Polycyclic aromatic compound

Abstract

To provide a novel compound as a material for organic devices such as an organic electroluminescent element.SOLUTION: A polycyclic aromatic compound has a structure composed of one or two or more structural units represented by a formula (1). (A ring, B ring, C ring and D ring each denote a substituted / unsubstituted aryl ring or heteroaryl ring; Y1 is B or the like; X1 and X2 each denote >N-R, >C(-R)2 or the like; the R is a substituted / unsubstituted aryl, alkyl or the like; X3 is a single bond, >O, >S or the like).SELECTED DRAWING: None

Description

[Technical field]

[0001] The present invention relates to a polycyclic aromatic compound. In particular, the present invention relates to a polycyclic aromatic compound containing nitrogen and boron. 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 containing the polycyclic aromatic compound. [Background technology]

[0002] Conventionally, display devices using electroluminescent light-emitting elements have been extensively studied because they can be made thin and energy-efficient, and organic electroluminescent elements made of organic materials have been actively studied because they can be easily made lighter and larger. In particular, there has been active research into the development of organic materials that have the luminescence properties of blue, 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.

[0003] An organic electroluminescent device has a structure consisting of a pair of electrodes consisting of an anode and a cathode, and one or more layers containing an organic compound disposed between the pair of electrodes. The layers containing the organic compound include 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 a polycyclic aromatic compound containing boron is useful as a material for organic electroluminescent devices, etc. It has been reported that the organic electroluminescent device containing this polycyclic aromatic compound has good external quantum efficiency. [Prior art documents] [Patent documents]

[0005] [Patent Document 1] JP 2018-043984 A Summary of the Invention [Problem to be solved by the invention]

[0006] As described above, various materials have been developed for use in organic EL elements. However, 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 compound 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 novel polycyclic aromatic compound having a structure similar to that of the compound described in Patent Document 1, which has better light-emitting properties. The inventors 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 compound, and further provides an organic device material containing the following polycyclic aromatic compound.

[0008] <1> A polycyclic aromatic compound having a structure consisting of one or more structural units represented by the following formula (1): [ka]

[0009] In formula (1), ring A, ring B, ring C and ring D are each independently an aryl ring or a heteroaryl ring, and at least one hydrogen atom of the aryl ring or the heteroaryl ring in ring A, ring B, ring C and ring D may be substituted; Y 1 is B, P, P=O, P=S, Al, Ga, As, Si-R, Ge-R or Sn-R, and R of Si-R, Ge-R and Sn-R is optionally substituted aryl, optionally substituted heteroaryl, optionally substituted alkyl or optionally substituted cycloalkyl; X 1 and X 2 is >O, >S, >Se, >NR, >Si(-R)2, >C(-R)2, or >C=O, and R in >NR, >Si(-R)2, and >C(-R)2 is each independently hydrogen, optionally substituted aryl, optionally substituted heteroaryl, alkyl, or cycloalkyl, and two R in each of >Si(-R)2 and >C(-R)2 may be bonded to each other to form a ring; X 3 is a single bond, >O, >S, >Se, >NR, >Si(-R)2, >C(-R)2, or >C=O, and R in >NR, >Si(-R)2, and >C(-R)2 is each independently hydrogen, optionally substituted aryl, optionally substituted heteroaryl, alkyl, or cycloalkyl, and two R in each of >Si(-R)2 and >C(-R)2 may be bonded to each other to form a ring; At least one selected from the group consisting of aryl rings and heteroaryl rings in the above structure may be fused with at least one cycloalkane, at least one hydrogen in the cycloalkane may be replaced, and at least one -CH2- in the cycloalkane may be replaced with -O-; At least one hydrogen in the above structure may be replaced with deuterium, cyano, or halogen. <2> Having a structure consisting of one of the structural units represented by formula (1), <1> The polycyclic aromatic compound according to claim 1.

[0010] <3> It has a structure consisting of 1 to 3 structural units represented by the following formula (1-1): <1> or <2> 4. The polycyclic aromatic compound according to claim 1 ; [ka]

[0011] In formula (1-1), R 1 ~R 12are 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 replaced by an aryl, heteroaryl, alkyl, cycloalkyl, or substituted silyl; R 1 ~R 12 adjacent groups among the above may be bonded to each other to form an aryl ring or a heteroaryl ring together with the a ring, the b ring, the c ring or the d ring, and at least one hydrogen atom in the formed ring may be 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 or a substituted silyl, and at least one hydrogen atom in these may be replaced by an aryl, a heteroaryl, an alkyl, a cycloalkyl or a substituted silyl; X 1 and X 2 is >O, >S, >Se, >NR, >Si(-R)2, >C(-R)2, or >C=O, and R in >NR, >Si(-R)2, and >C(-R)2 is each independently hydrogen, optionally substituted aryl, optionally substituted heteroaryl, alkyl, or cycloalkyl, and two R in each of >Si(-R)2 and >C(-R)2 may be bonded to each other to form a ring; X 3 is a single bond, >O, >S, >Se, >NR, >Si(-R)2, >C(-R)2, or >C=O, and R in >NR, >Si(-R)2, and >C(-R)2 is each independently hydrogen, optionally substituted aryl, optionally substituted heteroaryl, alkyl, or cycloalkyl, and two R in each of >Si(-R)2 and >C(-R)2 may be bonded to each other to form a ring; Y 1is B, P, P=O, P=S, Al, Ga, As, Si-R, Ge-R or Sn-R, in which R is aryl or alkyl; at least one selected from the group consisting of aryl rings and heteroaryl rings in the structure consisting of 1 to 3 structural units represented by formula (1-1) may be condensed with at least one cycloalkane having 3 to 24 carbon atoms, at least one hydrogen in the cycloalkane may be substituted with an aryl having 6 to 30 carbon atoms, a heteroaryl having 2 to 30 carbon atoms, an alkyl having 1 to 24 carbon atoms, or a cycloalkyl having 3 to 24 carbon atoms, and at least one -CH2- in the cycloalkane may be substituted with -O-; At least one hydrogen atom in the structure consisting of one to three structural units represented by formula (1-1) may be substituted with cyano, halogen, or deuterium.

[0012] <4> In formula (1-1), Y 1 is B, X 1 and X 2 are each independently >O, >S, >NR, or >C(-R)2, R of the >NR is an aryl having 6 to 12 carbon atoms, a heteroaryl having 2 to 15 carbon atoms, an alkyl having 1 to 6 carbon atoms, or a cycloalkyl having 3 to 14 carbon atoms, and the aryl having 6 to 12 carbon atoms and the heteroaryl having 2 to 15 carbon atoms in R of the >NR may each be substituted with an alkyl having 1 to 6 carbon atoms, a cycloalkyl having 3 to 14 carbon atoms, or a substituted silyl, and R of the >C(-R)2 is each independently represents hydrogen, an aryl having 6 to 12 carbon atoms, a heteroaryl having 2 to 15 carbon atoms, an alkyl having 1 to 6 carbon atoms, or a cycloalkyl having 3 to 14 carbon atoms; in the >C(-R)2, the aryl having 6 to 12 carbon atoms and the heteroaryl having 2 to 5 carbon atoms in R may each be substituted with an alkyl having 1 to 6 carbon atoms, a cycloalkyl having 3 to 14 carbon atoms, or a substituted silyl; and in the >C(-R)2, two Rs may be bonded to each other to form a ring; X 3is a single bond, >O, >S, >NR, or >C(-R)2, R of the >NR is an aryl having 6 to 12 carbon atoms, a heteroaryl having 2 to 15 carbon atoms, an alkyl having 1 to 6 carbon atoms, or a cycloalkyl having 3 to 14 carbon atoms, and the aryl having 6 to 12 carbon atoms and the heteroaryl having 2 to 15 carbon atoms in R of the >NR may each be substituted with an alkyl having 1 to 6 carbon atoms, a cycloalkyl having 3 to 14 carbon atoms, or a substituted silyl, and each R of the >C(-R)2 is independently and R is hydrogen, an aryl having 6 to 12 carbon atoms, a heteroaryl having 2 to 15 carbon atoms, an alkyl having 1 to 6 carbon atoms, or a cycloalkyl having 3 to 14 carbon atoms; in the above >C(-R)2, the aryl having 6 to 12 carbon atoms and the heteroaryl having 2 to 5 carbon atoms in R may each be substituted with an alkyl having 1 to 6 carbon atoms, a cycloalkyl having 3 to 14 carbon atoms, or a substituted silyl; and in the above >C(-R)2, two Rs may be bonded to each other to form a ring; <3> The polycyclic aromatic compound according to claim 1.

[0013] <5> X 1 and X 2 are all >NR, and R in the >NR is an aryl which may be substituted with an alkyl having 1 to 6 carbon atoms or a heteroaryl which may be substituted with an alkyl having 1 to 6 carbon atoms; X 3 is a single bond or >S, <4> The polycyclic aromatic compound according to claim 1.

[0014] <6> Represented by any of the following formulas: <5> 4. The polycyclic aromatic compound according to claim 1 ; [ka] In the formula, Me is methyl and tBu is t-butyl.

[0015] <7> X 1 and X 2is >C(-R)2, each R in the >C(-R)2 is independently hydrogen or alkyl having 1 to 6 carbon atoms, and two R in each >C(-R)2 may be bonded to each other to form a ring; X 3 is >O or >S, <4> The polycyclic aromatic compound according to claim 1.

[0016] <8> Represented by any of the following formulas: <7> 4. The polycyclic aromatic compound according to claim 1 ; [ka] In the formula, Me is methyl and tBu is t-butyl.

[0017] <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. <11> Main chain polymer <9> or a pendant-type crosslinked polymer obtained by further crosslinking the pendant-type polymer compound. <12> <1> ~ <8> The polycyclic aromatic compound according to any one of the above. <9> The reactive compound according to <10> or <11> 2. A material for an organic device, comprising the pendant type polymer compound or the pendant type crosslinked polymer according to claim 1. <13> The organic device material is a material for an organic electroluminescent element, a material for an organic field effect transistor, or a material for an organic thin-film solar cell. <12> The material for an organic device according to claim 1. <14> The material for an organic electroluminescent device is a material for a light-emitting layer. <13> The material for an organic device according to claim 1. <15> <1> ~ <8> The polycyclic aromatic compound according to any one of the above. <9> The reactive compound according to <10> or <11> 2. A composition comprising the pendant type polymer compound or the pendant type crosslinked polymer according to claim 1, and an organic solvent.

[0018] <16> 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. <17> 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 a light-emitting layer containing the pendant type polymer compound or the pendant type crosslinked polymer according to claim 1. <18> 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; <17> The organic electroluminescent device according to claim 1. <19> The host is an anthracene-based compound, a fluorene-based compound, or a dibenzochrysene-based compound; <18> The organic electroluminescent device according to claim 1.

[0019] <20> an electron transport layer and / or an electron injection layer disposed between the cathode and the light emitting layer, at least one of the electron transport layer and the electron injection layer containing 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, quinolinol metal complexes, thiazole derivatives, benzothiazole derivatives, silole derivatives and azoline derivatives; <17> ~ <19> 13. The organic electroluminescent device according to claim 12, <21> the electron transport layer and / or 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; <20> The organic electroluminescent device according to claim 1. <22> 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, <17> ~ <21> 13. The organic electroluminescent device according to claim 12, <23> <16> ~ <22> 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

[0020] The present invention provides a novel polycyclic aromatic compound useful as a material for organic devices such as organic electroluminescence elements. The polycyclic aromatic compound of the present invention can be used in the manufacture of organic devices such as organic electroluminescence elements. [Brief description of the drawings]

[0021] [Figure 1] FIG. 1 is a schematic cross-sectional view showing an example of an organic electroluminescent device. [Diagram 2] FIG. 1 is an energy level diagram showing the energy relationship among a host, an assisting dopant, and an emitting dopant in a TAF device using a common fluorescent dopant. [Diagram 3] FIG. 2 is an energy level diagram showing an example of the energy relationship among a host, an assisting dopant, and an emitting dopant in an organic electroluminescent element according to one embodiment of the present invention. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0022] 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)". In this specification, the organic electroluminescent element may be referred to as an organic EL element.

[0023] 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.

[0024] 1. Polycyclic aromatic compounds The polycyclic aromatic compound of the present invention has a structure consisting of one or more structural units represented by the following formula (1). The polycyclic aromatic compound of the present invention has a high luminescence quantum yield (PLQY), and in particular, compared to conventionally known polycyclic aromatic compounds, has a high luminescence quantum yield (PLQY) and a low ... 3 )) provides the compound with high robustness and excellent stability, and therefore the polycyclic aromatic compound of the present invention can provide an organic EL device with a long life. [ka]

[0025] In formula (1), Ring A, ring B, ring C and ring D are each independently an aryl ring or a heteroaryl ring, and at least one hydrogen atom of the aryl ring or heteroaryl ring in ring A, ring B, ring C and ring D may be substituted.

[0026] In the structural unit represented by formula (1), the A ring is a trivalent group having a ring member atom (an atom forming a ring structure) Y 1 , X 1 , and X 2The B ring is a trivalent group having a ring member atom Y 1 , X 1 and N are directly bonded to the ring, and the C ring is a tetravalent group with a ring member atom Y 1 , X 2 , X 3 and N are directly bonded to the ring, and the ring D is a divalent group with X at the ring member atom. 3 and a ring directly bonded to N. Therefore, the replacement of at least one hydrogen atom of the above aryl ring or heteroaryl ring means that Y 1 , X 1 , X 2 , X 3 and has at least one substituent at a position other than the position bonded to any of N. 1 , X 1 , X 2 , X 3 and the ring atom directly bonded to N may be a carbon atom.

[0027] In the structural unit represented by formula (1), the A ring is X 1 , X 2 and Y 1 It is preferable that ring B has a 5-membered or 6-membered ring directly bonded to X 1 , Y 1 and preferably has a 5- or 6-membered ring directly bonded to N, and the C ring is X 2 , X 3 and Y 1 and preferably has a 5- or 6-membered ring directly bonded to N, and ring D is X 3 and preferably has a 5- or 6-membered ring directly bonded to N.

[0028] In addition, the above aryl ring and heteroaryl ring may each be condensed with at least one cycloalkane as described below.

[0029] The above-mentioned "aryl ring" in ring A, ring B, ring C and ring D in formula (1) 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.

[0030] Specific examples of the "aryl ring" include a monocyclic benzene ring, a condensed bicyclic naphthalene ring, an indene ring, a condensed tricyclic anthracene ring, an acenaphthylene ring, a fluorene ring, a phenalene ring, a phenanthrene ring, a condensed tetracyclic triphenylene ring, a pyrene ring, a naphthacene ring, a benzofluorene ring, a chrysene ring, a condensed pentacyclic perylene ring, a pentacene ring, and the like. The fluorene ring and the benzofluorene ring also include a structure in which the fluorene ring and the benzofluorene ring are spiro-bonded, respectively. It is also preferable that the fluorene ring and the benzofluorene ring are substituted with methyl as the first substituent described below, respectively, to form a dimethylfluorene ring or a dimethylbenzofluorene ring, with two of the two hydrogen atoms of the methylene being substituted with methyl as the first substituent described below.

[0031] Examples of the "heteroaryl ring" in ring A, ring B, ring C and ring D in formula (1) 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.

[0032] 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, a tetrazine 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 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, an imidazopyridine ring (such as an imidazo[1,2-a]pyridine ring), a furan ring, a benzyl ring, a phenyl ... benzofuran ring, isobenzofuran ring, dibenzofuran ring, naphthobenzofuran ring, benzofurofuran ring, benzofurobenzofuran ring (benzofuro[3,2-b]benzofuran ring, etc.), thiophene ring, benzothiophene ring, dibenzothiophene ring, naphthobenzothiophene ring, thienobenzothiophene ring, benzothienobenzothiophene ring ([1]-benzothieno[3,2-b][1]benzothiophene ring, etc.), thienopyril ring, Examples of such rings include thieno[1,2-a]pyridine rings (e.g., thieno[1,2-a]pyridine rings), thienopyrimidine rings (e.g., thieno[3,2-d]pyrimidine rings), thienobenzofuran rings (e.g., thieno[3,2-b]benzofuran rings), benzophosphole rings, dibenzophosphole rings, benzophosphole oxide rings, dibenzophosphole oxide rings, furazan rings, thianthrene rings, selenophene rings, xanthene rings, thioxanthene rings, indenothiophene rings, etc. Xanthene and thioxanthene rings also include structures in which a fluorene ring or a benzofluorene ring is spiro-bonded, respectively. It is also preferred that two of the two hydrogen atoms of the methylene of the xanthene ring, thioxanthene ring, and indenothiophene ring are substituted with methyl as a first substituent described below to form a dimethylfluorene ring, a dimethylbenzofluorene ring, and a dimethylindenothiophene ring (dimethyl-4H-indeno[1,2-b]thiophene ring).

[0033] Ring A, ring B, ring C and ring D are preferably an optionally substituted benzene ring, an optionally substituted pyridine ring, an optionally substituted pyrimidine ring, an optionally substituted pyridazine ring or an optionally substituted triazine ring (1,2,3-triazine ring), more preferably an optionally substituted benzene ring.

[0034] In formula (1), at least one hydrogen atom of the aryl or heteroaryl ring in each of rings A, B, C and D may be substituted. At least one hydrogen atom of the aryl or heteroaryl ring in at least one selected from the group consisting of rings A, B, C and D is preferably substituted. At least one hydrogen atom of the aryl or heteroaryl ring in at least one selected from the group consisting of rings A, B and D is more preferably substituted, and one hydrogen atom of the aryl or heteroaryl ring in ring A or ring B is even more preferably substituted.

[0035] In formula (1), the substituent when at least one hydrogen atom of the aryl ring or heteroaryl ring in each of ring A, ring B, ring C and ring D is substituted may be, for example, a substituent selected from the group consisting of substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted diarylamino (two aryls may be bonded via a single bond or a linking group), substituted or unsubstituted diheteroarylamino, substituted or unsubstituted arylheteroarylamino, substituted or unsubstituted dialkylamino, 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 alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted aryloxy, substituted silyl, substituted or unsubstituted arylsulfonyl, substituted or unsubstituted diarylphosphine, substituted or unsubstituted diarylphosphine oxide, and substituted or unsubstituted diarylphosphine sulfide. In this specification, among the above-mentioned substituents, "aryl", "heteroaryl", "diarylamino (two aryls may be bonded via a single bond or a linking group)", "diheteroarylamino", "arylheteroarylamino", "dialkylamino", "diarylboryl (two aryls may be bonded via a single bond or a linking group)", "alkyl", "cycloalkyl", "alkoxy", "aryloxy" and the like that are directly bonded to an aryl ring or a heteroaryl ring are referred to as the first substituent. Also, as explained as "substituted or unsubstituted", the substituent that is substituted on the first substituent is referred to as the second substituent.

[0036] Examples of the "aryl" as the first substituent include the monovalent group of the "aryl ring" described above, as well as biphenylyl, m-terphenylyl, o-terphenylyl, p-terphenylyl, etc. Specific examples of the "aryl" as the first substituent include phenyl, which is a monocyclic ring; biphenylyl, which is a bicyclic ring; naphthyl (1-naphthyl or 2-naphthyl), which is a condensed bicyclic ring; terphenylyl (m-terphenylyl, o-terphenylyl, or p-terphenylyl), which is a tricyclic ring; acetylenyl, acenaphthylenyl, fluorenyl, phenalenyl, phenanthrenyl, which are condensed tricyclic rings; triphenylenyl, pyrenyl, naphthacenyl, chrysenyl, which are condensed tetracyclic rings; and perylenyl, pentacenyl, which are condensed pentacyclic rings. Further examples include a group in which a fluorene ring or a benzofluorene ring is spiro-bonded to a fluorenyl, and a group in which a fluorene ring or a benzofluorene ring is spiro-bonded to a benzofluorenyl.

[0037] Furthermore, examples of the "heteroaryl" as the first substituent include the monovalent group of the above-mentioned "heteroaryl ring". For example, the heteroaryl has 2 to 30 carbon atoms, preferably a heteroaryl has 2 to 25 carbon atoms, more preferably a heteroaryl has 2 to 20 carbon atoms, further preferably a heteroaryl has 2 to 15 carbon atoms, and particularly preferably a heteroaryl has 2 to 10 carbon atoms.

[0038] Specific examples of "heteroaryl" include pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, oxadiazolyl, thiadiazolyl, triazolyl, tetrazolyl, pyrazolyl, pyridinyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, indolyl, isoindolyl, 1H-indazolyl, benzimidazolyl, benzoxazolyl, benzothiazolyl, 1H-benzotriazolyl, quinolinyl, isoquinolinyl, cinnolinyl, quinolin ... Examples include nazolinyl, quinoxalinyl, phthalazinyl, naphthyridinyl, purinyl, pteridinyl, carbazolyl, acridinyl, phenoxathiinyl, phenoxazinyl, phenothiazinyl, phenazinyl, indolizinyl, furanyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, naphthobenzofuranyl, thienyl, benzothienyl, isobenzothienyl, dibenzothienyl, naphthobenzothienyl, furazanyl, thianthrenyl, xanthenyl, and thioxanthenyl.

