Polycyclic aromatic compounds and their polymers

Abstract

To provide a polycyclic aromatic compound excellent as an organic electroluminescent element material, and an organic electroluminescent element employing the same.SOLUTION: A novel polycyclic aromatic compound represented by general formula (1) is a polycyclic aromatic compound in which multiple aromatic rings are connected through, e.g., a boron atom and a nitrogen atom or an oxygen atom, and pyridine nitrogen is introduced into the aromatic rings. In the formula, Y1 to Y6 are each independently =C(-R)- or =N-, where at least one of them is =N- (pyridine nitrogen); R1 to R5 are hydrogen, aryl, or the like; and X1 and X2 are oxygen or the like.SELECTED DRAWING: None

Description

[Technical field]

[0001] The present invention relates to a polycyclic aromatic compound and a multimer thereof (hereinafter, these are also collectively referred to simply as "polycyclic aromatic compound"), and to an organic device using the same, such as an organic electroluminescent element, an organic field effect transistor, and an organic thin-film solar cell, as well as a display device and a lighting device. [Background technology]

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

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

[0004] As materials for the light-emitting layer, for example, benzofluorene-based compounds have been developed (WO 2004 / 061047), as hole-transporting materials, for example, triphenylamine-based compounds have been developed (JP 2001-172232), and as electron-transporting materials, for example, anthracene-based compounds have been developed (JP 2005-170911).

[0005] In recent years, a material that improves triphenylamine derivatives has also been reported as a material for use in organic electroluminescence devices and organic thin-film solar cells (WO 2012 / 118164). This material is characterized by its improved planarity, which is achieved by linking the aromatic rings that make up the triphenylamine, with reference to N,N'-diphenyl-N,N'-bis(3-methylphenyl)-1,1'-biphenyl-4,4'-diamine (TPD), which has already been put to practical use. For example, this document evaluates the charge transport properties of an NO-linked compound (compound 1 on page 63), but does not describe how to manufacture materials other than NO-linked compounds. In addition, since the electronic state of the entire compound differs depending on the linked element, the properties obtained from materials other than NO-linked compounds are not yet known. There are other examples of such compounds (WO 2011 / 107186). For example, compounds with a conjugated structure with a large triplet exciton energy (T1) can emit phosphorescence with a shorter wavelength, and are therefore useful as materials for blue light-emitting layers. In addition, compounds having a new conjugated structure with a large T1 are also required as electron transport materials and hole transport materials that sandwich the light-emitting layer.

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

[0007] In recent years, compounds in which multiple aromatic rings are condensed with a central atom such as boron have also been reported (WO 2015 / 102118). In this document, an organic EL device evaluation was carried out using a compound in which multiple aromatic rings are condensed as a dopant material for the light-emitting layer, but the document discloses an extremely large number of compounds, and it is useful to consider compounds that have excellent organic EL properties, such as light-emitting properties. The light-emitting properties are basically a narrow half-width emission spectrum, a high fluorescence quantum yield, a small delayed fluorescence lifetime, a large energy gap Eg, and a small ΔE ST It is desirable that one or more of these properties are excellent, and if the material has excellent properties overall, it is expected to be used as a thermally activated delayed fluorescence material. [Prior art documents] [Patent documents]

[0008] [Patent Document 1] International Publication No. 2004 / 061047 [Patent Document 2] JP 2001-172232 A [Patent Document 3] JP 2005-170911 A [Patent Document 4] International Publication No. 2012 / 118164 [Patent Document 5] International Publication No. 2011 / 107186 [Patent Document 6] International Publication No. 2015 / 102118 Summary of the Invention [Problem to be solved by the invention]

[0009] As described above, various materials have been developed as materials for use in organic EL elements. However, in order to further improve organic EL characteristics such as light-emitting characteristics and to increase the options for organic EL materials such as materials for the light-emitting layer, there is a need for the development of compounds that were not previously specifically known. [Means for solving the problem]

[0010] As a result of intensive research to solve the above problems, the present inventors have found that an excellent organic EL device can be obtained by introducing a pyridinic nitrogen into a polycyclic aromatic compound in which a plurality of aromatic rings are linked by a boron atom and a nitrogen atom or an oxygen atom, etc., and have completed the present invention. That is, the present invention provides the following polycyclic aromatic compounds, and further provides organic device materials containing the following polycyclic aromatic compounds.

[0011] In this specification, the chemical structure or the substituent may be expressed by the number of carbon atoms, but the number of carbon atoms in the case where a substituent is substituted on the chemical structure or where a substituent is further substituted on the substituent means the number of carbon atoms in each of the chemical structure and the substituent, and does not mean the total number of carbon atoms in the chemical structure and the substituent, or the total number of carbon atoms in the substituent and the substituent. For example, "substituent B of carbon number Y substituted with substituent A of carbon number X" means that "substituent B of carbon number Y" is substituted with "substituent A of carbon number X", and the carbon number Y is not the total number of carbon atoms in the substituent A and the substituent B. Also, for example, "substituent B of carbon number Y substituted with substituent A" means that "substituent B of carbon number Y" is substituted with "substituent A (without carbon number limit)", and the carbon number Y is not the total number of carbon atoms in the substituent A and the substituent B.

[0012] Section 1. A polycyclic aromatic compound represented by the following general formula (1), or a multimer of a polycyclic aromatic compound having a plurality of structures represented by the following general formula (1). [ka] In the above formula (1), R 1 , R 2 , R 3 , R 4 and R 5 are each independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl (two aryls may be bonded via a single bond or a linking group), alkyl, cycloalkyl, alkoxy or aryloxy, in which at least one hydrogen may be further substituted with an aryl, heteroaryl, alkyl or cycloalkyl; X 1 and X 2 are independently >NR, >O, >C(-R) 2 , >S or >Se, X 1 and X 2 Both are > C(-R) 2 It will not be, The above >NR and >C(-R) 2 R in the formula (I) is independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl (two aryls may be bonded via a single bond or a linking group), alkyl, cycloalkyl, alkoxy or aryloxy, and at least one hydrogen in these formulas may be further substituted with an aryl, heteroaryl, alkyl or cycloalkyl. 2 R may each independently be bonded to at least one of the ring a, ring b and ring c via a linking group or a single bond; Y 1 , Y 2 , Y 3 , Y 4 , Y 5 and Y6 are each independently =C(-R)- or =N-, and at least one is =N-; R in the =C(-R)- is independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl (two aryls may be bonded via a single bond or a linking group), alkyl, cycloalkyl, alkoxy or aryloxy, and at least one hydrogen in these may be further substituted with aryl, heteroaryl, alkyl or cycloalkyl; R 1 , R 2 , R 3 , R 4 and R 5 , and the Y 1 ~Y 6 adjacent groups among R in =C(-R)- as the formula may be bonded to each other to form an aryl ring or a heteroaryl ring together with at least one of the a ring, the b ring, and the c ring, at least one hydrogen atom in the formed ring may be substituted with an aryl, a heteroaryl, a diarylamino, a diheteroarylamino, an arylheteroarylamino, a diarylboryl (two aryls may be bonded via a single bond or a linking group), an alkyl, a cycloalkyl, an alkoxy, or an aryloxy, at least one hydrogen atom in these may be further substituted with an aryl, a heteroaryl, an alkyl, or a cycloalkyl, and At least one hydrogen atom in the compound and structure represented by the general formula (1) may be substituted with cyano, halogen or deuterium.

[0013] Section 2. In the above formula (1), R 1 , R 2 , R 3 , R 4 and R 5each independently represents a hydrogen atom, an aryl having 6 to 30 carbon atoms, a heteroaryl having 2 to 30 carbon atoms, a diarylamino (wherein each aryl has 6 to 12 carbon atoms), a diarylboryl (wherein the aryl has 6 to 12 carbon atoms, and the two aryls may be bonded via a single bond or a linking group), an alkyl having 1 to 12 carbon atoms, a cycloalkyl having 3 to 16 carbon atoms, an alkoxy having 1 to 12 carbon atoms, or an aryloxy having 6 to 30 carbon atoms, in which at least one hydrogen atom may be further substituted by 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 16 carbon atoms; X 1 and X 2 are independently >NR, >O, >C(-R) 2 , >S or >Se, X 1 and X 2 Both are > C(-R) 2 It will not be, The above >NR and >C(-R) 2 R in the formula (I) is independently hydrogen, an aryl having 6 to 30 carbon atoms, a heteroaryl having 2 to 30 carbon atoms, a diarylamino (wherein each aryl has 6 to 12 carbon atoms), a diarylboryl (wherein the aryl has 6 to 12 carbon atoms, and the two aryls may be bonded via a single bond or a linking group), an alkyl having 1 to 12 carbon atoms, a cycloalkyl having 3 to 16 carbon atoms, an alkoxy having 1 to 12 carbon atoms, or an aryloxy having 6 to 30 carbon atoms, in which at least one hydrogen may be further substituted by 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 16 carbon atoms, and the above-mentioned >NR and >C(-R) 2 R is independently -O-, -S-, -C(-R) 2 or may be bonded to at least one of the ring a, ring b and ring c via a single bond, and the -C(-R) 2 R in - is hydrogen, alkyl having 1 to 6 carbon atoms, or cycloalkyl having 3 to 14 carbon atoms; Y 1, Y 2 , Y 3 , Y 4 , Y 5 and Y 6 are each independently =C(-R)- or =N-, and at least one is =N-; R in the =C(-R)- is each independently hydrogen, aryl having 6 to 30 carbon atoms, heteroaryl having 2 to 30 carbon atoms, diarylamino (wherein each aryl has 6 to 12 carbon atoms), diarylboryl (wherein the aryl has 6 to 12 carbon atoms, and two aryls may be bonded via a single bond or a linking group), alkyl having 1 to 12 carbon atoms, cycloalkyl having 3 to 16 carbon atoms, alkoxy having 1 to 12 carbon atoms, or aryloxy having 6 to 30 carbon atoms, in which at least one hydrogen may be further substituted by aryl having 6 to 30 carbon atoms, heteroaryl having 2 to 30 carbon atoms, alkyl having 1 to 12 carbon atoms, or cycloalkyl having 3 to 16 carbon atoms; R 1 , R 2 , R 3 , R 4 and R 5 , and the Y 1 ~Y 6 adjacent groups among R in =C(-R)- as the formula may be bonded to each other to form an aryl ring having 9 to 16 carbon atoms or a heteroaryl ring having 6 to 15 carbon atoms together with at least one of the rings a, b and c, at least one hydrogen atom in the formed ring may be substituted with an aryl group having 6 to 30 carbon atoms, a heteroaryl group having 2 to 30 carbon atoms, a diarylamino (wherein each aryl group has 6 to 12 carbon atoms), a diarylboryl (wherein the aryl group is an aryl group having 6 to 12 carbon atoms, and the two aryl groups may be bonded via a single bond or a linking group), an alkyl group having 1 to 12 carbon atoms, a cycloalkyl group having 3 to 16 carbon atoms, an alkoxy group having 1 to 12 carbon atoms, or an aryloxy group having 6 to 30 carbon atoms, at least one hydrogen atom in these rings may be further substituted with an aryl group having 6 to 30 carbon atoms, a heteroaryl group having 2 to 30 carbon atoms, an alkyl group having 1 to 12 carbon atoms, or a cycloalkyl group having 3 to 16 carbon atoms, At least one hydrogen atom in the compound and structure represented by the general formula (1) may be substituted with cyano, halogen or deuterium. Item 1. A polycyclic aromatic compound or a multimer thereof according to item 1.

[0014] Section 3. X 1 and X 2 Each of the above is independently >NR or >O.

[0015] Section 4. X 1 and X 2 are each independently >NR or >O; Y 2 , Y 3 , Y 4 and Y 5 are each independently =C(-R)-; Y 1 and Y 6 are each independently =C(-R)- or =N-, and at least one is =N-; Item 4. The polycyclic aromatic compound or a multimer thereof according to any one of Items 1 to 3.

[0016] Section 5. 5. The polycyclic aromatic compound or a multimer thereof according to any one of items 1 to 4, comprising a partial structure represented by any one of the following formulae: [ka] [ka]

[0017] Section 6. Item 2. The polycyclic aromatic compound or a multimer thereof according to item 1, which is represented by any one of the following formulas: [ka] [ka] [ka]

[0018] Section 7. Item 7. A reactive compound in which the polycyclic aromatic compound or a multimer thereof according to any one of Items 1 to 6 is substituted with a reactive substituent.

[0019] Section 8. Item 8. A polymer compound obtained by polymerizing the reactive compound described in item 7 as a monomer, or a crosslinked polymer obtained by further crosslinking the polymer compound.

[0020] Section 9. Item 7. A pendant polymer compound in which a reactive compound described in item 7 is substituted on a main chain polymer, or a pendant polymer crosslinked product in which the pendant polymer compound is further crosslinked.

[0021] Section 10. Item 7. A material for an organic device, comprising the polycyclic aromatic compound or a multimer thereof according to any one of Items 1 to 6.

[0022] Section 11. Item 8. A material for an organic device, comprising the reactive compound according to item 7.

[0023] Section 12. Item 9. A material for an organic device, comprising the polymer compound or crosslinked polymer according to item 8.

[0024] Section 13. Item 10. A material for an organic device, comprising the pendant polymer compound or the pendant polymer crosslinked body according to item 9.

[0025] Section 14. Item 14. The material for an organic device according to any one of items 10 to 13, wherein the material for an organic device 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.

[0026] Section 15. Item 15. The material for an organic device according to item 14, wherein the material for an organic electroluminescent element is a material for a light-emitting layer.

[0027] Section 16. 7. An ink composition comprising the polycyclic aromatic compound or a multimer thereof according to any one of items 1 to 6, and an organic solvent.

[0028] Section 17. Item 8. An ink composition comprising the reactive compound according to item 7 and an organic solvent.

[0029] Section 18. Item 8. An ink composition comprising a main chain polymer, the reactive compound according to item 7, and an organic solvent.

[0030] Section 19. Item 9. An ink composition comprising the polymer compound or crosslinked polymer according to item 8 and an organic solvent.

[0031] Section 20. Item 10. An ink composition comprising the pendant polymer compound or the pendant polymer crosslinked product according to item 9 and an organic solvent.

[0032] Section 21. An organic electroluminescence device comprising a pair of electrodes consisting of an anode and a cathode, and an organic layer disposed between the pair of electrodes and containing the polycyclic aromatic compound or a polymer thereof described in any one of items 1 to 6, the reactive compound described in item 7, the polymer compound or crosslinked polymer described in item 8, or the pendant polymer compound or crosslinked polymer described in item 9.

[0033] Section 22. Item 22. The organic electroluminescent device according to item 21, wherein the organic layer is a light-emitting layer.

[0034] Section 23. Item 23. The organic electroluminescence device according to item 22, wherein the light-emitting layer further contains at least one selected from the group consisting of a compound represented by the following general formula (H1), a compound represented by the following general formula (H2), a compound represented by the following general formula (H3), a compound having a structure represented by the following general formula (H4), a compound represented by the following general formula (H5), and a TADF material: [ka] In the above general formula (H1), L 1 is an arylene having 6 to 30 carbon atoms or a heteroarylene having 2 to 30 carbon atoms, In the above general 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, In the above general formula (H3), each MU is independently a divalent group represented by removing any two hydrogen atoms from an aromatic compound, each EC is independently a monovalent group represented by removing any one hydrogen atom from an aromatic compound, two hydrogen atoms in MU are replaced by EC or MU, and k is an integer of 2 to 50,000, In the above general formula (H4), each G is independently =C(-H)- or =N-, and H in the =C(-H)- may be substituted with a substituent or another structure represented by formula (H4), In the above general formula (H5), R 1 ~R 11 are each independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, alkyl or cycloalkyl, at least one hydrogen of which may be further substituted with aryl, heteroaryl, diarylamino, alkyl or cycloalkyl; R 1 ~R 11adjacent 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 or the c ring, and at least one hydrogen in the formed ring may be replaced by an aryl, a heteroaryl, a diarylamino, a diheteroarylamino, an arylheteroarylamino, an alkyl or a cycloalkyl, and at least one hydrogen in these may be further replaced by an aryl, a heteroaryl, a diarylamino, an alkyl or a cycloalkyl, and At least one hydrogen atom in the compound or structure represented by each of the above formulas may be substituted with alkyl having 1 to 6 carbon atoms, cycloalkyl having 3 to 14 carbon atoms, cyano, halogen or deuterium.

[0035] Section 24. Item 24. The organic electroluminescence device according to item 22 or 23, comprising at least one 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 derivatives, anthracene derivatives, benzofluorene derivatives, phosphine oxide derivatives, pyrimidine derivatives, carbazole derivatives, triazine derivatives, benzimidazole derivatives, phenanthroline derivatives, and quinolinol metal complexes.

[0036] Section 25. Item 25. The organic electroluminescence device according to item 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 alkali metals, alkaline earth metals, rare earth metals, alkali metal oxides, alkali metal halides, alkaline earth metal oxides, alkaline earth metal halides, rare earth metal oxides, rare earth metal halides, alkali metal organic complexes, alkaline earth metal organic complexes, and rare earth metal organic complexes.

[0037] Section 26. 26. The organic electroluminescence device according to any one of items 21 to 25, wherein at least one layer of the hole injection layer, the hole transport layer, the light-emitting layer, the electron transport layer and the electron injection layer comprises a polymer compound obtained by polymerizing a low molecular weight compound capable of forming each layer as a monomer, or a crosslinked polymer obtained by further crosslinking the polymer compound, or a pendant-type polymer compound obtained by reacting a low molecular weight compound capable of forming each layer with a main-chain polymer, or a pendant-type crosslinked polymer obtained by further crosslinking the pendant-type polymer compound.

[0038] Section 27. Item 27. A display device or lighting device comprising the organic electroluminescent device according to any one of items 21 to 26. Effect of the Invention

[0039] According to a preferred embodiment of the present invention, the polycyclic aromatic compound represented by the general formula (1), which has not been specifically known in the past, can further improve organic EL properties such as light-emitting properties and increase the options of organic EL materials such as materials for the light-emitting layer. Specific examples of the light-emitting properties include the half-width of the emission spectrum, the fluorescence quantum yield, the delayed fluorescence lifetime, the energy gap Eg and ΔE ST According to a preferred embodiment of the present invention, excellent effects can be obtained in any one or more of these properties, and when the material has excellent properties overall, it can be expected to be used as a thermally activated delayed fluorescence material. [Brief description of the drawings]

[0040] [Figure 1] FIG. 1 is a schematic cross-sectional view showing an organic EL element according to an embodiment of the present invention. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0041] 1. Polycyclic aromatic compounds represented by general formula (1) and their multimers The present invention relates to a polycyclic aromatic compound represented by the following general formula (1), or a multimer of a polycyclic aromatic compound having a plurality of structures represented by the following general formula (1). [ka]

[0042] (1) Overview of the Invention For example, three types of luminescent materials are used for organic electroluminescence displays: fluorescent materials, phosphorescent materials, and thermally activated delayed fluorescence (TADF) materials. Fluorescent materials have a low luminous efficiency of about 25 to 62.5%. On the other hand, phosphorescent and TADF materials can reach 100% luminous efficiency, but both have the problem of low color purity (wide emission spectrum). Displays express various colors by mixing the three primary colors of light, red, green, and blue, but if the color purity of each color is low, colors that cannot be reproduced will be created, and the image quality of the display will be greatly reduced. Therefore, in commercially available displays, unnecessary colors are removed from the emission spectrum with an optical filter to increase the color purity (narrow the spectrum width) before use. Therefore, if the original spectrum width is wide, the proportion of colors to be removed increases, so even if the luminous efficiency is high, the actual efficiency will be greatly reduced. For example, the half-width of the blue emission spectrum of commercially available smartphones is approximately 20 to 25 nm, while the half-width of typical fluorescent materials is approximately 40 to 60 nm, that of phosphorescent materials is approximately 60 to 90 nm, and that of TADF materials is approximately 70 to 100 nm. When using fluorescent materials, the half-width is relatively narrow, so it is sufficient to remove only a portion of the unwanted color, but when using phosphorescent or TADF materials, it is necessary to remove more than half of the color. Against this background, there was a demand for the development of a luminescent material that combines both luminous efficiency and color purity.

[0043] In general, TADF materials are designed to localize the HOMO and LUMO within the molecule using electron-donating substituents called donors and electron-accepting substituents called acceptors, thereby causing efficient reverse intersystem crossing. However, the use of donors or acceptors increases structural relaxation in the excited state (since the stable structures of some molecules differ between the ground state and the excited state, 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), resulting in a broad emission spectrum with low color purity.

[0044] Therefore, Patent Document 6 (WO 2015 / 102118) proposes a new molecular design that dramatically improves the color purity of TADF materials. For example, in compound (1-401) disclosed in the document, by utilizing the multiple resonance effect of boron (electron-accepting) and nitrogen (electron-donating), it has succeeded in localizing the HOMO on three carbons (black circles) on a benzene ring consisting of six carbons, and the LUMO on the remaining three carbons (white circles). Due to this efficient reverse intersystem crossing, the emission efficiency of the compound reaches a maximum of 100%. Furthermore, the boron and nitrogen in compound (1-401) not only localize the HOMO and LUMO, but also play a role in maintaining a robust planar structure by condensing the three benzene rings and suppressing structural relaxation in the excited state, and as a result, it has been successful in obtaining an emission spectrum with a small Stokes shift of the absorption and emission peaks and high color purity. The half-width of the emission spectrum is 28 nm, which is a level of color purity that surpasses that of fluorescent materials with high color purity that are in practical use. In addition, in the dimer compound (1-422), two boron atoms and two nitrogen atoms are bonded to the central benzene ring, which further enhances the multiple resonance effect in the central benzene ring, resulting in emission with an extremely narrow emission peak width. [ka]

[0045] On the other hand, compound (1-401) has an energy difference between the excited singlet energy and the excited triplet energy, ΔE ST However, due to its high planarity and small spin-orbit coupling (SOC), the delayed fluorescence lifetime (Tau(Delay)) is long, and there was a problem that the efficiency was low or the roll-off was large when it was used as a light-emitting material for an organic electroluminescent device using thermally activated delayed fluorescence (TADF).

[0046] As a result of intensive research, we have achieved adjustment of the emission wavelength and half-width of the emission spectrum, high emission efficiency, and short delayed fluorescence lifetime in polycyclic aromatic compounds by appropriately combining three approaches: (i) introducing elements that enhance the multiple resonance effect at appropriate positions, (ii) bridging aromatic rings to increase the planarity of the molecule, and (iii) introducing substituents at appropriate positions to distort the molecule and decrease the planarity. As a result, we have achieved appropriate emission wavelength and half-width of the emission spectrum, high device efficiency, and small roll-off in devices.

[0047] Regarding (i) above, in order to strengthen the multiple resonance effect, an amine nitrogen, which is an electron-donating element, and boron, which is an electron-accepting element, are introduced into an appropriate position in the molecule. Specifically, electron-donating elements or electron-withdrawing elements are arranged in meta positions, and an electron-donating element and an electron-withdrawing element are arranged in ortho or para positions. In addition to boron, pyridinic nitrogen is also an electron-accepting element. Pyridinic nitrogen is nitrogen that replaces the carbon that constitutes a benzene ring. This pyridinic nitrogen is arranged in the meta position relative to boron (i.e., the central elements B and Y in the above formula (1) are arranged in the meta position relative to boron). 1 ~Y 6 By arranging the pyridine nitrogen and boron in the same position, the electron-accepting properties of the pyridine nitrogen and boron are strengthened, resulting in a stronger multiple resonance effect. As a result, ΔE ST This makes it possible to design TADF dopant materials with higher efficiency and longer life. At the same time, the half-width becomes narrower, which leads to higher light extraction efficiency.

[0048] In addition, when an electron-donating substituent is bonded to a carbon atom with a LUMO (a carbon atom in the ortho or para position relative to an existing electron-accepting substituent), the electron orbital of the electron-donating substituent exerts a stronger perturbation on the LUMO than on the HOMO, greatly increasing the LUMO. This widens the gap between the HOMO and LUMO, making it possible to shorten the emission wavelength.

[0049] Similarly, when an electron-accepting substituent is bonded to a carbon atom with a HOMO (a carbon atom in the ortho or para position relative to an existing electron-donating substituent), the electron orbital of the electron-accepting substituent exerts a stronger perturbation on the HOMO than on the LUMO, lowering the HOMO significantly. This widens the gap between the HOMO and LUMO, and shortens the emission wavelength.

[0050] By utilizing the multiple resonance effect achieved by placing pyridinic nitrogen at the meta position relative to boron and by binding electron donating and accepting substituents to specific carbon atoms, it is possible to design dopant materials that exhibit shorter wavelength emission characteristics.

[0051] Regarding the above-mentioned (ii), specifically, the polycyclic aromatic compound represented by the general formula (1) of the present invention is X 1 and X 2 >NR and >C(-R) as 2 R may be bonded to at least one of the rings a, b, and c by a linking group or a single bond. This linking structure extends the conjugation and increases the planarity of the molecule. This increases the overlap of the orbitals of the ground state and excited state, increasing the transition probability and improving the luminescence efficiency. On the other hand, extending the conjugation leads to a longer emission wavelength. In addition, the planarity and flexibility of the condensed ring formed by this linking structure change depending on the type of linking group, including single bonds. If the planarity is high, the luminescence efficiency is expected to improve, but the emission wavelength may become longer, and if the flexibility is high, intermolecular stacking is reduced, but the half-width of the emission spectrum may become wider.

