Polycyclic aromatic compound

Abstract

To provide a new compound that is useful as a material for organic devices, in particular, as a material for luminescent layers, which is to form luminescent layers of organic EL elements.SOLUTION: The present invention discloses a polycyclic aromatic compound represented by, for example, formula (1-161).SELECTED DRAWING: None

Description

[Technical field]

[0001] The present invention relates to a polycyclic aromatic compound. The present invention also relates to a material for an organic device, an organic electroluminescent device, and a display device and a lighting device, each of which contains the polycyclic aromatic compound. [Background technology]

[0002] Conventionally, display devices using electroluminescent light-emitting elements have been extensively studied because they can be made more energy-efficient and thinner, and organic electroluminescent elements (sometimes referred to as "organic EL elements" or simply "elements" in this specification) made of organic materials have been actively studied because they can be easily made lighter and larger. In particular, the development of organic materials that have the luminescence properties of blue, one of the three primary colors of light, and organic materials that have the ability to transport charges such as holes and electrons (potential to become semiconductors or superconductors), regardless of whether they are polymeric or low molecular weight compounds, has been actively studied.

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

[0004] Among them, Patent Document 1 discloses that polycyclic aromatic compounds in which aromatic rings are linked by hetero elements such as boron, phosphorus, oxygen, nitrogen, and sulfur are useful as materials for organic electroluminescent devices and the like. These polycyclic aromatic compounds have a large HOMO-LUMO gap and high triplet excitation energy (E T ) and exhibits thermally activated delayed fluorescence, it has been reported that they are particularly useful as fluorescent materials for organic electroluminescent devices. [Prior art documents] [Patent documents]

[0005] [Patent Document 1] International Publication No. 2015 / 102118 Summary of the Invention [Problem to be solved by the invention]

[0006] As described above, various materials have been developed as materials for use in organic EL elements, but in order to increase the options for materials for organic EL elements, it is desirable to develop materials made of compounds different from conventional ones. An object of the present invention is to provide a novel material useful as a material for organic devices such as organic EL elements. [Means for solving the problem]

[0007] The present inventors have conducted extensive research to solve the above problems, and have succeeded in producing a new compound as a polycyclic aromatic compound in which aromatic rings are linked by hetero elements such as boron, phosphorus, oxygen, nitrogen, and sulfur. They have also found that an excellent organic EL device can be obtained by disposing a layer containing this polycyclic aromatic compound between a pair of electrodes to form an organic EL device, and have completed the present invention. That is, the present invention provides the following polycyclic aromatic compounds, and further provides materials for organic devices containing the following polycyclic aromatic compounds.

[0008] <1> A polycyclic aromatic compound having a partial structure represented by formula (1A) and at least one partial structure represented by formula (1B); [ka] In formula (1A) and formula (1B), ring A and ring B are each independently an optionally substituted aryl ring or an optionally substituted heteroaryl ring; R XD is an optionally substituted aryl, an optionally substituted heteroaryl, an optionally substituted alkyl or an optionally substituted cycloalkyl, and the dashed line may be -X- or a single bond to be bonded to at least one of ring A or ring B; A ring, B ring or R XD wherein the aryl or heteroaryl ring in at least one of the above is bonded to a moiety represented by formula (1B), The partial structure represented by formula (1B) is bonded at the two * positions to two adjacent atoms on the aryl or heteroaryl ring, respectively; each C ring is independently an optionally substituted aryl ring or an optionally substituted heteroaryl ring; R XE is an optionally substituted aryl, an optionally substituted heteroaryl, an optionally substituted alkyl or an optionally substituted cycloalkyl, and the dashed line may be -X- or a single bond to be bonded to the C ring, or the dashed line may be -X- or a single bond to be bonded to the ring to which the partial structure represented by formula (1B) is bonded at the (*) position, each Y is independently B, P, P=O or P=S; X is, independently, >C(-R)2, >NR, >O, >Si(-R)2 or >S, R of >NR is an optionally substituted aryl, an optionally substituted heteroaryl, an optionally substituted alkyl or an optionally substituted cycloalkyl, R of >C(-R)2 and >Si(-R)2 are, independently, hydrogen, an optionally substituted aryl, an optionally substituted alkyl or an optionally substituted cycloalkyl, and may be bonded to each other by a linking group, and at least one of R of >NR, >C(-R)2 and >Si(-R)2 is connected to ring A, ring B, ring C, ring R by a linking group or a single bond. XD , or R XE and At least one of X is >NR, and R in at least one of X which is >NR is the ring A, ring B, ring C, or ring R XD , or R XE In formula (A10), R A1 ~R A4are each independently hydrogen, optionally substituted alkyl, or optionally substituted cycloalkyl; R A1 ~R A4 any 2 to 4 of the above may be bonded to each other via a linking group or a single bond, and the partial structure represented by formula (A10) is bonded to one ring at the two * positions and to the other ring at the ** position, At least one selected from the group consisting of an aryl ring and a heteroaryl ring in the polycyclic aromatic compound may be condensed with at least one cycloalkane, at least one hydrogen in the cycloalkane may be substituted, and at least one -CH- in the cycloalkane may be substituted with -O-; At least one hydrogen in the polycyclic aromatic compound may be substituted with deuterium, cyano or halogen.

[0009] <2> R XD is an optionally substituted aryl or an optionally substituted heteroaryl, the dashed line is -X- and is bonded to ring A; and R XE is an optionally substituted aryl or an optionally substituted heteroaryl, and the dashed line is -X- which is bonded to the C ring; <1> The polycyclic aromatic compound according to claim 1. <3> R A1 and R A4 are bonded to each other, and R A2 and R A3 are each independently hydrogen or optionally substituted alkyl; <1> or <2> The polycyclic aromatic compound according to claim 1. <4> R A1 and R A4 are bonded together to form -(CH2)4-, and R A2 and R A3 are all methyl, <1> or <2> The polycyclic aromatic compound according to claim 1. <5> Substituents when ring A, ring B and ring C are substituted aryl rings or substituted heteroaryl rings, and R XD and R XEis a substituted aryl or a substituted heteroaryl, each of the substituents being selected from the group consisting of substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted diarylamino, substituted or unsubstituted diheteroarylamino, substituted or unsubstituted arylheteroarylamino, substituted or unsubstituted diarylboryl (two aryls may be bonded via a single bond or a linking group), substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryloxy, substituted silyl, and -L-Ak; L is >NR, >O or >S, R of >NR is optionally substituted aryl, optionally substituted heteroaryl, optionally substituted alkyl or optionally substituted cycloalkyl, R of >NR is optionally bonded to Ak via a linking group or a single bond; Ak is hydrogen, optionally substituted alkyl, or optionally substituted cycloalkyl, in which at least one hydrogen in the alkyl and cycloalkyl is optionally substituted, and at least one -CH2- in the alkyl and cycloalkyl is optionally substituted with -O- and -S-; A ring, B ring, C ring, R XD and R XE are each bonded to either X or Y at a 5-membered or 6-membered ring. <1> ~ <4> 2. The polycyclic aromatic compound according to claim 1 .

[0010] <6> Represented by any one of the following formulas (3-1-1), (3-1-2), and (3-2-1): <1> 4. The polycyclic aromatic compound according to claim 1 ; [ka] In formula (3-1-1), formula (3-1-2), formula (3-2-1), X 1are each independently >C(-R)2, >NR, >O, >Si(-R)2 or >S, R of the >NR is an aryl having 6 to 12 carbon atoms which may be substituted with an alkyl having 1 to 6 carbon atoms or a cycloalkyl having 3 to 14 carbon atoms, a heteroaryl having 2 to 15 carbon atoms which may be substituted with an alkyl having 1 to 6 carbon atoms or a cycloalkyl having 3 to 14 carbon atoms, an alkyl having 1 to 6 carbon atoms or a cycloalkyl having 3 to 14 carbon atoms, R of the >C(-R)2 and >Si(-R)2 are each independently hydrogen, an aryl having 6 to 12 carbon atoms, an alkyl having 1 to 6 carbon atoms or a cycloalkyl having 3 to 14 carbon atoms, each Y is independently B, P, P=O or P=S; Z is independently -C(-R Z )= or -N=, and two adjacent Zs are -C(-R Z )2-, -Si(-R Z )2-, -N(-R Z )-, -O-, or -S-, R Z are each independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl (two aryls may be bonded via a single bond or a linking group), alkyl, cycloalkyl, alkoxy, aryloxy, substituted silyl, or -L-Ak, in which at least one hydrogen may be substituted with an aryl, heteroaryl, alkyl, or cycloalkyl; and R Zadjacent 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 c ring, the d ring, or the e ring, and at least one hydrogen atom in the formed ring may be replaced by an aryl, a heteroaryl, a diarylamino, a diheteroarylamino, an arylheteroarylamino, a diarylboryl (two aryls may be bonded via a single bond or a linking group), an alkyl, a cycloalkyl, an alkoxy, an aryloxy, a substituted silyl, or -L-Ak, and at least one hydrogen atom in these may be replaced by an aryl, a heteroaryl, an alkyl, or a cycloalkyl; L is >NR, >O or >S, R of >NR is optionally substituted aryl, optionally substituted heteroaryl, optionally substituted alkyl or optionally substituted cycloalkyl, R of >NR is optionally bonded to Ak via a linking group or a single bond; Ak is hydrogen, optionally substituted alkyl, or optionally substituted cycloalkyl, in which at least one hydrogen in the alkyl and cycloalkyl is optionally substituted, and at least one -CH2- in the alkyl and cycloalkyl is optionally substituted with -O- and -S-; At least one hydrogen atom in the compounds represented by formula (3-1-1), formula (3-1-2) and formula (3-2-1) may be substituted with deuterium, cyano or halogen.

[0011] <7> Y is B, Z is independently -C(-R Z )= or -N=, where Z at the o-position or p-position to Y is -C(-R Z )= <6> The polycyclic aromatic compound according to claim 1. <8> Z is -C(-R Z )= <7> The polycyclic aromatic compound according to claim 1. <9> <1> ~ <8> 2. A reactive compound in which the polycyclic aromatic compound according to any one of claims 1 to 11 is substituted with a reactive substituent. <10> <9> A polymer compound obtained by polymerizing the reactive compound described above as a monomer, or a crosslinked polymer obtained by further crosslinking the polymer compound.

[0012] <11> Main chain polymer <9> or a pendant-type crosslinked polymer obtained by further crosslinking the pendant-type polymer compound. <12> <1> ~ <8> 2. A material for an organic device, comprising the polycyclic aromatic compound according to claim 1. <13> <9> A material for an organic device, comprising the reactive compound according to claim 1. <14> <10> 2. A material for an organic device, comprising the polymer compound or crosslinked polymer described in 1. <15> <11> 2. A material for an organic device, comprising the pendant type polymer compound or the pendant type crosslinked polymer according to claim 1. <16> The organic device material is a material for an organic electroluminescent element, a material for an organic field effect transistor, or a material for an organic thin-film solar cell. <12> ~ <15> 2. The material for an organic device according to claim 1 . <17> The material for an organic electroluminescent device is a material for a light-emitting layer. <16> The material for an organic device according to claim 1. <18> <1> ~ <8> 2. A composition comprising the polycyclic aromatic compound according to claim 1 and an organic solvent. <19> <9> and an organic solvent. <20> A main chain polymer, <9> and an organic solvent.

[0013] <21> <10> 2. A composition comprising the polymer compound or crosslinked polymer according to claim 1 and an organic solvent. <22> <11> A composition comprising the pendant type polymer compound or the pendant type crosslinked polymer according to claim 1, and an organic solvent. <23> A pair of electrodes consisting of an anode and a cathode, and a gas sensor disposed between the pair of electrodes, <1> ~ <8> The polycyclic aromatic compound according to any one of the above. <9> The reactive compound according to <10> or <11> and an organic layer containing the pendant type polymer compound or the pendant type crosslinked polymer according to claim 1. <24> The organic layer is an emitting layer. <23> The organic electroluminescent device according to claim 1. <25> 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; <24> The organic electroluminescent device according to claim 1.

[0014] <26> The host is an anthracene-based compound, a fluorene-based compound, or a dibenzochrysene-based compound; <25> The organic electroluminescent device according to claim 1. <27> at least one of an electron transport layer and an electron injection layer disposed between the cathode and the light emitting layer, and at least one of the electron transport layer and the electron injection layer contains at least one selected from the group consisting of borane derivatives, pyridine derivatives, fluoranthene derivatives, BO derivatives, anthracene derivatives, benzofluorene derivatives, phosphine oxide derivatives, pyrimidine derivatives, arylnitrile derivatives, triazine derivatives, benzimidazole derivatives, phenanthroline derivatives and quinolinol metal complexes; <24> ~ <26> 13. The organic electroluminescent device according to claim 12, <28> At least one of the electron transport layer and the electron injection layer further contains at least one selected from the group consisting of an alkali metal, an alkaline earth metal, a rare earth metal, an oxide of an alkali metal, a halide of an alkali metal, an oxide of an alkaline earth metal, a halide of an alkaline earth metal, an oxide of a rare earth metal, a halide of a rare earth metal, an organic complex of an alkali metal, an organic complex of an alkaline earth metal, and an organic complex of a rare earth metal. <27> The organic electroluminescent device according to claim 1. <29> At least one of the hole injection layer, the hole transport layer, the light emitting layer, the electron transport layer and the electron injection layer comprises a polymer compound obtained by polymerizing a low molecular weight compound capable of forming each layer as a monomer, or a crosslinked polymer obtained by further crosslinking the polymer compound, or a pendant type polymer compound obtained by reacting a low molecular weight compound capable of forming each layer with a main chain polymer, or a pendant type crosslinked polymer obtained by further crosslinking the pendant type polymer compound, <24> ~ <28> 13. The organic electroluminescent device according to claim 12, <30> <23> ~ <29> A display device or a lighting device comprising the organic electroluminescent device according to any one of claims 1 to 4. Effect of the Invention

[0015] The present invention provides a novel polycyclic aromatic compound. The polycyclic aromatic compound of the present invention is useful as a material for an organic device, particularly as a material for a light-emitting layer for forming a light-emitting layer of an organic electroluminescent device. [Brief description of the drawings]

[0016] [Figure 1] FIG. 1 is a schematic cross-sectional view showing an example of an organic EL element. [Diagram 2] FIG. 1 is a diagram illustrating a method for producing an organic EL element on a substrate having a bank by using an inkjet method. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0017] The present invention will be described in detail below. The following description of the constituent elements may be based on representative embodiments or specific examples, but the present invention is not limited to such embodiments. In this specification, a numerical range expressed using "~" means a range including the numerical values ​​before and after "~" as the lower and upper limits. In this specification, "hydrogen" in the explanation of the structural formula means "hydrogen atom (H)".

[0018] 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.

[0019] 1. Polycyclic aromatic compounds The polycyclic aromatic compound of the present invention is a polycyclic aromatic compound having a partial structure represented by the following formula (1A) and at least one partial structure represented by the following formula (1B).

[0020] [ka]

[0021] In formula (1A) and formula (1B), "A", "B", and "C" are symbols indicating ring structures. In addition, in formula (1A) and formula (1B), the dashed lines indicate that the rings or groups at both ends of the dashed lines may or may not be bonded to each other. In formula (1A) and formula (1B), * indicates a position, but in formula (1B), the (*) at one end of the dashed line indicates that the position may or may not be present.

[0022] In the polycyclic aromatic compound of the present invention, at least one of Xs connecting ring structures to each other is >NR, where R is an optionally substituted alkyl or an optionally substituted cycloalkyl, and A ring, B ring, C ring, R ring, and R ring are connected by a linking group or a single bond. XD , or R XEAt least one of the aryl or heteroaryl rings is linked to the aryl or heteroaryl ring. Specifically, the polycyclic aromatic compound of the present invention has the following partial structure (A10) due to the above-mentioned linkage.

[0023] [ka]

[0024] In formula (A10), R A1 ~R A4 are each independently hydrogen, optionally substituted alkyl, or optionally substituted cycloalkyl; R A1 ~R A4 Any 2 to 4 of may be bonded to each other by a linking group or a single bond, and X is bonded to one of the two rings at the two * positions and to the other ring at the ** position. That is, N in formula (A10) is N of >NR when X is >NR. The atoms on the rings bonded at the two * positions may be adjacent atoms (preferably carbon atoms). Although the partial structure represented by formula (A10) contains an N-C bond with a weak bond dissociation energy (BDE), the presence of another bond forming a ring promotes a reverse reaction (recombination reaction) even when the N-C bond is broken, so that the polycyclic aromatic compound of the present invention has a more stable structure. Therefore, it is expected that an organic EL device manufactured using the polycyclic aromatic compound of the present invention will have a longer device life. The number of partial structures represented by formula (A10) formed by the above-mentioned linkage contained in the polycyclic aromatic compound of the present invention is 1 to "the number of X", and is preferably 1 or 2.

[0025] In formula (A10), R A1 ~R A4 is hydrogen, optionally substituted alkyl or optionally substituted cycloalkyl; R A1 ~R A4 Any two to four of these may be linked to each other via a linking group. R A1 ~R A4is any two (R A1 and R A4 , R A1 and R A4 And R A1 and R A4 , R A1 and R A2 , R A3 and R A4 , R A1 and R A4 And R A1 and R A4 ) are preferably bonded to each other via a linking group or a single bond, and R A1 and R A4 are more preferably bonded to each other by a linking group or a single bond. An example of a divalent group formed by bonding to each other is alkylene. At least one hydrogen in the alkylene may be substituted with an alkyl or cycloalkyl, and at least one (preferably one) -CH2- in the alkane may be substituted with -O- and -S-. As the linking group, a straight chain alkylene having 2 to 5 carbon atoms is preferred, a straight chain alkylene having 3 or 4 carbon atoms is more preferred, and a straight chain alkylene having 4 carbon atoms (-(CH2)4-) is even more preferred. It is particularly preferred that the straight chain alkylene having 4 carbon atoms (-(CH2)4-) is unsubstituted.

[0026] The remaining R that is not involved in the linkage through the linking group A1 ~R A4 are each independently preferably hydrogen or an optionally substituted alkyl, more preferably an optionally substituted alkyl having 1 to 6 carbon atoms, further preferably an unsubstituted alkyl having 1 to 6 carbon atoms, and most preferably methyl. That is, as the partial structure represented by formula (A10), a structure represented by the following formula (A11) is preferable.

[0027] [ka] In formula (A11), Me is methyl, and is bonded to one of the two rings to which X is bonded at the two * positions and to the other ring at the ** position.

[0028] In formula (1A) and formula (1B), ring A, ring B and ring C are each independently an optionally substituted aryl ring or an optionally substituted heteroaryl ring. In formula (1A), R XD R is optionally substituted aryl, optionally substituted heteroaryl, optionally substituted alkyl or optionally substituted cycloalkyl. XD R may be bonded to at least one of ring A or ring B via the dashed line -X- or a single bond. XD is preferably an optionally substituted aryl or an optionally substituted heteroaryl. XD In formula (1B), it is preferable that the broken line is -X- and is bonded to ring A. XE R is each independently an optionally substituted aryl, an optionally substituted heteroaryl, an optionally substituted alkyl, or an optionally substituted cycloalkyl. XE may be bonded to the C ring via the dashed line -X- or a single bond, or may be bonded to the ring to which the partial structure represented by formula (1B) is bonded at the (*) position via the dashed line -X- or a single bond. XE is preferably an optionally substituted aryl or an optionally substituted heteroaryl. XE is preferably bonded to ring C via the dashed line -X-. That is, formula (1A) is preferably the following formula (2A), and formula (1B) is preferably the following formula (2B).

[0029] [ka]

[0030] In formula (2A), an aryl or heteroaryl ring in at least one of rings A, B, or D is bonded to a partial structure represented by formula (2B), The partial structure represented by formula (2B) is bonded at the two * positions to two adjacent atoms on the aryl or heteroaryl ring. In formula (2A), the same symbols as those in formula (1A) have the same meanings as those in formula (1A). "D" is a symbol representing a ring structure, and R in formula (1A) XD In formula (2B), the same symbols as those in formula (1B) have the same meanings as those in formula (1B). "E" is a symbol representing a ring structure, and R in formula (1B) XE This is one aspect.

[0031] Ring A, ring B, ring C, and R in formula (1A) and formula (1B) XD and R XE is preferably bonded to any of X and Y in a 5-membered or 6-membered ring (ring A, ring B, ring C, ring D, and ring E in formula (2A) and formula (2B)). Here, "bonded to any of X and Y in a 5-membered or 6-membered ring" means that a ring is formed only with the 5-membered or 6-membered ring, or that other rings are condensed to include the 5-membered or 6-membered ring to form ring A, ring B, ring C, ring R, ring B, ring C, ring D, ring E, ring E, ring F ... XD or R XE and the aryl or heteroaryl ring is bonded to any of X and Y at a ring-constituting atom on the 5- or 6-membered ring.

[0032] The rings A, B, and C in formula (1A) and (1B), and the rings A, B, C, D, and E in formula (2A) and (2B) are each independently an optionally substituted aryl ring or an optionally substituted heteroaryl ring.

[0033] Ring A, ring B, ring C, and R in formula (1A) and formula (1B) XD and R XEFurthermore, the "aryl ring" in ring A, ring B, ring C, ring D and ring E in formula (2A) and formula (2B) includes, for example, an aryl ring having 6 to 30 carbon atoms, preferably an aryl ring having 6 to 16 carbon atoms, more preferably an aryl ring having 6 to 12 carbon atoms, and particularly preferably an aryl ring having 6 to 10 carbon atoms.

[0034] Specific examples of the "aryl ring" include a monocyclic benzene ring, a bicyclic bicyclic bicyclic naphthalene ring, an indene ring, a tricyclic terphenyl ring (m-terphenyl, o-terphenyl, p-terphenyl), a condensed tricyclic acenaphthylene ring, a fluorene ring, a phenalene ring, a phenanthrene ring, an anthracene ring, a condensed tetracyclic triphenylene ring, a pyrene ring, a naphthacene ring, a chrysene ring, a condensed pentacyclic perylene ring, a pentacene ring, etc. In addition, the fluorene ring, the benzofluorene ring, and the indene ring each include a structure in which a fluorene ring, a benzofluorene ring, a cyclopentane ring, etc. are spiro-bonded. In addition, the fluorene ring, benzofluorene ring, and indene ring also include rings in which two of the two hydrogen atoms of the methylene are replaced by alkyl such as methyl as the first substituent described below, resulting in a dimethylfluorene ring, a dimethylbenzofluorene ring, a dimethylindene ring, and the like.

[0035] Ring A, ring B, ring C, and R in formula (1A) and formula (1B) XD and R XE Furthermore, examples of the "heteroaryl ring" in ring A, ring B, ring C, ring D and ring E in formula (2A) and formula (2B) include heteroaryl rings having 2 to 30 carbon atoms, preferably heteroaryl rings having 2 to 25 carbon atoms, more preferably heteroaryl rings having 2 to 20 carbon atoms, further preferably heteroaryl rings having 2 to 15 carbon atoms, and particularly preferably heteroaryl rings having 2 to 10 carbon atoms. Examples of the "heteroaryl ring" include heterocycles containing, as ring-constituting atoms other than carbon, 1 to 5 heteroatoms selected from oxygen, sulfur and nitrogen.

[0036] 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 phthalazine ring, a naphthyl ring, a phenyl ... Examples of the ring include a dimethyldihydroacridine ring, a purine ring, a pteridine ring, a carbazole ring, an acridine ring, a phenoxathiin ring, a phenoxazine ring, a phenothiazine ring, a phenazine ring, a phenazasiline ring, an indolizine ring, a furan ring, a benzofuran ring, an isobenzofuran ring, a dibenzofuran ring, a thiophene ring, a benzothiophene ring, a dibenzothiophene ring, a furazan ring, a thianthrene ring, an indolocarbazole ring, a benzoindolocarbazole ring, a benzobenzoindolocarbazole ring, a naphthobenzofuran ring, a dioxin ring, a dihydroacridine ring, a xanthene ring, a thioxanthene ring, a dibenzodioxin ring, etc. In addition, it is also preferable that two of the two hydrogen atoms of the methylene are substituted with an alkyl such as methyl as the first substituent described later, to form a dimethyldihydroacridine ring, a dimethylxanthene ring, a dimethylthioxanthene ring, etc. In addition, bicyclic rings such as bipyridine ring, phenylpyridine ring, and pyridylphenyl ring, and tricyclic rings such as terpyridyl ring, bispyridylphenyl ring, and pyridylbiphenyl ring are also included as the "heteroaryl ring". The "heteroaryl ring" also includes a pyran ring.

