Polycyclic aromatic compound

Abstract

To provide a novel polycyclic aromatic compound.SOLUTION: Provided is a polycyclic aromatic compound represented by formula (1) or a multimer thereof. (In the formula, A ring, B ring, and C ring are aryl rings and the like, which may be substituted; Y1 is B and the like; X1 is formula (1a) and the like and at least one X1 is formula (1a); D ring and E ring are aryl rings and the like which may be substituted; and X2 is a single bond and the like).SELECTED DRAWING: None

Description

[Technical field]

[0001] The present invention relates to a polycyclic aromatic compound. The present invention also relates to an organic electroluminescent element, an organic field effect transistor, an organic thin-film solar cell, a display device, and a lighting device, each using the polycyclic aromatic compound. [Background technology]

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

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

[0004] As materials for the light-emitting layer, for example, benzofluorene-based compounds have been developed (Patent Document 1). As hole-transporting materials, for example, triphenylamine-based compounds have been developed (Patent Document 2). As electron-transporting materials, for example, anthracene-based compounds have been developed (Patent Document 3).

[0005] In recent years, a material obtained by improving a triphenylamine derivative has also been reported as a material for use in organic EL devices and organic thin-film solar cells (Patent Document 4). This material is characterized by having its planarity enhanced by linking aromatic rings constituting triphenylamine with each other, based on N,N'-diphenyl-N,N'-bis(3-methylphenyl)-1,1'-biphenyl-4,4'-diamine (TPD), which has already been put to practical use. In this document, for example, the charge transport properties of an NO-linked compound (Compound 1 on page 63) are evaluated, but there is no description of a method for producing materials other than NO-linked compounds, and since the electronic state of the entire compound differs depending on the linked element, the properties obtained from materials other than NO-linked compounds are not yet known. There are other examples of such compounds (Patent Document 5). For example, a compound having a conjugated structure with a large triplet exciton energy (T1) can emit phosphorescence with a shorter wavelength, and is therefore useful as a material for a blue light-emitting layer. In addition, compounds having a new conjugated structure with a large T1 are also required as electron transport materials and hole transport materials sandwiching the light-emitting layer.

[0006] The host material for organic EL devices is generally a molecule in which multiple existing aromatic rings such as benzene or carbazole are linked together with single bonds or phosphorus or silicon atoms. This is because linking a large number of relatively small conjugated aromatic rings ensures the large HOMO-LUMO gap (band gap Eg in a thin film) required for the host material. Furthermore, host materials for organic EL devices that use phosphorescent materials or thermally activated delayed fluorescent materials have high triplet excitation energy (E T ) is also required, but by linking a donor or acceptor aromatic ring or substituent to the molecule, the SOMO1 and SOMO2 in the triplet excited state (T1) are localized, and the exchange interaction between the two orbitals is reduced, allowing the triplet excitation energy (E T) can be improved. However, small aromatic rings in the conjugated system do not have sufficient redox stability, and devices using molecules formed by linking existing aromatic rings as host materials do not have sufficient life spans. On the other hand, polycyclic aromatic compounds with extended π-conjugated systems generally have excellent redox stability, but they have poor HOMO-LUMO gaps (band gaps in thin films, Eg) and triplet excitation energies (E T ) is low, it has been considered unsuitable as a host material. [Prior art documents] [Patent documents]

[0007] [Patent Document 1] International Publication No. 2004 / 061047 [Patent Document 2] JP 2001-172232 A [Patent Document 3] JP 2005-170911 A [Patent Document 4] International Publication No. 2012 / 118164 [Patent Document 5] International Publication No. 2011 / 107186 [Patent Document 6] International Publication No. 2015 / 102118 Summary of the Invention [Problem to be solved by the invention]

[0008] As described above, various materials have been developed for use in organic EL devices, but in order to increase the options for materials for organic EL devices, it is desirable to develop materials made of compounds different from conventional ones. In particular, the organic EL characteristics obtained from materials other than the NO-linked compounds reported in Patent Documents 1 to 4 and the manufacturing methods thereof are not yet known.

[0009] In addition, Patent Document 6 reports a boron-containing polycyclic aromatic compound and an organic EL device using the same. However, in order to further improve the device characteristics, there is a demand for a material for an emission layer, in particular a dopant material, that can improve the luminous efficiency and device life. An object of the present invention is to provide a polycyclic aromatic compound having a novel structure and an organic EL device using the same. [Means for solving the problem]

[0010] As a result of intensive research to solve the above problems, the present inventors have found that an excellent organic EL element can be obtained by, for example, constructing an organic EL element by disposing a layer containing a polycyclic aromatic compound having a spiro structure between a pair of electrodes, and have completed the present invention. That is, the present invention provides the following polycyclic aromatic compound having a spiro structure or a multimer thereof, and further provides a material for an organic device, such as a material for an organic EL element, which contains the following polycyclic aromatic compound having a spiro structure or a multimer thereof.

[0011] [1] A polycyclic aromatic compound represented by the following formula (1), or a multimer of a polycyclic aromatic compound having a plurality of structures represented by the following formula (1): [ka]

[0012] (In formula (1), ring A, ring B and ring C are each independently an aryl ring or a heteroaryl ring, and at least one hydrogen atom in these rings may be substituted; Y 1 is B, P, P=O, P=S, Al, Ga, As, Si-R or Ge-R, X 1 are each independently a group represented by formula (1a), >O, >NR, >C(-R) 2 , >S, >Si(-R) 2 ,>S(=O) 2 or >Se and at least one X 1 is a group represented by formula (1a), In formula (1a), ring D and ring E are each independently an aryl ring or a heteroaryl ring, and at least one hydrogen atom in these rings may be substituted; X 2 is a single bond, >O, >NR, >C(-R) 2 , -C(-R) 2 -C(-R) 2 -, -C(-R)=C(-R)-, >S, >Si(-R) 2 ,>S(=O) 2 or >Se, * indicates the bond position, R in the >NR is each independently an optionally substituted aryl, an optionally substituted heteroaryl, an optionally substituted alkyl, or an optionally substituted cycloalkyl; The above-mentioned Si-R, Ge-R, and C(-R) 2 , -C(-R) 2 -C(-R) 2 -, -C(-R)=C(-R)- and >Si(-R) 2 R is each independently hydrogen, optionally substituted aryl, optionally substituted alkyl, or optionally substituted cycloalkyl; >NR, Si-R, Ge-R, >C(-R) 2 , -C(-R) 2 -C(-R) 2 -, -C(-R)=C(-R)- and >Si(-R) 2 R may be bonded to at least one ring selected from the group consisting of ring A, ring B, ring C, ring D and ring E via a linking group or a single bond; In the compound or structure represented by formula (1), at least one selected from the group consisting of aryl rings and heteroaryl rings may be fused with at least one cycloalkane; At least one hydrogen in the cycloalkane may be replaced; and At least one -CH in the cycloalkane 2 - may be replaced by -O-; At least one hydrogen atom in the compound or structure represented by formula (1) may be replaced with deuterium, cyano, or halogen.

[0013] [2] Ring A, ring B, ring C, ring D and ring E are each independently an aryl ring or a heteroaryl ring, and at least one hydrogen atom in these rings may be replaced by a substituted or unsubstituted aryl, a substituted or unsubstituted heteroaryl, a substituted or unsubstituted diarylamino, a substituted or unsubstituted diheteroarylamino, a substituted or unsubstituted arylheteroarylamino, a substituted or unsubstituted diarylboryl (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, or a substituted silyl, and these rings are each independently selected from the group consisting of Y 1 , and two X's 1 A 5- or 6-membered ring shares a bond with the central fused 2-ring structure of the above formula In the case of a polymer, it is a dimer or trimer having two or three structures represented by formula (1). The polycyclic aromatic compound or a multimer thereof according to [1].

[0014] [3] The polycyclic aromatic compound or a multimer thereof according to [1] or [2], which is a polycyclic aromatic compound represented by the following formula (2) or a multimer of a polycyclic aromatic compound having a plurality of structures represented by the following formula (2).

[0015] [ka]

[0016] (In formula (2), Y 1 is B, P, P=O, P=S, Al, Ga, As, Si-R or Ge-R, X 1 are each independently a group represented by formula (2a), >O, >NR, >C(-R) 2, >S, >Si(-R) 2 ,>S(=O) 2 or >Se and at least one X 1 is a group represented by formula (2a), In formula (2a), X 2 is a single bond, >O, >NR, >C(-R) 2 , -C(-R) 2 -C(-R) 2 -, -C(-R)=C(-R)-, >S, >Si(-R) 2 ,>S(=O) 2 or >Se, * indicates the bond position, In formula (2) and formula (2a), R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 , R 15 , R 16 , R 17 , R 18 , and R 19 are each independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl (two aryls may be bonded via a single bond or a linking group), alkyl, cycloalkyl, alkoxy, aryloxy, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, or alkyldicycloalkylsilyl, in which at least one hydrogen may be replaced by an aryl, heteroaryl, alkyl, or cycloalkyl; and R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8, R 9 , R 10 , R 11 , R 12 , R 13 , R 14 , R 15 , R 16 , R 17 , R 18 , and R 19 adjacent groups among the above may be bonded to each other to form an aryl ring or a heteroaryl ring together with the a ring, the b ring, the c ring, the d ring or the e ring, and at least one hydrogen atom in the formed ring may be replaced by an aryl, a heteroaryl, a diarylamino, a diheteroarylamino, an arylheteroarylamino, a diarylboryl (two aryls may be bonded via a single bond or a linking group), an alkyl, a cycloalkyl, an alkoxy, an aryloxy, a trialkylsilyl, a tricycloalkylsilyl, a dialkylcycloalkylsilyl or an alkyldicycloalkylsilyl, and at least one hydrogen atom in these may be replaced by an aryl, a heteroaryl, an alkyl or a cycloalkyl; R in the >NR is each independently an optionally substituted aryl, an optionally substituted heteroaryl, an optionally substituted alkyl, or an optionally substituted cycloalkyl; The above-mentioned Si-R, Ge-R, and C(-R) 2 , -C(-R) 2 -C(-R) 2 -, -C(-R)=C(-R)- and >Si(-R) 2 R is each independently hydrogen, optionally substituted aryl, optionally substituted alkyl, or optionally substituted cycloalkyl; >NR, Si-R, Ge-R, >C(-R) 2 , -C(-R) 2 -C(-R) 2 -, -C(-R)=C(-R)- and >Si(-R) 2 R may be bonded to at least one ring selected from the group consisting of ring a, ring b, ring c, ring d, and ring e via a linking group or a single bond; In the compound or structure represented by formula (2), at least one selected from the group consisting of an aryl ring and a heteroaryl ring may be condensed with at least one cycloalkane having 3 to 24 carbon atoms, at least one hydrogen in the cycloalkane may be substituted with an aryl having 6 to 30 carbon atoms, a heteroaryl having 2 to 30 carbon atoms, an alkyl having 1 to 24 carbon atoms, or a cycloalkyl having 3 to 24 carbon atoms, and at least one -CH in the cycloalkane 2 - may be replaced by -O-; At least one hydrogen atom in the compound or structure represented by formula (2) may be replaced with deuterium, cyano, or halogen.

[0017] [4] Y 1 The polycyclic aromatic compound or a multimer thereof according to any one of [1] to [3], wherein [5] X 1 is a group represented by formula (1a), and the other X 1 >O, >NR, >C(-R) 2 , >S, >Si(-R) 2 ,>S(=O) 2 or >Se. [6] The other X 1 The polycyclic aromatic compound or a multimer thereof according to [5], wherein [7] X 2 [6] The polycyclic aromatic compound or a multimer thereof according to [6], wherein [8] X 2 >O, >NR, >C(-R) 2 , -C(-R) 2 -C(-R) 2 -, -C(-R)=C(-R)-, >S, >Si(-R) 2 ,>S(=O) 2 or >Se.

[0018] [9] The polycyclic aromatic compound according to [1], or a multimer thereof, represented by any one of formula (1-1), formula (1-3), formula (1-21), formula (1-23), formula (1-41), formula (1-61), formula (1-83), and formula (1-103). [ka]

[0019]

[10] A material for an organic device, comprising the polycyclic aromatic compound or a multimer thereof according to any one of [1] to [9].

[11] The material for an organic device according to

[10] , which is a material for an organic electroluminescent element, a material for an organic field effect transistor, or a material for an organic thin-film solar cell.

[12] The material for an organic device according to

[11] , wherein the material for an organic electroluminescent element is a material for a light-emitting layer.

[13] An organic electroluminescence device comprising a pair of electrodes consisting of an anode and a cathode, and an organic layer disposed between the pair of electrodes and containing the polycyclic aromatic compound or a multimer thereof according to any one of [1] to [9].

[14] An organic electroluminescence device comprising a pair of electrodes consisting of an anode and a cathode, and a light-emitting layer disposed between the pair of electrodes and containing the polycyclic aromatic compound or a multimer thereof according to any one of [1] to [9].

[15] The organic electroluminescent device according to

[14] , wherein the light-emitting layer contains a host and the polycyclic aromatic compound or a polymer thereof as a dopant.

[16] The organic electroluminescent device according to

[15] , wherein the host is an anthracene-based compound, a fluorene-based compound or a dibenzochrysene-based compound.

[0020]

[17] The organic electroluminescence device according to any one of

[14] to

[16] , further comprising an electron transport layer and / or an electron injection layer disposed between the cathode and the light-emitting layer, wherein at least one of the electron transport layer and the electron injection layer contains at least one selected from the group consisting of borane derivatives, pyridine derivatives, fluoranthene derivatives, BO-based derivatives, anthracene derivatives, benzofluorene derivatives, phosphine oxide derivatives, pyrimidine derivatives, arylnitrile derivatives, triazine derivatives, benzimidazole derivatives, phenanthroline derivatives, quinolinol-based metal complexes, thiazole derivatives, benzothiazole derivatives, silole derivatives and azoline derivatives.

[18] The organic electroluminescent device according to

[17] , wherein the electron transport layer and / or the electron injection layer further contains at least one selected from the group consisting of an alkali metal, an alkaline earth metal, a rare earth metal, an oxide of an alkali metal, a halide of an alkali metal, an oxide of an alkaline earth metal, a halide of an alkaline earth metal, an oxide of a rare earth metal, a halide of a rare earth metal, an organic complex of an alkali metal, an organic complex of an alkaline earth metal, and an organic complex of a rare earth metal.

[19] A display device comprising the organic electroluminescent device according to any one of

[13] to

[18] .

[20] A lighting device comprising the organic electroluminescent element according to any one of

[13] to

[18] . Effect of the Invention

[0021] The present invention provides a novel polycyclic aromatic compound or a multimer thereof. The polycyclic aromatic compound or a multimer thereof can be used as a material for organic devices, such as a material for an organic EL device. By using the polycyclic aromatic compound or a multimer thereof of the present invention as a material for an organic EL device, an organic EL device having excellent luminous efficiency and device life can be provided. [Brief description of the drawings]

[0022] [Figure 1] FIG. 1 is a schematic cross-sectional view showing an organic EL element according to an embodiment of the present invention. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0023] 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)".

[0024] 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.

[0025] 1. Polycyclic aromatic compounds and their polymers The polycyclic aromatic compound of the present invention is a compound in which a spiro structure is introduced into the basic skeleton of a polycyclic aromatic compound in which aromatic rings are linked by hetero elements such as boron, phosphorus, oxygen, nitrogen, and sulfur. The inventors have demonstrated that the basic skeleton of such polycyclic aromatic compounds has a large HOMO-LUMO gap (band gap in a thin film, Eg) and a high triplet excitation energy (E T) which is believed to be due to the fact that the six-membered ring containing a heteroatom has low aromaticity, which suppresses the decrease in the HOMO-LUMO gap accompanying the expansion of the conjugated system, and that the SOMO1 and SOMO2 in the triplet excited state (T1) are localized due to electronic perturbation of the heteroatom. In addition, polycyclic aromatic compounds having the above basic skeleton portion have a small energy difference between the triplet excited state (T1) and the singlet excited state (S1) and exhibit thermally activated delayed fluorescence, as a result of the small exchange interaction between the two orbitals due to the localization of SOMO1 and SOMO2 in the triplet excited state (T1). As a result, the compounds are also useful as fluorescent materials for organic electroluminescence (EL) devices, including those that utilize thermally activated delayed fluorescence, as they exhibit high triplet excitation energy (E T Materials having the above structure are also useful as electron transport layers or hole transport layers in phosphorescent organic EL devices or organic EL devices that use thermally activated delayed fluorescence. Furthermore, by introducing a substituent into the basic skeleton of these polycyclic aromatic compounds, the HOMO and LUMO energies can be arbitrarily adjusted, making it possible to optimize the ionization potential and electron affinity according to the surrounding materials.

[0026] In addition to the characteristics of the basic skeleton portion, the polycyclic aromatic compound of the present invention has a spiro structure, which suppresses concentration quenching, and is expected to improve the element life and luminous efficiency. The element life and luminous efficiency are important characteristic values ​​of organic devices, and the use of the polycyclic aromatic compound of the present invention is expected to have an effect of improving the characteristics of the device. In addition, a decrease in melting point and sublimation temperature can be expected. This means that in sublimation purification, which is almost essential as a purification method for materials for organic devices such as organic EL elements that require high purity, purification can be performed at a relatively low temperature, so that thermal decomposition of the material can be avoided. This is also true for the vacuum deposition process, which is a powerful means for producing organic devices such as organic EL elements, and since the process can be performed at a relatively low temperature, thermal decomposition of the material can be avoided, and as a result, a high-performance organic device can be obtained. In addition, since many of the multimers of polycyclic aromatic compounds have a high sublimation temperature due to their molecular weight and high planarity, the reduction in sublimation temperature by introducing a spiro structure becomes more effective. In addition, since the solubility in organic solvents is improved by the introduction of the spiro structure, it becomes possible to apply it to the production of elements using a coating process. However, the present invention is not particularly limited to these principles.

[0027] The polycyclic aromatic compound or multimer of the present invention is a polycyclic aromatic compound represented by the following formula (1), or a multimer of a polycyclic aromatic compound having a plurality of structures represented by the following formula (1).

[0028] [ka]

[0029] In formula (1), X 1 At least one of the above is a group represented by formula (1a). The group represented by formula (1a) is bonded to ring A and ring B, or ring A and ring C of formula (1) at two *.

[0030] The polycyclic aromatic compound represented by formula (1) or a multimer of a polycyclic aromatic compound having a plurality of structures represented by the following formula (1) is preferably a polycyclic aromatic compound represented by formula (2) or a multimer of a polycyclic aromatic compound having a plurality of structures represented by formula (2).

[0031] [ka]

[0032] In formula (2), X 1 At least one of the above is a group represented by formula (2a). The group represented by formula (2a) is bonded to the a ring and the b ring, or the a ring and the c ring of formula (2) at two *.

[0033] The A ring, the B ring, and the C ring in formula (1) are each independently the a ring and its substituent R in formula (2). 1 ~R 3 , ring b and its substituent R 8 ~R 11 , and ring c and its substituent R 4 ~R 7 The D ring and the E ring in formula (1a) correspond to the d ring and its substituent R in formula (2a), respectively. 16 ~R 19 , and the e ring and its substituent R 12 ~R 15 That is, formula (2) corresponds to a structure in which "rings A to E having 6 members" are selected as rings A to E of formula (1). In that sense, each ring in formula (2) is represented by lowercase letters a to e.

[0034] In formula (1) and formula (1a), ring A, ring B, ring C, ring D and ring E are each independently an aryl ring or a heteroaryl ring, and at least one hydrogen atom in these rings may be substituted. The substituent is preferably 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 (an amino having an aryl and a heteroaryl), 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, or a substituted silyl. In the case where these groups have a substituent, examples of the substituent include an aryl, a heteroaryl, an alkyl, or a cycloalkyl. In addition, the aryl ring or the heteroaryl ring may be selected from the group consisting of Y 1 , and two X's 1 It is preferred that the formula (1) comprises a 5- or 6-membered ring sharing a bond with the central fused two-ring structure.

[0035] Here, the "fused two-ring structure" refers to the Y 1 and two X's 1 means a structure in which two saturated hydrocarbon rings are fused together. In addition, the term "six-membered ring sharing a bond with the fused two-ring structure" means, for example, an a-ring (benzene ring (six-membered ring)) fused to the fused two-ring structure as shown in the above formula (2). In addition, the term "an aryl ring or heteroaryl ring (A-ring) has this six-membered ring" means that the A-ring is formed only from this six-membered ring, or that the A-ring is formed by further condensing other rings to this six-membered ring so as to include this six-membered ring. In other words, the term "an aryl ring or heteroaryl ring (A-ring) having a six-membered ring" means that the six-membered ring constituting all or part of the A-ring is fused to the fused two-ring structure. The same explanation applies to "B-ring (b-ring)", "C-ring (c-ring)", and "five-membered ring".

[0036] In the formula (2) and the formula (2a), the substituents R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 , R 15 , R 16 , R 17 , R 18 , and R 19 Adjacent groups among may be bonded to each other to form an aryl ring or a heteroaryl ring together with the a ring, the b ring, the c ring, the d ring, or the e ring, and at least one hydrogen atom in the formed ring may be substituted with an aryl, a heteroaryl, a diarylamino, a diheteroarylamino, an arylheteroarylamino, a diarylboryl (two aryls may be bonded via a single bond or a linking group), an alkyl, a cycloalkyl, an alkoxy, an aryloxy, a trialkylsilyl, a tricycloalkylsilyl, a dialkylcycloalkylsilyl, or an alkyldicycloalkylsilyl, and at least one hydrogen atom in these may be substituted with an aryl, a heteroaryl, an alkyl, or a cycloalkyl. Therefore, the polycyclic aromatic compound represented by formula (2) has a ring structure that constitutes the compound that changes as shown in the following formulas (2-1) and (2-2) depending on the mutual bonding form of the substituents in the a ring, the b ring, the c ring, the d ring, and the e ring. The A' ring, the B' ring, and the C' ring in each formula correspond to the A ring, the B ring, and the C ring in formula (1), respectively.

[0037] [ka]

[0038] The A' ring, B' ring and C' ring in the above formula (2-1) and formula (2-2) are each independently a substituent R1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , and R 11 Adjacent groups among these are bonded to each other to form an aryl or heteroaryl ring together with the ring a, ring b, and ring c, respectively (they may also be considered as condensed rings formed by condensing other ring structures to the ring a, ring b, or ring c). Although not shown in the formula, there are also compounds in which the ring a, ring b, and ring c are all changed to ring A', ring B', and ring C'. As can be seen from the above formulas (2-1) and (2-2), for example, R in ring b 8 and R in c-ring 7 , R in ring b 11 and a-ring R 1 , R in ring c 4 and a-ring R 3 etc. are not considered to be "adjacent groups" and are not bonded to each other. In other words, "adjacent groups" refers to groups adjacent to each other on the same ring.

[0039] The compounds represented by the above formula (2-1) or formula (2-2) are compounds having ring A' (or ring B' or ring C') formed by condensing a benzene ring, which is ring a (or ring b or ring c), with a benzene ring, an indole ring, a pyrrole ring, a furan ring, a thiophene ring, a benzofuran ring, a benzothiophene ring, a cyclopentadiene ring, or an indene ring, and the condensed ring A' (or condensed ring B' or condensed ring C') thus formed is a naphthalene ring, a carbazole ring, an indole ring, a benzofuran ring, a benzothiophene ring, a dibenzofuran ring, a dibenzothiophene ring, an indene ring, or a fluorene ring, respectively.

[0040] Y in formula (1) 1is B, P, P=O, P=S, Al, Ga, As, Si-R or Ge-R, and R of the Si-R and Ge-R is an optionally substituted aryl, an optionally substituted alkyl or an optionally substituted cycloalkyl. In the case of P=O, P=S, Si-R or Ge-R, the atom bonded to the A ring, the B ring or the C ring is P, Si or Ge. Y 1 is preferably B, P, P=O, P=S or Si-R, and particularly preferably B.

[0041] X in formula (1) 1 is a group represented by formula (1a), >O, >NR, >C(-R) 2 , >S, >Si(-R) 2 ,>S(=O) 2 or >Se, and at least one is a group represented by formula (1a). 1 is a group represented by formula (1a) on one side and >O, >NR, >C(-R) 2 , >S, >Si(-R) 2 ,>S(=O) 2 Or >Se. This explanation is based on X in formula (2). 1 That is, it is preferable that formula (1) is the following formula (1-A), and it is preferable that formula (2) is the following formula (2-A).

[0042] [ka]

[0043] In formula (1-A), ring A, ring B, ring C, ring D and ring E have the same meanings as ring A, ring B, ring C, ring D and ring E in formula (1), respectively, and the preferred ranges are also the same. 1 is Y in formula (1). 1 The same definition and preferred range are also the same. X 2 is X in formula (1a) 2 The same definition and preferred range are also the same. X 1A are >O, >NR, >C(-R) 2 , >S, >Si(-R) 2 ,>S(=O)2 or >Se. R of the >NR is an optionally substituted aryl, an optionally substituted heteroaryl, an optionally substituted alkyl or an optionally substituted cycloalkyl. The Si-R, Ge-R, >C(-R) 2 , -C(-R) 2 -C(-R) 2 -, -C(-R)=C(-R)- and >Si(-R) 2 R is hydrogen, optionally substituted aryl, optionally substituted alkyl, or optionally substituted cycloalkyl.

[0044] [ka]

[0045] In formula (2-A), Y 1 is Y in formula (1). 1 The same definition and preferred range are also the same. X 2 is X in formula (1a) 2 The same definition and preferred range are also the same. X 1A is X in formula (1-A). 1A The same definition and preferred range are also the same. 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 , R 15 , R 16 , R 17 , R 18 , and R 19 are R in Eq. (2), 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 , R 15 , R 16 , R 17 , R 18 , and R 19 The same definition and preferred range are also the same.

