Cycloalkane-condensed polycyclic aromatic compound

Abstract

To provide a material for providing an organic EL element having excellent luminous efficiency and element life.SOLUTION: Provided is a polycyclic aromatic compound represented by the following general formula (1) or a multimer of polycyclic aromatic compounds, comprising a plurality of structures represented by the following general formula (1). (In the formula (1), ring A, ring B and ring C are each an aryl ring or a heteroaryl ring; Y1 is B, P, P=O, P=S or the like; X1 and X2 are each >O, >N-R or the like, where R in >N-R is aryl or the like; and at least one of the rings in the compound or the structure represented by formula (1) is condensed with at least one cycloalkane, where at least one hydrogen in the cycloalkane may be substituted and at least one -CH2- in the cycloalkane may be substituted with -O-.)SELECTED DRAWING: None

Description

[Technical field]

[0001] The present invention relates to a cycloalkane-fused polycyclic aromatic compound and a multimer thereof (hereinafter, also collectively referred to as "polycyclic aromatic compound"), and an organic electroluminescent device, an organic field effect transistor, an organic thin-film solar cell, a display device, and a lighting device using the same. In this specification, the "organic electroluminescent device" may be referred to as an "organic EL device" or simply as an "device". [Background technology]

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

[0003] An organic 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 that has 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 linking a large number of relatively small conjugated aromatic rings ensures the large HOMO-LUMO gap (band gap Eg in a thin film) required for the host material. Furthermore, host materials for organic EL devices that use phosphorescent materials or thermally activated delayed fluorescent materials have high triplet excitation energy (E T ) is also required, but by linking a donor or acceptor aromatic ring or substituent to the molecule, the SOMO1 and SOMO2 in the triplet excited state (T1) are localized, and the exchange interaction between the two orbitals is reduced, allowing the triplet excitation energy (E T) can be improved. However, small aromatic rings in the conjugated system do not have sufficient redox stability, and devices using molecules formed by linking existing aromatic rings as host materials do not have sufficient life spans. On the other hand, polycyclic aromatic compounds with extended π-conjugated systems generally have excellent redox stability, but they have poor HOMO-LUMO gaps (band gaps in thin films, Eg) and triplet excitation energies (E T ) is low, it has been considered unsuitable as a host material. [Prior art documents] [Patent documents]

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

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

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

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

[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), ring A, ring B and ring C are each independently an aryl ring or a heteroaryl ring, and at least one hydrogen atom in these rings may be substituted; Y 1 is B, P, P=O, P=S, Al, Ga, As, Si-R or Ge-R, wherein R of Si-R and Ge-R is aryl, alkyl or cycloalkyl; X 1 and X 2 are each independently >O, >NR, >C(-R)2, >S or >Se, R of the >NR is an optionally substituted aryl, an optionally substituted heteroaryl, an optionally substituted alkyl or an optionally substituted cycloalkyl, R of the >C(-R)2 is a hydrogen atom, an optionally substituted aryl, an optionally substituted alkyl or an optionally substituted cycloalkyl, and at least one of R of the >NR and R of the >C(-R)2 may be bonded to at least one of the A ring, the B ring and the C ring via a linking group or a single bond, At least one hydrogen atom in the compound or structure represented by formula (1) may be replaced with deuterium, cyano or halogen; and In the compound or structure represented by formula (1), at least one of the A ring, the B ring, the C ring, the aryl and the heteroaryl is condensed with at least one cycloalkane, at least one hydrogen in the cycloalkane may be substituted, and at least one -CH2- in the cycloalkane may be substituted with -O-.

[0013] Section 2. In the above formula (1), Ring A, ring B and ring C are each independently an aryl ring or a heteroaryl ring, and at least one hydrogen atom in these rings may be substituted with a substituted or unsubstituted aryl, a substituted or unsubstituted heteroaryl, a substituted or unsubstituted diarylamino, a substituted or unsubstituted diheteroarylamino, a substituted or unsubstituted arylheteroarylamino, a substituted or unsubstituted diarylboryl (two aryls may be bonded via a single bond or a linking group), a substituted or unsubstituted alkyl, a substituted or unsubstituted cycloalkyl, a substituted or unsubstituted alkoxy, a substituted or unsubstituted aryloxy, or a substituted silyl, and these rings may be substituted with Y 1 , X 1 and X 2 A 5- or 6-membered ring shares a bond with the central fused 2-ring structure of the above formula Y 1 is B, P, P=O, P=S, Al, Ga, As, Si-R or Ge-R, wherein R of Si-R and Ge-R is aryl, alkyl or cycloalkyl; X 1 and X 2 are each independently >O, >NR, >C(-R)2, >S or >Se, R of the >NR is aryl which may be substituted with alkyl or cycloalkyl, heteroaryl which may be substituted with alkyl or cycloalkyl, alkyl or cycloalkyl, R of the >C(-R)2 is hydrogen, aryl which may be substituted with alkyl or cycloalkyl, alkyl or cycloalkyl, at least one of R of the >NR and R of the >C(-R)2 may be bonded to at least one of the A ring, the B ring and the C ring by -O-, -S-, -C(-R)2- or a single bond, R of the -C(-R)2- is hydrogen, alkyl or cycloalkyl, At least one hydrogen atom in the compound or structure represented by formula (1) may be replaced by deuterium, cyano or halogen; In the case of a polymer, it is a dimer or trimer having two or three structures represented by general formula (1), and In the compound or structure represented by formula (1), at least one of ring A, ring B, ring C, aryl and heteroaryl is condensed with at least one cycloalkane, at least one hydrogen in the cycloalkane may be substituted, and at least one -CH2- in the cycloalkane may be substituted with -O-; Item 1. A polycyclic aromatic compound or a multimer thereof according to item 1.

[0014] Section 3. Item 3. The polycyclic aromatic compound according to item 1, which is represented by the following general formula (2): [ka] (In the above formula (2), In the ring a, the ring b, and the ring c, any "-C(-R)=" (where R is R in formula (2) 1 ~R 11 ) may be replaced with "-N=", and any "-C(-R)=C(-R)-" (where R is R in formula (2) 1 ~R 11 may be replaced with "-N(-R)-", "-O-", or "-S-", where R in "-N(-R)-" is aryl, alkyl, or cycloalkyl; R 1 ~R 11 are each independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl (two aryls may be bonded via a single bond or a linking group), alkyl, cycloalkyl, alkoxy, aryloxy, triarylsilyl, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, or alkyldicycloalkylsilyl, in which at least one hydrogen may be replaced by an aryl, heteroaryl, alkyl, or cycloalkyl; and R 1 ~R 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 replaced by an aryl, a heteroaryl, a diarylamino, a diheteroarylamino, an arylheteroarylamino, a diarylboryl (two aryls may be bonded via a single bond or a linking group), an alkyl, a cycloalkyl, an alkoxy, an aryloxy, a triarylsilyl, a trialkylsilyl, a tricycloalkylsilyl, a dialkylcycloalkylsilyl or an alkyldicycloalkylsilyl, and at least one hydrogen atom in these may be replaced by an aryl, a heteroaryl, an alkyl or a cycloalkyl; Y 1 is B, P, P=O, P=S, Al, Ga, As, Si-R or Ge-R, and R of the Si-R and Ge-R is an aryl having 6 to 12 carbon atoms, an alkyl having 1 to 6 carbon atoms or a cycloalkyl having 3 to 14 carbon atoms; X 1 and X 2 are each independently >O, >NR, >C(-R)2, >S or >Se, R of the >NR is an aryl having 6 to 12 carbon atoms, a heteroaryl having 2 to 15 carbon atoms, an alkyl having 1 to 6 carbon atoms or a cycloalkyl having 3 to 14 carbon atoms, R of the >C(-R)2 is hydrogen, an aryl having 6 to 12 carbon atoms, an alkyl having 1 to 6 carbon atoms or a cycloalkyl having 3 to 14 carbon atoms, at least one of R of the >NR and R of the >C(-R)2 may be bonded to at least one of the ring a, ring b and ring c via -O-, -S-, -C(-R)2- or a single bond, R of the -C(-R)2- is an alkyl having 1 to 6 carbon atoms or a cycloalkyl having 3 to 14 carbon atoms, At least one hydrogen atom in the compound represented by formula (2) may be replaced by deuterium, cyano or halogen, and In the compound represented by formula (2), at least one of the ring a, the ring b, the ring c, the formed ring, the aryl and the heteroaryl is condensed with at least one cycloalkane having 3 to 24 carbon atoms, at least one hydrogen in the cycloalkane may be substituted with an aryl having 6 to 30 carbon atoms, a heteroaryl having 2 to 30 carbon atoms, an alkyl having 1 to 24 carbon atoms or a cycloalkyl having 3 to 24 carbon atoms, and at least one -CH2- in the cycloalkane may be substituted with -O-.

[0015] Section 4. In the above formula (2), In the ring a, the ring b, and the ring c, any "-C(-R)=" (where R is R in formula (2) 1 ~R 11 ) may be replaced with "-N=", and any "-C(-R)=C(-R)-" (where R is R in formula (2) 1 ~R 11 (which is a radical) may be replaced with "-N(-R)-", "-O-", or "-S-", and R in the "-N(-R)-" is an aryl having 6 to 12 carbon atoms, an alkyl having 1 to 6 carbon atoms, or a cycloalkyl having 3 to 14 carbon atoms; R 1 ~R 11 are each independently hydrogen, 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), a diarylboryl (wherein the aryl is an aryl having 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 24 carbon atoms, a cycloalkyl having 3 to 24 carbon atoms, a triarylsilyl (wherein the aryl is an aryl having 6 to 12 carbon atoms), or a trialkylsilyl (wherein the alkyl is an alkyl having 1 to 6 carbon atoms); and 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 aryl having 6 to 10 carbon atoms, alkyl having 1 to 12 carbon atoms, cycloalkyl having 3 to 16 carbon atoms, triarylsilyl (wherein aryl is 6 to 12 carbon atoms), or trialkylsilyl (wherein alkyl is 1 to 5 carbon atoms); Y 1 is B, P, P=O, P=S or Si-R, wherein R of the Si-R is an aryl having 6 to 10 carbon atoms, an alkyl having 1 to 5 carbon atoms or a cycloalkyl having 5 to 10 carbon atoms; X 1 and X 2 are each independently >O, >NR, >C(-R)2 or >S, R of the >NR is an aryl having 6 to 10 carbon atoms, an alkyl having 1 to 5 carbon atoms or a cycloalkyl having 5 to 10 carbon atoms, and R of the >C(-R)2 is a hydrogen atom, an aryl having 6 to 10 carbon atoms, an alkyl having 1 to 5 carbon atoms or a cycloalkyl having 5 to 10 carbon atoms, At least one hydrogen atom in the compound represented by formula (2) may be replaced by deuterium, cyano or halogen, and In the compound represented by formula (2), at least one of the ring a, the ring b, the ring c, the formed ring, the aryl and the heteroaryl is condensed with at least one cycloalkane having 3 to 20 carbon atoms, and at least one hydrogen in the cycloalkane may be substituted with an aryl having 6 to 16 carbon atoms, a heteroaryl having 2 to 22 carbon atoms, an alkyl having 1 to 12 carbon atoms or a cycloalkyl having 3 to 16 carbon atoms. Item 3. The polycyclic aromatic compound according to item 3.

[0016] Section 5. In the above formula (2), In the ring a, the ring b, and the ring c, any "-C(-R)=" (where R is R in formula (2) 1 ~R 11) may be replaced with "-N=", and any "-C(-R)=C(-R)-" (where R is R in formula (2) 1 ~R 11 (which is a radical) may be replaced with "-N(-R)-", "-O-", or "-S-", and R in the "-N(-R)-" is an aryl having 6 to 10 carbon atoms, an alkyl having 1 to 5 carbon atoms, or a cycloalkyl having 5 to 10 carbon atoms; R 1 ~R 11 each independently represents hydrogen, an aryl having 6 to 16 carbon atoms, a heteroaryl having 2 to 20 carbon atoms, a diarylamino (wherein the aryl has 6 to 10 carbon atoms), an alkyl having 1 to 12 carbon atoms, or a cycloalkyl having 3 to 16 carbon atoms; Y 1 is B, P, P=O or P=S, X 1 and X 2 are each independently >O, >NR or >C(-R)2, R of the >NR is an aryl having 6 to 10 carbon atoms, an alkyl having 1 to 5 carbon atoms or a cycloalkyl having 5 to 10 carbon atoms, and R of the >C(-R)2 is a hydrogen atom, an aryl having 6 to 10 carbon atoms, an alkyl having 1 to 5 carbon atoms or a cycloalkyl having 5 to 10 carbon atoms, At least one hydrogen atom in the compound represented by formula (2) may be replaced by deuterium, cyano or halogen, and In the compound represented by formula (2), at least one of the ring a, the ring b, the ring c, and the aryl having 6 to 10 carbon atoms as R of >NR is condensed with at least one cycloalkane having 3 to 16 carbon atoms, and at least one hydrogen atom in the cycloalkane may be substituted with an alkyl having 1 to 6 carbon atoms or a cycloalkyl having 3 to 14 carbon atoms. Item 3. The polycyclic aromatic compound according to item 3.

[0017] Section 6. R 1 ~R 11each independently represents a hydrogen atom, an aryl having 6 to 16 carbon atoms, a diarylamino (wherein the aryl has 6 to 10 carbon atoms), an alkyl having 1 to 12 carbon atoms, or a cycloalkyl having 3 to 16 carbon atoms; Y 1 is B, X 1 and X 2 are both >NR or X 1 is >NR and X 2 is >O, and R of the >NR is an aryl having 6 to 10 carbon atoms, an alkyl having 1 to 5 carbon atoms, or a cycloalkyl having 5 to 10 carbon atoms, At least one hydrogen atom in the compound represented by formula (2) may be replaced by deuterium or halogen, and In the compound represented by formula (2), at least one of the ring a, the ring b, the ring c, and the aryl having 6 to 10 carbon atoms as R of >NR is condensed with a cycloalkane having 3 to 14 carbon atoms, and at least one hydrogen atom in the cycloalkane may be substituted with an alkyl having 1 to 5 carbon atoms. Item 3. The polycyclic aromatic compound according to item 3.

[0018] Section 7. Item 7. The polycyclic aromatic compound or a multimer thereof according to any one of Items 1 to 6, which is substituted with a diarylamino group fused with a cycloalkane, a carbazolyl group fused with a cycloalkane, or a benzocarbazolyl group fused with a cycloalkane.

[0019] Section 8. R 2 Item 7. The polycyclic aromatic compound according to any one of Items 3 to 6, wherein R is a diarylamino group condensed with a cycloalkane or a carbazolyl group condensed with a cycloalkane.

[0020] Section 9. Item 9. The polycyclic aromatic compound according to item 7 or 8, wherein the cycloalkane is a cycloalkane having 3 to 20 carbon atoms.

[0021] Section 10. Item 9. The polycyclic aromatic compound or a multimer thereof according to any one of items 1 to 8, wherein the halogen is fluorine.

[0022] Section 11. Item 3. The polycyclic aromatic compound according to item 1, which is represented by any one of the following structural formulas: [ka] [ka] [ka] [ka] (In the above structural formulas, "Me" represents a methyl group and "tBu" represents a t-butyl group.)

[0023] Section 12. 12. A reactive compound in which the polycyclic aromatic compound or a multimer thereof according to any one of items 1 to 11 is substituted with a reactive substituent.

[0024] Section 13. Item 13. A polymer compound obtained by polymerizing the reactive compound according to item 12 as a monomer, or a crosslinked polymer obtained by further crosslinking the polymer compound.

[0025] Section 14. Item 13. A pendant polymer compound in which a reactive compound described in item 12 is substituted on a main chain polymer, or a pendant polymer crosslinked product in which the pendant polymer compound is further crosslinked.

[0026] Section 15. Item 12. A material for an organic device, comprising the polycyclic aromatic compound or a multimer thereof according to any one of items 1 to 11.

[0027] Section 16. Item 13. A material for an organic device, comprising the reactive compound according to item 12.

[0028] Section 17. Item 14. A material for an organic device, comprising the polymer compound or crosslinked polymer according to item 13.

[0029] Section 18. Item 15. A material for an organic device, comprising the pendant polymer compound or the pendant polymer crosslinked body according to item 14.

[0030] Section 19. Item 19. The material for an organic device according to any one of items 15 to 18, 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.

[0031] Section 20. Item 20. The material for an organic device according to item 19, wherein the material for an organic electroluminescent element is a material for a light-emitting layer.

[0032] Section 21. 12. An ink composition comprising the polycyclic aromatic compound or a multimer thereof according to any one of items 1 to 11 and an organic solvent.

[0033] Section 22. Item 13. An ink composition comprising the reactive compound according to item 12 and an organic solvent.

[0034] Section 23. Item 13. An ink composition comprising a main chain polymer, the reactive compound according to item 12, and an organic solvent.

[0035] Section 24. Item 14. An ink composition comprising the polymer compound or crosslinked polymer according to item 13 and an organic solvent.

[0036] Section 25. Item 15. An ink composition comprising the pendant polymer compound or the pendant polymer crosslinked product according to item 14 and an organic solvent.

[0037] Section 26. 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 according to any one of items 1 to 11, the reactive compound according to item 12, the polymer compound or crosslinked polymer according to item 13, or the pendant polymer compound or crosslinked polymer according to item 14.

[0038] Section 27. Item 27. The organic electroluminescent device according to item 26, wherein the organic layer is a light-emitting layer.

[0039] Section 28. Item 28. The organic electroluminescent device according to item 27, wherein the light-emitting layer contains a host and the polycyclic aromatic compound, its multimer, reactive compound, polymer compound, crosslinked polymer, pendant polymer compound, or pendant crosslinked polymer as a dopant.

[0040] Section 29. Item 29. The organic electroluminescent device according to item 28, wherein the host is an anthracene-based compound, a fluorene-based compound, or a dibenzochrysene-based compound.

[0041] Section 30. 30. The organic electroluminescence device according to any one of items 26 to 29, 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 derivatives, anthracene derivatives, benzofluorene derivatives, phosphine oxide derivatives, pyrimidine derivatives, carbazole derivatives, triazine derivatives, benzimidazole derivatives, phenanthroline derivatives, and quinolinol metal complexes.

[0042] Section 31. Item 31. The organic electroluminescence device according to item 30, 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.

[0043] Section 32. Item 32. The organic electroluminescence device according to any one of items 26 to 31, 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.

[0044] Section 33. 33. A display or lighting device comprising the organic electroluminescent device according to any one of items 26 to 32. Effect of the Invention

[0045] According to a preferred embodiment of the present invention, it is possible to provide a novel cycloalkane-fused polycyclic aromatic compound that can be used as a material for organic devices such as a material for an organic electroluminescence (EL) element, and by using this cycloalkane-fused polycyclic aromatic compound, it is possible to provide an excellent organic device such as an organic electroluminescence (EL) element.

[0046] Specifically, the inventors have demonstrated that polycyclic aromatic compounds (basic skeleton parts) in which aromatic rings are linked by heteroatoms such as boron, phosphorus, oxygen, nitrogen, and sulfur have a large HOMO-LUMO gap (band gap Eg in a thin film) and high triplet excitation energy (E T). This is believed to be due to the fact that the 6-membered ring containing a hetero element has low aromaticity, which suppresses the decrease in the HOMO-LUMO gap accompanying the expansion of the conjugated system, and that the SOMO1 and SOMO2 in the triplet excited state (T1) are localized due to electronic perturbation of the hetero element. In addition, the polycyclic aromatic compound (basic skeleton portion) containing a hetero element according to the present invention has a small energy difference between the triplet excited state (T1) and the singlet excited state (S1), and exhibits thermally activated delayed fluorescence, making it useful as a fluorescent material for organic EL devices (including devices using thermally activated delayed fluorescence). In addition, the high triplet excitation energy (E T Materials having the above property are also useful as electron transport layers or hole transport layers in phosphorescent organic EL devices and organic EL devices that use thermally activated delayed fluorescence. Furthermore, the HOMO and LUMO energies of these polycyclic aromatic compounds (basic skeleton parts) can be arbitrarily shifted by introducing substituents, so that the ionization potential and electron affinity can be optimized according to the surrounding materials.

[0047] In addition to the characteristics of the basic skeleton portion, the compound of the present invention is expected to suppress concentration quenching by condensing cycloalkane, and to improve the element life and luminous efficiency. The element life and luminous efficiency are important characteristic values ​​of organic devices, and the use of the compound of the present application is expected to have an effect of improving the characteristics of the device. In addition, a decrease in melting point and sublimation temperature can be expected. This means that in sublimation purification, which is almost essential as a purification method for materials for organic devices such as organic EL elements that require high purity, purification can be performed at a relatively low temperature, so that thermal decomposition of the material can be avoided. This is also true for the vacuum deposition process, which is a powerful means for producing organic devices such as organic EL elements, and since the process can be performed at a relatively low temperature, thermal decomposition of the material can be avoided, and as a result, high-performance organic device materials can be obtained. In addition, since many of the multimers of polycyclic aromatic compounds have a high sublimation temperature due to their molecular weight and high planarity, the decrease in sublimation temperature by condensing cycloalkane is more effective. In addition, since the solubility in organic solvents is improved by condensation of cycloalkane, it becomes possible to apply it to the production of elements using a coating process. However, the present invention is not particularly limited to these principles. [Brief description of the drawings]

[0048] [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

[0049] 1. Cycloalkane-condensed polycyclic aromatic compounds and their polymers 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), preferably a polycyclic aromatic compound represented by the following general formula (2), or a multimer of a polycyclic aromatic compound having a plurality of structures represented by the following general formula (2), in which at least one of ring A, ring B, ring C, aryl, and heteroaryl in these compounds or structures is condensed with at least one cycloalkane. [ka]

[0050] In general formula (1), ring A, ring B and ring C are each independently an aryl ring or a heteroaryl ring, and at least one hydrogen atom in these rings may be substituted with a substituent. The substituent is preferably a substituted or unsubstituted aryl, a substituted or unsubstituted heteroaryl, a substituted or unsubstituted diarylamino, a substituted or unsubstituted diheteroarylamino, a substituted or unsubstituted arylheteroarylamino (an amino group having an aryl and a heteroaryl), a substituted or unsubstituted diarylboryl (two aryls may be bonded via a single bond or a linking group), a substituted or unsubstituted alkyl, a substituted or unsubstituted cycloalkyl, a substituted or unsubstituted alkoxy, a substituted or unsubstituted aryloxy, or a substituted silyl. When these groups have a substituent, examples of the substituent include aryl, heteroaryl, alkyl or cycloalkyl. In addition, the aryl ring or heteroaryl ring may be selected from the group consisting of Y 1 , X 1 and X 2 It is preferable that the fused two-ring structure in the center of the formula (1) has a 5- or 6-membered ring sharing a bond therewith.

[0051] Here, the "fused two-ring structure" refers to the Y 1 , X 1 and X 2means a structure in which two saturated hydrocarbon rings are fused together. In addition, the term "six-membered ring sharing a bond with the fused two-ring structure" means, for example, an a-ring (benzene ring (six-membered ring)) fused to the fused two-ring structure as shown in the above general formula (2). In addition, the term "an aryl ring or heteroaryl ring (A-ring) has this six-membered ring" means that the A-ring is formed only from this six-membered ring, or that the A-ring is formed by further condensing other rings to this six-membered ring so as to include this six-membered ring. In other words, the term "an aryl ring or heteroaryl ring (A-ring) having a six-membered ring" means that the six-membered ring constituting all or part of the A-ring is fused to the fused two-ring structure. The same explanation applies to "B-ring (b-ring)", "C-ring (c-ring)", and "five-membered ring".

[0052] The ring A (or ring B or ring C) in the general formula (1) is the ring a and its substituent R 1 ~R 3 (or ring b and its substituent R 8 ~R 11 , ring c and its substituent R 4 ~R 7 ). In other words, general formula (2) corresponds to a structure in which "rings A to C having 6 members" are selected as rings A to C of general formula (1). In that sense, each ring in general formula (2) is represented by lowercase letters a to c.

[0053] In the general formula (2), the substituents R 1 ~R 11Adjacent groups among may be bonded together 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, a diarylboryl (two aryls may be bonded via a single bond or a linking group), an alkyl, a cycloalkyl, an alkoxy, an aryloxy, a triarylsilyl, a trialkylsilyl, a tricycloalkylsilyl, a dialkylcycloalkylsilyl or an alkyldicycloalkylsilyl, and at least one hydrogen atom in these may be substituted with an aryl, a heteroaryl, an alkyl or a cycloalkyl. Therefore, the ring structure constituting the polycyclic aromatic compound represented by the general formula (2) changes depending on the mutual bonding form of the substituents in the a ring, the b ring and the c ring, as shown in the following formula (2-1) and formula (2-2). The A' ring, the B' ring and the C' ring in each formula correspond to the A ring, the B ring and the C ring in the general formula (1), respectively.

[0054] [ka]

[0055] The A' ring, B' ring and C' ring in the above formula (2-1) and formula (2-2) are each independently a substituent R 1 ~R 11 Adjacent groups among these are bonded to each other to form an aryl or heteroaryl ring together with the ring a, ring b, and ring c, respectively (they may also be considered as condensed rings formed by condensing other ring structures to the ring a, ring b, or ring c). Although not shown in the formula, there are also compounds in which the ring a, ring b, and ring c are all changed to ring A', ring B', and ring C'. As can be seen from the above formulas (2-1) and (2-2), for example, R in ring b 8 and R in c-ring 7 , R in ring b 11 and a-ring R 1 , R in ring c 4 and a-ring R 3etc. are not considered to be "adjacent groups" and are not bonded to each other. In other words, "adjacent groups" refers to groups adjacent to each other on the same ring.

[0056] The compounds represented by the above formula (2-1) or formula (2-2) are compounds having ring A' (or ring B' or ring C') formed by condensing a benzene ring, which is ring a (or ring b or ring c), with a benzene ring, an indole ring, a pyrrole ring, a benzofuran ring or a benzothiophene ring, and the condensed ring A' (or condensed ring B' or condensed ring C') thus formed is a naphthalene ring, a carbazole ring, an indole ring, a dibenzofuran ring or a dibenzothiophene ring, respectively.

[0057] Y in general formula (1) 1 is B, P, P=O, P=S, Al, Ga, As, Si-R or Ge-R, and R of the Si-R and Ge-R is aryl, alkyl or cycloalkyl. In the case of P=O, P=S, Si-R or Ge-R, the atom bonded to the A ring, B ring or C ring is P, Si or Ge. Y 1 is preferably B, P, P=O, P=S or Si-R, and particularly preferably B. This explanation is based on the general formula (2) Y 1 But it's the same.