[0037] When at least one hydrogen atom in the above aryl ring or heteroaryl ring is substituted with a substituent, the substituent is preferably substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted diarylamino, substituted or unsubstituted diheteroarylamino, substituted or unsubstituted arylheteroarylamino (amino having aryl and heteroaryl), substituted or unsubstituted diarylboryl (two aryls may be bonded via a single bond or a linking group), substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryloxy, substituted silyl, or -L-Ak. When these groups have a substituent, the substituent may be aryl, heteroaryl, alkyl or cycloalkyl, or diarylamino.

[0038] At least one hydrogen atom in the above "aryl ring" or "heteroaryl ring" may be substituted with a first substituent, which is a substituted or unsubstituted "aryl", a substituted or unsubstituted "heteroaryl", a substituted or unsubstituted "diarylamino", a substituted or unsubstituted "diheteroarylamino", a substituted or unsubstituted "arylheteroarylamino", a substituted or unsubstituted "diarylboryl (two aryls may be bonded via a single bond or a linking group)", a substituted or unsubstituted "alkyl", a substituted or unsubstituted "cycloalkyl", a substituted or unsubstituted "alkoxy", a substituted or unsubstituted "aryloxy", a substituted "silyl", or -L-Ak. The aryl of the first substituent, the "aryl" or "heteroaryl", the aryl of the "diarylamino", the heteroaryl of the "diheteroarylamino", the aryl and heteroaryl of the "arylheteroarylamino", the aryl of the "diarylboryl", and the aryl of the "aryloxy" include the monovalent group of the above-mentioned "aryl ring" or "heteroaryl ring".

[0039] 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.

[0040] Specific examples of the aryl include phenyl, which is a monocyclic aryl; (2-, 3-, 4-) biphenylyl, which is a bicyclic aryl; (1-, 2-) naphthyl, (2-, 3-, 4-, 5-, 6-, 7-) indenyl, which is a condensed bicyclic aryl; and terphenylyl, which is a tricyclic aryl (m-terphenyl-2'-yl, m-terphenyl-4'-yl, m-terphenyl-5'-yl, o-terphenyl-3'-yl, o-terphenyl-4'-yl, p-terphenyl-2'-yl, m-terphenyl-2-yl, m-terphenyl-3-yl, m-terphenyl-4-yl, o-terphenyl-2-yl, o-terphenyl-3-yl, o-terphenyl-4-yl, p-terphenyl-2-yl, p-terphenyl-3-yl, p ... aryl-4-yl), fused tricyclic aryls, acenaphthylene-(1-,3-,4-,5-)yl, fluoren-(1-,2-,3-,4-,9-)yl, phenalen-(1-,2-)yl, (1-,2-,3-,4-,9-)phenanthryl, tetracyclic aryls, quaterphenylyl (5'-phenyl-m-terphenyl-2-yl, 5'-phenyl-m-terphenylyl), Examples of fused tetracyclic aryls include triphenylene-(1-, 2-)yl, pyrene-(1-, 2-, 4-)yl, naphthacene-(1-, 2-, 5-)yl, and fused pentacyclic aryls include perylene-(1-, 2-, 3-)yl and pentacene-(1-, 2-, 5-, 6-)yl.

[0041] Furthermore, examples of "heteroaryl" include heteroaryls having 2 to 30 carbon atoms, preferably heteroaryls having 2 to 25 carbon atoms, more preferably heteroaryls having 2 to 20 carbon atoms, further preferably heteroaryls having 2 to 15 carbon atoms, and particularly preferably heteroaryls having 2 to 10 carbon atoms. Furthermore, examples of heteroaryls include heterocycles containing, as ring-constituting atoms other than carbon, 1 to 5 heteroatoms selected from oxygen, sulfur, and nitrogen.

[0042] Specific examples of heteroaryl include furyl, thienyl, pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, pyrazolyl, oxadiazolyl, furazanyl, thiadiazolyl, triazolyl, tetrazolyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, benzo[b]thienyl, dibenzothienyl, indyl, and aryl. Examples of the aryl include isoindolyl, 1H-indazolyl, benzimidazolyl, benzoxazolyl, benzothiazolyl, 1H-benzotriazolyl, quinolyl, isoquinolyl, cinnolyl, quinazolyl, quinoxalinyl, phthalazinyl, naphthyridinyl, purinyl, pteridinyl, carbazolyl, acridinyl, phenoxazinyl, phenothiazinyl, phenazinyl, phenoxathiinyl, thianthrenyl, and indolizinyl.

[0043] The "alkyl" as the first substituent may be either linear or branched, and examples thereof include linear alkyl having 1 to 24 carbon atoms or branched alkyl having 3 to 24 carbon atoms. An alkyl having 1 to 18 carbon atoms (branched alkyl having 3 to 18 carbon atoms) is preferred, an alkyl having 1 to 12 carbon atoms (branched alkyl having 3 to 12 carbon atoms) is more preferred, an alkyl having 1 to 8 carbon atoms (branched alkyl having 3 to 8 carbon atoms) is even more preferred, an alkyl having 1 to 6 carbon atoms (branched alkyl having 3 to 6 carbon atoms) is particularly preferred, and an alkyl having 1 to 5 carbon atoms (branched alkyl having 3 to 5 carbon atoms) is most preferred.

[0044] Specific examples of alkyl include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, t-butyl, n-pentyl, isopentyl, neopentyl, t-pentyl (t-amyl), n-hexyl, 1-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, n-heptyl, 1-methylhexyl, n-octyl, t-octyl (1,1,3,3-tetramethylbutyl), and the like. ), 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 2,6-dimethyl-4-heptyl, 3,5,5-trimethylhexyl, n-decyl, n-undecyl, 1-methyldecyl, n-dodecyl, n-tridecyl, 1-hexylheptyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, n-heptadecyl, n-octadecyl, and n-eicosyl.

[0045] 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.

[0046] As the substituent containing the above-mentioned "alkyl", a tertiary alkyl represented by the following formula (tR) is one of the particularly preferred substituents when at least one hydrogen atom in the above-mentioned aryl ring or heteroaryl ring is substituted with a substituent. This is because such a bulky substituent increases the intermolecular distance, thereby improving the luminescence quantum yield (PLQY). In addition, a substituent in which a tertiary alkyl represented by the formula (tR) is substituted with another substituent as a second substituent is also preferred. Specifically, examples include a diarylamino substituted with a tertiary alkyl represented by (tR), a carbazolyl (preferably N-carbazolyl) substituted with a tertiary alkyl represented by (tR), or a benzocarbazolyl (preferably N-benzocarbazolyl) substituted with a tertiary alkyl represented by (tR). Examples of the "diarylamino" include the group described below as the "first substituent". Substitution of the group of formula (tR) on diarylamino, carbazolyl and benzocarbazolyl includes examples in which some or all of the hydrogen atoms on the aryl ring or benzene ring in these groups are substituted with the group of formula (tR).

[0047] [ka]

[0048] In the formula (tR), R a , R b , and R c are each independently an alkyl having 1 to 24 carbon atoms, any -CH2- in the alkyl may be replaced with -O-, and a group represented by formula (tR) replaces at least one hydrogen in a compound consisting of a partial structure represented by formula (1A) and at least one partial structure represented by formula (1B) at *.

[0049] R a , R b and R cThe "alkyl having 1 to 24 carbon atoms" may be either linear or branched, and examples thereof include linear alkyl having 1 to 24 carbon atoms or branched alkyl having 3 to 24 carbon atoms, alkyl having 1 to 18 carbon atoms (branched alkyl having 3 to 18 carbon atoms), alkyl having 1 to 12 carbon atoms (branched alkyl having 3 to 12 carbon atoms), alkyl having 1 to 6 carbon atoms (branched alkyl having 3 to 6 carbon atoms), and alkyl having 1 to 4 carbon atoms (branched alkyl having 3 to 4 carbon atoms).

[0050] R in formula (tR) a , R b , and R c The total number of carbon atoms is preferably 3 to 20, and particularly preferably 3 to 10.

[0051] R a , R b , and R c Specific examples of alkyl include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, t-butyl, n-pentyl, isopentyl, neopentyl, t-pentyl, n-hexyl, 1-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, n-heptyl, 1-methylhexyl, n-octyl, t-octyl, 1-methylheptyl, 2 Examples of the aryl group include n-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 2,6-dimethyl-4-heptyl, 3,5,5-trimethylhexyl, n-decyl, n-undecyl, 1-methyldecyl, n-dodecyl, n-tridecyl, 1-hexylheptyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, n-heptadecyl, n-octadecyl, and n-eicosyl.

[0052] Examples of the group represented by the formula (tR) include t-butyl, t-amyl, 1-ethyl-1-methylpropyl, 1,1-diethylpropyl, 1,1-dimethylbutyl, 1-ethyl-1-methylbutyl, 1,1,3,3-tetramethylbutyl, 1,1,4-trimethylpentyl, 1,1,2-trimethylpropyl, 1,1-dimethyloctyl, 1,1-dimethylpentyl, 1,1-dimethylheptyl, 1,1,5-trimethylhexyl, 1-ethyl- Examples include 1-methylhexyl, 1-ethyl-1,3-dimethylbutyl, 1,1,2,2-tetramethylpropyl, 1-butyl-1-methylpentyl, 1,1-diethylbutyl, 1-ethyl-1-methylpentyl, 1,1,3-trimethylbutyl, 1-propyl-1-methylpentyl, 1,1,2-trimethylpropyl, 1-ethyl-1,2,2-trimethylpropyl, 1-propyl-1-methylbutyl, 1,1-dimethylhexyl, etc. Among these, t-butyl and t-amyl are preferred.

[0053] Examples of the "cycloalkyl" as the first substituent include cycloalkyl having 3 to 24 carbon atoms, cycloalkyl having 3 to 20 carbon atoms, cycloalkyl having 3 to 16 carbon atoms, cycloalkyl having 3 to 14 carbon atoms, cycloalkyl having 5 to 10 carbon atoms, cycloalkyl having 5 to 8 carbon atoms, cycloalkyl having 5 to 6 carbon atoms, and cycloalkyl having 5 carbon atoms.

[0054] Specific examples of cycloalkyl include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, and alkyl (particularly methyl) substituted derivatives of these having 1 to 5 carbon atoms, as well as norbornenyl, bicyclo[1.0.1]butyl, bicyclo[1.1.1]pentyl, bicyclo[2.0.1]pentyl, bicyclo[1.2.1]hexyl, bicyclo[3.0.1]hexyl, bicyclo[2.1.2]heptyl, bicyclo[2.2.2]octyl, adamantyl, diamantyl, decahydronaphthalenyl, and decahydroazulenyl.

[0055] Furthermore, examples of the "alkoxy" as the first substituent include linear alkoxy having 1 to 24 carbon atoms or branched alkoxy having 3 to 24 carbon atoms. An alkoxy having 1 to 18 carbon atoms (branched alkoxy having 3 to 18 carbon atoms) is preferred, an alkoxy having 1 to 12 carbon atoms (branched alkoxy having 3 to 12 carbon atoms) is more preferred, an alkoxy having 1 to 6 carbon atoms (branched alkoxy having 3 to 6 carbon atoms) is even more preferred, and an alkoxy having 1 to 5 carbon atoms (branched alkoxy having 3 to 5 carbon atoms) is particularly preferred.

[0056] Specific alkoxy includes methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, s-butoxy, t-butoxy, t-amyloxy, pentyloxy, hexyloxy, heptyloxy, octyloxy, and the like.

[0057] The "substituted silyl" as the first substituent includes, for example, silyl substituted with three substituents selected from the group consisting of alkyl, cycloalkyl, and aryl, such as trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, alkyldicycloalkylsilyl, triarylsilyl, dialkylarylsilyl, and alkyldiarylsilyl.

[0058] The "trialkylsilyl" refers to a group in which three hydrogen atoms in a silyl group are each independently substituted with an alkyl, and the alkyl can be cited from the groups described as the "alkyl" in the first substituent above. The alkyl preferably used for substitution is an alkyl having 1 to 5 carbon atoms, and specific examples thereof include methyl, ethyl, propyl, i-propyl, butyl, sec-butyl, t-butyl, and t-amyl.

[0059] Specific examples of trialkylsilyl include trimethylsilyl, triethylsilyl, tripropylsilyl, tri-i-propylsilyl, tributylsilyl, trisec-butylsilyl, tri-t-butylsilyl, tri-t-amylsilyl, ethyldimethylsilyl, propyldimethylsilyl, i-propyldimethylsilyl, butyldimethylsilyl, sec-butyldimethylsilyl, t-butyldimethylsilyl, t-amyldimethylsilyl, methyldiethylsilyl, propyldiethylsilyl, i-propyldiethylsilyl, and butyldiethylsilyl. Examples of the silyl group include butyldiethylsilyl, sec-butyldiethylsilyl, t-butyldiethylsilyl, t-amyldiethylsilyl, methyldipropylsilyl, ethyldipropylsilyl, butyldipropylsilyl, sec-butyldipropylsilyl, t-butyldipropylsilyl, t-amyldipropylsilyl, methyldi-i-propylsilyl, ethyldi-i-propylsilyl, butyldi-i-propylsilyl, sec-butyldi-i-propylsilyl, t-butyldi-i-propylsilyl, and t-amyldi-i-propylsilyl.

[0060] Examples of "tricycloalkylsilyl" include groups in which three hydrogen atoms in a silyl group are independently replaced with cycloalkyl, and the cycloalkyl can be cited as the group described as "cycloalkyl" in the first substituent above. Preferred cycloalkyl groups for substitution are cycloalkyl groups having 5 to 10 carbon atoms, specifically cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, bicyclo[1.1.1]pentyl, bicyclo[2.0.1]pentyl, bicyclo[1.2.1]hexyl, bicyclo[3.0.1]hexyl, bicyclo[2.1.2]heptyl, bicyclo[2.2.2]octyl, adamantyl, decahydronaphthalenyl, and decahydroazulenyl.

[0061] Specific examples of tricycloalkylsilyl include tricyclopentylsilyl and tricyclohexylsilyl.

[0062] Specific examples of dialkylcycloalkylsilyl substituted with two alkyls and one cycloalkyl and alkyldicycloalkylsilyl substituted with one alkyl and two cycloalkyls include silyl substituted with a group selected from the specific alkyls and cycloalkyls mentioned above.

[0063] Specific examples of dialkylarylsilyl substituted with two alkyls and one aryl, alkyldiarylsilyl substituted with one alkyl and two aryls, and triarylsilyl substituted with three aryls include silyl substituted with a group selected from the above-mentioned specific alkyls and aryls. Specific examples of triarylsilyl include triphenylsilyl.

[0064] As for the "aryl" in the "diarylboryl" of the first substituent, the above description of the aryl can be cited. In addition, the two aryls may be bonded via a single bond or a linking group (e.g., >C(-R)2, >O, >S, or >NR). Here, R in >C(-R)2 and >NR is aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, alkoxy, or aryloxy (above, the first substituent), and the first substituent may be further substituted with aryl, heteroaryl, alkyl, or cycloalkyl (above, the second substituent), and as specific examples of these groups, the above description of the aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, alkoxy, or aryloxy as the first substituent can be cited.

[0065] In the first substituent -L-Ak, L is >NR, >O or >S, and R of >NR is optionally substituted aryl, optionally substituted heteroaryl, optionally substituted alkyl or optionally substituted cycloalkyl. Also, R of >NR may be bonded to Ak via a linking group or a single bond.

[0066] Ak is hydrogen, optionally substituted alkyl, or optionally substituted cycloalkyl, in which at least one hydrogen in the alkyl and cycloalkyl may be substituted, and at least one -CH2- in the alkyl and cycloalkyl may be substituted with -O- and -S-.

[0067] Preferably L is >NR. When L is >NR, R is preferably aryl optionally substituted with alkyl or cycloalkyl, heteroaryl optionally substituted with alkyl or cycloalkyl, alkyl or cycloalkyl, more preferably aryl optionally substituted with alkyl, heteroaryl optionally substituted with alkyl, alkyl or cycloalkyl, even more preferably aryl optionally substituted with alkyl, and particularly preferably phenyl optionally substituted with methyl.

[0068] Ak is preferably alkyl having 1 to 6 carbon atoms or cycloalkyl having 3 to 14 carbon atoms, more preferably alkyl having 1 to 4 carbon atoms or cycloalkyl having 3 to 8 carbon atoms, more preferably alkyl having 1 to 4 carbon atoms, and further preferably methyl.

[0069] When L is >NR, R may be bonded to Ak via a linking group or a single bond. In this case, examples of the linking group include >O, >S, and >Si(-R)2. R in >Si(-R)2 is hydrogen, an aryl having 6 to 12 carbon atoms, an alkyl having 1 to 6 carbon atoms, or a cycloalkyl having 3 to 14 carbon atoms. Examples of the structure in which R in >NR is bonded to Ak via a linking group or a single bond include the following.

[0070] [ka]

[0071] In the above formulas, Me is methyl, and * represents ring A, ring B, ring C, or ring R.XD or R XE is bonded to an atom constituting an aryl or heteroaryl ring in the

[0072] As explained above, the first substituent, substituted or unsubstituted "aryl", substituted or unsubstituted "heteroaryl", substituted or unsubstituted "diarylamino", substituted or unsubstituted "diheteroarylamino", substituted or unsubstituted "arylheteroarylamino", substituted or unsubstituted "diarylboryl (two aryls may be bonded via a single bond or a linking group)", substituted or unsubstituted "alkyl", substituted or unsubstituted "cycloalkyl", substituted or unsubstituted "alkoxy", substituted or unsubstituted "aryloxy", or substituted "silyl" may have at least one hydrogen atom substituted with a second substituent. Examples of the second substituent include aryl, heteroaryl, alkyl, or cycloalkyl, and specific examples thereof can be found in the above-mentioned explanation of the monovalent group of the "aryl ring" or "heteroaryl ring", and the explanation of the "alkyl" or "cycloalkyl" as the first substituent. The aryl and heteroaryl as the second substituent also include structures in which at least one hydrogen atom in the aryl and heteroaryl as the second substituent is substituted with an aryl such as phenyl (specific examples are the groups mentioned above), an alkyl such as methyl and t-butyl (specific examples are the groups mentioned above), or a cycloalkyl such as cyclohexyl (specific examples are the groups mentioned above). As an example, when the second substituent is carbazolyl, the heteroaryl as the second substituent also includes a carbazolyl in which at least one hydrogen atom at the 9-position is substituted with an aryl such as phenyl, an alkyl such as methyl, or a cycloalkyl such as cyclohexyl.

[0073] The emission wavelength can be adjusted by the steric hindrance, electron donating property and electron withdrawing property of the structure of the first substituent. The group represented by the following structural formula is preferable, and more preferable 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, carbazolyl (particularly N-carbazolyl), 3,6-dimethylcarbazolyl, and the like. 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.

[0074] In the structural formula below, "Me" is methyl, "tBu" is t-butyl, "tAm" is t-amyl, "tOct" is t-octyl, and * indicates the bond position. [ka]

[0075] [ka]

[0076] [ka]

[0077]

change

[0078]

change

[0079]

change

[0080]

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[0081]

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[0082]

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[0083]

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[0084]

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[0085]

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[0086]

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[0087] In formula (1A) and formula (1B), Y is each independently B, P, P=O or P=S, preferably B or P=O, more preferably B. This explanation also applies to Y in formula (2A) and formula (2B).

[0088] X in formula (1A) and formula (1B) are each independently >C(-R)2, >NR, >O, >Si(-R)2 or >S, R of the >NR is an optionally substituted aryl, an optionally substituted heteroaryl, an optionally substituted alkyl or an optionally substituted cycloalkyl, R of the >C(-R)2 and >Si(-R)2 are each independently hydrogen, an optionally substituted aryl, an optionally substituted alkyl or an optionally substituted cycloalkyl, and may be bonded to each other by a linking group, and at least one of R of the >NR, the >C(-R)2 and the >Si(-R)2 is connected to the A ring, the B ring, the C ring, the R ring, or the R ring by a linking group or a single bond. XD , or R XE As described above, at least one of X is >NR, where R is an optionally substituted alkyl or an optionally substituted cycloalkyl, and R is connected to ring A, ring B, ring C, or ring R by a linking group or a single bond. XD , or R XE The description of X in formula (1A) and formula (1B) and the description of the preferred ranges below also apply to X in formula (2A) and formula (2B). XD , or R XE In formula (2A) and formula (2B), "at least one of" is read as "at least one selected from the group consisting of ring A, ring B, ring C, ring D and ring E."

[0089] R of >Si(-R)2, which is X in formula (1A) and formula (1B), is an aryl, heteroaryl, alkyl, or cycloalkyl, which may be substituted with the second substituent described above. Examples of the aryl, heteroaryl, alkyl, or cycloalkyl include the groups described above. In particular, an aryl having 6 to 10 carbon atoms (e.g., phenyl, naphthyl, etc.), a heteroaryl having 2 to 15 carbon atoms (e.g., carbazolyl, etc.), an alkyl having 1 to 5 carbon atoms (e.g., methyl, ethyl, etc.), or a cycloalkyl having 5 to 10 carbon atoms (preferably cyclohexyl or adamantyl) is preferred. This explanation also applies to R of >Si(-R)2 in X in formula (2A) and formula (2B).

[0090] R of >C(-R)2, which is X in formula (1A) and formula (1B), is hydrogen, aryl, heteroaryl, alkyl, or cycloalkyl, which may be substituted with the second substituent described above. Examples of the aryl, heteroaryl, alkyl, or cycloalkyl include the groups described above. In particular, aryl having 6 to 10 carbon atoms (e.g., phenyl, naphthyl, etc.), heteroaryl having 2 to 15 carbon atoms (e.g., carbazolyl, etc.), alkyl having 1 to 5 carbon atoms (e.g., methyl, ethyl, etc.), or cycloalkyl having 5 to 10 carbon atoms (preferably cyclohexyl or adamantyl) are preferred. This explanation also applies to R of >C(-R)2 in X in formula (2A) and formula (2B).

[0091] In formula (1A) and formula (1B), at least one X is the above-mentioned >NR, and the other Xs are each preferably independently >O or >NR, more preferably at least one of them is >NR, and further preferably all of them are >NR.

[0092] For the aryl, heteroaryl, alkyl, and cycloalkyl in R of >NR which is X, the explanation of them as the first substituent can be referred to. R of >NR in X is preferably an aryl which may be substituted, a heteroaryl which may be substituted, or a cycloalkyl which may be substituted, and more preferably an aryl which may be substituted. Here, as the aryl, phenyl, biphenylyl (particularly, 2-biphenylyl), and terphenylyl (particularly, terphenyl-2'-yl) are preferable, and phenyl and biphenylyl are more preferable. When the aryl is substituted, the substituent is preferably methyl or a tertiary alkyl represented by the above formula (tR). The number of substituents in the aryl is preferably 0 to 3, and more preferably 1 to 2.

[0093] Particularly preferred R of >NR which is X is unsubstituted phenyl, phenyl having methyl bonded to the ortho- or para-position, and phenyl having methyl bonded to one or two ortho-positions.

[0094] R in at least one of X, >NR, >Si(-R)2, and >C(-R)2, is a linking group or a single bond that is connected to ring A, ring B, ring C, or ring R. XD , or R XE may be bonded to at least one ring in the above formula (A10). The linking group is preferably -O-, -S-, or -C(-R)2-. In addition, R in the above "-C(-R)2-" is hydrogen, alkyl, or cycloalkyl. Specific examples of such structures include the structure represented by the above formula (A10). In addition, more generally, compounds having a ring structure in which X is incorporated into fused ring B', as represented by the following formula (1-3-1), and compounds having a ring structure in which X is incorporated into fused ring A', as represented by the following formula (1-3-2), may be mentioned. The fused ring B' (or fused ring A') formed is, for example, a carbazole ring, a phenoxazine ring, a phenothiazine ring, or an acridine ring.