[0039] 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 6 carbon atoms (branched alkyl having 3 to 6 carbon atoms) is even more preferred, and an alkyl having 1 to 4 carbon atoms (branched alkyl having 3 to 4 carbon atoms) is particularly preferred.

[0040] 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.

[0041] 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.

[0042] Furthermore, examples of the "cycloalkyl" as the first substituent include cycloalkyl having 3 to 12 carbon atoms. A preferred cycloalkyl is cycloalkyl having 3 to 10 carbon atoms. A more preferred cycloalkyl is cycloalkyl having 3 to 8 carbon atoms. An even more preferred cycloalkyl is cycloalkyl having 3 to 6 carbon atoms.

[0043] 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.

[0044] In addition, by introducing a cycloalkyl into the polycyclic aromatic compound of the present invention, a decrease in melting point and sublimation temperature can be expected. This means that in the sublimation purification, which is almost essential as a purification method for materials for organic devices such as organic EL elements that require high purity, purification can be performed at a relatively low temperature, so that thermal decomposition of the material can be avoided. This is also true for the vacuum deposition process, which is a powerful means for producing organic devices such as organic EL elements, and since the process can be performed at a relatively low temperature, thermal decomposition of the material can be avoided, and as a result, high-performance organic devices can be obtained. In addition, since the solubility in organic solvents is improved by the introduction of a cycloalkyl, it can also be applied to the production of elements using a coating process. However, the present invention is not particularly limited to these principles.

[0045] 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 4 carbon atoms (branched alkoxy having 3 to 4 carbon atoms) is particularly preferred.

[0046] Specific alkoxy includes methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, s-butoxy, t-butoxy, pentyloxy, hexyloxy, heptyloxy, octyloxy, and the like.

[0047] The "alkenyl" as the first substituent includes, for example, unsaturated aliphatic hydrocarbon groups containing a double bond such as vinyl, allyl, butadienyl, etc. The number of carbon atoms in the alkenyl is not particularly limited, but is usually in the range of 2 to 20.

[0048] The "alkynyl" as the first substituent is, for example, an unsaturated aliphatic hydrocarbon group containing a triple bond such as acetylenyl. The number of carbon atoms in the alkynyl is not particularly limited, but is usually in the range of 2 to 20.

[0049] In addition, for details of the "aryl" and "heteroaryl" in the "diarylamino", "diheteroarylamino", "arylheteroarylamino", "diarylboryl", "aryloxy", "arylsulfonyl", "diarylphosphine", "diarylphosphine oxide", and "diarylphosphine sulfide" as the first substituent, the explanation of the "aryl" and "heteroaryl" mentioned above can be cited.

[0050] The two aryls in the "diarylamino" of the first substituent may be bonded via a single bond or a linking group (e.g., >C(-R)2, >O, >S, or >NR). The two aryls in the "diarylboryl" of the first substituent 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 specific examples of these groups can be cited from the explanation of aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, alkoxy, or aryloxy as the first substituent described above.

[0051] The alkyl of "dialkylamino" as the first substituent can be cited from the above description of "alkyl".

[0052] The "substituted silyl" includes silyl substituted with three substituents selected from the group consisting of alkyl, cycloalkyl, and aryl. Specific examples include trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, alkyldicycloalkylsilyl, triarylsilyl, dialkylarylsilyl, and alkyldiarylsilyl.

[0053] The "trialkylsilyl" refers to a group in which three hydrogen atoms in an unsubstituted silyl 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.

[0054] 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.

[0055] The "tricycloalkylsilyl" includes a group in which three hydrogen atoms in an unsubstituted silyl are each independently substituted with a cycloalkyl, and the cycloalkyl can be cited as the group described as the "cycloalkyl" in the first substituent above. The cycloalkyl preferably used for substitution is a cycloalkyl 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, decahydroazulenyl, and the like.

[0056] Specific examples of tricycloalkylsilyl include tricyclopentylsilyl and tricyclohexylsilyl.

[0057] 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.

[0058] 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.

[0059] Examples of the second substituent include aryl, heteroaryl, alkyl, and cycloalkyl. Specific examples of these groups include the above-mentioned descriptions of aryl, heteroaryl, alkyl, and cycloalkyl as the first substituent.

[0060] The first substituent can adjust the emission wavelength. The first substituent (including those substituted with a second substituent) is preferably a group represented by the following structural formula, and more preferably, methyl, tertiary alkyl (tR) (t-butyl, t-amyl, t-octyl, etc.), 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, carbamate, etc. Preferred are azolyl, 3,6-dimethylcarbazolyl, 3,6-di-t-butylcarbazolyl and phenoxy, and more preferred are methyl, t-butyl, t-amyl, t-octyl, 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, 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.

[0061] 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]

[0062] [ka]

[0063] [ka]

[0064] [ka]

[0065]

change

[0066]

change

[0067]

change

[0068]

change

[0069]

change

[0070]

change

[0071]

change

[0072]

change

[0073]

change

[0074] Tertiary alkyl (tR), some of the examples of which are given above, are particularly preferred as substituents. This is because such bulky substituents prevent inactivation due to aggregation between molecules and improve the luminescence quantum yield (PLQY). Tertiary alkyl can be represented by the following formula (tR). [ka]

[0075] In the formula (tR), R a , R b , and R c are each independently an alkyl group having 1 to 24 carbon atoms, any -CH2- in the alkyl group may be replaced with -O-, and the group represented by formula (tR) replaces at least one hydrogen atom in the aryl ring or heteroaryl ring at *.

[0076] R a , R b , and R c The "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).

[0077] 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.

[0078] R a , R b , and R cSpecific 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.

[0079] 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.

[0080] Other preferred examples include diarylamino substituted with a group of formula (tR), carbazolyl substituted with a group of formula (tR), and benzocarbazolyl substituted with a group of formula (tR). "Examples of the substitution of the group of formula (tR) on diarylamino, carbazolyl, and benzocarbazolyl include those in which some or all of the hydrogen atoms on the aryl ring or benzene ring in these groups are substituted with a group of formula (tR).

[0081] At least one selected from the group consisting of aryl rings and heteroaryl rings in the structure consisting of one or more structural units represented by formula (1) may be condensed with at least one cycloalkane. For example, the aryl and heteroaryl rings (Y 1 Or X 3 At least one of the aryl and heteroaryl rings included as the first and second substituents, as well as the ring directly bonded to the aryl or heteroaryl group, may be fused to at least one cycloalkane.

[0082] 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.

[0083] 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.

[0084] Among these, for example, a structure in which at least one hydrogen atom is substituted on the carbon atom at the α-position of a cycloalkane (the carbon atom at the position adjacent to the carbon atom at the condensation site in a cycloalkyl condensed to an aromatic ring or a heteroaromatic ring) is preferred, a structure in which two hydrogen atoms are substituted on the carbon atom at the α-position is more preferred, and a structure in which a total of four hydrogen atoms are substituted on the two carbon atoms at the α-position is even more preferred. Examples of this substituent include an alkyl (particularly methyl) substituent having 1 to 5 carbon atoms, a halogen (particularly fluorine) substituent, and a deuterium substituent.

[0085] The number of cycloalkanes fused to one aryl ring or heteroaryl ring is preferably 1 to 3, more preferably 1 or 2, and even more preferably 1. As an example of condensation to a ring that is a monovalent group, an example in which one or more cycloalkanes are fused to one benzene ring (phenyl) is shown below. * indicates a bonding position, and may be any position of a carbon atom that constitutes a benzene ring and does not constitute a cycloalkane. Cycloalkanes fused to each other as in formula (Cy-1-4) and formula (Cy-2-4) may be condensed. The same applies even if the condensed ring (group) is an aromatic ring or heteroaromatic ring other than a benzene ring (phenyl), or even if the condensed cycloalkane is a cycloalkane other than cyclopentane or cyclohexane.

[0086] [ka]

[0087] At least one -CH2- in the cycloalkane may be replaced with -O-. For example, the following shows an example in which one or more -CH2- in a cycloalkane fused to one benzene ring (phenyl) are replaced with -O-. The same applies even when the fused ring (group) is an aromatic ring or heteroaromatic ring other than a benzene ring (phenyl) or when the fused cycloalkane is a cycloalkane other than cyclopentane or cyclohexane.

[0088] [ka]

[0089] At least one hydrogen atom in the cycloalkane may be substituted, and examples of the substituent include 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, deuterium, cyano, and halogen. For details, the description of the first substituent mentioned above can be cited. Among these substituents, alkyl (e.g., alkyl having 1 to 6 carbon atoms), cycloalkyl (e.g., cycloalkyl having 3 to 14 carbon atoms), halogen (e.g., fluorine), and deuterium are preferred. In addition, when cycloalkyl is substituted, it may be substituted to form a spiro structure, and examples of this are shown below.

[0090] [ka]

[0091] Specific examples include those in which the first substituent is a diarylamino fused to a cycloalkane (fused to the aryl moiety) or a carbazolyl fused to a cycloalkane (fused to the benzene ring moiety).

[0092] In formula (1), Y 1 is B, P, P=O, P=S, Al, Ga, As, Si-R, Ge-R or Sn-R, and R in the Si-R, Ge-R and Sn-R is an optionally substituted aryl, an optionally substituted heteroaryl, an optionally substituted alkyl or an optionally substituted cycloalkyl. 1 is preferably B, P, P=O or P=S, and is more preferably B.

[0093] In formula (1), X 1 and X 2 are each independently >O, >S, >Se, >NR, >Si(-R)2, >C(-R)2, or >C=O, and R in the >NR, >Si(-R)2, and >C(-R)2 is each independently hydrogen, an optionally substituted aryl, an optionally substituted heteroaryl, an alkyl, or a cycloalkyl, and two R may be joined together to form a ring. 1 and X 2 are each independently preferably >O, >S, >NR, >C(-R)2, or >C=O, more preferably >O, >S, >NR, >C(-R)2, or >C=O, further preferably >O or >S, and particularly preferably >S. 1 and X 2 Each R in >NR is preferably an optionally substituted aryl, more preferably an optionally substituted phenyl. 1 and X 2 Each R in >C(-R)2 is preferably independently hydrogen, alkyl, or optionally substituted aryl, more preferably alkyl or optionally substituted aryl, even more preferably alkyl, and particularly preferably methyl. From the viewpoint of ease of synthesis, X 1 and X 2 are preferably the same. For example, X 1 and X 2 are both >N-(4-t-butyl-phenyl), are both >N-(4-methyl-phenyl), are both >C(-Me)2 (Me is methyl), and the like.

[0094] In formula (1), X 3 is a single bond, >O, >S, >Se, >NR, >Si(-R)2, >C(-R)2, or >C=O, and R in the >NR, >Si(-R)2, and >C(-R)2 are each independently hydrogen, an optionally substituted aryl, an optionally substituted heteroaryl, an alkyl, or a cycloalkyl, and two Rs may form a ring together. X 3 is preferably a single bond, >O, >S, >NR, >C(-R)2, or >C=O, more preferably a single bond, >O, >S, >NR, >C(-R)2, or >C=O, further preferably a single bond, >O, or >S, and particularly preferably >S. 3 In the formula >NR, R is preferably an optionally substituted aryl, more preferably an optionally substituted phenyl. 3 R in >C(-R)2 is preferably independently hydrogen, alkyl or optionally substituted aryl, more preferably alkyl or optionally substituted aryl, even more preferably alkyl, and particularly preferably methyl.

[0095] X 1 and X 2 are both >NR and X 3 is preferably a single bond or >S. In this case, it is preferable that each R in the >NR is independently an aryl which may be substituted with an alkyl having 1 to 6 carbon atoms or a heteroaryl which may be substituted with an alkyl having 1 to 6 carbon atoms. 1 and X2 are all >C(-R)2 and X 3 is also preferably >O or >S. In this case, it is preferable that each R in the >C(-R)2 is independently hydrogen or an alkyl having 1 to 6 carbon atoms, and the two R in each of the >C(-R)2 may be bonded to each other to form a ring. It is preferable that each R in the >C(-R)2 is methyl.

[0096] All or a part of hydrogen in the structure consisting of one or more structural units represented by formula (1) may be cyano, halogen, or deuterium. For example, all or a part of hydrogen in the aryl ring, heteroaryl ring, or cyclohexane ring contained in the structure may be replaced with cyano, halogen, or deuterium, all or a part of hydrogen in the first and second substituents may be replaced with cyano, halogen, or deuterium, and when at least one of the aryl ring and heteroaryl ring is condensed with at least one cycloalkane, all or a part of hydrogen in the cycloalkane may be replaced with cyano, halogen, or deuterium (described above). The halogen is fluorine, chlorine, bromine, or iodine, preferably fluorine, chlorine, or bromine, and more preferably fluorine.

[0097] A preferred example of the structural unit represented by formula (1) is a structural unit represented by the following formula (1-1). [ka]

[0098] In formula (1-1), R 1 ~R 12are 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 replaced by an aryl, heteroaryl, alkyl, cycloalkyl, or substituted silyl; R 1 ~R 12 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 b, the ring c, or the ring d, 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, or a substituted silyl, and at least one hydrogen atom in these may be replaced by an aryl, a heteroaryl, an alkyl, a cycloalkyl, or a substituted silyl.

[0099] In formula (1-1), X 1 ~X 3 and Y 1 is X in formula (1). 1 ~X 3 and Y 1 and the preferred ranges thereof are also the same.

[0100] In formula (1-1), R 1 ~R 12For the first substituents "aryl", "heteroaryl", "diarylamino (two aryls may be bonded via a single bond or a linking group)", "diheteroarylamino", "arylheteroarylamino", "dialkylamino", "diarylboryl (two aryls may be bonded via a single bond or a linking group)", "alkyl", "cycloalkyl", "alkoxy", and "aryloxy" in the above, the explanation of the "first substituent" can be referred to. For the substituents of aryl, heteroaryl, alkyl, and cycloalkyl, the explanation of the "second substituent" can be referred to. For the substituted silyl, the explanation of the above formula (1) can be referred to.

[0101] In formula (1-1), R 1 ~R 12 Adjacent groups among may be bonded together to form an aryl or heteroaryl ring together with the a, b, c or d ring, and at least one hydrogen in the formed ring may be substituted with an 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, and at least one hydrogen in these may be substituted with an aryl, heteroaryl, alkyl, cycloalkyl, or substituted silyl. The above description of the "first substituent" and "first substituent" may also be referred to for the substituent in this case. R 1 ~R 12 Among the adjacent groups, R 1 and R 2 , R 2 and R 3 , R 4 and R 5 , R 6 and R 7 , R 7 and R 8 , R 8 and R 9 , R 10and R 11 And R 11 and R 12 For example, the combination of R on ring b is 10 and d-ring R 9 do not correspond to "adjacent groups" and are not bonded to each other. In other words, "adjacent groups" means groups adjacent to each other on the same ring.

[0102] For example, R 1 and R 2 , or R 2 and R 3 When R is bonded to the a ring to form an aryl or heteroaryl ring as the a' ring, the structure is represented by formula (1-1-1). 10 and R 11 , or R 11 and R 12 are bonded together with ring b to form an aryl or heteroaryl ring as ring b', and R 4 and R 5 When R is bonded to the ring c to form an aryl or heteroaryl ring as the ring c', the structure is represented by formula (1-1-2). 6 and R 7 , R 7 and R 8 , or R 8 and R 9 When the rings are bonded together to form an aryl or heteroaryl ring as the ring d', the structure is represented by formula (1-1-3). The definitions of the symbols in formulas (1-1-1), (1-1-2) and (1-1-3) are the same as those in formula (1-1).

[0103] [ka]

[0104] Although not shown in the formula, there are also compounds in which the rings a, b, c and d are all changed to rings a', b', c' and d'.

[0105] The compounds represented by formula (1-1-1), formula (1-1-2) and formula (1-1-3) are compounds having ring b' (or ring a', or ring c' or ring d') 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, which is ring b (or ring a, or ring c or ring d), and the condensed ring b' (condensed ring a', or condensed ring c' or condensed ring d') formed 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.

[0106] Specific examples of the structural unit represented by formula (1) include polycyclic aromatic compounds represented by any one of the following formulas selected from the group consisting of formula (1-a), formula (1-b), formula (1-c), formula (1-d), formula (1-e), formula (1-f), formula (1-g), formula (1-h), formula (1-i), formula (1-j), and formula (1-k).

[0107] [ka]

[0108] In the above formula, X 3 is X in formula (1-1) 3 Synonymous with R. 21 are each independently a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, an aryl group having 5 to 16 carbon atoms which may be substituted with an alkyl group having 1 to 6 carbon atoms, a heteroaryl group having 5 to 20 carbon atoms which may be substituted with an alkyl group having 1 to 6 carbon atoms, or a diarylamino group having 5 to 20 carbon atoms which may be substituted with an alkyl group having 1 to 6 carbon atoms; R 22 are each independently hydrogen or alkyl having 1 to 6 carbon atoms.

[0109] Preferred specific examples of the structural unit represented by formula (1) include the following. [ka]

[0110] In the above formula, R 21 are each independently a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, an aryl group having 5 to 16 carbon atoms which may be substituted with an alkyl group having 1 to 6 carbon atoms, a heteroaryl group having 5 to 20 carbon atoms which may be substituted with an alkyl group having 1 to 6 carbon atoms, or a diarylamino group having 5 to 20 carbon atoms which may be substituted with an alkyl group having 1 to 6 carbon atoms; R 22 are each independently hydrogen or alkyl having 1 to 6 carbon atoms; R 41 is hydrogen or alkyl having 1 to 10 carbon atoms.

[0111] The polycyclic aromatic compound of the present invention is a polycyclic aromatic compound having a structure consisting of one or more structural units represented by formula (1). Examples of polycyclic aromatic compounds having a structure consisting of one of the structural units include polycyclic aromatic compounds represented by the formulas described above as the structural unit represented by formula (1). Examples of polycyclic aromatic compounds having a structure consisting of two or more structural units represented by formula (1) include compounds corresponding to the multimers of polycyclic aromatic compounds represented by the formulas described above as the structural unit represented by formula (1). The multimer is preferably a dimer to hexamer, more preferably a dimer to trimer, and particularly preferably a dimer. The multimer may be in a form having a plurality of the above unit structures in one compound, and may be in a form in which any ring (A ring, B ring, C ring or D ring, a ring, b ring, c ring or d ring) contained in the above structural unit is bonded so as to be shared by a plurality of unit structures, or may be in a form in which any ring (A ring, B ring, C ring or D ring, a ring, b ring, c ring or d ring) contained in the above unit structure is bonded so as to be condensed with each other. Moreover, the above unit structure may be in a form in which a plurality of units are bonded together via a linking group such as a single bond, alkylene having 1 to 3 carbon atoms, phenylene, or naphthylene. Examples of structures consisting of two or more structural units represented by formula (1) include structures represented by the following formulas (1-1-1), (1-1-2) and (1-1-3), in which the structural unit represented by formula (1) is a structural unit represented by formula (1-1). In each of the following formulas, the ring a, ring b, ring c, ring d, and Y1 , X 1 , X 2 , X 3 , R 1 ~R 12 represents the a ring, the b ring, the c ring, the d ring, and Y in formula (1-1). 1 , X 1 , X 2 , X 3 , R 1 ~R 12 are synonymous with each other.

[0112] [ka]

[0113] The multimeric compound represented by formula (1-1-1), when explained using formula (1-1), is a multimeric compound (dimer) having a plurality of unit structures represented by formula (1-1) in one compound, with the benzene ring being the a-ring being shared. The multimeric compound represented by formula (1-1-2), when explained using formula (1-1), is a multimeric compound (dimer) having two unit structures represented by formula (1-1) in one compound, with the benzene ring being the a-ring being shared. The multimeric compound represented by formula (1-1-3), when explained using formula (1-1), is a multimeric compound (trimer) having three unit structures represented by formula (1-1) in one compound, with the benzene ring being the a-ring being shared.

[0114] The polycyclic aromatic compound of the present invention having a structure consisting of one or two or more structural units represented by formula (1) is preferably a polycyclic aromatic compound having a structure consisting of one to three structural units represented by formula (1), more preferably a polycyclic aromatic compound having a structure consisting of one or two structural units represented by formula (1), and even more preferably a polycyclic aromatic compound having a structure consisting of one of the above structural units.

[0115] Further specific examples of the polycyclic aromatic compound represented by formula (1) of the present invention include the following compounds. In the following structural formula, "Me" represents methyl, "tBu" represents t-butyl, "tAm" represents t-amyl, and "D" represents deuterium. Note that the following structure is only one example.

