Polycyclic aromatic compound

Abstract

To provide a novel compound used for an organic device such as an organic EL element.SOLUTION: A polycyclic aromatic compound represented by the formula (1), where A ring, B ring, C ring and D ring each denote an optionally substituted aryl ring or heteroaryl ring, Z1 and Z2 each denote -CH= or -N= or the like, X1-X4 each denote >N-R1X or the like, R1X is aryl, heteroaryl, alkyl or cycloalkyl, at least one R1X is a substituent represented by formula (A-1), (A-2), (A-3) or (A-4), R21-R28 each denote hydrogen or the like, Y1-Y5 each denote -CR1Y= or -N= or the like, R1Y is heteroaryl or the like, W1 is >O, >S, or a fluorene ring having carbon as a spiro atom, or the like, W2 is >O, >S or >N-R2W, Y11-Y13 each denote -CR11Y= or -N=, R2W and R11Y are fluorene ring hydrogen, aryl or the like.SELECTED DRAWING: None

Description

[Technical field]

[0001] The present invention relates to a polycyclic aromatic compound. The present invention also relates to a polymer compound having a repeating unit of a structure derived from the polycyclic aromatic compound. The present invention further relates to a material for an organic device, a material for a light-emitting layer, a composition for forming a light-emitting layer, and an organic electroluminescent element, an organic field-effect transistor, or an organic thin-film solar cell, each of which contains the compound or the polymer compound in its light-emitting layer, and a display device and a lighting device that include the organic electroluminescent element. [Background technology]

[0002] Conventionally, display devices using electroluminescent light-emitting elements have been extensively studied because they can be made more energy-efficient and thinner, and organic electroluminescent elements (hereinafter sometimes referred to as "organic EL elements") made of organic materials have been actively studied because they can be easily made lighter and larger. In particular, the development of organic materials that have the luminescence properties of blue, one of the three primary colors of light, and organic materials that have the ability to transport charges such as holes and electrons, 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] There are two main emission mechanisms for organic EL elements: fluorescence, which uses light emitted from an excited singlet state, and phosphorescence, which uses light emitted from an excited triplet state. General fluorescent materials have a low exciton utilization efficiency of approximately 25%, and even when triplet-triplet fusion (TTF: Triplet-Triplet Fusion, or triplet-triplet annihilation, TTA: Triplet-Triplet Annihilation) is used, the exciton utilization efficiency is only 62.5%. On the other hand, phosphorescent materials can reach an exciton utilization efficiency of 100%, but it is difficult to achieve deep blue light emission, and in addition, the emission spectrum is wide, resulting in low color purity.

[0005] As compounds for use in organic EL devices, for example, the compounds described in Patent Document 1 or Non-Patent Documents 1 to 4 are known. [Prior art documents] [Patent documents]

[0006] [Patent Document 1] Patent No. 5669163 [Non-patent literature]

[0007] [Non-Patent Document 1] Nature 2012, 492, 234-238 [Non-Patent Document 2] Chemistry of Materials, 2016, 28 (15), pp 5400-5405 [Non-Patent Document 3] Nature Photonics, 2019, 13, 540-546 (https: / / doi.org / 10.1038 / s41566-019-0415-5) [Non-Patent Document 4] Advanced Optical Materials. 2019, 1900130 Summary of the Invention [Problem to be solved by the invention]

[0008] Therefore, Professor Adachi Chihaya of Kyushu University proposed a donor-acceptor type (DA type) thermally activated delayed fluorescence (TADF) mechanism (see Non-Patent Document 1). DA type TADF compounds have a structure in which a donor structure and an acceptor structure are bonded directly or via a π or σ bond, and are compounds that absorb thermal energy, undergo reverse intersystem crossing from an excited triplet state to an excited singlet state, and radiatively deactivate from the excited singlet state to emit fluorescence (delayed fluorescence). By using such TADF compounds, the energy of triplet excitons can also be effectively used for fluorescent emission, so that the exciton utilization efficiency of emission has reached 100%. A characteristic of DA type TADF compounds is that they give a wide emission spectrum with low color purity due to their structure, but the speed of reverse intersystem crossing is extremely fast.

[0009] In addition, Professor Hatakeyama of Kwansei Gakuin University has proposed molecular design of TADF-active compounds that utilize the multiple resonance effect (Non-Patent Document 3 and Patent Document 1). In molecular design that utilizes the multiple resonance effect, boron (electron-withdrawing) and nitrogen (electron-donating) are bonded to each other at the o-position. As a result, the HOMO and LUMO formed by each are strengthened and localized on the atom, resulting in separation of the HOMO and LUMO and TADF properties. The robust planar structure formed provides an emission spectrum with small Stokes shifts of the absorption and emission peaks and high color purity. On the other hand, the speed of reverse intersystem crossing is inferior to that of DA-type TADF compounds.

[0010] In DA-type TADF compounds, an emission spectrum with high color purity can be achieved by utilizing a DA structure with limited structural change and rotation (Non-Patent Document 2). Based on a similar idea, compounds with narrow emission half-widths using acceptor structures with boron atoms have been proposed (Patent Document 1, Non-Patent Documents 3 and 4), and the emission half-widths have been improved. On the other hand, even if a similar donor structure is used, a narrow emission half-width, a fast reverse intersystem crossing rate, and blue emission cannot be obtained (Non-Patent Document 4). As described above, it is difficult to achieve a narrow emission half-width, high TADF activity, and blue emission all at once, and there is room for improvement in optimizing the partial structure to achieve these goals.

[0011] An object of the present invention is to provide a novel compound as a material for use in organic devices such as organic EL elements.

[0012] As a result of intensive research conducted by the present inventors to solve the above problems, they discovered a novel combination of a donor structure and an acceptor structure. The present invention has been proposed based on such findings, and specific examples thereof have the following configurations.

[0013] [1] A polycyclic aromatic compound represented by the following formula (1): [ka]

[0014] (In formula (1), ring A, ring B, ring C and ring D are each independently an aryl ring or a heteroaryl ring, and at least one hydrogen atom in these rings may be substituted; Z 1 and Z 2 are each independently -CH= or -N=, and hydrogen in -CH= may be substituted; X 1 ~X 4 are each independently >O or >NR 1X However, not all of them are >O, and R 1Xis aryl, heteroaryl, alkyl or cycloalkyl; R 1X At least one of the substituents is represented by formula (A-1), (A-2), (A-3) or (A-4), and Wavy line indicates the bond position, In formula (A-1), R 21 ~R 28 are each independently hydrogen, aryl, heteroaryl, alkyl, cycloalkyl, cyano, or halogen; R 21 ~R 28 adjacent two of these may be bonded to each other to form a ring, In formula (A-2), Y 1 ~Y 5 are each independently -CR 1Y = or -N = and R 1Y is hydrogen, aryl, heteroaryl, alkyl, cycloalkyl, cyano, or halogen, and two adjacent R 1Y may be bonded to each other to form a ring, provided that Y 1 ~Y 5 is everything - CR 1Y = at least one R 1Y is fluorine, cyano, -BR 2 , -CO-R, -SO 2 -R, pyridyl, piperidyl or pyrazinyl, or any two adjacent R 1Y are bonded to each other to form a nitrogen-containing heteroaromatic ring, 2 , -CO-R, and -SO 2 R of -R is aryl, heteroaryl, alkyl, or cycloalkyl; In formula (A-3), W 1 >O, >S, >PR 1W or a ring with a carbon as a spiro atom, R 1W and R 31 ~R 38 are each independently hydrogen, aryl, heteroaryl, alkyl, cycloalkyl, cyano, or halogen; and R 31 ~R38 adjacent two of these may be bonded to each other to form a ring, In formula (A-4), W 2 is >O, >S or >NR 2W And Y 11 ~Y 13 are each independently -CR 11Y = or -N = and R 2W and R 11Y are each independently hydrogen, aryl, heteroaryl, alkyl, or cycloalkyl, and adjacent R 2W and R 11Y or two R's 11Y may be bonded to each other to form a ring, At least one selected from the group consisting of aryl rings and heteroaryl rings in the compound represented by formula (1) may be condensed with at least one cycloalkane, at least one hydrogen in the cycloalkane may be substituted, and at least one -CH 2 - may be replaced by -O-; At least one hydrogen atom in the compound represented by formula (1) may be substituted with a halogen atom or deuterium.

[0015] [2] The polycyclic aromatic compound according to [1], represented by the following formula (2): [ka]

[0016] (In formula (2), R 1 ~R 14 are each independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, alkyl, cycloalkyl, alkoxy, aryloxy, or diarylboryl (two aryls may be bonded via a single bond or a linking group), in which at least one hydrogen may be replaced by an aryl, heteroaryl, or alkyl; and R 3 ~R 14adjacent two of these may be bonded to each other to form a ring, X 1 ~X 4 are each independently >O or >NR 1X However, not all of them are >O, and R 1X is an aryl having 6 to 20 carbon atoms, a heteroaryl having 2 to 15 carbon atoms, an alkyl having 1 to 20 carbon atoms, or a cycloalkyl having 3 to 8 carbon atoms; R 1X at least one of is a substituent represented by formula (A-1), (A-2), (A-3) or (A-4); In formula (A-1), R 21 ~R 28 are each independently hydrogen, aryl, heteroaryl, alkyl, cycloalkyl, cyano, or halogen; and R 21 ~R 28 adjacent two of these may be bonded to each other to form a ring, In formula (A-2), Y 1 ~Y 5 are each independently -CR 1Y = or -N=, where Y 1 ~Y 5 At least one of is -N=R 1Y is hydrogen, aryl, heteroaryl, alkyl, cycloalkyl, cyano, or halogen, and two adjacent R 1Y may be bonded to each other to form a ring, In formula (A-3), W 1 is a ring with >O, ​​>S or carbon as a spiro atom, and R 31 ~R 38 are each independently hydrogen, aryl, heteroaryl, alkyl, cycloalkyl, cyano, or halogen; and R 31 ~R 38 adjacent two of these may be bonded to each other to form a ring, In formula (A-4), W 2 is >O, >S or >NR 2W And Y 11 ~Y 13 are each independently -CR 11Y= or -N = and R 2W and R 11Y are each independently hydrogen, aryl, heteroaryl, alkyl, or cycloalkyl, and adjacent R 2W and R 11Y or two R's 11Y may be bonded together to form an aryl or heteroaryl ring; At least one selected from the group consisting of aryl rings and heteroaryl rings in the compound represented by formula (2) may be condensed with at least one cycloalkane, at least one hydrogen in the cycloalkane may be substituted, and at least one -CH 2 - may be replaced by -O-; At least one hydrogen atom in the compound represented by formula (2) may be substituted with a halogen atom or deuterium.

[0017] [3] R 1 ~R 14 each independently represents a hydrogen atom, an aryl having 6 to 30 carbon atoms, a heteroaryl having 2 to 30 carbon atoms, a diarylamino (wherein the aryl has 6 to 12 carbon atoms), an alkyl having 1 to 12 carbon atoms, a cycloalkyl having 3 to 20 carbon atoms, or an aryloxy having 6 to 12 carbon atoms, in which at least one hydrogen atom is optionally substituted by an aryl having 6 to 12 carbon atoms or an alkyl having 1 to 8 carbon atoms; X 1 ~X 4 are each independently >O or >NR 1X However, not all of them are >O, and R 1X is an aryl having 6 to 12 carbon atoms or an alkyl having 1 to 8 carbon atoms, and R 1X at least one of is a substituent represented by formula (A-1), (A-2), (A-3) or (A-4); In formula (A-1), R 21 ~R 28each independently represents hydrogen, an aryl having 6 to 30 carbon atoms, a heteroaryl having 2 to 30 carbon atoms, an alkyl having 1 to 12 carbon atoms, a cycloalkyl having 3 to 20 carbon atoms, cyano, or halogen; In formula (A-2), R 1Y is hydrogen, aryl having 6 to 30 carbon atoms, heteroaryl having 2 to 30 carbon atoms, alkyl having 1 to 12 carbon atoms, cycloalkyl having 3 to 20 carbon atoms, cyano, or halogen, and two adjacent R 1Y may be bonded to each other to form an aromatic or heteroaromatic ring having 6 to 10 carbon atoms, In formula (A-3), W 1 is a fluorene ring with >O, ​​>S or carbon as a spiro atom, and R 31 ~R 38 each independently represents an aryl having 6 to 30 carbon atoms, a heteroaryl having 2 to 30 carbon atoms, an alkyl having 1 to 12 carbon atoms, a cycloalkyl having 3 to 20 carbon atoms, cyano, or halogen; In formula (A-4), W 2 is >O, >S or >NR 2W And Y 11 ~Y 13 are each independently -CR 11Y = or -N = and R 2W and R 11Y are each independently hydrogen, an aryl having 6 to 30 carbon atoms, a heteroaryl having 2 to 30 carbon atoms, an alkyl having 1 to 12 carbon atoms, or a cycloalkyl having 3 to 20 carbon atoms; and 2W and R 11Y or two R's 11Y may be bonded to each other to form a benzene ring or a pyridine ring, At least one hydrogen atom in the compound represented by formula (2) may be substituted with a halogen atom or a deuterium atom. The polycyclic aromatic compound according to [2]. [4]X 1 ~X 4 One or two of the 1X is a substituent represented by formula (A-1), (A-2), (A-3) or (A-4), >NR 1XThe polycyclic aromatic compound according to [2] or [3], [5] R 1X is any one of the structures shown below, in which any hydrogen may be independently substituted with an alkyl group having 1 to 8 carbon atoms, deuterium, or fluorine. Wavy line The polycyclic aromatic compound according to any one of [2] to [4], wherein the moiety indicates a bonding position.

[0018] [ka]

[0019] [6]X 1 and X 2 are all N-Ph, and X 3 and X 4 are each independently NR 1X or X 1 and X 2 are each independently NR 1X And X 3 and X 4 All of them are N-Ph. Ph is phenyl, Multiple R 1X The polycyclic aromatic compound according to [5], wherein the structures and bonding positions of [7] The polycyclic aromatic compound according to any one of [1] to [6], wherein each of the halogens is fluorine. [8] A polycyclic aromatic compound or a multimer thereof according to any one of [1] to [6], in which at least one hydrogen atom is substituted with a chlorine atom, a bromine atom, or an iodine atom. [9] A polycyclic aromatic compound in which at least one hydrogen atom of the polycyclic aromatic compound or a multimer thereof according to any one of [1] to [7] above is substituted with a substituent represented by formula (B):

[0020] [ka]

[0021] (In formula (B), R 40 and R 41 are each independently an alkyl group or are joined together to form an alkylene group; R 40 and R 41 The total number of carbon atoms is 2 to 10, and the wavy lines indicate binding sites.

[10] A polymer compound comprising a structure derived from the polycyclic aromatic compound according to any one of [1] to [9] as a repeating unit.

[11] The polymer compound according to

[10] , comprising, as a repeating unit, at least one structure derived from a compound selected from the group consisting of unsubstituted or optionally substituted triarylamine, unsubstituted or optionally substituted fluorene, unsubstituted or optionally substituted anthracene, unsubstituted or optionally substituted tetracene, unsubstituted or optionally substituted triazine, unsubstituted or optionally substituted carbazole, unsubstituted or optionally substituted tetraphenylsilane, unsubstituted or optionally substituted spirofluorene, unsubstituted or optionally substituted triphenylphosphine, unsubstituted or optionally substituted dibenzothiophene, and unsubstituted or optionally substituted dibenzofuran.

[12] A material for an organic device, comprising the polycyclic aromatic compound according to any one of [1] to [9], or the polymer compound according to

[10] or

[11] .

[13] The material for an organic device according to

[12] , 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.

[14] A material for an emission layer of an organic electroluminescent device, comprising the polycyclic aromatic compound according to any one of [1] to [9] or the polymer compound according to

[10] or

[11] .

[15] An organic electroluminescent element, an organic field effect transistor, or an organic thin-film solar cell, comprising the polycyclic aromatic compound according to any one of [1] to [9], or the polymer compound according to

[10] or

[11] .

[16] An organic electroluminescent device comprising a pair of electrodes consisting of an anode and a cathode, and a light-emitting layer disposed between the pair of electrodes, the light-emitting layer containing the material for a light-emitting layer according to

[14] .

[17] The organic electroluminescent device according to

[16] , wherein the light-emitting layer contains at least one compound represented by the following formulas (H1) to (H5), or contains at least one polymer compound having a repeating unit derived from at least one of the following structures (H1) to (H5).

[0022] [ka]

[0023] (In formula (H1), L 1 is an arylene having 6 to 24 carbon atoms, Z is CH, C-R', or N, In formula (H2), L 2 and L 3 each independently represents an aryl having 6 to 30 carbon atoms or a heteroaryl having 2 to 30 carbon atoms, At least one hydrogen atom in the compounds represented by the above formulas may be substituted with an alkyl group having 1 to 6 carbon atoms, a cyano group, a halogen atom, or a deuterium atom. In formula (H3), J is >O, >S, >N-R', >C(-R') 2 or >Si(-R') 2 and Y is a single bond, >O, >S, >C(-R') 2 or >Si(-R') 2 and Z is CH, C-R' or N; In formula (H4), Z is CH, C—R′ or N; Said, C-R', >N-R', >C(-R') 2 or >Si(-R') 2 R' in the formula (I) is aryl, heteroaryl, alkyl or cycloalkyl; In formula (H5), R 101 ~R 111are each independently hydrogen or a substituent which is an aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino or alkyl, at least one hydrogen in these substituents may be further substituted with an aryl, heteroaryl, diarylamino or alkyl; R 101 ~R 111 adjacent groups among the above may be bonded to each other to form an aryl ring or a heteroaryl ring together with the benzene ring to which they are bonded, and at least one hydrogen atom in the formed ring may be replaced by an aryl, a heteroaryl, a diarylamino, a diheteroarylamino, an arylheteroarylamino or an alkyl, and at least one hydrogen atom in these rings may be further replaced by an aryl, a heteroaryl, a diarylamino or an alkyl, At least one hydrogen atom in the compound represented by formula (H5) may be independently replaced with a halogen atom or a deuterium atom.

[18] The organic electroluminescent device according to

[16] or

[17] , wherein the light-emitting layer contains at least one compound represented by any one of the following formulae (AD1), (AD2) and (AD3):

[0024] [ka]

[0025] (In the formulas (AD1), (AD2) and (AD3), M is independently a single bond, -O-, >N-Ar, or >CAr 2 At least one of J's are each independently an arylene having 6 to 18 carbon atoms, and the arylene is optionally substituted with phenyl, alkyl having 1 to 6 carbon atoms, and cycloalkyl having 3 to 12 carbon atoms; Each Q is independently =C(-H)- or =N-; Ar each independently represents hydrogen, an aryl having 6 to 18 carbon atoms, a heteroaryl having 6 to 18 carbon atoms, an alkyl having 1 to 6 carbon atoms, or a cycloalkyl having 3 to 12 carbon atoms, and at least one hydrogen atom in the aryl and heteroaryl may be substituted by a phenyl, an alkyl having 1 to 6 carbon atoms, or a cycloalkyl having 3 to 12 carbon atoms; m is 1 or 2; n is an integer from 2 to (6-m); At least one hydrogen atom in the compounds represented by the above formulas may be substituted with a halogen or deuterium.

[19] A composition for forming an emission layer, comprising at least one of the polycyclic aromatic compound according to any one of [1] to [9], or the polymer compound according to

[10] or

[11] , and a solvent.

[20] The composition for forming a light-emitting layer according to

[19] , wherein the solvent contains an organic solvent having a boiling point of 150° C. or higher.

[21] The composition for forming an emission layer according to

[19] or

[20] , wherein the solvent is a mixed solvent containing a good solvent and a poor solvent for at least one of the polycyclic aromatic compound or the polymer compound, and the boiling point of the good solvent is lower than the boiling point of the poor solvent.

[22] The composition for forming an emission layer according to any one of

[19] to

[21] , which contains at least one compound represented by formulae (H1) to (H5), or contains at least one polymer compound having a repeating unit derived from at least one of the structures represented by formulae (H1) to (H5).

[0026] [ka]

[0027] (In formula (H1), L 1 is an arylene having 6 to 24 carbon atoms, Z is CH, C-R', or N, In formula (H2), L 2 and L 3 each independently represents an aryl having 6 to 30 carbon atoms or a heteroaryl having 2 to 30 carbon atoms, At least one hydrogen atom in the compounds represented by the above formulas may be substituted with an alkyl group having 1 to 6 carbon atoms, a cyano group, a halogen atom, or a deuterium atom. In formula (H3), J is >O, >S, >N-R', >C(-R') 2 or >Si(-R') 2 and Y is a single bond, >O, >S, >C(-R') 2 or >Si(-R') 2 and Z is CH, C-R' or N; In formula (H4), Z is CH, C—R′ or N; Said, C-R', >N-R', >C(-R') 2 or >Si(-R') 2 R' in the formula (I) is aryl, heteroaryl, alkyl or cycloalkyl; In formula (H5), R 101 ~R 111 are each independently hydrogen or a substituent which is an aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino or alkyl, at least one hydrogen in these substituents may be further substituted with an aryl, heteroaryl, diarylamino or alkyl; R 101 ~R 111 adjacent groups among the above may be bonded to each other to form an aryl ring or a heteroaryl ring together with the benzene ring to which they are attached, and at least one hydrogen atom in the formed ring may be replaced by an aryl, a heteroaryl, a diarylamino, a diheteroarylamino, an arylheteroarylamino or an alkyl, and at least one hydrogen atom in these rings may be further replaced by an aryl, a heteroaryl, a diarylamino or an alkyl, At least one hydrogen atom in the compound represented by formula (H5) may be independently replaced with a halogen atom or a deuterium atom.

[23] An organic electroluminescent device comprising a pair of electrodes consisting of an anode and a cathode, and a light-emitting layer disposed between the pair of electrodes, the light-emitting layer being formed from the composition for forming a light-emitting layer according to any one of

[19] to

[22] .

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

[16] to

[18] and

[23] , further comprising at least one layer selected from the group consisting of an electron transport layer and 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, and quinolinol-based metal complexes.

[25] The organic electroluminescent device according to

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

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

[16] to

[18] and

[23] to

[25] .

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

[16] to

[18] and

[23] to

[25] . Effect of the Invention

[0028] The present invention provides a novel polycyclic aromatic compound. The present invention also provides a novel polymer compound having a repeating unit of a structure derived from the above polycyclic aromatic compound. The polycyclic aromatic compound and the polymer compound of the present invention are useful as materials for organic devices that can be used in the manufacture of organic devices such as organic electroluminescent elements, organic field effect transistors, or organic thin-film solar cells. [Brief description of the drawings]

[0029] [Figure 1] FIG. 1 is a schematic cross-sectional view showing an example of an organic EL element. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0030] The present invention will be described in detail below. The following description of the components may be based on representative embodiments or specific examples, but the present invention is not limited to such embodiments. As used herein, combinations of preferred aspects are more preferred aspects. In this specification, a numerical range expressed using "to" means a range that includes the numerical values ​​before and after "to" as the lower and upper limits. In this specification, "hydrogen" in the explanation of structural formulae means "hydrogen atom (H)". In the present specification, a structure derived from a specific compound in describing a polymer compound refers to a structure that includes most of the structure of the compound and can be a repeating unit of the polymer compound. For example, a structural unit derived from the monomer in a polymer compound obtained by polymerizing a monomer having a structure in which any one hydrogen of the compound is substituted with a polymerizable group, or a structural unit derived from the reactive compound in the case where a polymer compound is formed by bonding different reactive groups to each other in a reactive compound in which any two or more hydrogens of the compound are independently substituted with reactive groups, can be mentioned. As used herein, combinations of preferred aspects are more preferred aspects.

[0031] In this specification, the term "thermally activated delayed fluorescent substance" (TADF compound) refers to a compound that absorbs thermal energy, undergoes reverse intersystem crossing from an excited triplet state to an excited singlet state, and is radiatively deactivated from the excited singlet state to emit delayed fluorescence. Here, the term "thermally activated delayed fluorescent substance" also includes those that undergo a higher-order triplet in the process of excitation from the excited triplet state to the excited singlet state. The light emission mechanism that emits fluorescence via higher triplet is called the FvHT (Fluorescence via Higher Triplet) mechanism, and is described in, for example, a paper by Monkman et al. of Durham University (NATURE COMMUNICATIONS,7:13680,DOI: 10.1038 / ncomms13680), a paper by Hosokai et al. of the National Institute of Advanced Industrial Science and Technology (Hosokai et al., Sci. Adv. 2017;3: e1603282), a paper by Sato et al. of Kyoto University (Scientific Reports,7:4820, DOI:10.1038 / s41598-017-05007-7), and a conference presentation by Sato et al. of Kyoto University (98th Annual Meeting of the Chemical Society of Japan, Presentation No.: 2I4-15, Mechanism of highly efficient light emission in organic electroluminescence using DABNA as an emitting molecule, Graduate School of Engineering, Kyoto University). In the present invention, when a sample containing a target compound is measured for its fluorescence lifetime at 300K, if a slow fluorescent component is observed, the target compound is determined to be a "thermally activated delayed fluorescent substance". Here, "slow fluorescent component" refers to a fluorescent component having a fluorescence lifetime of 0.1 μs or more. In contrast, the fluorescence emitted from an excited singlet state generated by direct transition from a ground singlet state usually has a fluorescence lifetime of 0.1 μs or less (e.g., 10 ns). In the following description, the fluorescence having a lifetime of 0.1 μs or less is referred to as a "fast fluorescent component". The fluorescence emitted by the "thermally activated delayed fluorescent substance" used in the present invention may contain a fast fluorescent component as well as a slow fluorescent component.

