Polycyclic aromatic compound and organic electroluminescent element

Abstract

To provide a novel material for use in organic EL elements having high external quantum efficiency.SOLUTION: A polycyclic aromatic compound has a structure composed of one or more structural units represented by formula (1), wherein rings A to E are aryl rings or heteroaryl rings, where at least one of the ring B and ring C has a group represented by formula (JABC) as a substituent, X is O, S, or Se, and Ar is a group represented by formula (Ar).SELECTED DRAWING: None

Description

[Technical field]

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

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

[0003] An organic EL element has a structure consisting of a pair of electrodes consisting of an anode and a cathode, and one or more layers containing an organic compound disposed between the pair of electrodes. The layer containing the organic compound (sometimes referred to as the "organic layer" in this specification) includes a light-emitting layer and a charge transport / injection layer that transports or injects charges such as holes and electrons, and various organic materials suitable for these layers have been developed.

[0004] Among them, Patent Document 1 discloses that polycyclic aromatic compounds in which aromatic rings are linked by hetero elements such as boron, phosphorus, oxygen, nitrogen, and sulfur are useful as materials for organic electroluminescent devices, etc. It has been reported that these polycyclic aromatic compounds have a large HOMO-LUMO gap and a high lowest excited triplet energy level (ET) and at the same time exhibit thermally activated delayed fluorescence, and are therefore particularly useful as fluorescent materials for organic electroluminescent devices. [Prior art documents] [Patent documents]

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

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

[0007] Another object of the present invention is to provide an organic electroluminescence device using a new combination of materials.An object of the present invention is to provide an organic EL device having a particularly high external quantum efficiency. [Means for solving the problem]

[0008] The present inventors have conducted extensive research to solve the above problems, and have succeeded in producing a new compound as a polycyclic aromatic compound in which aromatic rings are linked by hetero elements such as boron, oxygen, nitrogen, and sulfur. They have also found that an excellent organic EL device can be obtained by disposing a layer containing this polycyclic aromatic compound between a pair of electrodes to form an organic EL device, and have completed the present invention. That is, the present invention provides the following polycyclic aromatic compounds, and further provides materials for organic devices containing the following polycyclic aromatic compounds.

[0009] <1> A polycyclic aromatic compound having a structure consisting of one or more structural units represented by formula (1): [ka]

[0010] In formula (1), ring A, ring B, ring C, ring D and ring E each independently represent a substituted or unsubstituted aryl ring, or a substituted or unsubstituted heteroaryl ring; However, at least one selected from the group consisting of ring B and ring C is represented by at least the formula (J ABC or an aryl ring having a group represented by the formula (J ABC ) as a substituent, Each X is independently O, S or Se; Each Ar is independently a group represented by formula (Ar), The above formula (J ABC ) * indicates the point of attachment to the aryl or heteroaryl ring; ring P and ring Q each independently represent a substituted or unsubstituted aryl ring, or a substituted or unsubstituted heteroaryl ring; In the formula (Ar), # represents the position of attachment to nitrogen, Ring F is a substituted or unsubstituted aryl ring, or a substituted or unsubstituted heteroaryl ring; G is substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted arylthio, substituted or unsubstituted heteroarylthio, substituted or unsubstituted aryloxy, substituted or unsubstituted heteroaryloxy, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl; At least one selected from the group consisting of aryl and heteroaryl rings in the structure may be fused with at least one cycloalkane, the cycloalkane may be substituted with at least one substituent, and at least one -CH 2 - may be replaced by -O-; At least one hydrogen in the structure may be replaced with deuterium or a halogen, and at least one nitrogen is replaced with nitrogen-15 ( 15 N), and at least one sulfur may be replaced by sulfur-33 (33 S), Sulfur-34( 34 S) or sulfur-36( 36 S), at least one oxygen is oxygen-17( 17 O) or oxygen-18( 18 O), at least one carbon is carbon-13 ( 13 C), at least one boron is boron-11( 11 B) may be substituted.

[0011] <2> A polycyclic aromatic compound, wherein all X's are O, all X's are S, or all X's are Se.

[0012] <3> The formula (1) is a polycyclic aromatic compound represented by the following formula (2X): [ka]

[0013] In the formula (2X), Each X is independently O or S; Ar is defined as Ar in formula (1), Z a , Z b , Z c , Z d and Z e are each independently -C(-R Z )= or -N=, R J is the formula (J ABC ) is a group represented by R Z are each independently selected from the group consisting of hydrogen, deuterium, a halogen, a nitro group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amino group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms, with the proviso that the substituents substituted on adjacent atoms may be bonded to each other to form a ring.

[0014] <4> The formula (1) is a polycyclic aromatic compound represented by the following formula (2XJ): [ka]

[0015] In the formula (2XJ), Each X is independently O or S; Ar is defined as Ar in formula (1), Z a , Z b , Z c , Z d , Z e and Z j are each independently -C(-R Z )= or -N=, R Z are each independently selected from the group consisting of hydrogen, deuterium, a halogen, a nitro group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amino group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms, with the proviso that the substituents substituted on adjacent atoms may be bonded to each other to form a ring.

[0016] <5> A polycyclic aromatic compound represented by any of the following formulas: [ka]

[0017] [ka]

[0018] [ka]

[0019] [ka]

[0020] [ka]

[0021] [ka]

[0022] In the above formula, tBu is t-butyl.

[0023] <6> The present invention has a pair of electrodes consisting of an anode and a cathode, and an organic layer disposed between the pair of electrodes, the organic layer being <1> ~ <5> 13. An organic electroluminescence device comprising the polycyclic aromatic compound according to claim 12.

[0024] <7> The organic electroluminescent device, wherein the organic layer is a light-emitting layer.

[0025] <8> The light-emitting layer includes at least one selected from the group consisting of an assisting dopant and a phosphorescent material. <7> The organic electroluminescent device according to claim 1.

[0026] <9> <6> A display device or a lighting device comprising the organic electroluminescent device according to claim 1. Effect of the Invention

[0027] The present invention provides a novel polycyclic aromatic compound. The polycyclic aromatic compound of the present invention is useful as a material for an organic device, particularly as a material for a light-emitting layer for forming a light-emitting layer of an organic electroluminescent element. [Brief description of the drawings]

[0028] [Figure 1] FIG. 1 is a schematic cross-sectional view showing an example of an organic EL element. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0029] 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)".

[0030] In this specification, the term "adjacent groups" refers to two groups bonded to two adjacent atoms (two atoms directly bonded by a covalent bond) in a structural formula.

[0031] 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.

[0032] <Description of Substituents> First, the substituents used in this specification will be described in detail below.

[0033] In this specification, a substituent may be substituted with an additional substituent. For example, a specific substituent may be described as "substituted or unsubstituted". This means that the specific substituent is substituted with at least one additional substituent or is not substituted. In the same sense, "optionally substituted" may also be used. In this specification, the specific substituent may be referred to as a "first substituent" and the additional substituent may be referred to as a "second substituent".

[0034] In this specification, the substituent group Zα is composed of the substituents of the substituent group Z and the substituent represented by the formula (A30) described later.

[0035] In the present specification, the substituent group Z is an aryl optionally substituted with at least one group selected from the group consisting of aryl, heteroaryl, alkyl, cycloalkyl, cyano and halogen; heteroaryl optionally substituted with at least one group selected from the group consisting of aryl, heteroaryl, alkyl, cycloalkyl, cyano and halogen; diarylamino which may be substituted with at least one group selected from the group consisting of aryl, heteroaryl, alkyl, cycloalkyl, cyano and halogen (two aryls can be bonded to each other via a linking group); diheteroarylamino optionally substituted with at least one group selected from the group consisting of aryl, heteroaryl, alkyl, cycloalkyl, cyano and halogen (two heteroaryls can be bonded to each other via a linking group); arylheteroarylamino which may be substituted with at least one group selected from the group consisting of aryl, heteroaryl, alkyl, cycloalkyl, cyano and halogen (aryl and heteroaryl can be bonded to each other via a linking group); diarylboryl optionally substituted with at least one group selected from the group consisting of aryl, heteroaryl, alkyl, cycloalkyl, cyano and halogen (two aryls can be bonded via a single bond or a linking group); an alkyl group optionally substituted with at least one group selected from the group consisting of aryl, heteroaryl, cycloalkyl, cyano, and halogen; cycloalkyl optionally substituted with at least one group selected from the group consisting of aryl, heteroaryl, alkyl, cycloalkyl, cyano, and halogen; alkoxy optionally substituted with at least one group selected from the group consisting of aryl, heteroaryl, cycloalkyl, cyano and halogen; aryloxy optionally substituted with at least one group selected from the group consisting of aryl, heteroaryl, alkyl, cycloalkyl, cyano, and halogen; It is composed of substituted silyl, cyano and halogen.

[0036] The aryl of the second substituent in each group of the substituent group Z may be further substituted with an aryl, heteroaryl, alkyl, cycloalkyl, cyano, or halogen; similarly, the heteroaryl of the second substituent may be substituted with an aryl, heteroaryl, alkyl, cycloalkyl, cyano, or halogen.

[0037] In the present specification, when referring to a "substituent", the type of the substituent is not particularly limited, but unless otherwise specified, it may be any one group selected from the substituent group Z. For example, when a "substituted or unsubstituted" group is substituted, the group may be substituted with at least one group selected from the substituent group Z.

[0038] In this specification, "aryl" refers to, for example, an aryl having 6 to 30 carbon atoms, and preferably an aryl having 6 to 20 carbon atoms, an aryl having 6 to 16 carbon atoms, an aryl having 6 to 12 carbon atoms, or an aryl having 6 to 10 carbon atoms.

[0039] Specific examples of "aryl" include monovalent groups in which one hydrogen has been removed from the above-mentioned "aryl ring". For example, the monocyclic phenyl, the bicyclic ... , fluoren-(1-, 2-, 3-, 4-, or 9-)yl, phenalen-(1- or 2-)yl, phenanthrene-(1-, 2-, 3-, 4-, or 9-)yl, or anthracene-(1-, 2-, or 9-)yl; the tetracyclic ring system quaterphenylyl (5'-phenyl-m-terphenyl2-yl, 5'-phenyl-m-terphenyl3-yl, 5'-phenyl-m-terphenyl4-yl, or m-quaterphenyl); the fused tetracyclic ring system triphenylene-(1- or 2-)yl, pyrene-(1-, 2-, or 4-)yl, or naphthacene-(1-, 2-, or 5-)yl; and the fused pentacyclic ring system ferrylen-(1-, 2-, or 3-)yl, or pentacene-(1-, 2-, 5-, or 6-)yl. Other examples include monovalent groups of spirofluorene.

[0040] The aryl as the second substituent also includes a structure in which the aryl is substituted with at least one group selected from the group consisting of aryl such as phenyl (specific examples are the groups described above), alkyl such as methyl (specific examples are the groups described below), and cycloalkyl such as cyclohexyl or adamantyl (specific examples are the groups described below).

[0041] An example of such a group is a group in which the 9-position of fluorenyl as the second substituent is substituted with an aryl such as phenyl, an alkyl such as methyl, or a cycloalkyl such as cyclohexyl or adamantyl.

[0042] The "arylene" is, for example, an arylene having 6 to 30 carbon atoms, and preferably an arylene having 6 to 20 carbon atoms, an arylene having 6 to 16 carbon atoms, an arylene having 6 to 12 carbon atoms, or an arylene having 6 to 10 carbon atoms.

[0043] Specific examples of "arylene" include divalent groups obtained by removing one hydrogen from the above-mentioned "aryl" (monovalent group).

[0044] The "heteroaryl" is, for example, a heteroaryl having 2 to 30 carbon atoms, preferably a heteroaryl having 2 to 25 carbon atoms, a heteroaryl having 2 to 20 carbon atoms, a heteroaryl having 2 to 15 carbon atoms, or a heteroaryl having 2 to 10 carbon atoms. The "heteroaryl" contains, as a ring-constituting atom other than carbon, one or more heteroatoms selected from oxygen, sulfur, nitrogen, etc., and preferably 1 to 5 heteroatoms.

[0045] Specific examples of the "heteroaryl" include monovalent groups obtained by removing one hydrogen atom from the above-mentioned "heteroaryl ring". For example, pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, oxadiazolyl, thiadiazolyl, triazolyl, tetrazolyl, pyrazolyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, indolyl, isoindoleyl, 1H-indazolyl, benzimidazolyl, benzoxazolyl, benzothiazolyl, 1H-benzotriazolyl, quinolinyl, isoquinolinyl, cinnolinyl, quinazolinyl, quinoxalinyl, phenanthrolinyl, phthalazinyl, naphthyridinyl, purinyl, phthalidinyl, carbazolyl, etc. aryl, acridinyl, phenoxathiinyl, phenoxazinyl, phenothiazinyl, phenazinyl, phenazasilinyl, indolizinyl, furanyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, naphthobenzofuranyl, thienyl, benzothienyl, isobenzothienyl, dibenzothienyl, naphthobenzothienyl, monovalent groups of benzophosphole oxide rings, monovalent groups of dibenzophosphole oxide rings, furazanyl, thianthrenyl, indolocarbazolyl, benzoindolocarbazolyl, dibenzoindolocarbazolyl, imidazolinyl, or oxazolinyl. Other examples include monovalent groups of spiro[fluorene-9,9'-xanthene], monovalent groups of spirobi[silafluorene], and monovalent groups of benzoselenophene.

[0046] In addition, the heteroaryl as the second substituent also includes a structure in which the heteroaryl is substituted with at least one group selected from the group consisting of aryl such as phenyl (specific examples are the groups described above), alkyl such as methyl (specific examples are the groups described below), and cycloalkyl such as cyclohexyl or adamantyl (specific examples are the groups described below).

[0047] An example of such a group is a group in which the 9-position of the carbazolyl as the second substituent is substituted with an aryl such as phenyl, an alkyl such as methyl, or a cycloalkyl such as cyclohexyl or adamantyl. In addition, the heteroaryl as the second substituent also includes groups in which a nitrogen-containing heteroaryl such as pyridyl, pyrimidinyl, triazinyl, or carbazolyl is further substituted with a phenyl or biphenylyl.

[0048] The "heteroarylene" is, for example, a heteroarylene having 2 to 30 carbon atoms, and preferably a heteroarylene having 2 to 25 carbon atoms, a heteroarylene having 2 to 20 carbon atoms, a heteroarylene having 2 to 15 carbon atoms, or a heteroarylene having 2 to 10 carbon atoms. In addition, the "heteroarylene" is, for example, a divalent group such as a heterocycle containing, as a ring-constituting atom other than carbon, 1 to 5 heteroatoms selected from oxygen, sulfur, and nitrogen.

[0049] Specific examples of "heteroarylene" include divalent groups obtained by removing one hydrogen from the above-mentioned "heteroaryl" (monovalent group).

[0050] The term "diarylamino" refers to an amino substituted with two aryls, and the details of the aryls can be found in the above description of the "aryl".

[0051] The term "diheteroarylamino" refers to an amino group substituted with two heteroaryls. For details of the heteroaryl, the above description of the "heteroaryl" can be referred to.

[0052] The term "arylheteroarylamino" refers to an amino group substituted with an aryl and a heteroaryl. For details of the aryl and the heteroaryl, the above descriptions of "aryl" and "heteroaryl" can be cited.

[0053] The two aryls in the diarylamino as the first substituent can be bonded to each other via a linking group, the two heteroaryls in the diheteroarylamino as the first substituent can be bonded to each other via a linking group, and the aryl and heteroaryl in the arylheteroarylamino as the first substituent can be bonded to each other via a linking group. Here, "bonded via a linking group" means that, for example, the two phenyls in diphenylamine form a bond with a linking group, as shown below. This explanation also applies to diheteroarylamino and arylheteroarylamino formed by aryl or heteroaryl.

[0054] [ka]

[0055] Specific examples of the linking group include >O and >NR X ,>C(-R X ) 2 , -(CR X )=(CR X )-, >Si(-R X ) 2 , >S, >CO, >CS, >SO, >SO 2 , and >Se. X are each independently an alkyl, cycloalkyl, aryl, or heteroaryl, which may be substituted with an alkyl, cycloalkyl, aryl, or heteroaryl; and >C(-R) X 2 , -(CR X )=(CR X )-, >Si(-R) X 2 The two R's in each X is a single bond or a linking group X Y They may be bonded to each other via X to form a ring. Y As for the above, >O, >NR Y ,>C(-R) Y 2 , >Si(-R) Y 2 , >S, >CO, >CS, >SO, >SO2 , and >Se, R Y are each independently alkyl, cycloalkyl, aryl, or heteroaryl, which may be substituted with alkyl, cycloalkyl, aryl, or heteroaryl, provided that X Y >C(-R) Y 2 and >Si(-R) Y 2 If so, then two R Y does not bond to form a ring. In addition, the linking group may be alkenylene. Any hydrogen of the alkenylene is independently R 2X and R 2X are each independently an alkyl, a cycloalkyl, a substituted silyl, an aryl, or a heteroaryl, which may be substituted with an alkyl, a cycloalkyl, a substituted silyl, or an aryl. -(CR X )=(CR X )- Two R's X may be bonded together to form an aryl (such as a benzene ring) or heteroaryl ring together with the C=C to which they are attached. That is, -(CR X )=(CR X )- can be arylene (such as 1,2-phenylene) or heteroarylene.

[0056] In addition, in the present specification, when "diarylamino", "diheteroarylamino", or "arylheteroarylamino" is simply described, unless otherwise specified, it is assumed that the following explanation is added: "two aryls of the diarylamino can be bonded to each other via a linking group", "two heteroaryls of the diheteroarylamino can be bonded to each other via a linking group", and "aryl and heteroaryls of the arylheteroarylamino can be bonded to each other via a linking group", respectively.

[0057] "Diarylboryl" is a boryl substituted with two aryls, and the details of the aryls can be found in the above description of "aryl". In addition, the two aryls are not bound by a single bond or a linking group (e.g., -CH=CH-, -CR=CR-, -C≡C-, >NR, >O, >S, >C(-R) 2 , >Si(-R) 2 , or >Se), where R in -CR=CR-, R in >NR, >C(-R) 2 R in and R in >Si(-R) are aryl, heteroaryl, diarylamino, alkyl, alkenyl, alkynyl, cycloalkyl, alkoxy or aryloxy, and at least one hydrogen atom in R can be further substituted with aryl, heteroaryl, alkyl, alkenyl, alkynyl or cycloalkyl. In addition, two adjacent R can be bonded to each other to form a ring to form a cycloalkylene, arylene and heteroarylene. For details of the substituents listed here, the above explanations of "aryl", "arylene", "heteroaryl", "heteroarylene" and "diarylamino" and the below explanations of "alkyl", "alkenyl", "alkynyl", "cycloalkyl", "cycloalkylene", "alkoxy" and "aryloxy" can be cited. In addition, when simply described as "diarylboryl" in this specification, unless otherwise specified, the explanation that "the two aryls of diarylboryl can be bonded to each other via a single bond or a linking group" is added.

[0058] The "alkyl" may be either a straight chain or a branched chain, for example, a straight chain alkyl having 1 to 24 carbon atoms or a branched chain alkyl having 3 to 24 carbon atoms, and preferably an alkyl having 1 to 18 carbon atoms (branched chain alkyl having 3 to 18 carbon atoms), an alkyl having 1 to 12 carbon atoms (branched chain alkyl having 3 to 12 carbon atoms), an alkyl having 1 to 6 carbon atoms (branched chain alkyl having 3 to 6 carbon atoms), an alkyl having 1 to 5 carbon atoms (branched chain alkyl having 3 to 5 carbon atoms), an alkyl having 1 to 4 carbon atoms (branched chain alkyl having 3 to 4 carbon atoms), etc.

[0059] Specific examples of "alkyl" include methyl, ethyl, n-propyl, isopropyl, 1-ethyl-1-methylpropyl, 1,1-diethylpropyl, 1,1,2-trimethylpropyl, 1,1,2,2-tetramethylpropyl, 1-ethyl-1,2,2-trimethylpropyl, n-butyl, isobutyl, s-butyl, t-butyl, 2-ethylbutyl, 1,1-dimethylbutyl, 3,3-dimethylbutyl, 1,1-diethylbutyl, 1-ethyl-1-methylbutyl, 1-propyl-1-methylbutyl, 1,1,3-trimethylbutyl, 1-ethyl-1,3-dimethylbutyl, n-pentyl, isopentyl, neopentyl, t-pentyl (t-amyl), 1-methylpentyl, 2-propylpentyl, 1,1-dimethylpentyl, 1-ethyl-1-methylpentyl, 1-propyl-1 -Methylpentyl, 1-butyl-1-methylpentyl, 1,1,4-trimethylpentyl, n-hexyl, 1-methylhexyl, 2-ethylhexyl, 1,1-dimethylhexyl, 1-ethyl-1-methylhexyl, 1,1,5-trimethylhexyl, 3,5,5-trimethylhexyl, n-heptyl, 1-methylheptyl, 1-hexylheptyl, 1,1-dimethylheptyl, 2,2-dimethylhexyl Examples of the alkyl groups include methylheptyl, 2,6-dimethyl-4-heptyl, n-octyl, t-octyl (1,1,3,3-tetramethylbutyl), 1,1-dimethyloctyl, n-nonyl, n-decyl, 1-methyldecyl, n-undecyl, n-dodecyl, n-tridecyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, n-heptadecyl, n-octadecyl, and n-eicosyl.

[0060] An "alkylene" is a divalent group obtained by removing any hydrogen from an "alkyl", such as methylene, ethylene, or propylene.

[0061] For "alkenyl", the explanation of "alkyl" above can be referred to. It is a group in which a C--C single bond in the "alkyl" structure is replaced with a C=C double bond, and also includes groups in which not only one but two or more single bonds are replaced with double bonds (also called alkadiene-yl or alkatriene-yl).

[0062] An "alkenylene" is a divalent group obtained by removing any one hydrogen from an "alkenyl", and examples thereof include vinylene.

[0063] For "alkynyl", the explanation of "alkyl" above can be referred to. It is a group in which the C-C single bond in the "alkyl" structure is replaced with a C≡C triple bond, and also includes groups in which not only one but two or more single bonds are replaced with triple bonds (also called alkadiyn-yl or alkatriyn-yl).

[0064] The "cycloalkyl" is, for example, a cycloalkyl having 3 to 24 carbon atoms, and preferably a cycloalkyl having 3 to 20 carbon atoms, a cycloalkyl having 3 to 16 carbon atoms, a cycloalkyl having 3 to 14 carbon atoms, a cycloalkyl having 3 to 12 carbon atoms, a cycloalkyl having 5 to 10 carbon atoms, a cycloalkyl having 5 to 8 carbon atoms, a cycloalkyl having 5 to 6 carbon atoms, or a cycloalkyl having 5 carbon atoms.

[0065] Specific examples of "cycloalkyl" include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, or alkyl (particularly methyl) substituted derivatives thereof having 1 to 5 carbon atoms or 1 to 4 carbon atoms, bicyclo[1.0]butyl, bicyclo[1.1.1]pentyl, bicyclo[2.1.0]pentyl, bicyclo[2.1.1]hexyl, bicyclo[3.1.0]hexyl, bicyclo[2.2.1]heptyl (norbornyl), bicyclo[2.2.2]octyl, adamantyl, diamantyl, decahydronaphthalenyl, and decahydroazulenyl.

[0066] "Cycloalkylene" is, for example, cycloalkylene having 3 to 24 carbon atoms, and preferably cycloalkylene having 3 to 20 carbon atoms, cycloalkylene having 3 to 16 carbon atoms, cycloalkylene having 3 to 14 carbon atoms, cycloalkylene having 3 to 12 carbon atoms, cycloalkylene having 5 to 10 carbon atoms, cycloalkylene having 5 to 8 carbon atoms, cycloalkylene having 5 to 6 carbon atoms, or cycloalkylene having 5 carbon atoms.

[0067] Specific examples of "cycloalkylene" include structures obtained by removing one hydrogen from the above-mentioned "cycloalkyl" (monovalent group) to form a divalent group.

[0068] "Cycloalkenyl" refers to a group having a structure in which at least one pair of single bonds between two carbon atoms is replaced with a double bond from the above-mentioned "cycloalkyl" (e.g., -CH 2 -CH 2 Examples of the group in which - is replaced by -CH=CH- include groups that do not fall under the category of aryl. Specific examples include 1-cyclohexenyl, 1-cyclopentenyl, etc.

[0069] "Alkoxy" is a group represented by "Alk-O-(Alk is alkyl)". For details of the alkyl, the above explanation of "alkyl" can be cited.

[0070] "Aryloxy" is a group represented by "Ar-O-(Ar is aryl)", and the above explanation of "aryl" can be cited for details of the aryl.

[0071] The "substituted silyl" is, for example, a silyl substituted with at least one of an aryl, an alkyl, and a cycloalkyl, and is preferably a triarylsilyl, a trialkylsilyl, a tricycloalkylsilyl, a dialkylcycloalkylsilyl, or an alkyldicycloalkylsilyl.

[0072] The term "triarylsilyl" refers to a silyl group substituted with three aryl groups. For details of the aryl groups, see the above description of the "aryl group."

[0073] Specific "triarylsilyl" includes, for example, triphenylsilyl, diphenylmononaphthylsilyl, monophenyldinaphthylsilyl, trinaphthylsilyl, and the like.

[0074] The term "trialkylsilyl" refers to a silyl group substituted with three alkyl groups. For details of the alkyl group, see the above description of the "alkyl".

[0075] Specific examples of "trialkylsilyl" include trimethylsilyl, triethylsilyl, tri-n-propylsilyl, triisopropylsilyl, tri-n-butylsilyl, triisobutylsilyl, tri-s-butylsilyl, tri-t-butylsilyl, ethyldimethylsilyl, n-propyldimethylsilyl, isopropyldimethylsilyl, n-butyldimethylsilyl, isobutyldimethylsilyl, s-butyldimethylsilyl, t-butyldimethylsilyl, methyldiethylsilyl, n-propyldiethylsilyl, isopropyldiethylsilyl, n-butyldiethylsilyl, s-butyldiethylsilyl, t-butyldiethylsilyl, methyldi-n-propylsilyl, ethyldi-n-propylsilyl, n-butyldi-n-propylsilyl, s-butyldi-n-propylsilyl, t-butyldi-n-propylsilyl, methyldiisopropylsilyl, ethyldiisopropylsilyl, n-butyldiisopropylsilyl, s-butyldiisopropylsilyl, and t-butyldiisopropylsilyl.

[0076] The term "tricycloalkylsilyl" refers to a silyl group substituted with three cycloalkyl groups. For details of this cycloalkyl, see the above description of "cycloalkyl."

[0077] Specific "tricycloalkylsilyl" includes, for example, tricyclopentylsilyl or tricyclohexylsilyl.

[0078] The "dialkylcycloalkylsilyl" is a silyl group substituted with two alkyls and one cycloalkyl. For details of the alkyl and cycloalkyl, refer to the above descriptions of "alkyl" and "cycloalkyl".