[0095] [ka]

[0096] X in formula (1A) and formula (1B) is ring A, ring B, ring C, R XD , or R XE Examples of the linking group when X is bonded to at least one ring in formula (2A) and formula (2B) include -O-, -S-, -C(-R)2-, and a single bond, and R in "-C(-R)2-" is hydrogen, alkyl, or cycloalkyl, and the alkyl or cycloalkyl includes the above-mentioned groups. In particular, alkyl having 1 to 5 carbon atoms (e.g., methyl, ethyl, etc.) or cycloalkyl having 5 to 10 carbon atoms (preferably cyclohexyl or adamantyl) is preferred. This explanation also applies to the linking group "-C(-R)2-" when X in formula (2A) and formula (2B) is bonded to at least one ring in at least one ring in ring A, ring B, ring C, ring D, or ring E.

[0097] At least one selected from the group consisting of an aryl ring and a heteroaryl ring in a compound consisting of a partial structure represented by formula (1A) and at least one partial structure represented by formula (1B) may be condensed with at least one cycloalkane, at least one hydrogen in the cycloalkane may be substituted, and at least one -CH2- in the cycloalkane may be substituted with -O-. This explanation also applies to compounds in which formula (1A) and formula (1B) are formula (2A) and formula (2B), respectively.

[0098] 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.

[0099] Specific examples of cycloalkanes include cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclooctane, cyclononane, cyclodecane, norbornene, bicyclo[1.0.1]butane, bicyclo[1.1.1]pentane, bicyclo[2.0.1]pentane, bicyclo[1.2.1]hexane, bicyclo[3.0.1]hexane, bicyclo[2.1.2]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.

[0100] Among these, a structure in which at least one hydrogen atom is substituted on the carbon atom at the α-position of the cycloalkane (the carbon atom at the position adjacent to the carbon atom at the condensation site in the cycloalkyl fused to an aryl ring or heteroaryl 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. In particular, a structure in which a partial structure represented by the following formula (B10) is bonded to adjacent carbon atoms in an aryl ring or heteroaryl ring is preferred.

[0101] [ka] In formula (B10), Me represents methyl, and * represents the bonding position.

[0102] The hydrogen atoms in the chemical structure of the polycyclic aromatic compound consisting of the partial structure represented by formula (1A) and at least one partial structure represented by formula (1B) may be substituted in whole or in part with deuterium, cyano, or halogen. For example, in the polycyclic aromatic compound consisting of the partial structure represented by formula (1A) and at least one partial structure represented by formula (1B), the A ring, the B ring, the C ring, the R ring, the XD , or R XEIn the above, hydrogen atoms in the aryl or heteroaryl ring, the substituents on these rings, and R (= alkyl, cycloalkyl, aryl) when X is >NR, >C(-R)2, or >Si(-R)2 can be replaced with deuterium, cyano, or halogen, and among these, there is an embodiment in which all or a part of the hydrogen atoms in the aryl or heteroaryl are replaced with deuterium, cyano, or halogen. The halogen is fluorine, chlorine, bromine, or iodine, preferably fluorine, chlorine, or bromine, more preferably fluorine or chlorine, and even more preferably fluorine. In addition, from the viewpoint of durability, it is also preferable that all or a part of the hydrogen atoms in the chemical structure of the polycyclic aromatic compound consisting of the partial structure represented by formula (1A) and at least one partial structure represented by formula (1B) are deuterium. This explanation also applies to compounds in which formula (1A) and formula (1B) are formula (2A) and formula (2B), respectively.

[0103] Examples of polycyclic aromatic compounds having a partial structure represented by formula (1A) and at least one partial structure represented by formula (1B) include polycyclic aromatic compounds represented by any of the following formulas (3-1) to (3-4). [ka]

[0104] In formulas (3-1) to (3-4), the same symbols as those in formulas (1A) and (1B) have the same meanings as those in formulas (1A) and (1B), respectively, and the preferred ranges are also the same. XD and R XE shall be read as ring a, ring b, ring c, ring d and ring e, or ring a, ring b, ring c (ring c'), ring d and ring e (ring e'), respectively. In formulas (3-1) to (3-4), each Z is independently -C(-R Z )= or -N=, and two adjacent Zs are -C(-R Z )2-, -Si(-R Z )2-, -N(-RZ )-, -O-, or -S-. Two adjacent Z's may be replaced with -C(-R Z )2-, -Si(-R Z )2-, -N(-R Z Examples of structures in which -, -O-, or -S- is substituted include a cyclopentadiene ring, a pyrrole ring, a furan ring, a thiophene ring, a thiazole ring, and an oxazole ring.

[0105] In formula (3-1) to formula (3-4), each Z is independently -C(-R Z )= or -N=, and two adjacent Zs are -C(-R Z )2-, -Si(-R Z )2-, -N(-R Z In this case, Z at the o (ortho) or p (para) position relative to Y is preferably not replaced with -C(-R Z )= is preferable. In addition, in a ring (monocyclic ring) containing Z where -N=, it is preferable that one or two of the multiple Zs are -N=, and when two are -N=, it is preferable that the two -N=s are not adjacent to each other. When a 6-membered ring is a ring containing Z where -N=, it is preferable that the ring is a pyridine ring, a pyrazine ring, a pyrimidine ring, a pyridazine ring, or a 1,2,3-triazine ring, and more preferable that the ring is a pyridine ring, a pyrazine ring, or a pyrimidine ring. The number of rings (monocyclic rings) containing Z where -N= is preferably 0 to 4, more preferably 0 to 3, even more preferably 0 to 2, and particularly preferably 0 to 1.

[0106] Specifically, Z is any of -C(-R Z In addition, in both formulas (3-1) and (3-2), it is preferable that -C(-R Z In addition, one or more Z in ring b is -N=, and the other Z is each independently -C(-R Z It is also preferred that:

[0107] R Z are each independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl (two aryls may be bonded via a single bond or a linking group), alkyl, cycloalkyl, alkoxy, aryloxy or substituted silyl, in which at least one hydrogen may be substituted with an aryl, heteroaryl, alkyl or cycloalkyl; and R Z Adjacent groups among these may be bonded to each other to form an aryl ring or a heteroaryl ring together with the ring a, the ring c, the ring d, the ring e, or the ring a, the ring c, the ring d, the ring e, the ring c', and the ring e', and at least one hydrogen atom in the formed ring may be substituted with an aryl, a heteroaryl, a diarylamino, a diheteroarylamino, an arylheteroarylamino, a diarylboryl (two aryls may be bonded via a single bond or a linking group), an alkyl, a cycloalkyl, an alkoxy, an aryloxy, or a substituted silyl, and at least one hydrogen atom in these may be substituted with an aryl, a heteroaryl, an alkyl, or a cycloalkyl.

[0108] R Z For details and preferred ranges of the above, the explanation of the first substituent and the second substituent can be referred to.

[0109] In formula (3-1) to formula (3-4), Z is -C(-R Z ) = R Z are each independently preferably hydrogen, an aryl having 6 to 30 carbon atoms, a heteroaryl having 2 to 30 carbon atoms, a diarylamino (wherein the aryl is an aryl having 6 to 12 carbon atoms), a diarylboryl (wherein the aryl is an aryl having 6 to 12 carbon atoms, and the two aryls may be bonded via a single bond or a linking group), an alkyl having 1 to 24 carbon atoms, a cycloalkyl having 3 to 24 carbon atoms, a triarylsilyl (wherein the aryl is an aryl having 6 to 12 carbon atoms), or a trialkylsilyl (wherein the alkyl is an alkyl having 1 to 6 carbon atoms), provided that adjacent R Zmay be bonded together 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 by an aryl having 6 to 10 carbon atoms, an alkyl having 1 to 12 carbon atoms, a cycloalkyl having 3 to 16 carbon atoms, triarylsilyl (wherein the aryl is an aryl having 6 to 12 carbon atoms), or trialkylsilyl (wherein the alkyl is an alkyl having 1 to 5 carbon atoms); More preferably, each independently represents hydrogen, an aryl having 6 to 16 carbon atoms, a heteroaryl having 2 to 20 carbon atoms, a diarylamino (wherein the aryl has 6 to 10 carbon atoms), an alkyl having 1 to 12 carbon atoms, or a cycloalkyl having 3 to 16 carbon atoms; More preferably, they are each independently hydrogen, aryl having 6 to 16 carbon atoms, diarylamino (wherein aryl is aryl having 6 to 10 carbon atoms), alkyl having 1 to 12 carbon atoms or cycloalkyl having 3 to 16 carbon atoms.

[0110] In each of the rings a, b, c (ring c'), d, and e (ring e') in the formulas (3-1) to (3-4), R in each ring Z is preferably 0 to 2 substituents other than hydrogen and the rest are hydrogen, and more preferably 0 to 1 substituent other than hydrogen and the rest are hydrogen. In the rings a, b, c (c') ring, d ring, and e (e') ring in each of the formulas (3-1) to (3-4), which are bonded to R of >NR as X to form the structure represented by the above formula (A10), Z other than the bonding portion is preferably CH.

[0111] In each of formulas (3-1) to (3-4), R bonded to adjacent C (carbon atom) Z They may be bonded to each other to form an aryl ring or a heteroaryl ring together with the ring a, ring b, ring c (ring c'), ring d, or ring e (ring e'). As an example of the compound represented by formula (3-1), R ZAs a structure in which rings a and a are bonded together to form an aryl ring or a heteroaryl ring, the structure shown in the following formula (3-1-a) is Z together with the d ring, and R Z The structures shown in the following formula (3-1-b) are examples of structures in which the rings are bonded together to form an aryl or heteroaryl ring together with the ring e. The rings A', D', and E' in each formula correspond to the ring a, ring d, and ring e in formula (3-1), respectively. The definitions of Z, a, b, c, d, e, Y, X, and Z in each formula are the same as those in formula (3-1).

[0112] [ka]

[0113] In formula (3-1-a) and formula (3-1-b), the A' ring, the D' ring and E' ring are R bonded to the adjacent C (carbon atom) as explained in formula (3-1). Z These rings are bonded to each other to form an aryl or heteroaryl ring together with the a, b, and e rings, respectively (they can also be considered fused rings formed by fusing other ring structures to the a, b, and e rings). Although not shown in the formula, there are also compounds in which the b and c rings are changed to the B' and C' rings, and compounds in which the a, b, c (c') rings, d, or e (e') rings are all changed to the A', B', C', D', and E' rings.

[0114] For example, the fused ring A' ring (or B' ring, C' ring, D' ring or E' ring) formed by condensing a benzene ring, an indole ring, a pyrrole ring, a furan ring, a thiophene ring, a benzofuran ring, a benzothiophene ring, a cyclopentadiene ring or an indene ring to a benzene ring a ring (or b ring, c ring (c' ring), d ring or e ring (e' ring)) is a naphthalene ring, a carbazole ring, an indole ring, a benzofuran ring, a benzothiophene ring, a dibenzofuran ring, a dibenzothiophene ring, an indene ring or a fluorene ring, respectively.

[0115] In addition, for example, in a ring a (or ring b, ring c (ring c'), ring d, or ring e (ring e')), a cyclopentadiene ring, a pyrrole ring, a furan ring, or a thiophene ring, R bonded to an adjacent C Z When these rings are bonded to each other to form a benzene ring, examples of the condensed ring include an indene ring, an indole ring, a benzofuran ring, and a benzothiophene ring.

[0116] Preferred examples of the polycyclic aromatic compounds represented by any one of formulas (3-1) to (3-4) include polycyclic aromatic compounds represented by any one of formulas (3-1-1), (3-1-2), and (3-2-1).

[0117] [ka]

[0118] In formulae (3-1-1), (3-1-2) and (3-2-1), the same symbols as those in formulae (3-1) to (3-4) have the same meanings and preferred ranges as those in formulae (3-1) to (3-4), respectively. In formula (3-1-1), formula (3-1-2), and formula (3-2-1), X 1 are each independently >C(-R)2, >NR, >O, >Si(-R)2 or >S, R of the >NR is an aryl having 6 to 12 carbon atoms which may be substituted with an alkyl having 1 to 6 carbon atoms or a cycloalkyl having 3 to 14 carbon atoms, a heteroaryl having 2 to 15 carbon atoms which may be substituted with an alkyl having 1 to 6 carbon atoms or a cycloalkyl having 3 to 14 carbon atoms, an alkyl having 1 to 6 carbon atoms or a cycloalkyl having 3 to 14 carbon atoms, and R of the >C(-R)2 and >Si(-R)2 are each independently hydrogen, an aryl having 6 to 12 carbon atoms, an alkyl having 1 to 6 carbon atoms or a cycloalkyl having 3 to 14 carbon atoms. X 1For the preferred range of X, the preferred range of X in formula (1A) and formula (1B) can be referred to, but specifically, >NR or >O is preferable, and in this case, R of >NR is preferably an aryl having 6 to 12 carbon atoms which may be substituted with an alkyl having 1 to 6 carbon atoms or a heteroaryl having 2 to 15 carbon atoms which may be substituted with an alkyl having 1 to 6 carbon atoms, more preferably an aryl having 6 to 12 carbon atoms which may be substituted with an alkyl having 1 to 6 carbon atoms, and even more preferably phenyl which may be substituted with methyl or t-butyl.

[0119] Specific examples of polycyclic aromatic compounds having a partial structure represented by formula (1A) and at least one partial structure represented by formula (1B) include polycyclic aromatic compounds represented by any of the following formulas.

[0120] [ka]

[0121] [ka]

[0122] [ka]

[0123] In each of the above structural formulas, the hydrogen bonded to the benzene ring may be replaced by methyl or t-butyl, and consecutive hydrogens may be replaced by the partial structure represented by the above formula (B10).

[0124] More specific examples of the polycyclic aromatic compound of the present invention include compounds represented by the following structural formulas: In the structural formulas, "Me" represents methyl and "tBu" represents t-butyl.

[0125] [ka]

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[0147] [ka]

[0148] [ka]

[0149] [ka]

[0150] [ka]

[0151] The polycyclic aromatic compound having a partial structure represented by formula (1A) and at least one partial structure represented by formula (1B) can 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).

[0152] 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 include unsaturated alkenyl, alkynyl, and cycloalkyl (e.g., cyclobutenyl), groups in which at least one -CH2- in cycloalkyl is replaced with -O- (e.g., epoxy), and unsaturated condensed cycloalkane (e.g., condensed cyclobutene), and the following structures are preferred. * in each structural formula indicates a bond position.

[0153] [ka]

[0154] 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.

[0155] 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.

[0156] 2. Method for producing polycyclic aromatic compounds A polycyclic aromatic compound consisting of a partial structure represented by formula (1A) and at least one partial structure represented by formula (1B) is basically formed by first dividing an A ring (a ring), a B ring (b ring), a C ring (c ring), R XD (D ring, d ring), R XE(Ring E, Ring e) are bonded with a bonding group (a group containing X) to produce an intermediate (first reaction), and then Ring A (ring a), Ring B (ring b), Ring C (ring c), and Ring R XD (D ring, d ring), R XE The final product can be produced by bonding (E ring, e ring) with a bonding group (a group containing Y) (second reaction). In the first reaction, for example, a general reaction such as a nucleophilic substitution reaction or an Ullmann reaction can be used for an etherification reaction, and a general reaction such as a Buchwald-Hartwig reaction can be used for an amination reaction. In addition, in the second reaction, a tandem hetero Friedel-Crafts reaction (sequential aromatic electrophilic substitution reaction, the same applies below) can be used. For the production method of these, refer to the method described in the prior art such as International Publication No. 2015 / 102118. A compound having a partial structure represented by formula (A10) can be produced by using a raw material having a partial structure represented by formula (A10) somewhere in the reaction process or by adding a process of introducing a partial structure represented by formula (A10). The partial structure represented by formula (A10) can be synthesized by using Fischer's indole synthesis and addition reaction.

[0157] 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.

[0158] 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.

[0159] 3-1-1. Structure of organic electroluminescent device The organic EL element 100 shown in FIG. 1 has a substrate 101, an anode 102 provided on the substrate 101, a hole injection layer 103 provided on the anode 102, a hole transport layer 104 provided on the hole injection layer 103, an emitting layer 105 provided on the hole transport layer 104, an electron transport layer 106 provided on the emitting layer 105, an electron injection layer 107 provided on the electron transport layer 106, and a cathode 108 provided on the electron injection layer 107.

[0160] 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.

[0161] 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.

[0162] 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".

[0163] 3-1-2. Substrate in organic electroluminescent device The substrate 101 is a support for the organic EL element 100, and is usually made of quartz, glass, metal, plastic, or the like. The substrate 101 is formed into a plate, film, or sheet shape depending on the purpose, and for example, a glass plate, a metal plate, a metal foil, a plastic film, a plastic sheet, or the like is used. Among them, a glass plate and a plate made of a transparent synthetic resin such as polyester, polymethacrylate, polycarbonate, or polysulfone are preferable. For a glass substrate, soda-lime glass or 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.

[0164] 3-1-3. Anode in organic electroluminescent device The anode 102 plays a role in injecting holes into the light-emitting layer 105. When the hole injection layer 103 and / or the hole transport layer 104 are provided between the anode 102 and the light-emitting layer 105, the holes are injected into the light-emitting layer 105 through these layers.

[0165] 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.

[0166] 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.

[0167] 3-1-4. Hole injection layer and hole transport layer in organic electroluminescent device The hole injection layer 103 plays a role of efficiently injecting holes moving from the anode 102 into the light emitting layer 105 or the hole transport layer 104. The hole transport layer 104 plays a role of efficiently transporting holes injected from the anode 102 or holes injected from the anode 102 via the hole injection layer 103 to the light emitting layer 105. The hole injection layer 103 and the hole transport layer 104 are each formed by laminating and mixing one or more types of hole injection / transport materials, or by a mixture of a hole injection / transport material and a polymer binder. Alternatively, a layer may be formed by adding an inorganic salt such as iron (III) chloride to the hole injection / transport material.

[0168] A hole injection / transport material is required to efficiently inject / transport holes from the positive electrode between electrodes to which an electric field is applied, and it is desirable for the material to have high hole injection efficiency and efficiently transport the injected holes. For this purpose, it is preferable for the material to have a small ionization potential, a large hole mobility, excellent stability, and a low probability of generating impurities that act as traps during manufacture and use.

[0169] 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, N4 ,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, N-([1,1'-biphenyl]-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluoren-2-amine, N,N-bis(4-(dibenzo[b,d]furan-4-yl)phenyl)-[1,1':4',1"-terphenyl]- triphenylamine derivatives such as 4-amine, 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 (for example, 1,4,5,8,9,12-hexaazatriphenylene-2,3,6,7,10,11-hexacarbonitrile, etc.), heterocyclic compounds such as porphyrin derivatives, polysilanes, etc. As for polymers, polycarbonates and styrene derivatives having the above-mentioned monomers in the side chains, polyvinylcarbazole, polysilanes, etc. are preferable, but there is no particular limitation as long as the compound can form a thin film necessary for the production of a light-emitting element, can inject holes from the anode, and can transport holes.

[0170] It is also known that the electrical conductivity of organic semiconductors is strongly influenced by doping. Organic semiconductor matrix substances consist of compounds with good electron donating or accepting properties. For doping with electron donating substances, strong electron acceptors such as tetracyanoquinone dimethane (TCNQ) or 2,3,5,6-tetrafluorotetracyano-1,4-benzoquinone dimethane (F4TCNQ) are known (see, for example, the references "M. Pfeiffer, A. Beyer, T. Fritz, K. Leo, Appl. Phys. Lett., 73(22), 3202-3204 (1998)" and "J. Blochwitz, M. Pfeiffer, T. Fritz, K. Leo, Appl. Phys. Lett., 73(6), 729-731 (1998)"). These generate so-called holes by an electron transfer process in the electron donating base substance (hole transport substance). The conductivity of the base material varies considerably depending on the number and mobility of holes. Matrix materials having hole transport properties are known, for example, benzidine derivatives (TPD, etc.) or starburst amine derivatives (TDATA, etc.), or certain metal phthalocyanines (especially zinc phthalocyanine (ZnPc) and the like) (JP 2005-167175 A).

[0171] 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 consisting of a partial structure represented by formula (1A) and at least one partial structure represented by formula (1B). The applications of such polymer compounds and crosslinked polymers will be described in detail below.

[0172] 3-1-5. Light-emitting layer in organic electroluminescent device The light-emitting layer 105 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 by the recombination of holes and electrons to emit light, and is preferably a compound that can form a stable thin film shape and shows strong light-emitting (fluorescence) efficiency in a solid state. The light-emitting layer may be a single layer or multiple layers, each of which is formed from a material 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. For example, an emitting dopant and an assisting dopant may be used as the dopant material. The dopant material may be contained in the entire host material or may be contained partially in the host material. As a doping method, the light-emitting layer may be formed by co-evaporation with the host material, but it may also be mixed with the host material in advance and then evaporated at the same time. The light-emitting layer can also be formed by a wet film-forming method using a composition for forming a light-emitting layer prepared by dissolving materials in an organic solvent.

[0173] The polycyclic aromatic compound of the present invention can be preferably used as a material for forming the light-emitting layer of an organic electroluminescent device. The polycyclic aromatic compound of the present invention is more preferably used as an emitting dopant or an assisting dopant in the light-emitting layer, and is further preferably used as an emitting dopant.

[0174] The light-emitting layer containing the polycyclic aromatic compound of the present invention may contain a host compound. Here, the host compound may be one type or two or more types. The light-emitting layer may be a single layer or multiple layers. The host compound, the emitting dopant material, and the assisting dopant material may be contained in the same layer, or at least one component may be contained in each of multiple layers. The host compound and the dopant material (emitting dopant or assisting dopant) contained in the light-emitting layer may each be one type or a combination of multiple types. The assisting dopant and the emitting dopant may be entirely or partially contained in the host compound as a matrix.

[0175] The amount of the host material used varies depending on the type of the host material and may be determined according to the properties of the host material. The amount of the host material used is preferably 50 to 99.999% by mass, more preferably 80 to 99.95% by mass, and even more preferably 90 to 99.9% by mass, of the total material for the light-emitting layer.

[0176] The amount of the dopant material used varies depending on the type of the dopant material, and may be determined according to the characteristics of the dopant material. The amount of the dopant used is preferably 0.001 to 50% by mass, more preferably 0.05 to 20% by mass, and even more preferably 0.1 to 10% by mass, based on the total material for the light-emitting layer. The above range is preferable in that, for example, concentration quenching can be prevented.

[0177] On the other hand, in an organic electroluminescent device using a TADF material as a dopant material, a low concentration of the dopant material is preferable in terms of preventing concentration quenching, but a high concentration of the dopant material is preferable in terms of the efficiency of the thermally activated delayed fluorescence mechanism. Furthermore, in an organic electroluminescent device using a TADF material as an assisting dopant, a low concentration of the emitting dopant is preferable compared to the assisting dopant in terms of the efficiency of the thermally activated delayed fluorescence mechanism of the assisting dopant.

[0178] When an assisting dopant material is used, the amounts of the host material, the emitting dopant and the assisting dopant used are approximately 40 to 99.999 mass%, 59 to 1 mass% and 20 to 0.001 mass% of the total material for the light-emitting layer, respectively, preferably 60 to 99.99 mass%, 39 to 5 mass% and 10 to 0.01 mass%, and more preferably 70 to 99.95 mass%, 29 to 10 mass% and 5 to 0.05 mass%, respectively.

[0179] 3-1-5-1. Host compound 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.

[0180] From the viewpoint of promoting rather than inhibiting the generation of TADF in the light-emitting layer, the T1 energy of the host material is preferably higher than the T1 energy of the dopant or assisting dopant having the highest T1 energy in the light-emitting layer. Specifically, the T1 energy of the host is preferably 0.01 eV or more, more preferably 0.03 eV or more, and even more preferably 0.1 eV or more. In addition, a TADF active compound may be used as the host material.

[0181] Examples of the host material include a compound represented by the following formula (H1), a compound represented by the following formula (H2), a compound represented by the following formula (H3), a compound including a structure represented by the following formula (H4), a compound represented by the following formula (H5), and a compound represented by the following formula (H6). [ka]

[0182] 3-1-5-1-1. Compound represented by formula (H1) [ka]

[0183] In formula (H1), L 1 is an arylene having 6 to 24 carbon atoms, preferably an arylene having 6 to 16 carbon atoms, more preferably an arylene having 6 to 12 carbon atoms, and particularly preferably an arylene having 6 to 10 carbon atoms. Specific examples thereof 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. 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.