[0032] The fluorescence lifetime can be measured, for example, using a fluorescence lifetime measuring device (manufactured by Hamamatsu Photonics KK, C11367-01). In this specification, unless otherwise specified, "E S1" indicates the excited singlet energy level obtained from the intersection of the tangent line passing through the inflection point on the short wavelength side of the fluorescence spectrum at 77 K and the baseline, and "E T1 " indicates the excited triplet energy level obtained from the intersection of the tangent line passing through the inflection point on the short wavelength side of the phosphorescence spectrum at 77 K and the baseline, and "ΔE ST " is their energy difference, i.e., E S1 -E T1 This means the value calculated by ΔE ST is 0.20 eV or less, preferably 0.15 eV or less, and more preferably 0.10 eV or less. The term "phosphor" refers to a compound that can radiatively deactivate from an excited singlet state to emit fluorescence. The phosphor may be a normal phosphor in which only a fast fluorescent component is observed when the fluorescence lifetime is measured at 300K, or a delayed fluorescent substance in which both a fast fluorescent component and a delayed fluorescent component are observed. The phosphor preferably has an excited singlet energy level determined from the shoulder on the short wavelength side of the peak of the fluorescence spectrum lower than that of the host compound as the first component and the thermally activated delayed fluorescent substance as the second component.

[0033] In this specification, the term "emitter" refers to a compound that is contained in the light-emitting layer in an organic EL element and emits light that is finally extracted outside the element, and may be a plurality of compounds, and may have different emission wavelengths. In particular, the emitter used in the "TAF element" (TADF Assisting Fluorescence element) described later is called the "emitting dopant". The compound of the present invention can be used as an emitter, and in particular, in the TAF element, it can function as an emitting dopant or an "assisting dopant". The "thermally activated delayed phosphor" can function as an assisting dopant that assists the emission of the phosphor. In particular, in the TAF element, the assisting dopant performs reverse intersystem crossing of the electrons and holes received from the host from the excited triplet state to the excited singlet state following recombination on the assisting dopant, and transfers the energy to the emitting dopant. In the following description, an organic electroluminescent element using a thermally activated delayed phosphor as an assisting dopant may be referred to as a "TAF element". In the TAF element, triplet energy is converted to singlet energy by reverse intersystem crossing in the thermally activated delayed phosphor, so that the singlet energy can be efficiently supplied to the phosphor to assist in light emission, resulting in high luminous efficiency.

[0034] The energy levels of the host, assisting dopant and emitting dopant used in the present invention preferably satisfy at least one of the following formulae (a) to (d), and more preferably satisfy all of the conditions. |Ip(H)|≧|Ip(AD)| ...Formula (a) In formula (a), Ip(H) represents the ionization potential of the host compound, and Ip(AD) represents the ionization potential of the assisting dopant. |Ea(H)|≦|Ea(AD)| ····Formula (b) In formula (b), Ea(H) represents the electron affinity of the host compound, and Ea(AD) represents the electron affinity of the assisting dopant. |Eg(H)|≧|Eg(AD)|≧|Eg(ED)| ...Formula (c) In formula (c), Eg(H) represents the energy difference between the ionization potential and the electron affinity of the host, Eg(AD) represents the energy difference between the ionization potential and the electron affinity of the assisting dopant, and Eg(ED) represents the energy difference between the ionization potential and the electron affinity of the emitting dopant. E T1 (H)≧E T1 (AD)≧E T1 (ED) ··· formula (d) In formula (d), E T1 (H) represents the energy of the excited triplet level of the host compound, and E T1 (AD) represents the energy of the excited triplet level of the assisting dopant, and E T1 (ED) represents the energy of the excited triplet level of the emitting dopant.

[0035] On the other hand, the emitting dopant preferably has an emission peak in the range of 440 to 590 nm in its fluorescence spectrum, with a full width at half maximum (FWHM) of 80 nm or less. For use as a blue light-emitting device, the emission peak is more preferably 450 to 475 nm, and even more preferably 455 to 465 nm. For use as a green light-emitting device, the emission peak is more preferably 490 to 590 nm, and even more preferably 510 to 550 nm. The emission peak having a full width at half maximum (FWHM) of 35 nm or less means that the color purity of the emitted light is high. Therefore, by using such a phosphor, an organic light-emitting device with good color can be realized.

[0036] In this specification, ionization potential (Ip) means the ionization potential (Ip) determined by photoelectron yield spectroscopy, energy gap (Eg) means the optical band gap determined from the intersection between the tangent to the absorption peak on the longest wavelength side of the spectrum determined by ultraviolet-visible absorption spectroscopy and the baseline, and electron affinity (Ea) means the electron affinity determined by subtracting Eg from Ip.

[0037] In this specification, as a measurement sample for measuring each energy level, when the target compound is a host compound or an assisting dopant, a single film of the target compound (neat film, thickness: 50 nm) formed on a glass substrate is used, and when the target compound is an emitting dopant, an inert polymer film (e.g., polymethyl methacrylate film. Other examples include polystyrene, Cytop, and Zeonex. Thickness: 10 μm, concentration of target compound: 1 mass%) formed on a glass substrate in which the target compound is dispersed is used. The thickness of the polymethyl methacrylate film in which the target compound is dispersed may be a thickness that provides sufficient strength for measuring the absorption spectrum, fluorescence spectrum, and phosphorescence spectrum, and may be thicker when the strength is weak, and thinner when the strength is strong. For the excitation light, the wavelength of the absorption peak obtained in the absorption spectrum is used, and among the emission peaks appearing in the fluorescence spectrum or phosphorescence spectrum, data obtained from emission peaks appearing in the range of 400 to 500 nm for blue emission, 480 to 600 nm for green emission, and 580 to 700 nm for red emission are used to determine each energy level. In addition, when the absorption peak and the emission peak are close to each other and the excitation light is mixed into the emission peak, the absorption peak or absorption shoulder on the shorter wavelength side may be used. [1] The excited singlet energy level E, calculated from the intersection of the tangent on the short wavelength side of the peak of the fluorescence spectrum and the baseline S1 A measurement sample containing the target compound is irradiated with excitation light at 77K and the fluorescence spectrum is observed. A tangent line is drawn through the inflection point on the short wavelength side of the emission peak that appears in the fluorescence spectrum, and the wavelength at which the tangent line intersects with the baseline (B Sh ) [nm], the excited singlet energy level E S1 Calculate. E S1 [eV]=1240 / B Sh [2] The excited triplet energy level E, calculated from the intersection of the tangent line on the short wavelength side of the phosphorescence spectrum peak and the baseline T1 A measurement sample containing the target compound is irradiated with excitation light at 77 K and the phosphorescence spectrum is observed. A tangent line is drawn through the inflection point on the short wavelength side of the emission peak that appears in the phosphorescence spectrum, and the wavelength (C Sh ) [nm], the excited triplet energy level E T1 Calculate. E T1 [eV]=1240 / C Sh

[0038] Here, because the emission widths of the fluorescence and phosphorescence spectra differ between DA (donor-acceptor) type TADF materials and MRE (Multi Resonance Effect) type compounds due to the robustness of the molecules, it is believed that even if the maximum emission wavelengths are the same, the DA type TADF compounds have a wider range of molecular energy than the MRE type compound molecules. In TAF elements, it is necessary to accurately estimate the energy transfer between each component and design the configuration, so the excited singlet energy levels and excited triplet energy levels are estimated from the short wavelength side of the spectrum.

[0039] In this specification, the reverse intersystem crossing rate refers to the rate of reverse intersystem crossing from an excited triplet to an excited singlet. The reverse intersystem crossing rate of a thermally activated delayed fluorescent substance can be calculated by transient fluorescence spectroscopy using the method described in Nat. Commun. 2015, 6, 8476. or Organic Electronics 2013, 14, 2721-2726. Specifically, the reverse intersystem crossing rate of a thermally activated delayed fluorescent substance is 10 5 s -1 More than 10, preferably 6 s -1 That's all.

[0040] In this specification, the emission rate refers to the rate of transition from an excited singlet state to a ground state via fluorescence emission without going through a TADF process. The emission rate of a thermally activated delayed fluorescent substance can be calculated using the method described in Nat. Commun. 2015, 6, 8476. or Organic Electronics 2013, 14, 2721-2726, similar to the reverse intersystem crossing rate. Specifically, the emission rate of a thermally activated delayed fluorescent substance is calculated using the method described in Nat. Commun. 2015, 6, 8476. or Organic Electronics 2013, 14, 2721-2726. 7 s -1 More than 10, preferably 8 s -1 That's all.

[0041] In this specification, the compounds of the present invention are described using terms such as HOMO / LUMO, energy gap, (lowest) excited singlet energy, and (lowest / highest) excited triplet energy, each having a prefix such as "partial" / "localized" / "charge transfer transition". Some of these are values ​​obtained by molecular orbital calculations, not optically or electrochemically obtained values ​​by measuring the compounds of the present invention, and although there is a correlation with actual measurements (or it can be assumed that there is a correlation with actual measurements), the numerical values ​​may not match. For ease of designing and verifying the molecular structure, the structures are decomposed into donor structures and acceptor structures, and calculations, measurements, and explanations are performed. Therefore, when explaining the partial structure of the acceptor or donor, only the acceptor structure or only the donor structure may be considered.

[0042] <<Polycyclic aromatic compounds>> The polycyclic aromatic compound of the present invention has a structure represented by formula (1), and thus has both a narrow emission half-width and high TADF properties. The polycyclic aromatic compound of the present invention has a donor structure (D) and an acceptor structure (A), and is a compound having a robust cyclic structure or a structure utilizing a multiple resonance effect having at least a hetero element at the center, and is a multiple resonance effect type delayed fluorescent material. By appropriately selecting the donor structure (D) and the acceptor structure (A), the high-order excited triplet energy level and the excited singlet energy level are brought closer to each other, thereby obtaining high TADF properties. More specifically, it is possible to obtain a compound having high luminous efficiency, a fast delayed fluorescence lifetime, blue light emission, and a short emission half-width. It is presumed that the polycyclic aromatic compound of the present invention can be included in the light-emitting layer as an emitter or assisting dopant in, for example, an organic EL device, and can realize high external quantum efficiency and a long lifetime.

[0043] The polycyclic aromatic compound of the present invention has a structure represented by formula (1), and thus achieves both an extremely narrow emission half-width and high TADF properties using LE transitions in the donor structure. The term "LE transitions" refers to local energy transitions between HOMO-LUMOs that exist on the same partial structure in a molecule. The LE state (locally excited state) refers to S1 when the S0-S1 transition, which is an LE transition, is observed. In general, the emission obtained by the "LE transition" has one or more emission peaks with a narrow half-width or a spectrum in which these peaks overlap, and a clear vibration peak is often observed. On the other hand, the CT state (charge transfer state) refers to S1 when the S0-S1 transition, which is a CT transition, is observed. The "CT transitions" refer to energy transitions between HOMO-LUMOs that exist spatially apart on different partial structures in a molecule. In general, the emission obtained by the "CT transitions" has a spectrum with a wide half-width emission peak, and no clear vibration peak is observed.

[0044] In the present invention, the higher excited triplet energy (E Tn) is important. In other words, by bringing the LUMO+n (partial structure A) level closer to the LUMO (main skeleton) level, S1 and Tn can be brought closer together, and the upconversion from excited triplet to excited singlet by TADF can be accelerated. More specifically, the first is to accelerate the upconversion of T1(CT) → Tn(LE) → S1(CT), and the other is to accelerate the upconversion of T1(LE) → Tn(CT) → S1(LE). Specifically, E S1 -E T1 is 0.20 eV or less, |E S1 -E T2 |(or |E S1 -E T3 |) is preferably 0.20 eV or less, and E S1 -E T1 is 0.15 eV or less, |E S1 -E T2 |(or |E S1 -E T3 |) is more preferably 0.10 eV or less. S1 -E T1 is 0.1 eV or less, |E S1 -E T2 |(or |E S1 -E T3 |) is more preferably 0.05 eV or less. In particular, the energy level difference between S1 and T1 (E S1 -E T1 ) is 0.1 eV or less, and the energy level difference between S1 and T2 (|E S1 -E T2 |) or the energy level difference between S1 and T3 (|E S1 -E T3 |) is preferably 0.05 eV or less, and S1 is preferably in a locally excited state.

[0045] The polycyclic aromatic compound of the present invention is represented by formula (1). [ka]

[0046] In formula (1), Ring A, ring B, ring C and ring D are each independently an aryl ring or a heteroaryl ring, and at least one hydrogen atom in these rings may be substituted. Z 1 and Z 2 are each independently -CH= or -N=, and the hydrogen in -CH= may be substituted. X 1 ~X 4 are each independently >O or >NR 1X However, not all of them are >O, and R 1X is aryl, heteroaryl, alkyl or cycloalkyl; R 1X At least one of the groups is a substituent represented by formula (A-1), (A-2), (A-3) or (A-4). In formula (A-1), R 21 ~R 28 are each independently hydrogen, aryl, heteroaryl, alkyl, cycloalkyl, cyano, or halogen; R 21 ~R 28 Adjacent two of these may be bonded to each other to form a ring. In formula (A-2), Y 1 ~Y 5 are each independently -CR 1Y = or -N = and R 1Y is hydrogen, aryl, heteroaryl, alkyl, cycloalkyl, cyano, or halogen, and two adjacent R 1Y may be bonded to each other to form a ring, provided that Y 1 ~Y 5 All are -CR 1Y = at least one R 1Y is fluorine, cyano, -BR 2 , -CO-R, -SO 2 -R, pyridyl, piperidyl or pyrazinyl, or any two adjacent R 1Y are bonded to each other to form a nitrogen-containing heteroaromatic ring, 2 , -CO-R, and -SO 2R in -R is aryl, heteroaryl, alkyl, or cycloalkyl. In formula (A-3), W 1 >O, >S, >PR 1W or a ring with a carbon as a spiro atom, R 1W and R 31 ~R 38 are each independently hydrogen, aryl, heteroaryl, alkyl, cycloalkyl, cyano, or halogen; and R 31 ~R 38 Adjacent two of these may be bonded to each other to form a ring. In formula (A-4), W 2 is >O, >S or >NR 2W And Y 11 ~Y 13 are each independently -CR 11Y = or -N = and R 2W and R 11Y are each independently hydrogen, aryl, heteroaryl, alkyl, or cycloalkyl, and adjacent R 2W and R 11Y or two R's 11Y may be bonded to each other to form a ring. In the formulas (A-1), (A-2), (A-3) and (A-4), Wavy line The parts indicate the bond positions. At least one hydrogen in the compound represented by formula (1) may be substituted with a halogen or deuterium.

[0047] The polycyclic aromatic compound of the present invention has, in the structure represented by formula (1), an acceptor structure (A) as a substituent represented by formula (A-1), (A-2), (A-3) or (A-4), and a donor structure (D) as a portion other than the substituent represented by formula (A-1), (A-2), (A-3) or (A-4). Adachi et al. of Kyushu University have clarified the necessary features for thermally activated delayed fluorescent compounds with high TADF properties in a series of papers (Nature 2012, 492, 234-238, Science Advances, 2017:3, e1603282, Science Advances 2018:4, eaao6910). In addition to the features described in these papers, namely, the HOMO localized on the donor and the LUMO localized on the acceptor, small ΔE ST It is believed that the polycyclic aromatic compound of the present invention also has the feature of having a spin inversion process via a localized transition.

[0048] In formula (1), ring A, ring B, ring C and ring D are each independently an aryl ring that may have a substituent or a heteroaryl ring that may have a substituent.In formula (1), ring A, ring B, ring C and ring D are each independently preferably an aryl ring that may have a substituent.Ring A, ring B, ring C and ring D are each preferably a benzene ring that may have a substituent.

[0049] Examples of the "aryl ring" include an aryl ring having 6 to 30 carbon atoms, preferably an aryl ring having 6 to 16 carbon atoms, more preferably an aryl ring having 6 to 12 carbon atoms, and particularly preferably an aryl ring having 6 to 10 carbon atoms. Specific examples of the "aryl ring" include a monocyclic benzene ring, a bicyclic bicyclic bicyclic naphthalene ring, a tricyclic terphenyl ring (m-terphenyl, o-terphenyl, p-terphenyl), a fused tricyclic acenaphthylene ring, a fluorene ring, a phenalene ring, a phenanthrene ring, a fused tetracyclic triphenylene ring, a pyrene ring, a naphthacene ring, a fused pentacyclic perylene ring, a pentacene ring, and the like.

[0050] Examples of the "heteroaryl ring" include heteroaryl rings having 2 to 30 carbon atoms, preferably heteroaryl rings having 2 to 25 carbon atoms, more preferably heteroaryl rings having 2 to 20 carbon atoms, further preferably heteroaryl rings having 2 to 15 carbon atoms, and particularly preferably heteroaryl rings having 2 to 10 carbon atoms. Examples of the "heteroaryl ring" include heterocycles containing, as ring-constituting atoms other than carbon, 1 to 5 heteroatoms selected from oxygen, sulfur, and nitrogen. The "heteroaryl ring" may contain a selenium atom.

[0051] 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-benzo Examples of the ring include a triazole ring, a quinoline ring, an isoquinoline ring, a cinnoline ring, a quinazoline ring, a quinoxaline ring, a phthalazine ring, a naphthyridine ring, a purine ring, a pteridine ring, a carbazole ring, an acridine ring, a phenoxathiin ring, a phenoxazine ring, a phenothiazine ring, a phenazine ring, an indolizine ring, a furan ring, a benzofuran ring, an isobenzofuran ring, a dibenzofuran ring, a thiophene ring, a benzothiophene ring, a dibenzothiophene ring, a furazan ring, and a thianthrene ring.

[0052] At least one hydrogen atom in the above-mentioned "aryl ring" or "heteroaryl ring" in ring A, ring B, ring C, and ring D may be substituted with a substituent. Examples of the substituent include aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, alkyl, cycloalkyl, alkoxy, aryloxy, or diarylboryl (two aryls may be bonded via a single bond or a linking group) (above, first substituent), and at least one hydrogen atom in the aryl, heteroaryl, and diarylamino may be substituted with aryl, heteroaryl, alkyl, or cycloalkyl (above, second substituent).

[0053] Examples of the "aryl" (first substituent) include aryl having 6 to 30 carbon atoms, preferably aryl having 6 to 24 carbon atoms, more preferably aryl having 6 to 20 carbon atoms, further preferably aryl having 6 to 16 carbon atoms, particularly preferably aryl having 6 to 12 carbon atoms, and most preferably aryl having 6 to 10 carbon atoms.

[0054] Specific examples of the aryl include phenyl, which is a monocyclic aryl, (2-, 3-, 4-)biphenylyl, which is a bicyclic aryl, (1-, 2-)naphthyl, which is a condensed bicyclic aryl, terphenylyl (m-terphenyl-2'-yl, m-terphenyl-4'-yl, m-terphenyl-5'-yl, o-terphenyl-3'-yl, o-terphenyl-4'-yl, p-terphenyl-2'-yl, m-terphenyl-2-yl, m-terphenyl-3-yl, m-terphenyl-4-yl, o-terphenyl-2-yl, o-terphenyl-3-yl, o-terphenyl-4-yl, p-terphenyl-2-yl, p-terphenyl-3-yl, p-terphenyl-4-yl), which is a tricyclic aryl, acenaphthylene-(1-,3-,4-,5-)yl, fluorene-(1-,2-,3-,4-,9-)yl, phenalene-(1-,2-)yl, (1-,2-,3-,4-,9-)phenanthryl; tetracyclic aryl quaterphenylyl (5'-phenyl-m-terphenyl-2-yl, 5'-phenyl-m-terphenyl-3-yl, 5'-phenyl-m-terphenyl-4-yl, m-quaterphenylyl); condensed tetracyclic aryl triphenylene-(1-,2-)yl, pyrene-(1-,2-,4-)yl, naphthacene-(1-,2-,5-)yl; condensed pentacyclic aryl perylene-(1-,2-,3-)yl, pentacene-(1-,2-,5-,6-)yl, etc.

[0055] The above description of "aryl" as a first substituent can also be applied to "aryl" in diarylamino, "aryl" in arylheteroarylamino, "aryl" in aryloxy, "aryl" in diarylboryl, and "aryl" as a second substituent as a first substituent.

[0056] Examples of the "heteroaryl" (first substituent) 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.

[0057] Specific examples of heteroaryl include furyl, thienyl, pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, pyrazolyl, oxadiazolyl, furazanyl, thiadiazolyl, triazolyl, tetrazolyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, benzo[b]thienyl, dibenzothienyl, indyl, and aryl. Examples of the aryl include isoindolyl, 1H-indazolyl, benzimidazolyl, benzoxazolyl, benzothiazolyl, 1H-benzotriazolyl, quinolyl, isoquinolyl, cinnolyl, quinazolyl, quinoxalinyl, phthalazinyl, naphthyridinyl, purinyl, pteridinyl, carbazolyl, acridinyl, phenoxazinyl, phenothiazinyl, phenazinyl, phenoxathiinyl, thianthrenyl, and indolizinyl.

[0058] The above description of the "heteroaryl" as the first substituent can be similarly cited for the "heteroaryl" in diheteroarylamino and the "heteroaryl" in arylheteroarylamino as the first substituent. The above description of the "heteroaryl" as the first substituent can also be similarly cited for the "heteroaryl" as the second substituent. In addition, the "heteroaryl" as the second substituent includes a group in which at least one hydrogen atom in the heteroaryl is substituted with an aryl such as phenyl (specific examples are the groups described above) or an alkyl such as methyl (specific examples are the groups described below). As an example, when the second substituent is a carbazolyl group, a carbazolyl group in which at least one hydrogen atom at the 9-position is substituted with an aryl such as phenyl or an alkyl such as methyl is also included in the heteroaryl as the second substituent.

[0059] The "alkyl" (first substituent) may be either linear or branched, and examples thereof include alkyl having 1 to 24 carbon atoms (branched chain alkyl having 3 to 24 carbon atoms), preferably alkyl having 1 to 18 carbon atoms (branched chain alkyl having 3 to 18 carbon atoms), more preferably alkyl having 1 to 12 carbon atoms (branched chain alkyl having 3 to 12 carbon atoms), still more preferably alkyl having 1 to 6 carbon atoms (branched chain alkyl having 3 to 6 carbon atoms), particularly preferably alkyl having 1 to 4 carbon atoms (branched chain alkyl having 3 to 4 carbon atoms), and most preferably methyl.

[0060] 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, and 1-methylheptyl. , 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 2,6-dimethyl-4-heptyl, 3,5,5-trimethylhexyl, n-decyl, n-undecyl, 1-methyldecyl, n-dodecyl, n-tridecyl, 1-hexylheptyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, n-heptadecyl, n-octadecyl, and n-eicosyl.

[0061] The above description of the "alkyl" as the first substituent can be applied to the "alkyl" as the second substituent. The position of the alkyl as the second substituent on the first substituent is not particularly limited, but the second or third position is preferable, and the second position is more preferable, based on the bonding position (1st position) of the first substituent to the ring (the a ring, the b ring, the c ring, and the d ring in the formula (2)).

[0062] The "cycloalkyl" (first substituent) may be any of cycloalkyl consisting of one ring, cycloalkyl consisting of multiple rings, cycloalkyl containing a double bond that is not conjugated within the ring, and cycloalkyl containing a branch outside the ring, and examples thereof include cycloalkyl having 3 to 20 carbon atoms, preferably cycloalkyl having 3 to 12 carbon atoms, more preferably cycloalkyl having 5 to 10 carbon atoms, and further preferably cycloalkyl having 6 to 10 carbon atoms.

[0063] Specific cycloalkyl groups include, for example, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, bicyclo[2.2.1]heptyl, bicyclo[2.2.2]octyl, decahydronaphthyl, and adamantyl.

[0064] The above description of "cycloalkyl" as the first substituent can be similarly applied to "cycloalkyl" as the second substituent.

[0065] Examples of the "alkoxy" (first substituent) include an alkoxy having 1 to 24 carbon atoms (branched chain alkoxy having 3 to 24 carbon atoms), preferably an alkoxy having 1 to 18 carbon atoms (branched chain alkoxy having 3 to 18 carbon atoms), more preferably an alkoxy having 1 to 12 carbon atoms (branched chain alkoxy having 3 to 12 carbon atoms), still more preferably an alkoxy having 1 to 6 carbon atoms (branched chain alkoxy having 3 to 6 carbon atoms), and particularly preferably an alkoxy having 1 to 4 carbon atoms (branched chain alkoxy having 3 to 4 carbon atoms).