[0079] The "alkyldicycloalkylsilyl" is a silyl group substituted with one alkyl and two cycloalkyl. For details of the alkyl and cycloalkyl, refer to the above descriptions of "alkyl" and "cycloalkyl".

[0080] "Halogen" is fluorine, chlorine, bromine or iodine, preferably fluorine, chlorine or bromine, more preferably fluorine or chlorine, even more preferably fluorine.

[0081] In the case of substitution with cyano or halogen, an embodiment in which all or a part of the hydrogen atoms in the aryl ring or heteroaryl ring in the structure are substituted with cyano or halogen is also preferred.

[0082] The substituent represented by formula (A30) has the following structure. [ka]

[0083] In the formula (A30), Ak is hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted cycloalkyl, or substituted or unsubstituted cycloalkenyl, and at least one of the alkyl, cycloalkyl, and cycloalkenyl is -CH 2 - may be replaced by -O- or -S-; R Ak is a substituted or unsubstituted aryl, a substituted or unsubstituted heteroaryl, a substituted or unsubstituted alkyl, or a substituted or unsubstituted cycloalkyl; R Akcan be bonded to Ak via a linking group or a single bond, and * indicates the bonding position.

[0084] In formula (A30), since Ak is the above-mentioned substituent, it does not conjugate with the unshared electron pair on N, so that the unshared electron pair can be conjugated with the π electron of the bonded destination, and a larger wavelength shift is possible compared to when an aryl or the like is present at the same position. The same applies to the influence on the multiple resonance effect, and a larger improvement in thermally activated delayed fluorescence (TADF) properties is possible.

[0085] R Ak is preferably aryl optionally substituted with alkyl or cycloalkyl, heteroaryl optionally substituted with alkyl or cycloalkyl, alkyl or cycloalkyl, more preferably aryl optionally substituted with alkyl, heteroaryl optionally substituted with alkyl, alkyl or cycloalkyl, even more preferably aryl optionally substituted with alkyl, and particularly preferably phenyl optionally substituted with methyl.

[0086] In formula (A30), Ak is preferably an alkyl group having 1 to 6 carbon atoms or a cycloalkyl group having 3 to 14 carbon atoms, preferably an alkyl group having 1 to 4 carbon atoms or a cycloalkyl group having 3 to 8 carbon atoms, more preferably an alkyl group having 1 to 4 carbon atoms, and further preferably methyl.

[0087] R Ak and Ak may be the same or different, and are preferably different.

[0088] R Ak can be bonded to Ak through a linking group or a single bond. In this case, the linking group is >O, >S or >Si(-R) 2 >Si(-R) 2 R is hydrogen, an aryl having 6 to 12 carbon atoms, an alkyl having 1 to 6 carbon atoms, or a cycloalkyl having 3 to 14 carbon atoms. AkExamples of the structure in which is bonded to Ak via a linking group or a single bond include the following.

[0089] [ka] In each of the above formulas, * indicates a bonding position.

[0090] 1. Polycyclic aromatic compounds 1-1. Polycyclic aromatic compounds 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). This polycyclic aromatic compound is useful as a compound for forming highly efficient and long-life elements. In addition, it is less likely to decompose during deposition compared to similar compounds having the same molecular weight. Hereinafter, in this specification, a polycyclic aromatic compound having a structure consisting of one or more structural units represented by formula (1) may be referred to as a "polycyclic aromatic compound represented by formula (1)".

[0091] [ka]

[0092] In formula (1), "A", "B", "C", "D" and "E" are each independently a symbol indicating a ring structure. In the structure represented by formula (1), at least one selected from the group consisting of ring B and ring C is at least represented by the formula (J ABC or an aryl ring having a group represented by the formula (J ABC ) is a condensed ring structure composed of a heteroaryl ring having a group represented by the formula:

[0093] In the formula (1), "A", "B", "C", "D" and "E", the rings A, B, C, D and E are each independently a substituted or unsubstituted aryl ring, or a substituted or unsubstituted heteroaryl ring. However, at least one selected from the group consisting of the rings B and C is at least one of the rings represented by the formula (J ABCor an aryl ring having a group represented by the formula (J ABC ) as a substituent.

[0094] Examples of the "aryl ring" of ring A, ring B, ring C, ring D and ring E in formula (1) include 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.

[0095] Specific examples of the "aryl ring" include a monocyclic benzene ring, a bicyclic bicyclic bicyclic bicyclic naphthalene ring, an indene ring, a tricyclic terphenyl ring (m-terphenyl, o-terphenyl, p-terphenyl), a condensed tricyclic acenaphthylene ring, a fluorene ring, a phenalene ring, a phenanthrene ring, an anthracene ring, a condensed tetracyclic triphenylene ring, a pyrene ring, a naphthacene ring, a chrysene ring, a condensed pentacyclic perylene ring, a pentacene ring, etc. In addition, the fluorene ring, the benzofluorene ring, and the indene ring each include a structure in which a fluorene ring, a benzofluorene ring, a cyclopentane ring, etc. are spiro-bonded. In addition, the fluorene ring, benzofluorene ring, and indene ring also include rings in which two of the two hydrogen atoms of the methylene are replaced by alkyl such as methyl as the first substituent described below, resulting in a dimethylfluorene ring, a dimethylbenzofluorene ring, a dimethylindene ring, and the like.

[0096] Examples of the "heteroaryl ring" of ring A, ring B, ring C, ring D and ring E 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.

[0097] Specific examples of the "heteroaryl ring" include a pyrrole ring, an oxazole ring, an isoxazole ring, a thiazole ring, an isothiazole ring, an imidazole ring, an oxadiazole ring, a thiadiazole ring, a triazole ring, a tetrazole ring, a pyrazole ring, a pyridine ring, a pyrimidine ring, a pyridazine ring, a pyrazine ring, a triazine ring, an indole ring, an isoindole ring, a 1H-indazole ring, a benzimidazole ring, a benzoxazole ring, a benzothiazole ring, a 1H-benzotriazole ring, a quinoline ring, an isoquinoline ring, a cinnoline ring, a quinazoline ring, a quinoxaline ring, a phthalazine ring, a naphthyridine ring, a purine ring, and a pteridine ring. Examples of the ring include a carbazole ring, an acridine ring, a phenoxathiin ring, a phenoxazine ring, a phenothiazine ring, a phenazine ring, a phenazasiline ring, an indolizine ring, a furan ring, a benzofuran ring, an isobenzofuran ring, a dibenzofuran ring, a thiophene ring, a benzothiophene ring, a dibenzothiophene ring, a furazan ring, a thianthrene ring, an indolocarbazole ring, a benzoindolocarbazole ring, a benzobenzoindolocarbazolyl, a naphthobenzofuran ring, a dioxin ring, a dihydroacridine ring, a xanthene ring, a thioxanthene ring, a dibenzodioxin ring, a dibenzazepine ring, a tribenzoazepine ring, and an iminodibenzyl ring. In addition, the dihydroacridine ring, the xanthene ring, and the thioxanthene ring are preferably such that two of the two hydrogen atoms of the methylene are replaced by alkyl such as methyl as the first substituent described later, to form a dimethyldihydroacridine ring, a dimethylxanthene ring, and a dimethylthioxanthene ring. In addition, bicyclic rings such as bipyridine ring, phenylpyridine ring, and pyridylphenyl ring, and tricyclic rings such as terpyridyl ring, bispyridylphenyl ring, and pyridylbiphenyl ring are also included as the "heteroaryl ring". The "heteroaryl ring" also includes a pyran ring.

[0098] Among the rings A, B, C, D and E, the aryl ring may be selected from the group consisting of a benzene ring, a biphenyl ring, an indene ring, a naphthalene ring, a fluorene ring, an anthracene ring and a phenanthrene ring, and the heteroaryl ring may be selected from the group consisting of a benzofuran ring, a benzothiophene ring, an indole ring, a dibenzofuran ring, a dibenzothiophene ring, a carbazole ring, a naphthofuran ring, a naphthothiophene ring, a benzoindole ring and a benzoselenophene ring. As the aryl or heteroaryl ring in the rings A, B, C, D and E, a benzene ring is preferred.

[0099] When at least one hydrogen atom in the aryl ring or heteroaryl ring is substituted with a substituent, the substituent is preferably substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted diarylamino, substituted or unsubstituted diheteroarylamino, substituted or unsubstituted arylheteroarylamino (amino having aryl and heteroaryl), substituted or unsubstituted diarylboryl (two aryls may be bonded via a single bond or a linking group), substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryloxy, substituted silyl, halogen, or -L-Ak. When these groups have a substituent, the substituent may be aryl, heteroaryl, alkyl or cycloalkyl, cyano, halogen, or diarylamino.

[0100] At least one selected from the group consisting of aryl and heteroaryl rings in the above structure may be fused with at least one cycloalkane, the cycloalkane may be substituted with at least one substituent, and at least one -CH 2 - may be replaced by -O-.

[0101] At least one hydrogen in the structure may be replaced with deuterium, and at least one nitrogen may be replaced with nitrogen-15 ( 15N), and at least one sulfur may be replaced by sulfur-33 ( 33 S), Sulfur-34( 34 S) or sulfur-36( 36 S), and at least one oxygen may be replaced by oxygen-17 ( 17 O) or oxygen-18( 18 O), at least one carbon is carbon-13 ( 13 C), at least one boron is boron-11( 11 B) may be substituted.

[0102] Examples of the "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.

[0103] Specific examples of cycloalkanes include cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclooctane, cyclononane, cyclodecane, norbornane (bicyclo[2.2.1]heptane), bicyclo[1.1.0]butane, bicyclo[1.1.1]pentane, bicyclo[2.1.0]pentane, bicyclo[2.1.1]hexane, bicyclo[3.1.0]hexane, bicyclo[2.2.1]heptane, bicyclo[2.2.2]octane, adamantane, diamantane, decahydronaphthalene, and decahydroazulene, as well as alkyl (particularly methyl) substituted, halogen (particularly fluorine) substituted, and deuterium substituted derivatives of these having 1 to 5 carbon atoms.

[0104] Among the above examples, a structure in which at least one hydrogen atom is substituted on the carbon atom at the α-position of the cycloalkane (the carbon atom at the position adjacent to the carbon atom at the condensation site in the cycloalkane fused to an aryl ring or heteroaryl ring) is preferred, a structure in which two hydrogen atoms are substituted on the carbon atom at the α-position is more preferred, and a structure in which a total of four hydrogen atoms are substituted on the two carbon atoms at the α-position is even more preferred. Examples of this substituent include an alkyl (particularly methyl) substituent having 1 to 5 carbon atoms, a halogen (particularly fluorine) substituent, and a deuterium substituent. In particular, a structure in which a partial structure represented by the following formula (B10) is bonded to adjacent carbon atoms in an aryl ring or heteroaryl ring is preferred.

[0105] [ka]

[0106] In formula (B10), Me represents methyl, and * represents the bonding position.

[0107] At least one hydrogen atom in the "aryl ring" or "heteroaryl ring" may be substituted with a first substituent, which is a substituted or unsubstituted "aryl", a substituted or unsubstituted "heteroaryl", a substituted or unsubstituted "diarylamino", a substituted or unsubstituted "diheteroarylamino", a substituted or unsubstituted "arylheteroarylamino", a substituted or unsubstituted "diarylboryl (two aryls may be bonded via a single bond or a linking group)", a substituted or unsubstituted "alkyl", a substituted or unsubstituted "cycloalkyl", a substituted or unsubstituted "alkoxy", a substituted or unsubstituted "aryloxy", a substituted "silyl", or -L-Ak. The aryl of the "aryl" or "heteroaryl" or "diarylamino" as the first substituent, the heteroaryl of the "diheteroarylamino", the aryl and heteroaryl of the "arylheteroarylamino", the aryl of the "diarylboryl", or the aryl of the "aryloxy" may be exemplified by the monovalent group of the "aryl ring" or "heteroaryl ring" described above.

[0108] Specifically, examples of "aryl" include aryl having 6 to 30 carbon atoms, preferably aryl having 6 to 24 carbon atoms, more preferably aryl having 6 to 20 carbon atoms, further preferably aryl having 6 to 16 carbon atoms, particularly preferably aryl having 6 to 12 carbon atoms, and most preferably aryl having 6 to 10 carbon atoms.

[0109] Specific examples of the aryl include phenyl, which is a monocyclic aryl, (2-, 3-, 4-)biphenylyl, which is a bicyclic aryl, (1-, 2-)naphthyl, (2-, 3-, 4-, 5-, 6-, 7-)indenyl, which is a condensed bicyclic aryl, and terphenylyl, which is a tricyclic aryl (m-terphenyl-2'-yl, m-terphenyl-4'-yl, m-terphenyl-5'-yl, o-terphenyl-3'-yl, o-terphenyl-4'-yl, p-terphenyl-2'-yl, m-terphenyl-2-yl, m-terphenyl-3-yl, m-terphenyl-4-yl, o-terphenyl-2-yl, o-terphenyl-3-yl, o-terphenyl-4-yl, p-terphenyl-2-yl, p-terphenyl-3-yl, p ... aryl-4-yl), fused tricyclic aryls, acenaphthylene-(1-,3-,4-,5-)yl, fluoren-(1-,2-,3-,4-,9-)yl, phenalen-(1-,2-)yl, (1-,2-,3-,4-,9-)phenanthryl, tetracyclic aryls, quaterphenylyl (5'-phenyl-m-terphenyl-2-yl, 5'-phenyl-m-terphenylyl), aryls such as fused tetracyclic aryls, triphenylene-(1-, 2-)yl, pyrene-(1-, 2-, 4-)yl, naphthacene-(1-, 2-, 5-)yl, and fused pentacyclic aryls such as perylene-(1-, 2-, 3-)yl and pentacene-(1-, 2-, 5-, 6-)yl.

[0110] Furthermore, examples of "heteroaryl" include heteroaryls having 2 to 30 carbon atoms, preferably heteroaryls having 2 to 25 carbon atoms, more preferably heteroaryls having 2 to 20 carbon atoms, further preferably heteroaryls having 2 to 15 carbon atoms, and particularly preferably heteroaryls having 2 to 10 carbon atoms. Furthermore, examples of heteroaryls include heterocycles containing, as ring-constituting atoms other than carbon, 1 to 5 heteroatoms selected from oxygen, sulfur, and nitrogen.

[0111] Specific examples of heteroaryl include furyl, thienyl, pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, pyrazolyl, oxadiazolyl, furazanyl, thiadiazolyl, triazolyl, tetrazolyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, benzo[b]thienyl, dibenzothienyl, indyl, and aryl. Examples of the aryl include isoindolyl, 1H-indazolyl, benzimidazolyl, benzoxazolyl, benzothiazolyl, 1H-benzotriazolyl, quinolyl, isoquinolyl, cinnolyl, quinazolyl, quinoxalinyl, phthalazinyl, naphthyridinyl, purinyl, pteridinyl, carbazolyl, acridinyl, phenoxazinyl, phenothiazinyl, phenazinyl, phenoxathiinyl, thianthrenyl, and indolizinyl.

[0112] Furthermore, the "alkyl" as the first substituent may be either linear or branched, and examples thereof include linear alkyl having 1 to 24 carbon atoms or branched alkyl having 3 to 24 carbon atoms. An alkyl having 1 to 18 carbon atoms (branched alkyl having 3 to 18 carbon atoms) is preferred, an alkyl having 1 to 12 carbon atoms (branched alkyl having 3 to 12 carbon atoms) is more preferred, an alkyl having 1 to 8 carbon atoms (branched alkyl having 3 to 8 carbon atoms) is even more preferred, an alkyl having 1 to 6 carbon atoms (branched alkyl having 3 to 6 carbon atoms) is particularly preferred, and an alkyl having 1 to 5 carbon atoms (branched alkyl having 3 to 5 carbon atoms) is most preferred.

[0113] Specific examples of alkyl include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, t-butyl, n-pentyl, isopentyl, neopentyl, t-pentyl (t-amyl), n-hexyl, 1-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, n-heptyl, 1-methylhexyl, n-octyl, t-octyl (1,1,3,3-tetramethylbutyl), and the like. ), 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 2,6-dimethyl-4-heptyl, 3,5,5-trimethylhexyl, n-decyl, n-undecyl, 1-methyldecyl, n-dodecyl, n-tridecyl, 1-hexylheptyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, n-heptadecyl, n-octadecyl, and n-eicosyl.

[0114] 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.

[0115] As the substituent containing the "alkyl", a tertiary alkyl represented by the following formula (tR) is one of the particularly preferred substituents when at least one hydrogen atom in the above-mentioned aryl ring or heteroaryl ring is substituted with a substituent. This is because such a bulky substituent increases the intermolecular distance, thereby improving the luminescence quantum yield (PLQY). In addition, a substituent in which the tertiary alkyl represented by formula (tR) is substituted with another substituent as a second substituent is also preferred. Specifically, diarylamino substituted with a tertiary alkyl represented by formula (tR), carbazolyl (preferably N-carbazolyl) substituted with a tertiary alkyl represented by formula (tR), or benzocarbazolyl (preferably N-benzocarbazolyl) substituted with a tertiary alkyl represented by formula (tR) can be mentioned.

[0116] For "diarylamino", examples include the groups described below as "first substituent". Examples of the substitution of the group of formula (tR) on diarylamino, carbazolyl, and benzocarbazolyl include examples in which some or all of the hydrogen atoms on the aryl ring or benzene ring in these groups are substituted with the group of formula (tR).

[0117] [ka]

[0118] In the formula (tR), R a , R b , and R c are each independently an alkyl group having 1 to 24 carbon atoms, and any -CH 2 - may be replaced by -O-, and * is the attachment position.

[0119] R a , R b , and R cThe "alkyl having 1 to 24 carbon atoms" in the above formula 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).

[0120] 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.

[0121] R a , R b , and R c Specific examples of alkyl include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, t-butyl, n-pentyl, isopentyl, neopentyl, t-pentyl, n-hexyl, 1-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, n-heptyl, 1-methylhexyl, n-octyl, t-octyl, 1-methylheptyl, 2 Examples of aryl groups include 1-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.

[0122] 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 of the alkyl group 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.

[0123] Examples of the "cycloalkyl" as the first substituent include cycloalkyl having 3 to 24 carbon atoms, cycloalkyl having 3 to 20 carbon atoms, cycloalkyl having 3 to 16 carbon atoms, cycloalkyl having 3 to 14 carbon atoms, cycloalkyl having 5 to 10 carbon atoms, cycloalkyl having 5 to 8 carbon atoms, cycloalkyl having 5 to 6 carbon atoms, and cycloalkyl having 5 carbon atoms.

[0124] Specific examples of cycloalkyl include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, or alkyl (particularly methyl) substituted derivatives of these having 1 to 5 carbon atoms, norbornyl (bicyclo[2.2.1]heptyl), bicyclo[1.1.0]butyl, bicyclo[1.1.1]pentyl, bicyclo[2.1.0]pentyl, bicyclo[2.1.1]hexyl, bicyclo[3.1.0]hexyl, bicyclo[2.2.2]octyl, adamantyl, diamantyl, decahydronaphthalenyl, and decahydroazulenyl.

[0125] Furthermore, examples of the "alkoxy" as the first substituent include linear alkoxy having 1 to 24 carbon atoms or branched alkoxy having 3 to 24 carbon atoms. An alkoxy having 1 to 18 carbon atoms (branched alkoxy having 3 to 18 carbon atoms) is preferred, an alkoxy having 1 to 12 carbon atoms (branched alkoxy having 3 to 12 carbon atoms) is more preferred, an alkoxy having 1 to 6 carbon atoms (branched alkoxy having 3 to 6 carbon atoms) is even more preferred, and an alkoxy having 1 to 5 carbon atoms (branched alkoxy having 3 to 5 carbon atoms) is particularly preferred.

[0126] Specific alkoxy includes methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, s-butoxy, t-butoxy, t-amyloxy, pentyloxy, hexyloxy, heptyloxy, octyloxy, and the like.

[0127] In addition, examples of the "substituted silyl" as the first substituent include silyl substituted with three substituents selected from the group consisting of alkyl, cycloalkyl, and aryl, such as trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, alkyldicycloalkylsilyl, triarylsilyl, dialkylarylsilyl, and alkyldiarylsilyl.

[0128] The "trialkylsilyl" refers to a group in which three hydrogen atoms in a silyl group are each independently substituted with an alkyl, and the alkyl can be cited from the groups described above as the "alkyl" in the first substituent. 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.

[0129] 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 isopropylsilyl 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.

[0130] Examples of "tricycloalkylsilyl" include groups in which three hydrogen atoms in a silyl group are each independently substituted with a cycloalkyl, and examples of the cycloalkyl include the groups described as "cycloalkyl" in the first substituent. Preferred cycloalkyl groups for substitution are cycloalkyl groups having 5 to 10 carbon atoms, and specific examples include cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, bicyclo[1.1.1]pentyl, bicyclo[2.1.0]pentyl, bicyclo[2.1.1]hexyl, bicyclo[3.1.0]hexyl, bicyclo[2.2.1]heptyl, bicyclo[2.2.2]octyl, adamantyl, decahydronaphthalenyl, and decahydroazulenyl.

[0131] Specific examples of tricycloalkylsilyl include tricyclopentylsilyl and tricyclohexylsilyl.

[0132] 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.

[0133] 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 specific alkyl and aryl groups mentioned above. Specific examples of triarylsilyl include triphenylsilyl.

[0134] In addition, the "aryl" in the "diarylboryl" of the first substituent can be quoted from the above description of the aryl. In addition, the two aryls can be bonded together by a single bond or a linking group (e.g., >C(-R) 2 , >O, >S or >NR), where >C(-R) 2 And R in >NR is aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, alkoxy, or aryloxy (the above, first substituent), and the first substituent may be further substituted with aryl, heteroaryl, alkyl, or cycloalkyl (the above, second substituent). As specific examples of these groups, the above-mentioned explanations of aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, alkoxy, or aryloxy as the first substituent can be cited.

[0135] In the first substituent -L-Ak, L is >NR, >O or >S, and R of >NR is optionally substituted aryl, optionally substituted heteroaryl, optionally substituted alkyl or optionally substituted cycloalkyl. Also, R of >NR may be bonded to Ak via a linking group or a single bond.

[0136] Ak is hydrogen, an optionally substituted alkyl, or an optionally substituted cycloalkyl, and at least one hydrogen in the alkyl and cycloalkyl may be substituted, and at least one -CH 2 - may be substituted with -O- and -S-.

[0137] Preferably, L is >NR.

[0138] When L is >NR, R is preferably aryl optionally substituted with alkyl or cycloalkyl, heteroaryl optionally substituted with alkyl or cycloalkyl, alkyl or cycloalkyl, more preferably aryl optionally substituted with alkyl, heteroaryl optionally substituted with alkyl, alkyl or cycloalkyl, even more preferably aryl optionally substituted with alkyl, and particularly preferably phenyl optionally substituted with methyl.

[0139] Ak is preferably alkyl having 1 to 6 carbon atoms or cycloalkyl having 3 to 14 carbon atoms, more preferably alkyl having 1 to 4 carbon atoms or cycloalkyl having 3 to 8 carbon atoms, more preferably alkyl having 1 to 4 carbon atoms, and even more preferably methyl.

[0140] When L is >NR, R may be bonded to Ak via a linking group or a single bond. In this case, the linking group may be >O, >S or >Si(-R) 2 >Si(-R) 2 R is hydrogen, aryl having 6 to 12 carbon atoms, alkyl having 1 to 6 carbon atoms, or cycloalkyl having 3 to 14 carbon atoms. Examples of the structure in which R of >NR is bonded to Ak via a linking group or a single bond include the following.

[0141] [ka]

[0142] In each of the above formulas, Me is methyl and is bonded to an atom constituting a ring of an aryl ring or a heteroaryl ring in ring A, ring B, ring C, ring D or ring E at the position *.

[0143] As explained above, at least one hydrogen atom in the first substituent, substituted or unsubstituted "aryl", substituted or unsubstituted "heteroaryl", substituted or unsubstituted "diarylamino", substituted or unsubstituted "diheteroarylamino", substituted or unsubstituted "arylheteroarylamino", substituted or unsubstituted "diarylboryl (two aryls may be bonded via a single bond or a linking group)", substituted or unsubstituted "alkyl", substituted or unsubstituted "cycloalkyl", substituted or unsubstituted "alkoxy", substituted or unsubstituted "aryloxy", or substituted "silyl", may be substituted with a second substituent. Examples of the second substituent include aryl, heteroaryl, alkyl, or cycloalkyl, and specific examples of these can be found in the explanation of the monovalent group of the "aryl ring" or "heteroaryl ring" described above, and the "alkyl" or "cycloalkyl" as the first substituent. In addition, the aryl and heteroaryl as the second substituent also include structures in which at least one hydrogen atom in these is substituted with an aryl such as phenyl (specific examples are the groups described above), an alkyl such as methyl and t-butyl (specific examples are the groups described above), or a cycloalkyl such as cyclohexyl (specific examples are the groups described above). As an example, when the second substituent is carbazolyl, a carbazolyl in which at least one hydrogen atom at the 9-position is substituted with an aryl such as phenyl, an alkyl such as methyl, or a cycloalkyl such as cyclohexyl is also included in the heteroaryl as the second substituent.

[0144] The emission wavelength can be adjusted by the structural steric hindrance, electron donating property and electron withdrawing property of the first substituent. The group represented by the following structural formula is preferable, and more preferable are methyl, t-butyl, t-amyl, t-octyl, neopentyl, adamantyl, phenyl, o-tolyl, p-tolyl, 2,4-xylyl, 2,5-xylyl, 2,6-xylyl, 2,4,6-mesityl, diphenylamino, di-p-tolylamino, bis(p-(t-butyl)phenyl)amino, carbazolyl (particularly N-carbazolyl), 3,6-dimethylcarbazolyl, and the like. Preferred are methyl, t-butyl, t-amyl, t-octyl, neopentyl, adamantyl, phenyl, o-tolyl, 2,6-xylyl, 2,4,6-mesityl, diphenylamino, di-p-tolylamino, bis(p-(t-butyl)phenyl)amino, carbazolyl, 3,6-dimethylcarbazolyl, and 3,6-di-t-butylcarbazolyl. From the viewpoint of ease of synthesis, larger steric hindrance is preferred for selective synthesis, and specifically, t-butyl, t-amyl, t-octyl, adamantyl, o-tolyl, p-tolyl, 2,4-xylyl, 2,5-xylyl, 2,6-xylyl, 2,4,6-mesityl, di-p-tolylamino, bis(p-(t-butyl)phenyl)amino, 3,6-dimethylcarbazolyl and 3,6-di-t-butylcarbazolyl are preferred.