[0184] 3-1-5-1-2. Compound represented by formula (H2) [ka]

[0185] In formula (H2), L 2 and L 3are 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 benzo Examples of monovalent groups include an imidazole 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 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, 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, and a thianthrene 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.

[0186] 3-1-5-1-3. Compound represented by formula (H3) [ka]

[0187] In formula (H3), Each MU is independently a divalent aromatic group, each EC is independently a monovalent aromatic group, and k is an integer of 2 to 50,000.

[0188] More specifically, Each MU is independently arylene, heteroarylene, diarylenarylamino, diarylenarylboryl, oxaborine-diyl, or azaborine-diyl; each EC 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.

[0189] 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.

[0190] Examples of MU include divalent derivatives of the following structures (e.g., a divalent group represented by removing any two hydrogen atoms from any of the compounds of the following structures, a divalent group composed of a combination of two or more divalent groups represented by removing any two hydrogen atoms from any of the compounds of the following structures, and a divalent group in which at least one hydrogen in such a group is substituted with an alkyl or the like). [ka]

[0191] More specifically, the divalent group may have any one of the following structures: In these, MU is bonded to another MU or EC at *.

[0192] [ka]

[0193] [ka]

[0194] [ka]

[0195] [ka]

[0196] [ka]

[0197] [ka]

[0198] [ka]

[0199] [ka]

[0200] [ka]

[0201] Examples of EC include groups represented by the following formulas: In these, EC is bonded to MU at *.

[0202] [ka]

[0203] [ka]

[0204] 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 a carbon number of 1 to 24, more preferably 30 to 100% of the total number of MUs (k) in the molecule have an alkyl having a carbon number of 1 to 18 (branched chain alkyl having a carbon number of 3 to 18), and even more preferably 50 to 100% of the total number of MUs (k) in the molecule have an alkyl having a carbon number of 1 to 12 (branched chain alkyl having a carbon number of 3 to 12). 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 a carbon number of 7 to 24, and more preferably 30 to 100% of the total number of MUs (k) in the molecule have an alkyl having a carbon number of 7 to 24 (branched chain alkyl having a carbon number of 7 to 24).

[0205] 3-1-5-1-4. Compounds containing the structure represented by formula (H4) The compound containing a structure represented by formula (H4) contains a plurality of structures represented by formula (H4), preferably 1 to 5 structures, more preferably 1 to 3 structures, even more preferably 1 to 2 structures, and most preferably 1 structure. When a plurality of structures are contained, the structures are directly bonded to each other via a single bond or are bonded to each other via a specific linking group.

[0206] [ka]

[0207] In formula (H4), G is "=C(-H)-" or "=N-", and the H in the "=C(-H)-" may be substituted with a substituent or another structure represented by formula (H4).

[0208] As the compound containing the structure represented by formula (H4), for example, the compounds described in WO 2012 / 153780 and WO 2013 / 038650 can be used, and can be produced according to the methods described in the above-mentioned documents.

[0209] Examples of the substituent when H in "=C(-H)-" of G is substituted include aryl, heteroaryl, substituted silyl, substituted phosphine oxide group, and substituted carboxy.

[0210] Specific examples of the "aryl" 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 having a substituent include tolyl, xylyl, and 9,9-dimethylfluorenyl. As shown in the specific examples, aryl includes both fused and non-fused aryl.

[0211] Specific examples of the substituent "heteroaryl" include pyrrolyl, pyrazolyl, pyrazinyl, pyrimidinyl, pyridazinyl, pyridyl, triazinyl, indolyl, isoindolyl, imidazolyl, benzimidazolyl, indazolyl, imidazo[1,2-a]pyridinyl, furyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, azadibenzofuranyl, thienyl, benzothienyl, dibenzothienyl, azadibenzothienyl, quinolyl, isoquinolyl, quinoxalinyl, quinazolinyl, and naphthyridinyl. Examples of the aryl include carbazolyl, azacarbazolyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, phenothiazinyl, phenoxazinyl, oxazolyl, oxadiazolyl, furazanyl, benzoxazolyl, thiazolyl, thiadiazolyl, benzothiazolyl, triazolyl, and tetrazolyl. Preferred examples include dibenzofuranyl, dibenzothienyl, carbazolyl, pyridyl, pyrimidinyl, triazinyl, azadibenzofuranyl, and azadibenzothienyl. Dibenzofuranyl, dibenzothienyl, azadibenzofuranyl, and azadibenzothienyl are more preferred.

[0212] The substituent "substituted silyl" is also preferably a group selected from the group consisting of substituted or unsubstituted trialkylsilyl, substituted or unsubstituted arylalkylsilyl, and substituted or unsubstituted triarylsilyl.

[0213] Specific examples of the substituted or unsubstituted trialkylsilyl include trimethylsilyl and triethylsilyl. Specific examples of the substituted or unsubstituted arylalkylsilyl include diphenylmethylsilyl, ditolylmethylsilyl, and phenyldimethylsilyl. Specific examples of the substituted or unsubstituted triarylsilyl include triphenylsilyl and tritolylsilyl.

[0214] 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.

[0215] The substituent "substituted carboxy" includes, for example, benzoyloxy and the like.

[0216] 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.

[0217] Specific examples of the compound containing the structure represented by formula (H4) are shown below. [ka]

[0218] 3-1-5-1-5. Compounds represented by formula (H5) and compounds represented by formula (H6) 3-1-5-1-5-1. Compound represented by formula (H5) [ka]

[0219] In formula (H5), R 1 ~R 11 are each independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino or aryloxy, in which at least one hydrogen may be further substituted with aryl, heteroaryl or diarylamino; R 1 ~R 11Adjacent groups among these may be bonded to each other to form an aryl ring or a heteroaryl ring together with the a ring, the b ring or the c ring, and at least one hydrogen atom in the formed ring may be replaced by an aryl, a heteroaryl, a diarylamino, a diheteroarylamino, an arylheteroarylamino or an aryloxy, and at least one hydrogen atom in these rings may be further replaced by an aryl, a heteroaryl or a diarylamino. In addition, at least one (preferably 1 to 3) of any -C(R n )= (n is 1 to 11) may be substituted with -N=. Furthermore, at least one hydrogen in the compound represented by formula (H5) may be substituted with a group represented by formula (FG-1), a group represented by formula (FG-2), or an alkyl having 1 to 24 carbon atoms, and further, any -CH2- in the alkyl may be substituted with -O- or -Si(CH3)2-, any -CH2- in the alkyl except for the -CH2- directly bonded to the compound represented by formula (H5) may be substituted with an arylene having 6 to 24 carbon atoms, and any hydrogen in the alkyl may be substituted with fluorine. In addition, at least one hydrogen in the compound represented by formula (H5) may be substituted with a halogen or deuterium.

[0220] In formula (H5), the substituents R 1 ~R 11Adjacent 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 substituted with an aryl, a heteroaryl, a diarylamino, a diheteroarylamino, an arylheteroarylamino, or an aryloxy, and at least one hydrogen in these may be further substituted with an aryl, a heteroaryl, or a diarylamino. However, here, "adjacent groups" refers to groups adjacent to each other on the same ring, and a compound in which "adjacent groups are 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" corresponds to, for example, compounds represented by formulas (H5-2) to (H5-17) listed as specific compounds to be described later. That is, for example, it is a compound formed by condensing a benzene ring, an indole ring, a pyrrole ring, a benzofuran ring, or a benzothiophene ring to the a ring (or the b ring or the c ring), and the condensed ring formed is a naphthalene ring, a carbazole ring, an indole ring, a dibenzofuran ring, or a dibenzothiophene ring, respectively.

[0221] 3-1-5-1-5-2. Compound represented by formula (H6) [ka]

[0222] In formula (H6), R 1 ~R 16 are each independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino or aryloxy, in which at least one hydrogen may be further substituted with aryl, heteroaryl or diarylamino; R 1 ~R 16Adjacent groups among these may be bonded to each other to form an aryl ring or a heteroaryl ring together with the a ring, the b ring, the c ring or the d ring, and at least one hydrogen atom in the formed ring may be substituted by an aryl, a heteroaryl, a diarylamino, a diheteroarylamino, an arylheteroarylamino or an aryloxy, and at least one hydrogen atom in these rings may be further substituted by an aryl, a heteroaryl or a diarylamino. Furthermore, at least one hydrogen in the compound represented by formula (H-6) may be substituted with a group represented by formula (FG-1), a group represented by formula (FG-2), or an alkyl having 1 to 24 carbon atoms, and further, any -CH2- in the alkyl may be substituted with -O- or -Si(CH3)2-, any -CH2- in the alkyl except for the -CH2- directly bonded to the compound represented by formula (H6) may be substituted with an arylene having 6 to 24 carbon atoms, and any hydrogen in the alkyl may be substituted with fluorine. In addition, at least one hydrogen in the compound represented by formula (H6) may be substituted with a halogen or deuterium.

[0223] In formula (H6), the substituents R 1 ~R 16Adjacent groups among may be bonded to each other to form an aryl or heteroaryl ring together with the a, b, c or c ring, and at least one hydrogen in the formed ring may be substituted with an aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino or aryloxy, and at least one hydrogen in these may be further substituted with an aryl, heteroaryl or diarylamino. However, here, "adjacent groups" refers to groups adjacent to each other on the same ring, and a compound in which "adjacent groups are bonded to each other to form an aryl or heteroaryl ring together with the a, b, c or d ring" can be explained with reference to, for example, compounds represented by formulas (H6-2) to (H6-5) listed below as specific compounds of formula (H6). That is, for example, it is a compound formed by condensing a benzene ring, an indole ring, a pyrrole ring, a benzofuran ring, or a benzothiophene ring to ring a (or ring b, ring c, or ring d), and the condensed ring formed is a naphthalene ring, a carbazole ring, an indole ring, a dibenzofuran ring, or a dibenzothiophene ring, respectively.

[0224] 3-1-5-1-5-3. R in formula (H5) 1 ~R 11 " and "R in formula (H6) 1 ~R 16 」 "R in formula (H5) 1 ~R 11 " and "R in formula (H6) 1 ~R 16" are each independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino or aryloxy, and are preferably an aryl having 6 to 30 carbon atoms, a heteroaryl having 2 to 30 carbon atoms, diarylamino (amino having two aryl groups having 6 to 30 carbon atoms), diheteroarylamino (amino having two heteroaryl groups having 2 to 30 carbon atoms), arylheteroarylamino (amino having an aryl group having 6 to 30 carbon atoms and a heteroaryl group having 2 to 30 carbon atoms) or aryloxy having 6 to 30 carbon atoms.

[0225] Examples of the aryl of "aryl", "diarylamino", the aryl of "arylheteroarylamino", and the aryl of "aryloxy" include a monocyclic benzene ring, a bicyclic bicyclic bicyclic naphthalene ring, a tricyclic terphenyl ring (m-terphenyl, o-terphenyl, p-terphenyl), a fused tricyclic acenaphthylene ring, a fluorene ring, a phenalene ring, a phenanthrene ring, a fused tetracyclic tricyclic triphenylene ring, a pyrene ring, a naphthacene ring, a fused pentacyclic perylene ring, a pentacene ring, and the like. Furthermore, as described below, those aryls substituted with a heteroaryl as defined below are also defined as aryls in formula (H5) and formula (H6).

[0226] Examples of the heteroaryl in "heteroaryl" and "diheteroarylamino" and the heteroaryl in "arylheteroarylamino" 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, quinoline ring, isoquinoline ring, cinnoline ring, quinazoline ring, quinoxaline ring, phthalazine ring, naphthyridine ring, purine ring, pteridine ring, carbazole ring, acridine ring, phenoxathiin ring, phenoxazine ring, phenothiazine ring, phenazine ring, indolizine ring, furan ring, benzofuran ring, isobenzofuran ring, dibenzofuran ring, thiophene ring, benzothiophene ring, dibenzothiophene ring, furazan ring, oxadiazole ring, thianthrene ring, and monovalent groups such as the heteroaryl substituted with N-aryl.Furthermore, as described below, those heteroaryl substituted with the aryl defined above are also defined as heteroaryl in formula (H5) and formula (H6).

[0227] In addition, R in formula (H5) 1 ~R 11 and R in formula (H6) 1 ~R 16 At least one hydrogen atom in the aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, or aryloxy described above may be further substituted with an aryl, heteroaryl, or diarylamino. The aryl, heteroaryl, or diarylamino to be substituted in this manner includes R 1 ~R 11 Or R 1 ~R 16 The same items as those explained in the previous section can be mentioned.

[0228] R 1 ~R11 Or R 1 ~R 16 Specific examples of the groups include groups represented by the following formulae (RG-1) to (RG-10). The groups represented by the following formulae (RG-1) to (RG-10) are bonded to the groups represented by the formulae (H5) and (H6) at *.

[0229] [ka]

[0230] The definitions of "aryl" and "heteroaryl" in formulae (H5) and (H6) are explained with reference to the above-mentioned specific groups. Formulae (RG-1), (RG-4) and (RG-7) are aryl, formulae (RG-2), (RG-3) and (RG-6) are heteroaryl, formula (RG-9) is heteroaryl substituted with heteroaryl, and formula (RG-10) is aryl substituted with heteroaryl. Formula (RG-5) is aryl (phenyl) substituted with diarylamino (diphenylamino), and formula (RG-8) is diarylamino (diphenylamino).

[0231] [ka]

[0232] 3-1-5-1-5-4. In formula (H5), a ring formed by bonding adjacent groups of ring a, ring b, or ring c, and in formula (H6), a ring formed by bonding adjacent groups of ring a, ring b, ring c, or ring d In formula (H5), "R 1 ~R 11 "An aryl ring formed together with the ring a, ring b or ring c by bonding adjacent groups among these" and "R 1 ~R 16 Examples of the aryl ring formed together with ring a, ring b, ring c or ring d by bonding adjacent groups among the above include aryl rings having 6 to 30 carbon atoms, preferably aryl rings having 6 to 16 carbon atoms, more preferably aryl rings having 6 to 12 carbon atoms, and particularly preferably aryl rings having 6 to 10 carbon atoms. However, the number of carbon atoms in the formed aryl ring includes the 6 carbon atom in ring a, ring b, ring c or d.

[0233] Specific examples of the aryl ring formed include a naphthalene ring which is a fused bicyclic ring; an acenaphthylene ring, a fluorene ring, a phenalene ring, a phenanthrene ring which is a fused tricyclic ring; a triphenylene ring, a pyrene ring, a naphthacene ring which is a fused tetracyclic ring; a perylene ring and a pentacene ring which are fused pentacyclic rings.

[0234] In formula (H5), "R 1 ~R 11 and "a heteroaryl ring formed together with ring a, ring b or ring c by bonding adjacent groups among the above" in formula (H6). 1 ~R 16 Examples of the "aryl ring formed together with ring a, ring b, ring c, or ring d by bonding adjacent groups among the above" include heteroaryl rings having 6 to 30 carbon atoms, preferably heteroaryl rings having 6 to 25 carbon atoms, more preferably heteroaryl rings having 6 to 20 carbon atoms, further preferably heteroaryl rings having 6 to 15 carbon atoms, and particularly preferably heteroaryls having 6 to 10 carbon atoms. Examples of the "heteroaryl ring" include heterocycles containing, in addition to carbon, 1 to 5 heteroatoms selected from oxygen, sulfur, and nitrogen as ring-constituting atoms. However, the number of carbon atoms in the formed heteroaryl ring includes the 6 carbon atoms in ring a, ring b, ring c, or ring d.

[0235] Specific examples of the formed heteroaryl ring include, for example, 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 phthalazine ring, a carbazole ring, an acridine ring, a phenoxathiin ring, a phenoxazine ring, a phenothiazine ring, a phenazine ring, a benzofuran ring, an isobenzofuran ring, a dibenzofuran ring, a benzothiophene ring, a dibenzothiophene ring, and a thianthrene ring.

[0236] At least one hydrogen atom in the ring formed may be replaced by aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, or aryloxy, and at least one hydrogen atom in each of these may be further replaced by aryl, heteroaryl, or diarylamino. For this explanation, R 1 ~R 11 and R in formula (H6) 1 ~R 16 The explanation in the above can be cited.

[0237] 3-1-5-1-5-5. Specific examples of compounds A more specific structure of the compound represented by formula (H5) or formula (H6) is shown below. The specific structure of the compound represented by the following formula (H5) or formula (H6) may be substituted with alkyl having 1 to 24 carbon atoms.

[0238] [ka]

[0239] [ka]

[0240] [ka]

[0241] [ka]

[0242] [ka]

[0243] [ka]

[0244]

change

[0245]

change

[0246]

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[0247]

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[0248]

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[0249]

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[0250]

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[0251]

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[0252]

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[0253]

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[0254]

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[0255]

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[0256]

change

[0257]

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[0258]

change

[0259]

change

[0260]

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[0261]

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[0262]

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[0263]

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[0264]

change

[0265]

change

[0266]

change

[0267]

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[0268]

change

[0269]

change

[0270]

change

[0271]

change

[0272] 3-1-5-1-5-6. Method for producing a compound represented by formula (H5) or formula (H6) For the compound represented by formula (H5), first, the rings a to c are bonded with a bonding group (-O-) to produce an intermediate (first reaction), and then the rings a to c are bonded with a bonding group (group containing B) to produce the final product (second reaction). For the compound represented by formula (H6), first, the rings a to d are bonded with a bonding group (>NH or single bond) to produce an intermediate (first reaction), and then the rings a to d are bonded with a bonding group (group containing B) to produce the final product (second reaction). For the first reaction, for example, if it is an etherification reaction, a general reaction such as a nucleophilic substitution reaction or an Ullmann reaction can be used, and if it is an amination reaction, a general reaction such as a Buchwald-Hartwig reaction can be used. For the second reaction, a tandem hetero Friedel-Crafts reaction (successive aromatic electrophilic substitution reaction, the same applies below) can be used.

[0273] <Production method: Example of the second reaction of the compound represented by formula (H5)> The second reaction is a reaction to introduce B (boron) that bonds the a, b and c rings, as shown in the following scheme (1). For example, the case of the compound represented by formula (H5) is shown below. First, the hydrogen atom between the two Os is orthometalated with n-butyllithium, sec-butyllithium or t-butyllithium. Next, boron trichloride, boron tribromide or the like is added to carry out lithium-boron metal exchange, and then a tandem boron-Friedel-Crafts reaction is carried out by adding a Bronsted base such as N,N-diisopropylethylamine to obtain the target product. In the second reaction, a Lewis acid such as aluminum trichloride may be added to promote the reaction.

[0274] [ka]

[0275] In the above scheme, lithium was introduced into the desired position by orthometalation. However, as shown in the following scheme (2), lithium can also be introduced into the desired position by introducing a bromine atom or the like into the desired position and then by halogen-metal exchange.

[0276] [ka]

[0277] By appropriately selecting the above-mentioned synthesis method and the raw materials to be used, a compound having a substituent at a desired position and represented by formula (H-5) can be synthesized.

[0278] <Production method: Example of a method for producing the compound represented by formula (H6)> The first and second reactions in the method for producing the compound represented by formula (H5) described above can also be applied to the method for producing the compound represented by formula (H6). In other words, the second reaction is a reaction for introducing B (boron) which bonds NH to the c and d rings, and the hydrogen atom of NH is orthometalated with n-butyllithium, sec-butyllithium, t-butyllithium, or the like, and then boron trichloride, boron tribromide, or the like is added to carry out lithium-boron metal exchange, and then a tandem boron-Friedel-Crafts reaction is carried out by adding a Bronsted base such as N,N-diisopropylethylamine, to obtain the target product. Here too, a Lewis acid such as aluminum trichloride may be added in the second reaction to promote the reaction.

[0279] 3-1-5-2.TADF material The light-emitting layer also preferably contains a TADF material. In this specification, TADF material means a material that is a "thermally activated delayed fluorescent material." In "thermally activated delayed fluorescent material," the energy difference between the excited singlet state and the excited triplet state is reduced, thereby efficiently transferring energy from the excited triplet state, which usually has a low transition probability, to the excited singlet state, and light emission from the singlet state (thermally activated delayed fluorescence, TADF) is generated. In normal fluorescent emission, 75% of the triplet excitons generated by electric current excitation pass through a thermal deactivation pathway and cannot be extracted as fluorescent light. On the other hand, in TADF, all excitons can be used for fluorescent emission, making it possible to realize highly efficient organic electroluminescence devices.

[0280] 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.

[0281] In this specification, the term "electron-donating substituent" (donor) refers to a substituent or partial structure in which the HOMO 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 LUMO orbital is localized in a TADF compound molecule.

[0282] 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.

[0283] However, by using the polycyclic aromatic compound of the present invention at the same time, the polycyclic aromatic compound of the present invention functions as an emitting dopant and the TADF material functions as an assisting dopant, thereby providing high color purity. The TADF material may be a compound whose emission spectrum at least partially overlaps with the absorption spectrum of the polycyclic aromatic compound of the present invention. The polycyclic aromatic compound of the present invention and the TADF material may both be contained in the same layer or in adjacent layers.

[0284] Examples of TADF materials that can be used for such purposes include a compound represented by the following formula (H7) or a compound having the following formula (H7) as a partial structure.

[0285] [ka]

[0286] In formula (H7), ED is an electron donating group, Ln is a linking group, and EA is an electron accepting group. The singlet energy (S 1 ) and triplet energy (T 1 ) energy difference (ΔS 1 T 1 ) is less than 0.2 eV (Hiroki Uoyama, Kenichi Goushi, Katsuyuki Shizu, Hiroko Nomura, Chihaya Adachi, Nature, 492, 234-238 (2012)). The energy difference (ΔS 1 T 1 ) is preferably 0.15 eV or less, more preferably 0.10 eV or less, and further preferably 0.08 eV or less.

[0287] As the electron donating group (donor structure) and the electron accepting group (acceptor structure) 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-tert-butylcarbazole, dimethoxycarbazole, tetramethylcarbazole, benzofluorocarbazole, benzothienocarbazole, phenyldihydroindolocarbazole, phenylbicarbazole, bicarbazole, tercarbazole, diphenylcarbazolylamine, tetraphenylcarbazolyldiamine, phenoxazine, dihydrophenazine, phenothiazine, dimethyldihydroacridine, diphenylamine, bis(tert-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 with ketones and cyano, 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. In formula (H7), the linking group Ln functions as a spacer structure that separates the donor partial structure and the acceptor partial structure.

[0288] More specifically, the compound represented by formula (H7) may be any of the compounds represented by formulas (H7-1), (H7-2) and (H7-3). [ka]

[0289] In formula (H7-1), formula (H7-2) and formula (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 linking group corresponding to Ln in formula (H7), and each J is independently an arylene having 6 to 18 carbon atoms. From the viewpoint of the magnitude of conjugation exuded from the donor partial structure and the acceptor partial structure, an arylene having 6 to 12 carbon atoms is 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-tert-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.

[0290] Examples of the compound represented by formula (H7) include compounds represented by the following structures: In the structural formula, * denotes a bond position, "Me" denotes methyl, and "tBu" denotes t-butyl.

[0291] [ka]

[0292] [ka]

[0293] [ka]

[0294] [ka]

[0295] [ka]

[0296] [ka]

[0297] [ka]

[0298] [ka]

[0299] [ka]

[0300] Among the specific compounds represented by formula (H7), PIC-TRZ, TXO-TPA, TXO-PhCz, PXZD SO2, ACRD SO2, DTC-DBT, DTAO, 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 preferred.

[0301] 3-1-5-3.Dopant materials The polycyclic aromatic compound of the present invention is preferably used as a dopant material. Dopant materials that can be used other than the polycyclic aromatic compound of the present invention are not particularly limited, and known compounds can be used, and can be selected from a variety of 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.

[0302] 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 include aromatic heterocyclic compounds such as lysine and thioxanthene and their derivatives, distyrylbenzene derivatives, tetraphenylbutadiene derivatives, stilbene derivatives, aldazine derivatives, coumarin derivatives, azole derivatives such as imidazole, thiazole, thiadiazole, carbazole, oxazole, oxadiazole, and triazole and their metal complexes, and aromatic amine derivatives typified by N,N'-diphenyl-N,N'-di(3-methylphenyl)-4,4'-diphenyl-1,1'-diamine.

[0303] 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.

[0304] 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 preferred examples of the compounds exemplified above as the 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.

[0305] In addition, the dopant may be appropriately selected from the compounds described in Chemical Industry, June 2004, p. 13 and the references cited therein.

[0306] 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.