[0052] Regarding the above (iii), specifically, R 3 or R4 The introduction of certain substituents distorts the molecule, and as a result, both the singlet and triplet orbitals are distorted. This orbital distortion leads to greater spin-orbit coupling, and the greater the spin-orbit coupling, the more likely TADF occurs. The transition from triplet to singlet (or singlet to triplet) is accompanied by an inversion of the electron spin, but due to the laws of conservation of energy and conservation of angular momentum, a change in orbital angular momentum equal to the electron spin is required between the transitioning orbitals. The molecular and orbital distortion induced by the substituents leads to the generation of greater orbital angular momentum during the transition, which induces a greater magnetic moment and generates greater spin-orbit coupling (also known as spin-orbit coupling). In addition, the large molecular distortion reduces the planarity, which also leads to a reduction in intermolecular stacking.

[0053] By appropriately combining these approaches (i) to (iii), it has become possible to adjust the emission wavelength and the half-width of the emission spectrum, realize high emission efficiency and short delayed fluorescence lifetime in the compound, and realize suitable emission wavelength and half-width of the emission spectrum, high device efficiency and small roll-off in the device. However, the effect of the polycyclic aromatic compound of the present invention is not limited to the above principle.

[0054] (2) Description of the general formula (1) representing the compound of the present invention In the above general formula (1), R 1 , R 2 , R 3 , R 4 and R 5 (Hereinafter referred to as “R 1 and the like) are each independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl (the two aryls may be bonded via a single bond or a linking group), alkyl, cycloalkyl, alkoxy, or aryloxy (all of which are first substituents), and at least one hydrogen in these may be further substituted with aryl, heteroaryl, alkyl, or cycloalkyl (all of which are second substituents). X 1 and X 2 are each independently >NR (amine nitrogen), >O, >C (-R) 2 , >S or >Se, X 1 and X 2 Both are > C(-R) 2 It will not be, The above >NR and >C(-R) 2 R in the formula (I) is independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl (two aryls may be bonded via a single bond or a linking group), alkyl, cycloalkyl, alkoxy or aryloxy (all of the above, first substituents), and at least one hydrogen in these may be further substituted with an aryl, heteroaryl, alkyl or cycloalkyl (all of the above, second substituents), and the above >NR and >C(-R) 2 Each R may be independently bonded to at least one of the ring a, ring b and ring c via a linking group or a single bond. Y 1 , Y 2 , Y 3 , Y 4 , Y 5 and Y 6 (hereinafter, "Y 1 etc." are each independently =C(-R)- or =N- (pyridine nitrogen), and at least one is =N- (pyridine nitrogen); R in the =C(-R)- is each independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl (two aryls may be bonded via a single bond or a linking group), alkyl, cycloalkyl, alkoxy, or aryloxy (all of which are first substituents), and at least one hydrogen in these may be further substituted by aryl, heteroaryl, alkyl, or cycloalkyl (all of which are second substituents). R 1 , R 2 , R 3 , R4 and R 5 , and the Y 1 ~Y 6 Adjacent groups among R in =C(-R)- as the formula may be bonded to each other to form an aryl ring or a heteroaryl ring together with at least one of the ring a, ring b, and ring c, and at least one hydrogen atom in the formed ring may be substituted with an aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl (two aryls may be bonded via a single bond or a linking group), alkyl, cycloalkyl, alkoxy, or aryloxy (all of these, first substituents), and at least one hydrogen atom in these may be further substituted with an aryl, heteroaryl, alkyl, or cycloalkyl (all of these, second substituents). At least one hydrogen atom in the compound and structure represented by the general formula (1) may be substituted with cyano, halogen or deuterium.

[0055] (2-1)Y 1 ~Y 6 Description of the combination Y 1 etc. are each independently =C(-R)- or =N-, and at least one is =N-. 1 ~Y 6 Any of Y may be =N-. 1 and Y 6 =N-(a ring is a pyrimidine ring), Y 1 or Y 6 =N-(a ring is a pyridine ring), Y 2 and Y 5 =N- (ring b and ring c are pyridine rings), Y 3 and Y 4 =N- (ring b and ring c are pyridine rings), Y 2 ~Y 5 =N-(ring b and ring c are pyrimidine rings), Y 1 , Y 3 , Y 4 and Y 6=N- (ring a is a pyrimidine ring, rings b and c are pyridine rings), Y 1 , Y 2 , Y 5 and Y 6 =N- (ring a is a pyrimidine ring, rings b and c are pyridine rings), Y 1 ~Y 6 =N-(ring a, ring b and ring c are pyrimidine rings), Y 2 or Y 5 is =N-(ring b or ring c is a pyridine ring).

[0056] In addition to the above =N- arrangement, X 1 and X 2 is preferably >O, and a polycyclic aromatic compound containing a partial structure represented by any one of the following formulas is preferred. [ka]

[0057] In particular, polycyclic aromatic compounds containing the partial structure represented by formula (1-1601-R) are promising as blue TADF assist dopants, TADF hosts and phosphorescent hosts because they have high S1, high T1 and small ΔE(ST) compared to structures without N. They also have deep HOMO and deep LUMO, making them promising hole blocking materials and electron transporting materials.

[0058] In addition to the above =N- arrangement, X 1 and X 2 is preferably >NR (R=phenyl, pyridyl or pyrimidyl), and is preferably a polycyclic aromatic compound containing a partial structure represented by any one of the following formulas or a multimer thereof. [ka]

[0059] Each of the above formulas shows a "partial structure" of a polycyclic aromatic compound or a multimer thereof. Therefore, R defined in general formula (1) 1 etc;Y1 Equivalently, =C(-R)-R;R 1 ~R 5 and Y 1 ~Y 6 an aryl ring or heteroaryl ring that can be formed by bonding adjacent groups among the R in =C(-R)- as the above, and further substituents thereon (first and second substituents); X 1 and X 2 A second substituent to R in >NR as above, or a linking group or single bond between said R and at least one of the a, b and c rings; and further cyano, halogen or deuterium which may be substituted in the compound are omitted.

[0060] From a synthetic viewpoint, preferred are polycyclic aromatic compounds having a partial structure represented by the above formula (1-1601-R), formula (1-841-R), formula (1-1-R) or formula (1-381-R), which do not contain nitrogen in the aromatic rings (ring b and ring c) that undergo the Friedel-Crafts reaction on boron and are not electron deficient, and more preferred are polycyclic aromatic compounds having a partial structure represented by the above formula (1-1601-R) or formula (1-381-R).

[0061] From the viewpoint of physical properties, the more nitrogen there is, the stronger the multiple resonance effect can be, so polycyclic aromatic compounds having a partial structure represented by the above formula (1-601-R) in which all meta positions relative to boron are replaced by nitrogen are preferred.

[0062] The more bulky the alkyl group is, the higher the photoluminescence quantum yield (PLQY) is, and the higher the external quantum efficiency is when the compound is made into a device. For example, a methyl group is preferable, a t-butyl group is more preferable, and an adamantyl group is most preferable.

[0063] Compounds containing nitrogen as an electron-accepting element have a low LUMO and tend to become electron trap sites when made into a device. Therefore, when the polycyclic aromatic compound of the above formula (1) is used as a dopant material, the host material is preferably a compound with a low LUMO, for example, as shown in the following structural formula. "Me" in the formula is a methyl group. [ka]

[0064] (2-2)R 1 ~R 5 Description of R 1 The "aryl" (first substituent) is, for example, an aryl having 6 to 30 carbon atoms, preferably an aryl having 6 to 20 carbon atoms, more preferably an aryl having 6 to 16 carbon atoms, still more preferably an aryl having 6 to 12 carbon atoms, and particularly preferably an aryl having 6 to 10 carbon atoms.

[0065] Specific examples of aryl include phenyl, which is a monocyclic ring system, biphenylyl, which is a bicyclic ring system, naphthyl, which is a fused bicyclic ring system, terphenylyl (m-terphenylyl, o-terphenylyl, p-terphenylyl), which is a tricyclic ring system, acenaphthylenyl, fluorenyl, phenalenyl, phenanthrenyl, which are fused tricyclic ring systems, triphenylenyl, pyrenyl, and naphthacenyl, which are fused tetracyclic ring systems, and perylenyl and pentacenyl, which are fused pentacyclic ring systems.

[0066] R 1 The "heteroaryl" (first substituent) is, for example, a heteroaryl having 2 to 30 carbon atoms, preferably a heteroaryl having 2 to 25 carbon atoms, more preferably a heteroaryl having 2 to 20 carbon atoms, further preferably a heteroaryl having 2 to 15 carbon atoms, and particularly preferably a heteroaryl having 2 to 10 carbon atoms. In addition, the heteroaryl is, for example, a heterocycle containing, as a ring-constituting atom other than carbon, 1 to 5 heteroatoms selected from oxygen, sulfur, and nitrogen.

[0067] Specific examples of heteroaryl include pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, oxadiazolyl, thiadiazolyl, triazolyl, tetrazolyl, pyrazolyl, pyridinyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, indolyl, isoindolyl, 1H-indazolyl, benzimidazolyl, benzoxazolyl, benzothiazolyl, 1H-benzotriazolyl, quinolinyl, isoquinolinyl, cinnolinyl, quinazolinyl, quinoxalinyl, phthalazinyl, naphthyridinyl, purinyl, pteridinyl, carbazolyl, and acridinyl. Examples of the alkyl group include phenyl, phenoxathiinyl, phenoxazinyl, phenothiazinyl, phenazinyl, phenazasilinyl, indolizinyl, furanyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, naphthobenzofuranyl, thiophenyl, benzothiophenyl, isobenzothiophenyl, dibenzothiophenyl, naphthobenzothiophenyl, benzophosphoryl, dibenzophosphoryl, a monovalent group of a benzophosphole oxide ring, a monovalent group of a dibenzophosphole oxide ring, furazanyl, thianthrenyl, indolocarbazolyl, benzoindolocarbazolyl, and benzobenzoindolocarbazolyl.

[0068] R 1 For the "aryl" in "diarylamino" (first substituent), the "heteroaryl" in "diheteroarylamino" (first substituent), the "aryl" and "heteroaryl" in "arylheteroarylamino" (first substituent), and the "aryl" in "aryloxy" (first substituent), the above-mentioned explanations of aryl and heteroaryl can be cited.

[0069] R 1The "alkyl" (first substituent) may be either linear or branched, and is, for example, a linear alkyl having 1 to 24 carbon atoms or a branched alkyl having 3 to 24 carbon atoms. An alkyl having 1 to 18 carbon atoms (branched alkyl having 3 to 18 carbon atoms) is preferred, an alkyl having 1 to 12 carbon atoms (branched alkyl having 3 to 12 carbon atoms) is more preferred, an alkyl having 1 to 6 carbon atoms (branched alkyl having 3 to 6 carbon atoms) is even more preferred, and an alkyl having 1 to 5 carbon atoms (branched alkyl having 3 to 5 carbon atoms) or an alkyl having 1 to 4 carbon atoms (branched alkyl having 3 to 4 carbon atoms) is particularly preferred.

[0070] Specific examples of alkyl include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, t-butyl, n-pentyl, isopentyl, neopentyl, t-pentyl (t-amyl), n-hexyl, 1-methylpentyl, 3,3-dimethylbutyl, 2-ethylbutyl, n-heptyl, 1-methylhexyl, n-octyl, t-octyl (1,1,3,3-tetramethylbutyl), 1-methyl heptyl, 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. Further, for example, 1-ethyl-1-methylpropyl, 1,1-diethylpropyl, 1,1-dimethylbutyl, 1-ethyl-1-methylbutyl, 1,1,4-trimethylpentyl, 1,1,2-trimethylpropyl, 1,1-dimethyloctyl, 1,1-dimethylpentyl, 1,1-dimethylheptyl, 1,1,5-trimethylhexyl, 1-ethyl-1-methylhexyl, 1-ethyl-1,3-dimethylbutyl, 1,1,2,2-tetramethylpropyl, 1-butyl-1-methylpentyl, 1,1-diethylbutyl, 1-ethyl-1-methylpentyl, 1,1,3-trimethylbutyl, 1-propyl-1-methylpentyl, 1,1,2-trimethylpropyl, 1-ethyl-1,2,2-trimethylpropyl, 1-propyl-1-methylbutyl, and 1,1-dimethylhexyl.

[0071] R 1 Examples of the "cycloalkyl" (first substituent) include cycloalkyl having 3 to 24 carbon atoms, cycloalkyl having 3 to 20 carbon atoms, cycloalkyl having 3 to 16 carbon atoms, cycloalkyl having 3 to 14 carbon atoms, cycloalkyl having 5 to 10 carbon atoms, cycloalkyl having 5 to 8 carbon atoms, cycloalkyl having 5 to 6 carbon atoms, and cycloalkyl having 5 carbon atoms.

[0072] Specific examples of cycloalkyl include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, and alkyl (particularly methyl) substituted derivatives of these having 1 to 4 carbon atoms, as well as norbornenyl, bicyclo[1.0.1]butyl, bicyclo[1.1.1]pentyl, bicyclo[2.0.1]pentyl, bicyclo[1.2.1]hexyl, bicyclo[3.0.1]hexyl, bicyclo[2.1.2]heptyl, bicyclo[2.2.2]octyl, adamantyl, diamantyl, decahydronaphthalenyl, and decahydroazulenyl.

[0073] R 1The "alkoxy" (first substituent) is, for example, a straight chain alkoxy having 1 to 24 carbon atoms or a branched chain alkoxy having 3 to 24 carbon atoms. An alkoxy having 1 to 18 carbon atoms (branched chain alkoxy having 3 to 18 carbon atoms) is preferred, an alkoxy having 1 to 12 carbon atoms (branched chain alkoxy having 3 to 12 carbon atoms) is more preferred, an alkoxy having 1 to 6 carbon atoms (branched chain alkoxy having 3 to 6 carbon atoms) is even more preferred, and an alkoxy having 1 to 5 carbon atoms (branched chain alkoxy having 3 to 5 carbon atoms) or an alkoxy having 1 to 4 carbon atoms (branched chain alkoxy having 3 to 4 carbon atoms) is particularly preferred.

[0074] Specific examples of alkoxy include methoxy, ethoxy, propoxy, isopropoxy, n-butoxy, isobutoxy, s-butoxy, t-butoxy, t-amyloxy, n-pentyloxy, isopentyloxy, neopentyloxy, t-pentyloxy, n-hexyloxy, 1-methylpentyloxy, 3,3-dimethylbutoxy, 2-ethylbutoxy, n-heptyloxy, 1-methylhexyloxy, n-octyloxy, t-octyloxy, 1-methylheptyloxy, and 2-ethylhexyl. Examples of the aryloxy group include oxy, 2-propylpentyloxy, n-nonyloxy, 2,2-dimethylheptyloxy, 2,6-dimethyl-4-heptyloxy, 3,5,5-trimethylhexyloxy, n-decyloxy, n-undecyloxy, 1-methyldecyloxy, n-dodecyloxy, n-tridecyloxy, 1-hexylheptyloxy, n-tetradecyloxy, n-pentadecyloxy, n-hexadecyloxy, n-heptadecyloxy, n-octadecyloxy, and n-eicosyloxy.

[0075] R 1 The above explanation of aryl can be cited for the "aryl" in the "diarylboryl" (first substituent) such as. In addition, the two aryls are connected by a single bond or a linking group (e.g., >C(-R) 2 , >O, >S or >NR), where >C(-R) 2and R in >NR is aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, alkyl, cycloalkyl, alkoxy, or aryloxy (all of the above, first substituent), and the first substituent may be further substituted with aryl, heteroaryl, alkyl, or cycloalkyl (all of the above, second substituent). As specific examples of these groups, the above-mentioned explanations of aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, alkyl, cycloalkyl, alkoxy, or aryloxy as the first substituent can be cited.

[0076] R 1 For the aryl, heteroaryl, alkyl, or cycloalkyl (above, second substituent) that further substitutes the above (first substituent), the above description of the aryl, heteroaryl, alkyl, or cycloalkyl as the first substituent can be cited.

[0077] (2-3)Y 1 ~Y 6 Description of Y 1 Examples of R in =C(-R)- include aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl (two aryls may be bonded via a single bond or a linking group), alkyl, cycloalkyl, alkoxy, and aryloxy (all of which are first substituents), and aryl, heteroaryl, alkyl, or cycloalkyl (all of which are second substituents) which further substitute at least one hydrogen atom in these groups include the above-mentioned R 1 etc. (first substituent) can be cited as examples of aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl, alkyl, cycloalkyl, alkoxy or aryloxy.

[0078] (2-4)R 1 ~R5 and Y 1 ~Y 6 One concrete example of Specifically, R 1 etc. (first substituent) and Y 1 The emission wavelength can be adjusted by the steric hindrance, electron donating property and electron accepting property of the R (first substituent) structure in =C(-R)- such as, and a group represented by the following structural formula is preferable: In the following structural formula, "Me" represents methyl, "tBu" represents t-butyl, "tAm" represents t-amyl, "tOct" represents t-octyl, and * represents a bonding position.

[0079] [ka] [ka] [ka]

[0080] More preferred are methyl, t-butyl, t-amyl, t-octyl, 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 even more preferred are methyl, t-butyl, t-amyl, t-octyl, phenyl, o-tolyl, 2,6-xylyl, 2,4,6-mesityl, diphenylamino, di-p-tolylamino, bis(p-(t-butyl)phenyl)amino, carbazolyl, 3,6-dimethylcarbazolyl and 3,6-di-t-butylcarbazolyl. From the viewpoint of ease of synthesis, larger steric hindrance is preferred for selective synthesis, and specifically, t-butyl, t-amyl, t-octyl, o-tolyl, p-tolyl, 2,4-xylyl, 2,5-xylyl, 2,6-xylyl, 2,4,6-mesityl, di-p-tolylamino, bis(p-(t-butyl)phenyl)amino, 3,6-dimethylcarbazolyl and 3,6-di-t-butylcarbazolyl are preferred.

[0081] (2-5)R 3 and R 4 Adjustment of molecular distortion by By distorting the molecule, it is possible to increase the spin-orbit interaction. This shortens the delayed fluorescence lifetime, allows the TADF mechanism to be expressed, and increases the luminous efficiency of the device. For this purpose, in the general formula (1), R 3 and R 4 A substituent group Z described below is introduced into at least one of the above.

[0082] In the general formula (1), R 3 and R 4At least one of the above is Z, and Z is halogen, alkyl having 1 to 6 carbon atoms, cycloalkyl having 3 to 14 carbon atoms, aryl having 6 to 10 carbon atoms, or heteroaryl having 2 to 10 carbon atoms. Specifically, groups of the following partial structural formulae (m), (e), (v), (t), (h), (p), (q), (r), (s), (y), (u), (w), (j), (k), (f), (c), (b), (i) and (n) are preferred, and among these, groups of formulae (m), (t), (p), (f) and (n) are more preferred, and groups of formulae (m) and (t) are further preferred. In the following structural formula, "Me" stands for methyl, "Et" stands for ethyl, "iPr" stands for isopropyl, "tBu" stands for t-butyl, "CN" stands for cyano, and * stands for the bond position. [ka]

[0083] From the viewpoint of shortening the delayed fluorescence lifetime and expressing the TADF mechanism by applying strain to the molecule, R 3 and R 4 It is preferable that both of R are Z. From the viewpoint of obtaining a high PLQY and the stability of the molecule, 3 and R 4 It is preferred that only one of these is Z.

[0084] From the viewpoints of ease of synthesis and stability, the smaller the substituent, the more preferable, and the groups of the above formula (m), (e), (v), (t), (h), (p), (q), (r), (s), (j), (k), (f), (c), (b), (i) and (n) are preferred, and among these, the groups of the formulas (m), (e), (v), (t), (p), (f) and (n) are more preferable, the groups of the formulas (m) and (t) are even more preferable, and the group of the formula (m) is most preferable.

[0085] (2-6) Formation of a condensed ring by bonding adjacent groups In general formula (1), R 1 ~R 5 , and Y 1 ~Y 6Adjacent groups among the R in =C(-R)- as the ring may be bonded to each other to form an aryl ring or a heteroaryl ring together with at least one of the rings a, b, and c. Therefore, in the polycyclic aromatic compound represented by the general formula (1), the ring structure constituting the compound changes as shown in the following formulas (1'-1) and (1'-2) depending on the mutual bonding form of the substituents in the rings a, b, and c. Note that R in each formula 1 ~R 5 , Y 1 ~R 6 , a, b, c, X 1 and X 2 is the same as in general formula (1). [ka]

[0086] The ring a', ring b' and ring c' in the above formula (1'-1) and formula (1'-2) each independently represent a substituent R 1 ~R 5 and Y 1 ~Y 6 In =C(-R)-, adjacent R groups bond together to form an aryl or heteroaryl ring together with the a, b, and c rings (the rings may also be considered condensed rings formed by condensing the a, b, or c rings with other ring structures). Although not shown in the formula, there are also compounds in which the a, b, and c rings are all changed to the a', b', and c' rings.

[0087] As can be seen from the above formulas (1'-1) and (1'-2), for example, Y in ring a 1 R in =C(-R)- and Y in the b-ring 2 R in =C(-R)- as the ring, R in the b ring 3 and R in c-ring 4 , Y in the c-ring 5 R in =C(-R)- and Y in a-ring 6 Groups that span rings, such as the R in =C(-R)-, are not considered to be "adjacent groups" and cannot be bonded to each other. 1 and Y in a-ring1 R in =C(-R)- as Y in the b ring 2 R in =C(-R)- as a function of R in the b-ring 2 , R in ring b 2 and Y in b-algebras 3 R in =C(-R)- as Y in the b ring 3 R in =C(-R)- as a function of R in the b-ring 3 , R in ring c 4 and Y in c-algebras 4 R in =C(-R)- as Y in the c ring 4 R in =C(-R)- and R in c-ring as 5 , R in ring c 5 and Y in c-algebras 5 R in =C(-R)- as a, Y in the a ring 6 R in =C(-R)- and R in a-ring 1 That is, "adjacent groups" means groups adjacent to each other on the same ring.

[0088] The compounds represented by the above formula (1'-1) or (1'-2) can be, for example, a 6-membered ring (Y 1 and Y 6 It is a compound having a ring a' (or ring b' or ring c') formed by condensing a benzene ring, indole ring, pyrrole ring, benzofuran ring, benzothiophene ring, etc. to the ring a (or ring b or ring c) (a benzene ring when =C(-R)-). The condensed ring a' (or condensed ring b' or condensed ring c') formed is a naphthalene ring, carbazole ring, indole ring, dibenzofuran ring, dibenzothiophene ring, etc., when the ring a (or ring b or ring c) is a benzene ring. In addition, for example, the ring a (or ring b or ring c) is a pyridine ring (Y 1 and Y 6 In the case where either of Y is =N-, a benzene ring, an indole ring, a pyrrole ring, a benzofuran ring, a benzothiophene ring, or the like may be condensed. As described later, two Ys on one ring (for example, Y on the a ring) may be condensed. 1 and Y 6 When both of the formula (I) and (II) are =N-, no fused ring is formed.

[0089] Y 1 ~Y 6 R if and only if =C(-R)- 1 ~R 5 can be bonded to form a fused ring, Y 1 ~Y 6 When Y is =N-, a condensed ring originating from this =N- is not formed. For example, as shown in the example of the structural formula below, 1 and Y 6 When both are =N-, the fused ring a' is not formed, and Y 1 and Y 6 When at least one of the groups is ═C(—R)—, a fused ring a′ is formed. [ka]

[0090] Examples of the "aryl ring" (ring a', ring b' or ring c') thus formed include an aryl ring having 9 to 30 carbon atoms, an aryl ring having 9 to 16 carbon atoms, an aryl ring having 9 to 12 carbon atoms and an aryl ring having 9 to 10 carbon atoms. The lower limit of the number of carbon atoms in the aryl ring is 9 when ring a, ring b or ring c is a benzene ring having 6 carbon atoms (Y 1 ~Y 6 corresponds to a total of 9 carbon atoms in the fused ring formed by condensing a 5-membered ring (5 carbon atoms) to =C(-R)-).

[0091] Specific examples of the "aryl ring" include a fused bicyclic ring such as a naphthalene ring, a fused tricyclic ring such as an acenaphthylene ring, a fluorene ring, a phenalene ring, and a phenanthrene ring, a fused tetracyclic ring such as a triphenylene ring, a pyrene ring, and a naphthacene ring, and a fused pentacyclic ring such as a perylene ring and a pentacene ring.

[0092] Examples of the "heteroaryl ring" (ring a', ring b' or ring c') formed include a heteroaryl ring having 5 to 30 carbon atoms, a heteroaryl ring having 5 to 25 carbon atoms, a heteroaryl ring having 5 to 20 carbon atoms, a heteroaryl ring having 5 to 15 carbon atoms and a heteroaryl ring having 5 to 10 carbon atoms. Examples of the "heteroaryl ring" include a heterocycle containing, in addition to carbon, 1 to 5 heteroatoms selected from oxygen, sulfur and nitrogen as ring-constituting atoms. The lower limit of 5 carbon atoms in the heteroaryl ring is set when ring a, ring b or ring c is a pyridine ring (one Y on each ring). 1 ~Y 6 This is the lower limit when the pyridine ring having 5 carbon atoms is fused with a 5-membered ring, and the total number of carbon atoms in the fused ring is 5. Therefore, for example, for the a ring, Y 1 and Y 6 If both are =C(-R)-, the lower limit is changed to 6 (Y 1 and Y 6 When both are =N-, no fused ring is formed.