[0058] X in general formula (1) 1 and X 2are each independently >O, >NR, >C(-R)2, >S or >Se, R of the >NR is an aryl which may be substituted, a heteroaryl which may be substituted, an alkyl which may be substituted or a cycloalkyl which may be substituted, R of the >C(-R)2 is hydrogen, an aryl which may be substituted, an alkyl which may be substituted or a cycloalkyl which may be substituted, and at least one of R of the >NR and R of the >C(-R)2 may be bonded to at least one of the A ring, the B ring and the C ring by a linking group or a single bond, and the linking group is preferably -O-, -S- or -C(-R)2-. Note that R of the "-C(-R)2-" is hydrogen, an alkyl or a cycloalkyl. This explanation is based on X in general formula (2). 1 and X 2 But it's the same.

[0059] Here, the provision in general formula (1) that "at least one of R of >NR and R of >C(-R)2 is bonded to at least one of ring A, ring B and ring C via a linking group or a single bond" corresponds to the provision in general formula (2) that "at least one of R of >NR and R of >C(-R)2 is bonded to at least one of ring a, ring b and ring c via -O-, -S-, -C(-R)2- or a single bond."

[0060] This provision is expressed by the following formula (2-3-1), X 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 compound having X in the benzene ring which is the b ring (or the c ring) in the general formula (2) 1 (or X 2 The compound has a ring B' (or ring C') formed by condensing another ring so as to incorporate the ring A. The condensed ring B' (or condensed ring C') formed is, for example, a phenoxazine ring, a phenothiazine ring, or an acridine ring.

[0061] In addition, the above provision is expressed by the following formula (2-3-2) or formula (2-3-3), X1 and X 2 In other words, for example, the compound having a ring structure in which X is incorporated into the fused ring A' in the benzene ring that is the a ring in the general formula (2) 1 (or X 2 , or X 1 and X 2 The compound has a ring A' formed by condensing another ring so as to incorporate the ring A'. The condensed ring A' formed is, for example, a phenoxazine ring, a phenothiazine ring, or an acridine ring.

[0062] [ka]

[0063] In formula (2), any "-C(-R)=" (where R is R in formula (2)) in the a ring, the b ring, and the c ring 1 ~R 11 ) may be replaced with "-N=". [ka] As shown above, for example, "-C(-R 5 In this manner, the c-ring shown as a benzene ring in formula (2) may be changed to a pyridine ring, a pyrimidine ring, a pyridazine ring, a pyrazine ring, or other nitrogen-containing heteroaryl ring. Also, when there is an adjacent group on the c-ring (R 6 and R 7 ) are bonded to form a heteroaryl ring (a quinoline ring in the above formula) together with ring c, and the formed ring may be further substituted (represented by n Rs), as described above. In addition, there are the following variations: [ka] The same applies when other parts are replaced with "-N=" or when the a or b ring changes.

[0064] In formula (2), any of "-C(-R)=C(-R)-" (where R is R in formula (2)) in the ring a, ring b, and ring c 1 ~R 11 The substituents listed here may be replaced with "-N(-R)-", "-O-" or "-S-", and R in the "-N(-R)-" is aryl, alkyl or cycloalkyl. Details of the substituents listed here will be described below. [ka] As shown above, for example, "-C(-R 7 )=C(-R 6 In this manner, the c-ring, which is represented as a benzene ring in formula (2), may be changed to an R-substituted pyrrole ring, furan ring, thiophene ring, or other nitrogen-oxygen-sulfur containing heteroaryl ring. Also, when an adjacent group is present on the c-ring (R in the above formula), 4 and R 5 ) are bonded to ring c to form a heteroaryl ring (in the above formula, an R-substituted indole ring, benzofuran ring, or benzothiophene ring), and the formed ring may be further substituted (represented by n Rs), as described above. In addition, there are the following variations: [ka] The same applies when other positions are replaced with "-N(-R)-", "-O-", or "-S-", or when the a or b ring changes.

[0065] In the above explanation of formula (2-1), formula (2-2), formula (2-3-1), formula (2-3-2), and formula (2-3-3), the ring a, the ring b, and the ring c are described as benzene rings, but the same applies when the ring a to the ring c are changed to a nitrogen-containing heteroaryl ring (6-membered ring or 5-membered ring) or an oxygen-sulfur-containing heteroaryl ring (5-membered ring).

[0066] The "aryl ring" which is the ring A, ring B and ring C in the general formula (1) is, for example, an aryl ring having 6 to 30 carbon atoms, preferably an aryl ring having 6 to 16 carbon atoms, more preferably an aryl ring having 6 to 12 carbon atoms, and particularly preferably an aryl ring having 6 to 10 carbon atoms. The "aryl ring" is defined as "R 1 ~R 11 In addition, since ring a (or ring b, ring c) is already composed of a benzene ring having six carbon atoms, the lower limit of the carbon number is the total carbon number of the fused rings formed by condensing the five-membered ring to this, which is nine.

[0067] Specific examples of the "aryl ring" include a monocyclic benzene ring, a bicyclic ...

[0068] Examples of the "heteroaryl ring" which is the ring A, ring B and ring C in general formula (1) include heteroaryl rings having 2 to 30 carbon atoms, preferably heteroaryl rings having 2 to 25 carbon atoms, more preferably heteroaryl rings having 2 to 20 carbon atoms, further preferably heteroaryl rings having 2 to 15 carbon atoms, and particularly preferably heteroaryl rings having 2 to 10 carbon atoms. Examples of the "heteroaryl ring" include heterocycles containing, in addition to carbon, 1 to 5 heteroatoms selected from oxygen, sulfur and nitrogen as ring-constituting atoms. The "heteroaryl ring" can be defined as "R 1 ~R 11In addition, since ring a (or ring b, ring c) is already composed of a benzene ring having 6 carbon atoms, the lower limit of the carbon number is the total carbon number of the fused rings fused to this 5-membered ring, which is 6.

[0069] Specific examples of the "heteroaryl ring" include a pyrrole ring, an oxazole ring, an isoxazole ring, a thiazole ring, an isothiazole ring, an imidazole ring, an oxadiazole ring, a thiadiazole ring, a triazole ring, a tetrazole ring, a pyrazole ring, a pyridine ring, a pyrimidine ring, a pyridazine ring, a pyrazine ring, a triazine ring, an indole ring, an isoindole ring, a 1H-indazole ring, a benzimidazole ring, a benzoxazole ring, a benzothiazole ring, a 1H-benzotriazole ring, a quinoline ring, an isoquinoline ring, a cinnoline ring, a quinazoline ring, a quinoxaline ring, a phenanthroline ring, a phthalazine ring, a naphthyridine ring, a purine ring, a pteridine ring, a carbazole ... Examples of such rings include a benzol 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 naphthobenzofuran ring, a thiophene ring, a benzothiophene ring, an isobenzothiophene ring, a dibenzothiophene ring, a naphthobenzothiophene ring, a benzophosphole ring, a dibenzophosphole ring, a benzophosphole oxide ring, a dibenzophosphole oxide ring, a furazan ring, a thianthrene ring, an indolocarbazole ring, a benzoindolocarbazole ring, a benzobenzoindolocarbazole ring, an imidazoline ring, and an oxazoline ring.

[0070] At least one hydrogen atom in the above-mentioned "aryl ring" or "heteroaryl ring" may be substituted with a first substituent, which is a substituted or unsubstituted "aryl", a substituted or unsubstituted "heteroaryl", a substituted or unsubstituted "diarylamino", a substituted or unsubstituted "diheteroarylamino", a substituted or unsubstituted "arylheteroarylamino", a substituted or unsubstituted "diarylboryl (two aryls may be bonded via a single bond or a linking group)", a substituted or unsubstituted "alkyl", a substituted or unsubstituted "cycloalkyl", a substituted or unsubstituted "alkoxy", a substituted or unsubstituted "aryloxy", or a substituted "silyl". Examples of the first substituent, the "aryl" or "heteroaryl" in the "diarylamino", the heteroaryl in the "diheteroarylamino", the aryl and heteroaryl in the "arylheteroarylamino", the aryl in the "diarylboryl", and the aryl in the "aryloxy" include the monovalent groups of the above-mentioned "aryl ring" or "heteroaryl ring".

[0071] The "alkyl" as the first substituent may be either linear or branched, and examples thereof include linear alkyl having 1 to 24 carbon atoms or branched alkyl having 3 to 24 carbon atoms. An alkyl having 1 to 18 carbon atoms (branched alkyl having 3 to 18 carbon atoms) is preferred, an alkyl having 1 to 12 carbon atoms (branched alkyl having 3 to 12 carbon atoms) is more preferred, an alkyl having 1 to 6 carbon atoms (branched alkyl having 3 to 6 carbon atoms) is even more preferred, and an alkyl having 1 to 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.

[0072] 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 include 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.

[0073] Furthermore, examples of the "cycloalkyl" as the first substituent include cycloalkyl having 3 to 24 carbon atoms, cycloalkyl having 3 to 20 carbon atoms, cycloalkyl having 3 to 16 carbon atoms, cycloalkyl having 3 to 14 carbon atoms, cycloalkyl having 3 to 12 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.

[0074] 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 or 1 to 5 carbon atoms, as well as norbornenyl, bicyclo[1.0.1]butyl, bicyclo[1.1.1]pentyl, bicyclo[2.0.1]pentyl, bicyclo[1.2.1]hexyl, bicyclo[3.0.1]hexyl, bicyclo[2.1.2]heptyl, bicyclo[2.2.2]octyl, adamantyl, diamantyl, decahydronaphthalenyl, and decahydroazulenyl.

[0075] Furthermore, examples of the "alkoxy" as the first substituent include linear alkoxy having 1 to 24 carbon atoms or branched alkoxy having 3 to 24 carbon atoms. An alkoxy having 1 to 18 carbon atoms (branched alkoxy having 3 to 18 carbon atoms) is preferred, an alkoxy having 1 to 12 carbon atoms (branched alkoxy having 3 to 12 carbon atoms) is more preferred, an alkoxy having 1 to 6 carbon atoms (branched alkoxy having 3 to 6 carbon atoms) is even more preferred, and an alkoxy having 1 to 5 carbon atoms (branched alkoxy having 3 to 5 carbon atoms) or an alkoxy having 1 to 4 carbon atoms (branched alkoxy having 3 to 4 carbon atoms) is particularly preferred.

[0076] 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.

[0077] Furthermore, examples of the "substituted silyl" as the first substituent include triarylsilyl, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, and alkyldicycloalkylsilyl, which are silyl substituted with at least one of aryl, alkyl, and cycloalkyl.

[0078] The "triarylsilyl" refers to a silyl group in which three hydrogen atoms are each independently substituted with an aryl, and the aryl can be any of the groups described above as the "aryl" in the first substituent. Specific "triarylsilyl" includes, for example, triphenylsilyl, diphenylmononaphthylsilyl, monophenyldinaphthylsilyl, trinaphthylsilyl, and the like.

[0079] An example of the "trialkylsilyl" is a group in which three hydrogen atoms in a silyl group are each independently substituted with an alkyl, and the alkyl can be cited from the groups described as the "alkyl" in the first substituent above. Preferred alkyl groups for substitution are those having 1 to 5 carbon atoms or 1 to 4 carbon atoms, and specific examples thereof include methyl, ethyl, propyl, i-propyl, butyl, sec-butyl, t-butyl, and cyclobutyl.

[0080] Specific examples of trialkylsilyl include trimethylsilyl, triethylsilyl, tripropylsilyl, tri-i-propylsilyl, tributylsilyl, tri-sec-butylsilyl, tri-t-butylsilyl, ethyldimethylsilyl, propyldimethylsilyl, i-propyldimethylsilyl, butyldimethylsilyl, sec-butyldimethylsilyl, t-butyldimethylsilyl, methyldiethylsilyl, propyldiethylsilyl, i-propyldiethylsilyl, butyldiethylsilyl, sec-butyldiethylsilyl, t-butyldiethylsilyl, methyldipropylsilyl, ethyldipropylsilyl, butyldipropylsilyl, sec-butyldipropylsilyl, t-butyldipropylsilyl, methyldi-i-propylsilyl, ethyldi-i-propylsilyl, butyldi-i-propylsilyl, sec-butyldi-i-propylsilyl, and t-butyldi-i-propylsilyl.

[0081] Examples of "tricycloalkylsilyl" include groups in which three hydrogen atoms in a silyl group are independently replaced with cycloalkyl, and the cycloalkyl can be cited as the group described as "cycloalkyl" in the first substituent above. Preferred cycloalkyl groups for substitution are cycloalkyl groups having 5 to 10 carbon atoms, specifically cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, bicyclo[1.1.1]pentyl, bicyclo[2.0.1]pentyl, bicyclo[1.2.1]hexyl, bicyclo[3.0.1]hexyl, bicyclo[2.1.2]heptyl, bicyclo[2.2.2]octyl, adamantyl, decahydronaphthalenyl, and decahydroazulenyl.

[0082] Specific examples of tricycloalkylsilyl include tricyclopentylsilyl and tricyclohexylsilyl.

[0083] Specific examples of dialkylcycloalkylsilyl substituted with two alkyls and one cycloalkyl and alkyldicycloalkylsilyl substituted with one alkyl and two cycloalkyls include silyl substituted with a group selected from the specific alkyls and cycloalkyls mentioned above.

[0084] As for the "aryl" in the "diarylboryl" of the first substituent, the above description of the aryl can be cited. In addition, the two aryls may be bonded via a single bond or a linking group (for example, >C(-R)2, >O, >S, or >NR). Here, R in >C(-R)2 and >NR is hydrogen (only in the case of >C(-R)2), aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, alkoxy, or aryloxy (the above, the first substituent), and the first substituent may be further substituted with aryl, heteroaryl, alkyl, or cycloalkyl (the above, the second substituent), and as specific examples of these groups, the above description of the aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, alkoxy, or aryloxy as the first substituent can be cited.

[0085] As explained above, the first substituent, substituted or unsubstituted "aryl", substituted or unsubstituted "heteroaryl", substituted or unsubstituted "diarylamino", substituted or unsubstituted "diheteroarylamino", substituted or unsubstituted "arylheteroarylamino", substituted or unsubstituted "diarylboryl (two aryls may be bonded via a single bond or a linking group)", substituted or unsubstituted "alkyl", substituted or unsubstituted "cycloalkyl", substituted or unsubstituted "alkoxy", substituted or unsubstituted "aryloxy", or substituted "silyl", may have at least one hydrogen atom substituted with a second substituent. Examples of the second substituent include aryl, heteroaryl, alkyl, or cycloalkyl, and specific examples thereof can be found in the above-mentioned explanation of the monovalent group of the "aryl ring" or "heteroaryl ring", and the explanation of the "alkyl" or "cycloalkyl" as the first substituent. The aryl and heteroaryl as the second substituent also include structures in which at least one hydrogen atom in the aryl and heteroaryl as the second substituent is substituted with an aryl such as phenyl (specific examples are the groups mentioned above), an alkyl such as methyl (specific examples are the groups mentioned above), or a cycloalkyl such as cyclohexyl (specific examples are the groups mentioned above). As an example, when the second substituent is a carbazolyl group, a carbazolyl group in which at least one hydrogen atom at the 9-position is substituted with an aryl such as phenyl, an alkyl such as methyl, or a cycloalkyl such as cyclohexyl is also included in the heteroaryl as the second substituent.

[0086] R in general formula (2) 1 ~R 11 The aryl, heteroaryl, aryl of diarylamino, heteroaryl of diheteroarylamino, aryl and heteroaryl of arylheteroarylamino, aryl of diarylboryl, and aryl of aryloxy in the formula (1) include the monovalent groups of "aryl ring" or "heteroaryl ring" described in the formula (1). 1 ~R 11For the alkyl, cycloalkyl, or alkoxy in R , the explanation of "alkyl," "cycloalkyl," or "alkoxy" as the first substituent in the explanation of the above general formula (1) can be referred to. 1 ~R 11 For the triarylsilyl, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, or alkyldicycloalkylsilyl in the above, the explanation of "substituted silyl" as the first substituent in the explanation of the above general formula (1) can be referred to. Furthermore, the same applies to aryl, heteroaryl, alkyl, or cycloalkyl as substituents to these groups. In addition, R 1 ~R 11 When adjacent groups among these are bonded to form an aryl ring or heteroaryl ring together with the a ring, the b ring or the c ring, the same applies to the substituents on these rings, such as heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl (the two aryls may be bonded via a single bond or a linking group), alkyl, cycloalkyl, alkoxy, aryloxy, triarylsilyl, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl or alkyldicycloalkylsilyl, and the further substituents, aryl, heteroaryl, alkyl or cycloalkyl.

[0087] Specifically, the emission wavelength can be adjusted by the steric hindrance, electron donating property and electron withdrawing property of the structure of the first substituent, and the first substituent is preferably a group represented by the following structural formula, and more preferably, methyl, t-butyl, t-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 more preferably 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.

[0088] In the structural formulas below, "Me" represents methyl, "tBu" represents t-butyl, "tAm" represents t-amyl, and "tOct" represents t-octyl, and * represents the bond position. [ka] [ka] [ka] [ka] [ka]

[0089] In the general formula (2), any "-C(-R)=C(-R)-" (where R is R in formula (2) 1 ~R 11 R in "-N(-R)-" which may be substituted by "-N(-R)-" is aryl, alkyl, or cycloalkyl, and examples of this aryl, alkyl, or cycloalkyl include the groups described above. In particular, aryl having 6 to 10 carbon atoms (e.g., phenyl, naphthyl, etc.), alkyl having 1 to 5 or 1 to 4 carbon atoms (e.g., methyl, ethyl, etc.), or cycloalkyl having 5 to 10 carbon atoms (preferably cyclohexyl or adamantyl) are preferred.

[0090] Y in general formula (1) 1 In the above formula, R in Si-R and Ge-R is aryl, alkyl or cycloalkyl, and examples of the aryl, alkyl or cycloalkyl include the groups described above. In particular, aryl having 6 to 10 carbon atoms (e.g., phenyl, naphthyl, etc.), alkyl having 1 to 5 or 1 to 4 carbon atoms (e.g., methyl, ethyl, etc.), or cycloalkyl having 5 to 10 carbon atoms (preferably cyclohexyl or adamantyl) are preferred. This explanation is based on Y in general formula (2). 1 But it's the same.

[0091] X in general formula (1) 1 and X 2In the above, R in >NR is an aryl, heteroaryl, alkyl or cycloalkyl which may be substituted by the second substituent described above, and at least one hydrogen in the aryl, heteroaryl, alkyl or cycloalkyl may be substituted by, for example, an alkyl or cycloalkyl. Examples of the aryl, heteroaryl, alkyl or cycloalkyl include the groups described above. In particular, an aryl having 6 to 10 carbon atoms (e.g., phenyl, naphthyl, etc.), a heteroaryl having 2 to 15 carbon atoms (e.g., carbazolyl, dibenzofuranyl, dibenzothiophenyl, etc.), an alkyl having 1 to 5 carbon atoms or 1 to 4 carbon atoms (e.g., methyl, ethyl, etc.), or a cycloalkyl having 5 to 10 carbon atoms (preferably cyclohexyl or adamantyl) is preferred, with phenyl, naphthyl, carbazolyl, dibenzofuranyl or dibenzothiophenyl being more preferred, and dibenzofuranyl or dibenzothiophenyl being even more preferred. In addition, it is particularly preferable that dibenzofuranyl or dibenzothiophenyl is substituted with a second substituent, and specifically, examples of the second substituent include t-butyl, phenyl, or d5-phenyl, and these substituents are preferably substituted at the para position of the oxygen atom or sulfur atom. 1 and X 2 But it's the same.

[0092] X in general formula (1) 1 and X 2 In the formula, R in >C(-R)2 is hydrogen, an aryl, an alkyl or a cycloalkyl which may be substituted with the second substituent described above, and at least one hydrogen in the aryl may be substituted with, for example, an alkyl. Examples of the aryl, alkyl or cycloalkyl include the groups described above. In particular, an aryl having 6 to 10 carbon atoms (e.g., phenyl, naphthyl, etc.), an alkyl having 1 to 5 or 1 to 4 carbon atoms (e.g., methyl, ethyl, etc.) or a cycloalkyl having 5 to 10 carbon atoms (preferably cyclohexyl or adamantyl) is preferred. This explanation is given for X in the general formula (2). 1 and X 2 But it's the same.

[0093] In the general formula (1), R in the linking group "-C(-R)2-" is hydrogen, alkyl, or cycloalkyl, and examples of this alkyl or cycloalkyl include the groups described above. In particular, alkyl having 1 to 5 or 1 to 4 carbon atoms (e.g., methyl, ethyl, etc.) or cycloalkyl having 5 to 10 carbon atoms (preferably cyclohexyl or adamantyl) is preferred. This explanation also applies to the linking group "-C(-R)2-" in the general formula (2).

[0094] The present invention also relates to a multimer of a polycyclic aromatic compound having a plurality of unit structures represented by general formula (1), preferably a multimer of a polycyclic aromatic compound having a plurality of unit structures represented by general formula (2). The multimer is preferably a dimer to hexamer, more preferably a dimer to trimer, and particularly preferably a dimer. The multimer may have a form having a plurality of the above unit structures in one compound. For example, in addition to a form in which a plurality of the above unit structures are bonded together via a linking group such as a single bond, an alkylene group having 1 to 3 carbon atoms, a phenylene group, or a naphthylene group (linked multimer), the multimer may have a form in which any ring (ring A, ring B or ring C, ring a, ring b or ring c) contained in the above unit structure is bonded together so as to be shared by the plurality of unit structures (ring-shared multimer), or may have a form in which any ring (ring A, ring B or ring C, ring a, ring b or ring c) contained in the above unit structure is bonded together so as to be condensed (ring-condensed multimer). However, ring-shared multimers and ring-condensed multimers are preferred, and ring-shared multimers are more preferred.

[0095] Examples of such multimers include multimer compounds represented by the following formula (2-4), formula (2-4-1), formula (2-4-2), formula (2-5-1) to formula (2-5-4), or formula (2-6). The multimer compound represented by the following formula (2-4) is a multimer compound (ring-sharing multimer) having a plurality of unit structures represented by general formula (2) in one compound, with the benzene ring being the a-ring being shared, as explained in the general formula (2). The multimer compound represented by the following formula (2-4-1) is a multimer compound (ring-sharing multimer) having two unit structures represented by general formula (2) in one compound, with the benzene ring being the a-ring being shared, as explained in the general formula (2). Moreover, the multimeric compound represented by the following formula (2-4-2) is a multimeric compound (ring-sharing type multimer) having three unit structures represented by the general formula (2) in one compound, with the benzene ring being the a ring shared, when described in the general formula (2). Moreover, the multimeric compound represented by any one of the following formulas (2-5-1) to (2-5-4) is a multimeric compound (ring-sharing type multimer) having a plurality of unit structures represented by the general formula (2) in one compound, with the benzene ring being the b ring (or the c ring) shared, when described in the general formula (2). Moreover, the multimeric compound represented by the following formula (2-6) is a multimeric compound (ring-condensed type multimer) having a plurality of unit structures represented by the general formula (2) in one compound, with the benzene ring being the b ring (or the a ring, the c ring) of a certain unit structure condensed with the benzene ring being the b ring (or the a ring, the c ring) of a certain unit structure.

[0096] [ka]

[0097] The multimeric compound may be a multimer in which a multimerization form represented by formula (2-4), formula (2-4-1) or formula (2-4-2) is combined with a multimerization form represented by any one of formulas (2-5-1) to (2-5-4) or formula (2-6), a multimer in which a multimerization form represented by any one of formulas (2-5-1) to (2-5-4) is combined with a multimerization form represented by formula (2-6), or a multimer in which a multimerization form represented by formula (2-4), formula (2-4-1) or formula (2-4-2), a multimerization form represented by any one of formulas (2-5-1) to (2-5-4), and a multimerization form represented by formula (2-6).

[0098] In addition, all or a part of hydrogen atoms in the chemical structure of the polycyclic aromatic compound and its multimer represented by general formula (1) or (2) may be deuterium, cyano, or halogen. For example, in formula (1), ring A, ring B, and ring C (rings A to C are aryl rings or heteroaryl rings), substituents on rings A to C, Y 1 is Si-R or Ge-R, R (=alkyl, cycloalkyl, aryl), and X 1 and X 2 When is >NR or >C(-R)2, hydrogen in R (=alkyl, cycloalkyl, aryl) can be replaced by deuterium, cyano or halogen, among which, all or a part of hydrogen in aryl or heteroaryl is replaced by deuterium, cyano or halogen. Halogen is fluorine, chlorine, bromine or iodine, preferably fluorine, chlorine or bromine, more preferably fluorine or chlorine.

[0099] The polycyclic aromatic compound and its multimer according to the present invention can be used as a material for an organic device. Examples of the organic device include an organic electroluminescence device, an organic field effect transistor, and an organic thin-film solar cell. In particular, in an organic electroluminescence device, Y is preferably used as a dopant material for the light-emitting layer. 1 B, X 1 and X 2 Compounds where Y is >NR 1B, X 1 >O,X 2 Compounds where Y is >NR 1 B, X 1 and X 2 As a host material of the light-emitting layer, a compound in which Y 1 B, X 1 >O,X 2 Compounds where Y is >NR 1 B, X 1 and X 2 As the electron transport material, a compound in which Y 1 B, X 1 and X 2 Compounds in which Y is >O 1 P=O, X 1 and X 2 Compounds in which is >O are preferably used.

[0100] In addition, at least one of the aromatic rings and heteroaromatic rings in the chemical structure of the polycyclic aromatic compound represented by general formula (1) or (2) and its multimer is condensed with at least one cycloalkane.

[0101] For example, aryl and heteroaryl rings which are ring A, ring B, ring C, ring a, ring b and ring c, aryl groups (aryl moieties in aryl, diarylamino, arylheteroarylamino, diarylboryl or aryloxy) and heteroaryl groups (heteroaryl moieties in heteroaryl, diheteroarylamino or arylheteroarylamino) as the first and second substituents on ring A to ring C, aryl groups (similar to above) and heteroaryl groups (similar to above) as the first and second substituents on ring a to ring c, Y 1 Aryl groups as R in Si—R and Ge—R (as above), and X 1 and X 2 At least one of the aryl group (as above) and the heteroaryl group (as above) as R in >NR and >C(-R)2 is fused with at least one cycloalkane.