[0307] 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, trisubstituted silyl (silyl trisubstituted with aryl, alkyl and / or cycloalkyl) or cyano, and m is an integer from 1 to 4.

[0308] 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 may be substituted with aryl, heteroaryl, alkyl, cycloalkyl, trisubstituted silyl (silyl trisubstituted with aryl, alkyl and / or cycloalkyl) or cyano.

[0309] 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.

[0310] 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. Examples of such aryl-4,4'-diaminostilbene include 4,4'-bis[4"-bis(diphenylamino)styryl]-biphenyl, 1,4-bis[4'-bis(diphenylamino)styryl]-benzene, 2,7-bis[4'-bis(diphenylamino)styryl]-9,9-dimethylfluorene, 4,4'-bis(9-ethyl-3-carbazovinylene)-biphenyl, and 4,4'-bis(9-phenyl-3-carbazovinylene)-biphenyl. Furthermore, amines having a stilbene structure, such as those described in JP-A Nos. 2003-347056 and 2001-307884, may also be used.

[0311] 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.

[0312] 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.

[0313] 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, trisubstituted silyl (silyl trisubstituted with aryl, alkyl and / or cycloalkyl) or cyano, and n is an integer from 1 to 4.

[0314] 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 aryl, alkyl and / or cycloalkyl) or cyano, and n is 2.

[0315] 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.

[0316] 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.

[0317] 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.

[0318] 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 the anthracene-9,10-diamine include 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.

[0319] 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.

[0320] 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.

[0321] Examples of pyran derivatives 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.

[0322] 3-1-6. Electron injection layer and electron transport layer in organic electroluminescent device The electron injection layer 107 plays a role of efficiently injecting electrons moving from the cathode 108 into the light-emitting layer 105 or the electron transport layer 106. The electron transport layer 106 plays a role of efficiently transporting electrons injected from the cathode 108 or electrons injected from the cathode 108 via the electron injection layer 107 to the light-emitting layer 105. The electron transport layer 106 and the electron injection layer 107 are each formed by laminating or mixing one or more types of electron transport / injection materials, or by a mixture of an electron transport / injection material and a polymer binder.

[0323] 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.

[0324] The material (electron transport material) for forming the electron transport layer 106 or the electron injection layer 107 can be arbitrarily selected from compounds conventionally used as electron transport compounds in photoconductive materials and known compounds used in the electron injection layer and electron transport layer of organic EL elements.

[0325] Materials used in the electron transport layer or electron injection layer preferably contain at least one selected from compounds consisting of aromatic rings or heteroaromatic rings composed of one or more atoms selected from carbon, hydrogen, oxygen, sulfur, silicon, and phosphorus, pyrrole derivatives and their condensed ring derivatives, and metal complexes having electron-accepting nitrogen. Specific examples include condensed ring aromatic ring derivatives such as naphthalene and anthracene, styryl aromatic ring derivatives such as 4,4'-bis(diphenylethenyl)biphenyl, perinone derivatives, coumarin derivatives, naphthalimide derivatives, quinone derivatives such as anthraquinone and diphenoquinone, phosphorus oxide derivatives, arylnitrile derivatives, and indole derivatives. Examples of metal complexes having electron-accepting nitrogen include hydroxyazole complexes such as hydroxyphenyloxazole complexes, azomethine complexes, tropolone metal complexes, flavonol metal complexes, and benzoquinoline metal complexes. These materials can be used alone or in combination with different materials.

[0326] Specific examples of other electron transport compounds include pyridine derivatives, naphthalene derivatives, anthracene derivatives, benzofluorene derivatives, phenanthroline derivatives, perinone derivatives, coumarin derivatives, naphthalimide derivatives, anthraquinone derivatives, diphenoquinone derivatives, diphenylquinone derivatives, perylene derivatives, oxadiazole derivatives (1,3-bis[(4-t-butylphenyl)1,3,4-oxadiazolyl]phenylene, etc.), thiophene derivatives, triazole derivatives (N-naphthyl-2,5-diphenyl-1,3,4-triazole, etc.), thiadiazole derivatives, metal complexes of oxine derivatives, quinolinol-based metal complexes, quinoxaline derivatives, polymers of quinoxaline derivatives, benzazole compounds, gallium complexes, pyrazole derivatives, perfluorinated phenylene derivatives, triazine derivatives, etc. Examples of the compound include pyrazine derivatives, benzoquinoline derivatives (2,2'-bis(benzo[h]quinolin-2-yl)-9,9'-spirobifluorene, etc.), imidazopyridine derivatives, borane derivatives, benzimidazole derivatives (tris(N-phenylbenzimidazol-2-yl)benzene, etc.), benzoxazole derivatives, benzothiazole derivatives, quinoline derivatives, oligopyridine derivatives such as terpyridine, bipyridine derivatives, terpyridine derivatives (1,3-bis(4'-(2,2':6'2"-terpyridinyl))benzene, etc.), naphthyridine derivatives (bis(1-naphthyl)-4-(1,8-naphthyridin-2-yl)phenylphosphine oxide, etc.), aldazine derivatives, arylnitrile derivatives, indole derivatives, phosphine oxide derivatives, and bisstyryl derivatives.

[0327] Furthermore, metal complexes having an electron-accepting nitrogen atom can also be used, and examples thereof include hydroxyazole complexes such as quinolinol metal complexes and hydroxyphenyloxazole complexes, azomethine complexes, tropolone metal complexes, flavonol metal complexes, and benzoquinoline metal complexes.

[0328] The above-mentioned materials may be used alone or in combination with different materials.

[0329] Among the above-mentioned materials, borane derivatives, pyridine derivatives, fluoranthene derivatives, BO-based derivatives, anthracene derivatives, benzofluorene derivatives, phosphine oxide derivatives, pyrimidine derivatives, arylnitrile derivatives, triazine derivatives, benzimidazole derivatives, phenanthroline derivatives, and quinolinol-based metal complexes are preferable.

[0330] <Borane derivatives> The borane derivative is, for example, a compound represented by the following formula (ETM-1), and is disclosed in detail in JP-A-2007-27587. [ka] In formula (ETM-1), R 11 and R 12 are each independently at least one of hydrogen, alkyl, cycloalkyl, optionally substituted aryl, substituted silyl, optionally substituted nitrogen-containing heterocycle, or cyano; R 13 ~R 16 are each independently an optionally substituted alkyl, an optionally substituted cycloalkyl, or an optionally substituted aryl, X is an optionally substituted arylene, Y is an optionally substituted aryl having 16 or less carbon atoms, a substituted boryl, or an optionally substituted carbazolyl, and each n is independently an integer of 0 to 3. In addition, examples of the substituent in the case of "optionally substituted" or "substituted" include aryl, heteroaryl, alkyl, and cycloalkyl.

[0331] Among the compounds represented by formula (ETM-1), compounds represented by the following formula (ETM-1-1) and compounds represented by the following formula (ETM-1-2) are preferred. [ka] In formula (ETM-1-1), R 11 and R 12are each independently at least one of hydrogen, alkyl, cycloalkyl, optionally substituted aryl, substituted silyl, optionally substituted nitrogen-containing heterocycle, or cyano; R 13 ~R 16 are each independently optionally substituted alkyl, optionally substituted cycloalkyl, or optionally substituted aryl; R 21 and R 22 are each independently at least one of hydrogen, alkyl, cycloalkyl, optionally substituted aryl, substituted silyl, optionally substituted nitrogen-containing heterocycle, or cyano; X 1 is an optionally substituted arylene having 20 or less carbon atoms, each n is independently an integer of 0 to 3, and each m is independently an integer of 0 to 4. In addition, examples of the substituent in the case where "optionally substituted" or "substituted" include aryl, heteroaryl, alkyl, and cycloalkyl. [ka] In formula (ETM-1-2), R 11 and R 12 are each independently at least one of hydrogen, alkyl, cycloalkyl, optionally substituted aryl, substituted silyl, optionally substituted nitrogen-containing heterocycle, or cyano; R 13 ~R 16 are each independently an optionally substituted alkyl, an optionally substituted cycloalkyl, or an optionally substituted aryl; X 1 is an optionally substituted arylene having 20 or less carbon atoms, and each n is independently an integer of 0 to 3. Examples of the substituent in the case where it is "optionally substituted" or "substituted" include aryl, heteroaryl, alkyl, and cycloalkyl.

[0332] X 1 Specific examples of the group include divalent groups represented by any of the following formulae (X-1) to (X-9). [ka] (In each formula, R a are each independently alkyl, cycloalkyl, or optionally substituted phenyl, and * represents the bonding position.

[0333] Specific examples of the borane derivative include the following compounds: [ka]

[0334] The borane derivative can be produced using known raw materials and known synthesis methods.

[0335] <Pyridine derivatives> The pyridine derivative is, for example, a compound represented by the following formula (ETM-2), preferably a compound represented by formula (ETM-2-1) or formula (ETM-2-2). [ka]

[0336] φ is an n-valent aryl ring (preferably an n-valent benzene ring, naphthalene ring, anthracene ring, fluorene ring, benzofluorene ring, phenalene ring, phenanthrene ring or triphenylene ring), and n is an integer of 1 to 4.

[0337] In formula (ETM-2-1), R 11 ~R 18 are each independently hydrogen, alkyl (preferably alkyl having 1 to 24 carbon atoms), cycloalkyl (preferably cycloalkyl having 3 to 12 carbon atoms) or aryl (preferably aryl having 6 to 30 carbon atoms).

[0338] In formula (ETM-2-2), R 11 and R 12are each independently hydrogen, alkyl (preferably alkyl having 1 to 24 carbon atoms), cycloalkyl (preferably cycloalkyl having 3 to 12 carbon atoms) or aryl (preferably aryl having 6 to 30 carbon atoms); R 11 and R 12 may be bonded to form a ring.

[0339] In each formula, the "pyridine-based substituent" is any one of the following formulae (Py-1) to (Py-15) (in the formula, * indicates a bonding position), and each pyridine-based substituent may be independently substituted with an alkyl having 1 to 4 carbon atoms or a cycloalkyl having 5 to 10 carbon atoms. Specific examples include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, and t-butyl, and methyl is preferred. In addition, the pyridine-based substituent may be bonded to the φ, anthracene ring, or fluorene ring in each formula via phenylene or naphthylene.

[0340] [ka]

[0341] The pyridine-based substituent is any one of the formulae (Py-1) to (Py-15) (wherein * represents a bonding position), and among these, any one of the following formulae (Py-21) to (Py-44) is preferable. [ka]

[0342] At least one hydrogen atom in each pyridine derivative may be replaced by deuterium, and one of the two "pyridine-based substituents" in formulae (ETM-2-1) and (ETM-2-2) may be replaced by aryl.

[0343] R 11 ~R 18The "alkyl" in the above may be either linear or branched, and examples thereof include linear alkyl having 1 to 24 carbon atoms or branched alkyl having 3 to 24 carbon atoms. A preferred "alkyl" is an alkyl having 1 to 18 carbon atoms (branched alkyl having 3 to 18 carbon atoms). A more preferred "alkyl" is an alkyl having 1 to 12 carbon atoms (branched alkyl having 3 to 12 carbon atoms). An even more preferred "alkyl" is an alkyl having 1 to 6 carbon atoms (branched alkyl having 3 to 6 carbon atoms). An especially preferred "alkyl" is an alkyl having 1 to 4 carbon atoms (branched alkyl having 3 to 4 carbon atoms).

[0344] Specific examples of "alkyl" include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, t-butyl, n-pentyl, isopentyl, neopentyl, t-pentyl, n-hexyl, 1-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, n-heptyl, 1-methylhexyl, n-octyl, t-octyl, 1-methylheptyl, Examples include 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 2,6-dimethyl-4-heptyl, 3,5,5-trimethylhexyl, n-decyl, n-undecyl, 1-methyldecyl, n-dodecyl, n-tridecyl, 1-hexylheptyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, n-heptadecyl, n-octadecyl, and n-eicosyl.

[0345] As for the alkyl having 1 to 4 carbon atoms with which the pyridine-based substituent is substituted, the above description of the alkyl can be cited.

[0346] R 11 ~R 18 In the above, the "cycloalkyl" is, for example, a cycloalkyl having 3 to 12 carbon atoms. A preferred "cycloalkyl" is a cycloalkyl having 3 to 10 carbon atoms. A more preferred "cycloalkyl" is a cycloalkyl having 3 to 8 carbon atoms. An even more preferred "cycloalkyl" is a cycloalkyl having 3 to 6 carbon atoms. Specific examples of "cycloalkyl" include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, methylcyclopentyl, cycloheptyl, methylcyclohexyl, cyclooctyl, and dimethylcyclohexyl.

[0347] R 11 ~R 18 As for the "aryl" in the above, a preferable aryl is an aryl having 6 to 30 carbon atoms, a more preferable aryl is an aryl having 6 to 18 carbon atoms, an even more preferable aryl is an aryl having 6 to 14 carbon atoms, and an especially preferable aryl is an aryl having 6 to 12 carbon atoms.

[0348] Specific examples of the "aryl having 6 to 30 carbon atoms" include monocyclic aryl phenyl, fused bicyclic aryl (1-, 2-)naphthyl, fused tricyclic aryl acenaphthylene-(1-, 3-, 4-, 5-)yl, fluoren-(1-, 2-, 3-, 4-, 9-)yl, phenalene-(1-, 2-)yl, (1-, 2-, 3-, 4-, 9-)phenanthryl, fused tetracyclic aryl triphenylene-(1-, 2-)yl, pyrene-(1-, 2-, 4-)yl, naphthacene-(1-, 2-, 5-)yl, fused pentacyclic aryl perylene-(1-, 2-, 3-)yl, pentacene-(1-, 2-, 5-, 6-)yl, and the like.

[0349] Preferred examples of the "aryl having 6 to 30 carbon atoms" include phenyl, naphthyl, phenanthryl, chrysenyl, and triphenylenyl, more preferably phenyl, 1-naphthyl, 2-naphthyl, and phenanthryl, and particularly preferably phenyl, 1-naphthyl, and 2-naphthyl.

[0350] R in formula (ETM-2-2) 11 and R 12 may be bonded to form a ring, and as a result, cyclobutane, cyclopentane, cyclopentene, cyclopentadiene, cyclohexane, fluorene, indene, or the like may be spiro-bonded to the five-membered ring of the fluorene skeleton.

[0351] Specific examples of this pyridine derivative include, for example, the following compounds.

Chemical formula

[0352] This pyridine derivative can be produced using known raw materials and known synthesis methods.

[0353] <Fluoranthene derivative> The fluoranthene derivative is, for example, a compound represented by the following formula (ETM-3), and in detail, it is disclosed in International Publication No. 2010 / 134352.

Chemical formula

[0354] In formula (ETM-3), X 12 ~X 21 represents hydrogen, halogen, linear, branched or cyclic alkyl, linear, branched or cyclic alkoxy, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl. Here, examples of the substituent when it is substituted include aryl, heteroaryl, alkyl or cycloalkyl.

[0355] Specific examples of this fluoranthene derivative include, for example, the following compounds.

Chemical formula

[0356] <BO-based derivative> The BO-based derivative is, for example, a polycyclic aromatic compound represented by the following formula (ETM-4), or a multimer of a polycyclic aromatic compound having a plurality of structures represented by the following formula (ETM-4).

Chemical formula

[0357] R 1 ~R 11 are each independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, alkyl, cycloalkyl, alkoxy, or aryloxy, in which at least one hydrogen may be substituted with aryl, heteroaryl, alkyl, or cycloalkyl.

[0358] Also, R 1 ~R 11 Adjacent groups among these may be bonded to each other to form an aryl ring or a heteroaryl ring together with the a ring, the b ring, or the c ring, and at least one hydrogen atom in the formed ring may be substituted with an aryl, a heteroaryl, a diarylamino, a diheteroarylamino, an arylheteroarylamino, an alkyl, a cycloalkyl, an alkoxy, or an aryloxy, and at least one hydrogen atom in these rings may be substituted with an aryl, a heteroaryl, an alkyl, or a cycloalkyl.

[0359] In addition, at least one hydrogen in the compound or structure represented by formula (ETM-4) may be substituted with a halogen or deuterium.

[0360] For an explanation of the substituents and the form of ring formation in formula (ETM-4), the explanation of the polycyclic aromatic compounds represented by formulas (1A) and (1B) can be cited.

[0361] Specific examples of the BO derivative include the following compounds: [ka]

[0362] The BO derivative can be produced using known raw materials and known synthesis methods.

[0363] <Anthracene derivatives> One of the anthracene derivatives is, for example, a compound represented by the following formula (ETM-5). [ka]

[0364] Ar 1 are each independently a single bond, or a divalent benzene, naphthalene, anthracene, fluorene, or phenalene.

[0365] Ar 2are each independently an aryl having 6 to 20 carbon atoms, preferably an aryl having 6 to 16 carbon atoms, more preferably an aryl having 6 to 12 carbon atoms, and particularly preferably an aryl having 6 to 10 carbon atoms. Specific examples of "aryl having 6 to 20 carbon atoms" include monocyclic aryls such as phenyl, (o-, m-, p-)tolyl, (2,3-, 2,4-, 2,5-, 2,6-, 3,4-, 3,5-)xylyl, mesityl (2,4,6-trimethylphenyl), and (o-, m-, p-)cumenyl, bicyclic aryls such as (2-, 3-, 4-)biphenylyl, condensed bicyclic aryls such as (1-, 2-)naphthyl, and tricyclic aryls such as terphenylyl (m-terphenyl-2'-yl, m-terphenyl-4'-yl, m-terphenyl-5'-yl, o-terphenyl-3'-yl, o-terphenyl-4'-yl, p-terphenyl-2'-yl, m-terphenyl-2-yl, m-terphenyl-3-yl, m-terphenyl-4'-yl, p-terphenyl-2 ...4'-yl, p-terphenyl-2-yl, m-terphenyl-2-yl, m-terphenyl-3-yl, m-terphenyl-4'-yl, p-terphenyl-2-yl, m-terphenyl-4'-yl, p-terphenyl-2-yl, m-terphenyl-2-yl, m-terphenyl-3-yl, m aryl, o-terphenyl-4-yl, o-terphenyl-2-yl, o-terphenyl-3-yl, o-terphenyl-4-yl, p-terphenyl-2-yl, p-terphenyl-3-yl, p-terphenyl-4-yl; condensed tricyclic aryls, anthracene-(1-,2-,9-)yl, acenaphthylene-(1-,3-,4-,5-)yl, fluorene-(1-,2-,3-,4-,9-)yl, phenalene-(1-,2-)yl, (1-,2-,3-,4-,9-)phenanthryl; condensed tetracyclic aryls, triphenylene-(1-,2-)yl, pyrene-(1-,2-,4-)yl, tetracene-(1-,2-,5-)yl; condensed pentacyclic aryls, perylene-(1-,2-,3-)yl, and the like. Specific examples of the "aryl having 6 to 10 carbon atoms" include phenyl, biphenylyl, naphthyl, terphenylyl, anthracenyl, acenaphthylenyl, fluorenyl, phenalenyl, phenanthryl, triphenylenyl, pyrenyl, tetracenyl, and perylenyl.

[0366] R 1 ~R 4 are each independently hydrogen, alkyl having 1 to 6 carbon atoms, cycloalkyl having 3 to 6 carbon atoms, or aryl having 6 to 20 carbon atoms. R 1 ~R4 The alkyl having 1 to 6 carbon atoms in the formula (I) may be either linear or branched. That is, it is a linear alkyl having 1 to 6 carbon atoms or a branched alkyl having 3 to 6 carbon atoms. More preferably, it is an alkyl having 1 to 4 carbon atoms (branched alkyl having 3 to 4 carbon atoms). Specific examples include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, t-butyl, n-pentyl, isopentyl, neopentyl, t-pentyl, n-hexyl, 1-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, and 2-ethylbutyl. Methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, and t-butyl are preferred, and methyl, ethyl, and t-butyl are more preferred.

[0367] R 1 ~R 4 Specific examples of the cycloalkyl having 3 to 6 carbon atoms include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, methylcyclopentyl, cycloheptyl, methylcyclohexyl, cyclooctyl, and dimethylcyclohexyl.

[0368] R 1 ~R 4 In the above, the aryl having 6 to 20 carbon atoms is preferably an aryl having 6 to 16 carbon atoms, more preferably an aryl having 6 to 12 carbon atoms, and particularly preferably an aryl having 6 to 10 carbon atoms. Specific examples of "aryl having 6 to 20 carbon atoms" include Ar 2 Specific examples of "aryl having 6 to 20 carbon atoms" in the above can be cited. Preferred "aryl having 6 to 20 carbon atoms" are phenyl, biphenylyl, terphenylyl, or naphthyl, more preferably phenyl, biphenylyl, 1-naphthyl, 2-naphthyl, or m-terphenyl-5'-yl, further preferably phenyl, biphenylyl, 1-naphthyl, or 2-naphthyl, and most preferably phenyl.

[0369] Specific examples of these anthracene derivatives include the following compounds. [ka]

[0370] These anthracene derivatives can be produced using known raw materials and known synthesis methods.

[0371] <Benzofluorene derivatives> The benzofluorene derivative is, for example, a compound represented by the following formula (ETM-6). [ka]

[0372] Ar 1 are each independently an aryl having 6 to 20 carbon atoms, and Ar 2 The same explanation as for "aryl having 6 to 20 carbon atoms" in the above can be cited. An aryl having 6 to 16 carbon atoms is preferable, an aryl having 6 to 12 carbon atoms is more preferable, and an aryl having 6 to 10 carbon atoms is particularly preferable. Specific examples include phenyl, biphenylyl, naphthyl, terphenylyl, anthracenyl, acenaphthylenyl, fluorenyl, phenalenyl, phenanthryl, triphenylenyl, pyrenyl, tetracenyl, perylenyl, etc.

[0373] Ar 2 are each independently hydrogen, alkyl (preferably alkyl having 1 to 24 carbon atoms), cycloalkyl (preferably cycloalkyl having 3 to 12 carbon atoms) or aryl (preferably aryl having 6 to 30 carbon atoms), and two Ar 2 may be bonded to form a ring.

[0374] Ar 2The "alkyl" in the above may be either linear or branched, and examples thereof include linear alkyl having 1 to 24 carbon atoms or branched alkyl having 3 to 24 carbon atoms. A preferred "alkyl" is an alkyl having 1 to 18 carbon atoms (branched alkyl having 3 to 18 carbon atoms). A more preferred "alkyl" is an alkyl having 1 to 12 carbon atoms (branched alkyl having 3 to 12 carbon atoms). An even more preferred "alkyl" is an alkyl having 1 to 6 carbon atoms (branched alkyl having 3 to 6 carbon atoms). An especially preferred "alkyl" is an alkyl having 1 to 4 carbon atoms (branched alkyl having 3 to 4 carbon atoms). Specific examples of "alkyl" include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, t-butyl, n-pentyl, isopentyl, neopentyl, t-pentyl, n-hexyl, 1-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, n-heptyl, 1-methylhexyl, and the like.

[0375] Ar 2 In the above, the "cycloalkyl" is, for example, a cycloalkyl having 3 to 12 carbon atoms. A preferred "cycloalkyl" is a cycloalkyl having 3 to 10 carbon atoms. A more preferred "cycloalkyl" is a cycloalkyl having 3 to 8 carbon atoms. An even more preferred "cycloalkyl" is a cycloalkyl having 3 to 6 carbon atoms. Specific examples of the "cycloalkyl" include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, methylcyclopentyl, cycloheptyl, methylcyclohexyl, cyclooctyl, and dimethylcyclohexyl.

[0376] Ar 2 As for the "aryl" in the above, a preferable aryl is an aryl having 6 to 30 carbon atoms, a more preferable aryl is an aryl having 6 to 18 carbon atoms, an even more preferable aryl is an aryl having 6 to 14 carbon atoms, and an especially preferable aryl is an aryl having 6 to 12 carbon atoms.

[0377] Specific examples of the "aryl having 6 to 30 carbon atoms" include phenyl, naphthyl, acenaphthylenyl, fluorenyl, phenalenyl, phenanthryl, triphenylenyl, pyrenyl, naphthacenyl, perylenyl, and pentacenyl.

[0378] Two Ar 2 may be bonded to form a ring, and as a result, cyclobutane, cyclopentane, cyclopentene, cyclopentadiene, cyclohexane, fluorene, indene, or the like may be spiro-bonded to the five-membered ring of the fluorene skeleton.