[0066] Specific alkoxy includes methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, s-butoxy, t-butoxy, pentyloxy, hexyloxy, heptyloxy, octyloxy, and the like.

[0067] The first substituent (including those substituted with a second substituent) is preferably a group represented by the following structural formula, and more preferably methyl, tertiary alkyl (t-butyl, t-amyl, t-octyl, etc.), phenyl, o-tolyl, p-tolyl, 2,4-xylyl, 2,5-xylyl, 2,6-xylyl, 2,4,6-mesityl, diphenylamino, di-p-tolylamino, bis(p-(t-butyl)phenyl)amino, carbazolyl. , 3,6-dimethylcarbazolyl, 3,6-di-t-butylcarbazolyl, and phenoxy, and more preferably methyl, t-butyl, t-amyl, t-octyl, phenyl, o-tolyl, 2,6-xylyl, 2,4,6-mesityl, diphenylamino, di-p-tolylamino, and bis(p-(t-butyl)phenyl)amino, carbazolyl, 3,6-dimethylcarbazolyl, and 3,6-di-t-butylcarbazolyl. From the viewpoint of ease of synthesis, larger steric hindrance is preferred for selective synthesis, and specifically, t-butyl, t-amyl, t-octyl, o-tolyl, p-tolyl, 2,4-xylyl, 2,5-xylyl, 2,6-xylyl, 2,4,6-mesityl, di-p-tolylamino, bis(p-(t-butyl)phenyl)amino, 3,6-dimethylcarbazolyl and 3,6-di-t-butylcarbazolyl are preferred.

[0068] 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.

[0069] [ka]

[0070] [ka]

[0071] [ka]

[0072] [ka]

[0073] [ka]

[0074] In formula (1), Z 1 and Z 2 are each independently -CH= or -N=, and -CH= is preferred from the viewpoint of ease of synthesis and stability of the compound. -N= is preferred from the viewpoint of a wide energy gap of the compound. The hydrogen atom in the -CH= may be substituted, and examples of the substituent include the first substituent described above. At least one hydrogen atom in the first substituent may be substituted with the second substituent described above.

[0075] X 1 ~X 4 are each independently >O or >NR 1X However, not all of them are >O. X 1 ~X 4 At least one of the following is >NR 1X This makes it easy to obtain a narrow emission half-width. X 1 ~X 4 All of the above are >NR 1X From the viewpoint of a wide energy gap, it is more preferable that X 1 ~X 4 It is preferred that at least one of the following is >O.

[0076] R 1X is aryl, heteroaryl, alkyl or cycloalkyl; R 1XAt least one of is a substituent represented by formula (A-1), (A-2), (A-3) or (A-4). For aryl, heteroaryl, alkyl or cycloalkyl, the respective explanations in the above first substituent can be cited. In formula (A-1), (A-2), (A-3) and (A-4), Wavy line The R moiety indicates a bonding position. The number of the substituents represented by formula (A-1), (A-2), (A-3) or (A-4) is 1 to 4, and preferably 1 to 2. 1X When at least one of R is a substituent represented by formula (A-1), (A-2), (A-3) or (A-4), good TADF properties can be obtained. 1X At least one of these is preferably a substituent represented by formula (A-1), (A-2), or (A-3).

[0077] The polycyclic aromatic compound represented by formula (1) is preferably a polycyclic aromatic compound represented by formula (2). [ka]

[0078] In formula (2), R 1 ~R 14 are each independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, alkyl, cycloalkyl, alkoxy, aryloxy, or diarylboryl (two aryls may be bonded via a single bond or a linking group), in which at least one hydrogen may be replaced by an aryl, heteroaryl, or alkyl; and R 3 ~R 14 adjacent two of these may be bonded to each other to form a ring. X 1 ~X 4 are each independently >O or >NR 1X However, not all of them are >O, and R 1Xis an aryl having 6 to 20 carbon atoms, a heteroaryl having 2 to 15 carbon atoms, an alkyl having 1 to 20 carbon atoms, or a cycloalkyl having 3 to 8 carbon atoms; R 1X At least one of the groups is a substituent represented by formula (A-1), (A-2) or (A-3). In formula (A-1) of formula (2), R 21 ~R 28 are each independently hydrogen, aryl, heteroaryl, alkyl, cycloalkyl, cyano, or halogen; and R 21 ~R 28 Adjacent two of these may be bonded to each other to form a ring. In formula (A-2) of formula (2), Y 1 ~Y 5 are each independently -CR 1Y = or -N=, where Y 1 ~Y 5 At least one of is -N=R 1Y is hydrogen, aryl, heteroaryl, alkyl, cycloalkyl, cyano, or halogen, and two adjacent R 1Y may be bonded to each other to form a ring. In formula (A-3) of formula (2), W 1 is a ring with >O, ​​>S or carbon as a spiro atom, and R 31 ~R 38 are each independently hydrogen, aryl, heteroaryl, alkyl, cycloalkyl, cyano, or halogen; and R 31 ~R 38 Adjacent two of these may be bonded to each other to form a ring. In formula (A-4) of formula (2), W 2 is >O, >S or >NR 2W And Y 11 ~Y 13 are each independently - CR 11Y = or -N = and R 2W and R 11Y are each independently hydrogen, aryl, heteroaryl, alkyl, or cycloalkyl, and adjacent R 2W and R 11Y or two R's11Y may be bonded to each other to form an aryl ring or a heteroaryl ring. At least one hydrogen in the compound represented by formula (2) may be substituted with a halogen or deuterium.

[0079] In formula (2), R 1 ~R 14 are each independently hydrogen or a substituent that is an aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, alkyl, cycloalkyl, alkoxy, aryloxy, or diarylboryl (two aryls may be bonded via a single bond or a linking group), and are specifically similar to the description of the "first substituent" above. In addition, in the "first substituent", adjacent substituents may be bonded to each other to form a ring structure. In addition, at least one hydrogen atom in the "first substituent" may be substituted with an aryl, heteroaryl, or alkyl, and the substituent bonded to the "first substituent" is similar to the description of the "second substituent" above.

[0080] R 1 is preferably hydrogen. 2 In formula (2), R is preferably hydrogen. 1 , R 2 R is preferably hydrogen. 3 is preferably hydrogen. 9 In formula (2), R is preferably hydrogen. 3 , R 9 R is preferably hydrogen. 5 is preferably hydrogen. 11 In formula (2), R is preferably hydrogen. 5 , R 11 R is preferably hydrogen. 6 is preferably hydrogen. 12 In formula (2), R is preferably hydrogen. 6 , R 12 R is preferably hydrogen. 8 is preferably hydrogen. 14In formula (2), R is preferably hydrogen. 8 , R 14 are preferably all hydrogen. In formula (2), R 1 , R 2 , R 3 , R 9 , R 5 , R 11 , R 6 , R 12 , R 8 , R 14 are preferably all hydrogen. Also, R 1 ~R 14 Of these, R 4 , R 10 All except for are hydrogen, or R 7 , R 13 It is preferable that all except for R are hydrogen. 4 , R 10 It is more preferable that all except R are hydrogen. 4 , R 10 is preferably diarylamine, alkyl, or cycloalkyl. R 1 ~R 14 It is also preferred that both are hydrogen.

[0081] In formula (2), R 3 ~R 11 Adjacent groups among may be bonded to each other to form an aryl ring or a heteroaryl ring together with the a ring, the b ring, the c ring, or the d ring, and at least one hydrogen in the formed ring may be substituted with an aryl, a heteroaryl, a diarylamino, an alkyl, a cycloalkyl, an alkoxy, an aryloxy, or a diarylboryl (two aryls may be bonded via a single bond or a linking group) (all of these, a first substituent), and at least one hydrogen in these may be substituted with an aryl, a heteroaryl, an alkyl, or a cycloalkyl (all of these, a second substituent). 3 ~R 11 Among the adjacent groups, R 3 and R 4 , R 6and R 7 , R 7 and R 8 , R 9 and R 10 , R 10 and R 11 , R 12 and R 13 , and R 13 and R 14 A combination of the following is included.

[0082] Formula (2) preferably contains a partial structure represented by the following formula (4-B2X4-0000). [ka]

[0083] Each X is independently O or N, and from the viewpoint of a narrow emission half width, at least one X is N, preferably three Xs are N, and more preferably all Xs are N. Also, from the viewpoint of a wide energy gap, it is preferable that at least one X is O. The substitution position of the substituent represented by formula (A-1), (A-2), (A-3) or (A-4) on the above partial structure may be the position represented by R' below. [ka]

[0084] In addition, the substitution position of the substituent represented by formula (A-1), (A-2), (A-3) or (A-4) in the compound represented by formula (2) is preferably a position that makes the entire structure symmetrical from the viewpoint of synthesis.

[0085] <Substituent represented by formula (A-1), (A-2), (A-3) or (A-4): Acceptor structure (A)> [ka]

[0086] R in formula (A-1)21 ~R 28 are each independently any one selected from the group consisting of hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, alkyl, cycloalkyl, alkoxy, aryloxy, diarylboryl (two aryls may be bonded via a single bond or a linking group), cyano, and halogen, and specifically, are as described above for the "first substituent." 21 ~R 28 are preferably each independently hydrogen, aryl, heteroaryl, alkyl, cycloalkyl, cyano, or halogen; R 21 ~R 28 is preferably hydrogen, since a smaller molecular weight is preferable from the viewpoint of synthesis. In addition, at least one hydrogen atom in the "first substituent" may be substituted with an aryl, heteroaryl, alkyl, or cycloalkyl, and the substituent bonded to the "first substituent" is similar to the description of the "second substituent" above. Wavy line The parts indicate the bond positions. Also, R 21 ~R 28 Among these, adjacent two may be bonded to each other to form a ring structure. The ring is preferably formed by linking with an alkylene having 2 to 5 carbon atoms. 21 ~R 28 Among the adjacent groups, R 21 and R 22 , R 22 and R 23 , R 23 and R 24 , R 24 and R 25 , R 25 and R 26 , R 26 and R 27 , R 27 and R 28 , and R 28 and R 21 A combination of the following is included.

[0087] From the viewpoint of physical properties, it is preferable that the LUMO of the partial structure consisting of the substituent represented by formula (A-1) is close to the LUMO of the main skeleton (4-B2X4-0000). When all X's are N (4-B2N4-0000), R 21 ~R 28 is preferably hydrogen. Preferred examples of the substituent represented by formula (A-1) include the following. In the following structure, any hydrogen may be independently substituted with alkyl having 1 to 8 carbon atoms, deuterium or fluorine, and among these, it is preferable that it is substituted with fluorine. The number of substitutions is not particularly limited, but is preferably 0 to 2, more preferably 0 to 1, and even more preferably 0.

[0088] [ka]

[0089] [ka]

[0090] Y in formula (A-2) 1 ~Y 5 are each independently -CR 1Y = or -N=. R 1Y are each independently any one selected from the group consisting of hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, alkyl, cycloalkyl, alkoxy, aryloxy, diarylboryl (two aryls may be bonded via a single bond or a linking group), cyano, and halogen, and specifically, are as described above for the "first substituent." 1Y is preferably hydrogen, aryl, heteroaryl, alkyl, cycloalkyl, cyano, or halogen. However, Y 1 ~Y 5 All are -CR 1Y = at least one R 1Y is fluorine, cyano, -BR 2, -CO-R, -SO 2 -R, pyridyl, piperidinyl or pyrazinyl, or adjacent R 1Y The nitrogen-containing heteroaromatic rings are bonded to each other at the -BR = group. Examples of the nitrogen-containing heteroaromatic ring include a pyrrole ring, an imidazole ring, a pyridine ring, a pyrazine ring, and an isoxazole ring. 2 , -CO-R, and -SO 2 R in -R is aryl, heteroaryl, alkyl, or cycloalkyl, and specifically corresponds to the description of the "first substituent" above. Also, two adjacent R 1Y may be bonded to each other to form a ring, for example, -BR 2 , -CO-R and -SO 2 -R, -CR 1Y or adjacent substituents on the pyridyl, piperidinyl and pyrazinyl may be linked to form a ring. In (A-2) Wavy line The parts indicate the bond positions.

[0091] From the viewpoint of physical properties, it is preferable that the LUMO of the partial structure consisting of the substituent represented by formula (A-2) is close to the LUMO of the main skeleton (4-B2X4-0000), and when all Xs are N (4-B2N4-0000), the following structure is preferable. Preferred examples of the substituent represented by formula (A-2) include the following. In the following structure, any hydrogen may be independently substituted with alkyl having 1 to 8 carbon atoms, deuterium or fluorine, and is preferably substituted with fluorine. The number of substitutions is not particularly limited, but is preferably 0 to 1, and more preferably 0.

[0092] [ka]

[0093] [ka]

[0094] In formula (A-3), W 1 >O, >S, >PR 1W or a ring with a carbon as a spiro atom, R 1W and R 31 ~R 38 are each independently hydrogen, aryl, heteroaryl, alkyl, cycloalkyl, cyano, or halogen, and are specifically the same as those described above for the "first substituent." 31 ~R 38 Adjacent two of R may be bonded to each other to form a ring structure. 31 ~R 38 Among the adjacent groups, R 31 and R 32 , 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 , and R 37 and R 38 , R 28 A combination of the following is included. The ring having a carbon as a spiro atom is preferably a polycyclic ring, more preferably a polycyclic hydrocarbon ring, and further preferably a fluorene ring. In (A-3) Wavy line The parts indicate the bond positions.

[0095] From the viewpoint of physical properties, it is preferable that the LUMO of the partial structure consisting of the substituent represented by formula (A-3) is close to the LUMO of the main skeleton (4-B2X4-0000), and when all Xs are N (4-B2N4-0000), the following structure is preferable. Preferred examples of the substituent represented by formula (A-3) include the following. In the following structure, any hydrogen may be independently substituted with alkyl having 1 to 8 carbon atoms, deuterium or fluorine, and is preferably substituted with fluorine. The number of substitutions is not particularly limited, but is preferably 0 to 2, more preferably 0 to 1, and even more preferably 0.

[0096] [ka]

[0097] [ka]

[0098] In formula (A-4), W 2 is >O, >S or >NR 2W And Y 11 ~Y 13 are each independently -CR 11Y = or -N = and R 2W and R 11Y are each independently hydrogen, aryl, heteroaryl, alkyl or cycloalkyl, and specifically, are the same as those described above for the "first substituent". 2W and R 11Y or two R's 11Y may be bonded to each other to form a ring structure. The ring structure is preferably an aryl ring or a heteroaryl ring, and more preferably includes a benzene ring or a pyridine ring. 11 ~Y 13 Of these, Y 12 and Y 13 All are -CR 11Y = and these two R 11Y are preferably bonded to each other to form a ring structure.

[0099] In (A-4) Wavy line The parts indicate the bond positions. Preferred examples of the substituent represented by formula (A-4) include the following. In the following structure, any hydrogen may be independently substituted with alkyl having 1 to 8 carbon atoms, deuterium or fluorine, and is preferably substituted with fluorine. The number of substitutions is not particularly limited, but is preferably 0 to 2, more preferably 0 to 1, and even more preferably 0.

[0100] [ka]

[0101] Examples of the substituent represented by formula (A-1), (A-2), (A-3) or (A-4) include the following. In the following structures, any hydrogen may be independently substituted with alkyl having 1 to 8 carbon atoms, deuterium or fluorine, and is preferably substituted with fluorine. The number of substitutions is not particularly limited, but is preferably 0 to 2, more preferably 0 to 1, and even more preferably 0.

[0102] [ka]

[0103] Of the above, preferred structures include the following: [ka]

[0104] <Substituents other than those represented by formula (A-1), (A-2), (A-3) or (A-4)> Substituents other than those represented by formula (A-1), (A-2), (A-3) or (A-4) in the polycyclic aromatic compound represented by formula (2) play an important role in adjusting the energy of the donor structure (D). From a synthetic viewpoint, it is also preferable to have a substituent other than those represented by formula (A-1), (A-2), (A-3) or (A-4) at a position where the entire structure is symmetrical, and in this case, the number of substitutions is preferably 2 or 4. The number of substituents other than those represented by formula (A-1), (A-2), (A-3) or (A-4) in the compound represented by formula (2) is preferably 0 or 2, more preferably 0. The substituent other than the substituent represented by formula (A-1), (A-2), (A-3) or (A-4) is preferably the first substituent described above. More specifically, it is sufficient to adjust the LUMO of the donor structure (D) and bring it closer to the LUMO of the acceptor structure (A). From the viewpoint of the partial energy gap of the substituent other than the substituent represented by formula (A-1), (A-2), (A-3) or (A-4), unsubstituted or substituted phenyl, unsubstituted or substituted pyridyl, unsubstituted or substituted diphenylamino, unsubstituted or substituted alkyl having 1 to 12 carbon atoms, unsubstituted or substituted cycloalkyl having 3 to 12 carbon atoms are preferred, and phenyl, tolyl, xylyl, mesityl, pyridyl, methylpyridyl, methyl, ethyl, propyl, butyl, pentyl, hexyl, cyclopentyl and cyclohexyl are more preferred. From the viewpoint of ease of synthesis, phenyl, tolyl, xylyl, mesityl, methyl, butyl and cyclohexyl are preferred.

[0105] <Characteristics of polycyclic aromatic compounds having an acceptor structure (A) and a partial structure (D)> The polycyclic aromatic compound of the present invention is a compound having a substituent represented by formula (A-1), (A-2), (A-3) or (A-4) as an acceptor structure (A) and a donor structure (D), and the partial HOMO and LUMO of the acceptor structure (A) and partial structure (D), respectively, HOMO(A), LUMO(A), HOMO(D) and LUMO(D), are preferably shallower than LUMO(D) and closer to LUMO(D). In addition, for high TADF activity, it is preferable that the high excited triplet energy (E Tn ) is the lowest excited singlet energy (E S1 It is preferable that the triplet energy is close to E. It is almost impossible to measure the higher excited triplet energy of an actual compound, so in practice, it is necessary to use values ​​calculated by molecular orbital calculations or to use model compounds. S1 -E T1 is 0.20 eV or less, |E S1 -E T2 |(or |E S1 -ET3 |) is preferably 0.20 eV or less, and E S1 -E T1 is 0.15 eV or less, |E S1 -E T2 |(or |E S1 -E T3 |) is more preferably 0.10 eV or less. S1 -E T1 is 0.1 eV or less, |E S1 -E T2 |(or |E S1 -E T3 |) is more preferably 0.05 eV or less.

[0106] <Other> At least one selected from the group consisting of aryl rings and heteroaryl rings in the polycyclic aromatic compound represented by formula (1) or (2) may be condensed with at least one cycloalkane, at least one hydrogen in the cycloalkane may be substituted, and at least one -CH 2 - may be replaced by -O-.

[0107] Examples of "cycloalkane" include cycloalkanes having 3 to 24 carbon atoms, cycloalkanes having 3 to 20 carbon atoms, cycloalkanes having 3 to 16 carbon atoms, cycloalkanes having 3 to 14 carbon atoms, cycloalkanes having 5 to 10 carbon atoms, cycloalkanes having 5 to 8 carbon atoms, cycloalkanes having 5 to 6 carbon atoms, and cycloalkanes having 5 carbon atoms.

[0108] Specific examples of cycloalkanes include cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclooctane, cyclononane, cyclodecane, norbornene, bicyclo[1.0.1]butane, bicyclo[1.1.1]pentane, bicyclo[2.0.1]pentane, bicyclo[1.2.1]hexane, bicyclo[3.0.1]hexane, bicyclo[2.1.2]heptane, bicyclo[2.2.2]octane, adamantane, diamantane, decahydronaphthalene, and decahydroazulene, as well as alkyl (particularly methyl) substituted, halogen (particularly fluorine) substituted, and deuterium substituted derivatives of these having 1 to 5 carbon atoms.

[0109] Among these, for example, as shown in the following structural formula, a structure in which at least one hydrogen atom is substituted on the carbon atom at the α-position of a cycloalkane (a carbon atom at a position adjacent to the carbon atom at the condensation site in a cycloalkyl fused to an aryl ring or heteroaryl ring) is preferred, a structure in which two hydrogen atoms are substituted on the carbon atom at the α-position is more preferred, and a structure in which a total of four hydrogen atoms are substituted on the two carbon atoms at the α-position is even more preferred. Examples of this substituent include an alkyl (particularly methyl) substituent having 1 to 5 carbon atoms, a halogen (particularly fluorine) substituent, and a deuterium substituent.

[0110] [ka]

[0111] Furthermore, a polycyclic aromatic compound represented by formula (1) in which at least one hydrogen atom is substituted with chlorine, bromine, or iodine can also be suitably used as the polycyclic aromatic compound of the present invention. Furthermore, a compound in which at least one hydrogen of the polycyclic aromatic compound represented by formula (1) is substituted with the following partial structure (B) is also preferably used as a compound according to another embodiment of the present invention. [ka] In the above partial structure (B), R 40 and R 41are each independently an alkyl group or are joined together to form an alkylene group; R 40 and R 41 The total number of carbon atoms is 2 to 10, and the wavy lines indicate bonding sites with other structures.

[0112] Examples of the polycyclic aromatic compound of the present invention are listed below, but the present invention is not limited to these specific examples. In the following examples, Me represents methyl.

[0113] [ka]

[0114] [ka]

[0115] [ka]

[0116] [ka]

[0117] [ka]

[0118] [ka]

[0119] [ka]

[0120] [ka]

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[0129]

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[0130]

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[0131]

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[0132]

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[0133]

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[0134]

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[0135]

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[0136]

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[0137]

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[0138]

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[0139]

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[0140]

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[0141]

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[0142]

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[0143]

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[0153] [ka]

[0154] [ka]

[0155] <Method of producing polycyclic aromatic compounds> The polycyclic aromatic compound of the present invention can basically produce an intermediate by bonding each ring structure to each other (first reaction), and then produce a final product by bonding each ring structure with a boron atom (second reaction). In the first reaction, for example, a general etherification reaction such as a nucleophilic substitution reaction or an Ullmann reaction, or a general amination reaction such as the Buchwald-Hartwig reaction can be used. In addition, in the second reaction, a tandem hetero Friedel-Crafts reaction (successive aromatic electrophilic substitution reaction, the same applies below) can be used. The symbols in the structural formulas in each of the following schemes have the same definition as those in formula (1) or formula (2).

[0156] The second reaction is a reaction for introducing a boron atom that bonds each ring structure, as shown in the following scheme (1). 1 and X 3 Between and X 2 and X 4 The hydrogen atom between the two is orthometalated with n-butyllithium, sec-butyllithium, or t-butyllithium. Then, boron trichloride or boron tribromide is added to carry out lithium-boron metal exchange, followed by the addition of a Brønsted base such as N,N-diisopropylethylamine to carry out a tandem boron-Friedel-Crafts reaction to obtain the desired product. In the second reaction, a Lewis acid such as aluminum trichloride may be added to promote the reaction.

[0157] [ka]

[0158] In scheme (1), lithium was introduced to the desired position by ortho-metallation, but as shown in scheme (2) below, a halogen atom (Hal) can be introduced in advance to the desired position, and lithium can be introduced to the desired position by halogen-metal exchange. This method is useful because it allows the synthesis of the target product even in cases where ortho-metallation is not possible due to the influence of substituents.

[0159] [ka]

[0160] By appropriately selecting the above synthesis method and the raw materials to be used, it is possible to obtain a compound having a substituent at a desired position, where Y is boron, X is a fluorine atom, 1 , X 2 , X 3 and X 4 are independently >O or >NR, it is possible to synthesize polycyclic aromatic compounds.

[0161] In addition, since the tandem boron-Friedel-Crafts reaction may occur at different positions due to, for example, rotation of the amino group in the intermediate, by-products may be generated. In such cases, the target polycyclic aromatic compound can be isolated from the mixture by chromatography, recrystallization, etc.

[0162] Examples of the orthometalation reagent used in the above scheme include alkyllithium such as methyllithium, n-butyllithium, sec-butyllithium, and t-butyllithium, and organic alkali compounds such as lithium diisopropylamide, lithium tetramethylpiperidide, lithium hexamethyldisilazide, and potassium hexamethyldisilazide.

[0163] The metal exchange reagent for metal-Y (boron) used in the above scheme includes boron halides such as boron trifluoride, trichloride, tribromide, and triiodide, CIPN(NEt 2 ) 2Examples of the aminated halide of Y, an alkoxylated product of Y, and an aryloxylated product of Y are mentioned.

[0164] The Bronsted base used in the above scheme includes 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, Ar 4 BNa, Ar 4 B.K., Ar 3 B, Ar 4 Si (wherein Ar is aryl such as phenyl).

[0165] The Lewis acid used in the above scheme 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.