[0093] Specific examples of the "heteroaryl ring" include an indole ring, an isoindole ring, a 1H-indazole ring, a benzimidazole ring, a benzoxazole ring, a benzothiazole ring, a 1H-benzotriazole ring, a quinoline ring, an isoquinoline ring, a cinnoline ring, a quinazoline ring, a quinoxaline ring, a phthalazine ring, a naphthyridine ring, a carbazole ring, an acridine ring, a phenoxathiin ring, a phenoxazine ring, a phenothiazine ring, a phenazine ring, a benzofuran ring, an isobenzofuran ring, a dibenzofuran ring, a benzothiophene ring, a dibenzothiophene ring, and a thianthrene ring.

[0094] Examples of the aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl (two aryls may be bonded via a single bond or a linking group), alkyl, cycloalkyl, alkoxy, or aryloxy (all of the above, first substituents) substituted on the formed aryl ring or heteroaryl ring, and the aryl, heteroaryl, alkyl, or cycloalkyl (all of the above, second substituents) further substituting at least one hydrogen atom in these groups include the above-mentioned R 1 etc. (first substituent) can be cited as examples of aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl, alkyl, cycloalkyl, alkoxy or aryloxy.

[0095] (2-7)X 1 and X 2 Description of X 1 and X 2 are each independently >NR (amine nitrogen), >O, >C (-R) 2 , >S or >Se, X 1 and X 2 Both are > C(-R) 2 Among these, >NR, >O or >C(-R) 2 is preferred, and >NR or >O is preferred. Particularly preferred is X 1 and X 2 are both >NR or >O, and most preferably X 1 and X 2 Both are >NR.

[0096] >NR and >C(-R) 2In the formula (I), R is aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl (two aryls may be bonded via a single bond or a linking group), alkyl, cycloalkyl, alkoxy, or aryloxy (all of the above, the first substituent), and in these, aryl, heteroaryl, alkyl, or cycloalkyl (all of the above, the second substituent) which further substitutes at least one hydrogen atom can be selected from the group consisting of R 1 etc. (first substituent) can be cited as aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl, alkyl, cycloalkyl, alkoxy or aryloxy.

[0097] (2-8)X 1 and X 2 and bonds with ring a, ring b and ring c In the general formula (1), "(X 1 and X 2 as)NR and >C(-R) 2 The provision that "each R is independently bonded to at least one of the ring a, ring b and ring c through a linking group or a single bond" refers to X represented by the following formula (1'-3) or formula (1'-4). 1 and X 2 In other words, for example, the compound having a ring structure in which X is a 6-membered ring that is the a ring in the general formula (1), 1 (or X 2 , or X 1 and X 2 ) to be incorporated into another ring. 1 >NR or >C(-R) as 2 R and Y 1 An example of the embodiment is where R in =C(-R)- as X is bonded via a linking group or a single bond. 2 and Y 6The same applies to the bond with. The formed fused ring a' is, for example, a phenoxazine ring, a phenothiazine ring, or an acridine ring. In addition, the above definition is based on the following formula (1'-5): 1 Or X 2 can be expressed as a compound having a ring structure in which X is incorporated into the fused ring b' and the fused ring c'. That is, for example, the 6-membered ring b (or c, or b and c) in the general formula (1) 1 (or X 2 , or X 1 and X 2 ) to be condensed with another ring. More specifically, for example, X 1 >NR or >C(-R) as 2 R and Y 2 An example of the embodiment is where R in =C(-R)- as X is bonded via a linking group or a single bond. 2 and Y 5 The same applies to the bond with. The formed fused ring b' (or fused ring c') is, for example, a phenoxazine ring, a phenothiazine ring, or an acridine ring. In addition, R in the following formulas (1'-3), (1'-4) and (1'-5) 1 ~R 5 , Y 1 ~Y 6 ,a,b,c,a',b',c',X 1 and X 2 is the same as in general formula (1). [ka]

[0098] The linking group is -O-, -S- or -C(-R) 2 In addition, the above-mentioned "-C(-R) 2 R in "-" is hydrogen, alkyl or cycloalkyl, and the details of these groups are described above. 1The explanation of alkyl or cycloalkyl as the first substituent can be cited. In particular, alkyl having 1 to 4 carbon atoms (for example, methyl, ethyl, etc.) is preferred.

[0099] (2-9) Description of polymers The present invention is also directed to a multimer of a polycyclic aromatic compound having a plurality of unit structures represented by general formula (1). The multimer is preferably a dimer to hexamer, more preferably a dimer to trimer, and particularly preferably a dimer. The multimer may be in a form having a plurality of the above unit structures in one compound, and may be, for example, in addition to a form in which the above unit structures are bonded together by a linking group such as a single bond, an alkylene group having 1 to 3 carbon atoms (e.g., a methylene group), a phenylene group, or a naphthylene group (linked multimer), a form in which any ring (a ring, b ring, or c ring) contained in the above unit structure is shared by a plurality of unit structures (ring-shared multimer), or a form in which any ring (a ring, b ring, or c ring) contained in the above unit structure is bonded together so as to be condensed (ring-condensed multimer).

[0100] Examples of such multimers include multimers represented by the following general formula (1A) or formula (1B). The multimer represented by the following formula (1A) is a multimer (ring-sharing multimer) having a plurality of (two in the following structural formula) unit structures represented by general formula (1) in one compound, with the six-membered ring being c-ring (a-ring or b-ring) when described in the general formula (1). The multimer represented by the following formula (1B) is a multimer (ring-condensed multimer) having a plurality of (two in the following structural formula) unit structures represented by general formula (1) in one compound, with the six-membered ring being a-ring (b-ring or c-ring) of a certain unit structure condensed with the six-membered ring being a-ring (b-ring or c-ring) of a certain unit structure. The definitions of the symbols in each formula are the same as those in the general formula (1).

[0101] [ka]

[0102] The multimer may be a combination of the multimer form represented by formula (1A) and the multimer form represented by formula (1B).

[0103] (2-9) Description of other substituents The hydrogen atoms in the chemical structure of the polycyclic aromatic compound represented by the general formula (1) and its multimer may be entirely or partially substituted with cyano, halogen or deuterium. The halogen atom is fluorine, chlorine, bromine or iodine, preferably fluorine, chlorine or bromine, more preferably fluorine.

[0104] (3) Specific Examples of the Polycyclic Aromatic Compound of the Present Invention More specific examples of the polycyclic aromatic compound of the present invention include compounds represented by the following structural formulas.

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[0174] The polycyclic aromatic compound represented by the general formula (1) according to the present invention and its multimer can also be used as a material for organic devices, for example, a material for organic electroluminescent elements, a material for organic field effect transistors, or a material for organic thin-film solar cells, in the form of a polymer compound obtained by polymerizing a reactive compound substituted with a reactive substituent as a monomer (the monomer for obtaining this polymer compound has a polymerizable substituent), a crosslinked polymer obtained by further crosslinking the polymer compound (the polymer compound for obtaining this crosslinked polymer has a crosslinkable substituent), a pendant polymer compound obtained by reacting a main-chain polymer with the reactive compound (the reactive compound for obtaining this pendant polymer compound has a reactive substituent), or a pendant crosslinked polymer obtained by further crosslinking the pendant polymer compound (the pendant polymer compound for obtaining this crosslinked pendant polymer has a crosslinkable substituent).

[0175] The reactive substituents mentioned above (including the polymerizable substituents, the crosslinkable substituents, and the reactive substituents for obtaining a pendant polymer, hereinafter also referred to simply as "reactive substituents") are not particularly limited as long as they are substituents capable of increasing the molecular weight of the polycyclic aromatic compound or its multimer, substituents capable of further crosslinking the polymer compound thus obtained, and substituents capable of pendant reaction with the main chain polymer, but are preferably those having the following structures: * in each structural formula indicates a bond position. [ka]

[0176] Each L is independently a single bond, -O-, -S-, >C=O, -OC(=O)-, an alkylene having 1 to 12 carbon atoms, an oxyalkylene having 1 to 12 carbon atoms, or a polyoxyalkylene having 1 to 12 carbon atoms. Among the above substituents, a group represented by formula (XLS-1), formula (XLS-2), formula (XLS-3), formula (XLS-9), formula (XLS-10) or formula (XLS-17) is preferred, and a group represented by formula (XLS-1), formula (XLS-3) or formula (XLS-17) is more preferred.

[0177] The uses of such polymer compounds, crosslinked polymers, pendant type polymer compounds and pendant type crosslinked polymers (hereinafter sometimes simply referred to as "polymer compounds and crosslinked polymers") will be described later in detail.

[0178] 2. Method for producing polycyclic aromatic compounds The polycyclic aromatic compound and its multimer of the present invention can be synthesized by applying the method disclosed in, for example, WO 2015 / 102118. That is, as shown in the following scheme, an intermediate in which rings a to c are bonded is synthesized, and the intermediate is cyclized by a tandem hetero Friedel-Crafts reaction (successive aromatic electrophilic substitution reaction), thereby synthesizing the desired polycyclic aromatic compound and its multimer. In the following scheme, the symbols in each formula are defined as above. [ka] [ka]

[0179] The intermediate before cyclization in the above scheme can also be synthesized by the method shown in WO 2015 / 102118 etc. That is, an intermediate having a desired substituent can be synthesized by appropriately combining the Buchwald-Hartwig reaction, Suzuki coupling reaction, or etherification reaction such as nucleophilic substitution reaction or Ullmann reaction.

[0180] The tandem hetero Friedel-Crafts cyclization shown in the above scheme is a reaction to introduce B (boron) which connects the a, b and c rings. 1 and X 2The hydrogen atom (-H) on the a-ring between the two is ortho-metallated with n-butyllithium, sec-butyllithium, or t-butyllithium. Then, boron trichloride or boron tribromide is added to carry out lithium-boron metal exchange, and a tandem boron-Friedel-Crafts reaction is carried out by adding a Brønsted base such as N,N-diisopropylethylamine to obtain the desired product. Here, a Lewis acid such as aluminum trichloride may be added to promote the reaction.

[0181] In addition to the method of introducing lithium into the desired position by orthometalation, lithium can also be introduced into the desired position by introducing a halogen such as a bromine atom into the position where lithium is to be introduced and then carrying out halogen-metal exchange.

[0182] 3. Organic Devices In the chemical structural formulas exemplified below, "Me" represents a methyl group and "tBu" represents a t-butyl group. The polycyclic aromatic compound according to the present invention can be used as a material for an organic device, such as an organic electroluminescent element, an organic field effect transistor, or an organic thin-film solar cell.

[0183] 3-1. Organic electroluminescent device The polycyclic aromatic compound according to the present invention can be used, for example, as a material for an organic electroluminescent device. The organic EL device according to the present embodiment will be described in detail below with reference to the drawings. Fig. 1 is a schematic cross-sectional view showing an organic EL device according to the present embodiment.

[0184] <Structure of organic electroluminescent device> The organic electroluminescent element 100 shown in FIG. 1 has a substrate 101, an anode 102 provided on the substrate 101, a hole injection layer 103 provided on the anode 102, a hole transport layer 104 provided on the hole injection layer 103, an emitting layer 105 provided on the hole transport layer 104, an electron transport layer 106 provided on the emitting layer 105, an electron injection layer 107 provided on the electron transport layer 106, and a cathode 108 provided on the electron injection layer 107.

[0185] The organic electroluminescent device 100 may be fabricated in the reverse order, for example, to have a substrate 101, a cathode 108 provided on the substrate 101, an electron injection layer 107 provided on the cathode 108, an electron transport layer 106 provided on the electron injection layer 107, an emitting layer 105 provided on the electron transport layer 106, a hole transport layer 104 provided on the emitting layer 105, a hole injection layer 103 provided on the hole transport layer 104, and an anode 102 provided on the hole injection layer 103.

[0186] Not all of the above layers are essential, and the minimum structural unit is a structure consisting of an anode 102, an emitting layer 105, and a cathode 108. The hole injection layer 103, the hole transport layer 104, the electron transport layer 106, and the electron injection layer 107 are layers that may be provided optionally. Each of the above layers may consist of a single layer or multiple layers.

[0187] In addition to the above-mentioned "substrate / anode / hole injection layer / hole transport layer / light emitting layer / electron transport layer / electron injection layer / cathode" configuration, the layer configuration of the organic electroluminescent device may be "substrate / anode / hole transport layer / light emitting layer / electron transport layer / electron injection layer / cathode", "substrate / anode / hole injection layer / light emitting layer / electron transport layer / electron injection layer / cathode", "substrate / anode / hole injection layer / light emitting layer / electron transport layer / electron injection layer / cathode", "substrate / anode / hole injection layer / hole transport layer / light emitting ... The configuration may be "substrate / anode / light-emitting layer / electron transport layer / electron injection layer / cathode", "substrate / anode / hole transport layer / light-emitting layer / electron injection layer / cathode", "substrate / anode / hole transport layer / light-emitting layer / electron injection layer / cathode", "substrate / anode / hole transport layer / light-emitting layer / electron transport layer / cathode", "substrate / anode / hole injection layer / light-emitting layer / electron injection layer / cathode", "substrate / anode / hole injection ...light-emitting layer / electron transport layer / cathode", or "substrate / anode / light-emitting layer / electron transport layer / cathode".

[0188] <Substrate for organic electroluminescence 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 have less ions eluted from the glass, so non-alkali glass is preferable, 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.

[0189] <Anode in organic electroluminescent device> The anode 102 serves to inject holes into the light-emitting layer 105. When at least one of the hole injection layer 103 and the hole transport layer 104 is provided between the anode 102 and the light-emitting layer 105, holes are injected into the light-emitting layer 105 via these layers.

[0190] 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.

[0191] 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.

[0192] <Hole injection layer and hole transport layer in organic electroluminescence 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.

[0193] 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.

[0194] As materials for forming the hole injection layer 103 and the hole transport layer 104, any compound can be selected from compounds conventionally used as charge transport materials for holes in photoconductive materials, p-type semiconductors, and known compounds used in hole injection layers and hole transport layers of organic electroluminescent devices.

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

[0196] It is also known that the electrical conductivity of organic semiconductors is strongly influenced by their doping. Such organic semiconductor matrix substances consist of compounds with good electron donating or accepting properties. For doping with electron donating substances, strong electron acceptors such as tetracyanoquinone dimethane (TCNQ) or 2,3,5,6-tetrafluorotetracyano-1,4-benzoquinone dimethane (F4TCNQ) are known (see, for example, the literature "M. Pfeiffer, A. Beyer, T. Fritz, K. Leo, Appl. Phys. Lett., 73(22), 3202-3204 (1998)" and the literature "J. Blochwitz, M. Pheiffer, 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 include, for example, benzidine derivatives (TPD, etc.), starburst amine derivatives (TDATA, etc.), and certain metal phthalocyanines (especially zinc phthalocyanine (ZnPc) and the like) (JP 2005-167175 A).

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

[0198] <Light-emitting layer in organic electroluminescent device> The light-emitting layer 105 is a layer that emits light by recombining holes injected from the anode 102 and electrons injected from the cathode 108 between electrodes to which an electric field is applied. The material for the light-emitting layer 105 may be a compound (light-emitting compound) that is excited and emits light by the recombination of holes and electrons, and is preferably a compound that can be formed into a stable thin film shape and exhibits strong light-emitting (fluorescence) efficiency in a solid state. In the present invention, the polycyclic aromatic compound represented by the above general formula (1) can be used as the material for the light-emitting layer.

[0199] The light-emitting layer may be a single layer or multiple layers, each of which is formed from materials for the light-emitting layer (host material, dopant material). The host material and the dopant material may each be one type or a combination of multiple types. The dopant material may be entirely contained in the host material or may be partially contained in the host material. As a doping method, the dopant material may be formed by co-evaporation with the host material, but it may also be mixed with the host material in advance and then simultaneously evaporated, or mixed with the host material together with an organic solvent in advance and then formed into a film by a wet film-forming method.

[0200] The amount of the host material used varies depending on the type of the host material and may be determined according to the properties of the host material. The amount of the host material used is preferably 50 to 99.999% by weight, more preferably 80 to 99.95% by weight, and even more preferably 90 to 99.9% by weight, of the total material for the light-emitting layer.

[0201] The amount of the dopant material used varies depending on the type of the dopant material, and may be determined according to the characteristics of the dopant material. The amount of the dopant used is preferably 0.001 to 50% by weight, more preferably 0.05 to 20% by weight, and even more preferably 0.1 to 10% by weight, based on the total material for the light-emitting layer. The above range is preferable in that, for example, concentration quenching can be prevented.

[0202] On the other hand, in the organic electroluminescence device using the thermally activated delayed fluorescence dopant material, the amount of the dopant material used is preferably low in terms of preventing concentration quenching phenomenon, but the amount of the dopant material used is preferably high in terms of the efficiency of the thermally activated delayed fluorescence mechanism.Furthermore, in the organic electroluminescence device using the thermally activated delayed fluorescence assist dopant material, the amount of the dopant material used is preferably low compared to the amount of the assist dopant material used in terms of the efficiency of the thermally activated delayed fluorescence mechanism of the assist dopant material.

[0203] When an assist dopant material is used, the amounts of the host material, the assist dopant material and the dopant material to be used are approximately 40 to 99.999% by weight, 59 to 1% by weight and 20 to 0.001% by weight, respectively, based on the total material for the light-emitting layer, preferably 60 to 99.99% by weight, 39 to 5% by weight and 10 to 0.01% by weight, respectively, more preferably 70 to 99.95% by weight, 29 to 10% by weight and 5 to 0.05% by weight. The compound according to the present invention and the polymer compound thereof can also be used as an assist dopant material.

[0204] Examples of host materials include condensed ring derivatives of anthracene and pyrene, which have long been known as light-emitting bodies, bisstyryl derivatives such as bisstyrylanthracene derivatives and distyrylbenzene derivatives, tetraphenylbutadiene derivatives, cyclopentadiene derivatives, fluorene derivatives, and benzofluorene derivatives.

[0205] From the viewpoint of promoting TADF generation in the light-emitting layer without inhibiting it, the T1 energy of the host material is preferably higher than the T1 energy of the dopant or assist dopant having the highest T1 energy in the light-emitting layer, and specifically, the T1 energy of the host is preferably 0.01 eV or more, more preferably 0.03 eV or more, and even more preferably 0.1 eV or more. A TADF-active compound may be used as the host material.

[0206] Examples of the host material include a compound represented by the following general formula (H1), a compound represented by the following general formula (H2), a compound represented by the following general formula (H3), a compound including a structure represented by the following general formula (H4), a compound represented by the following general formula (H5), and a TADF material. The compound represented by the general formula (H1) is preferred. [ka]

[0207] <Compound represented by general formula (H1)> [ka] In the above formula (H1), L 1is an arylene having 6 to 30 carbon atoms or a heteroarylene having 2 to 30 carbon atoms, preferably an arylene having 6 to 24 carbon atoms, more preferably an arylene having 6 to 16 carbon atoms, further preferably an arylene having 6 to 12 carbon atoms, particularly preferably an arylene having 6 to 10 carbon atoms, further preferably a heteroarylene having 2 to 25 carbon atoms, more preferably a heteroarylene having 2 to 20 carbon atoms, further preferably a heteroarylene having 2 to 15 carbon atoms, particularly preferably a heteroarylene having 2 to 10 carbon atoms. Specific examples of the arylene include divalent groups such as a benzene ring, a biphenyl ring, a naphthalene ring, a terphenyl ring, an acenaphthylene ring, a fluorene ring, a phenalene ring, a phenanthrene ring, a triphenylene ring, a pyrene ring, a naphthacene ring, a perylene ring, and a pentacene ring. Specific examples of 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 benzimidazole ring, a benzoxazole ring, a benzothiazole ring, a 1H-benzotriazole ring, a quinoline ring, an isoquinoline ring, a cinnoline ring, a quinazoline ring, and a quinoxaline ring. Examples of divalent groups include a phthalazine ring, a naphthyridine ring, a purine ring, a pteridine ring, a carbazole ring, an acridine ring, a phenoxathiin ring, a phenoxazine ring, a phenothiazine ring, a phenazine ring, a phenazasiline ring, an indolizine ring, a furan ring, a benzofuran ring, an isobenzofuran ring, a dibenzofuran ring, a thiophene ring, a benzothiophene ring, a dibenzothiophene ring, a furazan ring, an oxadiazole ring, a thianthrene ring, an indolocarbazole ring, a benzoindolocarbazole ring, a benzobenzoindolocarbazole ring, and a naphthobenzofuran ring. At least one hydrogen atom in the compound represented by formula (H1) may be substituted with alkyl having 1 to 6 carbon atoms, cycloalkyl having 3 to 14 carbon atoms, cyano, halogen or deuterium.

[0208] <Compound represented by general formula (H2)> [ka] In the above 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. The aryl is preferably an aryl having 6 to 24 carbon atoms, more preferably an aryl having 6 to 16 carbon atoms, further preferably an aryl having 6 to 12 carbon atoms, and particularly preferably an aryl having 6 to 10 carbon atoms, and specific examples thereof include monovalent groups such as a benzene ring, a biphenyl ring, a naphthalene ring, a terphenyl ring, an acenaphthylene ring, a fluorene ring, a phenalene ring, a phenanthrene ring, a triphenylene ring, a pyrene ring, a naphthacene ring, a perylene ring, and a pentacene ring. The heteroaryl is preferably a heteroaryl having 2 to 25 carbon atoms, more preferably a heteroaryl having 2 to 20 carbon atoms, still more preferably a heteroaryl having 2 to 15 carbon atoms, and particularly preferably a heteroaryl having 2 to 10 carbon atoms. Specific examples thereof include a pyrrole ring, an oxazole ring, an isoxazole ring, a thiazole ring, an isothiazole ring, an imidazole ring, an oxadiazole ring, a thiadiazole ring, a triazole ring, a tetrazole ring, a pyrazole ring, a pyridine ring, a pyrimidine ring, a pyridazine ring, a pyrazine ring, a triazine ring, an indole ring, an isoindole ring, a 1H-indazole ring, a benzimidazole ring, a benzoxazole ring, a benzothiazole ring, a 1H-benzyl ring, a benzophenyl ... and monovalent groups such as a 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, a phenazasiline ring, an indolizine ring, a furan ring, a benzofuran ring, an isobenzofuran ring, a dibenzofuran ring, a thiophene ring, a benzothiophene ring, a dibenzothiophene ring, a furazan ring, an oxadiazole ring, a thianthrene ring, an indolocarbazole ring, a benzoindolocarbazole ring, a benzobenzoindolocarbazole ring, and a naphthobenzofuran ring. At least one hydrogen atom in the compound represented by formula (H2) may be substituted with alkyl having 1 to 6 carbon atoms, cycloalkyl having 3 to 14 carbon atoms, cyano, halogen or deuterium.

[0209] <Compound represented by general formula (H3)> [ka]

[0210] In formula (H3), Each MU is independently a divalent group represented by removing any two hydrogen atoms from an aromatic compound, each EC is independently a monovalent group represented by removing any one hydrogen atom from an aromatic compound, in which two hydrogen atoms in MU are replaced by EC or MU, and k is an integer from 2 to 50,000.

[0211] More specifically, Each MU is independently arylene, heteroarylene, diarylenarylamino, diarylenarylboryl, oxaborine-diyl, or azaborine-diyl; each E C is independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, or aryloxy; At least one hydrogen in MU and EC may be further substituted with aryl, heteroaryl, diarylamino, alkyl, and cycloalkyl; k is an integer from 2 to 50,000. k is preferably an integer from 20 to 50,000, and more preferably an integer from 100 to 50,000.

[0212] At least one hydrogen atom in MU and EC in formula (H3) may be substituted with an alkyl group having 1 to 24 carbon atoms, a cycloalkyl group having 3 to 24 carbon atoms, a halogen atom, or a deuterium atom. 2 - is -O- or -Si(CH 3 ) 2-, and -CH directly bonded to EC in formula (H3) in the alkyl 2 Any -CH except 2 - may be substituted with an arylene having 6 to 24 carbon atoms, and any hydrogen in the alkyl may be substituted with a fluorine.

[0213] Examples of MU include a divalent group represented by removing any two hydrogen atoms from any of the following compounds: [ka]

[0214] More specifically, the divalent group may be any of the following structures: In these, MU bonds to another MU or EC at *.

[0215] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka]

[0216] Examples of EC include monovalent groups represented by any of the following structures: In these, EC is bonded to MU at *.

[0217] [ka] [ka]

[0218] From the viewpoint of solubility and coating film-forming property, the compound represented by formula (H3) is preferably such that 10 to 100% of the total number of MUs (k) in the molecule have an alkyl having 1 to 24 carbon atoms, more preferably 30 to 100% of the total number of MUs (k) in the molecule have an alkyl having 1 to 18 carbon atoms (branched chain alkyl having 3 to 18 carbon atoms), and even more preferably 50 to 100% of the total number of MUs (k) in the molecule have an alkyl having 1 to 12 carbon atoms (branched chain alkyl having 3 to 12 carbon atoms). On the other hand, from the viewpoint of in-plane orientation and charge transport, it is preferable that 10 to 100% of the total number of MUs (k) in the molecule have an alkyl having 7 to 24 carbon atoms, and more preferably 30 to 100% of the total number of MUs (k) in the molecule have an alkyl having 7 to 24 carbon atoms (branched chain alkyl having 7 to 24 carbon atoms).