[0102] Preferably, the aryl and heteroaryl rings are ring A, ring B, ring C, ring a, ring b and ring c, the aryl group (aryl group moiety in aryl, diarylamino, diarylboryl or aryloxy) and the heteroaryl group (heteroaryl moiety in heteroaryl or diheteroarylamino) as the first substituents on ring A to ring C, the aryl group (similar to above) and the heteroaryl group (similar to above) as the first substituents on ring a to ring c, and X 1 and X 2 At least one of the aryl group (as above) and the heteroaryl group (as above) as R in >NR and >C(-R)2 is fused with at least one cycloalkane.

[0103] More preferably, the rings A, B, C, a, b and c are aryl rings, the rings A to C are aryl groups (aryl group moieties in aryl or diarylamino) and heteroaryl groups (heteroaryl moieties in heteroaryl) are the first substituents, the rings A to C are aryl groups (similar to above) and heteroaryl groups (similar to above) are the first substituents, and X 1 and X 2 At least one of the >NR and the aryl group (as above) as R in >C(-R)2 is fused with at least one cycloalkane.

[0104] More preferably, the aryl rings are ring A, ring B, ring C, ring a, ring b and ring c, the aryl group as the first substituent on ring A to ring C (aryl group moiety in aryl or diarylamino), the aryl group as the first substituent on ring a to ring c (similar to the above), and X 1 and X 2 At least one of the >NR and the aryl group (as above) as R in >C(-R)2 is fused with at least one cycloalkane.

[0105] Examples of "cycloalkane" include cycloalkanes having 3 to 24 carbon atoms, cycloalkanes having 3 to 20 carbon atoms, cycloalkanes having 3 to 16 carbon atoms, cycloalkanes having 3 to 14 carbon atoms, cycloalkanes having 5 to 10 carbon atoms, cycloalkanes having 5 to 8 carbon atoms, cycloalkanes having 5 to 6 carbon atoms, and cycloalkanes having 5 carbon atoms.

[0106] Specific examples of cycloalkanes include cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclooctane, cyclononane, cyclodecane, norbornene, bicyclo[1.0.1]butane, bicyclo[1.1.1]pentane, bicyclo[2.0.1]pentane, bicyclo[1.2.1]hexane, bicyclo[3.0.1]hexane, bicyclo[2.1.2]heptane, bicyclo[2.2.2]octane, adamantane, diamantane, decahydronaphthalene, and decahydroazulene, as well as alkyl (particularly methyl) substituted derivatives having 1 to 5 carbon atoms or 1 to 4 carbon atoms, halogen (particularly fluorine) substituted derivatives, and deuterium substituted derivatives thereof.

[0107] Among these, for example, as shown in the following structural formula, a structure in which at least one hydrogen atom is substituted on the carbon atom at the α-position of a cycloalkane (a carbon atom at a position adjacent to the carbon atom at the condensation site in a cycloalkane fused to an aromatic ring or a heteroaromatic ring) is preferred, a structure in which two hydrogen atoms are substituted on the carbon atom at the α-position is more preferred, and a structure in which a total of four hydrogen atoms are substituted on the two carbon atoms at the α-position is even more preferred. Examples of this substituent include an alkyl (particularly methyl) substituent having 1 to 5 carbon atoms or 1 to 4 carbon atoms, a halogen (particularly fluorine) substituent, and a deuterium substituent. [ka]

[0108] The number of cycloalkanes condensed to one aromatic ring or heteroaromatic ring is preferably 1 to 3, more preferably 1 or 2, and even more preferably 1. For example, the following shows an example in which one or more cycloalkanes are condensed to one benzene ring (phenyl group). In each structural formula, * means a benzene ring contained in the skeleton structure of the compound when it is a benzene ring, and means a bond substituted on the skeleton structure of the compound when it is a phenyl group. Cycloalkanes condensed as in formula (Cy-1-4) and formula (Cy-2-4) may be condensed together. The same applies when the condensed ring (group) is an aromatic ring or heteroaromatic ring other than a benzene ring (phenyl group), or when the condensed cycloalkane is a cycloalkane other than cyclopentane or cyclohexane. [ka]

[0109] At least one -CH2- in a cycloalkane may be replaced with -O-. However, when multiple -CH2- are replaced with -O-, adjacent -CH2- are not replaced with -O-. For example, the following shows an example in which one or more -CH2- in a cycloalkane fused to one benzene ring (phenyl group) are replaced with -O-. In each structural formula, * means a benzene ring included in the skeletal structure of the compound when it is a benzene ring, and means a bond that substitutes for the skeletal structure of the compound when it is a phenyl group. The same applies when the fused ring (group) is an aromatic ring or heteroaromatic ring other than a benzene ring (phenyl group), and when the fused cycloalkane is a cycloalkane other than cyclopentane or cyclohexane. [ka]

[0110] At least one hydrogen atom in the cycloalkane may be substituted, and examples of the substituent include aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl (two aryls may be bonded via a single bond or a linking group), alkyl, cycloalkyl, alkoxy, aryloxy, substituted silyl, deuterium, cyano, and halogen. For details of these, the description of the first substituent can be cited. Among these substituents, alkyl (e.g., alkyl having 1 to 6 carbon atoms), cycloalkyl (e.g., cycloalkyl having 3 to 14 carbon atoms), halogen (e.g., fluorine), and deuterium are preferred. In addition, when cycloalkyl is substituted, it may be a substitution form that forms a spiro structure, and for example, an example in which a spiro structure is formed in a cycloalkane condensed to one benzene ring (phenyl group) is shown below. In each structural formula, * means that in the case of a benzene ring, it is a benzene ring included in the skeletal structure of the compound, and in the case of a phenyl group, it means a bond that substitutes in the skeletal structure of the compound. [ka]

[0111] Other forms of cycloalkane condensation include polycyclic aromatic compounds and multimers thereof represented by general formula (1) or (2) substituted with, for example, a diarylamino group condensed with a cycloalkane (condensed to the aryl group portion), a carbazolyl group condensed with a cycloalkane (condensed to the benzene ring portion), or a benzocarbazolyl group condensed with a cycloalkane (condensed to the benzene ring portion). Examples of the "diarylamino group" include the groups described above as the "first substituent."

[0112] Further, specific examples include polycyclic aromatic compounds represented by general formula (2) and R 2 is a diarylamino group fused with a cycloalkane (fused to the aryl group portion) or a carbazolyl group fused with a cycloalkane (fused to the benzene ring portion).

[0113] An example of this is a polycyclic aromatic compound represented by the following general formula (2-A), or a multimer of a polycyclic aromatic compound having a plurality of structures represented by the following general formula (2-A). In the following structural formula, Cy is a cycloalkane, n is an integer of 1 to 3 (preferably 1), and "=(Cy)n" means that n cycloalkanes are condensed at any position of the structure to be condensed (in the following structural formula, n cycloalkanes are condensed to a benzene ring (phenyl group)), and the definition of each symbol in the structural formula is the same as that of each symbol in general formula (2). [ka]

[0114] Specifically, compounds represented by the following formulae "1-Cy-(1)" to "1-Cy-(4401)" are included. In the following formulae, "Cy" represents a cycloalkane, and n is independently 0 to the maximum number that can be condensed (however, all n's are not 0), preferably 0 to 2 (however, all n's are not 0), more preferably 1, and "=(Cy)n" means that n cycloalkanes are condensed at any position of the structure to be condensed (for example, in the following formula "1-Cy-(1)", n cycloalkanes are condensed at any position of each benzene ring). In addition, in the following structural formulae, "OPh" represents a phenoxy group, "Me" represents a methyl group, and each compound may be substituted with the first and second substituents described above.

[0115] [ka]

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[0129] More specific examples of the cycloalkane-condensed polycyclic aromatic compound of the present invention include compounds represented by the following structural formulas. In the structural formulas below, "D" represents deuterium, "Me" represents a methyl group, "Et" represents an ethyl group, "iPr" represents an isopropyl group, "tBu" represents a t-butyl group, "tAm" represents a t-amyl group, "Ph" represents a phenyl group, "F" represents a fluorine group, "CN" represents a cyano group, "TMS" represents a trimethylsilyl group, and "TPhS" represents a triphenylsilyl group. In the structural formulas (1-1001) to (1-1265), the notation of the methyl group (Me) is omitted.

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[0323] In addition, (A) At least one of the rings A, B, and C in the above formula (1), and R in >NR is preferably a heteroaryl ring or a heteroaryl group, and the rings a, b, c, and R in the above formula (2) are preferably a heteroaryl ring or a heteroaryl group. 1 ~R 11 At least one of the rings formed together with the a, b or c ring by bonding adjacent groups among these, and R in >NR, is preferably a heteroaryl ring or a heteroaryl group. Also, (B) At least one "-C(-R)=" in the ring a, ring b, and ring c in the above formula (2) (wherein R is R in formula (2) 1 ~R 11 ) is replaced with "-N=" or at least one "-C(-R)=C(-R)-" (where R is R in formula (2) 1 ~R 11 It is preferred that the -N(-R)-, -O-, or -S- radical is replaced with -N(-R)-, -O-, or -S-. moreover, (C) At least one of "-C(-R)=C(-R)-" in the ring a, ring b, and ring c in the above formula (2) (wherein R is R in formula (2) 1 ~R 11 It is preferred that "-S-" is replaced with "-S-". The above (A) to (C) are Y 1 is B and X 1 and X 2 It is more preferable that >NR.

[0324] 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).

[0325] 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]

[0326] 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.

[0327] 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.

[0328] 2. Method for producing cycloalkane-condensed polycyclic aromatic compounds and their polymers The polycyclic aromatic compounds and their multimers represented by the general formula (1) or (2) are basically prepared by first bonding the A ring (a ring) to the B ring (b ring) and the C ring (c ring) through bonding groups (X 1 Or X 2 (a) to produce an intermediate (first reaction), and then, the A ring (a ring), the B ring (b ring) and the C ring (c ring) are bonded with a bonding group (Y 1 The final product can be produced by bonding with a group containing (second reaction). In the first reaction, for example, in the case of an etherification reaction, a general reaction such as a nucleophilic substitution reaction or an Ullmann reaction can be used, and in the case of an amination reaction, a general reaction such as a Buchwald-Hartwig reaction can be used. In addition, in the second reaction, a tandem hetero Friedel-Crafts reaction (sequential aromatic electrophilic substitution reaction, the same applies below) can be used. In addition, by using a cycloalkane-condensed raw material somewhere in these reaction steps or adding a step of condensing a cycloalkane, the compound of the present invention in which the desired position is condensed with a cycloalkane can be produced.

[0329] The second reaction is, as shown in the following schemes (1) and (2), a Y bond that bonds the A ring (ring a), the B ring (ring b), and the C ring (ring c). 1 This is a reaction that introduces Y 1 is a boron atom, X 1 and X 2 The case where X is an oxygen atom is shown below. First, 1 and X 2 The hydrogen atom between is orthometalated with n-butyllithium, sec-butyllithium, t-butyllithium, or the like. Then, boron trichloride, boron tribromide, or the like is added to carry out lithium-boron metal exchange, and then a tandem boron-Friedel-Crafts reaction can be carried out by adding a Bronsted base such as N,N-diisopropylethylamine to obtain the target compound. In the second reaction, a Lewis acid such as aluminum trichloride may be added to promote the reaction. The symbols in the structural formulae in the following schemes (1) and (2), and the subsequent schemes (3) to (28), are defined as above.

[0330] [ka] [ka]

[0331] The above schemes (1) and (2) mainly show the method for producing the polycyclic aromatic compounds represented by the general formulas (1) and (2), but the multimers can be produced by using intermediates having multiple A rings (a rings), B rings (b rings) and C rings (c rings). Details are explained in the following schemes (3) to (5). In this case, the target product can be obtained by doubling or tripling the amount of the reagent such as butyl lithium used.

[0332] [ka] [ka] [ka]

[0333] In the above scheme, lithium was introduced into the desired position by orthometalation. However, as in the following schemes (6) and (7), lithium can also be introduced into the desired position by introducing a bromine atom or the like into the desired position and then by halogen-metal exchange.

[0334] [ka] [ka]

[0335] In addition, in the method for producing a polymer explained in scheme (3), lithium can also be introduced into the desired position by introducing a halogen such as a bromine atom or a chlorine atom into the position where lithium is to be introduced as in the above schemes (6) and (7), and then by halogen-metal exchange (the following schemes (8), (9), and (10)).

[0336] [ka] [ka] [ka]

[0337] This method is useful because it allows the synthesis of the target compound even in cases where ortho-metallation is not possible due to the influence of substituents.

[0338] By appropriately selecting the above synthesis method and the raw materials to be used, the desired position is condensed with cycloalkane, and a substituent is provided at the desired position, and Y 1 is a boron atom, X 1 and X 2It is possible to synthesize polycyclic aromatic compounds and polymers thereof in which the ring is an oxygen atom.

[0339] Next, as an example, Y 1 is a boron atom, X 1 and X 2 The case where X is a nitrogen atom is shown in the following schemes (11) and (12). 1 and X 2 As in the case where X is an oxygen atom, first 1 and X 2 The hydrogen atom between is orthometalated with n-butyllithium or the like. Then, boron tribromide or the like is added to carry out lithium-boron metal exchange, and then a tandem boron-Friedel-Crafts reaction is carried out by adding a Bronsted base such as N,N-diisopropylethylamine to obtain the target compound. Here, a Lewis acid such as aluminum trichloride may be added to promote the reaction. In addition, by using a cycloalkane-condensed raw material somewhere in these reaction steps or by adding a step of condensing a cycloalkane, the compound of the present invention in which the desired position is condensed with a cycloalkane can be produced.

[0340] [ka] [ka]

[0341] Also, Y 1 is a boron atom, X 1 and X 2 For the polymers in which is a nitrogen atom, lithium can also be introduced to the desired position by introducing a halogen such as a bromine atom or a chlorine atom into the position where lithium is to be introduced as in the above schemes (6) and (7), and then by halogen-metal exchange (the following schemes (13), (14), and (15)).

[0342] [ka] [ka] [ka]

[0343] Next, as an example, Y 1 is phosphorus sulfide, phosphorus oxide or phosphorus atom, and X 1 and X 2 The cases where X is an oxygen atom are shown in the following schemes (16) to (19). 1 and X 2 The hydrogen atom between the two is orthometalated with n-butyllithium or the like. Next, phosphorus trichloride and sulfur are added in that order, and finally a Lewis acid such as aluminum trichloride and a Bronsted base such as N,N-diisopropylethylamine are added to carry out the tandem phospha-Friedel-Crafts reaction to give Y. 1 A compound in which Y is a phosphorus sulfide can be obtained. In addition, by treating the obtained phosphorus sulfide compound with m-chloroperbenzoic acid (m-CPBA), Y can be obtained. 1 is a phosphorus oxide, and by treating with triethylphosphine, Y 1 In addition, by using a cycloalkane-condensed raw material somewhere in these reaction steps or by adding a step of condensing a cycloalkane, the compound of the present invention in which the desired position is condensed with a cycloalkane can be produced.

[0344] [ka] [ka] [ka] [ka]

[0345] Also, Y 1is phosphorus sulfide, X 1 and X 2 For the polymers in which Y is an oxygen atom, lithium can be introduced to the desired position by introducing halogens such as bromine and chlorine atoms to the desired position as in the above schemes (6) and (7), and then by halogen-metal exchange (see the following schemes (20), (21), and (22)). 1 is phosphorus sulfide, X 1 and X 2 The polymers in which Y is an oxygen atom can also be obtained by treating Y with m-chloroperbenzoic acid (m-CPBA) as shown in schemes (18) and (19). 1 is a phosphorus oxide, and by treating with triethylphosphine, Y 1 It is possible to obtain a compound in which is a phosphorus atom.

[0346] [ka] [ka] [ka]

[0347] Here, Y 1 is B, P, P=O or P=S, and X 1 and X 2 Although the examples where is O or NR are described, by changing the raw material appropriately, Y 1 is Al, Ga, As, Si-R or Ge-R, or X 1 and X 2 Compounds in which is S can also be synthesized.

[0348] Specific examples of solvents that can be used in the above reactions include t-butylbenzene and xylene.

[0349] In addition, in the general formula (2), the substituents R 1 ~R 11Adjacent groups among the above may be bonded together to form an aryl or heteroaryl ring together with the a, b or c ring, and at least one hydrogen in the formed ring may be substituted with an aryl or heteroaryl. Therefore, the polycyclic aromatic compound represented by the general formula (2) has a ring structure that constitutes the compound, as shown in the formulas (2-1) and (2-2) of the following schemes (23) and (24), depending on the mutual bonding form of the substituents in the a, b and c rings. These compounds can be synthesized by applying the synthesis methods shown in the above schemes (1) to (19) to the intermediates shown in the following schemes (23) and (24). In addition, the compound of the present invention in which the desired position is condensed with a cycloalkane can be produced by using a raw material condensed with a cycloalkane somewhere in these reaction steps or adding a step of condensing a cycloalkane.

[0350] [ka] [ka]

[0351] The A' ring, the B' ring and the C' ring in the above formula (2-1) and formula (2-2) each independently represent a substituent R 1 ~R 11 Adjacent groups in the above are bonded to form an aryl or heteroaryl ring together with the a, b, and c rings (they can also be considered condensed rings formed by condensing the a, b, or c ring 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 A', B', and C' rings.

[0352] In addition, the provision in the general formula (2) that "at least one of R of the >NR and R of the >C(-R)2 is bonded to at least one of the ring a, ring b and ring c by -O-, -S-, -C(-R)2- or a single bond" is intended to mean X 1 Or X 2Compounds having a ring structure in which X is incorporated into the fused ring B' and the fused ring C', and compounds represented by formula (2-3-2) or formula (2-3-3), 1 Or X 2 can be expressed as a compound having a ring structure in which is incorporated into the fused ring A'. These compounds can be synthesized by applying the synthesis methods shown in the above schemes (1) to (19) to the intermediates shown in the following scheme (25). In addition, by using a raw material fused with a cycloalkane somewhere in these reaction steps or adding a step of condensing a cycloalkane, the compound of the present invention in which a desired position is fused with a cycloalkane can be produced.

[0353] [ka]

[0354] In the above synthesis schemes (1) to (17) and (20) to (25), before adding boron trichloride, boron tribromide, etc., X 1 and X 2 In the example shown here, the hydrogen atom (or halogen atom) between the rings was ortho-metallated with butyllithium or the like to perform the tandem hetero Friedel-Crafts reaction. However, the reaction can also be carried out by adding boron trichloride, boron tribromide, or the like without ortho-metallation using butyllithium or the like.

[0355] Also, Y 1 In the case of phosphorus-based, X is as shown in the following schemes (26) and (27). 1 and X 2The hydrogen atom between (O in the following formula) is orthometalated with n-butyllithium, sec-butyllithium, t-butyllithium, or the like, and then bisdiethylaminochlorophosphine is added to carry out lithium-phosphorus metal exchange, followed by adding a Lewis acid such as aluminum trichloride to carry out a tandem phosphine Friedel-Crafts reaction to obtain the target product. This reaction method is also described in International Publication No. 2010 / 104047 (e.g., page 27). In addition, by using a cycloalkane-condensed raw material somewhere in these reaction steps or adding a step of condensing a cycloalkane, the compound of the present invention in which the desired position is condensed with a cycloalkane can be produced.

[0356] [ka] [ka]

[0357] In the above schemes (26) and (27), a polymeric compound can be synthesized by using an orthometalation reagent such as butyllithium in a molar amount two or three times that of intermediate 1. In addition, a halogen such as a bromine atom or a chlorine atom is first introduced into the position where a metal such as lithium is to be introduced, and then a metal can be introduced into the desired position by halogen-metal exchange.

[0358] In addition, for the polycyclic aromatic compound represented by general formula (2-A), a cycloalkane-condensed intermediate can be synthesized and cyclized to synthesize a polycyclic aromatic compound condensed with a cycloalkane at a desired position, as shown in the following scheme (28). In scheme (28), X represents a halogen or hydrogen, and the definitions of the other symbols are the same as those of the symbols in general formula (2).

[0359] [ka]

[0360] The intermediate before cyclization in scheme (28) can also be synthesized by the method shown in scheme (1) etc. In other words, by appropriately combining the Buchwald-Hartwig reaction, Suzuki coupling reaction, or etherification reaction by nucleophilic substitution reaction, Ullmann reaction etc., an intermediate having a desired substituent can be synthesized. In these reactions, the raw material that becomes the cycloalkane condensed precursor can also be a commercially available product.

[0361] The compound of general formula (2-A) having a cycloalkane-condensed diphenylamino group can also be synthesized by the following method. That is, after introducing a cycloalkane-condensed diphenylamino group by an amination reaction such as the Buchwald-Hartwig reaction between a cycloalkane-condensed bromobenzene and a trihalogenated aniline, X 1 , X 2 When is NR, X can be used in an amination reaction such as the Buchwald-Hartwig reaction. 1 , X 2 When is O, it is possible to synthesize a compound of general formula (2-A) by tandem boron-Friedel-Crafts reaction using a metallation reagent such as butyllithium to convert the intermediate (M-3), a boron halide such as boron tribromide, and a Brønsted base such as diethylisopropylamine. These reactions can also be applied to other cycloalkane-fused compounds.

[0362] Examples of the ortho-metallation reagent used in the above schemes (1) to (28) include alkyllithiums such as methyllithium, n-butyllithium, sec-butyllithium, and t-butyllithium; organic alkali compounds such as lithium diisopropylamide, lithium tetramethylpiperidide, lithium hexamethyldisilazide, and potassium hexamethyldisilazide; and dispersed alkali metals such as organic solvent-dispersed Na.

[0363] The metal-Y used in the above schemes (1) to (28) 1 The metal exchange reagent for Y 1 trifluoride, Y 1 trichloride, Y 1 Tribromide of Y 1 of triiodide, etc. 1 Halides of Y such as CIPN(NEt2)2 1 Aminated halides of Y 1 Alkoxylated compounds of Y 1 and aryloxy compounds of the above.

[0364] Examples of the Bronsted base used in the above schemes (1) to (28) include N,N-diisopropylethylamine, triethylamine, 2,2,6,6-tetramethylpiperidine, 1,2,2,6,6-pentamethylpiperidine, N,N-dimethylaniline, N,N-dimethyltoluidine, 2,6-lutidine, sodium tetraphenylborate, potassium tetraphenylborate, triphenylborane, tetraphenylsilane, Ar4BNa, Ar4BK, Ar3B, and Ar4Si (Ar is an aryl such as phenyl).

[0365] Examples of Lewis acids used in the above schemes (1) to (28) include AlCl3, AlBr3, AlF3, BF3·OEt2, BCl3, BBr3, GaCl3, GaBr3, InCl3, InBr3, In(OTf)3, SnCl4, SnBr4, AgOTf, ScCl3, Sc(OTf)3, ZnCl2, ZnBr2, Zn(OTf)2, MgCl2, MgBr2, Mg(OTf)2, LiOTf, NaOTf, KOTf, Me3SiOTf, Cu(OTf)2, CuCl2, YCl3, Y(OTf)3, TiCl4, TiBr4, ZrCl4, ZrBr4, FeCl3, FeBr3, CoCl3, and CoBr3.

[0366] In the above schemes (1) to (28), a Brønsted base or Lewis acid may be used to promote the tandem hetero Friedel-Crafts reaction. 1 trifluoride, Y 1trichloride, Y 1 Tribromide of Y 1 of triiodide, etc. 1 When using halides of Y, acids such as hydrogen fluoride, hydrogen chloride, hydrogen bromide, and hydrogen iodide are generated as the aromatic electrophilic substitution reaction proceeds, so the use of a Brønsted base to capture the acid is effective. 1 Aminated halides of Y 1 When an alkoxylated compound of the above is used, since amines and alcohols are produced as the aromatic electrophilic substitution reaction proceeds, it is often not necessary to use a Brønsted base. However, since the amino and alkoxy groups have low ability to be eliminated, it is effective to use a Lewis acid that promotes their elimination.

[0367] The polycyclic aromatic compound and its multimer of the present invention also include compounds in which at least a portion of hydrogen atoms is substituted with deuterium or cyano, or compounds in which hydrogen atoms are substituted with halogens such as fluorine or chlorine. Such compounds can be synthesized in the same manner as described above by using raw materials in which desired positions are deuterated, cyanated, fluorinated or chlorinated.

[0368] 3. Organic Devices The cycloalkane-condensed polycyclic aromatic compound according to the present invention can be used as a material for an organic device, such as an organic electroluminescent device, an organic field effect transistor, or an organic thin-film solar cell.

[0369] 3-1. Organic electroluminescent device The organic EL element 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 the organic EL element according to the present embodiment.

[0370] <Structure of organic electroluminescent device> The organic EL element 100 shown in FIG. 1 has a substrate 101, an anode 102 provided on the substrate 101, a hole injection layer 103 provided on the anode 102, a hole transport layer 104 provided on the hole injection layer 103, an emitting layer 105 provided on the hole transport layer 104, an electron transport layer 106 provided on the emitting layer 105, an electron injection layer 107 provided on the electron transport layer 106, and a cathode 108 provided on the electron injection layer 107.

[0371] The organic EL element 100 may be fabricated in the reverse order, for example, to have a substrate 101, a cathode 108 provided on the substrate 101, an electron injection layer 107 provided on the cathode 108, an electron transport layer 106 provided on the electron injection layer 107, an emitting layer 105 provided on the electron transport layer 106, a hole transport layer 104 provided on the emitting layer 105, a hole injection layer 103 provided on the hole transport layer 104, and an anode 102 provided on the hole injection layer 103.

[0372] 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.

[0373] In addition to the above-mentioned "substrate / anode / hole injection layer / hole transport layer / light-emitting layer / electron transport layer / electron injection layer / cathode" configuration, the layers constituting the organic EL element may be configured as "substrate / anode / hole transport layer / light-emitting layer / electron transport layer / electron injection layer / cathode", "substrate / anode / hole injection ...hole transport layer / light-emitting layer / electron injection layer / cathode", "substrate / anode / hole injection layer / hole transport layer / light-emitting layer / electron injection layer / cathode", or "substrate / anode / hole injection layer / hole transport layer / light-emitting layer / electron transport The configuration may be, for example, "substrate / anode / light-emitting layer / electron transport layer / electron injection layer / cathode", "substrate / anode / hole transport layer / light-emitting layer / electron injection layer / cathode", "substrate / anode / hole transport layer / light-emitting layer / electron transport layer / cathode", "substrate / anode / hole transport layer / light-emitting layer / electron injection layer / cathode", "substrate / anode / hole injection layer / light-emitting layer / electron injection layer / cathode", "substrate / anode / hole injection layer / light-emitting layer / electron transport layer / cathode", "substrate / anode / hole injection layer / light-emitting layer / electron transport layer / cathode", "substrate / anode / light-emitting layer / electron transport layer / cathode", or "substrate / anode / light-emitting layer / electron injection layer / cathode".