[0046] X in formula (1) 1 is preferably a group represented by formula (1a) and the other is >O or >NR, and particularly preferably a group represented by formula (1a) and the other is >NR. This explanation is applicable to X in formula (2). 1 That is, in each of formulas (1-A) and (2-A), X 1A is preferably >O or >NR, more preferably >NR.

[0047] X in formula (1a) 2 is a single bond, >O, >NR, >C(-R) 2 , -C(-R) 2 -C(-R) 2 -, -C(-R)=C(-R)-, >S, >Si(-R) 2 ,>S(=O) 2 Or >Se. X 2 is preferably a single bond, >O, or >NR, and is particularly preferably a single bond. 1 When one of the groups is a group represented by formula (1a) and the other is >NR, X 2 is preferably a single bond, >O, or >NR, and is particularly preferably a single bond. 2 But it's the same.

[0048] From the viewpoint of ease of synthesis, formula (1a) is preferably a group having a symmetric structure that does not cause stereoisomerism in the compound represented by formula (1). Similarly, from the viewpoint of ease of synthesis, formula (2a) is preferably a group having a symmetric structure that does not cause stereoisomerism in the compound represented by formula (2). On the other hand, from the viewpoint of the light-emitting properties of the element, it may be a group having an asymmetric structure that causes stereoisomers, and the stereoisomers may be used separately or mixed. It is sufficient to use a stereoisomer ratio suited to the application.

[0049] X in formula (1) 1 and X in formula (1a) 2 In the above, R of >NR is (when multiple >NRs are present, each is independently) an optionally substituted aryl, an optionally substituted heteroaryl, an optionally substituted alkyl, or an optionally substituted cycloalkyl, and the above >C(-R) 2 , -C(-R) 2 -C(-R) 2 -, -C(-R)=C(-R)- and >Si(-R) 2 R is (when more than one is present, each independently) hydrogen, optionally substituted aryl, optionally substituted alkyl or optionally substituted cycloalkyl, and the above >NR, >C(-R) 2 , -C(-R) 2 -C(-R) 2 -, -C(-R)=C(-R)- and >Si(-R) 2 R may be bonded to at least one ring selected from the group consisting of ring A, ring B, ring C, ring D and ring E through a linking group or a single bond, and the linking group is -O-, -S- or -C(-R) 2 In addition, the above-mentioned "-C(-R) 2 R in "-" is hydrogen, alkyl or cycloalkyl. This explanation applies to X in formula (2) and formula (2a). 1 and X 2 But it's the same.

[0050] Here, in formula (1), "the above-mentioned >NR, >C(-R) 2, -C(-R) 2 -C(-R) 2 In formula (2), the provision that "R in -, -C(-R)=C(-R)- is bonded to at least one ring selected from the group consisting of the ring A, the ring B, the ring C, the ring D and the ring E through a linking group or a single bond" is understood to mean "the above-mentioned >NR, >C(-R) 2 , -C(-R) 2 -C(-R) 2 -, -C(-R)=C(-R)-, R is -O-, -S-, -C(-R) 2 - or a single bond to at least one ring selected from the group consisting of ring a, ring b, ring c, ring d and ring e."

[0051] Above >NR, >C(-R) 2 , -C(-R) 2 -C(-R) 2 -, -C(-R)=C(-R)- and >Si(-R) 2 Preferred examples of R bonded to at least one ring selected from the group consisting of ring A, ring B, ring C, ring D and ring E through a linking group or a single bond include X 1 >NR, >C(-R) in 2 , and >Si(-R) 2 In the formula (2), R is bonded to at least one ring selected from the group consisting of ring A, ring B, and ring C through a linking group or a single bond. 1 >NR, >C(-R) in 2 , and >Si(-R) 2 In the above, R is bonded to at least one ring selected from the group consisting of ring a, ring b, and ring c through a linking group or a single bond. 1 In the above formula, R in >NR is bonded to at least one ring selected from the group consisting of ring A, ring B, and ring C via a linking group or a single bond.

[0052] In addition, the above provision is expressed by the following formula (2-3-1), X 1and a compound having a ring structure in which X is incorporated into a condensed ring C', and 1 In other words, for example, the compound having X in the benzene ring, which is the c ring in formula (2), 1 The compound has a ring C' formed by condensing another ring so as to incorporate the ring C'. The condensed ring C' formed is, for example, a carbazole ring, a phenoxazine ring, a phenothiazine ring, or an acridine ring.

[0053] [ka]

[0054] The "aryl ring" which is the ring A, ring B, ring C, ring D and ring E in formula (1) can be, for example, an aryl ring having 6 to 30 carbon atoms, preferably an aryl ring having 6 to 16 carbon atoms, more preferably an aryl ring having 6 to 12 carbon atoms, and particularly preferably an aryl ring having 6 to 10 carbon atoms. The "aryl ring" can be defined as "R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 , R 15 , R 16 , R 17 , R 18 , and R 19 In addition, since ring a (or ring b, ring c, ring d, or ring e) is already composed of a benzene ring having six carbon atoms, the lower limit of the carbon number is the total carbon number of the fused rings formed by condensing a 5-membered ring to this, which is nine.

[0055] Specific examples of the "aryl ring" include a monocyclic benzene ring, a bicyclic bicyclic bicyclic naphthalene ring and an indene ring, a tricyclic terphenyl ring (m-terphenyl, o-terphenyl, p-terphenyl), a fused tricyclic acenaphthylene ring, a fluorene ring, a phenalene ring, and a phenanthrene ring, a fused tetracyclic triphenylene ring, a pyrene ring, and a naphthacene ring, and a fused pentacyclic perylene ring and a pentacene ring. Both ring D and ring E are preferably benzene rings which may have a substituent, and more preferably unsubstituted benzene rings.

[0056] Examples of the "heteroaryl ring" which is the 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, in addition to carbon, 1 to 5 heteroatoms selected from oxygen, sulfur and nitrogen as ring-constituting atoms. The "heteroaryl ring" is defined as "R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 , R 15 , R 16 , R 17 , R 18 , and R 19In addition, since ring a (or ring b, ring c, ring d, or ring e) is already composed of a benzene ring having 6 carbon atoms, the lower limit of the carbon number is the total carbon number of the fused rings fused to this 5-membered ring, which is 6.

[0057] 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-benzotriazo Examples of such rings include an isoquinol ring, a quinoline ring, an isoquinoline ring, a cinnoline ring, a quinazoline ring, a quinoxaline ring, a phthalazine ring, a naphthyridine ring, a purine ring, a pteridine ring, a carbazole ring, an acridine ring, a phenoxathiin ring, a phenoxazine ring, a phenothiazine ring, a phenazine ring, a phenazasiline ring, an indolizine ring, a furan ring, a benzofuran ring, an isobenzofuran ring, a dibenzofuran ring, a thiophene ring, a benzothiophene ring, a dibenzothiophene ring, a furazan ring, and a thianthrene ring.

[0058] In addition, when the "aryl ring" and the "heteroaryl ring" are fused rings in which two or more rings are fused, any of the rings may share a bond with the above-mentioned fused two-ring structure, but the ring sharing a bond with the fused two-ring structure is preferably a 5-membered or 6-membered ring as described above. That is, for example, in the formula (2), R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , and R 11When adjacent groups among the above are bonded to each other to form an aryl ring or heteroaryl ring together with the a ring, the b ring, or the c ring, the fused two-ring structure shares a bond with the 6-membered benzene ring, which is preferred. In addition, for example, it is also preferred that the indole ring, the benzofuran ring, and the benzothiophene ring share a bond with the fused two-ring structure with the 5-membered pyrrole ring, the furan ring, and the thiophene ring, respectively. Examples of such structures include compounds represented by any of the following formulas (1-412) to (1-419), which have a structure corresponding to the structure in which the benzene ring, which is the c ring (or the b ring), in formula (2) becomes a benzofuran ring or a benzothiophene ring.

[0059] At least one hydrogen atom in the above "aryl ring" or "heteroaryl ring" may be substituted. The number of substitutions is not particularly limited, but the total number of hydrogen atoms substituted in ring A, ring B, ring C, ring D and ring E is preferably 0 to 10, more preferably 0 to 5, further preferably 0 to 3, and particularly preferably 0 to 2. In each of ring A, ring B, ring C, ring D and ring E, it is preferable that 0 to 2 hydrogen atoms of the aryl ring or heteroaryl ring are substituted, and more preferably 0 to 1 hydrogen atom is substituted.

[0060] From the viewpoint of physical properties such as reducing intermolecular interactions and improving efficiency and lifetime during device fabrication, it is preferable that at least one hydrogen atom of the aryl ring or heteroaryl ring in at least one of ring A, ring B, ring C, ring D, or ring E is substituted. From the viewpoints of both synthesis and physical properties, it is preferable that 0 to 1 hydrogen atom in the aryl or heteroaryl ring is substituted in any of the A ring, B ring, C ring, D ring and E ring; It is more preferable that 0 to 1 hydrogen atom in the aryl or heteroaryl ring in any of rings A, B and C is substituted, and that the aryl or heteroaryl ring in rings D and E is unsubstituted.

[0061] Substituents when at least one hydrogen atom in an "aryl ring" or a "heteroaryl ring" is replaced include the 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 (the 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", or a substituted "silyl".

[0062] Examples of the "aryl" or "heteroaryl" as the first substituent include the aryl of "diarylamino", the heteroaryl of "diheteroarylamino", the aryl and heteroaryl of "arylheteroarylamino", the aryl of "diarylboryl", and the aryl of "aryloxy" include the monovalent groups of the "aryl ring" or "heteroaryl ring" described above.

[0063] The "alkyl" as the first substituent may be either linear or branched, and examples thereof include linear alkyl having 1 to 24 carbon atoms or branched alkyl having 3 to 24 carbon atoms. An alkyl having 1 to 18 carbon atoms (branched alkyl having 3 to 18 carbon atoms) is preferred, an alkyl having 1 to 12 carbon atoms (branched alkyl having 3 to 12 carbon atoms) is more preferred, an alkyl having 1 to 6 carbon atoms (branched alkyl having 3 to 6 carbon atoms) is even more preferred, and an alkyl having 1 to 4 carbon atoms (branched alkyl having 3 to 4 carbon atoms) is particularly preferred.

[0064] 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, and 1-methylheptyl. Examples of the aryl group include aryl, 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.

[0065] Furthermore, 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.

[0066] Specific examples of cycloalkyl include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, and alkyl (particularly methyl) substituted derivatives of these having 1 to 4 carbon atoms, as well as norbornenyl, bicyclo[1.0.1]butyl, bicyclo[1.1.1]pentyl, bicyclo[2.0.1]pentyl, bicyclo[1.2.1]hexyl, bicyclo[3.0.1]hexyl, bicyclo[2.1.2]heptyl, bicyclo[2.2.2]octyl, adamantyl, diamantyl, decahydronaphthalenyl, and decahydroazulenyl.

[0067] 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 4 carbon atoms (branched alkoxy having 3 to 4 carbon atoms) is particularly preferred.

[0068] Specific alkoxy includes methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, s-butoxy, t-butoxy, pentyloxy, hexyloxy, heptyloxy, octyloxy, and the like.

[0069] The "substituted silyl" as the first substituent may be a silyl substituted with three selected from the group consisting of alkyl, cycloalkyl, and aryl. Examples of the "substituted silyl" include trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, alkyldicycloalkylsilyl, triarylsilyl, dialkylarylsilyl, and alkyldiarylsilyl.

[0070] The "trialkylsilyl" includes a group in which three hydrogen atoms in a silyl group are each independently substituted with an alkyl, and the alkyl can be cited from the groups described as the "alkyl" in the first substituent above. The alkyl to be substituted is preferably an alkyl having 1 to 4 carbon atoms, and specific examples thereof include methyl, ethyl, propyl, i-propyl, butyl, sec-butyl, t-butyl, and cyclobutyl.

[0071] Specific examples of trialkylsilyl include trimethylsilyl, triethylsilyl, tripropylsilyl, tri-i-propylsilyl, tributylsilyl, tri-sec-butylsilyl, tri-t-butylsilyl, ethyldimethylsilyl, propyldimethylsilyl, i-propyldimethylsilyl, butyldimethylsilyl, sec-butyldimethylsilyl, t-butyldimethylsilyl, methyldiethylsilyl, propyldiethylsilyl, i-propyldiethylsilyl, butyldiethylsilyl, sec-butyldiethylsilyl, t-butyldiethylsilyl, methyldipropylsilyl, ethyldipropylsilyl, butyldipropylsilyl, sec-butyldipropylsilyl, t-butyldipropylsilyl, methyldi-i-propylsilyl, ethyldi-i-propylsilyl, butyldi-i-propylsilyl, sec-butyldi-i-propylsilyl, and t-butyldi-i-propylsilyl.

[0072] Examples of "tricycloalkylsilyl" include groups in which three hydrogen atoms in a silyl group are each independently substituted with a cycloalkyl, and the cycloalkyl can be cited as the group described as the "cycloalkyl" in the first substituent above. Preferred cycloalkyl groups for substitution are cycloalkyl groups having 5 to 10 carbon atoms, specifically cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, bicyclo[1.1.1]pentyl, bicyclo[2.0.1]pentyl, bicyclo[1.2.1]hexyl, bicyclo[3.0.1]hexyl, bicyclo[2.1.2]heptyl, bicyclo[2.2.2]octyl, adamantyl, decahydronaphthalenyl, and decahydroazulenyl.

[0073] Specific examples of tricycloalkylsilyl include tricyclopentylsilyl and tricyclohexylsilyl.

[0074] 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.

[0075] Specific examples of dialkylarylsilyl substituted with two alkyls and one aryl, alkyldiarylsilyl substituted with one alkyl and two aryls, and triarylsilyl substituted with three aryls include silyl substituted with a group selected from the above-mentioned specific alkyls and aryls. Specific examples of triarylsilyl include triphenylsilyl.

[0076] The "aryl" in the first substituent "diarylboryl" can be quoted from the above description of the aryl. In addition, the two aryls are not bound 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.

[0077] As explained above, the first substituent, substituted or unsubstituted "aryl", substituted or unsubstituted "heteroaryl", substituted or unsubstituted "diarylamino", substituted or unsubstituted "diheteroarylamino", substituted or unsubstituted "arylheteroarylamino", substituted or unsubstituted "diarylboryl (two aryls may be bonded via a single bond or a linking group)", substituted or unsubstituted "alkyl", substituted or unsubstituted "cycloalkyl", substituted or unsubstituted "alkoxy", substituted or unsubstituted "aryloxy", or substituted "silyl" may have at least one hydrogen atom substituted with a second substituent. Examples of the second substituent include aryl, heteroaryl, alkyl, or cycloalkyl, and specific examples thereof can be found in the above-mentioned explanation of the monovalent group of the "aryl ring" or "heteroaryl ring", and the explanation of the "alkyl" or "cycloalkyl" as the first substituent. The aryl and heteroaryl as the second substituent also include structures in which at least one hydrogen atom in the aryl and heteroaryl as the second substituent is substituted with an aryl such as phenyl (specific examples are the groups mentioned above), an alkyl such as methyl (specific examples are the groups mentioned above), or a cycloalkyl such as cyclohexyl (specific examples are the groups mentioned above). As an example, when the second substituent is carbazolyl, the heteroaryl as the second substituent also includes a carbazolyl in which at least one hydrogen atom at the 9-position is substituted with an aryl such as phenyl, an alkyl such as methyl, or a cycloalkyl such as cyclohexyl.

[0078] R in Equation (2) 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , and R 11 and R in formula (2a) 12 , R 13 , R 14 , R15 , R 16 , R 17 , R 18 , and R 19 The aryl, heteroaryl, aryl of diarylamino, heteroaryl of diheteroarylamino, aryl and heteroaryl of arylheteroarylamino, aryl of diarylboryl, and aryl of aryloxy in the formula (1) include the monovalent groups of "aryl ring" or "heteroaryl ring" described in formula (1). 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 , R 15 , R 16 , R 17 , R 18 , and R 19 For the alkyl, cycloalkyl, or alkoxy in R, the explanation of "alkyl," "cycloalkyl," or "alkoxy" as the first substituent in the explanation of formula (1) above can be referred to. Furthermore, the same applies to aryl, heteroaryl, alkyl, or cycloalkyl as substituents to these groups. 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , and R 11When adjacent groups among these are bonded to form an aryl ring or heteroaryl ring together with ring a, ring b or ring c, the same applies to the heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl (the two aryls may be bonded via a single bond or a linking group), alkyl, cycloalkyl, alkoxy or aryloxy as substituents on these rings, and the aryl, heteroaryl, alkyl or cycloalkyl as further substituents.

[0079] Specifically, the emission wavelength can be adjusted by the steric hindrance, electron donating property and electron withdrawing property of the structure of the first substituent, and the first substituent is preferably a group represented by the following structural formula, and more preferably, methyl, t-butyl, t-pentyl (t-amyl), 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, 3,6-dimethylcarbazolyl, 3,6-di-t-butylcarbazolyl and phenoxy are more preferred, and methyl, t-butyl, t-pentyl (t-amyl), 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 are more preferred. From the viewpoint of ease of synthesis, larger steric hindrance is preferred for selective synthesis, and specifically, t-butyl, t-pentyl (t-amyl), 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.

[0080] 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.

[0081] [ka]

[0082] [ka]

[0083] [ka]

[0084] In formula (2), R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , and R 11 Of these, it is preferred that 0 to 3 are groups represented by any one of the structural formulas above, and the remainder are hydrogen. 1 , R 2 , and R 3 Of these, 0 to 1 are a group represented by any one of the structural formulas above, and the rest are hydrogen; R 4 , R 5 , R 6 , and R 7 of which 0 to 1 are a group represented by any one of the structural formulas above, and the remainder are hydrogen, and R 8 , R 9 , R 10 , and R 11 It is preferable that 0 to 1 of R is a group represented by any one of the structural formulas above, and the rest are hydrogen. 1 , R 2 , and R 3 are all hydrogen or R 1 and R 3 are hydrogen, and R 2 It is more preferable that the group is represented by any one of the above structural formulas.

[0085] In addition, R in formula (2a) 12 , R 13 , R 14 , R 15 , R 16 , R 17 , R 18 , and R 19 It is preferable that any one to four of R are a group represented by any one of the structural formulas above, and the remainder are hydrogen; R 12 , R 13 , R 14 , and R 15 Among these, 0 to 2 are groups represented by any one of the structural formulas above, and the remainder are hydrogen, and R 16 , R 17 , R 18 , and R 19 It is more preferable that one or two of R are groups represented by any one of the structural formulas above, and the rest are hydrogen. 12 , R 13 , R 14 , R 15 , R 16 , R 17 , R 18 , and R 19 It is also preferred that both are hydrogen.

[0086] X in formula (1) 1 and X in formula (1a) 2 In the formula (2), R in >NR is an aryl, heteroaryl, alkyl or cycloalkyl which may be substituted with the second substituent described above, and at least one hydrogen in the aryl, heteroaryl, alkyl or cycloalkyl may be substituted with, for example, an alkyl or cycloalkyl. Examples of the aryl, heteroaryl, alkyl or cycloalkyl include the groups described above. In particular, an aryl having 6 to 10 carbon atoms (e.g., phenyl, naphthyl, etc.), a heteroaryl having 2 to 15 carbon atoms (e.g., carbazolyl, etc.), an alkyl having 1 to 5 carbon atoms (e.g., methyl, ethyl, etc.) or a cycloalkyl having 5 to 10 carbon atoms (preferably cyclohexyl or adamantyl) is preferred. This explanation is given in relation to X in formula (2). 1 and X in formula (2a) 2But it's the same.

[0087] X in formula (1) 1 and Y 1 and X in formula (1a) 2 Si-R in formula (1), Y in formula (1) 1 Ge-R in the formula (1), X 1 and X in formula (1a) 2 >C(-R) in 2 , -C(-R) 2 -C(-R) 2 R in - and -C(-R)=C(-R)- is hydrogen, an aryl, an alkyl or a cycloalkyl which may be substituted with the second substituent described above, and at least one hydrogen in the aryl may be substituted with, for example, an alkyl. Examples of the aryl, alkyl or cycloalkyl include the groups described above. In particular, an aryl having 6 to 10 carbon atoms (e.g., phenyl, naphthyl, etc.), an alkyl having 1 to 5 carbon atoms (e.g., methyl, ethyl, etc.) or a cycloalkyl having 5 to 10 carbon atoms (preferably cyclohexyl or adamantyl) is preferred. This explanation is given in relation to X in formula (2). 1 and Y 1 and X in formula (2a) 2 But it's the same.

[0088] The linking group in formula (1) is "-C(-R) 2 R in "-" is hydrogen, alkyl or cycloalkyl, and examples of the alkyl or cycloalkyl include the groups described above. In particular, alkyl having 1 to 4 carbon atoms (e.g., methyl, ethyl, etc.) or cycloalkyl having 5 to 10 carbon atoms (preferably cyclohexyl or adamantyl) is preferred. This explanation is based on the linking group "-C(-R)" in formula (2). 2 -" is also the same.

[0089] The compound of the present invention may be a multimer of a polycyclic aromatic compound having a plurality of unit structures represented by formula (1), and preferably a multimer of a polycyclic aromatic compound having a plurality of unit structures represented by formula (2). The multimer is preferably a dimer to hexamer, more preferably a dimer to trimer, and particularly preferably a dimer. The multimer may have a form having a plurality of the above unit structures in one compound. For example, in addition to a form in which a plurality of the above unit structures are bonded together via a linking group such as a single bond, an alkylene having 1 to 3 carbon atoms, phenylene, or naphthylene (linked multimer), the multimer may have a form in which any ring (ring A, ring B or ring C, ring a, ring b or ring c) contained in the above unit structure is bonded together so as to be shared by the plurality of unit structures (ring-shared multimer), or may have a form in which any ring (ring A, ring B or ring C, ring a, ring b or ring c) contained in the above unit structure is bonded together so as to be condensed (ring-condensed multimer). However, ring-shared multimers and ring-condensed multimers are preferred, and ring-shared multimers are more preferred.

[0090] Examples of such a multimer include those represented by the following formula (2-4), formula (2-4-1), formula (2-5-1) to formula (2-5-4), or formula (2-6): 1A multimeric compound in which at least one of the above is a group represented by formula (2a) can be mentioned. The multimeric compound represented by the following formula (2-4) is a multimeric compound (ring-sharing multimer) having a plurality of unit structures represented by formula (2) in one compound, with the benzene ring being the a-ring being shared, as explained in formula (2). The multimeric compound represented by the following formula (2-4-1) is a multimeric compound (ring-sharing multimer) having two unit structures represented by formula (2) in one compound, with the benzene ring being the a-ring being shared, as explained in formula (2). The multimeric compound represented by the following formula (2-4-2) is a multimeric compound (ring-sharing multimer) having three unit structures represented by formula (2) in one compound, with the benzene ring being the a-ring being shared, as explained in formula (2). Moreover, the multimeric compounds represented by the following formulae (2-5-1) to (2-5-4) are multimeric compounds (ring-sharing multimers) having a plurality of unit structures represented by formula (2) in one compound, by sharing a benzene ring, which is the b ring (or c ring), when explained by formula (2). Moreover, the multimeric compound represented by the following formula (2-6) is a multimeric compound (ring-condensed multimer) having a plurality of unit structures represented by formula (2) in one compound, by condensing a benzene ring, which is the b ring (or a ring, c ring) of a certain unit structure, with a benzene ring, which is the b ring (or a ring, c ring) of a certain unit structure.

[0091] [ka]

[0092] The multimeric compound may be a multimer in which a multimerization form represented by formula (2-4) or formula (2-4-1) is combined with a multimerization form represented by any one of formulas (2-5-1) to (2-5-4) or formula (2-6), a multimer in which a multimerization form represented by any one of formulas (2-5-1) to (2-5-4) is combined with a multimerization form represented by formula (2-6), or a multimer in which a multimerization form represented by formula (2-4) or formula (2-4-1), a multimerization form represented by any one of formulas (2-5-1) to (2-5-4), and a multimerization form represented by formula (2-6).

[0093] In addition, at least one selected from the group consisting of aryl rings and heteroaryl rings in the chemical structure of the polycyclic aromatic compound represented by formula (1) and a multimer thereof (preferably the polycyclic aromatic compound represented by formula (2) and a multimer thereof) may be condensed with at least one cycloalkane.

[0094] For example, aryl and heteroaryl rings which are ring A, ring B, ring C, ring a, ring b and ring c, aryl (aryl moiety in aryl, diarylamino, arylheteroarylamino, diarylboryl or aryloxy) and heteroaryl (heteroaryl moiety in heteroaryl, diheteroarylamino or arylheteroarylamino) as the first and second substituents on ring A to ring C, aryl (similar to above) and heteroaryl (similar to above) as the first and second substituents on ring a to ring c, Y 1 Aryl as R in Si-R and Ge-R (as above), and X 1 and X 2 >NR and >C(-R) 2 At least one of the aryl (as above) and heteroaryl (as above) as R in the formula (I) may be fused with at least one cycloalkane.

[0095] Preferably, the aryl and heteroaryl rings are ring A, ring B, ring C, ring a, ring b and ring c, the aryl (aryl moiety in aryl, diarylamino, diarylboryl or aryloxy) and the heteroaryl (heteroaryl moiety in heteroaryl or diheteroarylamino) as the first substituents on ring A to ring C, the aryl (similar to above) and the heteroaryl (similar to above) as the first substituents on ring a to ring c, and X 1 and X 2 >NR and >C(-R) 2 At least one of the aryl (as above) and heteroaryl (as above) as R is fused with at least one cycloalkane.

[0096] More preferably, the aryl rings are ring A, ring B, ring C, ring a, ring b and ring c, the aryl (aryl moiety in aryl or diarylamino) and the heteroaryl (heteroaryl moiety in heteroaryl) as the first substituents on ring A to ring C, the aryl (similar to above) and the heteroaryl (similar to above) as the first substituents on ring a to ring c, and X 1 and X 2 >NR and >C(-R) 2 At least one of the aryls (as above) as R is fused with at least one cycloalkane.