[0145] 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]

[0146] [ka]

[0147] [ka]

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[0159] [ka]

[0160] When two or three hydrogens bonded to consecutive (adjacent) carbon atoms are replaced, the substituent may be a group represented by formula (A20). [ka]

[0161] In formula (A20), L S are >NR, >O, >Si(-R) 2 or >S, wherein R of the >NR is an optionally substituted aryl, an optionally substituted heteroaryl, an optionally substituted alkyl or an optionally substituted cycloalkyl, and the >Si(-R) 2 R is hydrogen, an optionally substituted aryl, an optionally substituted alkyl, or an optionally substituted cycloalkyl, and may be bonded to each other to form a ring. 2 At least one of R is connected to ring A, ring B, ring C, ring D, ring E, and ring R by a linking group or a single bond. S and may be linked to at least one selected from the group consisting of r is an integer from 1 to 4; R S are each independently hydrogen, optionally substituted alkyl, or optionally substituted cycloalkyl, and any R S is any other R S and may be bonded to each other via a linking group or a single bond, The group represented by formula (A20) is bonded to two adjacent atoms on an aryl ring, a heteroaryl ring, or a cycloalkane ring at two *'s, respectively.

[0162] When the polycyclic aromatic compound represented by formula (1) contains a group represented by formula (A20), the number of the groups is preferably 1 or 2. The group represented by formula (A20) may be a substituent in any one of rings A, B, C, D, and E.

[0163] The group represented by formula (A20) is bonded to two adjacent atoms on the aryl ring or heteroaryl ring with two *. The group represented by formula (A20) is preferably bonded to two adjacent atoms on the aryl ring or heteroaryl ring with two *. In this case, it is preferable that both of the two adjacent atoms on the ring are carbon atoms. A fused ring structure is formed by bonding the group represented by formula (A20) to the aryl ring or heteroaryl ring. The compound represented by formula (1) having this fused ring structure has a harder structure. When the compound becomes harder, the vibration of the molecule is suppressed, the EQE is improved, the stability of the molecule is increased, and the element life is expected to be extended.

[0164] In formula (A20), L S are >NR, >O, >Si(-R) 2 or >S. L in the group represented by formula (A20) S By selecting the type of L, it is possible to control the HOMO and LUMO of the polycyclic aromatic compound represented by formula (1). S When is NR, >O, or >S, the HOMO and LUMO become shallower, and when is Si, the HOMO and LUMO become deeper. If the HOMO and LUMO are shallower, it is expected that the TTF element using them will have a longer life, higher efficiency, and lower driving voltage. On the other hand, if the HOMO and LUMO are deeper, the hole trapping properties of the dopant will disappear, and it is expected that the driving voltage will be significantly reduced.

[0165] L in formula (A20) S R in >NR is optionally substituted aryl, optionally substituted heteroaryl, optionally substituted alkyl or optionally substituted cycloalkyl. S >Si(-R)2 R is hydrogen, an optionally substituted aryl, an optionally substituted alkyl or an optionally substituted cycloalkyl, and two R may be bonded to each other to form a ring. 2 At least one of R is connected to ring A, ring B, ring C, ring D, ring E, and ring R by a linking group or a single bond. S L is preferably >NR, >O or >S, more preferably >NR or >O, and further preferably >NR.

[0166] L S When R is >NR, R is preferably aryl optionally substituted with alkyl or cycloalkyl, heteroaryl optionally substituted with alkyl or cycloalkyl, alkyl or cycloalkyl, more preferably aryl optionally substituted with alkyl or cycloalkyl, or heteroaryl optionally substituted with alkyl or cycloalkyl, even more preferably aryl optionally substituted with alkyl or cycloalkyl, and particularly preferably phenyl optionally substituted with alkyl or cycloalkyl.

[0167] In formula (A20), r represents an integer of 1 to 4, preferably 2 or 3, and more preferably 2.

[0168] In formula (A20), R S are each independently hydrogen, optionally substituted alkyl, or optionally substituted cycloalkyl, and any R S is any other R S and may be linked to each other via a linking group or a single bond.

[0169] R Sare preferably bonded to each other by a linking group or a single bond. Examples of the linking group include >O and >S. Examples of the divalent group formed by bonding to each other include alkylene. At least one hydrogen atom in the alkylene may be substituted with an alkyl or cycloalkyl, and at least one (preferably one) -CH 2 The - may be substituted with -O- and -S-. The divalent group formed by bonding to each other is preferably a linear alkylene having 2 to 5 carbon atoms, more preferably a linear alkylene having 3 or 4 carbon atoms, and particularly preferably a linear alkylene having 4 carbon atoms (-(CH 2 ) 4 More preferably, the straight chain alkylene having 4 carbon atoms (-(CH 2 ) 4 It is particularly preferred that -) is unsubstituted.

[0170] Two Rs bonded to adjacent carbon atoms S are bonded to each other by a linking group or a single bond, the remaining R S are each independently hydrogen or optionally substituted alkyl, or L S >NR or >Si(-R) 2 It is preferred that the R is bonded to the

[0171] Two Rs bonded to adjacent carbon atoms S are bonded to each other by a linking group or a single bond, the remaining R S As the optionally substituted alkyl as mentioned above, it is more preferable that it is an optionally substituted alkyl having 1 to 6 carbon atoms, further preferably an unsubstituted alkyl having 1 to 6 carbon atoms, and most preferably that all of them are methyl.

[0172] That is, a preferred example of the group represented by formula (A20) is a group represented by formula (A20-a). [ka]

[0173] In the formula, Me is methyl.

[0174] L S >NR and >Si(-R) 2 At least one of R is connected to ring A, ring B, ring C, ring D, ring E, and ring R by a linking group or a single bond. S and L S When is >NR, examples thereof include groups represented by any of the following formulae, and a group represented by formula (A20-b-1) is preferred.

[0175] [ka]

[0176] In each formula, Me is methyl. In each formula, * is bonded to two or three consecutive (adjacent) atoms on the ring of any one of the aryl ring, heteroaryl ring, or cycloalkane ring of ring A, ring B, ring C, ring D, and ring E.

[0177] In formula (1), X's are each independently O, S or Se. It is preferable that all X's are O, all X's are S or all X's are Se, and it is more preferable that all X's are O or all X's are S.

[0178] <Explanation of formula (2X)> [ka]

[0179] Preferred examples of polycyclic aromatic compounds having a structure consisting of one or more structural units represented by formula (1) include polycyclic aromatic compounds represented by formula (2X).

[0180] In formula (2X), each X is independently O or S, Ar is the same as defined in formula (1), and Za , Z b , Z c , Z d and Z e are each independently -C(-R Z )= or -N= and R J is the formula (J ABC ) is a group represented by R Z are each independently selected from the group consisting of hydrogen, deuterium, a halogen, a nitro group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amino group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms, with the proviso that substituents on adjacent atoms can be bonded to each other to form a ring.

[0181] <Explanation of formula (2XJ)> [ka]

[0182] A preferred example of a polycyclic aromatic compound having a structure consisting of one or more structural units represented by formula (1) is a polycyclic aromatic compound represented by formula (2XJ).

[0183] In formula (2XJ), each X is independently O or S, Ar is the same as defined in formula (1), and Z a , Z b , Z c , Z d , Z e and Z j are each independently -C(-R Z )= or -N= and R Zare each independently selected from the group consisting of hydrogen, deuterium, a halogen, a nitro group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amino group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms, with the proviso that substituents on adjacent atoms can be bonded to each other to form a ring.

[0184] <expression(J ABC ) Explanation> In the polycyclic aromatic compound structure represented by formula (1) of the present invention, at least one selected from the group consisting of ring B and ring C is represented by at least the formula (J ABC or an aryl ring having a group represented by the formula (J ABC ) as a substituent. [ka]

[0185] Formula (J ABC ), the * indicates the point of attachment to the aryl or heteroaryl ring.

[0186] Formula (J ABC ), the "P" and "Q" in the circles are symbols indicating the ring structures shown in each circle.

[0187] Formula (J ABC In the above formula, the P ring and the Q ring each form a divalent group having bonds to two adjacent elements (preferably carbon) on an aryl ring or heteroaryl ring in the structure. The two bonds bond to the carbon adjacent to the nitrogen.

[0188] Formula (J ABCIn the formula (1), the ring P and the ring Q are each independently a substituted or unsubstituted aryl ring, or a substituted or unsubstituted heteroaryl ring. For details of the "aryl ring" and the "heteroaryl ring", the explanation of the "aryl ring" and the "heteroaryl ring" of the ring A, the ring B, the ring C, the ring D and the ring E in the formula (1) can be cited.

[0189] In the above structure, at least one selected from the group consisting of an aryl ring and a heteroaryl ring may be fused with at least one cycloalkane, the cycloalkane may be substituted with at least one substituent, and at least one -CH in the cycloalkane may be fused with at least one -CH 2 - may be replaced by -O-.

[0190] In the above structure, at least one hydrogen may be replaced with deuterium and at least one nitrogen may be replaced with nitrogen-15( 15 N), and at least one sulfur may be replaced by sulfur-33 ( 33 S), Sulfur-34( 34 S) or sulfur-36( 36 S), and at least one oxygen may be replaced by oxygen-17 ( 17 O) or oxygen-18( 18 O), at least one carbon is carbon-13 ( 13 C), at least one boron is boron-11( 11 B) may be substituted.

[0191] In the substituted or unsubstituted aryl ring or substituted or unsubstituted heteroaryl ring in the P ring and the Q ring, the substituent when "substituted or unsubstituted (substituted or unsubstituted)" is used includes at least one substituent selected from the substituent group Zα. The substituent may be cyano or halogen. The ring having the element having two bonds as a ring constituent element is preferably a 5-membered ring or a 6-membered ring, more preferably a 6-membered ring. This ring may be further condensed with another ring. Examples of the 6-membered ring include a benzene ring, a pyridine ring, a pyrazine ring, and a pyrimidine ring. Examples of the 6-membered ring further condensed with another ring include a naphthalene ring, a quinoline ring, a benzofuran ring, a benzothiophene ring, an indole ring, a benzoselenophene ring, a dibenzofuran ring, a dibenzothiophene ring, a carbazole ring, and a dibenzoselenophene ring. Examples of the 5-membered ring include a furan ring, a thiophene ring, a pyrrole ring, a thiazole ring, and a selenophene ring. Examples of a five-membered ring condensed with another ring include a benzofuran ring, a benzothiophene ring, an indole ring, and a benzoselenophene ring.

[0192] The P ring and the Q ring are each independently preferably a substituted or unsubstituted benzene ring, a substituted or unsubstituted fluorene ring, a substituted or unsubstituted dibenzofuran ring, a substituted or unsubstituted dibenzothiophene ring, a substituted or unsubstituted dibenzoselenophene ring, a substituted or unsubstituted dibenzosilolane ring, or a substituted or unsubstituted N-phenylcarbazole ring. Any one of the P ring and the Q ring is preferably a substituted or unsubstituted benzene ring, more preferably an unsubstituted benzene ring. When any one of the P ring and the Q ring is an unsubstituted benzene ring, the other may be a substituted or unsubstituted benzene ring, a substituted or unsubstituted fluorene ring, a substituted or unsubstituted dibenzofuran ring, a substituted or unsubstituted dibenzothiophene ring, a substituted or unsubstituted dibenzoselenophene ring, or a substituted or unsubstituted N-phenylcarbazole ring. Here, the "substitution" in the substituted benzene ring, substituted fluorene ring, substituted dibenzofuran ring, substituted dibenzothiophene ring, substituted dibenzoselenophene ring, substituted dibenzosilorane ring, or substituted N-carbazole ring may be deuterium, carbazole, phenyl, biphenyl, or terphenyl, but is not limited to these examples.

[0193] Formula (J ABC Preferred examples of the group represented by the formula (J ABC -1), formula (J ABC -2), formula (J ABC -3), formula (J ABC -4) or the formula (J ABC -5). [ka]

[0194] Formula (J ABC -1)~Formula(J ABC -5), Z X -C(-R ZX )= or -N=, both of which are -C(-R ZX )= is preferred.

[0195] R ZX R is independently hydrogen or a substituent. ZX When R is a substituent, the substituent may be at least one substituent selected from the substituent group Zα, and is preferably a substituted or unsubstituted aryl, a substituted or unsubstituted heteroaryl, a substituted or unsubstituted alkyl, or a substituted or unsubstituted cycloalkyl, and more preferably an unsubstituted alkyl. ZX Preferably, each of them is hydrogen.

[0196] Y 1 >NR NY ,>C(-R CY ) 2 , >O, >Si(-R IY ) 2 , >PR PY , >P(=O)R POY , >S, >SO, >SO 2 or >Se and R NY , R CY , R IY , R PY and R POY are each independently hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl; CY may be bonded to each other to form a ring, and two R IY may be bonded to each other to form a ring. NY R is preferably a substituted or unsubstituted aryl having 6 to 18 carbon atoms, and more preferably an unsubstituted phenyl. CY and R IY are each independently preferably an aryl having 6 to 18 carbon atoms or an alkyl having 1 to 18 carbon atoms, and more preferably unsubstituted phenyl or methyl.

[0197] Y 1 As for the NY , >O or >S are preferred.

[0198] Z Eare each independently -C(-R ZE )= or -N= and R ZE R is independently hydrogen or a substituent. ZE When R is a substituent, the substituent may be at least one substituent selected from the substituent group Zα, and is preferably a substituted or unsubstituted aryl, a substituted or unsubstituted heteroaryl, a substituted or unsubstituted alkyl, a cyano, a halogen, or a substituted or unsubstituted cycloalkyl, and more preferably an unsubstituted alkyl. ZE Preferably, each of them is hydrogen.

[0199] -N = Z E is the formula (J ABC -1)~Formula(J ABC In each monocyclic ring in formula (J-5), it is preferable that the number is 0 to 2, more preferably 0 to 1, and further preferably 0. ABC -1)~Formula(J ABC -5), Z E are both -C(-R ZE )= is preferred.

[0200] Formula (J ABC -1)~Formula(J ABC In the formula (J ABC -1), formula (J ABC -2), formula (J ABC -3) and the formula (J ABC -5) is preferred, and the formula (J ABC -1), formula (J ABC -2) and the formula (J ABC -5) is more preferable.

[0201] Formula (J ABC -1)~Formula(J ABC Examples of -5) include structures represented by any one of the following: [ka]

[0202] [ka]

[0203] In formula (1), the formula (J ABC The number of groups represented by the formula (J) is preferably 1 to 3, and more preferably 1 to 2. ABC When a plurality of groups represented by the formula (J ABC From the viewpoint of ease of synthesis, the groups represented by the formula (J) may be the same or different. ABC ) are preferably the same as each other.

[0204] Formula (J ABC The substitution position of the group represented by the formula (J) is not particularly limited. ABC When the aryl ring to which the group represented by the formula (J) is bonded is a benzene ring, ABC ) is preferably substituted at the para position of boron (B).

[0205] In addition, the formula (J ABC The group represented by the formula (J) may be contained in any of the rings A, B, and C, but is preferably contained in at least one of the rings B and C. At least one of the rings B and C, and particularly both of them, is preferably represented by the formula (J ABC When the group represented by the formula (I) is a benzene ring substituted at the para position of boron (B), the interaction with adjacent molecules can be further suppressed.

[0206] <Explanation of formula (Ar)> In formula (1), each Ar is independently a group represented by the following formula (Ar): [ka]

[0207] In formula (Ar), # indicates the position of attachment to the nitrogen.

[0208] In formula (Ar), the "F" in a circle is a symbol representing the ring structure represented by the circle.

[0209] In formula (Ar), ring F may be a substituted or unsubstituted aryl ring or a substituted or unsubstituted heteroaryl ring.

[0210] In formula (Ar), G may be substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted arylthio, substituted or unsubstituted heteroarylthio, substituted or unsubstituted aryloxy, substituted or unsubstituted heteroaryloxy, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl. The explanations of the aryl, heteroaryl, arylthio, heteroarylthio, aryloxy, heteroaryloxy, and alkyl may be replaced with the parts common to the explanations of rings A to E. When G is unsubstituted alkyl, a bulky unsubstituted alkyl having 3 to 24 carbon atoms may be introduced into G.

[0211] In formula (Ar), ring F may be a substituted or unsubstituted aryl ring or a substituted or unsubstituted heteroaryl ring.

[0212] In formula (Ar), examples of the "aryl ring" of ring F include aryl rings having 6 to 30 carbon atoms, preferably aryl rings having 6 to 16 carbon atoms, more preferably aryl rings having 6 to 12 carbon atoms, and particularly preferably aryl rings having 6 to 10 carbon atoms.

[0213] In formula (Ar), examples of the "heteroaryl ring" of ring F 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. In addition, 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.

[0214] The aryl ring in the ring F may be selected from the group consisting of a benzene ring, a biphenyl ring, a terphenyl ring, an indene ring, a naphthalene ring, a fluorene ring, an anthracene ring and a phenanthrene ring, and the heteroaryl ring may be selected from the group consisting of a benzofuran ring, a benzothiophene ring, an indole ring, a dibenzofuran ring, a dibenzothiophene ring, a carbazole ring, a naphthofuran ring, a naphthothiophene ring, a benzoindole ring and a benzoselenophene ring. The ring F is preferably a substituted or unsubstituted benzene ring, a substituted or unsubstituted biphenyl ring, a substituted or unsubstituted terphenyl ring, a substituted or unsubstituted benzothiophene ring or a substituted or unsubstituted benzofuran ring.

[0215] When at least one hydrogen atom in the aryl ring or heteroaryl ring is substituted with a substituent, the substituent is preferably substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted diarylamino, substituted or unsubstituted diheteroarylamino, substituted or unsubstituted arylheteroarylamino (amino having aryl and heteroaryl), substituted or unsubstituted diarylboryl (two aryls may be bonded via a single bond or a linking group), substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryloxy, substituted silyl, or -L-Ak. When these groups have a substituent, the substituent may be aryl, heteroaryl, alkyl or cycloalkyl, or diarylamino.

[0216] In the above structure, at least one selected from the group consisting of an aryl ring and a heteroaryl ring may be fused with at least one cycloalkane, the cycloalkane may be substituted with at least one substituent, and at least one -CH 2 - may be replaced by -O-.

[0217] In the above structure, at least one hydrogen may be replaced with deuterium and at least one nitrogen may be replaced with nitrogen-15( 15 N), and at least one sulfur may be replaced by sulfur-33 ( 33 S), Sulfur-34( 34 S) or sulfur-36( 36 S), at least one oxygen is oxygen-17 ( 17 O) or oxygen-18( 18 O), at least one carbon is carbon-13 ( 13 C), at least one boron is boron-11( 11 B) may be substituted.

[0218] <Replacement with heavy stable isotopes> All or a part of the elements in the polycyclic aromatic compound containing the structural unit represented by formula (1) may be heavy stable isotopes. More specifically, at least one hydrogen may be replaced with deuterium, and at least one nitrogen may be replaced with nitrogen-15( 15 N), and at least one sulfur may be replaced by sulfur-33 ( 33 S), Sulfur-34( 34 S) or sulfur-36( 36 S), and at least one oxygen may be replaced by oxygen-17 ( 17 O) or oxygen-18( 18 O), and at least one carbon may be replaced by carbon-13 ( 13 C), and at least one boron may be replaced by boron-11 ( 11 B) may be substituted.

[0219] <Replacement with deuterium> All or a part of the hydrogen atoms in the polycyclic aromatic compound containing the structural unit represented by formula (1) may be deuterium atoms. The same applies to the polycyclic aromatic compound represented by formula (2X) or formula (2XJ).

[0220] For example, hydrogen atoms in the aryl or heteroaryl rings of ring A, ring B, ring C, ring D, or ring E, or in the substituents thereof, may be replaced with deuterium atoms. Among these, there may be mentioned embodiments in which all or a part of the hydrogen atoms in the aryl or heteroaryl are replaced with deuterium atoms. ABC In the formula (Ar), all or a part of the hydrogen atoms in the rings P and Q, or the aryl and heteroaryl rings in the ring F may be replaced with deuterium. From the viewpoint of durability, it is also preferable that all or a part of the hydrogen atoms in the polycyclic aromatic compound containing the structural unit represented by formula (1) are deuterated.

[0221] <Specific examples of polycyclic aromatic compounds> Examples of polycyclic aromatic compounds containing the structural unit represented by formula (1) include compounds represented by any of the following structural formulas: In the structural formulas, "Me" represents methyl, "tBu" represents t-butyl, and "D" represents deuterium.

[0222] [ka]

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[0289] 1-2.Reactive compounds, polymer compounds, crosslinked polymers, pendant polymer compounds, crosslinked pendant polymers The polycyclic aromatic compound represented by formula (1) can also be used as a material for organic devices, for example, a material for organic electroluminescent elements, a material for organic field effect transistors, or a material for organic thin-film solar cells, in the form of a polymer compound obtained by polymerizing a reactive compound substituted with a reactive substituent as a monomer (the monomer for obtaining this polymer compound has a polymerizable substituent), 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 polymer crosslinked polymer obtained by further crosslinking the pendant polymer compound (the pendant polymer compound for obtaining this pendant polymer crosslinked polymer has a crosslinkable substituent).

[0290] On the other hand, in this specification, a "polymer compound" refers to a polymer having a molecular weight distribution and a number average molecular weight of 1×10 3 ~1×10 8 (1×10^3 to 1×10^8) polymer. The number average molecular weight (Mn) of a polymer compound in terms of polystyrene can be determined by size exclusion chromatography (SEC) using tetrahydrofuran as the mobile phase. Specifically, the polymer compound to be measured is dissolved in tetrahydrofuran at a concentration of about 0.05% by mass, and 10 μL is injected into the SEC. The flow rate of the mobile phase is 1.0 mL / min, and a PLgelMIXED_B (Polymer Laboratories) column is used. A UV-VIS detector (Tosoh Corporation, product name: UV-8320GPC) can be used as the detector.

[0291] The polymer compound of the present invention has a number average molecular weight of 2000 to 1×10 8 It is preferable that the ratio is 5000 to 1×10 8 It is more preferable that:

[0292] The reactive substituents described 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 reacting as pendants with the main chain polymer, but are not particularly limited as long as they are unsaturated units of alkenyl, alkynyl, and cycloalkyl (e.g., cyclobutenyl), at least one -CH in cycloalkyl, 2 Examples of the substituents include a group in which - is replaced with -O- (e.g., epoxy), and an unsaturated product of a condensed cycloalkane (e.g., condensed cyclobutene), and the substituents having the following structures are preferred. In each structural formula, * indicates the bond position.

[0293] [ka]

[0294] 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.

[0295] 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.

[0296] 2. Method for producing polycyclic aromatic compounds The method for producing a polycyclic aromatic compound containing the structure represented by formula (1) can basically be carried out by either linking the A ring, B ring, and C ring linked with boron with a bonding group (N-Ar) and linking them to the D ring and E ring, and then linking the B ring, D ring, and E ring with boron (reaction a), or linking the B ring, D ring, and E ring linked with boron with a bonding group (N-Ar) and linking them to the A ring and C ring, and then linking the A ring, B ring, and C ring with boron (reaction b), or linking the A ring, B ring, C ring, D ring, and E ring with a bonding group (N-Ar), and then linking the A ring, B ring, and C ring with the B ring, D ring, and E ring simultaneously, and each with boron, to produce the final product (reaction c). When linking each ring with a linking group (N-Ar, O, S, and Se) in reaction a, reaction b, and reaction c, general reactions such as nucleophilic substitution reaction and Ullmann reaction can be used for etherification reaction, and general reactions such as Buchwald-Hartwig reaction can be used for amination reaction. In addition, when linking each ring with boron in reaction a, reaction b, and reaction c, tandem hetero Friedel-Crafts reaction (sequential aromatic electrophilic substitution reaction, the same applies below) can be used. For these production methods, reference can be made to the methods described in prior art such as International Publication No. WO 2015 / 102118.

[0297] 3. 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 element, an organic field effect transistor, or an organic thin-film solar cell.

[0298] 3-1. Organic electroluminescent device The organic electroluminescent element has at least a pair of electrodes consisting of an anode and a cathode, and a light-emitting layer disposed between the pair of electrodes. The organic EL element according to this embodiment will be described in detail below with reference to the drawings.

[0299] 3-1-1. 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), a light emitting layer (105) provided on the hole transport layer (104), an electron transport layer (106) provided on the light emitting layer (105), an electron injection layer (107) provided on the electron transport layer (106), and a cathode (108) provided on the electron injection layer (107).

[0300] 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), a light-emitting layer (105) provided on the electron transport layer (106), a hole transport layer (104) provided on the light-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).

[0301] Not all of the above layers are essential, and the minimum structural unit is an anode (102), a light-emitting layer (105), and a cathode (108), with the hole injection layer (103), hole transport layer (104), electron transport layer (106), and electron injection layer (107) being optional layers. Each of the above layers may consist of a single layer or multiple layers.

[0302] In addition to the aforementioned "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".

[0303] 3-1-2. Substrate in organic electroluminescent device The substrate (101) is a support for the organic EL element (100), and is usually made of quartz, glass, metal, plastic, or the like. The substrate (101) is formed into a plate, film, or sheet shape depending on the purpose, and for example, a glass plate, a metal plate, a metal foil, a plastic film, a plastic sheet, or the like is used. Among them, a glass plate and a plate made of a transparent synthetic resin such as polyester, polymethacrylate, polycarbonate, or polysulfone are preferable. For a glass substrate, soda lime glass or non-alkali glass is used, and the thickness is sufficient to maintain mechanical strength, for example, 0.2 mm or more. The upper limit of the thickness is, for example, 2 mm or less, and preferably 1 mm or less. As for the glass material, non-alkali glass is preferable because it is better to have fewer ions eluted from the glass, but SiO 2Soda lime glass coated with a barrier coat such as SiO2 is commercially available and can be used. 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 of the substrate (101), and it is particularly preferable to provide a gas barrier film when a synthetic resin plate, film or sheet with low gas barrier properties is used as the substrate (101).

[0304] 3-1-3. Anode in organic electroluminescent device The anode (102) serves to inject holes into the light-emitting layer (105). When a hole injection layer (103) and / or a hole transport layer (104) are provided between the anode (102) and the light-emitting layer (105), holes are injected into the light-emitting layer (105) through these layers.

[0305] 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.

[0306] 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 can function 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.

[0307] 3-1-4. Hole injection layer and hole transport layer in organic electroluminescent device The hole injection layer (103) plays a role of efficiently injecting holes moving from the anode (102) into the light emitting layer (105) or the hole transport layer (104). The hole transport layer (104) plays a role of efficiently transporting holes injected from the anode (102) or holes injected from the anode (102) through 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.

[0308] 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.