[0219] <Compound containing a structure represented by general formula (H4)> The compound is a compound containing a structure represented by the following formula (H4), and contains a plurality of such structures, preferably 1 to 5, more preferably 1 to 3, even more preferably 1 to 2, and most preferably 1. When the compound contains a plurality of such structures, the structures are directly bonded to each other via a single bond or a specific linking group. [ka]

[0220] In the above general formula (H4), G is "=C(-H)-" or "=N-", and the H in the "=C(-H)-" may be substituted with a substituent or a structure represented by another formula (H4).

[0221] Compounds containing a structure represented by general formula (H4) can be, for example, compounds described in WO 2012 / 153780 and WO 2013 / 038650, and can be produced according to the methods described in the above documents.

[0222] Examples of the substituent when H in "=C(-H)-" of G is substituted are as follows, but are not limited thereto.

[0223] Specific examples of the "aryl group" as a substituent include phenyl, tolyl, xylyl, naphthyl, phenanthryl, pyrenyl, chrysenyl, benzo[c]phenanthryl, benzo[g]chrysenyl, benzanthryl, triphenylenyl, fluorenyl, 9,9-dimethylfluorenyl, benzofluorenyl, dibenzofluorenyl, biphenylyl, terphenylyl, quaterphenylyl, fluoranthenyl, etc., and preferably phenyl, biphenylyl, terphenylyl, quaterphenylyl, naphthyl, triphenylenyl, and fluorenyl. Examples of aryl groups having a substituent include tolyl, xylyl, and 9,9-dimethylfluorenyl. As shown in the specific examples, the aryl group includes both fused and non-fused aryl groups.

[0224] Specific examples of the "heteroaryl group" as a substituent include pyrrolyl, pyrazolyl, pyrazinyl, pyrimidinyl, pyridazinyl, pyridyl, triazinyl, indolyl, isoindolyl, imidazolyl, benzimidazolyl, indazolyl, imidazo[1,2-a]pyridinyl, furyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, azadibenzofuranyl, thiophenyl, benzothienyl, dibenzothienyl, azadibenzothienyl, quinolyl, isoquinolyl, quinoxalinyl, quinazolinyl, and naphthyridinyl. , carbazolyl, azacarbazolyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, phenothiazinyl, phenoxazinyl, oxazolyl, oxadiazolyl, furazanyl, benzoxazolyl, thienyl, thiazolyl, thiadiazolyl, benzthiazolyl, triazolyl, tetrazolyl, etc., preferably dibenzofuranyl, dibenzothienyl, carbazolyl, pyridyl, pyrimidinyl, triazinyl, azadibenzofuranyl, azadibenzothienyl, etc. Dibenzofuranyl, dibenzothienyl, azadibenzofuranyl, or azadibenzothienyl is more preferred.

[0225] The "substituted silyl group" which is the substituent is also preferably a group selected from the group consisting of a substituted or unsubstituted trialkylsilyl group, a substituted or unsubstituted arylalkylsilyl group, and a substituted or unsubstituted triarylsilyl group.

[0226] Specific examples of the substituted or unsubstituted trialkylsilyl group include trimethylsilyl and triethylsilyl. Specific examples of the substituted or unsubstituted arylalkylsilyl group include diphenylmethylsilyl, ditolylmethylsilyl, and phenyldimethylsilyl. Specific examples of the substituted or unsubstituted triarylsilyl group include triphenylsilyl and tritolylsilyl.

[0227] The "substituted phosphine oxide group" as a substituent is also preferably a substituted or unsubstituted diarylphosphine oxide group. Specific examples of the substituted or unsubstituted diarylphosphine oxide group include diphenylphosphine oxide and ditolylphosphine oxide.

[0228] The "substituted carboxy group" as a substituent includes, for example, benzoyloxy and the like.

[0229] Examples of the linking group that bonds a plurality of structures represented by formula (H4) include divalent to tetravalent, divalent to trivalent, or divalent derivatives of the above-mentioned aryl or heteroaryl.

[0230] Specific examples of the compound containing the structure represented by general formula (H4) are shown below. [ka] [ka]

[0231] <Compound represented by general formula (H5)> [ka] In the above formula (H5), R 1 ~R 11 are each independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, alkyl, or cycloalkyl (all of which are first substituents), in which at least one hydrogen may be further substituted with aryl, heteroaryl, diarylamino, alkyl, or cycloalkyl (all of which are second substituents); R 1 ~R 11adjacent groups among the above may be bonded to each other to form an aryl ring or a heteroaryl ring together with the a ring, the b ring or the c ring, and at least one hydrogen atom in the formed ring may be substituted with an aryl, a heteroaryl, a diarylamino, a diheteroarylamino, an arylheteroarylamino, an alkyl or a cycloalkyl (all of which are referred to as a first substituent), and at least one hydrogen atom in these rings may be further substituted with an aryl, a heteroaryl, a diarylamino, an alkyl or a cycloalkyl (all of which are referred to as a second substituent); At least one hydrogen in the compound represented by formula (H5) may be independently replaced with a halogen or deuterium.

[0232] Preferably, in the above formula (H5), R 1 ~R 11 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 is an aryl having 6 to 12 carbon atoms), an alkyl having 1 to 12 carbon atoms, or a cycloalkyl having 3 to 16 carbon atoms, in which at least one hydrogen atom may be further substituted by an aryl having 6 to 30 carbon atoms, a heteroaryl having 2 to 30 carbon atoms, a diarylamino (wherein the aryl is an aryl having 6 to 12 carbon atoms), an alkyl having 1 to 12 carbon atoms, or a cycloalkyl having 3 to 16 carbon atoms; R 1 ~R 11Adjacent groups among these may be bonded to each other to form an aryl ring having 9 to 16 carbon atoms or a heteroaryl ring having 6 to 15 carbon atoms together with ring a, ring b or ring c, and at least one hydrogen in the formed ring may be substituted by an aryl having 6 to 30 carbon atoms, a heteroaryl having 2 to 30 carbon atoms, diarylamino (wherein aryl is an aryl having 6 to 12 carbon atoms), an alkyl having 1 to 12 carbon atoms or a cycloalkyl having 3 to 16 carbon atoms, and at least one hydrogen in these rings may be further substituted by an aryl having 6 to 30 carbon atoms, a heteroaryl having 2 to 30 carbon atoms, diarylamino (wherein aryl is an aryl having 6 to 12 carbon atoms), an alkyl having 1 to 12 carbon atoms or a cycloalkyl having 3 to 16 carbon atoms.

[0233] More preferably, in the above formula (H5), R 1 ~R 11 each independently represents a hydrogen atom, an aryl having 6 to 16 carbon atoms, a heteroaryl having 2 to 15 carbon atoms, a diarylamino (wherein the aryl is an aryl having 6 to 10 carbon atoms), an alkyl having 1 to 6 carbon atoms, or a cycloalkyl having 3 to 14 carbon atoms, in which at least one hydrogen atom may be further substituted by an aryl having 6 to 16 carbon atoms, a heteroaryl having 2 to 15 carbon atoms, a diarylamino (wherein the aryl is an aryl having 6 to 10 carbon atoms), an alkyl having 1 to 6 carbon atoms, or a cycloalkyl having 3 to 14 carbon atoms; R 1 ~R 11Adjacent groups among these may be bonded to each other to form an aryl ring having 9 to 12 carbon atoms or a heteroaryl ring having 6 to 12 carbon atoms together with ring a, ring b or ring c, and at least one hydrogen in the formed ring may be substituted by an aryl having 6 to 16 carbon atoms, a heteroaryl having 2 to 15 carbon atoms, diarylamino (wherein aryl is an aryl having 6 to 10 carbon atoms), an alkyl having 1 to 6 carbon atoms or a cycloalkyl having 3 to 14 carbon atoms, and at least one hydrogen in these rings may be further substituted by an aryl having 6 to 16 carbon atoms, a heteroaryl having 2 to 15 carbon atoms, diarylamino (wherein aryl is an aryl having 6 to 10 carbon atoms), an alkyl having 1 to 6 carbon atoms or a cycloalkyl having 3 to 14 carbon atoms.

[0234] In the above first and second substituents, examples of "aryl" and "heteroaryl" in aryl, heteroaryl, diarylamino, diheteroarylamino, and arylheteroarylamino include the following.

[0235] Specific examples of "aryl" include aryl having 6 to 30 carbon atoms, preferably aryl having 6 to 24 carbon atoms, more preferably aryl having 6 to 20 carbon atoms, further preferably aryl having 6 to 16 carbon atoms, particularly preferably aryl having 6 to 12 carbon atoms, and most preferably aryl having 6 to 10 carbon atoms. For example, phenyl is a monocyclic aryl, (2-, 3-, 4-)biphenylyl is a bicyclic aryl, (1-, 2-)naphthyl 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) is a tricyclic aryl, Examples of such aryl groups include 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 groups such as quaterphenylyl (5'-phenyl-m-terphenyl-2-yl, 5'-phenyl-m-terphenyl-3-yl, 5'-phenyl-m-terphenyl-4-yl, m-quaterphenylyl), condensed tetracyclic aryl groups such as triphenylene-(1-,2-)yl, pyrene-(1-,2-,4-)yl, and naphthacene-(1-,2-,5-)yl, and condensed pentacyclic aryl groups such as perylene-(1-,2-,3-)yl and pentacene-(1-,2-,5-,6-)yl.

[0236] Specific examples of "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. For example, pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, oxadiazolyl, thiadiazolyl, triazolyl, tetrazolyl, pyrazolyl, pyridinyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, indolyl, isoindolyl, 1H-indazolyl, benzimidazolyl, benzoxazolyl, benzothiazolyl, 1H-benzotriazolyl, quinolinyl, isoquinolinyl, cinnolinyl, quinazolinyl, quinoxalinyl, phthalazinyl, naphthyridinyl, purinyl, pteridinyl, carbazolyl, acridinyl, phenoxathiyl, Examples of the alkyl group include ynyl, phenoxazinyl, phenothiazinyl, phenazinyl, phenazasilinyl, indolizinyl, furanyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, naphthobenzofuranyl, thiophenyl, benzothiophenyl, isobenzothiophenyl, dibenzothiophenyl, naphthobenzothiophenyl, benzophosphoryl, dibenzophosphoryl, a monovalent group of a benzophosphole oxide ring, a monovalent group of a dibenzophosphole oxide ring, furazanyl, thianthrenyl, indolocarbazolyl, benzoindolocarbazolyl, and benzobenzoindolocarbazolyl.

[0237] In the above first and second substituents, the "alkyl" may be either linear or branched, and examples thereof include linear alkyl having 1 to 24 carbon atoms or branched alkyl having 3 to 24 carbon atoms. An alkyl having 1 to 18 carbon atoms (branched alkyl having 3 to 18 carbon atoms) is preferable, an alkyl having 1 to 12 carbon atoms (branched alkyl having 3 to 12 carbon atoms) is more preferable, an alkyl having 1 to 6 carbon atoms (branched alkyl having 3 to 6 carbon atoms) is even more preferable, an alkyl having 1 to 5 carbon atoms (branched alkyl having 3 to 5 carbon atoms) or an alkyl having 1 to 4 carbon atoms (branched alkyl having 3 to 4 carbon atoms) is particularly preferable, and methyl is most preferable. For example, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, t-butyl, n-pentyl, isopentyl, neopentyl, t-pentyl (t-amyl), n-hexyl, 1-methylpentyl, 3,3-dimethylbutyl, 2-ethylbutyl, n-heptyl, 1-methylhexyl, n-octyl, t-octyl (1,1,3,3-tetramethylbutyl), 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. Further, for example, 1-ethyl-1-methylpropyl, 1,1-diethylpropyl, 1,1-dimethylbutyl, 1-ethyl-1-methylbutyl, 1,1,4-trimethylpentyl, 1,1,2-trimethylpropyl, 1,1-dimethyloctyl, 1,1-dimethylpentyl, 1,1-dimethylheptyl, 1,1,5-trimethylhexyl, 1-ethyl-1-methylhexyl, 1-ethyl-1,3-dimethylbutyl, 1,1,2,2-tetramethylpropyl, 1-butyl-1-methylpentyl, 1,1-diethylbutyl, 1-ethyl-1-methylpentyl, 1,1,3-trimethylbutyl, 1-propyl-1-methylpentyl, 1,1,2-trimethylpropyl, 1-ethyl-1,2,2-trimethylpropyl, 1-propyl-1-methylbutyl, and 1,1-dimethylhexyl.

[0238] In the above first and second substituents, examples of "cycloalkyl" include cycloalkyl having 3 to 24 carbon atoms, cycloalkyl having 3 to 20 carbon atoms, cycloalkyl having 3 to 16 carbon atoms, cycloalkyl having 3 to 14 carbon atoms, cycloalkyl having 5 to 10 carbon atoms, cycloalkyl having 5 to 8 carbon atoms, cycloalkyl having 5 to 6 carbon atoms, and cycloalkyl having 5 carbon atoms. Examples include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, and alkyl (especially methyl) substituted derivatives of these having 1 to 4 carbon atoms, as well as bicyclo[1.0.1]butyl, bicyclo[1.1.1]pentyl, bicyclo[2.0.1]pentyl, bicyclo[1.2.1]hexyl, bicyclo[3.0.1]hexyl, bicyclo[2.1.2]heptyl, bicyclo[2.2.2]octyl, adamantyl, diamantyl, decahydronaphthalenyl, and decahydroazulenyl.

[0239] When the first substituent is an aryl, the substitution position is R 1 , R 3 , R 4 , R 5 , R 10 and R 11 is preferred, for example, R 1 and R 3 Substitution to R 5 and R 10 Substitution to R 4 and R 11 The substitution with is more preferred, and the aryl is preferably a phenyl group.

[0240] When the first substituent is a heteroaryl, the substitution position is R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 9 , R 10 and R 11 is preferred, for example, R 1 Substitution to R 2 Substitution to R3 substitution to, R 1 and R 3 substitution to, R 4 and R 11 substitution to, R 5 and R 10 substitution to, R 6 and R 9 Substitution to and R is more preferable, and the heteroaryl is preferably a carbazolyl group. This heteroaryl (e.g., carbazolyl) may be substituted at the above position via a phenylene group.

[0241] Specific examples of the compound represented by formula (H5) include, for example, compounds represented by the following structural formulas. In the formula, "Me" is a methyl group.

[0242]

Chemical formula

Chemical formula

[0243] The compound represented by formula (H5) can be prepared by first bonding the a to c rings with a linking group (-O-) to produce an intermediate (the first reaction), and then bonding the a to c rings with B (boron) to produce the final product (the second reaction). In the first reaction, general etherification reactions such as nucleophilic substitution reactions and Ullmann reactions can be used. In the second reaction, a tandem hetero Friedel-Crafts reaction (successive aromatic electrophilic substitution reaction) can be used. Details of the first and second reactions can be referred to the description described in International Publication No. WO2015 / 102118.

[0244] <TADF material> By reducing the energy difference between the excited singlet state and the excited triplet state, reverse energy transfer from the excited triplet state, which usually has a low transition probability, to the excited singlet state can be efficiently performed, resulting in emission from the singlet state (thermally activated delayed fluorescence, TADF). In normal fluorescence emission, 75% of the triplet excitons generated by current excitation pass through a thermal deactivation pathway and cannot be captured as fluorescence. On the other hand, with TADF, all excitons can be used for fluorescence emission, making it possible to realize highly efficient organic electroluminescence elements.

[0245] Examples of TADF materials that can be used for such purposes include a compound represented by the following general formula (H6) or a compound having the following general formula (H6) as a partial structure. [ka] In formula (H6), ED is an electron donating group, Ln is a bonding group, and EA is an electron accepting group. The singlet energy (S 1 ) and triplet energy (T 1 ) energy difference (ΔS 1 T 1 ) is less than 0.2 eV (Hiroki Uoyama, Kenichi Goushi, Katsuyuki Shizu, Hiroko Nomura, Chihaya Adachi, Nature, 492, 234-238 (2012)). The energy difference (ΔS 1 T 1 ) is preferably 0.15 eV or less, more preferably 0.10 eV or less, and further preferably 0.08 eV or less.

[0246] TADF materials are preferably donor-acceptor type TADF compounds (DA type TADF compounds) designed to localize the HOMO and LUMO within a molecule using electron-donating substituents called donors and electron-accepting substituents called acceptors, thereby allowing efficient reverse intersystem crossing to occur.

[0247] In this specification, the term "electron-donating substituent" (donor) refers to a substituent or partial structure in which the LUMO 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 HOMO orbital is localized in a TADF compound molecule.

[0248] In general, TADF compounds using donors or acceptors have a large spin orbit coupling (SOC) due to their structure, and the exchange interaction between HOMO and LUMO is small, resulting in a small ΔE(ST), resulting in a very fast reverse intersystem crossing rate. On the other hand, TADF compounds using donors or acceptors have a large structural relaxation in the excited state (in some molecules, the stable structure differs between the ground state and the excited state, so when an external stimulus causes a conversion from the ground state to the excited state, the structure then changes to the stable structure in the excited state), giving a wide emission spectrum, which may reduce the color purity when used as a light-emitting material.

[0249] When the color purity is reduced by the TADF material, a fluorescent compound may be added as the other component to the light-emitting layer or a layer adjacent to the light-emitting layer. The TADF material acts as an assisting dopant, and the other component acts as an emitting dopant. The other component may be a compound whose absorption spectrum at least partially overlaps with the emission peak of the assisting dopant.

[0250] As the donor and acceptor structures used in the TADF material, for example, the structures described in Chemistry of Materials, 2017, 29, 1946-1963 can be used. 3Examples of functional groups containing nitrogen include groups derived from carbazole, dimethylcarbazole, di-t-butylcarbazole, dimethoxycarbazole, tetramethylcarbazole, benzofluorocarbazole, benzothienocarbazole, phenyldihydroindolocarbazole, phenylbicarbazole, bicarbazole, tercarbazole, diphenylcarbazolylamine, tetraphenylcarbazolyldiamine, phenoxazine, dihydrophenazine, phenothiazine, dimethyldihydroacridine, diphenylamine, bis(t-butyl)phenyl)amine, (diphenylamino)phenyl)diphenylbenzenediamine, dimethyltetraphenyldihydroacridinediamine, tetramethyl-dihydro-indenoacridine, and diphenyl-dihydrodibenzoazasiline. Examples of EA include, for example, sp 2Nitrogen-containing aromatic rings, CN-substituted aromatic rings, rings having ketones and cyano groups, more specifically sulfonyldibenzene, benzophenone, phenylenebis(phenylmethanone), benzonitrile, isonicotinonitrile, phthalonitrile, isophthalonitrile, paraphthalonitrile, triazole, oxazole, thiadiazole, benzothiazole, benzobis(thiazole), benzoxazole, benzobis(oxazole), quinoline, benzimidazole, dibenzoquinoxaline, heptaazaphenalene, thioxanthone dioxane, Examples of Ln include groups derived from phenyl, dimethylanthracenone, anthracenedione, pyridine, cycloheptabipyridine, benzenetricarbonitrile, fluorene dicarbonitrile, pyrazine dicarbonitrile, pyridine dicarbonitrile, dibenzoquinoxaline dicarbonitrile, pyrimidine, phenylpyrimidine, methylpyrimidine, triazine, triphenyltriazine, bis(phenylsulfonyl)benzene, dimethylthioxanthene dioxide, thianthrene tetraoxide, and tris(dimethylphenyl)borane. Examples of Ln include single bonds and arylenes, more specifically, phenylene, biphenylene, naphthylene, and the like. In addition, in any of the structures, hydrogen may be substituted with alkyl, cycloalkyl, and aryl. In particular, it is preferable that the compound has at least one partial structure selected from carbazole, phenoxazine, acridine, triazine, pyrimidine, pyrazine, thioxanthene, benzonitrile, phthalonitrile, isophthalonitrile, diphenylsulfone, triazole, oxadiazole, thiadiazole, and benzophenone.

[0251] The compound represented by general formula (H6) is, more specifically, a compound represented by any one of the following general formulas (H6-1), (H6-2) and (H6-3). [ka]

[0252] In the above general formulas (H6-1), (H6-2) and (H6-3), Each M is independently a single bond, -O-, >N-Ar, or >C(-Ar). 2 and preferably a single bond, -O- or >N-Ar in terms of the HOMO depth and the height of the excited singlet energy level and the excited triplet energy level of the partial structure to be formed; J is a spacer structure separating the donor partial structure and the acceptor partial structure, and each independently is an arylene having 6 to 18 carbon atoms. From the viewpoint of the magnitude of conjugation exuded from the donor partial structure and the acceptor partial structure, an arylene having 6 to 12 carbon atoms is preferable, and more specific examples thereof include phenylene, methylphenylene, and dimethylphenylene. Q is each independently =C(-H)- or =N-, and is preferably =N- from the viewpoint of shallowness of the LUMO of the partial structure to be formed and height of the excited singlet energy level and the excited triplet energy level, Ar each independently represents hydrogen, an aryl having 6 to 24 carbon atoms, a heteroaryl having 2 to 24 carbon atoms, an alkyl having 1 to 12 carbon atoms, or a cycloalkyl having 3 to 18 carbon atoms; from the viewpoint of the HOMO depth and the height of the excited singlet energy level and the excited triplet energy level of the partial structure to be formed, Ar is preferably hydrogen, an aryl having 6 to 12 carbon atoms, a heteroaryl having 2 to 14 carbon atoms, an alkyl having 1 to 4 carbon atoms, or a cycloalkyl having 6 to 10 carbon atoms, more preferably hydrogen, phenyl, tolyl, xylyl, mesityl, biphenyl, pyridyl, bipyridyl, triazyl, carbazolyl, dimethylcarbazolyl, di-t-butylcarbazolyl, benzimidazole, or phenylbenzimidazole, and further preferably hydrogen, phenyl, or carbazolyl; m is 1 or 2; n is an integer of 2 to (6-m), and from the viewpoint of steric hindrance, is preferably an integer of 4 to (6-m). Furthermore, at least one hydrogen in the compounds represented by the above formulas may be substituted with a halogen or deuterium.

[0253] Examples of the compound represented by formula (H6) include compounds represented by the following structures: In the structural formula, * indicates a bond position, "Me" indicates a methyl group, and "tBu" indicates a t-butyl group.

[0254] [ka]

[0255] [ka]

[0256] [ka]

[0257] [ka]

[0258] [ka]

[0259] [ka]

[0260] [ka]

[0261] [ka]

[0262] [ka]

[0263] As the compound represented by general formula (H6), 4CzBN, 4CzBN-Ph, 5CzBN, 3Cz2DPhCzBN, 4CzIPN, 2PXZ-TAZ, Cz-TRZ3, BDPCC-TPTA, MA-TA, PA-TA, FA-TA, PXZ-TRZ, DMAC-TRZ, BCzT, DCzTrz, DDCzTrz, spiroAC-TRZ, Ac-HPM, Ac-PPM, Ac-MPM, TCzTrz, TmCzTrz and DCzmCzTrz are particularly preferred among the specific compounds mentioned above.

[0264] The dopant material is not particularly limited, and any known compound can be used, and can be selected from a variety of materials depending on the desired emission color.Specific examples of such compounds include condensed ring derivatives of phenanthrene, anthracene, pyrene, tetracene, pentacene, perylene, naphthopyrene, dibenzopyrene, rubrene, and chrysene, benzoxazole derivatives, benzothiazole derivatives, benzimidazole derivatives, benzotriazole derivatives, oxazole derivatives, oxadiazole derivatives, thiazole derivatives, imidazole derivatives, thiadiazole derivatives, triazole derivatives, pyrazoline derivatives, stilbene derivatives, thiophene derivatives, and tetraphenylbutadiene. derivatives, cyclopentadiene derivatives, bisstyryl derivatives such as bisstyrylanthracene derivatives and distyrylbenzene derivatives (JP Patent Publication No. 245087 / 1999), bisstyrylarylene derivatives (JP Patent Publication No. 247278 / 1990), diazaindacene derivatives, furan derivatives, benzofuran derivatives, isobenzofuran derivatives such as phenylisobenzofuran, dimesitylisobenzofuran, di(2-methylphenyl)isobenzofuran, di(2-trifluoromethylphenyl)isobenzofuran, and phenylisobenzofuran coumarin derivatives such as dibenzofuran derivatives, 7-dialkylaminocoumarin derivatives, 7-piperidinocoumarin derivatives, 7-hydroxycoumarin derivatives, 7-methoxycoumarin derivatives, 7-acetoxycoumarin derivatives, 3-benzothiazolylcoumarin derivatives, 3-benzimidazolylcoumarin derivatives, and 3-benzoxazolylcoumarin derivatives, dicyanomethylenepyran derivatives, dicyanomethylenethiopyran derivatives, polymethine derivatives, cyanine derivatives, oxobenzoanthracene derivatives, xanthene derivatives, and rhodamine derivatives. conductors, fluorescein derivatives, pyrylium derivatives, carbostyril derivatives, acridine derivatives, oxazine derivatives, phenylene oxide derivatives, quinacridone derivatives, quinazoline derivatives, pyrrolopyridine derivatives, furopyridine derivatives, 1,2,5-thiadiazolopyrene derivatives, pyrromethene derivatives, perinone derivatives, pyrrolopyrrole derivatives, squarylium derivatives, violanthrone derivatives, phenazine derivatives, acridone derivatives, deazaflavin derivatives, fluorene derivatives and benzofluorene derivatives.

[0265] 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.

[0266] 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.