[0166] In the above scheme, a Brönsted base or Lewis acid may be used to promote the tandem hetero Friedel-Crafts reaction. However, when a boron halide such as boron trifluoride, trichloride, tribromide, or triiodide is used, acids such as hydrogen fluoride, hydrogen chloride, hydrogen bromide, and hydrogen iodide are generated as the aromatic electrophilic substitution reaction proceeds, so it is effective to use a Brönsted base to capture the acid. On the other hand, when a boron amino halide or a boron alkoxylate is used, amines and alcohols are generated as the aromatic electrophilic substitution reaction proceeds, so it is not necessary to use a Brönsted base in many cases, but since the amino group and alkoxy group have low elimination ability, it is effective to use a Lewis acid to promote their elimination.

[0167] The polycyclic aromatic compounds represented by formula (1) or (2) also include compounds in which at least some of the hydrogen atoms are substituted with cyano, halogen, or deuterium. Such compounds can be synthesized in the same manner as described above by using raw materials in which the desired sites are cyanated, halogenated, or deuterated.

[0168] <<Polymer compounds with repeating units derived from polycyclic aromatic compounds>> The polymer compound having a repeating unit derived from the polycyclic aromatic compound of the present invention has the same properties as the polycyclic aromatic compound of the present invention, and further has polymer properties, and is therefore suitable for forming a layer by coating when used as a material for an organic device, which will be described later.

[0169] The polymer compound of the present invention preferably contains a repeating unit derived from at least one compound selected from the group consisting of unsubstituted or optionally substituted triarylamine, unsubstituted or optionally substituted fluorene, unsubstituted or optionally substituted anthracene, unsubstituted or optionally substituted tetracene, unsubstituted or optionally substituted triazine, unsubstituted or optionally substituted carbazole, unsubstituted or optionally substituted tetraphenylsilane, unsubstituted or optionally substituted spirofluorene, unsubstituted or optionally substituted triphenylphosphine, unsubstituted or optionally substituted dibenzothiophene, and unsubstituted or optionally substituted dibenzofuran. This repeating unit may be a repeating unit containing a structure represented by formula (1), or may be a repeating unit represented by formula (1). structure It may be a repeating unit different from the repeating unit containing the same. The polymer compound of the present invention having a repeating unit derived from a polycyclic aromatic compound can be synthesized by a known method using an aryl halide derivative and an arylboronic acid derivative as starting materials, or using an aryl halide boronic acid derivative, an aryl halide derivative and an arylboronic acid derivative as starting materials, in an appropriate combination of Suzuki-Miyaura coupling, Kumada-Tamao-Corleau coupling, Negishi coupling, halogenation reaction, or boration reaction.

[0170] In the Suzuki-Miyaura coupling, the reactive functional groups of the halide and the boronic acid derivative may be appropriately replaced, and in the Kumada-Tamao-Corleau coupling and the Negishi coupling, the functional groups involved in those reactions may be appropriately replaced. In addition, when converting to a Grignard reagent, the metallic magnesium and the isopropyl Grignard reagent may be appropriately replaced. The boronic acid ester may be used as it is, or may be hydrolyzed with an acid to be used as a boronic acid. When used as a boronic acid ester, the alkyl of the ester moiety may be any alkyl other than those exemplified.

[0171] A specific example of the palladium catalyst used in the reaction is tetrakis(triphenylphosphine)palladium(0):Pd(PPh 3 ) 4 , bis(triphenylphosphine)palladium(II) dichloride: PdCl 2 (PPh 3 ) 2 , Palladium(II) acetate: Pd(OAc) 2 , tris(dibenzylideneacetone)dipalladium(0):Pd 2 (dba) 3 , tris(dibenzylideneacetone)dipalladium(0) chloroform complex: Pd 2 (dba) 3 CHCl 3 , bis(dibenzylideneacetone)palladium(0):Pd(dba) 2 , Bis(tri-t-butylphosphino)palladium(0): Pd(t-Bu 3 P) 2 , [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II): Pd(dppf)Cl 2 , [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II) dichloromethane complex (1:1): Pd(dppf)Cl 2 ·CH 2 Cl 2 , PdCl 2 {P(t-Bu) 2 -(p-NMe 2 -Ph)} 2 :(A- ta Phos 2 PdCl 2 , palladium bis(dibenzylidene), [1,3-bis(diphenylphosphino)propane]nickel(II) dichloride, PdCl 2 [P(t-Bu) 2 -(p-NMe 2 -Ph)] 2 :(A- ta Phos 2 PdCl 2 (Pd-132: trademark; manufactured by Johnson Matthey).

[0172] In order to promote the reaction, a phosphine compound may be added to the palladium compound in some cases. Specific examples of the phosphine compound include tri(t-butyl)phosphine, tricyclohexylphosphine, 1-(N,N-dimethylaminomethyl)-2-(di-t-butylphosphino)ferrocene, 1-(N,N-dibutylaminomethyl)-2-(di-t-butylphosphino)ferrocene, 1-(methoxymethyl)-2-(di-t-butylphosphino)ferrocene, 1,1'-bis(di-t-butylphosphino)ferrocene, 2,2'-bis(di-t-butylphosphino)-1,1'-binaphthyl, 2-methoxy-2'-(di-t-butylphosphino)-1,1'-binaphthyl, or 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl.

[0173] Specific examples of the base used in the reaction include sodium carbonate, potassium carbonate, cesium carbonate, sodium bicarbonate, sodium hydroxide, potassium hydroxide, barium hydroxide, sodium ethoxide, sodium t-butoxide, sodium acetate, potassium acetate, tripotassium phosphate, or potassium fluoride.

[0174] Specific examples of the solvent used in the reaction include benzene, toluene, xylene, 1,2,4-trimethylbenzene, anisole, acetonitrile, dimethyl sulfoxide, N,N-dimethylformamide, tetrahydrofuran, diethyl ether, t-butyl methyl ether, 1,4-dioxane, methanol, ethanol, t-butyl alcohol, cyclopentyl methyl ether, isopropyl alcohol, dimethoxyethane, 2-(2-methoxyethoxy)ethane, 2-(2-ethoxyethoxy)ethane, etc. These solvents can be appropriately selected and may be used alone or as a mixed solvent.

[0175] Alternatively, the base may be added as an aqueous solution to carry out the reaction in a two-phase system. In the case of carrying out the reaction in a two-phase system, a phase transfer catalyst such as a quaternary ammonium salt may be added as necessary.

[0176] When producing a polymer compound having a repeating unit derived from a polycyclic aromatic compound of the present invention, the polymer compound may be produced in one step or in multiple steps. In addition, the polymer compound may be produced by a batch polymerization method in which all raw materials are put into a reaction vessel and then the reaction is started, a dropwise polymerization method in which 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 polymer compound. For example, when synthesizing a polymer compound having a repeating unit derived from a polycyclic aromatic compound of the present invention in one step, the target product is obtained by reacting a monomer having a polymerizable group bonded to a monomer unit (MU) and a monomer having a polymerizable group bonded to an end cap unit (EC) in a reaction vessel. In addition, when synthesizing a polymer compound having a repeating unit derived from a polycyclic aromatic compound of the present invention in multiple steps, the target product is obtained by polymerizing a monomer having a polymerizable group bonded to a monomer unit (MU) to a target molecular weight, and then adding a monomer having a polymerizable group bonded to an end cap unit (EC) and reacting the monomer.

[0177] In addition, the primary structure of the polymer can be controlled by selecting the monomer polymerizable group. For example, as shown in 1) to 3) of the synthesis scheme (20), it is possible to synthesize a polymer compound having a random primary structure (synthetic scheme (20) 1), a polymer compound having a regular primary structure (synthetic scheme (20) 2 and 3), etc., and these can be used in appropriate combination depending on the target object.

[0178] [ka]

[0179] The polymer compound containing a repeating unit derived from the compound represented by formula (1) is, for example, 1 ~R 11 A polymer compound can be produced by using a monomer having a polymerizable group introduced into R 1 ~R 11The substituent as is aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, alkoxy, aryloxy, or diarylboryl (two aryls may be bonded via a single bond or a linking group) (above, first substituent), and at least one hydrogen in the aryl, heteroaryl, and diarylamino may be substituted with an aryl, heteroaryl, alkyl, or cycloalkyl (above, second substituent). A polymer compound having a repeating unit containing the structure represented by formula (1) may be produced by using a comonomer in addition to the monomer containing the structure represented by formula (1). More specifically, the comonomer that may be used in the production of the polymer compound may be any of the following in which a polymerizable group has been introduced: unsubstituted or optionally substituted benzene, unsubstituted or optionally substituted triazine, unsubstituted or optionally substituted anthracene, unsubstituted or optionally substituted triarylamine, unsubstituted or optionally substituted carbazole, unsubstituted or optionally substituted spirofluorene, unsubstituted or optionally substituted dibenzofuran, unsubstituted or optionally substituted dibenzothiophene, unsubstituted or optionally substituted tetraarylsilane, unsubstituted or optionally substituted triarylphosphine, unsubstituted or optionally substituted phenoxazine, unsubstituted or optionally substituted phenothiazine, unsubstituted or optionally substituted phenylene ... Examples of the alkyl group include acridan which may be optionally substituted, alkyl which may be optionally unsubstituted or substituted, and cycloalkyl which may be optionally substituted. Among these, triarylamine which may be optionally unsubstituted or substituted, fluorene which may be optionally unsubstituted or substituted, anthracene which may be optionally unsubstituted or substituted, tetracene which may be optionally unsubstituted or substituted, triazine which may be optionally unsubstituted or substituted, carbazole which may be optionally unsubstituted or substituted, tetraphenylsilane which may be optionally unsubstituted or substituted, spirofluorene which may be optionally unsubstituted or substituted, triphenylphosphine which may be optionally unsubstituted or substituted, dibenzothiophene which may be optionally unsubstituted or substituted, and dibenzofuran which may be optionally unsubstituted or substituted are preferable.From another viewpoint, benzene, biphenyl, terphenyl, triarylamine, triphenyltriazine, or carbazole is also preferable. In addition, in the benzene, biphenyl, terphenyl, triarylamine, triphenyltriazine, or carbazole, it is more preferable that the benzene, biphenyl, terphenyl, triarylamine, triphenyltriazine, or carbazole has an alkyl group having 1 to 24 carbon atoms or a cycloalkyl group having 3 to 16 carbon atoms.

[0180] <<Materials for organic devices>> The polycyclic aromatic compound of the present invention and the polymer compound having a repeating unit derived from the polycyclic aromatic compound of the present invention can each be used as a material for an organic device. In the following, any compound selected from the group consisting of the polycyclic aromatic compound of the present invention and the polymer compound having a repeating unit derived from the polycyclic aromatic compound of the present invention may be referred to as the compound of the present invention. The compound of the present invention is a multiple resonance effect type thermally activated delayed fluorescent material having a donor (D) and an acceptor (A) having a specific structure, and has high luminescence efficiency, a short delayed fluorescence lifetime, blue emission and a short emission half-width, and is useful as a material for organic devices. The organic device may be an organic electroluminescent device, an organic field effect transistor, an organic thin-film solar cell, etc. The compound of the present invention may be used to form a light-emitting layer in an organic electroluminescent device, and may be used to form an active layer in an organic field effect transistor or an organic thin-film solar cell. The compound of the present invention is particularly preferably used in the light-emitting layer of an organic electroluminescent device.

[0181] <<Organic electroluminescent device>> The organic electroluminescent device has a pair of electrodes consisting of an anode and a cathode, and a light-emitting layer disposed between the pair of electrodes. The organic electroluminescent device may have one or more organic layers in addition to the light-emitting layer. Examples of the organic layers include an electron transport layer, a hole transport layer, an electron injection layer, and a hole injection layer, and may further have other organic layers. An example of the layer structure of an organic electroluminescent device having these organic layers is shown in Figure 1. In Figure 1, 101 denotes a substrate, 102 denotes an anode, 103 denotes a hole injection layer, 104 denotes a hole transport layer, 105 denotes a light emitting layer, 106 denotes an electron transport layer, 107 denotes an electron injection layer, and 108 denotes a cathode.

[0182] 1. Light-emitting layer in organic electroluminescent device The light-emitting layer 105 emits light by recombining holes injected from the anode 102 and electrons injected from the cathode 108 between electrodes to which an electric field is applied. The material for forming the light-emitting layer 105 may be a compound (light-emitting compound) that emits light when excited by the recombination of holes and electrons, and is preferably a compound that can form a stable thin film shape and shows strong light-emitting (fluorescence) efficiency in a solid state. The light-emitting layer may be a single layer or multiple layers, each of which is formed from a material for the light-emitting layer (host material, dopant material). The host material and the dopant material may each be one type or a combination of multiple types. The dopant material may be contained in the entire host material or may be contained partially in the host material. As a doping method, the light-emitting layer may be formed by a co-evaporation method with the host material, but it may also be mixed with the host material in advance and then evaporated at the same time. In addition, as described later, the light-emitting layer may also be formed by a wet film formation method using a light-emitting layer forming composition containing the host material and the dopant material.

[0183] The compound of the present invention can be preferably used as a material for forming the light-emitting layer of an organic electroluminescent device. An organic electroluminescent device can be produced by using the compound of the present invention as an emitter or assisting dopant in the light-emitting layer.

[0184] The light-emitting layer containing the compound of the present invention may contain a host compound, where the host compound may be one type or two or more types. The light-emitting layer may be a single layer or multiple layers. The host compound, the thermally activated delayed phosphor, and other components described later may be contained in the same layer, or at least one component may be contained in each of the multiple layers. The host compound and the thermally activated delayed phosphor contained in the light-emitting layer may each be one type or a combination of multiple types. The assisting dopant and the emitting dopant may be entirely or partially contained in the host compound as a matrix. The light-emitting layer may be formed by a deposition method, or may be formed by a wet film-forming method in which a paint prepared by dissolving in an organic solvent is applied.

[0185] 1-1. Host compound The light-emitting layer containing the compound of the present invention may contain a host compound. As the host compound, a known one can be used, for example, a compound having at least one of a carbazole ring and a furan ring can be mentioned, and among them, it is preferable to use a compound in which at least one of furanyl and carbazolyl is bonded to at least one of arylene and heteroarylene. Specific examples include mCP and mCBP.

[0186] As the host compound, for example, a compound represented by any one of the following formulae (H1), (H2), (H3), (H4) and (H5) can be used. These compounds may be polymer compounds having at least one structure selected from the group consisting of structures represented by the following formulae (H1), (H2), (H3), (H4) and (H5) as a repeating unit. The organic electroluminescent device of the present invention preferably contains at least one compound represented by the following formulas (H1) to (H5), or at least one polymer compound having at least one of the structures in the following formulas (H1) to (H5) as a repeating unit.

[0187] [ka]

[0188] In formula (H1), L 1 is an arylene having 6 to 24 carbon atoms, Z is CH, C-R' or N, and in formula (H2), L 2 and L 3 are each independently an aryl having 6 to 30 carbon atoms or a heteroaryl having 2 to 30 carbon atoms, at least one hydrogen atom in the compound represented by each of the above formulae may be substituted with an alkyl having 1 to 6 carbon atoms, cyano, halogen or deuterium, and in formula (H3), J is >O, >S, >N-R', >C(-R') 2 or >Si(-R') 2 and Y is a single bond, >O, >S, >C(-R') 2 or >Si(-R') 2 and Z is CH, C-R' or N. In formula (H4), Z is CH, C-R' or N, and the C-R', >N-R', >C(-R') 2 or >Si(-R') 2 R' in formula (H5) is aryl, heteroaryl, alkyl or cycloalkyl; 101 ~R 111 are each independently hydrogen or a substituent which is an aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino or alkyl, at least one hydrogen in these substituents may be further substituted with an aryl, heteroaryl, diarylamino or alkyl; R 101 ~R 111 Adjacent groups among these may be bonded to each other to form an aryl ring or a heteroaryl ring together with the benzene ring to which they are attached, and at least one hydrogen atom in the formed ring may be substituted with an aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino or alkyl, and at least one hydrogen atom in these may be further substituted with an aryl, heteroaryl, diarylamino or alkyl, and at least one hydrogen atom in the compound represented by formula (H5) may each independently be substituted with a halogen or deuterium. R in formula (H5) 101 ~R 111 As for the first substituent, the above description of the first substituent and the second substituent substituting the first substituent can be cited.

[0189] As the host compound, a compound represented by any one of the following formulae (H-1), (H-2) and (H-3) can also be used. [ka]

[0190] In formulas (H-1), (H-2) and (H-3), L 1represents an arylene having 6 to 24 carbon atoms, a heteroarylene having 2 to 24 carbon atoms, a heteroarylenearylene having 6 to 24 carbon atoms, and an aryleneheteroarylenearylene having 6 to 24 carbon atoms, preferably an arylene having 6 to 16 carbon atoms, more preferably an arylene having 6 to 12 carbon atoms, and particularly preferably an arylene having 6 to 10 carbon atoms. Specific examples thereof include divalent groups such as a benzene ring, a biphenyl ring, a terphenyl ring, and a fluorene ring. The heteroarylene is preferably a heteroarylene having 2 to 24 carbon atoms, more preferably a heteroarylene having 2 to 20 carbon atoms, still more preferably a heteroarylene having 2 to 15 carbon atoms, and particularly preferably a heteroarylene having 2 to 10 carbon atoms. Specific examples of the heteroarylene include a pyrrole ring, an oxazole ring, an isoxazole ring, a thiazole ring, an isothiazole ring, an imidazole ring, an oxadiazole ring, a thiadiazole ring, a triazole ring, a tetrazole ring, a pyrazole ring, a pyridine ring, a pyrimidine ring, a pyridazine ring, a pyrazine ring, a triazine ring, an indole ring, an isoindole ring, a 1H-indazole ring, a benzene ring, a phenyl ... and divalent groups such as a benzoimidazole ring, a benzoxazole ring, a benzothiazole ring, a 1H-benzotriazole ring, a quinoline ring, an isoquinoline ring, a cinnoline ring, a quinazoline ring, a quinoxaline ring, a phthalazine ring, a naphthyridine ring, a purine ring, a pteridine ring, a carbazole ring, an acridine ring, a phenoxathiin ring, a phenoxazine ring, a phenothiazine ring, a phenazine ring, an indolizine ring, a furan ring, a benzofuran ring, an isobenzofuran ring, a dibenzofuran ring, a thiophene ring, a benzothiophene ring, a dibenzothiophene ring, a furazan ring, an oxadiazole ring, and a thianthrene ring. At least one hydrogen atom in the compounds represented by the above formulas may be substituted with an alkyl group having 1 to 6 carbon atoms, cyano, halogen, or deuterium.

[0191] The host compound is preferably a compound represented by any one of the structural formulas listed below. In the structural formulas listed below, at least one hydrogen may be substituted with halogen, cyano, alkyl having 1 to 4 carbon atoms (e.g., methyl or t-butyl), phenyl, naphthyl, or the like.

[0192] [ka]

[0193] [ka]

[0194] [ka]

[0195] [ka]

[0196] [ka]

[0197] [ka]

[0198] [ka]

[0199] 1-2. Phosphors (emitting dopants) in TAF elements When the compound of the present invention is used as an assisting dopant, an emitting dopant may be used as an additional component in the light-emitting layer for the purpose of narrowing the half-width of the emission spectrum, improving the color tone, or extending the life.

[0200] The emitting dopant is not particularly limited, and a known compound can be used, and can be selected from various materials depending on the desired emission color.Specific examples of such compounds include condensed ring derivatives of phenanthrene, anthracene, pyrene, tetracene, pentacene, perylene, naphthopyrene, dibenzopyrene, rubrene, and chrysene, benzoxazole derivatives, benzothiazole derivatives, benzimidazole derivatives, benzotriazole derivatives, oxazole derivatives, oxadiazole derivatives, thiazole derivatives, imidazole derivatives, thiadiazole derivatives, triazole derivatives, pyrazoline derivatives, stilbene derivatives, thiophene derivatives, and tetraphenylbutadiene. derivatives, cyclopentadiene derivatives, bisstyryl derivatives such as bisstyrylanthracene derivatives and distyrylbenzene derivatives (JP Patent Publication No. 245087 / 1999), bisstyrylarylene derivatives (JP Patent Publication No. 247278 / 1990), diazaindacene derivatives, furan derivatives, benzofuran derivatives, isobenzofuran derivatives such as phenylisobenzofuran, dimesitylisobenzofuran, di(2-methylphenyl)isobenzofuran, di(2-trifluoromethylphenyl)isobenzofuran, and phenylisobenzofuran coumarin derivatives such as dibenzofuran derivatives, 7-dialkylaminocoumarin derivatives, 7-piperidinocoumarin derivatives, 7-hydroxycoumarin derivatives, 7-methoxycoumarin derivatives, 7-acetoxycoumarin derivatives, 3-benzothiazolylcoumarin derivatives, 3-benzimidazolylcoumarin derivatives, and 3-benzoxazolylcoumarin derivatives, dicyanomethylenepyran derivatives, dicyanomethylenethiopyran derivatives, polymethine derivatives, cyanine derivatives, oxobenzoanthracene derivatives, xanthene derivatives, and rhodamine derivatives. conductors, fluorescein derivatives, pyrylium derivatives, carbostyril derivatives, acridine derivatives, oxazine derivatives, phenylene oxide derivatives, quinacridone derivatives, quinazoline derivatives, pyrrolopyridine derivatives, furopyridine derivatives, 1,2,5-thiadiazolopyrene derivatives, pyrromethene derivatives, perinone derivatives, pyrrolopyrrole derivatives, squarylium derivatives, violanthrone derivatives, phenazine derivatives, acridone derivatives, deazaflavin derivatives, fluorene derivatives and benzofluorene derivatives.

[0201] Examples of dopant materials for each color of light emitted include aromatic hydrocarbon compounds such as naphthalene, anthracene, phenanthrene, pyrene, triphenylene, perylene, fluorene, indene, and chrysene, and derivatives thereof, furan, pyrrole, thiophene, silole, 9-silafluorene, 9,9'-spirobisilafluorene, benzothiophene, benzofuran, indole, dibenzothiophene, dibenzofuran, imidazopyridine, phenanthroline, pyrazine, naphthyridine, quinoxaline, pyrrolopyridine, and pyrrolopyridine. Examples of the aromatic heterocyclic compounds include lysine and thioxanthene, and their derivatives, distyrylbenzene derivatives, tetraphenylbutadiene derivatives, stilbene derivatives, aldazine derivatives, coumarin derivatives, azole derivatives such as imidazole, thiazole, thiadiazole, carbazole, oxazole, oxadiazole, and triazole, and metal complexes thereof, and aromatic amine derivatives typified by N,N'-diphenyl-N,N'-di(3-methylphenyl)-4,4'-diphenyl-1,1'-diamine.

[0202] In addition, examples of the green to yellow dopant material include coumarin derivatives, phthalimide derivatives, naphthalimide derivatives, perinone derivatives, pyrrolopyrrole derivatives, cyclopentadiene derivatives, acridone derivatives, quinacridone derivatives, and naphthacene derivatives such as rubrene. Further, preferred examples of the compounds exemplified as the above blue to blue-green dopant materials include compounds in which a substituent that enables a longer wavelength, such as aryl, heteroaryl, arylvinyl, amino, or cyano, has been introduced.

[0203] Further examples of orange to red dopant materials include naphthalimide derivatives such as bis(diisopropylphenyl)perylenetetracarboxylic acid imide, perinone derivatives, rare earth complexes such as Eu complexes having acetylacetone, benzoylacetone, and phenanthroline as ligands, 4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran and its analogs, metal phthalocyanine derivatives such as magnesium phthalocyanine and aluminum chlorophthalocyanine, rhodamine compounds, deazaflavin derivatives, coumarin derivatives, quinacridone derivatives, phenoxazine derivatives, oxazine derivatives, quinazoline derivatives, pyrrolopyridine derivatives, squarylium derivatives, violanthrone derivatives, phenazine derivatives, phenoxazone derivatives, and thiadiazolopyrene derivatives. Further preferred examples of the compounds exemplified above as blue to blue-green and green to yellow dopant materials include compounds in which a substituent that enables longer wavelengths, such as aryl, heteroaryl, arylvinyl, amino, and cyano, is introduced.

[0204] Other additional components may be appropriately selected from those described in Chemical Industry, June 2004, p. 13 and the references cited therein.

[0205] The amine having a stilbene structure is represented, for example, by the following formula. [ka] In the formula, Ar 1 is an m-valent group derived from an aryl having 6 to 30 carbon atoms, and Ar 2 and Ar 3 are each independently an aryl having 6 to 30 carbon atoms, 1 ~Ar 3 At least one of the groups has a stilbene structure, and Ar 1 ~Ar 3 may be substituted, and m is an integer from 1 to 4.

[0206] The amine having a stilbene structure is more preferably a diaminostilbene represented by the following formula. [ka] In the formula, Ar 2 and Ar 3 are each independently an aryl having 6 to 30 carbon atoms, and Ar 2 and Ar 3 may be substituted.