[0379] Specific examples of the benzofluorene derivative include the following compounds: [ka]

[0380] The benzofluorene derivative can be produced using known raw materials and known synthesis methods.

[0381] <Phosphine oxide derivatives> The phosphine oxide derivative is, for example, a compound represented by the following formula (ETM-7-1): The details are also described in WO 2013 / 079217 and WO 2013 / 079678. [ka]

[0382] R 5 is a substituted or unsubstituted alkyl having 1 to 20 carbon atoms, cycloalkyl having 3 to 16 carbon atoms, aryl having 6 to 20 carbon atoms, or heteroaryl having 5 to 20 carbon atoms, R 6 is CN, a substituted or unsubstituted alkyl having 1 to 20 carbon atoms, a cycloalkyl having 3 to 16 carbon atoms, a heteroalkyl having 1 to 20 carbon atoms, an aryl having 6 to 20 carbon atoms, a heteroaryl having 5 to 20 carbon atoms, an alkoxy having 1 to 20 carbon atoms, or an aryloxy having 6 to 20 carbon atoms, R 7 and R 8 each independently represents a substituted or unsubstituted aryl having 6 to 20 carbon atoms or a heteroaryl having 5 to 20 carbon atoms, R 9 is oxygen or sulfur, j is 0 or 1, k is 0 or 1, r is an integer of 0 to 4, and q is an integer of 1 to 3. When substituted, the substituent may be an aryl, heteroaryl, alkyl or cycloalkyl.

[0383] The phosphine oxide derivative may be, for example, a compound represented by the following formula (ETM-7-2). [ka]

[0384] R 1 ~R 3 may be the same or different and are selected from hydrogen, alkyl, cycloalkyl, aralkyl, alkenyl, cycloalkenyl, alkynyl, alkoxy, alkylthio, cycloalkylthio, aryl ether (aryl ether group), aryl thioether (aryl thioether group), aryl, heterocyclic group, halogen, cyano, aldehyde, carbonyl, carboxyl, amino, nitro, silyl, and a fused ring formed between adjacent substituents.

[0385] Ar 1 may be the same or different and are arylene or heteroarylene. Ar 2 may be the same or different and are aryl or heteroaryl, provided that Ar 1 and Ar 2 At least one of R has a substituent or forms a condensed ring with the adjacent substituent. n is an integer of 0 to 3. When n is 0, there is no unsaturated structural portion. When n is 3, R 1 does not exist.

[0386] Among these substituents, alkyl refers to saturated aliphatic hydrocarbon groups such as methyl, ethyl, propyl, and butyl, which may be unsubstituted or substituted. If substituted, the substituent is not particularly limited, and may be, for example, alkyl, aryl, or heterocyclic groups, which is also the case in the following description. The number of carbon atoms in the alkyl is not particularly limited, but is usually in the range of 1 to 20 in terms of availability and cost.

[0387] The term "cycloalkyl" refers to a saturated alicyclic hydrocarbon group, such as cyclopropyl, cyclohexyl, norbornyl, adamantyl, etc., which may be unsubstituted or substituted. The number of carbon atoms in the alkyl portion is not particularly limited, but is usually in the range of 3 to 20.

[0388] The term "aralkyl" refers to an aromatic hydrocarbon group mediated by an aliphatic hydrocarbon such as benzyl or phenylethyl, and both the aliphatic hydrocarbon and the aromatic hydrocarbon may be unsubstituted or substituted. The number of carbon atoms in the aliphatic portion is not particularly limited, but is usually in the range of 1 to 20.

[0389] The alkenyl refers to an unsaturated aliphatic hydrocarbon group containing a double bond, such as vinyl, allyl, butadienyl, which may be unsubstituted or substituted. The number of carbon atoms in the alkenyl is not particularly limited, but is usually in the range of 2 to 20.

[0390] Moreover, cycloalkenyl refers to an unsaturated alicyclic hydrocarbon group containing a double bond, such as cyclopentenyl, cyclopentadienyl, cyclohexenyl, etc., which may be unsubstituted or substituted.

[0391] The term "alkynyl" refers to an unsaturated aliphatic hydrocarbon group containing a triple bond, such as acetylenyl, which may be unsubstituted or substituted. The number of carbon atoms in the alkynyl is not particularly limited, but is usually within the range of 2 to 20.

[0392] The term "alkoxy" refers to an aliphatic hydrocarbon group, such as methoxy, which is bonded via an ether bond, and the aliphatic hydrocarbon group may be unsubstituted or substituted. The number of carbon atoms in the alkoxy is not particularly limited, but is usually in the range of 1 to 20.

[0393] Moreover, alkylthio is a group in which the oxygen atom of the ether bond of alkoxy is replaced with a sulfur atom.

[0394] Moreover, cycloalkylthio is a group in which the oxygen atom of the ether bond of cycloalkoxy is replaced with a sulfur atom.

[0395] The aryl ether refers to an aromatic hydrocarbon group, such as phenoxy, which is bonded via an ether bond, and the aromatic hydrocarbon group may be unsubstituted or substituted. The number of carbon atoms in the aryl ether is not particularly limited, but is usually in the range of 6 to 40.

[0396] An aryl thioether is a group in which the oxygen atom of the ether bond of an aryl ether is replaced with a sulfur atom.

[0397] The aryl group refers to an aromatic hydrocarbon group such as phenyl, naphthyl, biphenylyl, phenanthryl, terphenylyl, pyrenyl, etc. The aryl group may be unsubstituted or substituted. The number of carbon atoms in the aryl group is not particularly limited, but is usually in the range of 6 to 40.

[0398] The heterocyclic group refers to a cyclic structure group having atoms other than carbon, such as furanyl, thienyl, oxazolyl, pyridyl, quinolinyl, carbazolyl, etc., which may be unsubstituted or substituted. The number of carbon atoms in the heterocyclic group is not particularly limited, but is usually in the range of 2 to 30.

[0399] Halogen refers to fluorine, chlorine, bromine and iodine.

[0400] The aldehyde, carbonyl and amino groups may also include groups substituted with aliphatic hydrocarbons, alicyclic hydrocarbons, aromatic hydrocarbons, heterocycles and the like.

[0401] Furthermore, the aliphatic hydrocarbons, alicyclic hydrocarbons, aromatic hydrocarbons and heterocycles may be either unsubstituted or substituted.

[0402] Silyl refers to a silicon compound group such as trimethylsilyl, which may be unsubstituted or substituted. The number of carbon atoms in silyl is not particularly limited, but is usually in the range of 3 to 20. The number of silicon atoms is usually 1 to 6.

[0403] The condensed ring formed between adjacent substituents is, for example, Ar 1 and R 2 , Ar 1 and R 3 , Ar 2 and R 2 , Ar 2 and R 3 , R 2 and R 3 , Ar 1 and Ar 2 etc., where n is 1, two R 1 They may form conjugated or non-conjugated fused rings together. These fused rings may contain nitrogen, oxygen, or sulfur atoms in the ring structure, and may be fused to further rings.

[0404] Specific examples of the phosphine oxide derivative include the following compounds: [ka]

[0405] The phosphine oxide derivative can be produced using known raw materials and known synthesis methods.

[0406] <Pyrimidine derivatives> The pyrimidine derivative is, for example, a compound represented by the following formula (ETM-8), preferably a compound represented by the following formula (ETM-8-1). Details are also described in WO 2011 / 021689. [ka]

[0407] Each Ar is independently an optionally substituted aryl or an optionally substituted heteroaryl, and n is an integer of 1 to 4, preferably an integer of 1 to 3, and more preferably 2 or 3.

[0408] The "aryl" in the "optionally substituted aryl" includes, for example, an aryl having 6 to 30 carbon atoms, preferably an aryl having 6 to 24 carbon atoms, more preferably an aryl having 6 to 20 carbon atoms, and further preferably an aryl having 6 to 12 carbon atoms.

[0409] Specific examples of "aryl" include monocyclic aryl phenyl, bicyclic aryl (2-, 3-, 4-) biphenylyl, condensed bicyclic aryl (1-, 2-) naphthyl, tricyclic aryl terphenylyl (m-terphenyl-2'-yl, m-terphenyl-4'-yl, m-terphenyl-5'-yl, o-terphenyl-3'-yl, o-terphenyl-4'-yl, p-terphenyl-2'-yl, m-terphenyl-2-yl, m-terphenyl-3-yl, m-terphenyl-4-yl, o-terphenyl-2-yl, o-terphenyl-3-yl, o-terphenyl-4-yl, p-terphenyl-2-yl, p-terphenyl-3-yl, p-terphenyl-4-yl), condensed tricyclic aryl Examples of the aryl include acenaphthylene-(1-,3-,4-,5-)yl, fluorene-(1-,2-,3-,4-,9-)yl, phenalene-(1-,2-)yl, (1-,2-,3-,4-,9-)phenanthryl, the tetracyclic aryl group is quaterphenylyl (5'-phenyl-m-terphenyl-2-yl, 5'-phenyl-m-terphenyl-3-yl, 5'-phenyl-m-terphenyl-4-yl, m-quaterphenylyl), the condensed tetracyclic aryl group is triphenylene-(1-,2-)yl, pyrene-(1-,2-,4-)yl, naphthacene-(1-,2-,5-)yl, the condensed pentacyclic aryl group is perylene-(1-,2-,3-)yl, pentacene-(1-,2-,5-,6-)yl, and the like.

[0410] Examples of the "heteroaryl" in "optionally substituted heteroaryl" include heteroaryl having 2 to 30 carbon atoms, preferably heteroaryl having 2 to 25 carbon atoms, more preferably heteroaryl having 2 to 20 carbon atoms, further preferably heteroaryl having 2 to 15 carbon atoms, and particularly preferably heteroaryl having 2 to 10 carbon atoms. Examples of the heteroaryl include heterocycles containing, as ring-constituting atoms other than carbon, 1 to 5 heteroatoms selected from oxygen, sulfur, and nitrogen.

[0411] Specific examples of heteroaryl include furyl, thienyl, pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, pyrazolyl, oxadiazolyl, furazanyl, thiadiazolyl, triazolyl, tetrazolyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, benzofuranyl, isobenzofuranyl, benzo[b]thienyl, indolyl, isoindolyl, 1H-indazolyl, benzimidazolyl, benzoxazolyl, benzothiazolyl, 1H-benzotriazolyl, quinolyl, isoquinolyl, cinnolyl, quinazolyl, quinoxalinyl, phthalazinyl, naphthyridinyl, purinyl, pteridinyl, carbazolyl, acridinyl, phenoxazinyl, phenothiazinyl, phenazinyl, phenoxathiinyl, thianthrenyl, and indolizinyl.

[0412] The above aryl and heteroaryl may be substituted, for example, by the above aryl or heteroaryl, respectively.

[0413] Specific examples of the pyrimidine derivative include the following compounds: [ka]

[0414] The pyrimidine derivative can be produced using known raw materials and known synthesis methods.

[0415] <Aryl nitrile derivatives> The arylnitrile derivative is, for example, a compound represented by the following formula (ETM-9), or a multimer in which a plurality of such compounds are bonded together via single bonds, etc. Details are described in the specification of US Patent Publication No. 2014 / 0197386. [ka]

[0416] Ar niFrom the viewpoint of fast electron transporting property, it is preferable that the number of carbon atoms is large, and from the viewpoint of high T1, it is preferable that the number of carbon atoms is small. ni Specifically, it is preferable that the aryl group has a high T1 when used in a layer adjacent to the light-emitting layer, and is an aryl group having 6 to 20 carbon atoms, preferably an aryl group having 6 to 14 carbon atoms, and more preferably an aryl group having 6 to 10 carbon atoms. In addition, the number of nitrile group substitutions, n, is preferably large from the viewpoint of high T1, and is preferably small from the viewpoint of high S1. Specifically, the number of nitrile group substitutions, n, is an integer of 1 to 4, preferably an integer of 1 to 3, more preferably an integer of 1 to 2, and even more preferably 1.

[0417] Each Ar is independently an aryl which may be substituted or a heteroaryl which may be substituted. From the viewpoint of high S1 and high T1, it is preferable that the heteroaryl has donor properties, and it is preferable that the heteroaryl has few donor properties because it is used as an electron transport layer. From the viewpoint of charge transportability, it is preferable that the aryl or heteroaryl has many carbon atoms, and it is preferable that the aryl or heteroaryl has many substituents. The number of substitutions m of Ar is specifically an integer of 1 to 4, preferably an integer of 1 to 3, and more preferably 1 to 2.

[0418] The "aryl" in the "optionally substituted aryl" includes, for example, an aryl having 6 to 30 carbon atoms, preferably an aryl having 6 to 24 carbon atoms, more preferably an aryl having 6 to 20 carbon atoms, and further preferably an aryl having 6 to 12 carbon atoms.

[0419] Specific examples of "aryl" include monocyclic aryl phenyl, bicyclic aryl (2-, 3-, 4-) biphenylyl, condensed bicyclic aryl (1-, 2-) naphthyl, tricyclic aryl terphenylyl (m-terphenyl-2'-yl, m-terphenyl-4'-yl, m-terphenyl-5'-yl, o-terphenyl-3'-yl, o-terphenyl-4'-yl, p-terphenyl-2'-yl, m-terphenyl-2-yl, m-terphenyl-3-yl, m-terphenyl-4-yl, o-terphenyl-2-yl, o-terphenyl-3-yl, o-terphenyl-4-yl, p-terphenyl-2-yl, p-terphenyl-3-yl, p-terphenyl-4-yl), condensed tricyclic aryl Examples of the aryl include acenaphthylene-(1-,3-,4-,5-)yl, fluorene-(1-,2-,3-,4-,9-)yl, phenalene-(1-,2-)yl, (1-,2-,3-,4-,9-)phenanthryl, the tetracyclic aryl group is quaterphenylyl (5'-phenyl-m-terphenyl-2-yl, 5'-phenyl-m-terphenyl-3-yl, 5'-phenyl-m-terphenyl-4-yl, m-quaterphenylyl), the condensed tetracyclic aryl group is triphenylene-(1-,2-)yl, pyrene-(1-,2-,4-)yl, naphthacene-(1-,2-,5-)yl, the condensed pentacyclic aryl group is perylene-(1-,2-,3-)yl, pentacene-(1-,2-,5-,6-)yl, and the like.

[0420] Examples of the "heteroaryl" in "optionally substituted heteroaryl" include heteroaryl having 2 to 30 carbon atoms, preferably heteroaryl having 2 to 25 carbon atoms, more preferably heteroaryl having 2 to 20 carbon atoms, further preferably heteroaryl having 2 to 15 carbon atoms, and particularly preferably heteroaryl having 2 to 10 carbon atoms. Examples of the heteroaryl include heterocycles containing, as ring-constituting atoms other than carbon, 1 to 5 heteroatoms selected from oxygen, sulfur, and nitrogen.

[0421] Specific examples of heteroaryl include furyl, thienyl, pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, pyrazolyl, oxadiazolyl, furazanyl, thiadiazolyl, triazolyl, tetrazolyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, benzofuranyl, isobenzofuranyl, benzo[b]thienyl, indolyl, isoindolyl, 1H-indazolyl, benzimidazolyl, benzoxazolyl, benzothiazolyl, 1H-benzotriazolyl, quinolyl, isoquinolyl, cinnolyl, quinazolyl, quinoxalinyl, phthalazinyl, naphthyridinyl, purinyl, pteridinyl, carbazolyl, acridinyl, phenoxazinyl, phenothiazinyl, phenazinyl, phenoxathiinyl, thianthrenyl, and indolizinyl.

[0422] The above aryl and heteroaryl may be substituted, for example, by the above aryl or heteroaryl, respectively.

[0423] The arylnitrile derivative may be a polymer in which a plurality of compounds represented by formula (ETM-9) are bonded together via single bonds, etc. In this case, they may be bonded together via an aryl ring (preferably a polyvalent benzene ring, naphthalene ring, anthracene ring, fluorene ring, benzofluorene ring, phenalene ring, phenanthrene ring, or triphenylene ring) in addition to a single bond.

[0424] Specific examples of the arylnitrile derivative include the following compounds: [ka]

[0425] The arylnitrile derivatives can be produced using known raw materials and known synthesis methods.

[0426] The carbazole derivative can be produced using known raw materials and known synthesis methods.

[0427] <Triazine derivatives> The triazine derivative is, for example, a compound represented by the following formula (ETM-10), preferably a compound represented by the following formula (ETM-10-1), the details of which are described in the specification of US Patent Application Publication No. 2011 / 0156013. [ka]

[0428] Each Ar is independently an optionally substituted aryl or an optionally substituted heteroaryl, and n is an integer of 1 to 3, preferably 2 or 3.

[0429] The "aryl" in the "optionally substituted aryl" includes, for example, an aryl having 6 to 30 carbon atoms, preferably an aryl having 6 to 24 carbon atoms, more preferably an aryl having 6 to 20 carbon atoms, and further preferably an aryl having 6 to 12 carbon atoms.

[0430] Specific examples of "aryl" include monocyclic aryl phenyl, bicyclic aryl (2-, 3-, 4-) biphenylyl, condensed bicyclic aryl (1-, 2-) naphthyl, tricyclic aryl terphenylyl (m-terphenyl-2'-yl, m-terphenyl-4'-yl, m-terphenyl-5'-yl, o-terphenyl-3'-yl, o-terphenyl-4'-yl, p-terphenyl-2'-yl, m-terphenyl-2-yl, m-terphenyl-3-yl, m-terphenyl-4-yl, o-terphenyl-2-yl, o-terphenyl-3-yl, o-terphenyl-4-yl, p-terphenyl-2-yl, p-terphenyl-3-yl, p-terphenyl-4-yl), condensed tricyclic aryl Examples of the aryl include acenaphthylene-(1-,3-,4-,5-)yl, fluorene-(1-,2-,3-,4-,9-)yl, phenalene-(1-,2-)yl, (1-,2-,3-,4-,9-)phenanthryl, the tetracyclic aryl group is quaterphenylyl (5'-phenyl-m-terphenyl-2-yl, 5'-phenyl-m-terphenyl-3-yl, 5'-phenyl-m-terphenyl-4-yl, m-quaterphenylyl), the condensed tetracyclic aryl group is triphenylene-(1-,2-)yl, pyrene-(1-,2-,4-)yl, naphthacene-(1-,2-,5-)yl, the condensed pentacyclic aryl group is perylene-(1-,2-,3-)yl, pentacene-(1-,2-,5-,6-)yl, and the like.

[0431] Examples of the "heteroaryl" in "optionally substituted heteroaryl" include heteroaryl having 2 to 30 carbon atoms, preferably heteroaryl having 2 to 25 carbon atoms, more preferably heteroaryl having 2 to 20 carbon atoms, further preferably heteroaryl having 2 to 15 carbon atoms, and particularly preferably heteroaryl having 2 to 10 carbon atoms. Examples of the heteroaryl include heterocycles containing, as ring-constituting atoms other than carbon, 1 to 5 heteroatoms selected from oxygen, sulfur, and nitrogen.

[0432] Specific examples of heteroaryl include furyl, thienyl, pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, pyrazolyl, oxadiazolyl, furazanyl, thiadiazolyl, triazolyl, tetrazolyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, benzofuranyl, isobenzofuranyl, benzo[b]thienyl, indolyl, isoindolyl, 1H-indazolyl, benzimidazolyl, benzoxazolyl, benzothiazolyl, 1H-benzotriazolyl, quinolyl, isoquinolyl, cinnolyl, quinazolyl, quinoxalinyl, phthalazinyl, naphthyridinyl, purinyl, pteridinyl, carbazolyl, acridinyl, phenoxazinyl, phenothiazinyl, phenazinyl, phenoxathiinyl, thianthrenyl, and indolizinyl.

[0433] The above aryl and heteroaryl may be substituted, for example, by the above aryl or heteroaryl, respectively.

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

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

[0436] <Benzimidazole derivatives> The benzimidazole derivative is, for example, a compound represented by the following formula (ETM-11). [ka]

[0437] φ is an n-valent aryl ring (preferably an n-valent benzene ring, naphthalene ring, anthracene ring, fluorene ring, benzofluorene ring, phenalene ring, phenanthrene ring, or triphenylene ring), n is an integer from 1 to 4, and the "benzoimidazole-based substituent" is a substituent in which the pyridyl in the "pyridine-based substituent" in the formulae (ETM-2), (ETM-2-1), and (ETM-2-2) is replaced with benzimidazolyl, and at least one hydrogen in the benzimidazole derivative may be replaced with deuterium.

[0438] [ka]

[0439] R in the above benzimidazolyl 11 is hydrogen, alkyl having 1 to 24 carbon atoms, cycloalkyl having 3 to 12 carbon atoms, or aryl having 6 to 30 carbon atoms, and R in formula (ETM-2-1) and formula (ETM-2-2) 11 The explanation can be cited.

[0440] φ is preferably an anthracene ring or a fluorene ring. In this case, the structure can be as described in the formula (ETM-2-1) or the formula (ETM-2-2). R 11 ~R 18 The explanation for formula (ETM-2-1) or formula (ETM-2-2) can be cited. In addition, in formula (ETM-2-1) or formula (ETM-2-2), the two pyridine-based substituents are explained as being bonded, but when these are replaced with benzimidazole-based substituents, both pyridine-based substituents may be replaced with benzimidazole-based substituents (i.e., n=2), or one of the pyridine-based substituents may be replaced with a benzimidazole-based substituent and the other pyridine-based substituent may be replaced with R 11 ~R 18 (i.e., n=1). Furthermore, for example, R in formula (ETM-2-1) 11 ~R 18At least one of the above is replaced with a benzimidazole-based substituent to form a "pyridine-based substituent" R 11 ~R 18 may be substituted.

[0441] Specific examples of the benzimidazole derivative include 1-phenyl-2-(4-(10-phenylanthracen-9-yl)phenyl)-1H-benzo[d]imidazole, 2-(4-(10-(naphthalen-2-yl)anthracen-9-yl)phenyl)-1-phenyl-1H-benzo[d]imidazole, 2-(3-(10-(naphthalen-2-yl)anthracen-9-yl)phenyl)-1-phenyl-1H-benzo[d]imidazole, and 5-(10-(naphthalen-2-yl)anthracen-9-yl)-1,2-diphenyl-1H-benzo[d]imidazole. , 1-(4-(10-(naphthalene-2-yl)anthracen-9-yl)phenyl)-2-phenyl-1H-benzo[d]imidazole, 2-(4-(9,10-di(naphthalene-2-yl)anthracen-2-yl)phenyl)-1-phenyl-1H-benzo[d]imidazole, 1-(4-(9,10-di(naphthalene-2-yl)anthracen-2-yl)phenyl)-2-phenyl-1H-benzo[d]imidazole, 5-(9,10-di(naphthalene-2-yl)anthracen-2-yl)-1,2-diphenyl-1H-benzo[d]imidazole, and the like.

[0442] [ka]

[0443] The benzimidazole derivative can be produced using known raw materials and known synthesis methods.

[0444] <Phenanthroline derivatives> The phenanthroline derivative is, for example, a compound represented by the following formula (ETM-12) or formula (ETM-12-1), the details of which are described in WO 2006 / 021982. [ka]

[0445] φ is an n-valent aryl ring (preferably an n-valent benzene ring, naphthalene ring, anthracene ring, fluorene ring, benzofluorene ring, phenalene ring, phenanthrene ring or triphenylene ring), and n is an integer of 1 to 4.

[0446] R of each formula 11 ~R 18 are each independently hydrogen, alkyl (preferably alkyl having 1 to 24 carbon atoms), cycloalkyl (preferably cycloalkyl having 3 to 12 carbon atoms), or aryl (preferably aryl having 6 to 30 carbon atoms). 11 ~R 18 Either one of these bonds becomes a bond to the aryl ring φ.

[0447] At least one hydrogen atom in each of the phenanthroline derivatives may be replaced with deuterium.

[0448] R 11 ~R 18 As the alkyl, cycloalkyl and aryl in the formula (ETM-2), R 11 ~R 18 can be cited. In addition to the above examples, φ can have the following structural formula. In the structural formula, R is independently hydrogen, methyl, ethyl, isopropyl, cyclohexyl, phenyl, 1-naphthyl, 2-naphthyl, biphenylyl, or terphenylyl, and * indicates a bonding position.