[0097] More preferably, the aryl rings are ring A, ring B, ring C, ring a, ring b and ring c, the aryl as the first substituent on ring A to ring C (aryl or aryl moiety in diarylamino), the aryl as the first substituent on ring a to ring c (similar to the above), and X 1 and X 2 >NR and >C(-R) 2 At least one of the aryls (as above) as R is fused with at least one cycloalkane.

[0098] 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.

[0099] Specific examples of cycloalkanes include cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclooctane, cyclononane, cyclodecane, norbornene, bicyclo[1.0.1]butane, bicyclo[1.1.1]pentane, bicyclo[2.0.1]pentane, bicyclo[1.2.1]hexane, bicyclo[3.0.1]hexane, bicyclo[2.1.2]heptane, bicyclo[2.2.2]octane, adamantane, diamantane, decahydronaphthalene, and decahydroazulene, as well as alkyl (particularly methyl) substituted, halogen (particularly fluorine) substituted, and deuterium substituted derivatives of these having 1 to 4 carbon atoms.

[0100] In addition, all or a part of the hydrogen atoms in the chemical structure of the polycyclic aromatic compound and its multimer represented by formula (1) or (2) may be deuterium, cyano, or halogen. For example, in formula (1), the rings A, B, and C (rings A to C are aryl rings or heteroaryl rings), the substituents on rings A to C, Y 1 is Si-R or Ge-R, R (=alkyl, cycloalkyl, aryl), and X 1 and X 2 >NR or >C(-R) 2 In the above formula, hydrogen atoms in R (=alkyl, cycloalkyl, aryl) may be replaced by deuterium, cyano, or halogen atoms, and among these, examples include embodiments in which all or a part of hydrogen atoms in aryl or heteroaryl are replaced by deuterium, cyano, or halogen atoms. Halogen atoms are fluorine, chlorine, bromine, or iodine, preferably fluorine, chlorine, or bromine, and more preferably fluorine or chlorine.

[0101] The polycyclic aromatic compound and its multimer according to the present invention can be used as a material for an organic device. Examples of the organic device include an organic electroluminescence device, an organic field effect transistor, and an organic thin-film solar cell. In particular, in the organic electroluminescence device, Y is used as a dopant material for the light-emitting layer. 1 B, X 1 one of the groups represented by formula (1a) and the other is >NR, X 2 Compounds in which Y is a single bond 1 B, X 1 one of which is a group represented by formula (1a), and the other is >O, X 2 Compounds in which Y is a single bond 1 B, X 1 one of the groups represented by formula (1a) and the other is >NR, X 2 As a host material for the light-emitting layer, a compound in which Y 1 B, X 1 one of which is a group represented by formula (1a), and the other is >O, X 2 Compounds where Y is >NR 1 B, X 1 one of which is a group represented by formula (1a), and the other is >O, X 2 As the electron transport material, a compound in which Y 1 B, X 1 one of which is a group represented by formula (1a), and the other is >O, X 2 Compounds in which Y is >O 1 P=O, X 1 one of which is a group represented by formula (1a), and the other is >O, X 2 Compounds in which is >O are preferably used.

[0102] Specifically, the compounds include those represented by the following formulae (1-1) to (1-423): In the following structural formulae, "Me" represents methyl, and "D" represents deuterium.

[0103] [ka]

[0104] [ka]

[0105]

change

[0106]

change

[0107]

change

[0108]

change

[0109]

change

[0110]

change

[0111]

change

[0112]

change

[0113]

change

[0114]

change

[0115]

change

[0116]

change

[0117]

change

[0118]

change

[0119]

change

[0120]

change

[0121]

change

[0122]

change

[0123]

change

[0124]

change

[0125]

change

[0126]

change

[0127]

change

[0128]

change

[0129]

change

[0130]

change

[0131]

change

[0132]

change

[0133]

change

[0134]

change

[0135]

change

[0136]

change

[0137]

change

[0138]

change

[0139]

change

[0140]

change

[0141]

change

[0142]

change

[0143]

change

[0144]

change

[0145]

change

[0146]

change

[0147]

change

[0148]

change

[0149]

change

[0150]

change

[0151]

change

[0152]

change

[0153]

change

[0154]

change

[0155]

change

[0156]

change

[0157]

change

[0158] [ka]

[0159] [ka]

[0160] [ka]

[0161] [ka]

[0162] Among these, the compounds represented by formulas (1-1), (1-3), (1-21), (1-23), (1-41), (1-61), (1-83), and (1-103) are preferred, and the compounds represented by formulas (1-1), (1-3), (1-23), (1-83), and (1-103) are more preferred.

[0163] <Method for producing polycyclic aromatic compound represented by formula (1) and its multimer> The method for producing the polycyclic aromatic compound represented by formula (1) and its multimer will be described. Basically, an intermediate is produced by first bonding the A ring (ring a) and the B ring (ring b) to a condensed two-ring structure (first reaction: see schemes (1) and (2)). Next, the A ring (ring a), the C ring (ring c) and the bonding group (X 1 (See the second reaction: scheme (3)). Furthermore, the methoxy is converted to an OTf group (See the third reaction: scheme (4)), and the OTf group is converted to a boronic ester group such as a BPin group to obtain an intermediate compound (See the fourth reaction: scheme (5)). Then, the desired polycyclic aromatic compound can be obtained using a Lewis acid such as aluminum chloride (See the fifth reaction: scheme (6)).

[0164] A detailed description will be given with reference to Schemes 1 to 6. An alcohol is obtained by an addition reaction to a cyclic ketone (Scheme (1)), and then, by a Friedel-Crafts reaction with a B-ring (b-ring) precursor using an acid catalyst, the A-ring (a-ring) and the B-ring (b-ring) can be bonded to a condensed two-ring structure (Scheme (2)).

[0165] [ka]

[0166] In the second reaction, the A ring (a ring) and the C ring (c ring) are bonded to each other by a bonding group (X 1 The bond is formed by a reaction between a group containing X and a halogen atom (Hal). For example, for an etherification reaction, a general reaction such as a nucleophilic substitution reaction or an Ullmann reaction can be used, and for an amination reaction, a general reaction such as the Buchwald-Hartwig reaction can be used (Scheme (3)). 1 When is S or Se, known reactions can be used.

[0167] [ka]

[0168] In the third reaction, methoxy is converted to -OH using boron tribromide or the like, and trifluoromethanesulfonic anhydride (Tf 2 O) to an -OTf group (Scheme 4). Here, the methoxy may be another alkoxy, and the Tf group may be another sulfonic acid group such as a tosyl group.

[0169] [ka]

[0170] In the fourth reaction, the -OTf group is converted to the -Bpin group (Bpin is -B(OH)) by using a palladium catalyst such as the Miyaura reaction. 2The intermediate compound is obtained by converting the boronic acid ester group to a pinacol ester group (Scheme (5)). Here, the boronic acid ester group may be a boronic acid group or an ester group with another alcohol.

[0171] [ka]

[0172] In the fifth reaction, the intermediate compound can be converted to the desired polycyclic aromatic compound using a Lewis acid such as aluminum chloride by the method described in JP 2018-076281 A (Scheme (6)). In this reaction, a base such as diisopropylethylamine (DIPEA) may be added.

[0173] [ka]

[0174] Furthermore, by using a cycloalkane-condensed raw material somewhere in these reaction steps or by adding a step of condensing a cycloalkane, it is possible to produce the compound of the present invention in which the desired position is condensed with a cycloalkane.

[0175] Moreover, polymers can also be produced by appropriately changing the raw materials (Scheme (7)). [ka]

[0176] The Bronsted bases used in the above schemes (1) to (7) include N,N-diisopropylethylamine, triethylamine, 2,2,6,6-tetramethylpiperidine, 1,2,2,6,6-pentamethylpiperidine, N,N-dimethylaniline, N,N-dimethyltoluidine, 2,6-lutidine, sodium tetraphenylborate, potassium tetraphenylborate, triphenylborane, tetraphenylsilane, Ar4 BNa, Ar 4 B.K., Ar 3 B, Ar 4 Si (wherein Ar is aryl such as phenyl).

[0177] The Lewis acid used in the above schemes (1) to (7) is AlCl 3 , AlBr 3 , AlF 3 , B.F. 3 ·OEt 2 , BCl 3 , BBr 3 , GaCl 3 , GaBr 3 , InCl 3 , InBr 3 , In(OTf) 3 , SnCl 4 , SnBr 4 , AgOTf, ScCl 3 , Sc(OTf) 3 , ZnCl 2 , ZnBr 2 , Zn(OTf) 2 , MgCl 2 , MgBr 2 , Mg(OTf) 2 , LiOTf, NaOTf, KOTf, Me 3 SiOTf, Cu(OTf) 2 , CuCl 2 , Y.C.L. 3 , Y(OTf) 3 , TiCl 4 , TiBr 4 , ZrCl 4 , ZrBr 4 , FeCl 3 , FeBr 3 , CoCl 3 , CoBr 3 etc.

[0178] The polycyclic aromatic compound and its multimer of the present invention also include compounds in which at least a portion of hydrogen atoms is substituted with deuterium or cyano, or compounds in which hydrogen atoms are substituted with halogens such as fluorine or chlorine. Such compounds can be synthesized in the same manner as described above by using raw materials in which desired positions are deuterated, cyanated, fluorinated or chlorinated.

[0179] <Polymer compounds, crosslinked polymers, pendant polymer compounds> The polycyclic aromatic compound represented by formula (1) according to the present invention and its multimer 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 crosslinked polymer obtained by further crosslinking the pendant polymer compound (the pendant polymer compound for obtaining this crosslinked pendant polymer has a crosslinkable substituent).

[0180] The reactive substituents mentioned above (including the polymerizable substituents, the crosslinkable substituents, and the reactive substituents for obtaining a pendant polymer, hereinafter also referred to simply as "reactive substituents") are not particularly limited as long as they are substituents capable of increasing the molecular weight of the polycyclic aromatic compound or its multimer, substituents capable of further crosslinking the polymer compound thus obtained, and substituents capable of pendant reaction with the main chain polymer, but are preferably those having the following structures: * in each structural formula indicates a bond position.

[0181] [ka]

[0182] 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.

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

[0184] 2. Organic Devices The polycyclic aromatic compound according to the present invention can be used as a material for an organic device, such as an organic electroluminescent element, an organic field effect transistor, or an organic thin-film solar cell.

[0185] 2-1. Organic electroluminescent device 2-1-1. Structure of organic electroluminescent device FIG. 1 is a schematic cross-sectional view showing an organic EL element according to this embodiment. The organic EL element 100 shown in FIG. 1 has a substrate 101, an anode 102 provided on the substrate 101, a hole injection layer 103 provided on the anode 102, a hole transport layer 104 provided on the hole injection layer 103, an emitting layer 105 provided on the hole transport layer 104, an electron transport layer 106 provided on the emitting layer 105, an electron injection layer 107 provided on the electron transport layer 106, and a cathode 108 provided on the electron injection layer 107.

[0186] The organic EL element 100 may be fabricated in the reverse order, for example, to have a substrate 101, a cathode 108 provided on the substrate 101, an electron injection layer 107 provided on the cathode 108, an electron transport layer 106 provided on the electron injection layer 107, an emitting layer 105 provided on the electron transport layer 106, a hole transport layer 104 provided on the emitting layer 105, a hole injection layer 103 provided on the hole transport layer 104, and an anode 102 provided on the hole injection layer 103.

[0187] Not all of the above layers are essential, and the minimum structural unit is a structure consisting of an anode 102, an emitting layer 105, and a cathode 108. The hole injection layer 103, the hole transport layer 104, the electron transport layer 106, and the electron injection layer 107 are layers that may be provided optionally. Each of the above layers may consist of a single layer or multiple layers.

[0188] In addition to the above-mentioned "substrate / anode / hole injection layer / hole transport layer / light-emitting layer / electron transport layer / electron injection layer / cathode" configuration, the layers constituting the organic EL element may be configured as "substrate / anode / hole transport layer / light-emitting layer / electron transport layer / electron injection layer / cathode", "substrate / anode / hole injection ...hole transport layer / light-emitting layer / electron injection layer / cathode", "substrate / anode / hole injection layer / hole transport layer / light-emitting layer / electron injection layer / cathode", or "substrate / anode / hole injection layer / hole transport layer / light-emitting layer / electron transport The configuration may be, for example, "substrate / anode / light-emitting layer / electron transport layer / electron injection layer / cathode", "substrate / anode / hole transport layer / light-emitting layer / electron injection layer / cathode", "substrate / anode / hole transport layer / light-emitting layer / electron transport layer / cathode", "substrate / anode / hole transport layer / light-emitting layer / electron injection layer / cathode", "substrate / anode / hole injection layer / light-emitting layer / electron injection layer / cathode", "substrate / anode / hole injection layer / light-emitting layer / electron transport layer / cathode", "substrate / anode / hole injection layer / light-emitting layer / electron transport layer / cathode", "substrate / anode / light-emitting layer / electron transport layer / cathode", or "substrate / anode / light-emitting layer / electron injection layer / cathode".

[0189] 2-1-2. 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, and may be, 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 material of the glass, it is preferable to use non-alkali glass because less ions are eluted from the glass, but SiO 2 Soda lime glass coated with a barrier coat such as a silicon oxide film is commercially available and can be used. In order to improve the gas barrier properties, a gas barrier film such as a dense silicon oxide film may be provided on at least one side of the substrate 101. In particular, when a synthetic resin plate, film, or sheet with low gas barrier properties is used as the substrate 101, it is preferable to provide a gas barrier film.

[0190] 2-1-3. Anode in organic electroluminescent device The anode 102 plays a role in injecting holes into the light-emitting layer 105. When the hole injection layer 103 and / or the hole transport layer 104 are provided between the anode 102 and the light-emitting layer 105, the holes are injected into the light-emitting layer 105 through these layers.

[0191] 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 may be appropriately selected from those used as anodes in organic EL elements.

[0192] The resistance of the transparent electrode is not limited as long as it can supply a sufficient current for the light emission of the light emitting element, but it is desirable that the resistance is low from the viewpoint of the power consumption of the light emitting element. For example, an ITO substrate of 300Ω / □ or less functions as an element electrode, but since it is now possible to supply substrates of about 10Ω / □, it is particularly desirable to use a low resistance product of, for example, 100 to 5Ω / □, preferably 50 to 5Ω / □. The thickness of the ITO can be selected arbitrarily according to the resistance value, but it is usually used in the range of 50 to 300 nm.

[0193] 2-1-4. Hole injection layer and hole transport layer in organic electroluminescent device The hole injection layer 103 plays a role of efficiently injecting holes moving from the anode 102 into the light emitting layer 105 or the hole transport layer 104. The hole transport layer 104 plays a role of efficiently transporting holes injected from the anode 102 or holes injected from the anode 102 via the hole injection layer 103 to the light emitting layer 105. The hole injection layer 103 and the hole transport layer 104 are each formed by laminating and mixing one or more types of hole injection / transport materials, or by a mixture of a hole injection / transport material and a polymer binder. Alternatively, a layer may be formed by adding an inorganic salt such as iron (III) chloride to the hole injection / transport material.

[0194] 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.

[0195] As the material for forming the hole injection layer 103 and the hole transport layer 104, any compound can be selected from compounds conventionally used as charge transport materials for holes in photoconductive materials, p-type semiconductors, and known compounds used in hole injection layers and hole transport layers of organic EL elements. Specific examples of such compounds include carbazole derivatives (N-phenylcarbazole, polyvinylcarbazole, etc.), biscarbazole derivatives such as bis(N-arylcarbazole) or bis(N-alkylcarbazole), triarylamine derivatives (polymers having an aromatic tertiary amino in the main chain or side chain, 1,1-bis(4-di-p-tolylaminophenyl)cyclohexane, N,N'-diphenyl-N,N'-di(3-methylphenyl)-4,4'-diaminobiphenyl, N,N'-diphenyl-N,N'-dinaphthyl-4,4'-diaminobiphenyl, N,N'-diphenyl-N,N'-di(3-methylphenyl)-4,4'-diphenyl-1,1'-diamine, N,N'-dinaphthyl-N,N'-diphenyl-4,4'-diphenyl-1,1'-diamine, N 4 ,N 4' -Diphenyl-N 4 ,N 4' -Bis(9-phenyl-9H-carbazol-3-yl)-[1,1'-biphenyl]-4,4'-diamine, N 4 ,N 4 ,N 4' ,N 4'-Tetra[1,1'-biphenyl]-4-yl)-[1,1'-biphenyl]-4,4'-diamine, 4,4',4"-tris(3-methylphenyl(phenyl)amino)triphenylamine and other triphenylamine derivatives, starburst amine derivatives, etc.), stilbene derivatives, phthalocyanine derivatives (metal-free, copper phthalocyanine, etc.), pyrazoline derivatives, hydrazone compounds, benzofuran derivatives, thiophene derivatives, oxadiazole derivatives, quinoxaline derivatives Conductors (e.g., 1,4,5,8,9,12-hexaazatriphenylene-2,3,6,7,10,11-hexacarbonitrile, etc.), heterocyclic compounds such as porphyrin derivatives, polysilanes, etc. As polymers, polycarbonates and styrene derivatives having the above-mentioned monomers in their side chains, polyvinylcarbazole, polysilanes, etc. are preferred, but there are no particular limitations on the compounds as long as they can form a thin film required for fabricating a light-emitting device, can inject holes from the anode, and can transport holes.

[0196] It is also known that the electrical conductivity of organic semiconductors is strongly influenced by their doping. Such organic semiconductor matrix substances consist of compounds with good electron donating or accepting properties. For doping with electron donating substances, strong electron acceptors such as tetracyanoquinone dimethane (TCNQ) or 2,3,5,6-tetrafluorotetracyano-1,4-benzoquinone dimethane (F4TCNQ) are known (see, for example, the references "M. Pfeiffer, A. Beyer, T. Fritz, K. Leo, Appl. Phys. Lett., 73(22), 3202-3204 (1998)" and "J. Blochwitz, M. Pfeiffer, T. Fritz, K. Leo, Appl. Phys. Lett., 73(6), 729-731 (1998)"). These generate so-called holes by an electron transfer process in the electron donating base substance (hole transport substance). The conductivity of the base material varies considerably depending on the number and mobility of holes. Matrix materials having hole transport properties are known, for example, benzidine derivatives (TPD, etc.) or starburst amine derivatives (TDATA, etc.), or certain metal phthalocyanines (especially zinc phthalocyanine (ZnPc) and the like) (JP 2005-167175 A).

[0197] The above-mentioned hole injection layer material and hole transport layer material can be used as a hole layer material in the form of a polymer compound obtained by polymerizing a reactive compound substituted with a reactive substituent as a monomer, or a crosslinked polymer thereof, or a pendant polymer compound obtained by reacting a main chain polymer with the reactive compound, or a crosslinked pendant polymer thereof. In this case, the explanation of the polycyclic aromatic compound represented by formula (1) can be cited as the reactive substituent. The applications of such polymer compounds and crosslinked polymers will be described in detail below.

[0198] <Formula (H) compound> As the material for the hole injection layer and the material for the hole transport layer, for example, a compound represented by the following formula (H) can be suitably used.

[0199] [ka]

[0200] In formula (H), R 31 ~R 38 Among these, one or more pairs of adjacent two or more may form a substituted or unsubstituted saturated or unsaturated ring. 31 ~R 38 each independently represents a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms, a substituted or unsubstituted alkylthio group having 1 to 50 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 50 ring carbon atoms, a substituted or unsubstituted arylthio group having 6 to 50 ring carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, -Si(R 201 )(R 202 )(R 203 ), -C(=O)R 204 , -COOR 205 R is a halogen atom, a cyano atom, a nitro atom, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms. 201 ~R 205 R are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms. 201 ~R 205 If there are two or more, there are two or more R 201 ~R 205 Each of may be the same or different. 21 ~L 24are each independently a single bond, a substituted or unsubstituted alkylene having 1 to 50 carbon atoms, a substituted or unsubstituted arylene having 6 to 50 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms. 21 and Ar 22 each independently represents a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

[0201] In the description of the substituents in formula (H) in this specification, the "number of carbon atoms XX to YY" in the expression "a substituted or unsubstituted ZZ group having carbon atoms XX to YY" represents the number of carbon atoms when the ZZ group is unsubstituted, and does not include the number of carbon atoms of the substituent when the ZZ group is substituted. Here, "YY" is larger than "XX", and "XX" and "YY" each represent an integer of 1 or more.

[0202] In the description of the substituents in formula (H) in this specification, the "number of atoms XX to YY" in the expression "a substituted or unsubstituted ZZ group having the number of atoms XX to YY" represents the number of atoms when the ZZ group is unsubstituted, and does not include the number of atoms of the substituent when it is substituted. Here, "YY" is larger than "XX", and "XX" and "YY" each represent an integer of 1 or more.

[0203] In the case of "substituted or unsubstituted", "unsubstituted" means that it is not substituted with the above-mentioned substituents and is bonded to a hydrogen atom.

[0204] In the description of the substituents in formula (H) in this specification, specific examples of each substituent include the following. Examples of the unsubstituted alkyl having 1 to 50 (preferably 1 to 30, more preferably 1 to 18, and even more preferably 1 to 5) carbon atoms include methyl, ethyl, propyl, isopropyl, n-butyl, s-butyl, isobutyl, t-butyl, n-pentyl, n-hexyl, n-heptyl, and n-octyl.

[0205] Examples of the substituted alkyl having 1 to 50 (preferably 1 to 30, more preferably 1 to 18, and even more preferably 1 to 5) carbon atoms include hydroxymethyl, 1-hydroxyethyl, 2-hydroxyethyl, 2-hydroxyisobutyl, 1,2-dihydroxyethyl, 1,3-dihydroxyisopropyl, 2,3-dihydroxy-t-butyl, 1,2,3-trihydroxypropyl, chloromethyl, 1-chloroethyl, 2-chloroethyl, 2-chloroisobutyl, 1,2-dichloroethyl, 1,3-dichloroisopropyl, 2,3-dichloro-t-butyl, 1,2,3-trichloropropyl, bromomethyl, 1-bromoethyl, 2-bromoethyl, 2-bromoisobutyl, 1,2-dibromoethyl, 1,3-dibromoisopropyl, 2,3-dibromo-t-butyl, 1,2,3-tribromo ...bromopropyl, bromomethyl, 1-bromoethyl, 2-bromoethyl, 2-bromoisobutyl, 1,2-dibromoethyl, 1,3-dibromoisopropyl, 2 pyr, iodomethyl, 1-iodoethyl, 2-iodoethyl, 2-iodoisobutyl, 1,2-diiodoethyl, 1,3-diiodoisopropyl, 2,3-diiodo-t-butyl, 1,2,3-triiodopropyl, cyanomethyl, 1-cyanoethyl, 2-cyanoethyl, 2-cyanoisobutyl, 1,2-dicyanoethyl, 1,3-dicyanoisopropyl, 2,3-dicyano-t-butyl, 1,2,3-tricyanopropyl, nitromethyl, 1-nitroethyl, 2-nitroethyl, 2-nitroisobutyl, 1,2-dinitroethyl, 1,3-dinitroisopropyl, 2,3-dinitro-t-butyl, 1,2,3-trinitropropyl, 1-pyrrolylmethyl, 2-(1-pyrrolyl)ethyl, 1-hydroxy-2-phenylisopropyl, 1-chloro-2-phenylisopropyl, and the like.

[0206] Examples of the unsubstituted alkenyl having 2 to 50 (preferably 2 to 30, more preferably 2 to 18) carbon atoms include vinyl, allyl, 1-butenyl, 2-butenyl, 3-butenyl, 1,3-butadienyl, 1-methylvinyl, 1-methylallyl, 1,1-dimethylallyl, 2-methylallyl, and 1,2-dimethylallyl.

[0207] Examples of the unsubstituted alkynyl having 2 to 50 (preferably 2 to 30, more preferably 2 to 18) carbon atoms include ethynyl.

[0208] Examples of the unsubstituted cycloalkyl having 3 to 50 (preferably 3 to 30, more preferably 3 to 18, and still more preferably 3 to 6) ring carbon atoms include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, 4-methylcyclohexyl, 1-adamantyl, 2-adamantyl, 1-norbornyl, and 2-norbornyl.

[0209] Unsubstituted alkoxy having 1 to 50 carbon atoms (preferably 1 to 30, more preferably 1 to 18) is represented by -OX, and examples of X include the above alkyl having 1 to 50 carbon atoms.

[0210] Unsubstituted alkylthio having 1 to 50 carbon atoms (preferably 1 to 30, more preferably 1 to 18) is represented by -SX, and examples of X include the above alkyl having 1 to 50 carbon atoms.

[0211] Examples of the unsubstituted aryl having 6 to 50 (preferably 6 to 30, more preferably 6 to 18) ring carbon atoms include phenyl, 1-naphthyl, 2-naphthyl, 1-anthryl, 2-anthryl, 9-anthryl, 1-phenanthryl, 2-phenanthryl, 3-phenanthryl, 4-phenanthryl, 9-phenanthryl, 1-naphthacenyl, 2-naphthacenyl, 9-naphthacenyl, 1-pyrenyl, 2-pyrenyl, 4-pyrenyl, 2-biphenylyl, 3-biphenylyl, 4-biphenylyl, p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, m-terphenyl-4-yl, m-terphenyl-3-yl, m-terphenyl-2-yl, and the like. Of these, preferred are phenyl, naphthyl, biphenylyl, terphenyl, pyrenyl, phenanthryl and fluorenyl, and more preferred are phenyl, naphthyl, biphenylyl, terphenyl, pyrenyl and fluorenyl.