[0267] Further, examples of orange to red dopant materials include naphthalimide derivatives such as bis(diisopropylphenyl)perylenetetracarboxylic acid imide, perinone derivatives, rare earth complexes such as Eu complexes having acetylacetone, benzoylacetone, and phenanthroline as ligands, 4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran and analogs thereof, metal phthalocyanine derivatives such as magnesium phthalocyanine and aluminum chlorophthalocyanine, rhodamine compounds, deazaflavin derivatives, coumarin derivatives, quinacridone derivatives, phenoxazine derivatives, oxazine derivatives, quinazoline derivatives, pyrrolopyridine derivatives, squarylium derivatives, violanthrone derivatives, phenazine derivatives, phenoxazone derivatives, and thiadiazolopyrene derivatives. Further, suitable examples of the compounds exemplified as the above blue to blue-green and green to yellow dopant materials include compounds obtained by introducing a substituent that enables a longer wavelength, such as aryl, heteroaryl, arylvinyl, amino, or cyano.

[0268] In addition, the dopant may be appropriately selected from the compounds described in Chemical Industry, June 2004, page 13 and the references cited therein.

[0269] Among the above-mentioned dopant materials, amines having a stilbene structure, perylene derivatives, borane derivatives, aromatic amine derivatives, coumarin derivatives, pyran derivatives, or pyrene derivatives are particularly preferred.

[0270] The amine having a stilbene structure is represented, for example, by the following formula. [ka] In the formula, Ar 1 is an m-valent group derived from an aryl having 6 to 30 carbon atoms, and Ar 2 and Ar 3 are each independently an aryl having 6 to 30 carbon atoms, 1 ~Ar 3 At least one of the groups has a stilbene structure, and Ar1 ~Ar 3 may be substituted with aryl, heteroaryl, alkyl, cycloalkyl, tri-substituted silyl (silyl tri-substituted with at least one of aryl, alkyl, and cycloalkyl) or cyano, and m is an integer from 1 to 4.

[0271] 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 is optionally substituted with aryl, heteroaryl, alkyl, cycloalkyl, trisubstituted silyl (silyl trisubstituted with at least one of aryl, alkyl, and cycloalkyl) or cyano.

[0272] Specific examples of the aryl having 6 to 30 carbon atoms include phenyl, naphthyl, acenaphthylenyl, fluorenyl, phenalenyl, phenanthrenyl, anthryl, fluoranthenyl, triphenylenyl, pyrenyl, chrysenyl, naphthacenyl, perylenyl, stilbenyl, distyrylphenyl, distyrylbiphenylyl, and distyrylfluorenyl.

[0273] 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.

[0274] 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.

[0275] 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.

[0276] The aromatic amine derivative is represented, for example, by the following formula: [ka] In the formula, Ar 4 is an n-valent group derived from an aryl having 6 to 30 carbon atoms, and Ar 5 and Ar 6 are each independently an aryl having 6 to 30 carbon atoms, and Ar 4 ~Ar 6 may be substituted with aryl, heteroaryl, alkyl, cycloalkyl, tri-substituted silyl (silyl tri-substituted with at least one of aryl, alkyl, and cycloalkyl) or cyano, and n is an integer from 1 to 4.

[0277] In particular, Ar 4 is a divalent group derived from anthracene, chrysene, fluorene, benzofluorene, or pyrene, and Ar 5 and Ar 6 are each independently an aryl having 6 to 30 carbon atoms, and Ar 4 ~Ar 6 is optionally substituted with aryl, heteroaryl, alkyl, cycloalkyl, trisubstituted silyl (silyl trisubstituted with at least one of aryl, alkyl, and cycloalkyl) or cyano, and n is 2.

[0278] Specific examples of the aryl having 6 to 30 carbon atoms include phenyl, naphthyl, acenaphthylenyl, fluorenyl, phenalenyl, phenanthrenyl, anthryl, fluoranthenyl, triphenylenyl, pyrenyl, chrysenyl, naphthacenyl, perylenyl, and pentacenyl.

[0279] 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.

[0280] 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.

[0281] 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.

[0282] Other examples include [4-(4-diphenylamino-phenyl)naphthalen-1-yl]-diphenylamine, [6-(4-diphenylamino-phenyl)naphthalen-2-yl]-diphenylamine, 4,4'-bis[4-diphenylaminonaphthalen-1-yl]biphenyl, 4,4'-bis[6-diphenylaminonaphthalen-2-yl]biphenyl, 4,4"-bis[4-diphenylaminonaphthalen-1-yl]-p-terphenyl, and 4,4"-bis[6-diphenylaminonaphthalen-2-yl]-p-terphenyl. Furthermore, aromatic amine derivatives described in, for example, JP-A-2006-156888 may also be used.

[0283] 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.

[0284] 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.

[0285] The above-mentioned light-emitting layer materials (host material and dopant material) can be used as light-emitting layer materials as polymer compounds obtained by polymerizing a reactive compound substituted with a reactive substituent as a monomer, or as crosslinked polymers thereof, or as pendant polymer compounds obtained by reacting a main chain polymer with the reactive compound, or as crosslinked pendant polymers thereof. In this case, the explanation of the polycyclic aromatic compound represented by formula (1) can be cited as the reactive substituent. The applications of such polymer compounds and crosslinked polymers will be described in detail below.

[0286] <Electron injection layer and electron transport layer in organic electroluminescence device> The electron injection layer 107 plays a role of efficiently injecting electrons moving from the cathode 108 into the light-emitting layer 105 or the electron transport layer 106. The electron transport layer 106 plays a role of efficiently transporting electrons injected from the cathode 108 or electrons injected from the cathode 108 via the electron injection layer 107 to the light-emitting layer 105. The electron transport layer 106 and the electron injection layer 107 are each formed by laminating or mixing one or more types of electron transport / injection materials, or by a mixture of an electron transport / injection material and a polymer binder.

[0287] The electron injection / transport layer is a layer that injects electrons from the cathode and transports 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 hole and electron transport, 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.

[0288] 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.

[0289] Materials used in the electron transport layer or electron injection layer preferably contain at least one selected from compounds consisting of aromatic rings or heteroaromatic rings composed of one or more atoms selected from carbon, hydrogen, oxygen, sulfur, silicon, and phosphorus, pyrrole derivatives and their condensed ring derivatives, and metal complexes having electron-accepting nitrogen. Specific examples include condensed ring aromatic ring derivatives such as naphthalene and anthracene, styryl aromatic ring derivatives such as 4,4'-bis(diphenylethenyl)biphenyl, perinone derivatives, coumarin derivatives, naphthalimide derivatives, quinone derivatives such as anthraquinone and diphenoquinone, phosphorus oxide derivatives, carbazole 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.

[0290] Specific examples of other electron transport compounds include pyridine derivatives, naphthalene derivatives, anthracene derivatives, phenanthroline derivatives, perinone derivatives, coumarin derivatives, naphthalimide derivatives, anthraquinone derivatives, diphenoquinone derivatives, diphenylquinone derivatives, perylene derivatives, oxadiazole derivatives (e.g., 1,3-bis[(4-t-butylphenyl)1,3,4-oxadiazolyl]phenylene), thiophene derivatives, triazole derivatives (e.g., N-naphthyl-2,5-diphenyl-1,3,4-triazole), thiadiazole derivatives, metal complexes of oxine derivatives, quinolinol-based metal complexes, quinoxaline derivatives, polymers of quinoxaline derivatives, benzazole compounds, gallium complexes, pyrazole derivatives, perfluorinated phenylene derivatives, triazine derivatives, pyridine derivatives, etc. Examples of the compound include arylazine derivatives, benzoquinoline derivatives (such as 2,2'-bis(benzo[h]quinolin-2-yl)-9,9'-spirobifluorene), imidazopyridine derivatives, borane derivatives, benzimidazole derivatives (such as tris(N-phenylbenzimidazol-2-yl)benzene), benzoxazole 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, carbazole derivatives, indole derivatives, phosphorus oxide derivatives, and bisstyryl derivatives.

[0291] 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.

[0292] The above-mentioned materials may be used alone or in combination with different materials.

[0293] Among the above-mentioned materials, borane derivatives, pyridine derivatives, fluoranthene derivatives, BO-based derivatives, anthracene derivatives, benzofluorene derivatives, phosphine oxide derivatives, pyrimidine derivatives, carbazole derivatives, triazine derivatives, benzimidazole derivatives, phenanthroline derivatives, and quinolinol-based metal complexes are preferable.

[0294] <Borane derivatives> The borane derivative is, for example, a compound represented by the following general formula (ETM-1), and is disclosed in detail in JP-A-2007-27587. [ka] In the above formula (ETM-1), R 11 and R 12 are each independently at least one of hydrogen, alkyl, cycloalkyl, optionally substituted aryl, substituted silyl, optionally substituted nitrogen-containing heterocycle, or cyano; R 13 ~R 16 are each independently an optionally substituted alkyl, an optionally substituted cycloalkyl, or an optionally substituted aryl, X is an optionally substituted arylene, Y is an optionally substituted aryl having 16 or less carbon atoms, a substituted boryl, or an optionally substituted carbazolyl, and each n is independently an integer of 0 to 3. In addition, examples of the substituent in the case of "optionally substituted" or "substituted" include aryl, heteroaryl, alkyl, and cycloalkyl.

[0295] Among the compounds represented by the above general formula (ETM-1), compounds represented by the following general formula (ETM-1-1) and compounds represented by the following general formula (ETM-1-2) are preferred. [ka] In formula (ETM-1-1), R 11 and R 12are each independently at least one of hydrogen, alkyl, cycloalkyl, optionally substituted aryl, substituted silyl, optionally substituted nitrogen-containing heterocycle, or cyano; R 13 ~R 16 are each independently optionally substituted alkyl, optionally substituted cycloalkyl, or optionally substituted aryl; R 21 and R 22 are each independently at least one of hydrogen, alkyl, cycloalkyl, optionally substituted aryl, substituted silyl, optionally substituted nitrogen-containing heterocycle, or cyano; X 1 is an optionally substituted arylene having 20 or less carbon atoms, each n is independently an integer of 0 to 3, and each m is independently an integer of 0 to 4. In addition, examples of the substituent in the case where "optionally substituted" or "substituted" include aryl, heteroaryl, alkyl, and cycloalkyl. [ka] In formula (ETM-1-2), R 11 and R 12 are each independently at least one of hydrogen, alkyl, cycloalkyl, optionally substituted aryl, substituted silyl, optionally substituted nitrogen-containing heterocycle, or cyano; R 13 ~R 16 are each independently an optionally substituted alkyl, an optionally substituted cycloalkyl, or an optionally substituted aryl; X 1 is an optionally substituted arylene having 20 or less carbon atoms, and each n is independently an integer of 0 to 3. Examples of the substituent in the case where it is "optionally substituted" or "substituted" include aryl, heteroaryl, alkyl, and cycloalkyl.

[0296] X 1Specific examples of include divalent groups represented by any of the following formulae (X-1) to (X-9): In each structural formula, * represents the bonding position. [ka] (In each formula, R a are each independently an alkyl group, a cycloalkyl group, or an optionally substituted phenyl group.

[0297] Specific examples of the borane derivative include the following compounds: [ka]

[0298] The borane derivative can be produced using known raw materials and known synthesis methods.

[0299] <Pyridine derivatives> The pyridine derivative is, for example, a compound represented by the following formula (ETM-2), preferably a compound represented by formula (ETM-2-1) or formula (ETM-2-2). [ka]

[0300] 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.

[0301] In the above formula (ETM-2-1), R 11 ~R 18 are each independently hydrogen, alkyl (preferably alkyl having 1 to 24 carbon atoms), cycloalkyl (preferably cycloalkyl having 3 to 12 carbon atoms) or aryl (preferably aryl having 6 to 30 carbon atoms).

[0302] In the above formula (ETM-2-2), R11 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.

[0303] In each formula, the "pyridine-based substituent" is any one of the following formulae (Py-1) to (Py-15), and each pyridine-based substituent may be independently substituted with an alkyl having 1 to 4 carbon atoms or a cycloalkyl having 5 to 10 carbon atoms. The pyridine-based substituent may be bonded to the φ, anthracene ring, or fluorene ring in each formula via a phenylene group or naphthylene group. * in each structural formula indicates a bonding position. [ka]

[0304] The pyridine-based substituent is any one of the above formulae (Py-1) to (Py-15), and among these, any one of the following formulae (Py-21) to (Py-44) is preferable. In each structural formula, * indicates a bonding position. [ka]

[0305] At least one hydrogen atom in each pyridine derivative may be replaced by deuterium, and one of the two "pyridine-based substituents" in the above formulas (ETM-2-1) and (ETM-2-2) may be replaced by aryl.

[0306] R 11 ~R 18The "alkyl" in the above may be either linear or branched, and examples thereof include linear alkyl having 1 to 24 carbon atoms and branched alkyl having 3 to 24 carbon atoms. A preferred "alkyl" is an alkyl having 1 to 18 carbon atoms (branched alkyl having 3 to 18 carbon atoms). A more preferred "alkyl" is an alkyl having 1 to 12 carbon atoms (branched alkyl having 3 to 12 carbon atoms). An even more preferred "alkyl" is an alkyl having 1 to 6 carbon atoms (branched alkyl having 3 to 6 carbon atoms). An especially preferred "alkyl" is an alkyl having 1 to 4 carbon atoms (branched alkyl having 3 to 4 carbon atoms).

[0307] Specific examples of "alkyl" include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, t-butyl, n-pentyl, isopentyl, neopentyl, t-pentyl (t-amyl), n-hexyl, 1-methylpentyl, 3,3-dimethylbutyl, 2-ethylbutyl, n-heptyl, 1-methylhexyl, n-octyl, t-octyl (1,1,3,3-tetramethylbutyl), 1-methyl, Examples of the aryl ether include n-hexyl, n-butyl, n-butyl, n-butylheptyl, 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. Further, for example, 1-ethyl-1-methylpropyl, 1,1-diethylpropyl, 1,1-dimethylbutyl, 1-ethyl-1-methylbutyl, 1,1,4-trimethylpentyl, 1,1,2-trimethylpropyl, 1,1-dimethyloctyl, 1,1-dimethylpentyl, 1,1-dimethylheptyl, 1,1,5-trimethylhexyl, 1-ethyl-1-methylhexyl, 1-ethyl-1,3-dimethylbutyl, 1,1,2,2-tetramethylpropyl, 1-butyl-1-methylpentyl, 1,1-diethylbutyl, 1-ethyl-1-methylpentyl, 1,1,3-trimethylbutyl, 1-propyl-1-methylpentyl, 1,1,2-trimethylpropyl, 1-ethyl-1,2,2-trimethylpropyl, 1-propyl-1-methylbutyl, and 1,1-dimethylhexyl.

[0308] 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.

[0309] R 11 ~R 18 In the above, examples of the "cycloalkyl" include cycloalkyl having 3 to 12 carbon atoms. A preferred "cycloalkyl" is cycloalkyl having 3 to 10 carbon atoms. A more preferred "cycloalkyl" is cycloalkyl having 3 to 8 carbon atoms. An even more preferred "cycloalkyl" is cycloalkyl having 3 to 6 carbon atoms. Specific examples of "cycloalkyl" include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, methylcyclopentyl, cycloheptyl, methylcyclohexyl, cyclooctyl, and dimethylcyclohexyl.

[0310] As for the cycloalkyl having 5 to 10 carbon atoms with which the pyridine-based substituent is substituted, the above description of the cycloalkyl can be cited.

[0311] R 11 ~R 18As 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.

[0312] 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.

[0313] 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.

[0314] R in the above formula (ETM-2-2) 11 and R 12 may be bonded to form a ring, and as a result, cyclobutane, cyclopentane, cyclopentene, cyclopentadiene, cyclohexane, fluorene, indene, or the like may be spiro-bonded to the five-membered ring of the fluorene skeleton.

[0315] Specific examples of the pyridine derivative include the following compounds: [ka]

[0316] This pyridine derivative can be produced using known raw materials and known synthesis methods.

[0317] <Fluoranthene derivative> The fluoranthene derivative is, for example, a compound represented by the following general formula (ETM-3), and specifically, it is disclosed in International Publication No. 2010 / 134352.

Chemical formula

[0318] In the above formula (ETM-3), X 12 ~X 21 represents hydrogen, halogen, linear, branched or cyclic alkyl, linear, branched or cyclic alkoxy, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl. Here, examples of the substituent when it is substituted include aryl, heteroarylalkyl or cycloalkyl.

[0319] Specific examples of this fluoranthene derivative include, for example, the following compounds.

Chemical formula

[0320] <BO-based derivative> The BO-based derivative is, for example, a polycyclic aromatic compound represented by the following formula (ETM-4), or a multimer of a polycyclic aromatic compound having a plurality of structures represented by the following formula (ETM-4).

Chemical formula

[0321] R 1 ~R 11are each independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, alkyl, cycloalkyl, alkoxy, or aryloxy, in which at least one hydrogen may be substituted with aryl, heteroaryl, alkyl, or cycloalkyl.

[0322] Also, R 1 ~R 11 Adjacent groups among these may be bonded to each other to form an aryl ring or a heteroaryl ring together with the a ring, the b ring, or the c ring, and at least one hydrogen atom in the formed ring may be substituted with an aryl, a heteroaryl, a diarylamino, a diheteroarylamino, an arylheteroarylamino, an alkyl, a cycloalkyl, an alkoxy, or an aryloxy, and at least one hydrogen atom in these rings may be substituted with an aryl, a heteroaryl, an alkyl, or a cycloalkyl.

[0323] In addition, at least one hydrogen in the compound or structure represented by formula (ETM-4) may be substituted with a halogen or deuterium.

[0324] For the explanation of the substituents and ring formation form in formula (ETM-4), and the multimer formed by combining multiple structures of formula (ETM-4), the explanation of the compound represented by the above general formula (1) and its multimer can be cited.

[0325] Specific examples of the BO derivative include the following compounds. [ka]

[0326] The BO derivative can be produced using known raw materials and known synthesis methods.

[0327] <Anthracene derivatives> One of the anthracene derivatives is, for example, a compound represented by the following formula (ETM-5-1). [ka]

[0328] 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.

[0329] Each Ar can be independently selected from divalent benzene or naphthalene, and the two Ar may be different or the same, but it is preferable that they are the same from the viewpoint of ease of synthesis of the anthracene derivative. Ar is bonded to pyridine to form a "moiety consisting of Ar and pyridine", and this moiety is bonded to anthracene as a group represented by any one of the following formulas (Py-1) to (Py-12). * in each structural formula indicates a bonding position. [ka]

[0330] Among these groups, a group represented by any one of the above formulas (Py-1) to (Py-9) is preferred, and a group represented by any one of the above formulas (Py-1) to (Py-6) is more preferred. The two "Ar and pyridine moieties" bonded to anthracene may have the same or different structures, but from the viewpoint of ease of synthesis of anthracene derivatives, it is preferable that they have the same structure. However, from the viewpoint of element characteristics, it is preferable that the two "Ar and pyridine moieties" have the same or different structures.

[0331] R 1 ~R 4The alkyl having 1 to 6 carbon atoms in the formula (I) may be either linear or branched. That is, it is a linear alkyl having 1 to 6 carbon atoms or a branched alkyl having 3 to 6 carbon atoms. More preferably, it is an alkyl having 1 to 4 carbon atoms (branched alkyl having 3 to 4 carbon atoms). Specific examples include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, t-butyl, n-pentyl, isopentyl, neopentyl, t-pentyl (t-amyl), n-hexyl, 1-methylpentyl, 3,3-dimethylbutyl, and 2-ethylbutyl, and methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, and t-butyl are preferred, and methyl, ethyl, and t-butyl are more preferred.

[0332] 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.

[0333] 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.

[0334] 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.

[0335] 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.

[0336] One of the anthracene derivatives is, for example, a compound represented by the following formula (ETM-5-2). [ka]

[0337] Ar 1 are each independently a single bond, or a divalent benzene, naphthalene, anthracene, fluorene, or phenalene.

[0338] Ar 2 are each independently an aryl having 6 to 20 carbon atoms, and the same explanation as for "aryl having 6 to 20 carbon atoms" in the above formula (ETM-5-1) can be cited. An aryl having 6 to 16 carbon atoms is preferable, an aryl having 6 to 12 carbon atoms is more preferable, and an aryl having 6 to 10 carbon atoms is particularly preferable. Specific examples include phenyl, biphenylyl, naphthyl, terphenylyl, anthracenyl, acenaphthylenyl, fluorenyl, phenalenyl, phenanthryl, triphenylenyl, pyrenyl, tetracenyl, perylenyl, etc.

[0339] R 1 ~R 4 are each independently hydrogen, alkyl having 1 to 6 carbon atoms, cycloalkyl having 3 to 6 carbon atoms, or aryl having 6 to 20 carbon atoms, and the explanation in the above formula (ETM-5-1) can be cited.

[0340] Specific examples of these anthracene derivatives include the following compounds. [ka]

[0341] These anthracene derivatives can be produced using known raw materials and known synthesis methods.

[0342] <Benzofluorene derivatives> The benzofluorene derivative is, for example, a compound represented by the following formula (ETM-6). [ka]

[0343] Ar 1are each independently an aryl having 6 to 20 carbon atoms, and the same explanation as for "aryl having 6 to 20 carbon atoms" in the above formula (ETM-5-1) can be cited. An aryl having 6 to 16 carbon atoms is preferable, an aryl having 6 to 12 carbon atoms is more preferable, and an aryl having 6 to 10 carbon atoms is particularly preferable. Specific examples include phenyl, biphenylyl, naphthyl, terphenylyl, anthracenyl, acenaphthylenyl, fluorenyl, phenalenyl, phenanthryl, triphenylenyl, pyrenyl, tetracenyl, perylenyl, etc.

[0344] 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.

[0345] Ar 2 The "alkyl" in the above may be either linear or branched, and examples thereof include linear alkyl having 1 to 24 carbon atoms and branched alkyl having 3 to 24 carbon atoms. A preferred "alkyl" is an alkyl having 1 to 18 carbon atoms (branched alkyl having 3 to 18 carbon atoms). A more preferred "alkyl" is an alkyl having 1 to 12 carbon atoms (branched alkyl having 3 to 12 carbon atoms). An even more preferred "alkyl" is an alkyl having 1 to 6 carbon atoms (branched alkyl having 3 to 6 carbon atoms). An especially preferred "alkyl" is an alkyl having 1 to 4 carbon atoms (branched alkyl having 3 to 4 carbon atoms). Specific examples of "alkyl" include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, t-butyl, n-pentyl, isopentyl, neopentyl, t-pentyl (t-amyl), n-hexyl, 1-methylpentyl, 3,3-dimethylbutyl, 2-ethylbutyl, n-heptyl, 1-methylhexyl, and the like.

[0346] 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.

[0347] 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.

[0348] Specific examples of the "aryl having 6 to 30 carbon atoms" include phenyl, naphthyl, acenaphthylenyl, fluorenyl, phenalenyl, phenanthryl, triphenylenyl, pyrenyl, naphthacenyl, perylenyl, and pentacenyl.

[0349] 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.

[0350] Specific examples of the benzofluorene derivative include the following compounds. [ka]

[0351] The benzofluorene derivative can be produced using known raw materials and known synthesis methods.

[0352] <Phosphine oxide derivatives> The phosphine oxide derivative is, for example, a compound represented by the following formula (ETM-7-1), the details of which are also described in WO 2013 / 079217. [ka] R 5 is a substituted or unsubstituted alkyl having 1 to 20 carbon atoms, cycloalkyl having 3 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 cycloalkyl having 3 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, alkyl or cycloalkyl.

[0353] The phosphine oxide derivative may be, for example, a compound represented by the following formula (ETM-7-2). [ka]

[0354] R 1 ~R 3may be the same or different and are selected from hydrogen, an alkyl group, a cycloalkyl group, an aralkyl group, an alkenyl group, a cycloalkenyl group, an alkynyl group, an alkoxy group, an alkylthio group, a cycloalkylthio group, an aryl ether group, an aryl thioether group, an aryl group, a heterocyclic group, a halogen, a cyano group, an aldehyde group, a carbonyl group, a carboxyl group, an amino group, a nitro group, a silyl group, and a fused ring formed between an adjacent substituent.

[0355] Ar 1 may be the same or different and are an arylene or heteroarylene group; Ar 2 may be the same or different and are aryl or heteroaryl groups, 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.

[0356] Among these substituents, the alkyl group refers to a saturated aliphatic hydrocarbon group such as a methyl group, an ethyl group, a propyl group, or a butyl group, which may be unsubstituted or substituted. If substituted, the substituent is not particularly limited, and may be, for example, an alkyl group, an aryl group, or a heterocyclic group, which is also common to the following description. The number of carbon atoms in the alkyl group is not particularly limited, but is usually in the range of 1 to 20 from the viewpoint of availability and cost.

[0357] The cycloalkyl group 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 group is not particularly limited, but is usually in the range of 3 to 20.

[0358] The aralkyl group refers to an aromatic hydrocarbon group mediated by an aliphatic hydrocarbon, such as a benzyl group or a phenylethyl group, 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.

[0359] The alkenyl group refers to an unsaturated aliphatic hydrocarbon group containing a double bond, such as a vinyl group, an allyl group, or a butadienyl group, which may be unsubstituted or substituted. The number of carbon atoms in the alkenyl group is not particularly limited, but is usually in the range of 2 to 20.