[0207] Specific examples of the aryl having 6 to 30 carbon atoms include benzene, naphthalene, acenaphthylene, fluorene, phenalene, phenanthrene, anthracene, fluoranthene, triphenylene, pyrene, chrysene, naphthacene, perylene, stilbene, distyrylbenzene, distyrylbiphenyl, and distyrylfluorene.

[0208] Specific examples of the amine having a stilbene structure include N,N,N',N'-tetra(4-biphenylyl)-4,4'-diaminostilbene, N,N,N',N'-tetra(1-naphthyl)-4,4'-diaminostilbene, N,N,N',N'-tetra(2-naphthyl)-4,4'-diaminostilbene, N,N'-di(2-naphthyl)-N,N'-diphenyl-4,4'-diaminostilbene, and N,N'-di(9-phenanthryl)-N,N'-diphenyl-4,4'-diaminostilbene. nyl-4,4'-diaminostilbene, 4,4'-bis[4"-bis(diphenylamino)styryl]-biphenyl, 1,4-bis[4'-bis(diphenylamino)styryl]-benzene, 2,7-bis[4'-bis(diphenylamino)styryl]-9,9-dimethylfluorene, 4,4'-bis(9-ethyl-3-carbazovinylene)-biphenyl, 4,4'-bis(9-phenyl-3-carbazovinylene)-biphenyl, and the like. Furthermore, amines having a stilbene structure, such as those described in JP-A Nos. 2003-347056 and 2001-307884, may also be used.

[0209] Examples of perylene derivatives include 3,10-bis(2,6-dimethylphenyl)perylene, 3,10-bis(2,4,6-trimethylphenyl)perylene, 3,10-diphenylperylene, 3,4-diphenylperylene, 2,5,8,11-tetra-t-butylperylene, 3,4,9,10-tetraphenylperylene, 3-(1'-pyrenyl)-8,11-di(t-butyl)perylene, 3-(9'-anthryl)-8,11-di(t-butyl)perylene, and 3,3'-bis(8,11-di(t-butyl)perylenyl). Also usable are perylene derivatives described in JP-A-11-97178, JP-A-2000-133457, JP-A-2000-26324, JP-A-2001-267079, JP-A-2001-267078, JP-A-2001-267076, JP-A-2000-34234, JP-A-2001-267075, and JP-A-2001-217077.

[0210] Furthermore, examples of the compound used as the third component of the present invention include compounds containing a boron atom, such as borane derivatives, dioxaboranaphthoanthracene (DOBNA) derivatives and multimers thereof, diazaboranaphthoanthracene (DABNA) derivatives and multimers thereof, oxazaboranaphthoanthracene (OABNA) derivatives and multimers thereof, oxaboranaphthoanthracene (OBNA) derivatives and multimers thereof, azaboranaphthoanthracene (ABNA) derivatives and multimers thereof, trioxaborazibenzopyrene derivatives and multimers thereof, dioxaazaborabenzopyrene derivatives and multimers thereof, oxadiazaborabenzopyrene derivatives and multimers thereof, and the like.

[0211] Examples of borane derivatives include 1,8-diphenyl-10-(dimesitylboryl)anthracene, 9-phenyl-10-(dimesitylboryl)anthracene, 4-(9'-anthryl)dimesitylborylnaphthalene, 4-(10'-phenyl-9'-anthryl)dimesitylborylnaphthalene, 9-(dimesitylboryl)anthracene, 9-(4'-biphenylyl)-10-(dimesitylboryl)anthracene, and 9-(4'-(N-carbazolyl)phenyl)-10-(dimesitylboryl)anthracene. Also, borane derivatives described in, for example, International Publication No. 2000 / 40586 may be used.

[0212] The aromatic amine derivative is represented, for example, by the following formula: [ka] In the formula, Ar 4 is an n-valent group derived from an aryl having 6 to 30 carbon atoms, and Ar 5 and Ar 6 are each independently an aryl having 6 to 30 carbon atoms, and Ar 4 ~Ar 6 may be substituted, and n is an integer from 1 to 4.

[0213] In particular, Ar 4 is a divalent group derived from anthracene, chrysene, fluorene, benzofluorene, or pyrene, and Ar 5 and Ar 6 are each independently an aryl having 6 to 30 carbon atoms, and Ar 4 ~Ar 6 is optionally substituted and n is 2.

[0214] Specific examples of the aryl having 6 to 30 carbon atoms include benzene, naphthalene, acenaphthylene, fluorene, phenalene, phenanthrene, anthracene, fluoranthene, triphenylene, pyrene, chrysene, naphthacene, perylene, and pentacene.

[0215] Examples of aromatic amine derivatives include chrysene derivatives such as N,N,N',N'-tetraphenylchrysene-6,12-diamine, N,N,N',N'-tetra(p-tolyl)chrysene-6,12-diamine, N,N,N',N'-tetra(m-tolyl)chrysene-6,12-diamine, N,N,N',N'-tetrakis(4-isopropylphenyl)chrysene-6,12-diamine, N,N,N',N'-tetra(naphthalen-2-yl)chrysene-6,12-diamine, and N,N'-diphenyl -N,N'-di(p-tolyl)chrysene-6,12-diamine, N,N'-diphenyl-N,N'-bis(4-ethylphenyl)chrysene-6,12-diamine, N,N'-diphenyl-N,N'-bis(4-isopropylphenyl)chrysene-6,12-diamine, N,N'-diphenyl-N,N'-bis(4-t-butylphenyl)chrysene-6,12-diamine, N,N'-bis(4-isopropylphenyl)-N,N'-di(p-tolyl)chrysene-6,12-diamine and the like.

[0216] Examples of pyrene-based compounds include N,N,N',N'-tetraphenylpyrene-1,6-diamine, N,N,N',N'-tetra(p-tolyl)pyrene-1,6-diamine, N,N,N',N'-tetra(m-tolyl)pyrene-1,6-diamine, N,N,N',N'-tetrakis(4-isopropylphenyl)pyrene-1,6-diamine, N,N,N',N'-tetrakis(3,4-dimethylphenyl)pyrene-1,6-diamine, N,N'-diphenyl-N,N'-di(p-tolyl)pyrene-1,6-diamine, N,N'-diphenyl-N,N'-bis(4-ethylphenyl)pyrene-1, 6-diamine, N,N'-diphenyl-N,N'-bis(4-isopropylphenyl)pyrene-1,6-diamine, N,N'-diphenyl-N,N'-bis(4-t-butylphenyl)pyrene-1,6-diamine, N,N'-bis(4-isopropylphenyl)-N,N'-di(p-tolyl)pyrene-1,6-diamine, N,N,N',N'-tetrakis(3,4-dimethylphenyl)-3,8-diphenylpyrene-1,6-diamine, N,N,N,N-tetraphenylpyrene-1,8-diamine, N,N'-bis(biphenyl-4-yl)-N,N'-diphenylpyrene-1,8-diamine, N 1 ,N 6 -Diphenyl-N 1 ,N 6 -bis-(4-trimethylsilanyl-phenyl)-1H,8H-pyrene-1,6-diamine and the like. For example, specific examples include formulae (PYR1), (PYR2), (PYR3) and (PYR4).

[0217] [ka]

[0218] Examples of anthracene-based compounds include N,N,N,N-tetraphenylanthracene-9,10-diamine, N,N,N',N'-tetra(p-tolyl)anthracene-9,10-diamine, N,N,N',N'-tetra(m-tolyl)anthracene-9,10-diamine, N,N,N',N'-tetrakis(4-isopropylphenyl)anthracene-9,10-diamine, N,N'-diphenyl-N,N'-di(p-tolyl)anthracene-9,10-diamine, N,N'-diphenyl-N,N'-di(m-tolyl)anthracene-9,10 -diamine, N,N'-diphenyl-N,N'-bis(4-ethylphenyl)anthracene-9,10-diamine, N,N'-diphenyl-N,N'-bis(4-isopropylphenyl)anthracene-9,10-diamine, N,N'-diphenyl-N,N'-bis(4-t-butylphenyl)anthracene-9,10-diamine, N,N'-bis(4-isopropylphenyl)-N,N'-di(p-tolyl)anthracene-9,10-diamine, 2,6-di-t-butyl-N,N,N',N'-tetra(p-tolyl)anthracene-9,10-diamine , 2,6-di-t-butyl-N,N'-diphenyl-N,N'-bis(4-isopropylphenyl)anthracene-9,10-diamine, 2,6-di-t-butyl-N,N'-bis(4-isopropylphenyl)-N,N'-di(p-tolyl)anthracene-9,10-diamine, 2,6-dicyclohexyl-N,N'-bis(4-isopropylphenyl)-N,N'-di(p-tolyl)anthracene-9,10-diamine, 2,6-dicyclohexyl-N,N'-bis(4-isopropylphenyl)-N,N'-di(p-tolyl)anthracene-9,10-diamine, 2,6-dicyclohexyl-N,N'-bis(4-isopropylphenyl)-N,N'-bis(4-t-butylphenyl) Examples of such anthracene include anthracene-9,10-diamine, 9,10-bis(4-diphenylamino-phenyl)anthracene, 9,10-bis(4-di(1-naphthylamino)phenyl)anthracene, 9,10-bis(4-di(2-naphthylamino)phenyl)anthracene, 10-di-p-tolylamino-9-(4-di-p-tolylamino-1-naphthyl)anthracene, 10-diphenylamino-9-(4-diphenylamino-1-naphthyl)anthracene, and 10-diphenylamino-9-(6-diphenylamino-2-naphthyl)anthracene.

[0219] Other examples include [4-(4-diphenylamino-phenyl)naphthalene-1-yl]-diphenylamine, [6-(4-diphenylamino-phenyl)naphthalene-2-yl]-diphenylamine, 4,4'-bis[4-diphenylaminonaphthalene-1-yl]biphenyl, 4,4'-bis[6-diphenylaminonaphthalene-2-yl]biphenyl, 4,4"-bis[4-diphenylaminonaphthalene-1-yl]-p-terphenyl, 4,4"-bis[6-diphenylaminonaphthalene-2-yl]-p-terphenyl, and indenocarbazole derivatives. Furthermore, aromatic amine derivatives described in, for example, JP-A-2006-156888 may also be used.

[0220] The indenocarbazole derivative is a compound represented by the following formula (IDC1). Specific examples include compounds having the following partial structures (IDC11), (IDC12) and (IDC13). In the following formula (IDC1), Z is CR A or N, π1 and π2 each independently represent a substituted or unsubstituted aromatic hydrocarbon having 6 to 50 ring carbon atoms or a substituted or unsubstituted aromatic heterocycle having 5 to 50 ring carbon atoms, R A ,R B and R C is hydrogen or an arbitrary substituent, n and m are each independently an integer of 1 to 4, and two adjacent R A ,R B and R C may be bonded to each other to form a substituted or unsubstituted ring structure. More specifically, the formulae (IDC121), (IDC131), (IDC132), (IDC133) and (IDC134) are included.

[0221] [ka]

[0222] Coumarin derivatives include coumarin-6 and coumarin-334. Furthermore, coumarin derivatives described in JP-A-2004-43646, JP-A-2001-76876, JP-A-6-298758, and the like may also be used.

[0223] Examples of the pyran derivative include DCM and DCJTB shown below. [ka] Furthermore, pyran derivatives described in JP-A-2005-126399, JP-A-2005-097283, JP-A-2002-234892, JP-A-2001-220577, JP-A-2001-081090, JP-A-2001-052869, and the like may also be used.

[0224] The phosphor used in the present invention is preferably a compound having a boron atom. Examples of the compound having a boron atom used as a phosphor include dioxaboranaphthoanthracene (DOBNA) derivatives and multimers thereof, diazaboranaphthoanthracene (DABNA) derivatives and multimers thereof, oxazaboranaphthoanthracene (OABNA) derivatives and multimers thereof, oxaboranaphthoanthracene (OBNA) derivatives and multimers thereof, and azaboranaphthoanthracene (ABNA) derivatives and multimers thereof.

[0225] The emitting dopant preferably contains at least one compound represented by the following formulae (ED1), (ED1') and (ED2). [ka]

[0226] (In formula (ED1), R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 9 , R 10 and R 11are each independently hydrogen, aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, alkoxy, aryloxy, or diarylboryl (two aryls may be bonded via a single bond or a linking group), which may be further substituted with aryl, heteroaryl, or alkyl; and R 1 ~R 3 , R 4 ~R 6 and R 9 ~R 11 adjacent groups among these may be bonded to each other to form an aryl ring or a heteroaryl ring together with the a ring, the b ring or the c ring, and the ring formed may be substituted with an aryl, a heteroaryl, a diarylamino, an alkyl, a cycloalkyl, an alkoxy, an aryloxy or a diarylboryl (two aryls may be bonded via a single bond or a linking group), which may be further substituted with an aryl, a heteroaryl or an alkyl; X is >O or >NR, and R and R of >NR 13 is aryl, heteroaryl or alkyl, which may be substituted with aryl, heteroaryl or alkyl; However, when X is an amino group, R 2 does not become an amino group, and, At least one hydrogen atom in the compound and structure represented by formula (ED1) may be replaced with cyano, halogen, or deuterium.

[0227] [ka]

[0228] (In formula (ED1'), R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R10 , R 11 , R 12 , R 13 and R 14 are each independently hydrogen, aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, alkoxy, aryloxy, or diarylboryl (two aryls may be bonded via a single bond or a linking group), which may be further substituted with aryl, heteroaryl, or alkyl; and R 1 ~R 3 , R 4 ~R 7 , R 8 ~R 10 and R 11 ~R 14 adjacent groups among these may be bonded to each other to form an aryl ring or a heteroaryl ring together with the a ring, the b ring, the c ring or the d ring, and the ring formed may be substituted with an aryl, a heteroaryl, a diarylamino, an alkyl, a cycloalkyl, an alkoxy, an aryloxy or a diarylboryl (two aryls may be bonded via a single bond or a linking group), which may be further substituted with an aryl, a heteroaryl or an alkyl; X is >O or >NR, where R of >NR is aryl, heteroaryl or alkyl, which may be substituted with aryl, heteroaryl or alkyl; L is a single bond, >CR 2 , >O, >S and >NR, and said >CR 2 and R in >NR is each independently hydrogen, aryl, heteroaryl, diarylamino, alkyl, alkoxy, aryloxy, or diarylboryl (two aryls may be bonded via a single bond or a linking group), which may be further substituted with aryl, heteroaryl, or alkyl; and, At least one hydrogen atom in the compound and structure represented by formula (ED1') may be replaced with cyano, halogen, or deuterium.

[0229] [ka]

[0230] (In formula (ED2), 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 and R 14 are each independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, alkyl, cycloalkyl, alkoxy, aryloxy, heteroaryloxy, diarylboryl (two aryls may be bonded via a single bond or a linking group), arylthio, heteroarylthio, or alkyl-substituted silyl, in which at least one hydrogen may be substituted with an aryl, heteroaryl, or alkyl; and R 5 ~R 7 and R 10 ~R 12 adjacent groups among the above may be bonded to each other to form an aryl ring or a heteroaryl ring together with the b ring or the d ring, and at least one hydrogen atom in the formed ring may be substituted with an aryl, a heteroaryl, a diarylamino, a diheteroarylamino, an arylheteroarylamino, an alkyl, a cycloalkyl, an alkoxy, an aryloxy, a heteroaryloxy, a diarylboryl (two aryls may be bonded via a single bond or a linking group), an arylthio, a heteroarylthio, or an alkyl-substituted silyl, and at least one hydrogen atom in these may be substituted with an aryl, a heteroaryl, or an alkyl, X 1 , X 2 , X 3 and X 4are each independently >O, >NR or >CR 2 and R and >CR of the >NR. 2 R in the above >NR is an aryl having 6 to 12 carbon atoms, a heteroaryl having 2 to 15 carbon atoms, or an alkyl having 1 to 6 carbon atoms. 2 R is -O-, -S-, -C(-R) 2 or may be bonded to at least one of the ring a, ring b, ring c and ring d via a single bond, and the -C(-R) 2 R in - is hydrogen or alkyl having 1 to 6 carbon atoms; However, X 1 , X 2 , X 3 , and X 4 Of these, no more than two are >O, and, At least one hydrogen atom in the compound represented by formula (ED2) may be substituted with cyano, halogen or deuterium. X in formula (ED2) 1 , X 2 , X 3 and X 4 When >NR, this R is preferably a substituent other than the substituents represented by formula (A-1), (A-2), (A-3) or (A-4) in formula (1).

[0231] More specifically, examples of the compounds include compounds having structures represented by the following formulas (ED11) to (ED19), (ED21) to (ED28), (ED211), (ED212), (ED221) to (ED223), (ED231), (ED241), (ED242), (ED261) and (ED271).

[0232] [ka]

[0233] [ka]

[0234] [ka]

[0235] At least one hydrogen atom in the structures represented by formulae (ED11) to (ED19), (ED21) to (ED28), (ED211), (ED212), (ED221) to (ED223), (ED231), (ED241), (ED242), (ED261) and (ED271) may be independently replaced with an aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, alkoxy, aryloxy or diarylboryl (two aryls may be bonded via a single bond or a linking group), which may be further replaced with an aryl, heteroaryl or alkyl. The preferred range and specific examples of aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, alkoxy or aryloxy are described in R in formula (1). 1 ~R 11 Reference may be made to the corresponding description in Furthermore, the phosphor that is the additional component is preferably a compound having at least one structure selected from the partial structure group B below, and more preferably a compound having a structure represented by formula (ED11) to (ED19), (ED21) to (ED27), (ED211), (ED212), (ED221) to (ED223), (ED231), (ED241), (ED242), (ED261) or (ED271), and having at least one structure selected from the partial structure group B bonded to a benzene ring (including a benzene ring that constitutes a fused ring) in that structure.

[0236] Substructure group B: [ka]

[0237] [ka]

[0238] [ka]

[0239] [ka]

[0240] [ka]

[0241] 1-3. Assisting dopant (thermally activated delayed phosphor) When the compound of the present invention is used as an emitting dopant (ED) in a TAF element, the assisting dopant (thermally activated delayed fluorescent substance: TADF compound) that can be used is preferably a donor-acceptor type TADF compound (DA type TADF compound) designed to localize the HOMO (highest occupied molecular orbital) and LUMO (lowest unoccupied molecular orbital) in the molecule by using an electron-donating substituent called a donor and an electron-accepting substituent called an acceptor, thereby causing efficient reverse intersystem crossing. In this specification, the term "electron-donating substituent" (donor) refers to a substituent or partial structure in which the HOMO orbital is localized in a TADF compound molecule, and the term "electron-accepting substituent" (acceptor) refers to a substituent or partial structure in which the LUMO orbital is localized in a TADF compound molecule. In general, TADF compounds using donors and acceptors have large spin orbit coupling (SOC) due to their structure, and small exchange interaction between HOMO and LUMO, resulting in a low ΔE STSince the ΔT is small, a very fast reverse intersystem crossing rate can be obtained. On the other hand, TADF compounds using donors or acceptors have a large structural relaxation in the excited state (in some molecules, the stable structure differs between the ground state and the excited state, so when an external stimulus causes a transition from the ground state to the excited state, the structure then changes to the stable structure in the excited state), giving a wide emission spectrum, which may reduce the color purity when used as a light-emitting material.

[0242] When the compound of the present invention is used as an ED in a TAF element, the thermally activated delayed phosphor (TADF compound) can be used, for example, a compound in which a donor and an acceptor are bonded directly or via a spacer. As the donor and acceptor structures used in the thermally activated delayed phosphor, for example, the structures described in Chemistry of Materials, 2017, 29, 1946-1963 can be used. Examples of donor structures include carbazole, dimethylcarbazole, di-tert-butylcarbazole, dimethoxycarbazole, tetramethylcarbazole, benzofluorocarbazole, benzothienocarbazole, phenyldihydroindolocarbazole, phenylbicarbazole, bicarbazole, tercarbazole, diphenylcarbazolylamine, tetraphenylcarbazolyldiamine, phenoxazine, dihydrophenazine, phenothiazine, dimethyldihydroacridine, diphenylamine, bis(tert-butyl)phenylamine, (diphenylamino)phenyldiphenylbenzenediamine, dimethyltetraphenyldihydroacridinediamine, tetramethyldihydroindenoacridine, and diphenyldihydrodibenzoazasiline. Acceptor structures include sulfonyldibenzene, benzophenone, phenylenebis(phenylmethanone), benzonitrile, isonicotinonitrile, phthalonitrile, isophthalonitrile, paraphthalonitrile, benzenetricarbonitrile, triazole, oxazole, thiadiazole, benzothiazole, benzobis(thiazole), benzoxazole, benzobis(oxazole), quinoline, benzimidazole, dibenzoquinoxaline, heptaazaphenalene, thioxanthone dioxide, dimethylanthracenone, anthracenedione, cycloheptabipyridine, fluorene dicarbonitrile, triphenyltriazine, pyrazinedicarbonitrile, pyrimidine, phenylpyrimidine, methylpyrimidine, pyridinedicarbonitrile, dibenzoquinoxalinedicarbonitrile, bis(phenylsulfonyl)benzene, dimethylthioxanthene dioxide, thianthrene tetraoxide, and tris(dimethylphenyl)borane.In particular, the compound having thermally activated delayed fluorescence of the present invention is preferably a compound having at least one selected from carbazole, phenoxazine, acridine, triazine, pyrimidine, pyrazine, thioxanthene, benzonitrile, phthalonitrile, isophthalonitrile, diphenylsulfone, triazole, oxadiazole, thiadiazole, and benzophenone as a partial structure.

[0243] The compound used as the assisting dopant of the light-emitting layer of the present invention is preferably a thermally activated delayed phosphor, and its emission spectrum is at least partially overlapped with the absorption peak of the emitting dopant.The following shows examples of compounds that can be used as the assisting dopant of the light-emitting layer of the present invention.However, the compounds that can be used as the assisting dopant in the present invention are not limited to the following example compounds, and in the following formula, Me represents methyl, tBu represents t-butyl, Ph represents phenyl, and wavy line represents a bond position.

[0244] [ka]

[0245] [ka]

[0246] [ka]

[0247] [ka]

[0248] [ka]

[0249]

change

[0250]

change

[0251]

change

[0252]

change

[0253]

change

[0254]

change

[0255]

change

[0256]

change

[0257]

change

[0258]

change

[0259]

change

[0260] [ka]

[0261] [ka]

[0262] [ka]

[0263] Furthermore, as the thermally activated delayed phosphor, a compound represented by any one of the following formulae (AD1), (AD2) and (AD3) can also be used.

[0264] [ka]

[0265] In formulas (AD1), (AD2) and (AD3), Each M is independently a single bond, -O-, >N-Ar, or >CAr 2and preferably a single bond, -O- or >N-Ar from the viewpoint of the depth of the HOMO of the partial structure to be formed and the height of the excited singlet energy level and the excited triplet energy level. J is a spacer structure separating the donor partial structure and the acceptor partial structure, each of which is independently an arylene having 6 to 18 carbon atoms, and from the viewpoint of the magnitude of the conjugation exuded from the donor partial structure and the acceptor partial structure, an arylene having 6 to 12 carbon atoms is preferable. More specifically, phenylene, methylphenylene and dimethylphenylene are exemplified. Q is each independently =C(-H)- or =N-, and preferably =N- from the viewpoint of the shallowness of the LUMO of the partial structure to be formed and the height of the excited singlet energy level and the excited triplet energy level. Ar are each independently hydrogen, an aryl having 6 to 24 carbon atoms, a heteroaryl having 2 to 24 carbon atoms, an alkyl having 1 to 12 carbon atoms, or a cycloalkyl having 3 to 18 carbon atoms, and from the viewpoint of the HOMO depth and the height of the excited singlet energy level and the excited triplet energy level of the partial structure to be formed, preferably hydrogen, an aryl having 6 to 12 carbon atoms, a heteroaryl having 2 to 14 carbon atoms, an alkyl having 1 to 4 carbon atoms, or a cycloalkyl having 6 to 10 carbon atoms, more preferably hydrogen, phenyl, tolyl, xylyl, mesityl, biphenyl, pyridyl, bipyridyl, triazyl, carbazolyl, dimethylcarbazolyl, di-tert-butylcarbazolyl, benzimidazole, or phenylbenzimidazole, and further preferably hydrogen, phenyl, or carbazolyl. m is 1 or 2. n is an integer of 2 to (6-m), and from the viewpoint of steric hindrance, preferably an integer of 4 to (6-m). Furthermore, at least one hydrogen in the compounds represented by the above formulas may be substituted with a halogen or deuterium.

[0266] More specifically, the compound used as the second component of the light-emitting layer of the present invention is preferably 4CzBN, 4CzBN-Ph, 5CzBN, 3Cz2DPhCzBN, 4CzIPN, 2PXZ-TAZ, Cz-TRZ3, BDPCC-TPTA, MA-TA, PA-TA, FA-TA, PXZ-TRZ, DMAC-TRZ, BCzT, DCzTrz, DDCzTRz, spiroAC-TRZ, Ac-HPM, Ac-PPM, Ac-MPM, TCzTrz, TmCzTrz and DCzmCzTrz.