[0212] Examples of the substituted aryl having 6 to 50 (preferably 6 to 30, more preferably 6 to 18) ring carbon atoms include o-tolyl, m-tolyl, p-tolyl, para-isopropylphenyl, meta-isopropylphenyl, ortho-isopropylphenyl, pt-butylphenyl, meta-t-butylphenyl, ortho-t-butylphenyl, 3,4,5-trimethylphenyl, 4-phenoxyphenyl, 4-methoxyphenyl, 3,4-dimethoxyphenyl, 3,4,5-trimethoxyphenyl, 4-(phenylsulfanyl)phenyl, 4-(methylsulfanyl)phenyl, N',N'-dimethyl-N- Examples of the alkyl group include phenyl, N',N'-dimethyl-N-phenyl, 2,6-dimethylphenyl, (2-phenylpropyl)phenyl, 3-methyl-2-naphthyl, 4-methyl-1-naphthyl, 4-methyl-1-anthryl, 4'-methylbiphenylyl, 4"-t-butyl-p-terphenyl-4-yl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, 9,9'-spirobifluorenyl, 9,9-di(4-methylphenyl)fluorenyl, 9,9-di(4-isopropylphenyl)fluorenyl, 9,9-di(4-t-butylphenyl)fluorenyl, chrysenyl, and fluoranthenyl.

[0213] Examples of the unsubstituted arylene having 6 to 50 (preferably 6 to 30, more preferably 6 to 18) ring carbon atoms include divalent groups formed from an aromatic hydrocarbon ring constituting the above-mentioned aryl having 6 to 50 ring carbon atoms. Specifically, for example, divalent groups formed from phenyl include o-, m-, and p-phenylene, divalent groups formed from biphenyl include 2,4'-biphenylylene, 3,4'-biphenylylene, and 4,4'-biphenylylene, and divalent groups formed from naphthyl include naphthalene-1,2-diyl, naphthalene-1,3-diyl, naphthalene-1,4-diyl, naphthalene-1,5-diyl, naphthalene-1,6-diyl, naphthalene-1,7-diyl, naphthalene-1,8-diyl, naphthalene-2,3-diyl, naphthalene-2,6-diyl, and naphthalene-2,7-diyl.

[0214] Unsubstituted aryloxy having 6 to 50 (preferably 6 to 30, more preferably 6 to 18) ring carbon atoms is represented by -OY, and examples of Y include the above-mentioned aryl having 6 to 50 ring carbon atoms.

[0215] Unsubstituted arylthio having 6 to 50 (preferably 6 to 30, more preferably 6 to 18) ring carbon atoms is represented by -SY, and examples of Y include the above-mentioned aryl having 6 to 50 ring carbon atoms.

[0216] Examples of the unsubstituted aralkyl having 7 to 50 (preferably 7 to 30, more preferably 7 to 18) carbon atoms include benzyl, 1-phenylethyl, 2-phenylethyl, 1-phenylisopropyl, 2-phenylisopropyl, phenyl-t-butyl, α-naphthylmethyl, 1-α-naphthylethyl, 2-α-naphthylethyl, 1-α-naphthylisopropyl, 2-α-naphthylisopropyl, β-naphthylmethyl, 1-β-naphthylethyl, 2-β-naphthylethyl, 1-β-naphthylisopropyl, and 2-β-naphthylisopropyl.

[0217] Examples of the substituted aralkyl having 7 to 50 (preferably 7 to 30, more preferably 7 to 18) carbon atoms include p-methylbenzyl, m-methylbenzyl, o-methylbenzyl, p-chlorobenzyl, m-chlorobenzyl, o-chlorobenzyl, p-bromobenzyl, m-bromobenzyl, o-bromobenzyl, p-iodobenzyl, m-iodobenzyl, o-iodobenzyl, p-hydroxybenzyl, m-hydroxybenzyl, o-hydroxybenzyl, p-nitrobenzyl, m-nitrobenzyl, o-nitrobenzyl, p-cyanobenzyl, m-cyanobenzyl, o-cyanobenzyl, and the like.

[0218] Examples of the unsubstituted heterocyclic group having 5 to 50 (preferably 5 to 30, more preferably 5 to 18) ring atoms include pyrrolyl, pyrazinyl, pyridinyl, indolyl, isoindolyl, furyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, dibenzothienyl, quinolyl, isoquinolyl, quinoxalinyl, carbazolyl, phenanthridinyl, acridinyl, phenanthrolinyl, and thienyl, as well as a pyridine ring, a pyrazine ring, a pyrimidine ring, a pyridazine ring, a triazine ring, an indole ring, a quinoline ring, an acridine ring, a pyrrolidine ring, a dioxane ring, a piperidine ring, a morpholine ring, a cyclohexane ... Examples of monovalent groups formed from a phosphorus ring, piperazine ring, carbazole ring, furan ring, thiophene ring, oxazole ring, oxadiazole ring, benzoxazole ring, thiazole ring, thiadiazole ring, benzothiazole ring, triazole ring, imidazole ring, benzimidazole ring, pyran ring, dibenzofuran ring, benzo[a]dibenzofuran ring, benzo[b]dibenzofuran ring and benzo[c]dibenzofuran ring, 1,3-benzodioxole ring, 2,3-dihydro-1,4-benzodioxine ring, phenanthro[4,5-bcd]furan ring, benzophenoxazine ring, and the like.

[0219] Examples of the unsubstituted divalent heterocyclic group having 5 to 50 (preferably 5 to 30, more preferably 5 to 18) ring atoms include the groups exemplified above and divalent groups formed from a heterocycle, etc.

[0220] Substituted or unsubstituted heterocyclic groups having 5 to 50 ring atoms also include the following groups. Divalent heterocyclic groups having 5 to 50 ring atoms also include the following groups which have been converted into divalent groups. In the following formulae, * indicates the bonding position in the case of a monovalent group.

[0221] [ka]

[0222] [ka]

[0223] (In the formula, X 1A ~X 6A ,Y 1A ~Y 6A are each an oxygen atom, a sulfur atom, an -NZ- group, or an -NH- group. Z is a substituted or unsubstituted aryl having 6 to 50 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, or a substituted or unsubstituted alkyl having 1 to 50 carbon atoms. When there are two or more Z's, the two or more Z's may be the same or different.

[0224] Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.

[0225] In compound (H), L 23 and L 24 The positional relationship on the benzene ring to which is bonded may be ortho (o), meta (m), or para (p), preferably ortho or meta, and particularly preferably meta.

[0226] Here, in the compound represented by formula (H), "R 31 ~R 38 may form a substituted or unsubstituted saturated or unsaturated ring”. "R 31 ~R 38 For example, "a pair of two or more adjacent pairs of R 31 and R32 , R 32 and R 33 , R 33 and R 34 , R 34 and R 35 , R 35 and R 36 , R 36 and R 37 , R 37 and R 38 , R 31 and R 32 and R 33 , R 32 and R 33 and R 34etc. combinations. The "substituted or unsubstituted" substituents for the above saturated or unsaturated ring are as described below with respect to formula (H). A "saturated or unsaturated ring" is, for example, R 31 and R 32 When a ring is formed with R 31 and the carbon atom to which R is bonded. 32 It means a ring formed by the carbon atom to which R is bonded and one or more arbitrary elements. 31 and R 32 In the case where a ring is formed by R 31 and the carbon atom to which R is bonded. 32 When the carbon atom to which is bonded forms an unsaturated ring with four carbon atoms, R 31 and R 32 The ring formed by this is a benzene ring. The "arbitrary element" is preferably a C element, an N element, an O element, or an S element. When the arbitrary element is a C element or an N element, the bond not involved in ring formation may be terminated with a hydrogen atom or the like. The "one or more arbitrary elements" refers to any element preferably 2 or more and 15 or less, more preferably 3 or more and 12 or less, and even more preferably 3 or more and 5 or less.

[0227] R 32 and R 33 and R 34 When one pair of these forms a ring, the compound represented by formula (H) is, for example, a compound represented by the following formula (H-10). 61 is phenyl, R 32 and R 33 and R 34 A pair of these forms a substituted ring.

[0228] [ka]

[0229] [In formula (H-10), R 31 , R 35 ~R 38 , L21 ~L 24 , Ar 21 and Ar 22 is as defined in formula (H), R 61 ~R 66 has the same meaning as the substituent (any substituent of compound (H)) in the case of "substituted or unsubstituted" in compound (H) described below.]

[0230] "One or more sets" means, for example, R 31 and R 32 forms a ring, and at the same time R 37 and R 38 may form a ring. In that case, the compound represented by formula (H) is, for example, a compound represented by the following formula (H-11). In addition, in the following formula (H-11), for example, R 71 is phenyl, R 31 and R 32 thus forming a substituted ring.

[0231] [ka]

[0232] [In formula (H-11), R 33 ~R 36 , L 21 ~L 24 , Ar 21 and Ar 22 is as defined in formula (H), R 71 ~R 78 has the same meaning as the substituent (any substituent of compound (H)) in the case of "substituted or unsubstituted" in compound (H) described below.]

[0233] In one embodiment, compound (H) preferably includes either or both of a compound represented by the following formula (Ha) and a compound represented by the following formula (Hb) (hereinafter referred to as compounds (Ha) and (Hb)).

[0234] [ka]

[0235] [In the formulas (Ha) and (Hb), R 31 ~R 38 , L 21 ~L 24 , Ar 21 and Ar 22 is as defined in formula (H) above.]

[0236] In one embodiment, L in compound (H) 23 Or L 24 At least one of the is a single bond.

[0237] In one embodiment, compound (H) is a compound (Ha), i.e., L 23 and L 24 are preferably substituted at the meta positions of the benzene ring. In one embodiment, L in compound (H) 24 is preferably a single bond. In one embodiment, L in compound (H) 23 is preferably a single bond. In one embodiment, Ar in compound (H) 21 and Ar 22 and the other is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms. In one embodiment, R in compound (H) 31 ~R 38 is preferably a hydrogen atom.

[0238] In one embodiment, compound (H) is a compound represented by the following formula (Ha-1) and / or the following formula (Hb-1).

[0239] [ka]

[0240] [In the formulas (Ha-1) and (Hb-1), R 31 ~R 38 , L 21 ~L 23 , Ar 21 and Ar 22 is as defined in formula (H) above.]

[0241] In one embodiment, compound (H) is a compound represented by the following formula (Ha-2) and / or the following formula (Hb-2).

[0242] [ka]

[0243] [In formula (Ha-2) and (Hb-2), R 31 ~R 38 , L 21 , L 22 , L 24 , Ar 21 and Ar 22 is as defined in formula (H) above.]

[0244] In one embodiment, compound (H) is a compound represented by the following formula (Ha-3) and / or the following formula (Hb-3).

[0245] [ka]

[0246] [In formulas (Ha-3) and (Hb-3), L 21 ~L 24 , Ar 21 and Ar 22 is as defined in formula (H) above.]

[0247] In one embodiment, compound (H) is one or more selected from the group consisting of compounds represented by the following formula (Ha-4) and compounds represented by the following formula (Hb-4).

[0248] [ka]

[0249] [In formulas (Ha-4) and (Hb-4), L 21 , L 22 , L 24 , Ar 21 and Ar 22 is as defined in formula (H) above.]

[0250] In one embodiment, compound (H) is a compound represented by the following formula (Ha-4).

[0251] [ka]

[0252] [In formula (Ha-4), L 21 , L 22 , L 24 , Ar 21 and Ar 22 is as defined in formula (H) above.]

[0253] In one embodiment, L in formula (H) 23 and L 24 One of the groups is a single bond, and the other is a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms.

[0254] Examples of the substituent in the case of "substituted or unsubstituted" in the compounds (H), (Ha), (Hb), (Ha-1), (Hb-1), (Ha-2), (Hb-2), (Ha-3), (Hb-3), (Ha-4) and (Hb-4) (hereinafter also referred to as an arbitrary substituent in the compound (H)) include alkyl having 1 to 50 carbon atoms, alkenyl having 2 to 50 carbon atoms, alkynyl having 2 to 50 carbon atoms, cycloalkyl having 3 to 50 ring carbon atoms, alkoxy having 1 to 50 carbon atoms, alkylthio having 1 to 50 carbon atoms, aryloxy having 6 to 50 ring carbon atoms, arylthio having 6 to 50 ring carbon atoms, aralkyl having 7 to 50 carbon atoms, -Si(R 41 )(R 42 )(R 43 ), -C(=O)R 44 , -COOR 45 , -S(=O)2R 46 , -P(=O)(R 47 )(R 48 ), -Ge(R 49 )(R 50 )(R 51 ) (where R 41 ~R 51 R are each independently a hydrogen atom, an alkyl group having 1 to 50 carbon atoms, an aryl group having 6 to 50 ring carbon atoms, or a heterocyclic group having 5 to 50 ring atoms. 41 ~R 51 If there are two or more, there are two or more R 41 ~R 51 may be the same or different.) hydroxy, halogen, cyano, nitro, an aryl having 6 to 50 ring carbon atoms, and a heterocyclic group having 5 to 50 ring atoms. Among these, an alkyl group having 1 to 50 carbon atoms, an aryl group having 6 to 50 ring carbon atoms, or a heterocyclic group having 5 to 50 ring atoms is preferred, and an alkyl group having 1 to 18 carbon atoms, an aryl group having 6 to 18 ring carbon atoms, or a heterocyclic group having 5 to 18 ring atoms is more preferred.

[0255] Specific examples of the substituents, optional substituents, and halogen atoms in these compounds (H) are the same as those described above, but the substituents and optional substituents in compounds (H) do not include substituted or unsubstituted amino. Therefore, in compounds (H), there is only one amino. The compound represented by formula (H) is most preferably a compound represented by formula (H1).

[0256] [ka]

[0257] In formula (H1), L 121 and L 122 each independently represents a single bond or unsubstituted phenylene; L 123 is unsubstituted phenylene, and Ar 121 and Ar 122 Each independently is unsubstituted phenyl or unsubstituted biphenylyl. 121 and L 122 Each of L is preferably a single bond or unsubstituted 1,4-phenylene, and more preferably unsubstituted 1,4-phenylene. 123 is preferably unsubstituted 1,4-phenylene. 121 and Ar 122 are each independently preferably unsubstituted phenyl, or unsubstituted 4-biphenylyl, or 3-biphenylyl, and more preferably unsubstituted phenyl or unsubstituted 4-biphenylyl.

[0258] Examples of compounds represented by formula (H) include the following compounds:

[0259] [ka]

[0260] [ka]

[0261] [ka]

[0262] [ka]

[0263] 2-1-5. 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 compound of the present invention can be used as a material for the light-emitting layer. For example, a host material and a polycyclic aromatic compound represented by the above formula (1) or a multimer thereof as a dopant material can be used as a material for the light-emitting layer.

[0264] The light-emitting layer may be a single layer or multiple layers, each of which is formed from materials for the light-emitting layer (host material, dopant material). The host material and the dopant material may each be one type or a combination of multiple types. The dopant material may be contained in the entire host material or may be contained partially in the host material. As a doping method, the dopant material may be formed by co-evaporation with the host material, but it may also be mixed with the host material in advance and then vapor-deposited at the same time.

[0265] The amount of the host material used varies depending on the type of the host material and may be determined according to the properties of the host material. The amount of the host material used is preferably 50 to 99.999% by mass, more preferably 80 to 99.95% by mass, and even more preferably 90 to 99.9% by mass, of the total material for the light-emitting layer.

[0266] The amount of the dopant material used varies depending on the type of the dopant material, and may be determined according to the characteristics of the dopant material. The amount of the dopant used is preferably 0.001 to 50% by mass, more preferably 0.05 to 20% by mass, and even more preferably 0.1 to 10% by mass, based on the total material for the light-emitting layer. The above range is preferable in that, for example, concentration quenching can be prevented.

[0267] Examples of the host material include condensed ring derivatives of anthracene, pyrene, dibenzochrysene, fluorene, etc., which have been known as light emitters, bisstyryl derivatives such as bisstyrylanthracene derivatives and distyrylbenzene derivatives, tetraphenylbutadiene derivatives, cyclopentadiene derivatives, etc. In particular, anthracene-based compounds, fluorene-based compounds, and dibenzochrysene-based compounds are preferred.

[0268] <Anthracene compounds> The anthracene compound as the host is, for example, a compound represented by the following formula (3). [ka]

[0269] In formula (3), X and Ar 4 are each independently hydrogen, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted diarylamino, optionally substituted diheteroarylamino, optionally substituted arylheteroarylamino, optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted alkenyl, optionally substituted alkoxy, optionally substituted aryloxy, optionally substituted arylthio or optionally substituted silyl; and all X and Ar 4 cannot simultaneously become hydrogen, At least one hydrogen in the compound represented by formula (3) may be substituted with halogen, cyano, deuterium or an optionally substituted heteroaryl.

[0270] In addition, a polymer (preferably a dimer) may be formed using the structure represented by formula (3) as a unit structure. In this case, for example, the unit structures represented by formula (3) may be bonded to each other via X, and examples of X include a single bond, arylene (phenylene, biphenylene, naphthylene, etc.), and heteroarylene (a group having a divalent bond such as a pyridine ring, a dibenzofuran ring, a dibenzothiophene ring, a carbazole ring, a benzocarbazole ring, and a phenyl-substituted carbazole ring).

[0271] The details of the above aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, alkyl, cycloalkyl, alkenyl, alkoxy, aryloxy, arylthio, or silyl will be described in the following preferred embodiment section. The substituents on these include aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, alkyl, cycloalkyl, alkenyl, alkoxy, aryloxy, arylthio, or silyl, and the details of these are also described in the following preferred embodiment section.

[0272] Preferred embodiments of the above anthracene-based compounds are described below. The symbols in the structures below are defined as above. [ka]

[0273] In formula (3), X is each independently a group represented by the above formula (3-X1), formula (3-X2) or formula (3-X3), and the group represented by formula (3-X1), formula (3-X2) or formula (3-X3) is bonded to the anthracene ring of formula (3) at *. Preferably, two Xs are not simultaneously a group represented by formula (3-X3). More preferably, two Xs are not simultaneously a group represented by formula (3-X2).

[0274] In addition, a polymer (preferably a dimer) may be formed using the structure represented by formula (3) as a unit structure. In this case, for example, the unit structures represented by formula (3) may be bonded to each other via X, and examples of X include a single bond, arylene (phenylene, biphenylene, naphthylene, etc.), and heteroarylene (a group having a divalent bond such as a pyridine ring, a dibenzofuran ring, a dibenzothiophene ring, a carbazole ring, a benzocarbazole ring, and a phenyl-substituted carbazole ring).

[0275] The naphthylene moieties in formula (3-X1) and formula (3-X2) may be condensed with one benzene ring. The condensed structures are as follows: [ka]

[0276] Ar 1 and Ar 2 are each independently hydrogen, phenyl, biphenylyl, terphenylyl, quaterphenylyl, naphthyl, phenanthryl, fluorenyl, benzofluorenyl, chrysenyl, triphenylenyl, pyrenylyl, or a group represented by the above formula (A) (including carbazolyl, benzocarbazolyl, and phenyl-substituted carbazolyl). 1 or Ar 2 is a group represented by formula (A), the group represented by formula (A) is bonded to the naphthalene ring in formula (3-X1) or formula (3-X2) at the *.

[0277] Ar 3is phenyl, biphenylyl, terphenylyl, quaterphenylyl, naphthyl, phenanthryl, fluorenyl, benzofluorenyl, chrysenyl, triphenylenyl, pyrenylyl, or a group represented by the above formula (A) (including carbazolyl, benzocarbazolyl, and phenyl-substituted carbazolyl). 3 is a group represented by formula (A), the group represented by formula (A) is bonded to the single bond represented by a straight line in formula (3-X3) at the *. That is, the anthracene ring in formula (3) and the group represented by formula (A) are directly bonded.

[0278] Also, Ar 3 may have a substituent, and Ar 3 At least one hydrogen atom in may be further substituted with an alkyl group having 1 to 4 carbon atoms, a cycloalkyl group having 5 to 10 carbon atoms, phenyl, biphenylyl, terphenylyl, naphthyl, phenanthryl, fluorenyl, chrysenyl, triphenylenyl, pyrenylyl, or a group represented by the above formula (A) (including carbazolyl and phenyl-substituted carbazolyl). 3 is a group represented by formula (A), the group represented by formula (A) is Ar 3 and combine.

[0279] Ar 4 are each independently hydrogen, phenyl, biphenylyl, terphenylyl, naphthyl, or silyl substituted with alkyl having 1 to 4 carbon atoms (eg, methyl, ethyl, t-butyl) and / or cycloalkyl having 5 to 10 carbon atoms.

[0280] Examples of the alkyl group having 1 to 4 carbon atoms that substitutes for the silyl include methyl, ethyl, propyl, i-propyl, butyl, sec-butyl, t-butyl, and cyclobutyl, and three hydrogen atoms in the silyl are each independently substituted with these alkyl groups.

[0281] Specific examples of "silyl substituted with alkyl having 1 to 4 carbon atoms" include trimethylsilyl, triethylsilyl, tripropylsilyl, tri-i-propylsilyl, tributylsilyl, tri-sec-butylsilyl, tri-t-butylsilyl, ethyldimethylsilyl, propyldimethylsilyl, i-propyldimethylsilyl, butyldimethylsilyl, sec-butyldimethylsilyl, t-butyldimethylsilyl, methyldiethylsilyl, propyldiethylsilyl, i-propyldiethylsilyl, butyldiethylsilyl, sec-butyldiethylsilyl, t-butyldiethylsilyl, methyldipropylsilyl, ethyldipropylsilyl, butyldipropylsilyl, sec-butyldipropylsilyl, t-butyldipropylsilyl, methyldi-i-propylsilyl, ethyldi-i-propylsilyl, butyldi-i-propylsilyl, sec-butyldi-i-propylsilyl, t-butyldi-i-propylsilyl, and the like.

[0282] Examples of the cycloalkyl having 5 to 10 carbon atoms substituting the silyl include cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, norbornenyl, bicyclo[1.1.1]pentyl, bicyclo[2.0.1]pentyl, bicyclo[1.2.1]hexyl, bicyclo[3.0.1]hexyl, bicyclo[2.1.2]heptyl, bicyclo[2.2.2]octyl, adamantyl, decahydronaphthalenyl, and decahydroazulenyl, and three hydrogens in the silyl are each independently substituted with these cycloalkyls.

[0283] Specific examples of the "silyl substituted with cycloalkyl having 5 to 10 carbon atoms" include tricyclopentylsilyl and tricyclohexylsilyl.

[0284] Substituted silyls include dialkylcycloalkylsilyls substituted with two alkyls and one cycloalkyl, and alkyldicycloalkylsilyls substituted with one alkyl and two cycloalkyls, and specific examples of the alkyl and cycloalkyl substituents include the groups mentioned above.

[0285] In addition, hydrogen in the chemical structure of the anthracene compound represented by formula (3) may be substituted with a group represented by formula (A) above. When substituted with a group represented by formula (A), the group represented by formula (A) replaces at least one hydrogen in the compound represented by formula (3) at the *.

[0286] The group represented by formula (A) is one of the substituents that the anthracene compound represented by formula (3) can have. [ka]

[0287] In formula (A), Y is -O-, -S- or >NR 29 and R 21 ~R 28 are each independently hydrogen, optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted alkoxy, optionally substituted aryloxy, optionally substituted arylthio, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, alkyldicycloalkylsilyl, optionally substituted amino, halogen, hydroxy or cyano; R 21 ~R 28 adjacent groups among R may be bonded to each other to form a hydrocarbon ring, an aryl ring, or a heteroaryl ring; 29 is hydrogen or optionally substituted aryl.

[0288] R 21 ~R 28The "alkyl" in the "optionally substituted alkyl" may be either linear or branched, and examples thereof include linear alkyl having 1 to 24 carbon atoms or branched alkyl having 3 to 24 carbon atoms. An alkyl having 1 to 18 carbon atoms (branched alkyl having 3 to 18 carbon atoms) is preferred, an alkyl having 1 to 12 carbon atoms (branched alkyl having 3 to 12 carbon atoms) is more preferred, an alkyl having 1 to 6 carbon atoms (branched alkyl having 3 to 6 carbon atoms) is even more preferred, and an alkyl having 1 to 4 carbon atoms (branched alkyl having 3 to 4 carbon atoms) is particularly preferred.

[0289] 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.

[0290] R 21 ~R 28 Examples of the "cycloalkyl" in the "optionally substituted cycloalkyl" include cycloalkyl having 3 to 24 carbon atoms, cycloalkyl having 3 to 20 carbon atoms, cycloalkyl having 3 to 16 carbon atoms, cycloalkyl having 3 to 14 carbon atoms, cycloalkyl having 5 to 10 carbon atoms, cycloalkyl having 5 to 8 carbon atoms, cycloalkyl having 5 to 6 carbon atoms, and cycloalkyl having 5 carbon atoms.

[0291] Specific examples of "cycloalkyl" include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, and alkyl (especially methyl) substituted derivatives of these having 1 to 4 carbon atoms, as well as norbornenyl, bicyclo[1.0.1]butyl, bicyclo[1.1.1]pentyl, bicyclo[2.0.1]pentyl, bicyclo[1.2.1]hexyl, bicyclo[3.0.1]hexyl, bicyclo[2.1.2]heptyl, bicyclo[2.2.2]octyl, adamantyl, diamantyl, decahydronaphthalenyl, and decahydroazulenyl.

[0292] R 21 ~R 28 In the above, the "aryl" in the "optionally substituted aryl" includes, for example, aryl having 6 to 30 carbon atoms, preferably aryl having 6 to 16 carbon atoms, more preferably aryl having 6 to 12 carbon atoms, and particularly preferably aryl having 6 to 10 carbon atoms.