[0374] <Substrate for organic electroluminescence device> The substrate 101 is a support for the organic EL element 100, and is usually made of quartz, glass, metal, plastic, or the like. The substrate 101 is formed into a plate, film, or sheet shape depending on the purpose, and for example, a glass plate, a metal plate, a metal foil, a plastic film, a plastic sheet, or the like is used. Among them, a glass plate and a plate made of a transparent synthetic resin such as polyester, polymethacrylate, polycarbonate, or polysulfone are preferable. For a glass substrate, soda-lime glass or alkali-free glass is used, and the thickness is sufficient to maintain mechanical strength, so that it may be, for example, 0.2 mm or more. The upper limit of the thickness is, for example, 2 mm or less, preferably 1 mm or less. As for the material of the glass, it is preferable that the amount of ions eluted from the glass is small, so alkali-free glass is preferable, but soda-lime glass with a barrier coat such as SiO2 is also commercially available, and this can be used. In addition, in order to improve the gas barrier properties of the substrate 101, a gas barrier film such as a dense silicon oxide film may be provided on at least one side thereof. It is particularly preferable to provide a gas barrier film when a synthetic resin plate, film or sheet having poor gas barrier properties is used as the substrate 101.

[0375] <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.

[0376] Materials for forming the anode 102 include inorganic compounds and organic compounds. Examples of inorganic compounds include metals (aluminum, gold, silver, nickel, palladium, chromium, etc.), metal oxides (indium oxide, tin oxide, indium-tin oxide (ITO), indium-zinc oxide (IZO), etc.), metal halides (copper iodide, etc.), copper sulfide, carbon black, ITO glass, and Nesa glass. Examples of organic compounds include polythiophenes such as poly(3-methylthiophene), polypyrrole, polyaniline, and other conductive polymers. In addition, materials that are used as anodes in organic EL elements can be appropriately selected and used.

[0377] 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.

[0378] <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.

[0379] 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.

[0380] As the material for forming the hole injection layer 103 and the hole transport layer 104, any compound can be selected from compounds conventionally used as charge transport materials for holes in photoconductive materials, p-type semiconductors, and known compounds used in hole injection layers and hole transport layers of organic EL elements. Specific examples of such compounds include carbazole derivatives (N-phenylcarbazole, polyvinylcarbazole, etc.), biscarbazole derivatives such as bis(N-arylcarbazole) or bis(N-alkylcarbazole), triarylamine derivatives (polymers having an aromatic tertiary amino in the main chain or side chain, 1,1-bis(4-di-p-tolylaminophenyl)cyclohexane, N,N'-diphenyl-N,N'-di(3-methylphenyl)-4,4'-diaminobiphenyl, N,N'-diphenyl-N,N'-dinaphthyl-4,4'-diaminobiphenyl, N,N'-diphenyl-N,N'-di(3-methylphenyl)-4,4'-diphenyl-1,1'-diamine, N,N'-dinaphthyl-N,N'-diphenyl-4,4'-diphenyl-1,1'-diamine, N4 ,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.

[0381] 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 are known, for example, benzidine derivatives (TPD, etc.) or starburst amine derivatives (TDATA, etc.), or certain metal phthalocyanines (especially zinc phthalocyanine (ZnPc) and the like) (JP 2005-167175 A).

[0382] 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.

[0383] <Light-emitting layer in organic electroluminescent device> The light-emitting layer 105 is a layer that emits light by recombining holes injected from the anode 102 and electrons injected from the cathode 108 between electrodes to which an electric field is applied. The material for forming the light-emitting layer 105 may be a compound (light-emitting compound) that is excited 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 material for the light-emitting layer may be a host material and, for example, a polycyclic aromatic compound represented by the above general formula (1) as a dopant material.

[0384] The light-emitting layer may be a single layer or multiple layers, each of which is formed from materials for the light-emitting layer (host material, dopant material). The host material and the dopant material may each be one type or a combination of multiple types. The dopant material may be contained in the entire host material or may be contained partially in the host material. As a doping method, the dopant material may be formed by co-evaporation with the host material, but it may also be mixed with the host material in advance and then vapor-deposited at the same time.

[0385] 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.

[0386] 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.

[0387] Examples of the host material include condensed ring derivatives such as anthracene, pyrene, dibenzochrysene, and fluorene, which have been known as light emitters, bisstyryl derivatives such as bisstyrylanthracene derivatives and distyrylbenzene derivatives, tetraphenylbutadiene derivatives, and cyclopentadiene derivatives. In particular, anthracene-based compounds, fluorene-based compounds, and dibenzochrysene-based compounds are preferred.

[0388] <Anthracene compounds> The anthracene compound as the host is, for example, a compound represented by the following general formula (3). [ka]

[0389] In formula (3), X and Ar 4 are each independently hydrogen, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted diarylamino, optionally substituted diheteroarylamino, optionally substituted arylheteroarylamino, optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted alkenyl, optionally substituted alkoxy, optionally substituted aryloxy, optionally substituted arylthio or optionally substituted silyl; and all X and Ar 4 cannot simultaneously become hydrogen, At least one hydrogen in the compound represented by formula (3) may be substituted with halogen, cyano, deuterium or an optionally substituted heteroaryl.

[0390] In addition, a polymer (preferably a dimer) may be formed using the structure represented by formula (3) as a unit structure. In this case, for example, the unit structures represented by formula (3) may be bonded to each other via X, and examples of X include a single bond, arylene (phenylene, biphenylene, naphthylene, etc.), and heteroarylene (a group having a divalent bond such as a pyridine ring, a dibenzofuran ring, a dibenzothiophene ring, a carbazole ring, a benzocarbazole ring, and a phenyl-substituted carbazole ring).

[0391] The details of the above aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, alkyl, cycloalkyl, alkenyl, alkoxy, aryloxy, arylthio, or silyl will be described in the following preferred embodiment section. The substituents on these include aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, alkyl, cycloalkyl, alkenyl, alkoxy, aryloxy, arylthio, or silyl, and the details of these are also described in the following preferred embodiment section.

[0392] Preferred embodiments of the above anthracene-based compounds are described below. The symbols in the structures below are defined as above. [ka]

[0393] In the general formula (3), X is each independently a group represented by the above formula (3-X1), formula (3-X2) or formula (3-X3), and the group represented by formula (3-X1), formula (3-X2) or formula (3-X3) is bonded to the anthracene ring of formula (3) at *. Preferably, two Xs are not simultaneously a group represented by formula (3-X3). More preferably, two Xs are not simultaneously a group represented by formula (3-X2).

[0394] In addition, a polymer (preferably a dimer) may be formed using the structure represented by formula (3) as a unit structure. In this case, for example, the unit structures represented by formula (3) may be bonded to each other via X, and examples of X include a single bond, arylene (phenylene, biphenylene, naphthylene, etc.), and heteroarylene (a group having a divalent bond such as a pyridine ring, a dibenzofuran ring, a dibenzothiophene ring, a carbazole ring, a benzocarbazole ring, and a phenyl-substituted carbazole ring).

[0395] The naphthylene moieties in formula (3-X1) and formula (3-X2) may be condensed with one benzene ring. The condensed structures are as follows: [ka]

[0396] Ar 1 and Ar 2 are each independently hydrogen, phenyl, biphenylyl, terphenylyl, quaterphenylyl, naphthyl, phenanthryl, fluorenyl, benzofluorenyl, chrysenyl, triphenylenyl, pyrenylyl, or a group represented by the above formula (A) (including a carbazolyl group, a benzocarbazolyl group, and a phenyl-substituted carbazolyl group). 1 or Ar 2 is a group represented by formula (A), the group represented by formula (A) is bonded to the naphthalene ring in formula (3-X1) or formula (3-X2) at the *.

[0397] Ar 3 is phenyl, biphenylyl, terphenylyl, quaterphenylyl, naphthyl, phenanthryl, fluorenyl, benzofluorenyl, chrysenyl, triphenylenyl, pyrenylyl, or a group represented by the above formula (A) (including a carbazolyl group, a benzocarbazolyl group, and a phenyl-substituted carbazolyl group). 3is a group represented by formula (A), the group represented by formula (A) is bonded to the single bond represented by a straight line in formula (3-X3) at the *. That is, the anthracene ring in formula (3) and the group represented by formula (A) are directly bonded.

[0398] Also, Ar 3 may have a substituent, and Ar 3 At least one hydrogen atom in may be further substituted with an alkyl group having 1 to 4 carbon atoms, a cycloalkyl group having 5 to 10 carbon atoms, phenyl, biphenylyl, terphenylyl, naphthyl, phenanthryl, fluorenyl, chrysenyl, triphenylenyl, pyrenylyl, or a group represented by the above formula (A) (including a carbazolyl group and a phenyl-substituted carbazolyl group). 3 is a group represented by formula (A), the group represented by formula (A) is Ar 3 and combine.

[0399] Ar 4 are each independently hydrogen, phenyl, biphenylyl, terphenylyl, naphthyl, or silyl substituted with alkyl having 1 to 4 carbon atoms (eg, methyl, ethyl, t-butyl) and / or cycloalkyl having 5 to 10 carbon atoms.

[0400] Examples of the alkyl group having 1 to 4 carbon atoms that substitutes for the silyl include methyl, ethyl, propyl, i-propyl, butyl, sec-butyl, t-butyl, and cyclobutyl, and three hydrogen atoms in the silyl are each independently substituted with these alkyl groups.

[0401] Specific examples of "silyl substituted with alkyl having 1 to 4 carbon atoms" include trimethylsilyl, triethylsilyl, tripropylsilyl, tri-i-propylsilyl, tributylsilyl, tri-sec-butylsilyl, tri-t-butylsilyl, ethyldimethylsilyl, propyldimethylsilyl, i-propyldimethylsilyl, butyldimethylsilyl, sec-butyldimethylsilyl, t-butyldimethylsilyl, methyldiethylsilyl, propyldiethylsilyl, i-propyldiethylsilyl, butyldiethylsilyl, sec-butyldiethylsilyl, t-butyldiethylsilyl, methyldipropylsilyl, ethyldipropylsilyl, butyldipropylsilyl, sec-butyldipropylsilyl, t-butyldipropylsilyl, methyldi-i-propylsilyl, ethyldi-i-propylsilyl, butyldi-i-propylsilyl, sec-butyldi-i-propylsilyl, and t-butyldi-i-propylsilyl.

[0402] Examples of the cycloalkyl having 5 to 10 carbon atoms substituting the silyl include cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, norbornenyl, bicyclo[1.1.1]pentyl, bicyclo[2.0.1]pentyl, bicyclo[1.2.1]hexyl, bicyclo[3.0.1]hexyl, bicyclo[2.1.2]heptyl, bicyclo[2.2.2]octyl, adamantyl, decahydronaphthalenyl, and decahydroazulenyl, and three hydrogen atoms in the silyl are each independently substituted with these cycloalkyls.

[0403] Specific examples of the "silyl substituted with cycloalkyl having 5 to 10 carbon atoms" include tricyclopentylsilyl and tricyclohexylsilyl.

[0404] Substituted silyls include dialkylcycloalkylsilyls, which are substituted with two alkyl groups and one cycloalkyl group, and alkyldicycloalkylsilyls, which are substituted with one alkyl group and two cycloalkyl groups. Specific examples of the alkyl and cycloalkyl groups are as described above.

[0405] In addition, hydrogen in the chemical structure of the anthracene compound represented by general formula (3) may be substituted with a group represented by the above formula (A). When substituted with a group represented by formula (A), the group represented by formula (A) replaces at least one hydrogen in the compound represented by formula (3) at the *.

[0406] The group represented by formula (A) is one of the substituents that the anthracene compound represented by formula (3) can have. [ka]

[0407] In the above formula (A), Y is -O-, -S- or >NR 29 and R 21 ~R 28 are each independently hydrogen, optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted alkoxy, optionally substituted aryloxy, optionally substituted arylthio, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, alkyldicycloalkylsilyl, optionally substituted amino, halogen, hydroxy or cyano; R 21 ~R 28 adjacent groups among R may be bonded to each other to form a hydrocarbon ring, an aryl ring, or a heteroaryl ring; 29 is hydrogen or optionally substituted aryl.

[0408] R 21 ~R 28The "alkyl" in the "optionally substituted alkyl" may be either linear or branched, and examples thereof include linear alkyl having 1 to 24 carbon atoms or branched alkyl having 3 to 24 carbon atoms. An alkyl having 1 to 18 carbon atoms (branched alkyl having 3 to 18 carbon atoms) is preferred, an alkyl having 1 to 12 carbon atoms (branched alkyl having 3 to 12 carbon atoms) is more preferred, an alkyl having 1 to 6 carbon atoms (branched alkyl having 3 to 6 carbon atoms) is even more preferred, and an alkyl having 1 to 4 carbon atoms (branched alkyl having 3 to 4 carbon atoms) is particularly preferred.

[0409] 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 group include n-hexyl, n-butyl, n-hexyl, 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.

[0410] R 21 ~R 28 Examples of the "cycloalkyl" in the "optionally substituted cycloalkyl" include cycloalkyl having 3 to 24 carbon atoms, cycloalkyl having 3 to 20 carbon atoms, cycloalkyl having 3 to 16 carbon atoms, cycloalkyl having 3 to 14 carbon atoms, cycloalkyl having 5 to 10 carbon atoms, cycloalkyl having 5 to 8 carbon atoms, cycloalkyl having 5 to 6 carbon atoms, and cycloalkyl having 5 carbon atoms.

[0411] Specific examples of "cycloalkyl" include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, and alkyl (especially methyl) substituted derivatives of these having 1 to 4 carbon atoms, as well as norbornenyl, bicyclo[1.0.1]butyl, bicyclo[1.1.1]pentyl, bicyclo[2.0.1]pentyl, bicyclo[1.2.1]hexyl, bicyclo[3.0.1]hexyl, bicyclo[2.1.2]heptyl, bicyclo[2.2.2]octyl, adamantyl, diamantyl, decahydronaphthalenyl, and decahydroazulenyl.

[0412] R 21 ~R 28 In the above, the "aryl" in the "optionally substituted aryl" includes, for example, aryl having 6 to 30 carbon atoms, preferably aryl having 6 to 16 carbon atoms, more preferably aryl having 6 to 12 carbon atoms, and particularly preferably aryl having 6 to 10 carbon atoms.

[0413] Specific examples of "aryl" include a monocyclic ring system such as phenyl, a bicyclic ring system such as biphenylyl, a fused bicyclic ring system such as naphthyl, a tricyclic ring system such as terphenylyl (m-terphenylyl, o-terphenylyl, p-terphenylyl), a fused tricyclic ring system such as acenaphthylenyl, fluorenyl, phenalenyl, and phenanthrenyl, a fused tetracyclic ring system such as triphenylenyl, pyrenyl, and naphthacenyl, and a fused pentacyclic ring system such as perylenyl and pentacenyl.

[0414] R 21 ~R 28 Examples of the "heteroaryl" in the "optionally substituted heteroaryl" include heteroaryl having 2 to 30 carbon atoms, preferably heteroaryl having 2 to 25 carbon atoms, more preferably heteroaryl having 2 to 20 carbon atoms, further preferably heteroaryl having 2 to 15 carbon atoms, and particularly preferably heteroaryl having 2 to 10 carbon atoms. Examples of the heteroaryl include heterocycles containing, as ring-constituting atoms other than carbon, 1 to 5 heteroatoms selected from oxygen, sulfur, and nitrogen.

[0415] Specific examples of "heteroaryl" include pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, oxadiazolyl, thiadiazolyl, triazolyl, tetrazolyl, pyrazolyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, indolyl, isoindolyl, 1H-indazolyl, benzimidazolyl, benzoxazolyl, benzothiazolyl, 1H-benzotriazolyl, quinolyl, isoquinolyl, cinnolyl, quinazolyl, quinoxalinyl, phthalazinyl, naphthyridinyl, purinyl, pteridinyl, carbazolyl, acridin ... Examples of such radicals include 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.

[0416] R 21 ~R 28 Examples of the "alkoxy" in the "optionally substituted alkoxy" include linear alkoxy having 1 to 24 carbon atoms or branched alkoxy having 3 to 24 carbon atoms. An alkoxy having 1 to 18 carbon atoms (branched alkoxy having 3 to 18 carbon atoms) is preferred, an alkoxy having 1 to 12 carbon atoms (branched alkoxy having 3 to 12 carbon atoms) is more preferred, an alkoxy having 1 to 6 carbon atoms (branched alkoxy having 3 to 6 carbon atoms) is even more preferred, and an alkoxy having 1 to 4 carbon atoms (branched alkoxy having 3 to 4 carbon atoms) is particularly preferred.

[0417] Specific examples of "alkoxy" include methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, s-butoxy, t-butoxy, pentyloxy, hexyloxy, heptyloxy, octyloxy, and the like.

[0418] R 21 ~R 28 The "aryloxy" in the "optionally substituted aryloxy" is a group in which the hydrogen of the -OH group is replaced by an aryl, and this aryl is one of the above-mentioned R 21 ~R 28 The group described as "aryl" in the above formula can be used.

[0419] R 21 ~R 28 The "arylthio" in the "optionally substituted arylthio" is a group in which the hydrogen of the -SH group is replaced by an aryl, and this aryl is the same as R 21 ~R 28 The group described as "aryl" in the above formula can be used.

[0420] R 21 ~R 28 The "trialkylsilyl" in the above formula is a silyl group in which each of the three hydrogen atoms is independently replaced by an alkyl group, and the alkyl group is the same as R 21 ~R 28 The groups described as "alkyl" in the above can be cited. Preferred alkyl groups for substitution are alkyl groups having 1 to 4 carbon atoms, and specific examples thereof include methyl, ethyl, propyl, i-propyl, butyl, sec-butyl, t-butyl, and cyclobutyl.

[0421] Specific examples of the "trialkylsilyl" include trimethylsilyl, triethylsilyl, tripropylsilyl, tri-i-propylsilyl, tributylsilyl, tri-sec-butylsilyl, tri-t-butylsilyl, ethyldimethylsilyl, propyldimethylsilyl, i-propyldimethylsilyl, butyldimethylsilyl, sec-butyldimethylsilyl, t-butyldimethylsilyl, methyldiethylsilyl, propyldiethylsilyl, i-propyldiethylsilyl, butyldiethylsilyl, sec-butyldiethylsilyl, t-butyldiethylsilyl, methyldipropylsilyl, ethyldipropylsilyl, butyldipropylsilyl, sec-butyldipropylsilyl, t-butyldipropylsilyl, methyldi-i-propylsilyl, ethyldi-i-propylsilyl, butyldi-i-propylsilyl, sec-butyldi-i-propylsilyl, and t-butyldi-i-propylsilyl.

[0422] R 21 ~R 28 The "tricycloalkylsilyl" in the above formula is a silyl group in which each of the three hydrogen atoms is independently replaced by a cycloalkyl, and the cycloalkyl is the same as R 21 ~R 28 The groups described as "cycloalkyl" in the above can be cited. Preferred cycloalkyl for substitution is cycloalkyl having 5 to 10 carbon atoms, and specific examples thereof include cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, bicyclo[1.1.1]pentyl, bicyclo[2.0.1]pentyl, bicyclo[1.2.1]hexyl, bicyclo[3.0.1]hexyl, bicyclo[2.1.2]heptyl, bicyclo[2.2.2]octyl, adamantyl, decahydronaphthalenyl, and decahydroazulenyl.

[0423] Specific examples of the "tricycloalkylsilyl" include tricyclopentylsilyl, tricyclohexylsilyl, and the like.

[0424] Specific examples of dialkylcycloalkylsilyl substituted with two alkyls and one cycloalkyl and alkyldicycloalkylsilyl substituted with one alkyl and two cycloalkyls include silyl substituted with a group selected from the specific alkyls and cycloalkyls mentioned above.

[0425] R 21 ~R 28 The "substituted amino" in the "optionally substituted amino" in the above is, for example, an amino group in which two hydrogen atoms are substituted with aryl or heteroaryl. An amino group in which two hydrogen atoms are substituted with aryl is a diaryl-substituted amino, an amino group in which two hydrogen atoms are substituted with heteroaryl is a diheteroaryl-substituted amino, and an amino group in which two hydrogen atoms are substituted with an aryl and a heteroaryl is an arylheteroaryl-substituted amino. The aryl and heteroaryl are as defined above in R 21 ~R 28 The groups described above as "aryl" and "heteroaryl" can be cited.

[0426] Specific examples of the "substituted amino" include diphenylamino, dinaphthylamino, phenylnaphthylamino, dipyridylamino, phenylpyridylamino, naphthylpyridylamino, and the like.

[0427] R 21 ~R 28 "Halogen" in the above formula includes fluorine, chlorine, bromine, and iodine.

[0428] R 21 ~R 28 Some of the groups described as may be substituted as described above, in which case the substituents include alkyl, cycloalkyl, aryl, or heteroaryl. The alkyl, cycloalkyl, aryl, or heteroaryl may be any of the groups described above as R 21 ~R 28 In the above, reference can be made to a group described as "alkyl", "cycloalkyl", "aryl" or "heteroaryl".

[0429] Y as 'NR' 29 " R in 29 is hydrogen or an optionally substituted aryl, and the aryl is as defined above in R 21 ~R 28 The group described as "aryl" in the above formula can be cited, and the substituents thereof include R 21 ~R 28 The groups described above as substituents for the above can be cited.

[0430] R 21 ~R 28 Among these, adjacent groups may be bonded to each other to form a hydrocarbon ring, an aryl ring, or a heteroaryl ring. The group represented by the following formula (A-1) does not form a ring, and the group represented by any of the following formulas (A-2) to (A-14) may form a ring. In the formulas, Y and * are defined as above. In the group represented by any of formulas (A-1) to (A-14), at least one hydrogen atom may be substituted with an alkyl, cycloalkyl, aryl, heteroaryl, alkoxy, aryloxy, arylthio, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, alkyldicycloalkylsilyl, diaryl-substituted amino, diheteroaryl-substituted amino, arylheteroaryl-substituted amino, halogen, hydroxy, or cyano. In each structural formula, * indicates a bonding position. [ka]

[0431] Examples of rings formed by bonding adjacent groups to each other include a hydrocarbon ring such as a cyclohexane ring, and examples of aryl and heteroaryl rings include the above-mentioned R 21 ~R 28 Examples of the ring structures include those described for "aryl" and "heteroaryl" in the above formula (A-1), and these rings are formed so as to be condensed with one or two benzene rings in the above formula (A-1).

[0432] Examples of the group represented by formula (A) include groups represented by any of the above formulas (A-1) to (A-14). Groups represented by any of the above formulas (A-1) to (A-5) and (A-12) to (A-14) are preferred. Groups represented by any of the above formulas (A-1) to (A-4) are more preferred. Groups represented by any of the above formulas (A-1), (A-3) and (A-4) are even more preferred. Groups represented by the above formula (A-1) are particularly preferred.

[0433] The group represented by formula (A) is a naphthalene ring in formula (3-X1) or formula (3-X2), a single bond in formula (3-X3), Ar in formula (3-X3), 3 As described above, the naphthalene ring in formula (3-X1) or formula (3-X2), the single bond in formula (3-X3), and Ar in formula (3-X3) are substituted with at least one hydrogen atom in the compound represented by formula (3). 3 A form in which the compound is bound to at least one of the above is preferred.

[0434] In addition, in the structure of the group represented by formula (A), the naphthalene ring in formula (3-X1) or formula (3-X2), the single bond in formula (3-X3), Ar in formula (3-X3), 3 The position at which R is bonded, and the position at which at least one hydrogen atom in the compound represented by formula (3) is substituted in the structure of the group represented by formula (A), may be any position in the structure of formula (A), for example, any of the two benzene rings in the structure of formula (A) or R 21 ~R 28 Any of the rings formed by bonding adjacent groups to each other, or ">NR 29 " R in 29 The bond can be at any position within the

[0435] Examples of the group represented by formula (A) include the following groups: In the formula, Y and * are defined as above. [ka] [ka]

[0436] All or a part of the hydrogen atoms in the chemical structure of the anthracene compound represented by the general formula (3) may be deuterium atoms.

[0437] Specific examples of the anthracene-based compound include compounds represented by any of the following formulae (3-1) to (3-142): In the following structural formulae, "Me" represents a methyl group, "D" represents deuterium, and "tBu" represents a t-butyl group.

[0438] [ka]

[0439] [ka]

[0440] [ka]

[0441] [ka]

[0442] [ka]

[0443] [ka]

[0444] [ka]

[0445] The anthracene compound represented by formula (3) is a compound having a reactive group at a desired position of an anthracene skeleton, and X, Ar 4 The compound having a reactive group in a partial structure such as the structure of formula (A) can be used as a starting material to produce the compound by applying Suzuki coupling, Negishi coupling, or other known coupling reactions. Examples of reactive groups in these reactive compounds include halogens and boronic acids. As a specific production method, for example, the synthesis methods in paragraphs

[0089] to

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

[0446] <Fluorene-based compounds> The compound represented by the general formula (4) basically functions as a host. [ka]

[0447] In the above formula (4), R 1 From R 10 are each independently a hydrogen atom, an aryl atom, a heteroaryl atom (wherein the heteroaryl atom may be bonded to the fluorene skeleton in the above formula (4) via a linking group), a diarylamino atom, a diheteroarylamino atom, an arylheteroarylamino atom, an alkyl atom, a cycloalkyl atom, an alkenyl atom, an alkoxy atom, or an aryloxy atom, in which at least one hydrogen atom may be substituted with an aryl atom, a heteroaryl atom, an alkyl atom, or a cycloalkyl atom; Also, R 1 and R 2 , R 2 and R 3 , R 3 and R 4 , R 5 and R 6 , R 6 and R 7 , R 7 and R 8 or R 9 and R 10may each independently bond to form a fused ring or a spiro ring, at least one hydrogen in the formed ring may be replaced with an aryl, a heteroaryl (the heteroaryl may be bonded to the formed ring via a linking group), a diarylamino, a diheteroarylamino, an arylheteroarylamino, an alkyl, a cycloalkyl, an alkenyl, an alkoxy, or an aryloxy, at least one hydrogen in these may be replaced with an aryl, a heteroaryl, an alkyl, or a cycloalkyl, and At least one hydrogen in the compound represented by formula (4) may be substituted with halogen, cyano or deuterium.

[0448] For details of each group in the definition of the above formula (4), the explanation for the polycyclic aromatic compound of the above formula (1) can be cited.