[0116] [ka]

[0117] [ka]

[0118] [ka]

[0119] [ka]

[0120] [ka]

[0121] [ka]

[0122] [ka]

[0123] [ka]

[0124] [ka]

[0125]

change

[0126]

change

[0127]

change

[0128]

change

[0129]

change

[0130]

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[0131]

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[0132]

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[0133]

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[0134]

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[0135] The polycyclic aromatic compound having a structure consisting of one or more structural units represented by formula (1) 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), a crosslinked polymer obtained by further crosslinking the polymer compound (the polymer compound for obtaining this crosslinked polymer has a crosslinkable substituent), a pendant polymer compound obtained by reacting a main-chain polymer with the reactive compound (the reactive compound for obtaining this pendant polymer compound has a reactive substituent), or a pendant crosslinked polymer obtained by further crosslinking the pendant polymer compound (the pendant polymer compound for obtaining this pendant crosslinked polymer has a crosslinkable substituent).

[0136] 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.

[0137] [ka]

[0138] 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.

[0139] The applications 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.

[0140] A polycyclic aromatic compound having a structure consisting of one or more structural units represented by formula (1) can be produced by referring to the methods described in prior art documents such as International Publication No. WO 2015 / 102118.

[0141] 2. Organic Devices The polycyclic aromatic compound of the present invention can be used as a material for an organic device, such as an organic electroluminescent device, an organic field effect transistor, or an organic thin-film solar cell.

[0142] 2-1. Organic electroluminescent device 2-1-1. Structure of organic electroluminescent device FIG. 1 is a schematic cross-sectional view showing an example of an organic EL element. 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.

[0143] 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.

[0144] 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.

[0145] 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".

[0146] 2-1-2. Emitting layer in organic electroluminescent device The polycyclic aromatic compound of the present invention is preferably used as a material forming one or more organic layers in an organic electroluminescent device, and more preferably used as a material forming a light-emitting layer. The light-emitting layer 105 is a layer that emits light by recombining holes injected from the anode 102 and electrons injected from the cathode 108 between electrodes to which an electric field is applied. The material for the light-emitting layer 105 may be a compound (light-emitting compound) that is excited and emits light by the recombination of holes and electrons, and is preferably a compound that can be formed into a stable thin film shape and exhibits strong luminescence (fluorescence) efficiency in a solid state. The polycyclic aromatic compound of the present invention can be used as a material for a light-emitting layer, and may be used as a dopant material or may be used together with a host material.

[0147] In addition, although there are cases where the dopant is used in combination with an assisting dopant and an emitting dopant, in this specification, when the term "dopant" is simply used, it refers to a light-emitting dopant used alone.

[0148] The light-emitting layer may be a single layer or multiple layers, each of which is formed from materials for the light-emitting layer (host material, dopant material). The host material and the dopant material may each be one type or a combination of multiple types. The dopant material may be contained in the entire host material or may be contained partially in the host material. As a doping method, the dopant material may be formed by co-evaporation with the host material, but it may also be mixed with the host material in advance and then vapor-deposited at the same time.

[0149] 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.

[0150] 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.

[0151] Host Material Examples of the host material include condensed ring derivatives of anthracene, pyrene, dibenzochrysene, fluorene, and the like, which have long been known as light-emitting bodies; bisstyryl derivatives such as bisstyrylanthracene derivatives and distyrylbenzene derivatives; tetraphenylbutadiene derivatives, cyclopentadiene derivatives, fluorene derivatives, benzofluorene derivatives, and dibenzochrysene-based compounds.

[0152] As the host material, for example, a compound represented by any one of the following formulae (H1), (H2), and (H3) can be used. [ka]

[0153] In formulas (H1), (H2) and (H3), L 1represents an arylene having 6 to 24 carbon atoms, a heteroarylene having 2 to 24 carbon atoms, a heteroarylenearylene having 6 to 24 carbon atoms, and an aryleneheteroarylenearylene 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 terphenyl ring, and a fluorene ring. The heteroarylene is preferably a heteroarylene having 2 to 24 carbon atoms, more preferably a heteroarylene having 2 to 20 carbon atoms, still more preferably a heteroarylene having 2 to 15 carbon atoms, and particularly preferably a heteroarylene having 2 to 10 carbon atoms. Specific examples of the heteroarylene include a pyrrole ring, an oxazole ring, an isoxazole ring, a thiazole ring, an isothiazole ring, an imidazole ring, an oxadiazole ring, a thiadiazole ring, a triazole ring, a tetrazole ring, a pyrazole ring, a pyridine ring, a pyrimidine ring, a pyridazine ring, a pyrazine ring, a triazine ring, an indole ring, an isoindole ring, a 1H-indazole ring, a benzene ring, a phenyl ... Examples of divalent groups include a benzoimidazole 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 compounds represented by the above formulas may be substituted with an alkyl group having 1 to 6 carbon atoms, cyano, halogen, or deuterium.

[0154] Preferred specific examples include compounds represented by any of the structural formulas listed below. In the structural formulas listed below, at least one hydrogen may be substituted with halogen, cyano, alkyl having 1 to 4 carbon atoms (e.g., methyl or t-butyl), phenyl, naphthyl, or the like.

[0155] [ka]

[0156] [ka]

[0157] [ka]

[0158] [ka]

[0159] <Anthracene compounds> Examples of the anthracene-based compound as a host include a compound represented by formula (3-H) and a compound represented by formula (3-H2). [ka]

[0160] In formula (3-H), X and Ar 4 are each independently hydrogen, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted diarylamino, optionally substituted diheteroarylamino, optionally substituted arylheteroarylamino, optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted alkenyl, optionally substituted alkoxy, optionally substituted aryloxy, optionally substituted arylthio or optionally substituted silyl; and all X and Ar 4 cannot simultaneously become hydrogen, At least one hydrogen in the compound represented by formula (3-H) may be substituted with halogen, cyano, deuterium or an optionally substituted heteroaryl.

[0161] In addition, a polymer (preferably a dimer) may be formed using the structure represented by formula (3-H) as a unit structure. In this case, for example, the unit structures represented by formula (3-H) may be bonded to each other via X, and examples of X include a single bond, an arylene (phenylene, biphenylene, naphthylene, etc.), and a heteroarylene (a group having a divalent bond such as a pyridine ring, a dibenzofuran ring, a dibenzothiophene ring, a carbazole ring, a benzocarbazole ring, and a phenyl-substituted carbazole ring).

[0162] For details of each group in the compound represented by formula (3-H), the explanation for formula (1) above can be cited, and further explanations will be given in the section on preferred embodiments below.

[0163] Preferred embodiments of the above anthracene-based compounds are described below. The symbols in the structures below are defined as above. [ka]

[0164] In formula (3-H), X is each independently a group represented by formula (3-X1), formula (3-X2) or formula (3-X3), and the group represented by formula (3-X1), formula (3-X2) or formula (3-X3) is bonded to the anthracene ring of formula (3-H) at *. Preferably, two Xs are not simultaneously a group represented by formula (3-X3). More preferably, two Xs are not simultaneously a group represented by formula (3-X2).

[0165] In addition, a polymer (preferably a dimer) may be formed using the structure represented by formula (3-H) as a unit structure. In this case, for example, the unit structures represented by formula (3-H) may be bonded to each other via X, and examples of X include a single bond, an arylene (phenylene, biphenylene, naphthylene, etc.), and a heteroarylene (a group having a divalent bond such as a pyridine ring, a dibenzofuran ring, a dibenzothiophene ring, a carbazole ring, a benzocarbazole ring, and a phenyl-substituted carbazole ring).

[0166] The naphthylene moieties in formula (3-X1) and formula (3-X2) may be condensed with one benzene ring. The condensed structures are as follows: [ka]

[0167] Ar 1 and Ar 2 are each independently hydrogen, phenyl, biphenylyl, terphenylyl, quaterphenylyl, naphthyl, phenanthryl, fluorenyl, benzofluorenyl, chrysenyl, triphenylenyl, pyrenylyl, or a group represented by the formula (A) described below (including carbazolyl, benzocarbazolyl, and phenyl-substituted carbazolyl). 1 or Ar 2 is a group represented by formula (A), the group represented by formula (A) is bonded to the naphthalene ring in formula (3-X1) or formula (3-X2) at the *.

[0168] Ar 3 is phenyl, biphenylyl, terphenylyl, quaterphenylyl, naphthyl, phenanthryl, fluorenyl, benzofluorenyl, chrysenyl, triphenylenyl, pyrenylyl, or a group represented by formula (A) (including carbazolyl, benzocarbazolyl, and phenyl-substituted carbazolyl). 3is a group represented by formula (A), the group represented by formula (A) is bonded to the single bond represented by a straight line in formula (3-X3) at the *. That is, the anthracene ring of formula (3-H) and the group represented by formula (A) are directly bonded.

[0169] Also, Ar 3 may have a substituent, and Ar 3 At least one hydrogen atom in may be further substituted with an alkyl group having 1 to 4 carbon atoms, a cycloalkyl group having 5 to 10 carbon atoms, phenyl, biphenylyl, terphenylyl, naphthyl, phenanthryl, fluorenyl, chrysenyl, triphenylenyl, pyrenylyl, or a group represented by formula (A) (including carbazolyl and phenyl-substituted carbazolyl). 3 is a group represented by formula (A), the group represented by formula (A) is Ar 3 and combine.

[0170] Ar 4 are each independently hydrogen, phenyl, biphenylyl, terphenylyl, naphthyl, or silyl substituted with alkyl having 1 to 4 carbon atoms (eg, methyl, ethyl, t-butyl) and / or cycloalkyl having 5 to 10 carbon atoms.

[0171] Examples of the alkyl group having 1 to 4 carbon atoms that substitutes for the silyl include methyl, ethyl, propyl, i-propyl, butyl, sec-butyl, t-butyl, and cyclobutyl, and three hydrogen atoms in the silyl are each independently substituted with these alkyl groups.

[0172] Specific examples of "silyl substituted with alkyl having 1 to 4 carbon atoms" include trimethylsilyl, triethylsilyl, tripropylsilyl, tri-i-propylsilyl, tributylsilyl, tri-sec-butylsilyl, tri-t-butylsilyl, ethyldimethylsilyl, propyldimethylsilyl, i-propyldimethylsilyl, butyldimethylsilyl, sec-butyldimethylsilyl, t-butyldimethylsilyl, methyldiethylsilyl, propyldiethylsilyl, i-propyldiethylsilyl, butyldiethylsilyl, sec-butyldiethylsilyl, t-butyldiethylsilyl, methyldipropylsilyl, ethyldipropylsilyl, butyldipropylsilyl, sec-butyldipropylsilyl, t-butyldipropylsilyl, methyldi-i-propylsilyl, ethyldi-i-propylsilyl, butyldi-i-propylsilyl, sec-butyldi-i-propylsilyl, and t-butyldi-i-propylsilyl.

[0173] Examples of the cycloalkyl having 5 to 10 carbon atoms substituting the silyl include cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, norbornenyl, 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, and three hydrogen atoms in the silyl are each independently substituted with these cycloalkyls.

[0174] Specific examples of the "silyl substituted with cycloalkyl having 5 to 10 carbon atoms" include tricyclopentylsilyl and tricyclohexylsilyl.

[0175] Substituted silyls include dialkylcycloalkylsilyls, which are substituted with two alkyl groups and one cycloalkyl group, and alkyldicycloalkylsilyls, which are substituted with one alkyl group and two cycloalkyl groups. Specific examples of the alkyl and cycloalkyl groups are as described above.

[0176] In addition, hydrogen in the chemical structure of the anthracene compound represented by formula (3-H) may be substituted with a group represented by formula (A). When substituted with a group represented by formula (A), the group represented by formula (A) replaces at least one hydrogen in the compound represented by formula (3-H) at the *.

[0177] The group represented by formula (A) is one of the substituents that the anthracene compound represented by formula (3-H) may have. [ka]

[0178] In formula (A), Y is -O-, -S- or >NR 29 and R 21 ~R 28 are each independently hydrogen, optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted alkoxy, optionally substituted aryloxy, optionally substituted arylthio, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, alkyldicycloalkylsilyl, optionally substituted amino, halogen, hydroxy or cyano; R 21 ~R 28 adjacent groups among R may be bonded to each other to form a hydrocarbon ring, an aryl ring, or a heteroaryl ring; 29 is hydrogen or optionally substituted aryl. In formula (A), Y is preferably --O--.

[0179] R 21 ~R 28The "alkyl" in the "optionally substituted alkyl" may be either linear or branched, and examples thereof include linear alkyl having 1 to 24 carbon atoms or branched alkyl having 3 to 24 carbon atoms. An alkyl having 1 to 18 carbon atoms (branched alkyl having 3 to 18 carbon atoms) is 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 6 carbon atoms (branched alkyl having 3 to 6 carbon atoms) is even more preferred, and an alkyl having 1 to 4 carbon atoms (branched alkyl having 3 to 4 carbon atoms) is particularly preferred.

[0180] 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.

[0181] R 21 ~R 28 Examples of the "cycloalkyl" in the "optionally substituted cycloalkyl" include cycloalkyl having 3 to 24 carbon atoms, cycloalkyl having 3 to 20 carbon atoms, cycloalkyl having 3 to 16 carbon atoms, cycloalkyl having 3 to 14 carbon atoms, cycloalkyl having 5 to 10 carbon atoms, cycloalkyl having 5 to 8 carbon atoms, cycloalkyl having 5 to 6 carbon atoms, and cycloalkyl having 5 carbon atoms.

[0182] Specific examples of "cycloalkyl" include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, and alkyl (especially methyl) substituted derivatives of these having 1 to 4 carbon atoms, as well as 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.

[0183] R 21 ~R 28 In the above, the "aryl" in the "optionally substituted aryl" includes, for example, aryl having 6 to 30 carbon atoms, preferably aryl having 6 to 16 carbon atoms, more preferably aryl having 6 to 12 carbon atoms, and particularly preferably aryl having 6 to 10 carbon atoms.

[0184] Specific examples of "aryl" include a monocyclic ring system such as phenyl, a bicyclic ring system such as biphenylyl, a fused bicyclic ring system such as naphthyl, a tricyclic ring system such as terphenylyl (m-terphenylyl, o-terphenylyl, p-terphenylyl), a fused tricyclic ring system such as acenaphthylenyl, fluorenyl, phenalenyl, and phenanthrenyl, a fused tetracyclic ring system such as triphenylenyl, pyrenyl, and naphthacenyl, and a fused pentacyclic ring system such as perylenyl and pentacenyl.

[0185] R 21 ~R 28 Examples of the "heteroaryl" in the "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.

[0186] Specific examples of "heteroaryl" include pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, oxadiazolyl, thiadiazolyl, triazolyl, tetrazolyl, pyrazolyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, indolyl, isoindolyl, 1H-indazolyl, benzimidazolyl, benzoxazolyl, benzothiazolyl, 1H-benzotriazolyl, quinolyl, isoquinolyl, cyclohex ... Examples of such aryl groups include aryl, aryloxy, aryloxy, aryloxy, and aryloxy groups. Examples of such aryl groups include aryloxy, aryloxy, aryloxy, and aryloxy groups include aryloxy, aryloxy, and aryloxy groups. Examples of such aryl groups include aryloxy, aryloxy, and aryloxy groups include aryloxy, aryloxy, and aryloxy groups. Examples of such aryl groups include aryloxy, aryloxy, and aryloxy groups include aryloxy, aryloxy, and aryloxy groups.

[0187] R 21 ~R 28 Examples of the "alkoxy" in the "optionally substituted alkoxy" 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 4 carbon atoms (branched alkoxy having 3 to 4 carbon atoms) is particularly preferred.

[0188] Specific examples of "alkoxy" include methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, s-butoxy, t-butoxy, pentyloxy, hexyloxy, heptyloxy, octyloxy, and the like.

[0189] R 21 ~R 28The "aryloxy" in the "optionally substituted aryloxy" is a group in which the hydrogen of the -OH group is replaced by an aryl, and this aryl is the same as R 21 ~R 28 The group described as "aryl" in the above formula can be used.

[0190] R 21 ~R 28 The "arylthio" in the "optionally substituted arylthio" is a group in which the hydrogen of the -SH group is replaced by an aryl, and this aryl is the same as R 21 ~R 28 The group described as "aryl" in the above formula can be used.

[0191] R 21 ~R 28 The "trialkylsilyl" in the above formula is a silyl group in which each of the three hydrogen atoms is independently replaced by an alkyl group, and the alkyl group is the same as R 21 ~R 28 The groups described as "alkyl" in the above can be cited. Preferred alkyl groups for substitution are alkyl groups having 1 to 4 carbon atoms, and specific examples thereof include methyl, ethyl, propyl, i-propyl, butyl, sec-butyl, t-butyl, and cyclobutyl.

[0192] Specific examples of the "trialkylsilyl" include trimethylsilyl, triethylsilyl, tripropylsilyl, tri-i-propylsilyl, tributylsilyl, tri-sec-butylsilyl, tri-t-butylsilyl, ethyldimethylsilyl, propyldimethylsilyl, i-propyldimethylsilyl, butyldimethylsilyl, sec-butyldimethylsilyl, t-butyldimethylsilyl, methyldiethylsilyl, propyldiethylsilyl, i-propyldiethylsilyl, butyldiethylsilyl, sec-butyldiethylsilyl, t-butyldiethylsilyl, methyldipropylsilyl, ethyldipropylsilyl, butyldipropylsilyl, sec-butyldipropylsilyl, t-butyldipropylsilyl, methyldi-i-propylsilyl, ethyldi-i-propylsilyl, butyldi-i-propylsilyl, sec-butyldi-i-propylsilyl, and t-butyldi-i-propylsilyl.

[0193] R 21 ~R 28 The "tricycloalkylsilyl" in the above formula is a silyl group in which each of the three hydrogen atoms is independently replaced by a cycloalkyl, and the cycloalkyl is the same as R 21 ~R 28 The groups described as "cycloalkyl" in the above can be cited. Preferred cycloalkyl for substitution is cycloalkyl having 5 to 10 carbon atoms, and specific examples thereof include 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.

[0194] Specific examples of the "tricycloalkylsilyl" include tricyclopentylsilyl, tricyclohexylsilyl, and the like.

[0195] 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.

[0196] R 21 ~R 28 The "substituted amino" in the "optionally substituted amino" in the above is, for example, an amino in which two hydrogen atoms are substituted with aryl or heteroaryl. An amino in which two hydrogen atoms are substituted with aryl is a diaryl-substituted amino, an amino in which two hydrogen atoms are substituted with heteroaryl is a diheteroaryl-substituted amino, and an amino in which two hydrogen atoms are substituted with an aryl and a heteroaryl is an arylheteroaryl-substituted amino. The aryl and heteroaryl are as defined above in R 21 ~R 28 The groups described above as "aryl" and "heteroaryl" can be cited.

[0197] Specific examples of the "substituted amino" include diphenylamino, dinaphthylamino, phenylnaphthylamino, dipyridylamino, phenylpyridylamino, naphthylpyridylamino, and the like.

[0198] R 21 ~R 28 "Halogen" in the above formula includes fluorine, chlorine, bromine, and iodine.

[0199] R 21 ~R 28 Some of the groups described as may be substituted as described above, in which case the substituents include alkyl, cycloalkyl, aryl, or heteroaryl. The alkyl, cycloalkyl, aryl, or heteroaryl may be any of the groups described above as R 21 ~R 28 In the above, reference can be made to a group described as "alkyl", "cycloalkyl", "aryl" or "heteroaryl".

[0200] Y as 'NR' 29 " R in 29 is hydrogen or an optionally substituted aryl, and the aryl is as defined above in R 21 ~R 28 The group described as "aryl" in the above formula can be cited, and the substituents thereof include R 21 ~R 28 The groups described above as substituents for the above can be cited.

[0201] R 21 ~R 28 Among these, adjacent groups may be bonded to each other to form a hydrocarbon ring, an aryl ring, or a heteroaryl ring. The group represented by the following formula (A-1) does not form a ring, and the group represented by the following formulas (A-2) to (A-14) may be exemplified as the group formed with a ring. At least one hydrogen atom in the group represented by any of formulas (A-1) to (A-14) may be substituted with alkyl, cycloalkyl, aryl, heteroaryl, alkoxy, aryloxy, arylthio, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, alkyldicycloalkylsilyl, diaryl-substituted amino, diheteroaryl-substituted amino, arylheteroaryl-substituted amino, halogen, hydroxy, or cyano.

[0202] [ka]

[0203] Examples of rings formed by bonding adjacent groups to each other include a hydrocarbon ring such as a cyclohexane ring, and examples of aryl and heteroaryl rings include the above-mentioned R 21 ~R 28 Examples of the ring structures include those described in the "aryl" and "heteroaryl" in the formula (A-1), and these rings are formed so as to be condensed with one or two benzene rings in the formula (A-1).

[0204] The group represented by formula (A) is a group obtained by removing one hydrogen atom from any position of formula (A), and * indicates the position. In other words, the group represented by formula (A) may have any position as a bonding position. For example, any carbon atom on the two benzene rings in the structure of formula (A), R 21 ~R 28 An atom on any ring formed by bonding adjacent groups to each other, or ">NR 29 " R in 29 Any position in the 29 " in N(R 29 is a bond). The same applies to the groups represented by any of the formulae (A-1) to (A-14).