[0360] Moreover, the cycloalkenyl group refers to an unsaturated alicyclic hydrocarbon group containing a double bond, such as a cyclopentenyl group, a cyclopentadienyl group, or a cyclohexene group, which may be either unsubstituted or substituted.

[0361] The alkynyl group refers to an unsaturated aliphatic hydrocarbon group containing a triple bond, such as an acetylenyl group, which may be unsubstituted or substituted. The number of carbon atoms in the alkynyl group is not particularly limited, but is usually in the range of 2 to 20.

[0362] The alkoxy group refers to an aliphatic hydrocarbon group having an ether bond, such as a methoxy group, and the aliphatic hydrocarbon group may be unsubstituted or substituted. The number of carbon atoms in the alkoxy group is not particularly limited, but is usually in the range of 1 to 20.

[0363] An alkylthio group is a group in which the oxygen atom of the ether bond of an alkoxy group is substituted with a sulfur atom.

[0364] In addition, the cycloalkylthio group is a group in which the oxygen atom of the ether bond of a cycloalkoxy group is replaced with a sulfur atom.

[0365] The aryl ether group refers to an aromatic hydrocarbon group, such as a phenoxy group, 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.

[0366] An aryl thioether group is a group in which the oxygen atom of the ether bond of an aryl ether group is substituted with a sulfur atom.

[0367] The aryl group refers to an aromatic hydrocarbon group such as a phenyl group, a naphthyl group, a biphenylyl group, a phenanthryl group, a terphenyl group, or a pyrenyl group. 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.

[0368] The heterocyclic group refers to a cyclic structure group having atoms other than carbon, such as a furanyl group, a thiophenyl group, an oxazolyl group, a pyridyl group, a quinolinyl group, a carbazolyl group, 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.

[0369] Halogen refers to fluorine, chlorine, bromine and iodine.

[0370] The aldehyde group, carbonyl group and amino group may also include groups substituted with an aliphatic hydrocarbon, an alicyclic hydrocarbon, an aromatic hydrocarbon, a heterocycle or the like.

[0371] Furthermore, the aliphatic hydrocarbons, alicyclic hydrocarbons, aromatic hydrocarbons and heterocycles may be either unsubstituted or substituted.

[0372] The silyl group refers to a silicon compound group such as a trimethylsilyl group, which may be unsubstituted or substituted. The number of carbon atoms in the silyl group is not particularly limited, but is usually in the range of 3 to 20. The number of silicon atoms is usually 1 to 6.

[0373] The condensed ring formed between adjacent substituents is, for example, Ar 1 and R 2 , Ar 1 and R 3 , Ar 2 and R 2 , Ar 2 and R 3 , R 2 and R 3 , Ar 1 and Ar 2 etc., where n is 1, two R 1 They may form conjugated or non-conjugated fused rings together. These fused rings may contain nitrogen, oxygen, or sulfur atoms in the ring structure, and may be fused to further rings.

[0374] Specific examples of the phosphine oxide derivative include the following compounds. [ka]

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

[0376] <Pyrimidine derivatives> The pyrimidine derivative is, for example, a compound represented by the following formula (ETM-8), preferably a compound represented by the following formula (ETM-8-1). Details are also described in WO 2011 / 021689. [ka]

[0377] 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.

[0378] The "aryl" in the "optionally substituted aryl" includes, for example, aryl having 6 to 30 carbon atoms, preferably aryl having 6 to 24 carbon atoms, more preferably aryl having 6 to 20 carbon atoms, and further preferably aryl having 6 to 12 carbon atoms.

[0379] Specific examples of "aryl" include monocyclic aryl phenyl, bicyclic aryl (2-, 3-, 4-) biphenylyl, condensed bicyclic aryl (1-, 2-) naphthyl, tricyclic aryl terphenylyl (m-terphenyl-2'-yl, m-terphenyl-4'-yl, m-terphenyl-5'-yl, o-terphenyl-3'-yl, o-terphenyl-4'-yl, p-terphenyl-2'-yl, m-terphenyl-2-yl, m-terphenyl-3-yl, m-terphenyl-4-yl, o-terphenyl-2-yl, o-terphenyl-3-yl, o-terphenyl-4-yl, p-terphenyl-2-yl, p-terphenyl-3-yl, p-terphenyl-4-yl), condensed tricyclic aryl Examples of the aryl include acenaphthylene-(1-,3-,4-,5-)yl, fluorene-(1-,2-,3-,4-,9-)yl, phenalene-(1-,2-)yl, and (1-,2-,3-,4-,9-)phenanthryl; the tetracyclic aryl is quaterphenylyl (5'-phenyl-m-terphenyl-2-yl, 5'-phenyl-m-terphenyl-3-yl, 5'-phenyl-m-terphenyl-4-yl, and m-quaterphenylyl); the condensed tetracyclic aryl is triphenylene-(1-,2-)yl, pyrene-(1-,2-,4-)yl, and naphthacene-(1-,2-,5-)yl; and the condensed pentacyclic aryl is perylene-(1-,2-,3-)yl and pentacene-(1-,2-,5-,6-)yl.

[0380] 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.

[0381] 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.

[0382] The above aryl and heteroaryl may be substituted, for example, by the above aryl or heteroaryl, respectively.

[0383] Specific examples of the pyrimidine derivative include the following compounds: [ka]

[0384] The pyrimidine derivative can be produced using known raw materials and known synthesis methods.

[0385] <Carbazole derivatives> The carbazole 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 U.S. Patent Publication No. 2014 / 0197386. [ka]

[0386] Each Ar is independently an optionally substituted aryl or an optionally substituted heteroaryl, and each n is independently an integer of 0 to 4, preferably an integer of 0 to 3, and more preferably 0 or 1.

[0387] The "aryl" in the "optionally substituted aryl" includes, for example, aryl having 6 to 30 carbon atoms, preferably aryl having 6 to 24 carbon atoms, more preferably aryl having 6 to 20 carbon atoms, and further preferably aryl having 6 to 12 carbon atoms.

[0388] Specific examples of "aryl" include monocyclic aryl phenyl, bicyclic aryl (2-, 3-, 4-) biphenylyl, condensed bicyclic aryl (1-, 2-) naphthyl, tricyclic aryl terphenylyl (m-terphenyl-2'-yl, m-terphenyl-4'-yl, m-terphenyl-5'-yl, o-terphenyl-3'-yl, o-terphenyl-4'-yl, p-terphenyl-2'-yl, m-terphenyl-2-yl, m-terphenyl-3-yl, m-terphenyl-4-yl, o-terphenyl-2-yl, o-terphenyl-3-yl, o-terphenyl-4-yl, p-terphenyl-2-yl, p-terphenyl-3-yl, p-terphenyl-4-yl), condensed tricyclic aryl Examples of the aryl include acenaphthylene-(1-,3-,4-,5-)yl, fluorene-(1-,2-,3-,4-,9-)yl, phenalene-(1-,2-)yl, and (1-,2-,3-,4-,9-)phenanthryl; the tetracyclic aryl is quaterphenylyl (5'-phenyl-m-terphenyl-2-yl, 5'-phenyl-m-terphenyl-3-yl, 5'-phenyl-m-terphenyl-4-yl, and m-quaterphenylyl); the condensed tetracyclic aryl is triphenylene-(1-,2-)yl, pyrene-(1-,2-,4-)yl, and naphthacene-(1-,2-,5-)yl; and the condensed pentacyclic aryl is perylene-(1-,2-,3-)yl and pentacene-(1-,2-,5-,6-)yl.

[0389] 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.

[0390] 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.

[0391] The above aryl and heteroaryl may be substituted, for example, by the above aryl or heteroaryl, respectively.

[0392] The carbazole derivative may be a polymer in which a plurality of compounds represented by the above formula (ETM-9) are bonded together by single bonds, etc. In this case, they may be bonded together by an aryl ring (preferably a polyvalent benzene ring, naphthalene ring, anthracene ring, fluorene ring, benzofluorene ring, phenalene ring, phenanthrene ring, or triphenylene ring) other than a single bond.

[0393] Specific examples of the carbazole derivative include the following compounds. [ka]

[0394] The carbazole derivative can be produced using known raw materials and known synthesis methods.

[0395] <Triazine derivatives> The triazine derivative is, for example, a compound represented by the following formula (ETM-10), preferably a compound represented by the following formula (ETM-10-1), the details of which are described in US Patent Publication No. 2011 / 0156013. [ka]

[0396] 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.

[0397] The "aryl" in the "optionally substituted aryl" includes, for example, aryl having 6 to 30 carbon atoms, preferably aryl having 6 to 24 carbon atoms, more preferably aryl having 6 to 20 carbon atoms, and further preferably aryl having 6 to 12 carbon atoms.

[0398] Specific examples of "aryl" include monocyclic aryl phenyl, bicyclic aryl (2-, 3-, 4-) biphenylyl, condensed bicyclic aryl (1-, 2-) naphthyl, tricyclic aryl terphenylyl (m-terphenyl-2'-yl, m-terphenyl-4'-yl, m-terphenyl-5'-yl, o-terphenyl-3'-yl, o-terphenyl-4'-yl, p-terphenyl-2'-yl, m-terphenyl-2-yl, m-terphenyl-3-yl, m-terphenyl-4-yl, o-terphenyl-2-yl, o-terphenyl-3-yl, o-terphenyl-4-yl, p-terphenyl-2-yl, p-terphenyl-3-yl, p-terphenyl-4-yl), condensed tricyclic aryl Examples of the aryl include acenaphthylene-(1-,3-,4-,5-)yl, fluorene-(1-,2-,3-,4-,9-)yl, phenalene-(1-,2-)yl, and (1-,2-,3-,4-,9-)phenanthryl; the tetracyclic aryl is quaterphenylyl (5'-phenyl-m-terphenyl-2-yl, 5'-phenyl-m-terphenyl-3-yl, 5'-phenyl-m-terphenyl-4-yl, and m-quaterphenylyl); the condensed tetracyclic aryl is triphenylene-(1-,2-)yl, pyrene-(1-,2-,4-)yl, and naphthacene-(1-,2-,5-)yl; and the condensed pentacyclic aryl is perylene-(1-,2-,3-)yl and pentacene-(1-,2-,5-,6-)yl.

[0399] 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.

[0400] 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.

[0401] The above aryl and heteroaryl may be substituted, for example, by the above aryl or heteroaryl, respectively.

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

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

[0404] <Benzimidazole derivatives> The benzimidazole derivative is, for example, a compound represented by the following formula (ETM-11). [ka]

[0405] φ is an n-valent aryl ring (preferably an n-valent benzene ring, naphthalene ring, anthracene ring, fluorene ring, benzofluorene ring, phenalene ring, phenanthrene ring or triphenylene ring), n is an integer of 1 to 4, and the "benzoimidazole-based substituent" is a substituent in which the pyridyl group in the "pyridine-based substituent" in the above formula (ETM-2), formula (ETM-2-1) and formula (ETM-2-2) is replaced with a benzimidazole group, and at least one hydrogen in the benzimidazole derivative may be replaced with a deuterium. * in the following structural formula indicates a bond position. [ka]

[0406] R in the benzimidazole group 11 is hydrogen, alkyl having 1 to 24 carbon atoms, cycloalkyl having 3 to 12 carbon atoms, or aryl having 6 to 30 carbon atoms, and R 11 The explanation can be cited.

[0407] It is further preferable that φ is an anthracene ring or a fluorene ring. In this case, the structure can be as described in the above formula (ETM-2-1) or formula (ETM-2-2). 11 ~R 18 The explanation for formula (ETM-2-1) or formula (ETM-2-2) above can be cited. In addition, in formula (ETM-2-1) or formula (ETM-2-2) above, the two pyridine-based substituents are explained as being bonded, but when these are replaced with benzimidazole-based substituents, both pyridine-based substituents may be replaced with benzimidazole-based substituents (i.e., n=2), or one of the pyridine-based substituents may be replaced with a benzimidazole-based substituent and the other pyridine-based substituent may be replaced with R 11 ~R 18 (i.e., n=1). Furthermore, for example, R in the above formula (ETM-2-1) 11 ~R 18At least one of the above is replaced with a benzimidazole-based substituent to form a "pyridine-based substituent" R 11 ~R 18 may be substituted.

[0408] Specific examples of the benzimidazole derivative include 1-phenyl-2-(4-(10-phenylanthracen-9-yl)phenyl)-1H-benzo[d]imidazole, 2-(4-(10-(naphthalen-2-yl)anthracen-9-yl)phenyl)-1-phenyl-1H-benzo[d]imidazole, 2-(3-(10-(naphthalen-2-yl)anthracen-9-yl)phenyl)-1-phenyl-1H-benzo[d]imidazole, and 5-(10-(naphthalen-2-yl)anthracen-9-yl)-1,2-diphenyl-1H-benzo[d]imidazole. , 1-(4-(10-(naphthalene-2-yl)anthracen-9-yl)phenyl)-2-phenyl-1H-benzo[d]imidazole, 2-(4-(9,10-di(naphthalene-2-yl)anthracen-2-yl)phenyl)-1-phenyl-1H-benzo[d]imidazole, 1-(4-(9,10-di(naphthalene-2-yl)anthracen-2-yl)phenyl)-2-phenyl-1H-benzo[d]imidazole, 5-(9,10-di(naphthalene-2-yl)anthracen-2-yl)-1,2-diphenyl-1H-benzo[d]imidazole, and the like. [ka]

[0409] The benzimidazole derivative can be produced using known raw materials and known synthesis methods.

[0410] <Phenanthroline derivatives> The phenanthroline derivative is, for example, a compound represented by the following formula (ETM-12) or formula (ETM-12-1), the details of which are described in WO 2006 / 021982. [ka]

[0411] 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.

[0412] 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.

[0413] At least one hydrogen atom in each of the phenanthroline derivatives may be replaced with deuterium.

[0414] R 11 ~R 18 The alkyl, cycloalkyl and aryl in the above formula (ETM-2) are R 11 ~R 18 The explanation of the above can be cited. In addition to the above examples, φ may have the following structural formulas. In the structural formulas below, R is independently hydrogen, methyl, ethyl, isopropyl, cyclohexyl, phenyl, 1-naphthyl, 2-naphthyl, biphenylyl, or terphenylyl. In each structural formula, * indicates a bond position. [ka]

[0415] Specific examples of the phenanthroline derivative include 4,7-diphenyl-1,10-phenanthroline, 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline, 9,10-di(1,10-phenanthroline-2-yl)anthracene, 2,6-di(1,10-phenanthroline-5-yl)pyridine, 1,3,5-tri(1,10-phenanthroline-5-yl)benzene, 9,9'-difluoro-bis(1,10-phenanthroline-5-yl), bathocuproine, and 1,3-bis(2-phenyl-1,10-phenanthroline-9-yl)benzene. [ka]

[0416] The phenanthroline derivative can be produced using known raw materials and known synthesis methods.

[0417] <Quinolinol metal complexes> The quinolinol metal complex is, for example, a compound represented by the following general formula (ETM-13). [ka] In the formula, R 1 ~R 6 are each independently hydrogen, fluorine, alkyl, cycloalkyl, aralkyl, alkenyl, cyano, alkoxy or aryl; M is Li, Al, Ga, Be or Zn; and n is an integer of 1 to 3.

[0418] 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.

[0419] The quinolinol metal complex can be produced using known raw materials and known synthesis methods.

[0420] <Thiazole derivatives and benzothiazole derivatives> The thiazole derivative is, for example, a compound represented by the following formula (ETM-14-1). [ka] The benzothiazole derivative is, for example, a compound represented by the following formula (ETM-14-2). [ka]

[0421] In each formula, φ is an n-valent aryl ring (preferably an n-valent benzene ring, naphthalene ring, anthracene ring, fluorene ring, benzofluorene ring, phenalene ring, phenanthrene ring or triphenylene ring), n is an integer of 1 to 4, and the "thiazole-based substituent" or "benzothiazole-based substituent" is a substituent in which the pyridyl group in the "pyridine-based substituent" in the above formula (ETM-2), formula (ETM-2-1) and formula (ETM-2-2) is replaced with a thiazole group or a benzothiazole group, and at least one hydrogen atom in the thiazole derivative and the benzothiazole derivative may be replaced with a deuterium atom. * in the following structural formula indicates a bond position. [ka]

[0422] It is further preferable that φ is an anthracene ring or a fluorene ring. In this case, the structure can be as described in the above formula (ETM-2-1) or formula (ETM-2-2). 11 ~R 18 The explanation for formula (ETM-2-1) or formula (ETM-2-2) above can be cited. In addition, in formula (ETM-2-1) or formula (ETM-2-2) above, the two pyridine-based substituents are explained as being bonded together, but when these are replaced with a thiazole-based substituent (or a benzothiazole-based substituent), both pyridine-based substituents may be replaced with a thiazole-based substituent (or a benzothiazole-based substituent) (i.e., n=2), or one of the pyridine-based substituents may be replaced with a thiazole-based substituent (or a benzothiazole-based substituent) and the other pyridine-based substituent may be replaced with R 11 ~R 18 (i.e., n=1). Furthermore, for example, R in the above formula (ETM-2-1) 11 ~R 18 At least one of the above is replaced with a thiazole-based substituent (or a benzothiazole-based substituent) to form a "pyridine-based substituent" R 11 ~R 18 may be substituted.

[0423] These thiazole or benzothiazole derivatives can be produced using known raw materials and known synthesis methods.

[0424] The electron transport layer or the electron injection layer may further contain a substance capable of reducing the material forming the electron transport layer or the electron injection layer. As the reducing substance, various substances can be used as long as they have a certain degree of reducing ability, and for example, at least one selected from the group consisting of alkali metals, alkaline earth metals, rare earth metals, oxides of alkali metals, halides of alkali metals, oxides of alkaline earth metals, halides of alkaline earth metals, oxides of rare earth metals, halides of rare earth metals, organic complexes of alkali metals, organic complexes of alkaline earth metals, and organic complexes of rare earth metals can be suitably used.

[0425] Preferred reducing substances include alkali metals such as Na (work function 2.36 eV), K (2.28 eV), Rb (2.16 eV) or Cs (1.95 eV) and alkaline earth metals such as Ca (2.9 eV), Sr (2.0 to 2.5 eV) or Ba (2.52 eV), and substances with a work function of 2.9 eV or less are particularly preferred. Among these, more preferred reducing substances are alkali metals such as K, Rb or Cs, more preferably Rb or Cs, and most preferably Cs. These alkali metals have particularly high reducing ability, and by adding a relatively small amount to the material forming the electron transport layer or electron injection layer, the luminance of the organic EL element can be improved and the life can be extended. Furthermore, as a reducing substance having a work function of 2.9 eV or less, a combination of two or more of these alkali metals is also preferred, and in particular, a combination containing Cs is preferred, for example, a combination of Cs and Na, Cs and K, Cs and Rb, or a combination of Cs, Na and K. By containing Cs, the reducing ability can be efficiently exhibited, and by adding it to a material forming an electron transport layer or an electron injection layer, the luminance of the organic EL element can be improved and the life span can be extended.

[0426] The above-mentioned electron injection layer material and electron transport layer material can be used as an electron layer material in the form of a polymer compound obtained by polymerizing a reactive compound substituted with a reactive substituent as a monomer, or a crosslinked polymer thereof, or a pendant polymer compound obtained by reacting a main chain polymer with the reactive compound, or a crosslinked pendant polymer thereof. In this case, the explanation of the polycyclic aromatic compound represented by formula (1) can be cited as the reactive substituent. The applications of such polymer compounds and crosslinked polymers will be described in detail below.

[0427] <Cathode in organic electroluminescent device> The cathode 108 serves to inject electrons into the light-emitting layer 105 through the electron injection layer 107 and the electron transport layer 106 .

[0428] 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.

[0429] 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.

[0430] <Binding agents that may be used in each layer> The materials used for the hole injection layer, hole transport layer, light emitting layer, electron transport layer and electron injection layer can form each layer alone, but they can also be used as a polymer binder by being dispersed in a solvent-soluble resin such as polyvinyl chloride, polycarbonate, polystyrene, poly(N-vinylcarbazole), polymethyl methacrylate, polybutyl methacrylate, polyester, polysulfone, polyphenylene oxide, polybutadiene, hydrocarbon resin, ketone resin, phenoxy resin, polyamide, ethyl cellulose, vinyl acetate resin, ABS resin, polyurethane resin, or a curable resin such as phenol resin, xylene resin, petroleum resin, urea resin, melamine resin, unsaturated polyester resin, alkyd resin, epoxy resin, silicone resin, or the like.

[0431] <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.

[0432] When applying a DC voltage to the organic EL element obtained in this way, the anode should be set to + and the cathode to -. When a voltage of about 2 to 40 V is applied, light emission can be observed from the transparent or semi-transparent electrode side (anode or cathode, or both). This organic EL element also emits light when a pulse current or an AC current is applied. The waveform of the AC current applied may be any waveform.

[0433] Next, as an example of a method for producing an organic EL element, a method for producing an organic EL element consisting of an anode, a hole injection layer, a hole transport layer, an emitting layer consisting of a host material and a dopant material, an electron transport layer, an electron injection layer, and a cathode will be described.

[0434] <Vapor deposition method> A thin film of an anode material is formed on a suitable substrate by vapor deposition or the like to prepare an anode, and then a thin film of a hole injection layer and a hole transport layer is formed on the anode. A host material and a dopant material are co-deposited on the anode to form a thin film as a light-emitting layer, an electron transport layer and an electron injection layer are formed on the light-emitting layer, and a thin film of a cathode material is further formed by vapor deposition or the like to prepare a cathode, thereby obtaining a desired organic EL device. Note that in the preparation of the above-mentioned organic EL device, the preparation order can also be reversed, and the layers can be prepared in the order of cathode, electron injection layer, electron transport layer, light-emitting layer, hole transport layer, hole injection layer, and anode.

[0435] <Wet film formation method> The wet film formation method is carried out by preparing a low molecular weight compound capable of forming each organic layer of an organic EL element as a liquid composition for forming an organic layer, and using this. If there is no suitable organic solvent for dissolving this low molecular weight compound, the composition for forming an organic layer may be prepared from a polymer compound polymerized together with other monomers having a solubility function as a reactive compound obtained by substituting a reactive substituent on the low molecular weight compound or a main chain polymer.

[0436] In the wet film formation method, a coating film is generally formed through a coating step of coating a substrate with a composition for forming an organic layer and a drying step of removing the solvent from the coated composition for forming an organic layer. When the polymer compound has a crosslinkable substituent (also called a crosslinkable polymer compound), the polymer is further crosslinked by the drying step to form a crosslinked polymer. Depending on the difference in the coating step, a method using a spin coater is called a spin coat method, a method using a slit coater is called a slit coat method, a method using a plate is called a gravure, offset, reverse offset, or flexographic printing method, a method using an inkjet printer is called an inkjet method, and a method spraying in a mist form is called a spray method. The drying step includes air drying, heating, drying under reduced pressure, and the like. The drying step may be performed only once, or may be performed multiple times using different methods or conditions. In addition, different methods may be used in combination, such as baking under reduced pressure.

[0437] 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.

[0438] On the other hand, compared to the vacuum deposition method, wet film formation can be difficult to laminate. When producing laminated films using the wet film formation method, it is necessary to prevent the dissolution of the lower layer by the composition of the upper layer, and compositions with controlled solubility, crosslinking of the lower layer, and orthogonal solvents (solvents that do not dissolve in each other) are used. However, even with these technologies, it can be difficult to use the wet film formation method to apply all films.

[0439] 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.

[0440] For example, the procedure for producing an organic EL element by partially applying a wet film formation method will be described below. (Step 1) Formation of the anode by vacuum deposition (Step 2) Forming a film by a wet film formation method using a composition for forming a hole injection layer containing a material for the hole injection layer (Step 3) Forming a film by a wet film formation method using a composition for forming a hole transport layer containing a material for the hole transport layer (Step 4) Formation of a film by a wet film formation method using a composition for forming an emitting layer containing a host material and a dopant material (Step 5) Formation of the electron transport layer by vacuum deposition (Step 6) Formation of the electron injection layer by vacuum deposition (Step 7) Cathode deposition by vacuum deposition Through this procedure, an organic EL element consisting of an anode, a hole injection layer, a hole transport layer, an emitting layer made of a host material and a dopant material, an electron transport layer, an electron injection layer, and a cathode is obtained. Of course, if there is a means for preventing dissolution of the lower light-emitting layer, or if a means for forming a film from the cathode side is used in the opposite procedure to the above, a layer-forming composition containing a material for the electron transport layer and a material for the electron injection layer can be prepared and then the layer can be formed by a wet film formation method.

[0441] <Other film formation methods> The composition for forming an organic layer can be formed into a film by laser thermal imaging (LITI). LITI is a method in which a compound attached to a substrate is heated and evaporated by a laser, and the composition for forming an organic layer can be used as the material applied to the substrate.

[0442] <Optional process> Before and after each film-forming step, appropriate treatment steps, cleaning steps, and drying steps may be appropriately inserted. Examples of treatment steps include exposure treatment, plasma surface treatment, ultrasonic treatment, ozone treatment, cleaning treatment using an appropriate solvent, and heat treatment. Furthermore, a series of steps for preparing a bank may also be included.

[0443] Photolithography techniques can be used to fabricate the bank. Positive resist materials and negative resist materials can be used as bank materials that can be used in photolithography. In addition, patternable printing methods such as inkjet printing, gravure offset printing, reverse offset printing, and screen printing can also be used. In such cases, a permanent resist material can also be used. In addition, the bank may be formed using one material, or may be formed by combining multiple structures using multiple materials.