[0449] R 1 From R 10 Examples of the alkenyl in the above formula include alkenyl having 2 to 30 carbon atoms, preferably alkenyl having 2 to 20 carbon atoms, more preferably alkenyl having 2 to 10 carbon atoms, further preferably alkenyl having 2 to 6 carbon atoms, and particularly preferably alkenyl having 2 to 4 carbon atoms. Preferred alkenyls are vinyl, 1-propenyl, 2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, or 5-hexenyl.

[0450] Specific examples of heteroaryl include monovalent groups represented by removing any one hydrogen atom from a compound of the following formula (4-Ar1), formula (4-Ar2), formula (4-Ar3), formula (4-Ar4), or formula (4-Ar5). [ka] In formulas (4-Ar1) to (4-Ar5), Y 1are each independently O, S or NR, R is phenyl, biphenylyl, naphthyl, anthracenyl or hydrogen; At least one hydrogen atom in the structures of the above formulae (4-Ar1) to (4-Ar5) may be substituted with phenyl, biphenylyl, naphthyl, anthracenyl, phenanthrenyl, methyl, ethyl, propyl, or butyl.

[0451] These heteroaryls may be bonded to the fluorene skeleton in the above formula (4) via a linking group. That is, the fluorene skeleton in the formula (4) and the above heteroaryls may be bonded directly, or may be bonded to each other via a linking group. Examples of the linking group include phenylene, biphenylene, naphthylene, anthracenylene, methylene, ethylene, -OCH2CH2-, -CH2CH2O-, or -OCH2CH2O-.

[0452] In addition, R in formula (4) 1 and R 2 , R 2 and R 3 , R 3 and R 4 , R 5 and R 6 , R 6 and R 7 or R 7 and R 8 are each independently bonded to form a fused ring, R 9 and R 10 may be bonded to form a spiro ring. 1 From R 8 The condensed ring formed by is a ring condensed to the benzene ring in formula (4), and is an aliphatic ring or an aromatic ring. An aromatic ring is preferable, and examples of the structure including the benzene ring in formula (4) include a naphthalene ring and a phenanthrene ring. 9 and R 10 The spiro ring formed by the formula (4) is a ring that is spiro-bonded to the five-membered ring in the formula (4), and is an aliphatic ring or an aromatic ring. An aromatic ring, such as a fluorene ring, is preferred.

[0453] The compound represented by the general formula (4) is preferably a compound represented by the following formula (4-1), formula (4-2) or formula (4-3), 1 and R 2 A compound having a condensed benzene ring formed by bonding with R 3 and R 4 A compound having a condensed benzene ring formed by bonding with R 1 From R 8 is a compound in which none of the above is bound. [ka]

[0454] R in formula (4-1), formula (4-2) and formula (4-3) 1 From R 10 The definition of R in Eq. (4) corresponds to 1 From R 10 is the same as R in formula (4-1) and formula (4-2). 11 From R 14 The definition of R in Eq. (4) 1 From R 10 is the same as:

[0455] The compound represented by general formula (4) is more preferably a compound represented by the following formula (4-1A), formula (4-2A) or formula (4-3A), in which R 9 and R 10 is a compound in which a spiro-fluorene ring is formed by bonding. [ka]

[0456] R in formula (4-1A), formula (4-2A) and formula (4-3A) 2 From R 7 The definition of is the corresponding R in formula (4-1), formula (4-2) and formula (4-3). 2 From R 7and R in formula (4-1A) and formula (4-2A) 11 From R 14 The definition of R in formula (4-1) and formula (4-2) 11 From R 14 is the same as:

[0457] In addition, all or a part of the hydrogen atoms in the compound represented by formula (4) may be substituted with halogen, cyano or deuterium.

[0458] Specific examples of the fluorene-based compound include compounds represented by any of the following formulas (4-4) to (4-22): In addition, "Me" in the following structural formulas represents a methyl group. [ka]

[0459] <Dibenzochrysene compounds> The dibenzochrysene compound as the host is, for example, a compound represented by the following general formula (5). [ka]

[0460] In the above formula (5), R 1 From R 16 are each independently a hydrogen atom, an aryl, a heteroaryl (wherein the heteroaryl may be bonded to the dibenzochrysene skeleton in the above formula (5) via a linking group), a diarylamino, a diheteroarylamino, an arylheteroarylamino, an alkyl, a cycloalkyl, an alkenyl, an alkoxy, or an aryloxy, in which at least one hydrogen atom may be substituted with an aryl, a heteroaryl, an alkyl, or a cycloalkyl; Also, R 1 From R 16adjacent groups among these may be bonded to each other to form a condensed ring, at least one hydrogen atom in the formed ring may be substituted with an aryl, a heteroaryl (the heteroaryl may be bonded to the formed ring via a linking group), a diarylamino, a diheteroarylamino, an arylheteroarylamino, an alkyl, a cycloalkyl, an alkenyl, an alkoxy, or an aryloxy, at least one hydrogen atom in these may be substituted with an aryl, a heteroaryl, an alkyl, or a cycloalkyl, and At least one hydrogen in the compound represented by formula (5) may be substituted with halogen, cyano or deuterium.

[0461] For details of each group in the definition of the above formula (5), the explanation for the polycyclic aromatic compound of the above formula (1) can be cited.

[0462] The alkenyl in the definition of the above formula (5) is, for example, an alkenyl having 2 to 30 carbon atoms, preferably an alkenyl having 2 to 20 carbon atoms, more preferably an alkenyl having 2 to 10 carbon atoms, further preferably an alkenyl having 2 to 6 carbon atoms, and particularly preferably an alkenyl having 2 to 4 carbon atoms. Preferred alkenyls are vinyl, 1-propenyl, 2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, or 5-hexenyl.

[0463] Specific examples of heteroaryl include monovalent groups represented by removing any one hydrogen atom from a compound of the following formula (5-Ar1), formula (5-Ar2), formula (5-Ar3), formula (5-Ar4), or formula (5-Ar5). [ka] In formula (5-Ar1) to formula (5-Ar5), Y 1 are each independently O, S or NR, R is phenyl, biphenylyl, naphthyl, anthracenyl or hydrogen; At least one hydrogen atom in the structures of the above formulae (5-Ar1) to (5-Ar5) may be substituted with phenyl, biphenylyl, naphthyl, anthracenyl, phenanthrenyl, methyl, ethyl, propyl, or butyl.

[0464] These heteroaryls may be bonded to the dibenzochrysene skeleton in the above formula (5) via a linking group. That is, the dibenzochrysene skeleton and the above heteroaryls in the formula (5) may be bonded directly, or may be bonded to each other via a linking group. Examples of the linking group include phenylene, biphenylene, naphthylene, anthracenylene, methylene, ethylene, -OCH2CH2-, -CH2CH2O-, or -OCH2CH2O-.

[0465] The compound represented by the general formula (5) is preferably R 1 , R 4 , R 5 , R 8 , R 9 , R 12 , R 13 and R 16 is hydrogen. In this case, R in formula (5) 2 , R 3 , R 6 , R 7 , R 10 , R 11 , R 14 and R 15 are preferably each independently hydrogen, phenyl, biphenylyl, naphthyl, anthracenyl, phenanthrenyl, a monovalent group having the structure of the above formula (5-Ar1), (5-Ar2), (5-Ar3), (5-Ar4) or (5-Ar5) (the monovalent group having the structure may be bonded to the dibenzochrysene skeleton in the above formula (5) via phenylene, biphenylene, naphthylene, anthracenylene, methylene, ethylene, -OCHCH-, -CHCHO- or -OCHCHO-), methyl, ethyl, propyl or butyl.

[0466] The compound represented by the general formula (5) is more preferably R 1 , R 2 , R 4 , R 5 , R 7 , R 8 , R 9 , R 10 , R 12 , R 13 , R 15 and R 16 is hydrogen. In this case, R in formula (5) 3 , R 6 , R 11 and R 14 at least one (preferably one or two, more preferably one) of the formulae (5-Ar1), (5-Ar2), (5-Ar3), (5-Ar4) or (5-Ar5) is a monovalent group having a structure represented by the formula (5-Ar1), (5-Ar2), (5-Ar3), (5-Ar4) or (5-Ar5) via a single bond, phenylene, biphenylene, naphthylene, anthracenylene, methylene, ethylene, -OCHCH-, -CHCHO-, or -OCHCHO-; The other than the at least one (i.e., other than the position substituted by the monovalent group having the structure) is hydrogen, phenyl, biphenylyl, naphthyl, anthracenyl, methyl, ethyl, propyl, or butyl, and at least one hydrogen in these may be substituted with phenyl, biphenylyl, naphthyl, anthracenyl, methyl, ethyl, propyl, or butyl.

[0467] In addition, R in formula (5) 2 , R 3 , R 6 , R 7 , R 10 , R 11 , R 14 and R 15 When a monovalent group having a structure represented by the above formula (5-Ar1) to formula (5-Ar5) is selected as the aryl group, at least one hydrogen atom in the structure is R 1 From R 16 may be bonded to any one of the following to form a single bond.

[0468] Specific examples of the dibenzochrysene compound include compounds represented by any of the following formulas (5-1) to (5-39): In addition, "tBu" in the following structural formulas represents a t-butyl group. [ka]

[0469] [ka]

[0470] 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.

[0471] <Example of polymer host material> [ka]

[0472] In formula (SPH-1), 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.

[0473] 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.

[0474] At least one hydrogen atom in MU and EC in formula (SPH-1) may be substituted with an alkyl group having 1 to 24 carbon atoms, a cycloalkyl group having 3 to 24 carbon atoms, a halogen atom or a deuterium atom; further, any -CH2- in the alkyl group may be substituted with -O- or -Si(CH3)2-; any -CH2- in the alkyl group except for the -CH2- directly bonded to EC in formula (SPH-1) may be substituted with an arylene group having 6 to 24 carbon atoms; and any hydrogen atom in the alkyl group may be substituted with a fluorine atom.

[0475] Examples of MU include a divalent group represented by removing any two hydrogen atoms from any of the following compounds: [ka]

[0476] More specifically, the divalent group may be any of the following structures: In these, MU bonds to another MU or EC at *.

[0477] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka]

[0478] Examples of EC include monovalent groups represented by any of the following structures: In these, EC is bonded to MU at *.

[0479] [ka] [ka]

[0480] From the viewpoint of solubility and coating film-forming property, the compound represented by formula (SPH-1) is preferably such that 10 to 100% of the total number of MUs (k) in the molecule have an alkyl having 1 to 24 carbon atoms, more preferably 30 to 100% of the total number of MUs (k) in the molecule have an alkyl having 1 to 18 carbon atoms (branched chain alkyl having 3 to 18 carbon atoms), and even more preferably 50 to 100% of the total number of MUs (k) in the molecule have an alkyl having 1 to 12 carbon atoms (branched chain alkyl having 3 to 12 carbon atoms). On the other hand, from the viewpoint of in-plane orientation and charge transport, it is preferable that 10 to 100% of the total number of MUs (k) in the molecule have an alkyl having 7 to 24 carbon atoms, and more preferably 30 to 100% of the total number of MUs (k) in the molecule have an alkyl having 7 to 24 carbon atoms (branched chain alkyl having 7 to 24 carbon atoms).

[0481] The applications of such polymer compounds and crosslinked polymers will be described in detail below.

[0482] <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.

[0483] The electron injection / transport layer is a layer that is responsible for injecting electrons from the cathode and transporting the electrons. It is desirable that the electron injection efficiency is high and that the injected electrons are efficiently transported. For this purpose, it is preferable that the material has a large electron affinity, a large electron mobility, and excellent stability, and impurities that become traps are unlikely to occur during manufacture and use. However, when considering the balance of transport of holes and electrons, if the material mainly plays a role of efficiently preventing holes from flowing from the anode to the cathode without recombining, even if the electron transport ability is not so high, it has the effect of improving the luminous efficiency equivalent to a material with a high electron transport ability. Therefore, the electron injection / transport layer in this embodiment may also include the function of a layer that can efficiently block the movement of holes.

[0484] 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.

[0485] 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.

[0486] 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.

[0487] Furthermore, metal complexes having an electron-accepting nitrogen atom can also be used, and examples thereof include hydroxyazole complexes such as quinolinol metal complexes and hydroxyphenyloxazole complexes, azomethine complexes, tropolone metal complexes, flavonol metal complexes, and benzoquinoline metal complexes.

[0488] The above-mentioned materials may be used alone or in combination with different materials.

[0489] 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.

[0490] <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.

[0491] 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.

[0492] 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.

[0493] Specific examples of the borane derivative include the following compounds: [ka]

[0494] The borane derivative can be produced using known raw materials and known synthesis methods.

[0495] <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]

[0496] 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.

[0497] 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).

[0498] 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.

[0499] 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]

[0500] 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]

[0501] 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.

[0502] 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 or branched alkyl having 3 to 24 carbon atoms. A preferred "alkyl" is an alkyl having 1 to 18 carbon atoms (branched alkyl having 3 to 18 carbon atoms). A more preferred "alkyl" is an alkyl having 1 to 12 carbon atoms (branched alkyl having 3 to 12 carbon atoms). An even more preferred "alkyl" is an alkyl having 1 to 6 carbon atoms (branched alkyl having 3 to 6 carbon atoms). An especially preferred "alkyl" is an alkyl having 1 to 4 carbon atoms (branched alkyl having 3 to 4 carbon atoms).

[0503] 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 group include n-hexyl, n-butyl, n-hexyl, 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.

[0504] 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.

[0505] R 11 ~R 18 In the above, the "cycloalkyl" is, for example, a cycloalkyl having 3 to 12 carbon atoms. A preferred "cycloalkyl" is a cycloalkyl having 3 to 10 carbon atoms. A more preferred "cycloalkyl" is a cycloalkyl having 3 to 8 carbon atoms. An even more preferred "cycloalkyl" is a cycloalkyl having 3 to 6 carbon atoms. Specific examples of "cycloalkyl" include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, methylcyclopentyl, cycloheptyl, methylcyclohexyl, cyclooctyl, and dimethylcyclohexyl.

[0506] R 11 ~R 18 As for the "aryl" in the above, a preferable aryl is an aryl having 6 to 30 carbon atoms, a more preferable aryl is an aryl having 6 to 18 carbon atoms, an even more preferable aryl is an aryl having 6 to 14 carbon atoms, and an especially preferable aryl is an aryl having 6 to 12 carbon atoms.

[0507] Specific examples of the "aryl having 6 to 30 carbon atoms" include monocyclic aryl phenyl, fused bicyclic aryl (1-, 2-)naphthyl, fused tricyclic aryl acenaphthylene-(1-, 3-, 4-, 5-)yl, fluoren-(1-, 2-, 3-, 4-, 9-)yl, phenalene-(1-, 2-)yl, (1-, 2-, 3-, 4-, 9-)phenanthryl, fused tetracyclic aryl triphenylene-(1-, 2-)yl, pyrene-(1-, 2-, 4-)yl, naphthacene-(1-, 2-, 5-)yl, fused pentacyclic aryl perylene-(1-, 2-, 3-)yl, pentacene-(1-, 2-, 5-, 6-)yl, and the like.

[0508] Preferred examples of the "aryl having 6 to 30 carbon atoms" include phenyl, naphthyl, phenanthryl, chrysenyl, and triphenylenyl, more preferably phenyl, 1-naphthyl, 2-naphthyl, and phenanthryl, and particularly preferably phenyl, 1-naphthyl, and 2-naphthyl.

[0509] 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.

[0510] Specific examples of the pyridine derivative include the following compounds: [ka]

[0511] This pyridine derivative can be produced using known raw materials and known synthesis methods.

[0512] <Fluoranthene derivatives> The fluoranthene derivative is a compound represented by, for example, the following general formula (ETM-3), and is specifically disclosed in International Publication No. 2010 / 134352. [Chemical formula]

[0513] 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 in the case of being substituted include aryl, heteroaryl, alkyl or cycloalkyl.

[0514] Specific examples of this fluoranthene derivative include, for example, the following compounds. [Chemical formula]

[0515] <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]

[0516] R 1 ~R 11 are each independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, alkyl, cycloalkyl, alkoxy or aryloxy, and at least one hydrogen in these may be substituted with aryl, heteroaryl, alkyl or cycloalkyl.

[0517] Also, R 1 ~R 11Adjacent 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.

[0518] In addition, at least one hydrogen in the compound or structure represented by formula (ETM-4) may be substituted with a halogen or deuterium.

[0519] For an explanation of the substituents and the form of ring formation in formula (ETM-4), the explanation of the polycyclic aromatic compound represented by the above general formula (1) or formula (2) can be cited.

[0520] Specific examples of the BO derivative include the following compounds: [ka]

[0521] The BO derivative can be produced using known raw materials and known synthesis methods.

[0522] <Anthracene derivatives> One of the anthracene derivatives is, for example, a compound represented by the following formula (ETM-5-1). [ka]

[0523] 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.

[0524] 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]

[0525] 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.

[0526] R 1 ~R 4 The alkyl having 1 to 6 carbon atoms in the formula (I) may be either linear or branched. That is, it is a linear alkyl having 1 to 6 carbon atoms or a branched alkyl having 3 to 6 carbon atoms. More preferably, it is an alkyl having 1 to 4 carbon atoms (branched alkyl having 3 to 4 carbon atoms). Specific examples include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, t-butyl, n-pentyl, isopentyl, neopentyl, t-pentyl (t-amyl), n-hexyl, 1-methylpentyl, 3,3-dimethylbutyl, and 2-ethylbutyl. Methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, and t-butyl are preferred, and methyl, ethyl, and t-butyl are more preferred.

[0527] 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.

[0528] 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.

[0529] 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.

[0530] 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.

[0531] One example of the anthracene derivative is a compound represented by the following formula (ETM-5-2). [ka]

[0532] Ar 1 are each independently a single bond, or a divalent benzene, naphthalene, anthracene, fluorene, or phenalene.

[0533] 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.

[0534] 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.

[0535] Specific examples of these anthracene derivatives include the following compounds. [ka]

[0536] These anthracene derivatives can be produced using known raw materials and known synthesis methods.

[0537] <Benzofluorene derivatives> The benzofluorene derivative is, for example, a compound represented by the following formula (ETM-6). [ka]

[0538] Ar 1 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.

[0539] 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.

[0540] Ar 2The "alkyl" in the above may be either linear or branched, and examples thereof include linear alkyl having 1 to 24 carbon atoms or branched alkyl having 3 to 24 carbon atoms. A preferred "alkyl" is an alkyl having 1 to 18 carbon atoms (branched alkyl having 3 to 18 carbon atoms). A more preferred "alkyl" is an alkyl having 1 to 12 carbon atoms (branched alkyl having 3 to 12 carbon atoms). An even more preferred "alkyl" is an alkyl having 1 to 6 carbon atoms (branched alkyl having 3 to 6 carbon atoms). An especially preferred "alkyl" is an alkyl having 1 to 4 carbon atoms (branched alkyl having 3 to 4 carbon atoms). Specific examples of "alkyl" include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, t-butyl, n-pentyl, isopentyl, neopentyl, t-pentyl (t-amyl), n-hexyl, 1-methylpentyl, 3,3-dimethylbutyl, 2-ethylbutyl, n-heptyl, 1-methylhexyl, and the like.

[0541] Ar 2 In the above, the "cycloalkyl" is, for example, a cycloalkyl having 3 to 12 carbon atoms. A preferred "cycloalkyl" is a cycloalkyl having 3 to 10 carbon atoms. A more preferred "cycloalkyl" is a cycloalkyl having 3 to 8 carbon atoms. An even more preferred "cycloalkyl" is a cycloalkyl having 3 to 6 carbon atoms. Specific examples of the "cycloalkyl" include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, methylcyclopentyl, cycloheptyl, methylcyclohexyl, cyclooctyl, and dimethylcyclohexyl.

[0542] 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.

[0543] Specific examples of the "aryl having 6 to 30 carbon atoms" include phenyl, naphthyl, acenaphthylenyl, fluorenyl, phenalenyl, phenanthryl, triphenylenyl, pyrenyl, naphthacenyl, perylenyl, and pentacenyl.

[0544] 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.

[0545] Specific examples of the benzofluorene derivative include the following compounds: [ka]

[0546] The benzofluorene derivative can be produced using known raw materials and known synthesis methods.

[0547] <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 16 carbon atoms, aryl having 6 to 20 carbon atoms, or heteroaryl having 5 to 20 carbon atoms, R 6 is CN, a substituted or unsubstituted alkyl having 1 to 20 carbon atoms, a cycloalkyl having 3 to 16 carbon atoms, a heteroalkyl having 1 to 20 carbon atoms, an aryl having 6 to 20 carbon atoms, a heteroaryl having 5 to 20 carbon atoms, an alkoxy having 1 to 20 carbon atoms, or an aryloxy having 6 to 20 carbon atoms, R 7 and R 8each 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.

[0548] The phosphine oxide derivative may be, for example, a compound represented by the following formula (ETM-7-2). [ka]

[0549] R 1 ~R 3 may 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.

[0550] Ar 1 may be the same or different and are an arylene group or a 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.

[0551] 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 the case in 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 in terms of availability and cost.

[0552] 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.

[0553] 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.

[0554] 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.

[0555] 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.

[0556] 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.

[0557] 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.

[0558] 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.

[0559] 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.

[0560] 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.

[0561] 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.

[0562] The aryl group refers to an aromatic hydrocarbon group such as a phenyl group, a naphthyl group, a biphenyl 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.

[0563] 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.

[0564] Halogen refers to fluorine, chlorine, bromine and iodine.

[0565] 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.

[0566] Furthermore, the aliphatic hydrocarbons, alicyclic hydrocarbons, aromatic hydrocarbons and heterocycles may be either unsubstituted or substituted.

[0567] 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.

[0568] 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.

[0569] Specific examples of the phosphine oxide derivative include the following compounds: [ka]

[0570] The phosphine oxide derivative can be produced using known raw materials and known synthesis methods.

[0571] <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]

[0572] 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.

[0573] The "aryl" in the "optionally substituted aryl" includes, for example, an aryl having 6 to 30 carbon atoms, preferably an aryl having 6 to 24 carbon atoms, more preferably an aryl having 6 to 20 carbon atoms, and further preferably an aryl having 6 to 12 carbon atoms.

[0574] Specific examples of "aryl" include monocyclic aryl phenyl, bicyclic aryl (2-, 3-, 4-) biphenylyl, condensed bicyclic aryl (1-, 2-) naphthyl, tricyclic aryl terphenylyl (m-terphenyl-2'-yl, m-terphenyl-4'-yl, m-terphenyl-5'-yl, o-terphenyl-3'-yl, o-terphenyl-4'-yl, p-terphenyl-2'-yl, m-terphenyl-2-yl, m-terphenyl-3-yl, m-terphenyl-4-yl, o-terphenyl-2-yl, o-terphenyl-3-yl, o-terphenyl-4-yl, p-terphenyl-2-yl, p-terphenyl-3-yl, p-terphenyl-4-yl), condensed tricyclic aryl Examples of the aryl include acenaphthylene-(1-,3-,4-,5-)yl, fluorene-(1-,2-,3-,4-,9-)yl, phenalene-(1-,2-)yl, (1-,2-,3-,4-,9-)phenanthryl, the tetracyclic aryl group is quaterphenylyl (5'-phenyl-m-terphenyl-2-yl, 5'-phenyl-m-terphenyl-3-yl, 5'-phenyl-m-terphenyl-4-yl, m-quaterphenylyl), the condensed tetracyclic aryl group is triphenylene-(1-,2-)yl, pyrene-(1-,2-,4-)yl, naphthacene-(1-,2-,5-)yl, the condensed pentacyclic aryl group is perylene-(1-,2-,3-)yl, pentacene-(1-,2-,5-,6-)yl, and the like.

[0575] 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.

[0576] Specific examples of heteroaryl include pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, oxadiazolyl, thiadiazolyl, triazolyl, tetrazolyl, pyrazolyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, indolyl, isoindolyl, 1H-indazolyl, benzimidazolyl, benzoxazolyl, benzothiazolyl, 1H-benzotriazolyl, quinolyl, isoquinolyl, cinnolyl, quinazolyl, quinoxalinyl, phthalazinyl, naphthyridinyl, purinyl, pteridinyl, carbazolyl, acridinyl, and phenoxy. Examples of such alkyl groups include noxathiinyl, 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.

[0577] The above aryl and heteroaryl may be substituted, for example, by the above aryl or heteroaryl, respectively.

[0578] Specific examples of the pyrimidine derivative include the following compounds: [ka]

[0579] The pyrimidine derivative can be produced using known raw materials and known synthesis methods.

[0580] <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]

[0581] 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.

[0582] The "aryl" in the "optionally substituted aryl" includes, for example, an aryl having 6 to 30 carbon atoms, preferably an aryl having 6 to 24 carbon atoms, more preferably an aryl having 6 to 20 carbon atoms, and further preferably an aryl having 6 to 12 carbon atoms.

[0583] Specific examples of "aryl" include monocyclic aryl phenyl, bicyclic aryl (2-, 3-, 4-) biphenylyl, condensed bicyclic aryl (1-, 2-) naphthyl, tricyclic aryl terphenylyl (m-terphenyl-2'-yl, m-terphenyl-4'-yl, m-terphenyl-5'-yl, o-terphenyl-3'-yl, o-terphenyl-4'-yl, p-terphenyl-2'-yl, m-terphenyl-2-yl, m-terphenyl-3-yl, m-terphenyl-4-yl, o-terphenyl-2-yl, o-terphenyl-3-yl, o-terphenyl-4-yl, p-terphenyl-2-yl, p-terphenyl-3-yl, p-terphenyl-4-yl), condensed tricyclic aryl Examples of the aryl include acenaphthylene-(1-,3-,4-,5-)yl, fluorene-(1-,2-,3-,4-,9-)yl, phenalene-(1-,2-)yl, (1-,2-,3-,4-,9-)phenanthryl, the tetracyclic aryl group is quaterphenylyl (5'-phenyl-m-terphenyl-2-yl, 5'-phenyl-m-terphenyl-3-yl, 5'-phenyl-m-terphenyl-4-yl, m-quaterphenylyl), the condensed tetracyclic aryl group is triphenylene-(1-,2-)yl, pyrene-(1-,2-,4-)yl, naphthacene-(1-,2-,5-)yl, the condensed pentacyclic aryl group is perylene-(1-,2-,3-)yl, pentacene-(1-,2-,5-,6-)yl, and the like.

[0584] 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.