[0205] Examples of the group represented by formula (A) include groups represented by any of formulas (A-1) to (A-14). Groups represented by any of formulas (A-1) to (A-5) and (A-12) to (A-14) are preferred. Groups represented by any of formulas (A-1) to (A-4) are more preferred. Groups represented by any of formulas (A-1), (A-3) and (A-4) are even more preferred. Groups represented by formula (A-1) are particularly preferred.

[0206] Examples of the group represented by formula (A) include the following groups: In the formula, Y and * are defined as above. [ka]

[0207] [ka]

[0208] In the compound represented by formula (3-H), the group represented by formula (A) is a naphthalene ring in formula (3-X1) or formula (3-X2), a single bond in formula (3-X3), and / or Ar in formula (3-X3). 3 The form in which it is bound to is preferred.

[0209] All or a part of the hydrogen atoms in the chemical structure of the anthracene compound represented by formula (3-H) may be deuterium atoms.

[0210] The anthracene-based compound as the host may be, for example, a compound represented by the following formula (3-H2). [ka]

[0211] In formula (3-H2), Ar c is optionally substituted aryl or optionally substituted heteroaryl, R c is hydrogen, alkyl, or cycloalkyl; Ar 11 , Ar 12 , Ar 13 , Ar 14 , Ar 15 , Ar 16 , Ar 17 , and Ar 18 are each independently hydrogen, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted diarylamino, optionally substituted diheteroarylamino, optionally substituted arylheteroarylamino, optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted alkenyl, optionally substituted alkoxy, optionally substituted aryloxy, optionally substituted arylthio, or optionally substituted silyl, and at least one hydrogen in the compound represented by formula (3-H2) is optionally substituted with halogen, cyano, or deuterium.

[0212] In formula (3-H2), the definition of "optionally substituted aryl", "optionally substituted heteroaryl", "optionally substituted diarylamino", "optionally substituted diheteroarylamino", "optionally substituted arylheteroarylamino", "optionally substituted alkyl", "optionally substituted cycloalkyl", "optionally substituted alkenyl", "optionally substituted alkoxy", "optionally substituted aryloxy", "optionally substituted arylthio", or "optionally substituted silyl" is the same as that in formula (3-H) above, and the explanation in formula (1) can be cited.

[0213] The "optionally substituted aryl" is also preferably a group represented by any one of the following formulae (3-H2-X1) to (3-H2-X7).

[0214] [ka]

[0215] In formulae (3-H2-X1) to (3-H2-X7), * indicates a bond position. In the formulae (3-H2-X1) to (3-H2-X3), Ar 21 , Ar 22 , and Ar 23 are each independently hydrogen, phenyl, biphenylyl, terphenylyl, quaterphenylyl, naphthyl, phenanthryl, fluorenyl, benzofluorenyl, chrysenyl, triphenylenyl, pyrenyl, anthracenyl, or a group represented by formula (A). In the explanation of formula (3-H2), the group represented by formula (A) is the same as that explained in the anthracene compound represented by formula (3-H).

[0216] In the formulae (3-H2-X4) to (3-H2-X7), Ar 24 , Ar 25 , Ar 26 , Ar 27 and Ar 28are each independently hydrogen, phenyl, biphenylyl, terphenylyl, naphthyl, phenanthryl, fluorenyl, chrysenyl, triphenylenyl, pyrenyl, or a group represented by formula (A). In addition, any one or more hydrogen atoms in each of the groups represented by formulae (3-H2-X1) to (3-H2-X7) may be substituted with an alkyl group having 1 to 6 carbon atoms (preferably methyl or t-butyl).

[0217] Furthermore, preferred examples of the "optionally substituted aryl" include terphenylyl (particularly m-terphenyl-5'-yl) which may be substituted with one or more substituents selected from the group consisting of phenyl, biphenylyl, terphenylyl, naphthyl, phenanthryl, fluorenyl, chrysenyl, triphenylenyl, pyrenyl, and a group represented by formula (A).

[0218] The "optionally substituted heteroaryl" also includes a group represented by formula (A). Other specific examples of the "optionally substituted aryl" and the "optionally substituted heteroaryl" include dibenzofuryl, naphthobenzofuryl, phenyl-substituted dibenzofuryl, and the like.

[0219] At least one hydrogen atom in the compound represented by formula (3-H2) may be replaced by a halogen atom, a cyano atom, or a deuterium atom. In this case, "halogen" includes fluorine, chlorine, bromine, and iodine. In particular, the compound represented by formula (3-H2) in which all hydrogen atoms are replaced by deuterium atoms is preferred.

[0220] In formula (3-H2), R c is hydrogen, alkyl, or cycloalkyl, preferably hydrogen, methyl, or t-butyl, and more preferably hydrogen. In formula (3-H2), Ar 11 ~Ar 18It is preferable that at least two of the groups are optionally substituted aryl or optionally substituted heteroaryl. That is, it is preferable that the anthracene compound represented by formula (3-H2) has a structure in which at least three substituents selected from the group consisting of optionally substituted aryl and optionally substituted heteroaryl are bonded to the anthracene ring.

[0221] The anthracene compound represented by formula (3-H2) is Ar 11 ~Ar 18 It is more preferable that two of the groups are optionally substituted aryl or optionally substituted heteroaryl, and the other six are hydrogen, optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted alkenyl, or optionally substituted alkoxy. That is, it is more preferable that the anthracene compound represented by formula (3-H2) has a structure in which three substituents selected from the group consisting of optionally substituted aryl and optionally substituted heteroaryl are bonded to the anthracene ring.

[0222] The anthracene compound represented by formula (3-H2) is Ar 11 ~Ar 18 It is more preferred that any two of are optionally substituted aryl or optionally substituted heteroaryl, and the other six are hydrogen, methyl, or t-butyl.

[0223] Furthermore, in formula (3-H2), R c is hydrogen and Ar 11 ~Ar 18 It is preferred that any six of these are hydrogen.

[0224] The anthracene compound represented by formula (3-H2) is preferably an anthracene compound represented by the following formula (3-H2-A), (3-H2-B), (3-H2-C), (3-H2-D), or (3-H2-E). [ka]

[0225] In the formula (3-H2-A), (3-H2-B), (3-H2-C), (3-H2-D) or (3-H2-E), Ar c ', Ar 11 ', Ar 12 ', Ar 13 ', Ar 14 ', Ar 15 ', Ar 17 ', and Ar 18 ' are each independently phenyl, biphenylyl, terphenylyl, quaterphenylyl, naphthyl, phenanthryl, fluorenyl, benzofluorenyl, chrysenyl, triphenylenyl, pyrenyl, or a group represented by formula (A), and at least one hydrogen atom in these groups may be substituted with phenyl, biphenylyl, terphenylyl, quaterphenylyl, naphthyl, phenanthryl, fluorenyl, benzofluorenyl, chrysenyl, triphenylenyl, pyrenyl, or a group represented by formula (A). Here, when both hydrogen atoms of the methylene in fluorenyl and benzofluorenyl are substituted with phenyl, these phenyls may be bonded to each other by a single bond. Ar c ', Ar 11 ', Ar 12 ', Ar 13 ', Ar 14 ', Ar 15 ', Ar 17 ', and Ar 18 Carbon atoms of the anthracene ring that are not bonded with ' may have methyl or t-butyl bonded instead of hydrogen.

[0226] Ar c ', Ar 11 ', Ar 12 ', Ar 13 ', Ar 14 ', Ar 15 ', Ar 17 ', and Ar 18When each of "1" and "2" is a substituted or unsubstituted phenyl or a substituted or unsubstituted naphthyl, it is preferably a group represented by any one of the above formulae (3-H2-X1) to (3-H2-X7).

[0227] Ar c ', Ar 11 ', Ar 12 ', Ar 13 ', Ar 14 ', Ar 15 ', Ar 17 ', and Ar 18 More preferably, each ' is independently phenyl, biphenylyl (particularly biphenyl-2-yl or biphenyl-4-yl), terphenylyl (particularly m-terphenyl-5'-yl), naphthyl, phenanthryl, fluorenyl, or a group represented by any one of the above formulas (A-1) to (A-4), and in this case, at least one hydrogen atom in these groups may be substituted by phenyl, biphenylyl, naphthyl, phenanthryl, fluorenyl, or a group represented by any one of the above formulas (A-1) to (A-4).

[0228] In addition, at least one hydrogen atom in the compound represented by formula (3-H2-A), (3-H2-B), (3-H2-C), (3-H2-D), or (3-H2-E) may be substituted with halogen, cyano, or deuterium.

[0229] Particularly preferred anthracene compounds represented by formula (3-H2) include anthracene compounds represented by formula (3-H2-Aa) below. [ka]

[0230] In formula (3-H2-Aa), Ar c ', Ar 14 ', and Ar 15Each of the ' is independently phenyl, biphenylyl, terphenylyl, naphthyl, phenanthryl, fluorenyl, benzofluorenyl, chrysenyl, triphenylenyl, pyrenyl, or a group represented by any one of the above formulas (A-1) to (A-14), and at least one hydrogen atom in these groups may be substituted with phenyl, biphenylyl, terphenylyl, naphthyl, phenanthryl, fluorenyl, benzofluorenyl, chrysenyl, triphenylenyl, pyrenyl, or a group represented by any one of the formulas (A-1) to (A-14). When both hydrogen atoms of the methylene in the fluorenyl and benzofluorenyl are substituted with phenyl, these phenyls may be bonded to each other by a single bond. In addition, Ar c ', Ar 14 ', and Ar 15 A carbon atom on the anthracene ring to which ' is not bonded may be substituted with methyl or t-butyl instead of hydrogen. At least one hydrogen in the compound represented by formula (3-H2-Aa) may be substituted with halogen or cyano, and at least one hydrogen in the compound represented by formula (3-H2-Aa) is substituted with deuterium.

[0231] In formula (3-H2-Aa), Ar c ', Ar 14 ', and Ar 15 Each ' is preferably independently phenyl, biphenylyl, terphenylyl, naphthyl, phenanthryl, fluorenyl, or a group represented by any one of the above formulas (A-1) to (A-4), and at least one hydrogen in these groups may be substituted by phenyl, naphthyl, phenanthryl, fluorenyl, or a group represented by any one of the above formulas (A-1) to (A-4).

[0232] In the compound represented by formula (3-H2-Aa), at least the carbon at the 10-position of the anthracene ring (Ar cIt is preferable that the hydrogen bonded to the carbon atom to which Ar′ is bonded (the carbon atom to which Ar′ is bonded is the 9th position) is replaced with deuterium. That is, the compound represented by formula (3-H2-Aa) is preferably a compound represented by the following formula (3-H2-Ab). In formula (3-H2-Ab), D is deuterium, and c ', Ar 14 ', and Ar 15 ' is the same as defined in formula (3-H2-Aa). D in formula (3-H2-Ab) indicates that at least this position is deuterium, and any one or more other hydrogens in formula (3-H2-Aa) may be deuterium at the same time, and it is also preferable that all hydrogens in formula (3-H2-Aa) are deuterium.

[0233] [ka]

[0234] Specific examples of anthracene compounds include compounds represented by the following formulas: In the structural formulas, "Me" represents methyl, "D" represents deuterium, and "tBu" represents t-butyl.

[0235] [ka]

[0236] [ka]

[0237] [ka]

[0238] [ka]

[0239] [ka]

[0240] [ka]

[0241] [ka]

[0242] [ka]

[0243] Other specific examples of the anthracene compounds include the compounds represented by the following formulae (3-131-Y) to (3-179-Y), the compounds represented by the following formulae (3-180-Y) to (3-182-Y), the compounds represented by the following formulae (3-183-N), the compounds represented by the following formulae (3-184-Y) to (3-254-Y), (3-254-Y) to (3-269-Y), and the compounds represented by the following formulae (3-500) to (3-557). In the compounds represented by the following formulae (3-131-Y) to (3-179-Y), the compounds represented by the following formulae (3-180-Y) to (3-182-Y), the compounds represented by the following formulae (3-183-N), the compounds represented by the following formulae (3-184-Y) to (3-254-Y), the compounds represented by the following formulae (3-254-Y) to (3-269-Y), and the compounds represented by the following formulae (3-500) to (3-557), hydrogen atoms may be partially or completely replaced with deuterium. In the formulae, Y is -O-, -S-, >NR 29 (R 29 is defined as above) or >C(-R 30 )2(R 30 R may be either an optionally linked aryl or an alkyl; 29 For example, phenyl, R 30 For example, is methyl. For formula numbers, for example, when Y is O, formula (3-131-Y) is formula (3-131-O), and Y is -S- or >NR 29 In the case of (3-131-S) or (3-131-N), respectively, use formula (3-131-S) or formula (3-131-N).

[0244]

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[0245]

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[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]

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[0257]

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[0258]

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[0259]

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[0260]

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[0261]

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[0262]

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[0263] Among these compounds, the compounds of formula (3-131-Y) to formula (3-134-Y), formula (3-138-Y), formula (3-140-Y) to formula (3-143-Y), formula (3-150-Y), formula (3-153-Y) to formula (3-156-Y), formula (3-166-Y), formula (3-168-Y), formula (3-173-Y), formula (3-177-Y), formula (3-180-Y) to formula (3-183-N), formula (3-185-Y), formula (3-19 Compounds represented by the formulas (3-0-Y), (3-223-Y), (3-241-Y), (3-250-Y), (3-252-Y) to (3-254-Y), (3-501), (3-507), (3-508), (3-509), (3-513), (3-514), (3-519), (3-521), (3-538) to (3-547), or (3-600) to (3-620) are preferred. Y is preferably -O-.

[0264] The above anthracene-based compound is a compound having a reactive group at a desired position of the anthracene skeleton, and an anthracene-based compound represented by formula (3-H) is a compound having a reactive group at a desired position of the anthracene skeleton, and X, Ar 4 The compound having a reactive group in a partial structure such as the structure of formula (A) can be used as a starting material to produce the compound by applying Suzuki coupling, Negishi coupling, or other known coupling reactions. Examples of reactive groups in these reactive compounds include halogens and boronic acids. As a specific production method, for example, the synthesis methods in paragraphs

[0089] to

[0175] of International Publication No. 2014 / 141725 can be used as a reference.

[0265] <Fluorene-based compounds> The compound represented by formula (4-H) basically functions as a host. [ka]

[0266] In formula (4-H), R 1 From R 10are each independently a hydrogen atom, an aryl atom, a heteroaryl atom (wherein the heteroaryl atom may be bonded to the fluorene skeleton in formula (4-H) via a linking group), a diarylamino atom, a diheteroarylamino atom, an arylheteroarylamino atom, an alkyl atom, a cycloalkyl atom, an alkenyl atom, an alkoxy atom, or an aryloxy atom, in which at least one hydrogen atom may be substituted with an aryl atom, a heteroaryl atom, an alkyl atom, or a cycloalkyl atom; Also, R 1 and R 2 , R 2 and R 3 , R 3 and R 4 , R 5 and R 6 , R 6 and R 7 , R 7 and R 8 or R 9 and R 10 may each independently bond to form a fused ring or a spiro ring, and at least one hydrogen in the formed ring may be replaced with an aryl, a heteroaryl (the heteroaryl may be bonded to the formed ring via a linking group), a diarylamino, a diheteroarylamino, an arylheteroarylamino, an alkyl, a cycloalkyl, an alkenyl, an alkoxy, or an aryloxy, and at least one hydrogen in these may be replaced with an aryl, a heteroaryl, an alkyl, or a cycloalkyl; At least one hydrogen in the compound represented by formula (4-H) may be substituted with halogen, cyano or deuterium.

[0267] For details of each group in the definition of formula (4-H), the explanation for formula (1) above can be cited.

[0268] R 1 From R 10Examples of the alkenyl in the above formula include alkenyl having 2 to 30 carbon atoms, preferably alkenyl having 2 to 20 carbon atoms, more preferably alkenyl having 2 to 10 carbon atoms, further preferably alkenyl having 2 to 6 carbon atoms, and particularly preferably alkenyl having 2 to 4 carbon atoms. Preferred alkenyls are vinyl, 1-propenyl, 2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, or 5-hexenyl.

[0269] Specific examples of heteroaryl include monovalent groups represented by removing any one hydrogen atom from a compound of the following formula (4-Ar1), formula (4-Ar2), formula (4-Ar3), formula (4-Ar4), or formula (4-Ar5).

[0270] [ka]

[0271] In formulas (4-Ar1) to (4-Ar5), Y 1 are each independently O, S or NR, R is phenyl, biphenylyl, naphthyl, anthracenyl or hydrogen; At least one hydrogen atom in the structures of formulae (4-Ar1) to (4-Ar5) may be substituted with phenyl, biphenylyl, naphthyl, anthracenyl, phenanthrenyl, methyl, ethyl, propyl, or butyl.

[0272] These heteroaryls may be bonded to the fluorene skeleton in formula (4-H) via a linking group. That is, the fluorene skeleton in formula (4-H) and the heteroaryl may be bonded directly, or may be bonded to each other via a linking group. Examples of the linking group include phenylene, biphenylene, naphthylene, anthracenylene, methylene, ethylene, -OCH2CH2-, -CH2CH2O-, or -OCH2CH2O-.

[0273] In addition, R in formula (4-H) 1 and R 2 , R 2 and R 3 , R 3 and R 4 , R 5 and R 6 , R 6 and R 7 or R 7 and R 8 are each independently bonded to form a fused ring, R 9 and R 10 may be bonded to form a spiro ring. 1 From R 8 The fused ring formed by is a ring fused to the benzene ring in formula (4-H), and is an aliphatic ring or an aromatic ring. An aromatic ring is preferable, and examples of the structure including the benzene ring in formula (4-H) include a naphthalene ring and a phenanthrene ring. 9 and R 10 The spiro ring formed by the formula (4-H) is a ring that is spiro-bonded to the five-membered ring in formula (4-H), and is an aliphatic ring or an aromatic ring. An aromatic ring, such as a fluorene ring, is preferred.

[0274] The compound represented by formula (4-H) is preferably a compound represented by the following formula (4-H-1), formula (4-H-2) or formula (4-H-3), 1 and R 2 In the formula (4-H), R 3 and R 4 In the formula (4-H), R 1 From R 8 is a compound in which none of the above is bound.

[0275] [ka]

[0276] R in formula (4-H-1), formula (4-H-2) and formula (4-H-3) 1From R 10 The definition of R in formula (4-H) corresponds to 1 From R 10 is the same as R in formula (4-H-1) and formula (4-H-2). 11 From R 14 The definition of R in formula (4-H) 1 From R 10 is the same as:

[0277] The compound represented by formula (4-H) is more preferably a compound represented by the following formula (4-H-1A), formula (4-H-2A) or formula (4-H-3A), in which R 9 and R 10 is a compound in which a spiro-fluorene ring is formed by bonding.

[0278] [ka]

[0279] R in formula (4-1A), formula (4-2A) and formula (4-3A) 2 From R 7 The definition of is the corresponding R in formula (4-1), formula (4-2) and formula (4-3). 2 From R 7 and R in formula (4-1A) and formula (4-2A) 11 From R 14 The definition of R in formula (4-1) and formula (4-2) 11 From R 14 is the same as:

[0280] In addition, all or a part of the hydrogen atoms in the compound represented by formula (4-H) may be substituted with halogen, cyano or deuterium.

[0281] More specific examples of the fluorene-based compound as the host of the present invention include compounds represented by the following structural formula: In addition, "Me" represents methyl. [ka]

[0282] <Dibenzochrysene compounds> The dibenzochrysene compound as the host is, for example, a compound represented by the following formula (5-H). [ka]

[0283] In formula (5-H), R 1 From R 16 are each independently a hydrogen atom, an aryl atom, a heteroaryl atom (wherein the heteroaryl atom may be bonded to the dibenzochrysene skeleton in formula (5-H) via a linking group), a diarylamino atom, a diheteroarylamino atom, an arylheteroarylamino atom, an alkyl atom, a cycloalkyl atom, an alkenyl atom, an alkoxy atom, or an aryloxy atom, in which at least one hydrogen atom may be substituted with an aryl atom, a heteroaryl atom, an alkyl atom, or a cycloalkyl atom; Also, R 1 From R 16 adjacent groups among these may be bonded to each other to form a condensed ring, and at least one hydrogen atom in the formed ring may be substituted with an aryl, a heteroaryl (the heteroaryl may be bonded to the formed ring via a linking group), a diarylamino, a diheteroarylamino, an arylheteroarylamino, an alkyl, a cycloalkyl, an alkenyl, an alkoxy, or an aryloxy, and at least one hydrogen atom in these may be substituted with an aryl, a heteroaryl, an alkyl, or a cycloalkyl; At least one hydrogen in the compound represented by formula (5-H) may be substituted with halogen, cyano or deuterium.