[0449] [ka]

[0450] Specific examples of the phenanthroline derivative include 4,7-diphenyl-1,10-phenanthroline, 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline, 9,10-di(1,10-phenanthroline-2-yl)anthracene, 2,6-di(1,10-phenanthroline-5-yl)pyridine, 1,3,5-tri(1,10-phenanthroline-5-yl)benzene, 9,9'-difluoro-bi(1,10-phenanthroline-5-yl), bathocuproine, 1,3-bis(2-phenyl-1,10-phenanthroline-9-yl)benzene, and compounds represented by the following structural formula. [ka]

[0451] The phenanthroline derivative can be produced using known raw materials and known synthesis methods.

[0452] <Quinolinol metal complexes> The quinolinol metal complex is, for example, a compound represented by the following formula (ETM-13). [ka] In the formula, R 1 ~R 6 are each independently hydrogen, fluorine, alkyl, cycloalkyl, aralkyl, alkenyl, cyano, alkoxy, or aryl; M is Li, Al, Ga, Be, or Zn; and n is an integer of 1 to 3.

[0453] Specific examples of quinolinol-based metal complexes include 8-quinolinol lithium, tris(8-quinolinolato)aluminum, tris(4-methyl-8-quinolinolato)aluminum, tris(5-methyl-8-quinolinolato)aluminum, tris(3,4-dimethyl-8-quinolinolato)aluminum, tris(4,5-dimethyl-8-quinolinolato)aluminum, tris(4,6-dimethyl-8-quinolinolato)aluminum, bis(2-methyl-8-quinolinolato)(phenolate)aluminum, bis(2-methyl-8-quinolinolato)(phenolate), and bis(2-methyl-8-quinolinolato). Bis(2-methylphenolate)aluminum, bis(2-methyl-8-quinolinate)(3-methylphenolate)aluminum, bis(2-methyl-8-quinolinate)(4-methylphenolate)aluminum, bis(2-methyl-8-quinolinate)(2-phenylphenolate)aluminum, bis(2-methyl-8-quinolinate)(3-phenylphenolate)aluminum, bis(2-methyl-8-quinolinate)(4-phenylphenolate)aluminum, bis(2-methyl-8-quinolinate)(2,3 -dimethylphenolate)aluminum, bis(2-methyl-8-quinolinate)(2,6-dimethylphenolate)aluminum, bis(2-methyl-8-quinolinate)(3,4-dimethylphenolate)aluminum, bis(2-methyl-8-quinolinate)(3,5-dimethylphenolate)aluminum, bis(2-methyl-8-quinolinate)(3,5-di-t-butylphenolate)aluminum, bis(2-methyl-8-quinolinate)(2,6-diphenylphenolate)aluminum, bis(2-methyl-8-quinolinate)(3,5-di-t-butylphenolate)aluminum linolate)(2,4,6-triphenylphenolate)aluminum, bis(2-methyl-8-quinolinolate)(2,4,6-trimethylphenolate)aluminum, bis(2-methyl-8-quinolinolate)(2,4,5,6-tetramethylphenolate)aluminum, bis(2-methyl-8-quinolinolate)(1-naphtholate)aluminum, bis(2-methyl-8-quinolinolate)(2-naphtholate)aluminum, bis(2,4-dimethyl-8-quinolinolate)(2-phenylphenolate)aluminum, bis(2,4-Dimethyl-8-quinolinolate)(3-phenylphenolate)aluminum, bis(2,4-dimethyl-8-quinolinolate)(4-phenylphenolate)aluminum, bis(2,4-dimethyl-8-quinolinolate)(3,5-dimethylphenolate)aluminum, bis(2,4-dimethyl-8-quinolinolate)(3,5-di-t-butylphenolate)aluminum, bis(2-methyl-8-quinolinolate)aluminum-μ-oxo-bis(2-methyl-8-quinolinolate)aluminum, bis(2,4-dimethyl-8-quinolinolate)aluminum-μ-oxo-bis(2,4-dimethyl-8-quinolinolate)aluminum, bis(2-methyl-4-ethyl-8- quinolinolate)aluminum-μ-oxo-bis(2-methyl-4-ethyl-8-quinolinolate)aluminum, bis(2-methyl-4-methoxy-8-quinolinolate)aluminum-μ-oxo-bis(2-methyl-4-methoxy-8-quinolinolate)aluminum, bis(2-methyl-5-cyano-8-quinolinolate)aluminum-μ-oxo-bis(2-methyl-5-cyano-8-quinolinolate)aluminum, bis(2-methyl-5-trifluoromethyl-8-quinolinolate)aluminum-μ-oxo-bis(2-methyl-5-trifluoromethyl-8-quinolinolate)aluminum, bis(10-hydroxybenzo[h]quinoline)beryllium, etc.

[0454] The quinolinol metal complex can be produced using known raw materials and known synthesis methods.

[0455] <Thiazole derivatives and benzothiazole derivatives> The thiazole derivative is, for example, a compound represented by the following formula (ETM-14-1). [ka] The benzothiazole derivative is, for example, a compound represented by the following formula (ETM-14-2). [ka]

[0456] In each formula, φ is an n-valent aryl ring (preferably an n-valent benzene ring, naphthalene ring, anthracene ring, fluorene ring, benzofluorene ring, phenalene ring, phenanthrene ring, or triphenylene ring), and n is an integer from 1 to 4. A "thiazole-based substituent" or a "benzothiazole-based substituent" is a substituent in which the pyridyl in the "pyridine-based substituent" in the formulae (ETM-2), (ETM-2-1), and (ETM-2-2) is replaced with the below-mentioned thiazolyl or benzothiazolyl, and at least one hydrogen in the thiazole derivative and the benzothiazole derivative may be replaced with a deuterium.

[0457] [ka]

[0458] φ is preferably an anthracene ring or a fluorene ring. In this case, the structure can be as described in the formula (ETM-2-1) or the formula (ETM-2-2). R 11 ~R 18 The explanation for formula (ETM-2-1) or formula (ETM-2-2) can be cited. In addition, in formula (ETM-2-1) or formula (ETM-2-2), two pyridine-based substituents are described as being bonded together, but when these are replaced with a thiazole-based substituent (or a benzothiazole-based substituent), both pyridine-based substituents may be replaced with a thiazole-based substituent (or a benzothiazole-based substituent) (i.e., n=2), or one of the pyridine-based substituents may be replaced with a thiazole-based substituent (or a benzothiazole-based substituent) and the other pyridine-based substituent may be replaced with R 11 ~R 18 (i.e., n=1). Furthermore, for example, R in formula (ETM-2-1) 11 ~R 18 At least one of the substituents is replaced with a thiazole-based substituent (or a benzothiazole-based substituent) to form a "pyridine-based substituent" R 11 ~R 18 may be substituted.

[0459] These thiazole or benzothiazole derivatives can be produced using known raw materials and known synthesis methods.

[0460] <Silole derivatives> The silole derivative is, for example, a compound represented by the following formula (ETM-15), the details of which are described in JP-A-9-194487. [ka]

[0461] X and Y are each independently alkyl, cycloalkyl, alkenyl, alkynyl, alkoxy, alkenyloxy, alkynyloxy, aryl, or heteroaryl, which may be substituted. For details of these groups, the explanations in formula (1A) and formula (1B) and further the explanation in formula (ETM-7-2) can be cited. In addition, alkenyloxy and alkynyloxy are groups in which the alkyl portion of alkoxy is replaced with alkenyl or alkynyl, respectively, and for details of these alkenyls and alkynyls, the explanations in formula (ETM-7-2) can be cited. Furthermore, X and Y, both of which are alkyl, may be bonded to form a ring.

[0462] R 1 ~R 4are each independently hydrogen, halogen, alkyl, cycloalkyl, alkoxy, aryloxy, amino, alkylcarbonyl, arylcarbonyl, alkoxycarbonyl, aryloxycarbonyl, azo group, alkylcarbonyloxy, arylcarbonyloxy, alkoxycarbonyloxy, aryloxycarbonyloxy, sulfinyl, sulfonyl, sulfanyl, silyl, carbamoyl, aryl, heteroaryl, alkenyl, alkynyl, nitro, formyl, nitroso, formyloxy, isocyano, cyanate group, isocyanate group, thiocyanate group, isothiocyanate group, or cyano, which may be substituted with alkyl, cycloalkyl, aryl or halogen, and may form a condensed ring with an adjacent substituent.

[0463] R 1 ~R 4 For details of halogen, alkyl, cycloalkyl, alkoxy, aryloxy, amino, aryl, heteroaryl, alkenyl and alkynyl in, the descriptions in formula (1A) and formula (1B) can be referred to.

[0464] R 1 ~R 4 For details of the alkyl, aryl and alkoxy in the alkylcarbonyl, arylcarbonyl, alkoxycarbonyl, aryloxycarbonyl, alkylcarbonyloxy, arylcarbonyloxy, alkoxycarbonyloxy and aryloxycarbonyloxy in the above, the explanations in the formula (1A) and the formula (1B) can be cited.

[0465] Examples of silyl include a silyl group and a group in which at least one of the three hydrogen atoms of the silyl group is independently substituted with an aryl, an alkyl, or a cycloalkyl, and tri-substituted silyl is preferable, such as triarylsilyl, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, and alkyldicycloalkylsilyl. For details of the aryl, alkyl, and cycloalkyl in these, the explanations in formula (1A) and formula (1B) can be cited.

[0466] The condensed ring formed between adjacent substituents is, for example, R 1 and R 2 , R 2 and R 3 , R 3 and R 4 etc. These fused rings may contain nitrogen, oxygen, or sulfur atoms in the ring structure, and may be fused with another ring.

[0467] However, preferably, R 1 and R 4 is phenyl, X and Y are not alkyl or phenyl. 1 and R 4 When R is a thienyl group, X and Y are alkyl groups, R 2 and R 3 is alkyl, aryl, alkenyl or R 2 and R 3 In addition, it is preferable that R 1 and R 4 When is a silyl group, R 2 , R 3 , X and Y are not each independently hydrogen or alkyl having 1 to 6 carbon atoms. 1 and R 2 In the case of a structure in which a benzene ring is condensed, X and Y are not alkyl and phenyl.

[0468] These silole derivatives can be produced using known raw materials and known synthesis methods.

[0469] <Azoline derivatives> The azoline derivative is, for example, a compound represented by the following formula (ETM-16), details of which are described in International Publication No. 2017 / 014226. [ka]

[0470] In formula (ETM-16), φ is an m-valent group derived from an aromatic hydrocarbon having 6 to 40 carbon atoms or an m-valent group derived from an aromatic heterocycle having 2 to 40 carbon atoms, and at least one hydrogen of φ is optionally substituted by alkyl having 1 to 6 carbon atoms, cycloalkyl having 3 to 14 carbon atoms, aryl having 6 to 18 carbon atoms, or heteroaryl having 2 to 18 carbon atoms; Y's are each independently -O-, -S- or >N-Ar, Ar is an aryl having 6 to 12 carbon atoms or a heteroaryl having 2 to 12 carbon atoms, at least one hydrogen of Ar may be substituted by an alkyl having 1 to 4 carbon atoms, a cycloalkyl having 5 to 10 carbon atoms, an aryl having 6 to 12 carbon atoms or a heteroaryl having 2 to 12 carbon atoms, R 1 ~R 5 are each independently hydrogen, alkyl having 1 to 4 carbon atoms, or cycloalkyl having 5 to 10 carbon atoms, provided that Ar in the >N-Ar and R 1 ~R 5 one of which is a site for binding to L; Each L is independently selected from the group consisting of a divalent group represented by the following formula (L-1) and a divalent group represented by the following formula (L-2): [ka]

[0471] In formula (L-1), X 1 ~X 6 are each independently =CR 6- or =N- and X 1 ~X 6 At least two of the =CR 6 - and X 1 ~X 6 Two of =CR 6 -R in 6 is the site of binding to φ or the azoline ring, and the other =CR 6 -R in 6 is hydrogen, In formula (L-2), X 7 ~X 14 are each independently =CR 6 - or =N- and X 7 ~X 14 At least two of the =CR 6 - and X 7 ~X 14 Two of =CR 6 -R in 6 is the site of binding to φ or the azoline ring, and the other =CR 6 -R in 6 is hydrogen, at least one hydrogen atom of L may be substituted with alkyl having 1 to 4 carbon atoms, cycloalkyl having 5 to 10 carbon atoms, aryl having 6 to 10 carbon atoms, or heteroaryl having 2 to 10 carbon atoms; m is an integer of 1 to 4, and when m is an integer of 2 to 4, the groups formed by the azoline ring and L may be the same or different, and At least one hydrogen atom in the compound represented by formula (ETM-16) may be substituted with deuterium.

[0472] Specific azoline derivatives are compounds represented by the following formula (ETM-16-1) or formula (ETM-16-2). [ka]

[0473] In formula (ETM-16-1) and formula (ETM-16-2), φ is an m-valent group derived from an aromatic hydrocarbon having 6 to 40 carbon atoms or an m-valent group derived from an aromatic heterocycle having 2 to 40 carbon atoms, and at least one hydrogen of φ is optionally substituted by alkyl having 1 to 6 carbon atoms, cycloalkyl having 3 to 14 carbon atoms, aryl having 6 to 18 carbon atoms, or heteroaryl having 2 to 18 carbon atoms; In formula (ETM-16-1), each Y is independently -O-, -S- or >N-Ar, Ar is an aryl having 6 to 12 carbon atoms or a heteroaryl having 2 to 12 carbon atoms, and at least one hydrogen of Ar is optionally substituted by an alkyl having 1 to 4 carbon atoms, a cycloalkyl having 5 to 10 carbon atoms, an aryl having 6 to 12 carbon atoms, or a heteroaryl having 2 to 12 carbon atoms; In formula (ETM-16-1), R 1 ~R 4 are each independently hydrogen, alkyl having 1 to 4 carbon atoms, or cycloalkyl having 5 to 10 carbon atoms, with the proviso that R 1 and R 2 are identical, and R 3 and R 4 are identical, In formula (ETM-16-2), R 1 ~R 5 are each independently hydrogen, alkyl having 1 to 4 carbon atoms, or cycloalkyl having 5 to 10 carbon atoms, with the proviso that R 1 and R 2 are identical, and R 3 and R 4 are identical, In formula (ETM-16-1) and formula (ETM-16-2), Each L is independently selected from the group consisting of a divalent group represented by the following formula (L-1) and a divalent group represented by the following formula (L-2):

[0474] [ka] In formula (L-1), X 1 ~X 6 are each independently =CR 6 - or =N- and X 1 ~X 6 At least two of the =CR6 - and X 1 ~X 6 Two of =CR 6 -R in 6 is the site of binding to φ or the azoline ring, and the other =CR 6 -R in 6 is hydrogen, In formula (L-2), X 7 ~X 14 are each independently =CR 6 - or =N- and X 7 ~X 14 At least two of the =CR 6 - and X 7 ~X 14 Two of =CR 6 -R in 6 is the site of binding to φ or the azoline ring, and the other =CR 6 -R in 6 is hydrogen, at least one hydrogen atom of L may be substituted with alkyl having 1 to 4 carbon atoms, cycloalkyl having 5 to 10 carbon atoms, aryl having 6 to 10 carbon atoms, or heteroaryl having 2 to 10 carbon atoms; m is an integer of 1 to 4, and when m is an integer of 2 to 4, the groups formed by the azoline ring and L may be the same or different, and At least one hydrogen atom in the compound represented by formula (ETM-16-1) or formula (ETM-16-2) may be replaced with deuterium.

[0475] Preferably, φ is selected from the group consisting of monovalent groups represented by the following formulas (φ1-1) to (φ1-18), divalent groups represented by the following formulas (φ2-1) to (φ2-34), trivalent groups represented by the following formulas (φ3-1) to (φ3-3), and tetravalent groups represented by the following formulas (φ4-1) to (φ4-2), and at least one hydrogen of φ may be substituted by alkyl having 1 to 6 carbon atoms, cycloalkyl having 3 to 14 carbon atoms, aryl having 6 to 18 carbon atoms, or heteroaryl having 2 to 18 carbon atoms.

[0476] [ka]

[0477] [ka] [ka]

[0478] In the formula, Z is >CR2, >N-Ar, >NL, -O- or -S-, R in >CR2 is each independently an alkyl having 1 to 4 carbon atoms, a cycloalkyl having 5 to 10 carbon atoms, an aryl having 6 to 12 carbon atoms or a heteroaryl having 2 to 12 carbon atoms, and R may be bonded to each other to form a ring, Ar in >N-Ar is an aryl having 6 to 12 carbon atoms or a heteroaryl having 2 to 12 carbon atoms, and L in >NL is L in formula (ETM-16), formula (ETM-16-1) or formula (ETM-16-2). * in the formula indicates a bonding position.

[0479] Preferably, L is a divalent ring group selected from the group consisting of benzene, naphthalene, pyridine, pyrazine, pyrimidine, pyridazine, triazine, quinoline, isoquinoline, naphthyridine, phthalazine, quinoxaline, quinazoline, cinnoline, and pteridine, and at least one hydrogen of L may be substituted with an alkyl group having 1 to 4 carbon atoms, a cycloalkyl group having 5 to 10 carbon atoms, an aryl group having 6 to 10 carbon atoms, or a heteroaryl group having 2 to 10 carbon atoms.

[0480] Preferably, Ar in >N-Ar as Y or Z is selected from the group consisting of phenyl, naphthyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, naphthyridinyl, phthalazinyl, quinoxalinyl, quinazolinyl, cinnolinyl, and pteridinyl, and at least one hydrogen of Ar in >N-Ar as Y may be substituted with alkyl having 1 to 4 carbon atoms, cycloalkyl having 5 to 10 carbon atoms, or aryl having 6 to 10 carbon atoms.

[0481] Preferably, R 1 ~R 4 are each independently hydrogen, alkyl having 1 to 4 carbon atoms, or cycloalkyl having 5 to 10 carbon atoms, with the proviso that R 1 and R 2 are identical, and R 3 and R 4 are identical, and R 1 ~R 4 are not all hydrogen at the same time, and m is 1 or 2. When m is 2, the groups formed by the azoline ring and L are the same.

[0482] Specific examples of azoline derivatives include the following compounds: In the structural formula, "Me" represents methyl. [ka]

[0483] More preferably, φ is selected from the group consisting of divalent groups represented by the following formulas (φ2-1), (φ2-31), (φ2-32), (φ2-33) and (φ2-34), and at least one hydrogen of φ may be substituted by an aryl having 6 to 18 carbon atoms.

[0484] [ka]

[0485] L is a divalent ring group selected from the group consisting of benzene, pyridine, pyrazine, pyrimidine, pyridazine, and triazine, and at least one hydrogen of L is optionally substituted by alkyl having 1 to 4 carbon atoms, cycloalkyl having 5 to 10 carbon atoms, aryl having 6 to 10 carbon atoms, or heteroaryl having 2 to 14 carbon atoms; Ar in >N-Ar as Y is selected from the group consisting of phenyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, and triazinyl, and at least one hydrogen of the Ar may be substituted by alkyl having 1 to 4 carbon atoms, cycloalkyl having 5 to 10 carbon atoms, or aryl having 6 to 10 carbon atoms; R 1 ~R 4 are each independently hydrogen, alkyl having 1 to 4 carbon atoms, or cycloalkyl having 5 to 10 carbon atoms, with the proviso that R 1 and R 2 are identical, and R 3 and R 4 are identical, and R 1 ~R 4 cannot all become hydrogen at the same time, and m is 2, and the groups formed by the azoline ring and L are the same.

[0486] Other specific examples of azoline derivatives include the following compounds: In the structural formula, "Me" represents methyl. [ka]

[0487] For details of alkyl, cycloalkyl, aryl or heteroaryl in the above formulas defining this azoline derivative, the explanations in formula (1A) and formula (1B) can be referred to.

[0488] The azoline derivative can be produced using known raw materials and known synthesis methods.

[0489] <Reducing substances> The electron transport layer or the electron injection layer may further contain a substance capable of reducing the material forming the electron transport layer or the electron injection layer. As the reducing substance, various substances can be used as long as they have a certain degree of reducing ability, and for example, at least one selected from the group consisting of alkali metals, alkaline earth metals, rare earth metals, oxides of alkali metals, halides of alkali metals, oxides of alkaline earth metals, halides of alkaline earth metals, oxides of rare earth metals, halides of rare earth metals, organic complexes of alkali metals, organic complexes of alkaline earth metals, and organic complexes of rare earth metals can be suitably used.

[0490] 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.

[0491] The above-mentioned electron injection layer material and electron transport layer material can be used as an electron layer material as a polymer compound obtained by polymerizing a reactive compound substituted with a reactive substituent as a monomer, or as a crosslinked polymer thereof, or as a pendant polymer compound obtained by reacting a main chain polymer with the reactive compound, or as a crosslinked pendant polymer thereof. In this case, the reactive substituent can be quoted from the explanation of the polycyclic aromatic compound consisting of a partial structure represented by formula (1A) and at least one partial structure represented by formula (1B). The applications of such polymer compounds and crosslinked polymers will be described in detail below.

[0492] 3-1-7. Cathode in organic electroluminescent device The cathode 108 serves to inject electrons into the light-emitting layer 105 through the electron injection layer 107 and the electron transport layer 106 .

[0493] 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.

[0494] 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.

[0495] 3-1-8. Binders that may be used in each layer The materials used for the hole injection layer, hole transport layer, light emitting layer, electron transport layer and electron injection layer can form each layer alone, but they can also be used as a polymer binder by being dispersed in a solvent-soluble resin such as polyvinyl chloride, polycarbonate, polystyrene, poly(N-vinylcarbazole), polymethyl methacrylate, polybutyl methacrylate, polyester, polysulfone, polyphenylene oxide, polybutadiene, hydrocarbon resin, ketone resin, phenoxy resin, polyamide, ethyl cellulose, vinyl acetate resin, ABS resin, polyurethane resin, or a curable resin such as phenol resin, xylene resin, petroleum resin, urea resin, melamine resin, unsaturated polyester resin, alkyd resin, epoxy resin, silicone resin, or the like.

[0496] 3-1-9. Method for producing organic electroluminescent device Each layer constituting an organic EL element can be formed by forming the material to be formed into a thin film by a method such as vapor deposition, resistance heating vapor deposition, electron beam vapor deposition, sputtering, molecular lamination, printing, spin coating or casting, coating, etc. The thickness of each layer thus formed is not particularly limited and can be set appropriately according to the properties of the material, but is usually in the range of 2 nm to 5000 nm. The thickness of the film can usually be measured with a quartz crystal oscillation type film thickness measuring device, etc. When forming a thin film by vapor deposition, the vapor deposition conditions vary depending on the type of material, the desired crystal structure and association structure of the film, etc. The vapor deposition conditions are generally a boat heating temperature of +50 to +400°C, a vacuum degree of 10, and a vacuum of 10. -6 ~10-3 It is preferable to appropriately set the pressure, pressure Pa, deposition rate 0.01 to 50 nm / sec, substrate temperature -150 to +300°C, and film thickness 2 nm to 5 µm.

[0497] 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.

[0498] 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.

[0499] <Vapor deposition method> A thin film of an anode material is formed on a suitable substrate by vapor deposition or the like to prepare an anode, and then a thin film of a hole injection layer and a hole transport layer is formed on the anode. A host material and a dopant material are co-deposited on the anode to form a thin film as a light-emitting layer, an electron transport layer and an electron injection layer are formed on the light-emitting layer, and a thin film of a cathode material is further formed by vapor deposition or the like to prepare a cathode, thereby obtaining a desired organic EL device. Note that in the preparation of the above-mentioned organic EL device, the preparation order can also be reversed, and the layers can be prepared in the order of cathode, electron injection layer, electron transport layer, light-emitting layer, hole transport layer, hole injection layer, and anode.

[0500] <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.

[0501] 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 is called a spray method.

[0502] As an example, a method of forming a coating film on a substrate having banks using an inkjet method will be described with reference to FIG. 2. First, banks (200) are provided on electrodes (120) on a substrate (110). In this case, ink droplets (310) are dropped between the banks (200) from an inkjet head (300) and dried to produce a coating film (130). This process is repeated to produce the next coating film (140) and then the light-emitting layer (150), and an electron transport layer, an electron injection layer, and electrodes are formed using a vacuum deposition method, making it possible to produce an organic EL element in which the light-emitting site is separated by the bank material.