[0585] Specific examples of heteroaryl include pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, oxadiazolyl, thiadiazolyl, triazolyl, tetrazolyl, pyrazolyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, indolyl, isoindolyl, 1H-indazolyl, benzimidazolyl, benzoxazolyl, benzothiazolyl, 1H-benzotriazolyl, quinolyl, isoquinolyl, cinnolyl, quinazolyl, quinoxalinyl, phthalazinyl, naphthyridinyl, purinyl, pteridinyl, carbazolyl, acridinyl, and phenoxy. Examples of such alkyl groups include noxathiinyl, 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.

[0586] The above aryl and heteroaryl may be substituted, for example, by the above aryl or heteroaryl, respectively.

[0587] 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.

[0588] Specific examples of the carbazole derivative include the following compounds. [ka]

[0589] The carbazole derivative can be produced using known raw materials and known synthesis methods.

[0590] <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]

[0591] 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.

[0592] The "aryl" in the "optionally substituted aryl" includes, for example, an aryl having 6 to 30 carbon atoms, preferably an aryl having 6 to 24 carbon atoms, more preferably an aryl having 6 to 20 carbon atoms, and further preferably an aryl having 6 to 12 carbon atoms.

[0593] Specific examples of "aryl" include monocyclic aryl phenyl, bicyclic aryl (2-, 3-, 4-) biphenylyl, condensed bicyclic aryl (1-, 2-) naphthyl, tricyclic aryl terphenylyl (m-terphenyl-2'-yl, m-terphenyl-4'-yl, m-terphenyl-5'-yl, o-terphenyl-3'-yl, o-terphenyl-4'-yl, p-terphenyl-2'-yl, m-terphenyl-2-yl, m-terphenyl-3-yl, m-terphenyl-4-yl, o-terphenyl-2-yl, o-terphenyl-3-yl, o-terphenyl-4-yl, p-terphenyl-2-yl, p-terphenyl-3-yl, p-terphenyl-4-yl), condensed tricyclic aryl Examples of the aryl include acenaphthylene-(1-,3-,4-,5-)yl, fluorene-(1-,2-,3-,4-,9-)yl, phenalene-(1-,2-)yl, (1-,2-,3-,4-,9-)phenanthryl, the tetracyclic aryl group is quaterphenylyl (5'-phenyl-m-terphenyl-2-yl, 5'-phenyl-m-terphenyl-3-yl, 5'-phenyl-m-terphenyl-4-yl, m-quaterphenylyl), the condensed tetracyclic aryl group is triphenylene-(1-,2-)yl, pyrene-(1-,2-,4-)yl, naphthacene-(1-,2-,5-)yl, the condensed pentacyclic aryl group is perylene-(1-,2-,3-)yl, pentacene-(1-,2-,5-,6-)yl, and the like.

[0594] 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.

[0595] Specific examples of heteroaryl include pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, oxadiazolyl, thiadiazolyl, triazolyl, tetrazolyl, pyrazolyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, indolyl, isoindolyl, 1H-indazolyl, benzimidazolyl, benzoxazolyl, benzothiazolyl, 1H-benzotriazolyl, quinolyl, isoquinolyl, cinnolyl, quinazolyl, quinoxalinyl, phthalazinyl, naphthyridinyl, purinyl, pteridinyl, carbazolyl, acridinyl, and phenoxy. Examples of such alkyl groups include noxathiinyl, 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.

[0596] The above aryl and heteroaryl may be substituted, for example, by the above aryl or heteroaryl, respectively.

[0597] Specific examples of the triazine derivative include the following compounds: [ka]

[0598] The triazine derivative can be produced using known raw materials and known synthesis methods.

[0599] <Benzimidazole derivatives> The benzimidazole derivative is, for example, a compound represented by the following formula (ETM-11). [ka]

[0600] 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]

[0601] 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.

[0602] 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 18 At 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.

[0603] 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]

[0604] The benzimidazole derivative can be produced using known raw materials and known synthesis methods.

[0605] <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]

[0606] 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.

[0607] 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.

[0608] At least one hydrogen atom in each of the phenanthroline derivatives may be replaced with deuterium.

[0609] R 11 ~R 18 The alkyl, cycloalkyl and aryl in the above formula (ETM-2) are R 11 ~R 18 can be cited. In addition to the above examples, φ can 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]

[0610] Specific examples of the phenanthroline derivative include 4,7-diphenyl-1,10-phenanthroline, 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline, 9,10-di(1,10-phenanthroline-2-yl)anthracene, 2,6-di(1,10-phenanthroline-5-yl)pyridine, 1,3,5-tri(1,10-phenanthroline-5-yl)benzene, 9,9'-difluoro-bi(1,10-phenanthroline-5-yl), bathocuproine, 1,3-bis(2-phenyl-1,10-phenanthroline-9-yl)benzene, and compounds represented by the following structural formula. [ka]

[0611] The phenanthroline derivative can be produced using known raw materials and known synthesis methods.

[0612] <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.

[0613] 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.

[0614] The quinolinol metal complex can be produced using known raw materials and known synthesis methods.

[0615] <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]

[0616] 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 from 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 the below-mentioned thiazole group or benzothiazole group, and at least one hydrogen in the thiazole derivative and benzothiazole derivative may be replaced with deuterium. * in the following structural formula indicates a bond position. [ka]

[0617] It is further preferable that φ is an anthracene ring or a fluorene ring. In this case, the structure can be as described in the above formula (ETM-2-1) or formula (ETM-2-2). 11 ~R 18 The explanation for formula (ETM-2-1) or formula (ETM-2-2) above can be cited. In addition, in formula (ETM-2-1) or formula (ETM-2-2) above, the two pyridine-based substituents are explained as being bonded together, but when these are replaced with a thiazole-based substituent (or a benzothiazole-based substituent), both pyridine-based substituents may be replaced with a thiazole-based substituent (or a benzothiazole-based substituent) (i.e., n=2), or one of the pyridine-based substituents may be replaced with a thiazole-based substituent (or a benzothiazole-based substituent) and the other pyridine-based substituent may be replaced with R 11 ~R 18 (i.e., n=1). Furthermore, for example, R in the above formula (ETM-2-1) 11 ~R 18 At least one of the substituents is replaced with a thiazole-based substituent (or a benzothiazole-based substituent) to form a "pyridine-based substituent" R 11 ~R 18 may be substituted.

[0618] These thiazole or benzothiazole derivatives can be produced using known raw materials and known synthesis methods.

[0619] 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.

[0620] 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.

[0621] 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.

[0622] <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 .

[0623] The material for forming the cathode 108 is not particularly limited as long as it is a substance that can efficiently inject electrons into the organic layer, but the same material as the material for forming the anode 102 can be used. Among them, metals such as tin, indium, calcium, aluminum, silver, copper, nickel, chromium, gold, platinum, iron, zinc, lithium, sodium, potassium, cesium, and magnesium, or alloys thereof (magnesium-silver alloy, magnesium-indium alloy, aluminum-lithium alloy such as lithium fluoride / aluminum, etc.), etc. are preferable. In order to increase the electron injection efficiency and improve the device characteristics, lithium, sodium, potassium, cesium, calcium, magnesium, or alloys containing these low work function metals are effective. However, these low work function metals are generally unstable in the air. To improve this point, for example, a method is known in which a trace amount of lithium, cesium, or magnesium is doped into the organic layer to use a highly stable electrode. As other dopants, inorganic salts such as lithium fluoride, cesium fluoride, lithium oxide, and cesium oxide can also be used. However, they are not limited to these.

[0624] 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.

[0625] <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.

[0626] <Method for producing organic electroluminescent device> Each layer constituting an organic EL element can be formed by forming the material to be formed into a thin film by a method such as vapor deposition, resistance heating vapor deposition, electron beam vapor deposition, sputtering, molecular lamination, printing, spin coating or casting, coating, etc. The thickness of each layer thus formed is not particularly limited and can be set appropriately according to the properties of the material, but is usually in the range of 2 nm to 5000 nm. The thickness of the film can usually be measured with a quartz crystal oscillation type film thickness measuring device, etc. When forming a thin film by vapor deposition, the vapor deposition conditions vary depending on the type of material, the desired crystal structure and association structure of the film, etc. The vapor deposition conditions are generally a boat heating temperature of +50 to +400°C, a vacuum degree of 10, and a vacuum of 10. -6 ~10-3 It is preferable to appropriately set the pressure, pressure Pa, deposition rate 0.01 to 50 nm / sec, substrate temperature -150 to +300°C, and film thickness in the range of 2 nm to 5 µm.

[0627] 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.

[0628] 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.

[0629] <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.

[0630] <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.

[0631] 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.

[0632] 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.

[0633] 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.

[0634] 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.

[0635] 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 the electron transport layer material and the electron injection layer material can be prepared and then the layer can be formed by a wet film formation method.

[0636] <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.

[0637] <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.

[0638] Photolithography techniques can be used to fabricate the banks. Positive resist materials and negative resist materials can be used as bank materials that can be used in photolithography. In addition, patternable printing methods such as inkjet printing, gravure offset printing, reverse offset printing, and screen printing can also be used. In this case, permanent resist materials can also be used.

[0639] Materials that can be used for the banks include, but are not limited to, polysaccharides and their derivatives, homopolymers and copolymers of hydroxyl-containing ethylenic monomers, biopolymers, polyacryloyl compounds, polyesters, polystyrenes, polyimides, polyamideimides, polyetherimides, polysulfides, polysulfones, polyphenylenes, polyphenyl ethers, polyurethanes, epoxy (meth)acrylates, melamine (meth)acrylates, polyolefins, cyclic polyolefins, acrylonitrile-butadiene-styrene copolymers (ABS), silicone resins, polyvinyl chloride, chlorinated polyethylene, chlorinated polypropylene, polyacetate, polynorbornene, synthetic rubber, fluorinated polymers such as polyfluorovinylidene, polytetrafluoroethylene, and polyhexafluoropropylene, copolymers of fluoroolefins and hydrocarbon olefins, and fluorocarbon polymers.

[0640] <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.

[0641] <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.

[0642] (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.

[0643] Furthermore, the organic solvent contains a good solvent (GS) and a poor solvent (PS) for at least one of the solutes, and the boiling point (BP) of the good solvent (GS) is GS ) is the boiling point (BP PS ) is particularly preferred. By adding a poor solvent with a high boiling point, the good solvent with a low boiling point volatilizes first during film formation, increasing the concentration of the components in the composition and the concentration of the poor solvent, promoting rapid film formation. This results in a coating film with few defects, small surface roughness, and high smoothness.

[0644] 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.

[0645] 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.

[0646] (2) Specific examples of organic solvents Examples of the organic solvent used in the composition for forming the organic layer include alkylbenzene solvents, phenyl ether solvents, alkyl ether solvents, cyclic ketone solvents, aliphatic ketone solvents, monocyclic ketone solvents, solvents having a diester skeleton, and fluorine-containing solvents. Specific examples include pentanol, hexanol, heptanol, octanol, nonanol, decanol, undecanol, dodecanol, tetradecanol, hexane-2-ol, heptan-2-ol, octan-2-ol, decan-2-ol, dodecan-2-ol, cyclohexanol, Sanol, α-terpineol, β-terpineol, γ-terpineol, δ-terpineol, terpineol (mixture), ethylene glycol monomethyl ether acetate, propylene glycol monomethyl ether acetate, diethylene glycol dimethyl ether, dipropylene glycol dimethyl ether, diethylene glycol ethyl methyl ether, diethylene glycol isopropyl methyl ether, dipropylene glycol monomethyl ether, diethylene glycol diethyl ether, diethylene glycol monomethyl ether , diethylene glycol butyl methyl ether, tripropylene glycol dimethyl ether, triethylene glycol dimethyl ether, diethylene glycol monobutyl ether, ethylene glycol monophenyl ether, triethylene glycol monomethyl ether, diethylene glycol dibutyl ether, triethylene glycol butyl methyl ether, polyethylene glycol dimethyl ether, tetraethylene glycol dimethyl ether, p-xylene, m-xylene, o-xylene, 2,6-lutidine, 2-fluoro-m-xylene, 3-fluoro-o-xylene, 2-chlorobenzotrifluoride, cumene, toluene, 2-chloro-6-fluorotoluene, 2-fluoroanisole, anisole, 2,3-dimethylpyrazine, bromobenzene, 4-fluoroanisole, 3-fluoroanisole, 3-trifluoromethylanisole, mesitylene, 1,2,4-trimethylbenzene, t-butylbenzene, 2-methylanisole, phenetole, benzodioxole, 4-methylanisole, s-butylbenzene, 3-methylanisole, 4-fluoro-3-methylanisole, cymene, 1,2,3-Trimethylbenzene, 1,2-Dichlorobenzene, 2-Fluorobenzonitrile, 4-Fluoroveratrol, 2,6-Dimethylanisole, n-Butylbenzene, 3-Fluorobenzonitrile, Decalin (Decahydronaphthalene), Neopentylbenzene, 2,5-Dimethylanisole, 2,4-Dimethylanisole, Benzonitrile, 3,5-Dimethylanisole, Diphenyl ether, 1-Fluoro-3,5-dimethoxybenzene, Methyl benzoate, Isopentylbenzene, 3,4-Dimethylanisole, o-Tolunitrile, n-Amylbenzene, Veratrol, 1,2,3,4-Tetrahydronaphthalene, Ethyl benzoate, n-Hexylbenzene, Propyl benzoate, Cyclohexylbenzene, 1- Examples of the solvent include, but are not limited to, methylnaphthalene, butyl benzoate, 2-methylbiphenyl, 3-phenoxytoluene, 2,2'-bitolyl, dodecylbenzene, dipentylbenzene, tetramethylbenzene, trimethoxybenzene, trimethoxytoluene, 2,3-dihydrobenzofuran, 1-methyl-4-(propoxymethyl)benzene, 1-methyl-4-(butyloxymethyl)benzene, 1-methyl-4-(pentyloxymethyl)benzene, 1-methyl-4-(hexyloxymethyl)benzene, 1-methyl-4-(heptyloxymethyl)benzene, benzyl butyl ether, benzyl pentyl ether, benzyl hexyl ether, benzyl heptyl ether, and benzyl octyl ether. The solvent may be used alone or in a mixture.

[0647] <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.

[0648] (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.

[0649] 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.

[0650] The binder used in the organic layer-forming composition may be of one type or a mixture of two or more types.

[0651] (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.

[0652] 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.

[0653] The surfactant may be used alone or in combination of two or more kinds.

[0654] <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.

[0655] 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.

[0656] 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.

[0657] 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).

[0658] The lower the surface tension of the composition for forming an organic layer, the better the film-forming properties and the more defect-free the coating film will be. On the other hand, the higher the surface tension, the better the ink-jet ejection properties will be. For this reason, the viscosity of the composition for forming an organic layer is preferably such that the surface tension at 25°C is 20 to 40 mN / m, more preferably 20 to 30 mN / m. In the present invention, the surface tension is a value measured using the hanging drop method.

[0659] <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 (SPH-1), except that the compound represented by formula (XLP-1) has at least one crosslinkable substituent (XLS), and preferably the content of the monovalent or divalent aromatic compound having a crosslinkable substituent is 0.1 to 80% by weight in the molecule.

[0660] 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.

[0661] 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]

[0662] 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.

[0663] 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]

[0664] <Methods of producing polymer compounds and crosslinkable polymer compounds> The manufacturing method of the polymer compound and the crosslinkable polymer compound will be described with reference to the compound represented by the above formula (SPH-1) and the compound represented by the above formula (XLP-1). These compounds can be synthesized by appropriately combining known manufacturing methods.

[0665] 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.

[0666] 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.

[0667] The compound of formula (SPH-1) and the compound of formula (XLP-1) may be produced in one step or in multiple steps. The compound may be produced by a batch polymerization method in which all the raw materials are put into a reaction vessel and then the reaction is started, a dropwise polymerization method in which the raw materials are added dropwise to a reaction vessel, or a precipitation polymerization method in which the product precipitates as the reaction proceeds, and these methods can be combined appropriately to synthesize the compound. For example, when the compound represented by formula (SPH-1) is synthesized in one step, the target product is obtained by carrying out the 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 represented by general formula (SPH-1) 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.

[0668] 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.

[0669] [ka]

[0670] 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.

[0671] 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.

[0672] <Applications of organic electroluminescent devices> The present invention can also be applied to a display device having an organic EL element or a lighting device having an organic EL element. A display device or lighting device including an organic EL element can be manufactured by a known method, for example by connecting the organic EL element according to this embodiment to a known driving device, and can be driven appropriately using a known driving method such as DC driving, pulse driving, or AC driving.

[0673] Examples of the display device include panel displays such as color flat panel displays, and flexible displays such as flexible color organic electroluminescent (EL) displays (see, for example, JP-A-10-335066, JP-A-2003-321546, JP-A-2004-281086, etc.). Examples of the display method include matrix and segment methods. Note that matrix display and segment display may coexist in the same panel.

[0674] 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.

[0675] 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.

[0676] Examples of the lighting device include lighting devices for indoor lighting, backlights for liquid crystal display devices, etc. (see, for example, JP 2003-257621 A, JP 2003-277741 A, JP 2004-119211 A, etc.). Backlights are mainly used for the purpose of improving the visibility of non-self-luminous display devices, and are used in liquid crystal display devices, clocks, audio devices, automobile panels, display boards, signs, etc. In particular, for liquid crystal display devices, particularly backlights for personal computers, where thinning is an issue, it is difficult to make them thin because conventional methods are made of fluorescent lamps and light guide plates, so the backlight using the light-emitting element according to this embodiment is characterized by its thinness and light weight.

[0677] 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.

[0678] 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.

[0679] 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.

[0680] 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

[0681] The present invention will be described in more detail below with reference to examples, but the present invention is not limited thereto. First, synthesis examples of polycyclic aromatic compounds will be described below.

[0682] Synthesis Example (1): Synthesis of Compound (1-411) [ka]

[0683] Under a nitrogen atmosphere, 2,3-dichloroaniline (6.0 g), 6-bromo-1,1,4,4-tetramethyl-2,3-dihydronaphthalene (25 g), dichlorobis[(di-t-butyl(4-dimethylaminophenyl)phosphino)palladium (Pd-132, 0.44 g), sodium-t-butoxide (NaOtBu, 14.8 g) and xylene (120 ml) were placed in a flask and heated at 120°C for 2 hours. After the reaction, water and ethyl acetate were added to the reaction solution and stirred, and then the organic layer was separated and washed with water. The organic layer was then concentrated to obtain a crude product. The crude product was purified using a silica gel short column (eluent: toluene), and methanol was added to the crude product obtained by concentrating the solvent and cooled on ice. The precipitated crystals were filtered and washed with methanol to obtain compound (IA) (17.0 g). [ka]

[0684] In a nitrogen atmosphere, compound (IA) (8.0 g), bis(4-t-butylphenyl)amine (25 g), Pd-132 (0.10 g), NaOtBu (2.1 g) and xylene (40 ml) were placed in a flask and heated at 120°C for 1 hour. After the reaction, water and ethyl acetate were added to the reaction solution and stirred, and then the organic layer was separated and washed with water. The organic layer was then concentrated to obtain a crude product. The crude product was purified using a silica gel short column (eluent: toluene), and methanol was added to the crude product obtained by concentrating the solvent and cooling with ice. The precipitated crystals were filtered and washed with methanol to obtain compound (IB) (9.7 g). [ka]

[0685] A 1.53M t-butyllithium pentane solution (15.2ml) was added to a flask containing compound (IB) (8.6g) and t-butylbenzene (80ml) under a nitrogen atmosphere at 0°C. After the dropwise addition, the temperature was raised to 60°C and stirred for 0.5 hours, and then components with a boiling point lower than that of t-butylbenzene were distilled off under reduced pressure. The mixture was cooled to -50°C, boron tribromide (5.8g) was added, and the mixture was heated to room temperature and stirred for 0.5 hours. The mixture was then cooled again to 0°C, N,N-diisopropylethylamine (2.6g) was added, and the mixture was stirred at room temperature until the heat generation subsided, and then the mixture was heated to 100°C and stirred for 1 hour. The reaction solution was cooled to room temperature, and an aqueous sodium acetate solution cooled in an ice bath was added, followed by ethyl acetate, and the mixture was stirred for 1 hour. The yellow suspension was filtered, and the precipitate was washed with methanol. The yellow crystals were dissolved in toluene by heating, and then purified with a silica gel short column (eluent: toluene). The obtained crude product was added to toluene and concentrated, and then Solmix (A-11) was added to precipitate crystals, which were filtered and further washed with methanol to obtain compound (1-411) (3.0 g). [ka]

[0686] The structure of the obtained compound was confirmed by NMR measurement. 1 H-NMR(CDCl3): δ=1.09(s,6H), 1.27(s,6H), 1.42(s,6H), 1.46(s,9H), 1.48(s,9H), 1.49(s,6H), 1.71-1.80(m,8H), 6.11(d,1H), 6.23(d,1H), 6.59(s,1H), 6.73(d,1H), 7.09(dd,1H), 7.25-7.30(m,5H), 7.51(dd,1H), 7.59(d,1H), 7.67(d,2H), 8.92(s,1H), 8.99(d,1H).

[0687] Synthesis Example (2): Synthesis of Compound (1-590) [ka]

[0688] Under a nitrogen atmosphere, 2,3-dichloro-5-methylaniline (6.6 g), 6-bromo-1,1,4,4-tetramethyl-2,3-dihydronaphthalene (25 g), Pd-132 (0.54 g), NaOtBu (9.0 g) and xylene (90 ml) were placed in a flask and heated at 120°C for 2 hours. After the reaction, water and ethyl acetate were added to the reaction solution and stirred, and then the organic layer was separated and washed with water. The organic layer was then concentrated to obtain a crude product. The crude product was purified using a silica gel short column (eluent: toluene), and methanol was added to the crude product obtained by concentrating the solvent and cooling with ice. The precipitated crystals were filtered and washed with methanol to obtain compound (IC) (13.0 g). [ka]

[0689] In a nitrogen atmosphere, compound (IC) (8.0 g), bis(4-t-butylphenyl)amine (4 g), Pd-132 (0.10 g), NaOtBu (2.1 g) and xylene (40 ml) were placed in a flask and heated at 120°C for 1 hour. After the reaction, water and ethyl acetate were added to the reaction solution and stirred, and then the organic layer was separated and washed with water. The organic layer was then concentrated to obtain a crude product. The crude product was purified using a silica gel short column (eluent: toluene), and ethyl acetate and then methanol were added to the crude product obtained by concentrating the solvent, and the precipitated crystals were filtered and washed with methanol to obtain compound (ID) (11.0 g). [ka]

[0690] A 1.53M t-butyllithium pentane solution (18.9ml) was added to a flask containing compound (ID) (11.0g) and t-butylbenzene (110ml) under a nitrogen atmosphere at 0°C. After the dropwise addition, the temperature was raised to 60°C and stirred for 0.5 hours, and then components with a boiling point lower than that of t-butylbenzene were distilled off under reduced pressure. The mixture was cooled to -50°C, boron tribromide (7.3g) was added, and the mixture was heated to room temperature and stirred for 0.5 hours. The mixture was then cooled again to 0°C, N,N-diisopropylethylamine (2.6g) was added, and the mixture was stirred at room temperature until the heat generation subsided, and then the mixture was heated to 100°C and stirred for 1 hour. The reaction solution was cooled to room temperature, and an aqueous sodium acetate solution cooled in an ice bath was added, followed by ethyl acetate, and the mixture was stirred for 1 hour. The organic layer was separated, washed with water (twice), and the solvent was distilled off under reduced pressure. Methanol was added to the resulting residue and cooled on ice, and the precipitate was filtered and washed with methanol. The yellow crystals were dissolved in toluene by heating, and then purified with a silica gel short column (eluent: toluene). The obtained crude product was added to toluene and concentrated, then ethyl acetate and then Solmix (A-11) were added, and the ethyl acetate was distilled off. The precipitated crystals were filtered and further washed with methanol to obtain compound (1-590) (4.0 g). [ka]

[0691] The structure of the obtained compound was confirmed by NMR measurement. 1 H-NMR(CDCl3): δ=1.08(s,6H), 1.27(s,6H), 1.42(s,6H), 1.46(s,9H), 1.47(s,9H), 1.48(s,6H), 1.69-1.81(m,8H), 2.18(s,3H), 5.97(s,1H), 6.06( s,1H), 6.52(s,1H), 6.67(d,1H), 7.08(dd,1H), 7.25-7.29(m,3H), 7.48(dd,1H), 7.59(d,1H), 7.67(d,2H), 8.89(s,1H), 8.97(d,1H).

[0692] Synthesis Example (3): Synthesis of Compound (1-1301) [ka]

[0693] In a nitrogen atmosphere, compound (IA) (8.0 g), compound (IE) (5.6 g), tris(dibenzylideneacetone)dipalladium(0) [Pd2(dba)3, 0.16 g], dicyclohexyl(2',6'-dimethoxy-[1,1'-biphenyl]-2-yl]phosphine (SPhos, 0.24 g), NaOtBu (2.1 g) and xylene (40 ml) were placed in a flask and heated at 120°C for 1 hour. After the reaction, water and toluene were added to the reaction solution and stirred, and then the organic layer was separated and washed with water. The organic layer was then concentrated to obtain a crude product. The crude product was purified using a silica gel short column (eluent: toluene), and the solvent was concentrated to obtain a crude product, which was then added with heptane and cooled on ice. The precipitated crystals were filtered and washed with heptane to obtain compound (IF) (10.5 g). [ka]

[0694] Compound (IF) (10.5 g) and t-butylbenzene (200 ml) were added to a flask at 0°C under a nitrogen atmosphere with 1.53 M t-butyllithium pentane solution (14.4 ml). After the dropwise addition, the mixture was heated to 60°C and stirred for 0.5 hours, and then components with a boiling point lower than that of t-butylbenzene were distilled off under reduced pressure. The mixture was cooled to -50°C, boron tribromide (5.9 g) was added, and the mixture was heated to room temperature and stirred for 0.5 hours. The mixture was then cooled again to 0°C, N,N-diisopropylethylamine (3.1 g) was added, and the mixture was stirred at room temperature until the heat generation subsided, and then the mixture was heated to 100°C and stirred for 1 hour. The reaction solution was cooled to room temperature, and an aqueous solution of sodium acetate cooled in an ice bath was added, followed by ethyl acetate, and the mixture was stirred for 1 hour. The organic layer was separated and washed twice with water. The organic layer was then concentrated, and the resulting crude product was purified using a silica gel (NH silica) short column (eluent: toluene / heptane = 1 / 9 (volume ratio)). After concentrating the resulting crude product, heptane was added to precipitate crystals, which were then filtered and washed with heptane to obtain compound (1-1301) (1.9 g). [ka]

[0695] The structure of the obtained compound was confirmed by NMR measurement. 1 H-NMR(CDCl3): δ=1.09(s,12H), 1.27(s,12H), 1.42(s,12H), 1.49(s,12H), 1.70-1.80(m,16H), 6. 20(d,2H), 6.56(s,2H), 7.09(dd,2H), 7.25-7.30(m,3H), 7.58(d,2H), 8.91(s,2H).

