amounts of the host material, the assist dopant material, and the dopant material used are 40 to 99.999% by weight, 59 to 1% by weight, and 20 to 0.001% by weight, respectively, based on the total material 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 compound represented by the above general formula (1A) or general formula (1B) and the polymer compound thereof can also be used as an assist dopant material.

[0222] Examples of host materials include condensed ring derivatives of anthracene and pyrene, which have long been known as light-emitting bodies, bisstyryl derivatives such as bisstyrylanthracene derivatives and distyrylbenzene derivatives, tetraphenylbutadiene derivatives, cyclopentadiene derivatives, fluorene derivatives, and benzofluorene derivatives.

[0223] 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 the triplet energy of the dopant or assist dopant having the highest triplet energy in the light-emitting layer, and 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 be used as the host material.

[0224] 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 including 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 the general formula (H1) is preferred. [ka]

[0225] <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, further preferably an arylene having 6 to 12 carbon atoms, particularly preferably an arylene having 6 to 10 carbon atoms, further preferably a heteroarylene having 2 to 25 carbon atoms, more preferably a heteroarylene having 2 to 20 carbon atoms, further preferably a heteroarylene having 2 to 15 carbon atoms, particularly preferably a heteroarylene having 2 to 10 carbon atoms. Specific examples of the 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.

[0226] <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, further 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 benzophenyl ... and monovalent groups such as a benzotriazole ring, a quinoline ring, an isoquinoline ring, a cinnoline ring, a quinazoline ring, a quinoxaline ring, a phthalazine ring, a naphthyridine ring, a purine ring, a pteridine ring, a carbazole ring, an acridine ring, a phenoxathiin ring, a phenoxazine ring, a phenothiazine ring, a phenazine ring, 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 (H2) may be substituted with alkyl having 1 to 6 carbon atoms, cycloalkyl having 3 to 14 carbon atoms, cyano, halogen or deuterium.

[0227] <Compound represented by general formula (H3) (an example of a polymer host material)> [ka]

[0228] In 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, in which two hydrogen atoms in MU are replaced by EC or MU, and k is an integer from 2 to 50,000.

[0229] More specifically, Each MU is independently arylene, heteroarylene, diarylenarylamino, diarylenarylboryl, oxaborine-diyl, or azaborine-diyl; each E C is independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, or aryloxy; At least one hydrogen in MU and EC may be further substituted with aryl, heteroaryl, diarylamino, alkyl, and cycloalkyl; k is an integer from 2 to 50,000. k is preferably an integer from 20 to 50,000, and more preferably an integer from 100 to 50,000.

[0230] At least one hydrogen atom in MU and EC in formula (H3) may be substituted with an alkyl group having 1 to 24 carbon atoms, a cycloalkyl group having 3 to 24 carbon atoms, a halogen atom or a deuterium atom; further, any -CH2- in the alkyl group may be substituted with -O- or -Si(CH3)2-; any -CH2- in the alkyl group except for the -CH2- directly bonded to EC in formula (H3) may be substituted with an arylene group having 6 to 24 carbon atoms; and any hydrogen atom in the alkyl group may be substituted with a fluorine atom.

[0231] Examples of MU include a divalent group represented by removing any two hydrogen atoms from any of the following compounds: [ka]

[0232] More specifically, the divalent group may be any of the following structures: In these, MU bonds to another MU or EC at *.

[0233] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka]

[0234] Examples of EC include monovalent groups represented by any of the following structures: In these, EC is bonded to MU at *.

[0235] [ka] [ka]

[0236] From the viewpoint of solubility and coating film-forming property, the compound represented by formula (H3) is preferably such that 10 to 100% of the total number of MUs (k) in the molecule have an alkyl having 1 to 24 carbon atoms, more preferably 30 to 100% of the total number of MUs (k) in the molecule have an alkyl having 1 to 18 carbon atoms (branched chain alkyl having 3 to 18 carbon atoms), and even more preferably 50 to 100% of the total number of MUs (k) in the molecule have an alkyl having 1 to 12 carbon atoms (branched chain alkyl having 3 to 12 carbon atoms). On the other hand, from the viewpoint of in-plane orientation and charge transport, it is preferable that 10 to 100% of the total number of MUs (k) in the molecule have an alkyl having 7 to 24 carbon atoms, and more preferably 30 to 100% of the total number of MUs (k) in the molecule have an alkyl having 7 to 24 carbon atoms (branched chain alkyl having 7 to 24 carbon atoms).

[0237] <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 to 2, and most preferably 1. When the compound contains a plurality of such structures, the structures are directly bonded to each other via a single bond or a specific linking group. [ka]

[0238] 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).

[0239] 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.

[0240] Examples of the substituent when H in "=C(-H)-" of G is substituted are as follows, but are not limited thereto.

[0241] Specific examples of the "aryl group" as a 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., and preferably phenyl, biphenylyl, terphenylyl, quaterphenylyl, naphthyl, triphenylenyl, and fluorenyl. Examples of aryl groups having a substituent include tolyl, xylyl, and 9,9-dimethylfluorenyl. As shown in the specific examples, the aryl group includes both fused and non-fused aryl groups.

[0242] 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.

[0243] The "substituted silyl group" which is 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.

[0244] Specific examples of the substituted or unsubstituted trialkylsilyl group include trimethylsilyl and triethylsilyl. Specific examples of the substituted or unsubstituted arylalkylsilyl group include diphenylmethylsilyl, ditolylmethylsilyl, and phenyldimethylsilyl. Specific examples of the substituted or unsubstituted triarylsilyl group include triphenylsilyl and tritolylsilyl.

[0245] 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.

[0246] The "substituted carboxy group" as a substituent includes, for example, benzoyloxy and the like.

[0247] Examples of the linking group that bonds a plurality of structures represented by formula (H4) include divalent to tetravalent, divalent to trivalent, or divalent derivatives of the above-mentioned aryl or heteroaryl.

[0248] Specific examples of the compound containing the structure represented by general formula (H4) are shown below. [ka] [ka]

[0249] <Compound represented by general formula (H5)> [ka] In the above formula (H5), R 1 ~R 11 are each independently hydrogen, aryl, heteroaryl, diarylamino (two aryls are not bonded to each other or are bonded via a linking group), diheteroarylamino (two heteroaryls of diheteroarylamino are not bonded to each other or are bonded via a linking group), arylheteroarylamino (aryls and heteroaryls are not bonded to each other or are bonded via a linking group), alkyl or cycloalkyl (all of the above, first substituents), in which at least one hydrogen may be further substituted with an aryl, heteroaryl, diarylamino, alkyl or cycloalkyl (all of the above, second substituents); R 1 ~R 11 adjacent groups among the above may be bonded to each other to form an aryl ring or a heteroaryl ring together with the a ring, the b ring or the c ring, and at least one hydrogen atom in the ring formed may be substituted with an aryl, a heteroaryl, a diarylamino (two aryls are not bonded to each other or are bonded via a linking group), a diheteroarylamino (two heteroaryls of the diheteroarylamino are not bonded to each other or are bonded via a linking group), an arylheteroarylamino (aryls and heteroaryls are not bonded to each other or are bonded via a linking group), an alkyl or a cycloalkyl (all of the above, first substituents), and at least one hydrogen atom in these may be further substituted with an aryl, a heteroaryl, a diarylamino, an alkyl or a cycloalkyl (all of the above, second substituents); In the a, b, and c rings, any "-C(-R)=" (where R is R 1 ~R 11 ) may be replaced with "-N=", At least one hydrogen in the compound represented by formula (H5) may be independently replaced with a halogen or deuterium.

[0250] In the formula (H5), any "-C(-R)=" (where R is R 1 ~R 11 (Is) 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, refer to the explanations in the above general formula (2A) and formula (2B).

[0251] Preferably, in the above formula (H5), R 1 ~R 11each independently represents a hydrogen atom, an aryl having 6 to 30 carbon atoms, a heteroaryl having 2 to 30 carbon atoms, a diarylamino (wherein the two aryl groups are not bonded to each other or are bonded via a linking group, and the aryl group is an aryl group having 6 to 12 carbon atoms), an alkyl group having 1 to 12 carbon atoms, or a cycloalkyl group having 3 to 16 carbon atoms, in which at least one hydrogen atom may be further substituted by an aryl group having 6 to 30 carbon atoms, a heteroaryl group having 2 to 30 carbon atoms, a diarylamino group (wherein the aryl group is an aryl group having 6 to 12 carbon atoms), an alkyl group having 1 to 12 carbon atoms, or a cycloalkyl group having 3 to 16 carbon atoms; R 1 ~R 11 Adjacent groups among these may be bonded to each other to form an aryl ring having 9 to 16 carbon atoms or a heteroaryl ring having 6 to 15 carbon atoms together with ring a, ring b or ring c, and at least one hydrogen in the formed ring may be substituted with an aryl having 6 to 30 carbon atoms, a heteroaryl having 2 to 30 carbon atoms, a diarylamino (wherein the two aryls are not bonded to each other or are bonded via a linking group, and the aryl is an 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 in these may be further substituted with 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), an alkyl having 1 to 12 carbon atoms or a cycloalkyl having 3 to 16 carbon atoms.

[0252] More preferably, in the above formula (H5), R 1 ~R 11are each independently a hydrogen atom, an aryl having 6 to 16 carbon atoms, a heteroaryl having 2 to 15 carbon atoms, a diarylamino (wherein the two aryls are not bonded to each other or are bonded via a linking group, and the aryl is an aryl having 6 to 10 carbon atoms), an alkyl having 1 to 6 carbon atoms, or a cycloalkyl having 3 to 14 carbon atoms, in which at least one hydrogen atom 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 two aryls are not bonded to each other or are bonded via a linking group, and the aryl is an aryl having 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 11 Adjacent groups among these may be bonded to each other to form an aryl ring having 9 to 12 carbon atoms or a heteroaryl ring having 6 to 12 carbon atoms together with ring a, ring b or ring c, and at least one hydrogen 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 (wherein the two aryls are not bonded to each other or are bonded via a linking group, and the aryl is an 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 in these may be further substituted with an aryl having 6 to 16 carbon atoms, a heteroaryl having 2 to 15 carbon atoms, diarylamino (wherein the two aryls are not bonded to each other or are bonded via a linking group, and the aryl is an aryl having 6 to 10 carbon atoms), an alkyl having 1 to 6 carbon atoms or a cycloalkyl having 3 to 14 carbon atoms.

[0253] In the above first and second substituents, examples of "aryl" and "heteroaryl" in aryl, heteroaryl, diarylamino, diheteroarylamino, and arylheteroarylamino include the following.

[0254] 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, further 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 condensed 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, Examples of such aryl groups include acenaphthylene-(1-,3-,4-,5-)yl, fluorene-(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), condensed tetracyclic aryl groups such as triphenylene-(1-,2-)yl, pyrene-(1-,2-,4-)yl, and naphthacene-(1-,2-,5-)yl, and condensed pentacyclic aryl groups such as perylene-(1-,2-,3-)yl and pentacene-(1-,2-,5-,6-)yl.

[0255] Specific examples of "heteroaryl" include heteroaryl having 2 to 30 carbon atoms, preferably heteroaryl having 2 to 25 carbon atoms, more preferably heteroaryl having 2 to 20 carbon atoms, further preferably heteroaryl having 2 to 15 carbon atoms, and particularly preferably heteroaryl having 2 to 10 carbon atoms. 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, phenoxathiyl, Examples of the alkyl group include ynyl, 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.