[0444] Materials that can be used for the bank include, but are not limited to, inorganic materials such as silicon oxide, silicon dioxide, silicon nitride, and silicon oxynitride, polysaccharides and their derivatives, homopolymers and copolymers of hydroxyl-containing ethylenic monomers, biopolymers, polyacryloyl compounds, polyesters, polystyrenes, polyimides, polyamideimides, polyetherimides, polysulfides, polysulfones, polyphenylenes, polyphenyl ethers, polyurethanes, epoxy (meth)acrylates, melamine (meth)acrylates, polyolefins, cyclic polyolefins, acrylonitrile-butadiene-styrene copolymers (ABS), silicone resins, polyvinyl chloride, chlorinated polyethylene, chlorinated polypropylene, polyacetates, polynorbornenes, synthetic rubbers, fluorinated polymers such as polyfluorovinylidene, polytetrafluoroethylene, and polyhexafluoropropylene, copolymers of fluoroolefins and hydrocarbon olefins, and fluorocarbon polymers.

[0445] <Composition for forming organic layer used in wet film formation method> The composition for forming an organic layer is obtained by dissolving a low molecular weight compound capable of forming each organic layer of an organic EL device, or a polymer compound obtained by polymerizing the low molecular weight compound, in an organic solvent. For example, the composition for forming an emitting layer contains at least one polycyclic aromatic compound (or a polymer compound thereof) as a first component, which is a dopant material, at least one host material as a second component, and at least one organic solvent as a third component. The first component functions as a dopant component of the emitting layer obtained from the composition, and the second component functions as a host component of the emitting layer. The third component functions as a solvent that dissolves the first and second components in the composition, and gives a smooth and uniform surface shape due to the controlled evaporation rate of the third component itself during application.

[0446] <Organic solvent> The organic layer forming composition contains at least one organic solvent. By controlling the evaporation rate of the organic solvent during film formation, it is possible to control and improve the film forming properties, the presence or absence of defects in the coating film, the surface roughness, and the smoothness. In addition, during film formation using the inkjet method, it is possible to control the meniscus stability at the pinhole of the inkjet head, and control and improve the ejection properties. In addition, by controlling the drying rate of the film and the orientation of the derivative molecules, it is possible to improve the electrical properties, light emitting properties, efficiency, and life of an organic EL element having an organic layer obtained from the organic layer forming composition.

[0447] (1) Physical properties of organic solvents The boiling point of at least one organic solvent is 130°C to 300°C, more preferably 140°C to 270°C, and further preferably 150°C to 250°C. When the boiling point is higher than 130°C, it is preferable from the viewpoint of inkjet dischargeability. Also, when the boiling point is lower than 300°C, it is preferable from the viewpoint of coating film defects, surface roughness, residual solvent, and smoothness. From the viewpoint of good inkjet dischargeability, film-forming property, smoothness, and low residual solvent, it is more preferable that the organic solvent contains two or more organic solvents. On the other hand, in some cases, the composition may be in a solid state by removing the solvent from the composition for forming the organic layer, taking into consideration transportability, etc.

[0448] Furthermore, the organic solvent contains a good solvent (GS) and a poor solvent (PS) for at least one of the solutes, and the boiling point (BP) of the good solvent (GS) is GS ) is the boiling point (BP PS ) is particularly preferred. By adding a poor solvent with a high boiling point, the good solvent with a low boiling point volatilizes first during film formation, increasing the concentration of the components in the composition and the concentration of the poor solvent, promoting rapid film formation. This results in a coating film with fewer defects, less surface roughness, and high smoothness.

[0449] Difference in solubility (S GS -S PS The boiling point difference (BP) is preferably 1% or more, more preferably 3% or more, and even more preferably 5% or more. PS -BP GS ) is preferably 10° C. or higher, more preferably 30° C. or higher, and even more preferably 50° C. or higher.

[0450] After the film is formed, the organic solvent is removed from the coating film by a drying process such as vacuum, reduced pressure, or heating. When heating is performed, from the viewpoint of improving the coating film-forming property, it is preferable to perform the heating at a temperature of at least one of the solutes at a glass transition temperature (Tg) +30°C or lower. From the viewpoint of reducing the residual solvent, it is preferable to heat at at least one of the solutes at a glass transition temperature (Tg) -30°C or higher. Even if the heating temperature is lower than the boiling point of the organic solvent, the organic solvent is sufficiently removed because the film is thin. Also, drying may be performed multiple times at different temperatures, and multiple drying methods may be used in combination.

[0451] (2) Specific examples of organic solvents Examples of the organic solvent used in the composition for forming the organic layer include alkylbenzene solvents, phenyl ether solvents, alkyl ether solvents, cyclic ketone solvents, aliphatic ketone solvents, monocyclic ketone solvents, solvents having a diester skeleton, and fluorine-containing solvents. Specific examples include pentanol, hexanol, heptanol, octanol, nonanol, decanol, undecanol, dodecanol, tetradecanol, hexane-2-ol, heptan-2-ol, octan-2-ol, decan-2-ol, dodecan-2-ol, cyclohexanol, Sanol, α-terpineol, β-terpineol, γ-terpineol, δ-terpineol, terpineol (mixture), ethylene glycol monomethyl ether acetate, propylene glycol monomethyl ether acetate, diethylene glycol dimethyl ether, dipropylene glycol dimethyl ether, diethylene glycol ethyl methyl ether, diethylene glycol isopropyl methyl ether, dipropylene glycol monomethyl ether, diethylene glycol diethyl ether, diethylene glycol monomethyl ether , diethylene glycol butyl methyl ether, tripropylene glycol dimethyl ether, triethylene glycol dimethyl ether, diethylene glycol monobutyl ether, ethylene glycol monophenyl ether, triethylene glycol monomethyl ether, diethylene glycol dibutyl ether, triethylene glycol butyl methyl ether, polyethylene glycol dimethyl ether, tetraethylene glycol dimethyl ether, p-xylene, m-xylene, o-xylene, 2,6-lutidine, 2-fluoro-m-xylene, 3-fluoro-o-xylene, 2-chlorobenzotrifluoride, cumene, toluene, 2-chloro-6-fluorotoluene, 2-fluoroanisole, anisole, 2,3-dimethylpyrazine, bromobenzene, 4-fluoroanisole, 3-fluoroanisole, 3-trifluoromethylanisole, mesitylene, 1,2,4-trimethylbenzene, t-butylbenzene, 2-methylanisole, phenetole, benzodioxole, 4-methylanisole, s-butylbenzene, 3-methylanisole, 4-fluoro-3-methylanisole, cymene, 1,2,3-Trimethylbenzene, 1,2-Dichlorobenzene, 2-Fluorobenzonitrile, 4-Fluoroveratrol, 2,6-Dimethylanisole, n-Butylbenzene, 3-Fluorobenzonitrile, Decalin (Decahydronaphthalene), Neopentylbenzene, 2,5-Dimethylanisole, 2,4-Dimethylanisole, Benzonitrile, 3,5-Dimethylanisole, Diphenyl ether, 1-Fluoro-3,5-dimethoxybenzene, Methyl benzoate, Isopentylbenzene, 3,4-Dimethylanisole, o-Tolunitrile, n-Amylbenzene, Veratrol, 1,2,3,4-Tetrahydronaphthalene, Ethyl benzoate, n-Hexylbenzene, Propyl benzoate, Cyclohexylbenzene, 1-Methoxybenzene, Examples of the solvent include, but are not limited to, ethylnaphthalene, 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.

[0452] <Optional ingredients> The composition for forming the organic layer may contain optional components, such as a binder and a surfactant, to the extent that the properties of the composition are not impaired.

[0453] (1) Binder The composition for forming an organic layer may contain a binder. The binder forms a film during film formation and bonds the resulting film to a substrate. The binder also plays a role in dissolving, dispersing, and binding other components in the composition for forming an organic layer.

[0454] Examples of binders used in the organic layer-forming composition include, but are not limited to, acrylic resins, polyethylene terephthalate, ethylene-vinyl acetate copolymers, ethylene-vinyl alcohol copolymers, acrylonitrile-ethylene-styrene copolymer (AES) resins, ionomers, chlorinated polyethers, diallyl phthalate resins, unsaturated polyester resins, polyethylene, polypropylene, polyvinyl chloride, polyvinylidene chloride, polystyrene, polyvinyl acetate, Teflon, acrylonitrile-butadiene-styrene copolymer (ABS) resins, acrylonitrile-styrene copolymer (AS) resins, phenolic resins, epoxy resins, melamine resins, urea resins, alkyd resins, polyurethanes, and copolymers of the above resins and polymers.

[0455] The binder used in the organic layer-forming composition may be of one type or a mixture of two or more types.

[0456] (2) Surfactants The organic layer forming composition may contain a surfactant, for example, to control the film surface uniformity, solvent affinity and liquid repellency of the organic layer forming composition. Surfactants are classified into ionic and nonionic based on the structure of the hydrophilic group, and further classified into alkyl, silicon and fluorine based on the structure of the hydrophobic group. In addition, based on the molecular structure, they are classified into monomolecular systems with relatively small molecular weight and simple structure, and polymer systems with large molecular weight and side chains or branches. In addition, based on the composition, they are classified into single systems and mixed systems in which two or more types of surfactants and base materials are mixed. All types of surfactants can be used as surfactants that can be used in the organic layer forming composition.

[0457] Examples of surfactants include Polyflow No. 45, Polyflow KL-245, Polyflow No. 75, Polyflow No. 90, Polyflow No. 95 (trade names, manufactured by Kyoeisha Chemical Industry Co., Ltd.), Disperbyk 161, Disperbyk 162, Disperbyk 163, Disperbyk 164, Disperbyk 166, Disperbyk 170, Disperbyk 180, Disperbyk 181, Disperbyk 182, BYK300, BYK 306, BYK310, BYK320, BYK330, BYK342, BYK344, BYK346 (trade name, manufactured by BYK Japan Co., Ltd.), KP-341, KP-358, KP-368, KF-96-50CS, KF-50-100CS (trade name, manufactured by Shin-Etsu Chemical Co., Ltd.), Surflon SC-101, Surflon KH-40 (trade name, manufactured by Seimi Chemical Co., Ltd.), Ftergent 222F, Ftergent 251, FTX-218 (trade name, manufactured by Neos Co., Ltd.), EFTOP EF-351, EFTOP EF-352, EFTOP EF-601, EFTOP EF-801, EFTOPEF-802 (product name, manufactured by Mitsubishi Materials Corporation), Megafac F-470, Megafac F-471, Megafac F-475, Megafac R-08, Megafac F-477, Megafac F-479, Megafac F-553, Megafac F-554 (product name, manufactured by DIC Corporation), fluoroalkylbenzenesulfonates, fluoroalkylcarboxylates, fluoroalkylpolyoxyethyleneethers, fluoroalkylammonium iodides, fluoroalkylbetaines, fluoroalkylsulfonates, diglycerol tetrakis (fluoroalkylpolyoxyethyleneether), fluoroalkyltrimethylammonium salts, fluoroalkylaminosulfonates, polyoxyethylene nonyl Examples of the alkyl ethers include polyoxyethylene octylphenyl ether, polyoxyethylene alkyl ethers, polyoxyethylene laurate, polyoxyethylene oleate, polyoxyethylene stearate, polyoxyethylene laurylamine, sorbitan laurate, sorbitan palmitate, sorbitan stearate, sorbitan oleate, sorbitan fatty acid esters, polyoxyethylene sorbitan laurate, polyoxyethylene sorbitan palmitate, polyoxyethylene sorbitan stearate, polyoxyethylene sorbitan oleate, polyoxyethylene naphthyl ether, alkyl benzene sulfonates, and alkyl diphenyl ether disulfonates.

[0458] The surfactant may be used alone or in combination of two or more kinds.

[0459] <Composition and Properties of the Organic Layer-Forming Composition> The content of each component in the composition for forming an organic layer is determined in consideration of the good solubility, storage stability and film-forming property of each component in the composition for forming an organic layer, the good film quality of the coating film obtained from the composition for forming an organic layer, the good discharge property when using an inkjet method, and the good electrical properties, light-emitting properties, efficiency and life of an organic EL element having an organic layer produced using the composition. For example, in the case of a composition for forming an emitting layer, it is preferable that the first component is 0.0001% by weight to 2.0% by weight based on the total weight of the composition for forming an emitting layer, the second component is 0.0999% by weight to 8.0% by weight based on the total weight of the composition for forming an emitting layer, and the third component is 90.0% by weight to 99.9% by weight based on the total weight of the composition for forming an emitting layer.

[0460] More preferably, the first component is 0.005% by weight to 1.0% by weight, the second component is 0.095% by weight to 4.0% by weight, and the third component is 95.0% by weight to 99.9% by weight, based on the total weight of the composition for forming the light-emitting layer. Even more preferably, the first component is 0.05% by weight to 0.5% by weight, the second component is 0.25% by weight to 2.5% by weight, and the third component is 97.0% by weight to 99.7% by weight, based on the total weight of the composition for forming the light-emitting layer.

[0461] The composition for forming an organic layer can be produced by appropriately selecting the above-mentioned components and subjecting them to stirring, mixing, heating, cooling, dissolving, dispersing, etc., by a known method. After preparation, filtration, degassing (also called degassing), ion exchange treatment, and inert gas replacement / filling treatment, etc. may be appropriately selected.

[0462] The higher the viscosity of the composition for forming an organic layer, the better the film-forming properties and the better the ejection properties when using an inkjet method. On the other hand, the lower the viscosity, the easier it is to form a thin film. For this reason, the viscosity of the composition for forming an organic layer at 25°C is preferably 0.3 to 3 mPa·s, and more preferably 1 to 3 mPa·s. In the present invention, the viscosity is a value measured using a cone-plate type rotational viscometer (cone-plate type).

[0463] The lower the surface tension of the composition for forming an organic layer, the better the film-forming properties and the more defect-free the coating film will be. On the other hand, the higher the surface tension, the better the ink-jet ejection properties will be. For this reason, the composition for forming an organic layer preferably has a surface tension at 25° C. of 20 to 40 mN / m, more preferably 20 to 30 mN / m. In the present invention, the surface tension is a value measured using the hanging drop method.

[0464] <Crosslinkable polymer compound: Compound represented by general formula (XLP-1)> Next, the case where the above-mentioned polymer compound has a crosslinkable substituent will be described. Such a crosslinkable polymer compound is, for example, a compound represented by the following general formula (XLP-1). [ka] In formula (XLP-1), MUx, ECx and k are defined the same as MU, EC and k in the above formula (H3), except that the compound represented by formula (XLP-1) has at least one crosslinkable substituent (XLS), and preferably the content of the monovalent or divalent aromatic compound having a crosslinkable substituent is 0.1 to 80% by weight in the molecule.

[0465] The content of the monovalent or divalent aromatic compound having a crosslinkable substituent is preferably from 0.5 to 50% by weight, more preferably from 1 to 20% by weight.

[0466] The crosslinkable substituent (XLS) is not particularly limited as long as it is a group that can further crosslink the above-mentioned polymer compound, but substituents having the following structures are preferred: In each structural formula, * indicates the bond position. [ka]

[0467] Each L is independently a single bond, -O-, -S-, >C=O, -OC(=O)-, an alkylene having 1 to 12 carbon atoms, an oxyalkylene having 1 to 12 carbon atoms, or a polyoxyalkylene having 1 to 12 carbon atoms. Among the above substituents, a group represented by formula (XLS-1), formula (XLS-2), formula (XLS-3), formula (XLS-9), formula (XLS-10) or formula (XLS-17) is preferred, and a group represented by formula (XLS-1), formula (XLS-3) or formula (XLS-17) is more preferred.

[0468] Examples of the divalent aromatic compound having a crosslinkable substituent include compounds having the following partial structures: In the following structural formula, * indicates the bonding position. [ka] [ka] [ka] [ka]

[0469] <Methods of producing polymer compounds and crosslinkable polymer compounds> The manufacturing method of the polymer compound and the crosslinkable polymer compound will be described with reference to the compound represented by the above formula (H3) and the compound represented by (XLP-1). These compounds can be synthesized by appropriately combining known manufacturing methods.

[0470] The solvent used in the reaction includes aromatic solvents, saturated / unsaturated hydrocarbon solvents, alcohol solvents, ether solvents, and the like, such as dimethoxyethane, 2-(2-methoxyethoxy)ethane, 2-(2-ethoxyethoxy)ethane, and the like.

[0471] The reaction may be carried out in a two-phase system. When the reaction is carried out in a two-phase system, a phase transfer catalyst such as a quaternary ammonium salt may be added, if necessary.

[0472] The compound of formula (H3) and the compound of formula (XLP-1) may be produced in one step or in multiple steps. The compound may be produced by a batch polymerization method in which all the raw materials are put into a reaction vessel and then the reaction is started, a dropwise polymerization method in which the raw materials are added dropwise to a reaction vessel, or a precipitation polymerization method in which the product precipitates as the reaction proceeds, and these methods can be combined appropriately to synthesize the compound. For example, when the compound of formula (H3) is synthesized in one step, the target product is obtained by carrying out a reaction in a state in which the monomer unit (MU) and the end cap unit (EC) are added to a reaction vessel. When the compound of formula (H3) is synthesized in multiple steps, the target product is obtained by polymerizing the monomer unit (MU) to the target molecular weight, and then adding the end cap unit (EC) and reacting it. If different types of monomer units (MU) are added and reacted in multiple steps, a polymer having a concentration gradient in the structure of the monomer unit can be produced. After preparing a precursor polymer, the target polymer can be obtained by a subsequent reaction.

[0473] In addition, the primary structure of the polymer can be controlled by selecting the polymerizable group of the monomer unit (MU). For example, as shown in synthesis schemes 1 to 3, it is possible to synthesize a polymer having a random primary structure (synthetic scheme 1) or a polymer having a regular primary structure (synthetic schemes 2 and 3), and these can be used in appropriate combination depending on the target object. Furthermore, by using a monomer unit having three or more polymerizable groups, it is possible to synthesize a hyperbranched polymer or a dendrimer.

[0474] [ka]

[0475] Examples of monomer units that can be used in the present invention include those described in JP2010-189630A, WO2012 / 086671A, WO2013 / 191088A, WO2002 / 045184A, WO2011 / 049241A, WO2013 / 146806A, WO2005 / 049546A, WO2015 / 14 It can be synthesized in accordance with the methods described in JP-A-2002 / 045184, JP-A-2010-215886, JP-A-2008-106241, JP-A-2010-215886, WO 2016 / 031639, JP-A-2011-174062, WO 2016 / 031639, WO 2016 / 031639, and WO 2002 / 045184.

[0476] In addition, specific polymer synthesis procedures are described in JP 2012-036388 A, WO 2015 / 008851 A, JP 2012-36381 A, JP 2012-144722 A, WO 2015 / 194448 A, WO 2013 / 146806 A, WO 2015 / 145871 A, WO 2016 / It can be synthesized in accordance with the methods described in WO 2016 / 031639, WO 2016 / 125560, WO 2016 / 031639, WO 2016 / 031639, WO 2016 / 125560, WO 2015 / 145871, WO 2011 / 049241, and JP 2012-144722 A.

[0477] <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. 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.

[0478] 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 matrix and segment methods. Note that matrix display and segment display may coexist in the same panel.

[0479] 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.

[0480] 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.

[0481] 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.

[0482] 3-2. Other organic devices The polycyclic aromatic compound according to the present invention can be used for producing the organic electroluminescent device described above, as well as an organic field effect transistor or an organic thin-film solar cell.

[0483] 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.

[0484] 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.

[0485] 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

[0486] The present invention will be described in detail below with reference to examples, but the present invention is not limited to these examples in any way.

[0487] <Synthesis examples of compounds> First, synthesis examples of the compounds of the present invention will be described below.

[0488] Synthesis Example (1): Synthesis of Compound (1-1627) [ka]

[0489] The structure of 3-bromo-2,4-di(3-chlorophenoxy)pyridine was confirmed by NMR measurement. 1 H-NMR (500MHz, CDCl 3 ): δ=6.43(d,J=5.2Hz,1H), 7.04(dd,J=2.3,8.0Hz,1H), 7.10(dd,J=2.3,8.3Hz,1H), 7.16(t,J =1.7Hz,1H), 7.20-7.29(m,3H),7.35(t,J=8.0Hz,1H),7.38(t,8.0Hz,1H),7.92(d,5.7Hz,1H) 13 C-NMR (126MHz, CDCl 3 ):δ=97.7(1C),108.2(1C),118.6(1C),119.7(1C),120.9(1C),122.0(1C),125.3(1C),125.9(1C),130 .2(1C),131.0(1C),134.8(1C),135.5(1C),146.4(1C),154.2(1C),154.8(1C),161.4(1C),163.2(1C).

[0490] Under a nitrogen atmosphere, a flask containing 3-bromo-2,4-di(3-chlorophenoxy)pyridine (3.29 mg, 8.0 mmol) and mesitylene (40 ml) was cooled to -30°C, n-butyllithium (5.61 ml, 1.57 M, 8.8 mmol) was added dropwise over 10 minutes, and the mixture was stirred at -30°C for 30 minutes. Boron tribromide (817 μl, 8.8 mmol) was added dropwise at -30°C, and the reaction solution was warmed to room temperature and then stirred for 2 hours. Then, low boiling components in the reaction solution were distilled off under reduced pressure. 2,6-di-tert-butylpyridine (970 μl, 4.4 mmol) was added at room temperature, and the mixture was warmed to 170°C and stirred for 6 hours. The reaction solution was allowed to cool to room temperature, and then poured into a saturated aqueous sodium bicarbonate solution, and the aqueous layer was extracted with dichloromethane. The resulting organic layer was washed with saturated saline and dried over anhydrous magnesium sulfate. This solution was concentrated under reduced pressure, and the resulting solid was washed with acetonitrile and then with methanol, yielding compound (1-1627), 3,11-dichloro-5,9-dioxa-6-aza-13b-boranaphtho[3,2,1-de]anthracene, as a white solid (515 mg, 19% yield). [ka]

[0491] The structure of the obtained compound was confirmed by NMR measurement. 1 H-NMR(500MHz,DMSO-d6):δ=7.00(d,J=5.7Hz,1H),7.25(dd,J=2.3,8.0Hz,1H),7.27(dd,J=2.3,8.0Hz,1H) ,7.31(d,J=2.3Hz,1H),7.32(d,J=2.3Hz,1H),8.09(d,J=8.0,1H),8.12(d,J=8.0,1H),8.17(d,J=5.7,1H). 13C-NMR(126MHz,DMSO-d6):δ=107.3(1C),117.0(1C),117.1(1C),123.3(1C),123.7(1C),132.6(1C) ,132.7(1C),134.4(1C),134.7(1C),148.1(1C),157.7(1C),158.6(1C),163.7(1C),164.2(1C),The NMR signal of carbon to the boron was not observable.. 11 B-NMR(160MHz,DMSO-d6):δ=-5.6.

[0492] Synthesis Example (2): Synthesis of Compound (1-1618) [ka]

[0493] In a nitrogen atmosphere, a flask containing compound (1-1627) (102 mg, 0.30 mmol), carbazole (110 mg, 0.66 mmol), bis(di-tert-butyl(3-methylbut-2-en-1-yl)phosphine)dichloropalladium(II) (10.9 mg, 0.018 mmol), sodium-tert-butoxide (63.4 mg, 0.66 mmol), and mesitylene (1.5 ml) was heated to 140° C. and stirred for 6 hours. The reaction solution was allowed to cool to room temperature, then poured into water, and the aqueous layer was extracted with dichloromethane. The resulting organic layer was washed with saturated saline and dried over anhydrous magnesium sulfate. This solution was concentrated under reduced pressure, and the residue was washed with acetonitrile by heating, and then purified with a silica gel short-pass column (eluent: dichloromethane / ethyl acetate = 1 / 1 (volume ratio)). Furthermore, by washing with ethyl acetate and dichloroethane under heating, 3,11-di(9H-carbazo-9-yl)-5,9-dioxa-6-aza-13b-boranaphtho[3,2,1-de]anthracene, compound (1-1618), was obtained as a yellow solid (94.8 mg, yield 53%). [ka]

[0494] The structure of the obtained compound was confirmed by NMR measurement. 1 H-NMR (500MHz, CDCl 3 ):δ=7.31(d,J=5.7Hz,1H), 7.37(dt,J=3.4,7.5Hz,4H), 7.47-7.52(m,4H), 7.70(t,J=8.6Hz,4H), 7.80(dt,J=2.3,8.0Hz,2H), 7.94(d ,J=2.3Hz,1H), 8.04(d,J=2.3Hz,1H), 8.20(dd,J=3.4,7.5Hz,4H),8.76(d,J=5.7Hz,1H),8.96(d,J=8.0Hz,1H),8.98(d,J=8.0Hz,1H).