[0293] Specific examples of "aryl" include phenyl, which is a monocyclic ring system; biphenylyl, which is a bicyclic ring system; naphthyl, which is a fused bicyclic ring system; terphenylyl, which is a tricyclic ring system (m-terphenylyl, o-terphenylyl, p-terphenylyl); acenaphthylenyl, fluorenyl, phenalenyl, phenanthrenyl, which are fused tricyclic ring systems; triphenylenyl, pyrenyl, and naphthacenyl, which are fused tetracyclic ring systems; and perylenyl and pentacenyl, which are fused pentacyclic ring systems.

[0294] R 21 ~R 28 Examples of the "heteroaryl" in the "optionally substituted heteroaryl" include heteroaryl having 2 to 30 carbon atoms, preferably heteroaryl having 2 to 25 carbon atoms, more preferably heteroaryl having 2 to 20 carbon atoms, further preferably heteroaryl having 2 to 15 carbon atoms, and particularly preferably heteroaryl having 2 to 10 carbon atoms. Examples of the heteroaryl include heterocycles containing, as ring-constituting atoms other than carbon, 1 to 5 heteroatoms selected from oxygen, sulfur, and nitrogen.

[0295] Specific examples of "heteroaryl" include pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, oxadiazolyl, thiadiazolyl, triazolyl, tetrazolyl, pyrazolyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, indolyl, isoindolyl, 1H-indazolyl, benzimidazolyl, benzoxazolyl, benzothiazolyl, 1H-benzotriazolyl, quinolyl, isoquinolyl, cyclohex ... Examples of the aryl group include aryl, aryl, aryloxy, aryloxy, and aryloxy. Examples of the aryl group include aryl, aryloxy, and aryloxy. Examples of the aryl group include aryl, aryloxy, and aryloxy. Examples of the aryl group include aryl, aryloxy, and aryloxy. Examples of the aryl group include aryl, aryloxy, and aryloxy. Examples of the aryl group include aryl, aryloxy, and aryloxy.

[0296] R 21 ~R 28 Examples of the "alkoxy" in the "optionally substituted alkoxy" include linear alkoxy having 1 to 24 carbon atoms or branched alkoxy having 3 to 24 carbon atoms. An alkoxy having 1 to 18 carbon atoms (branched alkoxy having 3 to 18 carbon atoms) is preferred, an alkoxy having 1 to 12 carbon atoms (branched alkoxy having 3 to 12 carbon atoms) is more preferred, an alkoxy having 1 to 6 carbon atoms (branched alkoxy having 3 to 6 carbon atoms) is even more preferred, and an alkoxy having 1 to 4 carbon atoms (branched alkoxy having 3 to 4 carbon atoms) is particularly preferred.

[0297] Particular "alkoxy" includes methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, s-butoxy, t-butoxy, pentyloxy, hexyloxy, heptyloxy, octyloxy, and the like.

[0298] R 21 ~R 28The "aryloxy" in the "optionally substituted aryloxy" is a group in which the hydrogen of the -OH group is replaced by an aryl, and this aryl is the same as R 21 ~R 28 The group described as "aryl" in the above formula can be used.

[0299] R 21 ~R 28 The "arylthio" in the "optionally substituted arylthio" is a group in which the hydrogen of the -SH group is replaced by an aryl, and this aryl is the same as R 21 ~R 28 The group described as "aryl" in the above formula can be used.

[0300] R 21 ~R 28 The "trialkylsilyl" in the above formula includes a silyl group in which three hydrogen atoms are independently replaced by alkyl, and the alkyl is as defined above in R 21 ~R 28 The groups described as "alkyl" in the above can be cited. Preferred alkyl groups for substitution are alkyl groups having 1 to 4 carbon atoms, and specific examples thereof include methyl, ethyl, propyl, i-propyl, butyl, sec-butyl, t-butyl, and cyclobutyl.

[0301] Specific examples of the "trialkylsilyl" include trimethylsilyl, triethylsilyl, tripropylsilyl, tri-i-propylsilyl, tributylsilyl, tri-sec-butylsilyl, tri-t-butylsilyl, ethyldimethylsilyl, propyldimethylsilyl, i-propyldimethylsilyl, butyldimethylsilyl, sec-butyldimethylsilyl, t-butyldimethylsilyl, methyldiethylsilyl, propyldiethylsilyl, i-propyldiethylsilyl, butyldiethylsilyl, sec-butyldiethylsilyl, t-butyldiethylsilyl, methyldipropylsilyl, ethyldipropylsilyl, butyldipropylsilyl, sec-butyldipropylsilyl, t-butyldipropylsilyl, methyldi-i-propylsilyl, ethyldi-i-propylsilyl, butyldi-i-propylsilyl, sec-butyldi-i-propylsilyl, and t-butyldi-i-propylsilyl.

[0302] R 21 ~R 28 The "tricycloalkylsilyl" in the formula (I) includes a silyl group in which three hydrogen atoms are each independently replaced by a cycloalkyl, and this cycloalkyl is as defined above for R 21 ~R 28 The groups described as "cycloalkyl" in the above can be cited. Preferred cycloalkyl for substitution is cycloalkyl having 5 to 10 carbon atoms, and specific examples thereof include cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, bicyclo[1.1.1]pentyl, bicyclo[2.0.1]pentyl, bicyclo[1.2.1]hexyl, bicyclo[3.0.1]hexyl, bicyclo[2.1.2]heptyl, bicyclo[2.2.2]octyl, adamantyl, decahydronaphthalenyl, and decahydroazulenyl.

[0303] Specific examples of the "tricycloalkylsilyl" include tricyclopentylsilyl, tricyclohexylsilyl, and the like.

[0304] 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.

[0305] R 21 ~R 28 The "substituted amino" in the "optionally substituted amino" in the above is, for example, an amino in which two hydrogen atoms are substituted with aryl or heteroaryl. An amino in which two hydrogen atoms are substituted with aryl is a diaryl-substituted amino, an amino in which two hydrogen atoms are substituted with heteroaryl is a diheteroaryl-substituted amino, and an amino in which two hydrogen atoms are substituted with an aryl and a heteroaryl is an arylheteroaryl-substituted amino. The aryl and heteroaryl are as defined above in R 21 ~R 28 The groups described above as "aryl" and "heteroaryl" can be cited.

[0306] Specific examples of the "substituted amino" include diphenylamino, dinaphthylamino, phenylnaphthylamino, dipyridylamino, phenylpyridylamino, naphthylpyridylamino, and the like.

[0307] R 21 ~R 28 The "halogen" in the above formula includes fluorine, chlorine, bromine, and iodine.

[0308] R 21 ~R 28 Some of the groups described as may be substituted as described above, in which case the substituents include alkyl, cycloalkyl, aryl, or heteroaryl. The alkyl, cycloalkyl, aryl, or heteroaryl may be any of the groups described above as R 21 ~R 28 In the above, reference can be made to a group described as "alkyl", "cycloalkyl", "aryl" or "heteroaryl".

[0309] Y as 'NR' 29 " R in 29 is hydrogen or an optionally substituted aryl, and the aryl is as defined above in R 21 ~R 28 The group described as "aryl" in the above formula can be cited, and the substituents thereof include R 21 ~R 28 The groups described above as substituents for the above can be cited.

[0310] R 21 ~R 28 Among these, adjacent groups may be bonded to each other to form a hydrocarbon ring, an aryl ring, or a heteroaryl ring. The group represented by the following formula (A-1) does not form a ring, and the group represented by the following formulas (A-2) to (A-14) may be exemplified as the group represented by any one of formulas (A-1) to (A-14). At least one hydrogen atom in the group represented by any one of formulas (A-1) to (A-14) may be substituted with alkyl, cycloalkyl, aryl, heteroaryl, alkoxy, aryloxy, arylthio, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, alkyldicycloalkylsilyl, diaryl-substituted amino, diheteroaryl-substituted amino, arylheteroaryl-substituted amino, halogen, hydroxy, or cyano.

[0311] [ka]

[0312] Examples of the ring formed by bonding adjacent groups to each other include a hydrocarbon ring such as a cyclohexane ring, and examples of the aryl ring and heteroaryl ring include the above-mentioned R 21 ~R 28 These rings are formed so as to be condensed with one or two benzene rings in the above formula (A-1).

[0313] Examples of the group represented by formula (A) include groups represented by any of the above formulas (A-1) to (A-14). Of these, groups represented by any of the above formulas (A-1) to (A-5) and (A-12) to (A-14) are preferred. Groups represented by any of the above formulas (A-1) to (A-4) are more preferred. Groups represented by any of the above formulas (A-1), (A-3) and (A-4) are even more preferred. Groups represented by the above formula (A-1) are particularly preferred.

[0314] The group represented by formula (A) is a naphthalene ring in formula (3-X1) or formula (3-X2), a single bond in formula (3-X3), Ar in formula (3-X3), 3 As described above, the naphthalene ring in formula (3-X1) or formula (3-X2), the single bond in formula (3-X3), and / or Ar in formula (3-X3) are bonded to the naphthalene ring in formula (3-X1) or formula (3-X2), and are substituted with at least one hydrogen atom in the compound represented by formula (3). 3 The form in which it is bound to is preferred.

[0315] In addition, in the structure of the group represented by formula (A), the naphthalene ring in formula (3-X1) or formula (3-X2), the single bond in formula (3-X3), Ar in formula (3-X3), 3 The position at which R is bonded, and the position at which at least one hydrogen atom in the compound represented by formula (3) is substituted in the structure of the group represented by formula (A), may be any position in the structure of formula (A), for example, any of the two benzene rings in the structure of formula (A) or R 21 ~R 28 Any of the rings formed by bonding adjacent groups to each other, or ">NR 29 " R in 29 The bond can be at any position within the

[0316] Examples of the group represented by formula (A) include the following groups: In the formula, Y and * are defined as above. [ka]

[0317] All or a part of the hydrogen atoms in the chemical structure of the anthracene compound represented by formula (3) may be deuterium atoms.

[0318] Specific examples of the anthracene-based compound include compounds represented by the following formulas (3-1) to (3-123): In the following structural formulas, "Me" represents methyl, "D" represents deuterium, and "tBu" represents t-butyl.

[0319] [ka]

[0320] [ka]

[0321] [ka]

[0322] [ka]

[0323] [ka]

[0324] [ka]

[0325] [ka]

[0326] [ka]

[0327] [ka]

[0328] [ka]

[0329] The anthracene compound represented by formula (3) is a compound having a reactive group at a desired position of an anthracene skeleton, and X, Ar 4 The compound having a reactive group in a partial structure such as the structure of formula (A) can be used as a starting material to produce the compound by applying Suzuki coupling, Negishi coupling, or other known coupling reactions. Examples of the reactive group in these reactive compounds include halogens and boronic acids. As a specific production method, for example, the synthesis methods in paragraphs

[0089] to

[0175] of International Publication No. 2014 / 141725 can be referred to.

[0330] <Fluorene-based compounds> The compound represented by formula (4) basically functions as a host. [ka]

[0331] In the above formula (4), R 1 From R 10 are each independently a hydrogen atom, an aryl atom, a heteroaryl atom (wherein the heteroaryl atom may be bonded to the fluorene skeleton in the above formula (4) via a linking group), a diarylamino atom, a diheteroarylamino atom, an arylheteroarylamino atom, an alkyl atom, a cycloalkyl atom, an alkenyl atom, an alkoxy atom, or an aryloxy atom, in which at least one hydrogen atom may be substituted with an aryl atom, a heteroaryl atom, an alkyl atom, or a cycloalkyl atom; Also, R 1 and R 2 , R 2 and R 3, R 3 and R 4 , R 5 and R 6 , R 6 and R 7 , R 7 and R 8 or R 9 and R 10 may each independently bond to form a fused ring or a spiro ring, at least one hydrogen in the formed ring may be replaced with an aryl, a heteroaryl (the heteroaryl may be bonded to the formed ring via a linking group), a diarylamino, a diheteroarylamino, an arylheteroarylamino, an alkyl, a cycloalkyl, an alkenyl, an alkoxy, or an aryloxy, at least one hydrogen in these may be replaced with an aryl, a heteroaryl, an alkyl, or a cycloalkyl, and At least one hydrogen in the compound represented by formula (4) may be substituted with halogen, cyano or deuterium.

[0332] For details of each group in the definition of the above formula (4), the explanation for the polycyclic aromatic compound of the above formula (1) can be cited.

[0333] R 1 From R 10 Examples of the alkenyl include alkenyl having 2 to 30 carbon atoms, preferably alkenyl having 2 to 20 carbon atoms, more preferably alkenyl having 2 to 10 carbon atoms, further preferably alkenyl having 2 to 6 carbon atoms, and particularly preferably alkenyl having 2 to 4 carbon atoms. Preferred alkenyls are vinyl, 1-propenyl, 2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, or 5-hexenyl.

[0334] Specific examples of heteroaryl include monovalent groups represented by removing any one hydrogen atom from a compound of the following formula (4-Ar1), formula (4-Ar2), formula (4-Ar3), formula (4-Ar4), or formula (4-Ar5).

[0335] [ka]

[0336] In formulas (4-Ar1) to (4-Ar5), Y 1 are each independently O, S or NR, R is phenyl, biphenylyl, naphthyl, anthracenyl or hydrogen; At least one hydrogen atom in the structures of the above formulae (4-Ar1) to (4-Ar5) may be substituted with phenyl, biphenylyl, naphthyl, anthracenyl, phenanthrenyl, methyl, ethyl, propyl, or butyl.

[0337] These heteroaryls may be bonded to the fluorene skeleton in the above formula (4) via a linking group. That is, the fluorene skeleton and the above heteroaryls in the formula (4) may be bonded directly, or may be bonded to each other via a linking group. Examples of the linking group include phenylene, biphenylene, naphthylene, anthracenylene, methylene, ethylene, -OCH 2 CH 2 -, -CH 2 CH 2 O- or -OCH 2 CH 2 O-, etc.

[0338] In addition, R in formula (4) 1 and R 2 , R 2 and R 3 , R 3 and R 4 , R 5 and R 6 , R 6 and R 7 or R 7 and R 8are each independently bonded to form a fused ring, R 9 and R 10 may be bonded to form a spiro ring. 1 From R 8 The fused ring formed by is a ring fused to the benzene ring in formula (4), and is an aliphatic ring or an aromatic ring. An aromatic ring is preferable, and examples of the structure including the benzene ring in formula (4) include a naphthalene ring and a phenanthrene ring. 9 and R 10 The spiro ring formed by the formula (4) is a ring that is spiro-bonded to the five-membered ring in the formula (4), and is an aliphatic ring or an aromatic ring. An aromatic ring, such as a fluorene ring, is preferable.

[0339] The compound represented by formula (4) is preferably a compound represented by the following formula (4-1), formula (4-2) or formula (4-3), 1 and R 2 A compound having a condensed benzene ring formed by bonding with 3 and R 4 A compound having a condensed benzene ring formed by bonding with 1 From R 8 is a compound in which none of the above is bound.

[0340] [ka]

[0341] R in formula (4-1), formula (4-2) and formula (4-3) 1 From R 10 The definition of R in Eq. (4) corresponds to 1 From R 10 is the same as R in formula (4-1) and formula (4-2). 11 From R 14 The definition of R in Eq. (4) 1 From R 10 is the same as:

[0342] The compound represented by formula (4) is more preferably a compound represented by the following formula (4-1A), formula (4-2A) or formula (4-3A), in which R 9 and R 10 is a compound in which a spiro-fluorene ring is formed by bonding.

[0343] [ka]

[0344] R in formula (4-1A), formula (4-2A) and formula (4-3A) 2 From R 7 The definition of is the corresponding R in formula (4-1), formula (4-2) and formula (4-3). 2 From R 7 and R in formula (4-1A) and formula (4-2A) 11 From R 14 The definition of R in formula (4-1) and formula (4-2) 11 From R 14 is the same as:

[0345] In addition, all or a part of the hydrogen atoms in the compound represented by formula (4) may be substituted with halogen, cyano or deuterium.

[0346] <Dibenzochrysene compounds> The dibenzochrysene compound as the host is, for example, a compound represented by the following formula (5). [ka]

[0347] In the above formula (5), R 1 From R 16are each independently a hydrogen atom, an aryl, a heteroaryl (wherein the heteroaryl may be bonded to the dibenzochrysene skeleton in the above formula (5) via a linking group), a diarylamino, a diheteroarylamino, an arylheteroarylamino, an alkyl, a cycloalkyl, an alkenyl, an alkoxy, or an aryloxy, in which at least one hydrogen atom may be substituted with an aryl, a heteroaryl, an alkyl, or a cycloalkyl; Also, R 1 From R 16 adjacent groups among these may be bonded to each other to form a condensed ring, at least one hydrogen atom in the formed ring may be substituted with an aryl, a heteroaryl (the heteroaryl may be bonded to the formed ring via a linking group), a diarylamino, a diheteroarylamino, an arylheteroarylamino, an alkyl, a cycloalkyl, an alkenyl, an alkoxy, or an aryloxy, at least one hydrogen atom in these may be substituted with an aryl, a heteroaryl, an alkyl, or a cycloalkyl, and At least one hydrogen in the compound represented by formula (5) may be substituted with halogen, cyano or deuterium.

[0348] For details of each group in the definition of the above formula (5), the explanation for the polycyclic aromatic compound of the above formula (1) can be cited.

[0349] The alkenyl in the definition of the above formula (5) includes, for example, alkenyl having 2 to 30 carbon atoms, preferably alkenyl having 2 to 20 carbon atoms, more preferably alkenyl having 2 to 10 carbon atoms, further preferably alkenyl having 2 to 6 carbon atoms, and particularly preferably alkenyl having 2 to 4 carbon atoms. Preferred alkenyl is vinyl, 1-propenyl, 2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, or 5-hexenyl.

[0350] Specific examples of heteroaryl include monovalent groups represented by removing any one hydrogen atom from a compound of the following formula (5-Ar1), formula (5-Ar2), formula (5-Ar3), formula (5-Ar4), or formula (5-Ar5).

[0351] [ka]

[0352] In formula (5-Ar1) to formula (5-Ar5), Y 1 are each independently O, S or NR, R is phenyl, biphenylyl, naphthyl, anthracenyl or hydrogen; At least one hydrogen atom in the structures of the above formulae (5-Ar1) to (5-Ar5) may be substituted with phenyl, biphenylyl, naphthyl, anthracenyl, phenanthrenyl, methyl, ethyl, propyl, or butyl.

[0353] These heteroaryls may be bonded to the dibenzochrysene skeleton in the above formula (5) via a linking group. That is, the dibenzochrysene skeleton and the above heteroaryl in the formula (5) may be bonded directly or via a linking group. Examples of the linking group include phenylene, biphenylene, naphthylene, anthracenylene, methylene, ethylene, -OCH 2 CH 2 -, -CH 2 CH 2 O- or -OCH 2 CH 2 O-, etc.

[0354] The compound represented by formula (5) is preferably R 1 , R 4 , R 5 , R 8 , R 9 , R 12 , R 13 and R 16 is hydrogen. In this case, R in formula (5) 2 , R 3 , R6 , R 7 , R 10 , R 11 , R 14 and R 15 each independently represents hydrogen, phenyl, biphenylyl, naphthyl, anthracenyl, phenanthrenyl, or a monovalent group having the structure of the above formula (5-Ar1), formula (5-Ar2), formula (5-Ar3), formula (5-Ar4), or formula (5-Ar5) (the monovalent group having the structure is phenylene, biphenylene, naphthylene, anthracenylene, methylene, ethylene, -OCH 2 CH 2 -, -CH 2 CH 2 O- or -OCH 2 CH 2 (which may be bonded to the dibenzochrysene skeleton in the above formula (5) via O-), methyl, ethyl, propyl, or butyl is preferred.

[0355] The compound represented by formula (5) is more preferably 1 , R 2 , R 4 , R 5 , R 7 , R 8 , R 9 , R 10 , R 12 , R 13 , R 15 and R 16 is hydrogen. In this case, R in formula (5) 3 , R 6 , R 11 and R 14 At least one (preferably one or two, more preferably one) of the above is a single bond, phenylene, biphenylene, naphthylene, anthracenylene, methylene, ethylene, -OCH 2 CH 2 -, -CH 2 CH 2 O- or -OCH 2 CH 2 a monovalent group having the structure of the above formula (5-Ar1), formula (5-Ar2), formula (5-Ar3), formula (5-Ar4) or formula (5-Ar5) via O-; The other than the at least one (i.e., other than the position substituted by the monovalent group having the structure) is hydrogen, phenyl, biphenylyl, naphthyl, anthracenyl, methyl, ethyl, propyl, or butyl, and at least one hydrogen in these may be substituted with phenyl, biphenylyl, naphthyl, anthracenyl, methyl, ethyl, propyl, or butyl.

[0356] In addition, R in formula (5) 2 , R 3 , R 6 , R 7 , R 10 , R 11 , R 14 and R 15 When a monovalent group having a structure represented by the above formula (5-Ar1) to formula (5-Ar5) is selected as the aryl group, at least one hydrogen atom in the structure is R 1 From R 16 may be bonded to any one of the following to form a single bond.

[0357] The above-mentioned light-emitting layer materials (host material and dopant material) can be used as light-emitting layer materials as polymer compounds obtained by polymerizing a reactive compound substituted with a reactive substituent as a monomer, or as crosslinked polymers thereof, or as pendant polymer compounds obtained by reacting a main chain polymer with the reactive compound, or as crosslinked pendant polymers thereof. In this case, the explanation of the polycyclic aromatic compound represented by formula (1) can be cited as the reactive substituent. The applications of such polymer compounds and crosslinked polymers will be described in detail below.

[0358] <Example of polymer host material> [ka]

[0359] In formula (SPH-1), Each MU is independently a divalent group represented by removing any two hydrogen atoms from an aromatic compound, and each EC is independently a monovalent group represented by removing any one hydrogen atom from an aromatic compound, in which two hydrogen atoms in MU are replaced by EC or MU, and k is an integer from 2 to 50,000.

[0360] More specifically, Each MU is independently arylene, heteroarylene, diarylenarylamino, diarylenarylboryl, oxaborine-diyl, or azaborine-diyl; each E C is independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, or aryloxy; At least one hydrogen in MU and EC may be further substituted with aryl, heteroaryl, diarylamino, alkyl, and cycloalkyl; k is an integer from 2 to 50,000. k is preferably an integer from 20 to 50,000, and more preferably an integer from 100 to 50,000.

[0361] At least one hydrogen atom in MU and EC in formula (SPH-1) may be substituted with an alkyl group having 1 to 24 carbon atoms, a cycloalkyl group having 3 to 24 carbon atoms, a halogen atom, or a deuterium atom. 2 - is -O- or -Si(CH 3 ) 2 -, and -CH directly bonded to EC in formula (SPH-1) 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.

[0362] Examples of MU include a divalent group represented by removing any two hydrogen atoms from any of the following compounds: [ka]

[0363] More specifically, the divalent group may be any of the following structures: In these, MU is bonded to another MU or EC at *.

[0364] [ka]

[0365] [ka]

[0366] [ka]

[0367] [ka]

[0368] [ka]

[0369] [ka]

[0370] [ka]

[0371] [ka] [ka]

[0372] Examples of EC include monovalent groups represented by any of the following structures: In these, EC is bonded to MU at *.

[0373] [ka]

[0374] [ka]

[0375] From the viewpoint of solubility and coating film-forming property, the compound represented by formula (SPH-1) is preferably such that 10 to 100% of the total number of MUs (k) in the molecule have an alkyl having 1 to 24 carbon atoms, more preferably 30 to 100% of the total number of MUs (k) in the molecule have an alkyl having 1 to 18 carbon atoms (branched chain alkyl having 3 to 18 carbon atoms), and even more preferably 50 to 100% of the total number of MUs (k) in the molecule have an alkyl having 1 to 12 carbon atoms (branched chain alkyl having 3 to 12 carbon atoms). On the other hand, from the viewpoint of in-plane alignment 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).

[0376] The applications of such polymer compounds and crosslinked polymers will be described in detail below.

[0377] 2-1-6. 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.

[0378] 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.

[0379] The material (electron transport material) for forming the electron transport layer 106 or the electron injection layer 107 can be arbitrarily selected from compounds conventionally used as electron transport compounds in photoconductive materials and known compounds used in the electron injection layer and electron transport layer of organic EL elements.

[0380] Materials used in the electron transport layer or electron injection layer preferably contain at least one selected from compounds consisting of aromatic rings or heteroaromatic rings composed of one or more atoms selected from carbon, hydrogen, oxygen, sulfur, silicon, and phosphorus, pyrrole derivatives and their condensed ring derivatives, and metal complexes having electron-accepting nitrogen. Specific examples include condensed ring aromatic ring derivatives such as naphthalene and anthracene, styryl aromatic ring derivatives such as 4,4'-bis(diphenylethenyl)biphenyl, perinone derivatives, coumarin derivatives, naphthalimide derivatives, quinone derivatives such as anthraquinone and diphenoquinone, phosphorus oxide derivatives, arylnitrile derivatives, and indole derivatives. Examples of metal complexes having electron-accepting nitrogen include hydroxyazole complexes such as hydroxyphenyloxazole complexes, azomethine complexes, tropolone metal complexes, flavonol metal complexes, and benzoquinoline metal complexes. These materials can be used alone or in combination with different materials.

[0381] Specific examples of other electron transfer compounds include borane derivatives, pyridine derivatives, naphthalene derivatives, fluoranthene derivatives, BO 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 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, benzimidazole derivatives (e.g., tris(N-phenylbenzimidazol-2-yl)benzene), benzoxazole derivatives, thiazole 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, pyrimidine derivatives, arylnitrile derivatives, indole derivatives, phosphorus oxide derivatives, bisstyryl derivatives, silole derivatives, and azoline derivatives.

[0382] 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.

[0383] The above-mentioned materials may be used alone or in combination with different materials.

[0384] Among the above-mentioned materials, borane derivatives, pyridine derivatives, fluoranthene derivatives, BO-based derivatives, anthracene derivatives, benzofluorene derivatives, phosphine oxide derivatives, pyrimidine derivatives, arylnitrile derivatives, triazine derivatives, benzimidazole derivatives, phenanthroline derivatives, quinolinol-based metal complexes, thiazole derivatives, benzothiazole derivatives, silole derivatives and azoline derivatives are preferred.