[0309] As materials for forming the hole injection layer (103) and the hole transport layer (104), any compound can be selected from compounds conventionally used as charge transport materials for holes in photoconductive materials, p-type semiconductors, and known compounds used in hole injection layers and hole transport layers of organic EL elements.Specific examples of such compounds include carbazole derivatives (N-phenylcarbazole, polyvinylcarbazole, etc.), biscarbazole derivatives such as bis(N-arylcarbazole) or bis(N-alkylcarbazole), triarylamine derivatives (polymers having an aromatic tertiary amino group in the main chain or side chain, 1,1-bis(4-di-p-tolylaminophenyl)cyclohexane, N,N'-diphenyl-N,N'-di(3-methylphenyl)-4,4'-diaminobiphenyl, and N,N'-diphenyl-N,N'-dinaphthyl-4,4'-diaminobiphenyl. , N,N'-diphenyl-N,N'-di(3-methylphenyl)-4,4'-diphenyl-1,1'-diamine, N,N'-dinaphthyl-N,N'-diphenyl-4,4'-diphenyl-1,1'-diamine, N4,N4'-diphenyl-N4,N4'-bis(9-phenyl-9H-carbazol-3-yl)-[1,1'-biphenyl]-4,4'-diamine, N4,N4,N4',N4'-tetra([1,1'-biphenyl]-4-yl)-[1,1'-biphenyl]-4,4'-diamine, 4,4',4"-tris(3-methylphenyl(phenyl) N-([1,1'-biphenyl]-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl(phenyl)-9H-fluoren-2-amine, N,N-bis(4-(dibenzo[b,d]furan-4-yl)phenyl)-[1,1':4',1"-terphenyl]-4-amine and other triphenylamine derivatives, starburst amine derivatives, etc.), stilbene derivatives, phthalocyanine derivatives (metal-free, copper phthalocyanine, etc.), pyrazoline derivatives, hydrazone compounds, benzo Examples of the polymer include heterocyclic compounds such as furan derivatives, thiophene derivatives, oxadiazole derivatives, quinoxaline derivatives (e.g., 1,4,5,8,9,12-hexaazatriphenylene-2,3,6,7,10,11-hexacarbonitrile, etc.), porphyrin derivatives, and polysilanes. As for the polymer system, polycarbonates and styrene derivatives having the above-mentioned monomers in their side chains, polyvinylcarbazole, and polysilanes are preferable, but there is no particular limitation as long as the compound can form a thin film required for fabricating a light-emitting device, can inject holes from the anode, and can transport holes.

[0310] It is also known that the electrical conductivity of organic semiconductors is strongly influenced by their doping. Organic semiconductor matrix substances consist of compounds with good electron donating or accepting properties. For doping with electron donating substances, strong electron acceptors such as tetracyanoquinone dimethane (TCNQ) or 2,3,5,6-tetrafluorotetracyano-1,4-benzoquinone dimethane (F4TCNQ) are known (see, for example, the references "M. Pfeiffer, A. Beyer, T. Fritz, K. Leo, Appl. Phys. Lett., 73(22), 3202-3204 (1998)" and "J. Blochwitz, M. Pfeiffer, T. Fritz, K. Leo, Appl. Phys. Lett., 73(6), 729-731 (1998)"). These generate so-called holes by an electron transfer process in an electron-donating base material (hole transport material). The conductivity of the base material varies considerably depending on the number and mobility of the holes. As matrix materials having hole transport properties, for example, benzidine derivatives (TPD, etc.) or starburst amine derivatives (TDATA, etc.) or certain metal phthalocyanines (especially zinc phthalocyanine (ZnPc) and the like) are known (JP 2005-167175 A).

[0311] The hole injection layer material and the hole transport layer material described above can be used as a hole layer material in the form of a polymer compound obtained by polymerizing a reactive compound substituted with a reactive substituent as a monomer, or a crosslinked polymer thereof, or a pendant polymer compound obtained by reacting a main chain polymer with the reactive compound, or a crosslinked pendant polymer thereof. In this case, the explanation of the polycyclic aromatic compound having the structure represented by formula (1) can be cited as the reactive substituent.

[0312] The applications of such polymer compounds and crosslinked polymers will be described in detail below.

[0313] 3-1-5. Light-emitting layer in organic electroluminescent device The light-emitting layer (105) is a layer that emits light by recombining holes injected from the anode (102) and electrons injected from the cathode (108) between electrodes to which an electric field is applied. The material for forming the light-emitting layer (105) may be a compound (light-emitting compound) that is excited by the recombination of holes and electrons to emit light, and is preferably a compound that can form a stable thin film shape and shows strong light-emitting (fluorescence) efficiency in a solid state. The light-emitting layer may be a single layer or multiple layers, each of which is formed from a material for the light-emitting layer (host material, dopant material). The host material and the dopant material may each be one type or a combination of multiple types. For example, an emitting dopant and an assisting dopant may be used as the dopant material. The dopant material may be contained in the entire host material or may be contained partially in the host material. As a doping method, the light-emitting layer may be formed by co-evaporation with the host material, but it may also be mixed with the host material in advance and then evaporated at the same time. The light-emitting layer can also be formed by a wet film-forming method using a composition for forming a light-emitting layer prepared by dissolving materials in an organic solvent.

[0314] The polycyclic aromatic compound represented by formula (1) can be preferably used as a material for forming the light-emitting layer of an organic electroluminescent device. The polycyclic aromatic compound represented by formula (1) is more preferably used as an emitting dopant or an assisting dopant in the light-emitting layer, and more preferably used as an emitting dopant.

[0315] The polycyclic aromatic compound represented by formula (1) may be used as an emitting dopant in an organic electroluminescence element (hereinafter, sometimes referred to as a "TADF element") that exhibits thermally activated delayed fluorescence (TADF) as a "thermally activated delayed phosphor." In a "thermally activated delayed phosphor," by reducing the energy difference between the lowest excited singlet state and the lowest excited triplet state, reverse intersystem crossing from the lowest excited triplet state, which usually has a low transition probability, to the lowest excited singlet state occurs with high efficiency, and light emission from the singlet state (thermally activated delayed fluorescence, TADF) is expressed. In normal fluorescent emission, 75% of triplet excitons generated by current excitation pass through a thermal deactivation pathway and cannot be extracted as fluorescence. On the other hand, in TADF, all excitons can be used for fluorescent emission, and a highly efficient organic electroluminescence element can be realized.

[0316] The polycyclic aromatic compound represented by formula (1) can be used as an emitting dopant for a "TADF element", an emitting dopant for a TADF element using two types of hosts, an emitting dopant for an organic electroluminescent element using a separate thermally activated delayed phosphor as an assisting dopant (TADF-assisted fluorescent element, TAF element), and an emitting dopant for an organic electroluminescent element using a phosphorescent material as an assisting dopant (phosphor-sensitized fluorescent element, PSF element). From the viewpoint that the fewer materials used in the element, the easier it is to manufacture, the emitting dopant for a TADF element and the emitting dopant for a TADF element using two types of hosts are preferred, and the emitting dopant for a TADF element is more preferred. From the viewpoint of efficiency, the emitting dopant for a TAF element and the emitting dopant for a phosphorescence-assisted element are preferred, and the emitting dopant for a TAF element is more preferred.

[0317] Generally, it is said that the faster the delayed fluorescence, the better the TADF properties. Specifically, when a light-emitting material with a delayed fluorescence lifetime of 20 μsec or less is used as an emitting dopant in a light-emitting device, high device efficiency and long device life can be obtained. In addition, generally, ΔE S1T1 The smaller the value, the better the TADF properties. S1T1 is the lowest excited singlet energy level (E S1 ) and the lowest excited triplet energy level (E T1 ) is the energy difference between the S1T1 The value is preferably 0.20 eV or less, and more preferably 0.15 eV or less.

[0318] The light-emitting layer may contain a host compound. Here, the host compound may be one type or two or more types. Any known host compound can be used as the host compound. A preferred example of the host compound is a high T1 compound described later.

[0319] The light-emitting layer may be a single layer or multiple layers. The host compound, the emitting dopant material, and the assisting dopant material may be contained in the same layer, or at least one of each may be contained in multiple layers. The host compound and the dopant material (emitting dopant or assisting dopant) contained in the light-emitting layer may each be one type or a combination of multiple types. The assisting dopant and the emitting dopant may be entirely or partially contained in the host compound as a matrix.

[0320] 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 mass of the materials for the light-emitting layer.

[0321] The amount of the dopant material used varies depending on the type of dopant material, and may be determined according to the characteristics of the dopant material. The amount of the dopant material 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 mass of the material for the light-emitting layer. The above range is preferable in that, for example, concentration quenching can be prevented.

[0322] On the other hand, in an organic electroluminescent device using a TADF material as a dopant material, a low concentration of the dopant material is preferable in terms of preventing concentration quenching, but a high concentration of the dopant material is preferable in terms of the efficiency of the thermally activated delayed fluorescence mechanism. Furthermore, in an organic electroluminescent device using a TADF material as an assisting dopant, from the viewpoint of the efficiency of the thermally activated delayed fluorescence mechanism of the assisting dopant, it is preferable that the amount of the emitting dopant is low compared to the amount of the assisting dopant.

[0323] When an assisting dopant material is used, the amounts of the host material, the assisting dopant, and the emitting dopant are approximately 40 to 99% by mass, 59 to 1% by mass, and 20 to 0.001% by mass, respectively, based on the total mass of the materials for the light-emitting layer, preferably 60 to 95% by mass, 39 to 5% by mass, and 10 to 0.01% by mass, respectively, and more preferably 70 to 90% by mass, 29 to 10% by mass, and 5 to 0.05% by mass. When an assisting dopant material is used, it may form an exciplex with the host material or the emitting dopant.

[0324] 3-1-5-1.Dopant materials The polycyclic aromatic compound represented by formula (1) is preferably used as a dopant material.

[0325] Dopant materials that can be used other than the polycyclic aromatic compound represented by formula (1) are not particularly limited, and known compounds can be used, and can be selected from various materials depending on the desired emission color.Specific examples of such compounds include condensed ring derivatives of phenanthrene, anthracene, pyrene, tetracene, pentacene, perylene, naphthopyrene, dibenzopyrene, rubrene, and chrysene, benzoxazole derivatives, benzothiazole derivatives, benzimidazole derivatives, benzotriazole derivatives, oxazole derivatives, oxadiazole derivatives, thiazole derivatives, imidazole derivatives, thiadiazole derivatives, triazole derivatives, pyrazoline derivatives, stilbene derivatives, thiophene derivatives, and tetraphenylbutadiene. derivatives, cyclopentadiene derivatives, bisstyryl derivatives such as bisstyrylanthracene derivatives and distyrylbenzene derivatives (JP Patent Publication No. 245087 / 1999), bisstyrylarylene derivatives (JP Patent Publication No. 247278 / 1990), diazaindacene derivatives, furan derivatives, benzofuran derivatives, isobenzofuran derivatives such as phenylisobenzofuran, dimesitylisobenzofuran, di(2-methylphenyl)isobenzofuran, di(2-trifluoromethylphenyl)isobenzofuran, and phenylisobenzofuran coumarin derivatives such as dibenzofuran derivatives, 7-dialkylaminocoumarin derivatives, 7-piperidinocoumarin derivatives, 7-hydroxycoumarin derivatives, 7-methoxycoumarin derivatives, 7-acetoxycoumarin derivatives, 3-benzothiazolylcoumarin derivatives, 3-benzimidazolylcoumarin derivatives, and 3-benzoxazolylcoumarin derivatives, dicyanomethylenepyran derivatives, dicyanomethylenethiopyran derivatives, polymethine derivatives, cyanine derivatives, oxobenzoanthracene derivatives, xanthene derivatives, and rhodamine derivatives. conductors, fluorescein derivatives, pyrylium derivatives, carbostyril derivatives, acridine derivatives, oxazine derivatives, phenylene oxide derivatives, quinacridone derivatives, quinazoline derivatives, pyrrolopyridine derivatives, furopyridine derivatives, 1,2,5-thiadiazolopyrene derivatives, pyrromethene derivatives, perinone derivatives, pyrrolopyrrole derivatives, squarylium derivatives, violanthrone derivatives, phenazine derivatives, acridone derivatives, deazaflavin derivatives, fluorene derivatives and benzofluorene derivatives.

[0326] Examples of dopant materials for each color of light emitted include aromatic hydrocarbon compounds such as naphthalene, anthracene, phenanthrene, pyrene, triphenylene, perylene, fluorene, indene, and chrysene, and derivatives thereof, furan, pyrrole, thiophene, silole, 9-silafluorene, 9,9'-spirobisilafluorene, benzothiophene, benzofuran, indole, dibenzothiophene, dibenzofuran, imidazopyridine, phenanthroline, pyrazine, naphthyridine, quinoxaline, pyrrolopyridine, and pyrrolopyridine. Examples of the aromatic heterocyclic compounds include lysine and thioxanthene, and their derivatives, distyrylbenzene derivatives, tetraphenylbutadiene derivatives, stilbene derivatives, aldazine derivatives, coumarin derivatives, azole derivatives such as imidazole, thiazole, thiadiazole, carbazole, oxazole, oxadiazole, and triazole, and metal complexes thereof, and aromatic amine derivatives typified by N,N'-diphenyl-N,N'-di(3-methylphenyl)-4,4'-diphenyl-1,1'-diamine.

[0327] In addition, examples of the green to yellow dopant material include coumarin derivatives, phthalimide derivatives, naphthalimide derivatives, perinone derivatives, pyrrolopyrrole derivatives, cyclopentadiene derivatives, acridone derivatives, quinacridone derivatives, and naphthacene derivatives such as rubrene. Further, preferred examples of the compounds exemplified as the blue to blue-green dopant materials include compounds in which a substituent that enables a longer wavelength, such as aryl, heteroaryl, arylvinyl, amino, or cyano, has been introduced.

[0328] Further examples of orange to red dopant materials include naphthalimide derivatives such as bis(diisopropylphenyl)perylenetetracarboxylic acid imide, perinone derivatives, rare earth complexes such as Eu complexes having acetylacetone, benzoylacetone, and phenanthroline as ligands, 4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran and analogs thereof, metal phthalocyanine derivatives such as magnesium phthalocyanine and aluminum chlorophthalocyanine, rhodamine compounds, deazaflavin derivatives, coumarin derivatives, quinacridone derivatives, phenoxazine derivatives, oxazine derivatives, quinazoline derivatives, pyrrolopyridine derivatives, squarylium derivatives, violanthrone derivatives, phenazine derivatives, phenoxazone derivatives, and thiadiazolopyrene derivatives. Further examples of suitable compounds include those obtained by introducing a substituent that enables longer wavelengths, such as aryl, heteroaryl, arylvinyl, amino, and cyano, into the compounds exemplified as the blue to blue-green and green to yellow dopant materials.

[0329] In addition, the dopant may be appropriately selected from the compounds described in Chemical Industry, June 2004, page 13 and the references cited therein.

[0330] Among the above-mentioned dopant materials, amines having a stilbene structure, perylene derivatives, borane derivatives, aromatic amine derivatives, coumarin derivatives, pyran derivatives, or pyrene derivatives are particularly preferred.

[0331] The amine having a stilbene structure is represented, for example, by the following formula. [ka]

[0332] In the formula, Ar 1 is an m-valent group derived from an aryl having 6 to 30 carbon atoms, and Ar 2 and Ar 3 are each independently an aryl having 6 to 30 carbon atoms, 1~Ar 3 At least one of the groups has a stilbene structure, and Ar 1 ~Ar 3 may be substituted with aryl, heteroaryl, alkyl, cycloalkyl, trisubstituted silyl (silyl trisubstituted with aryl, alkyl and / or cycloalkyl) or cyano, and m is an integer from 1 to 4.

[0333] The amine having a stilbene structure is more preferably a diaminostilbene represented by the following formula. [ka]

[0334] In the formula, Ar 2 and Ar 3 are each independently an aryl having 6 to 30 carbon atoms, and Ar 2 and Ar 3 may be substituted with aryl, heteroaryl, alkyl, cycloalkyl, trisubstituted silyl (silyl trisubstituted with aryl, alkyl and / or cycloalkyl) or cyano.

[0335] Specific examples of the aryl having 6 to 30 carbon atoms include phenyl, naphthyl, acenaphthylenyl, fluorenyl, phenalenyl, phenanthrenyl, anthryl, fluoranthenyl, triphenylenyl, pyrenyl, chrysenyl, naphthacenyl, perylenyl, stilbenyl, distyrylphenyl, distyrylbiphenyl, and distyrylfluorenyl.

[0336] Specific examples of the amine having a stilbene structure include N,N,N',N'-tetra(4-biphenylyl)-4,4'-diaminostilbene, N,N,N',N'-tetra(1-naphthyl)-4,4'-diaminostilbene, N,N,N',N'-tetra(2-naphthyl)-4,4'-diaminostilbene, N,N'-di(2-naphthyl)-N,N'-diphenyl-4,4'-diaminostilbene, N,N'-di(9-phenanthryl)-N,N'-diphenyl Examples of such fluorene compounds include 4,4'-bis(9-ethyl-3-carbazovinylene)-biphenyl, 4,4'-bis(9-phenyl-3-carbazovinylene)-biphenyl, and the like.

[0337] Furthermore, amines having a stilbene structure, such as those described in JP-A Nos. 2003-347056 and 2001-307884, may also be used.

[0338] Examples of perylene derivatives include 3,10-bis(2,6-dimethylphenyl)perylene, 3,10-bis(2,4,6-trimethylphenyl)perylene, 3,10-diphenylperylene, 3,4-diphenylperylene, 2,5,8,11-tetra-t-butylperylene, 3,4,9,10-tetraphenylperylene, 3-(1'-pyrenyl)-8,11-di(t-butyl)perylene, 3-(9'-anthryl)-8,11-di(t-butyl)perylene, and 3,3'-bis(8,11-di(t-butyl)perylenyl).

[0339] Also usable are perylene derivatives described in JP-A-11-97178, JP-A-2000-133457, JP-A-2000-26324, JP-A-2001-267079, JP-A-2001-267078, JP-A-2001-267076, JP-A-2000-34234, JP-A-2001-267075, and JP-A-2001-217077.

[0340] Examples of borane derivatives include 1,8-diphenyl-10-(dimesitylboryl)anthracene, 9-phenyl-10-(dimesitylboryl)anthracene, 4-(9'-anthryl)dimesitylborylnaphthalene, 4-(10'-phenyl-9'-anthryl)dimesitylborylnaphthalene, 9-(dimesitylboryl)anthracene, 9-(4'-biphenylyl)-10-(dimesitylboryl)anthracene, and 9-(4'-(N-carbazolyl)phenyl)-10-(dimesitylboryl)anthracene.

[0341] Furthermore, borane derivatives described in International Publication No. 2000 / 40586 may also be used.

[0342] The aromatic amine derivative is represented, for example, by the following formula: [ka]

[0343] In the formula, Ar 4 is an n-valent group derived from an aryl having 6 to 30 carbon atoms, and Ar 5 and Ar 6 are each independently an aryl having 6 to 30 carbon atoms, and Ar 4 ~Ar 6 may be substituted with aryl, heteroaryl, alkyl, cycloalkyl, trisubstituted silyl (silyl trisubstituted with aryl, alkyl and / or cycloalkyl) or cyano, and n is an integer from 1 to 4.

[0344] In particular, Ar 4is a divalent group derived from anthracene, chrysene, fluorene, benzofluorene, or pyrene, and Ar 5 and Ar 6 are each independently an aryl having 6 to 30 carbon atoms, and Ar 4 ~Ar 6 is optionally substituted with aryl, heteroaryl, alkyl, cycloalkyl, trisubstituted silyl (silyl trisubstituted with aryl, alkyl and / or cycloalkyl) or cyano, and n is 2.

[0345] Specific examples of the aryl having 6 to 30 carbon atoms include phenyl, naphthyl, acenaphthylenyl, fluorenyl, phenalenyl, phenanthrenyl, anthryl, fluoranthenyl, triphenylenyl, pyrenyl, chrysenyl, naphthacenyl, phenylenyl, and pentacenyl.

[0346] Examples of aromatic amine derivatives include chrysene derivatives such as N,N,N',N'-tetraphenylchrysene-6,12-diamine, N,N,N',N'-tetra(p-tolyl)chrysene-6,12-diamine, N,N,N',N'-tetra(m-tolyl)chrysene-6,12-diamine, N,N,N',N'-tetrakis(4-isopropylphenyl)chrysene-6,12-diamine, N,N,N',N'-tetra(naphthalen-2-yl)chrysene-6,12-diamine, and N,N'-diphenyl -N,N'-di(p-tolyl)chrysene-6,12-diamine, N,N'-diphenyl-N,N'-bis(4-ethylphenyl)chrysene-6,12-diamine, N,N'-diphenyl-N,N'-bis(4-isopropylphenyl)chrysene-6,12-diamine, N,N'-diphenyl-N,N'-bis(4-t-butylphenyl)chrysene-6,12-diamine, N,N'-bis(4-isopropylphenyl)-N,N'-di(p-tolyl)chrysene-6,12-diamine and the like.

[0347] Examples of pyrene-based compounds include N,N,N',N'-tetraphenylpyrene-1,6-diamine, N,N,N',N'-tetra(p-tolyl)pyrene-1,6-diamine, N,N,N',N'-tetra(m-tolyl)pyrene-1,6-diamine, N,N,N',N'-tetrakis(4-isopropylphenyl)pyrene-1,6-diamine, N,N,N',N'-tetrakis(3,4-dimethylphenyl)pyrene-1,6-diamine, N,N'-diphenyl-N,N'-di(p-tolyl)pyrene-1,6-diamine, N,N'-diphenyl-N,N'-bis(4-ethylphenyl)pyrene-1, 6-diamine, N,N'-diphenyl-N,N'-bis(4-isopropylphenyl)pyrene-1,6-diamine, N,N'-diphenyl-N,N'-bis(4-t-butylphenyl)pyrene-1,6-diamine, N,N'-bis(4-isopropylphenyl)-N,N'-di(p-tolyl)pyrene-1,6-diamine, N,N,N',N'-tetrakis(3,4-dimethylphenyl)-3,8-diphenylpyrene-1,6-diamine, N,N,N,N-tetraphenylpyrene-1,8-diamine, N,N'-bis(biphenyl-4-yl)-N,N'-diphenylpyrene-1,8-diamine, N 1 ,N 6 -Diphenyl-N 1 ,N 6 -bis-(4-trimethylsilanyl-phenyl)-1H,8H-pyrene-1,6-diamine and the like.

[0348] Examples of anthracene-based compounds include N,N,N,N-tetraphenylanthracene-9,10-diamine, N,N,N',N'-tetra(p-tolyl)anthracene-9,10-diamine, N,N,N',N'-tetra(m-tolyl)anthracene-9,10-diamine, N,N,N',N'-tetrakis(4-isopropylphenyl)anthracene-9,10-diamine, N,N'-diphenyl-N,N'-di(p-tolyl)anthracene-9,10-diamine, and N,N'-di Phenyl-N,N'-di(m-tolyl)anthracene-9,10-diamine, N,N'-diphenyl-N,N'-bis(4-ethylphenyl)anthracene-9,10-diamine, N,N'-diphenyl-N,N'-bis(4-ethylphenyl)anthracene-9,10-diamine, N,N'-diphenyl-N,N'-bis(4-isopropylphenyl)anthracene-9,10-diamine, N,N'-diphenyl-N,N'-bis(4-t-butylphenyl)anthracene-9,10 -diamine, N,N'-bis(4-isopropylphenyl)-N,N'-di(p-tolyl)anthracene-9,10-diamine, 2,6-di-t-butyl-N,N,N',N'-tetra(p-tolyl)anthracene-9,10-diamine, 2,6-di-t-butyl-N,N'-diphenyl-N,N'-bis(4-isopropylphenyl)anthracene-9,10-diamine, 2,6-di-t-butyl-N,N'-bis(4-isopropylphenyl)-N,N'-di(p-tolyl)anthracene helicalene-9,10-diamine, 2,6-dicyclohexyl-N,N'-bis(4-isopropylphenyl)-N,N'-di(p-tolyl)anthracene-9,10-diamine, 2,6-dicyclohexyl-N,N'-bis(4-isopropylphenyl)-N,N'-bis(4-t-butylphenyl)anthracene-9,10-diamine, 9,10-bis(4-diphenylamino-phenyl)anthracene, 9,10-bis(4-di(1-naphthylamino)phenyl)anthracene, 9,Examples of the anthracene include 10-bis(4-di(2-naphthylamino)phenyl)anthracene, 10-di-p-tolylamino-9-(4-di-p-tolylamino-1-naphthyl)anthracene, 10-diphenylamino-9-(4-diphenylamino-1-naphthyl)anthracene, and 10-diphenylamino-9-(6-diphenylamino-2-naphthyl)anthracene.

[0349] Other examples include [4-(4-diphenylamino-phenyl)naphthalen-1-yl]-diphenylamine, [6-(4-diphenylamino-phenyl)naphthalen-2-yl]-diphenylamine, 4,4'-bis[4-diphenylaminonaphthalen-1-yl]biphenyl, 4,4'-bis[6-diphenylaminonaphthalen-2-yl]biphenyl, 4,4"-bis[4-diphenylaminonaphthalen-1-yl]-p-terphenyl, and 4,4"-bis[6-diphenylaminonaphthalen-2-yl]-p-terphenyl.

[0350] Furthermore, aromatic amine derivatives described in, for example, JP-A-2006-156888 may also be used.

[0351] Coumarin derivatives include coumarin-6 and coumarin-334.

[0352] Furthermore, coumarin derivatives described in JP-A-2004-43646, JP-A-2001-76876, JP-A-6-298758, and the like may also be used.

[0353] Examples of the pyran derivative include DCM and DCJTB shown below. [ka]

[0354] Furthermore, pyran derivatives described in JP-A Nos. 2005-126399, 2005-097283, 2002-234892, 2001-220577, 2001-081090, and 2001-052869 may also be used.

[0355] As the dopant material, the following compounds may be used: [ka]

[0356] 3-1-5-2. High T1 compounds An organic electroluminescent device containing at least one polycyclic aromatic compound represented by formula (1) in an emission layer preferably further contains at least one high T1 compound having a lowest excited triplet energy level (ET1) (sometimes referred to as "T1 energy") that is at least 0.01 eV higher than the lowest excited triplet energy level of the polycyclic aromatic compound represented by formula (1) in the emission layer or in an organic layer adjacent to the emission layer.

[0357] The high T1 compound can be used as a host compound when the polycyclic aromatic compound represented by formula (1) is used as a dopant compound in the light-emitting layer. The high T1 compound may be contained in one type or two or more types in the light-emitting layer. When two or more types are contained, it is preferable to contain a hole-transporting host material and an electron-transporting host material that satisfy the following relationship.

[0358] The HOMO (Highest Occupied Molecular Orbital) of the hole-transporting host material (HH) is shallower than the HOMO of the electron-transporting host material (EH). The LUMO (Lowest Unoccupied Molecular Orbital) of the electron-transporting host material (EH) is deeper than the LUMO of the hole-transporting host material (HH).

[0359] E of high T1 compounds T1is the E of the polycyclic aromatic compound represented by formula (1). T1 It is preferably 0.03 eV or more higher than, and more preferably 0.1 eV or more higher than.

[0360] As the high T1 compound, a compound having at least one partial structure selected from partial structure group A, or having at least two partial structures selected from partial structure group A and partial structure group B, and further having at least one partial structure selected from partial structure group C as a linking group or a substituent is preferred. Meanwhile, at least one * in each of the following structures is bonded to other partial structures other than hydrogen, and the other * is bonded to hydrogen. As can be seen from the following structural formula, the carbon-carbon bond connecting the benzene rings in each partial structure and the bond connecting the partial structures are ortho or m-position. At this time, high T1 and high charge mobility are obtained. From the viewpoint of high T1, it is preferable to bond at the ortho position, and from the viewpoint of high charge mobility, it is preferable to bond at the m-position.