[0256] In the above 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. An alkyl having 1 to 18 carbon atoms (branched alkyl having 3 to 18 carbon atoms) is preferable, an alkyl having 1 to 12 carbon atoms (branched alkyl having 3 to 12 carbon atoms) is more preferable, an alkyl having 1 to 6 carbon atoms (branched alkyl having 3 to 6 carbon atoms) is even more preferable, an alkyl having 1 to 5 carbon atoms (branched alkyl having 3 to 5 carbon atoms) or an alkyl having 1 to 4 carbon atoms (branched alkyl having 3 to 4 carbon atoms) is particularly preferable, and methyl is most preferable. 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, and n-eicosyl. Further, for example, 1-ethyl-1-methylpropyl, 1,1-diethylpropyl, 1,1-dimethylbutyl, 1-ethyl-1-methylbutyl, 1,1,4-trimethylpentyl, 1,1,2-trimethylpropyl, 1,1-dimethyloctyl, 1,1-dimethylpentyl, 1,1-dimethylheptyl, 1,1,5-trimethylhexyl, 1-ethyl-1-methylhexyl, 1-ethyl-1,3-dimethylbutyl, 1,1,2,2-tetramethylpropyl, 1-butyl-1-methylpentyl, 1,1-diethylbutyl, 1-ethyl-1-methylpentyl, 1,1,3-trimethylbutyl, 1-propyl-1-methylpentyl, 1,1,2-trimethylpropyl, 1-ethyl-1,2,2-trimethylpropyl, 1-propyl-1-methylbutyl, and 1,1-dimethylhexyl.

[0257] 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.

[0258] When the first substituent is an 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 substitution with is more preferred, and the aryl is preferably a phenyl group.

[0259] When the first substituent is a 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 (eg, carbazolyl) may be substituted at the above-mentioned position via a phenylene group.

[0260] 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.

[0261] [ka] [ka]

[0262] The compound represented by formula (H5) can be produced by first bonding rings a to c with a bonding group (-O-) to produce an intermediate (first reaction), and then bonding rings a to c with B (boron) to produce a final product (second reaction). In the first reaction, for example, a general etherification reaction such as a nucleophilic substitution reaction or an Ullmann reaction can be used. In the second reaction, a tandem hetero Friedel-Crafts reaction (sequential aromatic electrophilic substitution reaction) can be used. For details of the first and second reactions, the explanations described in International Publication No. 2015 / 102118 can be referred to.

[0263] <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), in which at least one hydrogen may be further substituted with aryl, heteroaryl, diarylamino, alkyl, or cycloalkyl (all of which are second substituents); R 1 ~R 16 adjacent groups among the above may be bonded to each other to form an aryl ring or a heteroaryl ring together with the a ring, the b ring, 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 (all of which are referred to as a first substituent), and at least one hydrogen atom in these rings may be further substituted with an aryl, a heteroaryl, a diarylamino, an alkyl, or a cycloalkyl (all of which are referred to as a second substituent); At least one hydrogen in the compound represented by formula (H6) may be independently replaced with a halogen or deuterium.

[0264] Preferably, in the above formula (H6), R 1 ~R 16 are each independently a hydrogen atom, an aryl having 6 to 30 carbon atoms, a heteroaryl having 2 to 30 carbon atoms, a diarylamino (wherein the two aryls are not bonded to each other or are bonded via a linking group, and the aryl is an aryl having 6 to 12 carbon atoms), an alkyl having 1 to 12 carbon atoms, or a cycloalkyl having 3 to 16 carbon atoms, in which at least one hydrogen atom 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 two aryls are not bonded to each other or are bonded via a linking group, and the aryl is an aryl having 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 an aryl ring having 9 to 16 carbon atoms or a heteroaryl ring having 6 to 15 carbon atoms together with ring a, ring b, ring c, or ring d, and at least one hydrogen 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 (wherein the two aryls are not bonded to each other or are bonded via a linking group, and the aryl is an 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 in these may be further substituted with an aryl having 6 to 30 carbon atoms, a heteroaryl having 2 to 30 carbon atoms, diarylamino (wherein the two aryls are not bonded to each other or are bonded via a linking group, and the aryl is an aryl having 6 to 12 carbon atoms), an alkyl having 1 to 12 carbon atoms, or a cycloalkyl having 3 to 16 carbon atoms.

[0265] More preferably, in the above formula (H6), R 1 ~R 16 each independently represents a hydrogen atom, an aryl having 6 to 16 carbon atoms, a heteroaryl having 2 to 15 carbon atoms, a diarylamino (wherein the two aryl groups are not bonded to each other or are bonded via a linking group, and the aryl group is an aryl group having 6 to 10 carbon atoms), an alkyl group having 1 to 6 carbon atoms, or a cycloalkyl group having 3 to 14 carbon atoms, in which at least one hydrogen atom may be further substituted by an aryl group having 6 to 16 carbon atoms, a heteroaryl group having 2 to 15 carbon atoms, a diarylamino group (wherein the aryl group is an aryl group having 6 to 10 carbon atoms), an alkyl group having 1 to 6 carbon atoms, or a cycloalkyl group having 3 to 14 carbon atoms; R 1 ~R 16Adjacent groups among these may be bonded to each other to form an aryl ring having 9 to 12 carbon atoms or a heteroaryl ring having 6 to 12 carbon atoms together with ring a, ring b, ring c, or ring d, and at least one hydrogen 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 (wherein the two aryls are not bonded to each other or are bonded via a linking group, and the aryl is an 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 in these may be further substituted with an aryl having 6 to 16 carbon atoms, a heteroaryl having 2 to 15 carbon atoms, diarylamino (wherein the two aryls are not bonded to each other or are bonded via a linking group, and the aryl is an aryl having 6 to 10 carbon atoms), an alkyl having 1 to 6 carbon atoms, or a cycloalkyl having 3 to 14 carbon atoms.

[0266] In the above first and second substituents, examples of "aryl" and "heteroaryl" in aryl, heteroaryl, diarylamino (two aryls are not bonded to each other or are bonded via a linking group), diheteroarylamino (two heteroaryls in diheteroarylamino are not bonded to each other or are bonded via a linking group), and arylheteroarylamino (aryl and heteroaryl are not bonded to each other or are bonded via a linking group) include the following.

[0267] 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, further 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 condensed 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, Examples of such aryl groups include acenaphthylene-(1-,3-,4-,5-)yl, fluorene-(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), condensed tetracyclic aryl groups such as triphenylene-(1-,2-)yl, pyrene-(1-,2-,4-)yl, and naphthacene-(1-,2-,5-)yl, and condensed pentacyclic aryl groups such as perylene-(1-,2-,3-)yl and pentacene-(1-,2-,5-,6-)yl.

[0268] Specific examples of "heteroaryl" include heteroaryl having 2 to 30 carbon atoms, preferably heteroaryl having 2 to 25 carbon atoms, more preferably heteroaryl having 2 to 20 carbon atoms, further preferably heteroaryl having 2 to 15 carbon atoms, and particularly preferably heteroaryl having 2 to 10 carbon atoms. 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, phenoxathiyl, Examples of the alkyl group include ynyl, 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.

[0269] In the above 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. An alkyl having 1 to 18 carbon atoms (branched alkyl having 3 to 18 carbon atoms) is preferable, an alkyl having 1 to 12 carbon atoms (branched alkyl having 3 to 12 carbon atoms) is more preferable, an alkyl having 1 to 6 carbon atoms (branched alkyl having 3 to 6 carbon atoms) is even more preferable, an alkyl having 1 to 5 carbon atoms (branched alkyl having 3 to 5 carbon atoms) or an alkyl having 1 to 4 carbon atoms (branched alkyl having 3 to 4 carbon atoms) is particularly preferable, and methyl is most preferable. 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, and n-eicosyl. Further, for example, 1-ethyl-1-methylpropyl, 1,1-diethylpropyl, 1,1-dimethylbutyl, 1-ethyl-1-methylbutyl, 1,1,4-trimethylpentyl, 1,1,2-trimethylpropyl, 1,1-dimethyloctyl, 1,1-dimethylpentyl, 1,1-dimethylheptyl, 1,1,5-trimethylhexyl, 1-ethyl-1-methylhexyl, 1-ethyl-1,3-dimethylbutyl, 1,1,2,2-tetramethylpropyl, 1-butyl-1-methylpentyl, 1,1-diethylbutyl, 1-ethyl-1-methylpentyl, 1,1,3-trimethylbutyl, 1-propyl-1-methylpentyl, 1,1,2-trimethylpropyl, 1-ethyl-1,2,2-trimethylpropyl, 1-propyl-1-methylbutyl, and 1,1-dimethylhexyl.

[0270] In the above-mentioned first substituent and second substituent, examples of the "cycloalkyl" include cycloalkyl having 3 to 24 carbon atoms, cycloalkyl having 3 to 20 carbon atoms, cycloalkyl having 3 to 16 carbon atoms, cycloalkyl having 3 to 14 carbon atoms, cycloalkyl having 5 to 10 carbon atoms, cycloalkyl having 5 to 8 carbon atoms, cycloalkyl having 5 to 6 carbon atoms, cycloalkyl having 5 carbon atoms, and the like. For example, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, and their alkyl (especially methyl) substituents having 1 to 4 carbon atoms, bicyclo[1.1.0]butyl, bicyclo[1.1.1]pentyl, bicyclo[2.1.0]pentyl, bicyclo[2.1.1]hexyl, bicyclo[3.1.0]hexyl, bicyclo[2.2.1]heptyl, bicyclo[2.2.2]octyl, adamantyl, diamantyl, decahydronaphthalenyl, decahydroazulenyl, and the like can be mentioned.

[0271] The compound represented by the formula (H6) can be produced with reference to the description described in International Publication No. 2014 / 042197.

[0272] <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.

[0273] Examples of the TADF material that can be used for such a purpose 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

[0274] TADF materials are preferably donor-acceptor type TADF compounds (DA type TADF compounds) designed to localize the HOMO and LUMO within a molecule using electron-donating substituents called donors and electron-accepting substituents called acceptors, thereby allowing efficient reverse intersystem crossing to occur.

[0275] 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.

[0276] In general, TADF compounds using donors or acceptors have a large spin orbit coupling (SOC) due to their structure, and the exchange interaction between HOMO and LUMO is small, 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 have a large structural relaxation in the excited state (in some molecules, the stable structure differs between the ground state and the excited state, so when an external stimulus causes a conversion from the ground state to the excited state, the structure then changes to the stable structure in the excited state), giving a wide emission spectrum, which may reduce the color purity when used as a light-emitting material.

[0277] When the color purity is reduced by the TADF material, a fluorescent compound may be added as the other 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.

[0278] 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 functional groups containing nitrogen include groups derived from carbazole, dimethylcarbazole, di-t-butylcarbazole, dimethoxycarbazole, tetramethylcarbazole, benzofluorocarbazole, benzothienocarbazole, phenyldihydroindolocarbazole, phenylbicarbazole, bicarbazole, tercarbazole, diphenylcarbazolylamine, tetraphenylcarbazolyldiamine, phenoxazine, dihydrophenazine, phenothiazine, dimethyldihydroacridine, diphenylamine, bis(t-butyl)phenyl)amine, (diphenylamino)phenyl)diphenylbenzenediamine, dimethyltetraphenyldihydroacridinediamine, tetramethyl-dihydro-indenoacridine, and diphenyl-dihydrodibenzoazasiline. Examples of 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 dioxane, Examples of Ln include groups derived from phenyl, dimethylanthracenone, anthracenedione, pyridine, cycloheptabipyridine, benzenetricarbonitrile, fluorene dicarbonitrile, pyrazine dicarbonitrile, pyridine dicarbonitrile, dibenzoquinoxaline dicarbonitrile, pyrimidine, phenylpyrimidine, methylpyrimidine, triazine, triphenyltriazine, bis(phenylsulfonyl)benzene, dimethylthioxanthene dioxide, thianthrene tetraoxide, and tris(dimethylphenyl)borane. Examples of Ln include single bonds and arylenes, more specifically, phenylene, biphenylene, naphthylene, and the like. In addition, in any of the structures, hydrogen may be substituted with alkyl, cycloalkyl, and aryl. In particular, it is preferable that the compound has at least one partial structure selected from carbazole, phenoxazine, acridine, triazine, pyrimidine, pyrazine, thioxanthene, benzonitrile, phthalonitrile, isophthalonitrile, diphenylsulfone, triazole, oxadiazole, thiadiazole, and benzophenone.