[0385] <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.

[0386] [ka]

[0387] In formula (ETM-1), R 11 and R 12 are each independently at least one of hydrogen, alkyl, cycloalkyl, optionally substituted aryl, substituted silyl, optionally substituted nitrogen-containing heterocycle, or cyano; R 13 ~R 16 are each independently an optionally substituted alkyl, an optionally substituted cycloalkyl, or an optionally substituted aryl, X is an optionally substituted arylene, Y is an optionally substituted aryl having 16 or less carbon atoms, a substituted boryl, or an optionally substituted carbazolyl, and each n is independently an integer of 0 to 3. In addition, examples of the substituent in the case of "optionally substituted" or "substituted" include aryl, heteroaryl, alkyl, and cycloalkyl.

[0388] Among the compounds represented by the above formula (ETM-1), compounds represented by the following formula (ETM-1-1) and compounds represented by the following formula (ETM-1-2) are preferred.

[0389] [ka]

[0390] In formula (ETM-1-1), R 11 and R 12 are each independently at least one of hydrogen, alkyl, cycloalkyl, optionally substituted aryl, substituted silyl, optionally substituted nitrogen-containing heterocycle, or cyano; R 13 ~R 16 are each independently optionally substituted alkyl, optionally substituted cycloalkyl, or optionally substituted aryl; R 21 and R 22 are each independently at least one of hydrogen, alkyl, cycloalkyl, optionally substituted aryl, substituted silyl, optionally substituted nitrogen-containing heterocycle, or cyano; X 1 is an optionally substituted arylene having 20 or less carbon atoms, each n is independently an integer of 0 to 3, and each m is independently an integer of 0 to 4. In addition, examples of the substituent in the case where "optionally substituted" or "substituted" include aryl, heteroaryl, alkyl, and cycloalkyl.

[0391] [ka]

[0392] In formula (ETM-1-2), R 11 and R 12 are each independently at least one of hydrogen, alkyl, cycloalkyl, optionally substituted aryl, substituted silyl, optionally substituted nitrogen-containing heterocycle, or cyano; R 13 ~R16 are each independently an optionally substituted alkyl, an optionally substituted cycloalkyl, or an optionally substituted aryl; X 1 is an optionally substituted arylene having 20 or less carbon atoms, and each n is independently an integer of 0 to 3. In addition, examples of the substituent in the case where it is "optionally substituted" or "substituted" include aryl, heteroaryl, alkyl, and cycloalkyl.

[0393] X 1 Specific examples of the group include divalent groups represented by any of the following formulae (X-1) to (X-9).

[0394] [ka] (In each formula, R a are each independently alkyl, cycloalkyl, or optionally substituted phenyl, and * represents the bonding position.

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

[0396] The borane derivative can be produced using known raw materials and known synthesis methods.

[0397] <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]

[0398] 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.

[0399] In the above formula (ETM-2-1), R 11 ~R 18 are each independently hydrogen, alkyl (preferably alkyl having 1 to 24 carbon atoms), cycloalkyl (preferably cycloalkyl having 3 to 12 carbon atoms) or aryl (preferably aryl having 6 to 30 carbon atoms).

[0400] In the above 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.

[0401] In each formula, the "pyridine-based substituent" is any one of the following formulae (Py-1) to (Py-15) (in the formula, * represents 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. In addition, the pyridine-based substituent may be bonded to the φ, anthracene ring, or fluorene ring in each formula via phenylene or naphthylene.

[0402] [ka]

[0403] The pyridine-based substituent is any of the above formulas (Py-1) to (Py-15), and among these, any of the following formulas (Py-21) to (Py-44) (in the formulas, * indicates a bonding position) is preferable. [ka]

[0404] At least one hydrogen atom in each pyridine derivative may be replaced by deuterium, and one of the two "pyridine-based substituents" in the above formulas (ETM-2-1) and (ETM-2-2) may be replaced by aryl.

[0405] 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).

[0406] 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.

[0407] As for the alkyl having 1 to 4 carbon atoms with which the pyridine-based substituent is substituted, the above description of the alkyl can be cited.

[0408] 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. Particular "cycloalkyl" includes cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, methylcyclopentyl, cycloheptyl, methylcyclohexyl, cyclooctyl, dimethylcyclohexyl, and the like.

[0409] 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.

[0410] 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.

[0411] 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.

[0412] R in the above formula (ETM-2-2) 11 and R 12 may be bonded to form a ring, and as a result, cyclobutane, cyclopentane, cyclopentene, cyclopentadiene, cyclohexane, fluorene, indene, or the like may be spiro-bonded to the five-membered ring of the fluorene skeleton.

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

[0414] This pyridine derivative can be produced using known raw materials and known synthesis methods.

[0415] <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. [ka]

[0416] 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.

[0417] Specific examples of this fluoranthene derivative include, for example, the following compounds.

Chemical formula

[0418] <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).

[0419]

Chemical formula

[0420] R 1 ~R 11 Each independently represents 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.

[0421] Also, adjacent groups among R 1 ~R 11 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.

[0422] Also, at least one hydrogen in the compound or structure represented by the formula (ETM-4) may be substituted with halogen or deuterium.

[0423] For an explanation of the substituents and the form of ring formation in formula (ETM-4), the explanation of the polycyclic aromatic compound represented by formula (1) or formula (2) above can be cited.

[0424] Specific examples of the BO derivative include the following compounds. [ka]

[0425] The BO derivative can be produced using known raw materials and known synthesis methods.

[0426] <Anthracene derivatives> One of the anthracene derivatives is, for example, a compound represented by the following formula (ETM-5-1). [ka]

[0427] Ar is independently a divalent benzene or naphthalene; R 1 ~R 4 are each independently hydrogen, alkyl having 1 to 6 carbon atoms, cycloalkyl having 3 to 6 carbon atoms, or aryl having 6 to 20 carbon atoms.

[0428] Each Ar can be independently selected from divalent benzene or naphthalene, and the two Ar may be different or the same, but it is preferable that they are the same from the viewpoint of ease of synthesis of the anthracene derivative. Ar is bonded to pyridine to form a "moiety consisting of Ar and pyridine", and this moiety is bonded to anthracene as a group represented by any one of the following formulas (Py-1) to (Py-12). * in the following formulas indicates a bonding position.

[0429] [ka]

[0430] Among these groups, a group represented by any one of the above formulas (Py-1) to (Py-9) is preferred, and a group represented by any one of the above formulas (Py-1) to (Py-6) is more preferred. The two "Ar and pyridine moieties" bonded to anthracene may have the same or different structures, but from the viewpoint of ease of synthesis of anthracene derivatives, it is preferable that they have the same structure. However, from the viewpoint of element characteristics, it is preferable that the two "Ar and pyridine moieties" have the same or different structures.

[0431] R 1 ~R 4 The alkyl having 1 to 6 carbon atoms in the formula (I) may be either linear or branched. That is, it is a linear alkyl having 1 to 6 carbon atoms or a branched alkyl having 3 to 6 carbon atoms. More preferably, it is an alkyl having 1 to 4 carbon atoms (branched alkyl having 3 to 4 carbon atoms). Specific examples include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, t-butyl, n-pentyl, isopentyl, neopentyl, t-pentyl, n-hexyl, 1-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, and 2-ethylbutyl. Methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, and t-butyl are preferred, and methyl, ethyl, and t-butyl are more preferred.

[0432] R 1 ~R 4 Specific examples of the cycloalkyl having 3 to 6 carbon atoms include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, methylcyclopentyl, cycloheptyl, methylcyclohexyl, cyclooctyl, and dimethylcyclohexyl.

[0433] R 1 ~R 4 With regard to the aryl having 6 to 20 carbon atoms in the above formula, aryl having 6 to 16 carbon atoms is preferable, aryl having 6 to 12 carbon atoms is more preferable, and aryl having 6 to 10 carbon atoms is particularly preferable.

[0434] Specific examples of "aryl having 6 to 20 carbon atoms" include monocyclic aryls such as phenyl, (o-, m-, p-)tolyl, (2,3-, 2,4-, 2,5-, 2,6-, 3,4-, 3,5-)xylyl, mesityl (2,4,6-trimethylphenyl), and (o-, m-, p-)cumenyl, bicyclic aryls such as (2-, 3-, 4-)biphenylyl, condensed bicyclic aryls such as (1-, 2-)naphthyl, and tricyclic aryls such as terphenylyl (m-terphenyl-2'-yl, m-terphenyl-4'-yl, m-terphenyl-5'-yl, o-terphenyl-3'-yl, o-terphenyl-4'-yl, p-terphenyl-2'-yl, m-terphenyl-2-yl, m-terphenyl-3-yl, m-terphenyl-4'-yl, p-terphenyl-2 ...4'-yl, p-terphenyl-2-yl, m-terphenyl-2-yl, m-terphenyl-3-yl, m-terphenyl-4'-yl, p-terphenyl-2-yl, m-terphenyl-4'-yl, p-terphenyl-2-yl, m-terphenyl-2-yl, m-terphenyl-3-yl, m aryl, o-terphenyl-4-yl, o-terphenyl-2-yl, o-terphenyl-3-yl, o-terphenyl-4-yl, p-terphenyl-2-yl, p-terphenyl-3-yl, p-terphenyl-4-yl; condensed tricyclic aryls, anthracene-(1-,2-,9-)yl, acenaphthylene-(1-,3-,4-,5-)yl, fluorene-(1-,2-,3-,4-,9-)yl, phenalene-(1-,2-)yl, (1-,2-,3-,4-,9-)phenanthryl; condensed tetracyclic aryls, triphenylene-(1-,2-)yl, pyrene-(1-,2-,4-)yl, tetracene-(1-,2-,5-)yl; condensed pentacyclic aryls, perylene-(1-,2-,3-)yl, and the like.

[0435] The "aryl having 6 to 20 carbon atoms" is preferably phenyl, biphenylyl, terphenylyl or naphthyl, more preferably phenyl, biphenylyl, 1-naphthyl, 2-naphthyl or m-terphenyl-5'-yl, even more preferably phenyl, biphenylyl, 1-naphthyl or 2-naphthyl, and most preferably phenyl.

[0436] One example of the anthracene derivative is a compound represented by the following formula (ETM-5-2). [ka]

[0437] Ar 1 are each independently a single bond, or a divalent benzene, naphthalene, anthracene, fluorene, or phenalene.

[0438] Ar 2 are each independently an aryl having 6 to 20 carbon atoms, and the same explanation as for "aryl having 6 to 20 carbon atoms" in the above formula (ETM-5-1) can be cited. An aryl having 6 to 16 carbon atoms is 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.

[0439] R 1 ~R 4 are each independently hydrogen, alkyl having 1 to 6 carbon atoms, cycloalkyl having 3 to 6 carbon atoms, or aryl having 6 to 20 carbon atoms, and the explanation in the above formula (ETM-5-1) can be cited.

[0440] Specific examples of these anthracene derivatives include the following compounds. [ka]

[0441] These anthracene derivatives can be produced using known raw materials and known synthesis methods.

[0442] <Benzofluorene derivatives> The benzofluorene derivative is, for example, a compound represented by the following formula (ETM-6). [ka]

[0443] Ar1 are each independently an aryl having 6 to 20 carbon atoms, and the same explanation as for "aryl having 6 to 20 carbon atoms" in the above formula (ETM-5-1) can be cited. An aryl having 6 to 16 carbon atoms is 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.

[0444] 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.

[0445] Ar 2 The "alkyl" in the above may be either linear or branched, and examples thereof include linear alkyl having 1 to 24 carbon atoms and branched alkyl having 3 to 24 carbon atoms. A preferred "alkyl" is an alkyl having 1 to 18 carbon atoms (branched alkyl having 3 to 18 carbon atoms). A more preferred "alkyl" is an alkyl having 1 to 12 carbon atoms (branched alkyl having 3 to 12 carbon atoms). An even more preferred "alkyl" is an alkyl having 1 to 6 carbon atoms (branched alkyl having 3 to 6 carbon atoms). An especially preferred "alkyl" is an alkyl having 1 to 4 carbon atoms (branched alkyl having 3 to 4 carbon atoms). Specific examples of "alkyl" include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, t-butyl, n-pentyl, isopentyl, neopentyl, t-pentyl, n-hexyl, 1-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, n-heptyl, 1-methylhexyl, and the like.

[0446] Ar 2In the above, examples of the "cycloalkyl" include cycloalkyl having 3 to 12 carbon atoms. A preferred "cycloalkyl" is cycloalkyl having 3 to 10 carbon atoms. A more preferred "cycloalkyl" is cycloalkyl having 3 to 8 carbon atoms. An even more preferred "cycloalkyl" is cycloalkyl having 3 to 6 carbon atoms. Specific examples of the "cycloalkyl" include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, methylcyclopentyl, cycloheptyl, methylcyclohexyl, cyclooctyl, and dimethylcyclohexyl.

[0447] 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.

[0448] Specific examples of the "aryl having 6 to 30 carbon atoms" include phenyl, naphthyl, acenaphthylenyl, fluorenyl, phenalenyl, phenanthryl, triphenylenyl, pyrenyl, naphthacenyl, perylenyl, and pentacenyl.

[0449] 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.

[0450] Specific examples of the benzofluorene derivative include the following compounds. [ka]

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

[0452] <Phosphine oxide derivatives> The phosphine oxide derivative is, for example, a compound represented by the following formula (ETM-7-1): The details are also described in WO 2013 / 079217 and WO 2013 / 079678. [ka]

[0453] R 5 is a substituted or unsubstituted alkyl having 1 to 20 carbon atoms, cycloalkyl having 3 to 16 carbon atoms, aryl having 6 to 20 carbon atoms, or heteroaryl having 5 to 20 carbon atoms, R 6 is CN, a substituted or unsubstituted alkyl having 1 to 20 carbon atoms, a cycloalkyl having 3 to 16 carbon atoms, a heteroalkyl having 1 to 20 carbon atoms, an aryl having 6 to 20 carbon atoms, a heteroaryl having 5 to 20 carbon atoms, an alkoxy having 1 to 20 carbon atoms, or an aryloxy having 6 to 20 carbon atoms, R 7 and R 8 each independently represents a substituted or unsubstituted aryl having 6 to 20 carbon atoms or a heteroaryl having 5 to 20 carbon atoms, R 9 is oxygen or sulfur, j is 0 or 1, k is 0 or 1, r is an integer of 0 to 4, and q is an integer of 1 to 3. When substituted, the substituent may be an aryl, heteroaryl, alkyl, or cycloalkyl.

[0454] The phosphine oxide derivative may be, for example, a compound represented by the following formula (ETM-7-2). [ka]

[0455] R 1 ~R 3may be the same or different and are selected from hydrogen, alkyl, cycloalkyl, aralkyl, alkenyl, cycloalkenyl, alkynyl, alkoxy, alkylthio, cycloalkylthio, an aryl ether group, an aryl thioether group, aryl, a heterocyclic group, halogen, cyano, aldehyde, carbonyl, carboxyl, amino, nitro, silyl, and a fused ring formed between adjacent substituents.

[0456] Ar 1 may be the same or different and are arylene or heteroarylene. Ar 2 may be the same or different and are aryl or heteroaryl, provided that Ar 1 and Ar 2 At least one of R has a substituent or forms a condensed ring with the adjacent substituent. n is an integer of 0 to 3. When n is 0, there is no unsaturated structural portion. When n is 3, R 1 does not exist.

[0457] Among these substituents, alkyl refers to saturated aliphatic hydrocarbon groups such as methyl, ethyl, propyl, and butyl, which may be unsubstituted or substituted. If substituted, the substituent is not particularly limited, and may be, for example, alkyl, aryl, or heterocyclic groups, which is also 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.

[0458] 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.

[0459] 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.

[0460] The alkenyl refers to an unsaturated aliphatic hydrocarbon group containing a double bond, such as vinyl, allyl, butadienyl, which may be unsubstituted or substituted. The number of carbon atoms in the alkenyl is not particularly limited, but is usually in the range of 2 to 20.

[0461] 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.

[0462] The term "alkynyl" refers to an unsaturated aliphatic hydrocarbon group containing a triple bond, such as acetylenyl, which may be unsubstituted or substituted. The number of carbon atoms in the alkynyl is not particularly limited, but is usually within the range of 2 to 20.

[0463] The term "alkoxy" refers to an aliphatic hydrocarbon group, such as methoxy, which is bonded via an ether bond, and the aliphatic hydrocarbon group may be unsubstituted or substituted. The number of carbon atoms in the alkoxy is not particularly limited, but is usually in the range of 1 to 20.

[0464] Moreover, alkylthio is a group in which the oxygen atom of the ether bond of alkoxy is replaced with a sulfur atom.

[0465] Moreover, cycloalkylthio is a group in which the oxygen atom of the ether bond of cycloalkoxy is replaced with a sulfur atom.

[0466] The aryl ether group refers to an aromatic hydrocarbon group such as phenoxy, which is bonded via an ether bond, and the aromatic hydrocarbon group may be unsubstituted or substituted. The number of carbon atoms in the aryl ether group is not particularly limited, but is usually in the range of 6 to 40.

[0467] An aryl thioether group is a group in which the oxygen atom of the ether bond of an aryl ether group is substituted with a sulfur atom.

[0468] 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.

[0469] The heterocyclic group refers to a cyclic structure group having atoms other than carbon, such as furanyl, thienyl, oxazolyl, pyridyl, quinolinyl, carbazolyl, etc., which may be unsubstituted or substituted. The number of carbon atoms in the heterocyclic group is not particularly limited, but is usually in the range of 2 to 30.

[0470] Halogen refers to fluorine, chlorine, bromine and iodine.

[0471] The aldehyde, carbonyl and amino groups may also include groups substituted with aliphatic hydrocarbons, alicyclic hydrocarbons, aromatic hydrocarbons, heterocycles and the like.

[0472] Furthermore, the aliphatic hydrocarbons, alicyclic hydrocarbons, aromatic hydrocarbons and heterocycles may be either unsubstituted or substituted.

[0473] 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.

[0474] The condensed ring formed between adjacent substituents is, for example, Ar1 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.

[0475] Specific examples of the phosphine oxide derivative include the following compounds. [ka]

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

[0477] <Pyrimidine derivatives> The pyrimidine derivative is, for example, a compound represented by the following formula (ETM-8), preferably a compound represented by the following formula (ETM-8-1). Details are also described in WO 2011 / 021689. [ka]

[0478] 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.

[0479] 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.

[0480] 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.

[0481] 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.

[0482] 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.

[0483] The above aryl and heteroaryl may be substituted, for example, by the above aryl or heteroaryl, respectively.

[0484] Specific examples of the pyrimidine derivative include the following compounds: [ka]

[0485] The pyrimidine derivative can be produced using known raw materials and known synthesis methods.

[0486] <Aryl nitrile derivatives> The arylnitrile derivative is, for example, a compound represented by the following formula (ETM-9), or a multimer in which a plurality of such compounds are bonded together via single bonds, etc. Details are described in the specification of US Patent Publication No. 2014 / 0197386. [ka]

[0487] Ar ni From the viewpoint of fast electron transport property, it is preferable that the number of carbon atoms is large, and from the viewpoint of high T1, it is preferable that the number of carbon atoms is small. ni Specifically, it is preferable that the aryl group has a high T1 when used in a layer adjacent to the light-emitting layer, and is an aryl group having 6 to 20 carbon atoms, preferably an aryl group having 6 to 14 carbon atoms, and more preferably an aryl group having 6 to 10 carbon atoms. In addition, the number of nitrile group substitutions, n, is preferably large from the viewpoint of high T1, and is preferably small from the viewpoint of high S1. Specifically, the number of nitrile group substitutions, n, is an integer of 1 to 4, preferably an integer of 1 to 3, more preferably an integer of 1 to 2, and even more preferably 1.

[0488] Each Ar is independently an aryl which may be substituted or a heteroaryl which may be substituted. From the viewpoint of high S1 and high T1, it is preferable that the heteroaryl has donor properties, and it is preferable that the heteroaryl has few donor properties because it is used as an electron transport layer. From the viewpoint of charge transportability, it is preferable that the aryl or heteroaryl has many carbon atoms, and it is preferable that the aryl or heteroaryl has many substituents. The number of substitutions m of Ar is specifically an integer of 1 to 4, preferably an integer of 1 to 3, and more preferably 1 to 2.

[0489] 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.

[0490] 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.

[0491] 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.

[0492] 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.

[0493] The above aryl and heteroaryl may be substituted, for example, by the above aryl or heteroaryl, respectively.

[0494] 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.

[0495] Specific examples of the arylnitrile derivative include the following compounds: [ka]

[0496] The arylnitrile derivatives can be produced using known raw materials and known synthesis methods.

[0497] <Triazine derivatives> The triazine derivative is, for example, a compound represented by the following formula (ETM-10), preferably a compound represented by the following formula (ETM-10-1), the details of which are described in US Patent Publication No. 2011 / 0156013. [ka]

[0498] 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.

[0499] 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.

[0500] 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.

[0501] 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.

[0502] 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.

[0503] The above aryl and heteroaryl may be substituted, for example, by the above aryl or heteroaryl, respectively.

[0504] Specific examples of the triazine derivative include the following compounds: [ka]

[0505] The triazine derivative can be produced using known raw materials and known synthesis methods.

[0506] <Benzimidazole derivatives> The benzimidazole derivative is, for example, a compound represented by the following formula (ETM-11). [ka]

[0507] φ is an n-valent aryl ring (preferably an n-valent benzene ring, naphthalene ring, anthracene ring, fluorene ring, benzofluorene ring, phenalene ring, phenanthrene ring, or triphenylene ring), n is an integer from 1 to 4, and the "benzoimidazole-based substituent" is a substituent in which the pyridyl in the "pyridine-based substituent" in the above formulae (ETM-2), (ETM-2-1), and (ETM-2-2) is replaced with benzimidazolyl, and at least one hydrogen in the benzimidazole derivative may be replaced with deuterium.

[0508] [ka]

[0509] R in the above benzimidazolyl 11 is hydrogen, alkyl having 1 to 24 carbon atoms, cycloalkyl having 3 to 12 carbon atoms, or aryl having 6 to 30 carbon atoms, and R 11 The explanation can be cited.

[0510] It is further preferable that φ is an anthracene ring or a fluorene ring. In this case, the structure can be as described in the above formula (ETM-2-1) or formula (ETM-2-2). 11 ~R 18 The explanation for formula (ETM-2-1) or formula (ETM-2-2) above can be cited. In addition, in formula (ETM-2-1) or formula (ETM-2-2) above, the two pyridine-based substituents are explained as being bonded, but when these are replaced with benzimidazole-based substituents, both pyridine-based substituents may be replaced with benzimidazole-based substituents (i.e., n=2), or one of the pyridine-based substituents may be replaced with a benzimidazole-based substituent and the other pyridine-based substituent may be replaced with R 11 ~R 18 (i.e., n=1). Furthermore, for example, R in the above formula (ETM-2-1) 11 ~R 18At least one of the above is replaced with a benzimidazole-based substituent to form a "pyridine-based substituent" R 11 ~R 18 may be substituted.

[0511] 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.

[0512] [ka]

[0513] The benzimidazole derivative can be produced using known raw materials and known synthesis methods.

[0514] <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.

[0515] [ka]

[0516] 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.

[0517] R of each formula 11 ~R 18 are each independently hydrogen, alkyl (preferably alkyl having 1 to 24 carbon atoms), cycloalkyl (preferably cycloalkyl having 3 to 12 carbon atoms), or aryl (preferably aryl having 6 to 30 carbon atoms). 11 ~R 18 Either one of the rings is bonded to φ, which is an aryl ring.

[0518] At least one hydrogen atom in each of the phenanthroline derivatives may be replaced with deuterium.

[0519] R 11 ~R 18 The alkyl, cycloalkyl and aryl in the above formula (ETM-2) are R 11 ~R 18 can be cited. In addition to the above examples, φ may have the following structural formulas. In the structural formulas below, R is independently hydrogen, methyl, ethyl, isopropyl, cyclohexyl, phenyl, 1-naphthyl, 2-naphthyl, biphenylyl, or terphenylyl, and * indicates a bonding position.

[0520] [ka]

[0521] Specific examples of the phenanthroline derivative include 4,7-diphenyl-1,10-phenanthroline, 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline, 9,10-di(1,10-phenanthroline-2-yl)anthracene, 2,6-di(1,10-phenanthroline-5-yl)pyridine, 1,3,5-tri(1,10-phenanthroline-5-yl)benzene, 9,9'-difluoro-bi(1,10-phenanthroline-5-yl), bathocuproine, 1,3-bis(2-phenyl-1,10-phenanthroline-9-yl)benzene, and compounds represented by the following structural formula.

[0522] [ka]

[0523] The phenanthroline derivative can be produced using known raw materials and known synthesis methods.

[0524] <Quinolinol metal complexes> The quinolinol metal complex is, for example, a compound represented by the following formula (ETM-13). [ka]

[0525] In the formula, R 1 ~R 6 are each independently hydrogen, fluorine, alkyl, cycloalkyl, aralkyl, alkenyl, cyano, alkoxy or aryl; M is Li, Al, Ga, Be or Zn; and n is an integer of 1 to 3.

[0526] 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.

[0527] The quinolinol metal complex can be produced using known raw materials and known synthesis methods.

[0528] <Thiazole derivatives and benzothiazole derivatives> The thiazole derivative is, for example, a compound represented by the following formula (ETM-14-1). [ka] The benzothiazole derivative is, for example, a compound represented by the following formula (ETM-14-2). [ka]

[0529] In each formula, φ is an n-valent aryl ring (preferably an n-valent benzene ring, naphthalene ring, anthracene ring, fluorene ring, benzofluorene ring, phenalene ring, phenanthrene ring, or triphenylene ring), and n is an integer from 1 to 4. A "thiazole-based substituent" or a "benzothiazole-based substituent" is a substituent in which the pyridyl in the "pyridine-based substituent" in the above formulae (ETM-2), (ETM-2-1), and (ETM-2-2) is replaced with the below-mentioned thiazolyl or benzothiazolyl, and at least one hydrogen in the thiazole derivative and the benzothiazole derivative may be replaced with a deuterium.