[0361] Substructure group A [ka]

[0362] Substructure group B [ka]

[0363] substructure group C [ka]

[0364] The partial structure group A is preferably the partial structure group Aa, the partial structure group B is preferably the partial structure group Bb, and the partial structure group C is preferably the partial structure group Cc.

[0365] [ka]

[0366] Examples of high T1 compounds include compounds represented by the following formula (H1), compounds represented by the following formula (H3), compounds containing a structure represented by the following formula (H4), compounds represented by the following formula (H5), compounds represented by the following formula (H6), and compounds represented by the following formula (H8).

[0367] [ka]

[0368] 3-1-5-2-1. Compound represented by formula (H1) [ka]

[0369] In formula (H1), L 1 represents an arylene having 6 to 24 carbon atoms or a heteroarylene having 5 to 23 carbon atoms, preferably an arylene having 6 to 16 carbon atoms or a heteroarylene having 5 to 15 carbon atoms, more preferably an arylene having 6 to 12 carbon atoms or a heteroarylene having 5 to 11 carbon atoms, and particularly preferably an arylene having 6 to 10 carbon atoms or a heteroarylene having 5 to 9 carbon atoms. Specific examples thereof include divalent or trivalent groups such as a benzene ring, a biphenyl ring, a terphenyl ring, a fluorene ring, a spirofluorene ring, a phenalene ring, a triphenylene ring, a pyridine ring, a pyrimidine ring, a triazine ring, a biphenylpyridine ring, a biphenylpyrimidine ring, and a biphenyltriazine ring.

[0370] At least one hydrogen atom in the compound represented by formula (H1) may be substituted with alkyl having 1 to 6 carbon atoms, cycloalkyl having 3 to 14 carbon atoms, cyano, halogen or deuterium. [ka]

[0371] 3-1-5-2-2. Compound represented by formula (H3) [ka]

[0372] In formula (3H), Each MU is independently a divalent aromatic group, each EC is independently a monovalent aromatic group, and k is an integer of 2 to 50,000.

[0373] 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.

[0374] k is preferably an integer from 20 to 50,000, and more preferably an integer from 100 to 50,000.

[0375] At least one hydrogen atom in MU and EC in formula (H3) may be substituted with an alkyl group having 1 to 24 carbon atoms, a cycloalkyl group having 3 to 24 carbon atoms, a halogen atom, or a deuterium atom. 2 - is -O- or -Si(CH 3 ) 2 -, and -CH directly bonded to EC in formula (H3) in the alkyl 2 Any -CH except 2 - may be substituted with an arylene having 6 to 24 carbon atoms, and any hydrogen in the alkyl may be substituted with a fluorine.

[0376] 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 consisting of a combination of two or more of the 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).

[0377] [ka]

[0378] More specifically, the divalent group may have any one of the following structures: In these, MU is bonded to another MU or EC at *.

[0379] [ka]

[0380] [ka]

[0381] [ka]

[0382] [ka]

[0383] [ka]

[0384] [ka]

[0385] [ka]

[0386] Examples of EC include groups represented by the following formulas: In these, EC is bonded to MU at *. [ka]

[0387] From the viewpoint of solubility and coating film-forming property, the compound represented by formula (H3) is preferably such that 10 to 100% of the total number of MUs (k) in the molecule have an alkyl having 1 to 24 carbon atoms, more preferably 30 to 100% of the total number of MUs (k) in the molecule have an alkyl having 1 to 18 carbon atoms (branched chain alkyl having 3 to 18 carbon atoms), and even more preferably 50 to 100% of the total number of MUs (k) in the molecule have an alkyl having 1 to 12 carbon atoms (branched chain alkyl having 3 to 12 carbon atoms). On the other hand, from the viewpoint of in-plane orientation and charge transport, it is preferable that 10 to 100% of the total number of MUs (k) in the molecule have an alkyl having 7 to 24 carbon atoms, and more preferably 30 to 100% of the total number of MUs (k) in the molecule have an alkyl having 7 to 24 carbon atoms (branched chain alkyl having 7 to 24 carbon atoms).

[0388] 3-1-5-2-3. Compounds containing the structure represented by formula (H4) The compound containing a structure represented by formula (H4) contains a plurality of structures represented by formula (H4), preferably 1 to 5 structures, more preferably 1 to 3 structures, even more preferably 1 to 2 structures, and most preferably 1 structure. When a plurality of structures are contained, the structures are directly bonded to each other via a single bond or a specific linking group.

[0389] [ka]

[0390] In formula (H4), G is "=C(-H)-" or "=N-", and the H in the "=C(-H)-" may be substituted with a substituent or another structure represented by formula (H4).

[0391] As the compound containing a structure represented by formula (H4), for example, the compounds described in WO 2012 / 153780 and WO 2013 / 038650 can be used, and can be produced according to the methods described in the above documents.

[0392] When H in "=C(-H)-" of G is substituted, examples of the substituent include aryl, heteroaryl, substituted silyl, substituted phosphine oxide group, and substituted carboxy.

[0393] Specific examples of the "aryl" substituent include phenyl, tolyl, xylyl, triphenylenyl, fluorenyl, 9,9-dimethylfluorenyl, benzofluorenyl, dibenzofluorenyl, biphenylyl, terphenylyl, quaterphenylyl, etc., and preferably include phenyl, biphenylyl, terphenylyl, and fluorenyl. Examples of aryl having a substituent include tolyl, xylyl, and 9,9-dimethylfluorenyl. As shown in the specific examples, aryl includes both fused aryl and non-fused aryl.

[0394] Specific examples of the substituent "heteroaryl" include pyrrolyl, pyrazolyl, pyrazinyl, pyrimidinyl, pyridazinyl, pyridyl, triazinyl, indolyl, isoindolyl, imidazolyl, benzimidazolyl, indazolyl, imidazo[1,2-a]pyridinyl, furyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, azadibenzofuranyl, thienyl, benzothienyl, dibenzothienyl, azadibenzothienyl, quinolyl, isoquinolyl, quinoxalinyl, quinazolinyl, and naphthalene. Examples of the aryl group include phthyridinyl, carbazolyl, azacarbazolyl, phenanthridinyl, acridinyl, phenazinyl, phenothiazinyl, phenoxazinyl, oxazolyl, oxadiazolyl, furazanyl, benzoxazolyl, thiazolyl, thiadiazolyl, benzthiazolyl, triazolyl, and tetrazolyl. Preferred examples include dibenzofuranyl, dibenzothienyl, carbazolyl, pyridyl, pyrimidinyl, triazinyl, azadibenzofuranyl, and azadibenzothienyl. Dibenzofuranyl, dibenzothienyl, azadibenzofuranyl, and azadibenzothienyl are more preferred.

[0395] The substituent "substituted silyl" is also preferably a group selected from the group consisting of substituted or unsubstituted trialkylsilyl, substituted or unsubstituted arylalkylsilyl, and substituted or unsubstituted triarylsilyl.

[0396] Specific examples of the substituted or unsubstituted trialkylsilyl include trimethylsilyl and triethylsilyl. Specific examples of the substituted or unsubstituted arylalkylsilyl include diphenylmethylsilyl, ditolylmethylsilyl, and phenyldimethylsilyl. Specific examples of the substituted or unsubstituted triarylsilyl include triphenylsilyl and tritolylsilyl.

[0397] The "substituted phosphine oxide group" as a substituent is also preferably a substituted or unsubstituted diarylphosphine oxide group. Specific examples of the substituted or unsubstituted diarylphosphine oxide group include diphenylphosphine oxide and ditolylphosphine oxide.

[0398] The substituent "substituted carboxy" includes, for example, benzoyloxy and the like.

[0399] Examples of the linking group that bonds a plurality of structures represented by formula (H4) include divalent to tetravalent, divalent to trivalent, or divalent derivatives of the above-mentioned aryl or heteroaryl.

[0400] Specific examples of the compound containing the structure represented by formula (H4) are shown below. [ka]

[0401] [ka]

[0402] 3-1-5-2-4. Compounds represented by formula (H5) and compounds represented by formula (H6) 3-1-5-2-4-1. Compound represented by formula (H5) [ka]

[0403] In formula (H5), R 1 ~R 11 are each independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino or aryloxy, wherein at least one hydrogen may be further substituted with aryl, heteroaryl or diarylamino.

[0404] In addition, at least one (preferably 1 to 3) of any -C(Rn )= (n is 1 to 11) may be substituted with -N=.

[0405] At least one hydrogen atom in the compound represented by formula (H5) may be further substituted with an alkyl group having 1 to 24 carbon atoms, and any —CH 2 - is further -O- or -Si(CH 3 ) 2 -, and the alkyl group directly bonded to the compound represented by formula (H5) is -CH 2 Any -CH except 2 - may be substituted with an arylene having 6 to 24 carbon atoms, and any hydrogen in the alkyl may be substituted with fluorine.

[0406] In addition, at least one hydrogen in the compound represented by formula (H5) may be substituted with a halogen or deuterium.

[0407] 3-1-5-2-4-2. Compound represented by formula (H6) [ka]

[0408] In formula (H6), R 1 ~R 16 are each independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino or aryloxy, wherein at least one hydrogen may be further substituted with aryl, heteroaryl or diarylamino.

[0409] In addition, at least one hydrogen atom in the compound represented by formula (H-6) may be substituted with an alkyl group having 1 to 24 carbon atoms, and any —CH 2 - is further -O- or -Si(CH 3 ) 2 -, and the -CH directly bonded to the compound represented by formula (H6) in the alkyl 2Any -CH except 2 - may be substituted with an arylene having 6 to 24 carbon atoms, and any hydrogen in the alkyl may be substituted with fluorine.

[0410] In addition, at least one hydrogen in the compound represented by formula (H6) may be substituted with a halogen or deuterium.

[0411] 3-1-5-2-4-3. "R in formula (H5) 1 ~R 11 " and "R in formula (H6) 1 ~R 16 」 "R in formula (H5) 1 ~R 11 " and "R in formula (H6) 1 ~R 16 " are each independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino or aryloxy, and are preferably an aryl having 6 to 30 carbon atoms, a heteroaryl having 2 to 30 carbon atoms, diarylamino (amino having two aryl groups having 6 to 30 carbon atoms), diheteroarylamino (amino having two heteroaryl groups having 2 to 30 carbon atoms), arylheteroarylamino (amino having an aryl group having 6 to 30 carbon atoms and a heteroaryl group having 2 to 30 carbon atoms) or aryloxy having 6 to 30 carbon atoms.

[0412] Examples of the aryl of "aryl", "diarylamino", the aryl of "arylheteroarylamino", and the aryl of "aryloxy" include a monocyclic benzene ring, a bicyclic bicyclic bicyclic naphthalene ring, a tricyclic terphenyl ring (m-terphenyl, o-terphenyl, p-terphenyl), a fused tricyclic acenaphthylene ring, a fluorene ring, a phenalene ring, a phenanthrene ring, a fused tetracyclic triphenylene ring, a pyrene ring, a naphthacene ring, a fused pentacyclic perylene ring, a pentacene ring, and the like. As described below, the aryls substituted with the heteroaryls defined below are also defined as aryls in formula (H5) and formula (H6).

[0413] Examples of the heteroaryl in "heteroaryl" and "diheteroarylamino" and the heteroaryl in "arylheteroarylamino" include a pyrrole ring, an oxazole ring, an isoxazole ring, a thiazole ring, an isothiazole ring, an imidazole ring, an oxadiazole ring, a thiadiazole ring, a triazole ring, a tetrazole ring, a pyrazole ring, a pyridine ring, a pyrimidine ring, a pyridazine ring, a pyrazine ring, a triazine ring, an indole ring, an isoindole ring, a 1H-indazole ring, a benzimidazole ring, a benzoxazole ring, a benzothiazole ring, a 1H -benzotriazole ring, quinoline ring, isoquinoline ring, cinnoline ring, quinazoline ring, quinoxaline ring, phthalazine ring, naphthyridine ring, purine ring, pteridine ring, carbazole ring, acridine ring, phenoxathiin ring, phenoxazine ring, phenothiazine ring, phenazine ring, indolizine ring, furan ring, benzofuran ring, isobenzofuran ring, dibenzofuran ring, thiophene ring, benzothiophene ring, dibenzothiophene ring, furazan ring, oxadiazole ring, thianthrene ring and monovalent groups such as the heteroaryl substituted with N-aryl.In addition, as described below, those heteroaryls substituted with the aryls defined above are also defined as heteroaryls in formula (H5) and formula (H6).

[0414] In addition, R in formula (H5)1 ~R 11 and R in formula (H6) 1 ~R 16 The aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, or aryloxy described above may have at least one hydrogen atom further substituted with an aryl, heteroaryl, or diarylamino. The aryl, heteroaryl, or diarylamino thus substituted may include R 1 ~R 11 Or R 1 ~R 16 Examples include those explained in the section.

[0415] R 1 ~R 11 Or R 1 ~R 16 Specific examples of the groups include groups represented by the following formulae (RG-1) to (RG-10). The groups represented by the following formulae (RG-1) to (RG-10) are bonded to the rings a to d in formula (H5) or (H6) at *.

[0416] [ka]

[0417] The definitions of "aryl" and "heteroaryl" in formulae (H5) and (H6) are explained with reference to the specific groups mentioned above. Formulae (RG-1), (RG-4) and (RG-7) are aryl, formulae (RG-2), (RG-3) and (RG-6) are heteroaryl, formula (RG-9) is heteroaryl substituted with heteroaryl, and formula (RG-10) is aryl substituted with heteroaryl. Formula (RG-5) is aryl (phenyl) substituted with diarylamino (diphenylamino), and formula (RG-8) is diarylamino (diphenylamino).

[0418] [ka]

[0419] 3-1-5-2-4-4.Specific examples of compounds A more specific structure of the compound represented by formula (H5) or formula (H6) is shown below.

[0420] The specific structure of the compound represented by the following formula (H5) or formula (H6) may be substituted with alkyl having 1 to 24 carbon atoms. [ka]

[0421] [ka]

[0422] [ka]

[0423] [ka]

[0424] [ka]

[0425] [ka]

[0426] [ka]

[0427] [ka]

[0428] [ka]

[0429]

change

[0430]

change

[0431]

change

[0432]

change

[0433]

change

[0434]

change

[0435]

change

[0436]

change

[0437]

change

[0438]

change

[0439]

change

[0440]

change

[0441]

change

[0442]

change

[0443]

change

[0444]

change

[0445]

change

[0446] 3-1-5-2-4-5. Method for producing the compound represented by formula (H5) or formula (H6) For the compound represented by formula (H5), first, the rings a to c are bonded with a bonding group (-O-) to produce an intermediate (first reaction), and then the rings a to c are bonded with a bonding group (group containing B) to produce the final product (second reaction). For the compound represented by formula (H6), first, the rings a to d are bonded with a bonding group (>NH or single bond) to produce an intermediate (first reaction), and then the rings a to d are bonded with a bonding group (group containing B) to produce the final product (second reaction). For the first reaction, for example, if it is an etherification reaction, a general reaction such as a nucleophilic substitution reaction or an Ullmann reaction can be used, and if it is an amination reaction, a general reaction such as a Buchwald-Hartwig reaction can be used. For the second reaction, a tandem hetero Friedel-Crafts reaction (successive aromatic electrophilic substitution reaction, the same applies below) can be used.

[0447] <Production method: Example of the second reaction of the compound represented by formula (H5)> The second reaction is a reaction to introduce B (boron) that bonds the a, b, and c rings, as shown in the following scheme (1). As an example, the case of the compound represented by formula (H5) is shown below. First, the hydrogen atom between the two 0s is orthometalated with n-butyllithium, sec-butyllithium, t-butyllithium, or the like. Next, boron trichloride, boron tribromide, or the like is added to perform lithium-boron metal exchange, and then a tandem boron-Friedel-Crafts reaction is carried out by adding a Bronsted base such as N,N-diisopropylethylamine, thereby obtaining the target product. In the second reaction, a Lewis acid such as aluminum trichloride may be added to promote the reaction.

[0448] [ka]

[0449] In the above scheme, lithium was introduced to the desired position by orthometalation. However, as shown in the following scheme (2), lithium can also be introduced to the desired position by halogen-metal exchange after introducing a bromine atom or the like to the desired position.

[0450] [ka]

[0451] By appropriately selecting the above-mentioned synthesis method and the raw materials to be used, a compound having a substituent at a desired position and represented by formula (H-5) can be synthesized.

[0452] <Production method: Example of a method for producing the compound represented by formula (H6)> The first and second reactions in the method for producing the compound represented by formula (H5) described above can be applied to the method for producing the compound represented by formula (H6). In other words, the second reaction is a reaction for introducing B (boron) which bonds NH to the c and d rings, and the hydrogen atom of NH is orthometalated with n-butyllithium, sec-butyllithium, t-butyllithium, or the like, and then boron trichloride, boron tribromide, or the like is added to perform lithium-boron metal exchange, and a tandem boron-Friedel-Crafts reaction can be carried out by further adding a Bronsted base such as N,N-diisopropylethylamine to obtain the target product. Here again, a Lewis acid such as aluminum trichloride may be added in the second reaction to promote the reaction.

[0453] 3-1-5-2-5. Compounds containing the structure represented by formula (H8) The compound containing a structure represented by formula (H8) contains a plurality of structures represented by formula (H8), preferably 1 to 5 structures, more preferably 1 to 3 structures, even more preferably 1 to 2 structures, and most preferably 1 structure. When a plurality of structures are contained, the structures are directly bonded to each other via a single bond or a specific linking group.

[0454] [ka]

[0455] In formula (H8), Z is "=C(-H)-" or "=N-", and the H in the "=C(-H)-" may be substituted with a structure represented by a substituent.

[0456] When H in "=C(-H)-" which is Z is substituted, examples of the substituent include aryl, heteroaryl, substituted silyl, substituted phosphine oxide group, and substituted carboxy.

[0457] Specific examples of the "aryl" substituent include phenyl, tolyl, xylyl, triphenylenyl, fluorenyl, 9,9-dimethylfluorenyl, benzofluorenyl, dibenzofluorenyl, biphenylyl, terphenylyl, quaterphenylyl, and the like, and preferably phenyl, biphenylyl, terphenylyl, and fluorenyl. Examples of aryl having a substituent include tolyl, xylyl, and 9,9-dimethylfluorenyl. As shown in the specific examples, aryl includes both fused aryl and non-fused aryl.

[0458] Specific examples of the substituent "heteroaryl" include pyrrolyl, pyrazolyl, pyrazinyl, pyrimidinyl, pyridazinyl, pyridyl, triazinyl, indolyl, isoindolyl, imidazolyl, benzimidazolyl, indazolyl, imidazo[1,2-a]pyridinyl, furyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, azadibenzofuranyl, thienyl, benzothienyl, dibenzothienyl, azadibenzothienyl, quinolyl, isoquinolyl, quinoxalinyl, quinazolinyl, and naphthalene. Examples of the aryl group include phthyridinyl, carbazolyl, azacarbazolyl, phenanthridinyl, acridinyl, phenazinyl, phenothiazinyl, phenoxazinyl, oxazolyl, oxadiazolyl, furazanyl, benzoxazolyl, thiazolyl, thiadiazolyl, benzothiazolyl, triazolyl, and tetrazolyl. Preferred examples include dibenzofuranyl, dibenzothienyl, carbazolyl, pyridyl, pyrimidinyl, triazinyl, azadibenzofuranyl, and azadibenzothienyl. Dibenzofuranyl, dibenzothienyl, azadibenzofuranyl, and azadibenzothienyl are more preferred.

[0459] The substituent "substituted silyl" is also preferably a group selected from the group consisting of substituted or unsubstituted trialkylsilyl, substituted or unsubstituted arylalkylsilyl, and substituted or unsubstituted triarylsilyl.

[0460] Specific examples of the substituted or unsubstituted trialkylsilyl include trimethylsilyl and triethylsilyl. Specific examples of the substituted or unsubstituted arylalkylsilyl include diphenylmethylsilyl, ditolylmethylsilyl, and phenyldimethylsilyl. Specific examples of the substituted or unsubstituted triarylsilyl include triphenylsilyl and tritolylsilyl.

[0461] The "substituted phosphine oxide group" as a substituent is also preferably a substituted or unsubstituted diarylphosphine oxide group. Specific examples of the substituted or unsubstituted diarylphosphine oxide group include diphenylphosphine oxide and ditolylphosphine oxide.

[0462] The substituent "substituted carboxy" includes, for example, benzoyloxy and the like.

[0463] Examples of the linking group that bonds a plurality of structures represented by formula (H8) include divalent to tetravalent, divalent to trivalent, or divalent derivatives of the above-mentioned aryl or heteroaryl.

[0464] Specific examples of the compound containing the structure represented by formula (H8) are shown below.

[0465] [ka]

[0466] [ka]

[0467] 3-1-5-2-6.TADF material The high T1 compound may be a TADF material.

[0468] In this specification, TADF material means a material that is a "thermally activated delayed fluorescent material." In "thermally activated delayed fluorescent material," the energy difference between the excited singlet state and the excited triplet state is reduced, thereby allowing for highly efficient reverse energy transfer from the excited triplet state, which usually has a low transition probability, to the excited singlet state, resulting in emission from the singlet state (thermally activated delayed fluorescence, TADF). In normal fluorescent emission, 75% of the triplet excitons generated by current excitation pass through a thermal deactivation pathway and cannot be extracted as fluorescent light. On the other hand, in TADF, all excitons can be used for fluorescent emission, making it possible to realize highly efficient organic electroluminescence devices.

[0469] TADF materials are preferably donor-acceptor type TADF compounds (DA type TADF compounds) designed to localize the HOMO and LUMO within a molecule using electron-donating substituents called donors and electron-accepting substituents called acceptors, thereby allowing efficient reverse intersystem crossing to occur.

[0470] In this specification, the term "electron-donating substituent" (donor) refers to a substituent or partial structure in which the HOMO orbital is localized in a TADF compound molecule, and the term "electron-accepting substituent" (acceptor) refers to a substituent or partial structure in which the LUMO orbital is localized in a TADF compound molecule.

[0471] In general, TADF compounds using donors and acceptors have large spin orbit coupling (SOC) due to their structure, and small exchange interaction between HOMO and LUMO, resulting in a low ΔE STSince the ΔT is small, a very fast reverse intersystem crossing rate can be obtained. On the other hand, TADF compounds using donors or acceptors have a large structural relaxation in the excited state (in some molecules, the stable structure differs between the ground state and the excited state, so when an external stimulus causes a transition 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.

[0472] However, by simultaneously using the polycyclic aromatic compound represented by formula (1), the polycyclic aromatic compound represented by formula (1) functions as an emitting dopant and the TADF material functions as an assisting dopant, thereby enabling high color purity to be exhibited. The TADF material may be any compound whose emission spectrum at least partially overlaps with the absorption spectrum of the polycyclic aromatic compound represented by formula (1). The polycyclic aromatic compound represented by formula (1) and the TADF material may both be contained in the same layer or in adjacent layers.

[0473] Examples of TADF materials that can be used for such purposes include a compound represented by the following formula (H7) or a compound having the following formula (H7) as a partial structure. JPEG2025085631000170.jpg9170

[0474] In formula (H7), ED is an electron donating group, Ln is a bonding group, and EA is an electron accepting group. The lowest excited singlet energy level (E S1 ) and the lowest excited triplet energy level (E T1 ) energy difference (ΔE ST ) is less than 0.2 eV (Hiroki Uoyama, Kenichi Goushi, Katsuyuki Shizu, Hiroko Nomura, Chihaya Adachi, Nature, 492, 234-238 (2012)). The energy difference (ΔE ST) is preferably 0.15 eV or less, more preferably 0.10 eV or less, and further preferably 0.08 eV or less.

[0475] As the electron donating group (donor structure) and the electron accepting group (acceptor structure) used in the TADF material, for example, the structures described in Chemistry of Materials, 2017, 29, 1946-1963 can be used. 3 Examples of functional groups containing nitrogen include functional groups derived from carbazole, dimethylcarbazole, di-tert-butylcarbazole, dimethoxycarbazole, tetramethylcarbazole, benzofluorocarbazole, benzothienocarbazole, phenyldihydroindolocarbazole, phenylbicarbazole, bicarbazole, tercarbazole, diphenylcarbazolylamine, tetraphenylcarbazolyldiamine, phenoxazine, dihydrophenazine, phenothiazine, dimethyldihydroacridine, diphenylamine, bis(tert-butylphenyl)amine, N1-(4-(diphenylamino)phenyl)-N4,N4-diphenylbenzene-1,4-diamine, dimethyltetraphenyldihydroacridinediamine, tetramethyl-dihydro-indenoacridine, and diphenyl-dihydrodibenzoazasiline. Examples of EA include, for example, sp 2Nitrogen-containing aromatic rings, CN-substituted aromatic rings, rings with ketones and cyano, more specifically sulfonyldibenzene, benzophenone, phenylenebis(phenylmethanone), benzonitrile, isonicotinonitrile, phthalonitrile, isophthalonitrile, paraphthalonitrile, triazole, oxazole, thiadiazole, benzothiazole, benzobis(thiazole), benzoxazole, benzobis(oxazole), quinoline, benzimidazole, dibenzoquinoxaline, heptaazaphenalene, thioxanthone dioxide, dimethylanthone ... Examples of the groups include groups derived from thracenone, anthracenedione, pyridine, 5H-cyclopenta[1,2-b:5,4-b']dipyridine, benzenetricarbonitrile, fluorene dicarbonitrile, pyrazine dicarbonitrile, pyridine dicarbonitrile, dibenzoquinoxaline dicarbonitrile, pyrimidine, phenylpyrimidine, methylpyrimidine, triazine, triphenyltriazine, bis(phenylsulfonyl)benzene, dimethylthioxanthene dioxide, thianthrene tetraoxide, and tris(dimethylphenyl)borane. Examples of Ln include single bonds and arylenes, more specifically, phenylene, biphenylene, naphthylene, and the like. In addition, in any of the structures, hydrogen may be substituted with alkyl, cycloalkyl, and aryl. In particular, it is preferable that the compound has at least one partial structure selected from carbazole, phenoxazine, acridine, triazine, pyrimidine, pyrazine, thioxanthene, benzonitrile, phthalonitrile, isophthalonitrile, diphenylsulfone, triazole, oxadiazole, thiadiazole, and benzophenone.

[0476] In formula (H7), the linking group Ln functions as a spacer structure that separates the donor partial structure and the acceptor partial structure.