[0279] 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]

[0280] In the above general formulas (H7-1), (H7-2) and (H7-3), M is each independently 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 height of the excited singlet energy level and the 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 independently is 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 preferable, and more specific examples thereof include phenylene, methylphenylene, and dimethylphenylene. Q is each independently =C(-H)- or =N-, and is preferably =N- from the viewpoint of shallowness of the LUMO of the partial structure to be formed and height 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 height 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 further 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 in the compounds represented by the above formulas may be substituted with a halogen or deuterium.

[0281] Examples of the compound represented by formula (H7) include compounds represented by the following structures: In the structural formula, * indicates a bond position, "Me" indicates a methyl group, and "tBu" indicates a t-butyl group.

[0282] [ka]

[0283] [ka]

[0284] [ka]

[0285] [ka]

[0286] [ka]

[0287]

change

[0288]

change

[0289]

change

[0290]

change

[0291] As the compound represented by general formula (H7), 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 among the specific compounds mentioned above.

[0292] In addition, as the dopant material, in addition to the polycyclic aromatic compounds represented by the above general formula (1A) or general formula (1B), known compounds can also be used, and the dopant material can be selected from various materials depending on the desired emission color.Specific examples of such compounds include condensed 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 bisstyrylanthracene 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.

[0293] Examples of dopant materials for each color of light emitted 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, pyrrolopyridine, and pyrrolopyridine. Examples of the aromatic heterocyclic compounds include 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.

[0294] In addition, 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, preferred examples of the compounds exemplified as the above blue to blue-green dopant materials include compounds in which a substituent that enables a longer wavelength, such as aryl, heteroaryl, arylvinyl, amino, or cyano, has been introduced.

[0295] 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 analogs thereof, 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, suitable examples of the compounds exemplified as the above blue to blue-green and green to yellow dopant materials include compounds obtained by introducing a substituent that enables a longer wavelength, such as aryl, heteroaryl, arylvinyl, amino, or cyano.

[0296] In addition, the dopant may be appropriately selected from the compounds described in Chemical Industry, June 2004, page 13 and the references cited therein.

[0297] 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.

[0298] The amine having a stilbene structure is represented, for example, by 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, 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, tri-substituted silyl (silyl tri-substituted with at least one of aryl, alkyl, and cycloalkyl) or cyano, and m is an integer from 1 to 4.

[0299] The amine having a stilbene structure is more preferably a 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 is optionally substituted with aryl, heteroaryl, alkyl, cycloalkyl, trisubstituted silyl (silyl trisubstituted with at least one of aryl, alkyl, and cycloalkyl) or cyano.

[0300] 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.

[0301] 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, and N,N'-di(9-phenanthryl)-N,N'-diphenyl-4,4'-diaminostilbene. nyl-4,4'-diaminostilbene, 4,4'-bis[4"-bis(diphenylamino)styryl]-biphenyl, 1,4-bis[4'-bis(diphenylamino)styryl]-benzene, 2,7-bis[4'-bis(diphenylamino)styryl]-9,9-dimethylfluorene, 4,4'-bis(9-ethyl-3-carbazovinylene)-biphenyl, 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.

[0302] 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). Also usable are perylene derivatives described in JP-A-11-97178, JP-A-2000-133457, JP-A-2000-26324, JP-A-2001-267079, JP-A-2001-267078, JP-A-2001-267076, JP-A-2000-34234, JP-A-2001-267075, and JP-A-2001-217077.

[0303] 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. Also, borane derivatives described in, for example, International Publication No. 2000 / 40586 may be used.

[0304] The aromatic amine derivative is represented, for example, by 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, tri-substituted silyl (silyl tri-substituted with at least one of aryl, alkyl, and cycloalkyl) or cyano, and n is an integer from 1 to 4.

[0305] 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.

[0306] 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.

[0307] 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, N,N'-bis(4-isopropylphenyl)-N,N'-di(p-tolyl)chrysene-6,12-diamine and the like.

[0308] 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, 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 and the like.

[0309] Examples of anthracene-based 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, N,N'-diphenyl-N,N'-di(m-tolyl)anthracene-9,10 -diamine, N,N'-diphenyl-N,N'-bis(4-ethylphenyl)anthracene-9,10-diamine, N,N'-diphenyl-N,N'-bis(4-isopropylphenyl)anthracene-9,10-diamine, N,N'-diphenyl-N,N'-bis(4-t-butylphenyl)anthracene-9,10-diamine, N,N'-bis(4-isopropylphenyl)-N,N'-di(p-tolyl)anthracene-9,10-diamine, 2,6-di-t-butyl-N,N,N',N'-tetra(p-tolyl)anthracene-9,10-diamine , 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 of such anthracene 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.

[0310] 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. Furthermore, aromatic amine derivatives described in, for example, JP-A-2006-156888 may also be used.

[0311] Coumarin derivatives include coumarin-6 and coumarin-334. Furthermore, coumarin derivatives described in JP-A-2004-43646, JP-A-2001-76876, JP-A-6-298758, and the like may also be used.

[0312] Examples of the pyran derivative include DCM and DCJTB shown below. [ka] Furthermore, pyran derivatives described in JP-A-2005-126399, JP-A-2005-097283, JP-A-2002-234892, JP-A-2001-220577, JP-A-2001-081090, JP-A-2001-052869, and the like may also be used.

[0313] The above-mentioned light-emitting layer materials (host materials and dopant materials) can be used as light-emitting layer materials as polymer compounds obtained by polymerizing a reactive compound substituted with a reactive substituent as a monomer, or as crosslinked polymers thereof, or as pendant polymer compounds obtained by reacting a main chain polymer with the reactive compound, or as crosslinked pendant polymers thereof. In this case, the reactive substituents can be quoted from the explanation of the polycyclic aromatic compound represented by the above general formula (1A) or (1B). The applications of such polymer compounds and crosslinked polymers will be described in detail below.

[0314] <Electron injection layer and electron transport layer in organic electroluminescence device> The electron injection layer 107 plays a role of efficiently injecting electrons moving from the cathode 108 into the light-emitting layer 105 or the electron transport layer 106. The electron transport layer 106 plays a role of efficiently transporting electrons injected from the cathode 108 or electrons injected from the cathode 108 via the electron injection layer 107 to the light-emitting layer 105. The electron transport layer 106 and the electron injection layer 107 are each formed by laminating or mixing one or more types of electron transport / injection materials, or by a mixture of an electron transport / injection material and a polymer binder.

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

[0316] The material (electron transport material) 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 general formula (1B) can be used as the electron transport material.

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

[0318] 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, pyridine derivatives, etc. Examples of the compound include arylazine derivatives, benzoquinoline derivatives (such as 2,2'-bis(benzo[h]quinolin-2-yl)-9,9'-spirobifluorene), imidazopyridine derivatives, borane derivatives, benzimidazole derivatives (such as tris(N-phenylbenzimidazol-2-yl)benzene), benzoxazole derivatives, benzothiazole derivatives, quinoline derivatives, oligopyridine derivatives such as terpyridine, bipyridine derivatives, terpyridine derivatives (such as 1,3-bis(4'-(2,2':6'2"-terpyridinyl))benzene), naphthyridine derivatives (such as bis(1-naphthyl)-4-(1,8-naphthyridin-2-yl)phenylphosphine oxide), aldazine derivatives, carbazole derivatives, indole derivatives, phosphorus oxide derivatives, and bisstyryl derivatives.

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

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

[0321] Among the above-mentioned materials, borane derivatives, pyridine derivatives, fluoranthene derivatives, BO-based derivatives, anthracene derivatives, benzofluorene derivatives, phosphine oxide derivatives, pyrimidine derivatives, carbazole derivatives, triazine derivatives, benzimidazole derivatives, phenanthroline derivatives, and quinolinol-based metal complexes are preferable.

[0322] The electron transport layer or the electron injection layer may further contain a substance capable of reducing the material forming the electron transport layer or the electron injection layer. As the reducing substance, various substances can be used as long as they have a certain degree of reducing ability, and for example, at least one selected from the group consisting of alkali metals, alkaline earth metals, rare earth metals, oxides of alkali metals, halides of alkali metals, oxides of alkaline earth metals, halides of alkaline earth metals, oxides of rare earth metals, halides of rare earth metals, organic complexes of alkali metals, organic complexes of alkaline earth metals, and organic complexes of rare earth metals can be suitably used.

[0323] Preferred reducing substances include alkali metals such as Na (work function 2.36 eV), K (2.28 eV), Rb (2.16 eV) or Cs (1.95 eV) and alkaline earth metals such as Ca (2.9 eV), Sr (2.0 to 2.5 eV) or Ba (2.52 eV), and substances with a work function of 2.9 eV or less are particularly preferred. Among these, more preferred reducing substances are alkali metals such as K, Rb or Cs, more preferably Rb or Cs, and most preferably Cs. These alkali metals have particularly high reducing ability, and by adding a relatively small amount to the material forming the electron transport layer or electron injection layer, the luminance of the organic EL element can be improved and the life can be extended. Furthermore, as a reducing substance having a work function of 2.9 eV or less, a combination of two or more of these alkali metals is also preferred, and in particular, a combination containing Cs is preferred, for example, a combination of Cs and Na, Cs and K, Cs and Rb, or a combination of Cs, Na and K. By containing Cs, the reducing ability can be efficiently exhibited, and by adding it to a material forming an electron transport layer or an electron injection layer, the luminance of the organic EL element can be improved and the life span can be extended.

[0324] The above-mentioned electron injection layer material and electron transport layer material can be used as an electron layer material in the form of a polymer compound obtained by polymerizing a reactive compound substituted with a reactive substituent as a monomer, or a crosslinked polymer thereof, or a pendant polymer compound obtained by reacting a main chain polymer with the reactive compound, or a crosslinked pendant polymer thereof. In this case, the reactive substituent can be quoted from the description of the polycyclic aromatic compound represented by the above general formula (1A) or general formula (1B). The applications of such polymer compounds and crosslinked polymers will be described in detail below.

[0325] <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 .

[0326] The material for forming the cathode 108 is not particularly limited as long as it is a substance that can efficiently inject electrons into the organic layer, but the same material as the material for forming the anode 102 can be used. Among them, metals such as tin, indium, calcium, aluminum, silver, copper, nickel, chromium, gold, platinum, iron, zinc, lithium, sodium, potassium, cesium, and magnesium, or alloys thereof (magnesium-silver alloy, magnesium-indium alloy, aluminum-lithium alloy such as lithium fluoride / aluminum, etc.), etc. are preferable. In order to increase the electron injection efficiency and improve the device characteristics, lithium, sodium, potassium, cesium, calcium, magnesium, or alloys containing these low work function metals are effective. However, these low work function metals are generally unstable in the air. To improve this point, for example, a method is known in which a trace amount of lithium, cesium, or magnesium is doped into the organic layer to use a highly stable electrode. As other dopants, inorganic salts such as lithium fluoride, cesium fluoride, lithium oxide, and cesium oxide can also be used. However, they are not limited to these.

[0327] Further, for electrode protection, preferred examples include lamination of metals such as platinum, gold, silver, copper, iron, tin, aluminum, and indium, or alloys using these metals, inorganic substances such as silica, titania, and silicon nitride, polyvinyl alcohol, vinyl chloride, hydrocarbon polymer compounds, etc. The method of producing these electrodes is also not particularly limited as long as it can provide electrical continuity, and may be resistance heating, electron beam deposition, sputtering, ion plating, coating, or the like.