[0267] 2. 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 and mixing one or more types of electron transport / injection materials. The electron transport layer 106 and the electron injection layer 107 may be formed from a mixture of an electron transport / injection material and a polymer binder.

[0268] 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.

[0269] 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.

[0270] Materials used in the electron transport layer or electron injection layer preferably contain at least one selected from compounds consisting of aromatic rings or heteroaromatic rings composed of one or more atoms selected from carbon, hydrogen, oxygen, sulfur, silicon, and phosphorus, pyrrole derivatives and their condensed ring derivatives, and metal complexes having electron-accepting nitrogen. Specific examples include condensed ring aromatic ring derivatives such as naphthalene and anthracene, styryl aromatic ring derivatives such as 4,4'-bis(diphenylethenyl)biphenyl, perinone derivatives, coumarin derivatives, naphthalimide derivatives, quinone derivatives such as anthraquinone and diphenoquinone, phosphine oxide derivatives, arylnitrile derivatives, and indole derivatives. Examples of metal complexes having electron-accepting nitrogen include hydroxyazole complexes such as hydroxyphenyloxazole complexes, azomethine complexes, tropolone metal complexes, flavonol metal complexes, and benzoquinoline metal complexes. These materials can be used alone or in combination with different materials.

[0271] Specific examples of other electron transport 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 (such as 1,3-bis[(4-t-butylphenyl)1,3,4-oxadiazolyl]phenylene), thiophene derivatives, triazole derivatives (such as N-naphthyl-2,5-diphenyl-1,3,4-triazole), 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, Examples of suitable amines include pyrazine derivatives, benzoquinoline derivatives (such as 2,2'-bis(benzo[h]quinolin-2-yl)-9,9'-spirobifluorene), imidazopyridine derivatives, benzimidazole derivatives (such as tris(N-phenylbenzimidazol-2-yl)benzene), benzoxazole derivatives, thiazole derivatives, benzothiazole derivatives, quinoline derivatives, oligopyridine derivatives such as terpyridine, bipyridine derivatives, terpyridine derivatives (such as 1,3-bis(4'-(2,2':6'2"-terpyridinyl))benzene), naphthyridine derivatives (such as bis(1-naphthyl)-4-(1,8-naphthyridin-2-yl)phenylphosphine oxide), aldazine derivatives, pyrimidine derivatives, arylnitrile derivatives, indole derivatives, phosphine oxide derivatives, bisstyryl derivatives, silole derivatives, and azoline derivatives.

[0272] 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.

[0273] The above-mentioned materials may be used alone or in combination with different materials.

[0274] Among the above-mentioned materials, borane derivatives, pyridine derivatives, fluoranthene derivatives, BO-based derivatives, anthracene derivatives, benzofluorene derivatives, phosphine oxide derivatives, pyrimidine derivatives, arylnitrile derivatives, triazine derivatives, benzimidazole derivatives, phenanthroline derivatives, and quinolinol-based metal complexes are preferable.

[0275] <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.

[0276] [ka]

[0277] In formula (ETM-1), R 11 and R 12 are each independently at least one of hydrogen, alkyl, optionally substituted aryl, substituted silyl, optionally substituted nitrogen-containing heterocycle, or cyano; R 13 ~R 16 are each independently an optionally substituted alkyl 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, and alkyl.

[0278] Among the compounds represented by formula (ETM-1), compounds represented by the following formula (ETM-1-1) and compounds represented by the following formula (ETM-1-2) are preferred.

[0279] [ka]

[0280] In formula (ETM-1-1), R 11 and R 12 are each independently at least one of hydrogen, alkyl, optionally substituted aryl, substituted silyl, optionally substituted nitrogen-containing heterocycle, or cyano; R 13 ~R 16 are each independently an optionally substituted alkyl or an optionally substituted aryl; R 21 and R 22 are each independently at least one of hydrogen, alkyl, 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 the like.

[0281] [ka]

[0282] In formula (ETM-1-2), R 11 and R 12 are each independently at least one of hydrogen, alkyl, optionally substituted aryl, substituted silyl, optionally substituted nitrogen-containing heterocycle, or cyano; R 13 ~R 16 are each independently an optionally substituted alkyl or an optionally substituted aryl; X 1is an optionally substituted arylene having 20 or less carbon atoms, and each n is independently an integer of 0 to 3. In addition, examples of the substituent in the case where "optionally substituted" or "substituted" include aryl, heteroaryl, alkyl, and the like.

[0283] X 1 Specific examples of the divalent groups include those represented by the following formulae (X-1) to (X-9). [ka] (In each formula, R a are each independently alkyl or optionally substituted phenyl, and * represents the bonding position.

[0284] Specific examples of the borane derivative include the following: [ka]

[0285] The borane derivative can be produced using known raw materials and known synthesis methods.

[0286] <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).

[0287] [ka]

[0288] 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.

[0289] In formula (ETM-2-1), R 11 ~R18 are each independently hydrogen, alkyl (preferably alkyl having 1 to 24 carbon atoms), cycloalkyl (preferably cycloalkyl having 3 to 12 carbon atoms) or aryl (preferably aryl having 6 to 30 carbon atoms).

[0290] In formula (ETM-2-2), R 11 and R 12 are each independently hydrogen, alkyl (preferably alkyl having 1 to 24 carbon atoms), cycloalkyl (preferably cycloalkyl having 3 to 12 carbon atoms) or aryl (preferably aryl having 6 to 30 carbon atoms); R 11 and R 12 may be bonded to form a ring.

[0291] 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. In addition, the pyridine-based substituent may be bonded to φ, an anthracene ring, or a fluorene ring in each formula via a phenylene group or a naphthylene group.

[0292] [ka]

[0293] The pyridine-based substituent is any one of the formulae (Py-1) to (Py-15), and among these, any one of the following formulae (Py-21) to (Py-44) (in the formulae, * indicates a bonding position) is preferable. [ka]

[0294] At least one hydrogen atom in each pyridine derivative may be replaced by deuterium, and one of the two "pyridine-based substituents" in formulae (ETM-2-1) and (ETM-2-2) may be replaced by aryl.

[0295] R 11 ~R 18 The "alkyl" in the above may be either linear or branched, and examples thereof include linear alkyl having 1 to 24 carbon atoms or branched alkyl having 3 to 24 carbon atoms. A preferred "alkyl" is an alkyl having 1 to 18 carbon atoms (branched alkyl having 3 to 18 carbon atoms). A more preferred "alkyl" is an alkyl having 1 to 12 carbon atoms (branched alkyl having 3 to 12 carbon atoms). An even more preferred "alkyl" is an alkyl having 1 to 6 carbon atoms (branched alkyl having 3 to 6 carbon atoms). An especially preferred "alkyl" is an alkyl having 1 to 4 carbon atoms (branched alkyl having 3 to 4 carbon atoms).

[0296] 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.

[0297] 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.

[0298] R 11 ~R 18In 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 "cycloalkyl" include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, methylcyclopentyl, cycloheptyl, methylcyclohexyl, cyclooctyl, and dimethylcyclohexyl.

[0299] 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.

[0300] 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.

[0301] 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.

[0302] R in formula (ETM-2-2) 11 and R 12 may combine to form a ring, and as a result, a cyclobutane, cyclopentane, cyclopentene, cyclopentadiene, cyclohexane, fluorene, indene, etc. may be spiro-bonded to the 5-membered ring of the fluorene skeleton.

[0303] Specific examples of this pyridine derivative include, for example, the following.

Chemical formula

[0304] This pyridine derivative can be produced using known raw materials and known synthesis methods.

[0305] <Fluoranthene derivative> The fluoranthene derivative is, for example, a compound represented by the following formula (ETM-3), and details are disclosed in International Publication No. 2010 / 134352.

Chemical formula

[0306] In formula (ETM-3), X 12 ~X 21 represents hydrogen, halogen, linear, branched or cyclic alkyl, linear, branched or cyclic alkoxy, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl. Here, examples of the substituent when substituted include aryl, heteroaryl, or alkyl, etc.

[0307] Specific examples of this fluoranthene derivative include, for example, the following.

Chemical formula

[0308] <BO-based derivative> The BO derivative is, for example, a polycyclic aromatic compound represented by the following formula (ETM-4), or a polymer of a polycyclic aromatic compound having a plurality of structures represented by the following formula (ETM-4). [ka]

[0309] R 1 ~R 11 are each independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, alkyl, alkoxy, aryloxy, or diarylboryl (two aryls may be bonded via a single bond or a linking group), in which at least one hydrogen may be substituted with an aryl, heteroaryl, or alkyl.

[0310] Also, R 1 ~R 11 Adjacent groups among these may be bonded to each other to form an aryl ring or a heteroaryl ring together with the a ring, the b ring or the c ring, and at least one hydrogen atom in the formed ring may be replaced by an aryl, a heteroaryl, a diarylamino, a diheteroarylamino, an arylheteroarylamino, an alkyl, an alkoxy, an aryloxy or a diarylboryl (two aryls may be bonded via a single bond or a linking group), and at least one hydrogen atom in these may be replaced by an aryl, a heteroaryl or an alkyl.

[0311] In addition, at least one hydrogen in the compound or structure represented by formula (ETM-4) may be substituted with a halogen or deuterium.

[0312] For an explanation of the substituents and ring formation form in formula (ETM-4), as well as a multimer formed by combining a plurality of structures of formula (ETM-4), the explanation of the polycyclic aromatic compounds represented by formula (1) or formula (2) and their multimers can be cited.

[0313] Specific examples of the BO derivative include the following: [ka]

[0314] The BO derivative can be produced using known raw materials and known synthesis methods.

[0315] <Anthracene derivatives> One of the anthracene derivatives is, for example, a compound represented by the following formula (ETM-5-1). [ka]

[0316] 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.

[0317] Each Ar can be independently selected from divalent benzene or naphthalene, and the two Ar may be different or the same, but are preferably 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).

[0318] [ka]

[0319] Among these groups, a group represented by any one of formulas (Py-1) to (Py-9) is preferred, and a group represented by any one of 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 preferred that they have the same structure. However, from the viewpoint of element characteristics, it is preferred that the two "Ar and pyridine moieties" have the same or different structures.

[0320] R 1 ~R 4 The alkyl group having 1 to 6 carbon atoms may be either linear or branched. That is, it is a linear alkyl group having 1 to 6 carbon atoms or a branched alkyl group having 3 to 6 carbon atoms. More preferably, it is an alkyl group having 1 to 4 carbon atoms (branched alkyl group 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.

[0321] 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.

[0322] 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.

[0323] 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.

[0324] 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.

[0325] One example of the anthracene derivative is a compound represented by the following formula (ETM-5-2). [ka]

[0326] Ar 1 are each independently a single bond, or a divalent benzene, naphthalene, anthracene, fluorene, or phenalene.

[0327] 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 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.

[0328] 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 same explanation as in formula (ETM-5-1) can be cited.

[0329] Specific examples of these anthracene derivatives include the following: [ka]

[0330] These anthracene derivatives can be produced using known raw materials and known synthesis methods.

[0331] <Benzofluorene derivatives> The benzofluorene derivative is, for example, a compound represented by the following formula (ETM-6). [ka]

[0332] 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 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.

[0333] 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.

[0334] 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 or branched alkyl having 3 to 24 carbon atoms. A preferred "alkyl" is an alkyl having 1 to 18 carbon atoms (branched alkyl having 3 to 18 carbon atoms). A more preferred "alkyl" is an alkyl having 1 to 12 carbon atoms (branched alkyl having 3 to 12 carbon atoms). An even more preferred "alkyl" is an alkyl having 1 to 6 carbon atoms (branched alkyl having 3 to 6 carbon atoms). An especially preferred "alkyl" is an alkyl having 1 to 4 carbon atoms (branched alkyl having 3 to 4 carbon atoms). Specific examples of "alkyl" include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, t-butyl, n-pentyl, isopentyl, neopentyl, t-pentyl, n-hexyl, 1-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, n-heptyl, 1-methylhexyl, and the like.

[0335] 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.

[0336] 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.

[0337] Specific examples of the "aryl having 6 to 30 carbon atoms" include phenyl, naphthyl, acenaphthylenyl, fluorenyl, phenalenyl, phenanthryl, triphenylenyl, pyrenyl, naphthacenyl, perylenyl, and pentacenyl.

[0338] 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.

[0339] Specific examples of the benzofluorene derivative include the following: [ka]

[0340] The benzofluorene derivative can be produced using known raw materials and known synthesis methods.

[0341] <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]

[0342] R 5 is a substituted or unsubstituted alkyl having 1 to 20 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 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, or alkyl.

[0343] The phosphine oxide derivative may be, for example, a compound represented by the following formula (ETM-7-2). [ka]

[0344] R 1 ~R 3may be the same or different and are selected from hydrogen, alkyl, cycloalkyl, aralkyl, alkenyl, cycloalkenyl, alkynyl, alkoxy, alkylthio, aryl ether, aryl thioether, aryl, heterocyclic group, halogen, cyano, aldehyde, carbonyl, carboxyl, amino, nitro, silyl, and a fused ring formed between adjacent substituents.

[0345] 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.

[0346] 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.

[0347] 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.

[0348] 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.

[0349] 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.

[0350] Moreover, cycloalkenyl refers to an unsaturated alicyclic hydrocarbon group containing a double bond, such as cyclopentenyl, cyclopentadienyl, cyclohexene, etc., which may be unsubstituted or substituted.

[0351] 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.

[0352] 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.

[0353] Moreover, alkylthio refers to an alkoxy group in which the oxygen atom of the ether bond is replaced with a sulfur atom.

[0354] 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.

[0355] An aryl thioether group is an aryl ether group in which the oxygen atom of the ether bond is replaced with a sulfur atom.

[0356] The aryl group refers to an aromatic hydrocarbon group such as phenyl, naphthyl, biphenylyl, phenanthryl, terphenyl, 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.

[0357] 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.

[0358] Halogen refers to fluorine, chlorine, bromine and iodine.

[0359] The aldehyde, carbonyl, and amino may also include those substituted with aliphatic hydrocarbons, alicyclic hydrocarbons, aromatic hydrocarbons, heterocycles, and the like.

[0360] Furthermore, the aliphatic hydrocarbons, alicyclic hydrocarbons, aromatic hydrocarbons and heterocycles may be either unsubstituted or substituted.

[0361] 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.

[0362] The condensed ring formed between adjacent substituents is, for example, Ar 1 and R 2 , Ar 1 and R 3 , Ar 2 and R 2 , Ar 2 and R 3 , R 2 and R 3 , Ar1 and Ar 2 etc. form a conjugated or non-conjugated fused ring. Here, when 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.

[0363] Specific examples of the phosphine oxide derivative include the following: [ka]

[0364] The phosphine oxide derivative can be produced using known raw materials and known synthesis methods.

[0365] <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.

[0366] [ka]

[0367] 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.

[0368] The "aryl" in the "optionally substituted aryl" includes, for example, an aryl having 6 to 30 carbon atoms, preferably an aryl having 6 to 24 carbon atoms, more preferably an aryl having 6 to 20 carbon atoms, and further preferably an aryl having 6 to 12 carbon atoms.

[0369] Specific examples of "aryl" include monocyclic aryl phenyl, bicyclic aryl (2-, 3-, 4-) biphenylyl, condensed bicyclic aryl (1-, 2-) naphthyl, tricyclic aryl terphenylyl (m-terphenyl-2'-yl, m-terphenyl-4'-yl, m-terphenyl-5'-yl, o-terphenyl-3'-yl, o-terphenyl-4'-yl, p-terphenyl-2'-yl, m-terphenyl-2-yl, m-terphenyl-3-yl, m-terphenyl-4-yl, o-terphenyl-2-yl, o-terphenyl-3-yl, o-terphenyl-4-yl, p-terphenyl-2-yl, p-terphenyl-3-yl, p-terphenyl-4-yl), condensed tricyclic aryl Examples of the aryl include acenaphthylene-(1-,3-,4-,5-)yl, fluorene-(1-,2-,3-,4-,9-)yl, phenalene-(1-,2-)yl, (1-,2-,3-,4-,9-)phenanthryl, the tetracyclic aryl group is quaterphenylyl (5'-phenyl-m-terphenyl-2-yl, 5'-phenyl-m-terphenyl-3-yl, 5'-phenyl-m-terphenyl-4-yl, m-quaterphenylyl), the condensed tetracyclic aryl group is triphenylene-(1-,2-)yl, pyrene-(1-,2-,4-)yl, naphthacene-(1-,2-,5-)yl, the condensed pentacyclic aryl group is perylene-(1-,2-,3-)yl, pentacene-(1-,2-,5-,6-)yl, etc.

[0370] 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.

[0371] 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.

[0372] The above aryl and heteroaryl may be substituted, for example, by the above aryl or heteroaryl, respectively.

[0373] Specific examples of the pyrimidine derivative include the following: [ka]

[0374] The pyrimidine derivative can be produced using known raw materials and known synthesis methods.

[0375] <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.

[0376] [ka]

[0377] Ar niFrom the viewpoint of fast electron transport property, it is preferable that the number of carbon atoms is large, and from the viewpoint of high T1, it is preferable that the number of carbon atoms is small. ni Specifically, it is preferable that the aryl group has a high T1 when used in a layer adjacent to the light-emitting layer, and is an aryl group having 6 to 20 carbon atoms, preferably an aryl group having 6 to 14 carbon atoms, and more preferably an aryl group having 6 to 10 carbon atoms. In addition, the number of substitutions n of the nitrile is preferably large from the viewpoint of high T1, and is preferably small from the viewpoint of high S1. The number of substitutions n of the nitrile is specifically an integer of 1 to 4, preferably an integer of 1 to 3, more preferably an integer of 1 to 2, and further preferably 1.

[0378] 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.

[0379] The "aryl" in the "optionally substituted aryl" includes, for example, an aryl having 6 to 30 carbon atoms, preferably an aryl having 6 to 24 carbon atoms, more preferably an aryl having 6 to 20 carbon atoms, and further preferably an aryl having 6 to 12 carbon atoms.

[0380] Specific examples of "aryl" include monocyclic aryl phenyl, bicyclic aryl (2-, 3-, 4-) biphenylyl, condensed bicyclic aryl (1-, 2-) naphthyl, tricyclic aryl terphenylyl (m-terphenyl-2'-yl, m-terphenyl-4'-yl, m-terphenyl-5'-yl, o-terphenyl-3'-yl, o-terphenyl-4'-yl, p-terphenyl-2'-yl, m-terphenyl-2-yl, m-terphenyl-3-yl, m-terphenyl-4-yl, o-terphenyl-2-yl, o-terphenyl-3-yl, o-terphenyl-4-yl, p-terphenyl-2-yl, p-terphenyl-3-yl, p-terphenyl-4-yl), condensed tricyclic aryl Examples of the aryl include acenaphthylene-(1-,3-,4-,5-)yl, fluorene-(1-,2-,3-,4-,9-)yl, phenalene-(1-,2-)yl, (1-,2-,3-,4-,9-)phenanthryl, the tetracyclic aryl group is quaterphenylyl (5'-phenyl-m-terphenyl-2-yl, 5'-phenyl-m-terphenyl-3-yl, 5'-phenyl-m-terphenyl-4-yl, m-quaterphenylyl), the condensed tetracyclic aryl group is triphenylene-(1-,2-)yl, pyrene-(1-,2-,4-)yl, naphthacene-(1-,2-,5-)yl, the condensed pentacyclic aryl group is perylene-(1-,2-,3-)yl, pentacene-(1-,2-,5-,6-)yl, and the like.

[0381] 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.

[0382] 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.

[0383] The above aryl and heteroaryl may be substituted, for example, by the above aryl or heteroaryl, respectively.

[0384] 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.

[0385] Specific examples of the arylnitrile derivative include the following compounds: [ka]

[0386] The arylnitrile derivatives can be produced using known raw materials and known synthesis methods.

[0387] <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.

[0388] [ka]

[0389] 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.

[0390] The "aryl" in the "optionally substituted aryl" includes, for example, an aryl having 6 to 30 carbon atoms, preferably an aryl having 6 to 24 carbon atoms, more preferably an aryl having 6 to 20 carbon atoms, and further preferably an aryl having 6 to 12 carbon atoms.

[0391] Specific examples of "aryl" include monocyclic aryl phenyl, bicyclic aryl (2-, 3-, 4-) biphenylyl, condensed bicyclic aryl (1-, 2-) naphthyl, tricyclic aryl terphenylyl (m-terphenyl-2'-yl, m-terphenyl-4'-yl, m-terphenyl-5'-yl, o-terphenyl-3'-yl, o-terphenyl-4'-yl, p-terphenyl-2'-yl, m-terphenyl-2-yl, m-terphenyl-3-yl, m-terphenyl-4-yl, o-terphenyl-2-yl, o-terphenyl-3-yl, o-terphenyl-4-yl, p-terphenyl-2-yl, p-terphenyl-3-yl, p-terphenyl-4-yl), condensed tricyclic aryl Examples of the aryl include acenaphthylene-(1-,3-,4-,5-)yl, fluorene-(1-,2-,3-,4-,9-)yl, phenalene-(1-,2-)yl, (1-,2-,3-,4-,9-)phenanthryl, the tetracyclic aryl group is quaterphenylyl (5'-phenyl-m-terphenyl-2-yl, 5'-phenyl-m-terphenyl-3-yl, 5'-phenyl-m-terphenyl-4-yl, m-quaterphenylyl), the condensed tetracyclic aryl group is triphenylene-(1-,2-)yl, pyrene-(1-,2-,4-)yl, naphthacene-(1-,2-,5-)yl, the condensed pentacyclic aryl group is perylene-(1-,2-,3-)yl, pentacene-(1-,2-,5-,6-)yl, etc.

[0392] 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.

[0393] 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.

[0394] The above aryl and heteroaryl may be substituted, for example, by the above aryl or heteroaryl, respectively.

[0395] Specific examples of triazine derivatives include the following: [ka]

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

[0397] <Benzimidazole derivatives> The benzimidazole derivative is, for example, a compound represented by the following formula (ETM-11). [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), n is an integer from 1 to 4, and the "benzoimidazole-based substituent" is one in which the pyridyl group in the "pyridine-based substituent" in the formulae (ETM-2), (ETM-2-1) and (ETM-2-2) is replaced with benzimidazolyl, and at least one hydrogen in the benzimidazole derivative may be replaced with deuterium.

[0399] [ka]

[0400] R in the above benzimidazolyl 11 is hydrogen, alkyl having 1 to 24 carbon atoms, cycloalkyl having 3 to 12 carbon atoms, or aryl having 6 to 30 carbon atoms, and R in formula (ETM-2-1) and formula (ETM-2-2) 11 The explanation can be cited.

[0401] φ is preferably an anthracene ring or a fluorene ring, and in this case, the structure may be that of formula (ETM-2-1) or formula (ETM-2-2). R 11 ~R 18 can be cited from those described in formula (ETM-2-1) or formula (ETM-2-2). In formula (ETM-2-1) or formula (ETM-2-2), two pyridine-based substituents are described as being bonded together, but when these are replaced with benzimidazole-based substituents, both pyridine-based substituents may be replaced with benzimidazole-based substituents (i.e., n=2), or one of the pyridine-based substituents may be replaced with a benzimidazole-based substituent and the other pyridine-based substituent may be replaced with R 11 ~R 18 (i.e., n=1). Furthermore, for example, R in formula (ETM-2-1) 11 ~R 18At least one of the above is replaced with a benzimidazole-based substituent to form a "pyridine-based substituent" R 11 ~R 18 may be substituted.

[0402] Specific examples of benzimidazole derivatives include 1-phenyl-2-(4-(10-phenylanthracen-9-yl)phenyl)-1H-benzo[d]imidazole, 2-(4-(10-(naphthalene-2-yl)anthracen-9-yl)phenyl)-1-phenyl-1H-benzo[d]imidazole, 2-(3-(10-(naphthalene-2-yl)anthracen-9-yl)phenyl)-1-phenyl-1H-benzo[d]imidazole, 5-(10-(naphthalene-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.

[0403] [ka]

[0404] The benzimidazole derivatives can be produced using known raw materials and known synthesis methods.

[0405] <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.

[0406] [ka]

[0407] 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.

[0408] 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.

[0409] At least one hydrogen atom in each of the phenanthroline derivatives may be replaced with deuterium.

[0410] R 11 ~R 18 As the alkyl, cycloalkyl and aryl in the formula (ETM-2), R 11 ~R 18 The explanation of the above can be cited. In addition to the above, φ can be, for example, the following structural formula. In the following structural formula, R is each independently hydrogen, methyl, ethyl, isopropyl, cyclohexyl, phenyl, 1-naphthyl, 2-naphthyl, biphenylyl, or terphenylyl, and * indicates a bonding position.