[0477] More specifically, the compound represented by formula (H7) may be any of the compounds represented by formulas (H7-1), (H7-2) and (H7-3). [ka]

[0478] In formula (H7-1), formula (H7-2) and formula (H7-3), Each M is independently a single bond, -O-, >N-Ar, or >C(-Ar). 2 and from the viewpoint of the HOMO depth and the lowest excited singlet energy level and the lowest excited triplet energy level of the partial structure to be formed, it is preferably a single bond, -O- or >N-Ar; J is a linking group corresponding to Ln in formula (H7), and each J is independently an arylene having 6 to 18 carbon atoms. From the viewpoint of the magnitude of conjugation exuded from the donor partial structure and the acceptor partial structure, an arylene having 6 to 12 carbon atoms is preferable, and more specific examples thereof include phenylene, methylphenylene, and dimethylphenylene. Q is each independently =C(-H)- or =N-, and is preferably =N- from the viewpoint of shallowness of the LUMO of the partial structure to be formed and heights of the lowest excited singlet energy level and the lowest excited triplet energy level; Ar each independently represents hydrogen, an aryl having 6 to 24 carbon atoms, a heteroaryl having 2 to 24 carbon atoms, an alkyl having 1 to 12 carbon atoms, or a cycloalkyl having 3 to 18 carbon atoms; from the viewpoint of the HOMO depth and the height of the lowest excited singlet energy level and the lowest excited triplet energy level of the partial structure to be formed, Ar is preferably hydrogen, an aryl having 6 to 12 carbon atoms, a heteroaryl having 2 to 14 carbon atoms, an alkyl having 1 to 4 carbon atoms, or a cycloalkyl having 6 to 10 carbon atoms, more preferably hydrogen, phenyl, tolyl, xylyl, mesityl, biphenyl, pyridyl, bipyridyl, triazyl, carbazolyl, dimethylcarbazolyl, di-tert-butylcarbazolyl, benzimidazole, or phenylbenzimidazole, and further preferably hydrogen, phenyl, or carbazolyl; m is 1 or 2; n is an integer of 2 to (6-m), and from the viewpoint of steric hindrance, is preferably an integer of 4 to (6-m).

[0479] Furthermore, at least one hydrogen in the compounds represented by the above formulas may be substituted with a halogen or deuterium.

[0480] Examples of the compound represented by formula (H7) include compounds represented by the following structures: In the structural formula, * denotes a bond position, "Me" denotes methyl, and "tBu" denotes t-butyl.

[0481] [ka]

[0482] [ka]

[0483] [ka]

[0484] [ka]

[0485] [ka]

[0486] [ka]

[0487] [ka]

[0488] [ka]

[0489] [ka]

[0490] [ka]

[0491] As the compound represented by formula (H7), among the specific compounds, PIC-TRZ, TXO-TPA, TXO-PhCz, PXZD SO2, ACRD SO2, DTC-DBT, DTAO, 4CzBN, 4CzBN-Ph, 5CzBN, 3Cz2DPhCzBN, 4CzIPN, 2PXZ-TAZ, Cz-TRZ3, BDPCC-TPTA, MA-TA, PA-TA, FA-TA, PXZ-TRZ, DMAC-TRZ, BCzT, DCzTrz, DDCzTrz, spiroAC-TRZ, Ac-HPM, Ac-PPM, Ac-MPM, TCzTrz, TmCzTrz and DCzmCzTrz are preferred.

[0492] 3-1-5-3. Thermally activated delayed phosphor (assisting dopant) The light-emitting layer may contain a thermally activated delayed phosphor as an assisting dopant.

[0493] "Thermally activated delayed fluorescent material" refers to a compound that absorbs thermal energy, undergoes reverse intersystem crossing from the lowest excited triplet state to the lowest excited singlet state, and is radiatively deactivated from the lowest excited singlet state to emit delayed fluorescence. However, "thermally activated delayed fluorescent material" also includes compounds that undergo higher triplets in the process of excitation from the lowest excited triplet state to the lowest excited singlet state. For example, see a paper by Monkman et al. of Durham University (NATURE COMMUNICATIONS, 7:13680, DOI:10.1038 / ncomms 13680), 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 a paper by Sato et al. of Kyoto University (Scientific Reports, 7:4820, DOI:10.1038 / s41598-017-05007-7). Examples of such reviews include a conference presentation by Sato et al. (98th Spring Annual Meeting of the Chemical Society of Japan, presentation number: 2I4-15, Mechanism of Highly Efficient Emission in Organic Electroluminescence Using DABNA as an Emitting Molecule, Graduate School of Engineering, Kyoto University), a review by Bui et al. (DOI: 10.3762 / bjoc.14.18), a review by Duan et al. (DOI: 10.1063 / 1.5143501), a review by Ding et al. (DOI: 10.1088 / 1674-4926 / 42 / 5 / 050201), and a review by Xie et al. (DOI: 10.1002 / adom.202002204). In the present invention, when a sample containing the 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 material". Here, the term "slow fluorescent component" refers to a component whose fluorescent lifetime is 0.1 μsec or longer. The fluorescent lifetime can be measured, for example, using a fluorescent lifetime measuring device (manufactured by Hamamatsu Photonics KK, C11367-01).

[0494] The polycyclic aromatic compound represented by formula (1) 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 represented by formula (1).

[0495] 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).

[0496] The "host compound" in a TAF element means a compound whose lowest 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 fluorescent material as an assisting dopant and the emitting dopant.

[0497] 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.

[0498] The lowest excited 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 lowest excited triplet energy levels E(2,T,Sh) and E(3,T,Sh) of the emitting dopant or assisting dopant having the highest lowest excited triplet energy level in the emitting layer from the viewpoint of promoting TADF generation in the emitting layer without inhibiting it, and specifically, the lowest excited triplet energy level E(1,T,Sh) of the host compound is preferably 0.01 eV or higher, more preferably 0.03 eV or higher, and even more preferably 0.1 eV or higher than E(2,T,Sh) and E(3,T,Sh). In addition, a compound having TADF activity may be used as the host compound.

[0499] 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.

[0500] 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.

[0501] In general, thermally activated delayed phosphors using donors and acceptors have large spin-orbit coupling (SOC) due to their structure, and small exchange interaction between HOMO and LUMO, resulting in a low ΔE S1T1 Since the γ is small, a very fast reverse intersystem crossing rate can be obtained. On the other hand, thermally activated delayed fluorescent materials 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 transition 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.

[0502] As the thermally activated delayed phosphor in the TAF element, for example, a compound in which donor and acceptor are bonded directly or via a spacer can be used.As the electron donor group (donor structure) and electron acceptor group (acceptor structure) used in the thermally activated delayed phosphor of the present invention, for example, the structure described in Chemistry of Materials, 2017, 29, 1946-1963 can be used. 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-butylphenyl)amine, N1-(4-(diphenylamino)phenyl)-N4,N4-diphenylbenzene-1,4-diamine, 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, 5H-cyclopenta[1,2-b:5,4-b']dipyridine, fluorene dicarbonitrile, triphenyltriazine, 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.

[0503] The compound used as the assisting dopant in the light-emitting layer of the TAF element is preferably a thermally activated delayed phosphor, the emission spectrum of which at least partially overlaps with the absorption peak of the emitting dopant.

[0504] 3-1-5-4. Phosphorescent materials (assisting dopants) In the light-emitting layer, a phosphorescent material may be used as an assisting dopant. The phosphorescent material utilizes the intramolecular spin-orbit interaction (heavy atom effect) of a metal atom to obtain light emission from a triplet. For example, a luminescent metal complex can be used as such a phosphorescent material. For example, the luminescent metal complex can be a compound represented by the following formula (B-1) or (B-2).

[0505] [ka]

[0506] In formula (B-1), M is at least one selected from the group consisting of Ir, Pt, Au, Eu, Ru, Re, Ag, and Cu, n is an integer of 1 to 3, and each "XY" is independently a bidentate ligand.

[0507] In the formula (B-2), M is at least one selected from the group consisting of Pt, Re, and Cu, and "WXYZ" is a tetradentate ligand.

[0508] In the formula (B-1), M is preferably Ir and n is preferably 3 from the viewpoints of efficiency and life.

[0509] In the formula (B-2), M is preferably Pt from the viewpoints of efficiency and life.

[0510] The ligand (XY) in the formula (B-1) has at least one ligand selected from the group consisting of the following: The ligand (WXYZ) in the formula (B-2) has at least one ligand selected from the group consisting of the following as a part.

[0511] [ka]

[0512] During the ceremony, --- binds to the central metal M, Y is independently BRe , N.R. e , P.R. e , O, S, Se, C=O, S=O, SO 2 , C.R. e R f , SiR e R f , or GeR e R f and Each aromatic carbon CH in the ring may be independently replaced by N; R e and R f may be optionally fused or linked to form a ring, R a , R b , R c , and R d may each independently be unsubstituted or substituted with from 1 to the maximum number of possible substitutions; R a , R b , R c , R d , R e , and R f are each independently hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, aryl, heteroaryl, nitrile, isonitrile, sulfanyl, or combinations thereof; However, R a , R b , R c , and R d Any two adjacent substituents in may be fused or linked to form a ring or to form a multidentate ligand.

[0513] The compound represented by formula (B-1) is, for example, Ir(ppy) 3 , Ir(ppy) 2 (acac), Ir(mppy) 3 , Ir(PPy) 2 (m-bppy), BtpIr(acac), Ir(btp) 2 (acac), Ir(2-phq) 3, Hex-Ir(phq) 3 , Ir(fbi) 2 (acac), fac-Tris(2-(3-p-xylyl)phenyl)pyridine iridium(III), Eu(dbm) 3 (Phen), Ir(piq) 3 , Ir(piq) 2 (acac), Ir(Fliq) 2 (acac), Ir(Flq) 2 (acac), Ru(dtb-bpy) 3 2(PF 6 ), Ir(2-phq) 3 , Ir(BT) 2 (acac), Ir(DMP) 3 , Ir(Mphq) 3 IR(phq) 2 tpy, fac-Ir(ppy) 2 Pc, Ir(dp)PQ 2 , Ir(Dpm)(Piq) 2 , Hex-Ir(piq) 2 (acac), Hex-Ir(piq) 3 , Ir(dmpq) 3 , Ir(dmpq) 2 (acac), FPQIrpic, etc.

[0514] Other examples of the compound represented by formula (B-1) include the following compounds: [ka]

[0515] [ka]

[0516] [ka]

[0517] In addition, iridium complexes described in JP 2006-089398 A, JP 2006-080419 A, JP 2005-298483 A, JP 2005-097263 A, and JP 2004-111379 A, ​​U.S. Patent Application Publication No. 2019 / 0051845, etc., or platinum complexes described in Advanced Materials, 26:7116-7121, NPG Asia Materials 13, 53(2021), Applied Physics Letters, 117, 253301 (2020), Light-Emitting Diode-An Outlook On the Empirical Features and Its Recent Technological Advancements, Chapter 5 may be used.

[0518] 3-1-5-5. Other dopant materials The polycyclic aromatic compound containing the structural unit represented by formula (1) may be used in combination with other dopant materials. However, the other dopant materials are preferably less than 100% by mass, more preferably 50% by mass or less, even more preferably 30% by mass or less, and particularly preferably 10% by mass or less, based on the total mass of the polycyclic aromatic compound containing the structural unit represented by formula (1) in one light-emitting layer. Known compounds can be used as the other dopant materials, and several materials can be selected according to the desired emission color.

[0519] As other dopant materials, it is also preferable to use polycyclic aromatic compounds containing boron, such as those described in International Publication No. 2015 / 102118, International Publication No. 2020 / 162600, and paragraphs 0097 to 0269 of JP-A-2021-077890.

[0520] Examples of other dopant materials include the following compounds: [ka]

[0521] 3-1-6. Electron injection layer and electron transport layer in organic electroluminescent device The electron injection layer (107) plays a role of efficiently injecting electrons moving from the cathode (108) into the light emitting layer (105) or the electron transport layer (106). The electron transport layer (106) plays a role of efficiently transporting electrons injected from the cathode (108) or electrons injected from the cathode (108) via the electron injection layer (107) to the light emitting layer (105). The electron transport layer (106) and the electron injection layer (107) are each formed by laminating or mixing one or more types of electron transport / injection materials, or by a mixture of an electron transport / injection material and a polymer binder.

[0522] 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.

[0523] The material (electron transport material) forming the electron transport layer (106) or the electron injection layer (107) can be arbitrarily selected from compounds conventionally used as electron transport compounds in photoconductive materials and known compounds used in the electron injection layer and electron transport layer of organic EL elements.

[0524] 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, phosphine 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.

[0525] Specific examples of other electron transport compounds include pyridine derivatives, naphthalene derivatives, anthracene derivatives, benzofluorene derivatives, phenanthroline derivatives, perinone derivatives, coumarin derivatives, naphthalimide derivatives, anthraquinone derivatives, diphenoquinone derivatives, diphenylquinone derivatives, perylene derivatives, oxadiazole derivatives (1,3-bis[(4-t-butylphenyl)1,3,4-oxadiazolyl]phenylene, etc.), thiophene derivatives, triazole derivatives (N-naphthyl-2,5-diphenyl-1,3,4-triazole, etc.), thiadiazole derivatives, metal complexes of oxine derivatives, quinolinol-based metal complexes, quinoxaline derivatives, polymers of quinoxaline derivatives, benzazole compounds, gallium complexes, pyrazole derivatives, perfluorinated phenylene derivatives, triazine derivatives, etc. pyrazine derivatives, benzoquinoline derivatives (e.g., 2,2'-bis(benzo[h]quinolin-2-yl)-9,9'-spirobifluorene), imidazopyridine derivatives, borane derivatives, benzimidazole derivatives (e.g., tris(N-phenylbenzimidazol-2-yl)benzene), benzoxazole derivatives, benzothiazole derivatives, quinoline derivatives, oligopyridine derivatives such as terpyridine, bipyridine derivatives, terpyridine derivatives (e.g., 1,3-bis(4'-(2,2':6',2"-terpyridinyl))benzene), naphthyridine derivatives (e.g., bis(1-naphthyl)-4-(1,8-naphthyridin-2-yl)phenylphosphine oxide), aldazine derivatives, arylnitrile derivatives, indole derivatives, phosphine oxide derivatives, and bisstyryl derivatives.

[0526] Further, a metal complex having an electron-accepting nitrogen can also be used, and examples thereof include hydroxyazole complexes such as quinolinol metal complexes and hydroxyphenyloxazole complexes, azomethine complexes, tropolone metal complexes, flavonol metal complexes, and benzoquinoline metal complexes.

[0527] The above-mentioned materials may be used alone or in combination with different materials.

[0528] Among the above-mentioned materials, borane derivatives, pyridine derivatives, fluoranthene derivatives, BO-based derivatives, benzofluorene derivatives, phosphine oxide derivatives, pyrimidine derivatives, arylnitrile derivatives, triazine derivatives, benzimidazole derivatives, phenanthroline derivatives, and quinolinol-based metal complexes are preferable.

[0529] <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.

[0530] [ka]

[0531] In formula (ETM-1), R 11 and R 12 are each independently at least one of hydrogen, alkyl, cycloalkyl, optionally substituted aryl, substituted silyl, an optionally substituted heterocyclic compound having a nitrogen atom, 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, cycloalkyl, and the like.

[0532] 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.

[0533] [ka]

[0534] 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, an optionally substituted heterocyclic compound having a nitrogen atom, 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, an optionally substituted heterocyclic compound having a nitrogen atom, 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, cycloalkyl, and the like.

[0535] [ka]

[0536] 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, an optionally substituted heterocyclic compound having a nitrogen atom, 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. In addition, examples of the substituent in the case where "optionally substituted" or "substituted" include aryl, heteroaryl, alkyl, cycloalkyl, and the like.

[0537] X 1 Specific examples of the group include divalent groups represented by any of the following formulae (X-1) to (X-9).

[0538] [ka]

[0539] (In each formula, R a are each independently alkyl, cycloalkyl or optionally substituted phenyl, and * indicates the bonding position.)

[0540] Specific examples of the borane derivative include the following compounds: [ka]

[0541] The borane derivative can be produced using known raw materials and known synthesis methods.

[0542] <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]

[0543] 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.

[0544] In formula (ETM-2-1), R 11 ~R 18 are each independently hydrogen, alkyl (preferably alkyl having 1 to 24 carbon atoms), cycloalkyl (preferably cycloalkyl having 3 to 12 carbon atoms) or aryl (preferably aryl having 6 to 30 carbon atoms).

[0545] 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.

[0546] 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.

[0547] [ka]

[0548] The pyridine-based substituent is any one of the formulae (Py-1) to (Py-15) (wherein * indicates a bonding position), and among these, any one of the following formulae (Py-21) to (Py-44) is preferable. [ka]

[0549] 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.

[0550] 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 and branched alkyl having 3 to 24 carbon atoms. A preferred "alkyl" is an alkyl having 1 to 18 carbon atoms (branched alkyl having 3 to 18 carbon atoms). A more preferred "alkyl" is an alkyl having 1 to 12 carbon atoms (branched alkyl having 3 to 12 carbon atoms). An even more preferred "alkyl" is an alkyl having 1 to 6 carbon atoms (branched alkyl having 3 to 6 carbon atoms). An especially preferred "alkyl" is an alkyl having 1 to 4 carbon atoms (branched alkyl having 3 to 4 carbon atoms).

[0551] 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 of the alkyl ether 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.

[0552] As for the alkyl having 1 to 4 carbon atoms substituted with the pyridine-based substituent, the above description of the alkyl can be cited.

[0553] R 11~R 18 In the above, examples of the "cycloalkyl" include cycloalkyl having 3 to 12 carbon atoms. A preferred "cycloalkyl" is cycloalkyl having 3 to 10 carbon atoms. A more preferred "cycloalkyl" is cycloalkyl having 3 to 8 carbon atoms. An even more preferred "cycloalkyl" is cycloalkyl having 3 to 6 carbon atoms.

[0554] Specific examples of "cycloalkyl" include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, methylcyclopentyl, cycloheptyl, methylcyclohexyl, cyclooctyl, and dimethylcyclohexyl.

[0555] 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.

[0556] Specific examples of the "aryl having 6 to 30 carbon atoms" include monocyclic aryl such as phenyl, fused bicyclic aryl such as (1-, 2-)naphthyl, fused tricyclic aryl such as acenaphthylene-(1-, 3-, 4-, 5-)yl, fluoren-(1-, 2-, 3-, 4-, 9-)yl, phenalene-(1-, 2-)yl, and (1-, 2-, 3-, 4-, 9-)phenanthryl, fused tetracyclic aryl such as triphenylene-(1-, 2-)yl, pyrene-(1-, 2-, 4-)yl, and naphthacene-(1-, 2-, 5-)yl, and fused pentacyclic aryl such as perylene-(1-, 2-, 3-)yl and pentacene-(1-, 2-, 5-, 6-)yl.

[0557] Preferred "aryl having 6 to 30 carbon atoms" include phenyl, naphthyl, phenanthryl, chrysenyl, triphenylenyl, and the like, more preferably phenyl, 1-naphthyl, 2-naphthyl, or phenanthryl, and particularly preferably phenyl, 1-naphthyl, or 2-naphthyl.

[0558] R in formula (ETM-2-2) 11 and R 12 may be bonded to form a ring, and as a result, cyclobutane, cyclopentane, cyclopentene, cyclopentadiene, cyclohexane, fluorene, indene, or the like may be spiro-bonded to the five-membered ring of the fluorene skeleton.

[0559] Specific examples of the pyridine derivative include the following compounds: [ka]

[0560] This pyridine derivative can be produced using known raw materials and known synthesis methods.

[0561] <Fluoranthene derivatives> The fluoranthene derivative is, for example, a compound represented by the following formula (ETM-3), and is disclosed in detail in WO 2010 / 134352.

[0562] [ka]

[0563] In formula (ETM-3), X 12 ~X 21 represents hydrogen, halogen, linear, branched or cyclic alkyl, linear, branched or cyclic alkoxy, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl, where the substituent in the case of substitution includes aryl, heteroaryl, alkyl, cycloalkyl, etc.

[0564] Specific examples of the fluoranthene derivative include the following compounds. [ka]

[0565] <BO-based derivative> The BO-based derivative is, for example, a polycyclic aromatic compound represented by the following formula (ETM-4), or a multimer of a polycyclic aromatic compound having a plurality of structures represented by the following formula (ETM-4).

[0566]

Chemical formula

[0567] R 1 ~R 11 are each independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, alkyl, cycloalkyl, alkoxy or aryloxy, and at least one hydrogen in these may be substituted with aryl, heteroaryl, alkyl or cycloalkyl.

[0568] Also, among R 1 ~R 11 adjacent groups may be bonded to each other to form an aryl ring or a heteroaryl ring together with the a-ring, b-ring or c-ring, and at least one hydrogen in the formed ring may be substituted with aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, alkyl, cycloalkyl, alkoxy or aryloxy, and at least one hydrogen in these may be substituted with aryl, heteroaryl, alkyl or cycloalkyl.

[0569] Also, at least one hydrogen in the compound or structure represented by the formula (ETM-4) may be substituted with halogen or deuterium.

[0570] Regarding the description of the substituents and ring-forming forms in the formula (ETM-4), the description of the polycyclic aromatic compound composed of the partial structure represented by the formula (1) can be cited.

[0571] Specific examples of the BO derivative include the following compounds. [ka]

[0572] The BO derivative can be produced using known raw materials and known synthesis methods.

[0573] <Benzofluorene derivatives> The benzofluorene derivative is, for example, a compound represented by the following formula (ETM-6). [ka]

[0574] 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.

[0575] 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.

[0576] Ar 2The "alkyl" in the above may be either linear or branched, and examples thereof include linear alkyl having 1 to 24 carbon atoms and branched alkyl having 3 to 24 carbon atoms. A preferred "alkyl" is an alkyl having 1 to 18 carbon atoms (branched alkyl having 3 to 18 carbon atoms). A more preferred "alkyl" is an alkyl having 1 to 12 carbon atoms (branched alkyl having 3 to 12 carbon atoms). An even more preferred "alkyl" is an alkyl having 1 to 6 carbon atoms (branched alkyl having 3 to 6 carbon atoms). An especially preferred "alkyl" is an alkyl having 1 to 4 carbon atoms (branched alkyl having 3 to 4 carbon atoms). Specific examples of "alkyl" include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, t-butyl, n-pentyl, isopentyl, neopentyl, t-pentyl, n-hexyl, 1-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, n-heptyl, 1-methylhexyl, and the like.

[0577] Ar 2 In the above, the "cycloalkyl" can be, 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, dimethylcyclohexyl, and the like.

[0578] 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.

[0579] Specific examples of the "aryl having 6 to 30 carbon atoms" include phenyl, naphthyl, acenaphthylenyl, fluorenyl, phenalenyl, phenanthryl, triphenylenyl, pyrenyl, naphthacenyl, phenylenyl, and pentacenyl.

[0580] 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.

[0581] Specific examples of the benzofluorene derivative include the following compounds. [ka]

[0582] The benzofluorene derivative can be produced using known raw materials and known synthesis methods.

[0583] <Phosphine oxide derivatives> The phosphine oxide derivative is, for example, a compound represented by the following formula (ETM-7-1): Details are also described in WO 2013 / 079217 and WO 2013 / 079678. [ka]

[0584] 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.

[0585] When substituted, the substituent may be an aryl, heteroaryl, alkyl, or cycloalkyl.

[0586] The phosphine oxide derivative may be, for example, a compound represented by the following formula (ETM-7-2). [ka]

[0587] R 1 ~R 3 may be the same or different and are selected from among hydrogen, alkyl, cycloalkyl, aralkyl, alkenyl, cycloalkenyl, alkynyl, alkoxy, alkylthio, cycloalkylthio, aryl ether (aryl ether group), aryl thioether (aryl thioether group), aryl, heterocyclic group, halogen, cyano, aldehyde, carbonyl, carboxyl, amino, nitro, silyl, and a fused ring formed between adjacent substituents.

[0588] 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 1does not exist.

[0589] Among these substituents, alkyl refers to a saturated aliphatic hydrocarbon group such as methyl, ethyl, propyl, butyl, etc., which may be unsubstituted or substituted. If substituted, the substituent is not particularly limited, and may be, for example, an alkyl, aryl, or heterocyclic group, which is also common to 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 from the viewpoint of availability and cost.

[0590] 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.

[0591] 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.

[0592] The alkenyl refers to an unsaturated aliphatic hydrocarbon group containing a double bond, such as vinyl, allyl, butadienyl, etc., 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.

[0593] Furthermore, cycloalkenyl refers to an unsaturated alicyclic hydrocarbon group containing a double bond, such as cyclopentenyl, cyclopentadienyl, cyclohexenyl, etc., which may be unsubstituted or substituted.

[0594] 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 in the range of 2 to 20.

[0595] The alkoxy refers to an aliphatic hydrocarbon group with an ether bond such as methoxy, 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.

[0596] Moreover, alkylthio is a group in which the oxygen atom of the ether bond of alkoxy is replaced with a sulfur atom.

[0597] Moreover, cycloalkylthio is a group in which the oxygen atom of the ether bond of cycloalkoxy is replaced with a sulfur atom.

[0598] The aryl ether refers to an aromatic hydrocarbon group formed by an ether bond, such as phenoxy, 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.

[0599] 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.

[0600] The aryl group refers to an aromatic hydrocarbon group such as phenyl, naphthyl, biphenylyl, phenanthryl, terphenylyl, and pyrenyl. 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.

[0601] The heterocyclic group refers to a cyclic structural 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.

[0602] Halogen refers to fluorine, chlorine, bromine and iodine.

[0603] The aldehyde, carbonyl, and amino groups may include groups substituted with aliphatic hydrocarbons, alicyclic hydrocarbons, aromatic hydrocarbons, heterocycles, and the like.

[0604] Furthermore, the aliphatic hydrocarbons, alicyclic hydrocarbons, aromatic hydrocarbons and heterocycles may be either unsubstituted or substituted.

[0605] 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.

[0606] 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.

[0607] Specific examples of the phosphine oxide derivative include the following compounds. [ka]

[0608] The phosphine oxide derivative can be produced using known raw materials and known synthesis methods.

[0609] <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.

[0610] [ka]

[0611] 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.

[0612] The "aryl" in the "optionally substituted aryl" includes, for example, aryl having 6 to 30 carbon atoms, preferably aryl having 6 to 24 carbon atoms, more preferably aryl having 6 to 20 carbon atoms, and further preferably aryl having 6 to 12 carbon atoms.

[0613] 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, and (1-,2-,3-,4-,9-)phenanthryl; the tetracyclic aryl is quaterphenylyl (5'-phenyl-m-terphenyl-2-yl, 5'-phenyl-m-terphenyl-3-yl, 5'-phenyl-m-terphenyl-4-yl, and m-quaterphenylyl); the condensed tetracyclic aryl is triphenylene-(1-,2-)yl, pyrene-(1-,2-,4-)yl, and naphthacene-(1-,2-,5-)yl; and the condensed pentacyclic aryl is perylene-(1-,2-,3-)yl and pentacene-(1-,2-,5-,6-)yl.

[0614] 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.

[0615] 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.

[0616] The aryl and heteroaryl may be substituted, for example, by the above-mentioned aryl or heteroaryl, respectively.

[0617] Specific examples of the pyrimidine derivative include the following compounds: [ka]

[0618] The pyrimidine derivative can be produced using known raw materials and known synthesis methods.

[0619] <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.