[0328] <Binding agents that may be used in each layer> The materials used for the hole injection layer, hole transport layer, light emitting layer, electron transport layer and electron injection layer can form each layer alone, but they can also be used as a polymer binder by being dispersed in a solvent-soluble resin such as polyvinyl chloride, polycarbonate, polystyrene, poly(N-vinylcarbazole), polymethyl methacrylate, polybutyl methacrylate, polyester, polysulfone, polyphenylene oxide, polybutadiene, hydrocarbon resin, ketone resin, phenoxy resin, polyamide, ethyl cellulose, vinyl acetate resin, ABS resin, polyurethane resin, or a curable resin such as phenol resin, xylene resin, petroleum resin, urea resin, melamine resin, unsaturated polyester resin, alkyd resin, epoxy resin, silicone resin, or the like.

[0329] <Method for producing organic electroluminescent device> Each layer constituting an organic EL element can be formed by forming the material to be formed into a thin film by a method such as vapor deposition, resistance heating vapor deposition, electron beam vapor deposition, sputtering, molecular lamination, printing, spin coating or casting, coating, etc. The thickness of each layer thus formed is not particularly limited and can be set appropriately according to the properties of the material, but is usually in the range of 2 nm to 5000 nm. The thickness of the film can usually be measured with a quartz crystal oscillation type film thickness measuring device, etc. When forming a thin film by vapor deposition, the vapor deposition conditions vary depending on the type of material, the desired crystal structure and association structure of the film, etc. The vapor deposition conditions are generally a boat heating temperature of +50 to +400°C, a vacuum degree of 10, and a vacuum of 10. -6 ~10 -3 It is preferable to appropriately set the pressure, pressure Pa, deposition rate 0.01 to 50 nm / sec, substrate temperature -150 to +300°C, and film thickness 2 nm to 5 µm.

[0330] When applying a DC voltage to the organic EL element obtained in this way, the anode should be set to + and the cathode to -. When a voltage of about 2 to 40 V is applied, light emission can be observed from the transparent or semi-transparent electrode side (anode or cathode, or both). This organic EL element also emits light when a pulse current or an AC current is applied. The waveform of the AC current applied may be any waveform.

[0331] Next, as an example of a method for producing an organic EL element, a method for producing an organic EL element consisting of an anode, a hole injection layer, a hole transport layer, an emitting layer consisting of a host material and a dopant material, an electron transport layer, an electron injection layer, and a cathode will be described.

[0332] <Vapor deposition method> A thin film of an anode material is formed on a suitable substrate by vapor deposition or the like to prepare an anode, and then a thin film of a hole injection layer and a hole transport layer is formed on the anode. A host material and a dopant material are co-deposited on the anode to form a thin film as an emitting layer, and an electron transport layer and an electron injection layer are formed on the emitting layer, and a thin film of a cathode material is further formed by vapor deposition or the like to prepare a cathode, thereby obtaining the desired organic EL element. In the above-mentioned organic EL element, the order of preparation can be reversed to prepare the cathode, electron injection layer, electron transport layer, emitting layer, hole transport layer, hole injection layer, and anode in that order. In addition to the method of simultaneously evaporating a plurality of materials from separate vapor deposition sources, the above-mentioned co-evaporation method also includes a method of putting a mixture of the materials to be co-evaporated into one vapor deposition source and evaporating them all at once (premix method).

[0333] <Wet film formation method> The wet film formation method is carried out by preparing a low molecular weight compound capable of forming each organic layer of an organic EL element as a liquid composition for forming an organic layer, and using this. If there is no suitable organic solvent for dissolving this low molecular weight compound, the composition for forming an organic layer may be prepared from a polymer compound polymerized together with other monomers having a solubility function as a reactive compound obtained by substituting a reactive substituent on the low molecular weight compound or a main chain polymer.

[0334] In the wet film formation method, a coating film is generally formed through a coating step of coating a substrate with a composition for forming an organic layer and a drying step of removing the solvent from the coated composition for forming an organic layer. When the polymer compound has a crosslinkable substituent (also called a crosslinkable polymer compound), the polymer is further crosslinked by the drying step to form a crosslinked polymer. Depending on the difference in the coating step, a method using a spin coater is called a spin coat method, a method using a slit coater is called a slit coat method, a method using a plate is called a gravure, offset, reverse offset, or flexographic printing method, a method using an inkjet printer is called an inkjet method, and a method spraying in a mist form is called a spray method. The drying step includes air drying, heating, drying under reduced pressure, and the like. The drying step may be performed only once, or may be performed multiple times using different methods or conditions. In addition, different methods may be used in combination, such as baking under reduced pressure.

[0335] The wet film formation method is a film formation method using a solution, for example, some printing methods (inkjet methods), spin coating methods or casting methods, coating methods, etc. Unlike the vacuum deposition method, the wet film formation method does not require the use of expensive vacuum deposition equipment, and can form a film under atmospheric pressure. In addition, the wet film formation method allows for large area and continuous production, which leads to reduced manufacturing costs.

[0336] On the other hand, compared to the vacuum deposition method, wet film formation can be difficult to laminate. When producing laminated films using the wet film formation method, it is necessary to prevent the dissolution of the lower layer by the composition of the upper layer, and compositions with controlled solubility, crosslinking of the lower layer, and orthogonal solvents (solvents that do not dissolve in each other) are used. However, even with these technologies, it can be difficult to use the wet film formation method to apply all films.

[0337] Therefore, a method is generally adopted in which only some layers are formed by a wet film formation method and the remaining layers are formed by a vacuum deposition method when manufacturing an organic EL element.

[0338] For example, the procedure for producing an organic EL element by partially applying a wet film formation method will be described below. (Step 1) Formation of the anode by vacuum deposition (Step 2) Forming a film by a wet film formation method using a composition for forming a hole injection layer containing a material for the hole injection layer (Step 3) Forming a film by a wet film formation method using a composition for forming a hole transport layer containing a material for the hole transport layer (Step 4) Formation of a film by a wet film formation method using a composition for forming an emitting layer containing a host material and a dopant material (Step 5) Formation of the electron transport layer by vacuum deposition (Step 6) Formation of the electron injection layer by vacuum deposition (Step 7) Cathode deposition by vacuum deposition Through this procedure, an organic EL element consisting of an anode, a hole injection layer, a hole transport layer, an emitting layer made of a host material and a dopant material, an electron transport layer, an electron injection layer, and a cathode is obtained. Of course, if there is a means for preventing dissolution of the lower light-emitting layer, or if a means for forming a film from the cathode side is used in the opposite procedure to the above, a layer-forming composition containing the electron transport layer material and the electron injection layer material can be prepared and then the layer can be formed by a wet film formation method.

[0339] <Other film formation methods> The composition for forming an organic layer can be formed into a film by laser thermal imaging (LITI). LITI is a method in which a compound attached to a substrate is heated and evaporated by a laser, and the composition for forming an organic layer can be used as the material applied to the substrate.

[0340] <Optional process> Before and after each film-forming step, appropriate treatment steps, cleaning steps, and drying steps may be appropriately inserted. Examples of treatment steps include exposure treatment, plasma surface treatment, ultrasonic treatment, ozone treatment, cleaning treatment using an appropriate solvent, and heat treatment. Furthermore, a series of steps for preparing a bank may also be included.

[0341] Photolithography techniques can be used to fabricate the banks. Positive resist materials and negative resist materials can be used as bank materials that can be used in photolithography. In addition, patternable printing methods such as inkjet printing, gravure offset printing, reverse offset printing, and screen printing can also be used. In this case, permanent resist materials can also be used.

[0342] Materials that can be used for the banks include, but are not limited to, polysaccharides and their derivatives, homopolymers and copolymers of hydroxyl-containing ethylenic monomers, biopolymers, polyacryloyl compounds, polyesters, polystyrenes, polyimides, polyamideimides, polyetherimides, polysulfides, polysulfones, polyphenylenes, polyphenyl ethers, polyurethanes, epoxy (meth)acrylates, melamine (meth)acrylates, polyolefins, cyclic polyolefins, acrylonitrile-butadiene-styrene copolymers (ABS), silicone resins, polyvinyl chloride, chlorinated polyethylene, chlorinated polypropylene, polyacetate, polynorbornene, synthetic rubber, fluorinated polymers such as polyfluorovinylidene, polytetrafluoroethylene, and polyhexafluoropropylene, copolymers of fluoroolefins and hydrocarbon olefins, and fluorocarbon polymers.

[0343] <Composition for forming organic layer used in wet film formation method> The composition for forming an organic layer is obtained by dissolving a low molecular weight compound capable of forming each organic layer of an organic EL device, or a polymer compound obtained by polymerizing the low molecular weight compound, in an organic solvent. For example, the composition for forming an emitting layer contains at least one polycyclic aromatic compound (or a polymer compound thereof) as a first component, which is a dopant material, at least one host material as a second component, and at least one organic solvent as a third component. The first component functions as a dopant component of the emitting layer obtained from the composition, and the second component functions as a host component of the emitting layer. The third component functions as a solvent that dissolves the first and second components in the composition, and gives a smooth and uniform surface shape due to the controlled evaporation rate of the third component itself during application.

[0344] <Organic solvent> The organic layer forming composition contains at least one organic solvent. By controlling the evaporation rate of the organic solvent during film formation, it is possible to control and improve the film forming properties, the presence or absence of defects in the coating film, the surface roughness, and the smoothness. In addition, during film formation using the inkjet method, it is possible to control the meniscus stability at the pinhole of the inkjet head, and control and improve the ejection properties. In addition, by controlling the drying rate of the film and the orientation of the derivative molecules, it is possible to improve the electrical properties, light emitting properties, efficiency, and life of an organic EL element having an organic layer obtained from the organic layer forming composition.

[0345] (1) Physical properties of organic solvents The boiling point of at least one organic solvent is 130°C to 300°C, more preferably 140°C to 270°C, and further preferably 150°C to 250°C. When the boiling point is higher than 130°C, it is preferable from the viewpoint of inkjet dischargeability. Also, when the boiling point is lower than 300°C, it is preferable from the viewpoint of coating film defects, surface roughness, residual solvent, and smoothness. From the viewpoint of good inkjet dischargeability, film-forming property, smoothness, and low residual solvent, it is more preferable that the organic solvent contains two or more organic solvents. On the other hand, in some cases, the composition may be in a solid state by removing the solvent from the composition for forming the organic layer, taking into consideration transportability, etc.

[0346] Furthermore, the organic solvent contains a good solvent (GS) and a poor solvent (PS) for at least one of the solutes, and the boiling point (BP) of the good solvent (GS) is GS ) is the boiling point (BP PS ) is particularly preferred. By adding a poor solvent with a high boiling point, the good solvent with a low boiling point volatilizes first during film formation, increasing the concentration of the components in the composition and the concentration of the poor solvent, promoting rapid film formation. This results in a coating film with few defects, small surface roughness, and high smoothness.

[0347] Difference in solubility (S GS -S PS The boiling point difference (BP) is preferably 1% or more, more preferably 3% or more, and even more preferably 5% or more. PS -BP GS ) is preferably 10° C. or higher, more preferably 30° C. or higher, and even more preferably 50° C. or higher.

[0348] After the film is formed, the organic solvent is removed from the coating film by a drying process such as vacuum, reduced pressure, or heating. When heating is performed, from the viewpoint of improving the coating film-forming property, it is preferable to perform the heating at a temperature of at least one of the solutes at a glass transition temperature (Tg) +30°C or lower. From the viewpoint of reducing the residual solvent, it is preferable to heat at at least one of the solutes at a glass transition temperature (Tg) -30°C or higher. Even if the heating temperature is lower than the boiling point of the organic solvent, the organic solvent is sufficiently removed because the film is thin. Also, drying may be performed multiple times at different temperatures, and multiple drying methods may be used in combination.