[0530] [ka]

[0531] It is further preferable that φ is an anthracene ring or a fluorene ring. In this case, the structure can be as described in the above formula (ETM-2-1) or formula (ETM-2-2). 11 ~R 18 The explanation for formula (ETM-2-1) or formula (ETM-2-2) above can be cited. In addition, in formula (ETM-2-1) or formula (ETM-2-2) above, 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 the above formula (ETM-2-1) 11 ~R 18 At least one of the substituents is replaced with a thiazole-based substituent (or a benzothiazole-based substituent) to form a "pyridine-based substituent" R 11 ~R 18may be substituted.

[0532] These thiazole or benzothiazole derivatives can be produced using known raw materials and known synthesis methods.

[0533] <Silole derivatives> The silole derivative is, for example, a compound represented by the following formula (ETM-15), the details of which are described in JP-A-9-194487. [ka]

[0534] 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 explanation in formula (2) and the explanation in formula (ETM-7-2) can be 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 explanation in formula (ETM-7-2) can be cited. Furthermore, X and Y, both of which are alkyl, may be bonded to form a ring.

[0535] 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.

[0536] R 1 ~R 4 For details of halogen, alkyl, cycloalkyl, alkoxy, aryloxy, amino, aryl, heteroaryl, alkenyl and alkynyl in, the explanation in formula (2) can be cited.

[0537] R 1 ~R 4 For details of the alkyl, aryl and alkoxy in the alkylcarbonyl, arylcarbonyl, alkoxycarbonyl, aryloxycarbonyl, alkylcarbonyloxy, arylcarbonyloxy, alkoxycarbonyloxy and aryloxycarbonyloxy in the above, the explanation in formula (2) can be cited.

[0538] Examples of silyl include a silyl group and a group in which at least one of the three hydrogen atoms of the silyl group is independently substituted with an aryl, an alkyl, or a cycloalkyl, and tri-substituted silyl is preferable, such as triarylsilyl, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, and alkyldicycloalkylsilyl. For details of the aryl, alkyl, and cycloalkyl, see the explanation in formula (2).

[0539] The condensed ring formed between adjacent substituents is, for example, R 1 and R 2 , R 2 and R 3 , R 3 and R 4 etc. These fused rings may contain nitrogen, oxygen, or sulfur atoms in the ring structure, and may be fused with another ring.

[0540] However, preferably, R 1 and R 4 is phenyl, X and Y are not alkyl or phenyl. 1 and R 4 When R is thienyl, X and Y are alkyl, R is thienyl, 2 and R 3 is alkyl, aryl, alkenyl or R 2 and R 3 In addition, it is preferable that R 1 and R 4 When is a silyl group, R 2 , R 3 , X and Y are each independently not hydrogen or alkyl having 1 to 6 carbon atoms. 1 and R 2 In the case of a structure in which a benzene ring is condensed, X and Y are not alkyl and phenyl.

[0541] These silole derivatives can be produced using known raw materials and known synthesis methods.

[0542] <Azoline derivatives> The azoline derivative is, for example, a compound represented by the following formula (ETM-16), details of which are described in International Publication No. 2017 / 014226. [ka]

[0543] In formula (ETM-16), φ is an m-valent group derived from an aromatic hydrocarbon having 6 to 40 carbon atoms or an m-valent group derived from an aromatic heterocycle having 2 to 40 carbon atoms, and at least one hydrogen of φ is optionally substituted by alkyl having 1 to 6 carbon atoms, cycloalkyl having 3 to 14 carbon atoms, aryl having 6 to 18 carbon atoms, or heteroaryl having 2 to 18 carbon atoms; Y's are each independently -O-, -S- or >N-Ar, Ar is an aryl having 6 to 12 carbon atoms or a heteroaryl having 2 to 12 carbon atoms, at least one hydrogen of Ar may be substituted by an alkyl having 1 to 4 carbon atoms, a cycloalkyl having 5 to 10 carbon atoms, an aryl having 6 to 12 carbon atoms or a heteroaryl having 2 to 12 carbon atoms, R 1 ~R 5 are each independently hydrogen, alkyl having 1 to 4 carbon atoms, or cycloalkyl having 5 to 10 carbon atoms, provided that Ar in the >N-Ar and R 1 ~R 5 one of which is a site for binding to L; Each L is independently selected from the group consisting of a divalent group represented by the following formula (L-1) and a divalent group represented by the following formula (L-2): [ka]

[0544] In formula (L-1), X 1 ~X 6 are each independently =CR 6 - or =N- and X 1 ~X 6 At least two of the =CR 6 - and X 1 ~X 6 Two of =CR 6 -R in 6 is the site of binding to φ or the azoline ring, and the other =CR 6 -R in 6 is hydrogen, In formula (L-2), X 7 ~X 14are each independently =CR 6 - or =N- and X 7 ~X 14 At least two of the =CR 6 - and X 7 ~X 14 Two of =CR 6 -R in 6 is the site of binding to φ or the azoline ring, and the other =CR 6 -R in 6 is hydrogen, at least one hydrogen atom of L may be substituted with alkyl having 1 to 4 carbon atoms, cycloalkyl having 5 to 10 carbon atoms, aryl having 6 to 10 carbon atoms, or heteroaryl having 2 to 10 carbon atoms; m is an integer of 1 to 4, and when m is an integer of 2 to 4, the groups formed by the azoline ring and L may be the same or different, and At least one hydrogen atom in the compound represented by formula (ETM-16) may be substituted with deuterium.

[0545] Specific azoline derivatives are compounds represented by the following formula (ETM-16-1) or formula (ETM-16-2). [ka]

[0546] In formula (ETM-16-1) and formula (ETM-16-2), φ is an m-valent group derived from an aromatic hydrocarbon having 6 to 40 carbon atoms or an m-valent group derived from an aromatic heterocycle having 2 to 40 carbon atoms, and at least one hydrogen of φ is optionally substituted by alkyl having 1 to 6 carbon atoms, cycloalkyl having 3 to 14 carbon atoms, aryl having 6 to 18 carbon atoms, or heteroaryl having 2 to 18 carbon atoms; In formula (ETM-16-1), each Y is independently -O-, -S- or >N-Ar, Ar is an aryl having 6 to 12 carbon atoms or a heteroaryl having 2 to 12 carbon atoms, and at least one hydrogen of Ar is optionally substituted by an alkyl having 1 to 4 carbon atoms, a cycloalkyl having 5 to 10 carbon atoms, an aryl having 6 to 12 carbon atoms, or a heteroaryl having 2 to 12 carbon atoms; In formula (ETM-16-1), R 1 ~R 4 are each independently hydrogen, alkyl having 1 to 4 carbon atoms, or cycloalkyl having 5 to 10 carbon atoms, with the proviso that R 1 and R 2 are identical, and R 3 and R 4 are identical, In formula (ETM-16-2), R 1 ~R 5 are each independently hydrogen, alkyl having 1 to 4 carbon atoms, or cycloalkyl having 5 to 10 carbon atoms, with the proviso that R 1 and R 2 are identical, and R 3 and R 4 are identical, In formula (ETM-16-1) and formula (ETM-16-2), Each L is independently selected from the group consisting of a divalent group represented by the following formula (L-1) and a divalent group represented by the following formula (L-2):

[0547] [ka] In formula (L-1), X 1 ~X 6 are each independently =CR 6 - or =N- and X 1 ~X 6 At least two of the =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 6is hydrogen, In formula (L-2), X 7 ~X 14 are each independently =CR 6 - or =N- and X 7 ~X 14 At least two of the =CR 6 - and X 7 ~X 14 Two of =CR 6 -R in 6 is the site of binding to φ or the azoline ring, and the other =CR 6 -R in 6 is hydrogen, at least one hydrogen atom of L may be substituted with alkyl having 1 to 4 carbon atoms, cycloalkyl having 5 to 10 carbon atoms, aryl having 6 to 10 carbon atoms, or heteroaryl having 2 to 10 carbon atoms; m is an integer of 1 to 4, and when m is an integer of 2 to 4, the groups formed by the azoline ring and L may be the same or different, and At least one hydrogen atom in the compound represented by formula (ETM-16-1) or formula (ETM-16-2) may be replaced with deuterium.

[0548] 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.

[0549] [ka]

[0550] [ka]

[0551] [ka]

[0552] 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.

[0553] 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.

[0554] Preferably, Ar in >N-Ar as Y or Z is selected from the group consisting of phenyl, naphthyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, naphthyridinyl, phthalazinyl, quinoxalinyl, quinazolinyl, cinnolinyl, and pteridinyl, and at least one hydrogen of Ar in >N-Ar as Y may be substituted with alkyl having 1 to 4 carbon atoms, cycloalkyl having 5 to 10 carbon atoms, or aryl having 6 to 10 carbon atoms.

[0555] Preferably, R 1 ~R 4are each independently hydrogen, alkyl having 1 to 4 carbon atoms, or cycloalkyl having 5 to 10 carbon atoms, with the proviso that R 1 and R 2 are identical, and R 3 and R 4 are identical, and R 1 ~R 4 are not all hydrogen at the same time, and m is 1 or 2. When m is 2, the groups formed by the azoline ring and L are the same.

[0556] Specific examples of azoline derivatives include the following compounds: In the structural formula, "Me" represents methyl. [ka]

[0557] [ka]

[0558] More preferably, φ is selected from the group consisting of divalent groups represented by the following formulas (φ2-1), (φ2-31), (φ2-32), (φ2-33) and (φ2-34), and at least one hydrogen of φ may be substituted by an aryl having 6 to 18 carbon atoms: [ka] L is a divalent ring group selected from the group consisting of benzene, pyridine, pyrazine, pyrimidine, pyridazine, and triazine, and at least one hydrogen of L is optionally substituted by alkyl having 1 to 4 carbon atoms, cycloalkyl having 5 to 10 carbon atoms, aryl having 6 to 10 carbon atoms, or heteroaryl having 2 to 14 carbon atoms; Ar in >N-Ar as Y is selected from the group consisting of phenyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, and triazinyl, and at least one hydrogen of the Ar may be substituted by alkyl having 1 to 4 carbon atoms, cycloalkyl having 5 to 10 carbon atoms, or aryl having 6 to 10 carbon atoms; R 1 ~R 4 are each independently hydrogen, alkyl having 1 to 4 carbon atoms, or cycloalkyl having 5 to 10 carbon atoms, with the proviso that R 1 and R 2 are identical, and R 3 and R 4 are identical, and R 1 ~R 4 cannot all become hydrogen at the same time, and m is 2, and the groups formed by the azoline ring and L are the same. In the above formulae (φ2-1), (φ2-31), (φ2-32), (φ2-33) and (φ2-34), * indicates the bonding position.

[0559] Other specific examples of azoline derivatives include the following compounds: In the structural formula, "Me" represents methyl. [ka]

[0560] For details of the alkyl, cycloalkyl, aryl or heteroaryl in the above formulas defining this azoline derivative, the explanation in formula (2) can be cited.

[0561] The azoline derivative can be produced using known raw materials and known synthesis methods.

[0562] <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.

[0563] 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.

[0564] 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 represented by formula (1) can be cited as the reactive substituent. The applications of such polymer compounds and crosslinked polymers will be described in detail below.

[0565] 2-1-7. 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 .

[0566] 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.

[0567] 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.

[0568] 2-1-8. 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.

[0569] 2-1-9. 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.

[0570] 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.

[0571] 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.

[0572] <Vapor deposition method> A thin film of an anode material is formed on a suitable substrate by vapor deposition or the like to prepare an anode, and then a thin film of a hole injection layer and a hole transport layer is formed on the anode. A host material and a dopant material are co-deposited on the anode to form a thin film as a light-emitting layer, an electron transport layer and an electron injection layer are formed on the light-emitting layer, and a thin film of a cathode material is further formed by vapor deposition or the like to prepare a cathode, thereby obtaining a desired organic EL device. Note that in the preparation of the above-mentioned organic EL device, the preparation order can also be reversed, and the layers can be prepared in the order of cathode, electron injection layer, electron transport layer, light-emitting layer, hole transport layer, hole injection layer, and anode.

[0573] <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.

[0574] 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 crosslinked polymer), the polymer is further crosslinked by the drying step to form a crosslinked polymer. Depending on the difference in the coating step, a method using a spin coater is called a spin coat method, a method using a slit coater is called a slit coat method, a method using a plate is called a gravure, offset, reverse offset, or flexographic printing method, a method using an inkjet printer is called an inkjet method, and a method spraying in a mist form is called a spray method. The drying step includes air drying, heating, drying under reduced pressure, and the like. The drying step may be performed only once, or may be performed multiple times using different methods or conditions. In addition, different methods may be used in combination, such as baking under reduced pressure.

[0575] 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.

[0576] 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.

[0577] 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.

[0578] For example, the procedure for producing an organic EL element by partially applying a wet film formation method will be described below. (Step 1) Formation of the anode by vacuum deposition (Step 2) Forming a film by a wet film formation method using a composition for forming a hole injection layer containing a material for the hole injection layer (Step 3) Forming a film by a wet film formation method using a composition for forming a hole transport layer containing a material for the hole transport layer (Step 4) Formation of a film by a wet film formation method using a composition for forming an emitting layer containing a host material and a dopant material (Step 5) Formation of the electron transport layer by vacuum deposition (Step 6) Formation of the electron injection layer by vacuum deposition (Step 7) Cathode deposition by vacuum deposition Through this procedure, an organic EL element consisting of an anode, a hole injection layer, a hole transport layer, an emitting layer made of a host material and a dopant material, an electron transport layer, an electron injection layer, and a cathode is obtained. Of course, if there is a means for preventing dissolution of the lower light-emitting layer, or if a means for forming a film from the cathode side is used in the opposite procedure to the above, a layer-forming composition containing a material for the electron transport layer and a material for the electron injection layer can be prepared and then the layer can be formed by a wet film formation method.

[0579] <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.

[0580] <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.

[0581] 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.

[0582] Materials that can be used for the banks include, but are not limited to, polysaccharides and their derivatives, homopolymers and copolymers of hydroxyl-containing ethylenic monomers, biopolymers, polyacryloyl compounds, polyesters, polystyrenes, polyimides, polyamideimides, polyetherimides, polysulfides, polysulfones, polyphenylenes, polyphenyl ethers, polyurethanes, epoxy (meth)acrylates, melamine (meth)acrylates, polyolefins, cyclic polyolefins, acrylonitrile-butadiene-styrene copolymers (ABS), silicone resins, polyvinyl chloride, chlorinated polyethylene, chlorinated polypropylene, polyacetate, polynorbornene, synthetic rubber, fluorinated polymers such as polyfluorovinylidene, polytetrafluoroethylene, and polyhexafluoropropylene, copolymers of fluoroolefins and hydrocarbon olefins, and fluorocarbon polymers.

[0583] <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.

[0584] <Organic solvent> The organic layer forming composition contains at least one organic solvent. By controlling the evaporation rate of the organic solvent during film formation, it is possible to control and improve the film forming properties, the presence or absence of defects in the coating film, the surface roughness, and the smoothness. In addition, during film formation using the inkjet method, it is possible to control the meniscus stability at the pinhole of the inkjet head, and control and improve the ejection properties. In addition, by controlling the drying rate of the film and the orientation of the derivative molecules, it is possible to improve the electrical properties, light emitting properties, efficiency, and life of an organic EL element having an organic layer obtained from the organic layer forming composition.

[0585] (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.

[0586] Furthermore, the organic solvent contains a good solvent (GS) and a poor solvent (PS) for at least one of the solutes, and the boiling point (BP) of the good solvent (GS) is GS ) is the boiling point (BP PS ) is particularly preferred. By adding a poor solvent with a high boiling point, the good solvent with a low boiling point volatilizes first during film formation, increasing the concentration of the components in the composition and the concentration of the poor solvent, promoting rapid film formation. This results in a coating film with few defects, small surface roughness, and high smoothness.

[0587] 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.

[0588] After the film is formed, the organic solvent is removed from the coating film by a drying process such as vacuum, reduced pressure, or heating. When heating is performed, from the viewpoint of improving the coating film-forming property, it is preferable to perform the heating at a temperature of at least one of the solutes at a glass transition temperature (Tg) +30°C or lower. From the viewpoint of reducing the residual solvent, it is preferable to heat at at least one of the solutes at a glass transition temperature (Tg) -30°C or higher. Even if the heating temperature is lower than the boiling point of the organic solvent, the organic solvent is sufficiently removed because the film is thin. Also, drying may be performed multiple times at different temperatures, and multiple drying methods may be used in combination.

[0589] (2) Specific examples of organic solvents Examples of the organic solvent used in the composition for forming the organic layer include alkylbenzene solvents, phenyl ether solvents, alkyl ether solvents, cyclic ketone solvents, aliphatic ketone solvents, monocyclic ketone solvents, solvents having a diester skeleton, and fluorine-containing solvents. Specific examples include pentanol, hexanol, heptanol, octanol, nonanol, decanol, undecanol, dodecanol, tetradecanol, hexane-2-ol, heptan-2-ol, octan-2-ol, decan-2-ol, dodecan-2-ol, cyclohexanol, Sanol, α-terpineol, β-terpineol, γ-terpineol, δ-terpineol, terpineol (mixture), ethylene glycol monomethyl ether acetate, propylene glycol monomethyl ether acetate, diethylene glycol dimethyl ether, dipropylene glycol dimethyl ether, diethylene glycol ethyl methyl ether, diethylene glycol isopropyl methyl ether, dipropylene glycol monomethyl ether, diethylene glycol diethyl ether, diethylene glycol monomethyl ether , diethylene glycol butyl methyl ether, tripropylene glycol dimethyl ether, triethylene glycol dimethyl ether, diethylene glycol monobutyl ether, ethylene glycol monophenyl ether, triethylene glycol monomethyl ether, diethylene glycol dibutyl ether, triethylene glycol butyl methyl ether, polyethylene glycol dimethyl ether, tetraethylene glycol dimethyl ether, p-xylene, m-xylene, o-xylene, 2,6-lutidine, 2-fluoro-m-xylene, 3-fluoro-o-xylene, 2-chlorobenzotrifluoride, cumene, toluene, 2-chloro-6-fluorotoluene, 2-fluoroanisole, anisole, 2,3-dimethylpyrazine, bromobenzene, 4-fluoroanisole, 3-fluoroanisole, 3-trifluoromethylanisole, mesitylene, 1,2,4-trimethylbenzene, t-butylbenzene, 2-methylanisole, phenetole, benzodioxole, 4-methylanisole, s-butylbenzene, 3-methylanisole, 4-fluoro-3-methylanisole, cymene, 1,2,3-Trimethylbenzene, 1,2-Dichlorobenzene, 2-Fluorobenzonitrile, 4-Fluoroveratrol, 2,6-Dimethylanisole, n-Butylbenzene, 3-Fluorobenzonitrile, Decalin (Decahydronaphthalene), Neopentylbenzene, 2,5-Dimethylanisole, 2,4-Dimethylanisole, Benzonitrile, 3,5-Dimethylanisole, Diphenyl ether, 1-Fluoro-3,5-dimethoxybenzene, Methyl benzoate, Isopentylbenzene, 3,4-Dimethylanisole, o-Tolunitrile, n-Amylbenzene, Veratrol, 1,2,3,4-Tetrahydronaphthalene, Ethyl benzoate, n-Hexylbenzene, Propyl benzoate, Cyclohexylbenzene, 1- Examples of the solvent include, but are not limited to, methylnaphthalene, butyl benzoate, 2-methylbiphenyl, 3-phenoxytoluene, 2,2'-bitolyl, dodecylbenzene, dipentylbenzene, tetramethylbenzene, trimethoxybenzene, trimethoxytoluene, 2,3-dihydrobenzofuran, 1-methyl-4-(propoxymethyl)benzene, 1-methyl-4-(butyloxymethyl)benzene, 1-methyl-4-(pentyloxymethyl)benzene, 1-methyl-4-(hexyloxymethyl)benzene, 1-methyl-4-(heptyloxymethyl)benzene, benzyl butyl ether, benzyl pentyl ether, benzyl hexyl ether, benzyl heptyl ether, and benzyl octyl ether. The solvent may be used alone or in a mixture.

[0590] <Optional ingredients> The composition for forming the organic layer may contain optional components, such as a binder and a surfactant, to the extent that the properties of the composition are not impaired.

[0591] (1) Binder The composition for forming an organic layer may contain a binder. The binder forms a film during film formation and bonds the resulting film to a substrate. The binder also plays a role in dissolving, dispersing, and binding other components in the composition for forming an organic layer.

[0592] Examples of binders used in the organic layer-forming composition include, but are not limited to, acrylic resins, polyethylene terephthalate, ethylene-vinyl acetate copolymers, ethylene-vinyl alcohol copolymers, acrylonitrile-ethylene-styrene copolymer (AES) resins, ionomers, chlorinated polyethers, diallyl phthalate resins, unsaturated polyester resins, polyethylene, polypropylene, polyvinyl chloride, polyvinylidene chloride, polystyrene, polyvinyl acetate, Teflon, acrylonitrile-butadiene-styrene copolymer (ABS) resins, acrylonitrile-styrene copolymer (AS) resins, phenolic resins, epoxy resins, melamine resins, urea resins, alkyd resins, polyurethanes, and copolymers of the above resins and polymers.

[0593] The binder used in the organic layer-forming composition may be of one type or a mixture of two or more types.

[0594] (2) Surfactants The organic layer forming composition may contain a surfactant, for example, to control the film surface uniformity, solvent affinity and liquid repellency of the organic layer forming composition. Surfactants are classified into ionic and nonionic based on the structure of the hydrophilic group, and further classified into alkyl, silicon and fluorine based on the structure of the hydrophobic group. In addition, based on the molecular structure, they are classified into monomolecular systems with relatively small molecular weight and simple structure, and polymer systems with large molecular weight and side chains or branches. In addition, based on the composition, they are classified into single systems and mixed systems in which two or more types of surfactants and base materials are mixed. All types of surfactants can be used as surfactants that can be used in the organic layer forming composition.

[0595] Examples of surfactants include Polyflow No. 45, Polyflow KL-245, Polyflow No. 75, Polyflow No. 90, Polyflow No. 95 (trade names, manufactured by Kyoeisha Chemical Industry Co., Ltd.), Disperbyk 161, Disperbyk 162, Disperbyk 163, Disperbyk 164, Disperbyk 166, Disperbyk 170, Disperbyk 180, Disperbyk 181, Disperbyk 182, BYK300, BYK 306, BYK310, BYK320, BYK330, BYK342, BYK344, BYK346 (trade name, manufactured by BYK Japan Co., Ltd.), KP-341, KP-358, KP-368, KF-96-50CS, KF-50-100CS (trade name, manufactured by Shin-Etsu Chemical Co., Ltd.), Surflon SC-101, Surflon KH-40 (trade name, manufactured by Seimi Chemical Co., Ltd.), Ftergent 222F, Ftergent 251, FTX-218 (trade name, manufactured by Neos Co., Ltd.), EFTOP EF-351, EFTOP EF-352, EFTOP EF-601, EFTOP EF-801, EFTOPEF-802 (product name, manufactured by Mitsubishi Materials Corporation), Megafac F-470, Megafac F-471, Megafac F-475, Megafac R-08, Megafac F-477, Megafac F-479, Megafac F-553, Megafac F-554 (product name, manufactured by DIC Corporation), fluoroalkylbenzenesulfonates, fluoroalkylcarboxylates, fluoroalkylpolyoxyethyleneethers, fluoroalkylammonium iodides, fluoroalkylbetaines, fluoroalkylsulfonates, diglycerol tetrakis (fluoroalkylpolyoxyethyleneether), fluoroalkyltrimethylammonium salts, fluoroalkylaminosulfonates, polyoxyethylene nonyl Examples of the alkyl ethers include polyoxyethylene octylphenyl ether, polyoxyethylene alkyl ethers, polyoxyethylene laurate, polyoxyethylene oleate, polyoxyethylene stearate, polyoxyethylene laurylamine, sorbitan laurate, sorbitan palmitate, sorbitan stearate, sorbitan oleate, sorbitan fatty acid esters, polyoxyethylene sorbitan laurate, polyoxyethylene sorbitan palmitate, polyoxyethylene sorbitan stearate, polyoxyethylene sorbitan oleate, polyoxyethylene naphthyl ether, alkyl benzene sulfonates, and alkyl diphenyl ether disulfonates.

[0596] The surfactant may be used alone or in combination of two or more kinds.

[0597] <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.

[0598] More preferably, the first component is 0.005% by mass to 1.0% by mass, the second component is 0.095% by mass to 4.0% by mass, and the third component is 95.0% by mass to 99.9% by mass, more preferably, the first component is 0.05% by mass to 0.5% by mass, the second component is 0.25% by mass to 2.5% by mass, and the third component is 97.0% by mass to 99.7% by mass, based on the total mass of the composition for forming the light-emitting layer.

[0599] 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.

[0600] The higher the viscosity of the composition for forming an organic layer, the better the film-forming properties and the better the ejection properties when using an inkjet method. On the other hand, the lower the viscosity, the easier it is to form a thin film. For this reason, the viscosity of the composition for forming an organic layer at 25°C is preferably 0.3 to 3 mPa·s, and more preferably 1 to 3 mPa·s. In the present invention, the viscosity is a value measured using a cone-plate type rotational viscometer (cone-plate type).