[0620] [ka]

[0621] Arni From the viewpoint of high-speed electron transportability, 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, in order to use in a layer adjacent to the light-emitting layer, it is preferable that the aryl group has a high T1 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.

[0622] 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 it is a donor heteroaryl, and since it is used as an electron transport layer, it is preferable that there are few donor heteroaryls. From the viewpoint of charge transportability, it is preferable that it is an aryl or heteroaryl with a large number of carbon atoms, and it is preferable that it 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.

[0623] The "aryl" in the "optionally substituted aryl" includes, for example, aryl having 6 to 30 carbon atoms, preferably aryl having 6 to 24 carbon atoms, more preferably aryl having 6 to 20 carbon atoms, and further preferably aryl having 6 to 12 carbon atoms.

[0624] 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, and (1-,2-,3-,4-,9-)phenanthryl; the tetracyclic aryl is quaterphenylyl (5'-phenyl-m-terphenyl-2-yl, 5'-phenyl-m-terphenyl-3-yl, 5'-phenyl-m-terphenyl-4-yl, and m-quaterphenylyl); the condensed tetracyclic aryl is triphenylene-(1-,2-)yl, pyrene-(1-,2-,4-)yl, and naphthacene-(1-,2-,5-)yl; and the condensed pentacyclic aryl is perylene-(1-,2-,3-)yl and pentacene-(1-,2-,5-,6-)yl.

[0625] 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.

[0626] 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.

[0627] Additionally, the aryl and heteroaryl may be substituted, for example by the aryl or heteroaryl described above.

[0628] 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.

[0629] Specific examples of the arylnitrile derivative include the following compounds: [ka]

[0630] The arylnitrile derivatives can be produced using known raw materials and known synthesis methods.

[0631] <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). Details are described in the specification of U.S. Patent Application Publication No. 2011 / 0156013.

[0632] [ka]

[0633] 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.

[0634] The "aryl" in the "optionally substituted aryl" includes, for example, aryl having 6 to 30 carbon atoms, preferably aryl having 6 to 24 carbon atoms, more preferably aryl having 6 to 20 carbon atoms, and further preferably aryl having 6 to 12 carbon atoms.

[0635] 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, and (1-,2-,3-,4-,9-)phenanthryl; the tetracyclic aryl is quaterphenylyl (5'-phenyl-m-terphenyl-2-yl, 5'-phenyl-m-terphenyl-3-yl, 5'-phenyl-m-terphenyl-4-yl, and m-quaterphenylyl); the condensed tetracyclic aryl is triphenylene-(1-,2-)yl, pyrene-(1-,2-,4-)yl, and naphthacene-(1-,2-,5-)yl; and the condensed pentacyclic aryl is perylene-(1-,2-,3-)yl and pentacene-(1-,2-,5-,6-)yl.

[0636] 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.

[0637] 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.

[0638] Additionally, the aryl and heteroaryl may be substituted, for example by the aryl or heteroaryl described above.

[0639] Specific examples of the triazine derivative include the following compounds: [ka]

[0640] The triazine derivative can be produced using known raw materials and known synthesis methods.

[0641] <Benzimidazole derivatives> The benzimidazole derivative is, for example, a compound represented by the following formula (ETM-11). [ka]

[0642] 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 of 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 the following benzimidazolyl (in the formula, * indicates the bonding position), and at least one hydrogen in the benzimidazole derivative may be replaced with deuterium.

[0643] [ka]

[0644] R in the 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 11 The explanation can be cited.

[0645] Φ is further preferably an anthracene ring or a fluorene ring, and in this case, the structure can be quoted from the explanation in formula (ETM-2-1) or formula (ETM-2-2), and R 11 ~R 18 The explanation for formula (ETM-2-1) or formula (ETM-2-2) can be cited. 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 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 substituents is replaced with a benzimidazole-based substituent, and the "pyridine-based substituent" is R 11 ~R 18 may be replaced with.

[0646] 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.

[0647] [ka]

[0648] The benzimidazole derivative can be produced using known raw materials and known synthesis methods.

[0649] <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.

[0650] [ka]

[0651] 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.

[0652] 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 of these bonds becomes a bond to the aryl ring φ.

[0653] At least one hydrogen atom in each of the phenanthroline derivatives may be replaced with deuterium.

[0654] R 11 ~R 18 As the alkyl, cycloalkyl and aryl in the formula (ETM-2), R 11 ~R 18 The explanation of the above can be cited. In addition to the above-mentioned examples, φ may 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 the bond position.

[0655] [ka]

[0656] 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-bis(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.

[0657] [ka]

[0658] The phenanthroline derivative can be produced using known raw materials and known synthesis methods.

[0659] <Quinolinol metal complexes> The quinolinol metal complex is, for example, a compound represented by the following formula (ETM-13).

[0660] [ka]

[0661] In the formula, R 1 ~R 16 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.

[0662] 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.

[0663] The quinolinol metal complex can be produced using known raw materials and known synthesis methods.

[0664] <Thiazole derivatives and benzothiazole derivatives> The thiazole derivative is, for example, a compound represented by the following formula (ETM-14-1). [ka]

[0665] The benzothiazole derivative is, for example, a compound represented by the following formula (ETM-14-2). [ka]

[0666] 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 of 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 following thiazolyl or benzothiazolyl (* indicates a bonding position), and at least one hydrogen in the thiazole derivative and the benzothiazole derivative may be replaced with deuterium.

[0667] [ka]

[0668] It is further preferable that φ is an anthracene ring or a fluorene ring. In this case, the structure can be explained with reference to the explanation in formula (ETM-2-1) or formula (ETM-2-2). 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 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 18At 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.

[0669] These thiazole or benzothiazole derivatives can be produced using known raw materials and known synthesis methods.

[0670] <Silole derivatives> The silole derivative is, for example, a compound represented by the following formula (ETM-15): The details are described in JP-A-9-194487.

[0671] [ka]

[0672] 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 (ETM-7-2) can be further cited. In addition, alkenyloxy and alkynyloxy are groups in which the alkyl part of alkoxy is replaced with alkenyl or alkynyl, respectively, and for details of these alkenyl and alkynyl, the explanations in formula (ETM-7-2) can be cited.

[0673] In addition, X and Y, both of which are alkyl, may be bonded to form a ring.

[0674] 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.

[0675] R 1 ~R 4 For details of halogen, alkyl, cycloalkyl, alkoxy, aryloxy, amino, aryl, heteroaryl, alkenyl and alkynyl in, the explanation in formula (1) can be referred to.

[0676] R 1 ~R 4 Of the alkylcarbonyl, arylcarbonyl, alkoxycarbonyl, aryloxycarbonyl, alkylcarbonyloxy, arylcarbonyloxy, alkoxycarbonyloxy, and aryloxycarbonyloxy in the above formula, the details of alkyl, aryl, and alkoxy can be referenced from the explanation in formula (1).

[0677] 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, and examples thereof include triarylsilyl, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, and alkyldicycloalkylsilyl. For details of the aryl, alkyl, and cycloalkyl in these, the explanation in formula (1) can be cited.

[0678] 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 further fused with other rings.

[0679] However, preferably, R 1 and R 4 is phenyl, X and Y are not alkyl or phenyl. Also preferably, R 1 and R 4 When R is thienyl, X and Y are alkyl, R 2 and R 3 is alkyl, aryl, alkenyl or R 2 and R 3 In addition, it is preferable that R 1 and R 4 When R is a silyl group, 2 , R 3 X and Y are not each independently hydrogen or an alkyl group 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.

[0680] These silole derivatives can be produced using known raw materials and known synthesis methods.

[0681] <Azoline derivatives> The azoline derivative is, for example, a compound represented by the following formula (ETM-16). Details are described in WO 2017 / 014226.

[0682] [ka]

[0683] 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 an alkyl having 1 to 6 carbon atoms, a cycloalkyl having 3 to 14 carbon atoms, an aryl having 6 to 18 carbon atoms, or a heteroaryl having 2 to 18 carbon atoms; 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, 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 is a site that binds 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):

[0684] [ka]

[0685] In formula (L-1), X1 ~X 6 are each independently =CR 6 - or =N- and X 1 ~X 6 At least two of =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 =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 in L may be substituted by an alkyl group having 1 to 4 carbon atoms, a cycloalkyl group having 5 to 10 carbon atoms, an aryl group having 6 to 10 carbon atoms, or a heteroaryl group having 2 to 10 carbon atoms; m is an integer 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 of the compound represented by formula (ETM-16) may be substituted with deuterium.

[0686] Specific azoline derivatives are compounds represented by the following formula (ETM-16-1) or formula (ETM-16-2). [ka]

[0687] 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 an alkyl having 1 to 6 carbon atoms, a cycloalkyl having 3 to 14 carbon atoms, an aryl having 6 to 18 carbon atoms, or a 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): [ka]

[0688] In formula (L-1), X 1 ~X 6 are each independently =CR 6 - or =N- and X 1 ~X6 At least two of =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 =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 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 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 of the compound represented by formula (ETM-16-1) or formula (ETM-16-2) may be replaced with deuterium.

[0689] 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.

[0690] [ka]

[0691] [ka]

[0692] [ka]

[0693] In the formula, Z is >CR 2 , >N-Ar, >NL, -O- or -S-, >CR 2 R in the formula (1) is independently an alkyl group having 1 to 4 carbon atoms, a cycloalkyl group having 5 to 10 carbon atoms, an aryl group having 6 to 12 carbon atoms, or a heteroaryl group having 2 to 12 carbon atoms, and R may be bonded to each other to form a ring, Ar in >N-Ar is an aryl group having 6 to 12 carbon atoms or a heteroaryl group having 2 to 12 carbon atoms, and 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.

[0694] 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.

[0695] Preferably, Ar in >N-Ar as Y or Z is selected from the group consisting of phenyl, naphthyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, naphthyridinyl, phthalazinyl, quinoxalinyl, quinazolinyl, cinnolinyl, and pteridinyl, and at least one hydrogen atom of Ar in >N-Ar as Y may be substituted with alkyl having 1 to 4 carbon atoms, cycloalkyl having 5 to 10 carbon atoms, or aryl having 6 to 10 carbon atoms.

[0696] 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 group formed by the azoline ring and L is the same.

[0697] Specific examples of azoline derivatives include the following compounds: In the structural formula, "Me" represents methyl.

[0698] [ka]

[0699] More preferably, φ is selected from the group consisting of divalent groups represented by the following formulae (φ2-1), (φ2-31), (φ2-32), (φ2-33) and (φ2-34), and at least one hydrogen of φ may be substituted with an aryl having 6 to 18 carbon atoms. In the following formulae, * indicates a bonding position.

[0700] [ka]

[0701] 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, provided that R 1 and R 2 are identical, and R 3 and R 4 are identical and R 1 ~R 4 cannot all become hydrogen at the same time, and m is 2, and the group formed by the azoline ring and L is the same.

[0702] Other specific examples of azoline derivatives include the following compounds: In the structural formula, "Me" represents methyl.

[0703] [ka]

[0704] For details of the alkyl, cycloalkyl, aryl or heteroaryl in the above formulas defining this azoline derivative, the explanation in formula (1) can be cited.

[0705] The azoline derivative can be produced using known raw materials and known synthesis methods.

[0706] <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.

[0707] 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.

[0708] The above-mentioned electron injection layer material and electron transport layer material can be used as an electron layer material in the form of a polymer compound obtained by polymerizing a reactive compound substituted with a reactive substituent as a monomer, or a crosslinked polymer thereof, or a pendant polymer compound obtained by reacting a main chain polymer with the reactive compound, or a crosslinked pendant polymer thereof. In this case, the explanation of the polycyclic aromatic compound having a partial structure represented by formula (1) can be cited as the reactive substituent.

[0709] The applications of such polymer compounds and crosslinked polymers will be described in detail below.

[0710] 3-1-7. Cathode in organic electroluminescent device The cathode (108) serves to inject electrons into the light-emitting layer (105) through the electron injection layer (107) and the electron transport layer (106).

[0711] 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 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. Other dopants that can be used include inorganic salts such as lithium fluoride, cesium fluoride, lithium oxide, and cesium oxide. However, they are not limited to these.

[0712] Further, for electrode protection, preferred examples include lamination of metals such as platinum, gold, silver, copper, iron, tin, aluminum, and indium, or alloys using these metals, inorganic substances such as silica, titania, and silicon nitride, polyvinyl alcohol, vinyl chloride, hydrocarbon polymer compounds, etc. The method of producing these electrodes is also not particularly limited as long as it can provide electrical continuity, and may be resistance heating, electron beam deposition, sputtering, ion plating, coating, or the like.

[0713] 3-1-8. Binders that may be used in each layer The materials used for the hole injection layer, hole transport layer, light emitting layer, electron transport layer and electron injection layer can form each layer alone, but they can also be used as a polymer binder by being dispersed in a solvent-soluble resin such as polyvinyl chloride, polycarbonate, polystyrene, poly(N-vinylcarbazole), polymethyl methacrylate, polybutyl methacrylate, polyester, polysulfone, polyphenylene oxide, polybutadiene, hydrocarbon resin, ketone resin, phenoxy resin, polyamide, ethyl cellulose, vinyl acetate resin, ABS resin, polyurethane resin, or a curable resin such as phenol resin, xylene resin, petroleum resin, urea resin, melamine resin, unsaturated polyester resin, alkyd resin, epoxy resin, silicone resin, or the like.

[0714] 3-1-9. Method for producing organic electroluminescent device Each layer constituting an organic EL element can be formed by forming the material to be formed into a thin film by a method such as vapor deposition, resistance heating vapor deposition, electron beam vapor deposition, sputtering, molecular lamination, printing, spin coating or casting, coating, etc. The thickness of each layer thus formed is not particularly limited and can be set appropriately according to the properties of the material, but is usually in the range of 2 nm to 5000 nm. The thickness of the film can usually be measured with a quartz crystal oscillation type film thickness measuring device, etc. When forming a thin film by vapor deposition, the vapor deposition conditions vary depending on the type of material, the desired crystal structure and association structure of the film, etc. The vapor deposition conditions are generally a boat heating temperature of +50 to +400°C, a vacuum degree of 10, and a vacuum of 10. -6~10 -3 It is preferable to appropriately set the pressure, pressure Pa, deposition rate 0.01 to 50 nm / sec, substrate temperature -150 to +300°C, and film thickness 2 nm to 5 µm.

[0715] 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.

[0716] Next, as an example of a method for producing an organic EL element, a method for producing an organic EL element consisting of an anode, a hole injection layer, a hole transport layer, an emitting layer consisting of a host material and a dopant material, an electron transport layer, an electron injection layer, and a cathode will be described.

[0717] <Vapor deposition method> A thin film of an anode material is formed on a suitable substrate by vapor deposition or the like to prepare an anode, and then a thin film of a hole injection layer and a hole transport layer is formed on the anode. A host material and a dopant material are co-deposited on the anode to form a thin film as a light-emitting layer, an electron transport layer and an electron injection layer are formed on the light-emitting layer, and a thin film of a cathode material is further formed by vapor deposition or the like to prepare a cathode, thereby obtaining a desired organic EL device. Note that in the preparation of the organic EL device described above, the order of preparation can be reversed, and the layers can be prepared in the order of cathode, electron injection layer, electron transport layer, light-emitting layer, hole transport layer, hole injection layer, and anode.

[0718] <Wet film formation method> The wet film formation method is carried out by preparing a low molecular weight compound capable of forming each organic layer of an organic EL element as a liquid composition for forming an organic layer, and using this. If there is no suitable organic solvent for dissolving this low molecular weight compound, the composition for forming an organic layer may be prepared from a polymer compound polymerized together with other monomers having a solubility function as a reactive compound obtained by substituting a reactive substituent on the low molecular weight compound or a main chain polymer.

[0719] In the wet film formation method, a coating film is generally formed through a coating step of coating a substrate with a composition for forming an organic layer and a drying step of removing the solvent from the coated composition for forming an organic layer. When the polymer compound has a crosslinkable substituent (also called a crosslinkable polymer compound), the polymer is further crosslinked by the drying step to form a crosslinked polymer. Depending on the coating step, a method using a spin coater is called a spin coat method, a method using a slit coater is called a slit coat method, a method using a plate is called a gravure, offset, reverse offset, or flexographic printing method, a method using an inkjet printer is called an inkjet method, and a method spraying in a mist form is called a spray method.

[0720] The drying process may be carried out by air drying, heating, drying under reduced pressure, etc. The drying process may be carried out once or may be carried out multiple times using different methods and conditions. Also, different methods may be used in combination, such as calcination under reduced pressure.

[0721] The wet film formation method is a film formation method using a solution, for example, some printing methods (inkjet methods), spin coating methods or casting methods, coating methods, etc. Unlike the vacuum deposition method, the wet film formation method does not require the use of expensive vacuum deposition equipment, and can form a film under atmospheric pressure. In addition, the wet film formation method allows for large area and continuous production, which leads to reduced manufacturing costs.

[0722] On the other hand, compared to the vacuum deposition method, wet film formation can be difficult to laminate. When producing laminated films using the wet film formation method, it is necessary to prevent the dissolution of the lower layer by the composition of the upper layer, and compositions with controlled solubility, crosslinking of the lower layer, and orthogonal solvents (solvents that do not dissolve in each other) are used. However, even with these technologies, it can be difficult to use the wet film formation method to apply all films.

[0723] Therefore, a method is generally adopted in which only some layers are formed by a wet film formation method and the remaining layers are formed by a vacuum deposition method when manufacturing an organic EL element.

[0724] For example, the procedure for producing an organic EL element by partially applying a wet film formation method will be described below.

[0725] (Step 1) Formation of the anode by vacuum deposition (Step 2) Forming a film by a wet film formation method using a composition for forming a hole injection layer containing a material for the hole injection layer (Step 3) Forming a film by a wet film formation method using a composition for forming a hole transport layer containing a material for the hole transport layer (Step 4) Formation of a film by a wet film formation method using a composition for forming an emitting layer containing a host material and a dopant material (Step 5) Formation of the electron transport layer by vacuum deposition (Step 6) Formation of the electron injection layer by vacuum deposition (Step 7) Cathode deposition by vacuum deposition Through this procedure, an organic EL element consisting of an anode, a hole injection layer, a hole transport layer, an emitting layer made of a host material and a dopant material, an electron transport layer, an electron injection layer, and a cathode is obtained.

[0726] Of course, the electron transport layer and the electron injection layer may also be formed by a wet film formation method using layer-forming compositions containing the electron transport layer material and the electron injection layer material, respectively. In this case, it is preferable to use a means for preventing dissolution of the underlying light-emitting layer, or a means for forming the film from the cathode side in the opposite procedure to the above.

[0727] <Other film formation methods> The composition for forming an organic layer can be formed into a film by laser thermal imaging (LITI). LITI is a method in which a compound attached to a substrate is heated and evaporated by a laser, and the composition for forming an organic layer can be used as the material applied to the substrate.

[0728] <Optional process> Before and after each film-forming step, appropriate treatment steps, cleaning steps, and drying steps may be appropriately inserted. Examples of treatment steps include exposure treatment, plasma surface treatment, ultrasonic treatment, ozone treatment, cleaning treatment using an appropriate solvent, and heat treatment. Furthermore, a series of steps for preparing a bank may also be included.

[0729] Photolithography techniques can be used to fabricate the banks. Positive resist materials and negative resist materials can be used as bank materials that can be used in photolithography. In addition, patternable printing methods such as inkjet printing, gravure offset printing, reverse offset printing, and screen printing can also be used. In this case, permanent resist materials can also be used.

[0730] Materials that can be used for the banks include, but are not limited to, polysaccharides and their derivatives, homopolymers and copolymers of hydroxyl-containing ethylenic monomers, biopolymers, polyacryloyl compounds, polyesters, polystyrenes, polyimides, polyamideimides, polyetherimides, polysulfides, polysulfones, polyphenylenes, polyphenyl ethers, polyurethanes, epoxy (meth)acrylates, melamine (meth)acrylates, polyolefins, cyclic polyolefins, acrylonitrile-butadiene-styrene copolymers (ABS), silicone resins, polyvinyl chloride, chlorinated polyethylene, chlorinated polypropylene, polyacetates, polynorbornenes, synthetic rubbers, fluorinated polymers such as polyfluorovinylidene, polytetrafluoroethylene, and polyhexafluoropropylene, copolymers of fluoroolefins and hydrocarbon olefins, and fluorocarbon polymers.

[0731] <Composition for forming organic layer used in wet film formation method> The composition for forming an organic layer is obtained by dissolving a low molecular weight compound capable of forming each organic layer of an organic EL device, or a polymer compound obtained by polymerizing the low molecular weight compound, in an organic solvent. For example, the composition for forming an emitting layer contains at least one polycyclic aromatic compound (or a polymer compound thereof) as a first component, which is a dopant material, at least one host material as a second component, and at least one organic solvent as a third component. The first component functions as a dopant component of the emitting layer obtained from the composition, and the second component functions as a host component of the emitting layer. The third component functions as a solvent that dissolves the first and second components in the composition, and gives a smooth and uniform surface shape due to the controlled evaporation rate of the third component itself during application.

[0732] <Organic solvent> The composition for forming an organic layer contains at least one organic solvent. By controlling the evaporation rate of the organic solvent during film formation, it is possible to control and improve the film formability, the presence or absence of defects in the coating film, the surface roughness, and the smoothness. In addition, during film formation using the inkjet method, it is possible to control the meniscus stability at the pinhole of the inkjet head, and control and improve the ejection properties. In addition, by controlling the drying rate of the film and the orientation of the derivative molecules, it is possible to improve the electrical properties, light emitting properties, efficiency, and life of an organic EL element having an organic layer obtained from the composition for forming an organic layer.

[0733] (1) Physical properties of organic solvents The boiling point of at least one organic solvent is 130°C to 300°C, more preferably 140°C to 270°C, and further preferably 150°C to 250°C. When the boiling point is higher than 130°C, it is preferable from the viewpoint of inkjet dischargeability. Also, when the boiling point is lower than 300°C, it is preferable from the viewpoint of coating film defects, surface roughness, residual solvent, and smoothness. From the viewpoint of good inkjet dischargeability, film-forming property, smoothness, and low residual solvent, it is more preferable that the organic solvent contains two or more organic solvents. On the other hand, in some cases, the composition may be in a solid state by removing the solvent from the composition for forming the organic layer, taking into consideration transportability, etc.

[0734] Furthermore, the organic solvent contains a good solvent (GS) and a poor solvent (PS) for at least one of the solutes, and the boiling point (BP) of the good solvent (GS) is GS ) is the boiling point (BP PS ) is particularly preferred.

[0735] By adding a poor solvent with a high boiling point, the good solvent with a low boiling point volatilizes first during film formation, increasing the concentration of the components in the composition and the concentration of the poor solvent, facilitating rapid film formation. This results in a coating film with fewer defects, less surface roughness, and high smoothness.

[0736] Difference in solubility (S GS -S PS The boiling point difference (BP) is preferably 1% or more, more preferably 3% or more, and even more preferably 5% or more. PS -BP GS ) is preferably 10° C. or higher, more preferably 30° C. or higher, and even more preferably 50° C. or higher.

[0737] After the film is formed, the organic solvent is removed from the coating film by a drying process such as vacuum, reduced pressure, or heating. When heating is performed, it is preferable to perform the heating at a temperature of at least one of the solutes +30°C or lower from the viewpoint of improving the coating film-forming property. Moreover, it is preferable to heat at a temperature of at least one of the solutes -30°C or higher from the viewpoint of reducing the residual solvent. Even if the heating temperature is lower than the boiling point of the organic solvent, the organic solvent is sufficiently removed because the film is thin. Moreover, drying may be performed multiple times at different temperatures, and multiple drying methods may be used in combination.

[0738] (2) Specific examples of organic solvents Examples of the organic solvent used in the composition for forming an organic layer include alkylbenzene solvents, phenyl ether solvents, alkyl ether solvents, cyclic ketone solvents, aliphatic ketone solvents, monocyclic ketone solvents, solvents having a diester skeleton, and fluorine-containing solvents. Specific examples include pentanol, hexanol, heptanol, octanol, nonanol, decanol, undecanol, dodecanol, tetradecanol, hexane-2-ol, heptan-2-ol, octan-2-ol, decan-2-ol, dodecan-2-ol, cyclohexanol, α-terpineol, β-terpineol, γ-terpineol, δ-terpineol, terpineol (mixture), ethylene glycol monomethyl ether acetate, propylene glycol monomethyl ether acetate, diethylene glycol dimethyl ether, dipropylene glycol dimethyl ether, diethylene glycol ethyl methyl ether, diethylene glycol isopropyl methyl ether, dipropylene glycol ethyl ... glycol monomethyl ether, diethylene glycol diethyl ether, diethylene glycol monomethyl ether, diethylene glycol butyl methyl ether, tripropylene glycol dimethyl ether, triethylene glycol dimethyl ether, diethylene glycol monobutyl ether, ethylene glycol monophenyl ether, triethylene glycol monomethyl ether, diethylene glycol dibutyl ether, triethylene glycol butyl methyl ether, polyethylene glycol dimethyl ether, tetraethylene glycol dimethyl ether, p-xylene, m-xylene, o-xylene, 2,6-lutidine, 2-fluoro-m-xylene, 3-fluoro-o-xylene, 2-chlorobenzotrifluoride, cumene, toluene, 2-chloro-6-fluorotoluene, 2-fluoroanisole, anisole, 2,3-dimethylpyrazine, bromobenzene, 4-fluoroanisole, 3-fluoroanisole, 3-trifluoromethylanisole, mesitylene, 1,2,4-Trimethylbenzene, t-butylbenzene, 2-methylanisole, phenetole, benzodioxole, 4-methylanisole, s-butylbenzene, 3-methylanisole, 4-fluoro-3-methylanisole, cymene, 1,2,3-trimethylbenzene, 1,2-dichlorobenzene, 2-fluorobenzonitrile, 4-fluoroveratrol, 2,6-dimethylanisole, n-butylbenzene, 3-fluorobenzonitrile, decalin (decahydronaphthalene), neopentylbenzene, 2,5-dimethylanisole, 2,4-dimethylanisole, benzonitrile, 3,5-dimethylanisole, diphenyl ether, 1-fluoro-3,5-dimethoxybenzene, methyl benzoate, isopentylbenzene, 3,4-dimethylanisole, o-tolunitrile, n-amylbenzene, veratrol, 1,2,3,4-tetramethylanisole, Examples of the solvent include, but are not limited to, tetrahydronaphthalene, ethyl benzoate, n-hexylbenzene, propyl benzoate, cyclohexylbenzene, 1-methylnaphthalene, butyl benzoate, 2-methylbiphenyl, 3-phenoxytoluene, 2,2'-bitolyl, dodecylbenzene, dipentylbenzene, tetramethylbenzene, trimethoxybenzene, trimethoxytoluene, 2,3-dihydrobenzofuran, 1-methyl-4-(propoxymethyl)benzene, 1-methyl-4-(butyloxymethyl)benzene, 1-methyl-4-(pentyloxymethyl)benzene, 1-methyl-4-(hexyloxymethyl)benzene, 1-methyl-4-(heptyloxymethyl)benzene, benzyl butyl ether, benzyl pentyl ether, benzyl hexyl ether, benzyl heptyl ether, and benzyl octyl ether. The solvents may be used alone or in admixture.