[0349] (2) Specific examples of organic solvents Examples of the organic solvent used in the composition for forming the organic layer include alkylbenzene solvents, phenyl ether solvents, alkyl ether solvents, cyclic ketone solvents, aliphatic ketone solvents, monocyclic ketone solvents, solvents having a diester skeleton, and fluorine-containing solvents. Specific examples include pentanol, hexanol, heptanol, octanol, nonanol, decanol, undecanol, dodecanol, tetradecanol, hexane-2-ol, heptan-2-ol, octan-2-ol, decan-2-ol, dodecan-2-ol, cyclohexanol, Sanol, α-terpineol, β-terpineol, γ-terpineol, δ-terpineol, terpineol (mixture), ethylene glycol monomethyl ether acetate, propylene glycol monomethyl ether acetate, diethylene glycol dimethyl ether, dipropylene glycol dimethyl ether, diethylene glycol ethyl methyl ether, diethylene glycol isopropyl methyl ether, dipropylene glycol monomethyl ether, diethylene glycol diethyl ether, diethylene glycol monomethyl ether , diethylene glycol butyl methyl ether, tripropylene glycol dimethyl ether, triethylene glycol dimethyl ether, diethylene glycol monobutyl ether, ethylene glycol monophenyl ether, triethylene glycol monomethyl ether, diethylene glycol dibutyl ether, triethylene glycol butyl methyl ether, polyethylene glycol dimethyl ether, tetraethylene glycol dimethyl ether, p-xylene, m-xylene, o-xylene, 2,6-lutidine, 2-fluoro-m-xylene, 3-fluoro-o-xylene, 2-chlorobenzotrifluoride, cumene, toluene, 2-chloro-6-fluorotoluene, 2-fluoroanisole, anisole, 2,3-dimethylpyrazine, bromobenzene, 4-fluoroanisole, 3-fluoroanisole, 3-trifluoromethylanisole, mesitylene, 1,2,4-trimethylbenzene, t-butylbenzene, 2-methylanisole, phenetole, benzodioxole, 4-methylanisole, s-butylbenzene, 3-methylanisole, 4-fluoro-3-methylanisole, cymene, 1,2,3-Trimethylbenzene, 1,2-Dichlorobenzene, 2-Fluorobenzonitrile, 4-Fluoroveratrol, 2,6-Dimethylanisole, n-Butylbenzene, 3-Fluorobenzonitrile, Decalin (Decahydronaphthalene), Neopentylbenzene, 2,5-Dimethylanisole, 2,4-Dimethylanisole, Benzonitrile, 3,5-Dimethylanisole, Diphenyl ether, 1-Fluoro-3,5-dimethoxybenzene, Methyl benzoate, Isopentylbenzene, 3,4-Dimethylanisole, o-Tolunitrile, n-Amylbenzene, Veratrol, 1,2,3,4-Tetrahydronaphthalene, Ethyl benzoate, n-Hexylbenzene, Propyl benzoate, Cyclohexylbenzene, 1-Methoxybenzene, Examples of the solvent include, but are not limited to, ethylnaphthalene, butyl benzoate, 2-methylbiphenyl, 3-phenoxytoluene, 2,2'-bitolyl, dodecylbenzene, dipentylbenzene, tetramethylbenzene, trimethoxybenzene, trimethoxytoluene, 2,3-dihydrobenzofuran, 1-methyl-4-(propoxymethyl)benzene, 1-methyl-4-(butyloxymethyl)benzene, 1-methyl-4-(pentyloxymethyl)benzene, 1-methyl-4-(hexyloxymethyl)benzene, 1-methyl-4-(heptyloxymethyl)benzene, benzyl butyl ether, benzyl pentyl ether, benzyl hexyl ether, benzyl heptyl ether, and benzyl octyl ether. The solvent may be used alone or in a mixture.

[0350] <Optional ingredients> The composition for forming the organic layer may contain optional components, such as a binder and a surfactant, to the extent that the properties of the composition are not impaired.

[0351] (1) Binder The composition for forming an organic layer may contain a binder. The binder forms a film during film formation and bonds the resulting film to a substrate. The binder also plays a role in dissolving, dispersing, and binding other components in the composition for forming an organic layer.

[0352] 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.

[0353] The binder used in the organic layer-forming composition may be of one type or a mixture of two or more types.

[0354] (2) Surfactants The organic layer forming composition may contain a surfactant, for example, to control the film surface uniformity, solvent affinity and liquid repellency of the organic layer forming composition. Surfactants are classified into ionic and nonionic based on the structure of the hydrophilic group, and further classified into alkyl, silicon and fluorine based on the structure of the hydrophobic group. In addition, based on the molecular structure, they are classified into monomolecular systems with relatively small molecular weight and simple structure, and polymer systems with large molecular weight and side chains or branches. In addition, based on the composition, they are classified into single systems and mixed systems in which two or more types of surfactants and base materials are mixed. All types of surfactants can be used as surfactants that can be used in the organic layer forming composition.

[0355] Examples of surfactants include Polyflow No. 45, Polyflow KL-245, Polyflow No. 75, Polyflow No. 90, Polyflow No. 95 (trade names, manufactured by Kyoeisha Chemical Industry Co., Ltd.), Disperbyk 161, Disperbyk 162, Disperbyk 163, Disperbyk 164, Disperbyk 166, Disperbyk 170, Disperbyk 180, Disperbyk 181, Disperbyk 182, BYK300, BYK 306, BYK310, BYK320, BYK330, BYK342, BYK344, BYK346 (trade name, manufactured by BYK Japan Co., Ltd.), KP-341, KP-358, KP-368, KF-96-50CS, KF-50-100CS (trade name, manufactured by Shin-Etsu Chemical Co., Ltd.), Surflon SC-101, Surflon KH-40 (trade name, manufactured by Seimi Chemical Co., Ltd.), Ftergent 222F, Ftergent 251, FTX-218 (trade name, manufactured by Neos Co., Ltd.), EFTOP EF-351, EFTOP EF-352, EFTOP EF-601, EFTOP EF-801, EFTOPEF-802 (product name, manufactured by Mitsubishi Materials Corporation), Megafac F-470, Megafac F-471, Megafac F-475, Megafac R-08, Megafac F-477, Megafac F-479, Megafac F-553, Megafac F-554 (product name, manufactured by DIC Corporation), fluoroalkylbenzenesulfonate, fluoroalkylcarboxylate, fluoroalkylpolyoxyethyleneether, fluoroalkylammonium iodide, fluoroalkylbetaine, fluoroalkylsulfonate, diglycerol tetrakis(fluoroalkylpolyoxyethyleneether), fluoroalkyltrimethylammonium salt, fluoroalkylaminosulfonate, polyoxyethylenenonyl Examples of the alkyl ethers include polyoxyethylene octylphenyl ether, polyoxyethylene alkyl ethers, polyoxyethylene laurate, polyoxyethylene oleate, polyoxyethylene stearate, polyoxyethylene laurylamine, sorbitan laurate, sorbitan palmitate, sorbitan stearate, sorbitan oleate, sorbitan fatty acid esters, polyoxyethylene sorbitan laurate, polyoxyethylene sorbitan palmitate, polyoxyethylene sorbitan stearate, polyoxyethylene sorbitan oleate, polyoxyethylene naphthyl ether, alkyl benzene sulfonates, and alkyl diphenyl ether disulfonates.

[0356] The surfactant may be used alone or in combination of two or more kinds.

[0357] <Composition and Properties of the Organic Layer-Forming Composition> The content of each component in the composition for forming an organic layer is determined in consideration of the good solubility, storage stability and film-forming property of each component in the composition for forming an organic layer, the good film quality of the coating film obtained from the composition for forming an organic layer, the good discharge property when using an inkjet method, and the good electrical properties, light-emitting properties, efficiency and life of an organic EL element having an organic layer produced using the composition. For example, in the case of a composition for forming an emitting layer, it is preferable that the first component is 0.0001% by weight to 2.0% by weight based on the total weight of the composition for forming an emitting layer, the second component is 0.0999% by weight to 8.0% by weight based on the total weight of the composition for forming an emitting layer, and the third component is 90.0% by weight to 99.9% by weight based on the total weight of the composition for forming an emitting layer.

[0358] 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.

[0359] The composition for forming an organic layer can be produced by appropriately selecting the above-mentioned components and subjecting them to stirring, mixing, heating, cooling, dissolving, dispersing, etc., by a known method. After preparation, filtration, degassing (also called degassing), ion exchange treatment, and inert gas replacement / filling treatment, etc. may be appropriately selected.

[0360] 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).

[0361] The lower the surface tension of the composition for forming an organic layer, the better the film-forming properties and the more defect-free the coating film will be. On the other hand, the higher the surface tension, the better the ink-jet ejection properties will be. For this reason, the viscosity of the composition for forming an organic layer is preferably such that the surface tension at 25°C is 20 to 40 mN / m, more preferably 20 to 30 mN / m. In the present invention, the surface tension is a value measured using the hanging drop method.

[0362] <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 the above formula (H3), 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% by weight in the molecule.

[0363] The content of the monovalent or divalent aromatic compound having a crosslinkable substituent is preferably from 0.5 to 50% by weight, more preferably from 1 to 20% by weight.

[0364] The crosslinkable substituent (XLS) is not particularly limited as long as it is a group that can further crosslink the above-mentioned polymer compound, but substituents having the following structures are preferred: In each structural formula, * indicates the bond position. [ka]

[0365] Each L is independently a single bond, -O-, -S-, >C=O, -OC(=O)-, an alkylene having 1 to 12 carbon atoms, an oxyalkylene having 1 to 12 carbon atoms, or a polyoxyalkylene having 1 to 12 carbon atoms. Among the above substituents, a group represented by formula (XLS-1), formula (XLS-2), formula (XLS-3), formula (XLS-9), formula (XLS-10) or formula (XLS-17) is preferred, and a group represented by formula (XLS-1), formula (XLS-3) or formula (XLS-17) is more preferred.

[0366] Examples of the divalent aromatic compound having a crosslinkable substituent include compounds having the following partial structures: In the following structural formula, * indicates the bonding position. [ka] [ka] [ka] [ka]

[0367] <Methods of producing polymer compounds and crosslinkable polymer compounds> The manufacturing method of the polymer compound and the crosslinkable polymer compound will be described with reference to the compound represented by the above formula (H3) and the compound represented by (XLP-1). These compounds can be synthesized by appropriately combining known manufacturing methods.

[0368] The solvent used in the reaction includes aromatic solvents, saturated / unsaturated hydrocarbon solvents, alcohol solvents, ether solvents, and the like, such as dimethoxyethane, 2-(2-methoxyethoxy)ethane, 2-(2-ethoxyethoxy)ethane, and the like.

[0369] The reaction may be carried out in a two-phase system. When the reaction is carried out in a two-phase system, a phase transfer catalyst such as a quaternary ammonium salt may be added, if necessary.

[0370] The compound of formula (H3) and the compound of formula (XLP-1) may be produced in one step or in multiple steps. The compound may be produced by a batch polymerization method in which all the raw materials are put into a reaction vessel and then the reaction is started, a dropwise polymerization method in which the raw materials are added dropwise to a reaction vessel, or a precipitation polymerization method in which the product precipitates as the reaction proceeds, and these methods can be combined appropriately to synthesize the compound. For example, when the compound represented by formula (H3) is synthesized in one step, the target product is obtained by carrying out the reaction in a state in which the monomer unit (MU) and the end cap unit (EC) are added to a reaction vessel. When the compound represented by general formula (H3) is synthesized in multiple steps, the target product is obtained by polymerizing the monomer unit (MU) to the target molecular weight, and then adding the end cap unit (EC) and reacting it. If different types of monomer units (MU) are added and reacted in multiple steps, a polymer having a concentration gradient in the structure of the monomer unit can be produced. After preparing a precursor polymer, the target polymer can be obtained by a subsequent reaction.