[0495] Synthesis Example (3): Synthesis of Compound (1-1605) [ka]

[0496] Under a nitrogen atmosphere, compound (1-1627) (67.9 mg, 0.20 mmol), 3-biphenylboronic acid (95.1 mg, 0.48 mmol), bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II) ((AMPhos) 2 PdCl 2A flask containing 3,11-di([1,1'-biphenyl]-3-yl)-5,9-dioxa-6-aza-13b-boranaphtho[3,2,1-de]anthracene (1-1605) was heated and refluxed for 4 hours. The reaction solution was cooled to room temperature, poured into water, and the aqueous layer was extracted with dichloromethane. The organic layer was washed with saturated saline and dried over anhydrous magnesium sulfate. The solution was concentrated under reduced pressure, and the residue was purified with a silica gel short-path column (eluent: dichloromethane / ethyl acetate = 1 / 1 (volume ratio)). The compound (1-1605), which is 3,11-di([1,1'-biphenyl]-3-yl)-5,9-dioxa-6-aza-13b-boranaphtho[3,2,1-de]anthracene, was obtained as a white solid (91.7 mg, 80% yield). [ka]

[0497] The structure of the obtained compound was confirmed by NMR measurement. 1 H-NMR (500MHz, CDCl 3 ):δ=7.25(d,J=5.7Hz,1H),7.39-7.44(m,2H),7.51(t,J=8.2Hz,4H),7. 62(t,7.5Hz,2H),7.67-7.72(m,6H),7.76(d,7.5Hz,2H),7.80(dt,1.7,8 .0Hz,2H),7.93(d,J=1.7Hz,1H),7.99(d,J=1.7Hz,2H),8.02(d,1.7Hz,1H),8.71(d,J=5.7Hz,1H),8.80(d,J=8.0Hz,1H),8.82(d,J=8.0Hz,1H).

[0498] Synthesis Example (4): Synthesis of Compound (1-1603) [ka]

[0499] Under a nitrogen atmosphere, compound (1-1627) (67.9 mg, 0.20 mmol), 2-biphenylboronic acid (95.2 mg, 0.48 mmol), (AMPhos) 2 PdCl 2 A flask containing 1,2-dichloromethane (8.7 mg, 0.012 mmol), tripotassium phosphate (203 mg, 0.96 mmol), and 1,4-dioxane (2.0 ml) is heated under reflux and stirred for 4 hours. After cooling the reaction solution to room temperature, it is poured into water and the aqueous layer is extracted with dichloromethane. The resulting organic layer is washed with saturated saline and dried over anhydrous magnesium sulfate. The solution is concentrated under reduced pressure, and the residue is purified with a silica gel short-path column (eluent: dichloromethane / ethyl acetate = 1 / 1 (volume ratio)). Further, by washing with acetonitrile under heating, 3,11-di([1,1'-biphenyl]-2-yl)-5,9-dioxa-6-aza-13b-boranaphtho[3,2,1-de]anthracene, compound (1-1603), is obtained as a white solid. [ka]

[0500] Synthesis Example (5): Synthesis Example of Compound (1-382) Compound (1-382) is obtained in the same manner as in Synthesis Example 1, except that the n-butyllithium hexane solution is changed to a t-butyllithium hexane solution. [ka]

[0501] By appropriately changing the raw material compounds, other compounds of the present invention can be synthesized according to the methods of the above-mentioned synthesis examples.

[0502] <Effectiveness of the compound as a dopant and its oxidation stability> The structure of the TADF-active light-emitting material was designed using DFT calculations. After the ground state structure was optimized using the PBE0 / 6-31G(d) method, the vertical excitation energy from the ground state was calculated using the time-dependent DFT method. All calculations were performed using the quantum chemical calculation program Firefly (AA Granovsky, Firefly version 8).

[0503] When used as a blue fluorescent dopant or TADF dopant, the emission wavelength and ΔE ST It is important to consider the following. One of the causes of deterioration of organic EL elements is oxygen that has been mixed into the element, and it is known that the higher the HOMO of a compound, the more likely it is to undergo oxidation reactions due to oxygen. Therefore, the HOMO value is useful for evaluating the oxidative stability of a compound. First, these properties were calculated using a compound that does not contain a pyridine nitrogen, as in the structural formula below, as a comparison compound. [ka]

[0504] For the above comparative compound, emission wavelength = 382 nm, ΔE ST The calculated results were ΔE = 0.537 and HOMO = -4.985 eV. Therefore, in the calculation example of the compound into which pyridine nitrogen has been introduced, if the emission wavelength is made shorter than that of the comparative compound, it is evaluated as being effective as a fluorescent dopant, and ΔE ST A smaller HOMO was evaluated as being effective as a TADF dopant, and a lower HOMO was evaluated as being excellent in oxidation stability.

[0505] The following compounds were evaluated as compounds of the present invention having pyridinic nitrogen introduced therein. [ka] The above compounds (1-401-ph), (1-441-ph), (1-481-ph), (1-521-ph), (1-561-ph) and (1-601-ph) are compounds in which >NR (R = pyridyl or pyrimidyl) in the above compounds (1-401), (1-441), (1-481), (1-521), (1-561) and (1-601) have been replaced with >NR (R = phenyl). It has been confirmed that the difference between this phenyl group and the pyridyl or pyrimidyl group does not affect the calculation results.

[0506] <Calculation Example 1-1> For compound (1-1), the emission wavelength is 332 nm, ΔE ST =0.565 eV, which is expected to be an effective fluorescent dopant. In addition, the HOMO is -5.804 eV, which is expected to have excellent oxidation stability.

[0507] <Calculation Example 1-2> For compound (1-401-ph), emission wavelength = 400 nm, ΔE ST =0.513 eV, which is expected to be effective as a TADF dopant. In addition, the HOMO is -5.287 eV, which is expected to have excellent oxidation stability.

[0508] <Calculation Example 1-3> For compound (1-441-ph), the emission wavelength is 363 nm, ΔE ST =0.514 eV, which is expected to be effective as a fluorescent dopant and TADF dopant. In addition, the HOMO is -5.540 eV, which is expected to have excellent oxidation stability.

[0509] <Calculation Example 1-4> For compound (1-481-ph), emission wavelength = 380 nm, ΔE STIt was estimated to be 0.49 eV and was expected to be effective as a fluorescent dopant and a TADF dopant. Also, the HOMO was -5.851 eV, and it was expected to have excellent oxidation stability.

[0510] <Calculation Example 1-5> In compound (1-521-ph), the emission wavelength = 313 nm, ΔE ST was estimated to be 0.625 eV and was expected to be effective as a fluorescent dopant. Also, the HOMO was -6.465 eV, and it was expected to have excellent oxidation stability.

[0511] <Calculation Example 1-6> In compound (1-561-ph), the emission wavelength = 337 nm, ΔE ST was estimated to be 0.589 eV and was expected to be effective as a fluorescent dopant. Also, the HOMO was -6.180 eV, and it was expected to have excellent oxidation stability.

[0512] <Calculation Example 1-7> In compound (1-601-ph), the emission wavelength = 325 nm, ΔE ST was estimated to be 0.474 eV and was expected to be effective as a fluorescent dopant and a TADF dopant. Also, the HOMO was -6.827 eV, and it was expected to have excellent oxidation stability.

[0513] The polycyclic aromatic compound of the present invention having pyridinic nitrogen, which is an electron-withdrawing element, in the molecule has a low HOMO level and is more stable to oxygen. Therefore, an organic EL element produced using the compound has a longer lifespan.

[0514] <Neat Film Evaluation Example> The neat films of several compounds were evaluated. Compound (1-382) has a small ΔE(ST) compared to compound (ref_BN2), so it is promising as a TADF dopant. Compounds (1-1627) and (1-1618) have high Ip, Ea, S1, and T1 compared to compound (ref_BO2), so they are promising as hole-blocking materials (hole-stopping materials) and electron transport materials.

Table 1

Chemical Structure

[0515] <Prediction of Physical Property Values of Compounds by DFT Calculation> The physical property values of the compounds of this application were predicted using DFT calculations. After performing ground-state structure optimization using B3LYP / 6-31G(d), the vertical excitation energy from the ground state was calculated using the time-dependent DFT method. All calculations were performed using the quantum chemistry calculation program Gaussian 09 (J.M. Frisch, et al., Revision C.01.).

[0516] When comparing compound (calc_ref) with compounds (1-1601) and (1-841), compounds (1-1601) and (1-841) have higher S1, higher T1, deeper HOMO, and deeper LUMO. Therefore, the compounds of the present invention are promising as hole-blocking materials (hole-stopping materials) and electron transport materials. In addition, since compound (1-841) has a smaller ΔE(ST) than compound (calc_ref), it is also promising as a blue TADF assist dopant.

Table 2

Chemical Structure

[0517] <Evaluation of Solution-Processed Organic EL Devices> Next, an organic EL device obtained by forming an organic layer by coating will be described.

[0518] <Synthesis of polymer host compound: SPH-101> SPH-101 was synthesized according to the method described in International Publication No. 2015 / 008851. A copolymer was obtained in which M2 or M3 was bonded next to M1, and the ratio of each unit was estimated to be 50:26:24 (molar ratio) based on the feed ratio. [ka]

[0519] <Synthesis of polymer hole transport compound: XLP-101> XLP-101 was synthesized according to the method described in JP 2018-61028 A. A copolymer in which M5 or M6 was bonded next to M4 was obtained, and it is estimated from the feed ratio that each unit is 40:10:50 (molar ratio). [ka]

[0520] <Examples 2-1 to 2-8> A coating solution of the material for forming each layer is prepared to fabricate a coating type organic EL device.

[0521] <Preparation of Organic EL Devices of Examples 2-1 to 2-3> Table 3 shows the material composition of each layer in the organic EL element. [Table 3]

[0522] The structure of "ET1" in Table 3 is shown below. [ka]

[0523] <Preparation of composition for forming light-emitting layer (1)> The luminescent layer forming composition (1) is prepared by stirring the following components until a homogeneous solution is obtained. The prepared luminescent layer forming composition is spin-coated on a glass substrate and dried by heating under reduced pressure, whereby a coating film without film defects and excellent in smoothness can be obtained. Compound (A) 0.04 wt% SPH-101 1.96 wt% Xylene 69.00 wt% Decalin 29.00 wt%

[0524] Compound (A) is a polycyclic aromatic compound represented by the above general formula (1), a multimer thereof, a polymer compound obtained by polymerizing the polycyclic aromatic compound or its multimer as a monomer (i.e., the monomer has a reactive substituent), a polymer crosslinked body obtained by further crosslinking the polymer compound, a pendant polymer compound obtained by substituting the monomer into a main chain polymer, or a pendant polymer crosslinked body obtained by further crosslinking the pendant polymer compound. The polymer compound or pendant polymer compound for obtaining the polymer crosslinked body or pendant polymer crosslinked body has a crosslinkable substituent.

[0525] <PEDOT:PSS solution> A commercially available PEDOT:PSS solution (Clevios(TM) P VP AI4083, an aqueous dispersion of PEDOT:PSS, manufactured by Heraeus Holdings) is used.

Chemical formula

[0526] <Preparation of OTPD solution> OTPD (LT-N159, manufactured by Luminescence Technology Corp) and IK-2 (a photo cationic polymerization initiator, manufactured by San-Apro) are dissolved in toluene to prepare an OTPD solution with an OTPD concentration of 0.7 wt% and an IK-2 concentration of 0.007 wt%.

Chemical formula

[0527] <Preparation of XLP-101 Solution> Dissolve XLP-101 in xylene at a concentration of 0.6% by weight to prepare a 0.7% by weight XLP-101 solution.

[0528] <Preparation of PCz Solution> Dissolve PCz (polyvinylcarbazole) in dichlorobenzene to prepare a 0.7% by weight PCz solution.

Chemical formula

[0529] <Example 2-1> On a glass substrate with ITO vapor-deposited to a thickness of 150 nm, spin-coat the PEDOT:PSS solution and bake it on a hot plate at 200 °C for 1 hour to form a PEDOT:PSS film with a thickness of 40 nm (hole injection layer). Next, spin-coat the OTPD solution, dry it on a hot plate at 80 °C for 10 minutes, then expose it with an exposure intensity of 100 mJ / cm 2 and bake it on a hot plate at 100 °C for 1 hour to form an OTPD film with a thickness of 30 nm that is insoluble in the solution (hole transport layer). Next, spin-coat the composition (1) for forming the light-emitting layer and bake it on a hot plate at 120 °C for 1 hour to form a light-emitting layer with a thickness of 20 nm.

[0530] Fix the fabricated multilayer film to the substrate holder of a commercially available vapor deposition apparatus (manufactured by Showa Vacuum Co., Ltd.), and attach a molybdenum vapor deposition boat containing ET1, a molybdenum vapor deposition boat containing LiF, and a tungsten vapor deposition boat containing aluminum. After evacuating the vacuum chamber to 5×10 -4 Pa, heat ET1 and deposit it at a deposition rate of 1 nm / second to a thickness of 30 nm to form an electron transport layer. The deposition rate when forming the electron transport layer is set to 1 nm / second. Then, heat LiF and deposit it at a deposition rate of 0.01 - 0.1 nm / second to a thickness of 1 nm. Next, heat aluminum and deposit it to a thickness of 100 nm to form a cathode. In this way, an organic EL element is obtained.

[0531] <Example 2-2> An organic EL device is obtained in the same manner as in Example 2-1. The hole transport layer is formed by spin-coating an XLP-101 solution and baking it on a hot plate at 200° C. for 1 hour to form a film with a thickness of 30 nm.

[0532] <Example 2-3> An organic EL device is obtained in the same manner as in Example 2-1. The hole transport layer is formed by spin-coating a PCz solution and baking it on a hot plate at 120° C. for 1 hour to form a film with a thickness of 30 nm.

[0533] <Preparation of organic EL elements of Examples 2-4 to 2-6> Table 4 shows the material composition of each layer in the organic EL element. [Table 4]

[0534] <Preparation of compositions (2) to (4) for forming light-emitting layer> A composition for forming a light-emitting layer (2) is prepared by stirring the following components until a homogeneous solution is obtained. Compound (A) 0.02% by weight mCBP 1.98 wt% Toluene 98.00% by weight

[0535] The following components are stirred until a homogeneous solution is obtained, thereby preparing a composition (3) for forming a light-emitting layer. Compound (A) 0.02% by weight SPH-101 1.98% by weight Xylene 98.00% by weight

[0536] A composition for forming a light-emitting layer (4) is prepared by stirring the following components until a homogeneous solution is obtained. Compound (A) 0.02% by weight DOBNA 1.98% by weight Toluene 98.00% by weight

[0537] In Table 4, "mCBP" is 3,3'-bis(N-carbazolyl)-1,1'-biphenyl, "DOBNA" is 3,11-di-o-tolyl-5,9-dioxa-13b-boranaphtho[3,2,1-de]anthracene, and "TSPO1" is diphenyl[4-(triphenylsilyl)phenyl]phosphine oxide. The chemical structures are shown below. [ka]

[0538] <Example 2-4> A glass substrate on which an ITO film is formed to a thickness of 45 nm is spin-coated with an ND-3202 (Nissan Chemical Industries) solution, and then heated in an air atmosphere at 50°C for 3 minutes, and then heated at 230°C for 15 minutes to form a 50 nm thick ND-3202 film (hole injection layer). Next, an XLP-101 solution is spin-coated, and heated on a hot plate in a nitrogen gas atmosphere at 200°C for 30 minutes to form a 20 nm thick XLP-101 film (hole transport layer). Next, a composition for forming an emitting layer (2) is spin-coated, and heated in a nitrogen gas atmosphere at 130°C for 10 minutes to form a 20 nm thick emitting layer.

[0539] The prepared multilayer film is fixed to the substrate holder of a commercially available deposition device (Showa Vacuum Co., Ltd.), and a molybdenum deposition boat containing TSPO1, a molybdenum deposition boat containing LiF, and a tungsten deposition boat containing aluminum are installed. The vacuum chamber is heated to 5×10 -4 After reducing the pressure to 1 Pa, TSPO1 is heated and evaporated to a thickness of 30 nm to form an electron transport layer. The evaporation rate for forming the electron transport layer is 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. Next, aluminum is heated and evaporated to a thickness of 100 nm to form a cathode. In this manner, an organic EL device is obtained.

[0540] <Examples 2-5 and 2-6> An organic EL element is obtained by using the composition for forming a light-emitting layer (3) or (4) in the same manner as in Example 2-4.

[0541] <Preparation of Organic EL Devices of Examples 2-7 to 2-9> Table 5 shows the material composition of each layer in the organic EL element. [Table 5]

[0542] <Preparation of compositions (5) to (7) for forming light-emitting layer> A composition for forming a light-emitting layer (5) is prepared by stirring the following components until a homogeneous solution is obtained. Compound (A) 0.02% by weight 2PXZ-TAZ 0.18% by weight mCBP 1.80% by weight Toluene 98.00% by weight

[0543] A composition for forming a light-emitting layer (6) is prepared by stirring the following components until a homogeneous solution is obtained. Compound (A) 0.02% by weight 2PXZ-TAZ 0.18% by weight SPH-101 1.80% by weight Xylene 98.00% by weight

[0544] A composition for forming a light-emitting layer (7) is prepared by stirring the following components until a homogeneous solution is obtained. Compound (A) 0.02% by weight 2PXZ-TAZ 0.18% by weight DOBNA 1.80% by weight Toluene 98.00% by weight

[0545] In Table 5, "2PXZ-TAZ" is 10,10'-((4-phenyl-4H-1,2,4-triazole-3,5-diyl)bis(4,1-phenyl))bis(10H-phenoxazine). The chemical structure is shown below. [ka]

[0546] <Example 2-7> A glass substrate on which an ITO film is formed to a thickness of 45 nm is spin-coated with an ND-3202 (Nissan Chemical Industries) solution, and then heated at 50°C for 3 minutes in an air atmosphere, and then heated at 230°C for 15 minutes to form a 50 nm thick ND-3202 film (hole injection layer). Next, an XLP-101 solution is spin-coated, and heated on a hot plate at 200°C for 30 minutes in a nitrogen gas atmosphere to form a 20 nm thick XLP-101 film (hole transport layer). Next, a composition for forming an emitting layer (5) is spin-coated, and heated at 130°C for 10 minutes in a nitrogen gas atmosphere to form a 20 nm thick emitting layer.

[0547] The prepared multilayer film is fixed to the substrate holder of a commercially available deposition device (Showa Vacuum Co., Ltd.), and a molybdenum deposition boat containing TSPO1, a molybdenum deposition boat containing LiF, and a tungsten deposition boat containing aluminum are installed. The vacuum chamber is heated to 5×10 -4 After reducing the pressure to 1 Pa, TSPO1 is heated and evaporated to a thickness of 30 nm to form an electron transport layer. The evaporation rate for forming the electron transport layer is 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. Next, aluminum is heated and evaporated to a thickness of 100 nm to form a cathode. In this manner, an organic EL device is obtained.

[0548] <Examples 2-8 and 2-9> An organic EL device is obtained using the composition for forming a light emitting layer (6) or (7) in the same manner as in Example 2-7. [Industrial Applicability]

[0549] In the present invention, by providing a novel polycyclic aromatic compound, it is possible to increase the options of materials for organic electroluminescence devices. In addition, by using the novel polycyclic aromatic compound as a material for organic electroluminescence devices, it is possible to provide an excellent organic electroluminescence device, a display device including the same, and a lighting device including the same. [Explanation of symbols]

[0550] 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 general formula (1), excluding compounds of the following formulae A117, A121, and A135. 【Chemistry 1】 【Chemistry 2】 In the above formula (1), R １ , R ２ , R ３ , R ４ and R ５ each independently represents a hydrogen atom, an aryl having 6 to 20 carbon atoms, a heteroaryl having 2 to 15 carbon atoms, a diarylamino (wherein each aryl has 6 to 12 carbon atoms), an alkyl having 1 to 12 carbon atoms, a cycloalkyl having 3 to 16 carbon atoms, an alkoxy having 1 to 12 carbon atoms, or an aryloxy having 6 to 20 carbon atoms, in which at least one hydrogen atom may be further substituted by an aryl having 6 to 20 carbon atoms, a heteroaryl having 2 to 15 carbon atoms, an alkyl having 1 to 12 carbon atoms, or a cycloalkyl having 3 to 16 carbon atoms; X １ and X ２ are each independently >N-R Ｎ or >O, The R Ｎ each independently represents a hydrogen atom, an aryl having 6 to 20 carbon atoms, a heteroaryl having 2 to 15 carbon atoms, a diarylamino (wherein each aryl has 6 to 12 carbon atoms), an alkyl having 1 to 12 carbon atoms, a cycloalkyl having 3 to 16 carbon atoms, an alkoxy having 1 to 12 carbon atoms, or an aryloxy having 6 to 20 carbon atoms, in which at least one hydrogen atom may be further substituted by an aryl having 6 to 20 carbon atoms, a heteroaryl having 2 to 15 carbon atoms, an alkyl having 1 to 12 carbon atoms, or a cycloalkyl having 3 to 16 carbon atoms; Y １ , Y ２ , Y ３ , Y ４ , Y ５ and Y ６ are each independently =C(-R Ｙ )- or =N- in any combination of the following: ・Y １ and Y ６ is ═N- (ring a is a pyrimidine ring, ring b and ring c are benzene rings), ・Y １ Or Y ６ is ═N- (ring a is a pyridine ring, ring b and ring c are benzene rings), ・Y ２ and Y ５ is ═N-(ring b and ring c are pyridine rings, ring a is a benzene ring), ・Y ３ and Y ４ is ═N-(ring b and ring c are pyridine rings, ring a is a benzene ring), ・Y ２ ~Y ５ is ═N-(ring b and ring c are pyrimidine rings, ring a is a benzene ring), ・Y １ , Y ３ , Y ４ and Y ６ is ═N- (ring a is a pyrimidine ring, ring b and ring c are pyridine rings), ・Y １ , Y ２ , Y ５ and Y ６ is ═N- (ring a is a pyrimidine ring, ring b and ring c are pyridine rings), ・Y １ ~Y ６ is ═N-(ring a, ring b and ring c are pyrimidine rings), ・Y ２ Or Y ５ is ═N-(ring b or ring c is a pyridine ring, ring a is a benzene ring), The R Ｙ are each independently a hydrogen atom, an aryl having 6 to 20 carbon atoms, a heteroaryl having 2 to 15 carbon atoms, a diarylamino (wherein each aryl has 6 to 12 carbon atoms), an alkyl having 1 to 12 carbon atoms, a cycloalkyl having 3 to 16 carbon atoms, an alkoxy having 1 to 12 carbon atoms, or an aryloxy having 6 to 20 carbon atoms, in which at least one hydrogen atom may be further substituted by an aryl having 6 to 20 carbon atoms, a heteroaryl having 2 to 15 carbon atoms, an alkyl having 1 to 12 carbon atoms, or a cycloalkyl having 3 to 16 carbon atoms, and At least one hydrogen atom in the compound represented by the general formula (1) may be substituted with cyano, halogen or deuterium.

2. Y ２ , Y ３ , Y ４ and Y ５ are each independently =C(-R Ｙ )-, and Y １ and Y ６ are each independently =C(-R Ｙ )- or ═N-, at least one of which is ═N-; The polycyclic aromatic compound according to claim 1.

3. 2. The polycyclic aromatic compound according to claim 1, wherein a part of the formula (1) is a partial structure represented by any one of the following formulas: 【Chemistry 3】 【Chemistry 4】

4. A polycyclic aromatic compound represented by any one of the following formulas: 【Chemistry 5】 【Chemistry 6】 【Chemistry 7】

5. A material for an organic device, comprising the polycyclic aromatic compound according to any one of claims 1 to 4.

6. The material for an organic device according to claim 5 , 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.

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

8. 5. An ink composition comprising the polycyclic aromatic compound according to claim 1 and an organic solvent.

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

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

11. The organic electroluminescent device according to claim 10, wherein the light-emitting layer further contains at least one selected from the group consisting of a compound represented by the following general formula (H1), a compound represented by the following general formula (H2), a compound represented by the following general formula (H3), a compound including a structure represented by the following general formula (H4), a compound represented by the following general formula (H5), and a TADF material: 【Chemistry 9】 In the above general formula (H1), L １ is an arylene having 6 to 30 carbon atoms or a heteroarylene having 2 to 30 carbon atoms, In the above general 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; In the above general formula (H3), each MU is independently a divalent group represented by removing any two hydrogen atoms from an aromatic compound, each EC is independently a monovalent group represented by removing any one hydrogen atom from an aromatic compound, two hydrogen atoms in MU are replaced by EC or MU, and k is an integer of 2 to 50,000, In the above general formula (H4), each G is independently =C(-H)- or =N-, and H in the =C(-H)- may be substituted with a substituent or a structure represented by another formula (H4), In the above general formula (H5), R １ ~R １１ are each independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, alkyl or cycloalkyl, at least one hydrogen of which may be further substituted with aryl, heteroaryl, diarylamino, alkyl or cycloalkyl; R １ ~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 or the c ring, and at least one hydrogen in the formed ring may be replaced by an aryl, a heteroaryl, a diarylamino, a diheteroarylamino, an arylheteroarylamino, an alkyl or a cycloalkyl, and at least one hydrogen in these may be further replaced by an aryl, a heteroaryl, a diarylamino, an alkyl or a cycloalkyl, and At least one hydrogen atom in the compound or structure represented by each of the above formulas may be substituted with alkyl having 1 to 6 carbon atoms, cycloalkyl having 3 to 14 carbon atoms, cyano, halogen or deuterium.

12. 12. The organic electroluminescence device according to claim 10, further comprising at least one of an electron transport layer and an electron injection layer disposed between the cathode and the light emitting layer, 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, carbazole derivatives, triazine derivatives, benzimidazole derivatives, phenanthroline derivatives, and quinolinol-based metal complexes.

13. 13. The organic electroluminescent device according to claim 12, 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.

14. A display device or a lighting device comprising the organic electroluminescent device according to any one of claims 9 to 13.

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