[0696] Synthesis Example (4): Synthesis of Compound (1-1302) [ka]

[0697] In a nitrogen atmosphere, compound (IG) (8.0 g), compound (IE) (19.7 g), Pd2(dba)3 (0.52 g), SPhos (0.94 g), NaOtBu (5.5 g) and xylene (80 ml) were placed in a flask, heated and stirred at 120°C for 3 hours, and then stirred at 130°C for 1 hour. After the reaction, water and toluene were added to the reaction solution and stirred, and the organic layer was separated and washed with water. The organic layer was then concentrated to obtain a crude product. The crude product was purified using a silica gel column (eluent: toluene / heptane = 10 / 90 (volume ratio) → 15 / 85 (volume ratio)), and the solvent was concentrated to obtain compound (IH) (15.3 g). [ka]

[0698] A 1.53M t-butyllithium pentane solution (13.2ml) was added to a flask containing compound (IH) (15.3g) and t-butylbenzene (100ml) under a nitrogen atmosphere at 0°C. After the dropwise addition, the temperature was raised to 60°C and stirred for 0.5 hours, and then components with a boiling point lower than that of t-butylbenzene were distilled off under reduced pressure. The mixture was cooled to -50°C, boron tribromide (5.3g) was added, the temperature was raised to room temperature and stirred for 0.5 hours. Then, the mixture was cooled again to 0°C, N,N-diisopropylethylamine (2.7g) was added, and the mixture was stirred at room temperature until the heat generation subsided, and then the mixture was heated to 100°C and stirred for 1 hour. The reaction solution was cooled to room temperature, and an aqueous sodium acetate solution cooled in an ice bath was added, followed by ethyl acetate, and the mixture was stirred for 1 hour. The organic layer was separated, washed with water (twice), and the precipitate precipitated by adding heptane was filtered. The precipitate was washed with methanol and water, and the resulting yellow crystals were dissolved in toluene by heating, and then purified with a silica gel short column (eluent: toluene). The solvent was distilled off, and heptane was added to the crude product obtained. The resulting crystals were filtered and further washed with heptane to obtain compound (1-1302) (7.23 g). [ka]

[0699] The structure of the obtained compound was confirmed by NMR measurement. 1 H-NMR(CDCl3): δ=1.07(s,12H), 1.11(s,6H), 1.19(s,6H), 1.24(s,6H), 1.35(s,6H), 1.48(s,12H), 1.68-1.75(m,16H), 5.63(s,2H), 6.55(s,2H), 6.89(t,2H), 6.91-6.92(m,2H), 6.93-6.95(m,4H), 7.04(t,4H), 7.13(dd,2H), 7.37(d,2H), 8.85(s,2H).

[0700] Synthesis Example (5): Synthesis of Compound (1-1823) [ka]

[0701] In a nitrogen atmosphere, compound (II) (35.0 g), 3-bromo-5-t-butyl-benzo[b]thiophene (compound IJ: 17.4 g), Pd(dba)2 (1.86 g), NaOtBu (10.4 g), tri-t-butylphosphonium tetrafluoroborate ([(tBu)3PH]BF4): 1.87 g, and xylene (300 ml) were placed in a flask and heated at 120°C for 1 hour. After the reaction, water and toluene were added to the reaction solution and stirred, and then the organic layer was separated and washed with water. The organic layer was then concentrated to obtain a crude product. The crude product was purified with a silica gel column (eluent: toluene / heptane = 1 / 4 (volume ratio)), and the solvent was concentrated. The glassy solid was dried with a vacuum pump to obtain compound (IK) (35 g). [ka]

[0702] A 1.60M t-butyllithium pentane solution (25.0ml) was added to a flask containing compound (IK) (16.7g) and t-butylbenzene (400ml) under a nitrogen atmosphere at 0°C. After the dropwise addition, the temperature was raised to 60°C and stirred for 0.5 hours, and then components with a boiling point lower than that of t-butylbenzene were distilled off under reduced pressure. The mixture was cooled to -50°C and boron tribromide (10.0g) was added, and the mixture was heated to room temperature and stirred for 0.5 hours. Then, the mixture was cooled again to 0°C and N,N-diisopropylethylamine (5.2g) was added, and the mixture was stirred at room temperature until the heat generation subsided, and then the mixture was heated to 90°C and stirred for 1 hour. The reaction solution was cooled to room temperature, and an aqueous sodium acetate solution cooled in an ice bath was added, followed by toluene, and the mixture was stirred for 1 hour. The toluene solution was concentrated, followed by the addition of heptane, and the mixture was purified using a silica gel column (eluent: toluene / heptane = 1 / 4 (volume ratio)). The obtained crude product was repeatedly recrystallized from toluene to obtain compound (1-1823) (2.8 g). [ka]

[0703] The structure of the obtained compound was confirmed by NMR measurement. 1 H-NMR(CDCl3): δ=0.99(s,9H), 1.11(s,9H), 1.30(s,6H), 1.43(s,3H), 1.46(m,12H), 1.51(s,9H), 1.78-1.86(m,4H), 6.15(s,1H), 6.65(s ,1H), 6.74(s,1H), 7.23-7.29(d,4H), 7.41(d,1H), 7.46(d,1H), 7.53(s,1H), 7.66-7.68(m,3H), 7.90(d,1H), 8.78(s,1H).

[0704] Synthesis Example (6): Synthesis of Compound (1-1821) [ka]

[0705] In a nitrogen atmosphere, compound (IL) (71.0 g), compound (IJ) (37.8 g), Pd(dba)2 (2.14 g), NaOtBu (16.9 g), [(tBu)3PH]BF4 (1.36 g) and xylene (710 ml) were placed in a flask and heated to reflux at 130°C for 1 hour. After the reaction solution was cooled to room temperature, water and toluene were added, and the organic layer was separated and washed with water. This solution was concentrated under reduced pressure, and the residue was purified with a silica gel column (eluent: toluene) and further washed with heptane to obtain compound (IM) (71.3 g). [ka]

[0706] A 1.60M t-butyllithium pentane solution (50.0ml) was added to a flask containing compound (IM) (32.0g) and t-butylbenzene (400ml) under a nitrogen atmosphere at 0°C. After the dropwise addition, the temperature was raised to 60°C and stirred for 0.5 hours, and then components with a boiling point lower than that of t-butylbenzene were distilled off under reduced pressure. The mixture was cooled to -50°C, boron tribromide (20.0g) was added, the mixture was heated to room temperature and stirred for 0.5 hours. The mixture was then cooled again to 0°C, N,N-diisopropylethylamine (10.4g) was added, and the mixture was stirred at room temperature until the heat generation subsided, and then the mixture was heated to 70°C and stirred for 1 hour. The reaction solution was cooled to room temperature, and an aqueous sodium acetate solution cooled in an ice bath was added, followed by ethyl acetate, and the mixture was stirred for 1 hour. The organic layer was separated and washed with water. The solution was concentrated under reduced pressure, and the residue was washed with ethyl acetate, and then purified with a silica gel column (eluent: toluene / heptane = 1 / 1 (volume ratio)). The obtained crude product was washed with heptane to obtain compound (1-1821) (7.1 g). [ka]

[0707] Synthesis Example (7): Synthesis of Compound (1-3623) [ka]

[0708] In a nitrogen atmosphere, compound (IN) (60.0 g), compound (IJ) (28.6 g), Pd(dba)2 (2.93 g), NaOtBu (12.3 g), [(tBu)3PH]BF4 (2.96 g) and xylene (660 ml) were placed in a flask and heated at 120°C for 2 hours. After the reaction solution was cooled to room temperature, water and toluene were added, and the organic layer was separated and washed with water. The solution was concentrated under reduced pressure, and the residue was purified with a silica gel column (eluent: toluene / heptane = 1 / 3 (volume ratio)) and further washed with methanol to obtain compound (IO) (68.0 g). [ka]

[0709] A 1.61M t-butyllithium pentane solution (50.0ml) was added to a flask containing compound (IO) (35.8g) and t-butylbenzene (800ml) under a nitrogen atmosphere at 0°C. After the dropwise addition, the mixture was heated to 60°C and stirred for 0.5 hours, and then components with a boiling point lower than that of t-butylbenzene were distilled off under reduced pressure. The mixture was cooled to -50°C, boron tribromide (20.0g) was added, the mixture was heated to room temperature and stirred for 0.5 hours. The mixture was then heated to 50°C and stirred for 0.5 hours. The reaction solution was cooled to room temperature, and an aqueous sodium acetate solution cooled in an ice bath was added, followed by ethyl acetate, and the mixture was stirred for 1 hour. The organic layer was separated and washed with water. The solution was concentrated under reduced pressure, and the residue was washed with ethyl acetate and then purified with a silica gel column (eluent: toluene). Compound (1-3623) was obtained (9.3g) by further purifying it by recrystallization from toluene. [ka]

[0710] Synthesis Example (8): Synthesis of Compound (1-3621) [ka]

[0711] Under a nitrogen atmosphere, compound (IP) (65.0 g), compound (IJ) (31.7 g), Pd(dba)2 (1.79 g), NaOtBu (14.1 g), [(tBu)3PH]BF4 (1.14 g) and xylene (520 ml) were placed in a flask and heated at 130°C for 2 hours. After the reaction solution was cooled to room temperature, water and toluene were added, and the organic layer was separated and washed with water. The solution was concentrated under reduced pressure, and the residue was purified with a silica gel column (eluent: toluene / heptane = 1 / 4 (volume ratio)). The glassy solid was dried with a vacuum pump to obtain compound (IQ) (52 g). [ka]

[0712] Compound (IQ) (35.0 g) and t-butylbenzene (280 ml) were added to a flask containing 1.60 M t-butyllithium pentane solution (50.0 ml) at 0° C. under a nitrogen atmosphere, and the mixture was heated to 60° C. and stirred for 0.5 hours. The mixture was then cooled to -50° C., boron tribromide (20.6 g) was added, and the mixture was heated to room temperature and stirred for 0.5 hours. The mixture was then cooled again to 0° C., N,N-diisopropylethylamine (10.6 g) was added, and the mixture was stirred at room temperature until the heat generation subsided, and then the mixture was heated to 90° C. and stirred for 1 hour. The reaction solution was cooled to room temperature, and an aqueous sodium acetate solution cooled in an ice bath was added, followed by ethyl acetate, and the mixture was stirred for 1 hour. The organic layer was separated and washed with water. The solution was concentrated under reduced pressure, and the residue was washed with ethyl acetate, and then purified with a silica gel column (eluent: toluene / heptane = 1 / 1 (volume ratio)). The product was further purified by recrystallization from toluene to obtain compound (1-3621) (7.2 g). [ka]

[0713] The structure of the obtained compound was confirmed by NMR measurement. 1H-NMR(CDCl3): δ=1.11(s,9H), 1.19(s,9H), 1.26(s,3H), 1.28(s,3H), 1.37(s,18H), 1.4 4-1.47(m,6H), 1.77-1.86(m,4H), 2.21(s,3H), 6.08(s,1H), 6.10(s,1H), 6.53(d,1H), 6.61(d,1H), 7.20(d,2H), 7.26(dd,1H), 7.31(dd,1H), 7.40( dd,1H), 7.48(d,1H), 7.61(t,1H), 7.66(d,1H), 7.88(d,1H), 8.69(d,1H).

[0714] Synthesis Example (9): Synthesis of Compound (1-1828) [ka]

[0715] Under a nitrogen atmosphere, compound (IR) (63.8 g), compound (IJ) (24.2 g), Pd(dba)2 (0.939 g), NaOtBu (11.8 g), tri-t-butylphosphine ((tBu)3P: 3.27 ml) and toluene (630 ml) were placed in a flask and heated at 110°C for 4 hours. After the reaction solution was cooled to room temperature, water and toluene were added, and the organic layer was separated and washed with water. This solution was concentrated under reduced pressure, and the residue was purified with a silica gel column (eluent: toluene / heptane = 1 / 6 (volume ratio)). The glassy solid was dried with a vacuum pump to obtain compound (IS) (44 g). [ka]

[0716] Compound (IS) (44.3 g) and t-butylbenzene (400 ml) were added to a flask at 0°C under a nitrogen atmosphere with 1.61 M t-butyllithium pentane solution (56.7 ml). After the dropwise addition, the mixture was heated to 60°C and stirred for 0.5 hours, and then components with a boiling point lower than that of t-butylbenzene were distilled off under reduced pressure. The mixture was cooled to -50°C, boron tribromide (22.9 g) was added, and the mixture was heated to room temperature and stirred for 0.5 hours. The mixture was then cooled again to 0°C, N,N-diisopropylethylamine (16.0 g) was added, and the mixture was stirred at room temperature until the heat generation subsided, and then the mixture was heated to 120°C and stirred for 1 hour. The reaction solution was cooled to room temperature, and an aqueous sodium acetate solution and toluene cooled in an ice bath were added and stirred, after which the organic layer was separated and washed with water. The organic layer was then concentrated to obtain a crude product, which was then purified using a silica gel column (eluent: toluene / heptane = 1 / 4 (volume ratio)) and further purified by recrystallization from a mixed solvent of toluene and heptane (toluene / heptane = 1 / 1 (volume ratio)) to obtain compound (1-1828) (5.0 g). [ka]

[0717] The structure of the obtained compound was confirmed by NMR measurement. 1 H-NMR(CDCl3): δ=0.96-0.99(m,9H), 1.10(s,9H), 1.12(s,9H), 1.25-1.32(m,6H), 1.39-1.51(m,24H), 1.76-1.86(m,4H), 6.05-6.28(m,2H), 6.66 -6.80(m,2H), 7.01-7.08(m,2H), 7.12-7.24(m,4H), 7.37-7.47(m,2H), 7.48-7.69(m,3H), 7.70(s,1H), 7.88(d,1H), 8.70(s,1H).

[0718] Synthesis Example (10): Synthesis of Compound (1-3604) [ka]

[0719] Under a nitrogen atmosphere, compound (IT) (49.7 g), compound (IJ) (22.8 g), Pd(dba)2 (2.44 g), NaOtBu (13.6 g), [(tBu)3PH]BF4 (2.46 g) and xylene (600 ml) were placed in a flask and heated at 120°C for 3 hours. After the reaction solution was cooled to room temperature, water and toluene were added, and the organic layer was separated and washed with water. The solution was concentrated under reduced pressure, and the residue was purified with a silica gel column (eluent: heptane), and further purified by recrystallization from heptane to obtain compound (IU) (45 g). [ka]

[0720] A 1.60M t-butyllithium pentane solution (50.0ml) was added to a flask containing compound (IU) (40.4g) and t-butylbenzene (270ml) under a nitrogen atmosphere at 0°C. After the dropwise addition, the temperature was raised to 60°C and stirred for 0.5 hours, and then components with a boiling point lower than that of t-butylbenzene were distilled off under reduced pressure. The mixture was cooled to -50°C and boron tribromide (20.0g) was added, and the mixture was heated to 50°C and stirred for 0.5 hours. The mixture was then cooled again to 0°C and N,N-diisopropylethylamine (10.4g) was added, and the mixture was stirred at room temperature until the heat generation subsided, and then the mixture was heated to 80°C and stirred for 0.5 hours. The reaction solution was cooled to room temperature, and an aqueous solution of sodium acetate cooled in an ice bath was added, followed by ethyl acetate, and the mixture was stirred for 1 hour. The organic layer was separated and washed with water. The solution was concentrated under reduced pressure, and the residue was washed with ethyl acetate, and then purified with a silica gel column (eluent: toluene). The product was further purified by recrystallization from toluene to obtain compound (1-3604) (3.8 g). [ka]

[0721] Synthesis Example (11): Synthesis of Compound (1-1851) [ka]

[0722] In a nitrogen atmosphere, compound (IL) (29.0 g), compound (IV) (18.9 g), Pd(dba)2 (0.55 g), NaOtBu (6.9 g), [(tBu)3PH]BF4 (0.55 g) and xylene (100 ml) were placed in a flask and heated to reflux at 120°C for 1 hour. After the reaction solution was cooled to room temperature, water and ethyl acetate were added, and the organic layer was separated and washed with water. The solution was concentrated under reduced pressure, and the residue was purified with a silica gel column (eluent: toluene / heptane = 1 / 1 (volume ratio)), and after concentration, ethyl acetate was added to the crystals obtained, which were then filtered and washed with methanol to obtain compound (IW) (25.0 g). [ka]

[0723] A 1.60M t-butyllithium pentane solution (39.3ml) was added to a flask containing compound (IW) (25.0g) and t-butylbenzene (160ml) under a nitrogen atmosphere at 0°C. After the dropwise addition, the temperature was raised to 60°C and stirred for 0.5 hours, and then components with a boiling point lower than that of t-butylbenzene were distilled off under reduced pressure. The mixture was cooled to -50°C, boron tribromide (15.7g) was added, and the mixture was heated to room temperature and stirred for 0.5 hours. Then, the mixture was cooled again to 0°C, N,N-diisopropylethylamine (8.1g) was added, and the mixture was stirred at room temperature until the heat generation subsided, and then the mixture was heated to 80°C and stirred for 1 hour. The reaction solution was cooled to room temperature, and an aqueous sodium acetate solution cooled in an ice bath was added, followed by ethyl acetate, and the mixture was stirred for 1 hour. The organic layer was separated and washed with water. This solution was concentrated under reduced pressure, and the residue was washed with ethyl acetate, and then purified with a silica gel column (eluent: toluene / heptane = 2 / 8 (volume ratio)). The obtained crude product was washed with heptane to obtain compound (1-1851) (7.5 g). [ka]

[0724] The structure of the obtained compound was confirmed by NMR measurement. 1 H-NMR(CDCl3): δ=1.23(s,3H), 1.29(s,3H), 1.36(s,9H), 1.46(s,9H), 1.49(s,6H), 1. 51(s,9H), 1.82-1.89(m,4H), 2.22(s,3H), 5.80(d,1H), 5.99(s,1H), 6. 24(s,1H), 6.56(d,1H), 6.92(d,1H), 7.20(dd,1H), 7.22-7.28(m,2H), 7.44-7.47(m,2H), 7.63(d,1H), 7.68(d,2H), 7.96(s,1H), 8.78(d,1H).

[0725] Synthesis Example (12): Synthesis of Compound (1-5121) [ka]

[0726] In a nitrogen atmosphere, compound (IX) (10.0 g), bis(4-t-butylphenyl)amine (5.15 g), Pd-132 (0.13 g), NaOtBu (2.6 g) and xylene (40 ml) were placed in a flask and heated at 120° C. for 1 hour. After the reaction, water and ethyl acetate were added to the reaction solution and stirred, and then the organic layer was separated and washed with water. The organic layer was then concentrated to obtain a crude product. Solmix was added to the crude product, and the precipitated solid was filtered off and washed with methanol. After that, the crude product was purified with a silica gel short column (eluent: toluene / heptane = 1 / 1 (volume ratio)), and ethyl acetate was added to the crude product obtained by concentrating the solvent, and the precipitated crystals were filtered and washed with methanol to obtain compound (IY) (8.5 g). [ka]

[0727] A 1.60M t-butyllithium pentane solution (13.9ml) was added to a flask containing compound (IY) (8.5g) and t-butylbenzene (85ml) under a nitrogen atmosphere at 0°C. After the dropwise addition, the temperature was raised to 60°C and stirred for 0.5 hours, and then components with a boiling point lower than that of t-butylbenzene were distilled off under reduced pressure. The mixture was cooled to -50°C, boron tribromide (5.6g) was added, and the mixture was heated to room temperature and stirred for 0.5 hours. Then, the mixture was cooled again to 0°C, N,N-diisopropylethylamine (2.9g) was added, and the mixture was stirred at room temperature until the heat generation subsided, and then the mixture was heated to 80°C and stirred for 1 hour. The reaction solution was cooled to room temperature, and an aqueous sodium acetate solution cooled in an ice bath was added, followed by ethyl acetate, and the mixture was stirred for 1 hour. The organic layer was washed twice with water, and then concentrated to obtain a crude product. After concentration, Solmix was added, and the precipitated solid was filtered. The crude product was then purified using a silica gel column (eluent: toluene / heptane = 1 / 1 (volume ratio)). The process of adding Solmix to the obtained crude product and filtering the obtained crystals was repeated to obtain compound (1-5121) (3.0 g). [ka]

[0728] The structure of the obtained compound was confirmed by NMR measurement. 1 H-NMR(CDCl3): δ=1.19(s,6H), 1.32(s,6H), 1.46(s,30H), 1.97(s,2H), 2.06(s,2H), 2.18(s,3H), 5.95(s,1H), 6.05(s,1H), 6.36(s,1H) , 6.66(d,1H), 7.10(d,1H), 7.18(dd,1H), 7.27(d,2H), 7.39(d,1H), 7.48(d,1H), 7.67(d,2H), 8.67(s,1H), 8.96(d,1H).

[0729] Synthesis Example (13): Synthesis of Compound (1-2663) [ka]

[0730] In a nitrogen atmosphere, compound (IZ) (20.0 g), compound (IJ) (10.2 g), Pd(dba)2 (0.54 g), NaOtBu (4.6 g), [(tBu)3PH]BF4 (0.55 g) and xylene (60 ml) were placed in a flask and heated to reflux at 120°C for 1 hour. After the reaction solution was cooled to room temperature, water and ethyl acetate were added, and the organic layer was separated and washed with water. This solution was concentrated under reduced pressure, and the residue was purified with a silica gel column (eluent: toluene / heptane = 1 / 1 (volume ratio)), and after concentration, Solmix was added, and the resulting crystals were filtered and washed with methanol to obtain compound (I-1) (24.0 g). [ka]

[0731] A 1.60M t-butyllithium pentane solution (36.5ml) was added to a flask containing compound (I-1) (24.0g) and t-butylbenzene (200ml) under a nitrogen atmosphere at 0°C. After the dropwise addition, the temperature was raised to 60°C and stirred for 0.5 hours, and then components with a boiling point lower than that of t-butylbenzene were distilled off under reduced pressure. The mixture was cooled to -50°C, boron tribromide (14.6g) was added, the mixture was heated to room temperature and stirred for 0.5 hours. Then, the mixture was cooled again to 0°C, N,N-diisopropylethylamine (7.6g) was added, and the mixture was stirred at room temperature until the heat generation subsided, and then the mixture was heated to 80°C and stirred for 1 hour. The reaction solution was cooled to room temperature, and an aqueous sodium acetate solution cooled in an ice bath and then ethyl acetate were added and stirred for 1 hour, and the organic layer was separated and washed with water. The solution was concentrated under reduced pressure, heptane was added to the residue, the precipitated solid was washed with heptane, and then purified with a silica gel column (eluent: toluene / heptane = 1 / 1 (volume ratio)). The crude product obtained was repeatedly added with heptane and the precipitated solid was washed with heptane to obtain compound (1-2663) (5.7 g). [ka]

[0732] The structure of the obtained compound was confirmed by NMR measurement. 1 H-NMR(CDCl3): δ=1.09(s,9H), 1.18(d,6H), 1.32(d,6H), 1.46(d,6H), 1.50(s,9H), 1.52(s,6H), 1.96(s,2H), 2.06(s,2H), 2.21(s,3H), 6.07(s, 2H), 6.25(s,1H), 6.51(s,1H), 7.08(d,1H), 7.17(dd,1H), 7.38-7.41(m,2H), 7.47(d,2H), 7.65(d,2H), 7.88(d,1H), 8.51(s,1H).

[0733] Synthesis Example (14): Synthesis of Compound (1-1826) [ka]

[0734] A 1.60M t-butyllithium pentane solution (75.0ml) was added to a flask containing compound (I-2) (55.5g) and t-butylbenzene (450ml) under a nitrogen atmosphere at 0°C. After the dropwise addition, the mixture was heated to 60°C and stirred for 0.5 hours, and then components with a boiling point lower than that of t-butylbenzene were distilled off under reduced pressure. The mixture was cooled to -50°C, boron tribromide (30.0g) was added, the mixture was heated to room temperature and stirred for 0.5 hours, and then heated to 80°C and stirred for 1 hour. The reaction solution was cooled to room temperature, and an aqueous sodium acetate solution cooled in an ice bath and toluene were added and stirred, after which the organic layer was separated and washed with water. The organic layer was then concentrated, and the residue was purified using a silica gel column (eluent: toluene / heptane = 1 / 1 (volume ratio)). The crude product obtained was washed successively with acetone and heptane to obtain compound (1-1826) (6.60g). [ka]

[0735] The structure of the obtained compound was confirmed by NMR measurement. 1H-NMR(CDCl3): δ=1.09-1.16(m,18H), 1.25-1.34(m,6H), 1.42-1.50(m,24H), 1.76-1.86 (m,4H), 2.19(s,3H), 6.03-6.12(m,2H), 6.57-6.66(m,2H), 7.01-7.08(m, 2H), 7.12-7.25(m,4H), 7.37-7.44(m,2H), 7.48-7.54(m,1H), 7.58(dd,1 H), 7.60-7.67(m,1H), 7.67-7.71(m,1H), 7.88(d,1H), 8.68-8.72(m,1H).

[0736] Synthesis Example (15): Synthesis of Compound (1-3645) [ka]

[0737] A 1.60M t-butyllithium pentane solution (75.0ml) was added to a flask containing compound (I-3) (58.5g) and t-butylbenzene (300ml) under a nitrogen atmosphere at 0°C. After the dropwise addition, the temperature was raised to 60°C and stirred for 0.5 hours, and then components with a boiling point lower than that of t-butylbenzene were distilled off under reduced pressure. The mixture was cooled to -50°C, boron tribromide (30.0g) was added, the mixture was heated to room temperature and stirred for 0.5 hours. Then, the mixture was cooled again to 0°C, N,N-diisopropylethylamine (15.6g) was added, and the mixture was stirred at room temperature until the heat generation subsided, and then the mixture was heated to 80°C and stirred for 1 hour. The reaction solution was cooled to room temperature, and an aqueous sodium acetate solution and toluene cooled in an ice bath were added and stirred, after which the organic layer was separated and washed with water. The organic layer was then concentrated, and the residue was purified with a silica gel column (eluent: toluene / heptane = 1 / 1 (volume ratio)). The obtained crude product was washed with heptane to obtain compound (1-3645) (10.2 g). [ka]

[0738] The structure of the obtained compound was confirmed by NMR measurement. 1 H-NMR(CDCl3): δ=0.98-1.02(m,9H), 1.09-1.14(m,18H), 1.20(s,9H), 1.26-1.34(m,6H), 1.39-1.50(m,15H), 1.75-1.88(m,4H), 6.13-6.35(m,2H) , 6.66-6.73(m,2H), 7.00-7.07(m,2H), 7.12-7.26(m,5H), 7.39(dd,1H), 7.48-7.79(m,3H), 7.71(s,1H), 7.86(d,1H), 8.58(d,1H).