[0371] In addition, the primary structure of the polymer can be controlled by selecting the polymerizable group of the monomer unit (MU). For example, as shown in synthesis schemes 1 to 3, it is possible to synthesize a polymer having a random primary structure (synthetic scheme 1) or a polymer having a regular primary structure (synthetic schemes 2 and 3), and these can be used in appropriate combination depending on the target object. Furthermore, by using a monomer unit having three or more polymerizable groups, it is possible to synthesize a hyperbranched polymer or a dendrimer.

[0372] [ka]

[0373] Examples of monomer units that can be used in the present invention include those described in JP2010-189630A, WO2012 / 086671A, WO2013 / 191088A, WO2002 / 045184A, WO2011 / 049241A, WO2013 / 146806A, WO2005 / 049546A, WO2015 / 14 It can be synthesized in accordance with the methods described in JP-A-2002 / 045184, JP-A-2010-215886, JP-A-2008-106241, JP-A-2010-215886, WO 2016 / 031639, JP-A-2011-174062, WO 2016 / 031639, WO 2016 / 031639, and WO 2002 / 045184.

[0374] In addition, specific polymer synthesis procedures are described in JP 2012-036388 A, WO 2015 / 008851 A, JP 2012-36381 A, JP 2012-144722 A, WO 2015 / 194448 A, WO 2013 / 146806 A, WO 2015 / 145871 A, WO 2016 / It can be synthesized in accordance with the methods described in WO 2016 / 031639, WO 2016 / 125560, WO 2016 / 031639, WO 2016 / 031639, WO 2016 / 125560, WO 2015 / 145871, WO 2011 / 049241, and JP 2012-144722 A.

[0375] <Applications of organic electroluminescent devices> The present invention can also be applied to a display device having an organic EL element or a lighting device having 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.

[0376] Examples of the display device include panel displays such as color flat panel displays, and flexible displays such as flexible color organic electroluminescent (EL) displays (see, for example, JP-A-10-335066, JP-A-2003-321546, JP-A-2004-281086, etc.). Examples of the display method include matrix and segment methods. Note that matrix display and segment display may coexist in the same panel.

[0377] In a matrix, pixels for display are arranged two-dimensionally, such as in a grid or mosaic pattern, and a collection of pixels displays characters and images. The shape and size of the pixels are determined by the application. For example, square pixels with sides of 300 μm or less are usually used to display images and characters on computers, monitors, and televisions, and pixels with sides of mm order are used for large displays such as display panels. For monochrome display, pixels of the same color are arranged, but for color display, red, green, and blue pixels are displayed side by side. In this case, there are typically delta type and stripe type. The driving method for this matrix can be either line sequential driving method or active matrix. Line sequential driving has the advantage of being simpler in structure, but when considering the operating characteristics, active matrix may be superior, so it is necessary to use it according to the application.

[0378] In the segment type, a pattern is formed to display predetermined information, and a predetermined area is illuminated. Examples include time and temperature displays in digital clocks and thermometers, operating status displays in audio equipment and induction cookers, and panel displays in automobiles.

[0379] Examples of the lighting device include lighting devices for indoor lighting, backlights for liquid crystal display devices, etc. (see, for example, JP 2003-257621 A, JP 2003-277741 A, JP 2004-119211 A, etc.). Backlights are mainly used for the purpose of improving the visibility of non-self-luminous display devices, and are used in liquid crystal display devices, clocks, audio devices, automobile panels, display boards, signs, etc. In particular, for liquid crystal display devices, particularly backlights for personal computers, where thinning is an issue, it is difficult to make them thin because conventional methods are made of fluorescent lamps and light guide plates, so the backlight using the light-emitting element according to this embodiment is characterized by its thinness and light weight.

[0380] 3-2. Other organic devices The polycyclic aromatic compound according to the present invention can be used for producing the above-mentioned organic electroluminescent device, as well as an organic field effect transistor or an organic thin-film solar cell.

[0381] An organic field-effect transistor is a transistor that controls current by an electric field generated by voltage input, and has a gate electrode in addition to a source electrode and a drain electrode. When a voltage is applied to the gate electrode, an electric field is generated, and the flow of electrons (or holes) flowing between the source electrode and the drain electrode can be arbitrarily blocked to control the current. Field-effect transistors are easier to miniaturize than simple transistors (bipolar transistors), and are often used as elements that make up integrated circuits.

[0382] The structure of an organic field effect transistor is usually such that a source electrode and a drain electrode are provided in contact with an organic semiconductor active layer formed using the polycyclic aromatic compound according to the present invention, and a gate electrode is provided sandwiching an insulating layer (dielectric layer) in contact with the organic semiconductor active layer. Examples of the element structure include the following structure. (1) Substrate / gate electrode / insulating layer / source and drain electrodes / organic semiconductor active layer (2) Substrate / gate electrode / insulating layer / organic semiconductor active layer / source electrode and drain electrode (3) Substrate / organic semiconductor active layer / source electrode / drain electrode / insulator layer / gate electrode (4) Substrate / source electrode / drain electrode / organic semiconductor active layer / insulator layer / gate electrode The organic field effect transistor thus configured can be used as a pixel driving switching element for an active matrix driving type liquid crystal display or an organic electroluminescence display.

[0383] The organic thin-film solar cell has a structure in which an anode such as ITO, a hole transport layer, a photoelectric conversion layer, an electron transport layer, and a cathode are laminated on a transparent substrate such as glass. The photoelectric conversion layer has a p-type semiconductor layer on the anode side and an n-type semiconductor layer on the cathode side. The polycyclic aromatic compound according to the present invention can be used as a material for a hole transport layer, a p-type semiconductor layer, an n-type semiconductor layer, and an electron transport layer depending on its physical properties. The polycyclic aromatic compound according to the present invention can function as a hole transport material or an electron transport material in an organic thin-film solar cell. In addition to the above, the organic thin-film solar cell may appropriately include a hole blocking layer, an electron blocking layer, an electron injection layer, a hole injection layer, a smoothing layer, and the like. The organic thin-film solar cell can be used by appropriately selecting and combining known materials used in organic thin-film solar cells.

[0384] <Wavelength conversion material> The polycyclic aromatic compound of the present invention can be used as a wavelength converting material. Currently, the application of multi-color technology using color conversion methods to liquid crystal displays, organic electroluminescence displays, lighting, and the like is being actively considered. Color conversion refers to the wavelength conversion of light emitted from a light emitter to light with a longer wavelength, for example, converting ultraviolet light or blue light to green light or red light emission. By forming a wavelength conversion material with this color conversion function into a film and combining it with, for example, a blue light source, it becomes possible to extract the three primary colors of blue, green, and red from the blue light source, that is, to extract white light. By combining such a blue light source and a wavelength conversion film with a color conversion function as a light source unit, and combining it with a liquid crystal drive part and a color filter, it becomes possible to manufacture a full-color display. Furthermore, if there is no liquid crystal drive part, it can be used as a white light source as it is, and can be applied as a white light source for, for example, LED lighting. Furthermore, by using a blue organic electroluminescence element as a light source and combining it with a wavelength conversion film that converts blue light into green light and red light, it becomes possible to manufacture a full-color organic electroluminescence display without using a metal mask. Furthermore, by using blue microLEDs as a light source in combination with a wavelength conversion film that converts blue light into green and red light, it is possible to create low-cost full-color microLED displays. EXAMPLES

[0385] The present invention will be described in more detail below with reference to examples, but the present invention is not limited thereto. First, synthesis examples of polycyclic aromatic compounds will be described below.

[0386] Synthesis Example (1): Synthesis of compound (2A-szs-0004) To a flask containing compound (Int-2A-szs-0004) (2.95 g, 3.0 mmol, 1 eq.) and o-dichlorobenzene (400 ml), boron tribromide (1.13 ml, 12 mmol, 4 eq.) was added at room temperature under a nitrogen atmosphere. After the dropwise addition was completed, the temperature was raised to 180°C and the mixture was stirred for 20 hours. Then, the mixture was cooled again to room temperature, and N,N-diisopropylethylamine (7.70 ml, 45 mmol, 15 eq.) was added and the mixture was stirred until the heat generation subsided. Then, the reaction solution was distilled under reduced pressure at 60°C to obtain a crude product. The obtained crude product was washed with acetonitrile, methanol, and toluene in that order, and purified with a silica gel column (eluent: toluene), and the crude product was recrystallized twice with o-dichlorobenzene to obtain compound (2A-szs-0004) (0.22 g). MS confirmed that the target compound (2A-szs-0004) had an m / z (M+H) of 998.388. [ka]

[0387] Synthesis example (2): Synthesis of compound (2A-zsz-0004) Compound (2A-zsz-0004) (0.25 g) was obtained in the same manner as in Synthesis Example 1, except that compound (Int-2A-szs-0004) (2.95 g, 3.0 mmol, 1 eq.) was changed to compound (Int-2A-zsz-0004) (2.80 g, 3.0 mmol, 1 eq.). MS confirmed that the target compound (2A-zsz-0004) had an m / z (M+H) of 950.388949.380. [ka]

[0388] Synthesis Example (3): Synthesis of compound (2A-zzz-0002) Compound (2A-zzz-0002) (0.19 g) was obtained in the same manner as in Synthesis Example 1, except that compound (Int-2A-szs-0004) (2.95 g, 3.0 mmol, 1 eq.) was replaced with compound (Int-2A-zzz-0002) (2.66 g, 3.0 mmol, 1 eq.). MS confirmed that the target compound (2A-zzz-0002) had an m / z (M+H) of 902.388. [ka]

[0389] Synthesis Example (4): Synthesis of compound (2B-szs-0001) In a flask containing the compound (Int-2A-szs-0004) (2.95 g, 3.0 mmol, 1 eq.) and o-dichlorobenzene (400 ml), boron tribromide (1.70 ml, 18 mmol, 6 eq.) was added at room temperature under a nitrogen atmosphere. After the dropwise addition was completed, the temperature was raised to 180°C and the mixture was stirred for 20 hours. Then, the mixture was cooled again to room temperature, and N,N-diisopropylethylamine (11.6 ml, 68 mmol, 23 eq.) was added and the mixture was stirred until the heat generation subsided. Then, the reaction solution was distilled under reduced pressure at 60°C to obtain a crude product. The obtained crude product was washed with acetonitrile, methanol, and toluene in that order, and purified with a silica gel column (eluent: toluene), and the crude product was recrystallized twice with o-dichlorobenzene to obtain compound (2B-szs-0001) (0.24 g). MS confirmed that the target compound (2B-szs-0001) had an m / z (M+H) of 1006.374. [ka]

[0390] Synthesis Example (5): Synthesis of compound (2B-zsz-0001) Compound (2B-zsz-0001) was obtained (0.21 g) in the same manner as in Synthesis Example 4, except that compound (Int-2A-szs-0004) (2.95 g, 3.0 mmol, 1 eq.) was replaced with compound (Int-2A-zsz-0004) (2.80 g, 3.0 mmol, 1 eq.). MS confirmed that the target compound (2B-zsz-0001) had an m / z (M+H) of 958.374. [ka]

[0391] Synthesis Example (6): Synthesis of compound (2B-zzz-0001) Compound (2B-zzz-0001) was obtained (0.20 g) in the same manner as in Synthesis Example 4, except that compound (Int-2A-szs-0004) (2.95 g, 3.0 mmol, 1 eq.) was replaced with compound (Int-2A-zzz-0002) (2.66 g, 3.0 mmol, 1 eq.). MS confirmed that the target compound (2B-zzz-0001) had an m / z (M+H) of 910.374. [ka]

[0392] By appropriately changing the raw material compounds, other polycyclic aromatic compounds of the present invention can be synthesized according to the methods of the above-mentioned synthesis examples.