[0503] The drying process may be carried out by air drying, heating, drying under reduced pressure, etc. The drying process may be carried out once or may be carried out multiple times using different methods and conditions. Also, different methods may be used in combination, such as calcination under reduced pressure.

[0504] 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.

[0505] 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.

[0506] 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.

[0507] 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.

[0508] <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.

[0509] <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.

[0510] 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.

[0511] Materials that can be used for banks include, but are not limited to, polysaccharides and their derivatives, homopolymers and copolymers of hydroxyl-containing ethylenic monomers, biopolymers, polyacryloyl compounds, polyesters, polystyrenes, polyimides, polyamideimides, polyetherimides, polysulfides, polysulfones, polyphenylenes, polyphenyl ethers, polyurethanes, epoxy (meth)acrylates, melamine (meth)acrylates, polyolefins, cyclic polyolefins, acrylonitrile-butadiene-styrene copolymers (ABS), silicone resins, polyvinyl chloride, chlorinated polyethylene, chlorinated polypropylene, polyacetate, polynorbornene, synthetic rubber, fluorinated polymers such as polyfluorovinylidene, polytetrafluoroethylene, and polyhexafluoropropylene, fluoroolefin-hydrocarbonolefin copolymers, and fluorocarbon polymers.

[0512] <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.

[0513] <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.

[0514] (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.

[0515] 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.

[0516] 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.

[0517] 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.

[0518] (2) Specific examples of organic solvents Examples of the organic solvent used in the composition for forming the organic layer include alkylbenzene solvents, phenyl ether solvents, alkyl ether solvents, cyclic ketone solvents, aliphatic ketone solvents, monocyclic ketone solvents, solvents having a diester skeleton, and fluorine-containing solvents. Specific examples include pentanol, hexanol, heptanol, octanol, nonanol, decanol, undecanol, dodecanol, tetradecanol, hexane-2-ol, heptan-2-ol, octan-2-ol, decan-2-ol, dodecan-2-ol, cyclohexanol, Sanol, α-terpineol, β-terpineol, γ-terpineol, δ-terpineol, terpineol (mixture), ethylene glycol monomethyl ether acetate, propylene glycol monomethyl ether acetate, diethylene glycol dimethyl ether, dipropylene glycol dimethyl ether, diethylene glycol ethyl methyl ether, diethylene glycol isopropyl methyl ether, dipropylene glycol monomethyl ether, diethylene glycol diethyl ether, diethylene glycol monomethyl ether , diethylene glycol butyl methyl ether, tripropylene glycol dimethyl ether, triethylene glycol dimethyl ether, diethylene glycol monobutyl ether, ethylene glycol monophenyl ether, triethylene glycol monomethyl ether, diethylene glycol dibutyl ether, triethylene glycol butyl methyl ether, polyethylene glycol dimethyl ether, tetraethylene glycol dimethyl ether, p-xylene, m-xylene, o-xylene, 2,6-lutidine, 2-fluoro-m-xylene, 3-fluoro-o-xylene, 2-chlorobenzotrifluoride, cumene, toluene, 2-chloro-6-fluorotoluene, 2-fluoroanisole, anisole, 2,3-dimethylpyrazine, bromobenzene, 4-fluoroanisole, 3-fluoroanisole, 3-trifluoromethylanisole, mesitylene, 1,2,4-trimethylbenzene, t-butylbenzene, 2-methylanisole, phenetole, benzodioxole, 4-methylanisole, s-butylbenzene, 3-methylanisole, 4-fluoro-3-methylanisole, cymene, 1,2,3-Trimethylbenzene, 1,2-Dichlorobenzene, 2-Fluorobenzonitrile, 4-Fluoroveratrol, 2,6-Dimethylanisole, n-Butylbenzene, 3-Fluorobenzonitrile, Decalin (Decahydronaphthalene), Neopentylbenzene, 2,5-Dimethylanisole, 2,4-Dimethylanisole, Benzonitrile, 3,5-Dimethylanisole, Diphenyl ether, 1-Fluoro-3,5-dimethoxybenzene, Methyl benzoate, Isopentylbenzene, 3,4-Dimethylanisole, o-Tolunitrile, n-Amylbenzene, Veratrol, 1,2,3,4-Tetrahydronaphthalene, Ethyl benzoate, n-Hexylbenzene, Propyl benzoate, Cyclohexylbenzene, 1- Examples of the solvent include, but are not limited to, methylnaphthalene, butyl benzoate, 2-methylbiphenyl, 3-phenoxytoluene, 2,2'-bitolyl, dodecylbenzene, dipentylbenzene, tetramethylbenzene, trimethoxybenzene, trimethoxytoluene, 2,3-dihydrobenzofuran, 1-methyl-4-(propoxymethyl)benzene, 1-methyl-4-(butyloxymethyl)benzene, 1-methyl-4-(pentyloxymethyl)benzene, 1-methyl-4-(hexyloxymethyl)benzene, 1-methyl-4-(heptyloxymethyl)benzene, benzyl butyl ether, benzyl pentyl ether, benzyl hexyl ether, benzyl heptyl ether, and benzyl octyl ether. The solvent may be used alone or in a mixture.

[0519] <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.

[0520] (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.

[0521] 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.

[0522] The binder used in the organic layer-forming composition may be of one type or a mixture of two or more types.

[0523] (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.

[0524] Examples of surfactants include Polyflow No. 45, Polyflow KL-245, Polyflow No. 75, Polyflow No. 90, Polyflow No. 95 (trade names, manufactured by Kyoeisha Chemical Industry Co., Ltd.), Disperbyk 161, Disperbyk 162, Disperbyk 163, Disperbyk 164, Disperbyk 166, Disperbyk 170, Disperbyk 180, Disperbyk 181, Disperbyk 182, BYK300, BYK 306, BYK310, BYK320, BYK330, BYK342, BYK344, BYK346 (trade name, manufactured by BYK Japan Co., Ltd.), KP-341, KP-358, KP-368, KF-96-50CS, KF-50-100CS (trade name, manufactured by Shin-Etsu Chemical Co., Ltd.), Surflon SC-101, Surflon KH-40 (trade name, manufactured by Seimi Chemical Co., Ltd.), Ftergent 222F, Ftergent 251, FTX-218 (trade name, manufactured by Neos Co., Ltd.), EFTOP EF-351, EFTOP EF-352, EFTOP EF-601, EFTOP EF-801, EFTOPEF-802 (product name, manufactured by Mitsubishi Materials Corporation), Megafac F-470, Megafac F-471, Megafac F-475, Megafac R-08, Megafac F-477, Megafac F-479, Megafac F-553, Megafac F-554 (product name, manufactured by DIC Corporation), fluoroalkylbenzenesulfonate, fluoroalkylcarboxylate, fluoroalkylpolyoxyethyleneether, fluoroalkylammonium iodide, fluoroalkylbetaine, fluoroalkylsulfonate, diglycerol tetrakis(fluoroalkylpolyoxyethyleneether), fluoroalkyltrimethylammonium salt, fluoroalkylaminosulfonate, polyoxyethylenenonyl Examples of the alkyl ethers include polyoxyethylene octylphenyl ether, polyoxyethylene alkyl ethers, polyoxyethylene laurate, polyoxyethylene oleate, polyoxyethylene stearate, polyoxyethylene laurylamine, sorbitan laurate, sorbitan palmitate, sorbitan stearate, sorbitan oleate, sorbitan fatty acid esters, polyoxyethylene sorbitan laurate, polyoxyethylene sorbitan palmitate, polyoxyethylene sorbitan stearate, polyoxyethylene sorbitan oleate, polyoxyethylene naphthyl ether, alkylbenzene sulfonates, and alkyldiphenyl ether disulfonates.

[0525] The surfactant may be used alone or in combination of two or more kinds.

[0526] <Composition and Properties of the Organic Layer-Forming Composition> The content of each component in the composition for forming an organic layer is determined in consideration of the good solubility, storage stability and film-forming property of each component in the composition for forming an organic layer, the good film quality of the coating film obtained from the composition for forming an organic layer, the good discharge property when using an inkjet method, and the good electrical properties, light-emitting properties, efficiency and life of an organic EL device having an organic layer produced using the composition. For example, in the case of a composition for forming an emitting layer, it is preferable that the first component is 0.0001% by mass to 2.0% by mass relative to the total mass of the composition for forming an emitting layer, the second component is 0.0999% by mass to 8.0% by mass relative to the total mass of the composition for forming an emitting layer, and the third component is 90.0% by mass to 99.9% by mass relative to the total mass of the composition for forming an emitting layer.

[0527] More preferably, the first component is 0.005% by mass to 1.0% by mass, the second component is 0.095% by mass to 4.0% by mass, and the third component is 95.0% by mass to 99.9% by mass, more preferably, the first component is 0.05% by mass to 0.5% by mass, the second component is 0.25% by mass to 2.5% by mass, and the third component is 97.0% by mass to 99.7% by mass, based on the total mass of the composition for forming the light-emitting layer.

[0528] 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.

[0529] 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).

[0530] 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.

[0531] <Crosslinkable polymer compound: Compound represented by formula (XLP-1)> Next, the case where the above-mentioned polymer compound has a crosslinkable substituent will be described. Such a crosslinkable polymer compound is, for example, a compound represented by the following formula (XLP-1).

[0532] [ka]

[0533] In formula (XLP-1), MUx, ECx, and k are defined the same as MU, EC, and k in formula (SPH-1), with the proviso 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 group having a crosslinkable substituent is 0.1 to 80 mass% in the molecule.

[0534] The content of the monovalent or divalent aromatic compound having a crosslinkable substituent is preferably from 0.5 to 50 mass %, more preferably from 1 to 20 mass %.

[0535] 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]

[0536] 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.

[0537] Examples of the divalent aromatic compound having a crosslinkable substituent include compounds having the following partial structures: [ka]

[0538] [ka]

[0539] [ka]

[0540] [ka]

[0541] <Methods of producing polymer compounds and crosslinkable polymer compounds> The manufacturing method of the polymer compound and the crosslinkable polymer compound will be described with reference to the compound represented by the above formula (SPH-1) and the compound represented by the above formula (XLP-1). These compounds can be synthesized by appropriately combining known manufacturing methods.

[0542] 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.

[0543] 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.

[0544] The compound of formula (SPH-1) and the compound of formula (XLP-1) may be produced in one step or in multiple steps. The compound may be produced by a batch polymerization method in which all the raw materials are put into a reaction vessel and then the reaction is started, a dropwise polymerization method in which the raw materials are added dropwise to a reaction vessel, or a precipitation polymerization method in which the product precipitates as the reaction proceeds, and these methods can be combined appropriately to synthesize the compound. For example, when the compound of formula (SPH-1) is synthesized in one step, the target product is obtained by adding a monomer having a polymerizable group bonded to the monomer unit (MU) and a monomer having a polymerizable group bonded to the end cap unit (EC) to a reaction vessel and then reacting the monomer. When the compound of formula (SPH-1) is synthesized in multiple steps, the target product is obtained by polymerizing the monomer having a polymerizable group bonded to the monomer unit (MU) to the target molecular weight, and then adding and reacting the monomer having a polymerizable group bonded to the end cap unit (EC). By adding monomers with polymerizable groups to different types of monomer units (MU) in multiple stages and carrying out the reaction, it is possible to create a polymer with a concentration gradient in terms of the monomer unit structure. Also, after preparing a precursor polymer, the target polymer can be obtained by post-reaction.

[0545] In addition, the primary structure of the polymer can be controlled by selecting the polymerizable group of the monomer. For example, as shown in synthesis schemes 1 to 3, it is possible to synthesize a polymer having a random primary structure (synthetic scheme 1) or a polymer having a regular primary structure (synthetic schemes 2 and 3), and these can be used in appropriate combinations depending on the target object. Furthermore, if a monomer having three or more polymerizable groups is used, a hyperbranched polymer or a dendrimer can be synthesized.

[0546] [ka]

[0547] Monomers that can be used in the present invention include those described in JP2010-189630A, WO2012 / 086671A, WO2013 / 191088A, WO2002 / 045184A, WO2011 / 049241A, WO2013 / 146806A, WO2005 / 049546A, WO2015 / 1458 ...B, WO2015 / 1458B, WO2015 / 1458B, WO2015 / 1458B, WO2015 / 1458B, WO2015 / 1458B, WO2015 / 1458B, WO2015 / 1458B, W It can be synthesized in accordance with the methods described in JP-A-2002 / 045184, JP-A-2010-215886, JP-A-2008-106241, JP-A-2010-215886, WO 2016 / 031639, JP-A-2011-174062, WO 2016 / 031639, WO 2016 / 031639, and WO 2002 / 045184.

[0548] 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.

[0549] 3-1-10.Application examples 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.

[0550] Examples of the display device include panel displays such as color flat panel displays, and flexible displays such as flexible color organic electroluminescent (EL) displays (see, for example, JP-A-10-335066, JP-A-2003-321546, JP-A-2004-281086, etc.). Examples of the display system include a matrix and / or segment system. Note that matrix display and segment display may coexist in the same panel.

[0551] 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.

[0552] 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.

[0553] 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.

[0554] 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.

[0555] 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.

[0556] 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.

[0557] The organic thin-film solar cell has a structure in which an anode such as ITO, a hole transport layer, a photoelectric conversion layer, an electron transport layer, and a cathode are laminated on a transparent substrate such as glass. The photoelectric conversion layer has a p-type semiconductor layer on the anode side and an n-type semiconductor layer on the cathode side. The polycyclic aromatic compound according to the present invention can be used as a material for a hole transport layer, a p-type semiconductor layer, an n-type semiconductor layer, and an electron transport layer depending on its physical properties. The polycyclic aromatic compound according to the present invention can function as a hole transport material or an electron transport material in an organic thin-film solar cell. In addition to the above, the organic thin-film solar cell may appropriately include a hole blocking layer, an electron blocking layer, an electron injection layer, a hole injection layer, a smoothing layer, and the like. The organic thin-film solar cell can be used by appropriately selecting and combining known materials used in organic thin-film solar cells. EXAMPLES

[0558] 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.

[0559] Synthesis example (1): Compound (1-161) [ka]

[0560] 3.24g (2.5mmol) of compound (Int-1-161) was placed in a reaction vessel, and after replacing with nitrogen, 20mL of 1,2-dichlorobenzene was added. 3.13g of boron tribromide (BBr3) was added dropwise from a dropping funnel, and refluxed at 145℃ for 4.5 hours. The reaction was stopped with an aqueous sodium acetate solution, and extracted with dichloromethane. The residue obtained by distilling off the solvent was purified by silica gel short column chromatography (eluent: toluene). Compound (1-161) was obtained by heating and refluxing with heptane (1.02g, 31% yield). The target compound (1-161) was confirmed to be present at m / z=1311.73 by LC-MS. [ka]

[0561] Synthesis example (2): Compound (1-180) [ka]

[0562] In a reaction vessel, 2.98 g (2.5 mmol) of compound (Int-1-180) was placed, and the atmosphere was replaced with nitrogen, followed by the addition of 20 mL of 1,2-dichlorobenzene. 3.13 g of boron tribromide (BBr3) was added dropwise from a dropping funnel, and the mixture was refluxed at 145°C for 12 hours. The reaction was stopped with an aqueous solution of sodium acetate, and the mixture was extracted with dichloromethane. The residue obtained by distilling off the solvent was purified by silica gel short column chromatography (eluent: toluene / heptane = 1 / 1 (volume ratio)). Compound (1-180) was obtained by heating and refluxing the mixture with heptane (0.75 g, yield 25%). The target compound (1-180) was confirmed to have an m / z value of 1207.65 by LC-MS. [ka]

[0563] Synthesis example (3): Compound (1-256) [ka]

[0564] Compound (Int-1-256) 2.56g (2.5mmol) was placed in a reaction vessel, and after replacing with nitrogen, 1,2-dichlorobenzene 20mL was added. Boron tribromide (BBr3) 3.13g was added dropwise from a dropping funnel, and refluxed at 145℃ for 14 hours. The reaction was stopped with an aqueous sodium acetate solution, and extracted with dichloromethane. The residue obtained by distilling off the solvent was purified by silica gel short column chromatography (eluent: toluene). Compound (1-256) was obtained by heating and refluxing washing with heptane (0.38g, 14% yield). The target compound (1-256) was confirmed to exist at m / z=1076.61 by LC-MS. [ka]

[0565] 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.

[0566] (1) Preparation and evaluation of evaporated organic electroluminescence devices Organic EL devices according to the examples and comparative examples are fabricated, and voltage is applied to measure current density, luminance, chromaticity, external quantum efficiency, etc. As the configurations of the fabricated organic EL devices, the following configuration A (Table 1) and configuration B (Table 2) are selected and evaluated. However, application of the compound of the present invention is not limited to these configurations, 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.

[0567] <<Element configuration and evaluation of configuration A>> [Table 1]

[0568] In Table 1, "NPD" is N,N'-diphenyl-N,N'-dinaphthyl-4,4'-diaminobiphenyl; "TcTa" is 4,4',4"-tris(N-carbazolyl)triphenylamine; "mCP" is 1,3-bis(N-carbazolyl)benzene; "2CzBN" is 3,4-dicarbazolylbenzonitrile "BPy-TP2" is 2,7-di([2,2'-bipyridine]-5-yl)triphenylene. The chemical structures of "BH-1", "RBD-1", "RBD-2" and "RBD-3" are shown below.

[0569] [ka]

[0570] <Example 1> <Configuration A: Device using compound (1-161) as a dopant> 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 a substrate holder of a commercially available deposition apparatus (manufactured by Showa Vacuum Co., Ltd.), and a molybdenum deposition boat containing NPD, TcTa, mCP, BH-1, compound (1-161), 2CzBN, and BPy-TP2, and a tungsten deposition boat containing LiF and aluminum were attached.

[0571] The following layers were formed in order on the ITO film of the transparent support substrate. -4 The 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 to form a hole transport layer. Next, mCP was heated and evaporated to a thickness of 15 nm to form an electron blocking layer. Next, BH-1 and compound (1-161) were heated simultaneously and evaporated to a thickness of 20 nm to form an emitting layer. The evaporation rate was adjusted so that the weight ratio of BH-1 to compound (1-161) was approximately 99:1. Next, 2CzBN was heated and evaporated to a thickness of 10 nm, and then BPy-TP2 was heated and evaporated to a thickness of 20 nm to form an electron transport layer consisting of two layers. 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.

[0572] <Examples 2 and 3, Comparative Examples 1 to 3> The compound (1-161) used as the dopant in Example 1 was changed to a dopant shown in Table 1 to prepare a device.

[0573] <Evaluation> The fabricated element was subjected to DC voltage with the ITO electrode as the anode and the aluminum electrode as the cathode, and the brightness was 500 cd / m 2 The emission wavelength, half-width, driving voltage, current density, external quantum efficiency (EQE), and LT50 (initial luminance 500 cd / m 2 When continuously driven at a current density of 250 cd / m 2 The evaluation results are shown in Table 1.

[0574] <<Element configuration and evaluation of configuration B>> [Table 2]

[0575] In Table 2, "HI-1" is N 4 ,N 4' -Diphenyl-N 4 ,N 4' -bis(9-phenyl-9H-carbazol-3-yl)-[1,1'-biphenyl]-4,4'-diamine, "HAT-CN" is 1,4,5,8,9,12-hexaazatriphenylene hexacarbonitrile, "HT-1" is N-([1,1'-biphenyl]-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluoren-2-amine, and "HT-2" is N,N-bis(4-(dibenzo[b,d]furan-4-yl)phenyl)-[1,1':4',1"-terphenyl]-4-amine; "BH-2" is 9-phenyl-10-(4-phenylnaphthalen-1-yl)anthracene; "BH-3" is 2-(10-phenylanthracen-9-yl)dibenzo[b,d]furan "ET-1" is 4,6,8,10-tetraphenyl[1,4]benzoxaborinino[2,3,4-kl]phenoxaborinine; "ET-2" is 3,3'-((2-phenylanthracene-9,10-diyl)bis(4,1-phenylene))bis(4-methylpyridine); The chemical structure is shown below along with "Liq."

[0576] [ka]

[0577] <Example 4> <Configuration B: Element using compound (1-256) as a dopant> 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 a substrate holder of a commercially available deposition apparatus (manufactured by Showa Vacuum Co., Ltd.), and a molybdenum deposition boat containing HI-1, HAT-CN, HT-1, HT-2, BH-2, compound (1-256), ET-1, ET-2, and Liq, and a tungsten deposition boat containing LiF and aluminum were attached.

[0578] The following layers were formed in order on the ITO film of the transparent support substrate. -4The pressure was reduced to 10 Pa, and HI-1 was heated and evaporated to a thickness of 40 nm, and HAT-CN was heated and evaporated to a thickness of 5 nm to form a two-layer hole injection layer. HT-1 was then heated and evaporated to a thickness of 15 nm, and HT-2 was then heated and evaporated to a thickness of 10 nm to form a two-layer hole transport layer. BH-2 and compound (1-256) were then simultaneously heated and evaporated to a thickness of 25 nm to form a light-emitting layer. The evaporation rate was adjusted so that the weight ratio of BH-2 to compound (1-256) was approximately 99:1. ET-1 was then heated and evaporated to a thickness of 5 nm, and ET-2 and Liq were then heated and evaporated to a thickness of 25 nm to form a two-layer electron transport layer. The evaporation rate was adjusted so that the weight ratio of ET-2 to Liq was approximately 1:1. 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.

[0579] <Example 5, Comparative Examples 4 and 5> The dopant and host in Example 4 were changed to those shown in Table 2 to prepare a device.

[0580] <Evaluation> The fabricated element was subjected to DC voltage application with the ITO electrode as the anode and the aluminum electrode as the cathode at a current density of 20 mA / cm. 2 The emission wavelength, half-width, driving voltage, external quantum efficiency, and LT97 (current density 20 mA / cm 2 The time it took for the brightness to drop to 97% of the initial brightness when the device was continuously driven at 1000 Hz was measured. The evaluation results are shown in Table 2. [Industrial Applicability]

[0581] The polycyclic aromatic compound of the present invention is useful as a material for organic devices, particularly as a material for forming a light-emitting layer of an organic electroluminescent device. [Explanation of symbols]

[0582] 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 110 Substrate 120 electrodes 130 Paint film 140 Paint film 150 Light-emitting layer 200 Bank 300 Inkjet Head 310 Ink Droplets

Claims

1. A polycyclic aromatic compound represented by any one of the following formulas (3-1-1), (3-1-2), and (3-2-1): 【Chemistry 1】 In formula (3-1-1), formula (3-1-2), formula (3-2-1), X 1 are each independently >N-R or >O, and R of the >N-R is an aryl having 6 to 12 carbon atoms which may be substituted with an alkyl having 1 to 6 carbon atoms or a cycloalkyl having 3 to 14 carbon atoms, or a heteroaryl having 2 to 15 carbon atoms which may be substituted with an alkyl having 1 to 6 carbon atoms or a cycloalkyl having 3 to 14 carbon atoms; Each Y is independently B; Each Z is independently -C(-R Z )=; R Z 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 has 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 atom is optionally substituted by an aryl having 6 to 16 carbon atoms, a heteroaryl having 2 to 20 carbon atoms, an alkyl having 6 to 16 carbon atoms, or a cycloalkyl having 3 to 16 carbon atoms; At least one hydrogen atom in the compounds represented by formula (3-1-1), formula (3-1-2) and formula (3-2-1) may be replaced with deuterium.

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

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. A composition comprising the polycyclic aromatic compound according to 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. The organic electroluminescent device according to claim 9 , wherein the host is an anthracene-based compound, a fluorene-based compound, or a dibenzochrysene-based compound.

11. The organic electroluminescence device according to any one of claims 8 to 10, further comprising at least one of an electron transport layer and an electron injection layer disposed between the cathode and the light-emitting layer, and at least one of the electron transport layer and the electron injection layer contains at least one selected from the group consisting of borane derivatives, pyridine derivatives, fluoranthene derivatives, BO-based derivatives, anthracene derivatives, benzofluorene derivatives, phosphine oxide derivatives, pyrimidine derivatives, arylnitrile derivatives, triazine derivatives, benzimidazole derivatives, phenanthroline derivatives, and quinolinol-based metal complexes.

12. 12. The organic electroluminescent device according to claim 11, wherein at least one of the electron transport layer and the electron injection layer further contains at least one selected from the group consisting of alkali metals, alkaline earth metals, rare earth metals, 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.

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

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