[0739] Synthesis Example (16): Synthesis of Compound (1-5142) [ka]

[0740] A 1.61M t-butyllithium pentane solution (75.0ml) was added to a flask containing compound (I-4) (51.0g) and t-butylbenzene (610ml) under a nitrogen atmosphere at 0°C. After the dropwise addition, the temperature was raised to 60°C and stirred for 0.5 hours, and then components with a boiling point lower than that of t-butylbenzene were distilled off under reduced pressure. The mixture was cooled to -50°C, boron tribromide (30.0g) was added, and the mixture was heated to room temperature and stirred for 0.5 hours. Then, the mixture was cooled again to 0°C, N,N-diisopropylethylamine (14.9g) was added, and the mixture was stirred at room temperature until the heat generation subsided, and then the mixture was heated to 80°C and stirred for 1 hour. The reaction solution was cooled to room temperature, and an aqueous sodium acetate solution and toluene cooled in an ice bath were added and stirred, and the organic layer was separated and washed with water. The organic layer was then concentrated, and the residue was purified with a silica gel column (eluent: toluene / heptane = 7 / 1 (volume ratio)). The obtained crude product was washed with heptane and further purified by recrystallization from toluene to obtain compound (1-5142) (6.51 g). [ka]

[0741] The structure of the obtained compound was confirmed by NMR measurement. 1 H-NMR(CDCl3): δ=1.11(s,9H), 1.18-1.24(m,6H), 1.37-1.45(m,15H), 1.51(s,9H), 1.71-1.80(m,4H), 1.94(s,6H), 6.07(s,1H), 6.11(s,1H), 6.48-6. 55(m,2H), 6.97-7.09(m,3H), 7.23(d,2H), 7.30(dd,1H), 7.39-7.43(m,2H), 7.46(dd,1H), 7.57-7.64(m,3H), 7.91(d,1H), 8.82(d,1H).

[0742] Synthesis Example (17): Synthesis of Compound (1-5151) [ka]

[0743] A 1.61M t-butyllithium pentane solution (75.0ml) was added to a flask containing compound (I-5) (56.5g) and t-butylbenzene (670ml) under a nitrogen atmosphere at 0°C. After the dropwise addition, the temperature was raised to 60°C and stirred for 0.5 hours, and then components with a boiling point lower than that of t-butylbenzene were distilled off under reduced pressure. The mixture was cooled to -50°C, boron tribromide (30.0g) was added, and the mixture was heated to room temperature and stirred for 0.5 hours. Then, the mixture was cooled again to 0°C, N,N-diisopropylethylamine (15.5g) was added, and the mixture was stirred at room temperature until the heat generation subsided, and then the mixture was heated to 80°C and stirred for 1 hour. The reaction solution was cooled to room temperature, and an aqueous sodium acetate solution and toluene cooled in an ice bath were added and stirred, after which the organic layer was separated and washed with water. The organic layer was then concentrated, and the residue was purified with a silica gel column (eluent: toluene / heptane = 7 / 1 (volume ratio)). The obtained crude product was washed successively with acetone and heptane to obtain compound (1-5151) (6.34 g). [ka]

[0744] The structure of the obtained compound was confirmed by NMR measurement. 1 H-NMR(CDCl3): δ=1.11(s,9H), 1.17-1.24(m,15H), 1.32(s,18H), 1.37-1.45(m,6H), 1.71-1.80(m,4H), 1.97(s,6H), 6.11(s,1H), 6.14(s,1H), 6.52 (dd,2H), 6.97-7.09(m,3H), 7.18(d,2H), 7.28-7.34(m,2H), 7.38-7.43(m,2H), 7.52(t,1H), 7.60(d,1H), 7.89(d,1H), 8.72(d,1H).

[0745] Synthesis Example (18): Synthesis of Compound (1-1803) [ka]

[0746] A 1.61M t-butyllithium pentane solution (125ml) was added to a flask containing compound (I-6) (86.6g) and t-butylbenzene (520ml) under a nitrogen atmosphere at 0°C. After the dropwise addition, the temperature was raised to 60°C and stirred for 0.5 hours, and then components with a boiling point lower than that of t-butylbenzene were distilled off under reduced pressure. The mixture was cooled to -50°C, and boron tribromide (51.1g) was added, and the mixture was heated to room temperature and stirred for 2.5 hours. An aqueous sodium acetate solution cooled in an ice bath and toluene were added and stirred, and then the organic layer was separated and washed with water. The organic layer was then concentrated, and the residue was purified with a silica gel column (eluent: toluene / heptane = 1 / 1 (volume ratio)). The obtained crude product was washed successively with acetonitrile and heptane, and further purified by recrystallization from toluene to obtain compound (1-1803) (10.2g). [ka]

[0747] The structure of the obtained compound was confirmed by NMR measurement. 1H-NMR(CDCl3): δ=1.04-1.10(m,15H), 1.25(s,6H), 1.38-1.45(m,6H), 1.49(s,9H), 1.53(s,6H), 1.66-1.83(m,8H), 2.20(s,3H), 6.06(d,2H), 6.4 1(s,1H), 6.50(d,1H), 7.07(dd,1H), 7.26(d,1H), 7.38(dd,1H), 7.46(d,2H), 7.59(d,1H), 7.74(d,2H), 7.88(d,1H), 8.70(d,1H).

[0748] Synthesis Example (19): Synthesis of Compound (1-3644) [ka]

[0749] A 1.61M t-butyllithium pentane solution (150ml) was added to a flask containing compound (I-7) (110g) and t-butylbenzene (1000ml) under a nitrogen atmosphere at 0°C. After the dropwise addition, the temperature was raised to 60°C and stirred for 0.5 hours, and then components with a boiling point lower than that of t-butylbenzene were distilled off under reduced pressure. The mixture was cooled to -50°C, boron tribromide (60.0g) was added, the mixture was heated to room temperature and stirred for 0.5 hours. Then, the mixture was cooled again to 0°C, N,N-diisopropylethylamine (30.6g) was added, and the mixture was stirred at room temperature until the heat generation subsided, and then the mixture was heated to 80°C and stirred for 1 hour. The reaction solution was cooled to room temperature, and an aqueous sodium acetate solution and toluene cooled in an ice bath were added and stirred, after which the organic layer was separated and washed with water. The organic layer was then concentrated, and the residue was purified with a silica gel column (eluent: toluene / heptane = 1 / 5 (volume ratio)). The obtained crude product was washed successively with acetonitrile, acetone, and heptane to obtain compound (1-3644) (11.1 g). [ka]

[0750] The structure of the obtained compound was confirmed by NMR measurement. 1H-NMR(CDCl3): δ=1.10(s,9H), 1.11-1.13(m,9H), 1.16-1.18(m,9H), 1.25-1.36(m,6H), 1.43-1.4 7(m,6H), 1.48(s,9H), 1.77-1.87(m,4H), 2.22(s,3H), 6.07-6.11(m,1H), 6.20(s, 1H), 6.54-6.62(m,2H), 6.99-7.08(m,2H), 7.15-7.30(m,5H), 7.37(dd,1H), 7.46- 7.56(m,1H), 7.58-7.68(m,2H), 7.69-7.73(m,1H), 7.85(d,1H), 8.59-8.55(m,1H).

[0751] Synthesis Example (20): Synthesis of Compound (1-3812) [ka]

[0752] A 1.61M t-butyllithium pentane solution (25.0ml) was added to a flask containing compound (I-8) (21.2g) and t-butylbenzene (170ml) under a nitrogen atmosphere at 0°C. After the dropwise addition, the mixture was heated to 60°C and stirred for 0.5 hours, and then components with a boiling point lower than that of t-butylbenzene were distilled off under reduced pressure. The mixture was cooled to -50°C, boron tribromide (10.0g) was added, heated to room temperature and stirred for 0.5 hours. The mixture was then heated to 80°C and stirred for 1 hour. The reaction solution was cooled to room temperature, and an aqueous sodium acetate solution cooled in an ice bath and toluene were added and stirred, after which the organic layer was separated and washed with water. The organic layer was then concentrated to obtain a crude product, which was purified with a silica gel column (eluent: toluene) and further washed with acetone to obtain compound (1-3812) (5.0g). [ka]

[0753] The structure of the obtained compound was confirmed by NMR measurement. 1H-NMR(CDCl3): δ=0.97(s,9H), 1.10(s,9H), 1.27-1.34(m,33H), 1.40-1.47(m,6H), 1.75-1.90(m,4H), 6.00-6.28(m,2H), 6.36(s,1H), 6.65-6.80(m,1H) , 6.80-6.96(m,1H), 7.00(d,4H), 7.14(d,2H), 7.18-7.26(m,5H), 7.38(d,1H), 7.43-7.58(m,3H), 7.65(d,1H), 7.85(d,1H), 8.53(s,1H).

[0754] Synthesis Example (21): Synthesis of Compound (1-3847) [ka]

[0755] A 1.61M t-butyllithium pentane solution (25.0ml) was added to a flask containing compound (I-9) (23.0g) and t-butylbenzene (140ml) under a nitrogen atmosphere at 0°C. After the dropwise addition, the mixture was heated to 60°C and stirred for 0.5 hours, and then components with a boiling point lower than that of t-butylbenzene were distilled off under reduced pressure. The mixture was cooled to -50°C, boron tribromide (10.0g) was added, the mixture was heated to room temperature and stirred for 0.5 hours. The mixture was then heated to 80°C and stirred for 1 hour. The reaction solution was cooled to room temperature, and an aqueous sodium acetate solution cooled in an ice bath and toluene were added and stirred, after which the organic layer was separated and washed with water. The organic layer was then concentrated to obtain a crude product, which was purified with a silica gel column (eluent: toluene / heptane = 1 / 3 (volume ratio)) and further washed with acetone to obtain compound (1-3847) (2.5g). [ka]

[0756] The structure of the obtained compound was confirmed by NMR measurement. 1H-NMR(CDCl3): δ=1.10(s,9H), 1.17-1.20(m,9H), 1.25-1.38(m,33H), 1.42-1.48(m,6H), 1.76-1.88(m,4H), 2.19(s,3H), 6.02-6.16(m,3H), 6.57-6.62( m,2H), 6.86-6.96(m,7H), 7.01-7.14(m,3H), 7.20(d,4H), 7.36(dd,1H), 7.39-7.50(m,3H), 7.60-7.67(m,1H), 7.83(d,1H), 8.47(d,1H).

[0757] Synthesis Example (22): Synthesis of Compound (1-3842) [ka]

[0758] A 1.61M t-butyllithium pentane solution (50.0ml) was added to a flask containing compound (I-10) (36.6g) and t-butylbenzene (290ml) under a nitrogen atmosphere at 0°C. After the dropwise addition, the temperature was raised to 60°C and stirred for 0.5 hours, and then components with a boiling point lower than that of t-butylbenzene were distilled off under reduced pressure. The mixture was cooled to -50°C, boron tribromide (20.0g) was added, the mixture was heated to room temperature and stirred for 0.5 hours. Then, the mixture was cooled again to 0°C, N,N-diisopropylethylamine (30.6g) was added, and the mixture was stirred at room temperature until the heat generation subsided, and then the mixture was heated to 60°C and stirred for 1 hour. The reaction solution was cooled to room temperature, and an aqueous sodium acetate solution and toluene cooled in an ice bath were added and stirred, and the organic layer was separated and washed with water. The organic layer was then concentrated, and the residue was washed with heptane. The obtained crude product was purified by a silica gel column (eluent: toluene) and further washed with heptane to obtain compound (1-3842) (9.80 g). [ka]

[0759] The structure of the obtained compound was confirmed by NMR measurem...

Claims

1. A polycyclic aromatic compound represented by the following general formula (1), or a multimer of a polycyclic aromatic compound having a plurality of unit structures represented by the following general formula (1), wherein the multimer is a linked multimer in which the unit structures are linked by single bonds, alkylene groups having 1 to 3 carbon atoms, phenylene groups or naphthylene groups, a ring-sharing multimer in which the A ring, B ring or C ring contained in the unit structure is shared by a plurality of unit structures and bonded, or a ring-condensed multimer in which the A ring, B ring or C ring contained in the unit structure is condensed and bonded to each other. A polycyclic aromatic compound or a multimer thereof. 【Chemical 1】 In the above formula (1), The A ring, B ring and C ring are each independently an aryl ring or a heteroaryl ring, and at least one hydrogen in these rings may be substituted with aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl, alkyl, cycloalkyl, alkoxy, aryloxy, triarylsilyl, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl or alkyldicycloalkylsilyl, and at least one hydrogen in these substituents may be substituted with aryl, heteroaryl, alkyl or cycloalkyl. Y １ is B, P, P=O, or P=S, X １ and X ２ are each independently >O, >N-R, >C(-R) ２ , >S or >Se, wherein R of >N-R is a first group of aryl, heteroaryl, alkyl or cycloalkyl, which may be substituted with a second group of alkyl, cycloalkyl, aryl or heteroaryl, and R of >C(-R) ２ is a first group of aryl, alkyl or cycloalkyl, which may be substituted with a second group of hydrogen, alkyl, cycloalkyl, aryl or heteroaryl, and further, at least one of R of >N-R and R of >C(-R) ２ is -O-, -S-, -C(-R) ２ - or a single bond, and may be bonded to at least one of the A ring, B ring and C ring, and R of -C(-R) ２ is hydrogen, alkyl or cycloalkyl At least one hydrogen in the compound or unit structure represented by formula (1) may be substituted with deuterium, cyano or halogen, and In the compound or unit structure represented by formula (1), at least one of ring A, ring B, ring C, aryl and heteroaryl is condensed with at least one cycloalkane, and a total of four hydrogens at the two α-position carbons of the cycloalkane are each independently substituted with aryl, heteroaryl, alkyl or cycloalkyl, and at least one -CH ２ - may be substituted with -O-, However, the following (a) or (b) is essential. (a) Substitution by aryl or heteroaryl which is the second group in R of >N-R. (b) Substitution by aryl or heteroaryl which is the second group in R of >C(-R)2.

2. In the case of a multimer, it is a dimer or trimer having two or three unit structures represented by general formula (1). The polycyclic aromatic compound or a multimer thereof according to claim 1.

3. The polycyclic aromatic compound or a multimer thereof according to claim 1, represented by the following general formula (2). 【Chemical 2】 In the above formula (2), In the a-ring, b-ring, and c-ring, any "−C(−R)=" (where R is R in formula (2)) may be replaced by "−N=", and any "−C(−R)=C(−R)−" (where R is R in formula (2)) may be replaced by "−N(−R)−", "−O−", or "−S−", and the R in said "−N(−R)−" is aryl, alkyl, or cycloalkyl. １ ~R １１ is) may be replaced by "−N=", and any "−C(−R)=C(−R)−" (where R is R in formula (2)) １ ~R １１ is) may be replaced by "−N(−R)−", "−O−", or "−S−", and the R in said "−N(−R)−" is aryl, alkyl, or cycloalkyl. R １ to R １１ are each independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboril, alkyl, cycloalkyl, alkoxy, aryloxy, triarylsilyl, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl or alkyldicycloalkylsilyl, and at least one hydrogen in these may be substituted with aryl, heteroaryl, alkyl or cycloalkyl. Also, R １ to R １１ adjacent groups among them may be bonded to form an aryl ring or a heteroaryl ring together with the a-ring, b-ring or c-ring, and at least one hydrogen in the formed ring may be substituted with aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboril, alkyl, cycloalkyl, alkoxy, aryloxy, triarylsilyl, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl or alkyldicycloalkylsilyl, and at least one hydrogen in these may be substituted with aryl, heteroaryl, alkyl or cycloalkyl. Y １ is B, P, P=O, or P=S, and X １ and X ２ are each independently >O, >N-R, >C(-R) ２ , >S or >Se, wherein R of the >N-R is a first group of aryl having 6 to 12 carbon atoms, heteroaryl having 2 to 15 carbon atoms, alkyl having 1 to 6 carbon atoms or cycloalkyl having 3 to 14 carbon atoms, which may be substituted with a second group of aryl having 6 to 12 carbon atoms or heteroaryl having 2 to 15 carbon atoms, and R of the >C(-R) ２ is a first group of aryl having 6 to 12 carbon atoms, alkyl having 1 to 6 carbon atoms or cycloalkyl having 3 to 14 carbon atoms, which may be substituted with a second group of aryl having 6 to 12 carbon atoms or heteroaryl having 2 to 15 carbon atoms, and at least one of R of the >N-R and R of the >C(-R) ２ may be bonded to at least one of the a-ring, b-ring and c-ring by -O-, -S-, -C(-R) ２ -, or a single bond, and R of the -C(-R) ２ - is alkyl having 1 to 6 carbon atoms or cycloalkyl having 3 to 14 carbon atoms At least one hydrogen in the compound represented by formula (2) may be substituted with deuterium, cyano or halogen. In the case of a multimer, it is a dimer or trimer having two or three unit structures represented by general formula (2), and In the compound represented by formula (2), at least one of the a ring, the b ring, the c ring, the formed ring, the aryl, and the heteroaryl is condensed with at least one cycloalkane having 3 to 24 carbon atoms, and a total of four hydrogens at the two α-position carbons of the cycloalkane are each independently substituted with an aryl having 6 to 30 carbon atoms, a heteroaryl having 2 to 30 carbon atoms, an alkyl having 1 to 24 carbon atoms, or a cycloalkyl having 3 to 24 carbon atoms, and at least one -CH ２ - may be substituted with -O-, However, the following (a) or (b) is essential. Substitution by a second group at R in >N-R. Substitution by a second group at R in >C(-R)2. **Claim 4** In the above formula (2), In the a-ring, b-ring, and c-ring, any "-C(-R)=" (where R is R in formula (2)) １ ~R １１ may be replaced by "-N=", and any "-C(-R)=C(-R)-" (where R is R in formula (2)) １ ~R １１ may be replaced by "-N(-R)-", "-O-", or "-S-", and R in the "-N(-R)-" is aryl having 6 to 12 carbon atoms, alkyl having 1 to 6 carbon atoms, or cycloalkyl having 3 to 14 carbon atoms. R １ ~R １１ are each independently hydrogen, aryl having 6 to 30 carbon atoms, heteroaryl having 2 to 30 carbon atoms, diarylamino (wherein aryl is aryl having 6 to 12 carbon atoms), diarylboryl (wherein aryl is aryl having 6 to 12 carbon atoms), alkyl having 1 to 24 carbon atoms, cycloalkyl having 3 to 24 carbon atoms, triarylsilyl (wherein aryl is aryl having 6 to 12 carbon atoms), or trialkylsilyl (wherein alkyl is alkyl having 1 to 6 carbon atoms), and further, R １ ~R １１ adjacent groups among them may combine with the a-ring, b-ring or c-ring to form an aryl ring having 9 to 16 carbon atoms or a heteroaryl ring having 6 to 15 carbon atoms, and at least one hydrogen in the formed ring may be substituted with aryl having 6 to 10 carbon atoms, alkyl having 1 to 12 carbon atoms, cycloalkyl having 3 to 16 carbon atoms, triarylsilyl (wherein aryl is aryl having 6 to 12 carbon atoms), or trialkylsilyl (wherein alkyl is alkyl having 1 to 5 carbon atoms). Y １ is B, P, P=O, or P=S, and X １ and X ２ are each independently >O, >N-R, >C(-R) ２ or >S, wherein R in >N-R is a first group of aryl having 6 to 10 carbon atoms, alkyl having 1 to 5 carbon atoms or cycloalkyl having 5 to 10 carbon atoms, which may be substituted with a second group of aryl having 6 to 10 carbon atoms, and R in >C(-R) ２ is a first group of aryl having 6 to 10 carbon atoms, alkyl having 1 to 5 carbon atoms or cycloalkyl having 5 to 10 carbon atoms, which may be substituted with a second group of aryl having 6 to 10 carbon atoms, and is hydrogen at least one hydrogen in the compound represented by formula (2) may be substituted with deuterium, cyano or halogen, in the case of a multimer, it is a dimer or trimer having two or three unit structures represented by general formula (2), and in the compound represented by formula (2), at least one of the a-ring, the b-ring, the c-ring, the formed ring, the aryl and the heteroaryl is condensed with at least one cycloalkane having 3 to 20 carbon atoms, and a total of four hydrogens at the two α-position carbons of the cycloalkane are each independently substituted with an aryl having 6 to 16 carbon atoms, a heteroaryl having 2 to 22 carbon atoms, an alkyl having 1 to 12 carbon atoms or a cycloalkyl having 3 to 16 carbon atoms, provided that at least one of the following (a) or (b) is essential: Substitution by a second group at R in >N-R; Substitution by a second group at R in >C(-R)2; The polycyclic aromatic compound or its multimer according to claim 3. **Claim 5** In the above formula (2), In the a-ring, b-ring, and c-ring, any “-C(−R)=C(−R)-” (where R is R in formula (2)) １ ~R １１ may be replaced by “-S-”. R １ ~R １１ are each independently hydrogen, aryl having 6 to 16 carbon atoms, heteroaryl having 2 to 20 carbon atoms, diarylamino (wherein aryl is aryl having 6 to 10 carbon atoms), alkyl having 1 to 12 carbon atoms or cycloalkyl having 3 to 16 carbon atoms, Y １ is B, P, P=O or P=S, and X １ and X ２ is each independently >O, >N-R or >C(-R) ２ wherein R of >N-R is a first group of aryl having 6 to 10 carbon atoms, alkyl having 1 to 5 carbon atoms or cycloalkyl having 5 to 10 carbon atoms, which may be substituted with a second group of aryl having 6 to 10 carbon atoms, and R of >C(-R) ２ is a first group of aryl having 6 to 10 carbon atoms, alkyl having 1 to 5 carbon atoms or cycloalkyl having 5 to 10 carbon atoms, which may be substituted with a second group of aryl having 6 to 10 carbon atoms, and is hydrogen at least one hydrogen in the compound represented by formula (2) may be substituted with deuterium, cyano or halogen, in the case of a multimer, it is a dimer or trimer having two or three unit structures represented by general formula (2), and in the compound represented by formula (2), at least one of the a-ring, the b-ring, the c-ring, and the aryl having 6 to 10 carbon atoms as R in >N-R is condensed with at least one cycloalkane having 3 to 16 carbon atoms, and a total of four hydrogens at the two α-position carbons of the cycloalkane are each independently substituted with an alkyl having 1 to 6 carbon atoms or a cycloalkyl having 3 to 14 carbon atoms, provided that at least one of the following (a) or (b) is essential: Substitution by a second group at R in >N-R; Substitution by a second group at R in >C(-R)2; The polycyclic aromatic compound or its multimer according to claim 3. **Claim 6** R １ to R １１ each independently represents hydrogen, aryl having 6 to 16 carbon atoms, diarylamino (wherein aryl is aryl having 6 to 10 carbon atoms), alkyl having 1 to 12 carbon atoms or cycloalkyl having 3 to 16 carbon atoms, Y １ is B, X １ and X ２ are both > N-R, or X １ is > N-R and X ２ is > O, and the R in > N-R is a first group of aryl having 6 to 10 carbon atoms, alkyl having 1 to 5 carbon atoms or cycloalkyl having 5 to 10 carbon atoms, which may be substituted with a second group of aryl having 6 to 10 carbon atoms, At least one hydrogen in the compound represented by formula (2) may be substituted with deuterium or halogen, in the case of a multimer, it is a dimer or trimer having two or three unit structures represented by general formula (2), and In the compound represented by formula (2), at least one of the a-ring, the b-ring, the c-ring, and the aryl having 6 to 10 carbon atoms as R of the >N-R is condensed with a cycloalkane having 3 to 14 carbon atoms, and a total of 4 hydrogens at the two α-position carbons of the cycloalkane are substituted with an alkyl having 1 to 5 carbon atoms. However, the following (a) is essential. (a) Substitution by the second group in R of the >N-R; The polycyclic aromatic compound or its multimer according to claim 3.

7. The polycyclic aromatic compound or its multimer according to any one of claims 1 to 6, which is substituted with a diarylamino group condensed with a cycloalkane, a carbazolyl group condensed with a cycloalkane, or a benzocarbazolyl group condensed with a cycloalkane.

8. R ２ is the polycyclic aromatic compound or its multimer according to any one of claims 3 to 6, which is a diarylamino group condensed with a cycloalkane or a carbazolyl group condensed with a cycloalkane.

9. The polycyclic aromatic compound or its multimer according to claim 7 or 8, wherein the cycloalkane is a cycloalkane having 3 to 20 carbon atoms.

10. The polycyclic aromatic compound or its multimer according to any one of claims 1 to 9, wherein the halogen is fluorine.

11. A material for an organic device, containing the polycyclic aromatic compound or its multimer according to any one of claims 1 to 10.

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

13. The material for an organic device according to claim 12, wherein the material for an organic electroluminescent element is a material for a light emitting layer.

14. An ink composition containing the polycyclic aromatic compound or its multimer according to any one of claims 1 to 10 and an organic solvent.

15. An organic electroluminescent element having a pair of electrodes composed of an anode and a cathode, and an organic layer disposed between the pair of electrodes and containing the polycyclic aromatic compound or its multimer according to any one of claims 1 to 10.

16. The organic electroluminescent element according to claim 15, wherein the organic layer is a light emitting layer.

17. The organic electroluminescent element according to claim 16, wherein the light emitting layer contains a host and the polycyclic aromatic compound or its multimer as a dopant.

18. The organic electroluminescent element according to claim 17, wherein the host is an anthracene-based compound, a fluorene-based compound, or a dibenzocrisene-based compound.

19. having at least one layer of an electron transport layer and an electron injection layer disposed between the cathode and the light-emitting layer, and at least one of the electron transport layer and the electron injection layer contains at least one selected from the group consisting of 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, the organic electroluminescent device according to any one of claims 15 to 18.

20. The organic electroluminescent device according to claim 19, wherein at least one layer 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.

21. A display device or a lighting device including the organic electroluminescent device according to any one of claims 15 to 20.

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