[0411] [ka]

[0412] 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, and 1,3-bis(2-phenyl-1,10-phenanthroline-9-yl)benzene.

[0413] [ka]

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

[0415] <Quinolinol metal complexes> The quinolinol metal complex is, for example, a compound represented by the following formula (ETM-13). [ka]

[0416] In the formula, R 1 ~R 6 are each independently hydrogen, fluorine, alkyl, aralkyl, alkenyl, cyano, alkoxy or aryl; M is Li, Al, Ga, Be or Zn; and n is an integer of 1 to 3.

[0417] 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.

[0418] The quinolinol metal complex can be produced using known raw materials and known synthesis methods.

[0419] <Reducing substances> At least one of the electron transport layer and the electron injection layer may contain a substance capable of reducing the material forming the electron transport layer or the electron injection layer. As the reducing substance, various substances may 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 may be preferably used.

[0420] 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 those 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.

[0421] 3. Cathode in organic electroluminescent devices 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 .

[0422] The material for forming the cathode 108 is not particularly limited as long as it is a material 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.

[0423] 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.

[0424] 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.

[0425] 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.

[0426] Materials for forming the hole injection layer 103 and the hole transport layer 104 can be arbitrarily selected from compounds conventionally used as charge transport materials for holes in photoconductive materials, p-type semiconductors, and known materials used in hole injection layers and hole transport layers of organic electroluminescent devices. 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 ( For example, 1,4,5,8,9,12-hexaazatriphenylene-2,3,6,7,10,11-hexacarbonitrile, heterocyclic compounds such as porphyrin derivatives, polysilanes, etc. As for polymers, polycarbonates and styrene derivatives having the above-mentioned monomers in their side chains, polyvinylcarbazole, polysilanes, etc. are preferred, but there is no particular limitation as long as they are compounds that can form a thin film required for fabricating a light-emitting device, can inject holes from the anode, and can transport holes.

[0427] 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, etc.) (JP 2005-167175 A).

[0428] 5. Anode in organic electroluminescent device The anode 102 serves to inject 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, holes are injected into the light-emitting layer 105 via these layers.

[0429] 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 electroluminescent devices.

[0430] 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.

[0431] 6. Substrate for organic electroluminescent device The substrate 101 is a support for the organic electroluminescent device 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, preferably 1 mm or less. As for the material of the glass, it is preferable to use non-alkali glass because it is better to have fewer ions 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.

[0432] 7. Electron blocking layer in organic electroluminescent device An electron blocking layer for preventing diffusion of electrons and / or excitons from the light-emitting layer may be provided between the hole injection / transport layer and the light-emitting layer. The electron blocking layer may be formed from a compound represented by any one of the above formulas (H1), (H2) and (H3).

[0433] 8. Method for producing organic electroluminescent device Each layer constituting the organic electroluminescent device 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 heating temperature of the vapor deposition crucible of +50 to +400°C, a vacuum degree of 10, and a temperature of 100°C. -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.

[0434] Next, as an example of a method for producing an organic electroluminescent device, a method for producing an organic electroluminescent device consisting of an anode / hole injection layer / hole transport layer / host compound, a light-emitting layer containing a thermally activated delayed phosphor and a compound having a boron atom / electron transport layer / electron injection layer / cathode will be described.

[0435] 8-1. Vapor Deposition Method A thin film of an anode material is formed on a suitable substrate by 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 compound, a thermally activated delayed phosphor, and a compound having a boron atom are co-deposited on the anode to form a thin film as a light-emitting layer, and 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 formed by deposition or the like to prepare a cathode, thereby obtaining a desired organic electroluminescence device. In the preparation of the above-mentioned organic electroluminescence device, the preparation order can be reversed to prepare the cathode, electron injection layer, electron transport layer, light-emitting layer, hole transport layer, hole injection layer, and anode in that order.

[0436] 8-2.Wet film formation method In the case of the composition for forming a light-emitting layer, a film is formed by using a wet film-forming method.

[0437] In the wet film formation method, a coating film is generally formed through a coating process in which a composition for forming an emitting layer is applied to a substrate and a drying process in which the solvent is removed from the applied composition for forming an emitting layer. Depending on the difference in the coating process, the method using a spin coater is called the spin coat method, the method using a slit coater is called the slit coat method, the method using a plate is called the gravure, offset, reverse offset, or flexographic printing method, the method using an inkjet printer is called the inkjet method, and the method spraying in a mist form is called the spray method. The drying process includes air drying, heating, and drying under reduced pressure. The drying process 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. That is, the organic electroluminescent device of the present invention is also preferably an organic electroluminescent device having a pair of electrodes consisting of an anode and a cathode, and a light-emitting layer disposed between the pair of electrodes and formed from the composition for forming a light-emitting layer of the present invention.

[0438] 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.

[0439] On the other hand, compared to the vacuum deposition method, wet film formation is 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.

[0440] 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.

[0441] 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) Formation of the hole injection layer using a wet film formation method (Step 3) Formation of the hole transport layer using a wet film formation method (Step 4) Forming a film by a wet film formation method using a composition for forming an emission layer containing a host compound, a thermally activated delayed phosphor, and a compound having a boron atom (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.

[0442] 8-3. Organic Solvents The compound of the present invention can be dissolved in a solvent and used as a composition for forming a light-emitting layer. The composition for forming a light-emitting layer of the present invention contains at least one compound of the present invention and a solvent. In addition, the composition for forming an emitting layer of the present invention preferably contains at least one compound represented by formulas (H1) to (H5), or contains at least one polymer compound having a repeating unit derived from at least one of the structures represented by formulas (H1) to (H5). The composition for forming a light-emitting layer of the present invention may further contain other components such as an emitting dopant, an assistant dopant, etc., which are used as additional components of the light-emitting layer. For example, the composition for forming a light emitting layer of the present invention preferably contains at least one compound represented by any one of the above formulas (AD1), (AD2) and (AD3). The composition for forming a light-emitting layer of the present invention preferably contains at least one organic solvent as the solvent. By controlling the evaporation rate of the organic solvent during film formation, the film-forming properties, the presence or absence of defects in the coating film, surface roughness, and smoothness can be controlled and improved. In addition, during film formation using the inkjet method, the meniscus stability at the pinhole of the inkjet head can be controlled, and the ejection properties can be controlled and improved. In addition, by controlling the drying rate of the film and the orientation of the derivative molecules, the electrical properties, light-emitting properties, efficiency, and life of an organic EL element having a light-emitting layer obtained from the composition for forming a light-emitting layer can be improved.

[0443] 8-3-1. Physical properties of organic solvents The composition for forming a light-emitting layer of the present invention preferably contains an organic solvent having a boiling point of 130° C. or more, more preferably 140° C. or more, and even more preferably 150° C. or more as the solvent. The upper limit of the boiling point of the organic solvent is preferably 300° C. or less, more preferably 270° C. or less, and even more preferably 250° C. or less. If the boiling point is higher than 130° C., it is preferable from the viewpoint of inkjet dischargeability. If the boiling point is lower than 300° C., it is preferable from the viewpoint of defects, surface roughness, residual solvent, and smoothness of the coating film. From the viewpoint of good inkjet dischargeability, film-forming property, smoothness, and low residual solvent, it is more preferable that the 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 a light-emitting layer, taking into consideration transportability, etc.

[0444] The solvent is a mixed solvent containing a good solvent (GS) and a poor solvent (PS) for at least one of the compound of the present invention or the polymer compound of the present invention, and the boiling point (BP) of the good solvent (GS) is GS ) is the boiling point (BP PS ) is preferably lower than 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. The solubility (S) of at least one compound of the compound of the present invention or the polymer compound of the present invention in a good solvent (GS) GS , %) and the solubility (S PS , %) difference (S GS -S PS ) is preferably 1% or more, more preferably 3% or more, and even more preferably 5% or more. The boiling point (BP) of the above good solvent (GS) GS ) and the boiling point (BP) of the antisolvent (PS) PS ) difference (BP PS -BP GS ) is preferably 10° C. or higher, more preferably 30° C. or higher, and even more preferably 50° C. or higher.

[0445] Further, the solvent includes a good solvent (GS) and a poor solvent (PS) for the compound represented by formula (1), formula (H1), formula (H2), formula (H3) or formula (H4), 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.

[0446] The solubility (S GS ) and the solubility (S PS ) difference (S GS -SPS 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.

[0447] After the film is formed, the organic solvent is removed from the coating film by a drying process such as vacuum, reduced pressure, or heating. When heating is performed, it is preferable to perform the heating at a temperature of glass transition temperature (Tg) of the first component +30°C or lower from the viewpoint of improving the coating film-forming property. Moreover, it is preferable to heat at a temperature of glass transition temperature (Tg) of the first component -30°C or higher from the viewpoint of reducing the residual solvent. Even if the heating temperature is lower than the boiling point of the organic solvent, the organic solvent is sufficiently removed because the film is thin. Moreover, drying may be performed multiple times at different temperatures, and multiple drying methods may be used in combination.

[0448] 8-3-2.Specific examples of organic solvents Examples of organic solvents used in the composition for forming a light-emitting 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.

[0449] 9.Applications of organic electroluminescent devices The present invention can also be applied to a display device having an organic electroluminescent element or a lighting device having an organic electroluminescent element. The display device of the present invention or the lighting device of the present invention comprises the organic electroluminescent element of the present invention. A display device or lighting device including an organic electroluminescent element can be manufactured by a known method, for example by connecting the organic electroluminescent 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.

[0450] 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.

[0451] 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.

[0452] 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.

[0453] 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.

[0454] <<Other organic devices>> The compound of 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.

[0455] 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.

[0456] 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.

[0457] 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

[0458] The present invention will be described in detail below with reference to examples, but the present invention is not limited to these examples. Synthesis examples of the compounds used in the examples are shown below.

[0459] Synthesis Example 1: Synthesis of Compound (1-1) [ka]

[0460] N 1 ,N 1 '-(1,3-phenylene)bis(2-chloro-N 1 -(Naphthalen-1-yl)-N 3 ,N 3A flask containing t-diphenylbenzene-1,3-diamine (2.75 g, 3.0 mmol) and t-butylbenzene (400 ml) was cooled in an ice bath under a nitrogen atmosphere, and 1.6 M t-butyllithium pentane solution (7.6 ml) was added. After the dropwise addition was completed, the temperature was raised to 60°C and stirred for 2 hours, and then components with a boiling point lower than that of t-butylbenzene were distilled off under reduced pressure. The mixture was cooled to -50°C, and boron tribromide (1.13 ml, 12 mmol) was added, and the mixture was heated to room temperature and stirred for 0.5 hours. Then, the mixture was cooled again in an ice bath, and N,N-diisopropylethylamine (7.70 ml, 45 mmol) was added. The mixture was stirred at room temperature until the heat generation subsided, and then heated to 120°C and stirred for 1.5 hours. The reaction solution was then distilled off under reduced pressure at 60°C to obtain a crude product. The resulting crude product was washed with acetonitrile, methanol, and toluene, in that order, and purified by silica gel column chromatography (eluent: toluene). The crude product was then recrystallized twice from o-dichlorobenzene, and then eluted at 1 × 10 -4 Purification by sublimation at 440° C. under reduced pressure of mmHg yielded 1.12 g of compound (1-1).

[0461] The structure of the compound obtained was confirmed by NMR spectrum. 1 H-NMR (400MHz, CDCl 3 ):δ=5.84(s,1H), 6.11-6.16(m,4H), 6.75(d,2H), 6.83(d,2H), 7.22(t,2H), 7.32 -7.46(m,20H), 7.60(d,2H), 8.01(d,2H), 8.07(d,2H), 9.30(d,2H), 10.50(s,1H).

[0462] Synthesis Example 2: Synthesis of Compound (1-9) [ka]

[0463] N 1 ,N 1 '-(1,3-phenylene)bis(2-chloro-N 1 -(1,2-dihydroacenaphthylene-5-yl)-N3 ,N 3 A flask containing t-diphenylbenzene-1,3-diamine (2.90 g, 3.0 mmol) and t-butylbenzene (400 ml) was cooled in an ice bath under a nitrogen atmosphere, and 1.6 M t-butyllithium pentane solution (7.6 ml) was added. After the dropwise addition was completed, the temperature was raised to 60°C and stirred for 2 hours, and then components with a boiling point lower than that of t-butylbenzene were distilled off under reduced pressure. The mixture was cooled to -50°C, and boron tribromide (1.13 ml, 12 mmol) was added, and the mixture was heated to room temperature and stirred for 0.5 hours. Then, the mixture was cooled again in an ice bath, and N,N-diisopropylethylamine (7.70 ml, 45 mmol) was added. The mixture was stirred at room temperature until the heat generation subsided, and then heated to 120°C and stirred for 1.5 hours. The reaction solution was then distilled off under reduced pressure at 60°C to obtain a crude product. The resulting crude product was washed with acetonitrile, methanol, and toluene, in that order, and purified by silica gel column chromatography (eluent: toluene). The crude product was then recrystallized twice from o-dichlorobenzene, and then eluted at 1 × 10 -4 Purification by sublimation at 440° C. under reduced pressure of mmHg was carried out to obtain 1.23 g of compound (1-9).

[0464] The structure of the compound obtained was confirmed by NMR spectrum. 1 H-NMR (400MHz, CDCl 3 ):δ=3.51-3.52(m,8H), 5.84(s,1H), 6.12-6.16(m,4H), 6.56(d,2H), 6.81(d,2H), 7.25-7.48(m,24H), 9.31(d,2H), 10.51(s,1H).

[0465] Synthesis Example 3: Synthesis of Compound (1-49) [ka]

[0466] N 1 ,N 1 '-(1,3-phenylene)bis(2-chloro-N 3 ,N 3 -Diphenyl-N1 A flask containing -(pyrimidin-5-yl)benzene-1,3-diamine) (2.46 g, 3.0 mmol) and t-butylbenzene (400 ml) was cooled in an ice bath under a nitrogen atmosphere, and 1.6 M t-butyllithium pentane solution (7.6 ml) was added. After the dropwise addition was completed, the temperature was raised to 60°C and stirred for 2 hours, and then components with a boiling point lower than that of t-butylbenzene were distilled off under reduced pressure. The mixture was cooled to -50°C, and boron tribromide (1.13 ml, 12 mmol) was added, and the mixture was heated to room temperature and stirred for 0.5 hours. Then, the mixture was cooled again in an ice bath, and N,N-diisopropylethylamine (7.70 ml, 45 mmol) was added. The mixture was stirred at room temperature until the heat generation subsided, and then heated to 120°C and stirred for 1.5 hours. The reaction solution was then distilled off under reduced pressure at 60°C to obtain a crude product. The resulting crude product was washed with acetonitrile, methanol, and toluene, in that order, and purified by silica gel column chromatography (eluent: toluene). The crude product was then recrystallized twice from o-dichlorobenzene, and then eluted at 1 × 10 -4 Purification by sublimation at 440° C. under reduced pressure of mmHg was carried out to obtain 0.34 g of compound (1-49).

[0467] The structure of the compound obtained was confirmed by NMR spectrum. 1 H-NMR (400MHz, CDCl 3 ):δ=5.98(s,1H), 6.18(d,2H), 6.27(d,2H), 6.85(d,2H), 7.32-7.46(m,16H), 8.58(s,4H), 8.90(s,2H), 9.28(d,2H), 10.51(s,1H).

[0468] Synthesis Example 4: Synthesis of Compound (1-79) [ka]

[0469] N 1 ,N 1 '-(1,3-phenylene)bis(2-chloro-N 1 -(Dibenzo[b,d]furan-2-yl)-N 3,N 3 ,N 5 ,N 5 A flask containing t-tetraphenylbenzene-1,3,5-triamine (3.83 g, 3.0 mmol) and t-butylbenzene (400 ml) was cooled in an ice bath under a nitrogen atmosphere, and 1.6 M t-butyllithium pentane solution (7.6 ml) was added. After the dropwise addition was completed, the temperature was raised to 60°C and stirred for 2 hours, and then components with a boiling point lower than that of t-butylbenzene were distilled off under reduced pressure. The mixture was cooled to -50°C, and boron tribromide (1.13 ml, 12 mmol) was added, and the mixture was heated to room temperature and stirred for 0.5 hours. Then, the mixture was cooled again in an ice bath, and N,N-diisopropylethylamine (7.70 ml, 45 mmol) was added. The mixture was stirred at room temperature until the heat generation subsided, and then heated to 120°C and stirred for 1.5 hours. The reaction solution was then distilled off under reduced pressure at 60°C to obtain a crude product. The resulting crude product was washed with acetonitrile, methanol, and toluene, in that order, and purified by silica gel column chromatography (eluent: toluene). The crude product was then recrystallized twice from o-dichlorobenzene, and then eluted at 1 × 10 -4 Purification by sublimation at 440° C. under reduced pressure of mmHg was performed to obtain 0.66 g of compound (1-79).

[0470] The structure of the compound obtained was confirmed by NMR spectrum. 1 H-NMR (400MHz, CDCl 3 ):δ=5.70(s,2H), 5.77(s,2H), 5.85(s,1H), 6.59(d,2H), 6.86-6.93(m,14H), 7.11(dd,8H ), 7.29-7.45(m,20H), 7.55(d,2H), 7.84(d,2H), 7.95(d,2H), 9.31(d,2H), 10.51(s,1H).

[0471] Synthesis Example 5: Synthesis of Compound (1-116) [ka]

[0472] N 1 ,N 1'-(1,3-phenylene)bis(2-chloro-N 1 -(Dibenzo[b,d]thiophen-1-yl)-5-(methyl-d)-N 3 -(3-(methyl-d)phenyl)-N 3 A flask containing t-phenylbenzene-1,3-diamine (3.09 g, 3.0 mmol) and t-butylbenzene (400 ml) was cooled in an ice bath under a nitrogen atmosphere, and 1.6 M t-butyllithium pentane solution (7.6 ml) was added. After the dropwise addition was completed, the temperature was raised to 60°C and stirred for 2 hours, and then components with a boiling point lower than that of t-butylbenzene were distilled off under reduced pressure. The mixture was cooled to -50°C, and boron tribromide (1.13 ml, 12 mmol) was added, and the mixture was heated to room temperature and stirred for 0.5 hours. Then, the mixture was cooled again in an ice bath, and N,N-diisopropylethylamine (7.70 ml, 45 mmol) was added. The mixture was stirred at room temperature until the heat generation subsided, and then heated to 120°C and stirred for 1.5 hours. The reaction solution was then distilled off under reduced pressure at 60°C to obtain a crude product. The resulting crude product was washed with acetonitrile, methanol, and toluene, in that order, and purified by silica gel column chromatography (eluent: toluene). The crude product was then recrystallized twice from o-dichlorobenzene, and then eluted at 1 × 10 -4 Purification by sublimation at 440° C. under reduced pressure of mmHg was performed to obtain 1.15 g of compound (1-116).

[0473] The structure of the compound obtained was confirmed by NMR spectrum. 1 H-NMR (400MHz, CDCl 3 ):δ=2.11(s,6H), 2.13(s,6H), 5.86(s,1H), 6.03(s,2H), 6.06(s,2H), 6.78(s,2H), 7.05(d,2H) ), 7.30-7.40(m,12H), 7.47-7.54(m,8H), 7.92(d,2H), 8.45(d,2H), 9.29(d,2H), 10.52(s,1H).

[0474] Synthesis Example 6: Synthesis of Compound (1-374) [ka]

[0475] N 1 ,N 1 '-(1,3-phenylene)bis(2-chloro-N 3 ,N 3 -Diphenyl-N 1 A flask containing -(pyrimidin-4-yl)benzene-1,3-diamine) (2.07 g, 3.0 mmol) and t-butylbenzene (400 ml) was cooled in an ice bath under a nitrogen atmosphere, and 1.6 M t-butyllithium pentane solution (7.6 ml) was added. After the dropwise addition was completed, the temperature was raised to 60°C and stirred for 2 hours, and then components with a boiling point lower than that of t-butylbenzene were distilled off under reduced pressure. The mixture was cooled to -50°C, and boron tribromide (1.13 ml, 12 mmol) was added, and the mixture was heated to room temperature and stirred for 0.5 hours. Then, the mixture was cooled again in an ice bath, and N,N-diisopropylethylamine (7.70 ml, 45 mmol) was added. The mixture was stirred at room temperature until the heat generation subsided, and then heated to 120°C and stirred for 1.5 hours. The reaction solution was then distilled off under reduced pressure at 60°C to obtain a crude product. The resulting crude product was washed with acetonitrile, methanol, and toluene, in that order, and purified by silica gel column chromatography (eluent: toluene). The crude product was then recrystallized twice from o-dichlorobenzene, and then eluted at 1 × 10 -4 Purification by sublimation at 440° C. under reduced pressure of mmHg was performed to obtain 0.26 g of compound (1-374).

[0476] The structure of the compound obtained was confirmed by NMR spectrum. 1 H-NMR (400MHz, CDCl 3 ):δ=5.97(s,1H), 6.11(d,1H), 6.32-6.33(m,2H), 6.42(d,2H), 6.51(d,1H), 6.83(d,1H), 7.03(d,1H), 7.25 (t,1H), 7.32(d,2H), 7.39-7.53(m,8H), 8.34(d,2H), 8.40(d,2H), 9.31(d,1H), 9.46(d,1H), 10.62(s,1H).

[0477] Synthesis Example 7: Synthesis of Compound (1-734) [ka]

[0478] A flask containing N,N'-((1,3-phenylenebis(oxy))bis(2-chloro-3,1-phenylene))bis(N-phenylpyrimidin-4-amine) (1.84 g, 3.0 mmol) and t-butylbenzene (400 ml) was cooled in an ice bath under a nitrogen atmosphere, and 1.6 M t-butyllithium pentane solution (7.6 ml) was added. After the dropwise addition was completed, the temperature was raised to 60°C and stirred for 2 hours, and then components with a boiling point lower than that of t-butylbenzene were distilled off under reduced pressure. The mixture was cooled to -50°C, and boron tribromide (1.13 ml, 12 mmol) was added, and the mixture was heated to room temperature and stirred for 0.5 hours. Thereafter, the mixture was cooled again in an ice bath, and N,N-diisopropylethylamine (7.70 ml, 45 mmol) was added. The mixture was stirred at room temperature until the heat generation subsided, and then heated to 120°C and stirred for 1.5 hours. The reaction solution was then distilled off under reduced pressure at 60°C to obtain a crude product. The crude product was washed with acetonitrile, methanol, and toluene, in that order, and purified by silica gel column chromatography (eluent: toluene). The crude product was then recrystallized twice from o-dichlorobenzene, and then eluted with 1 × 10 -4 Purification by sublimation at 440° C. under reduced pressure of mmHg was performed to obtain 0.21 g of compound (1-734).

[0479] The structure of the compound obtained was confirmed by NMR spectrum. 1 H-NMR (400MHz, CDCl 3 ):δ=6.29(s,1H), 6.44-6.45(m,4H), 6.53(d,2H), 6.82(d,2H), 7.36-7.37 (m,4H), 7.44(t,2H), 8.34(s,2H), 8.41(d,2H), 9.28(d,2H), 10.74(s,1H).

[0480] <Evaluation methods for basic physical properties> Sample preparation When evaluating the absorption and emission characteristics (fluorescence and phosphorescence) of a compound to be evaluated, the compound to be evaluated may be dissolved in a solvent and evaluated in the solvent, or in a thin film state. Furthermore, when evaluating in a thin film state, depending on the manner in which the compound to be evaluated is used in an organic EL device, only the compound to be evaluated may be made into a thin film and evaluated, or the compound to be evaluated may be dispersed in an appropriate matrix material and made into a thin film and evaluated. Here, a thin film obtained by vapor-depositing only the compound to be evaluated is called a "single film," and a thin film obtained by applying and drying a coating liquid containing the compound to be evaluated and a matrix material is called a "coated film."

[0481] As the matrix material, commercially available PMMA (polymethyl methacrylate) can be used. In this example, PMMA and the compound to be evaluated are dissolved in toluene, and then a thin film is formed on a transparent support substrate (10 mm x 10 mm) made of quartz by spin coating to prepare a sample.

[0482] Furthermore, a thin film sample in which the matrix material is a host compound is prepared as follows. A transparent support substrate made of quartz (10 mm × 10 mm × 1.0 mm) was fixed to the substrate holder of a commercially available deposition device (manufactured by Choshu Sangyo Co., Ltd.), and a molybdenum deposition boat containing a host compound and a molybdenum deposition boat containing a dopant material were installed. The vacuum chamber was then opened to 5 × 10 -4 The pressure is reduced to 100 Pa. Next, the deposition boat containing the host compound and the deposition boat containing the dopant material are heated simultaneously, and the host compound and the dopant material are co-deposited to an appropriate film thickness to form a mixed thin film (sample) of the host compound and the dopant material. Here, the deposition rate is controlled according to the set mass ratio of the host compound and the dopant material.