[0601] The lower the surface tension of the composition for forming an organic layer, the better the film-forming properties and the more defect-free the coating film will be. On the other hand, the higher the surface tension, the better the ink-jet ejection properties will be. For this reason, the viscosity of the composition for forming an organic layer is preferably such that the surface tension at 25°C is 20 to 40 mN / m, more preferably 20 to 30 mN / m. In the present invention, the surface tension is a value measured using the hanging drop method.

[0602] <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). Note that the crosslinked polymer corresponds to a coating film that is crosslinked in a network shape by applying a solution containing a polymer compound (crosslinkable polymer compound) and evaporating the solvent.

[0603] [ka]

[0604] In formula (XLP-1), MUx, ECx, and k are defined the same as MU, EC, and k in the above formula (SPH-1), except that the compound represented by formula (XLP-1) has at least one crosslinkable substituent (XLS), and preferably the content of the monovalent or divalent aromatic compound having a crosslinkable substituent is 0.1 to 80 mass% in the molecule.

[0605] 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 %.

[0606] 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.

[0607] [ka]

[0608] 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.

[0609] Examples of the divalent aromatic compound having a crosslinkable substituent include compounds having the following partial structure: [ka]

[0610] [ka]

[0611] [ka]

[0612] [ka]

[0613] <Methods of producing polymer compounds and crosslinkable polymer compounds> The manufacturing method of the polymer compound and the crosslinkable polymer compound will be described with reference to the compound represented by the above formula (SPH-1) and the compound represented by the above formula (XLP-1). These compounds can be synthesized by appropriately combining known manufacturing methods.

[0614] The solvent used in the reaction includes aromatic solvents, saturated / unsaturated hydrocarbon solvents, alcohol solvents, ether solvents, and the like, such as dimethoxyethane, 2-(2-methoxyethoxy)ethane, 2-(2-ethoxyethoxy)ethane, and the like.

[0615] The reaction may be carried out in a two-phase system. When the reaction is carried out in a two-phase system, a phase transfer catalyst such as a quaternary ammonium salt may be added, if necessary.

[0616] The compound of formula (SPH-1) and the compound of formula (XLP-1) may be produced in one step or in multiple steps. The compound may be produced by a batch polymerization method in which all the raw materials are put into a reaction vessel and then the reaction is started, a dropwise polymerization method in which the raw materials are added dropwise to a reaction vessel, or a precipitation polymerization method in which the product precipitates as the reaction proceeds, and these methods can be combined appropriately to synthesize the compound. For example, when the compound of formula (SPH-1) is synthesized in one step, the target product is obtained by adding a monomer having a polymerizable group bonded to the monomer unit (MU) and a monomer having a polymerizable group bonded to the end cap unit (EC) to a reaction vessel and then reacting the monomer. When the compound of formula (SPH-1) is synthesized in multiple steps, the monomer having a polymerizable group bonded to the monomer unit (MU) is polymerized to the target molecular weight, and then a monomer having a polymerizable group bonded to the end cap unit (EC) is added and reacted to obtain the target product. If different types of monomer units (MU) are added and reacted in multiple steps, a polymer having a concentration gradient in the structure of the monomer units can be produced. Also, after preparing a precursor polymer, the target polymer can be obtained by a post-reaction.

[0617] In addition, the primary structure of the polymer can be controlled by selecting the polymerizable group of the monomer. For example, as shown in synthesis schemes 1 to 3, it is possible to synthesize a polymer having a random primary structure (synthetic scheme 1) or a polymer having a regular primary structure (synthetic schemes 2 and 3), and these can be used in appropriate combinations depending on the target object. Furthermore, if a monomer having three or more polymerizable groups is used, a hyperbranched polymer or a dendrimer can be synthesized.

[0618] [ka]

[0619] Monomers that can be used in the present invention include those described in JP2010-189630A, WO2012 / 086671A, WO2013 / 191088A, WO2002 / 045184A, WO2011 / 049241A, WO2013 / 146806A, WO2005 / 049546A, WO2015 / 1458 ...B, WO2015 / 1458B, WO2015 / 1458B, WO2015 / 1458B, WO2015 / 1458B, WO2015 / 1458B, WO2015 / 1458B, WO2015 / 1458B, W It can be synthesized in accordance with the methods described in JP-A-2002 / 045184, JP-A-2010-215886, JP-A-2008-106241, JP-A-2010-215886, WO 2016 / 031639, JP-A-2011-174062, WO 2016 / 031639, WO 2016 / 031639, and WO 2002 / 045184.

[0620] In addition, specific polymer synthesis procedures are described in JP 2012-036388 A, WO 2015 / 008851 A, JP 2012-36381 A, JP 2012-144722 A, WO 2015 / 194448 A, WO 2013 / 146806 A, WO 2015 / 145871 A, WO 2016 / It can be synthesized in accordance with the methods described in WO 2016 / 031639, WO 2016 / 125560, WO 2016 / 031639, WO 2016 / 031639, WO 2016 / 125560, WO 2015 / 145871, WO 2011 / 049241, and JP 2012-144722 A.

[0621] 2-1-10.Application examples of organic electroluminescent devices The present invention can also be applied to a display device having an organic EL element or a lighting device having an organic EL element. A display device or lighting device including an organic EL element can be manufactured by a known method, for example by connecting the organic EL element according to this embodiment to a known driving device, and can be driven appropriately using a known driving method such as DC driving, pulse driving, or AC driving.

[0622] 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.

[0623] 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.

[0624] 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.

[0625] Examples of the lighting device include lighting devices for indoor lighting, backlights for liquid crystal display devices, etc. (see, for example, JP-A-2003-257621, JP-A-2003-277741, JP-A-2004-119211, etc.). Backlights are mainly used for the purpose of improving the visibility of non-self-luminous display devices, and are used in liquid crystal display devices, clocks, audio devices, automobile panels, display boards, signs, etc. In particular, for 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.

[0626] 2-2. 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.

[0627] 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.

[0628] The structure of an organic field effect transistor is usually such that a source electrode and a drain electrode are provided in contact with an organic semiconductor active layer formed using the polycyclic aromatic compound according to the present invention, and a gate electrode is provided sandwiching an insulating layer (dielectric layer) in contact with the organic semiconductor active layer. Examples of the element structure include the following structure. (1) Substrate / gate electrode / insulating layer / source and drain electrodes / organic semiconductor active layer (2) Substrate / gate electrode / insulating layer / organic semiconductor active layer / source electrode and drain electrode (3) Substrate / organic semiconductor active layer / source electrode / drain electrode / insulator layer / gate electrode (4) Substrate / source electrode / drain electrode / organic semiconductor active layer / insulator layer / gate electrode The organic field effect transistor thus configured can be used as a pixel driving switching element for an active matrix driving type liquid crystal display or an organic electroluminescence display.

[0629] The organic thin-film solar cell has a structure in which an anode such as ITO, a hole transport layer, a photoelectric conversion layer, an electron transport layer, and a cathode are laminated on a transparent substrate such as glass. The photoelectric conversion layer has a p-type semiconductor layer on the anode side and an n-type semiconductor layer on the cathode side. The polycyclic aromatic compound according to the present invention can be used as a material for a hole transport layer, a p-type semiconductor layer, an n-type semiconductor layer, and an electron transport layer depending on its physical properties. The polycyclic aromatic compound according to the present invention can function as a hole transport material or an electron transport material in an organic thin-film solar cell. In addition to the above, the organic thin-film solar cell may appropriately include a hole blocking layer, an electron blocking layer, an electron injection layer, a hole injection layer, a smoothing layer, and the like. The organic thin-film solar cell can be used by appropriately selecting and combining known materials used in organic thin-film solar cells. EXAMPLES

[0630] The present invention will be described in more detail below with reference to examples, but the present invention is not limited thereto. First, synthesis examples of polycyclic aromatic compounds will be described below.

[0631] Synthesis example (1) Synthesis of compound (1-1) [ka]

[0632] Under a nitrogen atmosphere, 2-chloro-6-bromoanisole (10 g) was dissolved in THF (50 mL) and cooled to -78°C. To this was slowly added n-butyllithium / n-hexane solution (1.6 M). After stirring at the same temperature, 9-fluorenone (8.1 g) was added and further stirred. After the reaction, the reaction was stopped with saturated ammonium chloride, extracted with toluene, and purified by silica gel column chromatography to obtain intermediate A.

[0633] [ka]

[0634] Under a nitrogen atmosphere, intermediate A (10 g) was dissolved in benzene (50 mL), boron trifluoride diethyl ether complex (0.4 g) was added, and the mixture was heated to reflux. After the reaction, water was added to stop the reaction, and the organic layer was washed with water and separated. It was then purified by silica gel column chromatography to obtain intermediate B.

[0635] [ka]

[0636] Under a nitrogen atmosphere, intermediate B (10 g), sodium t-butoxide (6.3 g) and dichlorobis[(di-t-butyl(4-dimethylaminophenyl)phosphino)palladium (Pd-132, 0.18 g) as a palladium catalyst were dissolved in xylene (50 mL) and heated to reflux. After the reaction, the organic layer was washed with water, separated, and then purified by silica gel column chromatography to obtain intermediate C.

[0637] [ka]

[0638] Under a nitrogen atmosphere, intermediate C (10 g) was dissolved in dichloromethane (50 mL) and cooled to 0° C., and then boron tribromide (6.3 g) was slowly added. After the reaction, water was added to stop the reaction, and the organic layer was washed with water and separated, and then purified by silica gel column chromatography to obtain intermediate D.

[0639] [ka]

[0640] Under a nitrogen atmosphere, intermediate D (9.0 g) was dissolved in pyridine (50 mL) and cooled to 0°C, and then trifluoromethanesulfonic anhydride was slowly added. After the reaction, water was added to stop the reaction, and toluene was added for liquid separation and extraction. Intermediate E was obtained by purifying the mixture by silica gel column chromatography.

[0641] [ka]

[0642] Under a nitrogen atmosphere, intermediate E (10 g), [1,1'-bis(diphenylphosphino)ferrocene]palladium(II) dichloride (PdCl 2 (dppf), 0.12 g), potassium acetate (3.1 g), potassium carbonate (4.4 g) and bis-pinacol diboron (B 2 Pin 2 Cyclopentyl methyl ether (50 mL) was added to the reaction mixture (4.8 g) and the mixture was heated to reflux. After the reaction, water was added to stop the reaction, and the mixture was separated and purified using a silica gel column to obtain intermediate F.

[0643] [ka]

[0644] Under a nitrogen atmosphere, intermediate F (9 g) was dissolved in chlorobenzene (20 ml), and aluminum chloride (9.8 g) and N,N-diisopropylethylamine (DIPEA, 9.5 g) were added. After the reaction was completed, the reaction mixture was cooled to room temperature and poured into ice water, and toluene was added to extract the organic layer. The compound represented by formula (1-1) was obtained by purifying it with a silica gel column. EI-MS: m / z=493. 1 H-NMR (CDCl 3 ): δ=6.59(d,1H), 6.75(d,1H), 7.15(m,4H), 7.27-7.29(m,3H), 7.35-7.39(m, 5H), 7.51-7.59(m,4H), 7.79(d,2H), 7.88(dt,2H), 8.44(d,1H), 8.52(d,1H)

[0645] [ka]

[0646] Synthesis example (2) Synthesis of compound (1-3) The compound represented by formula (1-3) was obtained using compound (F-3) in the same manner as in Synthesis Example (1). EI-MS: m / z=605. 1 H-NMR (CDCl 3 ): δ=1.48(s,6H), 6.63(d,1H), 7.22-7.31(m,8H), 7.39(m,3H), 7.51-7.55 (m,3H), 7.74(d,1H), 7.81(d,2H), 7.89(d,2H), 8.42(d,1H), 8.49(d,1H)

[0647] [ka]

[0648] Synthesis example (3) Synthesis of compound (1-23) The compound represented by formula (1-23) was obtained using compound (F-23) in the same manner as in Synthesis Example (1). EI-MS: m / z=603. 1 H-NMR (CDCl 3 ): δ=1.48(s,6H), 6.60(d,1H), 7.00-7.02(m,2H), 7.29-7.33(m,4H), 7.40(m,2H), 7.48( d,2H), 7.56(dt,1H), 7.80(d,2H), 7.89(d,2H), 8.20(s,1H), 8.35(m,2H), 8.42(d,1H)

[0649] [ka]

[0650] Synthesis example (4) Synthesis of compound (1-83) The compound represented by formula (1-83) was obtained using compound (F-83) in the same manner as in Synthesis Example (1). EI-MS: m / z=621. 1H-NMR (CDCl 3 ): δ=1.49(s,6H), 6.63(d,1H), 7.01(dt,2H), 7.14-7.19(m,8H), 7.32(dt,2H), 7 .39(m,3H), 7.58(dt,1H), 7.73(d,1H), 7.82(d,2H), 8.42(d,1H), 8.49(d,1H)

[0651] [ka]

[0652] Synthesis example (5) Synthesis of compound (1-103) A compound represented by formula (1-103) was obtained using compound (F-103) in the same manner as in Synthesis Example (1). EI-MS: m / z=619. 1 H-NMR (CDCl 3 ): δ=1.45(s,6H), 6.61(d,1H), 6.99-7.03(m,3H), 7.13-7.22(m,5H), 7.31(dt,2H) , 7.41(m,2H), 7.55(dt,1H), 7.80(d,2H), 7.89(m,2H), 8.21(s,1H), 8.45(d,1H)

[0653] [ka]

[0654] Synthesis Example (5-1) Synthesis of compound (H1-1) [ka]

[0655] Compound (H1-1) was synthesized according to the method described in WO 2017 / 024703.

[0656] Synthesis Example (5-2) Synthesis of compound (H1-2) [ka]

[0657] Compound (H1-2) was synthesized according to the method described in WO 2017 / 061480.

[0658] Comparative compound-1 was synthesized according to the method described in WO 2015 / 102118.

[0659] By appropriately changing the raw material compounds, other compounds of the present invention can be synthesized according to the methods of the above-mentioned synthesis examples.

[0660] Next, in order to explain the present invention in more detail, examples of organic EL devices using the compounds of the present invention will be shown, but the present invention is not limited to these.

[0661] <Evaluation of deposition-type organic EL elements> Organic EL devices according to Examples 1 to 19 and Comparative Examples 1 to 4 were fabricated, and the luminance was 1000 cd / m 2 The characteristics of the light emission, such as voltage (V), emission wavelength (nm), and external quantum efficiency (%), were measured, and then the current was set at 10 mA / cm 2 The time for which the luminance was maintained at 90% or more of the initial luminance when the device was driven at a constant current density of 1000 Hz was measured.

[0662] The quantum efficiency of a light-emitting element includes internal quantum efficiency and external quantum efficiency, and the internal quantum efficiency indicates the ratio at which the external energy injected as electrons (or holes) into the light-emitting layer of the light-emitting element 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.

[0663] The external quantum efficiency was measured as follows: The luminance of the element was 1000 cd / m using an Advantest voltage / current generator R6144. 2The element was made to emit light by applying a voltage that would result in a value of 10 ...

[0664] <Examples 1 to 21 and Comparative Examples 1 to 2> The material configurations of the layers in the organic EL devices according to Examples 1 to 21 and Comparative Examples 1 and 2 are shown in Table 1 below. [Table 1]

[0665] In Table 1, (HI) is N 4 ,N 4' -Diphenyl-N 4 ,N 4'-bis(9-phenyl-9H-carbazol-3-yl)-[1,1'-biphenyl]-4,4'-diamine, (HAT-CN) is 1,4,5,8,9,12-hexaazatriphenylene hexacarbonitrile, (HT-1) is N-([1,1'-biphenyl]-4-yl-9,9-dimethyl-N-[4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluoren-2-amine[1,1'-biphenyl]-4-amine, (HT-2) is N,N-bis(4-(dibenzo[b,d]furan-4-yl)phenyl)-[1,1':4',1"-terphenyl]-4-amine, (BH-1) is 2-(10-phenylaza (BH-1) is 2-(10-phenylanthracen-9-yl) naphtho[2,3-b]benzofuran, (BH-2) is 2-(10-phenylanthracen-9-yl) dibenzo[b,d]furan, (BH-3) is 9-([2,2'-binaphthalene]-7-yl)-10-phenylanthracene, (ET-1) is 9,9'-(5-(6-(1,1'-biphenyl)-4-yl)-2-phenylpyrimidin-4-yl)-1,3-phenylene]bis(9H-carbazole), and (ET-2) is 2,2'-[(2-phenylanthracen-9,10-diyl) dibenzene-4,1-diyl] dipyridine. The chemical structures are shown below along with "Liq" and "Comparative Compound-1".

[0666] [ka]

[0667] [ka]

[0668] <Example 1> A 26 mm × 28 mm × 0.7 mm glass substrate (manufactured by Optoscience Co., Ltd.) on which an ITO film having a thickness of 180 nm was formed by sputtering and polished to 150 nm was used as a transparent support substrate. This transparent support substrate was fixed to a substrate holder of a commercially available deposition apparatus (manufactured by Showa Vacuum Co., Ltd.), and a molybdenum deposition boat containing HI, HAT-CN, HT-1, H1-1, BH-1, compound (1-1), ET-1, and ET-2, and an aluminum nitride deposition boat containing Liq, LiF, and aluminum, were attached.

[0669] The following layers are formed in order on the ITO film of the transparent support substrate. -4 The pressure was reduced to 10 Pa, and first, HI was heated and evaporated to a thickness of 40 nm, then HAT-CN was heated and evaporated to a thickness of 5 nm, then HT-1 was heated and evaporated to a thickness of 45 nm, and then H1-1 was heated and evaporated to a thickness of 10 nm to form a hole layer consisting of four layers. Next, BH-1 and compound (1-1) were heated simultaneously and evaporated to a thickness of 25 nm to form an emitting layer. The evaporation rate was adjusted so that the mass ratio of BH-1 to compound (1-1) was approximately 98:2. Furthermore, ET-1 was heated and evaporated to a thickness of 5 nm, and then ET-2 and Liq were heated simultaneously and evaporated to a thickness of 25 nm to form an electron layer consisting of two layers. The evaporation rate was adjusted so that the mass ratio of ET-2 to Liq was approximately 50:50. The evaporation rate of each layer was 0.01 to 1 nm / sec. Thereafter, LiF was heated and evaporated at a deposition rate of 0.01 to 0.1 nm / sec to a thickness of 1 nm, and then aluminum was heated and evaporated to a thickness of 100 nm to form a cathode, thereby obtaining an organic EL device.

[0670] 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, and the time during which the luminance was maintained at 90% or more of the initial luminance was also measured.

[0671] 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 When the light-emitting characteristics were measured, as shown in Table 1, the driving voltage was 3.72 V, the external quantum efficiency was 7.65%, and the time during which 90% or more of the initial luminance was retained was 132 hours.

[0672] <Examples 2 to 21> According to Example 1, each organic EL element was produced with the layer structure shown in Table 1, and the EL characteristic data was measured (Table 2).

[0673] <Comparative Examples 1 to 2> According to Example 1, each organic EL element was produced with the layer structure shown in Table 1, and the EL characteristic data was measured (Table 2).

[0674] [Table 2]

[0675] As shown in the above measurement results, it was confirmed that high external quantum efficiency and long life were achieved in an organic EL device having an emitting layer using the compound of the present invention as a dopant. [Industrial Applicability]

[0676] The present invention provides a novel polycyclic aromatic compound or a multimer thereof having a spiro structure. The present invention can increase the options of materials for organic devices, such as materials for organic EL elements. In addition, by using the polycyclic aromatic compound or a multimer thereof of the present invention as a material for organic EL elements, it is possible to provide, for example, an organic EL element having excellent luminous efficiency and element life, a display device including the same, and a lighting device including the same. [Explanation of symbols]

[0677] 100 Organic electroluminescent device 101 Substrate 102 Anode 103 Hole injection layer 104 Hole transport layer 105 Light-emitting layer 106 Electron transport layer 107 Electron injection layer 108 Cathode

Claims

1. A polycyclic aromatic compound represented by the following formula (1): 【Chemistry 1】 (In formula (1), ring A, ring B and ring C each independently represent an aryl ring or a heteroaryl ring, and at least one hydrogen atom in these rings may be substituted; Y 1 is B, X 1 one of which is a group represented by formula (1a) and the other is >O, >N—R, or >S, In formula (1a), ring D and ring E are each independently a benzene ring, and at least one hydrogen atom in these rings may be substituted; X 2 is a single bond, >O, >N-R, >C(-R) 2 , -C(-R) 2 -C(-R) 2 -, >S, or >Si (-R) 2 and * indicates the bond position. Each R in the >N-R is independently an optionally substituted aryl or an optionally substituted heteroaryl; Above>C(-R) 2 , -C(-R) 2 -C(-R) 2 -, and >Si(-R) 2 R is each independently hydrogen, optionally substituted aryl, optionally substituted alkyl, or optionally substituted cycloalkyl; >N-R as X 1 may be bonded to one ring selected from the group consisting of ring A, ring B, and ring C via -O-, -S-, or a single bond in R, and may form a phenoxazine ring, a phenothiazine ring, or a carbazole ring together with the bonded ring; In the compound or structure represented by formula (1), at least one selected from the group consisting of aryl rings and heteroaryl rings may be condensed with at least one cycloalkane; At least one hydrogen in the cycloalkane may be replaced; and At least one -CH in the cycloalkane 2 - may be replaced by -O-; At least one hydrogen atom in the compound or structure represented by formula (1) may be replaced with deuterium.

2. The polycyclic aromatic compound according to claim 1, wherein ring A, ring B, and ring C are each independently a benzene ring, a naphthalene ring, a benzofuran ring, or a benzothiophene ring, ring D and ring E are each independently a benzene ring, and at least one hydrogen in the benzene ring, naphthalene ring, benzofuran ring, or benzothiophene ring is optionally substituted with 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, or a substituted silyl.

3. The polycyclic aromatic compound according to claim 1 or 2, which is represented by the following formula (2): 【Chemistry 2】 (In formula (2), Y 1 is B, X 1 one of which is a group represented by formula (2a) and the other is >O, >N—R, or >S, In formula (2a), X 2 is a single bond, >O, >N-R, >C(-R) 2 , -C(-R) 2 -C(-R) 2 -, >S, or >Si (-R) 2 and * indicates the bond position. In formula (2) and formula (2a), R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 , R 15 , R 16 , R 17 , R 18 , and R 19 are each independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl (two aryls may be bonded via a single bond or a linking group), alkyl, cycloalkyl, alkoxy, aryloxy, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, or alkyldicycloalkylsilyl, in which at least one hydrogen may be replaced by an aryl, heteroaryl, alkyl, or cycloalkyl. Each R in the >N-R is independently an optionally substituted aryl or an optionally substituted heteroaryl; Above>C(-R) 2 , -C(-R) 2 -C(-R) 2 -, and >Si(-R) 2 R is each independently hydrogen, optionally substituted aryl, optionally substituted alkyl, or optionally substituted cycloalkyl; >N-R in X 1 may be bonded to one ring selected from the group consisting of ring a, ring b, and ring c in R via -O-, -S-, or a single bond, and may form a phenoxazine ring, a phenothiazine ring, or a carbazole ring together with the bonded ring; In the compound or structure represented by formula (2), at least one selected from the group consisting of an aryl ring and a heteroaryl ring may be condensed with at least one cycloalkane having 3 to 24 carbon atoms, at least one hydrogen in the cycloalkane may be substituted with an aryl having 6 to 30 carbon atoms, a heteroaryl having 2 to 30 carbon atoms, an alkyl having 1 to 24 carbon atoms, or a cycloalkyl having 3 to 24 carbon atoms, and at least one -CH 2 - may be replaced by -O-; At least one hydrogen atom in the compound or structure represented by formula (2) may be replaced with deuterium.

4. The other X 1 The polycyclic aromatic compound according to any one of claims 1 to 3, wherein is >N-R.

5. X 2 The polycyclic aromatic compound according to claim 4 , wherein is a single bond.

6. X 2 But, >O, >N-R, >C(-R) 2 , -C(-R) 2 -C(-R) 2 -, >S, or >Si (-R) 2 The polycyclic aromatic compound according to any one of claims 1 to 4,

7. The polycyclic aromatic compound according to claim 1, represented by any one of formulas (1-1), (1-3), (1-21), (1-23), (1-41), (1-61), (1-83), and (1-103). 【Chemistry 3】 【change】

8. A material for an organic device, comprising the polycyclic aromatic compound according to any one of claims 1 to 7.

9. The material for an organic device according to claim 8 , which is a material for an organic electroluminescent element, a material for an organic field effect transistor, or a material for an organic thin-film solar cell.

10. The material for an organic device according to claim 9 , wherein the material for an organic electroluminescent element is a material for a light-emitting layer.

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

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

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

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

15. The organic electroluminescence device according to any one of claims 12 to 14, further comprising an electron transport layer and / or an electron injection layer disposed between the cathode and the light emitting layer, and at least one of the electron transport layer and the electron injection layer contains at least one selected from the group consisting of borane derivatives, pyridine derivatives, fluoranthene derivatives, BO-based derivatives, anthracene derivatives, benzofluorene derivatives, phosphine oxide derivatives, pyrimidine derivatives, arylnitrile derivatives, triazine derivatives, benzimidazole derivatives, phenanthroline derivatives, quinolinol-based metal complexes, thiazole derivatives, benzothiazole derivatives, silole derivatives and azoline derivatives.

16. 16. The organic electroluminescent device according to claim 15, wherein the electron transport layer and / or the electron injection layer further contains at least one selected from the group consisting of alkali metals, alkaline earth metals, rare earth metals, oxides of alkali metals, halides of alkali metals, oxides of alkaline earth metals, halides of alkaline earth metals, oxides of rare earth metals, halides of rare earth metals, organic complexes of alkali metals, organic complexes of alkaline earth metals, and organic complexes of rare earth metals.

17. A display device comprising the organic electroluminescent device according to any one of claims 11 to 16.

18. A lighting device comprising the organic electroluminescent element according to any one of claims 11 to 16.

Images