[0393] Next, evaluation of the basic physical properties of the compound of the present invention and preparation and evaluation of an organic EL device using the compound of the present invention will be described. However, the application of the compound of the present invention is not limited to the examples shown below, and the film thickness and constituent materials of each layer can be appropriately changed depending on the basic physical properties of the compound of the present invention.

[0394] <Evaluation of deposition-type organic EL elements> Organic EL elements according to Examples 1-1 to 1-6 and Comparative Examples 1-1 to 1-4 were fabricated, and the luminance was 500 cd / m 2The emission wavelength, half-width, driving voltage, external quantum efficiency, and LT50 (initial luminance 500cd / m 2 When continuously driven at a current density of 250 cd / m 2 The time during which the brightness was maintained above this level was measured.

[0395] [Table 1]

[0396] In Table 1, the chemical structures of "NPD," "TcTa," "mCP," "Ir(ppy)3," "2CzBN," "BPy-TP2," and "GH-1" are shown below.

[0397] [ka]

[0398] The chemical structures of RGD-1, RGD-2, and RGD-3 in Table 1 are shown below. [ka]

[0399] <Example 1-1> A 26 mm × 28 mm × 0.7 mm glass substrate (manufactured by Optoscience Co., Ltd.) on which an ITO film having a thickness of 200 nm was formed by sputtering and polished to 50 nm was used as a transparent support substrate. This transparent support substrate was fixed to the substrate holder of a commercially available deposition device (manufactured by Showa Vacuum Co., Ltd.), and a molybdenum deposition boat containing NPD, TcTa, mCP, GH-1, compound (2A-szs-0004), 2CzBN, and BPy-TP2, and a tungsten deposition boat containing LiF and aluminum were attached.

[0400] The following layers were formed in order on the ITO film of the transparent support substrate. -4The pressure was reduced to 100 Pa, and first, NPD was heated and evaporated to a thickness of 40 nm to form a hole injection layer. Next, TcTa was heated and evaporated to a thickness of 15 nm, and mCP was further heated and evaporated to a thickness of 15 nm to form a two-layer hole transport layer. Next, GH-1 and compound (2A-szs-0004) were heated simultaneously and evaporated to a thickness of 20 nm to form a light-emitting layer. The evaporation rate was adjusted so that the weight ratio of GH-1 to compound (2A-szs-0004) was approximately 99:1. Next, 2CzBN was heated and evaporated to a thickness of 10 nm, and BPy-TP2 was further heated and evaporated to a thickness of 20 nm to form a two-layer electron transport layer. The evaporation rate of each layer was 0.01 to 1 nm / sec. Then, LiF was heated and evaporated at an evaporation rate of 0.01 to 0.1 nm / sec to a thickness of 1 nm, and then aluminum was heated and evaporated to a thickness of 100 nm to form a cathode, and an organic EL device was obtained. At this time, the deposition rate of aluminum was adjusted to be 1 to 10 nm / sec.

[0401] <Examples 1-2 to 1-6> The compound (2A-szs-0004) used as the dopant in Example 1 was changed to each dopant and each mixing ratio shown in Table 1 to prepare each device.

[0402] <Comparative Examples 1-1 to 1-4> The compound (2A-szs-0004) used as the dopant in Example 1 was changed to each of the dopants shown in Table 1 to fabricate each device.

[0403] The evaluation results for each element are shown in Table 2. [Table 2]

[0404] In Examples 1-1 to 1-6, the external quantum efficiency was higher and the element life was longer than in Comparative Examples 1-1 to 1-4.

[0405] <Evaluation of deposition-type organic EL elements> Organic EL elements according to Examples G2-1 to G2-6, Comparative Example G2-1, Examples G3-1 to G3-6, and Comparative Example G3-1 were fabricated, and the luminance was 500 cd / m 2 The emission wavelength, half-width, driving voltage, external quantum efficiency, and LT50 (initial luminance 500cd / m 2 When continuously driven at a current density of 250 cd / m 2 The time during which the brightness was maintained above this level was measured.

[0406] [Table 3]

[0407] In Table 3, the chemical structures of "HATCN", "TBB", "CBP", "TPBi" and "GH-2" are shown below.

[0408] [ka]

[0409] <Example G2-1> A 26 mm × 28 mm × 0.7 mm glass substrate (manufactured by Optoscience Co., Ltd.) on which an ITO film having a thickness of 200 nm was formed by sputtering and polished to 50 nm was used as a transparent support substrate. This transparent support substrate was fixed to the substrate holder of a commercially available deposition device (manufactured by Showa Vacuum Co., Ltd.), and a molybdenum deposition boat containing HATCN, TBB, TcTa, CBP, compound (2A-szs-0004), and TPBi, and a tungsten deposition boat containing LiF and aluminum were attached.

[0410] The following layers were formed in order on the ITO film of the transparent support substrate. -4 The pressure was reduced to 10 Pa, and first, HATCN was heated and evaporated to a thickness of 5 nm to form a hole injection layer. Next, TBB was heated and evaporated to a thickness of 65 nm, and further, TcTa was heated and evaporated to a thickness of 10 nm to form a two-layer hole transport layer. Next, CBP and compound (2A-szs-0004) were heated simultaneously and evaporated to a thickness of 30 nm to form a light-emitting layer. The evaporation rate was adjusted so that the weight ratio of CBP to compound (2A-szs-0004) was approximately 99:1. Next, TPBi was heated and evaporated to a thickness of 50 nm to form an electron transport layer. The evaporation rate of each layer was 0.01 to 1 nm / sec. Then, LiF was heated and evaporated at an evaporation rate of 0.01 to 0.1 nm / sec to a thickness of 1 nm, and then aluminum was heated and evaporated to a thickness of 100 nm to form a cathode, and an organic EL device was obtained. At this time, the evaporation rate of aluminum was adjusted to 1 to 10 nm / sec.

[0411] <Examples G2-2 to G2-6, Comparative Example G2-1, Examples G3-1 to G3-6, and Comparative Example G3-1> The host CBP, the dopant compound (2A-szs-0004), and the mixing ratio in Example G2-1 were changed to each host, each dopant, and each mixing ratio shown in Table 3 to prepare each device.

[0412] The evaluation results for each element are shown in Table 4. [Table 4]

[0413] In Examples G2-1 to G2-6 and Examples G3-1 to G3-6, higher efficiency and longer element life were obtained as compared with Comparative Example G2-1 and Comparative Example G3-1.

[0414] <Evaluation of deposition-type organic EL elements> Organic EL elements according to Examples G4-1 to G4-4 and Comparative Example G4-1 were prepared, and the luminance was 500 cd / m 2 The emission wavelength, half-width, driving voltage, external quantum efficiency, and LT50 (initial luminance 500cd / m 2 When continuously driven at a current density of 250 cd / m 2 The time during which the brightness was maintained above this level was measured.

[0415] [Table 5]

[0416] In Table 5, the chemical structures of "T2T", "4CzIPN", "BCC-TPTA" and "Liq" are shown below.

[0417] [ka]

[0418] <Example G4-1> A 26 mm × 28 mm × 0.7 mm glass substrate (manufactured by Optoscience Co., Ltd.) on which an ITO film having a thickness of 200 nm was formed by sputtering and polished to 50 nm was used as a transparent support substrate. This transparent support substrate was fixed to the substrate holder of a commercially available deposition device (manufactured by Showa Vacuum Co., Ltd.), and a molybdenum deposition boat containing HATCN, TBB, TcTa, 4CzIPN, compound (2A-szs-0004), T2T, Liq, and TPBi, and a tungsten deposition boat containing LiF and aluminum were attached.

[0419] The following layers were formed in order on the ITO film of the transparent support substrate. -4 The pressure was reduced to 10 Pa, and first, HATCN was heated and evaporated to a thickness of 5 nm to form a hole injection layer. Next, TBB was heated and evaporated to a thickness of 65 nm, and further, TcTa was heated and evaporated to a thickness of 10 nm to form a two-layer hole transport layer. Next, TcTa, 4CzIPN, and compound (2A-szs-0004) were heated simultaneously and evaporated to a thickness of 30 nm to form an emitting layer. The evaporation rate was adjusted so that the weight ratio of CBP, 4CzIPN, and compound (2A-szs-0004) was approximately 85:14:1. Next, T2T was heated and evaporated to a thickness of 10 nm, and then TPBi and Liq were heated and evaporated to a thickness of 40 nm to form a two-layer electron transport layer. The evaporation rate was adjusted so that the weight ratio of TPBi and Liq was approximately 70:30. The evaporation rate of each layer was 0.01 to 1 nm / sec. Then, LiF was heated and evaporated at a deposition rate of 0.01 to 0.1 nm / sec to a thickness of 1 nm, and then aluminum was heated and evaporated to a thickness of 100 nm to form a cathode, thereby obtaining an organic EL device. At this time, the evaporation rate of aluminum was adjusted to 1 to 10 nm / sec.

[0420] <Examples G4-2 to G4-4 and Comparative Example G4-1> The assisting dopant 4CzIPN and the dopant compound (2A-szs-0004) and their mixing ratios in Example G4-1 were changed to the assisting dopants, dopants, and mixing ratios shown in Table 5 to fabricate each device.

[0421] The evaluation results for each element are shown in Table 6. [Table 6]

[0422] In comparison with Comparative Example G4-1, Examples G4-1 to G4-4 exhibited higher efficiency and longer device life. As in Examples G4-3 and G4-4, devices using an exciplex and an assisting dopant can be realized.

[0423] <Evaluation of Coating-type Organic EL Devices> Next, an organic EL device obtained by forming an organic layer by coating will be described.

[0424] <Synthesis of polymer host compound: SPH-101> SPH-101 was synthesized according to the method described in International Publication No. 2015 / 008851. A copolymer in which M2 or M3 was bonded next to M1 was obtained, and it is estimated that each unit is 50:26:24 (molar ratio) based on the feed ratio. In the following structural formula, Me is a methyl group, Bpin is a pinacolatoboryl group, and * is the linking point of each unit. [ka]

[0425] <Synthesis of polymer hole transport compound: XLP-101> XLP-101 was synthesized according to the method described in JP 2018-61028 A. A copolymer in which M5 or M6 is bonded next to M4 was obtained, and it is estimated that each unit is 40:10:50 (molar ratio) based on the charge ratio. In the following structural formula, Me is a methyl group, Bpin is a pinacolatoboryl group, and * is the linking point of each unit. [ka]

[0426] <Examples 2-1 to 2-9> A coating solution of the material for forming each layer is prepared to fabricate a coating type organic EL device.

[0427] <Preparation of Organic EL Devices of Examples 2-1 to 2-3> Table 7 shows the material composition of each layer in the organic EL element. [Table 7]

[0428] The structure of "ET1" in Table 7 is shown below. [ka]

[0429] <Preparation of composition for forming light-emitting layer (1)> The composition for forming an emitting layer (1) is prepared by stirring the following components until a homogeneous solution is obtained. The prepared composition for forming an emitting layer is spin-coated on a glass substrate and dried by heating under reduced pressure to obtain a coating film with no film defects and excellent smoothness. Compound (A) 0.04% by weight SPH-101 1.96% by weight Xylene 69.00% by weight Decalin 29.00% by weight

[0430] Note that the compound (A) is a polycyclic aromatic compound represented by the general formula (1A) or general formula (1B) (for example, the compound (1A-32)), a polymer compound obtained by polymerizing the polycyclic aromatic compound as a monomer (that is, the monomer has a reactive substituent), or a polymer crosslinked body obtained by further crosslinking the polymer compound. The polymer compound for obtaining the polymer crosslinked body has a crosslinkable substituent.