[0483] Absorption and emission characterization The absorption spectrum of the sample is measured using an ultraviolet-visible-near infrared spectrophotometer (Shimadzu Corporation, UV-2600), and the fluorescence spectrum or phosphorescence spectrum of the sample is measured using a spectrofluorophotometer (Hitachi High-Tech Corporation, F-7000).

[0484] For measuring the fluorescence spectrum, the sample is excited at an appropriate excitation wavelength at room temperature and photoluminescence is measured. For measuring the phosphorescence spectrum, the sample is immersed in liquid nitrogen (temperature 77 K) using an attached cooling unit. To observe the phosphorescence spectrum, an optical chopper is used to adjust the delay time from irradiation with excitation light to the start of measurement. The sample is excited at an appropriate excitation wavelength and photoluminescence is measured.

[0485] In addition, the fluorescence quantum yield (PLQY) is measured using an absolute PL quantum yield measurement device (Hamamatsu Photonics KK, C9920-02G).

[0486] Evaluation of fluorescence lifetime (delayed fluorescence) The fluorescence lifetime was measured at 300K using a fluorescence lifetime measurement device (Hamamatsu Photonics, C11367-01). Specifically, emission components with fast and slow fluorescence lifetimes were observed at the maximum emission wavelength measured with an appropriate excitation wavelength. In fluorescence lifetime measurements at room temperature of typical organic EL materials that emit fluorescence, slow emission components involving triplet components derived from phosphorescence are rarely observed due to thermal deactivation of the triplet components. If a slow emission component is observed in the compound being evaluated, it indicates that triplet energy with a long excitation lifetime has been transferred to singlet energy by thermal activation and observed as delayed fluorescence.

[0487] Calculation of energy gap (Eg) Calculate Eg = 1240 / A from the long wavelength end A (nm) of the absorption spectrum obtained by the above method.

[0488] Ionization potential (Ip) measurement A transparent support substrate (28 mm × 26 mm × 0.7 mm) on which ITO (indium tin oxide) was evaporated was fixed to the substrate holder of a commercially available evaporation device (Choshu Sangyo Co., Ltd.), a molybdenum evaporation boat containing the target compound was attached, and the vacuum chamber was opened to 5 × 10 -4The pressure is reduced to 100 Pa. Next, the deposition boat is heated to evaporate the target compound, forming a film of the target compound alone (neat film).

[0489] The obtained single film is used as a sample, and the ionization potential of the target compound is measured using a photoelectron spectrometer (Sumitomo Heavy Industries, Ltd. PYS-201).

[0490] Calculation of electron affinity (Ea) The electron affinity can be estimated from the difference between the ionization potential measured by the above-mentioned method and the energy gap calculated by the above-mentioned method.

[0491] Measurement of excited singlet energy level E(S,Sh) and excited triplet energy level E(T,Sh) For a single film of the target compound formed on a glass substrate, the fluorescence spectrum is observed at 77 K using excitation light at a peak on the long wavelength side so that the fluorescence peak of the absorption spectrum does not overlap, and the excited singlet energy level E(S,Sh) is obtained from the shoulder on the short wavelength side of the peak of the fluorescence spectrum. In addition, a phosphorescence spectrum is observed for a single film of the target compound formed on a glass substrate at 77 K using excitation light with a peak on the long wavelength side of 1 nm so that the fluorescence peak of the absorption spectrum does not overlap, and the excited triplet energy level E(T,Sh) is determined from the shoulder on the short wavelength side of the peak of the phosphorescence spectrum.

[0492] <Evaluation of organic EL elements> As described above, the compound of the present invention has a suitable energy gap (Eg), a high triplet excitation energy (E T ) and small ΔE ST Therefore, it is expected to be applicable to, for example, a light-emitting layer and a charge transport layer, and particularly to a light-emitting layer.

[0493] Evaluation items and evaluation methods The evaluation items include driving voltage (V), emission wavelength (nm), CIE chromaticity (x, y), external quantum efficiency (%), maximum wavelength (nm) and half-width (nm) of the emission spectrum, etc. For these evaluation items, values ​​at appropriate emission luminance can be used.

[0494] The quantum efficiency of a light-emitting element includes internal quantum efficiency and external quantum efficiency, and the internal quantum efficiency indicates the ratio of external energy injected as electrons (or holes) into the light-emitting layer of the light-emitting element that is converted purely into photons. On the other hand, the external quantum efficiency is calculated based on the amount of these photons that are emitted to the outside of the light-emitting element, and since some of the photons generated in the light-emitting layer are absorbed or continue to be reflected inside the light-emitting element and are not emitted to the outside of the light-emitting element, the external quantum efficiency is lower than the internal quantum efficiency.

[0495] The method of measuring the spectral radiance (emission spectrum) and external quantum efficiency is as follows. The element was made to emit light by applying a voltage using an Advantest voltage / current generator R6144. The spectral radiance in the visible light region was measured from the direction perpendicular to the light-emitting surface using a TOPCON spectroradiometer SR-3AR. Assuming that the light-emitting surface is a perfect diffusion surface, the measured spectral radiance value of each wavelength component was divided by the wavelength energy and multiplied by π to obtain the number of photons at each wavelength. Next, the number of photons was integrated over the entire observed wavelength range to obtain the total number of photons emitted from the element. The value obtained by dividing the applied current value by the elementary charge was determined as the number of carriers injected into the element, and the value obtained by dividing the total number of photons emitted from the element by the number of carriers injected into the element was determined as the external quantum efficiency (EQE). The half-width (FWHM) of the emission spectrum was calculated as the width between the wavelengths above and below where the intensity was 50% with the maximum emission wavelength (EL wavelength) at the center.

[0496] [1] Fabrication and evaluation of organic electroluminescence (EL) elements In this example, an organic EL device was fabricated according to the structure described in Adv. Mater. 2016, 28, 2777-2781. The layer structure of the fabricated organic EL device and the 100 cd / m 2 Device characteristics and LT90 (initial luminance 100cd / m 2 When continuously driven at a current density of 90 cd / m 2 The time it took to reach a plateau is summarized in Table 1.

[0497] [Table 1]

[0498] In Table 1, "NPD" is N,N'-diphenyl-N,N'-dinaphthyl-4,4'-diaminobiphenyl, "TcTa" is 4,4',4"-tris(N-carbazolyl)triphenylamine, "mCP" is 1,3-bis(N-carbazolyl)benzene, "mCBP" is 3,3'-bis(N-carbazolyl)-1,1'-biphenyl, "BPy-TP2" is 2,7-di([2,2'-bipyridine]-5-yl)triphenylene, "2CzBN" is 3,4-dicarbazolylbenzonitrile, and (DOBNA1) is 3,11-di-o-tolyl-5,9-dioxa-13b-boranaphtho[3,2,1-de]anthracene.

[0499] [ka]

[0500] Example 1: Device using compound (1-1) as a dopant Each thin film was deposited by vacuum deposition on a glass substrate (26 mm × 28 mm × 0.7 mm) with an anode made of 50 nm thick ITO (indium tin oxide) at a vacuum degree of 5 × 10 -4 The laminate was placed at 100 Pa. First, NPD was evaporated on ITO to a thickness of 40 nm, and TcTa was evaporated on top of it to a thickness of 15 nm to form a two-layer hole injection transport layer. Then, mCP was evaporated to a thickness of 15 nm to form an electron blocking layer. Next, compound DOBNA1 as a host and compound (1-1) as a dopant were co-evaporated from different evaporation sources to form an emitting layer with a thickness of 20 nm. At this time, the mass ratio of the host and the emitting dopant was 99:1. Next, 2CzBN was evaporated to a thickness of 10 nm to form a hole blocking layer. Next, BPy-TP2 was evaporated to a thickness of 20 nm to form an electron transport layer. Next, LiF was evaporated to a thickness of 1 nm, and aluminum was evaporated on top of it to a thickness of 100 nm to form a cathode, and an organic EL device was obtained.

[0501] Examples 1 to 7 and Comparative Example 1 Compound (1-1) was changed to compound (1-9), compound (1-49), compound (1-79), compound (116), compound (1-374) and compound (1-734), respectively, to give Examples 2 to 7. Compound (1-1) was also changed to compound (ED28) to give Comparative Example 1. EL elements were obtained using the same procedure and configuration as in Example 1, except for changing the compound.

[0502] Comparing the evaluation results of Examples 1 to 7 and Comparative Example 1 in Table 1, it is evident that the compounds of the present invention having specific substituents can achieve a long lifetime even when differences in emission wavelengths are taken into consideration.

[0503] [2] Fabrication of TAF element [Table 2]

[0504] In Table 2, "TSPO1" is diphenyl[4-(triphenylsilyl)phenyl]phosphine oxide. The chemical structure is shown below.

[0505] [ka]

[0506] <Example 8> <Configuration A: Element in which the host compound is mCBP, the assisting dopant is 2PXZ-TAZ, and the emitting dopant is compound (1-1)> A 26 mm × 28 mm × 0.7 mm glass substrate (manufactured by Optoscience Co., Ltd.) on which an ITO film having a thickness of 200 nm was formed by sputtering and polished to 50 nm was used as a transparent support substrate. This transparent support substrate was fixed to the substrate holder of a commercially available deposition device (manufactured by Choshu Sangyo Co., Ltd.), and a tantalum deposition boat containing NPD, TcTa, mCP, mCBP, 2PXZ-TAZ, compound (1-1), and TSPO1, and an aluminum nitride deposition boat containing LiF and aluminum were attached.

[0507] The following layers are formed in order on the ITO film of the transparent support substrate. -4 The pressure is reduced to 100 Pa, and first, NPD is heated and evaporated to a thickness of 40 nm, and then TcTa is heated and evaporated to a thickness of 15 nm to form a two-layer hole injection transport layer. Next, mCP is heated and evaporated to a thickness of 15 nm to form an electron blocking layer. Next, mCBP as a host, 2PXZ-TAZ as an assisting dopant, and compound (1-1) as an emitting dopant are simultaneously heated and co-evaporated to a thickness of 20 nm to form an emitting layer. The evaporation rate is adjusted so that the mass ratio of the host, the assisting dopant, and the emitting dopant is approximately 90:9:1. Next, TSPO1 is heated and evaporated to a thickness of 30 nm to form an electron transport layer. The evaporation rate of each of the above layers is 0.01 to 1 nm / sec. Thereafter, LiF is heated and evaporated at an evaporation rate of 0.01 to 0.1 nm / sec to a thickness of 1 nm, and then aluminum is heated and evaporated to a thickness of 100 nm to form a cathode, thereby obtaining an organic EL device. At this time, the deposition rate of aluminum is adjusted to 1 nm to 10 nm / sec.

[0508] <Example 9> <Configuration A: Element in which the host compound is mCBP, the assisting dopant is compound (1-1), and the emitting dopant is compound (ED28)> An EL device can be obtained using the same procedure and structure as in Example 5, except that the assisting dopant was changed to compound (1-1) and the emitting dopant was changed to compound (ED28).

[0509] <Example 10> <Configuration A: Element in which the host compound is mCBP, the assisting dopant is compound (1-9), and the emitting dopant is compound (ED28)> An EL device can be obtained using the same procedure and structure as in Example 5, except that the assisting dopant was changed to compound (1-9) and the emitting dopant was changed to compound (ED28).

[0510] <Example 11> <Configuration A: Element in which the host compound is mCBP, the assisting dopant is compound (1-49), and the emitting dopant is compound (ED28)> An EL device can be obtained using the same procedure and structure as in Example 5, except that the assisting dopant was changed to compound (1-49) and the emitting dopant was changed to compound (ED28). [Explanation of symbols]

[0511] 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, ring C and ring D are each independently an aryl ring or a heteroaryl ring, and at least one hydrogen atom in these rings may be substituted; Z １ and Z ２ each independently represents -CH= or -N=, and hydrogen in -CH= may be substituted; X １ ~X ４ are each independently >O or >N-R １Ｘ However, not all of them are >O, and R １Ｘ is aryl, heteroaryl, alkyl or cycloalkyl; R １Ｘ At least one of the structures shown below is any one of the structures shown below, in which any hydrogen atom may be independently substituted with an alkyl group having 1 to 8 carbon atoms, deuterium, or fluorine, and in the structures shown below, the wavy line indicates a bonding position. 【Chemistry 2】 At least one selected from the group consisting of aryl rings and heteroaryl rings in the compound represented by formula (1) may be condensed with at least one cycloalkane, at least one hydrogen in the cycloalkane may be substituted, and at least one -CH ２ - may be replaced by -O-; At least one hydrogen atom in the compound represented by formula (1) may be substituted with a halogen atom or a deuterium atom.

2. The polycyclic aromatic compound according to claim 1, represented by the following formula (2): 【Chemistry 3】 (In formula (2), R １ ~R １４ are each independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, alkyl, cycloalkyl, alkoxy, aryloxy, or diarylboryl (two aryls may be bonded via a single bond or a linking group), in which at least one hydrogen may be replaced by an aryl, heteroaryl, or alkyl; and R ３ ~R １４ adjacent two of these may be bonded to each other to form a ring, X １ ~X ４ are each independently >O or >N-R １Ｘ However, not all of them are >O, and R １Ｘ is an aryl having 6 to 20 carbon atoms, a heteroaryl having 2 to 15 carbon atoms, an alkyl having 1 to 20 carbon atoms, or a cycloalkyl having 3 to 8 carbon atoms; R １Ｘ At least one of the structures shown below is any one of the structures shown below, in which any hydrogen atom may be independently substituted with an alkyl group having 1 to 8 carbon atoms, deuterium, or fluorine, and in the structures shown below, the wavy line indicates a bonding position. 【Chemistry 4】 At least one selected from the group consisting of an aryl ring and a heteroaryl ring in the compound represented by formula (2) may be condensed with at least one cycloalkane, at least one hydrogen in the cycloalkane may be substituted, and at least one -CH ２ - may be replaced by -O-; At least one hydrogen atom in the compound represented by formula (2) may be substituted with a halogen atom or a deuterium atom.

3. R １ ~R １４ each independently represents a hydrogen atom, an aryl having 6 to 30 carbon atoms, a heteroaryl having 2 to 30 carbon atoms, a diarylamino (wherein the aryl has 6 to 12 carbon atoms), an alkyl having 1 to 12 carbon atoms, a cycloalkyl having 3 to 20 carbon atoms, or an aryloxy having 6 to 12 carbon atoms, in which at least one hydrogen atom is optionally substituted by an aryl having 6 to 12 carbon atoms or an alkyl having 1 to 8 carbon atoms; X １ ~X ４ are each independently >O or >N-R １Ｘ However, not all of them are >O, and R １Ｘ is an aryl having 6 to 12 carbon atoms or an alkyl having 1 to 8 carbon atoms, R １Ｘ At least one of the structures shown below is any one of the structures shown below, in which any hydrogen atom may be independently substituted with an alkyl group having 1 to 8 carbon atoms, deuterium, or fluorine, and in the structures shown below, the wavy line indicates a bonding position. 【Chemistry 5】 At least one hydrogen atom in the compound represented by formula (2) may be substituted with a halogen atom or a deuterium atom. The polycyclic aromatic compound according to claim 2.

4. X １ ~X ４ One or two of the １Ｘ is any of the structures shown below: １Ｘ The polycyclic aromatic compound according to claim 2 or 3, 【Chemistry 6】 In the above structures, any hydrogen may be independently replaced with alkyl having 1 to 8 carbon atoms, deuterium or fluorine, and in the structures below, the wavy lines indicate the bonding positions.

5. X １ and X ２ are all N-Ph, and X ３ and X ４ are each independently N-R １Ｘ or X １ and X ２ are each independently N-R １Ｘ And X ３ and X ４ are all N-Ph, Ph is phenyl; Multiple R １Ｘ The polycyclic aromatic compound according to any one of claims 1 to 4, wherein the structures and bonding positions of the following are identical to each other:

6. The polycyclic aromatic compound according to any one of claims 1 to 5, wherein each of the halogens is fluorine.

7. A polycyclic aromatic compound according to claim 1, wherein at least one hydrogen atom is substituted with chlorine, bromine, or iodine.

8. A polycyclic aromatic compound according to any one of claims 1 to 7, in which at least one hydrogen atom is substituted with a substituent represented by formula (B). 【Chemistry 7】 (In formula (B), R ４０ and R ４１ are each independently an alkyl group or are linked together to form an alkylene group; R ４０ and R ４１ The total number of carbon atoms is 2 to 10, and the wavy line is the binding site.)

9. A polymeric compound comprising a structure derived from the polycyclic aromatic compound described in any one of claims 1 to 8 as a repeating unit.

10. The polymer compound according to claim 9, comprising, as a repeating unit, at least one structure derived from a compound selected from the group consisting of unsubstituted or optionally substituted triarylamine, unsubstituted or optionally substituted fluorene, unsubstituted or optionally substituted anthracene, unsubstituted or optionally substituted tetracene, unsubstituted or optionally substituted triazine, unsubstituted or optionally substituted carbazole, unsubstituted or optionally substituted tetraphenylsilane, unsubstituted or optionally substituted spirofluorene, unsubstituted or optionally substituted triphenylphosphine, unsubstituted or optionally substituted dibenzothiophene, and unsubstituted or optionally substituted dibenzofuran.

11. A material for an organic device, comprising the polycyclic aromatic compound according to any one of claims 1 to 8, or the polymer compound according to claim 9 or 10.

12. The material for an organic device according to claim 11, 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.

13. A material for a light-emitting layer of an organic electroluminescent device, comprising the polycyclic aromatic compound according to any one of claims 1 to 8 or the polymer compound according to claim 9 or 10.

14. An organic electroluminescent element, an organic field effect transistor, or an organic thin-film solar cell, comprising the polycyclic aromatic compound according to any one of claims 1 to 8, or the polymer compound according to claim 9 or 10.

15. 14. An organic electroluminescent device comprising a pair of electrodes consisting of an anode and a cathode, and a light-emitting layer disposed between the pair of electrodes, the light-emitting layer comprising the material for a light-emitting layer according to claim 13.

16. The organic electroluminescent device according to claim 15, wherein the light-emitting layer contains at least one compound represented by the following formulas (H1) to (H5), or contains at least one polymer compound having a repeating unit derived from at least one of the following structures (H1) to (H5). 【Chemistry 8】 (In formula (H1), L １ is an arylene having 6 to 24 carbon atoms, Z is C-H, C-R', or N, In formula (H2), L ２ and L ３ each independently represents an aryl having 6 to 30 carbon atoms or a heteroaryl having 2 to 30 carbon atoms; At least one hydrogen atom in the compound represented by each of the above formulas may be substituted with an alkyl group having 1 to 6 carbon atoms, a cyano group, a halogen atom, or a deuterium atom; In formula (H3), J is >O, >S, >N-R', >C(-R'). ２ Or >Si(-R') ２ and Y is a single bond, >O, >S, >C(-R') ２ Or >Si(-R') ２ and Z is C-H, C-R' or N; In formula (H4), Z is C—H, C—R′ or N; Said, CR', >NR', >C(-R') ２ Or >Si(-R') ２ R' in the formula (I) is aryl, heteroaryl, alkyl or cycloalkyl; In formula (H5), R １０１ ~R １１１ are each independently hydrogen or a substituent which is an aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino or alkyl, at least one hydrogen in these substituents may be further substituted with an aryl, heteroaryl, diarylamino or alkyl; R １０１ ~R １１１ adjacent groups among the above may be bonded to each other to form an aryl ring or a heteroaryl ring together with the benzene ring to which they are bonded, and at least one hydrogen atom in the formed ring may be replaced by an aryl, a heteroaryl, a diarylamino, a diheteroarylamino, an arylheteroarylamino or an alkyl, and at least one hydrogen atom in these rings may be further replaced by an aryl, a heteroaryl, a diarylamino or an alkyl, At least one hydrogen atom in the compound represented by formula (H5) may be independently replaced with a halogen atom or a deuterium atom.

17. The organic electroluminescent device according to claim 15 or 16, wherein the light-emitting layer contains at least one compound represented by any one of the following formulas (AD1), (AD2) and (AD3): 【Chemistry 9】 (In the formulae (AD1), (AD2) and (AD3), M is independently a single bond, —O—, >N—Ar, or >CAR. ２ At least one of J's are each independently an arylene having 6 to 18 carbon atoms, and the arylene is optionally substituted with phenyl, alkyl having 1 to 6 carbon atoms, and cycloalkyl having 3 to 12 carbon atoms; Each Q is independently ═C(—H)— or ═N—; Ar's each independently represent a hydrogen atom, an aryl having 6 to 18 carbon atoms, a heteroaryl having 6 to 18 carbon atoms, an alkyl having 1 to 6 carbon atoms, or a cycloalkyl having 3 to 12 carbon atoms, and at least one hydrogen atom in the aryl and heteroaryl may be substituted with a phenyl, an alkyl having 1 to 6 carbon atoms, or a cycloalkyl having 3 to 12 carbon atoms; m is 1 or 2; n is an integer from 2 to (6-m); At least one hydrogen atom in the compounds represented by the above formulas may be substituted with a halogen or deuterium.

18. A composition for forming a light-emitting layer, comprising at least one of the polycyclic aromatic compound according to any one of claims 1 to 8 or the polymer compound according to claim 9 or 10, and a solvent.

19. The composition for forming a light-emitting layer according to claim 18 , comprising, as the solvent, an organic solvent having a boiling point of 150° C. or higher.

20. 20. The composition for forming an emission layer according to claim 18 or 19, wherein the solvent is a mixed solvent containing a good solvent and a poor solvent for at least one of the polycyclic aromatic compound or the polymer compound, and the boiling point of the good solvent is lower than the boiling point of the poor solvent.

21. The composition for forming a light-emitting layer according to any one of claims 18 to 20, comprising at least one compound represented by formulas (H1) to (H5), or at least one polymer compound having a repeating unit derived from at least one of the structures represented by formulas (H1) to (H5). 【Chemistry 10】 (In formula (H1), L １ is an arylene having 6 to 24 carbon atoms, Z is C-H, C-R', or N, In formula (H2), L ２ and L ３ each independently represents an aryl having 6 to 30 carbon atoms or a heteroaryl having 2 to 30 carbon atoms; At least one hydrogen atom in the compound represented by each of the above formulas may be substituted with an alkyl group having 1 to 6 carbon atoms, a cyano group, a halogen atom, or a deuterium atom; In formula (H3), J is >O, >S, >N-R', >C(-R'). ２ Or >Si(-R') ２ and Y is a single bond, >O, >S, >C(-R') ２ Or >Si(-R') ２ and Z is C-H, C-R' or N; In formula (H4), Z is C—H, C—R′ or N; Said, CR', >NR', >C(-R') ２ Or >Si(-R') ２ R' in the formula (I) is aryl, heteroaryl, alkyl or cycloalkyl; In formula (H5), R １０１ ~R １１１ are each independently hydrogen or a substituent which is an aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino or alkyl, at least one hydrogen in these substituents may be further substituted with an aryl, heteroaryl, diarylamino or alkyl; R １０１ ~R １１１ adjacent groups among the above may be bonded to each other to form an aryl ring or a heteroaryl ring together with the benzene ring to which they are bonded, and at least one hydrogen atom in the formed ring may be replaced by an aryl, a heteroaryl, a diarylamino, a diheteroarylamino, an arylheteroarylamino or an alkyl, and at least one hydrogen atom in these rings may be further replaced by an aryl, a heteroaryl, a diarylamino or an alkyl, At least one hydrogen atom in the compound represented by formula (H5) may be independently replaced with a halogen atom or a deuterium atom.

22. An organic electroluminescent device comprising a pair of electrodes consisting of an anode and a cathode, and a light-emitting layer disposed between the pair of electrodes, the light-emitting layer being formed from the composition for forming a light-emitting layer according to any one of claims 18 to 21.

23. The organic electroluminescence device according to any one of claims 15 to 17 and claim 22, further comprising at least one layer selected from the group consisting of an electron transport layer and an electron injection layer disposed between the cathode and the light emitting layer, and at least one of the electron transport layer and the electron injection layer contains at least one selected from the group consisting of a borane derivative, a pyridine derivative, a fluoranthene derivative, a BO-based derivative, an anthracene derivative, a benzofluorene derivative, a phosphine oxide derivative, a pyrimidine derivative, an arylnitrile derivative, a triazine derivative, a benzimidazole derivative, a phenanthroline derivative, and a quinolinol-based metal complex.

24. 24. The organic electroluminescent device according to claim 23, wherein at least one of the electron transport layer and the electron injection layer further contains at least one selected from the group consisting of alkali metals, alkaline earth metals, rare earth metals, oxides of alkali metals, halides of alkali metals, oxides of alkaline earth metals, halides of alkaline earth metals, oxides of rare earth metals, halides of rare earth metals, organic complexes of alkali metals, organic complexes of alkaline earth metals, and organic complexes of rare earth metals.

25. A display device comprising an organic electroluminescent element according to any one of claims 15 to 17 and claims 22 to 24.

26. A lighting device comprising an organic electroluminescent element according to any one of claims 15 to 17 and claims 22 to 24.

Images