[0284] For details of each group in the definition of formula (5-H), the explanation for formula (1) above can be cited.

[0285] The alkenyl in the definition of formula (5-H) is, for example, an alkenyl having 2 to 30 carbon atoms, preferably an alkenyl having 2 to 20 carbon atoms, more preferably an alkenyl having 2 to 10 carbon atoms, further preferably an alkenyl having 2 to 6 carbon atoms, and particularly preferably an alkenyl having 2 to 4 carbon atoms. Preferred alkenyls are vinyl, 1-propenyl, 2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, or 5-hexenyl.

[0286] Specific examples of heteroaryl include monovalent groups represented by removing any one hydrogen atom from a compound of the following formula (5-Ar1), formula (5-Ar2), formula (5-Ar3), formula (5-Ar4), or formula (5-Ar5).

[0287] [ka]

[0288] In formula (5-Ar1) to formula (5-Ar5), Y 1 are each independently O, S or NR, R is phenyl, biphenylyl, naphthyl, anthracenyl or hydrogen; At least one hydrogen atom in the structures of formulae (5-Ar1) to (5-Ar5) may be substituted with phenyl, biphenylyl, naphthyl, anthracenyl, phenanthrenyl, methyl, ethyl, propyl, or butyl.

[0289] These heteroaryls may be bonded to the dibenzochrysene skeleton in formula (5-H) via a linking group. That is, the dibenzochrysene skeleton and the heteroaryl in formula (5-H) may be bonded directly, or may be bonded to each other via a linking group. Examples of the linking group include phenylene, biphenylene, naphthylene, anthracenylene, methylene, ethylene, -OCH2CH2-, -CH2CH2O-, or -OCH2CH2O-.

[0290] The compound represented by formula (5-H) is preferably R 1 , R 4 , R 5 , R 8 , R 9 , R 12 , R 13 and R 16 is hydrogen. In this case, R in formula (5-H) 2 , R 3 , R 6 , R 7 , R 10 , R 11 , R 14 and R 15 are preferably each independently hydrogen, phenyl, biphenylyl, naphthyl, anthracenyl, phenanthrenyl, a monovalent group having a structure of formula (5-Ar1), (5-Ar2), (5-Ar3), (5-Ar4) or (5-Ar5) (the monovalent group having the structure may be bonded to the dibenzochrysene skeleton in formula (5-H) via phenylene, biphenylene, naphthylene, anthracenylene, methylene, ethylene, -OCHCH-, -CHCHO- or -OCHCHO-), methyl, ethyl, propyl or butyl.

[0291] The compound represented by formula (5-H) is more preferably 1 , R 2 , R 4 , R 5 , R 7 , R 8 , R 9 , R 10 , R 12 , R 13 , R 15 and R 16 is hydrogen. In this case, R in formula (5-H) 3 , R 6 , R 11 and R 14at least one (preferably one or two, more preferably one) of is a single bond, phenylene, biphenylene, naphthylene, anthracenylene, methylene, ethylene, -OCHCH-, -CHCHO-, or a monovalent group having a structure of formula (5-Ar1), formula (5-Ar2), formula (5-Ar3), formula (5-Ar4) or formula (5-Ar5) via -OCHCHO-; The other than the at least one (i.e., other than the position substituted by the monovalent group having the structure) is hydrogen, phenyl, biphenylyl, naphthyl, anthracenyl, methyl, ethyl, propyl, or butyl, and at least one hydrogen in these may be substituted with phenyl, biphenylyl, naphthyl, anthracenyl, methyl, ethyl, propyl, or butyl.

[0292] In addition, R in formula (5-H) 2 , R 3 , R 6 , R 7 , R 10 , R 11 , R 14 and R 15 When a monovalent group having a structure represented by formula (5-Ar1) to formula (5-Ar5) is selected as the aryl group, at least one hydrogen atom in the structure is selected from the group represented by formula (5-Ar1) to formula (5-Ar5). 1 From R 16 may be bonded to any one of the following to form a single bond.

[0293] More specific examples of the dibenzochrysene compound as the host of the present invention include compounds represented by the following structural formula: In addition, "tBu" represents t-butyl. [ka]

[0294] [ka]

[0295] The above-mentioned light-emitting layer materials (host materials and dopant materials) can be used as light-emitting layer materials in the form of polymer compounds obtained by polymerizing a reactive compound substituted with a reactive substituent as a monomer, or crosslinked polymers thereof, or pendant polymer compounds obtained by reacting a main-chain polymer with the reactive compound, or crosslinked pendant polymers thereof. In this case, the above description of the polycyclic aromatic compound containing a structural unit represented by formula (1) can be cited as the reactive substituent. The applications of such polymer compounds and crosslinked polymers will be described in detail below.

[0296] <Example of polymer host material> [ka]

[0297] In formula (SPH-1), Each MU is independently a divalent aromatic group, each EC is independently a monovalent aromatic group, two hydrogens in MU are replaced by EC or MU, and k is an integer of 2 to 50,000.

[0298] More specifically, Each MU is independently arylene, heteroarylene, diarylenarylamino, diarylenarylboryl, oxaborine-diyl, or azaborine-diyl; each E C is independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, or aryloxy; At least one hydrogen in MU and EC may be further substituted with aryl, heteroaryl, diarylamino, alkyl, and cycloalkyl; k is an integer from 2 to 50,000. k is preferably an integer from 20 to 50,000, and more preferably an integer from 100 to 50,000.

[0299] At least one hydrogen atom in MU and EC in formula (SPH-1) 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 (SPH-1) 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.

[0300] 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]

[0301] More specifically, the divalent group may be any of the following structures: In these, MU bonds to another MU or EC at *.

[0302] [ka]

[0303] [ka]

[0304] [ka]

[0305] [ka]

[0306] [ka]

[0307] [ka]

[0308] [ka]

[0309] [ka]

[0310] [ka]

[0311] Examples of EC include a monovalent group represented by any of the following structures: In these, EC is bonded to MU at *.

[0312] [ka]

[0313] [ka]

[0314] From the viewpoint of solubility and coating film-forming property, the compound represented by formula (SPH-1) is preferably such that 10 to 100% of the total number of MUs (k) in the molecule have an alkyl having 1 to 24 carbon atoms, more preferably 30 to 100% of the total number of MUs (k) in the molecule have an alkyl having 1 to 18 carbon atoms (branched chain alkyl having 3 to 18 carbon atoms), and even more preferably 50 to 100% of the total number of MUs (k) in the molecule have an alkyl having 1 to 12 carbon atoms (branched chain alkyl having 3 to 12 carbon atoms). On the other hand, from the viewpoint of in-plane orientation and charge transport, it is preferable that 10 to 100% of the total number of MUs (k) in the molecule have an alkyl having 7 to 24 carbon atoms, and more preferably 30 to 100% of the total number of MUs (k) in the molecule have an alkyl having 7 to 24 carbon atoms (branched chain alkyl having 7 to 24 carbon atoms).

[0315] Light-emitting layer including an assisting dopant and an emitting dopant The light-emitting layer in the organic electroluminescent device may contain a host compound as a first component, an assisting dopant (compound) as a second component, and an emitting dopant (compound) as a third component. The polycyclic aromatic compound of the present invention is also preferably used as an emitting dopant. As the assisting dopant (compound), a thermally activated delayed phosphor can be used.

[0316] In the following description, an organic electroluminescent device that uses a thermally activated delayed fluorescent material as an assisting dopant may be referred to as a "TAF device" (TADF Assisting Fluorescence device). The "host compound" in a TAF element means a compound whose excited singlet energy level, determined from the shoulder on the short-wavelength side of the peak of the fluorescence spectrum, is higher than that of the thermally activated delayed phosphor as the second component and the emitting dopant as the third component. The term "thermally activated delayed fluorescent material" refers to a compound that absorbs thermal energy, undergoes reverse intersystem crossing from an excited triplet state to an excited singlet state, and is radiatively deactivated from the excited singlet state to emit delayed fluorescence. However, the term "thermally activated delayed fluorescent material" also includes compounds that undergo a higher triplet state during the excitation process from the excited triplet state to the excited singlet state. For example, there are a paper by Monkman et al. of Durham University (NATURE COMMUNICATIONS,7:13680,DOI: 10.1038 / ncomms13680), a paper by Hosokai et al. of the National Institute of Advanced Industrial Science and Technology (Hosokai et al., Sci. Adv. 2017;3: e1603282), a paper by Sato et al. of Kyoto University (Scientific Reports,7:4820, DOI:10.1038 / s41598-017-05007-7), and an academic presentation by Sato et al. of Kyoto University (98th Annual Meeting of the Chemical Society of Japan, presentation number: 2I4-15, Mechanism of highly efficient light emission in organic electroluminescence using DABNA as an emitting molecule, Graduate School of Engineering, Kyoto University). In the present invention, when a sample containing a target compound is measured for its fluorescence lifetime at 300K, if a slow fluorescent component is observed, the target compound is determined to be a "thermally activated delayed fluorescent substance." Here, a slow fluorescent component refers to a component whose fluorescence lifetime is 0.1 μsec or longer. The fluorescence lifetime can be measured, for example, using a fluorescence lifetime measuring device (manufactured by Hamamatsu Photonics, C11367-01). The polycyclic aromatic compound of the present invention can function as an emitting dopant, and the "thermally activated delayed phosphor" can function as an assisting dopant that assists the emission of the polycyclic aromatic compound of the present invention.

[0317] Figure 2 shows the energy level diagram of the emission layer of a TAF element using a general fluorescent dopant as the emitting dopant (ED). In the diagram, the ground state energy level of the host is E(1,G), the excited singlet energy level obtained from the short wavelength shoulder of the fluorescence spectrum of the host is E(1,S,Sh), the excited triplet energy level obtained from the short wavelength shoulder of the phosphorescence spectrum of the host is E(1,T,Sh), the ground state energy level of the assisting dopant, which is the second component, is E(2,G), the excited singlet energy level obtained from the short wavelength shoulder of the fluorescence spectrum of the assisting dopant, which is the second component, is E(2,S,Sh), and the excited triplet energy level obtained from the short wavelength shoulder of the fluorescence spectrum of the assisting dopant, which is the second component, is E(2,T,Sh). The excited triplet energy level obtained from the shoulder on the short wavelength side of the phosphorescence spectrum of the assisting dopant is E(2,T,Sh), the ground state energy level of the emitting dopant, which is the third component, is E(3,G), the excited singlet energy level obtained from the shoulder on the short wavelength side of the fluorescence spectrum of the emitting dopant, which is the third component, is E(3,S,Sh), and the excited triplet energy level obtained from the shoulder on the short wavelength side of the phosphorescence spectrum of the emitting dopant, which is the third component, is E(3,T,Sh). In a TAF element, when a general fluorescent dopant is used as an emitting dopant (ED), the energy upconverted by the assisting dopant is transferred to the excited singlet energy level E(3,S,Sh) of the emitting dopant and emits light. However, some of the excited triplet energy E(2,T,Sh) on the assisting dopant is transferred to the excited triplet energy level E(3,T,Sh) of the emitting dopant, or intersystem crossing occurs from the excited singlet energy level E(3,S,Sh) to the excited triplet energy level E(3,T,Sh) on the emitting dopant, and then thermally deactivates to the ground state E(3,G). Due to this pathway, some of the energy is not used for light emission, resulting in energy waste.

[0318] In contrast, in the organic electroluminescent device of this embodiment, the energy transferred from the assisting dopant to the emitting dopant can be efficiently utilized for light emission, thereby achieving high light emission efficiency. This is presumably due to the following light emission mechanism. A preferred energy relationship in the organic electroluminescent device of this embodiment is shown in FIG. 3. In the organic electroluminescent device of this embodiment, the compound having a boron atom as the emitting dopant has a high excited triplet energy level E(3,T,Sh). Therefore, even if the excited singlet energy upconverted by the assisting dopant undergoes intersystem crossing to the excited triplet energy level E(3,T,Sh) by the emitting dopant, it is upconverted on the emitting dopant or recovered to the excited triplet energy level E(2,T,Sh) on the assisting dopant (thermally activated delayed phosphor). Therefore, the generated excited energy can be used for emission without waste. In addition, by dividing the functions of upconversion and emission into two types of molecules that are good at each, it is expected that the residence time of high energy will be reduced and the burden on the compound will be reduced. In this embodiment, the host compound may be a known one, for example, a compound having at least one of a carbazole ring and a furan ring, and among them, it is preferable to use a compound in which at least one of a furanyl and a carbazolyl is bonded to at least one of an arylene and a heteroarylene.Specific examples include mCP and mCBP.

[0319] The triplet energy level E(1,T,Sh) obtained from the shoulder on the short wavelength side of the peak of the phosphorescence spectrum of the host compound is preferably higher than the triplet energy levels E(2,T,Sh) and E(3,T,Sh) of the emitting dopant or assisting dopant having the highest triplet energy level in the emitting layer, from the viewpoint of promoting TADF generation in the emitting layer without inhibiting it. Specifically, the triplet energy level E(1,T,Sh) of the host compound is preferably 0.01 eV or more, more preferably 0.03 eV or more, and even more preferably 0.1 eV or more, compared to E(2,T,Sh) and E(3,T,Sh). A TADF-active compound may be used as the host compound.

[0320] As the host compound, for example, a compound represented by any one of the above formulas (H1), (H2) and (H3) can be used.

[0321] <Thermal activated delayed phosphor (assisting dopant)> The thermally activated delayed phosphor (TADF compound) used in the TAF element is preferably a donor-acceptor type thermally activated delayed phosphor (DA type TADF compound) designed to localize the HOMO (highest occupied molecular orbital) and LUMO (lowest unoccupied molecular orbital) in the molecule using an electron-donating substituent called a donor and an electron-accepting substituent called an acceptor, thereby causing efficient reverse intersystem crossing. In this specification, the term "electron-donating substituent" (donor) refers to a substituent or partial structure in which the HOMO orbital is localized in the thermally activated delayed fluorescent substance molecule, and the term "electron-accepting substituent" (acceptor) refers to a substituent or partial structure in which the LUMO orbital is localized in the thermally activated delayed fluorescent substance molecule. In general, thermally activated delayed phosphors using donors or acceptors have a large spin orbit coupling (SOC) due to their structure, and a small exchange interaction between HOMO and LUMO, resulting in a small ΔE(ST), resulting in a very fast reverse intersystem crossing rate. On the other hand, thermally activated delayed phosphors 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.

[0322] As the thermally activated delayed phosphor in the TAF element, for example, a compound in which a donor and an acceptor are bonded directly or via a spacer can be used. As the donor and acceptor structures used in the thermally activated delayed phosphor of the present invention, for example, the structures described in Chemistry of Materials, 2017, 29, 1946-1963 can be used. Examples of donor structures include 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. Acceptor structures include sulfonyldibenzene, benzophenone, phenylenebis(phenylmethanone), benzonitrile, isonicotinonitrile, phthalonitrile, isophthalonitrile, paraphthalonitrile, benzenetricarbonitrile, triazole, oxazole, thiadiazole, benzothiazole, benzobis(thiazole), benzoxazole, benzobis(oxazole), quinoline, benzimidazole, dibenzoquinoxaline, heptaazaphenalene, thioxanthone dioxide, dimethylanthracenone, anthracenedione, cycloheptabipyridine, fluorene dicarbonitrile, triephenyltriazine, pyrazinedicarbonitrile, pyrimidine, phenylpyrimidine, methylpyrimidine, pyridinedicarbonitrile, dibenzoquinoxalinedicarbonitrile, bis(phenylsulfonyl)benzene, dimethylthioxanthene dioxide, thianthrene tetraoxide, and tris(dimethylphenyl)borane.In particular, the compound having thermally activated delayed fluorescence in the TAF element is preferably a compound having at least one partial structure selected from carbazole, phenoxazine, acridine, triazine, pyrimidine, pyrazine, thioxanthene, benzonitrile, phthalonitrile, isophthalonitrile, diphenylsulfone, triazole, oxadiazole, thiadiazole, and benzophenone.

[0323] The compound used as the second component of the light-emitting layer in the TAF element is preferably a thermally activated delayed phosphor, and the emission spectrum of the compound is at least partially overlapped with the absorption peak of the emitting dopant. In the following, compounds that can be used as the second component (thermally activated delayed phosphor) of the light-emitting layer in the TAF element are exemplified. However, the compounds that can be used as the thermally activated delayed phosphor in the TAF element are not limited to the following exemplified compounds. In the following formula, Me represents methyl, t-Bu represents t-butyl, Ph represents phenyl, and the wavy line represents a bond position.

[0324] [ka]

[0325] [ka]

[0326] [ka]

[0327] [ka]

[0328] [ka]

[0329]

change

[0330]

change

[0331]

change

[0332]

change

[0333]

change

[0334]

change

[0335]

change

[0336]

change

[0337]

change

[0338]

change

[0339]

change

[0340] [ka]

[0341] [ka]

[0342] [ka]

[0343] Furthermore, as the thermally activated delayed phosphor, a compound represented by any one of the following formulae (AD1), (AD2) and (AD3) can also be used. [ka]

[0344] In the above formulas (AD1), (AD2) and (AD3), M is each independently a single bond, -O-, >N-Ar or >CAr2, and is preferably a single bond, -O- or >N-Ar from the viewpoint of the depth of the HOMO of the partial structure to be formed and the height of the excited singlet energy level and the excited triplet energy level. J is a linking group that functions as a spacer structure that separates the donor partial structure and the acceptor partial structure, and is each independently an arylene having 6 to 18 carbon atoms, and is preferably an arylene having 6 to 12 carbon atoms from the viewpoint of the magnitude of the conjugation that exudes from the donor partial structure and the acceptor partial structure. More specifically, phenylene, methylphenylene and dimethylphenylene are exemplified. Q is each independently =C(-H)- or =N-, and is preferably =N- from the viewpoint of the shallowness of the LUMO of the partial structure to be formed and the height of the excited singlet energy level and the excited triplet energy level. Ar are each independently 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, and 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, 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 1 to (6-m), and from the viewpoint of steric hindrance, 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.

[0345] More specifically, the compounds used as the second component in this embodiment are preferably 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.

[0346] The compound used as the second component in this embodiment may be a donor-acceptor type TADF compound represented by DA in which one donor D and one acceptor A are bonded directly or via a linking group; however, a compound having a structure represented by the following formula (DAD1) in which multiple donors D are bonded directly or via a linking group to one acceptor A is preferred because it provides an organic electroluminescent device with better properties. (D 1 -L 1 )nA 1 (DAD1) Formula (DAD1) includes compounds represented by the following formula (DAD2). D 2 -L 2 -A 2 -L 3 -D 3 (DAD2) In the formula (DAD1) and the formula (DAD2), D 1 , D 2 and D. 3 Each independently represents a donor group. As the donor group, the above-mentioned donor structure can be used. A 1 and A 2 Each of L independently represents an acceptor group. As the acceptor group, the above-mentioned acceptor structure can be used. 1 , L 2 and L 3Each of L independently represents a single bond or a conjugated linking group. The conjugated linking group is a spacer structure that separates a donor group and an acceptor group, and is preferably an arylene having 6 to 18 carbon atoms, and more preferably an arylene having 6 to 12 carbon atoms. 1 , L 2 and L 3 More preferably, each independently represents phenylene, methylphenylene, or dimethylphenylene. 1 represents an integer equal to or less than the maximum number that can be substituted. For example, n may be selected within the range of 2 to 10, or within the range of 2 to 6. When n is 2, the compound is represented by formula (DAD2). 1 may be the same or different, and n L 1 may be the same or different. Preferred specific examples of the compounds represented by formula (DAD1) and formula (DAD2) include 2PXZ-TAZ and the following compounds, but the second component that can be used in the present invention is not limited to these compounds.

[0347] [ka]

[0348] In this embodiment, the light-emitting layer may be a single layer or multiple layers. The host compound, the thermally activated delayed phosphor, and the polycyclic aromatic compound of the present invention may be contained in the same layer, or at least one component may be contained in each of the multiple layers. The host compound, the thermally activated delayed phosphor, and the polycyclic aromatic compound of the present invention 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. The light-emitting layer doped with the assisting dopant and the emitting dopant can be formed by a method of forming a film by a ternary co-evaporation method of the host compound, the assisting dopant, and the emitting dopant, a method of mixing the host compound, the assisting dopant, and the emitting dopant in advance and then simultaneously evaporating them, or a wet film-forming method of applying a composition (paint) for forming a light-emitting layer prepared by dissolving the host compound, the assisting dopant, and the emitting dopant in an organic solvent, or the like.

[0349] The amount of the host compound used varies depending on the type of the host compound, and may be determined according to the properties of the host compound. The amount of the host compound used is preferably 40 to 99.999% by mass, more preferably 50 to 99.99% by mass, and even more preferably 60 to 99.9% by mass, based on the total amount of the light-emitting layer material. The above range is preferable in terms of, for example, efficient charge transport and efficient energy transfer to the dopant.