[0739] <Optional ingredients> The composition for forming the organic layer may contain any optional components, such as a binder and a surfactant, as long as the optional components do not impair the properties of the composition.

[0740] (1) Binder The composition for forming an organic layer may contain a binder. The binder forms a film during film formation and simultaneously bonds the obtained film to a substrate. The binder also plays a role in dissolving, dispersing and binding other components in the composition for forming an organic layer.

[0741] Examples of binders used in the organic layer-forming composition include, but are not limited to, acrylic resins, polyethylene terephthalate, ethylene-vinyl acetate copolymers, ethylene-vinyl alcohol copolymers, acrylonitrile-ethylene-styrene copolymer (AES) resins, ionomers, chlorinated polyethers, diaryl phthalate resins, unsaturated polyester resins, polyethylene, polypropylene, polyvinyl chloride, polyvinylidene chloride, polystyrene, polyvinyl acetate, Teflon, acrylonitrile-butadiene-styrene copolymer (ABS) resins, acrylonitrile-styrene copolymer (AS) resins, phenolic resins, epoxy resins, melamine resins, urea resins, alkyd resins, polyurethanes, and copolymers of the above resins and polymers.

[0742] The binder used in the composition for forming an organic layer may be of only one type, or a mixture of two or more types may be used.

[0743] (2) Surfactants The organic layer forming composition may contain a surfactant, for example, to control the film surface uniformity of the organic layer forming composition, the solvent affinity and liquid repellency of the film surface. Surfactants are classified into ionic and nonionic based on the structure of the hydrophilic group, and further classified into alkyl, silicon, and fluorine based based on the structure of the hydrophobic group. In addition, based on the molecular structure, they are classified into monomolecular systems with relatively small molecular weights and simple structures, and polymer systems with large molecular weights and side chains or branches. In addition, based on the composition, they are classified into single systems and mixed systems in which two or more types of surfactants and base materials are mixed. As the surfactant that can be used in the organic layer forming composition, any type of surfactant can be used.

[0744] Examples of surfactants include Polyflow No. 45, Polyflow KL-245, Polyflow No. 75, Polyflow No. 90, Polyflow No. 95 (trade names, manufactured by Kyoeisha Chemical Industry Co., Ltd.), DisperBYK 161, Disperbake 162, Disperbake 163, Disperbake 164, Disperbake 166, Disperbake 170, Disperbake 180, Disperbake 181, Disperbake 182, BYK300, BYK 306, BYK310, BYK320, BYK330, BYK342, BYK344, BYK346 (trade name, manufactured by BYK Japan Co., Ltd.), KP-341, KP-358, KP-368, KF-96-50CS, KF-50-100CS (trade name, manufactured by Shin-Etsu Chemical Co., Ltd.), Surflon SC-101, Surflon KH-40 (trade name, manufactured by Seimi Chemical Co., Ltd.), Ftergent 222F, Ftergent 251, FTX-218 (trade name, manufactured by Neos Co., Ltd.), EFTOP EF-351, EFTOP EF-352, EFTOP EF-601, EFTOP EF-801, EFTOPEF-802 (product name, manufactured by Mitsubishi Materials Corporation), Megafac F-470, Megafac F-471, Megafac F-475, Megafac R-08, Megafac F-477, Megafac F-479, Megafac F-553, Megafac F-554 (product name, manufactured by DIC Corporation), fluoroalkylbenzenesulfonates, fluoroalkylcarboxylates, fluoroalkylpolyoxyethyleneethers, fluoroalkylammonium iodides, fluoroalkylbetaines, fluoroalkylsulfonates, diglycerol tetrakis(fluoroalkylpolyoxyethyleneether), fluoroalkyltrimethylammonium salts, fluoroalkylaminosulfonates, polyoxyethylene nonylphenyl ether, polyoxyethylene octylphenyl ether, polyoxyethylene alkyl ether, polyoxyethylene laurate, polyoxyethylene oleate, polyoxyethylene stearate, polyoxyethylene laurylamine, sorbitan laurate, sorbitan palmitate, sorbitan stearate, sorbitan oleate, sorbitan fatty acid esters, polyoxyethylene sorbitan laurate, polyoxyethylene sorbitan palmitate, polyoxyethylene sorbitan stearate, polyoxyethylene sorbitan oleate, polyoxyethylene naphthyl ether, alkyl benzene sulfonates and alkyl diphenyl ether disulfonates.

[0745] The surfactant may be used alone or in combination of two or more kinds.

[0746] <Composition and Properties of the Organic Layer-Forming Composition> The content of each component in the composition for forming an organic layer is determined in consideration of the good solubility, storage stability and film-forming property of each component in the composition for forming an organic layer, the good film quality of the coating film obtained from the composition for forming an organic layer, the good discharge property when using an inkjet method, and the good electrical properties, light-emitting properties, efficiency and life of an organic EL device having an organic layer produced using the composition. For example, in the case of a composition for forming an emitting layer, it is preferable that the first component is 0.0001% by mass to 2.0% by mass relative to the total mass of the composition for forming an emitting layer, the second component is 0.0999% by mass to 8.0% by mass relative to the total mass of the composition for forming an emitting layer, and the third component is 90.0% by mass to 99.9% by mass relative to the total mass of the composition for forming an emitting layer.

[0747] More preferably, the first component is 0.005% by mass to 1.0% by mass, the second component is 0.095% by mass to 4.0% by mass, and the third component is 95.0% by mass to 99.9% by mass, more preferably, the first component is 0.05% by mass to 0.5% by mass, the second component is 0.25% by mass to 2.5% by mass, and the third component is 97.0% by mass to 99.7% by mass, more preferably, the first component is 0.05% by mass to 0.5% by mass, the second component is 0.25% by mass to 2.5% by mass, and the third component is 97.0% by mass to 99.7% by mass, more preferably, the first component is 0.05% by mass to 0.5% by mass, the second component is 0.25% by mass to 2.5% by mass, and the third component is 97.0% by mass to 99.7% by mass, more preferably, the second component is 0.095% by mass to 4.0% by mass, and the third component is 95.0% by mass to 99.9 ... third component is 95.0% by mass to 99.9% by mass, more preferably, the second component is 0.095% by mass to 4.

[0748] The composition for forming an organic layer can be produced by appropriately selecting the above-mentioned components and subjecting them to stirring, mixing, heating, cooling, dissolving, dispersing, etc., by a known method. After preparation, filtration, degassing (also called degassing), ion exchange treatment, and inert gas replacement / filling treatment, etc. may be appropriately selected.

[0749] The higher the viscosity of the composition for forming an organic layer, the better the film-forming properties and the better the ejection properties when using an inkjet method. On the other hand, the lower the viscosity, the easier it is to form a thin film. In this respect, the viscosity of the composition for forming an organic layer at 25°C is preferably 0.3 to 3 mPa·s, and more preferably 1 to 3 mPa·s. In the present invention, the viscosity is a value measured using a cone-plate type rotational viscometer (cone-plate type).

[0750] The lower the surface tension of the composition for forming an organic layer, the better the film-forming properties and the more defect-free the coating film will be. On the other hand, the higher the surface tension, the better the ink-jet ejection properties will be. From this point of view, the composition for forming an organic layer preferably has a surface tension at 25°C of 20 to 40 mN / m, more preferably 20 to 30 mN / m. In the present invention, the surface tension is a value measured using the hanging drop method.

[0751] <Crosslinkable polymer compound: Compound represented by formula (XLP-1)> Next, the case where the above-mentioned polymer compound has a crosslinkable substituent will be described. Such a crosslinkable polymer compound is, for example, a compound represented by the following formula (XLP-1).

[0752] [ka]

[0753] In formula (XLP-1), MUx, ECx, and k are defined the same as MU, EC, and k in formula (H3), except that the compound represented by formula (XLP-1) has at least one crosslinkable substituent (XLS), and preferably the content of the monovalent or divalent aromatic group having a crosslinkable substituent is 0.1 to 80 mass% in the molecule.

[0754] The content of the monovalent or divalent aromatic compound having a crosslinkable substituent is preferably from 0.5 to 50 mass %, more preferably from 1 to 20 mass %, in the molecule.

[0755] The crosslinkable substituent (XLS) is not particularly limited as long as it is a group that can further crosslink the above-mentioned polymer compound, but substituents having the following structures are preferred: In each structural formula, * indicates the bond position.

[0756] [ka]

[0757] 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.

[0758] Examples of the divalent aromatic compound having a crosslinkable substituent include compounds having the following partial structure: [ka]

[0759] [ka]

[0760] [ka]

[0761] <Method of producing polymer compound and crosslinkable polymer compound> The method for producing the polymer compound and the crosslinkable polymer compound will be described with reference to the compound represented by the above formula (H3) and the compound represented by the formula (XLP-1). These compounds can be synthesized by appropriately combining known production methods.

[0762] Solvents used in the reaction include aromatic solvents, saturated / unsaturated hydrocarbon solvents, alcohol solvents, and ether solvents, such as dimethoxyethane, 2-(2-methoxyethoxy)ethane, and 2-(2-ethoxyethoxy)ethane.

[0763] The reaction may also be carried out in a two-phase system. When the reaction is carried out in a two-phase system, a phase transfer catalyst such as a quaternary ammonium salt may be added as necessary.

[0764] The compound of formula (H3) and the compound of formula (XLP-1) may be produced in one step or in multiple steps. The compound may be produced by a batch polymerization method in which all the raw materials are put into a reaction vessel and then the reaction is started, a dropwise polymerization method in which the raw materials are added dropwise to a reaction vessel, or a precipitation polymerization method in which the product precipitates as the reaction proceeds, and these methods can be combined appropriately to synthesize the compound. For example, when the compound of formula (H3) is synthesized in one step, the target product is obtained by carrying out a reaction in a state in which a monomer having a polymerizable group bonded to a monomer unit (MU) and a monomer having a polymerizable group bonded to an end cap unit (EC) are added to a reaction vessel. When the compound of formula (H3) is synthesized in multiple steps, the target product is obtained by polymerizing the monomer having a polymerizable group bonded to a monomer unit (MU) to a desired molecular weight, and then adding and reacting a monomer having a polymerizable group bonded to an end cap unit (EC). By adding monomers with polymerizable groups bonded to different types of monomer units (MU) in multiple stages and carrying out the reaction, it is possible to prepare a polymer with a concentration gradient according to the structure of the monomer units. In addition, after preparing a precursor polymer, the target polymer can be obtained by post-reaction.

[0765] In addition, the primary structure of the polymer can be controlled by selecting the polymerizable group of the monomer. For example, as shown in synthesis schemes 1 to 3, it is possible to synthesize a polymer having a random primary structure (synthetic scheme 1) or a polymer having a regular primary structure (synthetic schemes 2 and 3), and these can be used in appropriate combination depending on the target object. In addition, if a monomer having three or more polymerizable groups is used, a hyperbranched polymer or a dendrimer can be synthesized.

[0766] [ka]

[0767] Monomers that can be used in the present invention include those described in JP 2010-189630 A, WO 2012 / 086671 A, WO 2013 / 191088 A, WO 2002 / 045184 A, WO 2011 / 049241 A, WO 2013 / 146806 A, WO 2005 / 049546 A, WO 2015 / 145871 A, JP 2010-215886 A, JP 2008-106241 A, WO 2016 / 031639 A, and JP 2011-174062 A. It can be synthesized in accordance with the methods described therein.

[0768] In addition, the specific polymer synthesis order can be synthesized in accordance with the methods described in JP 2012-036388 A, WO 2015 / 008851 A, JP 2012-36381 A, JP 2012-144722 A, WO 2015 / 194448 A, WO 2013 / 146806 A, WO 2015 / 145871 A, WO 2016 / 031639 A, WO 2016 / 125560 A, and WO 2011 / 049241 A.

[0769] 3-1-10.Application examples of organic electroluminescent devices The present invention can also be applied to a display device having an organic EL element or a lighting device having an organic EL element.

[0770] 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 according to this embodiment to a known driving device, and can be driven appropriately using a known driving method such as DC driving, pulse driving, or AC driving.

[0771] Examples of the display device include panel displays such as color flat panel displays, and flexible displays such as flexible color organic electroluminescence (EL) displays (see, for example, JP-A-10-335066, JP-A-2003-321546, JP-A-2004-281086, etc.). Examples of the display method include a matrix and / or segment method. Note that the matrix display and the segment display may coexist in the same panel.

[0772] 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.

[0773] 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.

[0774] Examples of the lighting device include lighting devices for indoor lighting, backlights for liquid crystal display devices, etc. (see, for example, JP 2003-257621 A, JP 2003-277741 A, JP 2004-119211 A, etc.). Backlights are mainly used for the purpose of improving the visibility of non-self-luminous display devices, and are used in liquid crystal display devices, clocks, audio devices, automobile panels, display boards, signs, etc. In particular, for liquid crystal display devices, particularly backlights for personal computers, where thinning is an issue, it is difficult to make them thin because conventional methods are made of fluorescent lamps and light guide plates, so the backlight using the light-emitting element according to this embodiment is characterized by its thinness and light weight.

[0775] 3-2. Other organic devices The polycyclic aromatic compound according to the present invention can be used for producing the organic electroluminescent device described above, as well as an organic field effect transistor or an organic thin-film solar cell.

[0776] 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.

[0777] 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.

[0778] (1) Substrate / gate electrode / insulator layer / source and drain electrodes / organic semiconductor active layer (2) Substrate / gate electrode / insulating layer / organic semiconductor active layer / source and drain electrodes (3) Substrate / organic semiconductor active layer / source and drain electrodes / 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.

[0779] 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.

[0780] 4. Wavelength conversion materials The polycyclic aromatic compound of the present invention can be used as a wavelength converting material.

[0781] Currently, the application of multi-color technology using color conversion methods to liquid crystal displays, organic electroluminescence displays, lighting, and the like is being actively considered. Color conversion refers to the wavelength conversion of light emitted from a light emitter to light with a longer wavelength, for example, converting ultraviolet light or blue light to green light or red light emission. By forming a wavelength conversion material with this color conversion function into a film and combining it with, for example, a blue light source, it becomes possible to extract the three primary colors of blue, green, and red from the blue light source, that is, to extract white light. By combining such a blue light source and a wavelength conversion film with a color conversion function as a light source unit, and combining it with a liquid crystal drive part and a color filter, it becomes possible to manufacture a full-color display. Furthermore, if there is no liquid crystal drive part, it can be used as a white light source as it is, and can be applied as a white light source such as 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.

[0782] 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 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.

[0783] 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 WO 2016 / 190283 can be used. As the other additives, the compounds described in paragraphs 0177 to 0181 of WO 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.

[0784] 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

[0785] The present invention will be described in more detail below with reference to examples, but the present invention is not limited to these.

[0786] <Synthesis Example> Synthesis Example (1): Synthesis of Compound (X1-1) [ka]

[0787] A 1.6M tert-butyllithium pentane solution (1.6ml) was added to a flask containing compound (S-X1-1) (1.5g) and tert-butylbenzene (7.0ml) under a nitrogen atmosphere at -30°C. After the dropwise addition, the temperature was raised to 60°C and stirred for 2 hours, and then components with a boiling point lower than that of tert-butylbenzene were distilled off under reduced pressure. The mixture was cooled to -30°C, boron tribromide (0.63g) was added, the mixture was heated to room temperature and stirred for 0.5 hours. Then, the mixture was cooled again to 0°C, N,N-diisopropylethylamine (0.43ml) was added, and the mixture was stirred at room temperature until the heat generation subsided, and then the mixture was heated to 120°C and stirred for 3 hours. The reaction solution was cooled to room temperature, and an aqueous sodium acetate solution cooled in an ice bath was added, followed by heptane, and the mixture was separated. Next, after purifying with a silica gel short-path column (eluent: toluene), the solvent was distilled off under reduced pressure, and the resulting solid was dissolved in toluene and reprecipitated by adding heptane to obtain compound (X1-1) (0.50 g).

[0788] Compounds (X1-2) to (X1-20), compounds (T1-1) to (T1-20), and compounds (C1-1) to (C1-14) were synthesized according to the method of Synthesis Example (1). 11 BBr with a B enrichment of 99% or more 3 Compounds (C1-1) to (C1-14) are compounds described in the specification of International Publication No. WO 2022 / 185896.

[0789] [ka]

[0790] The production of the target substance was confirmed by MALDI-TOF-MS (matrix-assisted laser desorption / ionization time-of-flight mass spectrometry).

[0791] [Table 1]

[0792] <Manufacture and Evaluation of Vapor Deposition-Type Organic EL Devices> Using each of the synthesized compounds of the present invention and comparative compounds, each of the organic EL devices of TADF, TAF, and PSF was manufactured.

[0793] <TADF Structure: Examples 1-X1-1 to 1-X1-20, Examples 1-T1-1 to 1-T1-20, and Comparative Examples 1-C1-1 to 1-C1-14> ITO (50 nm) / HAT-CN (10 nm) / HT-1 (60 nm) / SiCzCz (5 nm) / SiCzCz:SiTrzCz2: Each compound described in Table 2 (60:39:1) (35 nm) / mSiTrz (5 nm) / mSiTrz:Liq (1:1) (30 nm) / LiF (1 nm) / Al (100 nm) A glass substrate (manufactured by Opto Science Co., Ltd.) with a size of 26 mm × 28 mm × 0.7 mm, on which ITO with a thickness of 200 nm formed 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 vapor deposition apparatus (manufactured by Showa Vacuum Co., Ltd.), and molybdenum vapor deposition boats containing HAT-CN, HT-1, SiCzCz, SiTrzCz2, each compound described in Table 2, mSiTrz, and Liq, and tungsten vapor deposition boats containing LiF and aluminum were mounted.

[0794] The following layers were sequentially formed on the ITO film of the transparent support substrate. The vacuum chamber was 5×10 -4The pressure was reduced to Pa, and first, HAT-CN was heated and vapor-deposited to a thickness of 10 nm to form a hole injection layer. Next, HT-1 was heated and vapor-deposited to a thickness of 60 nm to form a hole transport layer (1), and further, SiCzCz was heated and vapor-deposited to a thickness of 5 nm to form a hole transport layer (2). Next, SiCzCz, SiTrzCz2, and each compound described in Table 2 were simultaneously heated and vapor-deposited to a thickness of 35 nm to form a light-emitting layer. The deposition rate was adjusted so that the mass ratio of SiCzCz, SiTrzCz2, and each compound described in Table 2 was approximately 60:39:1. Next, mSiTrz was heated and vapor-deposited to a thickness of 5 nm to form an electron transport layer (1), and further, mSiTrz and Liq were heated and vapor-deposited to a thickness of 30 nm to form an electron transport layer (2). The deposition rate was adjusted so that the mass ratio of SiTrz and Liq was approximately 1:1. The deposition rate of each layer was 0.01 - 1 nm / second. Thereafter, LiF was heated and vapor-deposited at a deposition rate of 0.01 - 0.1 nm / second to a thickness of 1 nm, and then, aluminum was heated and vapor-deposited to a thickness of 100 nm to form a cathode. Thereafter, an organic EL element was obtained. At this time, the deposition rate of aluminum was adjusted to be 1 - 10 nm / second. SiCzCz in the light-emitting layer corresponds to a hole-transporting host material, and SiTrzCz2 corresponds to an electron-transporting host material.

[0795] <TAF configuration: Examples 2-X1-1 to 2-X1-20, Examples 2-T1-1 to 2-T1-20, and Comparative Examples 2-C1-1 to 2-C1-14> ITO(50 nm) / HAT-CN(10 nm) / HT-1(60 nm) / SiCzCz(5 nm) / SiCzCz:SiTrzCz2:TADF-1: each compound described in Table 2(60:26:13:1)(35 nm) / mSiTrz(5 nm) / mSiTrz:Liq(1:1)(30 nm) / LiF(1 nm) / Al(100 nm) Except for the light-emitting layer, it was fabricated in the same manner as the TADF structure. In the light-emitting layer, SiCzCz, SiTrzCz2, (TADF-1), and each compound described in Table 2 were simultaneously heated and vapor-deposited to a film thickness of 35 nm. The deposition rate was adjusted so that the mass ratio of SiCzCz, SiTrzCz2, (TADF-1), and each compound described in Table 2 was approximately 60:26:13:1.

[0796] <PSF structure: Examples 3-X1-1 to 3-X1-20, Examples 3-T1-1 to 3-T1-20, and Comparative Examples 3-C1-1 to 3-C1-14> ITO(50 nm) / HAT-CN(10 nm) / HT-1(60 nm) / SiCzCz(5 nm) / SiCzCz:SiTrzCz2:PtON-TBBI: each compound described in Table 2 (60:26:13:1)(35 nm) / mSiTrz(5 nm) / mSiTrz:Liq(1:1)(30 nm) / LiF(1 nm) / Al(100 nm) The (TADF-1) in the TAF structure was replaced with PtON-TBBI, and the device was fabricated in the same manner.

[0797] The chemical structures of the compounds used in the manufacture of the above devices are shown below.

Chemical formula

[0798] [Evaluation] The evaluation items include driving voltage (V), emission wavelength (nm), CIE chromaticity (x, y), external quantum efficiency (%), maximum wavelength (nm) and full width at half maximum (nm) of the emission spectrum, etc. These evaluation items can use the values during emission, for example, at 1000 cd / m 2 The values during emission can be used.

[0799] 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.

[0800] The spectral radiance (emission spectrum) and external quantum efficiency were measured as follows. The device luminance was set to 1000 cd / m using an Advantest voltage / current generator R6144. 2 The device emits light by applying a voltage that is equal to the wavelength of the light emitted by the device. The spectral radiance of the visible light region is measured from a direction perpendicular to the light-emitting surface using a TOPCON SR-3AR spectroradiometer. Assuming that the light-emitting surface is a perfect diffusing surface, the measured spectral radiance value of each wavelength component is divided by the wavelength energy and multiplied by π to obtain the number of photons at each wavelength. The number of photons is then integrated over the entire wavelength range observed to obtain the total number of photons emitted from the device. The applied current value is divided by the elementary charge to obtain the number of carriers injected into the device, and the total number of photons emitted from the device is divided by the number of carriers injected into the device to obtain 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% of the maximum emission wavelength.

[0801] A DC voltage of 1000 cd / m was applied to the ITO electrode as the anode and the LiF / aluminum electrode as the cathode. 2 The characteristics of the light emission were measured. In addition, the time (lifetime) during which the TTF structure element maintained 95% or more of the initial brightness, and the time (lifetime) during which the TADF structure, TAF structure, and PSF structure elements maintained 50% or more of the initial brightness were measured. The emission peak of the elements was in the range of 450 to 470 nm in all cases.

[0802] The results are shown in Tables 2 to 4 below.

[0803] [Table 2] JPEG2025085631000244.jpg156170

[0804] [Table 3] JPEG2025085631000246.jpg154170

[0805] [Table 4] JPEG2025085631000248.jpg156170

[0806] The results show that the devices of the Examples have higher efficiency and longer life than the devices of the Comparative Examples which use compounds having a skeleton corresponding to that of the compounds of the Examples. [Explanation of symbols]

[0807] 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 having a structure consisting of one or more structural units represented by formula (1): 【Chemistry 1】 In formula (1), ring A, ring B, ring C, ring D and ring E each independently represent a substituted or unsubstituted aryl ring, or a substituted or unsubstituted heteroaryl ring; However, at least one selected from the group consisting of ring B and ring C is at least one of the groups represented by the formula (J ＡＢＣ or an aryl ring having a group represented by the formula (J ＡＢＣ ) as a substituent, Each X is independently O, S or Se; Each Ar is independently a group represented by formula (Ar), Formula (J ＡＢＣ ) in * indicates the point of attachment to the aryl or heteroaryl ring; ring P and ring Q each independently represent a substituted or unsubstituted aryl ring, or a substituted or unsubstituted heteroaryl ring; In formula (Ar), # represents the position of attachment to nitrogen, Ring F is a substituted or unsubstituted aryl ring, or a substituted or unsubstituted heteroaryl ring; G is a substituted or unsubstituted aryl, a substituted or unsubstituted heteroaryl, a substituted or unsubstituted arylthio, a substituted or unsubstituted heteroarylthio, a substituted or unsubstituted aryloxy, a substituted or unsubstituted heteroaryloxy, a substituted or unsubstituted alkyl, or a substituted or unsubstituted cycloalkyl; 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, the cycloalkane may be substituted with at least one substituent, and at least one -CH ２ - may be replaced by -O-; At least one hydrogen in the structure may be replaced with deuterium or a halogen, and at least one nitrogen is replaced with nitrogen-15 ( １５ N), and at least one sulfur may be replaced by sulfur-33 ( ３３ S), Sulfur-34 ( ３４ S) or sulfur-36 ( ３６ S), at least one oxygen is oxygen-17 ( １７ O) or oxygen-18 ( １８ O), at least one carbon is carbon-13 ( １３ C), at least one boron is boron-11 ( １１ B) may be substituted.

2. 2. The polycyclic aromatic compound according to claim 1, wherein X's are all O, all S, or all Se.

3. The polycyclic aromatic compound according to claim 1, characterized in that the formula (1) is represented by the following formula (2X): 【Chemistry 2】 In formula (2X), Each X is independently O or S; Ar is the same as defined in formula (1), Z ａ , Z ｂ , Z ｃ , Z ｄ and Z ｅ are each independently -C(-R Ｚ )= or -N=, R Ｊ is expressed by the formula (J ＡＢＣ ) is a group represented by R Ｚ are each independently selected from the group consisting of hydrogen, deuterium, a halogen, a nitro group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amino group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms, with the proviso that substituents on adjacent atoms may be bonded to each other to form a ring.

4. The polycyclic aromatic compound according to claim 1, characterized in that the formula (1) is represented by the following formula (2XJ): 【Chemistry 3】 In formula (2XJ), Each X is independently O or S; Ar is the same as defined in formula (1), Z ａ , Z ｂ , Z ｃ , Z ｄ , Z ｅ and Z ｊ are each independently -C(-R Ｚ )= or -N=, R Ｚ are each independently selected from the group consisting of hydrogen, deuterium, a halogen, a nitro group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amino group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms, with the proviso that substituents on adjacent atoms may be bonded to each other to form a ring.

5. The polycyclic aromatic compound according to claim 1, characterized in that it is represented by any one of the following formulas: 【Chemistry 4】 【Chemistry 5】 【Chemistry 6】 【Chemistry 7】 【Chemistry 8】 【Chemistry 9】 In the above formula, tBu is t-butyl.

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, the organic layer containing the polycyclic aromatic compound according to any one of claims 1 to 5.

7. The organic electroluminescent device according to claim 6, wherein the organic layer is a light-emitting layer.

8. The organic electroluminescent device according to claim 7, wherein the light-emitting layer includes at least one selected from the group consisting of an assisting dopant and a phosphorescent material.

9. A display device or a lighting device comprising the organic electroluminescent device according to claim 6.

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