[0431] <PEDOT:PSS solution> A commercially available PEDOT:PSS solution (Clevios(TM) P VP AI4083, an aqueous dispersion of PEDOT:PSS, manufactured by Heraeus Holdings) is used.

Chemical formula

[0432] <Preparation of OTPD solution> OTPD (LT-N159, manufactured by Luminescence Technology Corp) and IK-2 (a photo cationic polymerization initiator, manufactured by San-Apro) are dissolved in toluene to prepare an OTPD solution with an OTPD concentration of 0.7% by weight and an IK-2 concentration of 0.007% by weight.

Chemical formula

[0433] <Preparation of XLP-101 solution> XLP-101 is dissolved in xylene at a concentration of 0.6% by weight to prepare a 0.6% by weight XLP-101 solution.

[0434] <Preparation of PCz solution> PCz (polyvinyl carbazole) is dissolved in dichlorobenzene to prepare a 0.7% by weight PCz solution.

Chemical formula

[0435] <Example 2-1> A PEDOT:PSS solution is spin-coated onto a glass substrate on which ITO has been evaporated to a thickness of 150 nm, and then baked on a hot plate at 200°C for 1 hour to form a 40 nm thick PEDOT:PSS film (hole injection layer). Next, an OTPD solution is spin-coated, dried on a hot plate at 80°C for 10 minutes, and then exposed to light at an intensity of 100 mJ / cm using an exposure machine. 2 Then, the substrate is exposed to light at 4000 K and baked on a hot plate at 100° C. for 1 hour to form a solution-insoluble OTPD film with a thickness of 30 nm (hole transport layer). Next, the light-emitting layer-forming composition (1) is spin-coated and baked on a hot plate at 120° C. for 1 hour to form a light-emitting layer with a thickness of 20 nm.

[0436] The prepared multilayer film was fixed to the substrate holder of a commercially available deposition device (Showa Vacuum Co., Ltd.), and a molybdenum deposition boat containing ET1, a molybdenum deposition boat containing LiF, and a tungsten deposition boat containing aluminum were installed. The vacuum chamber was heated to 5×10 -4 After reducing the pressure to 1 Pa, ET1 is heated and evaporated to a thickness of 30 nm to form an electron transport layer. The evaporation rate for forming the electron transport layer is 1 nm / sec. Thereafter, LiF is heated and evaporated at an evaporation rate of 0.01 to 0.1 nm / sec to a thickness of 1 nm. Next, aluminum is heated and evaporated to a thickness of 100 nm to form a cathode. In this manner, an organic EL device is obtained.

[0437] <Example 2-2> An organic EL device is obtained in the same manner as in Example 2-1. The hole transport layer is formed by spin-coating an XLP-101 solution and baking it on a hot plate at 200° C. for 1 hour to form a film with a thickness of 30 nm.

[0438] <Example 2-3> An organic EL device is obtained in the same manner as in Example 2-1. The hole transport layer is formed by spin-coating a PCz solution and baking it on a hot plate at 120° C. for 1 hour to form a film with a thickness of 30 nm.

[0439] <Evaluation of Organic EL Devices of Examples 2-1 to 2-3> The coating type organic EL device obtained as described above is expected to have excellent driving voltage and external quantum efficiency, similar to the deposition type organic EL device.

[0440] <Preparation of Organic EL Devices of Examples 2-4 to 2-6> Table 8 shows the material composition of each layer in the organic EL element. [Table 8]

[0441] <Preparation of compositions (2) to (4) for forming light-emitting layer> A composition for forming a light-emitting layer (2) is prepared by stirring the following components until a homogeneous solution is obtained. Compound (A) 0.02% by weight mCBP 1.98% by weight Toluene 98.00% by weight

[0442] The following components are stirred until a homogeneous solution is obtained, thereby preparing a composition (3) for forming a light-emitting layer. Compound (A) 0.02% by weight SPH-101 1.98% by weight Xylene 98.00% by weight

[0443] A composition for forming a light-emitting layer (4) is prepared by stirring the following components until a homogeneous solution is obtained. Compound (A) 0.02% by weight DOBNA 1.98% by weight Toluene 98.00% by weight

[0444] In Table 8, "mCBP" is 3,3'-bis(N-carbazolyl)-1,1'-biphenyl, "DOBNA" is 3,11-di-o-tolyl-5,9-dioxa-13b-boranaphtho[3,2,1-de]anthracene, and "TSPO1" is diphenyl[4-(triphenylsilyl)phenyl]phosphine oxide. The chemical structures are shown below. [ka]

[0445] <Example 2-4> A glass substrate on which an ITO film is formed to a thickness of 45 nm is spin-coated with an ND-3202 (Nissan Chemical Industries) solution, and then heated in an air atmosphere at 50°C for 3 minutes, and then heated at 230°C for 15 minutes to form a 50 nm thick ND-3202 film (hole injection layer). Next, an XLP-101 solution is spin-coated, and heated on a hot plate in a nitrogen gas atmosphere at 200°C for 30 minutes to form a 20 nm thick XLP-101 film (hole transport layer). Next, a composition for forming an emitting layer (2) is spin-coated, and heated in a nitrogen gas atmosphere at 130°C for 10 minutes to form a 20 nm thick emitting layer.

[0446] The prepared multilayer film is fixed to the substrate holder of a commercially available deposition device (Showa Vacuum Co., Ltd.), and a molybdenum deposition boat containing TSPO1, a molybdenum deposition boat containing LiF, and a tungsten deposition boat containing aluminum are installed. The vacuum chamber is heated to 5×10 -4 After reducing the pressure to 1 Pa, TSPO1 is heated and evaporated to a thickness of 30 nm to form an electron transport layer. The evaporation rate for forming the electron transport layer is 1 nm / sec. Thereafter, LiF is heated and evaporated at an evaporation rate of 0.01 to 0.1 nm / sec to a thickness of 1 nm. Next, aluminum is heated and evaporated to a thickness of 100 nm to form a cathode. In this manner, an organic EL device is obtained.

[0447] <Examples 2-5 and 2-6> An organic EL element is obtained by using the composition for forming a light-emitting layer (3) or (4) in the same manner as in Example 2-4.

[0448] <Evaluation of Organic EL Devices of Examples 2-4 to 2-6> The coating type organic EL device obtained as described above is expected to have excellent driving voltage and external quantum efficiency, similar to the deposition type organic EL device.

[0449] <Preparation of Organic EL Devices of Examples 2-7 to 2-9> Table 9 shows the material composition of each layer in the organic EL element. [Table 9]

[0450] <Preparation of compositions (5) to (7) for forming light-emitting layer> A composition for forming a light-emitting layer (5) is prepared by stirring the following components until a homogeneous solution is obtained. Compound (A) 0.02% by weight 2PXZ-TAZ 0.18% by weight mCBP 1.80% by weight Toluene 98.00% by weight

[0451] A composition for forming a light-emitting layer (6) is prepared by stirring the following components until a homogeneous solution is obtained. Compound (A) 0.02% by weight 2PXZ-TAZ 0.18% by weight SPH-101 1.80% by weight Xylene 98.00% by weight

[0452] A composition for forming a light-emitting layer (7) is prepared by stirring the following components until a homogeneous solution is obtained. Compound (A) 0.02% by weight 2PXZ-TAZ 0.18% by weight DOBNA 1.80% by weight Toluene 98.00% by weight

[0453] In Table 9, "2PXZ-TAZ" is 10,10'-((4-phenyl-4H-1,2,4-triazole-3,5-diyl)bis(4,1-phenyl))bis(10H-phenoxazine). The chemical structure is shown below. [ka]

[0454] <Example 2-7> A glass substrate on which an ITO film is formed to a thickness of 45 nm is spin-coated with an ND-3202 (Nissan Chemical Industries) solution, and then heated at 50°C for 3 minutes in an air atmosphere, and then heated at 230°C for 15 minutes to form a 50 nm thick ND-3202 film (hole injection layer). Next, an XLP-101 solution is spin-coated, and heated on a hot plate at 200°C for 30 minutes in a nitrogen gas atmosphere to form a 20 nm thick XLP-101 film (hole transport layer). Next, a composition for forming an emitting layer (5) is spin-coated, and heated at 130°C for 10 minutes in a nitrogen gas atmosphere to form a 20 nm thick emitting layer.

[0455] The prepared multilayer film is fixed to the substrate holder of a commercially available deposition device (Showa Vacuum Co., Ltd.), and a molybdenum deposition boat containing TSPO1, a molybdenum deposition boat containing LiF, and a tungsten deposition boat containing aluminum are installed. The vacuum chamber is heated to 5×10 -4 After reducing the pressure to 1 Pa, TSPO1 is heated and evaporated to a thickness of 30 nm to form an electron transport layer. The evaporation rate for forming the electron transport layer is 1 nm / sec. Thereafter, LiF is heated and evaporated at an evaporation rate of 0.01 to 0.1 nm / sec to a thickness of 1 nm. Next, aluminum is heated and evaporated to a thickness of 100 nm to form a cathode. In this manner, an organic EL device is obtained.

[0456] <Examples 2-8 and 2-9> An organic EL device is obtained using the composition for forming a light emitting layer (6) or (7) in the same manner as in Example 2-7.

[0457] <Evaluation of Organic EL Devices of Examples 2-7 to 2-9> The coating type organic EL device obtained as described above is expected to have excellent driving voltage and external quantum efficiency, similar to the deposition type organic EL device.

[0458] As described above, some of the compounds according to the present invention have been evaluated as materials for organic EL devices and shown to be excellent materials, but other compounds that have not been evaluated also have the same basic skeleton and have similar structures overall, and it will be understood by those skilled in the art that they are similarly excellent materials for organic EL devices. [Industrial Applicability]

[0459] According to a preferred embodiment of the present invention, an organic EL device is produced using the novel polycyclic aromatic compound as, for example, a dopant material, thereby providing an organic EL device having a narrow half-width of the emission spectrum and excellent color purity, and further having excellent quantum efficiency and device life. In addition, since the novel polycyclic aromatic compound of the present invention has a rigid structure, many of the compounds have a sharper emission spectrum, a narrow half-width of the emission spectrum, and emit light with high color purity. [Explanation of symbols]

[0460] 100 Organic electroluminescent device 101 Substrate 102 Anode 103 Hole injection layer 104 Hole transport layer 105 Light-emitting layer 106 Electron transport layer 107 Electron injection layer 108 Cathode

Claims

1. A polycyclic aromatic compound represented by any one of the following structural formulas. 【Chemistry 1】 In each formula, R's are each independently a hydrogen atom, an aryl group having 6 to 16 carbon atoms, a heteroaryl group having 2 to 20 carbon atoms, a diarylamino group (wherein the aryl group is an aryl group having 6 to 10 carbon atoms), a diarylboryl group (wherein the aryl group is an aryl group having 6 to 10 carbon atoms), an alkyl group having 1 to 12 carbon atoms, or a cycloalkyl group having 3 to 16 carbon atoms, in which at least one hydrogen atom is optionally substituted by an alkyl group having 1 to 5 carbon atoms or a cycloalkyl group having 5 to 10 carbon atoms; Each o is independently an integer from 1 to 3; Each p is independently an integer from 1 to 4; Each q is independently an integer from 1 to 5; At least one hydrogen in the compounds represented by the above formulas may be substituted with deuterium, cyano, or halogen.

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

3. A material for organic devices containing the polycyclic aromatic compound described in claim 1 or 2.

4. The material for an organic device according to claim 3 , which is a material for an organic electroluminescent element, a material for an organic field effect transistor, or a material for an organic thin-film solar cell.

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

6. An ink composition comprising the polycyclic aromatic compound described in claim 1 or 2 and an organic solvent.

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

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. A display device or lighting device comprising the organic electroluminescent device according to claim 7.

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