[0350] The amount of the assisting dopant (thermally activated delayed phosphor) used varies depending on the type of the assisting dopant, and may be determined according to the characteristics of the assisting dopant. The amount of the assisting dopant used is preferably 1 to 60 mass % of the total material for the light emitting layer, more preferably 2 to 50 mass %, and even more preferably 5 to 30 mass %. The above range is preferable, for example, in that energy can be efficiently transferred to the emitting dopant.

[0351] The amount of the emitting dopant (a compound having a boron atom) used varies depending on the type of the emitting dopant, and may be determined according to the characteristics of the emitting dopant. The amount of the emitting dopant used is preferably 0.001 to 30% by mass, more preferably 0.01 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.

[0352] The amount of the emitting dopant used is preferably low in terms of preventing concentration quenching. The amount of the assisting dopant used is preferably high in terms of efficiency of thermally activated delayed fluorescence mechanism. Furthermore, from the viewpoint of efficiency of the thermally activated delayed fluorescence mechanism of the assisting dopant, the amount of the emitting dopant used is preferably low in comparison with the amount of the assisting dopant used.

[0353] 2-1-3. 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.

[0354] 2-1-4. 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.

[0355] 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.

[0356] 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.

[0357] 2-1-5. 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.

[0358] 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.

[0359] As the materials for forming the hole injection layer 103 and the hole transport layer 104, any compound can be selected from compounds conventionally used as charge transport materials for holes in photoconductive materials, p-type semiconductors, and known compounds used in hole injection layers and hole transport layers of organic EL 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 (4,4',4"-tris(N-carbazolyl)triphenylamine, polymers having aromatic tertiary amino in the main chain or side chain, 1,1-bis(4-di-p-tolylaminophenyl)cyclohexane, N,N'-diphenyl-N,N'-di(3-methylphenyl)-4,4'-diaminobiphenyl, N,N'-diphenyl-N,N'-dinaphthyl-4,4'-diaminobiphenyl, N,N'-diphenyl-N,N'-di(3-methylphenyl)-4,4'-diphenyl-1,1'-diamine, N,N'-dinaphthyl-N,N'-diphenyl-4,4'-diphenyl-1,1'-diamine, N 4 ,N 4’ -Diphenyl-N 4 ,N 4’ -Bis(9-phenyl-9H-carbazol-3-yl)-[1,1'-biphenyl]-4,4'-diamine, N 4 ,N 4 ,N 4’ ,N 4’-Tetra[1,1'-biphenyl]-4-yl)-[1,1'-biphenyl]-4,4'-diamine, 4,4',4"-tris(3-methylphenyl(phenyl)amino)triphenylamine and other triphenylamine derivatives, starburst amine derivatives, etc.), stilbene derivatives, phthalocyanine derivatives (metal-free, copper phthalocyanine, etc.), pyrazoline derivatives, hydrazone compounds, benzofuran derivatives, thiophene derivatives, oxadiazole derivatives, quinoxaline derivatives Conductors (e.g., 1,4,5,8,9,12-hexaazatriphenylene-2,3,6,7,10,11-hexacarbonitrile, etc.), heterocyclic compounds such as porphyrin derivatives, polysilanes, etc. As polymers, polycarbonates and styrene derivatives having the above-mentioned monomers in their side chains, polyvinylcarbazole, polysilanes, etc. are preferred, but there are no particular limitations on the compounds as long as they can form a thin film required for fabricating a light-emitting device, can inject holes from the anode, and can transport holes.

[0360] It is also known that the electrical conductivity of organic semiconductors is strongly influenced by their doping. Such organic semiconductor matrix substances consist of compounds with good electron donating or accepting properties. For doping with electron donating substances, strong electron acceptors such as tetracyanoquinone dimethane (TCNQ) or 2,3,5,6-tetrafluorotetracyano-1,4-benzoquinone dimethane (F4TCNQ) are known (see, for example, the 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). The polycyclic aromatic compound of the present invention may be used as a material for forming a hole injection layer or a material for forming a hole transport layer.

[0361] 2-1-6. Electron blocking layer in organic electroluminescent device An electron blocking layer for preventing diffusion of electrons from the light-emitting layer may be provided between the hole injection / transport layer and the light-emitting layer. The electron blocking layer may be formed using a compound represented by any one of the above formulas (H1), (H2) and (H3). The polycyclic aromatic compound of the present invention may be used as a material for forming an electron blocking layer.

[0362] 2-1-7. 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.

[0363] 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.

[0364] 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.

[0365] 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.

[0366] Specific examples of other electron transport compounds include pyridine derivatives, naphthalene derivatives, fluoranthene derivatives, BO derivatives, anthracene 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 metal complexes, quinoxaline derivatives, polymers of quinoxaline derivatives, benzazole compounds, gallium complexes, pyrazole derivatives, perfluorinated phenylene derivatives, triazine derivatives, pyrazine derivatives, benzoxazole ... Examples of the compound include quinolin 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, thiazole 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, pyrimidine derivatives, arylnitrile derivatives, indole derivatives, phosphorus oxide derivatives, bisstyryl derivatives, silole derivatives, and azoline derivatives.

[0367] 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.

[0368] The above-mentioned materials may be used alone or in combination with different materials.

[0369] 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, quinolinol-based metal complexes, thiazole derivatives, benzothiazole derivatives, silole derivatives and azoline derivatives are preferred.

[0370] The polycyclic aromatic compound of the present invention may be used as a material for forming an electron injection layer or an electron transport layer.

[0371] <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.

[0372] 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 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 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 1is 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.

[0373] 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.

[0374] Specific examples of the borane derivative include the following compounds: [ka]

[0375] The borane derivative can be produced using known raw materials and known synthesis methods.

[0376] <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]

[0377] 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.

[0378] In formula (ETM-2-1), R 11 ~R18 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).

[0379] In formula (ETM-2-2), R 11 and R 12 are each independently hydrogen, alkyl (preferably alkyl having 1 to 24 carbon atoms), cycloalkyl (preferably cycloalkyl having 3 to 12 carbon atoms) or aryl (preferably aryl having 6 to 30 carbon atoms); R 11 and R 12 may be bonded to form a ring.

[0380] 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.

[0381] [ka]

[0382] 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]

[0383] 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.

[0384] R 11 ~R 18 The "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).

[0385] 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.

[0386] 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.

[0387] R 11 ~R 18In 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.

[0388] 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.

[0389] 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.

[0390] 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.

[0391] R in formula (ETM-2-2) 11 and R 12 may combine to form a ring, and as a result, a cyclobutane, cyclopentane, cyclopentene, cyclopentadiene, cyclohexane, fluorene, indene, etc. may be spiro-bonded to the 5-membered ring of the fluorene skeleton.

[0392] Specific examples of this pyridine derivative include, for example, the following compounds.

Chemical formula

[0393] This pyridine derivative can be produced using known raw materials and known synthetic methods.

[0394] <Fluoranthene derivative> The fluoranthene derivative is, for example, a compound represented by the following formula (ETM-3), and specifically, it is disclosed in International Publication No. 2010 / 134352.

Chemical formula

[0395] In formula (ETM-3), X 12 ~X 21 represent hydrogen, halogen, linear, branched or cyclic alkyl, linear, branched or cyclic alkoxy, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl. Here, examples of the substituent when it is substituted include aryl, heteroaryl, alkyl or cycloalkyl, etc.

[0396] Specific examples of this fluoranthene derivative include, for example, the following compounds.

Chemical formula

[0397] <BO-based derivative> The BO derivative is, for example, a polycyclic aromatic compound represented by the following formula (ETM-4), or a polymer of a polycyclic aromatic compound having a plurality of structures represented by the following formula (ETM-4). [ka]

[0398] 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.

[0399] 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.

[0400] In addition, at least one hydrogen in the compound or structure represented by formula (ETM-4) may be substituted with a halogen or deuterium.

[0401] For an explanation of the substituents and the form of ring formation in formula (ETM-4), the explanation of the polycyclic aromatic compound represented by formula (1) etc. can be cited.

[0402] Specific examples of the BO derivative include the following compounds: [ka]

[0403] The BO derivative can be produced using known raw materials and known synthesis methods.

[0404] <Anthracene derivatives> One of the anthracene derivatives is, for example, a compound represented by the following formula (ETM-5). [ka]

[0405] Ar 1 are each independently a single bond, or a divalent benzene, naphthalene, anthracene, fluorene, or phenalene.

[0406] 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.

[0407] 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.

[0408] 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.

[0409] 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.

[0410] Specific examples of these anthracene derivatives include the following compounds. [ka]

[0411] These anthracene derivatives can be produced using known raw materials and known synthesis methods.

[0412] <Benzofluorene derivatives> The benzofluorene derivative is, for example, a compound represented by the following formula (ETM-6). [ka]

[0413] 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.

[0414] 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.

[0415] 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.

[0416] 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.

[0417] 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.

[0418] Specific examples of the "aryl having 6 to 30 carbon atoms" include phenyl, naphthyl, acenaphthylenyl, fluorenyl, phenalenyl, phenanthryl, triphenylenyl, pyrenyl, naphthacenyl, perylenyl, and pentacenyl.

[0419] 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.

[0420] Specific examples of the benzofluorene derivative include the following compounds: [ka]

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

[0422] <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]

[0423] 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.

[0424] The phosphine oxide derivative may be, for example, a compound represented by the following formula (ETM-7-2). [ka]

[0425] 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, formyl, carbonyl, carboxyl, amino, nitro, silyl, and a fused ring formed between adjacent substituents.

[0426] 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.

[0427] 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.

[0428] 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.

[0429] 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.

[0430] 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.

[0431] 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.

[0432] 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.

[0433] 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.

[0434] Moreover, alkylthio is a group in which the oxygen atom of the ether bond of alkoxy is replaced with a sulfur atom.

[0435] Moreover, cycloalkylthio is a group in which the oxygen atom of the ether bond of cycloalkoxy is replaced with a sulfur atom.

[0436] 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.

[0437] 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.

[0438] 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.

[0439] 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.

[0440] Halogen refers to fluorine, chlorine, bromine and iodine.

[0441] Formyl, carbonyl and amino may also include groups substituted with aliphatic hydrocarbons, alicyclic hydrocarbons, aromatic hydrocarbons, heterocycles and the like.

[0442] Furthermore, the aliphatic hydrocarbons, alicyclic hydrocarbons, aromatic hydrocarbons and heterocycles may be either unsubstituted or substituted.

[0443] 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.

[0444] 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.

[0445] Specific examples of the phosphine oxide derivative include the following compounds: [ka]

[0446] The phosphine oxide derivative can be produced using known raw materials and known synthesis methods.

[0447] <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]

[0448] 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.

[0449] 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.

[0450] 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.

[0451] 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.

[0452] 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.

[0453] The above aryl and heteroaryl may be substituted, for example, by the above aryl or heteroaryl, respectively.

[0454] Specific examples of the pyrimidine derivative include the following compounds: [ka]

[0455] The pyrimidine derivative can be produced using known raw materials and known synthesis methods.

[0456] <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]

[0457] Ar niFrom the viewpoint of fast electron transport 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.

[0458] 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.

[0459] 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.

[0460] 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.

[0461] 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.

[0462] 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.

[0463] The above aryl and heteroaryl may be substituted, for example, by the above aryl or heteroaryl, respectively.

[0464] 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.

[0465] Specific examples of the arylnitrile derivative include the following compounds: [ka]

[0466] The arylnitrile derivatives can be produced using known raw materials and known synthesis methods.

[0467] The carbazole derivative can be produced using known raw materials and known synthesis methods.

[0468] <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]

[0469] 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.

[0470] 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.

[0471] 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.

[0472] 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.

[0473] 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.

[0474] The above aryl and heteroaryl may be substituted, for example, by the above aryl or heteroaryl, respectively.

[0475] Specific examples of the triazine derivative include the following compounds: [ka]

[0476] The triazine derivative can be produced using known raw materials and known synthesis methods.

[0477] <Benzimidazole derivatives> The benzimidazole derivative is, for example, a compound represented by the following formula (ETM-11). [ka]

[0478] 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.

[0479] [ka]

[0480] 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.

[0481] 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.

[0482] 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.

[0483] [ka]

[0484] The benzimidazole derivative can be produced using known raw materials and known synthesis methods.

[0485] <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]

[0486] 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.

[0487] 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.

[0488] At least one hydrogen atom in each of the phenanthroline derivatives may be replaced with deuterium.

[0489] 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.

[0490] [ka]

[0491] 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]

[0492] The phenanthroline derivative can be produced using known raw materials and known synthesis methods.

[0493] <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.

[0494] 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.

[0495] The quinolinol metal complex can be produced using known raw materials and known synthesis methods.

[0496] <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]

[0497] 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.

[0498] [ka]

[0499] 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.

[0500] These thiazole or benzothiazole derivatives can be produced using known raw materials and known synthesis methods.

[0501] <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]

[0502] 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 (1) and formula (2) 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 explanation in formula (ETM-7-2) can be cited. Furthermore, X and Y, both of which are alkyl, may be bonded to form a ring.

[0503] 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.

[0504] R 1 ~R 4 For details of halogen, alkyl, cycloalkyl, alkoxy, aryloxy, amino, aryl, heteroaryl, alkenyl and alkynyl in, the descriptions in formula (1) and formula (2) can be cited.

[0505] 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 (1) and the formula (2) can be cited.

[0506] 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, see the explanations in formula (1) and formula (2).

[0507] 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.

[0508] However, preferably, R 1 and R 4 is phenyl, X and Y are not alkyl or phenyl. 1 and R 4 When R is thienyl, X and Y are alkyl, R is thienyl, 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 each independently not 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.

[0509] These silole derivatives can be produced using known raw materials and known synthesis methods.

[0510] <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]

[0511] 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]

[0512] 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.

[0513] Specific azoline derivatives are compounds represented by the following formula (ETM-16-1) or formula (ETM-16-2). [ka]

[0514] 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):

[0515] [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.

[0516] 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.

[0517] [ka]

[0518] [ka] [ka]

[0519] 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.

[0520] 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.

[0521] 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.

[0522] 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.

[0523] Specific examples of azoline derivatives include the following compounds: In the structural formula, "Me" represents methyl. [ka]

[0524] 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.

[0525] [ka]

[0526] 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.

[0527] Other specific examples of azoline derivatives include the following compounds: In the structural formula, "Me" represents methyl. [ka]

[0528] For details of the alkyl, cycloalkyl, aryl or heteroaryl in the above formulas defining this azoline derivative, the explanations in formula (1) and formula (2) can be cited.

[0529] The azoline derivative can be produced using known raw materials and known synthesis methods.

[0530] <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.

[0531] 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.

[0532] 2-1-8. 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 .

[0533] 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.

[0534] Further, for electrode protection, preferred examples include lamination of metals such as platinum, gold, silver, copper, iron, tin, aluminum, and indium, or alloys using these metals, inorganic substances such as silica, titania, and silicon nitride, polyvinyl alcohol, vinyl chloride, hydrocarbon polymer compounds, etc. The method for producing these electrodes is 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.

[0535] 2-1-9. 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.

[0536] 2-1-10. 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, inkjet, 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.

[0537] 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 / hole injection layer / hole transport layer / light-emitting layer consisting of a host material and a dopant material / electron transport layer / electron injection layer / cathode will be described. After forming a thin film of an anode material on a suitable substrate by a deposition method or the like to produce an anode, thin films of a hole injection layer and a hole transport layer are formed on the anode. A host material and a dopant material are co-deposited on the anode to form a thin film to produce a light-emitting layer, an electron transport layer and an electron injection layer are formed on the light-emitting layer, and a thin film consisting of a cathode material is further formed by a deposition method or the like to produce a cathode, thereby obtaining a desired organic EL element. In the production of the above-mentioned organic EL element, the production order can also be reversed, and the elements can be produced in the order of a cathode, an electron injection layer, an electron transport layer, a light-emitting layer, a hole transport layer, a hole injection layer, and an anode.

[0538] 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.

[0539] 2-1-11.Application examples of organic electroluminescent devices The organic EL element can also be applied to a display device or a lighting device. A display device or lighting device equipped with an organic EL element can be manufactured by a known method, such as by connecting the organic EL element to a known driving device, and can be driven appropriately using a known driving method such as DC driving, pulse driving, or AC driving.

[0540] 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.

[0541] 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.

[0542] 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.

[0543] Examples of lighting devices include lighting devices for indoor lighting, backlights for liquid crystal display devices, etc. (see, for example, JP-A-2003-257621, JP-A-2003-277741, JP-A-2004-119211, 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 backlights for liquid crystal display devices, particularly for personal computers where thinning is an issue, backlights using organic EL elements are characterized by their thinness and light weight, considering that conventional methods are made up of fluorescent lamps and light guide plates and therefore difficult to make thin.

[0544] 2-2. 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.

[0545] 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.

[0546] 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.

[0547] 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.

[0548] 3. Wavelength conversion materials The polycyclic aromatic compound of the present invention can be used as a wavelength converting material. Currently, the application of multi-color technology using color conversion methods to liquid crystal displays, organic electroluminescence displays, lighting, and the like is being actively studied. Color conversion refers to the wavelength conversion of light emitted from a light emitter to light with a longer wavelength, for example, converting ultraviolet light or blue light to green light or red light emission. By forming a wavelength conversion material with this color conversion function into a film and combining it with, for example, a blue light source, it becomes possible to extract the three primary colors of blue, green, and red from the blue light source, that is, to extract white light. By combining such a blue light source and a wavelength conversion film with a color conversion function as a light source unit, and combining it with a liquid crystal drive part and a color filter, it becomes possible to manufacture a full-color display. Furthermore, if there is no liquid crystal drive part, it can be used as a white light source as it is, and can be applied as a white light source for, for example, LED lighting. Furthermore, by using a blue organic electroluminescence element as a light source in combination with a wavelength conversion film that converts blue light into green light and red light, it becomes possible to manufacture a full-color organic electroluminescence display without using a metal mask. Furthermore, by using blue microLEDs as a light source in combination with a wavelength conversion film that converts blue light into green and red light, it is possible to create low-cost full-color microLED displays.

[0549] The polycyclic aromatic compound of the present invention can be used as this wavelength converting material. By using a wavelength converting material containing the polycyclic aromatic compound of the present invention, light from a light source or a light emitting element that generates ultraviolet light or a shorter wavelength blue light can be converted into blue light or green light with high color purity suitable for use in a display device (a display device using an organic EL element or a liquid crystal display device). The converted color can be adjusted by appropriately selecting the substituent of the polycyclic aromatic compound of the present invention, the binder resin used in the wavelength converting composition described below, and the like. The wavelength converting material can be prepared as a wavelength converting composition containing the polycyclic aromatic compound of the present invention. In addition, a wavelength converting film may be formed using this wavelength converting composition.

[0550] The wavelength conversion composition may contain a binder resin, other additives, and a solvent in addition to the polycyclic aromatic compound of the present invention. As the binder resin, for example, those described in paragraphs 0173 to 0176 of International Publication No. 2016 / 190283 can be used. As other additives, compounds described in paragraphs 0177 to 0181 of International Publication No. 2016 / 190283 can be used. As the solvent, the description of the solvent contained in the composition for forming the light-emitting layer can be referred to.

[0551] The wavelength conversion film includes a wavelength converting layer formed by curing the wavelength converting composition. Known film forming methods can be referred to as a method for producing a wavelength converting layer from a wavelength converting composition. The wavelength conversion film may consist only of a wavelength converting layer formed from a composition containing the polycyclic aromatic compound of the present invention, or may include other wavelength converting layers (e.g., a wavelength converting layer that converts blue light into green light or red light, or a wavelength converting layer that converts blue light or green light into red light). The wavelength conversion film may further include a substrate layer and a barrier layer for preventing deterioration of the color conversion layer due to oxygen, moisture, or heat. EXAMPLES

[0552] The present invention will be described in more detail below with reference to examples, but the present invention is not limited to these.

[0553] Synthesis example (1): 2-(tert-butyl)-4,14-bis(4-(tert-butyl)phenyl)-10-methyl-4,14-dihydro-4,7b,14-triaza-3a 2 -Synthesis of boradibenzo[fg,jk]indeno[1,2,3-cd]pyrene (compound (1-a-2) [ka]

[0554] [1st stage (A)] 1-Bromo-5-(tert-butyl)-2,3-dichlorobenzene (29.0 g, 100 mmol), sodium t-butoxide (28.8 g, 300 mmol), 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl [BINAP] (2.5 g, 4.0 mmol), bis(dibenzylideneacetone)palladium(0) [Pd2(dba)3] (1.83 g, 2.0 mmol) and toluene (400 ml) were added with 4-(tert-butyl)aniline (29.8 g, 200 mmol) at room temperature under a nitrogen atmosphere, and the mixture was heated and stirred at 100°C for 26 hours. The reaction solution was cooled to room temperature, filtered using silica gel column chromatography, and the solvent was distilled off under reduced pressure to obtain a crude product. After that, by washing with toluene, 5-(tert-butyl)-N was obtained as a white solid. 1 ,N 3 -Bis(4-(tert-butyl)phenyl)-2-chlorobenzene-1,3-diamine (compound (t-1), 42.1 g, yield 91%) was obtained.

[0555] [ka]

[0556] [1st stage (B)] 2-Bromo-6-methyl-9H-carbazole (26.0 g, 100 mmol), 1-chloro-3-fluorobenzene (13.1 g, 100 mol), and potassium carbonate (41.4 g, 300 mmol) were dissolved or dispersed in NMP (400 mL), and heated and stirred at 180° C. for 8 hours under a nitrogen atmosphere. The reaction solution was cooled to room temperature, filtered using silica gel column chromatography, and the solvent was distilled off under reduced pressure to obtain a crude product. Thereafter, recrystallization was performed with toluene / hexane (1:10 (volume ratio)) to obtain 2-bromo-9-(3-chlorophenyl)-6-methyl-9H-carbazole (compound (t-2), 34.1 g, yield 92%) as a white solid.

[0557] [ka]

[0558] [Second stage] 5-(tert-Butyl)-N 1 ,N 3 -Bis(4-(tert-butyl)phenyl)-2-chlorobenzene-1,3-diamine (compound (t-1), 11.6 g, 25 mmol), sodium t-butoxide (7.20 g, 75 mmol), tri-t-butylphosphine (0.212 g, 1.05 mmol), bis(dibenzylideneacetone)palladium(0) [Pd2(dba)3] (0.458 g, 0.50 mmol) and toluene (100 ml) were added at 0°C under a nitrogen atmosphere to 2-bromo-9-(3-chlorophenyl)-6-methyl-9H-carbazole (compound (t-2), 9.3 g, 25 mmol), and the mixture was stirred at room temperature for 24 hours. The reaction solution was filtered using silica gel column chromatography (developing solution: toluene / hexane = 1:1 (volume ratio)), and the solvent was distilled off under reduced pressure to obtain a crude product. Then, by washing with methanol, 5-(tert-butyl)-N was obtained as a white solid. 1 ,N 3 -Bis(4-(tert-butyl)phenyl)-2-chloro-N 1 -(9-(3-chlorophenyl)-6-methyl-9H-carbazol-2-yl)benzene-1,3-diamine (compound (t-3), 12.1 g, yield 64%) was obtained.

[0559] [ka]

[0560] [4th stage] Under a nitrogen atmosphere, a solution of sodium t-butoxide (0.577 g, 6.0 mmol), 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl (0.123 g, 0.3 mmol), bis(dibenzylideneacetone)palladium(0) (0.147 g, 0.16 mmol) and o-xylene (400 ml) was heated to 140°C with stirring to give 5-(tert-butyl)-N 1 ,N 3 -Bis(4-(tert-butyl)phenyl)-2-chloro-N1 A solution of -(9-(3-chlorophenyl)-6-methyl-9H-carbazol-2-yl)benzene-1,3-diamine (compound (t-3), 3.01 g, 4.0 mmol) and o-xylene (900 ml) was slowly added dropwise over 12 hours. The reaction solution was then cooled to room temperature, filtered using silica gel (developing solution: toluene), and the solvent was distilled off under reduced pressure. The crude product was purified by silica gel column chromatography (developing solution: toluene / hexane = 1 / 4 (volume ratio)) to obtain 4-methyl-1,3-diamine (4H-chlorophenyl)-1,3-diamine (compound (t-3), 3.01 g, 4.0 mmol) and o-xylene (900 ml). The reaction solution was then cooled to room temperature, filtered using silica gel (developing solution: toluene / hexane = 1 / 4 (volume ratio)), and the solvent was distilled off under reduced pressure. 5 -(tert-butyl)-3,5-bis(4-(tert-butyl)phenyl)-4 2 -Chloro-1 6 -Methyl-1 9 H-3,5-diaza-1(9,2)-carbazola-2,4(1,3)-dibenzenacyclopentaphane (compound (t-4), 1.55 g, yield 54%) was obtained.

[0561] [ka]

[0562] [5th ​​stage] 4 5 -(tert-butyl)-3,5-bis(4-(tert-butyl)phenyl)-4 2 -Chloro-1 6 -Methyl-1 9To a solution of H-3,5-diaza-1(9,2)-carbazola-2,4(1,3)-dibenzenacyclopentaphane (compound (t-4), 143 mg, 0.20 mmol) in tert-butylbenzene (4.0 ml), 1.6 M tert-butyllithium hexane solution (0.125 ml, 0.20 mmol) was added at -40°C under a nitrogen atmosphere. After heating and stirring at 50°C for 30 minutes, the reaction solution was cooled to -40°C, boron tribromide (37.5 μl, 0.40 mmol) was added, and the mixture was stirred for 30 minutes. Then, N,N-diisopropylamine (70.0 μl, 0.40 mmol) was added, and the mixture was heated and stirred at 165°C for 24 hours. The reaction solution was cooled to room temperature and filtered using Florisil (developing solution: dichloromethane). After the solvent was removed under reduced pressure, the mixture was washed with dichloromethane to give 2-(tert-butyl)-4,14-bis(4-(tert-butyl)phenyl)-10-methyl-4,14-dihydro-4,7b,14-triaza-3a as a white solid. 2 -Borazibenzo[fg,jk]indeno[1,2,3-cd]pyrene (compound (1-a-2) (75.1 mg, yield 52%)) was obtained.

[0563] [ka]

[0564] The structure of the compound obtained was confirmed by NMR spectrum. 1 H-NMR (400MHz, CDCl3): δ=1.33(s,27H), 2.44(s,3H), 6.01(d,5H),7.23(t,2H),7.44(d,5H),7.71(t,6H).

[0565] Synthesis example (2): 13-(tert-butyl)-4,4,9,10,15,15-hexamethyl-4,15-dihydro-7-thia-11b-aza-3a 2 Synthesis of boraphenaleno[5,4,3,2,1-pqrst]pentaphene (compound (1-b-9) [ka]

[0566] [1st stage] 2,3-Dimethyl-10H-phenothiazine (22.7g, 100mmol), 1-tert-butyl-3-fluorobenzene (15.2g, 100mol), potassium carbonate (41.4g, 300mmol) were dissolved or dispersed in NMP (400mL), and heated and stirred at 180°C for 12 hours under a nitrogen atmosphere. The reaction solution was cooled to room temperature, filtered using silica gel column chromatography, and the solvent was distilled off under reduced pressure to obtain a crude product. Thereafter, recrystallization was performed with toluene / hexane (1:5 (volume ratio)) to obtain 10-(3-(tert-butyl)phenyl)-2,3-dimethyl-10H-phenothiazine (compound (t-5), 27.6g, yield 77%) as a white solid.

[0567] [ka]

[0568] [2nd~3rd stage] 10-(3-(tert-butyl)phenyl)-2,3-dimethyl-10H-phenothiazine (18.0 g, 50 mmol) was dissolved in chlorobenzene (100 mL), and boron tribromide (37.6 g, 150 mmol) was added and stirred at room temperature for 12 hours. The temperature was raised to 100°C and the pressure was reduced to remove volatiles. The reaction mixture was used for the next step without purification. 2,6-di(propen-2-yl)phenyllithium (20.2 g, 45 mmol) and N-butyllithium (35.6 mL, 1.14 mmol) dissolved in chlorobenzene (100 mL) were added to the reaction mixture and stirred at 100°C for 24 hours. A saturated aqueous solution of ammonium chloride was added to the reaction liquid, stirred, and extracted with toluene. The reaction solution was subjected to silica gel column chromatography (eluent: toluene) to recover only the fraction containing the target substance, and 12-(tert-butyl)-9-(2,6-di(propyl-1-en-2-yl)phenyl)-2,3-dimethyl-9H-benzo[5,6][1,4]azaborinino[3,2,1-kl]phenothiazine (compound (t-6), 11.2 g, yield 43%) was obtained.

[0569] [ka]

[0570] [4th stage] 12-(tert-butyl)-9-(2,6-di(propyl-1-en-2-yl)phenyl)-2,3-dimethyl-9H-benzo[5,6][1,4]azaborinino[3,2,1-kl]phenothiazine (compound (t-6), 1.05 g, 2.0 mmol) and scandium triflate (0.98 g, 2.0 mmol) were dissolved in chlorobenzene (50 ml) and heated and stirred at 100°C for 6 hours. Saturated sodium bicarbonate was added and extracted with toluene. The crude product was concentrated under reduced pressure and purified by silica gel column chromatography (eluent: toluene / hexane = 1 / 5 (volume ratio)) to give 13-(tert-butyl)-4,4,9,10,15,15-hexamethyl-4,15-dihydro-7-thia-11b-aza-3a 2-Bora"phenaleno[5,4,3,2,1-pqrst]pentaphene (compound (1-b-9), 0.45 g, yield 43%) was obtained.

[0571] [ka]

[0572] The structure of the compound obtained was confirmed by NMR spectrum. 1 H-NMR (400MHz, CDCl3): δ=1.36(s,9H), 1.70(s,12H), 2.26(s,6H), 6.01(s,1H) ,6.25-6.33(m,2H), 7.01(s,1H), 7.10(s,1H), 7.23-7.33(m,3H), 7.71(t,1H).

[0573] By appropriately changing the raw material compounds, other compounds of the present invention can be synthesized by referring to the methods according to the above-mentioned synthesis examples and Yamaguchi et al., Organic & Biomolecular Chemistry, 2019, 17, 5500-5504.

[0574] By appropriately changing the raw material compounds, other compounds of the present invention can be synthesized according to the methods of the above-mentioned synthesis examples.

[0575] Compound (1-a-1) was synthesized by a method similar to Synthesis Example (1), except that 2-bromo-9-(3-chlorophenyl)-6-methyl-9H-carbazole in the second step of Synthesis Example (1) was changed to 2-bromo-9-(3-chlorophenyl)-9H-carbazole.

[0576] [ka]

[0577] The structure of the compound obtained was confirmed by NMR spectrum. 1H-NMR (400MHz, CDCl3): δ=1.33(s,27H), 6.40(d,1H), 7.08-7.10(m,2H), 7.03(s,1H), 7.11(s,1H), 7.23-7.62(m,12H), 8.19(d,1H), 8.40(d,1H).

[0578] Compound (1-a-3) was synthesized by a method similar to Synthesis Example (1), except that 2-bromo-9-(3-chlorophenyl)-6-methyl-9H-carbazole in the second step of Synthesis Example (1) was changed to 2-bromo-9-(3-chlorophenyl)-7-methyl-9H-carbazole.

[0579] [ka]

[0580] The structure of the compound obtained was confirmed by NMR spectrum. 1 H-NMR (400MHz, CDCl3): δ=1.32(s,27H), 2.44(s,3H), 6.41(d,1H),7.07-7.10( m,2H), 7.01(s,1H), 7.12(s,1H), 7.23-7.45(m,11H), 8.10(d,1H), 8.41(d,1H).

[0581] Compound (1-a-4) was synthesized by a method similar to Synthesis Example (1), except that 2-bromo-9-(3-chlorophenyl)-6-methyl-9H-carbazole in the second step of Synthesis Example (1) was changed to 7-bromo-9-(3-chlorophenyl)-2,3-dimethyl-9H-carbazole.

[0582] [ka]

[0583] The structure of the compound obtained was confirmed by NMR spectrum. 1H-NMR (400MHz, CDCl3): δ=1.32(s,27H), 2.25(s,3H), 2.47(s,3H), 6.40(d,1H),7.06- 7.10(m,2H), 7.01(s,1H), 7.11(s,1H), 7.23-7.46(m,10H), 7.96(d,1H), 8.39(d,1H).

[0584] Compound (1-a-5) was synthesized by a method similar to Synthesis Example (1) except that 1-chloro-3-fluorobenzene in the first step (b) of Synthesis Example (1) was changed to 1-chloro-3-fluoro-5-methylbenzene.

[0585] [ka]

[0586] The structure of the compound obtained was confirmed by NMR spectrum. 1 H-NMR (400MHz, CDCl3): δ=1.32(s,27H), 2.38(s,3H), 6.39(d,1H),7.07-7.10( m,2H), 7.00(s,1H), 7.11(s,1H), 7.22-7.59(m,11H), 8.20(d,1H), 8.41(d,1H).

[0587] Compound (1-a-6) was synthesized by a method similar to Synthesis Example (1), except that 1-chloro-3-fluorobenzene in the first step (b) of Synthesis Example (1) was changed to 1-(tert-butyl)-3-chloro-5-fluorobenzene.

[0588] [ka]

[0589] The structure of the compound obtained was confirmed by NMR spectrum. 1H-NMR (400MHz, CDCl3): δ=1.32(s,27H), 1.35(s,9H), 6.38(d,1H),7.08-7.10( m,2H), 7.01(s,1H), 7.11(s,1H), 7.22-7.58(m,11H), 8.19(d,1H), 8.42(d,1H).

[0590] Compound (1-a-25) was synthesized by a method similar to Synthesis Example (1), except that 2-bromo-9-(3-chlorophenyl)-6-methyl-9H-carbazole in the second step of Synthesis Example (1) was changed to 8-bromo-10-(3-chlorophenyl)-2,3-dimethyl-10H-phenothiazine.

[0591] [ka]

[0592] The structure of the compound obtained was confirmed by NMR spectrum. 1 H-NMR (400MHz, CDCl3): δ=1.32(s,27H), 2.18(s,3H), 2.32(s,3H), 6.80(s,1H), 6.84(s,1H), 7.08-7.12(m,14H), 7.28(d,1H).

[0593] Compound (1-b-4) was synthesized by a method similar to Synthesis Example (2) except that 2,3-dimethyl-10H-phenothiazine in the first step of Synthesis Example (2) was changed to 10H-phenoxazine.

[0594] [ka]

[0595] The structure of the compound obtained was confirmed by NMR spectrum. 1H-NMR (400MHz, CDCl3): δ=1.41(s,9H), 1.68(s,12H), 6.78-6.96(m,2H), 7.03(d,2H), 7.08(d,2H), 7.14(d,3H), 7.32(s,1H), 7.53(d,1H).

[0596] Compound (1-b-7) was synthesized by a method similar to Synthesis Example (2), except that 2,3-dimethyl-10H-phenothiazine in the first step of Synthesis Example (2) was changed to 10H-phenothiazine and 1-tert-butyl-3-fluorobenzene was changed to N-(3,5-dimethylphenyl)-N-(4-fluorophenyl)-3,5-dimethylaniline.

[0597] [ka]

[0598] The structure of the compound obtained was confirmed by NMR spectrum. 1 H-NMR (400MHz, CDCl3): δ=1.65(s,12H), 2.20(s,6H), 2.30(s,6H), 6.80(d,1H), 6.93-7.14(m,15H), 7.51(t,1H).

[0599] Compound (1-b-8) was synthesized by a method similar to Synthesis Example (2), except that 2,3-dimethyl-10H-phenothiazine in the first step of Synthesis Example (2) was changed to 10H-phenothiazine and -tert-butyl-3-fluorobenzene was changed to 4'-fluoro-2,6-dimethyl-1,1'-biphenyl.

[0600] [ka]

[0601] The structure of the compound obtained was confirmed by NMR spectrum. 1H-NMR (400MHz, CDCl3): δ=1.71(s,9H), 2.59(s,6H), 6.80(d,1H), 6.95-7.17(m,12H), 7.25(d,1H), 7.46(s,1H), 7.50(d,1H), 7.55(t,1H).

[0602] <Evaluation methods for basic physical properties> Sample preparation When evaluating the absorption and emission characteristics (fluorescence and phosphorescence) of a compound to be evaluated, the compound to be evaluated may be dissolved in a solvent and evaluated in the solvent, or in a thin film state. Furthermore, when evaluating in a thin film state, depending on the manner in which the compound to be evaluated is used in an organic EL device, only the compound to be evaluated may be made into a thin film and evaluated, or the compound to be evaluated may be dispersed in an appropriate matrix material and made into a thin film and evaluated. Here, a thin film obtained by vapor-depositing only the compound to be evaluated is called a "single film," and a thin film obtained by applying and drying a coating liquid containing the compound to be evaluated and a matrix material is called a "coated film."

[0603] As the matrix material, commercially available PMMA (polymethyl methacrylate) can be used. In this example, PMMA and the compound to be evaluated are dissolved in toluene, and then a thin film is formed on a transparent support substrate (10 mm x 10 mm) made of quartz by spin coating to prepare a sample.

[0604] Furthermore, a thin film sample in which the matrix material is a host compound is prepared as follows. A transparent support substrate made of quartz (10 mm × 10 mm × 1.0 mm) was fixed to the substrate holder of a commercially available deposition device (manufactured by Choshu Sangyo Co., Ltd.), and a molybdenum deposition boat containing a host compound and a molybdenum deposition boat containing a dopant material were installed. The vacuum chamber was then opened to 5 × 10 -4The pressure is reduced to 100 Pa. Next, the deposition boat containing the host compound and the deposition boat containing the dopant material are heated simultaneously, and the host compound and the dopant material are co-deposited to an appropriate film thickness to form a mixed thin film (sample) of the host compound and the dopant material. Here, the deposition rate is controlled according to the set mass ratio of the host compound and the dopant material.

[0605] Absorption and emission characterization The absorption spectrum of the sample is measured using an ultraviolet-visible-near infrared spectrophotometer (Shimadzu Corporation, UV-2600), and the fluorescence spectrum or phosphorescence spectrum of the sample is measured using a spectrofluorophotometer (Hitachi High-Tech Corporation, F-7000).

[0606] For measuring the fluorescence spectrum, the sample is excited at an appropriate excitation wavelength at room temperature and photoluminescence is measured. For measuring the phosphorescence spectrum, the sample is immersed in liquid nitrogen (temperature 77 K) using an attached cooling unit. To observe the phosphorescence spectrum, an optical chopper is used to adjust the delay time from irradiation with excitation light to the start of measurement. The sample is excited at an appropriate excitation wavelength and photoluminescence is measured.

[0607] In addition, the fluorescence quantum yield (PLQY) is measured using an absolute PL quantum yield measurement device (Hamamatsu Photonics KK, C9920-02G).

[0608] Next, the evaluation of the basic physical properties of the polycyclic aromatic compound of the present invention will be described.

[0609] Evaluation of fluorescence lifetime (delayed fluorescence) The fluorescence lifetime was measured at 300K using a fluorescence lifetime measurement device (Hamamatsu Photonics Co., Ltd., C11367-01). Specifically, emission components with fast and slow fluorescence lifetimes were observed at the maximum emission wavelength measured with an appropriate excitation wavelength. In fluorescence lifetime measurements at room temperature of typical organic EL materials that emit fluorescence, slow emission components involving triplet components derived from phosphorescence are rarely observed due to thermal deactivation of the triplet components. If a slow emission component is observed in the compound being evaluated, it indicates that triplet energy with a long excitation lifetime has been transferred to singlet energy by thermal activation and observed as delayed fluorescence.

[0610] Calculation of energy gap (Eg) Calculate Eg = 1240 / A from the long wavelength end A (nm) of the absorption spectrum obtained by the above method.

[0611] Measurement of ionization potential (Ip) A transparent support substrate (28 mm × 26 mm × 0.7 mm) on which ITO (indium tin oxide) was evaporated was fixed to the substrate holder of a commercially available evaporation device (Choshu Sangyo Co., Ltd.), a molybdenum evaporation boat containing the target compound was attached, and the vacuum chamber was opened to 5 × 10 -4 The pressure is reduced to 100 Pa. Next, the deposition boat is heated to evaporate the target compound, forming a film of the target compound alone (neat film).

[0612] The obtained single film is used as a sample, and the ionization potential of the target compound is measured using a photoelectron spectrometer (Sumitomo Heavy Industries, Ltd. PYS-201).

[0613] Calculation of electron affinity (Ea) The electron affinity can be estimated from the difference between the ionization potential measured by the above-mentioned method and the energy gap calculated by the above-mentioned method.

[0614] Measurement of excited singlet energy level E(S,Sh) and excited triplet energy level E(T,Sh) For a single film of the target compound formed on a glass substrate, the fluorescence spectrum is observed at 77 K using excitation light at a peak on the long wavelength side so that the fluorescence peak of the absorption spectrum does not overlap, and the excited singlet energy level E(S,Sh) is obtained from the shoulder on the short wavelength side of the peak of the fluorescence spectrum. In addition, a phosphorescence spectrum is observed for a single film of the target compound formed on a glass substrate at 77 K using excitation light with a peak on the long wavelength side of 1 nm so that the fluorescence peak of the absorption spectrum does not overlap, and the excited triplet energy level E(T,Sh) is determined from the shoulder on the short wavelength side of the peak of the phosphorescence spectrum.

[0615] <Evaluation of organic EL elements> As described above, the compound of the present invention has a suitable energy gap (Eg), a high triplet excitation energy (E T ) and a small ΔEST, they are expected to be useful in, for example, light-emitting layers and charge-transporting layers, and are particularly expected to be useful in light-emitting layers.

[0616] Evaluation items and evaluation methods The evaluation items include driving voltage (V), emission wavelength (nm), CIE chromaticity (x, y), external quantum efficiency (%), maximum wavelength (nm) and half-width (nm) of the emission spectrum, etc. For these evaluation items, values ​​at appropriate emission luminance can be used.

[0617] The quantum efficiency of a light-emitting element includes internal quantum efficiency and external quantum efficiency, and the internal quantum efficiency indicates the ratio of external energy injected as electrons (or holes) into the light-emitting layer of the light-emitting element that is converted purely into photons. On the other hand, the external quantum efficiency is calculated based on the amount of these photons that are emitted to the outside of the light-emitting element, and since some of the photons generated in the light-emitting layer are absorbed or continue to be reflected inside the light-emitting element and are not emitted to the outside of the light-emitting element, the external quantum efficiency is lower than the internal quantum efficiency.

[0618] The method of measuring the spectral radiance (emission spectrum) and external quantum efficiency is as follows. The element was made to emit light by applying a voltage using an Advantest voltage / current generator R6144. The spectral radiance in the visible light region was measured from the direction perpendicular to the light-emitting surface using a TOPCON spectroradiometer SR-3AR. Assuming that the light-emitting surface is a perfect diffusion surface, the measured spectral radiance value of each wavelength component was divided by the wavelength energy and multiplied by π to obtain the number of photons at each wavelength. Next, the number of photons was integrated over the entire wavelength range observed to obtain the total number of photons emitted from the element. The value obtained by dividing the applied current value by the elementary charge was determined as the number of carriers injected into the element, and the value obtained by dividing the total number of photons emitted from the element by the number of carriers injected into the element was determined as the external quantum efficiency. The half-width of the emission spectrum is calculated as the width between the wavelengths above and below where the intensity is 50% with the maximum emission wavelength as the center.

[0619] Next, the preparation and evaluation of an organic EL device using the polycyclic aromatic compound of the present invention will be described.

[0620] (1) Preparation and evaluation of evaporated organic electroluminescence devices Organic EL elements according to the examples and comparative examples are prepared, and voltage is applied to measure the emission wavelength and external quantum efficiency. The following three structures, Structure A (Table 1), Structure B (Table 2), and Structure C (Table 3), are selected as the structures of the prepared organic EL elements and evaluated. Structures A and C are structures suitable for thermally activated delayed fluorescence materials, and Structure B is a general structure using TTF (Triplet-Triplet-Fusion). However, the application of the compound of the present invention is not limited to these structures, 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.

[0621] [Table 1]

[0622] [Table 2]

[0623] 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, "mCBP" is 3,3'-bis(N-carbazolyl)-1,1'-biphenyl, "3,4-2CzBN" is 3,4-biscarbazolylbenzonitrile, and "BPy-TP2" is 2,7-di([2,2'-bipyridine]-5-yl)triphenylene. The chemical structures of each are shown below.

[0624] [ka]

[0625] The structures of the compounds used in Comparative Examples 1 to 6 are shown below. [ka]

[0626] <Example 1> <Configuration A: Device using compound (1-a-1) 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 device (manufactured by Showa Vacuum Co., Ltd.), and a molybdenum deposition boat containing NPD, TcTa, mCP, mCBP, compound (1-a-1), 3,4-2CzBN, and BPy-TP2, and a tungsten deposition boat containing LiF and aluminum were attached.

[0627] The following layers were formed in order on the ITO film of the transparent support substrate. -4The pressure was reduced to 100 Pa, and first, NPD was heated and evaporated to a thickness of 40 nm to form a hole injection layer. Next, TcTa was heated and evaporated to a thickness of 15 nm 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, mCBP and compound (1-a-1) were heated simultaneously and evaporated to a thickness of 20 nm to form an emitting layer. The evaporation rate was adjusted so that the mass ratio of mCBP to compound (1-a-1) was approximately 99:1. Next, 3,4-2CzBN was heated and evaporated to a thickness of 10 nm. Next, 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. Thereafter, LiF was heated and evaporated at an evaporation rate of 0.01 to 0.1 nm / sec to form 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.

[0628] <Example 2> <Configuration A: Element using compound (1-a-2) as a dopant> A device was produced in the same manner as in Example 1, except that the compound (1-a-1) was changed to the compound (1-a-2).

[0629] <Example 3> <Configuration A: Device using compound (1-a-3) as a dopant> A device was produced in the same manner as in Example 1, except that the compound (1-a-1) was changed to the compound (1-a-3).

[0630] <Example 4> <Configuration A: Element using compound (1-a-4) as a dopant> A device was produced in the same manner as in Example 1, except that the compound (1-a-1) was changed to the compound (1-a-4).

[0631] <Example 5> <Configuration A: Device using compound (1-a-5) as a dopant> A device was produced in the same manner as in Example 1, except that the compound (1-a-1) was changed to the compound (1-a-5).

[0632] <Example 6> <Configuration A: Element using compound (1-a-6) as a dopant> A device was produced in the same manner as in Example 1, except that the compound (1-a-1) was changed to the compound (1-a-6).

[0633] <Example 7> <Configuration A: Element using compound (1-a-7) as a dopant> A device was produced in the same manner as in Example 1, except that the compound (1-a-1) was changed to the compound (1-a-7).

[0634] <Comparative Example 1> <Configuration A: Device using compound (R-BD1) as a dopant> A device was produced in the same manner as in Example 1, except that compound (1) was changed to compound (R-BD1).

[0635] <Comparative Example 2> <Configuration A: Device using compound (R-BD2) as a dopant> A device was produced in the same manner as in Example 1, except that compound (1) was changed to compound (R-BD2).

[0636] The elements produced in Examples 1 to 7 and Comparative Examples 1 and 2 were subjected to DC voltage application using an ITO electrode as the anode and an aluminum electrode as the cathode, and the emission wavelength, emission half width (FWHM), external quantum efficiency (EQE) and LT90 (initial luminance 1000 cd / m 2 Continuous operation at 900cd / m 2 The time it takes for the light intensity to reach 1000cd / m 2 The measurement results are summarized in Table 1.

[0637] In Table 2, "HI-1" is N 4 ,N 4 '-Diphenyl-N 4 ,N 4"HT-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, "EMH2" is 9-phenyl-10-(4-phenylnaphthalen-1-yl)anthracene, "ET-1" is 4,6,8,10-tetraphenyl[1,4]benzoxaborinino[2,3,4-kl]phenoxaborinine, and "ET-2" is 3,3'-((2-phenylanthracene-9,10-diyl)bis(4,1-phenylene))bis(4-methylpyridine), the chemical structures of which are shown below along with "Liq."

[0638] [ka]

[0639] <Example 8> <Configuration B: Element using compound (1-a-2) as a dopant> A 26 mm × 28 mm × 0.7 mm glass substrate (manufactured by Optoscience Co., Ltd.) on which an ITO film formed to a thickness of 200 nm by sputtering was polished to 120 nm was used as a transparent support substrate. This transparent support substrate was fixed to a substrate holder of a commercially available deposition device (manufactured by Showa Vacuum Co., Ltd.), and a molybdenum deposition boat containing HI-1, HAT-CN, HT-1, HT-2, EMH1, compound (1-a-2), ET-1, and Liq, and a tungsten deposition boat containing LiF and aluminum were attached.

[0640] The following layers were formed in order on the ITO film of the transparent support substrate. -4The pressure was reduced to 10 Pa, and first, HI-1 was heated and evaporated to a thickness of 40 nm, and then HAT-CN was heated and evaporated to a thickness of 5 nm to form a hole injection layer consisting of two layers. Next, HT-1 was heated and evaporated to a thickness of 15 nm, and then HT-2 was heated and evaporated to a thickness of 10 nm to form a hole transport layer consisting of two layers. Next, EMH1 and compound (1-a-2) were heated simultaneously and evaporated to a thickness of 25 nm to form an emitting layer. The evaporation rate was adjusted so that the mass ratio of EMH1 to compound (1-a-2) was approximately 98:2. Next, ET-1 was heated and evaporated to a thickness of 5 nm, and then ET-2 and Liq were heated and evaporated to a thickness of 25 nm to form an electron transport layer consisting of two layers. The evaporation rate was adjusted so that the mass ratio of ET-2 to Liq was approximately 7:3. 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.

[0641] <Example 9> <Configuration B: Element using EMH2 as a host and compound (1-a-2) as a dopant> An element was produced in the same manner as in Example 8, except that EMH1 was changed to EMH2.

[0642] <Example 10> <Configuration B: Element using EMH2 as a host and compound (1-a-3) as a dopant> A device was prepared in the same manner as in Example 8, except that EMH1 was changed to EMH2 and compound (1-a-2) was changed to compound (1-a-3).

[0643] <Example 11> <Configuration B: Device using EMH2 as a host and compound (1-a-4) as a dopant> A device was prepared in the same manner as in Example 8, except that EMH1 was changed to EMH2 and compound (1-a-2) was changed to compound (1-a-4).

[0644] <Example 12> <Configuration B: Element using EMH2 as a host and compound (1-a-5) as a dopant> A device was prepared in the same manner as in Example 8, except that EMH1 was changed to EMH2 and compound (1-a-2) was changed to compound (1-a-5).

[0645] <Example 13> <Configuration B: Element using EMH2 as a host and compound (1-a-6) as a dopant> A device was prepared in the same manner as in Example 8, except that EMH1 was changed to EMH2 and compound (1-a-2) was changed to compound (1-a-6).

[0646] <Example 14> <Configuration B: Device using EMH2 as a host and compound (1-a-7) as a dopant> A device was prepared in the same manner as in Example 8, except that EMH1 was changed to EMH2 and compound (1-a-2) was changed to compound (1-a-7).

[0647] <Example 15> <Configuration B: Device using EMH2 as a host and compound (1-b-8) as a dopant> A device was prepared in the same manner as in Example 8, except that EMH1 was changed to EMH2 and compound (1-a-2) was changed to compound (1-b-8).

[0648] <Example 16> <Configuration B: Device using EMH2 as a host and compound (1-b-4) as a dopant> A device was prepared in the same manner as in Example 8, except that EMH1 was changed to EMH2 and compound (1-a-2) to compound (1-b-4).

[0649] <Example 17> <Configuration B: Device using EMH2 as a host and compound (1-b-7) as a dopant> A device was prepared in the same manner as in Example 8, except that EMH1 was changed to EMH2 and compound (1-a-2) was changed to compound (1-b-7).

[0650] <Example 18> <Configuration B: Device using EMH2 as a host and compound (1-b-8) as a dopant> A device was prepared in the same manner as in Example 8, except that EMH1 was changed to EMH2 and compound (1-a-2) was changed to compound (11).

[0651] <Comparative Example 3> <Configuration B: Element using compound (R-BD1) as a dopant> A device was produced in the same manner as in Example 8, except that the compound (1-a-2) was changed to the compound (R-BD1).

[0652] <Comparative Example 4> <Configuration B: Device using EMH2 as the host and compound (R-BD1) as the dopant> A device was prepared in the same manner as in Example 8, except that EHM1 was changed to EHM2 and compound (1-a-2) was changed to compound (R-BD1).

[0653] <Comparative Example 5> <Configuration B: Device using EMH2 as the host and compound (R-BD2) as the dopant> A device was prepared in the same manner as in Example 8, except that EHM1 was changed to EHM2 and compound (1-a-2) was changed to compound (R-BD2).

[0654] <Comparative Example 6> <Configuration B: Device using EMH2 as the host and compound (R-BD3) as the dopant> A device was prepared in the same manner as in Example 8, except that EHM1 was changed to EHM2 and compound (1-a-2) was changed to compound (R-BD3).

[0655] The elements produced in Examples 8 to 18 and Comparative Examples 3 to 6 were subjected to DC voltage application using an ITO electrode as the anode and an aluminum electrode as the cathode, and the emission wavelength, emission half width (FWHM), external quantum efficiency (EQE) and LT98 (initial luminance 1000 cd / m 2 Continuous operation at 980cd / m 2The time it takes for the light intensity to reach 1000cd / m 2 The measurement results are summarized in Table 2.

[0656] [Table 3]

[0657] In Table 3, "3Cz2DPhCzBN" is 2,4,6-tri(9H-carbazol-9-yl)-3,5-bis(3,6-diphenyl-9H-carbazol-9-yl)benzonitrile. The chemical structure is shown below. [ka]

[0658] <Example 19> <Configuration D: Element using 3Cz2DPhCzBN as the assisting dopant and compound (1-a-25) as the emitting dopant> A 26 mm x 28 mm x 0.7 mm glass substrate (Optoscience Co., Ltd.) on which an ITO film formed to a thickness of 200 nm by sputtering was polished to 50 nm was used as a transparent support substrate. This transparent support substrate was fixed to the substrate holder of a commercially available deposition device (Choshu Sangyo Co., Ltd.), and a tantalum deposition boat containing HAT-CN, Tris-PCz, mCBP, 3Cz2DPhCzBN, compound (1-a-25), T2T, and BPy-TP2, and an aluminum nitride deposition boat containing Liq, LiF, and aluminum, were attached.

[0659] The following layers are formed in order on the ITO film of the transparent support substrate. -4The pressure is reduced to 10 Pa, and first, HAT-CN is heated and evaporated to a thickness of 10 nm, and then Tris-PCz is heated and evaporated to a thickness of 30 nm to form a hole layer consisting of two layers. Next, mCBP as a host, 3Cz2DPhCzBN as an assisting dopant, and compound (1-a-25) as an emitting dopant are simultaneously heated and co-evaporated to a thickness of 30 nm to form an emitting layer. The evaporation rate is adjusted so that the mass ratio of the host, assisting dopant, and emitting dopant is approximately 80:19:1. Next, T2T is heated and evaporated to a thickness of 10 nm, and then BPy-TP2 and Liq are heated and evaporated to a thickness of 30 nm to form electron transport layers 1 and 2. The evaporation rate of each of the above layers is 0.01 to 1 nm / sec. Then, LiF is heated and evaporated at a deposition rate of 0.01 to 0.1 nm / sec to a thickness of 1 nm, and then aluminum is 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 is adjusted to 1 to 10 nm / sec.

[0660] The ITO electrode is the anode and the aluminum electrode is the cathode, and a DC voltage is applied to measure the luminance, chromaticity, and external quantum efficiency.

[0661] (2) Preparation and evaluation of compositions for forming light-emitting layers <Example S-1> As shown in Table 4, compositions for forming an emission layer with a solids concentration of 1 mass% can be prepared by mixing 0.98 mass% of the host as the first component, 0.02 mass% of the dopant as the second component, and 99 mass% of the solvent as the third component.

[0662] [Table 4]

[0663] In Table 4 above, "EMH3" is 9-(7-([1,1':3',1":3",1'"-quatrophenyl]-3-yl)naphthalen-2-yl)-10-phenylanthracene. The chemical structure is shown below. [ka]

[0664] The solvent "3PxT / c6B(7 / 3)" used in preparing the composition for forming the light-emitting layer is a mixed solution of 3-phenoxytoluene / cyclohexylbenzene=7 / 3 (volume ratio).

[0665] (3) Preparation and evaluation of solution-type organic electroluminescence devices Next, an organic EL device obtained by forming an organic layer by coating will be described.

[0666] <Synthesis of polymer hole transport compound: XLP-101> XLP-101 was synthesized according to the method described in JP 2018-61028 A. A copolymer in which M5 or M6 was bonded next to M4 was obtained, and it is estimated from the feed ratio that each unit is 40:10:50 (molar ratio). In the following formula, Bpin is pinacolatoboryl.

[0667] [ka]

[0668] <Polymer hole transport compound: Preparation of XLP-101 solution> XLP-101 synthesized according to the method described in JP 2018-61028 A is dissolved in a mixed solution of 3-phenoxytoluene / cyclohexylbenzene = 7 / 3 (volume ratio) to a concentration of 0.7 mass%.

[0669] <Preparation of Organic EL Device of Example SD-1> Table 5 shows the material composition of each layer in the organic EL element. [Table 5]

[0670] As the "PEDOT:PSS" which is the material for forming the hole injection layer in Table 5 above, a commercially available PEDOT:PSS solution (Clevios(TM) P VP AI4083, an aqueous dispersion of PEDOT:PSS represented by the following formula, manufactured by Heraeus Holdings) is used. [ka]

[0671] <Example SD-1> A PEDOT:PSS solution is spin-coated on a glass substrate on which ITO has been deposited to a thickness of 50 nm, and the substrate is baked on a hot plate at 200°C for 1 hour to form a hole injection layer having a thickness of 40 nm. Next, a XLP-101 solution is spin-coated, dried on a hot plate at 80°C for 10 minutes, and then baked on a hot plate at 200°C for 1 hour to form a hole transport layer having a thickness of 30 nm that is insoluble in the composition for forming an emitting layer. Next, the composition for forming an emitting layer prepared in Example S-1 is spin-coated, and the substrate is baked on a hot plate at 120°C for 1 hour to form a emitting layer having a thickness of 20 nm.

[0672] The multilayer film thus prepared is fixed to the substrate holder of a commercially available deposition apparatus (Showa Vacuum Co., Ltd.), and a molybdenum deposition boat containing ET-1, ET-2, Liq, and LiF, and a tungsten deposition boat containing aluminum are installed. The vacuum chamber is filled with 5×10 -4After the pressure is reduced to 1 Pa, ET-1 is heated and evaporated to a thickness of 10 nm to form the electron transport layer 1. Next, ET-2 and Liq are heated and evaporated to a thickness of 20 nm to form the electron transport layer 2. The evaporation rate is adjusted so that the mass ratio of ET-2 and Liq is approximately 1:1. The evaporation rate when forming the electron transport layer is 1 nm / sec. Then, LiF is heated and evaporated at an evaporation rate of 0.01 to 0.1 nm / sec to a thickness of 1 nm. Next, aluminum is heated and evaporated to a thickness of 100 nm to form the cathode. In this manner, an organic EL device is obtained. [Explanation of symbols]

[0673] 100 Organic electroluminescent device 101 Substrate 102 Anode 103 Hole injection layer 104 Hole transport layer 105 Light-emitting layer 106 Electron transport layer 107 Electron injection layer 108 Cathode

Claims

1. A polycyclic aromatic compound represented by the following formula (1-1): 【Chemistry 2】 In formula (1-1), R 1 ~R 12 each independently represents a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, an aryl group having 5 to 16 carbon atoms which may be substituted with an alkyl group having 1 to 6 carbon atoms, or a diarylamino group having 5 to 20 carbon atoms which may be substituted with an alkyl group having 1 to 6 carbon atoms; X 1 and X 2 are all >N-R or all >C(-R) 2 R in the >N-R is phenyl which may be substituted with alkyl having 1 to 6 carbon atoms, and >C(-R) 2 R is methyl; X 1 and X 2 When both are >N-R, X 3 is a single bond or >S, X 1 and X 2 All of them are >C(-R) 2 When X 3 is >O or >S, Y 1 is B; At least one selected from the group consisting of aryl rings and heteroaryl rings in formula (1-1) may be condensed with at least one cycloalkane having 3 to 24 carbon atoms, at least one hydrogen in the cycloalkane may be substituted with an aryl having 6 to 30 carbon atoms, a heteroaryl having 2 to 30 carbon atoms, an alkyl having 1 to 24 carbon atoms, or a cycloalkyl having 3 to 24 carbon atoms, and at least one -CH in the cycloalkane 2 - may be replaced by -O-; At least one hydrogen atom in the polycyclic aromatic compound represented by formula (1-1) may be substituted with cyano, halogen, or deuterium.

2. X 1 and X 2 are all >N-R, X 3 is a single bond or >S; The polycyclic aromatic compound according to claim 1 .

3. The polycyclic aromatic compound according to claim 2, which is represented by any one of the following formulas: 【Chemistry 3】 In the formula, Me is methyl and tBu is t-butyl.

4. X 1 and X 2 All of them are >C(-R) 2 and X 3 The polycyclic aromatic compound according to claim 1 , wherein is >O or >S.

5. The polycyclic aromatic compound according to claim 4, which is represented by any one of the following formulas: 【Chemistry 4】 In the formula, Me is methyl and tBu is t-butyl.

6. A material for an organic device, comprising the polycyclic aromatic compound according to any one of claims 1 to 5.

7. The material for an organic device according to claim 6 , 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.

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

9. A composition comprising the polycyclic aromatic compound according to any one of claims 1 to 5.

10. 6. 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.

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

12. The organic electroluminescent device according to claim 11 , wherein the light-emitting layer comprises a host and the polycyclic aromatic compound as a dopant.

13. The organic electroluminescent device according to claim 12, wherein the host is an anthracene-based compound, a fluorene-based compound, or a dibenzochrysene-based compound.

14. A display device or a lighting device comprising the organic electroluminescent device according to any one of claims 10 to 13.

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